Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2002-12-02
2004-07-06
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
Reexamination Certificate
active
06759371
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to water-based herbicidal preparations containing at least one agrochemical agent from the group consisting of bromoxynil and its derivatives and certain alkoxylated fatty acid esters, to the use of such fatty acid esters for increasing the penetration of bromoxynil and its derivatives into plant leaves and to a process for controlling unwanted plant growth.
It is known that weeds can be controlled with a variety of herbicides which often have little or no solubility in water. One important representative is bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) and its derivatives. Where herbicidal agents such as these are applied, penetration into the plant is minimal on account of their poor solubility in water, resulting in an inadequate herbicidal effect. Accordingly, agrochemical agents of the type in question are formulated as aqueous dispersions or emulsions so that they can be applied without difficulty, for example by spraying onto the plants, the emulsifier also acting as a wetting agent to improve uptake of the agent into the plant. The greater the penetration of the herbicide, the more effectively and efficiently it can be used. Accordingly, there is a general need for formulations which provide for substantially complete penetration of the herbicidal agent into the plant. DE-OS 29 24 403, for example, describes water-based preparations containing bromoxynil salts and—as formulation aids—alkali metal salts of alkyl polyglycol ether phosphate partial esters. EP 0 485 207 describes aqueous emulsions containing bromoxynil octanoate and heptanoate and, as emulsifiers, polyalkylene oxide-modified silanes or ethoxylated tall oil amides.
It has surprisingly been found that water-based preparations containing bromoxynil or derivatives thereof and, as emulsifiers, certain alkoxylated alcohols provide for very high penetration of the herbicide into the plant.
BRIEF SUMMARY OF THE INVENTION
This invention relates to water-based herbicidal preparations containing at least one agrochemical agent from the group consisting of bromoxynil and its derivatives and certain alkoxylated fatty acid esters, to the use of such fatty acid esters for increasing the penetration of bromoxynil and its derivatives into plant leaves and to a process for controlling unwanted plant growth.
Accordingly, the present invention relates to water-based preparations containing bromoxynil or derivatives thereof 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, n is a number of 1 to 50 and m is 0 or a number of 1 to 10.
DETAILED DESCRIPTION OF THE INVENTION
The preparations according to the invention contain bromoxynil and/or derivatives thereof, preferably bromoxynil alkyl esters or sodium and/or potassium salts of bromoxynil or sulfates and carbonates thereof. Preparations containing bromoxynil octanoate or heptanoate are particularly preferred.
The alkoxylated compounds corresponding to formula (I) are known substances which are described, for example, in U.S. Pat. Nos. 2,678,935, 3,539,518, 4,022,808 or GB 1,050,497 of which the disclosures are also part of the present invention.
The compounds corresponding to formula (I) may by 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. It is a two-stage process, the esterification reaction is very time-consuming and the products are colored by the high reaction temperatures. In addition, fatty acid methylester ethoxylates produced by this process have relatively high OH values after the esterification step which can be problematical for certain applications. Another possibility is the direct reaction of fatty acid esters with alkylene oxides in the presence of transition metal catalysts, as described in 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. These synthesis processes are described in detail in WO 90/13533 and WO 91/15441 of which the disclosure is also part of the present invention. The products formed are distinguished by a low OH value, the reaction is carried out in a single stage and light-colored products are obtained. The fatty acid alkyl esters used as starting materials may be obtained from natural oils and fats or may be synthetically produced.
The alkoxylated fatty acid esters contain at least 1 mol ethylene oxide groups per mol ester. Compounds of formula (I) containing between 1 and 30 mol ethylene oxide per mol ester are preferred. In addition to the ethylene oxide units, between 1 and 10 propylene oxide groups are also present in the molecule. Other preferred compounds corresponding to formula (I) are those which contain between 1 and 30 mol ethylene oxide per mol ester and 1 to 10 mol propylene oxide groups. For these mixed ethylene oxide/propylene oxide adducts, it is possible to use both compounds reacted with a mixture of ethylene oxide and propylene oxide and compounds reacted with ethylene oxide and propylene oxide in two separate steps. The alkoxides are statistically distributed between the OH groups present, depending on the production process.
If compounds corresponding to formula (I) containing polyols as the alcohol component RO are used, the quantitative data for the ethylene or propylene oxide units (indices n and m) are always based on the molecule as a whole. However, the exact distribution of the ethylene or propylene oxide units between the various hydroxyl groups of the polyols is known to comply with a distribution dependent on the synthesis process.
The fatty acid esters —CO—R″ contain alkyl groups R″ with 5 to 29 carbon atoms. Suitable fatty acid components are natural or synthetic fatty acids, more particularly straight-chain, saturated or unsaturated C
6-30
fatty acids, including technical mixtures thereof obtainable by lipolysis 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, capric, lauric, lauroleic, myristic, myristoleic, palmitic, palmitoleic, oleic, elaidic, arachic, gadoleic, behenic and erucic acid.
Suitable alcohol components RO are linear or branched, saturated or unsaturated monohydric alcohols 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 C
2-6
polyols 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 not all terminal alkoxide groups are capped by ester groups. Accordingly, if polyols, such as glycerol or ethylene glycol, are used as the alcohol component RO, the preparations may contain compounds corresponding to formula (I) obtained by reaction both of the full esters and of the partial esters with alkoxides. However, preferred compounds of formula (I) are those in which all the hydroxyl groups of the alcohols are alkoxylated and all terminal alkoxide groups are capped by ester groups with the formula —CO—R″. Accordingly, in these preferred compounds, R″ in formula (I) stands exclusively for a branched or linear, saturated or unsaturated alkyl group containing 5 to 29 ca
Abribat Benoit
De Ruiter Hans
Mainx Hans-Georg
Wollenweber Horst-Werner
Cognis Deutschland GmbH & Co. KG
Ettelman Aaron R.
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