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1.
Yoshiaki Nakagawa Katsuhiko Kitahara Takaaki Nishioka Hajime Iwamura Toshio Fujita 《Pesticide biochemistry and physiology》1984,21(3):309-325
The larvicidal activity of a series of N-2,6-difluoro- and N-2,6-dichlorobenzoyl-N′-(4-substituted phenyl)ureas against nondiapause larvae of the rice stem borer, Chilo suppressalis Walker, was measured by topical application and oral administration methods under conditions with and without piperonyl butoxide as an inhibitor of oxidative metabolism. The effects of substituents at the anilide moiety on the larvicidal activity were analyzed quantitatively using physicochemical substituent parameters and regression analysis. The results indicate that the oxidative metabolism in the larval body which is favored by electron-donating substituents is significant in determining the activity. The activity, when the metabolic factor is eliminated, is enhanced by electron-with-drawing and hydrophobic substituents and lowered by bulky groups. The inhibitory activity against new cuticle formation of the same series of compounds was also measured using cultured integument of the rice stem borer diapause larva. The comparison of the quantitative analyses between larvicidal and integument-level activities shows that inhibition of cuticular development is the most important factor governing larvicidal activity. 相似文献
2.
Yoshiaki Nakagawa Hajime Iwamura Toshio Fujita 《Pesticide biochemistry and physiology》1985,23(1):7-12
The larvicidal activity of a series of N-2,6-difluorobenzoyl-N′-[4-(substituted benzyloxy)-phenyl]-ureas against nondiapause larvae of the rice stem borer, Chilo suppressalis Walker, was measured by a topical application method under conditions in which oxidative metabolism was inhibited by piperonyl butoxide. The effects of the substituted-benzyloxy moiety on variations in the activity were analyzed quantitatively using physicochemical substituent parameters and regression analysis. Results were compared with those found previously for N-2,6-difluorobenzoyl-N′-(4-substituted phenyl)-ureas, indicating that the electron-withdrawing property of the anilide substituents participates in determining the activity through the inductive effect. The hydrophobicity of the total anilide substituents favors activity, whereas the steric dimension in terms of the width lowers it. Although inhibition of new cuticle formation on cultured integument of diapausing larva could not be determined accurately for most of the compounds because of their limited solubility in the assay medium, inhibitory activity seemed related to larvicidal activity, as was the case for previously investigated simpler congeners. 相似文献
3.
Ichiki Takemoto Ryo Yoshida Seizo Sumida Katsuzo Kamoshita 《Pesticide biochemistry and physiology》1985,23(3):341-348
Relationships between three types of herbicidal activity of N′-substituted phenyl-N-methoxy-N-methylureas and substitution at the benzene ring were analyzed by the Hansch-Fujita method. First, the Hill inhibitory activity was correlated with electronic (σ) as well as hydrophobic (π) substituent constants. The existence of an optimum value of hydrophobicity for substituents was suggested to reach the target site of action. Second, bliaching activity observed for the 3-substituted but not for 4-substituted compounds was correlated with π, σ, and steric substituent constant, Es. Third, the postemergent herbicidal activity was shown to correlate linearly with the Hill inhibitory activity, pI50, and hydrophobic parameter, π. 相似文献
4.
5.
The antifungal activity of 61 N-phenylsuccinimides and 16 N-phenyl-1,2-dimethylcyclopropanedicarboximides having various benzene ring substituents was determined against Botrytis cinerea by the agar medium dilution method. The structure-activity relationships were analyzed using such physicochemical substituent parameters as hydrophobic π, electronic σ0, steric E8, and HB (hydrogen bonding) values with the multiple regression technique. The π values were derived from log P (octanol-water partition coefficient) values for the N-monosubstituted-phenylsuccinimide system. The hydrophobic effect is significant only for m-substitutents. The stronger the electron withdrawal and the smaller the steric dimensions of the ring substituents, the greater is the activity. When substituents are hydrogen bond acceptors, the effect is to lower the activity. These features are almost identical between two series of compounds. 相似文献
6.
从对溴苯氧乙酸出发,先合成中间体酰基异硫氰酸酯,该中间体与2-氨基-5-芳基-1,3,4- 口 恶 二唑反应合成了10个新的苯氧乙酰基硫脲类化合物,其结构经元素分析、红外光谱、核磁共振氢谱和质谱确认。初步生物活性测试结果表明,在50 mg/L浓度下,所有目标化合物对水稻纹枯病菌Rhizatonia solani和黄瓜灰霉病菌Botrytis cinereapers的抑制率均达85％以上,部分化合物对黄瓜灰霉病菌的抑制率达100%。 相似文献
7.
Ian E. Clarke Gerhard Sandmann Peter M. Bramley Peter Böger 《Pesticide biochemistry and physiology》1985,23(3):335-340
Inhibition of carotenoid biosynthesis by herbicidal m-phenoxybenzamide derivatives has been investigated in a cell-free carotenogenic system from Aphanocapsa. Their target is the phytoenedesaturase reaction. Double-reciprocal plots of β-carotene biosynthesis (from 14C-labeled geranylgeranyl pyrophosphate) showed that 3-(2,5-dimethylphenoxy)-N-ethylbenzamide was a noncompetitive inhibitor of the phytoene-desaturase complex. The Ki value for cell-free inhibition of β-carotene formation was almost identical to the I50 value of intact cells. Furthermore, the influence of certain substituents on herbicidal activity has been investigated. Inhibition increased with the length of the unbranched N-alkyl chains. In addition, substituents at the phenoxy group with higher lipophilicities showed greater inhibitory activities. The presence of a phenoxy or trifluoromethyl moiety at position 3 is essential. 相似文献
8.
《Pesticide biochemistry and physiology》1986,25(1):112-124
Tridemorph and fenpropimorph as well as several related N-alkyl morpholines have been tested in vitro on the cycloeucalenol-obtusifoliol isomerase, a microsomal enzyme involved in higher plant sterol biosynthesis. The results showed that N-substituted morpholines inhibit powerfully the enzyme (I50 = 0.4 μM for fenpropimorph). The following important molecular parameters of the inhibition could be determined: (i) the inhibitory capacity was probably related to the presence of a positive charge on the nitrogen atom, (ii) the length of the alkyl group was critical, with a maximum activity for n = 13 carbons in the case of a linear hydrocarbon chain, (iii) the presence of bulky substituents at the proximity of the nitrogen atom led to a strong decrease of the inhibitory power, (iv) in the fenpropimorph series where a chiral center is present at C-2 of the alkyl chain, a remarkable enantiomeric selectivity of the inhibition was observed, (v) the N-oxide derivative of fenpropimorph was shown to be as active as the parent compound. The N-alkyl morpholines have been also assayed on suspension cultures of bramble cells and led to a strong accumulation of 9β, 19-cyclopropyl- and Δ8-sterols. This result confirmed that the cycloeucalenol-obtusifoliol isomerase was a major target of the N-substituted morpholines and suggested that the Δ8 → Δ7-sterol isomerase was also a target for these chemicals. The molecular parameters implied in the in vivo accumulation of 9β, 19-cyclopropyl sterols were very similar to those resulting from the in vitro study. The chemical structure-inhibitory activity relationship of N-alkyl morpholines was discussed with respect to their fungicidal activity which has been described in a previous study [E. H. Pommer, Pestic. Sci. 15, 285 (1984)]. The comparison revealed that the better the inhibitory capacity on the cycloeucalenol-obtusifoliol isomerase was, the higher was the fungicidal activity in vivo. 相似文献
9.
2H-1,2,4-噻二唑并[2,3-a]嘧啶衍生物的合成及除草活性研究(Ⅱ) 总被引：1，自引：0，他引：1
取代苯氧乙酸及其衍生物、酰基硫脲[1]和2H-1,2,4-噻二唑并嘧啶类化合物[2]都是具有很好生物活性的母体结构。前文[3]曾报道了2H-1,2,4-噻二唑并[2,3-a]嘧啶的苯甲酰亚胺衍生物的合成及除草活性测定。为了寻找高效、高选择性的新型除草剂,本文以2-氯苯氧乙酰异硫氰酸酯1为创制源合成了未见文献报道的4个2和4个3。化合物2和3的结构经元素分析、IR和1HNMR确证。合成路线如下:OCH2CNCSOCl NNH2NXZY丆lOCH2CNHOCSNHNNXZY 1 2Br2NNYZXNSOCH2CNOCl32/3abcdXCH… 相似文献
10.
《Pesticide biochemistry and physiology》1986,26(3):275-283
The quantitative relationship between the structure of 46 O-aryl O-ethyl N-isopropylphosphoramidothioates and their herbicidal activity on the barnyard grass, Echinochloa cruss-galli, was analyzed using physicochemical parameters of the aryl substituents and regression analysis. We found that the hydrophobicity of the whole molecule and the position-specific steric and hydrophobic effects of substituents are important to the activity. 相似文献
11.
《Pesticide biochemistry and physiology》1986,25(2):163-168
A series of carboxin-like compounds, the N-methylpyrazole carboxanilides and their mono- and dimethyl derivatives have been assayed as inhibitors of succinate dehydrogenase enzyme complexes (SDCs) isolated from Ustilago maydis, Rhizoctonia solani, Gaeumanomyces graminis, and Fusarium oxysporum. The pattern of inhibitory activity within the series was broadly similar for each of the fungi although minor differences indicated some structural variation between the enzyme complexes. There was a general correlation between inhibition of the SDCs isolated from R. solani and G. graminis and inhibition of mycelial growth of these same organisms which was consistent with the primary mode of action of these compounds being interference with mitochondrial electron transport. No such correlation was evident with F. oxysporum, where some of the compounds showed activity against the SDC but none had any effect on fungal growth. This suggests that if SDC inhibitory activity is the primary determinant of the anti-fungal activity of these compounds it does not necessarily determine their anti-fungal specificity: some possible explanations are offered. 相似文献
12.
《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
13.
Hyun-Joon Ha 《Pest management science》1993,37(3):289-292
Nine diethyl chloroacetylanilidomethylphosphonates and ten diethyl α-(chloroacetylanilido)benzylphosphonates were prepared by N-chloroacetylation of the corresponding diethyl anilinomethyl- and anilinobenzylphosphonates. These were tested for antifungal activity against six phytopathogenic fungi. Most of the compounds showed moderate protective properties. No significant difference in activity was observed for compounds with an extra aryl ring substituent on the methylene group of the backbone. Compounds with electron-withdrawing substituents, especially chlorine, on the aniline site (R1) showed higher fungicidal activity than the other compounds with electron-donating groups as substituents. 相似文献
14.
Riaz Hasan Keiichiro Nishimura Yoshiaki Nakagawa Norio Kurihara Tamio Ueno 《Pest management science》1996,46(3):221-225
N-Arylcarbamoylpyrazolines with various substituents at the para position of the carbamoyl benzene ring inhibited ATP-dependent Ca2+-uptake in synaptosomes prepared from the rat brain. The activity of these compounds was evaluated as log(1/I50), the reciprocal logarithm of half inhibitory concentration, I50 (m ), from the concentration–response curve for the inhibition of Ca2+-uptake. Among the compounds tested, methyl 3-(4-chlorophenyl)-4-methyl-1-[N-(4-trifluoromethylphenyl)carbamoyl]-2-pyrazoline-4-carboxylate was the most potent, the I50 value of which as 9·12×10−7 m . Variations in the activity in terms of log(1/I50) were quantitatively analysed using a substituent parameter, showing that the higher the electron-withdrawing effect of the substituent, the higher was the activity. The substituent effects were similar to those on insecticidal activity against the Americal cockroach. The higher the inhibitory activity against Ca2+ uptake, the higher seemed to be the insecticidal activity. Methyl(4S) - 3 - (4 - chlorophenyl) - 4 - methyl - 1 - [N - (4 - chlorophenyl)carbamoyl] - 2 - pyrazoline -4-carboxylate had higher inhibitory activity against Ca2+-uptake and higher in-secticidal activity than the R-isomer, but the difference was greater in theCa2+-uptake system. 相似文献
15.
Duane R. Romer Brian L. Aldrich R. Garth Pews Richard W. Walter 《Pest management science》1995,43(4):263-266
A series of eleven 1,4-dithiino[2,3-b]quinoxaline-2,3-dicarbonitriles was prepared by reaction of 2,3-dichloroquinoxalines with disodium (2)-2,3-dimercapto-2-butenedinitrile in N,N-dimethylformamide. These products were tested for in-vitro fungicidal activity by a Minimum Inhibitory Concentration (MIC) method. Several of these compounds showed broad-spectrum fungicidal activity. The activity exhibited by these compounds was greatly dependent upon the substituents of the quinoxaline ring, with the nitro-substituted derivatives showing the highest levels of antifungal activity. None of the compounds prepared, however, showed fungicidal activity comparable to that of the commercial fungicides screened. 相似文献
16.
The elevation of rat blood β-glucuronidase caused in vivo by O,O-dialkyl O-phenyl phosphates and phosphorothioates correlated well with the electron-withdrawing tendency (σ?) of leaving group substituents indicating the importance of a phosphorylation mechanism in the enzyme release. Hydrophobic bonding of these compounds may facilitate the phosphorylation since hydrophobicity (π) of substituents also correlated with the enzyme release. SKF 525-A decreased the elevation of β-glucuronidase by parathion through the suppression of paraoxon production. Pretreatment of rats with phenobarbital or DDE resulted in lower and delayed enzyme release caused by parathion. 相似文献
17.
设计了一条新的2-烯- 1 -酮-类伊比林-20-基-取代苯甲酸酯( 6 )土震素(Territrem)B类似化合物的合成方法。以甲磺化伊比林醛( 2 )为原料,经脱甲磺酸生成2-烯类伊比林-13-醛( 3 ),化合物 3 经溴代丁二酰亚胺(NBS)光照溴化一步法生成中间产物 4,4 不经分离直接与酚反应生成化合物 5,5 再经一步法水解氧化制得目标产物 6 。该方法不仅提高了 6 的收率(提高5%~30%),还合成了5个新化合物 3和5b~5e 。生物活性测试表明,在10-4 mol/L条件下,只有化合物 6a 对乙酰胆碱酯酶(AChE)显示出17%的抑制活性。 相似文献
18.
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
19.
《Pesticide biochemistry and physiology》1986,26(3):253-262
Twenty-one diazepam- and chlordimeform (CDM)-related compounds were synthesized by mimicking some parts of the 1,4-benzodiazepine tranquilizing drugs, and were tested for their insecticidal activity against the German cockroach. Some of these compounds showed knockdown effects and some were insecticidal. Against the German cockroach the most toxic CDM analog was N-propargyl CDM (compound 6), and that with a potent knockdown potency was compound 13 which has a structural resemblance to diazepam. Ligand-receptor binding assay was carried out, using [3H]diazepam as a ligand to examine the relation between CDM-related compounds and the 1,4-benzodiazepines. The [3H]diazepam binding to a specific site in the American cockroach brain was inhibited by the insecticidal compounds. Among these compounds a correlation exists between their inhibitory potency on specific [3H]diazepam binding and their insecticidal activity, suggesting a possible significance of such an interaction with the diazepam binding site for the toxicity of these compounds against cockroaches. 相似文献