• Korean Journal of Agricultural Science
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• v.48 no.2
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• pp.343-351
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• 2021

Screening was conducted using 200 kinds of plant extracts to explore herbicide-activated components of plant origin. We separated and purified active substances and elucidated chemical structures using Ligularia stenocephala M., which has strong activity and has not yet been studied. When the solvent fractions of the leaves of Ligularia stenocephala M. were tested for their herbicidal activity, ethyl acetate and chloroform layer showed an inhibition rate of 95.2% and 94.1%, respectively. In particular, the chloroform layer exerted more than 50% herbicidal activity at 10 ppm. From the chloroform layer with the highest herbicidal activity, we isolated three herbicidal active compounds using stepwise chromatography, specifically silica gel or octadecyl silica (ODS) column chromatography, Sep-pak cartridges, and high performance liquid chromatography (HPLC). Based on the analysis of the active compounds using electron ionization mass spectroscopy (EI-MS), ¹H-NMR, and ¹³C-NMR, we identified the active compounds as euparin, 5,6-dimethoxy-2-isopropenylbenzofuran, and liguhodgsonal. When the herbicidal activity of the identified compounds was tested, euparin showed selective herbicidal activity for lettuce at 10^-3 M, and both liguhogsonal and 5,6-dimethoxy-2-isoprophenylbenzofuran exerted selective activity for rice and Echinochloa crus-galli.

• The Korean Journal of Pesticide Science
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• v.4 no.3
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• pp.89-92
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• 2000

A series of 5-(2-metllyl-2-alkylindallyl)cyclohexane-1,3-diones were synthesized and evaluated for herbicidal activities in a green house. Under submerged paddy conditions, those compounds showed high herbicidal activity against barnyardgrass with good tolerance on rice.

• 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.

• The Korean Journal of Pesticide Science
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• v.4 no.3
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• pp.47-51
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• 2000

A some of synthesized 2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-5-yl substituents in 5-benzofuryl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclohex-2-en-1-one derivatives as substrates were found to show herbicidal activity against rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) with post emergence under submerged conditions. The substrate with $R_{1}$=methyl substituents, $1{\sim}5$ showed the higher herbicidal activity to the seed, 3 leaf stage of rice plant and barnyard grass. The structure activity relationships (SARs) on the herbicidal activity of $R_{1}$ and $R_{2}$ on the azomethine bond in substrate were analysized. In the condition of $R_{1}$ groups are same, the herbicidal activity against 3 leaf stage of rice plant were governed by the optimal hydrophobicity $(logP)_{opt.}=4.57$. Whereas, in the case of barnyard grass, the herbicidal activities were largely dependent upon the steric effect, $B_{2}$ constant than hydrophobicity. In order to take the selective herbicidal activity between rice plant and barnyard grass, it is assumed that the (S) should be a round shape with higher hydrophobicity (logP>4.57) than optimal value. Also, the $R_{1}$ groups must be small and the $R_{2}$ groups are advisable to be unsaturate.

• 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.

• Applied Biological Chemistry
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• v.49 no.3
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• pp.238-242
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• 2006

The herbicidal activities against the pre-emergence of rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-gall) with changing substituents $(R_1-R_4)$ of new 5-benzofuryl-2-[1-(alkoxyimino) alkyl]-3-hydroxycyclohex-2-en-1-one derivatives as substrate molecules were studied quantitatively using comparative molecular field analyses (CoMFA). The optimized CoMFA models (rice plant: A5 & barnyard grass: B3) were derived from atom based fit alignment and a combination of CoMFA fields. The two models for herbicidal activity against two plants showed the best predictability and fitness ($q^2$>0.6 & ${r^2}_{ncv.}$>0.94) for the herbicidal activities. Also, CoMFA-HINT contour maps showed that the selective herbicidal activity between rice plant and barnyard grass depends on the hydrophobicity of $R_2\;and\;R_3$ groups in molecule. Therefore, it is expected that the herbicidal activity against barnyard grass will be improved by the introduction of the steric bulk small and hydrophobic group.

• Weed & Turfgrass Science
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• v.1 no.4
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• pp.44-49
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• 2012

The objective of this study was to know the herbicidal activity of the essential oil from amyris (Amyris balsamifera). In a seed bioassay experiment, the amyris essential oil inhibited the growth of rapeseed (Brassica napus) by fifty percent at 8.8 ${\mu}g\;g^{-1}$. And in a greenhouse experiment, sorghum, barnyard grass and Indian jointvetch, which was applied in above-ground parts, with the amyris essential oil at 4,000 ${\mu}g\;ml^{-1}$ showed visual injuries of 90, 70, and 70, respectively (0, no damage; 100, total damage). However, soil application of the essential oil did not show such herbicidal injuries. In a field experiment, foliar application of the amyris essential oil at 5% controlled effectively weeds such as barnyardgrass, shepherd's purse, and clover in 24 hours. Our results indicated that the amyris essential oil had herbicidal activity. To understand the composition of the amyris essential oil, the oil was analyzed by gas chromatography-mass spectometry with solid-phase micro-extraction apparatus. There were 15 organic chemicals in the oil and the major constituents were calarene, elemol, ${\gamma}$-eudesmol, curcumene, ${\beta}$-sesquiphellandrene, zingiberene, selina-3,7(11)-diene, 1,3-diisopropenyl-6-methyl-cyclohexene, ${\beta}$-bisabolene, and ${\beta}$-maaliene. Overall results suggest that the amyris essential oil had a herbicidal activity with fast, contact, and non-selective mechanism.

• The Korean Journal of Pesticide Science
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• v.4 no.3
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• pp.34-39
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• 2000

A new fifteen 2,3-dihydro-2-ethyl-2,4,6,7-tetramethylbenzofuran-5-yl substituents in 5-benzofuryl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclohex-2-en-1-one derivatives as substrate were synthesized and their herbicidal activities against rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) with post emergence were measured under submerged conditions. The $R_{1}$=methyl substituents, $1{\sim}8$ showed the higher herbicidal activity to the rice plant and barnyard grass. The structure-activity relationships (SARs) on tile herbicidal activity of $R_{1}$ and $OR_{2}$ groups on the azomethine bond in substrates were analysized. From tile results of dicussed SAR, the herbicide activities against rice plant would depend largely on the steric factor, Whereas, in case of barnyard grass, the activities were governed by the hydrophobicity factor. The conditions of selective herbicide activity between the two plant species are assumed that the substrates should nave optimal hydrophobicity ( $(logP)_{opt.}=6.0$), a $R_{1}$ groups of small and a long $OR_{2}$ groups.

• Applied Biological Chemistry
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• v.48 no.4
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• pp.394-399
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• 2005

The comparative molecular field analyses (CoMFA) models for the herbicidal activities against barnyardgrass (Echinochloa crus-galli) and rice plant (Orysa sativa L.) by the substituent (R) on the hexahydroisoindol-1-one ring in a series of new 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-one derivatives were conducted and discussed for selectivity between both plants. The statistical results of the two best models (B2 & R7) showed the best predictability for the herbicidal activities based on the cross-validated value $q_2(r^2cv.=0.529{\sim}0.755)$ and none cross-validated value $({r^2}_{ncv.}=0.937{\sim}0.945)$, respectively. Based on the findings, the predictability and fitness of the model (B2) for barnyard grass was better than that of the model (R7) for rice plant. From the two models and contour maps, it is revealed that the novel selective character for herbicidal activity between the two plants depend on the electrostatic field and steric field for the substituent of ortho-positions on the S-phenyl group as R-substituent in hexahydroisoindol-1-one ring.

• Applied Biological Chemistry
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• v.39 no.6
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• pp.455-459
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• 1996

Nine hundred and eighty fungal strains were isolated from lesions of Trifolium repens L. and various weeds. Among them, F40362, F40496, F40497 strains were selected by the screening of herbicidal activity on Trifolium repens L. and Zoysia japonica. Selected three strains showed selective activity between Trifolium repens L. and Zoysia japonica, and were identified as Penicillium sp.