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1.
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2.
The optically active urea compounds R- and S-1-α-methylbenzyl-3-p-tolylurea (R- and S-MBTU) have qualitatively different effects on plant physiology, especially in Gramineae plants. To elucidate the mechanisms by which S-MBTU inhibits root growth of wheat (Triticum aestivum L. var. Chinese Spring), we used PCR-based suppression subtractive hybridization (SSH) and quantitative real-time RT-PCR (qPCR) analyses. Genes related to amino acid biosynthesis, cell cycle and skeleton, protein synthesis, cell wall biosynthesis, glycolysis, signaling, DNA modification, and detoxification were enantioselectively regulated. These expression profiles suggested that the putative mode of action of S-MBTU is disruption of primary amino acid biosynthesis, especially the glutamine synthetase (GS)- and acetohydroxyacid synthase (AHAS)-enzyme systems, and disruption of cell membrane skeleton homeostasis related to a putative α-tubulin 2 (α-TUB2), a putative β-actin (ACT) and β-tubulin 1 (β-TUB1). Other genes specifically affected by S-MBTU may result in disruption of metabolic processes, leading to inhibition of root growth.  相似文献   

3.
Bromination of the dichlorovinyl group of cypermethrin yielded a new compound which is a highly potent insecticide. This dibromo adduct has four asymmetric centres and therefore can exist as a mixture of 16 stereoisomers. To establish the influence of the absolute configuration at the chiral centres on the biological activities of these isomers, each of the isomers was isolated; their insecticidal activities against larvae of Heliothis virescens, and adult Calliphora erythrocephala and Blattella germanica were then determined and compared with those of (S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate (deltamethrin NRDC 161), of fenvalerate, and of the eight stereoisomers of cyper methrin.  相似文献   

4.
Cypermethrin and cyfluthrin were applied to wheat, which was stored for 52 weeks at 25 or 35°C, and either 12 or 15% moisture content. Total residues and the proportions of the four pairs of enantiomers, cis I [(αR),(1R)-cis + (αS),(1S)-cis], cis II [(αR),(1S)-cis + (αS),(1R)-cis], trans III [(αR),(1R)-trans + (αS),(1S)-trans], and trans IV [(αR),(1S)-trans + (αS),(1R)-trans] for each pyrethroid were determined at five intervals during storage. For all storage conditions, the cis I isomers were the most stable, and the trans IV isomers were the least stable. Calculated half-lives (weeks) for the pairs of enantiomers at 25°C (12% moisture) and 35°C (15% moisture) were: cypermethrin, cis I, 252, 62 and trans IV 66, 27; cyfluthrin, cis I, 114, 52 and trans IV 42, 23. The results suggested that one of the enantiomers of the cypermethrin trans IV pair was degraded faster than the other.  相似文献   

5.
Inhibition of the Δ8-Δ7 sterol isomerase in the ergosterol biosynthesis pathway is known to lead to fungistatic or even fungicidal effects. Our approach to the rational design of new putative inhibitors of the enzyme was based on the assumed mechanism of the enzymic transformation and in particular on the structure of the unstable carbocationic intermediate, i.e. the ‘transition-state-analogue’ principle. The synthesis and the biological properties of 1(R)-(2,6-cis- dimethylmorpholino)-3(S)-(p-tert-butylphenyl)cyclopentane, a representative of a novel, potent class of rationally designed fungicides, as well as the synthesis and biological activities of several other related compounds are described and discussed.  相似文献   

6.
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   

7.
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   

8.
Preparation of 3-phenoxybenzyl chrysanthemates and their dihalovinyl analogues substituted with a cyano group at the 2-, 6-, (R)-α-, or (S)-α- positions is described. The (R)- and (S)- isomers of α-cyano-3-phenoxybenzyl esters of 2,2-difluoro-, -dichloro-, and -dibromo-vinyl analogues of cis- and trans- chrysanthemic acid are separated chromatographically, as are the separate pairs of enantiomers of fenvalerate, (RS)-α- cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate. An optically active ester of α-cyano-3-phenoxybenzyl alcohol (obtained using D -oxynitrilase) with 2,2,3,3-tetramethylcyclopropanecarboxylic acid is synthesised.  相似文献   

9.
The insecticidal activities to Musca domestica L. and Phaedon cochleariae Fab. of a series of 3-phenoxybenzyl pyrethroid esters with a cyano substituent at the 2-, 6-. (R)-α-, or (S)-α-position are compared with those of the unsubstituted analogues. Only an (S)-α-substituent enhances activity; others diminish or almost eliminate it. (RS)-α-mixtures are generally less active than would be predicted from the potencies of their separate constituents.  相似文献   

10.
Various isomeric mixtures of pyrethroids were examined in topical application tests against houseflies, Musca domestica. On the basis of the activities of the separate isomers of 5-benzyl-3-furylmethyl (±)-cis,trans-chrysanthemate, it was shown that when combined in pairs to give the (±)-trans or (±)-cis or (+)-cis,trans mixtures the observed mortalities did not differ from those expected by simple additive action calculated by the harmonic mean. In contrast the (±)-cis,trans mixture showed considerable antagonism with a mortality only 60% of that expected. Similar evaluations using the separate and combined isomers of bioallethrin [(R,S)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (allethronyl) ( + )-trans-[(1R,3R)-chrysanthemate] and the corresponding (+)-cis-(1R,3S)-chrysanthemate indicate antagonism calculated to be correlated with the content of the (R)-isomer of the alcoholic moiety. Hence the activity of the most active isomer of the “allethrin” series, (S)-3-allyl-2-methyl-4-oxocyclopent-2-enyl ( + )-trans-(1R,3R)-chrysanthemate, (S)-bioallethrin, is not fully realised unless it is present in pure form and a substantial part of the value of bioresmethrin (5-benzyl-3-furylmethyl ( + )-trans-chrysanthemate] as a killing agent is lost when the racemic form is used. In racemic mixtures there is mutual antagonism between pairs of isomers so that considerable masking of activity occurs.  相似文献   

11.
The synthesis of (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid by dehydrohalogenation of 4,6,6,6-tetrahalohexanoates has been modified to produce stereo-selectively the cis-isomer. A new stereospecific synthesis of cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acids using a bicyclic lactone and its extension to the preparation of the optically active (1R)-cis acid are described.  相似文献   

12.
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   

13.
Laboratory experiments were conducted to analyze the iron (Fe) tolerance of paddy weeds and rice varieties (Oryza sativa) for germination and root elongation. Under a waterlogged soil condition, the Fe(II) content in a soil solution increased with an increase in the ratio of rice straw to the soil. In the presence of 0.9% (w/w) straw to soil, which corresponds approximately to 8 t of straw applied to an area of 1 ha × 10 cm depth in the field, ～80 mg L?1 of Fe(II) was produced in the soil solution. Based on this result, the seeds of rice and the weeds were incubated in a solution with <100 mg L?1 of Fe(II). The presence of 100 mg L?1 of Fe(II) suppressed the germination of Echinochloa crus‐galli var. crus‐galli, Cyperus serotinus, Cyperus difformis, and Monochoria korsakowii. However, it had no effect on the germination of Echinochloa oryzicola, Schoenoplectus juncoides (= Scirpus juncoides var. ohwianus), and Monochoria vaginalis. This level of Fe tolerance was the same as that of rice. These findings suggest that E. oryzicola, S. juncoides, and M. vaginalis can grow under more severe conditions than E. crus‐galli, C. serotinus, C. difformis, and M. korsakowii. In relation to seminal root elongation, the order of tolerance of Fe toxicity was O. sativa cv. Dunghan Shali > O. sativa cv. Hoshinoyume > E. oryzicola > M. vaginalis > S. juncoides. Thus, the results show that the tolerance of rice is greater than that of E. oryzicola, which had a comparatively strong tolerance among the weeds examined, and also that there are differences in tolerance among the rice varieties. These findings suggest that the difference in Fe tolerance is involved in weed control systems when organic materials are applied. If this difference is an important factor in the weed control system, Fe‐tolerant rice varieties, like cv. D. Shali, could facilitate weed control systems due to their higher Fe tolerance ability.  相似文献   

14.
The three commercial synthetic pyrethroids containing a carbon–carbon triple bond, α-ethynyl-2-methylpent-2-enyl (1R)-trans-chrysanthemate, (S)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1R)-trans,cis-chrysanthemate and [2,5-dioxo-3-(2-propynyl)-1-imidazolidinyl]methyl (1R)-trans-chrysanthemate are reviewed with emphasis on their inventive histories. Their chemistry and efficacy are described briefly. The relationship between stereochemistry and the biological activity is also discussed. © 1998 SCI.  相似文献   

15.
The baseline toxicity of 22 acetolactate synthase (ALS)-inhibiting herbicides and the cross-resistance patterns of chlorsulfuron- and imazapyr-resistant (R) lines on these 22 ALS-inhibiting herbicides were investigated using the model species Arabidopsis thaliana. The 22 herbicides consisted of 18 sulfonylureas (SU), three imidazolinones (IMI) and one triazolopyrimidine (TP). The ED50 values (doses of herbicides required to reduce dry matter by 50%) of the post-emergence-treated Col and Ler susceptible (S) lines ranged from 22 to 4822 mg ha−1 and from 17 to 3143 mg ha−1 respectively. The csr1-1 chlorsulfuron-resistant line (substitution of Pro197 to Ser) conferred a high resistance to the only TP tested as well as to nine SU herbicides (R:S ratio ≥30), a low resistance to two SU herbicides (R:S≥5 and <30) and little or no resistance to the three IMI and seven other SU herbicides (R:S <5). This result contradicts the expectation that an ALS mutation selected by an SU herbicide confers high cross-resistance to other SU herbicides. We found that the efficacy of specific ALS inhibitors was different for different species and therefore could not be predicted from our results with A. thaliana; however, the cross-resistance patterns in A. thaliana were highly correlated with cross-resistance patterns in unrelated species with the same resistance mutation. These results have implications for resistance management.  相似文献   

16.
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   

17.
The application of enantioselective catalytic methods for the technical preparation of chiral agrochemicals is illustrated for three active ingredients of the acylanilide type. The key step for the technical synthesis of the herbicide (S)-metolachlor is the enantioselective hydrogenation of an imine intermediate using a novel iridium ferrocenyldiphosphine catalyst with an unprecedented high activity and 80% ee. (R)-metalaxyl and (αS,3R)-clozylacon were synthesized via the enantioselective hydrogenation of corre-sponding enamide precursors with Rh and Ru/binap catalysts with >95% and 99% enantiomeric purity, respectively. © 1998 Society of Chemical Industry  相似文献   

18.
Due to the presence of an asymmetrically substituted C atom, dimethenamid [2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide], a recently introduced N-thienyl chloroacetamide herbicide, exists as two stereoisomers (S and R) having differing herbicidal activities as demonstrated with a selection of weeds and Lemna minor. The activity of the two isomers was investigated in greater detail with the green alga Scenedesmus acutus and compared to that of alachlor [2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide]. As with alachlor, the S isomer (5 μM ) strongly inhibited algal growth and fatty acid desaturation while the R isomer had no effect. In short-term experiments (up to 5·5 h), the S isomer and alachlor (100 μM ) inhibited [14C]acetate uptake and its incorporation into fatty acids in the same manner, while the R isomer did not. Incorporation of [14C]acetate into a non-lipid fraction of the algae was strongly inhibited by alachlor and the S isomer (100 μM ) and only slightly by the R isomer. A 50% inhibition of incorporation of [14C]oleic acid into the same non-lipid fraction was attained with less than 10-7 M of the S isomer while 10-5 M of the R form of dimethenamid achieved only a 40% inhibition. The same stereospecificity of the compound on growth, fatty acid desaturation, acetate uptake and oleic acid incorporation provides strong evidence that dimethenamid may act upon a primary, specific target in lipid metabolism. Furthermore, the comparable biological activities of dimethenamid and alachlor indicate that this target is common to both N-phenyl and N-thienyl chloroacetamide herbicides. © 1997 SCI.  相似文献   

19.
(E)-5-Benzyl-3- furylmethyl (1-R),3-S)-2,2-dimethyl-3-(2,3,4,5-tetrahydro-2-oxothien-3-ylidenemethyl)cyclopropanecarboxylate or RU-15525 is a new pyrethroid. The action of this compound was tested on Musca domestica and Aedes aegypti and a very strong knockdown effect was observed in comparison with the knockdown effect of allethrin, bioallethrin and (S)-bioallethrin.  相似文献   

20.
Chinese violet (Asystasia gangetica (L.) T. Anderson) is a perennial invasive weed belonging to Acanthaceae. Leaves of this weed have been suggested to possess phytotoxic activity. However, phytotoxic substances in this weed have not yet been reported. Therefore, the present study investigated phytotoxic activity of Chinese violet extracts and phytotoxic substances. The extracts of Chinese violet leaves inhibited the root and shoot growth of cress, lettuce, alfalfa, barnyard grass, ryegrass, and timothy, where the level of inhibition increased with increasing extract concentrations. Bioassay‐guided separations of the extracts led to isolation of two phytotoxic substances, indole‐3‐carboxaldehyde and (6R,9S)‐3‐oxo‐α‐ionol. Indole‐3‐carboxaldehyde significantly inhibited the root and shoot growth of cress at concentrations ≥100 and 30 μmol L?1, respectively, and concentrations of the substance required for 50% growth inhibition were 210 and 127 μmol L?1 for cress roots and shoots, respectively. The other substance, (6R,9S)‐3‐oxo‐α‐ionol, was reported to have strongly inhibited cress roots and shoots. The present results suggest that Chinese violet contains two phytotoxic substances indole‐3‐carboxaldehyde and (6R,9S)‐3‐oxo‐α‐ionol, and those substances may play an important role in the phytotoxic activity of Chinese violet.  相似文献   

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