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1.
Two series of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole were synthesized, and their structures were characterized by (1)H NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities, and their insecticidal activities against oriental armyworm, mosquito, and spider mite are comparable to those of the commercialized Chlorfenapyr.  相似文献   

2.
Milbemycins have received considerable interest in agricultural chemistry due to a special action mode, extremely high activity against arachnoide pests, low toxicity to mammals, and environmentally benign characteristics. Two series of novel milbemycin analogues (4Ia-6IIc) containing alkyl and aryl groups at the 4'- and 13-positions were designed and synthesized by five schemes. These analogues were identified by (1)H NMR, (13)C NMR, and elemental analysis (or HRMS). Their insecticidal activities against carmine spider mite, oriental armyworm, and black bean aphid were evaluated. The results showed that all of the title compounds had low acaricidal activity against carmine spider mite. However, most of them exhibited good insecticidal activities against oriental armyworm and black bean aphid at a concentration of 200 mg L(-1). The most potent substituents of 2,2-dimethylbutanoyl (4Ib), phenylacetyl (4IIm), and (Z)-1-(methoxyimino)-1-phenylacetyl (4IIn) exhibited the highest larvicidal activities, and its insecticidal LC(50) values against oriental armyworm were 0.250, 0.204, and 0.350 mg L(-1), while its insecticidal LC(50) values against black bean aphid were 0.150, 0.070, and 0.120 mg L(-1), respectively. These substituents provided some hints for further investigation on structure modification.  相似文献   

3.
A series of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety was designed and synthesized via the key intermediate 3-(2,4,6-trimethyl)-2-oxo-1-oxaspiro[4.4]-decyl-3-en-4-ol. The target compounds were identified by (1)H NMR and elemental analysis or high-resolution mass spectrum (HRMS). The results of bioassays indicated that most of the target compounds possessed excellent acaricidal activities against carmine spider mite larvae and eggs. Especially, diisopropylamino oxalyl compound 7g and piperidine oxalyl compound 7h were 1.4- and 2.3-fold as high as the activities of commercial Spiromesifen, respectively, against spider mite eggs. Moreover, most of the target compounds exhibited insecticidal activities against Lepidoptera pest. Interestingly, compounds containing alkylamino-substituted oxalyl moiety showed obvious selectivity between spider mite larvae and eggs because the activities against spider mite eggs of 7g and 7h were 25-fold those against spider mite larvae, whereas Spiromesifen had no significant differences in these activities. This meant that the introduction of an oxalyl moiety to spirocyclic tetronic acid might lead to novel biological activity characteristics.  相似文献   

4.
Enormous numbers of synthetic fluorine-containing compounds have been widely used in a variety of fields, especially in drug and pesticide design. To find novel insect growth regulators, a series of benzoylphenylureas with fluorinated substituents were designed and synthesized. The results of larvicidal activities of those novel fluoro-substituted benzoylphenylureas against oriental armyworm and mosquito revealed that most compounds exhibited excellent activities. It is worth mentioning that compounds 3 and 6 exhibited higher activities against oriental armyworm and mosquito than commercial Hexaflumuron. It can be further seen that the insecticidal activities would increase significantly by introducing fluorinated substituents into the structure of the designed benzoylphenylureas.  相似文献   

5.
On the basis of commercial insecticides tebufenpyrad and tolfenpyrad, two series of novel pyrazole-5-carboxamides containing α-hydroxymethyl-N-benzyl or α-chloromethyl-N-benzyl and pyrazoles containing 4,5-dihydrooxazole moieties were designed and synthesized via the key intermediate 2-amino-1-(4-substituted) phenyl ethanol. The structures of target compounds were confirmed by (1)H NMR and elemental analysis or high-resolution mass spectrum (HRMS), and their activities against cotton bollworm (Helicoverpa armigera), diamondback moth (Plutella xylostella), bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens), and spider mite (Tetranychus cinnabarinus) were tested. The results of bioassays indicated that compounds containing α-chloromethyl-N-benzyl and compounds containing 4,5-dihydrooxazole showed high insecticidal activity against cotton bollworm. Especially, stomach activities of compounds Ij, Il, and IIe were 60% at 5 mg kg(-1). Moreover, the target compounds exhibited high selectivity between cotton bollworm and diamondback moth, although both of them belong to the order Lepidoptera. Although the activities against diamondback moth were at a low level, some of the target compounds exhibited antifeedant activity. The compounds also had good activities against bean aphid, mosquito, and spider mite. The foliar contact activity of compounds Ic, Id, Ie, and IIf against bean aphid were 95, 95, 100, and 95%, respectively, at 200 mg kg(-1). The miticidal and ovicidal activities of compound IIi against spider mite were both 95% at 200 mg kg(-1). Furthermore, a trivial change at 4-position of pyrazole ring would lead to great changes in properties and activities, which can easily be deduced by comparing the activities of compounds in series I (4-chloro-pyrazole compounds) with corresponding compounds in series II (4-hydro-pyrazole compounds), especially from the miticidal and ovicidal activities of Ii and IIi against spider mite.  相似文献   

6.
Novel benzoylphenylureas containing an oxime ether group were designed and synthesized by four schemes. These benzoylphenylureas were identified by (1)H NMR spectroscopy and element analysis (or HRMS). The bioactivities of the new compounds were evaluated. These benzoylphenylureas exhibited excellent larvicidal activities against oriental armyworm, some of which were much better in comparison with the commercial Flucycloxuron. In particular, the larvicidal activities against oriental armyworm of compounds 1 and 23 were 5-10 times better than that of Flucycloxuron. Most of these benzoylphenyureas exhibited excellent larvicidal activities against mosquito. At the same time, some of these compounds have good plant growth regulatory activities as well.  相似文献   

7.
Two series of anthranilic diamides containing acylthiourea and acylurea linkers were designed and synthesized, with changed length and flexibility of the linkers to compare to known anthranilic diamide insecticides. In total, 26 novel compounds were synthesized, and all compounds were characterized by (1)H nuclear magnetic resonance and high-resolution mass spectrometry. Their insecticidal activities against oriental armyworm ( Mythimna separata ), mosquito larvae ( Culex pipiens pallens ), and diamondback moth ( Plutella xylostella ) were evaluated. The larvicidal activities against oriental armyworm indicated that the introduction of acylthiourea into some structures could retain their insecticidal activity; 8 of the 15 compounds (13a-13e, 14a-14e, and 15a-15e) exhibited 100% larvicidal activity at 10 mg/L. However, the introduction of acylurea decreased the insecticidal activity; only 3 of the 11 compounds (17a-17k) exhibited 100% larvicidal activity at 200 mg/L. The whole-cell patch-clamp technique indicated that compound 13b and chlorantraniliprole exhibited similar effects on the voltage-gated calcium channel. The calcium-imaging technique was also applied to investigate the effects of compounds 13b and 15a on the intracellular calcium ion concentration ([Ca(2+)](i)), which indicated that they released stored calcium ions from endoplasmic reticulum. Experimental results denoted that several new compounds are potential activators of the insect ryanodine receptor (RyR).  相似文献   

8.
A series of novel N-(alkyldithio) and N-aminothio derivatives of N'-tert-butyl-N,N'-diacylhydrazines were designed and synthesized as insect growth regulators via the key intermediates N-chlorosulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. A series of novel N,N-dithio derivatives were also designed and synthesized with N'-tert-butyl-N,N'-diacylhydrazines and sulfur chloride in the presence of sodium hydride. Compared to the parent compounds, these derivatives displayed better solubility and improved hydrophobicities. The insecticidal activities of the target compounds were evaluated. The results of bioassays showed that the target compounds possessed comparable activities against oriental armyworm with the corresponding parent compounds. In particular, N-(morpholinosulfenyl)-N'-tert-butyl-N-4-ethylbenzoyl-N'-3,5-dimethylbenzoylhydrazide (IIIk) has higher toxicities against oriental armyworm and diamondback moth than the parent compound, RH-5992.  相似文献   

9.
Twenty-two new benzoylphenylureas containing isoxazoline and the isoxazole group were designed and synthesized, and their structures were characterized by (1)H NMR and elemental analysis (or HRMS). The larvicidal activities against Oriental armyworm, mosquito, and diamondback moth of the new compounds were evaluated. Compounds I-1 and III-1 showed nearly the same level of insecticidal activity against Oriental armyworm as commercial insecticide Flucycloxuron and surprisingly exhibited much higher larvicidal activities against diamondback moth than Flucycloxuron.  相似文献   

10.
A series of novel N-alkoxysulfenyl-N'-tert-butyl-N, N'-diacylhydrazines were designed and synthesized as insect growth regulators by the key intermediates N-chlorosulfenyl-N'-tert-butyl-N, N'-diacylhydrazines, which were prepared for the first time. Compared to N'-tert-butyl-N, N'-diacylhydrazines, these N-alkoxysulfenyl derivatives displayed better solubility and improved hydrophobicities. The insecticidal activities of the new compounds were evaluated. The results of bioassays showed that the title compounds possessed a combination of strong stomach as well as contact poison property higher than the corresponding parent compounds. In particular, N-methoxysufenyl-N'-tert-butyl-N-4-ethylbenzoyl-N'-3,5-dimethylbenzoylhydrazide (IIIf) as a field testing candidate has higher stomach toxicities against oriental armyworm and beet armyworm than the corresponding parent compound RH-5992. Furthermore, the compound IIIf exhibits higher contact activities against oriental armyworm, Asian corn borer, tobacco cutworm, and cotton bollworm than RH-5992. The sulfenyl substituent was essential for high larvacidal activity.  相似文献   

11.
A series of novel N-substituted phenoxysulfenyl- N'- tert-butyl- N, N'-diacylhydrazines were designed and synthesized as insect growth regulators via the key intermediates N-chlorosulfenyl- N'- tert-butyl- N, N'-diacylhydrazines. Compared to the parent compounds, these N-substituted phenoxysulfenyl derivatives displayed better solubility and improved hydrophobicities. The insecticidal activities of the new compounds were evaluated. The results of bioassays showed that the title compounds possessed a combination of strong stomach as well as contact poison property higher than the corresponding parent compounds. In particular, N-(4-chlorophenoxy)sulfenyl -N'- tert-butyl- N-4-ethylbenzoyl- N'-3,5-dimethylbenzoylhydrazide ( IIIi) as a field testing candidate has higher stomach toxicities against oriental armyworm and tobacco cutworm than the corresponding parent compound RH-5992. Furthermore, the compound IIIi exhibits higher contact activities against Asian corn borer, tobacco cutworm, and cotton bollworm than RH-5992.  相似文献   

12.
A series of novel monohalovinylated pyrethroids are designed and synthesized to replace one halo atom with a hydrogen atom on the double bond of dihalopyrethroids. Bioassays indicate that some of the synthesized compounds, such as 3j and 1j, exhibit high insecticidal activities against mosquitoes ( Culex pipiens pallens ), oriental armyworms ( Mythimna separata ), alfalfa aphids ( Aphis medicagini ), and carmine spider mites ( Tetranychus cinnabarinus ). Photolytic results of E-cis-1j suggest that monohalovinylated pyrethroids are photodegraded more easily than compound 12.  相似文献   

13.
Several series of novel N'-tert-butyl-N'-substituted-benzoyl-N-[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide derivatives Ia, Ib, IIa-IIg, IIIa, IIIb, and Va-Vc were designed and synthesized. Their structures were confirmed by (1)H NMR spectra, HRMS, and X-ray single-crystal structures. The larvicidal activities against oriental armyworm, beet armyworm, diamond-back moth, and corn borer of these compounds were evaluated and contrasted with those of RH-2485, JS-118, and ANS-118. The larvicidal activities against oriental armyworm indicate that monosubstituent or multisubstituents and the substituting group position cannot promote increasing activities and that the cycle region in the general structure of IIa-IIg is much more sensitive to activity than that in the general structure of Ia and Ib. The space volume of the A ring in the structure of Va cannot be too large; if it is, the activity will be decreased significantly. Stomach toxicities against beet armyworm, diamond-back moth, and corn borer of compounds Ia, Ib and IIg indicate that benzoheterocyclic analogues of N-tert-butyl-N,N'-diacylhydrazines show significant selectivities to different lepidopterous pests.  相似文献   

14.
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15.
A series of novel pyrazole oxime derivatives containing a 2-chloro-5-thiazolyl moiety were synthesized. Their structures were confirmed by (1)H NMR, (13)C NMR, and elemental analysis. The preliminary bioassays showed that all of the title compounds had low acaricidal activity against Tetranychus cinnabarinus . However, most of them exhibited excellent insecticidal activity against Aphis medicagini at the dosage of 0.5 mg/mL, and some compounds still showed good insecticidal activity against A. medicagini even at the dosage of 0.2 mg/mL. Meanwhile, some title compounds displayed fungicidal and plant growth regulatory activities.  相似文献   

16.
On the basis of the structure of heterocyclic-fused cis configuration derivatives and chain-opening neonicotinoids, two series of novel chain-opening tetrahydropyridine analogues were designed and synthesized. The preliminary bioassay tests were determined on cowpea aphid (Aphis craccivora) and armyworm (Pseudaletia separata Walker). The results showed that some of the target compounds exhibited repellent effects, whereas others showed good insecticidal activities.  相似文献   

17.
Some essential oils obtained from the branches of four Pinus species (P. pinea L., P. halepensis Mill., P. pinaster Soil in Ait., and P. nigra Arnold) have been evaluated for their acaricidal activity by aerial diffusion against the stored food mite Tyrophagus putrescentiae (L.). All the essential oils showed a good efficacy, but P. pinea oil and its two constituents 1,8-cineole and limonene were the most effective compounds, showing 100% acaricidal activity at 8 microL; 1,8-cineole showed the same activity at 6 microL.  相似文献   

18.
The acaricidal effects of an active constituent derived from Petroselinum sativum seeds and its derivatives were determined using impregnated fabric disk bioassay against Dermatophagoides farinae , Dermatophagoides pteronyssinus , and Tyrophagus putrescentiae and compared with that of synthetic acaricide. The acaricidal constituent of P. sativum was isolated by various chromatographic techniques and identified as apiol. On the basis of LD(50) values against D. farinae and D. pteronyssinus, apiol (0.81 and 0.94 μg/cm(2)) was 12.4 and 10.2 times more toxic than benzyl benzoate (10.0 and 9.58 μg/cm(2)), respectively. In acaricidal studies of apiol derivatives, 3,4-methylenedioxybenzonitrile (0.04, 0.03, and 0.59 μg/cm(2)) was 250, 319, and 20.7 times more toxic than benzyl benzoate (10.0, 9.58, and 12.2 μg/cm(2)) against D. farinae, D. pteronyssinus, and T. putrescentiae. In structure-activity relationships, the acaricidal activities of apiol derivatives could be related to allyl (-C(3)H(5)) and methoxy (-OCH(3)) functional groups. Furthermore, apiol and its derivatives could be useful for natural acaricides against these three mite species.  相似文献   

19.
1-Acetyl-3,-5-diarylpyrazolines have received considerable interests from the fields of medicinal and agricultural chemistry due to their broad spectrum of biological activities. To discover new lead compounds exhibiting both fungicidal and insecticidal activities, a series of pyrazoline derivatives were designed and synthesized by introducing the beta-methoxyacrylate pharmacophore into the scaffold of 1-acetyl-3,5-diarylpyrazoline. The fungicidal activities against Pseudoperoniospora cubensis, Sphaerotheca fuliginea, Botrytis cinerea, and Rhizoctonia solani and the insecticidal activities against Aphis medicagini, Nilaparvata legen, Mythima separata, and Tetranychus cinnabarnus were screened. The most potent compound 13, 1-aceto-3-[m-[o-(E-1-methoxycarboxyl-2-methoxy)-1-yl]benzyloxy]phenyl-5-(benzo-[1,3]-dioxolyl)-4,5-dihydro- pyrazoline, was identified. Its fungicidal IC(50) values against P. cubensis and S. fuliginea are 26.6 and 57.6 microg mL(-1), respectively, while its insecticidal LC(50) value against M. separata is 26.6 microg mL(-1). These results indicated that compound 13 could be used as a lead for further developing new pyrazoline type products exhibiting both fungicidal and insecticidal activities.  相似文献   

20.
Acaricidal activities of materials derived from Chamaecyparis obtusa leaves against Dermatophagoides farinae and Dermatophagoides pteronyssinus were examined using the dry film method and compared with that of commercial benzyl benzoate and N,N-diethyl-m-toluamide (DEET). The active constituent of the C. obtusa leaves was identified as beta-thujaplicin (C10H12(O2)) by spectroscopic analyses. Responses varied with dose. On the basis of a 24 h LC50 value, acaricidal activity against D. farinaewas more pronounced with beta-thujaplicin (72.2 mg/m2) than benzyl benzoate (89.9 mg/m2) and DEET (377 mg/m2). Acaricidal activity against D. pteronyssinus was more pronounced in beta-thujaplicin (62.1 mg/m2) than benzyl benzoate (72.4 mg/m2) and DEET (193 mg/m2). These results indicate that acaricidal activity of C. obtusa leaves likely results from by beta-thujaplicin. Beta-thujaplicin merits further study as potential house dust mite control agents or lead compounds.  相似文献   

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