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1.
The insecticidal activities against houseflies (Musca domestica L.) and mustard beetles (Phaedon cochleariae Fab.) of the chrysanthemate bioresmethrin, and of 31 related 5-benzyl-3-furylmethyl 2,2-dimethylcyclopropanecarboxylates with alkenyl, alkadienyl or alkoxycarbonylalkenyl substituents at position 3 of the cyclopropane ring are compared to determine the relative influence of the isobutenyl sidechain (as in chrysanthemates) and of the other side chains. Several substituents, in particular (E)- or (Z)-butadienyl or -pentadienyl, give considerably greater activity than isobutenyl but alkoxycarbonyl compounds are less potent.  相似文献   

2.
New routes to the title compounds, involving improved conditions for the cyclopropanation, and a new method of constructing the central three-carbon unit (based on the coupling of a Grignard reagent with an allylic acetate) give access to products for which the previously reported route was not satisfactory. For the new route, a synthesis of 5-bromo-2-fluoro-diphenyl ether was developed. Previously deduced relationships between structure and insecticidal activity apply for the new compounds: alkenes are generally more active than corresponding alkanes; substitution at the 3- or 4-position (but not the 2-) of the 1-aryl group can enhance activity. In addition, some fluorine-containing substituents lead to high activity.  相似文献   

3.
The synthesis of a series of mono- and disubstituted biphenyl-3-ylmethyl esters of 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid is described. The bioactivity of these compounds against Spodoptera eridania, Epilachna varivestis, Oncopeltus fasciatus, Acrythosiphon pisum and Tetranychus urticae is presented and discussed. Substitution of fluorine, chlorine and methyl groups in the 2-position of the biphenyl ring generally led to an increase in activity over the unsubstituted parent biphenyl ester. In addition, pyrethroid esters derived from these 2-substituted biphenyl-3-ylmethanols appeared to have a broader spectrum of activity than ‘classical’ pyrethroids. For example, the (1RS)-cis-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopro-panecarboxylic acid ester of 2-methylbiphenyl-3-ylmethanol was acaricidal, while maintaining a level of activity against other insects that was equal to or greater than cis-permethiin. Biological data on other esters of this novel alcohol are also presented.  相似文献   

4.
为获得活性更佳且同时具备苯甲酰基脲类和氨基甲酸酯类活性的新型双靶标杀虫剂——N-氯磺基-N-甲基氨基甲酸酯衍生物,构建此类化合物的三维定量构效关系（three-dimensional quantitative structure-activity relationship,3D-QSAR）模型,以18种具有双靶标活性的N-氯磺基-N-甲基氨基甲酸酯衍生物为训练集,分别采用比较分子力场分析（comparative molecular field analysis,CoMFA）法和比较分子相似性指数分析（comparative molecular similarity index analysis,CoMSIA）法进行3D-QSAR模型的构建,基于3D-QSAR模型分析同一骨架取代基的变化带给化合物的活性变化,预测不同力场对化合物活性的影响,并对设计的衍生化合物进行活性预测分析。结果表明,经CoMFA法和CoMSIA法构建的3D-QSAR模型可信度高（交叉验证系数q2分别为0.728和0.563）,且有良好的活性预测能力（非交叉验证系数r2分别为0.954和0.981）。基于该模型得到的化合物预测活性与实际活性残差较小且存在良好的线性关系,进一步证明所得3D-QSAR模型的可靠性。通过分析3D-QSAR模型的力场分布,推测在R1基团处引入位阻较大的疏水性基团、在R2基团苯环的邻位引入同时具有负电性和疏水性但不含卤素原子的基团、用负电性的大位阻基团取代R基团等均可提高N-氯磺基-N-甲基氨基甲酸酯的活性。基于此设计的20种衍生化合物的活性变化从正反两方面印证了该推测的合理性。研究成果可用于指导兼具苯甲酰基脲类和氨基甲酸酯类杀虫剂作用机制的N-氯磺基-N-甲基氨基甲酸酯衍生物的设计。  相似文献   

5.
We present the results of a histochemical study comparing seedlings of races C and D of Orobanche cumana Wallr. (syn. O. cernua Loefl.) attacking sunflower (Helianthus annuus L.) in southern Russia. Three groups of O. cumana seedlings were distinguished according to the peroxidase content of the cells in the radicles: (1) those with neither extracellular nor intracellubr peroxidase and whose radicles have a smooth apex (these were classified as non-infective): (2) those with a high peroxidase content of the nuclei and the cytoplasm layer adjacent to the cell wall, as well as excretion of peroxidase from the apex of the radicles: (3) those with a similarly high peroxidase activity in the parasite cells, but without extracellular excretion. The apices of the radicles of the last two groups are swollen. It is suggested that these belong to O. cumana races C and D respectively. The extracellular peroxidase in O. cumana race C reacts with phenolic compounds, which are lignin precursors of the host, resulting in host resistance due to the formation of lignin layers in sunflowers possessing the Or3 gene for resistance. The absence of extracellular peroxidase in O. cumana race D prevents lignin formation and enables the parasite to attach to the host vascular system. Comparison of these data with the information on the earlier O. cumana races A and B, and older sunflower cultivars, points to a crucial role of peroxidase in the process of breeding new sunflower cultivars and the evolution of new O. cumana races.  相似文献   

6.
In the course of optimization studies around diafenthiuron, the central aromatic nucleus linked directly to the thiourea unit was replaced by a pyridine moiety. A series of N-(pyrid-3-yl)thioureas, -isothioureas and -carbodiimides was synthesised and evaluated for acaricidal activity. The synthetic methodology used and the screening results against some spider mites (Tetranychus spp. and Panonychus ssp.) are discussed.  相似文献   

7.
A series of 14 new 3-[4(3H)-quinazolinone-2-(yl)thiomethyl]-1,2,4-triazoles were prepared and characterized by elemental analyses, IR, [1H] NMR and mass spectral data. Four of the compounds showed insecticidal activity equivalent to that of malathion against the adult stage of the blow fly (Chrysomyia albiceps). However, their activity against the larval stages of this insect species was considerably weaker.  相似文献   

8.
The biological activity of a series of N-(pyrid-3-yl)thioureas and -carbodiimides, analogues of the insecticide/acaricide diafenthiuron, towards the carmine spider mite (Tetranychus cinnabarinus Boisd.) and the two-spotted spider mite (T. urticae Koch) was analysed using QSAR methodology. A canonical correlation analysis allowed for the establishment of a prediction model and the identification of outliers within that model. The chemodynamic behaviour of certain compounds in the two series, including these outliers, determined by using photochemical experiments in the laboratory as well as in the glasshouse, was shown to be responsible for anomalous results obtained in the biological tests. It was found from the above study that the biological activity towards both spider mite species is extremely sensitive to the kinetics of formation of the carbodiimides from the corresponding thioureas and to the photostability of the former. The results obtained with a thiourea which underwent no appreciable photochemical transformation into the corresponding carbodiimide supported the hypothesis that the thioureas are also in-vivo propesticides of the acaricidal carbodiimides.  相似文献   

9.
A cytokinin-like effect of chiral 2-α-methylbenzylamino-4-alkylamino-6-chloro-1,3,5-triazines was found using a rhizome-inducing assay with Cyperus serotinus Rottb. tubers. C. serotinus tubers germinated in distilled water yielded plantlets with roots and leaves. Secondary rhizomes were normally not observed within the regular 14-day incubation time in water culture, whereas after increasing incubation periods a very short rhizome appeared (controls). 6-Benzylaminopurine (BA) significantly stimulated rhizome induction, while other plant hormones were inactive. The (R)-isomers of the 1, 3, 5-triazine compounds also stimulated induction of the rhizomes, whereas the (S)-isomers did not. The described rhizome induction system seems to be suitable as a cytokinin bioassay. The (R)-1, 3, 5-triazine compounds showing rhizome-inducing activity (RI activity) inhibited root formation and plant growth at high concentrations with symptoms which were very similar to those of BA. Therefore, the (R)-isomers appear to act as cytokinins in the rhizome induction assay.  相似文献   

10.
A new series of substituted 2-anilino-3-methylbutyrates has been prepared; bioassay data for these compounds on Heliothis virescens, Musca domestica, Aphis fabae and Tetranychus urticae are presented and discussed. Some unexpected relationships were observed between the nature of the substituents and the biological activity. Increases in foliar stability were noted with certain substitution patterns. Both α-cyano-3-phenoxybenzyl 3-methyl-2-(α, α, α,2-tetrafluoro-p-toluidino)butyrate and the corresponding 2-(2-chloro-α, α, α-trifluoro-p-toluidino)-3-methylbutyrate showed good stability in air and light, and exhibited biological activities of a similar nature and potency to those of previously known synthetic pyrethroids. Esters of the (R)-2- anilino-3-methylbutyric acids are far more active than those prepared from the (S)-enantiomers. The (R)-configuration at C-2 in these acids is sterically equivalent to the active absolute configuration at the chiral carbon α to the carboxylate group in both the permethrin and the fenvalerate types of pyrethroids. A new class of insecticidal 2-(isoindolin-2-yl)alkanoates is also reported. In this series the most biologically active analogue was α-cyano-3-phenoxybenzyl 3-methyl-2-(4,5,6,7-tetrafluoroisoindolin-2-yl)butyrate. These esters were considerably less stable than the anilino analogues on exposure to air and light.  相似文献   

11.
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  相似文献   

12.
Close isosteres of fenvalerate [(RS)-α-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate], in which cyclopropyl groups replace isopropyl have insecticidal activity close to or greater than the parent compounds, and diminished intravenous toxicity to rats. A direct toxicological relationship of these compounds to fenvalerate itself and to chrysanthemate esters is indicated by the consistently greater activity of esters from one of an enantiomeric pair of acids. Other esters with larger alkyl or cycloalkyl groups, or spiropentane analogues of chrysanthemates are less active insecticides. 13C-Nuclear magnetic resonance spectra suggest that in the α-cyanobenzyl esters there is an intramolecular through-space interaction in solution. The relationships between the chemical structures of the compounds synthesised and their relative activities to different insect species and toxicity to rats are discussed.  相似文献   

13.
Fourteen oxime ethers and eleven other unsaturated compounds derived from 2,2-dimethyl-3-(3-phenoxybenzyloxy)propanal were synthesised and their insecticidal activity against Musca domestica, Locusta migratoria, Dysdercus cingulatus, Aedes aegypti, Plutella xylostella, Drosophila melanogaster, Tetranychus urticae and Spodoptera littoralis tested. Structural variations including chain length, branching and unsaturation of the oxime ether O-alkyl group and substituent exchange at the carbon-carbon double bond of the unsaturated compounds were made in order to examine the structure-activity relationship. All biological activities were compared with the activity of the ether pyrethroid MTI-500.  相似文献   

14.
BACKGROUND: Sterol 14α‐demethylase (CYP51), a key target of azole (DMI) fungicides, can be expressed in both prokaryotes and eukaryotes. Green mould of citrus, caused by Penicillium digitatum (Pers.) Sacc., is a serious post‐harvest disease. To develop specific and more effective fungicides against this disease, the characteristics of the interaction between sterol 14α‐demethylase from P. digitatum (PdCYP51) and possible new fungicides were analysed. The cyp51 gene of P. digitatum was cloned and expressed under different conditions in Escherichia coli (Mig.) Cast. & Chalm., and the binding spectra of PdCYP51 were explored by the addition of two commercial azoles and four new nitrogen compounds. RESULTS: The yield of soluble protein (PdCYP51) was largest when expressed in Rosetta (DE3) induced by 0.5 mM IPTG for 8 h at 30 °C. Compound B (7‐methoxy‐2H‐benzo[b][1,4]thiazine‐3‐amine) showed the strongest binding activity of the four new nitrogen compounds, with a Kd value of 0.268 µM . The Kd values of the six compounds were significantly correlated with their EC50 values. CONCLUSION: The spectral analysis and bioassay results could be used to screen the new chemical entities effectively. Compound B, selected by virtual screening from a commercial chemical library, is a candidate for a new DMI fungicide. These results provide a theoretical basis and new ideas for efficient design and development of new antifungal agents. Copyright © 2010 Society of Chemical Industry  相似文献   

15.
2-z-Substituted benzylamino-4-substituted-amino-6-chloro-1,3, 5-triazines are herbicidal compounds showing leaf-burning and/or growth inhibition with concomitant greening and stunting. Effects of chiral 1,3,5-triazine compounds in a light-independent seedling root elongation test with Echinochloa crus-galli var. frumentacea Wight demonstrated an interaction between chirality and root growth inhibition. The test compounds inhibited root growth, and this inhibition was due to interference with a system or systems other than photosynthesis. 4-(R)-sec-butylamino-2-(α,α-dimethylbenzyl)amino-6-chloro-1,3, 5-triazine showed the highest inhibitory activity, and 4-methylamino-2-(R)-a-methylbenzylamino-6-chloro-1,3,5-triazine was second. The chiral requirement for a strong inhibition of root growth was the (R)-configuration, contrasting with the requirement for the (S)-configuration for an inhibition of photosystem II.  相似文献   

16.
Following the discovery of insecticidal activity in (2E,4E)-N-(2-methylpropyl)-6-phenylhexa-2,4-dienamide, structural analogues containing variations of the central pentadiene system have been examined. They include the five compounds with extra methyl groups on each of the five carbons in turn, and compounds in which heteroatoms have been introduced instead of, or additional to, the original CH or CH2 groups. All were insecticidally inactive, indicating for the first time the severe limitations on this group if activity is to be retained.  相似文献   

17.
A series of 1-(3-pyridyl)-1-substituted-but-3-yn-1-ols and some related compounds were synthesised and tested for antifungal activity against eight phytopathogenic fungi of different taxonomic classes. High activity was shown in particular against Sphaerotheca fuliginea on Cucumis sativus. The compounds containing aromatic substituents gave the best results, not only in protectant but also in systemic and eradicant tests. The quantitative structure-activity relationship suggests that steric effects play an important role in determining fungicidal activity.  相似文献   

18.
BACKGROUND: Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin analogues with high activity, a series of new strobilurin derivatives containing substituted pyrazoles in the side chain were synthesised and bioassayed. RESULTS: The compounds were identified by 1H NMR, IR, MS and elemental analysis. Preliminary bioassays indicated that some title compounds exhibited excellent fungicidal activities against Pseudoperonospora cubensis (Burk. & Curt.) Rostovsev and Erysiphe graminis DC f. sp. tritici Marchal, protecting cucumber and wheat at 6.25 and 1.56 mg L?1 respectively, and showed a moderately high acaricidal activity against Tetranychus cinnabarinus (Boisd.) at 20 mg L?1. The relationship between structure and biological activity is discussed in terms of effects of the substituent of the pyrazole ring. CONCLUSION: The present work demonstrates that strobilurin analogues with substituted phenylpyrazolylmethoxymethyl side chains can be used as possible lead compounds for further developing novel fungicides and acaricides. Copyright © 2009 Society of Chemical Industry  相似文献   

19.
A new series of 5-(substituted phenoxy)pentyl 3-pyridyl ethers induced precocious metamorphosis in larvae of the silkworm, Bombyx mori. Both 2- and 4-pyridyl ethers were inactive, indicating that the 3-pyridine moiety was essential for the activity. Octyl, dodecyl and farnesyl 3-pyridyl ethers had no activity. Among the compounds tested so far, 5-(4-propylphenoxy)pentyl 3-pyridyl ether showed the highest activity. The activity fell off with increasing or decreasing length of the carbon chain between two oxygen atoms. Introduction of a methyl group at the 6 position of the pyridine ring completely eliminated the activity. Precocious metamorphosis induced by 3-pyridyl ethers was fully reversible by a simultaneous application of a small amount of tebufenozide, an ecdysteroid agonist, or methoprene, a JH agonist. © 1998 SCI.  相似文献   

20.
The quantitative relationship between the structure of 2-methoxy-5-(substituted-phenyl)-1, 3, 2-oxazaphospholidine 2-sulfides (5-PMOS) and their insecticidal activity against the house fly. Musca domestica L., was analyzed using reported physicochemical parameters and regression analysis. The electronic nature of the substituent on the phenyl group of 5-PMOS has the most significant effect on the activity, followed by hydrophobic and steric effects; the optimum value of Σρ is zero and the more hydrophobic the substituents on the phenyl group, the higher the insecticidal activity. The plots of observed pLD50, values against calculated pLD50 values for compounds having substituents in the ortho-position deviated downwards from those of compounds having substituents at the meta and/or para positions. This ortho-effect, which reduces the insecticidal activity of compounds having substituents at the ortho-position, was expressed by a dummy parameter D, which has the value 2 for di-ortho-substituted derivatives, 1 for mono-ortho-substituted derivatives and zero for others. Thus, the highest activity was obtained for 2-methoxy-5-phenyl-1, 3, 2-oxazaphospholidine 2-sulfide, and the activity was decreased by the introduction of any substituents on the phenyl group.  相似文献   

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