Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-11-08
2004-05-25
Pryor, Alton N. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C504S138000, C504S266000
Reexamination Certificate
active
06740671
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel fungicidal composition comprising a 2-aminothiazolecarboxamide derivative, N-(&agr;-cyano-2-thenyl)-4-ethyl-2-(ethylamino)-5-thiazolecarboxamide (ISO proposed name: ethaboxam) of the formula:
and as an adjuvant a suitable nonionic surfactant.
BACKGROUND ART
A compound of formula (I), ethaboxam, was already described as a fungicidal compound for crop protection in Korean Patent No. 124,552 (Korean patent application No. 94-19960). Further, ethaboxam-containing formulations, e.g. wettable powder (trade name: Guardian; marketed by Misung Ltd.) were known.
An adjuvant is a non-pesticidal compound for enhancing a total activity of a pesticide, differently from a co-formulant which controls physical properties of active ingredients to facilitate their handling. Presence of the adjuvant in a pesticidal formulation increases a total quantity of active ingredients which can be contacted with and/or penetrated into a target plant thereby to enhance the activity of pesticide and to remarkably reduce the quantity of active ingredients which needs to be applied. Currently, Envirornental Protection Agency in the U.S.A. and Ministry of Agriculture, Fisheries and Food in the United Kingdom are recognizing the employment of the adjuvant as a major tool for obtaining desired activity of novel active ingredients.
An adjuvant is widely used in leading advanced countries such as the U.S.A. and European countries and conventionally, is manufactured and marketed as a separate package for use as a tank-mix formulation in spraying herbicides. Recently, its application is also extended to fungicides, insecticides, growth regulators and fertilizers. However, the adjuvant for use as the tank-mix formulation is manufactured as a separate package and thus, its production and transportation costs are unavoidably increased and particularly, strict experimental data are required for its registration. Therefore, its development takes a long time and requires enormous expenses.
Recently, several leading agrochemical manufacturers are likely to formulate an adjuvant in combination with active ingredients in one package thereby to facilitate mixing, transportation and particularly, registration of products. A formulation containing the adjuvant in combination with the active ingredients in one package is referred to as a premixed one-pack formulation, a contrary concept to a tank-mixed formulation. An example of the premixed one-pack formulations is a round-up formulation containing as the adjuvant tallow amine and as the herbicidal compound glyphosate in one package.
Conventionally, an adjuvant for fungicides is added to a spray liquid when applied and a product containing 75-95% of a mineral oil and 5-25% of a surfactant is widely used. This adjuvant increases the fungicidal activity by improving the retention of active ingredients to plants rather than by increasing foliar penetration of active ingredients. However, such mineral oil-containing product may cause injury to plants and environmental contamination due to its low biodegradability.
Recently, in order to increase the efficacy of high-activity penetrative fungicides, it was suggested that non-ionic surfactants such as sorbitan esters of fatty acids, polyoxyethylene alkyl ethers, polyoxyethylene sorbitan esters, polyoxyethylene alkyl phenol ethers, polyoxyethylene amides be incorporated into the fungicides (see U.S. Pat. No. 5,905,072). Examples of fungicides which can be employed are as follows: triazoles, e.g. tetraconazole, triadimefon, triadimenol, propiconazole, penconazole, hexaconazole, cyproconazole, flusilazole, etc.; imidazoles, e.g. prochloraz, imazalil, etc.; morpholines, e.g. fenpropimorph, tridemorph, etc.; dicarboxyimides, e.g. iprodione, vinclozolin, etc.; piperidines, e.g. fenprodipin, etc.; acyl alanines, e.g. metalaxyl, benalaxyl, etc. In particular, it was disclosed that polyoxyethylene alkyl ethers selectively enhance the efficacy of the penetrative fungicide, benzyl triazolyl cyclopentanes (see U.S. Pat. No. 5,393,770).
Accordingly, in order to enhance the fungicidal activity of ethaboxam and to reduce the quantity thereof which needs to be applied, screening of an environment friendly adjuvant and development of a novel fungicidal composition using the same may provide many advantages in both commercial and environmental aspects.
DISCLOSURE OF THE INVENTION
In order to develop a compound enhancing the efficacy of ethaboxam and reducing its quantity which needs to be applied, the present inventors incorporated various potential compounds including anionic and nonionic surfactants into ethaboxarnp. and conducted experiments for their efficacy enhancement activity. As a result, they found that nonionic surfactants of polyoxyalkylene alkyl ether class cause enhancement of activity. Thus, they prepared a one-pack formulation containing them, and found that such formulation remarkably enhances the fungicidal activity at a given level of ethaboxam. Further, they found that the formulation containing a particular polyoxyalkylene alkyl ether has equivalent or superior efficacy evenat a half or less level of ethaboxam, as compared with polyoxyalkylene alkyl ether-free ethaboxam formulation and thus, completed the present invention.
Thus, it is an object of the present invention to provide a fungicidal composition comprising ethaboxam and a non-pesticidal adjuvant which is more cost-effective and readily biodegradable than active ingredients.
A first aspect of the present invention provides a fungicidal composition which comprises N-(&agr;-cyano-2-thenyl)-4ethyl-2-(ethylamino)-5-thiazolecarboxamide of the formula:
(hereinafter, referred to as ethaboxam) and a nonionic surfactant.
A further aspect of the present invention provides a method for enhancing the activity of ethaboxam, which comprises adding a nonionic surfactant to ethaboxam formulation.
A still further aspect of the present invention provides a method for controlling undesired phytopathogens which comprises applying a formulation prepared from the composition of the present invention to target plants.
The nonionic surfactant which can be employed in the present invention is classified into polyoxyalkylene alkyl ether having polyoxyalkylene as the hydrophilic moiety and aliphatic alcohol as the lipophilic moiety. Preferred polyoxyalkylene alkyl ether is derived from saturated or unsaturated alcohol having the alkyl chain of 12 to 18 carbon atoms or mixtures thereof More preferred polyoxyalkylene alkyl ether is derived from lauryl alcohol having 12 carbon atoms, cetyl alcohol having 16 carbon atoms, stearyl alcohol being saturated and having 18 carbon atoms or oleyl alcohol being unsaturated and having 18 carbon atoms. In the present invention, polyoxyethylene is representative polyoxyalkylene, but polyoxyethylene-polyoxypropylene copolymer wherein ethylene oxide and propylene oxide is copolymerized is also included. For example, polyoxyethylene has an average of 3 to 50, more preferably, 7 to 20, most preferably, 10 to 14 ethylene oxide units per molecule, depending upon the number of carbon atoms in the alkyl chain derived from aliphatic alcohol. In the present invention, particularly preferred is polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether or polyoxyethylene oleyl ether, each of which has an average of 7 to 20 ethylene oxide units per molecule. Polyoxyalkylene alkyl ether employed in the present invention may be obtained by copolymerization of ethylene oxide and natural or synthetic aliphatic alcohol having 12 to 18 carbon atoms and the purity of 50 to 98%.
The fungicidal composition of the present invention contains 1 to 80 wt %, preferably, 5 to 50 wt % of ethaboxam, 10 to 50 wt % of adjuvant, 10 to 89 wt/% of solid or liquid carrier or additive and 0 to 20 wt %, preferably, 0.1 to 10 wt % of surfactants. In case where the composition contains less than 1 wt % of ethaboxam, it is difficult to control the dilution fold. By contrast, in case where the composition contains mor
Cho Jin-Ho
Cho Kwang-Yun
Chun Sam-Jae
Kang Kyung-Goo
Kang Seung-Hun
Birch & Stewart Kolasch & Birch, LLP
LG Life Sciences Ltd.
Pryor Alton N.
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