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1.
P. R. Chadwick 《Pest management science》1971,2(1):16-19
The activities of natural and synthetic pyrethroids against male German cockroaches (Blattella germanica) were examined by means of dusting and direct spraying techniques. NRDC 107 (5-benzyl-3-furylmethyl (+)-trans-chrysanthemate) was the most active compound in killing cockroaches. Pyrethrins gave the most rapid knockdown and were 60% as active as NRDC 107 (Bioresmethrin) in killing power. Tetramethrin and the corresponding (+)-trans-ester gave rapid knockdown. Only (+)-trans-allethrin [(+)-trans-chrysan-themate of (±)-allethrolone] provided useful knockdown and killing power together. Piperonyl butoxide had a relatively stronger synergistic action with less active killing agents. The rate of knockdown during the first few minutes of exposure was not altered greatly by piperonyl butoxide. 相似文献
2.
To investigate the action of dinotefuran (MTI-446, 1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine), a recently developed insecticide, on insect nicotinic acetylcholine receptors (nAChRs), we determined the potencies of the compound and 15 analogues in inhibiting the specific binding of [3H]epibatidine (EPI), a nAChR agonist, and [3H]alpha-bungarotoxin (alpha-BGT), a competitive nAChR antagonist, to the nerve cord membranes of American cockroaches (Periplaneta americana). Racemic dinotefuran inhibited [3H]EPI binding with an IC50 of 890 nM and [3H]alpha-BGT binding with an IC50 of 36.1 microM. Scatchard analysis indicated that the dinotefuran inhibition of [3H]EPI binding was a competitive one. Slight structural modification caused a drastic reduction in potency; only four analogues were found to be equipotent to or more potent than dinotefuran. Chloropyridinyl and chlorothiazolyl neonicotinoid insecticides displayed two or three orders of magnitude higher potency than dinotefuran. There was a good correlation between the IC50 values of tested compounds obtained with [3H]EPI and those obtained with [3H]alpha-BGT. A better correlation was observed between 3-h knockdown activities (KD50) against German cockroaches (Blattella germanica) and IC50 values obtained from [3H]EPI assays than between 24-h lethal activities (LD50) and IC50 values. While the results indicate that dinotefuran and its analogues interact with the ACh-binding site in cockroach nAChRs, it remains to be elucidated why they displayed lower potencies than those expected based on their insecticidal activities. 相似文献
3.
Keiichiro Nishimura Tetsuo Kitahaba Nobuyuki Okajima Toshio Fujita 《Pesticide biochemistry and physiology》1985,23(3):314-327
Knockdown and lethal activities of meta- and para-substituted benzyl (1R)-trans-chrysanthemates against the house fly were measured under synergistic conditions using piperonyl butoxide as an inhibitor of oxidative metabolism and NIA 16388 as an inhibitor of hydrolytic degradation. The variations in these activities were quantitatively analyzed in terms of physicochemical substituent effects using electronic, hydrophobic, and steric parameters of the aromatic substituents, and regression analysis. The most significant parameter in determining these activities is the steric bulkiness represented by the van der Waals voluem, the effect of which is highly specific to substituent positions. The substituent effects on knockdown and lethal activities against the house fly are shown to correspond well, respectively, with those on the convulsive and lethal activities against the American cockroach. The relationship between these symptomatic activities against the house fly and the neurophysiological activities determined by using excised nerve cords from American cockroaches were also quantitatively analyzed. Each house fly symptomatic activity was found to be analyzable by a linear combination of the neuroexcitatory and neuroblocking activity indices when the transport factor was separated by using the hydrophobicity parameter. 相似文献
4.
Kazunori Tsushima Toshihiko Yano Kimitoshi Umeda Noritada Matsuo Masachika Hirano Nobuo Ohno 《Pest management science》1989,25(1):17-23
A novel range of trimethylstanniomethyl ethers of well known pyrethroid alcohols were synthesised, and their insecticidal activities and modes of action as insecticides were investigated. Among them, ethers from three types of alcohol (3-phenoxybenzyl, 4-fluoro-3-phenoxybenzyl and 6-phenoxy-2-pyridylmethyl) showed remarkable insecticidal activities against rice stem borers, houseflies and German cockroaches. According to electrophysiological studies on the abdominal nerve cords of German cockroaches, trimethylstanniomethyl 6-phenoxy-2-pyridylmethyl ether induced a rapid decline in spontaneous firing similar to that from tetramethrin. However, insecticidal trimethyltin chloride caused an entirely different response. These observations suggest that the present tin ether derivatives resemble pyrethroids, rather than the insecticidal tin compounds known so far. 相似文献
5.
Keiichiro Nishimura Hideki Masutani George Holan Toshio Fujita 《Pest management science》1992,34(3):249-255
The insecticidal activities of optical isomers of 3-phenoxybenzyl 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarboxylate and related compounds were measured with American cockroaches and their knockdown activities were evaluated with house flies. The activities of the S(?)-isomer of the dichlorocyclopropanecarboxylate were higher than those of the R(+)-isomer. The effects of the compounds on the inward membrane currents induced by a stepdepolarizing pulse in crayfish axonal membranes were examined under voltage clamp conditions by the sucrose gap method. The compounds induced a tail current upon step repolarization of the membrane. The tail current decayed to zero in each record, but developed with time after the start of application of the compound until a steady level was reached. The rate of decay of the tail current observed in axonal membranes treated with the S(?)-isomer was slower than with the R(+)-isomer. The rates of development of the tail current induced by the two isomers were not very different. 相似文献
6.
AbstractThe German cockroach, Blattella germanica L. (Dictyoptera: Blattellidae), an invasive pest of human habitats, is distributed throughout the world, except in Antarctica. They have developed resistance against chemical pesticides used for the management of their populations. Numerous essential oils and their constituents have been tested; however, the insecticidal activities of clove bud powder, oil, and their constituents have not yet been tested against the German cockroaches. Thus, in this study, clove bud powder, oil, and their major constituents, eugenol and eugenol acetate, were evaluated for their contact toxicity and repellancy against adult German cockroaches under laboratory conditions. The clove bud powder applied at 30?mg/cm2 killed 92% of German cockroaches at 6?hours after treatment (HAT). Similarly, clove bud oil, eugenol and eugenol acetate applied at 4.00?ml/cm2 provided 95%, 85%, and 87% German cockroach mortality at 24, 6, and 24 HAT, respectively. At 2.0?ml/cm2, clove bud oil repelled 80% of German cockroaches within 30?min. In contrast, eugenol and eugenol acetate repelled 85% at 1.0?ml/cm2 and 2.5?ml/cm2, respectively, at 0.5 HAT. Based on this study, clove bud powder, oil, eugenol, and eugenol acetate could be environmentally friendly tools for the management of German cockroaches. 相似文献
7.
The binding of the neonicotinoid insecticide dinotefuran to insect nicotinic acetylcholine receptors (nAChRs) was examined by a centrifugation method using the nerve cord membranes of American cockroaches and [3H]dinotefuran (78 Ci mmol-1). The Kd and Bmax values of [3H]dinotefuran binding were estimated to be 13.7 nM and 14.8 fmol 40 microg-1 protein respectively by Scatchard analysis. Epibatidine, an nAChR agonist, showed a rather lower affinity to the dinotefuran binding site (IC50=991 nM) than dinotefuran (IC50=5.02 nM). Imidacloprid and nereistoxin displayed lower potencies than dinotefuran but higher potencies than epibatidine. The potencies of five dinotefuran analogues in inhibiting the specific binding of [3H]dinotefuran to nerve cord membranes were determined. A good correlation (r2=0.970) was observed between the -log IC50 values of the tested compounds and their piperonyl butoxide-synergised insecticidal activities (-log LD50 values) against German cockroaches. The results indicate that a high-affinity binding site for dinotefuran is present in the nerve cord of the American cockroach and that the binding of ligands to the site leads to the manifestation of insecticidal activity. 相似文献
8.
Forty new organofluorine compounds, containing phosphorus, have been synthesised as potential pesticides. The compounds include esters of O,O-dialkyl phosphoramidic acids of the type (RO)2P(O)NHAr; thioesters of O,O-dialkyl thiophosphoramidic acids of the type (RO)2P(S)NHAr; esters of O,O-dialkyl phosphonic acid of the type (RO)2P(O)Ar and esters of O,O-dialkyl thiophosphonic acid (RO)2P(S)OAr. All the compounds have been screened for their insecticidal activity against adult cockroaches (Periplanata americana) and a few show appreciable activity. 相似文献
9.
Riaz Hasan Keiichiro Nishimura Masakazu Okada Miki Akamatsu Masafumi Inoue Tamio Ueno Tooru Taga 《Pest management science》1996,46(2):105-112
Methyl 3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate was converted to corresponding (1R)- and (1S)-phenethyl esters via its carboxylic acid and acid chloride at the C-4 atom to separate the diastereomers. Their configurations were confirmed by X-ray analysis. Both isomers of the (1R)methylbenzyl ester were subjected to transesterification with sodium methoxide to obtain enantiomers of the starting methyl ester. Their insecticidal activity was measured against American cockroaches (Periplaneta americana (L.)) by injection and against house flies (Musca domestica L.) by topical application under various synergistic conditions with metabolic inhibitors. The activity values of the four α-methylbenzyl esters and the R-isomer of the starting methyl ester were similar. The S-enantiomer of the methyl ester was about 10 and 100 times more active than the R-isomer against the cockroach and the fly, respectively. Some N-arylacetyl and N-aryloxyacetyl derivatives of the starting N-(4-chlorophenyl)carbamoyl compound gave very low activity. Conformation-energy profiles for some compounds suggested that the conformation of substituents on the N-1 atom in the pyrazoline ring has a specific role for the potential insecticidal effects. 相似文献
10.
F. Barlow M. Elliott A. W. Farnham A. B. Hadaway N. F. Janes P. H. Needham J. C. Wickham 《Pest management science》1971,2(3):115-118
A range of 5-benzyl-3-furylmethyl cyclopropane carboxylates and other esters are evaluated against house-flies, mustard beetles and two mosquito species. The results show the importance for activity of a gem-dimethyl group on the cyclopropane ring and that substitutions at C3 give wide variations in insecticidal activity and marked species specificity. Some of the compounds had considerable knockdown activity against houseflies, but the structural requirements for this type of action differ markedly from those for kill. 相似文献
11.
The insecticidal activities of imidacloprid derivatives with a wide range of substituents at the 5-position on the pyridine ring against American cockroaches, Periplaneta americana (L.), were measured by injection with and without synergists propyl 2-propynyl phenylphosphonate and piperonyl butoxide. The log(1/MLD) value (MLD = minimal lethal dose in mol) without synergists was 7.96 for the methyl derivative, and the values were lower for other derivatives. Synergists enhanced the potencies of all the compounds tested. Considering these compounds and those with other substituents at this position, the region for maximum activity was predicted to be in the conjunction of the pyridyl 6-chlorine atom with a lipophilic small group in the 5-position. 相似文献
12.
张兴甲 陕西省生物农药工程技术研究中心 陕西 杨凌 魏志敏 陕西省生物农药工程技术研究中心 陕西 杨凌 王宇佳 陕西省生物农药工程技术研究中心 陕西 杨凌 杨龙港 陕西省生物农药工程技术研究中心 陕西 杨凌 袁含笑 陕西省生物农药工程技术研究中心 陕西 杨凌 冯俊涛 陕西省生物农药工程技术研究中心 陕西 杨凌 高艳清 陕西省生物农药工程技术研究中心 陕西 杨凌 雷鹏 陕西省生物农药工程技术研究中心 陕西 杨凌 马志卿 陕西省生物农药工程技术研究中心 陕西 杨凌 《农药学学报》2022,24(1):59-65
为发现具有高抑菌活性的先导化合物,结合本课题组前期研究,设计并合成了18个新型3-二氟甲基-1-甲基吡唑-4-羧酸肟酯衍生物,其结构均经核磁共振氢谱、碳谱及高分辨质谱分析确证,化合物 9g 的单晶衍射结果证明肟酯的构型为E式。离体生物活性测定结果表明,目标化合物在50 μg/mL下对番茄灰霉病菌 Botrytis cinerea、苹果树腐烂病菌Valsa mali 和小麦全蚀病菌Gaeumannomyces graminis均表现出一定的抑制活性,其中化合物 9d 对苹果树腐烂病菌、 9r 对小麦全蚀病菌的EC50值分别为0.89 μg/mL和3.34 μg/mL,表现出比先导化合物 L1 (E-2-氯-6-氟苯甲醛-O-(1-甲基-3-苯基-1H-吡唑-5-羰基)肟)
13.
《Pesticide biochemistry and physiology》1987,29(3):217-232
The insecticidal activity of a series of m-phenobenzyl esters of iso-valeric and tert-butylacetic acids, the α-position of which was substituted with one of alkyl, alkoxyalkyl, alkoxy, benzyl, phenyl, phenoxy, and anilino groups, was measured by injection into American cockroaches under synergistic conditions to suppress possible oxidative and hydrolytic metabolism. Their neuroexcitatory activity on nerve preparations excised from the cockroaches was measured by an extracellular recording technique. The activities of the analogous esters of cyclopropanecarboxylic acids with a substituted vinyl side chain were also measured. The insecticidal activity was quantitatively analyzed with physicochemical parameters for the α-substituent or its counterpart of the acid moiety. Variations in the activity were related parabolically to both the hydrophobicity and the length of the substituent. The activity of compounds, the α-substituent of which is either a substituted phenyl or a phenoxy group, was about 10 times that of compounds with “physicochemically equipvalent” aliphatic substituents. α-Substitution with ring-substituted anilino groups, but not with N-methyl groups, enhanced the activity about 25 times, but the vinylcyclopropane structure raised the activity to about 60 times that of physicochemically equivalent aliphatic noncyclopropane substituents. Variations in the insecticidal activity were closely related to those in the neuroexcitatory activity when hydrophobic and steric factors were separated. The steric factor in addition to the hydrophobicity seemed to be important in the transport process. 相似文献
14.
Non-cyclopropane pyrethroid esters of different substituted 2-phenoxy-3-methylbutanoic acids have been synthesised using the three alcohols—3-phenoxybenzyl alcohol, α-cyano-3-phenoxybenzyl alcohol and 3, 4-methylene-dioxybenzyl alcohol. Among the 35 esters synthesised and tested against Culex quinquefasciatus Say, the Bancroftian filariasis vector, for both larvicidal and adulticidal activities, α-cyano-3-phenoxybenzyl 2-(4-fluorophenoxy)-3-methylbu-tanoate, with an LC50 value of 2.5 × 10?3 mg litre?1 for larvicidal activity, and α-cyano-3-phenoxybenzyl-2-(4-chlorophenoxy)-3-methylbutanoate, with an LD50 value of 30 times; 10?4 ug insect?1 for adulticidal activity, were found to be as effective as fenvalerate, a well-known non-cyclopropane pyrethroid ester. Structure-activity studies showed that the insecticidal activity is dependent on the nature and position of the substituent in the phenyl ring of the acid moiety and also on the type of alcohol moiety. 相似文献
15.
异噁唑是具有较好活性的五元杂环,本文设计并合成了15个5-甲基异噁唑-4-甲酸肟酯类新化合物,利用核磁氢谱、核磁碳谱和高分辨质谱对其结构进行确证,并测试了其对番茄灰霉病菌Botrytis cinerea、水稻纹枯病菌Rhizoctonia solani、苹果树腐烂病菌Valsa mali和小麦全蚀病菌Gaeumannomyces graminis的离体抑菌活性。结果表明,在50μg/mL下,目标化合物对供试病原菌均有一定的抑菌活性,其中化合物5g对番茄灰霉病菌的抑制活性优于先导化合物L1和肟菌酯,EC50值为1.95μg/mL。 相似文献
16.
17.
The toxicity of a promising new insecticide, imidacloprid, was evaluated against several susceptible and resistant strains of German cockroach and house fly. Imidacloprid rapidly immobilized German cockroaches followed by a period of about 72 h during which some cockroaches recovered. After 72 h there was no further recovery. Imidacloprid-treated houseflies were immobilized more slowly than treated cockroaches, with the maximum effect observed after 72 h, and there was no recovery. Based upon 72-h LD50 values imidacloprid was moderately toxic to German cockroaches (LD50 values were 6–8 ng mg-1) and had only low toxicity to house flies (LD50 140 ng mg-1). Piperonyl butoxide (PBO) blocked the observed recovery in German cockroaches. PBO also greatly enhanced the 72-h LD50 of imidacloprid from 43- to 59-fold in cockroaches and 86-fold in house flies. Two strains of German cockroach (Baygon-R and Pyr-R) showed >4-fold cross-resistance to imidacloprid. This cross-resistance could not be suppressed by PBO, suggesting that P450 monooxygenase-mediated detoxication is not responsible for this cross-resistance. Variation in the level of synergism observed with PBO (between strains) suggests the ‘basal’ level of monooxygenase-mediated detoxication of imidacloprid is quite variable between strains of German cockroach. The AVER and LPR strains of house fly showed significant cross-resistance to imidacloprid. PBO reduced the level of cross-resistance in AVER from >4·2-fold to 0·5-fold (i.e. the AVER strain LD50 was half that of the susceptible strain when both were treated with PBO), but PBO did not suppress the cross-resistance in LPR. These data suggest monooxygenases are the mechanism responsible for cross-resistance to imidacloprid in AVER, but not in the LPR strain. © of SCI. 相似文献
18.
Shoji Nakagawa Nobuyuki Okajima Tetsuo Kitahaba Keiichiro Nishimura Toshio Fujita Minoru Nakajima 《Pesticide biochemistry and physiology》1982,17(3):243-258
A number of substituted benzyl (1R)-trans-chrysanthemates and related compounds were synthesized. Their symptomatic activities in terms of levels which induce convulsions as well as cause death in American cockroaches were determined by injection with and without application of synergists as inhibitors of metabolism. The neuroexcitatory and neuroblocking activities were also determined in terms of minimum effective concentrations to induce repetitive train of impulses and conduction blockage, respectively, to central nerve cords excised from the cockroaches and immersed in Ringer's solution. Correlations between symptomatic and neurophysiological activities were analyzed quantitatively with the aid of molecular hydrophobicity parameter and regression analysis. Each symptomatic activity from which the effect of metabolism is eliminated was found to be analyzable by means of a linear combination of indices for two types of neurophysiological activity when the transport factor is separated by using the hydrophobicity parameter. A closer correlation was found between neuroblocking activity and the “convulsive” effect than between neuroexcitatory activity and the “convulsive” effect, whereas both neurophysiological effects operate together on the cockroaches resulting in paralysis and death. 相似文献
19.
Shoji Nakagawa Nobuyuki Okajima Keiichiro Nishimura Toshio Fujita Minoru Nakajima 《Pesticide biochemistry and physiology》1982,17(3):259-270
The substituent effects on the symptomatic and neurophysiological activities of a number of substituted benzyl (1R)-trans-chrysanthemates against American cockroaches were quantitatively analyzed using electronic, hydrophobic, and steric parameters. The effects were shown to be highly specific to substituent positions except for those on the neuroblocking activity. Steric effect of substituents represented by van der Waals volume was found to play the most significant role in determining the variation in each activity. Peculiar substituent effects depending upon the bulkiness and position of substituents, which had been observed in the toxicity of this class of compounds, can be rationalized by the present analysis indicating that the optimum van der Waals volume of substituents is largest at the ortho and smallest at the para position. 相似文献
20.
To investigate relationships between the molecular structure of pyrethroids and their mode of action, toxicities to adult male Periplaneta americana by topical application and injection were compared with toxicities to their giant fibre nerve axons. From the tests against intact insects it was concluded that: (i) although ED50S ranged from 0.04 to 65 μg/insect, each compound was equally toxic, with one exception, when administered by either route; (ii) esters of (1 R)-cis- were more toxic than esters of the corresponding (1 R)-trans-3-substituted-2, 2-dimethylcyclopropanecarboxylic acids; (iii) α-cyano-3-phenoxybenzyl esters were more toxic than the corresponding 3-phenoxybenzyl esters; (iv) changes in the alcoholic component of some compounds (particularly trans-isomers of esters of 5-benzyl-3-furylmethanol and esters of α-cyano-3-phenoxybenzyl alcohol) affected a recovery phase in their ED50/time curves more than changes in the acid component; (v) the amount of recovery was positively correlated with molecular polarity. The concentration required to decrease the amplitude of the action potential of giant fibres by 30% in 1 h ranged from 0.26 μM for the most active compound to 100 μM for the least active. There was no clear relationship between neurotoxicity and toxicity to whole insects and little association between neurotoxicity and features of molecular structure. Neurotoxicity was, however, positively correlated with polarity. Giant fibre axons seem unlikely to be critical sites of action of pyrethroids. 相似文献