WO2021224018A1

WO2021224018A1 - Co-emulsifier which readily micellises in water

Info

Publication number: WO2021224018A1
Application number: PCT/EP2021/060594
Authority: WO
Inventors: Gordon Alastair Bell
Original assignee: Syngenta Crop Protection Ag
Priority date: 2020-05-06
Filing date: 2021-04-22
Publication date: 2021-11-11
Also published as: GB202006704D0

Abstract

The present invention describes linear compounds comprising hydrophobic tails, multiple ethoxylates and a C4-C6 end cap. The invention also relates to compositions comprising these compounds, in particular watery compositions, across a wide range of temperatures and compositions, and their use as surfactants, emulsifiers or co-emulsifiers for agrochemical compositions.

Description

Co-emulsifier Which Readily Micellises in Water

Field of the Invention

The present invention describes linear or branched compounds comprising hydrophobic tails, multiple ethoxylates and a butyl, pentyl or hexyl end cap. These compounds surprisingly form micellar solutions but not lamellar or hexagonal phase liquid crystals upon dilution in water, across a wide range of temperatures and compositions. These compounds are therefore useful as surfactants, emulsifiers or co-emulsifiers.

Background of the Invention

A variety of adjuvants are available to enhance the biological effectiveness of active ingredients such as agrochemicals. Adjuvants commonly make use of surfactant properties to enhance the biological effectiveness of active ingredients.

Many surfactants used for oil-in-water emulsion formation require a co-surfactant in order to provide a stable and readily dilutable product. These co-emulsifiers enhance the use of an emulsifier. Typically an emulsifier for use in the preparation of oil-in-water emulsions will have a hydrophilic-lipophilic balance (HLB) value (Griffin) of between 8 and 16. Co emulsifiers however generally have lower HLB values, often from about 6 to 10.

A problem with co-emulsifiers is the formation of liquid crystalline phases on dilution in water which thereby potentially form gels or viscous compositions. Co-emulsifiers are used across a wide range of concentrations, compositions and temperatures and the existence of these liquid crystals leads to bulk phase separation of the co-emulsifier from the water, thereby negating their intended use.

One class of adjuvants combines a lipophilic alkyl or aryl group with a hydrophilic polyethoxylate group and are known in the art.

W02003022048 discloses long polyethoxylate or polypropoxylate containing surfactants having a long alkyl or alkenyl chain and a short alkyl end-cap, but does not show that these surfactants form micelles and not lamellar phase liquid crystals upon dilution in water across a wide range of temperatures and compositions. EP0577065A1 discloses certain silicone surfactants with a terminal tertiary butyl group. However, these surfactants are intended for manufacture of high resilience polyurethane foam and do not indicate the formation of micelles and the avoidance of the formation of lamellar phase liquid crystals or gelling in water.

US5847229A discloses a manufacturing method for the preparation of butyl end-capped surfactants with a long alkyl or alkenyl group. However, these surfactants are intended as anti-foaming agents and are structurally different from those of the non-gelling compounds of the present invention. Moreover, US5847229A describes a process of production and does not teach how to design compounds that form micelles and do not form lamellar phase liquid crystals or gel in water.

EP0054895A1 discloses polyethoxylate or polypropoxylate containing C1-C4 alkyl end- capped surfactants which have anti-foaming properties and are used in combination with quaternary ammonium cations. It does not teach that the surfactants form micelles and do not form lamellar phase liquid crystals or gel in water.

Therefore there remains a need to identify compounds that do not form lamellar phase liquid crystals, gel or become highly viscous upon dilution in water across a wide range of temperatures and compositions.

Summary of the Invention

The compounds of this invention do not form lamellar or hexagonal phase liquid crystals or gel on dilution into water, but surprisingly form micelles. As a result they are useful as for example co-emulsifiers in the preparation of an oil-in-water emulsion.

Aspects of the current invention provide linear or branched compounds comprising hydrophobic tails, multiple ethoxylates and a C4-C6 end cap. Compositions comprising these compounds as well as uses thereof and of the compounds themselves are also aspects of the present invention. Specifically, uses of the compounds and compositions for agriculture are provided.

The object of the present invention is therefore to provide compounds of formula (I):

wherein R is selected from C4-C18 alkyl, C4-C18 alkenyl or C4-Cisalkynyl;

R’ is selected from C4-C6 alkyl, C4-C6 alkenyl or C4-C6 alkynyl; and a is an integer of from 3 to 10.

It is a further object to provide a composition comprising the compound according to, wherein the concentration of the compound is from 1 to 99 % by weight.

It is yet a further object to provide a composition comprising the compound according to formula (I), wherein the temperature of the composition is from 0 to 40 °C.

In a further aspect, a composition comprising the compound according to formula (I) is provided, wherein the composition is a micellar solution at a temperature of from 10 to 30 °C.

In yet a further aspect, a composition comprising the compound according to formula (I) and a surfactant, emulsifier or co-emulsifier is provided.

In another aspect, an agrochemical composition comprising the compound according to formula (I) and a pesticide, fungicide, insecticide or a herbicide is provided.

It is a further object to provide a composition comprising the compound according to formula (I) and water.

It is yet a further object to provide a method of preparing an emulsion comprising the compound according to formula (I).

In a further aspect, a method of controlling pests or controlling or preventing undesirable plant growth, comprising applying an agrochemical composition comprising the compound according to formula (I) and a pesticide, fungicide, insecticide or a herbicide to pests or plants, to parts thereof or to the locus thereof with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body, is provided.

In an aspect, a method of protecting plant propagation material from the attack by pests, comprising treating the propagation material or the site, where the propagation material is planted, with an agrochemical composition comprising the compound according to formula (I) and a pesticide, fungicide, insecticide or a herbicide, is provided.

It is an object to provide a method of controlling pests or controlling or preventing undesirable plant growth, comprising the following steps: a. obtaining the compound according to formula (I) and obtaining a pesticide, fungicide, insecticide or herbicide; b. mixing the compound according to formula (I) and the pesticide, fungicide, insecticide or herbicide; and c. applying the resulting composition to pests or plants, to parts thereof or to the locus thereof with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

It is a further object to provide a use of the compound according to formula (I) as a surfactant, emulsifier or co-emulsifier.

It is yet a further object to provide a use of the compound according to formula (I) to encapsulate another compound.

It is yet a further object to provide a use of the compound according to formula (I) as an adjuvant.

It is yet a further object to provide a use of the compound according to formula (I) as a tank- mix adjuvant for an agrochemical composition.

And in yet another aspect of the invention, plant propagation material treated with an agrochemical composition comprising the compound according to formula (I) and a pesticide, fungicide, insecticide or a herbicide, is provided.

Detailed Description of the Invention

The present invention describes linear compounds comprising hydrophobic tails, multiple ethoxylates and a C₄-C₆ end cap. These compounds surprisingly form micelles and not lamellar or hexagonal phase liquid crystals upon dilution in water across a wide range of temperatures and compositions. These compounds are therefore useful as surfactants, emulsifiers or co-emulsifiers. The present invention accordingly relates to compounds of formula (I):

wherein R is selected from C4-C18 alkyl, C4-C18 alkenyl or C4-Cisalkynyl;

As used herein, the term "C4-C18 alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from four to eighteen carbon atoms, and which is attached to the rest of the molecule by a single bond. C4-C6 alkyl is to be construed accordingly. Examples of C4-C18 alkyl include, but are not limited to, pentyl, isobutyl, n-butyl, 1-dimethylethyl (t-butyl) and octadecyl.

As used herein, the term "C4-C18 alkenyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one double bond that can be of either the (E) or (Z) configuration, having from four to eighteen carbon atoms, which is attached to the rest of the molecule by a single bond. C4-C6 alkenyl is to be construed accordingly. Examples of C4-C18 alkenyl include, but are not limited to, but-1-enyl, deca-1,9-dienyl and 9-octadecenyl.

As used herein, the term "C4-C18 alkynyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from four to eighteen carbon atoms, which is attached to the rest of the molecule by a single bond. C4-C6 alkynyl is to be construed accordingly. Examples of C4-C18 alkynyl include, but are not limited to, 2-butynyl and octynyl.

Preferably a is an integer of from 3 to 10, from 4 to 10, from 5 to 10, from 6 to 10, from 7 to 10, from 8 to 10, from 9 to 10, from 3 to 9, from 4 to 9, from 5 to 9, from 6 to 9, from 7 to 9, from 8 to 9, from 3 to 8, from 4 to 8, from 5 to 8, from 6 to 8, from 7 to 8, from 3 to 7, from 4 to 7, from 5 to 7, from 6 to 7, from 3 to 6, from 4 to 6, from 5 to 6, from 3 to 5, from 4 to 5 or from 3 to 4.

Preferably R’ contains 4, 5 or 6 carbon atoms. Preferably R’ is linear. Preferably R’ is branched. Preferably R’ is selected from C4-C6 alkyl, C4-C6 alkenyl or C4-C6 alkynyl. Preferably R’ is selected from C4-C5 alkyl, C4-C5 alkenyl or C4-C5 alkynyl. Preferably R’ is selected from C₄ alkyl, C₄ alkenyl or C₄ alkynyl. Preferably R’ is C₄ alkyl. Preferably R’ is tert- butyl.

Preferably R is C4-C15 alkyl, C4-C15 alkenyl or C4-C15 alkynyl. Preferably R is C15-C18 alkyl, C15-C18 alkenyl or C15-C18 alkynyl. Preferably R is C4-C9 alkyl, C4-C9 alkenyl or C4-C9 alkynyl.

Preferably R is C4-C7 alkyl, C4-C7 alkenyl or C4-C7 alkynyl. Preferably R is C11-C18 alkyl, Cn- C18 alkenyl or C11-C18 alkynyl. Preferably R is C4-C11 alkyl, C4-C11 alkenyl or C4-C11 alkynyl. Preferably R is C13-C17 alkyl, C13-C17 alkenyl or C13-C17 alkynyl. Preferably R is linear. Preferably R is branched.

Preferably, when a is 7, 8, 9 or 10, then R is not C12 or C18 alkyl, C12 or C18 alkenyl or C12 or C18 alkynyl. Preferably, when a is 8, 9 or 10, then R is not Cie or C17 alkyl or Ci₆or C17 alkenyl. Preferably, when a is 8 or 10, then R is not Cs or C10 alkyl. Preferably, when a is 7, then R is not C10-C14 alkyl. Preferably, when a is 10, then R is not C10-C12 alkyl.

Compounds of formula (I) with preferred combinations of a and R are illustrated in the Tables 1 to 28 below, wherein Table A describes a and Table B describes R.

Table A:

Table B:

Table 1: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 3.10.R4 - 3.10.R18, wherein 3.10 is defined in table A, and R4 - R18 are defined in Table B. Table 2: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 4.10.R4 - 4.10.R18, wherein 4.10 is defined in table A, and R4 - R18 are defined in Table B.

Table 3: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 5.10.R4 - 5.10.R18, wherein 5.10 is defined in table A, and R4 - R18 are defined in Table B.

Table 4: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 6.10.R4 - 6.10.R18, wherein 6.10 is defined in table A, and R4 - R18 are defined in Table B.

Table 5: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 7.10.R4 - 7.10.R18, wherein 7.10 is defined in table A, and R4 - R18 are defined in Table B.

Table 6: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 8.10.R4 - 8.10.R18, wherein 8.10 is defined in table A, and R4 - R18 are defined in Table B. Table 7: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 9.10.R4 - 9.10.R18, wherein 9.10 is defined in table A, and R4 - R18 are defined in Table B. Table 8: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 3.9.R4 - 3.9.R18, wherein 3.9 is defined in table A, and R4 - R18 are defined in Table B.

Table 9: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 4.9.R4 - 4.9.R18, wherein 4.9 is defined in table A, and R4 - R18 are defined in Table B.

Table 10: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 5.9.R4 - 5.9.R18, wherein 5.9 is defined in table A, and R4 - R18 are defined in Table B.

Table 11: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 6.9.R4 - 6.9.R18, wherein 6.9 is defined in table A, and R4 - R18 are defined in Table B.

Table 12: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 7.9.R4 - 7.9.R18, wherein 7.9 is defined in table A, and R4 - R18 are defined in Table B.

Table 13: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 8.9.R4 - 8.9.R18, wherein 8.9 is defined in table A, and R4 - R18 are defined in Table B.

Table 14: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 3.8.R4 - 3.8.R18, wherein 3.8 is defined in table A, and R4 - R18 are defined in Table B.

Table 15: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 4.8.R4 - 4.8.R18, wherein 4.8 is defined in table A, and R4 - R18 are defined in Table B.

Table 16: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 5.8.R4 - 5.8.R18, wherein 5.8 is defined in table A, and R4 - R18 are defined in Table B.

Table 17: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 6.8.R4 - 6.8.R18, wherein 6.8 is defined in table A, and R4 - R18 are defined in Table B. Table 18: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 7.8.R4 - 7.8.R18, wherein 7.8 is defined in table A, and R4 - R18 are defined in Table B.

Table 19: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 3.7.R4 - 3.7.R18, wherein 3.7 is defined in table A, and R4 - R18 are defined in Table B.

Table 20: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 4.7.R4 - 4.7.R18, wherein 4.7 is defined in table A, and R4 - R18 are defined in Table B.

Table 21: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 5.7.R4 - 5.7.R18, wherein 5.7 is defined in table A, and R4 - R18 are defined in Table B.

Table 22: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 6.7.R4 - 6.7.R18, wherein 6.7 is defined in table A, and R4 - R18 are defined in Table B.

Table 23: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 3.6. R4 - 3.6.R18, wherein 3.6 is defined in table A, and R4 - R18 are defined in Table B.

Table 24: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 4.6. R4 - 4.6.R18, wherein 4.6 is defined in table A, and R4 - R18 are defined in Table B.

Table 25: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 5.6. R4 - 5.6.R18, wherein 5.6 is defined in table A, and R4 - R18 are defined in Table B.

Table 26: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 3.5.R4 - 3.5.R18, wherein 3.5 is defined in table A, and R4 - R18 are defined in Table B.

Table 27: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 4.5.R4 - 4.5.R18, wherein 4.5 is defined in table A, and R4 - R18 are defined in Table B. Table 28: This table discloses 15 preferred combinations of compounds of formula (I), here named formula 3.4. R4 - 3.4.R18, wherein 3.4 is defined in table A, and R4 - R18 are defined in Table B.

Because the compounds of the present invention readily form micelles upon dilution in water across a very wide range of temperatures and compositions, several embodiments can be foreseen.

One such embodiment of the present invention is a composition comprising the compound according to formula (I), wherein the concentration of the compound is from 1 to 99 % by weight. Preferably, the concentration of the compound by weight is in any range from 1 to 95 %, from 1 to 90 %, from 1 to 80 %, from 1 to 70 %, from 1 to 60 %, from 1 to 50 %, from 1 to 40 %, from 1 to 30 %, from 1 to 25 %, from 1 to 20 %, from 1 to 15 %, from 1 to 10 % or from 1 to 5 %. Preferably, the concentration of the compound by weight is in any range from 5 to 99 %, from 5 to 90 %, from 5 to 80 %, from 5 to 70 %, from 5 to 60 %, from 5 to 50 %, from 5 to 40 %, from 5 to 30 %, from 5 to 25 %, from 5 to 20 %, from 5 to 15 % or from 5 to 10 %. Preferably, the concentration of the compound by weight is in any range from 10 to 99 %, from 10 to 90 %, from 10 to 80 %, from 10 to 70 %, from 10 to 60 %, from 10 to 50 %, from 10 to 40 %, from 10 to 30 %, from 10 to 25 %, from 10 to 20 % or from 10 to 15 %.

Another embodiment of the present invention is a composition comprising the compound according to formula (I), wherein the temperature of the composition is maintained at from 0 to 40 °C. Preferably, the temperature of the composition is in any range from 0 to 35 °C, from 0 to 30 °C, from 0 to 25 °C, from 0 to 20 °C, from 0 to 15 °C, from 0 to 10 °C or from 0 to 5 °C. Preferably, the temperature of the composition is in any range from 5 to 40 °C, from 5 to 35 °C, from 5 to 30 °C, from 5 to 25 °C, from 5 to 20 °C, from 5 to 15 °C or from 5 to 10 °C. Preferably, the temperature of the composition is in any range from 10 to 40 °C, from 10 to 35 °C, from 10 to 30 °C, from 10 to 25 °C, from 10 to 20 °C or from 10 to 15 °C.

Another embodiment of the present invention is a composition comprising the compound according to formula (I), wherein the compound is a micellar solution at a temperature of from 0 to 40 °C. Preferably, the compound is a micellar solution at a temperature in any range of from 0 to 35 °C, from 0 to 30 °C, from 0 to 25 °C, from 0 to 20 °C, from 0 to 15 °C, from 0 to 10 °C or from 0 to 5 °C. Preferably, the compound is a micellar solution at a temperature in any range of from 5 to 40 °C, from 5 to 35 °C, from 5 to 30 °C, from 5 to 25 °C, from 5 to 20 °C, from 5 to 15 °C or from 5 to 10 °C. Preferably, the compound is a micellar solution at a temperature in any range of from 10 to 40 °C, from 10 to 35 °C, from 10 to 30 °C, from 10 to 25 °C, from 10 to 20 °C or from 10 to 15 °C.

Preferably, the compound according to formula (I) is a micellar solution, wherein the solution comprises water. Preferably, the compound according to formula (I) is a micellar solution in water.

Preferably the compound according to formula (I) is a homogeneous, opaque or transparent micellar solution.

A micellar solution is formed when the concentration of the compound according to formula (I) exceeds the critical micellar concentration and is maintained until the compound according to formula (I) forms a lyotropic liquid crystal phase such as a lamellar, hexagonal or cubic phase liquid crystal. A micellar solution can be confirmed by visual inspection by appearing homogeneous, opaque or transparent. A micellar solution ceases to be a micellar solution when the solution forms lamellar phase liquid crystals, gels or becomes viscous.

This may advantageously be determined by measuring the viscosity development by a suitable method, e.g. by using a rotational viscometer, or light diffraction, where the solution at gelation forms lamellar phase liquid crystals induces a change in the way it diffracts the light. Micellar solutions may usually be poured through a British standard 100 mesh sieve whereupon they will not leave a residue. Typically lamellar, hexagonal, cubic and many inverse phases will collect on the mesh.

Any composition comprising the compound according to formula (I) preferably comprises water.

Compounds according to formula (I) form micelles and not lamellar or hexagonal phase liquid crystals upon dilution in water and are therefore useful as surfactants, emulsifiers or co-emulsifiers.

An embodiment of the present invention is a composition comprising the compound according to formula (I) and a surfactant, emulsifier or co-emulsifier.

Another embodiment of the present invention is an agrochemical composition comprising the compound according to formula (I) and a pesticide, fungicide, insecticide or a herbicide. Such compositions are useful for controlling pests or controlling or preventing undesirable plant growth. An embodiment of the present invention is a method of controlling pests or controlling or preventing undesirable plant growth, comprising applying an agrochemical composition comprising the compound according to formula (I) and a pesticide, fungicide, insecticide or a herbicide to pests or plants, to parts thereof or to the locus thereof with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

Another embodiment is a method of protecting plant propagation material from the attack by pests, comprising treating the propagation material or the site, where the propagation material is planted, with an agrochemical composition comprising the compound according to formula (I) and a pesticide, fungicide, insecticide or a herbicide.

Therefore another embodiment of the present invention is plant propagation material treated with an agrochemical composition comprising the compound according to formula (I) and a pesticide, fungicide, insecticide or a herbicide.

Various methods of controlling pests or controlling or preventing undesirable plant growth are known in the art. One such a method is an embodiment of the present invention and is a method of controlling pests or controlling or preventing undesirable plant growth, comprising the following steps: a. obtaining the compound according to formula (I) and obtaining a pesticide, fungicide, insecticide or herbicide; b. mixing the compound according to formula (I) and the pesticide, fungicide, insecticide or herbicide; and c. applying the resulting composition to pests or plants, to parts thereof or to the locus thereof with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

The compounds according to formula (I) do not form lamellar or hexagonal phase liquid crystals on dilution into water. As a result they are valuable as co-emulsifiers in the preparation of an emulsion, preferably an oil-in-water emulsion. Therefore an embodiment of the present invention is a method of preparing an emulsion, preferably an oil-in-water emulsion, comprising a compound according to formula (I). Because compounds according to formula (I) readily form micelles in solution they can be used to encapsulate other compounds.

Use of compounds according to formula (I) can be foreseen as a surfactant, emulsifier or co emulsifier. In addition, their use can be foreseen as an adjuvant, preferably a tank-mix adjuvant for an agrochemical composition.

A tank-mix adjuvant for an agrochemical composition modifies a property of the composition prior to its intended use in an agricultural application. The modification improves the ability of the agrochemical composition or parts thereof to penetrate, target or protect a target organism. Surfactants, emulsifiers, co-emulsifiers, oils and salts are typically used as adjuvants. Each of these components modifies the composition to improve properties such as spreading, penetration, droplet size or other characteristics.

These additives may be included in a formulation with a pesticide or may be added separately to a tank.

Examples

The following examples show that compounds according to formula (I) surprisingly form micelles and not lamellar phase liquid crystals or gels upon dilution in water across a wide range of temperatures and compositions. In addition, the examples show that similar compounds that fall outside formula (I) do not readily form micelles upon dilution in water across a wide range of temperatures and compositions, but instead possess undesirable properties for use as surfactants, emulsifiers or co-emulsifiers.

Comparative example 1 :

A surfactant which falls within the scope of the present invention was formed from oleyl alcohol with an average of five ethoxylates and a terminal butyl group. The surfactant was a free-flowing liquid. It was poured into water whereupon it diluted to form a low concentration, opaque micellar solution. The process of dilution from concentrate down to 0.1 % w/w progressed rapidly with no evidence of gel formation or thickening. A 10 % w/w solution was stable with time and passed readily through a BS 100 mesh sieve. The sample did not leave a residue on the sieve. As a comparison oleyl alcohol with an average of five ethoxylates was diluted in water. This formed a two-phase mixture where one phase was like water and the other phase was gelled. The gelled phase was not dispersible in water and could be collected on a 100 mesh sieve.

Comparative example 2:

A surfactant which falls within the scope of the present invention was formed from oleyl alcohol with an average of ten ethoxylates and a terminal butyl group. The surfactant was a free-flowing liquid. It was poured into water whereupon it diluted to form a low concentration, opaque micellar solution. The process of dilution from concentrate down to 0.1 % w/w progressed rapidly with no evidence of gel formation or thickening. The solution that formed was stable with time.

As a comparison oleyl alcohol with an average of ten ethoxylates was diluted in water. This formed a viscous lump which remained in this state for over one hour. After this time the lump had dispersed, and a homogeneous solution remained; however the process of dilution was compromised by this significant delay and by the difficulty of processing the lump.

Comparative example 3:

The observation of phase separation, and of viscous or gelled phases is considered a problem when surfactants are diluted into water. Formulations are often diluted at the point of use and the aforesaid problems are limiting in terms of product quality. Similarly, the formation of such phases can be a problem on production plants when products are being manufactured.

The following table displays surfactants where these problems have been encountered and demonstrate that the problems are very common. The table shows the results for the temperature region 10 to 30 °C and from a concentration of 40 to 60 % w/w surfactant in water. Other regions of the phase diagram also show these problems. Table X:

Oleyl5EBu: A C18 alcohol with one unsaturated group and an average of five moles of ethoxylate. The surfactant has a butyl end cap.

Oleyl5E: A C18 alcohol with one unsaturated group and an average of five moles of ethoxylate. The surfactant terminates in a hydroxyl group.

OleyMOEBu: A C18 alcohol with a single unsaturated group and an average of 10 ethoxylates. The surfactant terminates in a butyl group. OleyHOE: A C18 alcohol with a single unsaturated group and an average of 10 ethoxylates. The surfactant terminates in a hydroxyl group.

Oleyl20EBu: A C18 alcohol with a single unsaturated group and an average of 20 ethoxylates. The surfactant terminates in a butyl group.

C12E4Me: A 12 carbon alcohol ethoxylate with an average of four ethoxylate groups and a terminal methyl group.

C12E4: A 12 carbon alcohol with an average of four ethoxylate groups. The terminal group is a hydroxyl.

C12E6Me: A 12 carbon alcohol with an average of six ethoxylate groups and a terminal methyl group. C12E6: A 12 carbon alcohol with an average of six ethoxylate groups. The terminal group is a hydroxyl. C12E8Me: A 12 carbon alcohol ethoxylate with an average of eight groups and a terminal methyl group.

C12E8: A 12 carbon alcohol with an average of eight ethoxylate groups. The terminal group is a hydroxyl. C10E5: A 10 carbon alcohol with an average of five ethoxylate groups.

Viscous: The surfactant forms a viscous phase when added to water Separates: The surfactant separates into two phases when added to water Gels: The surfactant forms a soft gel in water which is not redispersible. Pass: The surfactant dilutes in water to form a homogeneous, opaque or transparent micellar solution

Claims

1. A compound according to formula (I):

wherein R is selected from C4-C18 alkyl, C4-C18 alkenyl or C4-Cisalkynyl;

2. The compound according to claim 1 , wherein R is not C12 or C18 alkyl, C12 or C18 alkenyl or C12 or C18 alkynyl when a is 7, 8, 9 or 10; wherein R is not Cie or C17 alkyl or Cie or C17 alkenyl when a is 8, 9 or 10; wherein R is not Cs or C10 alkyl when a is 8 or 10; wherein R is not C10-C14 alkyl when a is 7; and wherein R is not C10-C12 alkyl when a is 10.

3. The compound according to claim 1 , wherein a is an integer of from 3 to 6.

4. The compound according to any of claims 1 to 3, wherein R’ contains 4 carbon atoms.

5. The compound according to any of claims 1 to 3, wherein R’ contains 5 or 6 carbon atoms.

6. The compound according to any of claims 1 to 4, wherein R’ is C4 alkyl.

7. The compound according to any of claims 1 to 6, wherein R’ is linear.

8. A composition comprising the compound according to any of claims 1 to 7, wherein the concentration of the compound is from 1 to 99 % by weight.

9. A composition comprising the compound according to any of claims 1 to 7, wherein the temperature of the composition is maintained in the range of from 0 to 40 °C.

10. A composition comprising the compound according to any of claims 1 to 7, wherein the composition is a micellar solution at a temperature in the range of from 5 to 35 °C.

11. A composition comprising a surfactant, emulsifier or co-emulsifier and the compound according to any of claims 1 to 7.

12. An agrochemical composition comprising a pesticide, fungicide, insecticide or a herbicide and the compound according to any of claims 1 to 7.

13. A composition according to any of claims 8 to 12 comprising water.

14. A method of preparing an emulsion comprising the compound according to any of claims 1 to 7.

15. A method of controlling pests or controlling or preventing undesirable plant growth, comprising applying the composition according to claim 12 to pests or plants, to parts thereof or to the locus thereof with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.