Effects of isoproturon on photosynthesis in susceptible and resistant biotypes of Phalaris minor and wheat

Wheat (cv. WH-147) and five biotypes of Phalaris minor Retz. (KR-1, H-4, K-2, H-2 and J-1) were treated with isoproturon in controlled environmental conditions to assess their level of resistance. Resistance of P. minor to isoproturon was found in the order of KR-1 > H-4 > K-2 > H-2 = J-1. Compared with the susceptible (S) biotype (H-2), the resistant (R) biotypes (KR-1. H-4 and K-2) of P. minor required 13.0, 4.5 and 2.7 times higher doses of isoproturon for a 50% reduction in growth (GR₅₀) and 2.4 times that of the S biotype (H-2) by wheat. The corresponding figures for KR-1, H-4, K-2 biotypes and wheat were 18, 4.1, 2.4 and 4.6 times based on dry weight reduction. The effect of isoproturon on photosynthesis was studied in vitro using five biotypes of P. minor and in viro with wheat. KR-1 (R) and H-2 (S) biotypes of P. minor. Under in vitro treatment conditions isoproturon inhibited the photosynthesis of all five P. minor biotypes, whereas in vivo the recovery was greater in the R biotype than in the wheat and the S biotype. Effects on chlorophyll fluorescence were also measured in wheat and the KR-1 (R) and H-2 (S) biotypes of P. minor. A 4-h treatment of excised leaves incubaled in isoproluron solution (0.025 and 0.05 mm concentration) resulted in a decreased fluorescence coefficient (F_v F_m ratio in which F_v= variable fluorescence (F_m - F^o): F_m= the maximum fluorescence and F_o= initial fiuorescence) in wheat (Triticum aestivum L.) and both biotypes of P. Minor. The recovery was, however, greater in the R biotype than in wheat and it was completely recovered within 24 h. No recovery was recorded in the case of the S biotype of P. minor and a greater recovery time was required for wheat than the R biotype. The higher dose required for growth inhibition in the R biotype and rapid recovery of oxygen evolution and fluorescence coeflicient under in viro conditions together with the absence of selectivity in vitro suggests that the target site was unaffected. It can be conjectured that resistance to isoproturon is most probably because of enhanced metabolism or sequestration of isoproturon, resulting in decreased target site delivery.     

Metabolism of chlorsulfuron by plants: Biological basis for selectivity of a new herbicide for cereals

A major factor responsible for the selectivity of chlorsulfuron [2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide] (formerly DPX-4189), as a postemergence herbicide for small grains is the ability of the crop plants to metabolize the herbicide. Chlorsulfuron is the active ingredient in Du Pont “Glean” weed killer. Tolerant plants such as wheat, oats, and barley rapidly metabolize chlorsulfuron to a polar, inactive product. This metabolite has been characterized as the O-glycoside of chlorsulfuron in which the phenyl ring has undergone hydroxylation followed by conjugation with a carbohydrate moiety. Sensitive broadleaf plants show little or no metabolism of chlorsulfuron.     

Transformations of 4-chloro-o-toluidine in soil: Generation of coupling products by one-electron oxidation

Four coupling products formed by one-electron oxidation of 4-chloro-o-toluidine were isolated from soil samples after 90 days of incubation with [¹⁴C]chlordimeform (200 mg/kg). The metabolic compounds were identified as 4,4′-dichloro-2,2′-dimethyl-azobenzene, 4-chloro-6-nitro-o-toluidine, N-(4-chloro-o-tolyl)-2-methyl-p-benzoquin-one monoimine and 2-(4-chloro-o-toluidino)-N-(4-chloro-o-tolyl)-6-methyl-p-benzo-quinone monoimine, respectively. Mechanisms of formation and possible significance of these substances as indicators for metabolic pathways to mineralisation of aniline derivatives are discussed. The chlordimeform soil concentrations (70–100 mg/kg) necessary for the formation of the azobenzene and the benzoquinone monoimines are at least 10 times higher than those occurring after actual field application.     

氟氯吡啶酯与双氟磺草胺复配的田间除草效果及其对作物安全性评价

氟氯吡啶酯属于人工合成激素类除草剂全新类别,是芳香基吡啶甲酸类家族的第1位成员,为明确其作用特点、除草活性、与双氟磺草胺复配后的除草效果以及对小麦和后茬作物的安全性,连续2年分别于小麦越冬前和返青初期施药,在冬小麦田进行了田间试验。结果表明,7.5 g/L氟氯吡啶酯EC在7.5 g/hm2用量下,对猪殃殃、播娘蒿防效较好,2次施药末次调查对猪殃殃防效为96.5%和100%,对播娘蒿防效为94.1%和81.1%;对麦瓶草防效较差,末次调查为57.1%和27.9%,对麦家公无效。复配制剂20%氟氯吡啶酯·双氟磺草胺WG在15、20、30 g/hm2用量下,对猪殃殃、播娘蒿、麦瓶草防效均较好,株防效为90.5%~100%,对麦家公防效略差,越冬前施药株防效为78.8%~98.6%,返青初期施药株防效为20.9%~82.5%;末次调查时杂草总鲜重防效为90.1%~98.2%,2次施药结果差异不显著。小麦田喷施该复配制剂15~45 g/hm2剂量,对小麦安全,未见任何药害症状;且对后茬作物玉米、大豆、花生、棉花、谷子均安全。     

Studies on the mechanism of selectivity of the auxin herbicide quinmerac

Investigations were conducted to elucidate the mechanism of selectivity of the auxin herbicide, quinmerac, in cleavers (Galium aparine) and the tolerant crops sugarbeet (Beta vulgaris), oilseed rape (Brassica napus) and wheat (Triticum aestivum). After root treatment with the herbicide, the selectivity has been quantified as approximately 400-fold between oilseed rape and Galium and 1000-fold between sugarbeet or wheat and the weed species. When 1 and 10 μM [¹⁴C]quinmerac were applied for 4 h, no significant differences between root absorption and translocation of ¹⁴C by Galium and the crop species were found. After 16 h, metabolism of [¹⁴C]quinmerac to the biologically inactive hydroxymethyl and dicarboxylic acid derivatives was more rapid in wheat and sugarbeet than in Galium. In oilseed rape, a lower rate of herbicide metabolism was observed. In Galium, accumulations of abscisic acid (ABA), triggered by quinmerac-stimulated ethylene biosynthesis, were found to cause the herbicidal growth inhibition which develops during 24 h of application. Within 1 h of treatment, quinmerac stimulated 1-aminocyclopropane-1-carboxylic acid (ACC) synthase activity and ACC concentration specifically in Galium shoot tissue. During the next 4 h, ACC synthase activity was increased up to 50-fold, relative to the control. Within 3 h of exposure to quinmerac, increased ethylene formation followed by higher ABA levels was detected. In sugarbeet, oilseed rape and wheat, quinmerac did not stimulate ACC synthase activity and ACC and ABA levels. It is suggested that (i) the selectivity of quinmerac is primarily based upon the lower sensitivity to the herbicide of the tissue/target in the crop species, (ii) the induction process of the ACC synthase activity in the shoot tissue is the primary target of herbicidal interference. In wheat and sugarbeet, tolerance to quinmerac is additionally increased by a more rapid metabolism. © 1998 SCI.     

Synthesis of benzylaminopyrimidines and their fungicidal activities against wheat brown rust and barley powdery mildew

Members of a new class of fungicide containing benzylaminopyrimidine as a core structure were synthesized and their fungicidal potencies against wheat brown rust, Puccinia recondita, and barley powdery mildew, Erysiphe graminis, were assessed. Among these fungicides, N-(fluoroalkoxy or fluorophenoxybenzyl)-4-pyrimidinamines showed notable preventive activities. The potency of the new pyrimidines was increased when a difluoromethoxy or tetrafluorophenoxy group was introduced at the 4- or 3-position of the phenyl moiety and a methyl or ethyl group was introduced at the benzyl position. Structure–activity relationships are discussed. © 1998 Society of Chemical Industry     

Evaluation of novel sulfonylurea derivatives with a fused heterocyclic moiety as paddy herbicides that control sulfonylurea‐resistant weeds

Herbicidal activity and acetolactate synthase (ALS) inhibition of sulfonylurea derivatives with a fused heterocyclic moiety bonded to a sulfonyl group were investigated. Some compounds that had an imidazo[1,2‐b]pyridazine moiety substituted at the 2‐position by chlorine or methyl controlled sulfonylurea‐resistant (SU‐R) weeds and showed inhibitory activity to ALS prepared from SU‐R Schoenoplectus juncoides shoot. There was a correlation between in vitro and whole‐plant herbicidal activity of the compounds mentioned above against SU‐R Schoenoplectus juncoides. Among them 1‐(2‐chloro‐6‐propylimidazo[1,2‐b]pyridazin‐3‐ylsulfonyl)‐3‐(4,6‐dimethoxypyrimidin‐2‐yl)urea, propyrisulfuron, was selected for further evaluation. Propyrisulfuron effectively controlled paddy weeds at doses of 70 and 140 g a.i. ha^?1 with good rice selectivity in a field trial.     

Selectivity of SMY 1500 (4-amino-6-tert-butyl-3-ethylthio-l,2,4,triazin-5(4H)-one) in Triticum durum

Susceptibility to SMY 1500 (4-amino-6-tert-butyl-3-ethylthio-1.2.4-triazin-5(4H)-one) was studied in durum wheat (Triticum durum Desf.) cultivars in growth-chamber assays. Weight reduction, photosynthesis inhibition and herbicide levels were determined at various times after a 24-h herbicide treatment in two cultivars of durum wheat, one cultivar of spring wheat (Triticum aestivum L). and in the weed Bromus diandrus (Roth). Measurements of weight reduction distinguished between plants tolerant and plants susceptible to SMY 1500. Tolerant cultivars showed a lower herbicide content and photosynthesis inhibition than susceptible plants after the 24-h treatment. Thereafter, herbicide levels and photosystem II inhibition decreased faster in tolerant plants. Comparison with previous work showed that plants tolerated doses of SMY 1500 about four times higher than of its analogue, metribuzin. Herbicide content in leaves just after treatment, and rate of detoxification may explain the selectivity of SMY 1500 in these cereals.     

Resistance to Wheat streak mosaic virus– a survey of resources and development of molecular markers

Wheat streak mosaic virus (WSMV) has been newly documented in Australia. The vulnerability of contemporary Australian elite wheat germplasm prompted a survey for effective resistance against an Australian isolate, WSMV‐ACT. This study confirms the effectiveness of previously reported sources of resistance and shows that new sources of resistance also confer protection. The resistance derived from Thinopyrum intermedium (Wsm1) as a 4D translocation and a new 4A translocation, and two bread wheat resistances, Wsm2 and the new source c2652, were effective against WSMV‐ACT in glasshouse experiments. Wsm1 was effective at lower temperatures but ineffective above 20°C, a temperature sensitivity shared with many of the derivatives of Wsm2 except for one new selection which was effective at 26°C. True wheats c2652 and Wsm2 selection CA745, and amphiploids Zhong1, Zhong2, Zhong4, Zhong5, TAF46, Summer1, Ot38 and OK7211542 were uniformly resistant at 20, 25 and 28°C. New sources of resistance were identified in a Th. scirpeum‐wheat amphiploid, B84‐994, and in chromosome addition lines Z2, Z6 and TAi27, derived from wheat‐Th. intermedium partial amphiploids. Several new, tightly linked SSR, RAPD and EST‐ILP PCR markers were developed for tracking the various Th. intermedium translocations associated with Wsm1, including the smaller translocations on wheat chromosome 4AS and 4DS. Three markers for the 4A‐Wsm1 translocation were validated on a segregating breeding population.     

The synthesis and fungicidal activity of derivatives of o- and p-Cyclohexylphenyl phosphorodichloridates and dichloridophosphorothioates

The synthesis of o- and p-cyclohexyphenyl phosphorodichloridates and dichloridophosphorothioates and their conversion into the corresponding dimethyl phosphates, phosphorodihydrazides, and phosphorodihydrazones, is discussed. o- and p-Cyclohexylphenyl N-phenylphosphoramidic chlorides were converted to the hydrazide and the O-methyl ester. The phosphorodichloridates were converted to the dihydrogen phosphates, but the dichloridophosphorothioates could not be hydrolysed in an analogous manner. Structure-activity relationships have been briefly discussed; the most active compound was o-cyclohexylphenyl O-methyl phosphoroisopropylidene hydrazone.     

Significance of PWT4–Rwt4 interaction in the species specificity of Avena isolates of Magnaporthe oryzae on wheat

We examined whether PWT4, an avirulence gene of Avena isolates of Magnaporthe oryzae toward wheat, corresponded to Rwt4, a resistance gene identified in wheat cultivar Norin 4, in a one-to-one manner. Twelve wheat cultivars were inoculated with 65X1, an F₁ culture with PWT4 derived from a cross between an Avena isolate (Br58) and a Triticum isolate (Br48). Three wheat cultivars (Norin 26, Shin-chunaga, Cheyenne) were resistant and therefore selected as possible carriers of Rwt4. The three cultivars were then inoculated with a population derived from a backcross of 61M2 carrying PWT4 with Br48 carrying pwt4. Segregation analyses revealed that PWT4 operates against the three cultivars. If PWT4 corresponds to Rwt4 in a one-to-one manner, all three cultivars should carry Rwt4. To test if this is the case, the three cultivars were crossed with Chinese Spring (a noncarrier of Rwt4) and Norin 4. When F₂ seedlings from Chinese Spring × Norin 26, Chinese Spring × Shin-chunaga, and Chinese Spring × Cheyenne were inoculated with 61M2, resistant and susceptible seedlings segregated in a 3 : 1 ratio. On the other hand, crosses between the three cultivars and Norin 4 yielded no susceptible F₂ seedlings. These results indicate that all three cultivars carry Rwt4. Considering all results, we concluded that PWT4 corresponds to Rwt4 in a one-to-one manner. An inoculation test with Chinese Spring–Cheyenne chromosome substitution lines indicated that Rwt4 is located on chromosome 1D.     

Studies of the New Herbicide KIH-6127. Part III. Synthesis and Structure–Activity Studies of Analogues of KIH-6127 against Barnyard Grass (Echinochloa oryzicola)*

The previously evaluated prototype, methyl 6-acetyl-2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate, was modified by the introduction of an oximino group. Further extensive synthetic modifications were then made to the 6-alkyl moiety (R¹), the ester moiety (R²), the alkoxyimino moiety (R³), the bridge-atom (X) and the 4,6-disubstituted-pyrimidine moiety (A, B, Z). Structure–activity relationships of the synthesized compounds were studied by examining their herbicidal activity against Barnyard grass (Echinochloa oryzicola) in paddy rice at various growth stages, including pre-emergence. The novel herbicide methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(methoxyimino)ethyl]benzoate, (KIH-6127) was found to be the most effective compound. The commercial development of this compound is currently in progress. © 1997 SCI.     

Investigations into carbamate insecticide selectivity: II: Differential degradation of selectophores in insect and mammal

Investigations were made of the effects of various modifications of the ether moiety alkoxyiminomethylphenyl N-methylcarbamates on the selective toxicity of the compounds to mouse vs. housefly. The highest mammalian selectivity ratio was found with o-(isopropyloxyiminomethyl)-phenyl N-methylcarbamate which was about 30-fold more toxic to fly than to mouse. The o-(1-propynyloxyiminomethyl)-phenyl N-methyl-carbamate was the most toxic compound to the housefly. The biochemcial basis for selective action was investigated.     

Comparative studies on chlorpyrifos and methyl parathion induced oxidative stress in different parts of rat brain: Attenuation by antioxidant vitamins

Organophosphate (OP) pesticides are among the most widely used synthetic chemicals for controlling a wide variety of pests. Chlorpyrifos (o,o′-diethyl-o-3,5,6-trichloro-2-pyridyl phosphorothionate, CPF) is among the leading OP pesticides used extensively throughout the world including India while methyl parathion (o,o-di methyl-o-p-nitrophenyl phosphorothioate, MPT) another OP compound, widely used as insecticide and acaricide to control many biting or sucking pests of agricultural crops. Present study was carried out to compare the chronic toxicity of CPF and MPT, their potential to generate oxidative stress and ameliorating effects of antioxidant vitamins in brain of rats. Results of the present study clearly demonstrated that the oral exposure of CPF or MPT, generated oxidative stress in different parts of rat brain consequently accumulating malondialdehyde (MDA) and 4-hydroxynonanal (4HNE), the two major end products of lipid peroxidation, in all the three brain regions i.e. fore-, mid- and hind-brain. The levels of hydrogen peroxide (H₂O₂) were also increased in all the three brain regions when compared with control. CPF and MPT exposure caused decrease in the levels of reduced glutathione (GSH) and increase in the levels of oxidized glutathione (GSSG) in all the three brain regions. The increase in the levels of MDA, 4HNE, H₂O₂ and GSSG was less pronounced when CPF or MPT was given to the rats fed with a mixture of vitamin A, E and C. The present findings clearly show that oral intake of a mixture of vitamin A, E and C protects the rats from MPT or CPF induced oxidative stress and suggest that this treatment alleviates the toxicity of these pesticides to a greater extent.     

KHAPLI在小麦抗病育种中的利用

普通小麦(Triticum aeslivum,2n=6x=42)与二粒小麦Khapli (T. dicoccum,2n=4x=28)杂交,因普通小麦品种不同,传递给杂交种的基因数也不同。抗贵白4号、16号和20号小种的两个显性抗白粉病基因,容易遗传给六倍体小麦遗传背景。抗贵白64号小种的可能有1个隐性基因,较难遗传给普通小麦的杂种后代。     

吡草醚室内除草生物活性测定及对小麦安全性评价

为探讨原卟啉原氧化酶抑制剂类除草剂—吡草醚防除小麦田阔叶杂草的生物活性及其对小麦的安全性,采用室内生物活性测定法研究了吡草醚对我国北方小麦田常见5种阔叶杂草的除草活性及对3个小麦品种的安全性。结果表明:吡草醚对播娘蒿Descurainia sophia、荠菜Capsella bursa-pastoris和麦瓶草Silene conoidea的防效好,GR_(90)值分别为3.66、4.21、2.57 g(a.i.)/hm~2,对猪殃殃Galium aparine、麦家公Lithospermum arvense的防效略差,GR_(90)值分别为11.41、17.39 g(a.i.)/hm~2,其活性是苯磺隆的2.27~9.07倍;吡草醚对抗苯磺隆荠菜有一定的控制作用,GR_(90)值为47.55 g(a.i.)/hm~2。该药剂对小麦安全性好,当剂量为384、192 g(a.i.)/hm~2时,小麦出现轻微触杀性药害;济麦22、良星66和矮抗58对吡草醚的耐药性分别为对苯磺隆的2.00、2.41和1.18倍。吡草醚在供试3个小麦品种与5种杂草之间的选择性指数在22.80~309.73之间,优于苯磺隆。表明吡草醚茎叶喷雾处理对温室盆栽阔叶杂草具有速效性好、活性高、选择性强等优点,是具有开发前景的一种麦田除草剂。     

Efficacy of five different formulations of clopyralid on Cirsium arvense (L.) Scop, and Polygonum convolvulus L

Experiments were conducted in a controlled environment growth room to compare the phytotoxicity of five formulations of clopyralid and to determine the effect of post-treatment simulated rainfall applications on the efficacy of these formulations. Clopyralid, formulated as the acid, monoethanolamine salt, potassium salt, 2-ethylhexyl ester or 1-decyl ester was applied to Cirsium arvense or Polygonum convolvulus at the 8–10 and 4–6 leaf stage of development, respectively. Based on the shoot and root dry weight data from both species, the 2-ethylhexyl ester was consistently less phytotoxic than the other four formulations. With respect to Cirsium arvense shoot and root dry weight, there was no difference in efficacy between the acid, monoethanolamine salt, potassium salt and 1-decyl ester. Root dry weight changes of Polygonum convolvulus did not correlate well with an increase in dose of the five formulations. Maximum increase in stem diameter of Polygonum convolvulus occurred after application of 100 g a.e. ha^?1 of the acid, monoethanolamine salt, potassium salt and 1-decyl ester whereas with the 2-ethylhexyl ester, the maximum increase occurred after application of 200 g a.e. ha^?1. Simulated rainfall was applied 3, 6, 9 or 12 h after application of 200 g a.e. ha^?1 of the five clopyralid formulations to both species. Rainfall reduced the efficacy of clopyralid, regardless of the formulation or species. The 2-ethylhexyl ester was less efficacious than the other four formulations, irrespective of the timing of simulated rainfall.     

小麦抗赤霉病3B-QTL和6B-QTL的遗传互作模式分析

为明确来自抗赤霉病的小麦品种望水白的2个主效抗扩展3B-QTL和6B-QTL的抗性遗传和互作模式,基于分子标记辅助选择方法,构建了回交分离群体,以病小穗数(NDS)和病轴长(LDR)为鉴定指标,采用单花滴注接种法对携带3B-QTL和6B-QTL的BC_3F_1、BC_3F_2、BC_3F_3世代以及抗感对照进行了抗赤霉病扩展的表型鉴定和评价。结果表明,3B-QTL和6B-QTL在烟农19和矮抗58不同的背景中,杂合基因型与纯合望水白基因型之间的NDS和LDR差异显著;携带3B-QTL和6B-QTL株系的抗扩展性与只含有单个3B-QTL的株系无显著差异,但显著高于只携带单个6B-QTL株系的抗性,抗感分离比经卡方检验符合4∶3∶9的分离比例,遵循2个独立孟德尔遗传因子控制的隐性遗传模式,且3B-QTL隐性上位于6B-QTL。研究表明,望水白的3B-QTL和6B-QTL抗扩展效应强且稳定,可以作为抗赤霉病基因资源在育种实践中充分利用。     

Response of wheat and oat seedlings to root-applied diclofop-methyl and 2,4-dichlorophenoxyacetic acid

Roots of wheat and oat seedlings were treated with diclofop-methyl (methyl 2-[4-(2′,4′-dichlorophenoxy)phenoxy]propanoate) in a specially designed Plexiglas treatment apparatus. Diclofopmethyl severely inhibited the root growth of susceptible oat seedlings but roots of resistant wheat seedlings were unaffected. Diclofop-methyl at 0.3 μM reduced the growth of oat roots to 50% of the control. Direct contact between diclofop-methyl and the inhibited root zone was necessary for growth inhibition since other parts of the seedling (roots and shoots) isolated from contact with diclofop-methyl solution by a physical barrier were unaffected. Diclofop (2-[4-(2′,4′-dichlorophenoxy)phenoxy]propionic acid), the free acid metabolite of diclofop-methyl, was somewhat more phytotoxic than the parent compound. The herbicide, 2,4-dichlorophenoxyacetic acid (2,4-D), which engenders auxin responses, slightly enhanced the inhibition of oat root growth by diclofop-methyl. The primary wheat metabolite, ring-hydroxylated diclofop, was nonphytotoxic to oat root growth, whereas the acetylated derivative of the primary water-soluble oat metabolite (neutral glucose ester of diclofop) inhibited oat root growth to the same extent as diclofop-methyl. These results support the hypothesis that the basis for selectivity between resistant wheat and susceptible oat is the metabolism of diclofop-methyl by aryl hydroxylation and conjugation but not glucose ester conjugation. Translocation is also not an important factor in the phytotoxic activity of diclofop-methyl.     

棉籽壳中除草活性物质提取及鉴定

为了开发利用棉籽壳中的除草活性物质,分别以无水乙醇、正丁醇、石油醚和乙酸乙酯为溶剂,采用索氏提取法对棉籽壳中的活性物质进行了提取,并对各溶剂粗提物进行了除草活性测定。结果发现:用无水乙醇提取的粗提物对稗草生长的抑制活性最高,经气相色谱-质谱(GC-MS)联用分析,发现该粗提物中主要含有甘油、三环己基3-烯-6-辛酮、4-乙烯基-2-甲氧基苯酚、(邻甲基苯酚)-2-溴-2氯-乙酰酯、十四酸、十四酸乙酯、十六烷酸、辛酸异戊酯和亚油酸9种化合物。进一步的除草活性测定结果表明,亚油酸、辛酸异戊酯、4-乙烯基-2-甲氧基苯酚和(邻甲基苯酚)-2-溴-2氯-乙酰酯4种化合物对稗草表现出一定的除草活性,其中亚油酸活性最强,其IC₅₀值为14.5 mg/L。