Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2001-08-02
2002-05-07
Lambkin, Deborah C. (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S280000, C504S288000, C504S291000
Reexamination Certificate
active
06383987
ABSTRACT:
The present invention relates to a novel substantially water-free formulation of crop protection agents, comprising essentially
a) cyclohexenone oxime ether of the formula I
where the variables are defined as follows:
R
1
is ethyl or propyl;
R
2
is hydrogen or an equivalent of an agriculturally useful cation;
R
3
is 2-(thioethyl)propyl, tetrahydrathiopyran-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 1-(methylthio)cyclopropyl, 5-(isopropyl)isoxazol-3-yl, 2,5-dimethylpyrazol-3-yl, 2,4,6-trimethylphenyl or 2,4,6-trimethyl-3-butyrylphenyl;
R
4
and R
5
independently of one another are each hydrogen, methyl or methoxycarbonyl;
Alk is CH
2
CH
2
, CH
2
CH(CH
3
), CH
2
CH═CH, CH
2
CH═C(Cl) or CH
2
CH
2
CH═CH;
R
6
is hydrogen, phenyl, halophenyl, dihalophenyl, phenoxy, halophenoxy or dihalophenoxy;
b) N-phosphonamethylglycine (glyphosate), an ester or salt thereof, DL-homoalanin-4-yl(methyl)phosphinic acid (glufosinate) or its ammonium salt:
c) from 20 to 80% by weight of an aprotic or weakly protic solvent in which the components a) and b) are dissolved or suspended;
d) if desired emulsifiers, surfactants, surface-active and/or activity-enhancing auxiliaries.
Moreover, the invention relates to processes for preparing a spray liquor for controlling undesirable plants.
It is known that herbicides from the substance class of the cyclohexenone oxime ethers have the tendency to undergo hydrolytic decomposition or chemical degradation reactions in aqueous or protic solvents. For this reason, cyclohexenone oxime ethers have hitherto only been prepared and employed as water-free emulsion concentrates.
A possible alternative is offered by formulations of solids, as described in WO 96/29869.
However, formulations of solids have the disadvantage that it is either not possible or possible only in very small amounts to incorporate activity-enhancing additives, for example lipophilic esters, such as methyl oleate, lauric and adipic esters, as well as paraffin oil or fatty acid esters, if appropriate in combination with selected emulsifiers
However, mixtures of the cyclohexenone oxime ethers I and glyphosate, glufosinate or a derivative thereof would allow better control of undesirable grasses than glyphosate/glufosinate on its own. It is even an essential precondition for the economical control of “Round up Ready”, self-sown maize in “Round up Ready” soya beans. This generally applies to grasses which are resistant (tolerant) to glyphosate.
It is an object of the present invention to provide a liquid finished formulation which comprises a cyclohexenone oxime ether herbicide, N-phosphonomethylglycine or a derivative thereof and, if desired, an activity-enhancing auxiliary and is sufficiently storage-stable.
We have found that this object is achieved by the suspension concentrates defined at the outset. Furthermore, we have found a process for preparing a herbicidally active spray liquor.
The present suspension concentrates are characterized by the fact that the proportion of free water (which is not bound as water of crystallization) is from 0 to 5% by weight, preferably from 0 to 2% by weight and in particular only from 0 to 0.5% by weight.
Preferred herbicide components a) are cyclohexenone oxime ethers selected from the group consisting of: sethoxydim, cycloxydim, clethodim, tralkoxydim, butroxydim, 2-(1-(3-chloroallyloxy)iminopropyl)-5-(tetrahydropyran-4-yl)-3-hydroxycyclohex-2-enone, 2-[1-(2-p-chlorophenoxypropyloxy)iminobutyl]-5-(tetrahydrothiopyran-3-yl)-3-hydroxycyclohex-2-enone or mixtures thereof, in particular clethodim or 2-(1-(3-chloroallyloxy)iminopropyl)-5-(tetrahydropyran-4-yl)-3-hydroxycyclohex-2-enone. These active ingredients are usually soluble in the oil phase. Also suitable, however, are the alkali metal or alkaline earth metal salts of the preferably or particularly mentioned cyclohexanone oxime ethers, which, in combination with selected assistants, are substantially insoluble in the continuous oil phase, with the result that the degradation of the active ingredients I is substantially prevented. Thus, preferred cyclohexanone oxime ether salts are those which are present in solution in the oil phase and in an amount of <1%, very particularly preferably <0.1-0.5%.
The salts of the cyclohexenone oxime ethers I are generally obtainable by reacting the free compounds I (R
2
=hydrogen) with basic metal salt solutions. Suitable sources of basic metal salts are typically hydroxides, carbonates or phosphates of alkali metals, alkaline earth metals or transition metals. Cations of a higher valence, such as calcium and magnesium, which were employed in approximately equimolar amounts to the compounds I, may additionally, for charge neutralization, be associated with anions of mineral acids or organic acids. By spray drying of the aqueous solution of a potassium or a calcium salt, it is then possible to prepare granules which contain approximately 100% by weight of cyclohexenone oxime ether metal salt.
The component b) consists of known commercial products. The common names are glyphosate, sulfosate and glufosinate, and the corresponding trademarks are RoundUp®, Touchdown® and Basta® respectively.
In the context of the present invention, particular preference is given to mixtures which comprise, as derivative of N-phosphonomethylglycine, the isopropylammonium salt of N-phosphonomethylglycine which is known as glyphosate. Other known derivatives of phosphonomethylglycine are the trimethylsulfonium salt, which is known under the name sulfosate, and the ammonium salt. However, particular preference is given to the product mentioned at the outset, which is known as glyphosate, in particular its ammonium salt.
A mono-, di- or trideprotonated salt of glyphosate, in particular alkali metal, alkaline earth metal, transition metal or ammonium salts, has been found to be a useful herbicide component b). The ammonium salt of glyphosate is very particularly preferred.
In general, an excess of component b) is employed, up to approximately 10 times the molar amount, in particular approximately 7 to 8 times the molar amount, based on the amount of component a).
Suitable aprotic or weakly protic solvents which serve as component c) are nonpolar, polar or dipolar aliphatic or aromatic solvents which exhibit only low solubilizing power, if any at all, toward the component b). To obtain storage-stable formulations, the solubility of the active compound b) in the oil phase should be below it by weight (based on the total formulation). This also applies to component a), as long as the salts of the compounds I are used. Preference is given to hydrocarbons, such as benzene, alkylbenzene and naphthalene, and their mono- and polyalkyl-substituted and/or partially hydrogenated derivatives, n- or isoparaffins having 8 to 30 carbon atoms, aliphatic or aromatic esters of mono- or dicarboxylic acids, such as methyl oleate, octyl laurate and octyl adipate and benzoic esters, or to unmodified or modified natural fats and oils, such as soya oil, sunflower oil and rapeseed oil methyl ester.
Particular preference is given to aromatic solvents of the benzene and naphthalene series, such as Solvesso® 150 and Solvesso® 200 (alkylaromatics from Exxon).
In addition to the component c), the formulations according to the invention generally comprise emulsifiers, surfactants and surface-active auxiliaries such as wetting agents and dispersants as further components.
Suitable surfactants, wetting agents and dispersants are, for example:
1. anionic surfactants and dispersants, especially
soaps (alkali metal, alkaline earth metal or ammonium salts of fatty acids), for example potassium stearate;
alkyl sulfates;
alkyl ether sulfates, for example sulfated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers;
alkyl- or isoalkylsulfonates;
alkali metal, alkaline earth metal or ammonium salts of arylsulfonic acids or alkylbenzenesulfonic acids, for example ligno-, phenolsulfonic acids, naphthalene- and dibutylnaphthalenesulfonic acids or Na-dode
Berghaus Rainer
Bratz Matthias
Fries Jürgen
Jäger Karl-Friedrich
Kober Reiner
BASF - Aktiengesellschaft
Keil & Weinkauf
Lambkin Deborah C.
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