• The Korean Journal of Mycology
• /
• v.32 no.1
• /
• pp.8-15
• /
• 2004

This study was conducted to discover new phytotoxins which may be used as lead molecules for the development of new herbicides. A total of 187 endophytic fungi were isolated from 11 plant species, which were collected from 8 locations in Korea. Their herbicidal activities were screened in vivo by herbicidal and duckweed bioassays after they were cultured in potato dextrose broth and rice solid media. Both fermentation broth and solid culture extract of Gliocladium catenulatum F0006 isolated from red pine (Pinus densiflora) showed 70% herbicidal activity only against cocklebur (Xanthium strumarium) out of the 10 weeds tested. Solid culture extract of F0034 isolated from arrowroot (Pueraria thunbergiana) exhibited 20 to 100% herbicidal activities against all of the weeds. Especially, shattercane (Sorghum bicolor), barnyardgrass (Echinochloa crus-galli), large crabgrass (Digitaria sanguinalis), and fall pauicum (Panicum dichtomiflorum) were sensitive to the solid culture extract of F0034. In addition, solid culture extract of F0043 isolated from red pine displayed 20% to 70% herbicidal activities only against 5 grass species, but not against 5 broad-leaf plant species. On the other hand, as the results of duckweed assay, 8 fermentation broths showed 100% growth inhibitory activity at concentrations less than 5.0% of culture supernatants and 12 solid cultures had a potent inhibitory activity against duckweed growth. A toxic metabolite was purified from the solid cultures of G. catenulatum F0006 by repeated column chromatography and bioassay. It caused a phytotoxic syndrome only on cocklebur out of the 10 weeds tested; it completely killed cocklebur seedlings at $500\;{\mu}g/ml$ and showed 85% herbicidal activity against cocklebur at $100\;{\mu}g/ml$. The molecular weight of the toxic metabolite is 238 daltons and its structure determination is underway.

• Applied Biological Chemistry
• /
• v.38 no.6
• /
• pp.570-576
• /
• 1995

The new sixteen herbicidal N-2-(1-hydroxy-2-fluoroethyl)-6-substituted(X)-benzenesulfonyl-N'-4,6-dimethoxypyrimidinyl-2-yl urea derivatives(S) were synthesized and thier herbicidal activities$(pI_{50})$ in vivo against rice(Orysa Sativa L.), Barnyard grass(Echninochloa orizicola) and Bulrush(Scirpus juncoides) were measured by the pot test under paddy conditions. The structure activity relationship(SAR) were studied using the physicochemical parameters of ortho-substituents(X) and hydrolysis rate constant(logk) and herbicidal activities by the multiple regression technique. The SAR suggested that the herbicidal activities were more dependant on the hydrolysis rate constant(logk>0) than the steric constants $(Es, small width($B_4$) and length($L_1$). Among them, halogens(2 & 5), methyl(15) and non(H) substituent(1) showed higher herbicidal activity for weeds which was not tolerent to rise and weeds. The herbicidal activity was increased and the persistency in aqueous solution was decreased by electron donating(${\sigma}0<0$) groups as ortho-substituent(X). From the relationship equation between herbicidal activity and hydrolysis rate constant, it was assumed that the both reactions would be proceeds with similar process. And the conditions on the ortho substituents to show higher herbicidal activity and the persistency in aqueous solution were also discussed.

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

• The Korean Journal of Pesticide Science
• /
• v.10 no.4
• /
• pp.262-265
• /
• 2006

A series of N-[4-chloro-2-fluoro-5-(2-(substituted)pyrimidinyloxy)phenyl]-3,4,5,6-tetrahydrophthalimides was synthesized, and the herbicidal activities of those derivatives were evaluated through pre- and post-emergence application under upland conditions in a greenhouse. The results showed that most compounds resulted in stronger herbicidal activities on broadleaf weeds than on grass weeds. The N-[4-chloro-2-fluoro-5-(2-pyrimidinyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide showed the best weed control efficacy and marginal corn safety at a rate of 60 g/ha through pre-emergence application.

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

• The Korean Journal of Pesticide Science
• /
• v.6 no.3
• /
• pp.183-192
• /
• 2002

Herbicidal effect of KSC-35089, a newly synthesized N-arylphthalimide compound, was examined, and its interaction with quizalofop-P-ethyl when foliar applied as a tank-mixture was evaluated under a greenhouse condition. KSC-35089 showed stronger herbicidal activity on broadleaves than grasses, suggesting that it would be an appropriate partner for non-selective weed control with quizalofop-P-ethyl, a strong grasskilling ageant. In general, the interaction between KSC-35089 and quizalofop-P-ethyl appeared to be additive, which indicates each compound acts on whole plant level independently. This additive interaction was confirmed in a spectrum test using 19 grasses and 26 broadleaves. Under the greenhouse condition, all tested plants were controlled around 90% level through a foliar application with a tank-mixture of KSC-35089 at 64 g ai/ha and quizalofop-P-ethyl at 32 g ai/ha. Further study would be required on the action mechanism of this additive interaction.

• Weed & Turfgrass Science
• /
• v.2 no.1
• /
• pp.30-37
• /
• 2013

The objective of this research was to understand herbicidal activity of essential oils isolated from leaves of pine (Pinus densiflora), nut pine (Pinus koraiensis), larch (Larix kaempferi) and khingan fir (Abies nephrolepsis) in Korea. In a seed bioassay, essential oils of nut pine, larch and khingan fir inhibited the growth of rapeseed (Brassica napus) seedlings by 50% at 4,766, 1,865, $5,934{\mu}g\;ml^{-1}$, respectively, however, that of pine did not show any herbicidal effect. In a green house experiment, fall panicum, Southern crabgrass, sorghum, barnyardgrass, quackgrass, black nightshade, Indian jointvetch, velvet leaf, and Japanese morningglory were controlled in 24 hours by the foliar application of 10% essential oils from pine, nut pine, larch and khingan fir. The treated plant parts showed burndown effect, however, new shoots appeared 3 days after treatment. Results of GC-MS analysis showed that essential oils from pine, nut pine, larch and khingan fir contained 16, 25, 25, and 16 compounds, respectively, with hydrocarbons, alcohols, ketones, and esters. The major compounds of the essential oils were 3-carene, bornyl acetate, camphene, limonene, ${\alpha}$-pinene, ${\beta}$-pinene and ${\beta}$-phellandrene.

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