The use of piperonyl butoxide and MGK-264 to improve the efficacy of some plant-derived molluscicides

Synergism of an oil of Azadirachta indica, a powdered extract of Allium sativum bulbs and an oleoresin of Zingiber officinale rhizomes by piperonyl butoxide and MGK-264 was studied against the snails Lymnaea acuminata and Indoplanorbis exustus. The active components of these plant-derived molluscicides, respectively azadirachtin, allicin and [6]gingerol, were also combined with these synergists. Both piperonyl butoxide and MGK-264 enhanced the toxicity of all of the test compounds. The response of snails to the synergised mixtures was both time- and dose-dependent. © 1998 Society of Chemical Industry     

Effect of binary combination of some plant-derived molluscicides with MGK-264 or piperonyl butoxide on the reproduction of the snail Lymnaea acuminata

The effects of sub-lethal treatments (20 and 60% of 24-h LC(50)) with plant-derived molluscicides Annona squamosa, acetogenins, Argemone mexicana seed and protopine, in combination (1 + 5) with MGK-264 (ENT 8184) or piperonyl butoxide on the reproduction of Lymnaea acuminata has been studied. The plant-derived molluscicides and their active molluscicidal components, protopine and acetogenins, in combination with ENT 8184 or piperonyl butoxide caused a significant reduction in the fecundity, hatchability and survival of young snails. Combination of A squamosa seed powder with piperonyl butoxide was very effective as it caused a complete arrest of snail fecundity within 24 h of treatment. Removal of the snails to fresh water after the 96-h treatments caused a significant recovery in the fecundity of L acuminata.     

The effect of single, binary, and tertiary combination of few plant derived molluscicides alone or in combination with synergist on different enzymes in the nervous tissues of the freshwater snail Lymnaea (Radix) acuminata (Lamark)

The effect of single, binary, and tertiary combination of few plant derived molluscicides alone or in combination with synergist on different enzymes (acetylcholinesterase—AChE, lactic dehydrogenase—LDH, and acid/alkaline phosphatase—ACP/ALP in the nervous tissue of the freshwater snail Lymnaea acuminata were studied. Sublethal in vivo 24 h exposure to 40 and 80% of LC₅₀ of Azadirachta indica oil (AI), oleoresin of Zingiber officinale (OL), Cedrus deodara oil (CD), Allium sativum (AS), and Polianthes tuberosa (PT) bulb powder singly, their binary combination of AI + OL, AS + CD, AS + PT, CD + OL, CD + PT, OL + PT, and tertiary combination of these binary combinations with the synergist piperonyl butoxide (PB) or MGK-264 significantly altered the activity of these enzymes. Tertiary combination with PB or MGK was very effective. Combination of CD + PT + MGK was more effective against AChE whereas, the combination of CD + OL + PB, CD + AS + PB, and CD + PT + PB were more effective against LDH, ACP, and ALP, respectively.     

Enzyme inhibition by molluscicidal component of Areca catechu and Carica papaya in the nervous tissue of vector snail Lymnaea acuminata

In the present study toxic effects of active molluscicidal component of Areca catechu and Carica papaya was studied on certain enzymes in the nervous tissue of freshwater snail Lymnaea acuminata. In in vivo and in vitro exposure of arecoline (active component of Areca catechu seed) and papain (C. papaya latex and seed) significantly inhibited the acetylcholinesterase (AChE), acid and alkaline phosphatase (ACP/ALP) activity in the nervous tissue of L. acuminata. The inhibition kinetics of these enzymes indicate that arecoline and papain caused competitive and uncompetitive inhibition of AChE, respectively, whereas arecoline caused competitive-non-competitive inhibition of ACP/ALP and papain caused non-competitive inhibition of ACP/ALP. Thus the inhibition of AChE, ACP and ALP by arecoline and papain in the nervous tissue of L. acuminata may be the cause of molluscicidal activity of A. catechu and C. papaya, respectively.     

Enzyme inhibition by molluscicidal component of Areca catechu and Carica papaya in the nervous tissue of vector snail Lymnaea acuminata

In the present study toxic effects of active molluscicidal component of Areca catechu and Carica papaya was studied on certain enzymes in the nervous tissue of freshwater snail Lymnaea acuminata. In in vivo and in vitro exposure of arecoline (active component of Areca catechu seed) and papain (C. papaya latex and seed) significantly inhibited the acetylcholinesterase (AChE), acid and alkaline phosphatase (ACP/ALP) activity in the nervous tissue of L. acuminata. The inhibition kinetics of these enzymes indicate that arecoline and papain caused competitive and uncompetitive inhibition of AChE, respectively, whereas arecoline caused competitive–non-competitive inhibition of ACP/ALP and papain caused non-competitive inhibition of ACP/ALP. Thus the inhibition of AChE, ACP and ALP by arecoline and papain in the nervous tissue of L. acuminata may be the cause of molluscicidal activity of A. catechu and C. papaya, respectively.     

Effects of azadirachtin on the regulation of midgut peristalsis by the stomatogastric nervous system inLocusta migratoria

A single injection of azadirachtin into nymphal and adult locusts results in a decrease of food intake but not in reduced food utilization. Feeding deterrency is correlated with a gradual inhibition of midgut peristalsis. Gut movement is under the control of the stomatogastric nervous system, especially the ingluvial ganglion, as demonstrated in anin vitro system. Serotonin is the most potent peristalsis-stimulating drugin vitro. Concurrent with the cessation of midgut peristalsis after azadirachtin injection, a depletion of the serotoninergic cell bodies in the frontal ganglion can be observed. Midgut preparations which show strongly inhibited contractions due to previous azadirachtin treatmentin vivo are minimally, or not at all, stimulatedin vitro by serotonin, depending on the amount of time that has elapsed since treatment. When midgut preparations of untreated locusts are challenged with azadirachtinin vitro, peristalsis is suppressed in a dose-dependent manner. Simultaneous application of azadirachtin and serotonin results in a slight stimulation of midgut peristalsis. We propose the hypothesis that azadirachtin interferes with the serotoninergic system of the stomatogastric ganglia and thus inhibits midgut peristalsis. The molecular mechanism of the action of azadirachtin remains to be determined.     

Pesticidal seed coats based on azadirachtin‐A: release kinetics,storage life and performance

BACKGROUND: Infestation of seeds by pests during storage leads to deterioration in quality. Seed coating is an effective option to overcome the menace. Unlike synthetic fungicidal seed coats, little is known of those based on botanicals. This study aims at developing azadirachtin‐A‐based pesticidal seed coats to maintain seed quality during storage. RESULTS: Polymer‐ and clay‐based coats containing azadirachtin‐A were prepared and evaluated for quality maintenance of soybean seed during storage. Gum acacia, gum tragacanth, rosin, ethyl cellulose, hydroxyethyl cellulose, polyethyl methacrylate, methyl cellulose, polyethylene glycol, polyvinyl chloride, polyvinyl acetate, polyvinyl pyrrolidone and Agrimer VA 6 polymers and the clay bentonite were used as carriers. The time for 50% release (t_1/2) of azadirachtin‐A into water from the seeds coated with the different coats ranged from 8.02 to 21.36 h. The half‐life (T_1/2) of azadirachtin‐A in the coats on seed ranged from 4.37 to 11.22 months, as compared with 3.45 months in azadirachtin‐A WP, showing an increase by a factor of nearly 1.3–3.3 over the latter. The coats apparently acted as a barrier to moisture to reduce azadirachtin‐A degradation and prevented proliferation of storage fungi. Polyethyl methacrylate, polyvinyl acetate and polyvinyl pyrrolidone were significantly superior to the other polymers. Azadirachtin‐A showed a significant positive correlation with seed germination and vigour, and negative correlation with moisture content. CONCLUSION: Effective polymeric carriers for seed coats based on azadirachtin‐A are reported. These checked seed deterioration during storage by acting as a barrier to moisture and reduced the degradation of azadirachtin‐A. Copyright © 2008 Society of Chemical Industry     

Effects of azadirachtin on Tetranychus urticae (Acari: Tetranychidae) and its compatibility with predatory mites (Acari: Phytoseiidae) on strawberry

BACKGROUND: The spider mite, Tetranychus urticae, is the major strawberry pest in Brazil. The main strategies for its control comprise synthetic acaricides and predatory mites. The recent register of a commercial formula of azadirachtin (Azamax^® 12 g L^?1) can be viable for control of T. urticae. In this work, the effects of azadirachtin on T. urticae and its compatibility with predatory mites Neoseiulus californicus and Phytoseiulus macropilis in the strawberry crop were evaluated. RESULTS: Azadirachtin was efficient against T. urticae, with a mortality rate similar to that of abamectin. In addition, the azadirachtin showed lower biological persistence (7 days) than abamectin (21 days). Azadirachtin did not cause significant mortality of adult predatory mites (N. californicus and P. macropilis), but it did reduce fecundity by 50%. However, egg viability of the azadirachtin treatments was similar to that of the control (>80% viability). The use of azadirachtin and predatory mites is a valuable tool for controlling T. urticae in strawberry crop. CONCLUSIONS: Azadirachtin provided effective control of T. urticae and is compatible with the predatory mites N. californicus and P. macropilis. It is an excellent tool to be incorporated into integrated pest management for strawberry crop in Brazil. Copyright © 2012 Society of Chemical Industry     

Control of plant diseases by natural products: Allicin from garlic as a case study

This review aims to increase awareness of the potential for developing plant protection strategies based on natural products. Selected examples of commercial successes are given and recent data from our own laboratory using allicin from garlic are presented. The volatile antimicrobial substance allicin (diallylthiosulphinate) is produced in garlic when the tissues are damaged and the substrate alliin (S-allyl-l-cysteine sulphoxide) mixes with the enzyme alliin-lyase (E.C.4.4.1.4). Allicin is readily membrane-permeable and undergoes thiol-disulphide exchange reactions with free thiol groups in proteins. It is thought that these properties are the basis of its antimicrobial action. We tested the effectiveness of garlic juice against a range of plant pathogenic bacteria, fungi and oomycetes in vitro. Allicin effectively controlled seed-borne Alternaria spp. in carrot, Phytophthora leaf blight of tomato and tuber blight of potato as well as Magnaporthe on rice and downy mildew of Arabidopsis. In Arabidopsis the reduction in disease was apparently due to a direct action against the pathogen since no accumulation of salicylic acid (a marker for systemic acquired resistance, SAR) was observed after treatment with garlic extract. We see a potential for developing preparations from garlic for use in organic farming, e.g. for reducing the pathogen inoculum potential in planting material such as seeds and tubers. We have tested various encapsulation formulations in comparison to direct treatment. Note added in proof: The complete chemical synthesis of azadirachtin has now been achieved. Nature (2007) 448: 630–631     

Effect of azadirachtin on the control of <Emphasis Type="Italic">Anticarsia gemmatalis</Emphasis> and its impact on <Emphasis Type="Italic">Trichogramma pretiosum</Emphasis>

Anticarsia gemmatalis has great potential to reduce soybean productivity, and the egg parasitoid Trichogramma pretiosum is a major agent in the biological control of this pest in soybean fields. We show that azadirachtin is able to control velvetbean caterpillars in soybean plants and also that it has no effects on the parasitoid T. pretiosum. Soybean plants were sprayed with solutions containing control (water), 50 and 100 mg.l ⁻¹ of azadirachtin (AzaMax™ 12 g a.i.l ⁻¹). Third instar larvae of A. gemmatalis were confined to soybean plants after the spraying. Leaf consumption and larval mortality of A. gemmatalis were evaluated. Newly emerged females of T. pretiosum were placed for 24 h in tubes with a piece of cardboard containing the same doses of azadirachtin used against velvetbean caterpillars. After 24 h, cardboard with 20 eggs of A. gemmatalis was offered for parasitism during 24 h, and the emergence and sex ratio of progenies were determined. Azadirachtin at 50 or 100 mg.l ⁻¹ reduced leaf consumption and caused 100% mortality in A. gemmatalis larva. Azadirachtin did not negatively affect the parasitism, emergence or sex ratio of the progeny. This indicates that the product can be used with mass release of T. pretiosum to control A. gemmatalis.     

Synthesis of 2-amino-6-oxocyclohexenylsulfonamides and their activity against Botrytis cinerea

BACKGROUND: With the objective of exploring the fungicidal activity of 2‐oxocyclohexylsulfonamides (2), a series of novel 2‐amino‐6‐oxocyclohexenylsulfonamides (6 to 23) were synthesised, and their fungicidal activities against Botrytis cinerea Pers. were evaluated in vitro and in vivo. RESULTS: The compounds were characterised by IR, ¹H NMR and elemental analysis. Bioassay results of mycelial growth showed that compounds 6 to 23 had a moderate antifungal activity against B. cinerea. N‐(2‐methylphenyl)‐2‐(2‐methylphenylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (13) and N‐(2‐chlorophenyl)‐2‐(2‐chlorophenylamino)‐6‐oxocyclohexenylsulfonamide (21) showed best antifungal activities, with EC₅₀ values of 8.05 and 10.56 µg mL^?1 respectively. Commercial fungicide procymidone provided an EC₅₀ value of 0.63 µg mL^?1. The conidial germination assay showed that most of compounds 6 to 23 possessed excellent inhibition of spore germination and germ‐tube elongation of conidia of B. cinerea. For in vivo control of B. cinerea colonising cucumber leaves, the compound N‐cyclohexyl‐2‐(cyclohexylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (19) showed a better control effect than the commercial fungicide procymidone. CONCLUSION: The present work demonstrated that 2‐amino‐6‐oxocyclohexenylsulfonamides can be used as possible new lead compounds for further developing novel fungicides against B. cinerea. Copyright © 2011 Society of Chemical Industry     

Resistance sources to Fusarium oxysporum f. sp. cubense tropical race 4 in banana wild relatives

Target trait evaluation in crop wild relatives is an important prerequisite for efficiently using the potential useful genes located in this valuable germplasm. Over recent decades, Fusarium oxysporum f. sp. cubense tropical race 4 (Foc‐TR4) has seriously threatened worldwide banana plantations. Breeding new resistant cultivars from wild banana species is expected to provide invaluable additional resources. However, knowledge on resistance to Foc‐TR4 in wild Musa species is very limited. In this study, eight genotypes of wild banana relatives (Musa acuminata subsp. burmannica, M. balbisiana, M. basjoo, M. itinerans, M. nagensium, M. ruiliensis, M. velutina and M. yunnanensis) were characterized for resistance to Foc‐TR4 in both greenhouse and field conditions. Most wild bananas showed higher resistance levels to Foc‐TR4 than the reference cultivars ‘Brazilian’ (AAA, susceptible) and ‘Goldfinger’ (AAAB, moderate resistance). Among the wild species, M. balbisiana showed the highest levels of disease intensity followed by M. acuminata subsp. burmannica. Some individuals of M. yunnanensis, M. nagensium, M. ruiliensis and M. velutina showed low levels of rhizome discolouration in greenhouse conditions, but were resistant in the field. No symptoms were observed on M. basjoo and M. itinerans, suggesting higher levels of resistance to Foc‐TR4. The results revealed different sources of resistance to Foc‐TR4 in banana wild relatives, which constitute a valuable genetic resource for banana breeding programmes aiming to produce cultivars resistant to fusarium wilt.     

Towards the primary target of chloroacetamides –new findings pave the way

This review reports on research of the last ten years to find the primary target enzyme for chloroacetamides. As could be shown first with the green alga Scenedesmus, the formation of very‐long‐chain fatty acids (VLCFAs) is severely impaired. Subsequently, in short‐term experiments, labelled malonate or stearate could be incorporated into leaf discs of cucumber, barley or leek seedlings. While the formation of ‘normal’ long‐chain fatty acids (up to C18) was not influenced, phytotoxic chloroacetamides strongly inhibited the synthesis of VLCFAs of C20, 22 and 24, with I₅₀ values of 10–100 nM . Inhibition depends on the amide structure and on stereospecificity. Also cafenstrole or recently developed tetrazolinones and phosphosulfonates were found active to inhibit fatty‐acid elongation. Subsequently, a cell‐free elongase assay was developed using a microsomal preparation from leek seedlings (Allium porrum L), [¹⁴C]malonyl‐CoA and C18, 20, or C22 acyl‐CoA primer substrates. All elongation steps were strongly affected by those phytotoxic herbicides which were also active in vivo. The inhibitors form a tight‐binding complex with the condensing elongase enzyme system which develops with time and lowers the I₅₀ values markedly. Apparently, a nucleophilic attack of the inhibitor takes place at the specific target enzyme. Acyl‐CoA elongation inhibition is correlated with growth inhibition of the intact cell. Due to the low I₅₀ values and the specific inhibition, we assume that impaired VLCFA‐formation is the primary phytotoxic impact of chloroacetamides and functionally related structures. © 2000 Society of Chemical Industry     

五种药剂对黏虫卵的室内触杀效果及胚胎发育的影响

为有效防控黏虫Mythimna separata,选用灭多威、苦参·印楝素、苏云金芽胞杆菌Bacillus thuringiensis、甲维盐和高效氯氟氰菊酯5种药剂对其卵进行室内触杀试验,比较这5种药剂对黏虫卵和初孵幼虫的触杀效果及对卵的毒力,测定不同药剂处理后黏虫卵初孵幼虫存活率、发育历期、化蛹率、蛹重和羽化率;并通过冷冻切片技术观察不同药剂处理后黏虫卵的外部形态和胚胎发育情况。室内触杀试验结果表明,苦参·印楝素浓度大于0.1 mg/L时,对产后不同时间黏虫卵的校正死亡率介于42.89%～97.34%之间,苏云金芽胞杆菌浓度为0.01 mg/L时对产后72 h黏虫卵的校正死亡率已达71.99%;各浓度苦参·印楝素和苏云金芽胞杆菌处理产后24、48和72 h黏虫卵后,其初孵幼虫校正死亡率介于39.02%～83.59%之间。苦参·印楝素对产后24、48 h黏虫卵的毒力最大,致死中浓度LC_(50)分别为0.018、0.109 mg/L;苏云金芽胞杆菌对产后72 h黏虫卵的毒力最大,LC_(50)为0.004 mg/L。黏虫卵经5种药剂处理后,幼虫化蛹率、蛹重和羽化率分别介于91.07%～93.64%、0.272～0.284 g和86.60%～87.78%之间,与对照差异不显著,幼虫存活率较对照显著下降43.02%～60.27%,幼虫发育历期较对照延长0.23～0.88 d,其中灭多威、苦参·印楝素、苏云金芽胞杆菌处理的幼虫发育历期较对照显著延长。苦参·印楝素、苏云金芽胞杆菌使胚胎无法形成正常胚带,同时会使已发育的虫体出现蜷缩、腹部皱缩;高效氯氟氰菊酯会延缓胚胎发育时间,使已形成的虫体畸形或使其肠道断裂;甲维盐影响虫体对营养物质的吸收,造成虫体萎缩,使其不能正常孵化。在黏虫卵防治中推荐使用苏云金芽胞杆菌和苦参·印楝素。     

A molecular diagnostic for tropical race 4 of the banana fusarium wilt pathogen

This study analysed genomic variation of the translation elongation factor 1α (TEF‐1α) and the intergenic spacer region (IGS) of the nuclear ribosomal operon of Fusarium oxysporum f. sp. cubense (Foc) isolates, from different banana production areas, representing strains within the known races, comprising 20 vegetative compatibility groups (VCG). Based on two single nucleotide polymorphisms present in the IGS region, a PCR‐based diagnostic tool was developed to specifically detect isolates from VCG 01213, also called tropical race 4 (TR4), which is currently a major concern in global banana production. Validation involved TR4 isolates, as well as Foc isolates from 19 other VCGs, other fungal plant pathogens and DNA samples from infected tissues of the Cavendish banana cultivar Grand Naine (AAA). Subsequently, a multiplex PCR was developed for fungal or plant samples that also discriminated Musa acuminata and M. balbisiana genotypes. It was concluded that this diagnostic procedure is currently the best option for the rapid and reliable detection and monitoring of TR4 to support eradication and quarantine strategies.     

Binary combination of carbohydrates and amino acids as snail attractant in pellets containing molluscicides against the snail Lymnaea acuminata

Snail control is one of the important methods in the campaign to reduce the incidence of fascioliasis and schistosomiasis. In order to achieve this objective, the method of bait formulation containing an attractant and a molluscicide is an appropriate approach to lure the target snail population to the molluscicide. In the present study snail attractant pellets (SAP) were prepared from binary combination of carbohydrates (10 mM) and amino acids (20 mM) in 2% agar solution. These were tested on Lymnaea acuminata, an intermediate host of the digenean trematodes Fasciola hepatica and Fasciola gigantica. The behavioral responses of snails to these binary combination were examined. The fraction of snails that was in contact with the SAP at different times was used as a measure of attraction. Among all the binary combination of carbohydrates; (sucrose + starch)—72.9%, binary combination of amino acids; (proline + serine)—48.0% and binary combination of carbohydrates and amino acids; (sucrose + serine)—69.5%, emerged as the strongest attractant pellets. Toxicity of these SAP containing different concentrations of molluscicides were used as bait against the snail, L. acuminata. Thymol containing SAP emerged as the strongest bait formulation (96 h LC₅₀ 0.540%, 0.318% and 0.305%) against L. acuminata.     

Comparative molluscicidal action of extract of Ginko biloba sarcotesta, arecoline and niclosamide on snail hosts of Schistosoma japonicum

In search for new local plant molluscicides for the control of the vectors of schistosomiasis, we compared the molluscicidal action of the extract of Ginkgo biloba sarcotesta by benzinum (EGSB) to that of arecoline (ARE) and niclosamide (NIC) against Oncomelania hupensis snails. NIC showed the highest toxicity on snails with 24 h LC₅₀ vales of 0.12 mg/L and LC₉₀ of 0.98 mg/L, while the LC₅₀ and LC₉₀ of EGSB were much lower than that of ARE. Sublethal in vivo 24 h exposure to 40% and 80% LC₅₀ of NIC, EGSB and ARE altered the activities of different enzymes in different body tissues of snails. EGSB could significantly inhibit Choline esterase (ChE), Alanine aminotransferase (ALT), Alkaline phosphatase (ALP) and Malic dehydrogenase (MDH) activities both in the cephalopodium and liver. ARE could significantly cause a reduction in ChE, ALP activities in the cephalopodium and ChE, ALT, ALP, Succinodehydrogenase (SDH), MDH activities in the liver. NIC significantly altered activities of ChE, ALT, ALP, SDH, and MDH in the cephalopodium and ChE, ALT, ALP, SDH activities in the liver. All molluscicides could not affect Lactate dehydrogenase (LDH) activity in the cephalopodium and the liver. Maximum inhibition of ALT and MDH activities was found in the cephalopodium and liver of snails treated with 80% of 24 h LC₅₀ of EGSB. However, NIC and ARE caused maximum reduction in ALP and SDH activities, respectively. The results indicated that molluscicidal action of EGSB was different to that of ARE and NIC in some extent.     

Response of the tomato miner Tuta absoluta (Lepidoptera: Gelechiidae) to thirteen insecticides in semi‐natural conditions in Tunisia

Experiments on larvicide and ovicide activity of 13 insecticides in semi‐natural conditions showed a medium to low efficacy of bio‐insecticides on all instars of Tuta absoluta (Meyrick) except for Bacillus thuringiensis Berliner var. kurstaki which was distinguished by an average mortality of 72.5%. Spinosad and Spinetoram based insecticides showed high efficiency in controlling all instars of larvae with respectively an average mortality of 66.5% and 85.6%. However, this study revealed a unique ovicide effect of azadirachtin‐neem oil based insecticide with 43.8% egg mortality.     

印楝素对马铃薯甲虫的控制作用

为探讨植物源杀虫剂印楝素对马铃薯甲虫的防治作用,采用叶碟法测定印楝素乳油对其成虫的拒食作用,并通过药效试验测定印楝素乳油对马铃薯甲虫的控制效果。结果显示,印楝素对马铃薯甲虫成虫有较强的非选择性拒食作用,且拒食率随取食时间的增加而升高。在取食36 h后,浓度为6、7.5、10、15和30 mg/L印楝素的拒食率分别为55.5%、59.1%、53.4%、76.1%和63.3%,拒食率与浓度无显著相关性;但印楝素对马铃薯甲虫的选择性拒食率较低,各浓度处理间均无显著差异,取食36 h时,选择拒食率约20%;在田间10 mg/L印楝素溶液施药1 d和3 d后,虫口减退率分别为26.52%和50.76%,显著高于对照组,施药9 d后,马铃薯甲虫的校正防治效果为48.86%。表明印楝素对马铃薯甲虫有一定的控制效果。     

Synthesis and characterisation of some 4‐keto derivatives of 1,3,4(2H)‐isoquinolinetrione redox mediator herbicides

Derivatives of 2‐ethyl‐1,3,4(2H)‐isoquinolinetrione in which the 4‐keto group has been modified to (Z)‐oxime, (E)‐ and (Z)‐O‐methyl oxime, (Z)‐N,N‐dimethyl hydrazone, cyano‐imine and dicyanomethylene moieties have been prepared and evaluated as redox mediator herbicides. All of the compounds have the free‐radical properties required to function as redox mediators, as determined by cyclic voltammetry, though only the O‐methyl oximes, the N,N‐dimethyl hydrazone and the cyano‐imine have reduction potentials in the range required to stimulate the light‐dependent consumption of oxygen at photosystem I in isolated chloroplasts. The O‐methyl oximes and the cyano‐imine are fast‐acting post‐emergence herbicides, producing symptoms of rapid desiccation; the (E)‐O‐methyl oxime is the most active herbicide, being somewhat more potent than the parent isoquinolinetrione. Hydrolysis studies indicate that it is unlikely that any compound generates the parent isoquinolinetrione in vivo. Attempts to explain differences between in vitro and in vivo activities using hydrolytic stabilities and physical properties were unsuccessful, and it was concluded that these factors probably play a less significant role in moderating the herbicidal activity of isoquinolinetrione derivatives than originally thought. © 2000 Society of Chemical Industry