Synthesis and Evaluation of New Ethyl 2,3- Dihydro-3-oxoisothiazolo[5,4-b]pyridine- 2-alkanoate Derivatives as Potential Herbicides

Several ethyl 2,3-dihydro-3-oxoisothiazolo[5,4-b]pyridine-2-alkanoate derivatives were synthesized as herbicides. Only 5-methyl derivatives inhibited both hypocotyl and root growth in the lettuce (Lactuca sativa L.) seedling test at 100 mg litre^-1. Only ethyl propionate and valerate derivatives showed significant inhibition at 0·1 mg litre^-1, whereas ethyl acetate or butyrate derivatives were inactive. Contrary to unoxidized derivatives, the inhibitory effect of 1-oxide and 1,1-dioxide derivatives was strongly dependent on concentration; ethyl 2,3-dihydro-5-methyl-3-oxoisothiazolo[5,4-b]pyridine-2-propionate 1,1-dioxide inhibited 100% of germination at 100 mg litre^-1 and 45% of lettuce seedling growth at 0·1 mg litre^-1. Quantitative structure–inhibition of growth relationship analysis carried out by adaptive least-squares (ALS) method gave a good correlation with small and hydrophobic 5-substituents as well as with odd carbon-chain ethyl alkanoates in position 2. Active compounds did not show auxin-like activity from 0·1 to 100 mg litre^-1. © 1997 SCI.     

Effect of short exposures to a high concentration on the subsequent toxicity of low concentrations of methyl bromide to diapausing larvae of the warehouse moth,Ephestia elutella (Hübner)

Ephestia elutella larvae in diapause were exposed at 25°C to methyl bromide at 12 mg litre^?1 for 3.5 or 7.5 h and then immediately exposed to a lower concentration. The minimum effective concentration (that at which Haber's rule, concentration × time = k, a constant for mortality, still applied) was about 3 mg litre^?1 in tests with no previous exposure toa high concentration, but it was about 2.5 mg litre^?1 for individuals surviving a 3.5 h exposure to 12 mg litre^?1, and was about 1.6 mg litre^?1 for those surviving a 7.5 h exposure to 12 mg litre^?1. These exposures to 12 mg litre^?1, respectively, killed 2–20% and 50–75% of larvae exposed, and hence the smaller the proportion of survivors of exposure to a high concentration, the lower the minimum effective concentration needed against them. Thus the low concentration persisting at the end of a practical fumigation should contribute significantly to the success of the treatment and be much more effective than any similar low concentration present soon after the introduction of gas.     

Comparative fungitoxicity of the insecticide permethrin and ten degradation products

The toxic effects of permethrin and ten of its degradation products on the growth of ten fungi were determined. Permethrin was relativelynon-toxic, with an EC₅₀ of > 100 mg litre^?1 but six of the degradation products were significantly (P= 0.05) more inhibitory. The ester hydrolysis products, 3-phenoxybenzyl alcohol and 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid, had EC₅₀ values ranging from 8 to > 100 and 20 to > 50 mg litre^?1, respectively. Other degradation products that were more toxic than permethrin included 3-phenoxybenzaldehyde and 3-phenoxybenzoic acid, with EC₅₀ values as low as < 1 mg lite^?1. Hydroxylated and substituted-benzene metabolites were non-toxic. Combinations of selected test compounds yielded both synergistic, antagonistic and additive interaction responses, depending upon the test system employed.     

A rapid bioassay for the detection of photosynthesis inhibitors in water

A modified leaf disc buoyancy procedure for the detection of photosynthesis-inhibiting residues in water is described. The modifications proposed, mainly the presence of sodium hydrogen carbonate in the infiltration solution, increased the sensitivity of the method and reduced the time required. The substituted urea and 1,3,5-triazine herbicides diuron, linuron, monuron, atrazine, ametryn and atraton were detected below 0.7 mg litre^?1 using cucumber (Cucumis sativus L., cv. ‘Dalia’) leaf discs. A concentration as low as 0.09 mg diuron litre^?1 could be detected. Although bean (Phaseolus vulgaris L., cv. ‘Bulgarian’) leaf tissue was less sensitive in this bioassay than cucumber, 0.3 mg diuron litre^?1 could still be detected. The test, being very rapid (less than 30 min per determination) and relatively sensitive, could be used for the detection of photosynthesis inhibitors in recycled water used for irrigation.     

Non-target effect of herbicides: I. effect of glyphosate and hexazinone on soil microbial activity. Microbial population,and in-vitro growth of ectomycorrhizal fungi

The effects of two herbicides, glyphosate (as a 359 g litre^?1 SL) and hexazinone (as a 50gkg^?1 granule) on soil microbial population, carbon dioxide evolution, and in-vitro growth of five species of ectomycorrhizal fungi were investigated. Glyphosate at 0–54 and 3.23 kg a.i. ha^?1 and hexazinone at 1. 2 and 8 kg a.i. ha^?1 did not reduce soil microbial population or carbon dioxide evolution in the long term (6 months). However, there was a significant short-term (2 months) effect of glyphosate on both fungal and bacterial counts at the 0.54 kg ha^?1 treatment. In in-vitro tests, Cenococcum graniforme. Hebeloma crustuliniforme and Laccaria laccata were more susceptible to both herbicides than was Suillus tomentosus. which was, in turn, more susceptible than Paxillus involutus. The growth of all five ectomycorrhizal fungi was significantly reduced when subjected to concentrations above 50 μl formulation litre^?1 (glyphosate) or 50 μg formulation litre^?1 (hexazinone).     

The response of three soil fungi to dalapon and diuron treatments

Dalapon and diuron are two common herbicides used for the control of weeds. A study of the response of Gliocladium virens, Trichoderma hamatum and T. koningii in cultures to the herbicides was carried out. Changes in fungal colony morphology and growth and sporulation rates in the presence of up to 10⁵ mg herbicide litre^?1 were monitored. The three fungi were not adversely affected at a concentration of 10³ mg litre^?1. Changes in colony morphology and decreases in growth and sporulation rates were evident at the maximum test concentration (10⁵ mg litre^?1) of both herbicides. These generally recovered when the fungi were replated in the absence of the herbicides.     

Diflubenzuron: Some aspects of its ovicidal and larvicidal mode of action and an evaluation of its practical possibilities

Diflubenzuron, 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea, possesses larvicidal and ovicidal activities. On larvae it acts mainly as a stomach poison, yet it sometimes exhibits important contact activity. Though all instars can be controlled, older instars are generally less susceptible than younger ones. Histological inspections of Leptinotarsa decemlineata larvae revealed that after ending exposure to the compound, distortions in newly deposited cuticular layers decreased gradually. Ovicidal effects resulted from direct contact of diflubenzuron with eggs or from contamination of females by contact or feeding. Electron microscopic observations of embryos of Leptinotarsa decemlineata, contaminated via the female, also showed disturbed cuticule formation, suggesting a similar activity of the compound in larvae and in eggs. Spraying the eggs of Leucoptera scitella shows the compound to be mainly ovidical at a rate of 100 mg litre^?1, whilst with lower concentrations (10 and 1 mg litre^?1) the young larval instar will be killed. The levels of cross-resistance to diflubenzuron as a larvicide are low and the compound can be used effectively in the field against populations that are highly resistant to conventional insecticides. Laboratory and field results, based on larvicidal and ovicidal activities of diflubenzuron, are discussed in respect of species belonging to the Diptera, Lepidoptera, Coleoptera, Acarina (Phyllocoptruta oleivora) and Hemiptera (Eurydema oleraceum and Psylla piri).     

Depression of the minimum concentration of methyl bromide effective against diapausing warehouse moth larvae at 15°c by prior exposure at a moderate concentration

Warehouse moth (Ephestia elutella) larvae in diapause were exposed at 15°C to methyl bromide at 8 mg litre^?1 for 14.5 h and then immediately exposed at a lower concentration. The exposure at 8 mg litre^?1 killed 44–69% of the larvae treated. Subsequent concentrations down to 1.1 mg litre^?1 obeyed Haber's rule (concentration × time= k, a constant for mortality), but a higher concentration-time product (ct) was required for over 90% kill at 0.8 mg litre^?1. Only concentrations down to 1.9 mg litre^?1 obey Haber's rule if there is no prior exposure at a higher concentration. Although minimum effective concentrations are lower at 15°C than at 25°C, exposure at a higher concentration depresses the subsequent level to a similar extent at each temperature. The contribution to the efficacy of a treatment, of low concentrations persisting at the end of fumigation, is thus likely to be even greater at moderate to low temperatures than at 25°C. The implications for the development of resistance to methyl bromide are discussed.     

Activity against plant pathogenic fungi of phomalactone isolated from Nigrospora sphaerica

Phomalactone, 5,6‐dihydro‐5‐hydroxy‐6‐prop‐2‐enyl‐2H‐pyran‐2‐one, produced by the fungus Nigrospora sphaerica, was tested in vitro against nine plant pathogenic fungi, and specifically inhibited the mycelial growth of Phytophthora infestans, with an MIC value of 2.5 mg litre^?1. Its inhibitory activities against sporangium and zoospore germination of P infestans were similar to those against Phytophthora capsici. In vivo, at 100 and 500 mg litre^?1, it reduced the development of tomato late blight caused by P infestans. © 2001 Society of Chemical Industry     

A monoclonal antibody‐based ELISA for the analysis of the insecticide flucythrinate in environmental and crop samples

A competitive enzyme‐linked immunosorbent assay (ELISA) has been developed for the detection of the insecticide flucythrinate in environmental and food samples. Two types of haptens, the acid moiety that is the hydrolyzed product of flucythrinate, and the carboxylated propyl derivative of the alcohol moiety, were used to prepare monoclonal antibodies (MAbs). Five MAbs, which raised against the former hapten, were reactive with flucythrinate. Among them, MAb F1A27‐4 showed the highest activity toward flucythrinate, and did not cross‐react with other pyrethroids such as cycloprothrin, fenvalerate, fluvalinate, etofenprox and silafluofen. The assay conditions of indirect competitive ELISA with MAb F1A27‐4 were studied to optimize the detection of flucythrinate in environmental and food samples. Incubation at 4 °C in the assay buffer, pH 8, with 300 mM sodium chloride improved the sensitivity. The addition of rabbit serum albumin or rabbit antiserum and the presence of 50 ml litre^?1 of methanol reduced matrix effects of the samples. Under optimized conditions, the ELISA detected flucythrinate spiked in water, soil, and extracts of apple and tea samples down to 10 mg litre^?1, 0.2 mg litre^?1, 0.3 mg litre^?1 and 0.3 mg litre^?1, respectively. The mean recovery and CV ranged from 91% to 120% and from 5% to 12%, respectively. The ELISA results in apple samples correlated well with those from LC–MS analysis (r² = 0.99, n = 12). © 2001 Society of Chemical Industry     

Effect of fipronil seed treatments on the germination and early growth of rice

Fipronil seed treatments were evaluated to determine whether they directly influence germination and subsequent seedling growth in rice (Oryza sativa L). Continuous seed exposure to fipronil (four days) at 2 000 mg litre⁻¹ significantly impaired germination (P < 0.001). When exposure was restricted to a 1-h period 48 h after the initiation of germination, early post-germination growth was also impaired (assessment two days after exposure, P < 0.05). The proportion of seeds satisfying our criteria for normal germination fell by 2.3 and 2.6% respectively across 17 cultivars. Cultivar effects were highly significant (P < 0.001). When exposure to fipronil (2 000 mg litre⁻¹) was restricted to 2 h at initial seed wetting no significant growth impairment occurred. No significant differences (P > 0.05) were found between shoot lengths or root system dry weights of control plants and plants developing from seed exposed continuously (two days) to fipronil at rates of up to 2 000 mg litre⁻¹ during germination and harvested nine days after sowing. Treating germinated seed with fipronil for 1 h immediately prior to sowing at rates of up to 4 000 mg litre⁻¹ did not result in significant changes (P < 0.05) in plant growth parameters at either nine or 25 days after sowing. No evidence of fipronil having a direct phytostimulatory effect on rice was obtained. © 1999 Society of Chemical Industry     

DPX-MP062—a potent compound for controlling the Egyptian cotton leafworm Spodoptera littoralis (Boisd.)

The effects of DPX-MP062 [methyl 7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)carbamoyl] indeno[1,2-e][1,3,4] oxadiazine-4a-carboxylate] a broad-spectrum insecticide with a novel mode of action, on the Egyptian cotton leafworm, Spodoptera littoralis, were studied in laboratory experiments. Egg hatch was affected by high concentrations (125 mg AI litre^-1) of DPX-MP062. Larvae that hatched from treated eggs were significantly affected at concentrations of 12·5 mg AI litre^-1 and greater. Larvae were fed castor bean leaves treated with DPX-MP062; 1st-instar larvae were the most susceptible development stage. Pupation and adult formation were determined in assays with 5th-instar larvae. There was strong suppression of adult formation; 65 and 91% at 0·5 and 0·75 mg AI litre^-1, respectively. Highly affected larvae died before pupation; slightly affected ones reached pupation 2–4 days later, were smaller than larvae in the untreated control, and were sometimes unable to develop into normal adults. Comparatively high concentrations (50 and 100 mg AI litre^-1) of the test compound were necessary to affect adults by ingestion, but no effects from contact application could be determined at a concentration of 100 mg AI litre^-1. © 1998 Society of Chemical Industry     

Effect of temperature on the toxicity of low concentrations of methyl bromide to diapausing larvae of the warehouse moth Ephestia elutella (Hübner)

The performance of low concentrations of methyl bromide against diapausing larvae of Ephestia elutella at 15 and 25°C was assessed in extended exposure periods. At concentrations of 1.9 mg litre^?1 and below, test batches required higher concentration-time (ct) products for 100% kill at 25°C than at 15°C. The minimum concentration at which the concentration: time relationship still applied was between 1.3 and 1.9 mg litre^?1 at 15°C, whereas at 25°C it was between 2.7 and 4.0 mg litre^?1. For many individuals within each population sample, however, lower concentrations at moderate dosage levels remained lethal. At 25°C, a ct product of about 90 mg litre^?1 h gave between 53 and 77% kill at 6.1, 4.0, 2.7 and 1.9 mg litre^?1. The trends observed suggest that the most tolerant members of the population have an enhanced ability to detoxify methyl bromide at the higher temperature. The implications of the results for the build-up of resistance and for practical control measures are discussed.     

Some physicochemical factors influencing foliar uptake enhancement of glyphosatemono(isopropylammonium) by polyoxyethylene surfactants

Structure-concentration–foliar uptake enhancement relationships between commercial polyoxyethylene primary aliphatic alcohol (A), nonylphenol (NP), primary aliphatic amine (AM) surfactants and the herbicide glyphosatemono(isopropylammonium) were studied in experiments with wheat (Triticum aestivum L.) and field bean (Vicia faba L.) plants growing under controlled-environment conditions. Candidate surfactants had mean molar ethylene oxide (EO) contents ranging from 5 to 20 and were added at concentrations varying from 0·2 to 10 g litre^?-1 to [¹⁴C]glyphosate formulations in acetone–water. Rates and total amounts of herbicide uptake from c. 0·2–μl droplet applications of formulations to leaves were influenced by surfactant EO content, surfactant hydrophobe composition, surfactant concentration, glyphosate concentration and plant species, in a complex manner. Surfactant effects were most pronounced at 0·5 g acid equivalent (a.e.) glyphosate litre^?-1 where, for both target species, surfactants of high EO content (15–20) were most effective at enhancing herbicide uptake: surfactants of lower EO content (5–10) frequently reduced, or failed to improve, glyphosate absorption. Whereas, at optimal EO content, AM surfactants caused greatest uptake enhancement on wheat, A surfactants gave the best overall performance on field bean; NP surfactants were generally the least efficient class of adjuvants on both species. Threshold concentrations of surfactants needed to increase glyphosate uptake were much higher in field bean than wheat (c. 2 g litre^?-1 and < 1 g litre^?-1, respectively); less herbicide was taken up by both species at high AM surfactant concentrations. At 5 and 10 g a.e. glyphosate litre^?-1, there were substantial increases in herbicide absorption and surfactant addition could cause effects on uptake that were different from those observed at lower herbicide doses. In particular, the influence of EO content on glyphosate uptake was now much less marked in both species, especially with AM surfactants. The fundamental importance of glyphosate concentration for its uptake was further emphasised by experiments using formulations with constant a.i./surfactant weight ratios. Any increased foliar penetration resulting from inclusion of surfactants in 0·5 g litre^?-1 [¹⁴C]glyphosate formulations gave concomitant increases in the amounts of radiolabel that were translocated away from the site of application. At these low herbicide doses, translocation of absorbed [¹⁴C]glyphosate in wheat was c. twice that in field bean; surfactant addition to the formulation did not increase the proportion transported in wheat but substantially enhanced it in field bean.     

Effect of ABT on the activity and rate of degradation of isoproturon in susceptible and resistant biotypes of Phalaris minor and in wheat

The effect of the monooxygenase inhibitor, 1-aminobenzotriazole (ABT) on isoproturon phytotoxicity and metabolism was studied in resistant (R) and susceptible (S) biotypes of Phalaris minor and in wheat (Triticum aestivum). Addition of ABT (2·5, 5 and 10 mg litre^-1) to isoproturon (0·25, 0·5, 1, 2 and 4 mg litre^-1) in the nutrient solution significantly enhanced the phytotoxicity of isoproturon against the R biotype. Isoproturon at 0·25 mg litre^-1 reduced the dry weight (DW) of the S biotype by 77%, whereas the R biotype required 4·0 mg litre^-1 for similar reduction. Addition of 10 mg litre^-1 of ABT to the 0·25 mg litre^-1 isoproturon caused 71 and 82% reduction in DW of R and S biotypes, respectively. Wheat was more sensitive to the mixture of isoproturon and ABT than the R biotype of P. minor. Reduced concentrations of ABT in the mixture from 10 to 2·5 mg litre^-1 increased the DW of the R biotype more than that of the S biotype. The R biotype metabolised [¹⁴C]isoproturon at a faster rate than the S biotype. ABT (5 mg litre^-1) inhibited the degradation of [¹⁴C]isoproturon in both biotypes of P. minor and in wheat. In the presence of ABT, about half of the applied [¹⁴C]isoproturon remained as parent herbicide in all the three species after two days. The metabolites were similar in the R and S biotypes and wheat as determined by co-chromatography with reference standards and mass spectroscopy (MS). ABT inhibited the appearance of the hydroxy and monomethyl metabolites and their conjugates in all the test plants. These results suggest that the activity of the enzymes responsible for the degradation of isoproturon is greater in the R than in the S biotype of P. minor, resulting in its rapid detoxification. Incorporation of the monooxygenase inhibitor ABT into the nutrient solution greatly inhibited the degradation of [¹⁴C]isoproturon in the R biotype and increased its phytotoxicity. Both hydroxylation and N-dealkylation reactions were found to be sensitive to ABT; inhibition of hydroxylation was greater than that of demethylation. Since ABT could not completely suppress isoproturon degradation, it is possible that more than one monooxygenase is involved. © 1998 SCI     

Residues of diflubenzuron and two of its metabolites in a forest ecosystem after control of the pine looper moth,Bupalus piniarius L

Diflubenzuron, 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea was used to control the pine looper population in about 1160 ha of Scots pine stand in eastern Finland in summer 1984. The control measure was effective, resulting in the collapse of the population in the treated area. Residues of diflubenzuron and two of its metabolites, 4-chloroaniline and 4-chlorophenylurea, were determined in water, pine needles, litter, humus, boleti and other wild mushrooms, bilberry (Vaccinium myrtillus L.) and cowberry (Vaccinium vitis-idaea L.) samples taken from this area. In water samples taken from the treated area diflubenzuron was still detected at concentrations of 0.1 μg litre^?1 2 months after application. No diflubenzuron was detected in this area the following year, nor outside the treated area. Neither metabolite was detected at any time. The sum of diflubenzuron and its metabolites in the litter layer was, on average, 0.7mg kg^?1 both 1 week and 1 month after the application. The next year, however, it had increased to 1.4 mg kg^?1. Diflubenzuron and its metabolites were not detected in the humus layer. The amount of diflubenzuron residues in the pine needles was, on average, 3.0 mg kg ^?1 1 day after the application, but in 2 months the level had decreased to 0.2-0.3 mg kg ^?1 or was not detectable. The following year the sum of diflubenzuron and its metabolites in two pine-needle samples was 0.3 and 1.6 mg kg ^?1. The sum of diflubenzuron and its metabolites in wild mushrooms was, on average, 0.07 mg kg ^?1 1 week after the application, but the following year no residues were detected. No residues were found in the boletus samples. The residues of diflubenzuron and its two metabolites in bilberries totalled, on average, 0.2 mg kg ^?1 1 day after the application, and 6 μg kg ^?1 the following year. The sum of diflubenzuron and metabolites in cowberries was, on average, 0.2 mg kg ^?1 1 month after application.     

Residues of the algicide endothal in water,soil and rice,after paddy field applications

In order to obtain residue data from the application of the algicide endothal in Italian rice paddy fields, two experiments were carried out using a 50 g kg^?1 granular formulation in a small pond and the same granular and two liquid formulations in actual paddy fields of the Italian rice growing area. Endothal decay in the pond water was very rapid, reaching residue levels of 0·01-1·02 mg litre^?1 in two days and 0·004-0·01 mg litre^?1 at the third day. The muddy soil of the pond was free from measurable endothal residues( <0·02 mg kg^?1). In the paddy-field waters, the endothal decay was slower, with an average half-life time of 3·3 days, independently of the type of formulation. The actual residues in water after 6 days ranged from 0·3 to 1·3 mg litre^?1 according to the initial amount of product applied, and, consequently, to the initial concentration in water. Rice samples collected at the normal harvest time from the two paddy fields, treated with three different formulations, showed no endothal residue at the minimum detectable level of 0·01 mg kg^?1.     

Structure—activity relationships in pyrethroid esters derived from substituted 2-phenoxy-3-methylbutanoic acids

Non-cyclopropane pyrethroid esters of different substituted 2-phenoxy-3-methylbutanoic acids have been synthesised using the three alcohols—3-phenoxybenzyl alcohol, α-cyano-3-phenoxybenzyl alcohol and 3, 4-methylene-dioxybenzyl alcohol. Among the 35 esters synthesised and tested against Culex quinquefasciatus Say, the Bancroftian filariasis vector, for both larvicidal and adulticidal activities, α-cyano-3-phenoxybenzyl 2-(4-fluorophenoxy)-3-methylbu-tanoate, with an LC₅₀ value of 2.5 × 10^?3 mg litre^?1 for larvicidal activity, and α-cyano-3-phenoxybenzyl-2-(4-chlorophenoxy)-3-methylbutanoate, with an LD₅₀ value of 30 times; 10^?4 ug insect^?1 for adulticidal activity, were found to be as effective as fenvalerate, a well-known non-cyclopropane pyrethroid ester. Structure-activity studies showed that the insecticidal activity is dependent on the nature and position of the substituent in the phenyl ring of the acid moiety and also on the type of alcohol moiety.     

The toxicity of cyromazine to Chironomus zealandicus (chironomidae) and Deleatidium sp. (leptophlebiidae)

The toxicity of cyromazine and a commercial formulation, ‘Vetrazin’®, to Chironomus zealandicus (thummi) Hudson and Deleatidium sp. was investigated. Under acute test conditions, the LC₅₀ values for each species were quite comparable. For C. zealandicus, the value varied according to instar, 100–400 mg litre^?1 for second- and third-instar to 1000–10000 mg litre^?1 for older fourth-instars. For the one size class of Deleatidium tested (c.10 mm long), the value was 300–400 mg litre^?1. High control mortalities of C. zealandicus limit that species' usefulness as an acute bioassay candidate. Under chronic test conditions, cyromazine showed a high toxicity to eggs or early-instar larvae of C. zealandicus. The maximum acceptable toxicant concentration for cyromazine against C. zealandicus was approximately 17.5 μg litre^?1. The possibility of water contamination at this level is discussed. Whole-of-life chronic tests with C. zealandicus indicated that the most susceptible stage was in the egg or soon after larval emergence. These results highlight the dangers of using short-term acute toxicity results to formulate environmental exposure limits for modern pesticides that do not have dysfunction of the nervous system as their mode of action.     

Effects of some foliar fungicides on the chrysomelid beetle Gastrophysa polygoni (L.)

The effects of the fungicides benomyl, thiophanate-methyl and triadimefon on the chrysomelid beetle Gastrophysa polygoni were investigated in the laboratory. Contact with a suspension of benomyl (1.5 g a. i. litre^?1 did not affect the hatchability of the eggs. Larvae were reared on shoots of knotgrass (Polygonum aviculare) that had been sprayed with suspensions of benomyl, ranging in concentration from 0.1 to 5.0 g a. i. litre^?1. The mortality to the adult stage, of larvae reared on shoots treated with concentrations of benomyl of 0.5 g a. i. litre^?1 and above, was significantly higher than that of control larvae. At concentrations of 2.0 g a. i. litre^?1 and above, no larvae survived to the adult stage. The LD₅₀ was 0.78 g a. i. benomyl litre^?1. The LT₅₀ values at concentrations of 1.0, 2.0 and 5.0 g a. i. benomyl litre^?1 were 22.6, 12.6 and 5.3 days, respectively. The mean weights of adults bred from larvae that had been reared on shoots treated with benomyl (0.5 and 1.0 g a. i. litre^?1) were significantly less than those of adults bred from control larvae. The mortality of larvae, reared on shoots of P. aviculare treated with triadimefon (0.5 g a. i. litre^?1) or thiophanate-methyl (1.0 g a. i. litre^?1), was also significantly higher than that of control larvae. Females kept on plants of P. aviculare treated with benomyl (1.5 g a. i. litre^?1) laid similar numbers of eggs to those kept on untreated plants, and the hatchability of the eggs was not affected.