Determination of individual esters of 2, 4-D and 2, 4, 5-T in commercial crops

A rapid gas chromatographic method for the determination of the individual esters of 2, 4-D and 2, 4, 5-T in tomato plants and other commercial crops is described. Several suitable esters can be determined at one time. Separation is by steam distillation into a hexane trap followed by clean-up on a column of “Florisil”. Using a sample of plant material (100 g), 1 μg of each of the esters in the mixture can be determined with recoveries of 72–96% for 2, 4-D esters and 66–84% for 2, 4, 5-T esters.     

苯甲醛类、苯甲酸类和苯甲醛缩氨基硫脲类昆虫酚氧化酶抑制剂的2D-QSAR研究

采用Hansch-Fujita的定量构效关系方法,以电性参数(Hammett σ)、疏水性参数(clogP)、立体效应参数(MR)、氢键受体和供体等物理化学参数作为变量,对苯甲醛衍生物、苯甲酸衍生物和苯甲醛缩氨基硫脲衍生物进行了构效关系研究。结果表明,苯甲酸衍生物和苯甲醛缩氨基硫脲衍生物的结构与活性的关系非常相似。在此三类化合物中,氢键受体、立体效应(MR)参数和疏水效应(clogP)参数是影响化合物抑制活性的最主要因子。     

Cover Image,Volume 74, Issue 2

The cover image, by Chenxi Wu et al., is based on the Research Article Limited fitness costs of herbicide‐resistance traits in Amaranthus tuberculatus facilitate resistance evolution, DOI: 10.1002/ps.4706 . Photo Credit: Chenxi Wu.

     

Cover Image,Volume 76, Issue 2

The cover image of an adult deer tick, Oxodes scapularis, is by Scott Bauer, USDA Agricultural Research Service, Image Number K8002–3.

     

Cover Image,Volume 73, Issue 2

The cover image, by Eugênio E. Oliveira et al., is based on the Research Article Pyrethroid resistance is associated with a kdr‐type mutation (L1014F) in the potato tuber moth Tecia solanivora, DOI: 10.1002/ps.4414 . Photo Credit: Edison Torrado‐Leon.

     

Cover Image,Volume 75, Issue 2

The front cover image is based on the Spotlight Discovery of highly insecticidal synthetic spinosyn mimics ‐ CAMD enabled de novo design simplifying a complex natural product by Thomas C Sparks et al., DOI: 10.1002/ps.5217 .

     

Degradation of the insecticide SD 8280, 2-chloro-1-(2, 4-dichlorophenyl)vinyl dimethyl phosphate,in soils

The degradation of the insecticide SD 8280 [2-chloro-1-(2,4-dichlorophenyl)vinyl dimethyl phosphate] in soil has been examined under laboratory conditions using two soils from rice-growing areas in Japan and one UK soil. In all soils SD 8280 underwent degradation to 1-(2,4-dichlorophenyl)ethanol, 2,4-dichlorobenzoic acid, 2-chloro-1-(2,4-dichlorophenyl)vinyl methyl hydrogen phosphate and 2′,4′-dichloro-acetophenone. These degradation products were present in the soils as free (extractable) compounds and as bound forms and soil binding occurred most extensively with 2,4-dichlorobenzoic acid. Polar products were also formed and these appeared to be in part the result of complexing of degradation products with the soil organic matter. The effect on the degradation of the insecticide of varying the moisture content of one soil was also examined. In soil incubated at 11, 17, 30 and 62% moisture the recovery of SD 8280 after 60 days was 71.0, 12.3, 9.0 and 11.3%, respectively. Although the rate of degradation varied, the same degradation products were detected in all samples.     

茉莉酸对PR-1、PR-2、PR-5和Ta-JA2基因 表达以及小麦白粉病抗性的诱导

 为了探索小麦抗白粉病分子机理,明确茉莉酸对小麦白粉病抗性的诱导作用、对植物抗病性标志基因PR-1、PR-2、PR-5和本实验室克隆的1个新基因Ta-JA2的激活作用,以及抗病性变化与基因表达变化之间的相关性,本研究以感白粉病的小麦品种“中国春”、“濮麦9号” 和“周麦18”为材料,用茉莉酸甲酯（methyl jasmonate,MeJA）喷洒小麦幼苗叶片进行诱导,通过离体叶段培养法接种白粉菌（Blumeria graminis f. sp. tritici,Bgt）进行抗性鉴定;用实时定量PCR技术检测小麦叶片中PR-1、PR-2、PR-5和Ta-JA2基因的表达变化。结果表明MeJA处理可以显著提高“中国春”、“濮麦9号”和“周麦18”对白粉菌的抗病水平。茉莉酸处理显著激活了PR-1、PR-2、PR-5和Ta-JA2的转录。茉莉酸诱导的抗病性提高与抗病标志基因PR-1、PR-2、PR-5及Ta-JA2的表达增强呈正相关。植物激素茉莉酸是小麦抗白粉病反应的信号分子。     

Inhibition of ergosterol biosynthesis in Ustilago maydis by the fungicide 1-[2-(2, 4-dichlorophenyl)-4-ethyl-1, 3-dioxolan-2-ylmethyl]-1H-1, 2, 4-triazole

Inhibition of sporidial multiplication in cultures of Ustilago maydis by 1-[2-(2, 4-dichlorophenyl)-4-ethyl-1, 3-dioxolan-2-ylmethyl]-1H-1, 2, 4-triazole^a (CGA-64251), at concentrations of 0.1, 1.0 and 5.0 μg ml^?1, increased from about 15% during the first 4 h, to 58–70% during the subsequent 4 to 12-h period. Sporidia became swollen and highly branched in the presence of the fungicide. Total lipid content as a percentage of the dry weight was not affected after exposure of the sporidia to the fungicide at 0.1 or 5 μg ml^?1 for 4 h, but synthesis of ergosterol and other demethyl-sterols was inhibited by 87–92%. Large quantities of methyl-sterol precursors of ergosterol and of free fatty acids accumulated in the treated sporidia. Fungitoxicity of CGA-64251 is attributed to inhibition of ergosterol biosynthesis at the stage of sterol C-14 demethylation.     

CO_2,CH_4 and N_2O flux changes in degraded grassland soil of Inner Mongolia,China

The main purpose of this study was to explore the dynamic changes of greenhouse gas(GHG)from grasslands under different degradation levels during the growing seasons of Inner Mongolia, China.Grassland degradation is associated with the dynamics of GHG fluxes, e.g., CO_2, CH_4 and N_2O fluxes. As one of the global ecological environmental problems, grassland degradation has changed the vegetation productivity as well as the accumulation and decomposition rates of soil organic matter and thus will influence the carbon and nitrogen cycles of ecosystems, which will affect the GHG fluxes between grassland ecosystems and the atmosphere. Therefore, it is necessary to explore how the exchanges of CO_2,CH_4 and N_2O fluxes between soil and atmosphere are influenced by the grassland degradation. We measured the fluxes of CO_2, CH_4 and N_2O in lightly degraded, moderately degraded and severely degraded grasslands in Inner Mongolia of China during the growing seasons from July to September in 2013 and 2014. The typical semi-arid grassland of Inner Mongolia plays a role as the source of atmospheric CO_2 and N_2O and the sink for CH_4. Compared with CO_2 fluxes, N_2O and CH_4 fluxes were relatively low. The exchange of CO_2, N_2O and CH_4 fluxes between the grassland soil and the atmosphere may exclusively depend on the net exchange rate of CO_2 in semi-arid grasslands. The greenhouse gases showed a clear seasonal pattern, with the CO_2 fluxes of –33.63–386.36 mg/(m·h), CH_4 uptake fluxes of 0.113–0.023 mg/(m·h) and N_2O fluxes of –1.68–19.90 μg/(m·h). Grassland degradation significantly influenced CH_4 uptake but had no significant influence on CO_2 and N_2O emissions. Soil moisture and temperature were positively correlated with CO_2 emissions but had no significant effect on N_2O fluxes.Soil moisture may be the primary driving factor for CH_4 uptake. The research results can be in help to better understand the impact of grassland degradation on the ecological environment.     

S-Ethyl dipropylthiocarbamate, N,N-Diallyl-2-chloroacetamide,and 2-chloroallyl diethyldithiocarbamate influence on sulfhydryl-dependent sucrose accumulation

l-[U-¹⁴C]sucrose accumulation by phloem sieve tube members (PSTM) of wheat (Triticum aestivum L. ‘Holley’) and sorghum (Sorghum bicolor L. ‘G522 DR’) was inhibited by the nonpermeant sulfhydryl inhibitor p-chloromercuribenzenesulfonic acid (PCMBS), and this inhibition was reversed by the permeant sulfhydryl protectants dithiothreitol (DTT) and dithioerythritol (DTE). S-Ethyl dipropylthiocarbamate (EPTC) (≤0.1 mM) did not inhibit [¹⁴C]sucrose accumulation by wheat or sorghum PSTM. N-N-Diallyl-2-chloroacetamide (CDAA) (1 mM) inhibited [¹⁴C]sucrose accumulation by sorghum but not by wheat PSTM. The inhibition of [¹⁴C]sucrose accumulation in sorghum PSTM by the membrane permeant CDAA was reversed by DTT. Sorghum growth was inhibited by <1 μM CDAA. Membrane permeant 2-chloroallyl diethyldithiocarbamate (CDEC) (0.1 mM) inhibited [¹⁴C]sucrose accumulation by PSTM of sorghum but not wheat. The inhibition of sucrose accumulation in sorghum PSTM by 0.1 mM CDEC was reversed by DDT.     

The basis of selectivity of 4-(2, 6-dichlorobenzyloxymethyl)-4-ethyl-2, 2-dimethyl-1, 3-dioxolan (WL 29, 226), a new pre-emergence herbicide for use in cereals

A series of pot experiments were undertaken to assess the selectivity of the pre-emergence herbicide 4-(2, 6-dichlorobenzyloxymethyl)-4-ethyl-2, 2, -dimethyl-1, 3-dioxolan (WL 29,226) against a number of annual weeds in wheat. When applied at dose rates of 0.5–2 kg/ha it gave good control of a number of annual monocotyledonous weeds, including Alopecurus myosuroides (blackgrass), without any adverse effects on the crop. WL 29,226 is relatively immobile in soil, remaining at the soil surface and thus favouring uptake via the emerging shoot. Since WL 29,226 is transported predominantly via the xylem, to reach its site of action in the regions of cell division, and hence to be effective, the compound has to penetrate the shoot either at or below the stem apex. The roots are inhibited only when these come into direct contact with the compound. Selectivity of the herbicide is dependent upon the relative anatomical positions of the stem apices of the weeds and the crop with respect to the soil surface. Mesocotyl elongation in many of the weed species was such that the meristematic tissue was raised to the soil surface and into contact with the compound during the emergence of the shoot. In contrast, the stem apex of wheat remained some distance below the soil surface until considerably later, by which time the leaf sheaths offered protection to the meristematic tissue from direct contact with the herbicide. Selectivity is further enhanced in the field as a result of both the depth of planting for wheat and the tendency of many annual weed species to germinate more readily when near the soil surface. Tolerance of the wheat is lost where it germinates in direct contact with the herbicide, due to the lack of any biochemical selectivity. Under field conditions WL 29,226 gives good control of many dicotyledonous species. In pot experiments, however, these exhibit some tolerance to the compound. Radio-tracer studies indicate that the tolerance shown by the shoots of these plants is due to limited transport of the herbicide from the shoot to its site of action at the apex. This suggests that control of broad-leaved weeds occurs predominantly through an inhibition of root growth. However, in species such as sugar-beet, soyabean and cotton a rapid rate of root elongation confers increased tolerance to the compound. Availability of WL 29,226 for uptake by young seedlings is favoured by soil moisture. Low temperatures further improve performance by reducing the rate of shoot emergence and hence prolonging contact with the compound at the most sensitive stage of growth. After emergence uptake of the compound via the shoot becomes a less efficient mode of entry.     

N-(2,4,5-三氯苯基)-2-氧代环己烷基磺酰胺对灰葡萄孢的抑制作用

研究了新型环烷基磺酰胺类化合物N-(2,4,5-三氯苯基)-2-氧代环己烷基磺酰胺(简称化合物108)对灰葡萄孢菌丝生长、孢子形成和萌发以及菌核产生等不同生育阶段的抑制作用及其对菌丝致病力和形态结构的影响。结果表明:化合物108对灰葡萄孢菌丝生长和孢子形成及孢子萌发具有明显的抑制作用,其EC50值分别为6.90、4.70和4.11μg/mL;菌核形成受到明显抑制,当药剂质量浓度达20μg/mL时,无菌核产生。经化合物108处理后的灰葡萄孢菌丝致病力下降,40μg/mL处理的菌丝致病力显著低于对照。超微结构观察结果表明,化合物108能导致灰葡萄孢菌丝萎缩、塌陷和变形,菌体细胞壁增厚、皱缩及分层。     

Modulation of Mouse P450 Isoforms CYP1A2, CYP2B10, CYP2E1, and CYP3A by the Environmental Chemicals Mirex, 2,2-Bis(p-chlorophenyl)-1,1-dichloroethylene, Vinclozolin, and Flutamide

Several environmental chemicals are disruptive to the reproductive and endocrine systems of many species, including humans. Mechanisms for endocrine disruption are presently under scrutiny. Xenobiotic inducible mammalian cytochrome P450 (CYP) enzymes metabolize a variety of substrates including environmental chemicals, pesticides, and drugs. The metabolism, and thus the effect, of endogenous chemicals including steroid hormones, vitamins, etc. that are transformed by CYP enzymes can be influenced by environmental exposure to CYP-inducing chemicals. This study demonstrated that structurally diverse environmental chemicals including mirex, 2,2-Bis(p-chlorophenyl)-1,1-dichloroethylene (DDE), vinclozolin, and flutamide are capable of inducing several mouse liver CYP isozymes. As demonstrated by Western blotting, mirex induced CYP1A2, 2B10, 2E1, and 3A and vinclozolin induced 1A2 and 2B10. The only isoforms significantly induced by DDE and flutamide were 3A and 1A2, respectively. Since some of these isoforms are known to be involved in metabolism of endogenous hormones, we also studied the effects of these CYP inducers on testosterone metabolism and seminal vesicle weights. Mirex and DDE treatments had profound effects on the metabolism of testosterone, resulting in 2.5- to 3-fold more hydroxylated products than controls. Lesser, but significant, increases in specific metabolites of testosterone were also observed following treatment with vinclozolin and flutamide. Seminal vesicle weights were lower for all treatment groups except DDE. Results of this study demonstrate that, due to their CYP-inducing potential, these chemicals may significantly impact testosterone metabolism and this may be a contributing factor in their antiandrogenic effects.     

Quantitative structure-activity study of insecticidal 2-methoxy-5-(substituted-phenyl)-1, 3, 2-oxazaphospholidine 2-sulfides against Musca domestica L. by topical application

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.     

Methyl benzimidazol-2-ylcarbamate,the fungitoxic principle of thiophanate-methyl

A correlation was found between the formation of benzimidazol-2-ylcarbamate esters from the thiophanate fungicides [thiophanate, thiophanate-methyl and 2-(3-methoxycarbonylthioureido)aniline] and the fungitoxie activity of these fungicides. Fungitoxic activity of the thiophanates is increased by ageing in aqueous media while fungitoxicity as well as conversion rate decrease at lower pH. It is concluded that it is not the thiophanates themselves but the corresponding benzimidazol-2-ylcarbamate esters that are responsible for the fungitoxic effect. Hence thiophanate-methyl, like benomyl, is a precursor of the fungitoxic agent methyl benzimidazol-2-ylcarbamate (MBC). Indications were obtained that fungal metabolic activity can increase the rate of conversion of thiophanate-methyl into MBC.     

稻瘟病流行的模拟模型SIMBLAST-2

 稻瘟病(Pyricularia oryzae Cav.)流行的模拟模型SIMBLAST-2主要由5个子模型组成:(1)水稻生长的子模型GROWTH,(2)稻瘟病日传染率的子模型INFECTION,(3)潜育期和显症率的子模型INCUBATION,(4)病斑扩展的子模型LESION,(5)空中孢子捕获的子模型SPORE。
SIMBLAST-2经两年的检验和模拟试验,认为其结构合理、实用性强。
最后讨论了该模型的不足之处和改进途径。     

Synthesis and insecticidal activity of new 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives

BACKGROUND: A series of 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized as potential new agents to control insects. Their structures were confirmed on the basis of IR, NMR and MS analyses. RESULTS: Ten 3-benzylfuran-2-ylN,N,N',N'-tetraethyl derivatives were prepared from the compound furan-2-yl N' (N,N,N',N'-tetraethyldiamidophosphate). The contact toxicity of all derivatives, at a dose of 10 microg mg(-1) insect, was evaluated against four insect species, Ascia monuste orseis Latr. (Lepidoptera: Pyralidae), Diaphania hyalinata (L.) (Lepidoptera: Pyralidae), Sitophilus zeamais Mots. (Coleoptera: Bruchidae) and Solenopsis saevissima (Smith) (Hymenoptera: Formicidae). The mortality range observed for some derivatives, such as 3-(3-methylbenzyl)furan-2-yl N,N,N',N'-tetraethyldiamidophosphate (82.5% mortality against D. hyalinata; 100% mortality against S. saevissima), was comparable with that of the commercial insecticide chlorpyrifos-methyl. The biological activity of the derivatives depended on the substitution pattern of the benzylic ring. Furan-2-yl N,N,N',N'-tetraethyldiamidophosphate, furan-2-yl N,N-diethylamidochlorophosphate and difuran-2-yl N,N-diethylamidophosphate were also evaluated, displaying, in some cases, activity comparable with that of chlorpyrifos-methyl (90%, 100% and 97.5% respectively against A. monuste orseis). Considerable activity was observed for some furan-2(5H)-ones evaluated. CONCLUSION: Ten 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized and fully characterized from a chemical point of view. The results obtained from the biological assays indicate that this class of compounds can be utilized for the design of new substances endowed with insecticidal activity.