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A series of novel alpha,alpha,alpha-trifluoro-m-tolyl pyridazinone derivatives was synthesised. Herbicidal activities of the two intermediate compounds and 15 pyridazinone derivatives were evaluated through barnyardgrass and rape cup tests and Spirodela polyrrhiza (L.) Schleiden tests. Selected compounds were also evaluated under greenhouse conditions. Bleaching activities were observed at 10 microg ml(-1) and some compounds exhibited herbicidal activities at a rate of 300 g ha(-1). The relationship between crystal structures and herbicidal activities is discussed through a comparison of two compounds (5a and 5f).  相似文献   

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A series of novel types of 7‐(4,6‐dimethoxypyrimidin‐2‐yl)oxy ‐ and ‐thio‐3‐methyl‐1 (3H)‐isobenzofuranones were discovered at Dr R Maag AG. From the thio‐isobenzofuranyl series, CGA 279 233—BSI‐proposed common name pyriftalid—was chosen for further development as a grass herbicide for use in rice. General synthetic approaches to these new phthalic acid‐derived compounds are given, with emphasis on the synthesis of pyriftalid and its physico‐chemical behaviour. © 2001 Society of Chemical Industry  相似文献   

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The discovery of dinotefuran: a novel neonicotinoid   总被引:1,自引:0,他引:1  
Dinotefuran (MTI-446: (RS)-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine) is a new neonicotinoid commercialized by Mitsui Chemicals. Research led to this novel neonicotinoid by the removal of the chloropyridine or chlorothiazole ring that had been considered as indispensable for neonicotinoides. The research advanced as follows; (1) selection of acetylcholine for the lead compound, (2) recognition of the insecticidal advantages of 3-methoxypropyl compounds, (3) synthesis of (+/-)-tetrahydro-3-furylmethyl compounds by cyclization of the 3-methoxypropyl moiety. It resulted in dinotefuran which has a (+/-)-tetrahydro-3-furylmethyl moiety instead of a halogenated aromatic heterocyclic ring, and belongs to the third-generation neonicotinoids (sub-class: furanicotinyl compounds).  相似文献   

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The cowpea bruchid (Callosobruchus maculatus F.) (Chrysomelidae: Bruchini) is a major pest of stored cowpea grain. With limited available technologies for controlling the bruchid, transgenic cowpeas with bruchid resistance genes engineered into them could become the next management tools. An investigation was made of two different sets of potential transgenic insecticidal compounds using an artificial seed system: (i) CIP-PH-BT-J and recombinant egg white avidin, and (ii) avidin and wheat alpha-amylase inhibitor. CIP-PH-BT-J (0.1%; 1000 mg kg(-1)) and recombinant egg white avidin (0.006%; 60 mg kg(-1)) incorporated separately into artificial seeds caused 98.2 and 99% larval mortality rates respectively. Combining CIP-PH-BT-J and avidin in the same artificial seed provided additional mortality compared with each factor incorporated singly; no insects survived in seeds with the combined toxins. Similarly, when avidin and wheat alpha-amylase inhibitor (alphaAI) (1%; 10 g kg(-1)) were incorporated separately into artificial seeds, this caused 99.8 and 98% mortality respectively. However, in combination, avidin and alphaAI did not increase mortality, but they did cause a significant increase in developmental time of the cowpea bruchids. These results emphasize that the joint action of potential insecticidal compounds cannot be predicted from results obtained separately for each compound, and they suggest potential transgenes for further consideration.  相似文献   

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The insecticidal activities of essential oil extracts from leaves and flowers of aromatic plants against fourth-instar larvae of the mosquito Culex pipiens molestus Forskal were determined. Extracts of Myrtus communis L were found to be the most toxic, followed by those of Origanum syriacum L, Mentha microcorphylla Koch, Pistacia lentiscus L and Lavandula stoechas L with LC50 values of 16, 36, 39, 70 and 89 mg litre-1, respectively. Over 20 major components were identified in extracts from each plant species. Eight pure components (1,8-cineole, menthone, linalool, terpineol, carvacrol, thymol, (1S)-(-)-alpha-pinene and (1R)-(+)-alpha-pinene) were tested against the larvae. Thymol, carvacrol, (1R)-(+)-alpha-pinene and (1S)-(-)-alpha-pinene were the most toxic (LC50 = 36-49 mg litre-1), while menthone, 1,8-cineole, linalool and terpineol (LC50 = 156-194 mg litre-1) were less toxic.  相似文献   

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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.  相似文献   

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BACKGROUND: Recent studies have focused on materials derived from plant extracts as mite control products against house dust and stored food mites because repeated use of synthetic acaricides had led to resistance and unwanted activities on non‐target organisms. The aim of this study was to evaluate the acaricidal activity of materials derived from Lycopus lucidus against Dermatophagoides farinae, D. pteronyssinus and Tyrophagus putrescentiae. RESULTS: The LD50 values of L. lucidus oil were 2.19, 2.25 and 8.45 µg cm?2 against D. farinae, D. pteronyssinus and T. putrescentiae. The acaricidal constituent of L. lucidus was isolated by chromatographic techniques and identified as 1‐octen‐3‐ol. In a fumigant method against D. farinae, the acaricidal activity of 1‐octen‐3‐ol (0.25 µg cm?2) was more toxic than N,N‐diethyl‐m‐toluamide (DEET) (36.84 µg cm?2), followed by 3,7‐dimethyl‐1‐octen‐3‐ol (0.29 µg cm?2), 1‐octen‐3‐yl butyrate (2.32 µg cm?2), 1‐octen‐3‐yl acetate (2.42 µg cm?2), 3,7‐dimethyl‐1‐octene (9.34 µg cm?2) and benzyl benzoate (10.02 µg cm?2). In a filter paper bioassay against D. farinae, 1‐octen‐3‐ol (0.63 µg cm?2) was more effective than DEET (20.64 µg cm?2), followed by 3,7‐dimethyl‐1‐octen‐3‐ol (1.09 µg cm?2). CONCLUSION: 1‐Octen‐3‐ol and 3,7‐dimethyl‐1‐octen‐3‐ol could be useful as natural agents for the management of three mite species. Copyright © 2011 Society of Chemical Industry  相似文献   

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Antibiosis has been shown to be an important mode of action by Trichoderma species used in the protection of grapevine pruning wounds from infection by trunk pathogens. The major active compound from Trichoderma isolates known to protect grapevine pruning wounds from trunk pathogen infection was isolated and identified. The compound, a 6‐pentyl‐α‐pyrone (6PP), was found to be the major secondary metabolite, by quantity, which accumulated in the culture filtrate of Tharzianum isolate T77 and the two Tatroviride isolates UST1 and UST2. Benzimidazole resistant mutants generated from these isolates also produced 6PP as their main secondary metabolite, except for a mutant of T77 that had lost its ability to produce 6PP. The isolates UST1 and UST2 were co‐cultured with the grapevine trunk pathogens Eutypa lata and Neofusicoccum parvum in a minimal defined medium and a grapevine cane‐based medium (GCBM). Co‐culturing UST1 with Nparvum induced 6PP production in the minimal defined medium and the GCBM. The production of 6PP by UST2 was induced in the GCBM, while co‐culturing with the two trunk pathogens either reduced or had no effect on 6PP production. Mycelial growth and ascospore/conidia germination of Elata, Naustrale, Nparvum and Phaeomoniella chlamydospora were inhibited by 6PP in a concentration‐dependent manner. The results show that the presence of Nparvum and grapevine wood elicits the production of 6PP, suggesting that this metabolite is involved in Trichoderma–pathogen interactions on grapevine pruning wounds.  相似文献   

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Phytophthora root rot (PRR) of avocado, caused by Phytophthora cinnamomi, is a significant threat to sustainable production wherever the crop is grown. Resistant rootstocks in combination with phosphite applications are the most effective options for managing this disease. Recently, the mechanisms underpinning PRR resistance have been investigated by the avocado community. Here, biochemical assays and confocal and scanning electron microscopy were used to investigate early defence responses in PRR resistant and ‐susceptible avocado rootstocks. Zoospore germination and subsequent hyphal growth for the pathogen were significantly inhibited on the surface of resistant avocado roots. When penetration occurred in the resistant R0.06 rootstock, callose was deposited in the epidermal cells, parenchyma and cortex of roots. In addition, β‐1,3‐glucanase was released early (6 h post‐inoculation, hpi) in response to the pathogen, followed by a significant increase in catalase by 24 hpi. In contrast, susceptible R0.12 roots responded only with the deposition of lignin and phenolic compounds incapable of impeding pathogen colonization. In this study, PRR resistance was attributed to a timely multilayered response to infection by P. cinnamomi.  相似文献   

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N3-substituted imidacloprid congeners containing C1-C6 alkyl groups or various analogous groups, and their corresponding nitromethylene analogues, were used in this study. Their insecticidal activity against the housefly, Musca domestica, and their binding activity toward the nicotinic acetylcholine receptor were determined. The insecticidal test was conducted using the synergists piperonyl butoxide and propargyl propyl phenylphosphonate. The binding assay was performed with housefly head membrane preparations using radio-labelled alpha-bungarotoxin. Both insecticidal and binding activities were drastically lowered by the introduction of alkyl/allyl groups at the imidazolidine NH sites of both nitroimino and nitromethylene compounds. The binding activity of N3-substituted nitromethylene analogues was much higher than that of the corresponding nitroimino analogues. However, the insecticidal activity of both series of compounds with a given substituent was nearly identical. The insecticidal activity correlated positively with the binding activity after taking into account the structural difference of the nitroimino and nitromethylene moieties and a structural feature of the N3-substituents.  相似文献   

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All isomers of α‐asarone [(E)‐4‐prop‐1‐enyl‐1,2,5‐trimethoxybenzene] were tested for their feeding deterrent activity against adults of Sitophilus granarius and Tribolium confusum and larvae of Trogoderma granarium and Tribolium confusum. (E)‐2‐prop‐1‐enyl‐1,3,5‐trimethoxybenzene exhibited the strongest deterrent activity against all the species tested. The total coefficients of deterrency for this compound were 140.6 and 169.7 for Tribolium confusum adults and larvae, respectively, and 144.9 and 104.6 for larvae of Trogoderma granarium and adults of Sitophilus granarius, respectively. © 2000 Society of Chemical Industry  相似文献   

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Ambient air concentrations of nine selected pesticides used in potato cultivation were investigated on Prince Edward Island by collecting samples during the summer of 1998 at three potato farm sites and one non-agricultural site. In 1999, air samples were collected at a single potato farm site during local application of pesticides. The fungicide chlorothalonil was the only pesticide detected in every sample in both years, even in samples with a duration as little as 5 h. In 1998, maximum (45-458 ng m(-3)) and mean (22-193 ng m(-3)) concentrations of chlorothalonil from composite 42 h samples were one to two orders of magnitude greater at agricultural sites than at the non-agricultural site (3.9 and 2.5 ng m(-3), respectively). Maximum and mean concentrations of chlorothalonil from combined 24 h samples at the farm site in 1999 were higher than those measured in 1998 (636 and 284 ng m(-3), respectively). The ubiquitous presence in air of relatively high concentrations of chlorothalonil in agricultural areas on Prince Edward Island is likely related to its repeated use on potato farms where fungicides account for 80-90% of pesticides applied. Eight of nine pesticides were detected at farm sites in 1998 and they are ranked by mean concentration from highest to lowest as follows: chlorothalonil, methamidophos, azinphos-methyl, alpha-endosulfan, beta-endosulfan, pirimicarb, metobromuron, metribuzin, metalaxyl and fluazifop-P-butyl. Concentrations of metalaxyl, pirimicarb, metobromuron and fluazifop-P-butyl in air are among the first reported values for these pesticides. Five pesticides were detected at the Summerside farm in 1999, but only two fungicides (chlorothalonil and metalaxyl) were used locally, while the presence of metribuzin, alpha-endosulfan and methamidophos in air was not associated with local application. Evidence of pesticide drift was observed for chlorothalonil, alpha-endosulfan and methamidophos, and these pesticides were identified as being of high concern in terms of potential wildlife exposure on the Island.  相似文献   

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