• Journal of the Korean Chemical Society
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• v.54 no.6
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• pp.727-730
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• 2010

A tricyclic ring system bearing new stereogenic center namely 2,3-dihydro[1]benzothieno[3,2-b]pyrrole 4,4-dioxide was synthesized by asymmetric photoisomerization of 2,3-dihydropyrrolo[1,2-b]benzisothiazole 5,5-dioxide by irradiation with 245 nm emission of the low-pressure mercury lamp. The chemical structure and the purity of the photoproduct were delineated preliminarily by IR, NMR, and MS and finally confirmed by single crystal X-ray crystallography.

• Applied Biological Chemistry
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• v.27 no.2
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• pp.95-99
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• 1984

Some derivatives of 3-oxo-1,2-benzisothiazole-1,1-dioxide were synthesized, and their antifungal activities against Pyricularia oryzae was determined by the agar medium dilution method. $I_{50}$ values of the candidate derivatives were shown to be as follows; 3-chloro(37.8ppm), 2-chloro(318.7ppm), MCS(20.1ppm), 2-allyl(946.2ppm), 3-(p-nitrophenyloxy) (35.4ppm), 3-(o-nitrophenyloxy) (11.8ppm), 3-(p-aminophenyloxy) (1643.2ppm), 2-chloromethyl(192.7ppm) and 2-hydroxymethyl derivative(248.4ppm).

• Applied Biological Chemistry
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• v.29 no.2
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• pp.164-174
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• 1986

도열병균에 의한 벼의 목 및 잎도열병에 효과가 좋은 새로운 살균제의 개발을 시도하였다. 농약으로 예상되는 몇몇 3-oxo-1, 2-benzisothiazole-1, 1-dioxide의 새로운 유도체들을 합성하고, 이들 유도체들의 도열병균 (Pyricularia oryzae)에 대한 항균성을 agar medium dilution 방법에 의해 측정하였다. 3-oxo-1, 2-benzisothiazole-1, 1-dioxide의 5 원자 고리의 3개 구조 단위중에서 가장 항균성이 큰 단위는 $R-S-C=N-SO_2-$단위이며, 3개 구조 단위의 항균성 순서는 $RS-C=N-SO_2-\;{\geq}\;RO-C=N-SO_2-\;>\;-CNR-SO_2-$였다. 30개 후보화합물 가운데서 14개의 유도체가 도열병균에 효능이 좋은 것으로 알려진 oryzemate 보다 우수한 항균성을 나타냈다.

• Archives of Pharmacal Research
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• v.28 no.12
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• pp.1317-1323
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• 2005

In an attempt to examine the ability of benzisothiazole-based drugs to interact with $\beta$-adrenoceptors, a series of 1,2-benzisothiazole derivatives, which were substituted with various propanolamine or oxypropanolamine side chains in the 2 or 3 position, were synthesised and tested. The pharmacological activity of these compounds at the ,$\beta$-adrenoceptors was examined using isolated rat atria and small intestinal segments, which preferentially express the $\beta_{1}$- and $\beta_{3}$-adrenoceptor-mediated responses, respectively. None of these products showed any $\beta$-adrenoceptor agonistic activity. In contrast, the 2- and 3-substituted isopropyl, tert-butyl, benzyl, and piperonyl derivatives 2a-d and 3a-d elicited surmountable inhibition of the isoprena­line-induced chronotropic effects in the atria, suggesting competitive antagonism at the $\beta_{1}$­recognition site. The $pA_{2}$ values revealed tert-butyl 3b and the isopropyl substituted piperonyl derivatives 3a to be the most effective. Remarkably, many of the 2-substituted propanolamines were less active than the corresponding 3-substituted oxypropanolamines. With the exception of compound 3b, none of these drugs antagonised the muscle relaxant activity of isoprenaline in the intestine, suggesting no effect on the $\beta_{3}$-adrenoceptors. These results confirm the ability of the benzisothiazole ring to interact with the $\beta$-adrenoceptors, and demonstrate that 2-substitution with propanolamine or 3-substitution with oxypropanolamine groups yields compounds with preferential antagonistic activity at the cardiac $\beta_{1}$adrenoceptors. The degree of antagonism depends strongly on both the nature of the substituent and its position on the benzisothiazole ring.

• Journal of the Korean Chemical Society
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• v.30 no.3
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• pp.296-300
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• 1986

The pseudo-first order rate constants have been obtained for the solvolysis of pseudo-saccharinechloride in MeOH-$H_2O$, EtOH-$H_2O$, MeOH-MeCN and MeOH-$(Me)_2$CO solvents mixtures at various temperatures. Values of n and m in the Kivinen and Grunwald-Winstein plots, respectively, have been determined and the Taft's solvatochromic parameters were obtained; based on these solvent effect parameters as well as on the activation parameters it was concluded that reaction proceeds via an $S_N2$ mechanism.

• Journal of Life Science
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• v.14 no.2
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• pp.351-355
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• 2004

Saccharin derivatives were synthesized by means of 4 reaction steps involved the reaction of 1-methylurea (or 1-methylthiourea) and oxalyl chloride. 1-Alkyl(or phenyl)-3-(1,1,3-trioxo-1,3-dihydro-1$^{6}$ -benzo[d]isothiazol-2-ylmethyl)-imidazolidine-2,4,5-trione 5 and 1-alkyl(or phenyl)-2-thioxo- 3-(1,1,3-trioxo-1,3-dihydro-1$^{6}$ -benzo-[d]isothiazol-2-ylmethyl)-imidazolidine-4,5-dione 12 were obtained by means of 4 reaction steps involved the reaction of 1-methyl-urea(or 1-methylthiourea) and oxalyl chloride.

• Journal of Life Science
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• v.13 no.1
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• pp.54-58
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• 2003

1-Methyl-3-(1,1,3-trioxo-1,3-dihydro-1λ$^6$-benzo[d]isothiazol-2-ylmethyl)-imidazolidine-2,4,5-triones 5a, 1-ethy1-3-(1,1,3-trioxo-1,3-dihydro-lλ$^6$/-benzo[d]isothiazol-2-ylmethyl)-imidazolidine-2,4,5-triones 5b 1-phenyl-3-(1,1,3-trioxo-1,3-dihydro-1λ$^6$-benzo [d]isothiazol-2-ylmethyl)-imidazolidine-2,4,5-triones 5c were obtained by means of 4 reaction steps involved the reaction of 1-methyl-urea and oxalyl chloride. Biological tests(Plant Response Screening Result, Insect Primary Screening Result and Fungicide Primary Screening Result) of synthesized sacccarin derivatives were executed.

• Applied Biological Chemistry
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• v.29 no.1
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• pp.90-95
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• 1986

A comparative study of chemical characteristics, efficacy and relative merits of extruded and coated granules, containing fungicide and insecticide, was conducted under laboratory and field conditions. Probenzole (3-allyloxy-1,2-benzisothiazole 1,1-dioxide) and carbofuran (2,3-dihydro-2,2-dimethyl-7-benzofuranyl methyl carbamate) were chosen as toxicants for rice blast(Pyricularia oryzae) and brown planthopper (Nilaparvata lugens) control, respectively. Stability of active ingredients in coated granule was superior to the extruded one under accelerated temperature. Active ingredient dissolution of coated one into distilled water showed slow release pattern. Pesticide residues in rice (Oryzae sativa, Chucheongbyeo) shoot applied with extruded one at the dosage of 3kg/10a retained higher levels than those with coated one on two days after application, while the residue levels were a reversed tendency on eight days after application. Efficacy on rice blast exhibited minute differences between the granules, on the other hand efficacy on brown planthopper by coated one was of higher rank than that by extruded one. Production cost of the combined pesticide granule by coating method could be cut down by 6% as compared to extrusion method.