Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1990-09-26
1992-03-10
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548163, C07D27782, A01N 4718, A01N 4736, A01N 4378
Patent
active
050950258
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The invention relates to a benzothiazole derivative which is useful as an agricultural and horticultural fungicide.
BACKGROUND ART
Thanks to fertilizers, pesticides and various agricultural materials, a high productivity has been achieved in recent agriculture. On the other hand, there are some serious problems in this field including the appearance of chemical-tolerant strains caused by repetitive application of pesticides and disease damage caused by continuous cropping (i.e. by continuous annual culture of a single crop). Under these circumstances, it has been urgently required to develop a highly safe chemical. Thus, the present invention provides a means for solving these problems.
DISCLOSURE OF THE INVENTION
The present invention provides a benzothiazole derivative represented by the following general formula, and furthermore provides an agricultural and horticultural fungicide containing the benzothiazole derivative as an active ingredient: ##STR2## wherein X represents --NHR, --R or --OR group in which R is a lower alkyl, cycloalkyl, aryl or substituted aryl group;
Y represents a lower alkyl, alkenyl, alkyloxycarbonylalkyl, benzyl or substituted benzyl group; and
Z represents a lower alkoxy group or a hydrogen atom.
The compound of the present invention may be synthesized in the following manner. First, a 2-aminobenzothiazole represented by the following general formula [I]: ##STR3##
wherein Z is as defined above, 3-substituted 2-iminobenzothiazole [II]: ##STR4##
wherein Z and Y are each as defined above.
Next, the compound [II] is reacted with the corresponding isocyanate, acid halide or halogenoformate in an appropriate solvent.
BEST MODE FOR CARRYING OUT THE INVENTION
Examples of the organic solvent to be used in the reaction of the 3-substituted 2-iminobenzothiazole with the isocyanate include dioxane, tetrahydrofuran, acetone, methyl ethyl ketone, benzene, toluene, xylene, monochlorobenzene, dichlorobenzene, dimethylformamide, acetonitrile and the like. Furthermore, examples of a catalyst effective for this reaction include organometallic compounds such as dibutyltin dilaurate and tertiary amines such as triethylamine.
The solvent for the reaction between the 3-substituted 2-iminobenzothiazole and the acid halide or the halogenoformate may be selected from among those described above for the reaction of the 3-substituted 2-iminobenzothiazole with the isocyanate. Examples of a deacidifying agent effective for this reaction include tertiary amines such as triethylamine and alkali metal carbonates or alkaline earth metal carbonates such as sodium hydrogencarbonate, potassium carbonate and calcium carbonate.
The above-described reaction between the 3-substituted 2-iminobenzothiazole and the isocyanate, acid halide or halogenoformate may be preferably conducted at a temperature of from 0.degree. to 100.degree. C.
Now typical examples for the synthesis of the benzothiazole derivative of the present invention will be given. Table 1 summarizes the compounds thus synthesized.
SYNTHESIS EXAMPLE 1
Synthesis of 3-allyl-2-methoxycarbonyliminobenzothiazole (compound No. 4 in Table 1):
To a mixture comprising 3.8 g of 3-allyl-2-iminothiazole, 3.4 g of sodium hydrogencarbonate and 50 ml of tetrahydrofuran was added 1.9 g of methyl chloroformate dropwise at room temperature under stirring. After reacting for two hours, the reaction mixture was poured into approximately 200 ml of water. The crystals precipitated were collected by filtering to thereby obtain 4.5 g of the objective compound.
Yield: 91%.
m.p.: 121.degree.-124.degree. C.
IR (cm.sup.-1): 1638.
SYNTHESIS EXAMPLE 2
Synthesis of 3-benzyl-2-[(N-cyclohexylcarbamoyl)-imino]benzothiazole (compound No. 13 in Table 1):
To a solution of 1.8 g of 3-benzyl-2-iminobenzothiazole and a catalytic amount of dibutyltin dilaurate in 30 ml of acetone was added 0.95 g of cyclohexyl isocyanate dropwise. After seven hours, the reaction mixture was poured into approximately 100 ml of water. The crystals precipitated were collected by filteri
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Kawada Hiroshi
Nishimura Shinji
Tanaka Ken'ichi
Yamazaki Mitsumasa
Gerstl Robert
Hodogaya Chemical Co. Ltd.
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