Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-11-01
1998-07-07
Powers, Fiona T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5483667, 5483671, 5483681, 5483701, 5483704, A01N 4356, C07D23118
Patent
active
057769656
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Technical Field
The present invention relates to novel propenoic ester derivatives having a 4-hydroxypyrazole group of the following formula(l) which have active fungicidal properties. ##STR2## wherein: R.sup.1 represents hydrogen, halogen, nitro, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms; group having 1 to 6 carbon atoms, or an alkylthio group having 1 to 6 carbon atoms; group, a benzyl group, a phenyl group, or a substituted phenyl group which is substituted by a substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, nitro and halogen; atoms, a phenyl group, or a substituted phenyl group which is substituted by a substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, nitro and halogen, having 1 to 6 carbon atoms, a phenyl group, or a substituted phenyl group which is substituted by a substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, nitro and halogen; and X represents a CH group or nitrogen.
2. DESCRIPTION OF THE PRIOR ART
Even though the known fungicides possess excellent fungicidal properties, the development of compounds based upon a similar basic structure has given rise to the problem of resistance development by the target fungi due to long exposure to these compounds with a common basic structure.
As a result of a continuous effort to solve this problem, a series of novel propenoic ester derivatives was disclosed firstly in European Patent No. 472300 of ICI Co., U.S. Pat. No. 4994495, European Patent No. 422597 of BASF Co., U.S. Pat. No. 5003101 and European Patent No. 460575 of Ciba-Geigy Co., but the fungicidal activity of the reported compounds was too low and limited in its application therefore, there is a need for potent fungicides which possess effective fungicidal activity, low toxicity and good economy.
Therefore, in consideration of the aforesaid points, the present inventors have made efforts to develop new fungicidal compounds which have powerful fungicidal activities to various target fungi and low toxicity, we have applied for a patent about propenoic ester derivatives having a pyrazole group and the use thereof (Korean laid-open patent No. 94-432, PCT/KR93/00052).
As the result, the inventors of the present invention synthesized novel propenoic ester derivatives by using 4-hydroxypyrazole compounds which have not been so far known.
SUMMARY OF THE INVENTION
The objective of the present invention is to provide novel propenoic ester derivatives with strong fungicidal activities toward various fungi and broad fungicidal spectrum and a simple manufacturing process.
Another objective is to provide fungicidal compositions containing the derivatives as an active compound.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is identified as propenoic ester derivatives having 4-hydroxypyrazole group which correspond to the following formula(I), and agricultural preparations containing compounds of formula(I) as an active ingredient: ##STR3## In formula (I), R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and X are respectively defined as above.
In the formula(I) according to the present invention, the preferred derivatives with greatest fungicidal activities are those where R.sup.1 and R.sup.4 represent hydrogen, R.sup.2 represents a methyl or methylthio group, R.sup.3 represents a phenyl or substituted phenyl group which is substituted by a substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms, and R.sup.5 represents a trifluoromethyl or methyl group.
According to the present invention, propenoic ester derivatives of the above formula(I) can be prepared by the following two methods.
As shown in the following reaction pathway 1, the first method is the preparation of propeno
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Hwang Ki Jun
Kim Byung Sup
Kim Sung Soo
Korea Research Institute of Chemical Technology
Powers Fiona T.
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