Use of low-volatility pyrazole derivatives having hydrophilic gr

Details Use of low-volatility pyrazole derivatives having hydrophilic gr Use of low-volatility pyrazole derivatives having hydrophilic gr

1997-08-06

1999-10-26

Richter, Johann

Chemistry: fertilizers

Processes and products

Organic material-containing

5483771, 5483761, 5483721, 5483725, C07C 1108, C07D23116, C07D23120, C07D23122

Patent

active

059720646

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention relates to the use of pyrazole derivatives of the formula I ##STR1## or their acid addition salts as nitrification inhibitors, where the radicals R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the following meanings: C.sub.20 -alkyl, C.sub.3 - to C.sub.8 -cycloalkyl, C.sub.5 - to C.sub.20 -aryl or alkylaryl, it being possible for these 4 radicals to be monosubstituted or disubstituted by halogen and/or hydroxyl ##STR2## where R.sup.5 and R.sup.6 are hydrogen, C.sub.1 - to C.sub.20 -alkyl which can be monosubstituted or disubstituted by halogen and/or hydroxyl, a carboxyl group, a carboxymethyl group or a functional derivative of the two last-mentioned groups, and radical or a functional derivative of these groups or ##STR3## where R.sup.8 and R.sup.9 are hydrogen, C.sub.1 - to C.sub.20 -alkyl, C.sub.3 - to C.sub.8 -cycloalkyl, C.sub.5 - to C.sub.20 -aryl or alkylaryl, it being possible for these 4 radicals to be monosubstituted or disubstituted by halogen and radical whose terminal hydroxyl group can be etherified by an aliphatic C.sub.1 - to C.sub.10 -alkohol or esterified by a C.sub.1 - to C.sub.10 -carboxylic acid.
The invention furthermore relates to novel pyrazole derivatives which are suitable for this intended use, processes for their preparation and fertilizer mixtures which contain such pyrazole. derivatives.
2. Description of the Background
In order to make available to plants the nitrogen needed by them, they are fertilized, as is known, with ammonium compounds. Ammonium compounds, however, are microbially converted to nitrate in the soil in a relatively short time (nitrification).
Because nitrate is leached from the soil more easily than ammonium and the leached portion is no longer available for plant nutrition, however, rapid nitrification is undesirable. In order that the fertilizer is utilized better, it was therefore proposed to add nitrification inhibitors to the soil.
EP-A 474 037 discloses 3-methylpyrazole derivatives in which one nitrogen atom of the pyrazole ring carries a methyl, cycloalkyl, aryl or aralkyl radical. It is proposed to use these compounds as intermediates for the preparation of pharmaceutical products or crop protection agents.
U.S. Pat. No. 3,635,690 discloses the employment of various pyrazole derivatives for the inhibition of nitrification. In the pyrazole derivatives proposed, the nitrogen atoms in the pyrazole ring do not carry any substituents or one of the nitrogen atoms carries a saturated or unsaturated C.sub.1 - to C.sub.3 -hydrocarbon radical. One or more carbon atoms in the pyrazole ring can be substituted by hydrocarbon radicals which may carry halogens as substituents. Examples of these are 3-methylpyrazoles such as 4-chloro-3-methylpyrazole.
U.S. Pat. No. 4,969,946 also describes the use of pyrazole derivatives as nitrification inhibitors. In these derivatives, the nitrogen atoms in the pyrazole ring are unsubstituted, and several of the ring carbon atoms are substituted by halogen or methyl.
DE-A 3 704 359 relates to compositions which inhibit nitrification. As active compound, they contain pyrazole derivatives which, on one nitrogen atom of the pyrazole ring, carry a radical of the formula ##STR4##
where R' is a substituted or unsubstituted organic radical or a hydroxyl radical.
Further nitrification inhibitors are disclosed in EP-A 0 160 804. They are pyrazole derivatives in which a nitrogen atom in the pyrazole ring carries a substituted oxycarbonyl, sulfinyl or sulfonyl radical.
DE-A 4 018 395 mentions derivatives of 1-cyano-3-methylpyrazole and its acid addition products or coordination compounds as nitrification inhibitors.
SU-A 1 470 737 discloses N-hydroxymethyl derivatives of pyrazole.
These active compounds are still not entirely satisfactory as nitrification inhibitors as they have one or more of the following disadvantages: action in the soil and the stability on storage is reduced. This relates especially to pyrazole derivatives such as N-glyoxylpyrazoles and N-hydroxy

REFERENCES:
patent: 3303200 (1967-02-01), Wolf et al.
patent: 3635690 (1972-01-01), Griffith
patent: 4084955 (1978-04-01), Kornis et al.
DM. Huber et al, "New Tools for Food Production", BioScience vol. 27, No. 8, pp. 523-529, Aug. 1977.

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