Acrylate-type fungicide

Details Acrylate-type fungicide Acrylate-type fungicide

2001-12-14

2002-10-22

Kumar, Shailendra (Department: 1609)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S134000, C564S163000, C564S165000, C514S619000, C514S620000

Reexamination Certificate

active

06469209

ABSTRACT:

This patent application claims a benefit of priority from Korean Patent Application No. 1999/26946 filed Jul. 5, 1999, through PCT Application Serial No. PCT/KR00/00716 filed Jul. 4, 2000, the contents of each of which are incorporated herein by reference.
FIELD OF THE INVENTION
The present invention relates to novel acrylate-type N-methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxyl amide O-methyl oxime represented by the following formula 1, its preparation method and its use as fungicides. The compound of the present invention has not only stronger fungicidal effect on plant pathogens at low concentrations but also broader fungicidal spectrum than the conventional fungicides. Especially, because the compound has excellent systemic and curative effect as well as no toxicity, it can be used an efficacious agricultural fungicide. In addition, the compound of the present invention can be useful as environmental-friendly fungicide capable of causing less environmental pollution fungicide due to its strong fungicidal effect at low concentrations.
BACKGROUND
In spite of their strong fungicidal effect, agricultural fungicides currently in use have been a source of problems, because the required amount is ever increasing as tolerance of target plant pathogens increases. Thus, there is a need to develop new fungicides with strong fungicidal effect and broad fungicidal spectrum. Acrylate-type compounds have been developed as an environment-friendly alternative to the conventional fungicides.
The acrylate fungicides currently in use have strong fungicidal effect on pathogenic fungi of plant origin with broad fungicidal spectrum [EP patent No.: 382, 375 (ICIA5504), U.S. Pat. No.: 4,829,085 (BAS490F), EP patent No.: 398,692 (SSE-126)]. There have been continuing developments of more effective acrylate fungicides.
Among those recently developed, alkoxyiminoaceteamide derivatives with two aryl groups and an ether linkage, have been shown to have strong fungicidal effect on pathogenic fungi at low concentrations with broad fungicidal spectrum. The conventional techniques of their use are described in international publication No.: WO 9617851 and WO 9534526, German publication No.: DE 4312637 and DE 4030038, and European publication No.: EP 398692. The inventors of the present invention also had applied for a patent on alkoxyiminoaceteamide derivative compounds (Korean patent application No.: 98-21068)
The inventors of the present invention developed novel acrylate-type N-methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylamide O-methyl oxime with outstanding fungicidal effect at low concentrations with broad fungicidal spectrum, especially the compound is superior to the conventional fungicides in terms of systemic as well as curative effect.
SUMMARY OF THE INVENTION
It is an object of this invention to provide novel acrylate-type N-methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylamide O-methyl oxime represented by the formula 1.
It is a further object of this invention to provide a method for preparing novel acrylate-type N-methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylamide O-methyl oxime.
It is an additional object of this invention to provide agricultural fungicides, containing acrylate-type N-methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylamide O-methyl oxime as an active ingredient.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
Hereinafter, the present invention is described in detail.
The present invention provides novel acrylate-type N-methyl E-2-((2-methylphenyl) oxymethyl)-6-methylphenylglyoxyl amide O-methyl oxime represented by the formula 1.
The acrylate-type compound represented by the formula 1 of the present invention, namely N-methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylamide O-methyl oxime, shows broad fungicidal spectrum as well as strong fungicidal effect on plant pathogens at low concentrations. The compound also has excellent curative effect and remarkable systemic effect in plant body.
The compound of the present invention is especially superior to the conventional fungicides such as triazole-type flusilazole or acrylate-type kresoxim methyl (BAS490F) in the protection from barley powder mildew and wheat leaf rust at low concentrations. In addition, the compound of the present invention shows remarkable control efficacy on rice blast, tomato late blight and rice sheath blight at low concentrations. Thus, the compound has been shown to be remarkably effective on various kinds of plant pathogens.
The present invention provides a method of preparation for the novel acrylate-type N-methyl E-2-((2-methylphenyl) oxymethyl)-6-methylphenylglyoxylamide O-methyl oxime represented by the formula 1.
The method for preparing the compound according to the present invention is summarized in the following steps.
1) methyl E-2-bromomethyl-6-methylphenylglyoxylate O-methyl oxime is reacted with o-cresol under a basic condition to give methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylate O-methyl oxime (step 1); and
2) methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylate O-methyl oxime prepared in the step 1 is reacted with methylamine (NH
2
Me) to give N-methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylamide O-methyl oxime of the present invention (step 2).
The preparation of methyl E-2-((2-methylphenyl) oxymethyl)-6-methylphenylglyoxylate O-methyl oxime (formula 2) of the step 1 may be done as in the scheme 1.
Methyl E-2-bromomethyl-6-methylphenylglyoxylate O-methyl oxime of the formula 3 is reacted with o-cresol of the formula 4 under an appropriate basic condition to give the compound of the formula 2. The base may be preferably selected from the group comprising K
2
CO
2
, Na
2
CO
3
, triethylamine (TEA) and sodium hydride (NaH), etc. A variety of reaction solvents including dimethylformamide (DMF), tetrahydrofuran (THF), chloroform (CHC
3
) and etc. may be used. The reaction temperature may be −20~100° C., preferably −10~30° C.
Methyl alkoxyiminoacetate of the formula 2 prepared in the scheme 1 is reacted with methylamine to give N-methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylamide O-methyl oxime of the formula 1 as represented in the scheme 2.
In the above reaction, the number of equivalent of methylamine may be 1-10, preferably 5. The reaction solvents are preferably used dimethylforamide (DMF), tetrahydrofuran (THF), chloroform (CHCl
3
), etc. The reaction temperature may be 0~100° C., preferably 0~30° C.
Methyl E-2-bromomethyl-6-methylphenylglyoxylate O-methyl oxime (formula 3), the reactant of the scheme 1, can be prepared by the method in the scheme 3.
Methyl 2,6-dimethylphenylglyoxylate of the formula 6 is obtained by the reaction of 2-bromo-m-xylene of the formula 5 with buthyllithium (BuLi), followed by the reaction with dimethyl oxalate [(CO
2
Me)
2
]. The compound of the formula 6 is reacted with methoxylamine hydrochloride (MeONH
2
.HCl) to give methyl E-2,6-dimethylphenylglyoxylate O-methyl oxime of the formula 7 [U.S. Pat. No.: 5,371,223 (1994)]. The compound of the formula 7 is reacted with N-bromosuccinimide (NBS) to give the compound of the formula 3 [U.S. Pat. No.: 5,371,223 (1994); L. Horner Angew. Chem. 71 (1959), 349].
The present invention also provides agricultural fungicides, containing N-methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenylglyoxylamide O-methyl oxime as an active ingredient.
N-Methyl E-2-((2-methylphenyl)oxymethyl)-6-methylphenyl glyoxylamide O-methyl oxime of the present invention can be a useful agricultural fungicides due to its strong fungicidal effect at low concentrations, broad fungicidal spectrum, especially, excellent curative and systemic effect, and no phytotoxicity.
Agricultural fungicides can be formulated as a single compound of the formula 1, or as a mixture with other compounds to improve the fungicidal effect and to broaden the spectrum of target pathogens.
The compound of the present invention can be used to control and reduce damage in the case

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