• The Korean Journal of Pesticide Science
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• v.4 no.2
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• pp.69-71
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• 2000

The herbicidal activities ($pI_{50}$) with alkoxy (RO-) groups on the azomethine nitrogen atom in 5-(2,3-dihydro-2,2-dimethylbenzothiophene-7-yl)-2-(1-(alkoxyimino)butyl)-3-hydroxy-2-cyclohexene-1-one derivatives against various weeds were measured in the flooded and in the paddy conditions. Particularly, i-propoxy subsutuent, 5 of them showed excellent herbicidal activity at a rate of 4kg/ha with pre-emergence against barnyard grass (Echinochloa crus-galli) with good selectivity on rice plant (Oryza sativa). The results of the structure-activity relationships (SAR) analyses are shown that the alkyl subsituents with higher hydrophobicity (logp>0) and electron donating (${\sigma}^*<0$) group as a new substrate rather than alkoxy substituents seems to be contribute to the herbicidal activity with pre-emergence.

• The Korean Journal of Pesticide Science
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• v.6 no.2
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• pp.58-63
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• 2002

New photodynamic herbicidal 2,3-dihydro-2,2,4,5,6-pentamethylbenzofuran-5-yl, (I) and 2,3-dihydro-2-ethyl-2,4,5,6-tetramethylbenzofuran-5-yl, (II) substituents in 6-benzofury-2-[1-( alkoxyimino )alkyl]-3 hydroxycyclohex-2-en-1-one derivatives were synthesized and their herbicidal activities against rice plant (Oryza sativa L.), barnyard grass (Echinochloa crus-galli) and pickerel weed (Monochoria vaginalis presl.) were measured under submerged pre and post-emergence conditions. Particularly, a series of (I) compounds showed good selective herbicidal activities between the 3 leaf stage of rice plant and barnyard grass at rates of $0.25{\sim}0.0007kg/ha$. The structure activity relationships (SAR) on the herbicidal activity with changing N-alkoxy groups were discussed quantitatively. According to the SAR results, it was expected that the selectivity factor between seed of rice plant and barnyard grass should be rely on the N-alkoxy groups with bigger dipole moment and bigger (or smaller) $B_3$ constant than optimal value $(B_3)_{opt.}=4.41{\AA}$. Compared with (I), the (II) substituents showed more superior herbicidal activities.

• The Korean Journal of Pesticide Science
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• v.3 no.1
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• pp.1-12
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• 1999

Herbicidal activities of newly synthesized experimental compound, KSC-13906 [Erythro N-{(4,6-dimethoxy pyrimidin-2-yl)aminocarbgnyl}-2-(2-fluoro-1- hydroxy-n-propyl)benzenesulfonamide, US Patent 5,461,025], were investigated in greenhouse and field for development as a paddy herbicide. KSC-13906 exihibited excellent weeding effects and selectivity to rice under submerged paddy condition in geenhouse. At the application rate of $2.5{\sim}5$ g ai/ha treated on surface of water, KSC-13906 effectively controlled three annual weeds such as Echinochloa crus-galli var. oryzicola. Scirpus juncoides, and Monochoria vaginalis as well as five perennial weeds such as Cyperus serotinus, Sagittaria pygmaea, Eleocharis kuroguwai, Potamogeton distinctus, and S. trifolia. However, there was no effect on Aneilema keisak and Lindernia procumbens. Especially, KSC-13906 effectively controlled Echinochloa crus-galli var. oryzicola at growth stages ranging from pre-emergence to 3-leaf stage. Antagonistic interaction was found between pyrazosulfuron-ethyl and mefenacet, but not between KSC-13906 ana mefenacet. KSC-13906 had high selectivity to transplanted rice, but caused phytotoxic effect on direct-seeded rice when treated before 3-leaf stage. Herbicidal activity of KSC-13906 on the Echinochloa crus-galli var. oryzicola was 7-folds greater than that of pyrazosulfuron-ethyl in terms of relative dose ratio of the herbicides. These results suggest that KSC-13906 possesses selective herbicidal potency in rice.

• Korean Journal of Agricultural Science
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• v.37 no.1
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• pp.1-6
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• 2010

Allelopathic activity of rotation crop residues to common weeds and selectivity of crops were studied for developing an alternative weed control strategy in upland organic farming. All rotation crop residues with various ratios suppressed weed growth, but the growth of crop species stimulated a little when those were grown with the mixture of rotation crop residues except a few crop species. Among the rotation crop residues used in this study hairy vetch was the most effective, followed by Chinese milkvetch, barley and rye in suppression of weed growth. The 90:10 (crop:soil, v/v) treatments incorporation rate of crop residues such as hairy vetch and Chinese milkvetch suppressed completely the growth of all weed species tested in this study. The effect of crop residues on suppression of weed growth reduced to 90% when the incorporation rates decreased to 60% [60:40 (crop:soil, v/v). It was noticed that broadleaf weed species were more susceptible to rotation crop residues than grass weed species. In the influence of crop residues on the crop growth, no growth inhibition was found in red pepper, lettuce and perllia at any incorporation rates, but tomato, cucumber and corn were slightly inhibited in a few cases at their highest incorporation levels. This study demonstrated that rotation crop residues especially hairy vetch and Chinese milkvetch have high herbicidal effects against weeds without inhibiting the growth of crop species.

• The Korean Journal of Pesticide Science
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• v.8 no.3
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• pp.175-183
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• 2004

The characteristics of the experimental compound EK-5439 [3-Chloro-2-[4-chloro-2-fluoro-5-(5-methyl-3-phenyl-4,5-dihydroisoxazol-5-yl-methoxy)-phenyl]-4,5,6,7-tetrahydro-2H-indazole] was investigated to characterize as a new herbicide to use in rice field. The selectivity between rice and barnyardgrass was very good when treated from 0 to 4 days after seeding under soil application. In the overflowing experiment, herbicidal efficacy of EK-5439 was stabilized 12 hrs after application. Vertical migrations in submerged paddy soil of EK-5439 and oxadiazon were equally observed below a soil depth of 1 cm under 5 cm/day leaching condition. Half-lives for herbicidal efficacy of EK-5439 and oxadiazon were 6.1, and 9.6 days, respectively, under submerged paddy condition. EK-5439 showed rapid adsorption to the soil clay, such as bentonite.

• 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.

• The Korean Journal of Pesticide Science
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• v.4 no.2
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• pp.32-36
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• 2000

A series of synthesized N-(2-fluoro-4-chloro-5-alkyloxyphenyl)-3,4-dimethyl-2-arylthio-5-oxo-2,5-dihydropyrrole derivatives as substrates were found to selectivity significantly with both rice plant (Oryza sativa L.) and weeds, barnyard grass (Echinochloa crus-galli) and bulrush (Scriptus juncoides) for those herbicidal activities at a rate of 0.1 kg/ha with post emergence under submerged conditions. The structure activity relationships (SARs) on herbicidal activity of $SR_{2}$=2-arylthio substituents on the pyrrole ring were analysized. From the results, the relative contribute orders of the $SR_{2}$ with phenyl group on the activity are meta > para > ortho-substituents. Among these compounds, the $R_{1}=propargyl$ (IA) subsrituents, $1{\sim}12$ showed higher activity than the $R_{1}$=2-chloro-2-propenyl (IB) substituents, $13{\sim}16$. The $SR_{2}$ groups of IA substituents shown that the optimal steric constant, $(Es)_{opt.}=3.25$ and m-phenylthio substituents were found to be -contribute the activity against barnyard grass. But the herbicidal activity of IB substituents against bulrush would depend upon the molar refractivity, $M_{R}$ constant of $SR_{2}$ group.

• Korean Journal of Weed Science
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• v.30 no.4
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• pp.421-428
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• 2010

A foliage contact herbicidal substance was separated from ethyl ether fraction in n-hexane extract of Saussurea lappa roots and identified as dehydrocostus lactone [(3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[5,4-d]furan-2-one](DHCL). When DHCL at 4,000 ppm was foliage-applied to two grasses and two broadleaf plants, greater than 85% necrotic injury was obtained from large crabgrass, maize and soybean, whereas only about 40% necrotic injury appeared in black nightshade, indicating that DHCL has no gross morphological selectivity, but shows difference in contact response among the plant species tested. Conductivity in incubation medium of the leaf disks treated with DHCL increased as the incubation time continued. Relatively low contact injury in black nightshade as compared with the other three plant species tested was attributed to decrease in absorption of DHCL due to relatively high amount of cuticle. DHCL did not require light in the herbicidal action and there were no inhibitory effects on seed germination and cell elongation. Acetyl-CoA carboxylase activity was inhibited by 30% and 58% at $100\;{\mu}M$ and $1000\;{\mu}M$ DHCL, respectively. These results suggested that the herbicidal action of DHCL was related with inhibition of fatty acid synthesis which in turn caused to weaken cell membrane integrity.

• 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.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.23 no.3
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• pp.2-4
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• 1978

Some of the remarkable accomplishments mentioned in the special lecture recalling 38 years of my research on the development of herbicides can be summarized as follows; 1) The physiology, movement in the soil, and decomposition and/or inactivation of the phenoxy and other herbicides by the invention of the Raphanus test were elucidated. And these findings led to the establishment of the theory of herbicidal treatment layer with the result of the origination of the application of PCP in flooded lowland paddy, which opened new era of soil application of herbicides in lowland paddy. 2) The granulation of herbicides for lowland paddy including PCP urea was developed. 3) The fact that propanil has generic selectivity in gramineae was found. And propanil was distributed in rice growing regions of the world. In addition, satanil for upland and propanil/NAC for flooded lowland paddy, propanil mixtures, were developed. 4) 15 kinds of new herbicides derived from plant hormones developed in my laboratory were develop ed, and the research trends in the future were presented.