• The Korean Journal of Pesticide Science
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• v.4 no.2
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• pp.21-28
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• 2000

A new fourty six 2-(4-(6-chloro-2-benzoxazolyloxy)phenoxy)-N-phenylpro- pionamide derivatives were synthesized and the herbicidal activities against rice plant and barnyard grass with pre-emergence in down land were measured. The structure activity relationships (SAR) between the activities and physicochemical parameters of the substituted(X) N-phenyl group in substrates were analyzed and discussed by Free- Wilson and Hansch method from the basis on the former study (Sung. et. al., 1999). The conditions of selective herbicide activity both the barnyard grass and rice plant are shown that the optimal hydrophobicity, $({\pi})_{opt.}=1.34$ and electron donating with field effect (F<0) of meta and ortho, para-substituted mono or disubstituent on the N-phenyl ring were found to contribute significantly. The herbicidal activities against barnyard grass are roughly the same as the results in up land whereas damage to rice plant in down land more increase than that of up land. Degradation products in water are 2-(4-(6-chloro-2-benzoxazolyloxy)phenoxy)propionic acid ((A)) (obs. pKa=4.35 & obs. logP=4.77) and 6-chloro-2-benzoxazolone (B) (obs. pKa=8.40 & obs. logP=2.90). These results were supposing that the hydrolysis product of substrates, (A) is comparatively absorbed in rice plant but not in barnyard grass. And it is assumed from the SAR equations that the 2,6-dimethyl-4-methoxymethyl group substituent ($pI_{50}=5.41$, 3g/ha) is selected as the most highest herbicidal activity against barnyard grass in green house.

• 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.

• Proceedings of the Korean Society of Crop Science Conference
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• 2017.06a
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• pp.40-40
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• 2017

Rice (Oryza sativa L.) is one of major crops of Vietnam. Rice plant contains many secondary metabolites that are potent to inhibit growth of other plants. This study was carried out to find potential plant growth inhibitors from rice plants. Seven rice varieties were cultivated in the fields affiliated to Hiroshima University, Japan; Mature stems and leaves from each variety were collected, and then they were extracted with methanol, hexane, ethyl acetate, butanol, and water. Total phenolic content and total flavonoid content were the highest in ethyl acetate extract. DPPH antioxidant assay results showed that the ethyl acetate extract also had higher $IC_{50}$ value. Therefore, the ethyl acetate extracts were selected for laboratory bioassay. Results showed that the two-local variety Re nuoc and Nan chon inhibited the germination of radish and barnyard grass seedlings at the greatest levels, as compared to other cultivars. HPLC quantification indicated that the ethyl acetate extracts of Re nuoc and Nan chon rice plant parts consists of phenolic and flavonoids compounds which are potent as plant growth inhibitors. Further laboratory bioassay and field experimentation will be conducted to validate the laboratory bioassay findings.

• Korean Journal of Environmental Agriculture
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• v.25 no.3
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• pp.268-275
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• 2006

ALA (5-aminolevulinic acid) has been proposed as a tetrapyrrole-dependent photodynamic herbicide by the action of the protoporphyrinogen IX oxidase (Protox IX). A study was conducted to determine photodynamic herbicidal effect of ALA on seedling growth of rice (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli Beauv. var. oryzicola Ohwi) under dry and wet conditions. ALA effect on early plant growth of rice and barnyardgrass was greatly concentration dependant, suggesting that it promotes plant growth at very low concentration and inhibits at high concentration. No significant difference in herbicidal activity of biologically and synthetically produced ALAs on plant lengths of test plants was observed ALA exhibited significant photodynamic activity regardless of PSDIP and its duration. Significant shoot growth inhibition by ALA soaking treatment exhibited apparently, indicating that ALA absorbed through root system was translocated into shoot part of plants. ALA reduced plant heights of rice and barnyardgrass seedlings by 6% and 27%, respectively, showing more tolerant to ALA in rice under wet condition. Leaf thickness was reduced markedly by ALA with increasing of ALA concentration, due to mainly membrane destruction and severe loss of turgidity in mesophyll cells, although the epidermal was little affected. It was observed that photodynamic herbicidal activity of ALA applied by pre-and post-emergence application exhibited differently on plant species, and that the activity of ALA against susceptible plants was highly correlated with growing condition.

• The Korean Journal of Pesticide Science
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• v.5 no.3
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• pp.12-17
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• 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
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• v.7 no.2
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• pp.108-116
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• 2003

A series of new quinclorac family, herbicidal 3-phenyl-5-(3,7-dichloro-8-quinolinyl)-1,2,4-oxadiazole derivatives as substrate were synthesized and their growth inhibition activity $(pI_{50})$ against root and shoot of rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) were determined. And then comparative molecular field analysis (CoMFA) and molecular holographic quantitative structure- activity relationship (HQSAR) were compared in terms of their potential for predictiability. The statistical results were suggested that HQSAR based model had better predictability than CoMFA model. The selective factors to remove barnyard grass take electron withdrawing groups which can be created positive charge and steric bulky on the phenyl ring. Results revealed that the unknown 2,6-dichloro-substituent, U5 and 2,4,6-trichloro-substituent, U6(${\Delta}pI_{50}$=CoMFA: 1.18 & HQSAR: 1.82) were predicted as compound with higher activity and selectivity.

• The Korean Journal of Pesticide Science
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• v.7 no.2
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• pp.100-107
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• 2003

To improve the growth inhibitory activity against the shoot and root of rice plant (Oryza sativa L) and barnyard grass (Echinochloa crus-galli), a series of N-substituted phenyl-3,4-dimethylmaleimdes derivatives as substrates were synthesized and then their the inhibitory activities of protoporphyrinogen oxidase (1.3.3.4), protox were measured. The quantitative structure-activity relationships (QSAR) between structures and the inhibitory activities were studied quantitatively using the 2D-QSAR method. And also, molecular sharp similarity between the substrate derivatives and protogen, substrare of protox enzyme were studied. The activities of the two plants indicated that barnyard grass had a higher activity than the rice plant and their correlation relationships have shown in proportion for each. Accordingly, the results of SARs suggest that the electron donating groups as $R_2=Sub.X$ group will bind to phenyl ring because the bigger surface area of negative charged atoms in the substrate molecule derivatives may increase to the higher the activity against barnyard grass. Based on the molecular shape similarity, when the derivatives and protogen, subsbrate of protox enzyme were superimposed by atom fitting, the similarity indices (S) were above 0.8 level but the correlation coefficients (r) between S values and the activities showed not good.

• The Korean Journal of Pesticide Science
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• v.7 no.2
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• pp.75-82
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• 2003

We discuss that the growth inhibition activities against root and shoot of rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) by N-phenyl-3,4,5,6-tetrahydrophthalimide (A) and N-phenyl-3,4-dimethylmaleimide (B) derivatives with changing substituents can be explained and predicted using comparative molecular field analyses (CoMPA) method. And the results show that the cross-validation value, $q^2$ at three components and Pearson correlation coefficient, $r^2$ were rice plant: shoot; $r^2=0.987$, $q^2=0.387$ & root; $r^2=0.923$, $q^2=0.307$ and barnyard grass: shoot; $r^2=0.902$, $q^2=0.535$ & root; $r^2=0.900$, $q^2=0.450$, respectively. In addition, The activities of unknown compounds were predicted by CoMFA method. From the contour map of (A) derivatives, the selective factors to remove barnyard grass takes positive charge on the benzylic carbon atom (C27), negative charged carbon atom (C29) of meta position and steric bulky groups on the cyclic imino ring (C7-C8).

• Applied Biological Chemistry
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• v.47 no.4
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• pp.414-421
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• 2004

3D QSAR studies for protox inhibition activities against root and shoot of the rice plant (Orysa sativa L.) and barnyardgrass (Echinochloa crus-galli) by a series of new 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene derivatives were conducted based on the results (Sung, N. D. et al.'s, (2004) J. Korean Soc. Appl. Biol. Chem. 47(3), 351-356) using comparative molecular similarity indices analysis (CoMSIA) methodology. Four CoMSIA models, without hydrogen bond donor field for the protox inhibition activities against root and shoot of the two plants, were derived from the combination of several fields using steric field, hydrophobic field, hydrogen bond acceptor field, LUMO molecular orbital field, dipole moment (DM) and molar refractivity (MR) as additional descriptors. The predictabilities and fitness of CoMSIA models for protox inhibition activities against barnyard-grass were higher than that of rice plant. The statistical results of these models showed the best predictability of the protox inhibition activities against barnyard-grass based on the cross-validated value $r^2\;_{cv}\;(q^2=0.635{\sim}0.924)$, non cross-validated, conventional coefficient $r^2\;_{ncv.}$ value $(r^2=0.928{\sim}0.977)$ and PRESS value $(0.255{\sim}0.273)$. The protox inhibition activities exhibited a strong correlation with the steric $(5.4{\sim}15.7%)$ and hydrophobic $(68.0{\sim}84.3%)$ factors of the molecules. Particularly, the CoMSIA models indicated that the groups of increasing steric bulk at ortho-position on the C-phenyl ring will enhance the protox inhibition activities against barnyard-grass and subsequently increase the selectivity.

• Applied Biological Chemistry
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• v.51 no.3
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• pp.219-222
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• 2008

In the search for third generation herbicidal cyclic imide derivatives, the average values of herbicidal activity ($pI_{50}$) in vivo (pre-emergence) of 40 new peroxidizing herbicides, 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)thiourea derivatives (1-40) against rice plant (Orysa sativa) and barnyard grass (Echinochlor crus-galli) were studied. The molecular similarity between protoporphyrinogen IX (protogen) as the substrate of protox enzyme and Urea derivatives (1-40) was discussed quantitatively. The diallyl (20) and 3-nitro substituent (33) showed the selective herbicidal activity against barnyard grass. Allyl substituent (8) and their molecular similarity in dice (S=0.81) showed the highest levels of herbicidal activity ($pI_{50}$=4.71). Also, similarity indices (S) and superimposed volume (C) of protogen and aryl-substituents (21-40) showed good correlation.