Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-09-23
1999-11-09
Dees, Jose' G.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504140, 504142, 504344, 504139, A01N 4356, A01N 4302, A01N 3700, A01N 3510
Patent
active
059814403
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to crop protection active compound formulations, comprising a cyclohexenone oxime ether of the general formula I ##STR2## where the radicals R.sup.1 -R.sup.6 have the following meanings: R.sup.1 is ethyl or propyl; cation; tetrahydrothiopyran-4-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 1-methylthiocyclopropyl, 5-isopropylisoxazol-3-yl, 2,5-dimethylpyrazol-3-yl, 2,4,6-trimethylphenyl or 2,4,6-trimethyl-3-butyrylphenyl; methoxycarbonyl; CH.sub.2 CH.dbd.C(Cl) or CH.sub.2 CH.sub.2 CH.dbd.CH; or dihalophenoxy; 5, and their preparation and use as herbicides.
Cyclohexenone oxime ethers of the general formula I have been known as herbicides for a long time. Moreover, in small amounts they act as growth regulators.
The herbicidally active cyclohexenone oxime ethers of the general formula I are disclosed, inter alia, in DE-A 24 39 104, DE-A 28 22 304, DE-A 38 08 072, DE-A 38 38 309, EP-A 046 860, EP-A 066 195, EP-A 071 707, EP-A 088 299, EP-A 088 301, EP-A 115 808, EP-A 125 094, EP-A 137 174, EP-A 142 741, EP-A 177 913, EP-A 228 598, EP-A 230 235, EP-A 230 260, EP-A 238 021, EP-A 243 313, EP-A 254 514, EP-A 319 835, EP-A 456 068, EP-A 456 069, EP-A 456 112, EP-A 456 118,
U.S. Pat. No. 4,440,566, JP-A 54/191 945 and Proceedings Brit. Crop Protection Conference--Weeds 1985, Vol. 1, pages 93-98.
Metal salts of cyclohexenone oxime ethers are also disclosed, inter alia, in the earlier German Patent Application having the file reference 195 45 212.7.
These compounds are in general used in the form of water-dispersible powders (WP) or water-dispersible granules (WG), and also as emulsifiable concentrates (EC). Some compounds of this class of substances are marketed as water-soluble formulations in which the active compound is present as the alkali metal salt. A disadvantage of the emulsifiable concentrates is that, beside the actual active compound, large amounts of organic solvents are also applied during use. It has additionally been shown that the active compounds are unstable in organic solvents in the presence of emulsifiers or of water present in traces and decompose (cf., for example, EP-A 394 847 and EP-A 266 068).
Water-dispersible solid formulations (WP or WG) do avoid the use of organic solvents, but require a higher expenditure on preparation of the formulation. The often low-melting or liquid active compounds must be absorbed on carrier material in order to be accessible to the necessary fine grinding. The addition of auxiliaries and carriers additionally leads to the fact that the active compound contents in the formulations have to precipitate to a low extent, which leads to increased packaging and transportation costs. Examples of such formulations are found, inter alia, in EP-A 488 645.
Water-soluble formulations have also been described previously. It is also seen here that the chemical instability of the cyclohexenone oxime ethers stands in the way of a practical solution. A lithium salt, for example, is thus described in JP 62089 635.
The preparation of various salts, among these salts of transition metals, by double decomposition is described in various applications. In practice, this process appears unsuitable as in the end sufficient stability is not achieved. (JP 59 1633 63, JP 8144 384, U.S. Pat. No. 4,741,768, DE 3941160).
The preferred manner of preparation of alkali metal salts is the extraction of the active compounds from organic solution using an aqueous solution of the alkali metal hydroxides (eg. DE 3941160).
It is an object of the present invention to develop storage-stable solid formulations of cyclohexenone oxime ethers of the general formula I and a process for their preparation.
We have found that this object is surprisingly achieved by the crop protection active compound formulation described at the out-set.
Within the meaning of the present invention, the cyclohexenone oxime ethers are weak organic acids having pK.sub.a s between 4 and 5. Their low solubility in water in the neutral range distinctly increases at basic pHs. It is thus possible by su
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Berghaus Rainer
Bratz Matthias
Jager Karl-Friedrich
Ziegler Hans
BASF - Aktiengesellschaft
Dees Jos,e G.
Pryor Alton
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