• The Journal of Natural Sciences
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• v.12 no.1
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• pp.81-84
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• 2002

We developed new process for the large scale preparation of pyrazole sulfonyl urea and pyrazole sulfonyl urea carboalkoxyl benzene sulfonyl urea 1) in high yields and convenience. As compound with know procedure this procedure have found to be far large scale preparation. During the preparation we obtains two new sulfonyl urea 5a and 5b in 70% and 74% ( purified by crystallization).

• Applied Chemistry for Engineering
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• v.3 no.1
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• pp.100-110
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• 1992

Arylsulfonyl urea derivatives can be easily prepared in good yield by treating amines with arylsulfonyl carbamates in aqueous solution : 1) N-Arylsulfonyl-N'-aryl urea derivatives, 2) N-Arylsulfony-N'-alkyl urea derivatives, 3) N-Arylsulfonyl-N'- heterocyclic urea derivatives. The proposed reaction mechanisms for preparing arylsulfonyl ureas involve formation of an ion-pair conformation by initial acid-base reaction, then formation of a so-called tetrahedral intermediate by nucleophilic addition, followed by an acid-catalyzed elimination of an alkoxide ion and loss of a proton.

• Korean Journal of Weed Science
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• v.7 no.2
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• pp.208-219
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• 1987

Newly developed several herbicides were evaluated as paddy rice herbicide at the Yeongnam Crop Experiment in 1986. And also, the general situation of rice cultivation between Korea and Japan was compared. Twenty-nine herbicides of the total 59 herbicides were used as paddy rice field in Korea while these were 100 and 187, respectively, in Japan. Among paddy rice herbicides, butachlor was the most important herbicide in both countries. However, the degree of concentration to a particular herbicide was greater in Korea compared to Japan; consumption rate of single butachlor to the total herbicide were 66.5% for Korea and 11.9%r for Japan, respectively. Pyrazolate, pyrazoxyfen and quinclorac were the most promising hebicides in pressed-type rice nurserybed in terms of herbicidal efficacy and phytotoxic effect. For transplanted paddy rice field, single application of NC-311 or combining applications of NC-311 with butachlor or quinclorac gave excellent results at the weed community that was dominated by Echinochloa crus-galli, Aneilema japonica, Ludwigia prostrata, Scirpus hotarui, Cyperus serotinus, Potamogeton distinctus and Eleocharis kuroguwai. Particularly the above combining applications maintained their excellent herbicidal effect up to 3 leaf stage of E. crus-galli without arising herbicidal phytotoxicity. Pyrazolate and three sulfonyl urea herbicides (DPX-5384, NC-311 and CGA 142464) exhibited very high safety against rice. However, Japonica type rice cultivar was a little bit more sensitive than Indica/Japonica type rice cultivar. On the other hand, the effect of these herbicides against E. crus-galli was very strong. Herbicidal effect against E. crus-galli was enhanced through shoot absorption for sulfonyl urea herbicides and root abosorption for pyrazolate and quinclorac, respectively.

• Archives of Pharmacal Research
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• v.29 no.9
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• pp.721-727
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• 2006

To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)-4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate 2-phenoxycarbonylaminobut-3-enyl p-toluenesulfonate (10) with arylsulfonamide in the presence of potassium carbonate produced corresponding 2 and N-(4-vinyloxazolidin-2-yl)arylsulfonamide 11 in approximately equal ratio. This reaction is believed to undergo through urea intermediate 16 as shown in scheme 3. 1-Arylsufonyl-4-vinylimidazolidinones 2 show much reduced activity against human colon carcinoma (Colo205), human chronic myelogenous leukemia (K562), and human ovarian adenocarcinoma (SK-OV-3) and compatible activity against human lung carcinoma (A549) compared to 1. Therefore phenyl at 4-position should be the optimum planar motif for the activity of 1.

• Applied Biological Chemistry
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• v.39 no.3
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• pp.235-240
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• 1996

The most stable stereo conformer in non substituted benzenesulfonyl urea, 1 was the II-keto form, which the molecule was intramolecular associated(H-bond) coformer between imide group and N atom on the Pyrimidine ring. The hydrolytic degradation of 2 derivatives were proceeds by nucleophilic addition reaction(p<0) with orbital controlled intermolecular interaction between LUMO with electron donating$(\sigma<0)$ groups of 2 and HOMO of water molecule. N-(4,6-disub. pyrimid ine-2-yl)aminocarbonyl-2-(1,1-dimethoxy-2-fluoro)ethylbenze nesulfonamides,3 and N-(4,6-disub. triazine-2-yl)aminocarbonyl-2-(1,1-d imethoxy-2-fluoro)ethylbenzenesulfonamides,4 we re synthesized and their herbicidal activities in vivo against bulrush (Scirpus juncoides.) were measured by the pot test under the paddy conditions And the structure activity relationships(SAR) were analyzed by the multiple regression technique. The results of the SAR suggested that the 3 and 4 derivatives indicated dependent on the hydrophobicity of the 4,6-disubstituents and the heterocyclo group, where the optimal value $((log\;P)_{opt.}=0.89)$ of hydrophobicity was 0.89. The pyrimidine substituents, 3 showed higher herbicidal activity than the triazine substituents, 4. Among them, 4,6-dimethoxypyrimidine substituent, 3a showed the best herbicidal activity.

• Proceedings of the Korean Society of Plant Pathology Conference
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• 2003.10a
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• pp.111-111
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• 2003

Several fungal isolates were isolated from diseased monochoria(Monochoria vaginalis, weed of paddy field), which has an resistance to sulfonyl urea(S.U.) herbicide, and were evaluated in the laboratory and greenhouse as potential mycoherbicide. Eight fungi, Alternaria sp., Colletotrichum sp., Curvularia sp., Paenicillium sp and etc. were observed in the isolates. Pathogenicity testing were done on the monochorias in the greenhouse. Monochorias were inoculated with suspensions containing conidia of each isolate at the rates of 1.0 ${\times}$ 10$\^$5/ conidia/ml and 0.1％ Tween 80 with hand-gun sprayer. Curvularia sp. and an unidentified fungal isolate caused 90-95％ mortality on the monochorias 15∼20 days after inoculation. However the other isolates induced slight symptom of disease on the monochorias. In the early stage of disease development sun-burn appearance was shown at the infected site and the last infected leaves and stems were withered to death. Subsequently the pathogenicity on the rice was evaluated with above two effective isolates. From the test an unidentified isolate showed pathogenicity on the rice but Curvularia sp., named as DBB2003, didn't. Now the mass production and formulation using Curvularia sp. DBB2003 are in progress and the field test will be followed. Combination product with Curvularia sp. DBB2003 and chemical herbicide will be more effect to control the monochoria resisted on S.U. herbicide and need to be further tested.

• The Korean Journal of Pesticide Science
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• v.9 no.2
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• pp.153-158
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• 2005

Safening activities of optically active ${\alpha}$-methylbenzylphenylureas on crop injury of rice (Oryza sativa L., cv. Tsukinohikari, japonica) caused by bensulfuron-methyl (methyl 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoate) and pyribenzoxim (benzophenone o-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoyl]oxime) were investigated. Some derivatives of the optically active compounds exhibited strong safening activity against growth inhibition of rice by bensulfuron-methyl. Out of the derivatives tested, (S)-2,3-diCl and (S)-2-F-4-Me derivatives showed greater relieving activity than that of dymuron. In addition, the stress relieving activity was also obtained when they were applied at 4 days after bensulfuron-methyl treatment. On the other hand, crop injury caused by pyribenzoxim was relieved by about 95% with (S)-2-F-4-Me derivative in shoots and roots of rice seedlings.

• Korean Journal of Weed Science
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• v.10 no.4
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• pp.255-260
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• 1990

Seventeen different herbicides were screened to select promising ones for the control of weeds, which may be used in paddy fields transplanted with 8 days old young rice seedlings. Four classes of herbicides were chosen and tested with seedlings grown under different cultivating conditions. Contact herbicides such as diphenyl-ether and oxadiazol showed severe growth retardation of rice seedlings. Carbamate class(dimepiperate), quinoline class (quinclorac), pyrazol class(pyrazolate), acid amide class(mefenacet and pretilachlor), addition of safener (pretilachlor+fenclorim and mefenacet+bensulfuron+dymuron) and unknown class (KC-7079) exhibited normal growth of seedlings. Sulfonyl urea herbicide class(cimosulfuron, bensulfuron, pyrazosulfuron), and oxarane class(tridiphane) showed the slight growth inhibition but recovered shortly.

• Environmental Mutagens and Carcinogens
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• v.24 no.1
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• pp.33-39
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• 2004

To validate and to estimate the chemical hazard playa very important role to environment and human health. The detection of many synthetic chemicals including agrochemicals that may pose a genetic hazard in our environment is of great concern at present. Since these substances are not limited to the original products, and enter the environment, they have become widespread environmental pollutants, thus leading to a variety of chemicals that possibly threaten the public health. Pyrazosulfuron-ethyl [Ethyl-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate, $C_{14}H_{18}N{6}O_{7}S,$ M.W. =414.39, CAS No. 93697-74-6], is one of well known rice herbicide belong in the sulfonyl urea group. To clarify the genotoxicity of this agrochemical, Ames bacterial reversion assay, in vitro chromosomal aberration assay with Chinese hamster lung (CHL) fibroblast and bone marrow micronucleus assay in mice were subjected. In Ames assay, although pyrazosulfuron-ethyl revealed cytotoxic at 5,000-140 $\mug/plate$ in Salmonella typhimurium TA100, no dose-dependent mutagenic potential in 4.4～70 $\mug/plate$ of S. typhimurium TA 98, TA 100, TA1535 and TA 1537 both in the absence and presence of S-9 metabolic activation system was observed. Using CHL fibroblasts, the 50% cell growth inhibition concentration $(IC_{50})$ of pyrazosulfuron-ethyl was determined as 1,243 $\mug/mL,$ and no chromosomal aberration was observed both in the absence and presence of S-9 mixture in the concentration range of 311-1,243 $\mug/mL.$ And also, in vivo micronucleus assay using mouse bone marrow, pyrazosulfuron-ethyl revealed no remarkable induction of MNPCE (micronucleated polychromatic erythrocytes/1000 polychromatic erythrocytes) in the dose range of 625-2,500 mg/kg body weight when administered orally. Consequently, Ames bacterial gene mutation with Salmonella typhimurium, in vitro chromosome aberration with mammalian cells and in vivo bone marrow micronucleus assay revealed no clastogenic potential of pyrazosulfuron-ethyl in this study.

• The Korean Journal of Pesticide Science
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• v.2 no.1
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• pp.32-39
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• 1998

This study was performed to develop jumbo granules floated and spreaded on the water surface after application, having low production and formulation cost, and safe to environment for paddy herbicides and to establish the formulation recipe. The jumbo granules of azimsulfuron with molinate(0.075+7.5%) was formulated by KCl as water soluble carrier and paraffin oil as solvent to impose the floating and spreading force to granules. That showed 100% of total granules to be floated on and spreaded upto the water surface within 25 minutes after application. Change in carriers, surfactants and pH did not affected to improve the time-course degradation of azimsulfuron in jumbo granules, but salt formation of azimsulfuron added by 1.15M solution of NaOH a little. Addition of N-methyl acrylate and modification of formulation process affected decrease in degradation of azimsulfuron upto 1.2, 2.1, and 7.2% after 2, 6 and 12 weeks under storage at $40{\pm}2^{\circ}C$, respectively, which showed the establishment of formulation recipe of the jumbo granules.