Synthesis of 2-amino-6-oxocyclohexenylsulfonamides and their activity against Botrytis cinerea

BACKGROUND: With the objective of exploring the fungicidal activity of 2‐oxocyclohexylsulfonamides (2), a series of novel 2‐amino‐6‐oxocyclohexenylsulfonamides (6 to 23) were synthesised, and their fungicidal activities against Botrytis cinerea Pers. were evaluated in vitro and in vivo. RESULTS: The compounds were characterised by IR, ¹H NMR and elemental analysis. Bioassay results of mycelial growth showed that compounds 6 to 23 had a moderate antifungal activity against B. cinerea. N‐(2‐methylphenyl)‐2‐(2‐methylphenylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (13) and N‐(2‐chlorophenyl)‐2‐(2‐chlorophenylamino)‐6‐oxocyclohexenylsulfonamide (21) showed best antifungal activities, with EC₅₀ values of 8.05 and 10.56 µg mL^?1 respectively. Commercial fungicide procymidone provided an EC₅₀ value of 0.63 µg mL^?1. The conidial germination assay showed that most of compounds 6 to 23 possessed excellent inhibition of spore germination and germ‐tube elongation of conidia of B. cinerea. For in vivo control of B. cinerea colonising cucumber leaves, the compound N‐cyclohexyl‐2‐(cyclohexylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (19) showed a better control effect than the commercial fungicide procymidone. CONCLUSION: The present work demonstrated that 2‐amino‐6‐oxocyclohexenylsulfonamides can be used as possible new lead compounds for further developing novel fungicides against B. cinerea. Copyright © 2011 Society of Chemical Industry     

Synthesis and antifungal activity of new nitro-alcohol derivatives

Thirty-six new nitro-alcohol derivatives were synthesised. Tested in vitro against Helminthosporium sativum, the compounds had high antifungal activities; the EC₅₀ values varied between 10^?2 and 10^?6 M , and for the majority of the compounds between 10^?4 and 10^?6 M . The EC₅₀ values were calculated by probit analysis, except for the compounds with low activity, for which the values were estimated. Interesting relationships between the structure and antifungal action of the compounds were established.     

The discovery of SYP‐10913 and SYP‐11277: novel strobilurin acaricides

BACKGROUND: As previously reported, methyl (E)‐2‐[2‐(2‐phenylamino‐6‐trifluoromethylpyrimidin‐4‐yloxymethyl)phenyl]‐3‐methoxyacrylate has proven to be a new lead with highly acaricidal activity. Following on from this, in an effort to discover new strobilurin analogues with improved activity, a series of substituted pyrimidines were synthesised and bioassayed. RESULTS: All compounds were characterised by ¹H NMR, IR, MS and elemental analysis. Preliminary bioassays demonstrated that some of the title compounds exhibited notable control of Tetranychus cinnabarinus (Boisd.) at 1.25 mg L^?1. The relationship between structure and acaricidal activity is discussed. CONCLUSION: Two compounds of particular interest, 6j (SYP‐10913) and 6k (SYP‐11277), exhibited potent acaricidal activity. The acaricidal potencies of these analogues are higher than that of fluacrypyrim in greenhouse applications, and are comparable with those of commercial acaricides such as spirodiclofen and propargite in field trials. Copyright © 2011 Society of Chemical Industry     

Structure–biological activity relationships in triterpenic saponins: the relative activity of protobassic acid and its derivatives against plant pathogenic fungi

BACKGROUND: Triterpenic saponins from Sapindus mukorossi Gaertn. and Diploknema butyracea JF Gmelin were evaluated for in vitro antifungal activity against four phytopathogenic fungi. The study of the structure–antifungal activity relationships of protobassic acid saponins was widened by including semi‐synthetic derivatives. RESULTS: Diploknema butyracea saponins exhibited significant antifungal activity against three fungi (ED₅₀ 230–455 µg mL^?1), whereas S. mukorossi saponin was effective against two fungi (ED₅₀ 181–407 µg mL^?1). The n‐butanol extract after preparative HPLC separation provided two saponins from D. butyracea saponin mixture: 3‐O‐[β‐D ‐glucopyarnosyl‐β‐D ‐glucopyranosyl]‐16‐α‐hydroxyprotobassic acid‐28‐O‐[arabinopyranosyl‐glucopyranosyl‐xylopyranosyl]‐arabinopyranoside (MI‐I), and 3‐O‐β‐D ‐glucopyranosyl‐glucopyranosyl‐glucopyranosyl‐16‐α‐hydroxyprotobassic acid‐28‐O‐[arabinopyranosyl‐xylopyranosyl‐arabinopyranosyl]‐apiofuranoside (MI‐III). The single saponin extracted from S. mukorossi saponin mixture was identified as 3‐O‐[O‐acetyl‐β‐D ‐xylopyranosyl‐β‐D ‐arabinopyranosyl‐β‐D ‐rhamnopyranosyl] hederagenin‐28‐O[β‐D ‐glucopyranosyl‐β‐D ‐glucopyranosyl‐β‐D ‐rhamnopyranosyl] ester (SM‐I). Monodesmosides resulting from the partial degradation of hederagenin and hydroxyprotobassic acid bisdesmosides exhibited significant reduction in antifungal effect. Further removal of sugar moiety yielded complete loss in activity. The antifungal activity of the triterpenic saponins was associated with their aglycone moieties, and esterification of the hydroxyl group led to change in antifungal activity. CONCLUSION: Sapindus mukorossi saponin, which is effective against Rhizoctonia bataticola (Taub.) Briton Jones and Sclerotium rolfsii Sacc., can be exploited for the development of a natural fungicide. A sugar moiety is a prerequisite for the antifungal activity of triterpenic saponin. Copyright © 2010 Society of Chemical Industry     

Design, synthesis and structure-activity relationship of novel coumarin derivatives

BACKGROUND: The lead coumarin derivative (E)‐methyl 3‐methoxy‐2‐[2‐(4‐methylcoumarin‐7‐yloxymethyl)phenyl]acrylate was discovered by using an intermediate derivatisation method. To discover new coumarin derivatives with improved activity, a series of substituted coumarins were synthesised and bioassayed. RESULTS: The compounds were identified by ¹H NMR, IR, MS and elemental analysis. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activity against cucumber downy mildew at 25 mg L^?1. The relationship between structure and fungicidal activity is reported. CONCLUSION: The present work demonstrates that coumarin derivatives containing methoxyacrylate moieties can be used as possible lead compounds for developing novel fungicides. Copyright © 2011 Society of Chemical Industry     

Mechanism of herbicidal activity of a new cyclohexane-1,3-dione, tepraloxydim to Poa annua L.

Tepraloxydim [(EZ)‐(RS)‐2‐{1‐[(2E)‐3‐chloroallyloxyimino]propyl}‐3‐hydroxy‐5‐perhydropyran‐4‐ylcyclohex‐2‐en‐1‐one] showed high activity against annual bluegrass (Poa annua L.), which is relatively tolerant to sethoxydim [(±)‐2‐(1‐ethoxyiminobutyl)‐5‐[2‐(ethylthio)propyl]‐3‐hydroxycyclohex‐2‐en‐1‐one]. Absorption and translocation rates of tepraloxydim and sethoxydim were higher in P. annua than in Setaria faberi, but the absorption and translocation patterns of tepraloxydim in the two plants were similar to those of sethoxydim. Metabolic rates of tepraloxydim and sethoxydim in P. annua and S. faberi were found to be similar. The concentration for 50% inhibition (I₅₀) of acetyl‐coenzyme A carboxylase (ACCase) with tepraloxydim was approximately 3 × 10^?6 mol L^?1 for P. annua and 7 × 10^?7 mol L^?1 for S. faberi. For sethoxydim, the I₅₀ was found to be 2 × 10^?6 mol L^?1 with the enzyme of S. faberi, while sethoxydim showed a slight effect on ACCase from P. annua activity, even at 10^?4 mol L^?1. The strong inhibition of ACCase with tepraloxydim is considered to be the major factor contributing to the high herbicidal activity against P. annua. Measuring the whole plant growth response, the ratio of the tepraloxydim I₅₀ dose of P. annua to that of S. faberi (P/S) was found to be 2.4, while the P/S ratio of sethoxydim and a tepraloxydim analog with a propyl chain at R₂ were 56.3 and 73.3, respectively. The herbicidal activity against P. annua was remarkably influenced by the length of the R₂ alkyl chain, while the effect on S. faberi was not affected. Acetyl‐coenzyme A carboxylase from P. annua also exhibited a higher resistance to the tepraloxydim analog with a propyl chain than to tepraloxydim. These results suggest that a binding site structure of cyclohexane‐1,3‐diones in the ACCase differs between P. annua and S. faberi.     

Isolation and identification of two phytotoxic compounds from the medicinal plant Cassia alata L.

Cassia alata (Caesalpiniaceae), an ornamental shrub, has many biological properties such as antifungal and antibacterial activities. Several bioactive and phytotoxic compounds have already been isolated from C. alata. Phytotoxic substances from plants have drawn attention as an alternative biological approach to control weeds. Thus, we conducted this research to explore other phytotoxic compounds in C. alata leaves. Aqueous methanol extracts of C. alata leaves strongly inhibited the seedling growth of broccoli, cabbage, cress, radish and rapeseed, in which the level of inhibition correlated with concentration. Two active compounds were isolated through chromatographies and identified using spectral data as (S)‐4‐(3‐hydroxybutyl)phenol [(+)‐rhododendrol] and (E)‐4‐((1R,4R)‐4‐hydroxy‐2,6,6‐trimethylcyclohex‐2‐en‐1‐yl)but‐3‐en‐2‐one [3‐hydroxy‐α‐ionone]. These two active compounds inhibited the growth of cress seedlings in a concentration‐dependent manner. The required concentrations for 50% growth inhibition (I₅₀ value) of cress seedlings were 192.0–296.1 μM for (+)‐rhododendrol and 132.4–195.3 μM for 3‐hydroxy‐α‐ionone. These results indicate that the two phytotoxic compounds play a part in the phytotoxic activity of C. alata leaves.     

Identification of new limonoids from Swietenia and their biological activity against insects

BACKGROUND: Natural limonoids are one group of compounds being studied for their insecticidal properties. To discover new limonoids with better activities, analogs were prepared via acylation and hydrolysis, and bioassayed. RESULTS: Analogs were identified using one‐ and two‐dimensional (COSY, HMQC and HMBC) ¹H and ¹³C NMR, IR and MS. 3‐O‐Isovalerylswietenolide (13) and 3‐O‐isobutyrylswietenolide (14) showed excellent antifeedant activity, with DC₅₀ values of 0.19 and 0.009 mg L^?1 respectively, compared with the natural limonoid swietenolide (80.6 mg L^?1) against fourth‐instar Spodoptera frugiperda (JE Smith) larvae. CONCLUSION: This work shows that limonoid analogs prepared through semi‐synthesis can be used as lead compounds for the development of new insecticides. Copyright © 2010 Society of Chemical Industry     

10种N-取代氨基香豆素的合成及生物活性

基于结构拼接思想,设计合成了10个N-取代氨基香豆素类化合物,并测定了其抑菌及除草活性。6-硝基香豆素经Fe/NH4Cl还原得6-氨基香豆素,再与不同醛缩合得Schiff碱,最后经硼氢化钠还原制得10个N-取代氨基香豆素类化合物(4a~4J),其中9个未见文献报道,其结构均经红外光谱、核磁共振氢谱和质谱确认。抑菌活性测试结果表明,所有化合物对苹果腐烂病菌Valsa mali、葡萄白腐病菌Coniothyrium diplodiella、棉花枯萎病菌Fusarium oxysporium和柑橘炭疽病菌Citrusanthrax bacteria均有一定抑制作用,其中 4e 的抑菌活性最强,对苹果腐烂病菌和柑橘炭疽病菌的EC50值分别为7.53和12.93 mg/L,对其余2种植物病原菌的EC50值均小于25 mg/L;化合物 4f 次之,对苹果腐烂病菌和葡萄白腐病菌的EC50值均约为11 mg/L。除草活性测试结果表明,除 4f 外,所有目标化合物均有一定除草作用,其中 4c 的活性最强,100 mg/L下对反枝苋Amaranthus retroflexus种子根、茎生长的抑制率均为99%。     

Relationship between chemical structure and biological activity of triazole fungicides against Botrytis cinerea

The inhibitory activity of commercial and experimental triazole fungicides on the target enzyme, sterol 14α-demethylase (P450_14DM), was studied in a cell-free sterol synthesis assay of Botrytis cinerea Pers. ex Fr. In order to assess structure-activity relationships, the inhibitory activities of the compounds on radial growth of the fungus were tested as well. The EC₅₀ values (concentrations of fungicide inhibiting radial growth of B. cinerea on PDA by 50%) of all triazoles tested ranged between 10^?8 and 10^?5 m. IC₅₀ values (concentrations of fungicide inhibiting incorporation of [2-¹⁴C]mevalonate into C4-desmethyl sterols by 50%) generally ranged between 10^?9 and 10^?7 M and correlated with inhibition of radial mycelial growth. However, differences in IC₅₀ values did not reflect quantitatively the observed differences in EC₅₀ values, since the ratio between EC₅₀ and IC₅₀ increased with decreasing fungitoxicity. For a limited number of compounds the correlation between intrinsic inhibitory activity and fungitoxicity was low. Both in-vitro tests were used to investigate structure-activity relationships for stereoisomers of cyproconazole, SSF-109 and tebucona-zole. Fungitoxicity and the potency to inhibit cell-free C4-desmethyl sterol synthesis correlated for all stereoisomers tested. Mixtures of isomers of tebucona-zole or cyproconazole were slightly less active than the most potent isomer. The high activity of several commercial triazoles in both experiments implies that poor field performance of triazole fungicides against B. cinerea is due neither to insensitivity of the P450_14DM nor to low in-vitro sensitivity of the fungus.     

Sensitivity of Botrytis cinerea to chitosan and acibenzolar‐S‐methyl

BACKGROUND: The antifungal properties of chitosan and acibenzolar‐S‐methyl were evaluated to assess their potential for protecting grapes against Botrytis cinerea Pers.: Fr. isolated from Vitis vinifera L. The objectives were to determine the effects of these compounds on the in vitro development of B. cinerea and to assess their effectiveness at controlling grey mould on grapes stored at different temperatures. RESULTS: Both agents significantly inhibited the radial growth of this fungus species. The EC₅₀ was 1.77 mg mL^?1 for chitosan and 3.44 mg mL^?1 for acibenzolar‐S‐methyl. In addition, single grapes treated with aqueous solutions of chitosan (1.0 and 2.5 mg mL^?1) and acibenzolar‐S‐methyl (1.0 and 3.0 mg mL^?1) were inoculated with B. cinerea and incubated at both 4 and 24 °C. After 4 days at 24 °C, all the concentrations of chitosan and acibenzolar‐S‐methyl significantly reduced B. cinerea growth. However, at 4 °C, significant differences were only observed between chitosan at 2.5 mg mL^?1 and acibenzolar‐S‐methyl at both 1.0 and 3.0 mg mL^?1 and the corresponding controls. After 3 days at 24 °C, the greatest reduction in lesion size was obtained in grapes pretreated with acibenzolar‐S‐methyl at 3.0 mg mL^?1. Only the highest doses of these products significantly reduced the lesion diameters when grapes were stored for 3 days at 4 °C. CONCLUSIONS: Chitosan and acibenzolar‐S‐methyl could directly inhibit the growth of Botrytis cinerea in vitro and confer resistance on grapes against grey mould. Pretreatment with these compounds could be an alternative to traditional fungicides in post‐harvest disease control in grapes. Copyright © 2010 Society of Chemical Industry     

Composition of essential oil of Chinese Chenopodium ambrosioides and insecticidal activity against maize weevil, Sitophilus zeamais

BACKGROUND: In a screening programme for new agrochemicals from Chinese medicinal herbs, Chenopodium ambrosioides L. was found to possess strong fumigant activity against the maize weevil Sitophilus zeamais (Motsch.). Essential oil of C. ambrosioides was obtained by hydrodistillation, and the constituents were determined by GC‐MS analysis. The active compounds were isolated and identified by bioassay‐directed fractionation. RESULTS: Five active compounds [(Z)‐ascaridole, 2‐carene, ρ‐cymene, isoascaridole and α‐terpinene] were isolated and identified from the essential oil from Chinese C. ambrosioides. The LC₅₀ values (fumigation) of the crude essential oils and the active compound (Z)‐ascaridole against S. zeamais adults were 3.08 and 0.84 mg L^?1 air respectively. The LD₅₀ values (contact toxicity) of the crude essential oil and (Z)‐ascaridole against S. zeamais adults were 2.12 and 0.86 µg g^?1 body weight respectively. CONCLUSION: The findings suggested that the essential oil of Chenopodium ambrosioides and its main active constituent, (Z)‐ascaridole, may be explored as a natural potential fumigant. Copyright © 2011 Society of Chemical Industry     

1-甲基-3-二氟甲基吡唑酰胺类化合物的合成及抑菌活性

以1-甲基-3-二氟甲基吡唑-4-甲酸为原料,经过1-甲基-3-二氟甲基吡唑-4-甲酰氯与相应的氨基苯并杂环类、芳胺类化合物反应,得到了14个未见文献报道的吡唑-4-甲酰胺类化合物(6a~6g、7a~7g),其结构均通过1H NMR、MS和IR表征。抑菌活性测试结果表明,在100 mg/L下,目标化合物对供试植物病原菌均有不同程度的抑制作用,其中7a~7g的抑菌活性较高,部分对苹果炭疽病菌的抑制率在90%以上。     

The role of syringic acid in the interaction between oil palm and Ganoderma boninense,the causal agent of basal stem rot

Novel inoculation and assessment methods for Ganoderma boninense infection of oil palm are reported. The involvement of phenolic acids in the interaction was examined. HPLC was used to monitor changes in the concentrations of three specific phenolics: syringic acid (SA), caffeic acid and 4‐hydroxybenzoic acid, identified as the main compounds that accumulated. The work reported here focuses on SA, the most antifungal of the molecules detected. The oil palm cv. AVROS, reported by local planters to be less susceptible than others, showed higher accumulation of SA than cvs Ekona and Calabar. Accumulation was promoted by addition of chitosan to the plant growing medium. By the end of the time‐course, the concentration of SA decreased in the oil palm tissues inoculated with G. boninense, suggesting possible metabolism by the pathogen. This loss was, however, not detected in tissues treated with chitosan alone and was greatly reduced when G. boninense was combined with this polymer. In vitro studies on antifungal activity of SA were done using concentrations ranging from 50 to 110 μg mL^?1, those typically recorded in oil palm roots. SA was found to be antifungal (EC₅₀ 90–100 μg mL^?1). The concentration of SA detected in root tissues, especially in the presence of chitosan, could inhibit growth of G. boninense. The pathogen was shown to degrade SA in vitro. However, at the highest concentration tested, metabolism was greatly delayed, only occurring after a lag phase in pathogen growth. Accumulation of phenolic acids, especially SA, may prove a useful trait in breeding resistant oil palm cultivars.     

基于丁香酚的异(口恶)唑啉类化合物的设计合成及抑菌活性

为了探索新型异齅唑啉类化合物作为杀菌剂候选化合物开发的潜力,本研究以廉价易得的芳香醛类化合物为原料制备了32个氯代肟类化合物,通过其与天然产物丁香酚的1,3-偶极环加成反应和后期官能团化反应,制备了35个异齅唑啉类化合物 ( D1 ~ D32 , E1 ~ E3 ),其中34个为新化合物。所有化合物的结构均经过液相色谱-电喷雾质谱 (LC-ESI-MS)、核磁共振氢谱 (1H NMR) 及元素分析确认。初步抑菌活性测试结果表明:多数目标化合物对油菜菌核病菌、水稻纹枯病菌、番茄早疫病菌和辣椒疫霉病菌具有较好的抑菌活性,其中化合物 D26 对油菜菌核病菌的活性最高,有效抑制中浓度 (EC₅₀) 为14.3 mg/L,具有进一步研究的价值。     

Synergistic and antagonistic interactions of terpenes against Meloidogyne incognita and the nematicidal activity of essential oils from seven plants indigenous to Greece

BACKGROUND: Biorational means for phytonematode control were studied within the context of an increasingly ecofriendly pest management global approach. The nematicidal activity and the chemical composition of essential oils (EOs) isolated from seven plants grown in Greece and ten selected compounds extracted from them against second‐stage juveniles (J2) of Meloidogyne incognita (Kof. & White) Chitwood were evaluated using juvenile paralysis experiments. Additionally, synergistic and antagonistic interactions between nematicidal terpenes were studied using an effect addition model, with the comparison made at one concentration level. RESULTS: The 96 h EC₅₀ values of Foeniculum vulgare Mill., Pimpinella anisum L., Eucalyptus meliodora A Cunn ex Schauer and Pistacia terebinthus L. were 231, 269, 807 and 1116 µg mL^?1, respectively, in an immersion bioassay. Benzaldehyde (9 µg mL^?1) was the most toxic compound, followed by γ‐eudesmol (50 µg mL^?1) and estragole (180 µg mL^?1), based on 96 h EC₅₀ values. The most potent terpene pairs between which synergistic actions were found, in decreasing order, were: trans‐anethole/geraniol, trans‐anethole/eugenol, carvacrol/eugenol and geraniol/carvacrol. CONCLUSION: This is the first report on the activity of F. vulgare, P. anisum, E. meliodora and P. terebinthus, and additionally on synergistic/antagonistic nematicidal terpene interactions, against M. incognita, providing alternative methods for nematode control. Copyright © 2010 Society of Chemical Industry     

Studies on pesticides based on coumarin. II. Synthesis and antifungal activity of ten 2-alkyl-7, 8-dihydro-3-hydroxynaphtho[1,2-c]chromen-6-ones

A series of 2-alkyl-7, 8-dihydro-3-hydroxynaphtho[1,2-c]chromen-6-ones was synthesised by the condensation of ethyl 3, 4-dihydro-1-oxonaphthalene-2-carboxylate with substituted phenols in the presence of POCl₃. The compounds were characterised and tested for their toxicity towards the mycelial growth of seven phytopathogenic fungi in culture. Drechslera oryzae, Rhizoctonia solani and Colletotrichum falcatum exhibited maximum sensitivity to these compounds whereas Macro-phomina phaseolina, Fusarium solani, Alternaria alternata and Pythium aphanidermatum were less sensitive. 2-Ethyl-7, 8-dihydro-3-hydroxy-naphtho[1,2-c]chromen-6-ones possessed greatest toxicity with EC₅₀ values ranging from 0.2 to 2.5 μg ml^?1 against all fungi except A. alternata and P. aphanidermatum.     

Baseline sensitivity of natural populations and resistance of mutants of Xanthomonas oryzae pv. oryzae to a novel bactericide,zinc thiazole

During 2009–2010, a total of 323 isolates of Xanthomonas oryzae pv. oryzae were obtained from rice with symptoms of bacterial leaf blight (BLB) in four provinces (Zhejiang, Jiangsu, Anhui and Hubei) in China. These isolates were tested for baseline sensitivity to zinc thiazole, a novel bactericide with strong antibacterial activity against Xanthomonas. The sampled pathogenic population had similar sensitivity to zinc thiazole (0·1–16·8 mg L^?1) in all four regions and over the whole two‐year study period. The baseline sensitivity was distributed as a unimodal curve with a mean EC₅₀ value of 6·79 ± 1·61 mg L^?1. The risk of mutation to resistance of zinc thiazole in X. oryzae pv. oryzae was further evaluated in vitro and in vivo. Twelve zinc thiazole‐resistant mutants were obtained through ultraviolet (UV) irradiation, culturing on zinc thiazole‐amended nutrient agar (NA) plates, and culturing on zinc thiazole‐treated rice plants. These zinc thiazole‐resistant mutants had resistance factors (RF = EC₅₀ value of a mutant / EC₅₀ value of the wildtype parent of this mutant) of 12·4 to 186·1 with a mean RF value of 44·1. Mutants obtained via UV irradiation, culturing on NA plates and culturing on rice plants had mean RF values of 51·8, 24·5 and 14·4, respectively. All mutants showed decreases in resistance to zinc thiazole after 20 successive transfers on bactericide‐free media or 10 successive inoculation–reisolations on bactericide‐free rice plants. No significant difference was found in bacterial growth and sensitivity to bismerthiazol between zinc thiazole‐resistant mutants and their parents. However, a significant decrease was observed in the pathogenicity of zinc thiazole‐resistant mutants compared with their parents, especially for mutants obtained via UV irradiation.     

Contribution of militarine and dactylorhin A to the plant growth‐inhibitory activity of a weed‐suppressing orchid,Bletilla striata

The methanol extract of Bletilla striata, an ornamental orchid in eastern Asia, exhibited plant growth‐inhibitory activity. It was purified by continuous chromatography, based on the inhibitory activity against the growth of lettuce seedlings, resulting in two glycosidic compounds, militarine and dactylorhin A. The EC₅₀ values of militarine and dactylorhin A against the radicle elongation of the lettuce seedlings were 0.28 and 0.88 mmol L^?1, respectively. The amount of militarine and dactylorhin A in the methanol extract of the aerial part of B. striata was calculated to be 5.6 and 7.5 mg g^?1 fresh weight, respectively. The inhibitory activity of militarine and its content in the methanol extract revealed that the plant growth‐inhibitory activity of the extract of B. striata was mainly related to militarine. The inhibitory activity of militarine against the growth of Italian ryegrass and timothy were of the same level as that of lettuce.     

新型含苯并咪唑的(S,S)-2,8-二氮杂双环[4.3.0]壬烷类衍生物的合成及生物活性

通过N-烷基化反应合成了一系列新型含苯并咪唑的(S,S)-2,8-二氮杂双环[4.3.0]壬烷类衍生物,中间体化合物通过环化反应和酰化反应合成得到。所有新型化合物的结构均通过熔点测定、核磁共振氢谱和高分辨质谱确认。生物活性测试结果显示,目标化合物拥有中等的抗植物真菌活性,对东方粘虫Mythimna separata Walker和蚊幼虫Culex pipiens pallens具有中等到良好的杀虫活性。其中化合物6e和6f对油菜菌核Sclerotinia sclerotiorum、马铃薯晚疫Phytophthora infestans、小麦赤霉Fusarium graminearum等真菌具有良好的抗菌活性。化合物6e和6k在200mg/L下对东方粘虫的致死率为100%,化合物6h和6k在2mg/L下对蚊幼虫的致死率为75%。