• Applied Biological Chemistry
• /
• v.39 no.4
• /
• pp.297-303
• /
• 1996

A series of the herbicidal N-(4,6-disubstituted pyrimidin-2-yl)aminocarbonyl-2-(1,1-ethylenedioxy-2-fluoro)ethyIbenzenesulfonamides, 1 and N-(4,6-disubstituted triazin-2-yl)aminocarbonyl-2-(1,1-ethylenodioxy-2-flu ore)ethylbenzenosuIfonamides, 2 were synthesized and their herbicidal activities in-vivo against rice(Oryza sativa L.), barnyard grass (Echinochloa crus-galli), bulrush(Scripus juncoides) and pickerel weed(Monochoria vaginalis presl.) were measured by the pot test under the paddy conditions. The structure activity relationships(SAR) between the herbicidal activity$(pI_{50})$ and a various physicochemical parameters of the hetero group and 4,6-disubstituents on the heterocyclic group were analyzed by the multiple regression technique. The SAR suggest that the 4,6-dimethoxypyrimidine substituent, 1a showed selective$({\Delta}obs.pI_{50}=1.12)$ and the most highest activity against barnyard grass, which depend on the hydrophobicity(log P<0) of heterocyclo group and molecular refractivity$((M_R)_{opt.}=14.58cm^3/mol)$ constant of 4,6-disubstituents on the heterocyclic group.

• The Korean Journal of Pesticide Science
• /
• v.12 no.2
• /
• pp.103-110
• /
• 2008

To develop the third generation herbicidal cyclic imide (Cyl) derivatives, the new 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3-thiourea derivatives were synthesized and measured their herbicidal activities ($pI_{50}$) in vivo (preemergence) against rice plant (Orysa Sativa) and barnyard grass (Echinochlor crus-galli). The synthetic yields (%) of aryl derivatives (21-40) in general was higher than that of alkyl derivatives (1-20). In case of alkyl derivatives, the synthetic yield depended on the structural forms of alkyl amine groups. From the results of correlation analysis between herbicidal activities and substituents, the compound 8 and 24 showed the highest herbicidal activity against the shoot and root of barnyard grass. Especially, the compounds 11 and 6 showed the selective herbicidal activities between rice plant and barnyard grass.

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

• The Korean Journal of Pesticide Science
• /
• v.5 no.3
• /
• pp.12-17
• /
• 2001

A new 2,3-dihydro-2,3,4,6,7-pentamethylbenzofuran-5-yl substituents in 5-benzofuryl-2-[1-(alkoxyimine) alkyl]-3-hydroxycyclohex-2-en-1-ones were found to have herbicidal activity against rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) under submerged conditions. The structure activity. relationships (SARs) on the herbicidal activity of $R_1\;and\;R_2$ on the azomethine bond of 2,3-dihydro-2,3,4,6,7-pentamethylbenzofuran-5-yl subsituents were analysized. The conditions of the selective herbicide activity between rice plant (seed) and barnyard grass from the basis on the analysized SARs are assumed that the $R_2$ group of ethyl substituent ($R_1$ ) should have optimal asymmetry parameter, $(L/B_1)_{opt.}=3.96{\AA}$. And also, the $R_2$ groups consist of $C_1{\sim}C_3$ and unsaturated group such as 3-chloro-2-propenyl group was contribution to the herbicide activity.

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

• Journal of Microbiology and Biotechnology
• /
• v.15 no.2
• /
• pp.434-437
• /
• 2005

During the screening for the inhibitors of cellulose biosynthesis as herbicides, we discovered a Streptomyces sp. A6497 with a selective antifungal activity against cellulose containing Phytophthora parasitica, but not against cellulose lacking Candida albicans. The inhibitor was isolated and identified, using a series of chromatographies. Based on structure analyses with UV spectrophotometry, mass and various NMR, the inhibitor was identified as sangivamycin. The compound exhibited strong antifungal activities against P. parasitica (MIC; 3.125 $\mu$g/ml). In particular, it showed strong herbicidal activities against various weeds in the greenhouse experiment. Taken together, these results suggest that sangivamycin is a useful lead compound for the development of new herbicides.

• Korean Journal of Weed Science
• /
• v.31 no.1
• /
• pp.112-117
• /
• 2011

A series of experiments was conducted to investigate the herbicidal activity of natural compound chrysophanic acid under the greenhouse condition in 16 weed species. Chrysophanic acid showed non-selective herbicidal activity. While chrysophanic acid exhibited severe injury by foliar treatment, little or no injury was found by the soil treatment. Among the tested weeds, the most effective activity was found in grass and broad leaf weeds, a lower significant difference in herbicidal activity was found in sedge. At early post-emergence, weeds appeared to be very susceptible to chrysophanic acid with $2,000{\mu}g\;mL^{-1}$. The higher the natural compound concentrations, the lower weed growth. At middle post-emergence, weeds appeared to be very effective to chrysophanic acid with $30,000{\mu}g\;mL^{-1}$.

• The Korean Journal of Pesticide Science
• /
• v.6 no.4
• /
• pp.279-286
• /
• 2002

To improve the growth inhibition activities and selectivities for quinclorac family, novel 3-substituted phenyl-5-(3,7-dichloro-8-quinolinyl)-1,2,4-oxadiazole derivatives as the substrate were synthesized and their the activities ($pI_{50}$) against shoot and root of rice plant (Oryza sativa L.) and barn-yard grass (Echinochloa crus-galli) were measured. And the quantitative structure-activity relationships (QSARs) between physicochemical parameters of the substitutents (R) on phenyl group and the activities ($pI_{50}$) were analyzed quantitatively. According to the SAR analyses, the substrates of planar conformation showed higher herbicidal activities against barnyard grass than rice plant. The activities against rice plant depend on the electronic effect (shoots: ${\sigma}_{opt.}=0.49$ & root: $R_{opt.}=-0.15$) of substituents, whereas the activities against shoots and roots of barnyard grass depend on hydrophobicity (${\pi}_{opt.}=0.37{\sim}2.40$). There were conditions of selective growth inhibition activity against barnyard grass when such a ortho-substituted electron donating substituents showing the hydrophobicity value, ${\pi}=2.40$ were introduced on the phenyl ring. The 2-tolyl substituent predicted from SAR equations was expected to have better growth inhibition activity and selectivity (${\Delta}pI_{50}=1.26$) for barnyard grass.

• The Korean Journal of Pesticide Science
• /
• v.3 no.3
• /
• pp.11-19
• /
• 1999

A some of synthesized 2-(4-(6-chloro-2-benzoxazolyloxy)phenoxy)-N-phenyl propionamide derivativesa substrates were found to selectivity significantly with both rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) for those her- bicidal activities with post emergence in up land. The selectivity of substrates against rice plant better than that of Fenoxaprop-ethyl. The structure activity relationship (SAR) n the selectivity of N-phenyl substituents were analyzed by the Free-Wilson and Hansch method. The SAR approach against barnyard grass is shown that the optimal ($({\pi})_{opt.}=1.60$) hydrophobicity and electron donating effects ($0<{\sigma}$ & 0$(ES)_{opt.}=0.87$) so that the herbicidal activity against rice plant can be decreased. The significance of these results on the selectivity between barnyard grass and rice plant is discussed. And it is assumed that the 2-ethoxy-3-methoxy-4-dimethylamino group substituent ($pI_{50}$=6.60, 1g/ha) is selected as the most highest herbicidal activity against barngard grass in green house.

• The Korean Journal of Pesticide Science
• /
• v.2 no.3
• /
• pp.107-116
• /
• 1998

Based on the differential growth response to exogenous gibberellic acid ($GA_{3}$) between semi-dwarf wheat(Triticum aestivum) and wild oat(Avena fatua), we examined the possibility of improving the selective performance of several herbicides by $GA_{3}$ application and the physiological background of $GA_{3}$-induced increase in herbicidal activity. Growth of wild oat was 4 to 5 times higher than that of wheat by $GA_{3}$ treatment. Pretreatment of wild oat seed with 300 ppm $GA_{3}$ increased the herbicidal activities of trifluralin and isoproturon by soil-surface application, but not of alachor and metsulfuron-methyl. $GA_{3}$ applied simultaneously with post-emergence herbicides resulted in a significant or moderate improvement of the efficacy of such herbicides as tralkoxydim, fenoxaprop-ethyl, metsulfuron-methyl, metribuzine and isoproturon, but not in the mixtures of oxyfluorfen or paraquat with $GA_{3}$. In the sequencial treatment of tralkoxydim and $GA_{3}$ at interval of one-day, $GA_{3}$ applied prior to tralkoxydim significantly increased a chlorosis and desiccation of leaf without affecting the growth inhibition by tralkoxydim. Tralkoxydim followed by $GA_{3}$ application had lower herbicidal activity than that of $GA_{3}$ followed by tralkoxydim treatment. Electrolyte leakage response of $GA_{3}$-pretreated or $GA_{3}$-untreated wild oat leaf against several compounds inducing membrane. peroxidation was compared. Differencial responses were observed in oxyfluorfen and isoproturon treatments with an increased electrolyte leakage in $GA_{3}$-pretreated tissue, but not in paraquat and rose bengal treatments. These results suggest that $GA_{3}$-induced increase in herbicidal activity is likely to be dependent on a herbicide type and may be due to activation of a metabolic ability related with herbicidal reponse as well as an increase in the herbicide absorbtion and translocation, rather than due to membrane and cell wall extention induced by $GA_{3}$, which in turn makes the herbicides easily enter.