3(2H)-furanone derivatives

Details 3(2H)-furanone derivatives 3(2H)-furanone derivatives

1997-12-29

1999-03-30

McKane, Joseph K.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

5462844, A61K 3144, C07D40704

Patent

active

058890270

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/KR95/00083 filed Jun. 30, 1995.


BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention relates to novel 3(2H)-furanone derivatives of the following formula (I) useful as fungicides having excellent activities to plant fungi and a process for preparing them. ##STR1## wherein, R is C.sub.1 .about.C.sub.2 alkyl, allyl or 2-chloroallyl group; or nitro group; and
2. Description of the Prior Art
Prior to the present invention, furanone derivatives of the following formula (a) were known as herbicides, but the compounds (a) had not been used as fungicides. ##STR2## wherein, R.sup.1 is alkyl group; and


SUMMARY OF THE INVENTION

The object of this invention is to provide novel 3(2H)-furanone compounds of the above formula(I) which have a preventive effect against various kinds of plant fungi, in particular which have selectively excellent fungicidal activities to specific plant fungi.
Another object of this invention is to provide novel fungicidal composition comprising one or more compounds of the above formula(I) as an effective ingredient in combination with an inert carrier.
The present invention relates to 3(2H)-furanone derivatives of the formula(I). ##STR3## wherein, R, X and Y are respectively defined as described previously.


DETAILED DESCRIPTION OF THE INVENTION

According to the present invention, 3(2H)-furanone derivatives of the formula (I) are novel compounds, and have an excellent preventive and fungicidal effect against plant fungi, in particular against rice sheath blight, cucumber gray mold, etc. Therefore, the derivatives are useful as an agricultural and floricultural fungicide ingredient.
In the present invention, 3(2H)-furanone derivatives of the formula(I) may be prepared by the following reaction scheme. ##STR4##
In the above reaction scheme, X, Y and R are respectively defined as described previously.
According to the above reaction scheme, N-oxide compound of the formula(II) prepared by the well-known process is converted into chloropyridine by treating with p-toluenesulfonyl chloride and then it was reacted with potassium cyanide(KCN) in dimethyl sulfoxide(DMSO) to obtain cyanopyridine compound of the formula(III).
The obtained cyanopyridine compound(III) is reacted with hydroxymethylaromatic acid ester compound of the formula(IV) in the presence of a base to prepare aminofuranone of the formula(V). A substituent is introduced at the position of amino group of the formula(V) by reacting with an alkyl or alkenyl halide compound in the presence of a phase transfer catalyst to obtain the desired 3(2H)-furanone derivatives of the formula(I).
According to the present invention, sodium methoxide(NaOMe) may preferably be used as a base, and tetrabutylammonium bromide may preferably be used as a phase transfer catalyst.
In the above formula(I), it may be the preferable compound that X and R are respectively methyl group and Y is chlorine atom.
New compounds of the formula(I) prepared by the present invention may typically be listed in following Table 1. ##STR5##


TABLE 1 __________________________________________________________________________ Compound No. X R Y mp(.degree.C.) .sup.1 H NMR(ppm) __________________________________________________________________________ 1 4-CH.sub.3 CH.sub.3 H 2.37(s, 3H), 3.20(s, 3H), 5.33 (s, 1H), 6.80.about.8.17(m, 8H), 10.23(s, 1H) 2 4-CH.sub.3 CH.sub.2 CH.sub.3 H 1.30(t, 3H), 2.27(s, 3H), 3.55 (q, 2H), 5.43(s, 1H), 6.67.about. 8.17(m, 8H), 10.17(s, 1H) 3 4-CH.sub.3 CH.sub.2 --CH.dbd.CHCl H 2.36(s, 3H), 4.30(q, 2H), 5.90 (s, 1H), 6.13(m, 2H), 6.85.about. 8.27(m, 8H), 10.55(s, 1H) 4 4-CH.sub.3 CH.sub.2 --CH.dbd.CH.sub.2 H 2.27(s, 3H), 4.13(t, 2H), 5.06, 5.23(m, 3H), 5.43(s, 1H), 6.67.about.8.07(m, 8H), 10.33(s, 1H) 5 4-CH.sub.3 CH.sub.2 --CH.dbd.CHCl 4-CH.sub.3 2.34(s, 3H), 2.37(s, 3H), 4.30(m, 2H), 5.53(s, 1H), 6.17(m, 2H), 6.70.about.8.23(m, 7H), 10.46(s, 1H) 6 4-CH.sub.3 CH.sub.3 4-CH.sub.3 2.30(s, 3H), 2.33(s, 3H), 3.17 (s, 3H), 5.53(s, 1H), 6.7.about. 8.30(m, 7

REFERENCES:
patent: 4568376 (1986-02-01), Ward
patent: 4568377 (1986-02-01), Ward
patent: 4663466 (1987-05-01), Pomidor et al.
patent: 5189035 (1993-02-01), Curtze et al.
patent: 5648486 (1997-07-01), Cai et al.

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