Surfactant compounds and agrochemical compositions
Compounds of the formula: R 1 R 2 N—CH 2 —CHO[(AO) m1 R 4 ]—CH 2 —OR 3 where R 1 is alkoxylated polyhydroxy hydrocarbyl; R 2 is as defined for R 1 , or hydrocarbyl, particularly alkyl or alkoxyalkyl, alkoxylated hydroxyalkyl, or a group: —CH 2 —CHO[(AO) ml R 4 ]—CH 2 —OR 3 ; R 3 is hydrocarbyl; AO is alkyleneoxy; ml is from 0 to 50; such that the average total number of alkyleneoxy groups in the molecule is from 3 to 50; and R 4 is hydrogen, or alkyl, are useful as agrochemical adjuvants. The agrochemical can be a plant growth regulator, herbicide, and/or pesticide, for example insecticide, fungicide, acaricide, nematocide, miticide, rodenticide, bactericide, molluscicide and/or bird repellent. Particularly useful formulations include water soluble herbicide(s), particularly such as glyphosate, glufosinate and paraquat.
1 . A compound of the formula (I):
R 1 R 2 N—CH 2 —CHO[(AO) m1 R 4 ]—CH 2 —OR 3 (I)
where
R 1 is an alkoxylated polyhydroxy hydrocarbyl group; or
R 2 is independently a group as defined for R 1 ; hydrocarbyl, particularly alkyl; alkoxyalkyl; optionally end-capped alkoxylated hydroxyalkyl; or
R 2 is a group of the formula: —CH 2 —CHO[(AO) m1 R 4 ]—CH 2 —OR 3 where AO, m1, R 4 and R 3 are each independently as defined below;
R 3 is hydrocarbyl, usually C 6 to C 30 , particularly C 8 to C 30 , more particularly C 10 to C 20 , especially alkyl, alkenyl, alkaryl, aryl or aralkyl;
each AO is independently an alkyleneoxy group, particularly a C 2 to C 4 alkyleneoxy group, especially a C 2 or C 3 alkyleneoxy group, or a mixture of C 2 and C 3 alkyleneoxy groups;
m1 is from 0 to 50, but usually at least 0.1, and desirably from 0.5 to 20; and
R 4 is hydrogen, or alkyl;
such that the average total number of alkyleneoxy groups in the molecule is at least 3.
2 . An alkoxylated compound of the formula (II)
R 1a R 2a N—CH 2 —CHOH—CH 2 —OR 3 (II)
where
R 1a is a polyhydroxy hydrocarbyl group;
R 2a is independently a group as defined for R a, or is hydrocarbyl, particularly alkyl or alkoxyalkyl or hydroxyalkyl, or is a group of the formula: —CH 2 —CHOH—CH 2 —OR 3 where R 3 is hydrocarbyl,
in which the average total number of alkyleneoxy groups in the molecule is at least 3.
3 . A compound as claimed in claim 1 wherein R 1 is a group of the formula (III):
—R 5 [—O(AO) m3 —R 6 ]n (III)
where
R 5 is the residue of a hydrocarbyl group;
R 6 is hydrogen, or alkyl;
AO is an alkyleneoxy group;
m3 is an average value of from 1 to 20; and
n is from 3 to 10.
4 . A compound as claimed in claim 3 wherein R 5 is the residue (notionally obtained by removing hydroxyl groups from the parent group) of a polyhydroxy alkyl group having a linear C 4 to C 7 chain.
5 . A compound as claimed in claim 3 wherein n is from 3 to 6.
6 . A compound as claimed in claim 1 wherein R 2 is an alkyl group and R 3 is a C 10 to C 30 alkyl, alkenyl, alkaryl, aryl or aralkyl group.
7 . A compound as claimed in claim 1 wherein the alkyleneoxy group (s) AO is(are) ethyleneoxy, propyleneoxy or mixtures of ethyleneoxy and propyleneoxy groups.
8 . A compound as claimed in claim 6 wherein the total number of alkyleneoxy groups in the compound of the formula (I) is from 5 to 30.
9 . An agrochemical composition including as adjuvant a compound of the formula (I) as claimed in claim 1 .
10 . A composition as claimed in claims 9 wherein the agrochemically active compound is one or more plant growth regulators, herbicides, and/or pesticides, for example insecticides, fungicides, acaricides, nematocides, miticides, rodenticides, bactericides, molluscicides and/or bird repellants.
11 . A composition as claimed in claim 9 wherein the agrochemically active compound is or includes at least one water soluble herbicide.
12 . A composition as claimed in claim 10 wherein the water soluble herbicide is or includes at least one phosphonomethyl glycine ; at least one phosphinyl amino acid; and/or at least one bipyridinium compound.
13 . A composition as claimed in any claim 9 which additionally includes at least one further surfactant.
14 . A composition as claimed in claim 13 which additionally includes at least one alkylpolysaccharide surfactant.
15 . A method of treating vegetation by applying to plants and/or soil a composition as claimed in claim 9 .
16 . A method of killing or inhibiting vegetation by applying a formulation as claimed in claim 9 which includes one or more growth regulators and/or herbicides and at least one compound of the general formula (I) as defined in any one of claims 1 to 6 as an adjuvant.
17 . A method of killing plant pests by applying a formulation as claimed in claim 9 which includes one or more pesticides, fungicides or acaricides, and at least one compound of the general formula (I) as defined in any one of claims 1 to 6 as an adjuvant.