Aqueous, agrochemical agents containing active ingredients

Details Aqueous, agrochemical agents containing active ingredients Aqueous, agrochemical agents containing active ingredients

2001-01-29

2002-06-11

Pryor, Alton (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

C504S142000, C424S405000

Reexamination Certificate

active

06403529

ABSTRACT:

The application is a 371 of PCT/EP99/03328 filed May. 14, 1999.
BACKGROUND OF THE INVENTION
This invention relates to water-based compositions which contain at least one agricultural chemical (“agrochemical”) and certain alkoxylated fatty acids esters, to the use of such fatty acid esters for the production of compositions containing agrochemicals and to a process for applying agrochemicals to plants.
There are various known agents for protecting crops against pests and weeds. Unfortunately, they often show little or no solubility in water. Accordingly, these products are often marketed in the form of compositions based on mineral oils. On account of the environmental problems this involves and particularly on account of the inadequate biodegradability of the solvent, attempts are now being made to stop using these products. Instead, the agrochemicals are formulated as an aqueous dispersion or emulsion and may thus be readily be applied to the plants, for example by spraying.
Numerous auxiliaries are known to the expert for dispersing or emulsifying various active substances in water. In order to obtain stable dispersions or emulsions, however, very intensive shear forces often have to be applied in the production of the compositions. In addition, separation of the emulsion or dispersion can occur in the event of significant temperature differences during the storage and use of the compositions. In many cases, the plant protection compositions are also marketed as concentrates which are only diluted to the required extent in situ. In cases such as these, however, machines suitable for obtaining compositions in the required, stably emulsified form, such as high-speed mixers, are often not available.
Accordingly, WO 96/22109 describes the use of ethoxylated fatty acid esters having certain HLB values for the production of plant protection compositions or pharmaceutical preparations. These esters are biodegradable and self-emulsifying. However, plant protection compositions containing these esters as emulsifiers do not always have sufficient stability, particularly at high temperatures. Accordingly, there is still a need for water-based plant protection compositions which are stable in storage, even at high temperatures, and which are easy to produce.
It has surprisingly been found that compositions containing agrochemicals and certain propoxylated fatty acid ester as dispersants or emulsifiers satisfy the above-mentioned requirements in regard to stability and handling behavior.
BRIEF SUMMARY OF THE INVENTION
Accordingly, the present invention relates to water-based compositions containing water-insoluble agrochemicals and one or more compounds corresponding to general formula (I):
RO—(C
2
H
4
O)
n
(C
3
H
6
O)
m
—R′  (I)
in which RO is an alcohol selected from the group of branched or linear, saturated or unsaturated monohydric alcohols containing
1
to
6
carbon atoms or polyols containing 2 to 12 carbon atoms and 2 to 6 hydroxyl groups and R′ is hydrogen and/or a group —CO—R″, where R″ is a branched or linear, saturated or unsaturated alkyl group containing 5 to 29 carbon atoms, m is a number of 1 to 10 and n is 0 or a number of 1 to 40.
The compositions according to the invention may contain both solid and liquid water-insoluble ingredients. Accordingly, they form both dispersions and emulsions. In the present specification, dispersions and emulsions are collectively referred to as dispersions.
DETAILED DESCRIPTION OF THE INVENTION
The alkoxylated fatty acid esters corresponding to formula (I) are known substances which are described, for example, in U.S. Pat. No. 2,678,935, U.S. Pat. No. 3,539,518, U.S. Pat. No. 4,022,808 and GB 1,050,497, of which the disclosures are also part of the present application.
The alkoxylated fatty acid esters may be prepared by any methods known to the expert, for example by esterification of fatty acids with alkoxylated methanol, as described in U.S. Pat. No. 3,539,518. Unfortunately, this process has certain disadvantages, i.e. it comprises two steps, the esterification step takes a very long time and the products are colored by the high reaction temperatures. In addition, correspondingly produced fatty acids methyl ester ethoxylates have relatively high OH values after esterification which can be problematical for certain applications. Another method comprises directly reacting fatty acid esters with alkylene oxide in the presence of transition metal catalysts (cf. U.S. Pat. No. 4,022,808). However, the fatty acid alkyl ester alkoxylates are preferably produced by the heterogeneously catalyzed direct alkoxylation of fatty acid alkyl esters with ethylene oxide and/or propylene oxide on calcined or hydrophobicized hydrotalcites. This synthesis process is described in detail in WO 90/13533 and WO 91/15441, of which the disclosure is also part of the present application. The products obtained are distinguished by the low OH value, the reaction is carried out in a single stage and light-colored products are obtained. The fatty acid alkyl esters serving as starting materials may be obtained from natural oils and fats or may be synthesized.
The alkoxylated fatty acid esters contain at least 1 mole of propylene oxide groups per mole of ester. Compounds of formula (I) which contain between 1 and 10 moles of propylene oxide per mole of ester are preferred. In addition to the propylene oxide units, between 1 and 40 ethylene oxide groups are also preferably present in the molecule. Compounds corresponding to formula (I) containing between 1 and 30 moles of ethylene oxide per mole of ester are preferred. Both compounds which have been reacted with a mixture of ethylene oxide and propylene oxide and compounds which have been reacted with ethylene oxide and propylene oxide in two separate steps may be used as these mixed ethylene oxide/propylene oxide adducts. Where compounds of formula (I) which contain polyols as the alcohol component RO are used, the quantity data relating to the ethylene or propylene oxide units (indices n and m) are always based on the molecule as a whole. However, it is known that the exact distribution of the ethylene or propylene oxide units among the various hydroxyl groups obeys a distribution dependent on the synthesis.
The fatty acid esters —CO—R″ contain alkyl groups R″ with 5 to 29 carbon atoms. Suitable fatty acid components are natural and synthetic fatty acids, more particularly straight-chain, saturated or unsaturated C
6-30
fatty acids, including the technical mixtures thereof obtainable by lypolysis from animal and vegetable fats and oils, for example from coconut oil, palm kernel oil, soybean oil, sunflower oil, rapeseed oil, cottonseed oil, fish oil, bovine tallow and lard; special examples are caprylic acid, capric acid, lauric acid, lauroleic acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, oleic acid, elaidic acid, arachic acid, gadoleic acid, behenic acid and erucic acid.
The alcohol component RO may be selected from linear or branched, saturated or unsaturated monoalcohols containing 1 to 6 carbon atoms, for example methanol, ethanol, n- and i-propanol, n- and i-butanol, pentanol, hexanol, 2-ethylhexanol and cyclohexanol. Suitable polyols containing 2 to 6 carbon atoms are, for example, ethylene glycol, 1,2-propylene glycol, 1,2-butylene glycol, glycerol or trimethylol propane and pentaerythritol. Basically, all the hydroxyl groups of the alcohols are substituted by the alkoxides, although the terminal alkoxide groups are not all end-capped by ester groups. Accordingly, if polyols, such as glycerol or ethylene glycol, are used as the alcohol component RO, the compositions may contain compounds of formula (I) obtained by reaction of the full esters and also the partial esters with alkoxides. However, preferred compounds corresponding to formula (I) are those in which all the hydroxyl groups of the alcohols are alkoxylated and all terminal alkoxide groups are endcapped by ester groups with the formula —CO—R″. Accordingly, in these preferr

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