• Journal of the Korean Chemical Society
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• v.21 no.3
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• pp.180-186
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• 1977

The preparation of 1-chloro-2-iodoperfluorocycloalkenes was achieved with a short reaction time and a high yield when the starting compound was iodinated via the metalation process using an alkyllithium reagent. Especially, the high yield of 1-chloro-2-iodo-perfluorocyclohexene was obtained when 1,2-dichloroperfluorocyclohexene was iodinated via the same reaction conditions. The coupling reaction of 1,2-dihaloperfluorocycloalkenes was also achieved with a lower reaction temperature and a shorter reaction time when the equal slurry mixture of fluorocycloolefines and DMF was reacted at a high pressure in a sublimer. The yield of the coupling product was greatly improved by this process. For a typical example, the coupling reaction of the 1-chloro-2-iodotetrafluorocyclobutene was proceeded with a higher yield of the product than that of the reported reaction, when the present method was adopted. A plausible reaction mechanism of the present coupling reactiont was proposed and the physical characteristics of the coupling product were confirmed.

• YAKHAK HOEJI
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• v.34 no.1
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• pp.15-21
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• 1990

-4,9-dione derivatives were prepared from $2-chloro-3-({\alpha}-accetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ and 2-chloro-3-N-phenylamino-1,4-naphthoquinone. $2-Chloro-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ was reacted with amines to give $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ derivatives. Subsequent treatment of $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ with sodium ethoxide gave -4,9-dione derivatives. When 2-chloro-3-N-phenylamino-1,4-naphthoquinone reacted with sodium ${\alpha}-cyano$ ethyl acetate, 2-amino-3-ethoxycarbonyl-N-phenyl--4,9-dione was obtained. However, with sodium diethyl malonate, not -4,9-dione but 2-chloro-3-bis-(methoxycarbonyl)-methyl-2H-3-N-phenylamino-1,4-naphthoquinone was obtained.

• The Korean Journal of Pesticide Science
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• v.8 no.2
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• pp.145-149
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• 2004

A series of 2-[4-(6-chloro-2-benzoxazolyloxy)phenoxy]-propionamide were synthesized and evaluated for post herbicidal activity under upland condition. 2-[4-(6-chloro-2-benzoxazolyloxy)phenoxy]-N-(2-fluorophenyl)-N methyl propionamide showed high herbicidal activity against barnyardgrass with good selectivity on rice.

• Applied Biological Chemistry
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• v.47 no.3
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• pp.351-356
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• 2004

Holographic quantitative structure activity relationships (HQSAR) as 2D QSAR between the herbicidal activities against root and shoot of rice plant (Orysa sativa L.) and barnyardgrass (Echinochloa crus-galli), and structures of A=3,4,5,6-tetra-hydrophthalimino, B = 3-chloro-4,5,6,7-tetrahydro-2H-indazolyl and C = 3,4-dimethylmaleimino substituents in 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene derivatives were studied and discussed. The statistical results of four HQSAR models for the herbicidal activities against root and shoot of the two plants showed the best predictability of the herbicidal activities based on the cross-validated $r^2\;_{cv}\;(q^2=\;0.760{\sim}0.924)$, non cross-validated conventional coefficient $(r^2\;_{ncv}\;=\;0.868{\sim}0.970)$ and PRESS values $(0.123{\sim}0.261)$. The results indicated that the qualities of HQSAR models for barnyardgrass were slightly higher than that of rice plant. And also, the predictability of HQSAR models were higher $(q^2\;=\;HQSAR\;>\;CoMFA)$ than CoMFA but the conventional coefficients of HQSAR models lower $(r^2\;=\;HQSAR\;<\;CoMFA)$ than CoMFA. Moreover, from the contribution maps, it was founded that the selectivity between the two plants depends upon the 2-fluoro-4-chloro-5-alkoxyanilino and $R_3$ substituent on the C-phenyl ring. These features suggest where to modify a molecular structure in order to improve its selective of herbicidal activities against barnyardgrass.

• Applied Biological Chemistry
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• v.35 no.2
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• pp.87-91
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• 1992

Twenty-six N-substituted-5-chloro-1,3-dimethylpyrazole-4-carboxamide were synthesized and their antifungal activity against Rhizoctonia solani, Pyricularia oryzae, Botrytis cinerea and Colletotricum gleosporiodes was compared. N-phenyl-5-chloro-l,3-dimethylpyrazole-4-carboxamides having electron releasing group at the meta position of phenyl ring demonstrated good fugicidal activity against R. solani.

• Bulletin of the Korean Chemical Society
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• v.13 no.6
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• pp.676-680
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• 1992

Irradiation of N-t-butyl-N-chloro-3-phenylpropanesulfonamide (1a) in benzene at $20^{\circ}C$ using 450 W high pressure mercury arc lamp in the presence of oxygen affored N-t-butyl-3-phenylpropanesulfonamide (2), N-t-butyl-3-chloro-3-phenylpropanesulfonamide (3), and N-t-butyl-3-oxo-3-phenylpropanesulfonamide (4). Similarly, N-t-butyl-4- (5), N-t-butyl-4-chloro-4- (6), and N-t-butyl-4-phenylbutanesulfonamides (7) were obtained from N-t-butyl-N-chloro-4-phenylbutanesulfonamide (1b). However, irradiation of N-t-butyl-N-chloro-5-phenylpentanesulfonamide (1c) under the same conditions gave complex mixtures. These results indicate that sulfonamidyl radical generated from each of 1a and 1b can abstract intramolecularly a hydrogen atom from the benzylic position only by forming six and seven-membered transition states, respectively.

• Journal of the Korean Chemical Society
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• v.40 no.11
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• pp.681-685
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• 1996

New 6-cyanomethyl-1,3,5-triazine derivatives 4 containing amino, n-propylamino, isopropylamino and anilino groups at 2-and 4-position on the 6-cyanomethyl-1,3,5-triazine ring were prepared from 6-chloro-l,3,5-triazine derivatives 2' and 3 with tert-butyl cyanoacetate. The derivatives of 6-chloro-l,3,5-triazine 2' and 3 containing amino, n-propylamino, isopropylamino and anilino groups at 2- and 4-position on the 6-chloro-1,3,5-triazine ring were prepared from 2,4,6-trichloro-1,3,5-triazine as well as 4,6-dichloro-1,3,5-triazine derivatives 2 with amine derivatives.

• Bulletin of the Korean Chemical Society
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• v.19 no.12
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• pp.1334-1336
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• 1998

Kinetic studies are carried out on the reactions of 2-chloro-2-propen-1-yl arenesulfonates with anilines and N,N-dimethylanilines in acetonitrilile at 45.0 ℃. The 2-chloro substituent is found to deactive the allyl moiety with considerable decrease in the rates. The sign and magnitude of the cross-interaction constant (ρxz 0.3) and the inverse secondary kinetic isotope effect (kH/kD 0.92) support an SN2 mechanism with a relatively tight transition state. The possibility of an SN2' mechanism can be safely precluded based on the ρxz values observed.

• Applied Chemistry for Engineering
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• v.9 no.4
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• pp.603-607
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• 1998

Cellulose was reacted with ethylene oxide to get hydroxyethylcellulose. Quaternary ammonium salt was produced by reaction of epichlorohydrin and trialkylamine. The epoxide ring was opened by acid addition to 3-chloro-2-hydroxypropyltrialkylammonium chloride. Previously unreported two compounds, hydroxyethylcellulose-2-hydroxypropylammonium chloride ether and hydroxyethylcellulose-2-hydroxypropyltriethylammonium chloride ether were synthesized by substitution reaction of hydroxyethylcellulose with glycidyltrialkylammonium chloride or 3-chloro-2-hydroxypropyl-glycidyltrialkylammonium trialkylammonium chloride. All of the compounds including starting materials and reaction intermediates were characterized by $^1H$-NMR and FT-IR spectroscopy.

• Journal of the Korean Chemical Society
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• v.39 no.9
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• pp.728-733
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• 1995

The derivatives of 2-amino-4-methylcyano-5-methylsulfonylpyrimidine 6 containing chloro, methoxy, ethoxy, phenoxy, amino and anilino groups at 6-position on the pyrimidine ring were prepared from 2-amino-4-chloro-5-methylsulfonylpyrimidine derivatives 4 and tert-butylcyanoacetate. The derivatives of 2-amino-4-chloro-5-methylsulfonylpyrimidine 4 containing methoxy, ethoxy, isopropoxy, phenoxy, amino and anilino groups at 6-position on the pyrimidine ring were prepared from 2-amino-4,6-dichloro-5-methylsulfonylpyrimidine 3.