• Korean Journal of Weed Science
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• v.30 no.3
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• pp.183-190
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• 2010

The objective of this study was to isolate a herbicidally active compound from curly dock (Rumex crispus), a native weed in Korea and to identify its' chemistry. The $GR_{50}$ value of methanol extracts which is determined by a seed bioassay using rapeseed (Brassica napus) seedlings was $935\;{\mu}g\;g^{-1}$. Activity-directed isolation of ethylacetate extract led to the isolation of ECDA fraction with $GR_{50}$ value $53\;{\mu}g\;g^{-1}$. Based on data of GC-MS, $^1H$-NMR and $^{13}C$-NMR, the chemical structure of ECDA was determined as 2H-furo[2,3-H]-[1]-benzopyran-2-one which is known as angelicin. The $GR_{50}$ values of angelicin to barnyardgrass (Echinochloa crus-galli), southern crabgrass (Digitaria ciliaris), and indian jointvetch (Aeschynomene indica) were 426, 66 and $216\;{\mu}g\;g^{-1}$, respectively. Our results suggest that angelicin could be used as a lead compound for the development of new herbicides.

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

• 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.

• Korean Journal of Weed Science
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• v.9 no.2
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• pp.108-115
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• 1989

An experiment was carried out at the International Rice Research Institute in 1987 to understand the seed germination and seedling development of rice and Echinochloa species. The percentage germination of rice cultivars(IR64 for lowland-type and UPLRi-5 for upland-type) was extremely high(>90%) regardless of temperature while that of Echinochloa species ranged from 10 to 80% depending on the species. Among these, E. crus-galli ssp. kispidula had the lowest germination with less than 20% at the high temperatures ($30^{\circ}C$, $35^{\circ}C$) and about 45% at the low temperature ($25^{\circ}C$). Original seed weight gradually decreased with time white root and shoot weight increased for both rice and Echinochloa species. However, increase in root and shoot weight did not compensate for the loss of stored carbohydrate during the experimental period. The root of E. glabrescens grew from the seed on the opposite side of the shoot while for rice it grew from the same side of the seed as the shoot. Echinochloa glabrescens had a leaf blade-like expanded first leaf that contained chlorophyll while rice had an incomplete first leaf that had no leaf blade and no chlorophyll. Due to this E. glabrescens could grow independently 2 to 3 days earlier than rice.

• Korean Journal of Weed Science
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• v.18 no.1
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• pp.1-11
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• 1998

This experiment was conducted to investigate weed infestation and to determine effective weed control methods in direct-seeded rice. Twenty two weed species occurred in dry- and water-seeded rice, which was mainly composed of annual weeds. Dominant weed species in dry-seeded rice were Cyperus difformis, Echinochloa crus-galli, Aneilema keisak and Digitaria sanguinalis in discending order. Dominant weed species in water-seeded lice were E. crus-galli, C. difformis, Monochoria vaginalis and Scirpus juncoides. E. crus-galli emerged at 7 days after sowing. In water-seeded rice, E. crus-galli emerged at 5 days after sowing, and M vaginalis, S. juncoides and C. difformis at 8~10 days after sowing. Mean days to emerge important weeds was 20 days in dry-seeded rice and 13 days in water-seeded rice. Leaf development of weeds was faster than that of rice in dry-seeded rice. In water-seeded rice, E eras-galli was more vigorous than rice, but leaf development of other weeds were slower than that of rice. Changes in number of weeds and dry weight oil weed species varied depending upon weed species in the direct-seeded rice. Dry weight of weeds were increased greatly from 30 days to 60 days after sowing in dry-seeded rice. Number of weeds tended to increase up to 40 days after sowing drastically, and then trend of the increase was dull thereafter. Dry weight and number of weeds increased up to 20~60 days after sowing in water-seeded rice. Most effective herbicide treatments was foliar application of cyhalofop/bentazon at 20 days after sowing followed by fenoxaprop/bentazon at 45 days after sowing in dry-seeded rice. All herbicide treatments except foliar applications were very effective to control weeds in water-seeded rice. Slight phytotoxicity was observed in foliar applied fenoxaprop/bentazon at 45 days after sowing in water-seeded rice, but it did not affect rice yield.

• Applied Biological Chemistry
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• v.30 no.4
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• pp.351-356
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• 1987

This study was conducted to investigate the absorption and translocation of pretilachlor [2-chloro-2, 6-diethyl-N-(n-propoxyethyl)-acetanilide] in plants and to evaluate the mobility in soil using the $^{14}C-or$ non-labelled compound in laboratory. Rice plant(Oryza sativa L.) was very tolerant to pretilachlor. Echinochloa crus-galli P. Beauv. was completely controlled by pretilachlor at 60g a.i./10a. At the 120g a.i./l0a, growth of Cyperus serotinus Rottb. and Sagittaria pygmaea Miq. was inhibited by 75% and 25%, respectively. The growth inhibition depended on absorbed amount of $^{14}C-pretilachlor$. The greatest concentration of $^{14}C$ was found in E. crus-galli, whereas the lowest was determined in rice plant. The rate of absorption and translocation in E. curs-galli was faster than in rice plan. Pretilachlor moved to 6cm deep in sandy clay loam, clay loam and loam soils, but to 10cm in sandy loam soil. In the soils herbicide-treated layer was found 0 to 2cm profile.

• Journal of Bio-Environment Control
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• v.15 no.3
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• pp.277-282
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• 2006

For searching the natural herbicide-components, the seed germination and seedling growth of receptor plant species (Brassica campestris, Sesamum indicum, Perilla frutescens and Echinochloa crus-galli) were investigated in four solvent-extracts extracted from Coptis chinensis Franch. The seed germination of receptor plant species was largely inhibited in 2,000 ppm of ethyl acetate compared to the control, and it was inhibited in order of P. frutescens, B. campestris, E. crux-galli, and S. indicum. In seedling growth, the shoot and root elongations of receptor plant species were inhibited in order of S. indicum, P. frutescens, B. campostris, and E. crus-galli. Root elongation was remarkably reduced in order of $H_2O$, butyl alcohol, and hexane, ethyl acetate extracts. Of four receptor plant species, seed germination and seedling growth of B. campestris and S. indicum showed the species-specific reaction to the solvent-extracts extracted from C. chinemis. $H_2O$ extract had a natural herbicide potential to the seed germination or root elongation in B. campestris and S. indicum. The result can be provided a basic data f3r the development of natural herbicide.

• Korean Journal of Weed Science
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• v.18 no.3
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• pp.197-204
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• 1998

This study was conducted to determine the activity of ALS, content of endogenous free amino acids and fatty acids affected by herbicide mixture of cyhalofop-butyl, pyribenzoxim and pyrazosulfuron-ethyl. $I_{50}$ values (concentration required for 50% inhibition of ALS activity) of pyribenzoxim herbicide on the activity of ALS in Echinochloa crus-galli and Cyperus serotinus in vitro were recorded at 4${\times}$100 nM and 5${\times}$10 nM, respectively, while $I_{50}$ values of pyrazosulfuron against E crus-galli and C. serotinus were 4.5${\times}$10 nM and 4${\times}$10 nM, respectively, and the mixture of two herbicides showed additive effect on ALS activity at the low application rate, and independent effect at the high application rates of two herbicides. The inhibition rates of the three herbicides mixture treatment on the three branch-chain amino acids such as valine, leucine and isoleucine were 74.6%, 66.6% and 57.9% in C. serotinus and 36.6% 51.1% and 48.1% in E. crus-galli, respectively. A little bit higher inhibitory effect on the three branch-chain amino acids in C. serotinus and E. crus-galli seedlings was observed in two herbicide mixture of pyribenzoxim with pyrazosulfuron than three herbicide mixture of cyhalofop with pyribenzoxim and pyrazosulfuron. The interaction among three herbicides showed non-antagonism on the amounts of endogenous free amino acids.