Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-10-28
1995-12-26
McKane, Joseph K.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548237, 548239, C07D26310, A01N 4376
Patent
active
054788552
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a certain kind of oxazoline derivative, and more detailedly to 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline represented by the following formula (I) ##STR1## , and a miticide containing it.
BACKGROUND ART
Heretofore, several reports have been made about 2,4-diphenyl-2-oxazoline compounds. See, for example, Tetrahedron Letters, 22 (45), 4471-4474 (1981); Chemical Abstracts, 98, 160087k (1983); and J. Chem., 52, 2523-2530 (1987), etc.
Japanese Patent Official Announcement No. 501962/1982 (=PCT International Publication No. WO 82/02046) discloses .DELTA..sup.2 -N-heterocyclic compounds, for example 2,4-diphenyl-2-oxa- or -thia-zoline derivatives and 2-Phenyl-4-benzyl-2-oxa- or -thia-zoline derivatives, useful as intermediates for preparation of effective ingredients of pharmaceuticals and/or as compounds having, as they are, biological actions, e.g. as an antidiabetic drug.
However, the above-mentioned literatures do not mention at all activities of the compounds disclosed therein on pests noxious to agrohorticultural crops, for example insects, mites, etc.
On the other hand, the present inventors found that a series of 2,4-diphenyl-2-oxa- or -thia-zoline derivatives represented by the following general formula (A) ##STR2## wherein, X.sup.1 and X.sup.2 are the same or different, and each denote a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a trifluoromethyl group or a trifluoromethoxy group; atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a cyano group, a nitro group, a halogen atom or a trifluoromethyl group; X.sup.1 and X.sup.2 are the same or different and each are a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom, Y.sup.1 and Y.sup.2 are the same or different, and each denote a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a cyano group, an iodine atom or a trifluoromethyl group, and having 4 to 6 carbon atoms at the 2- or 6-position of the benzene ring, have excellent insecticidal and miticidal activities against harmful insects which are parasitic on useful plants, and proposed them (see Japanese Laid-Open patent Publication No. 85268/1990=U.S. Pat. No. 4,977,171 and EP 345775A1).
SUMMARY OF THE INVENTION
The compounds of the general formula (A) exhibit high activities against insects and mites noxious to plants in comparatively small doses. However, the present inventors have further investigated the insecticidal and miticidal activities of the compounds of the general formula (A); as a result, they have found, now, that 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline represented by the following formula (I) ##STR3## which is included in the general formula (A) but not specifically disclosed in the above laid-open publication, exhibits a remarkably high miticidal activity, and especially, has an excellent miticidal activity even against resistant Panonychus citri and resistant Tetra-nychus kanzawai which are thought at present to be hard to control; and have completed this invention.
DETAILED DESCRIPTION
The compound of the above formula (I) provided by this invention has an extremely remarkable miticidal activity; can control noxious mites in low doses; moreover has extremely high safety on warm-blooded animals; and is useful as an active ingredient of a miticide.
The compound of the formula (I) of this invention can, for example, be prepared according to the following reaction formula A. ##STR4## wherein, in the above formula,
X.sup.1 and X.sup.2 each denote a halogen atom. In the reaction formula A, the first stage reaction of 2-amino-2-(2-ethoxy-4-tert-butylphenyl)ethanol of the formula (II) with a 2,6-difluorobenzoyl halide of the formula (III) and, usually, be carried cut in a suitable solvent in the presence of a base. As the solvent and, for example, there can be used an ether such as diethyl ether or tetrahydrofuran, an aromatic hydrocarbon such as benzene, toluene or xylene, or the like, and as the base can,
REFERENCES:
patent: 4977171 (1990-12-01), Suzuki et al.
patent: 5141948 (1992-08-01), Miyamoto et al.
CA 112:235287u Preparation . . . virucides. Sinharay et al., p. 623, 1990.
CA 115: 159127m Preparation . . . insecticides. Miyamoto et al., p. 939, 1991.
CA 117: 131181s Preparation . . . acaricides. Miyamoto et al. p. 745, 1992.
CA 120: 127813u Domestic . . . derivatives. Suzuki et al., p. 390, 1994.
Vorbruggen et al., "A Simple Synthesis of .DELTA..sup.2 -Oxazolines, .DELTA..sup.2 -Oxazines, .DELTA..sup.2 -Thiazolines and .DELTA..sup.2 -Imidazolines", Tetrahedron Letters, vol. 22, No. 45, pp. 4471-4474, 1981.
Chemical Abstracts 98:160087k (1983).
Tsuge et al, "Regioselective Cycloadditions of N-Protonated Azomethine Ylides and 2-Azaallyl Anions Generated from N-(Silylmethyl) Thioimidates, Synthetic Equivalents of Nonstabilized Nitrile Ylides", J. Org. Chem. 1987, 52,2523-2530.
Chemical Abstracts 98:16670c (1983).
Ikeda Tatsufumi
Ishida Tatsuya
Itoh Yoshiaki
Kikuchi Yasuo
Suzuki Junji
McKane Joseph K.
Yashima Chemical Industry Co., Ltd.
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