Photolysis of chlorsulfuron and metsulfuron-methyl in methanol

Photolysis of chlorsulfuron and metsulfuron-methyl was studied in methanol under UV light. Their rates of primary photolysis followed first-order kinetics. The main photoproducts were identified as 2-methoxy-4-methyl-1,3,5-triazin-6-amine, 2-chloro-benzenesulfonamide and methyl 2-(aminosulfonyl)benzoate, which entailed the cleavage of the two N–C ureic bonds. Further photolysis of benzenesulfonamide derivatives involved oxidation of −NH₂, cyclisation with loss of CH₃OH, and scission of the C–S bond A trace of methyl o-mercaptobenzoate was also detected. The corresponding photolysis pathways of chlorsulfuron and metsulfuron-methyl were tentatively proposed. © 1999 Society of Chemical Industry     

Response of Brassica napus in tissue culture to metsulfuron-methyl and chlorsulfuron

A herbicide bioassay based on tissue cultures of Brassica napus L. was evaluated with selected sulfonylurea herbicides. Data were analysed by fitting the results to a log-logistic dose–response model. Within an experiment, the non-linear regression models were fitted simultaneously to the individual dose–response curves. The results obtained showed good response to even low concentrations of herbicide, with detection limits in the range 0.008–0.69 nmol L^?1 for chlorsulfuron and 0.02–0.13 nmol L^?1 for metsulfuron. The reproducibility of the assays, on the basis of coefficient of variation of the ED₅₀ values, was found to be 44% for chlorsulfuron and 48% for metsulfuron measurements. Assay of herbicide dissolved in aqueous soil extract showed significant interference from this matrix on the response, requiring a five times dilution of the extract to overcome this matrix effect.     

Adsorption and degradation of chlorsulfuron and metsulfuron-methyl in soils from different depths

Adsorption and degradation rates of chlorsulfuron and metsulfuron-methyl were measured in soil taken from depths of 0–20, 20–40 and 40–60 cm at eight sites. Adsorption of both herbicides was negatively correlated with soil pH, and positively correlated with soil organic matter content. When two soils with very high organic matter were excluded from the calculations, the correlations with organic matter content were no longer statistically significant but those with soil pH were affected only slightly. Degradation rates of both herbicides generally decreased with increasing depth in the soil and were positively correlated with microbial biomass and negatively correlated with soil pH. The possible significance of the results to persistence of the herbicides in the field is discussed.     

The relative movement and persistence in soil of chlorsulfuron, metsulfuron-methyl and triasulfuron

Summary. Adsorption and degradation rates of triasulfuron in 8 different soils were negatively correlated with soil pH and were generally lower in subsoils than in soils from the plough layer. The half-life at 20°C varied from 33 days in a top soil at pH 5·8 to 120 days in a subsoil at pH 7·4. Adsorption distribution coefficients in these two soils were 0·55 and 0·19, respectively. Movement and persistence of residues of chlorsulfuron, triasulfuron and metsulfuron-methyl were compared in a field experiment prepared in spring 1987. Triasulfuron was less mobile in the soil than the other two compounds. Residues of all three herbicides were largely confined to the upper 40–50 cm soil 148 days after application. With an initial dose of 32 g ha⁻¹, residues in the surface soil layers were sufficient to affect growth of lettuce and sugar-beet sown approximately one year after application. Laboratory adsorption and degradation data were used with appropriate weather data in a computer model of herbicide transport in soil. The model gave good predictions of total soil residues during the first five months following application, and also predicted successfully the maximum depth of penetration of the herbicides into the soil during this period. However, more herbicide was retained close to the soil surface than was predicted by the model. The model predicted extensive movement of the herbicides in the soil during winter but did not predict that residues sufficient to affect crop growth could be present in the upper 15–20 cm soil after one year.     

Kinetics and mechanism of the hydrolysis of imidacloprid

The kinetics of the hydrolysis of imidacloprid were studied at different pH values and under various temperatures. Imidacloprid was found to be stable in acidic and neutral water, but readily hydrolysed in alkaline water. The main hydrolysis product was found to be 1-[(6-chloro-3-pyridinyl)methyl]-2-imidazolidone, and a mechanism for its formation is proposed. © 1999 Society of Chemical Industry     

Determination of the sulfonylurea herbicides chlorsulfuron and metsulfuron-methyl in soil,water and plant material by gas chromatography of their pentafluorobenzyl derivatives

The measurement of the sulfonyl urea herbicides, chlorsulfuron and metsulfuron-methyl as pentafluorobenzyl derivatives has been investigated and the kinetics of reaction optimised. The reaction product was identified by mass spectroscopy as N,N-bis(pentafluorobenzyl)-2-chlorobenzenesulfonamide. Amounts of herbicide derivative as low as 0·1 pg per injection can be detected. Suitable conditions for both packed and capillary chromatography are given. Application of the method to residue determination is discussed and the method is shown to be suitable for residues in soil and water but less so for plant material.     

The mechanism of differential response of wheat cultivars to chlorsulfuron

Wheat (Triticum aestivum L.) cultivars showed differential tolerance to chlorsulfuron. Cultivar Kotare showed no injury symptoms following foliar applications of chlorsulfuron at 15 or 60 g a.i. ha^?1, while cultivars Rongotea and Lancer showed early damage in pot and field experiments at both rates of chlorsulfuron. Cultivars Abele and Jasper were intermediate in their response. The number of spikelets per ear was the only yield component affected by chlorsulfuron and was reduced in Lancer and Rongotea. Retention, uptake and transiocation of chlorsulfuron were not different between Kotare and Ron-gotea. Within 48 h of application, Kotare metabolized 92–2% of [¹⁴C]chlorsulfuron, while Lancer and Rongotea metabolized only 43–5% and 63% of the herbicide, respectively. The concentration of chlorsulfuron in young tissues of Kotare, Lancer and Rongotea, 48 h after application was calculated as 1.2, 31.9 and 15.6 ng g^?1 dry weight, respectively. It is concluded that differential rates of metabolism are the main reason for differences in sensitivity to chlorsulfuron between the wheat cultivars tested. Le mécanisme des différences de tolérance au chlorsulfuron entre variétés de blé Des variétés de blé (Triticum aestivum L.) ont montré des différences de tolérance au chlorsul-furon. On n'a aucun symptôme de phytotoxicité sur la variété‘Kotare’ après une application foliaire de chlorsulfuron à 15 ou 60 g m.a. ha^?1, alors que les variétés ‘Rongotea’ et ‘Lancer’ présentaient des symptômes précoces aux deux doses, dans des expériences en pot et au champ. La réponse des variété‘Abele’ et ‘Jasper’était intermédiaire. Le nombre de grains par épillet était la seule composante du rendement affectée parle chlorsulfuron et était réduit chez Lancer et Rongotea. La rétention, la pénétration et la migration de chlorsulfuron n'était pas différentes entre Kotare et Rongotea. Quarante huit heures après le traitement, Kotare avait metabolise 92,2% du [¹⁴C]chlorsulfuron, alors que Lancer et Rongotea ne métabolisaient que respectivement 43,5 et 63% de l'herbicide. La concentration de chlorsulfuron dans les tissus jeunes de Kotare, Lancer et Rongotea 48 h après la traitement a étéévaluée à respectivement 1,2,31,9 et 15,6 ng g^?1 de matière sèche. Il est conclu que des différences de vitesse de métabolisation sont la raison principale des différences de sensibilité au chlorsulfuron observées chez les variétés de blé testées. Mechanismen der unterschiedlichen Reaktion von Weizensorten auf Chlorsulfuron-Behandlun-gen Es wurde eine unterschiedliche Toleranz bei Weizensorten (Triticum aestivum L.) gegenüber Chlorsulfuron-Behandlungen beobachtet. Bei der Sorte ‘Kotare’ traten nach Behandlungen mit 15 oder 60 g AS ha keine Schadsymtome auf, während die Sorten ‘Rongotea’ und ‘Lancer’ sowohl in Topfals auch in Freilandversuchen bei beiden Dosen frühe Schädigungen erlitten; die Sorten ‘Abel’ und ‘Jasper’ reagierten mittelstark. Unter den Ertragskomponenten war nur die Zahl der Ährchen pro Ähre betroffen, sie war bei ‘Lancer’ und ‘Rongotea’ reduziert. Aufnahme und Translokation des Wirkstoffs waren bei ‘Kotare’ und ‘Rongotea’ gleich. Bei ‘Kotare’ war [¹⁴C]Chlorsulfuron 48 h nach der Applikation zu 92,2 % metabolisiert, bei ‘Rongotea’ zu 63 % und bei ‘Lancer’ zu 43,5 %. In jungen Geweben dieser Sorten lagen die Chlor-sulfuron-Konzentrationen 48 h nach der Anwendung bei 1,2, 15,6 und 31,9 ng g^?1 TM. Die unterschiedlichen Metabolisierungsraten bei den untersuchten Weizensorten wurden für den Hauptgrund für die Toleranzunterschiede gegenüber Chlorsulfuron gehalten.     

光敏型氯磺隆与普通氯磺隆的控草效果比较

比较了光敏型氯磺隆与普通氯磺隆不同剂量对各种杂草的控制效果。结果显示在低剂量下,普通氯磺隆的控草效果略高于光敏型氯磺隆。在中量、高量和倍量下,两种制剂控草效果差异不大。     

Aerobic soil metabolism of metsulfuron-methyl

A laboratory study was conducted to determine the degradation rates and identify major metabolites of the herbicide metsulfuron-methyl in sterile and non-sterile aerobic soils in the dark at 20°C. Both [phenyl-U-¹⁴C]- and [triazine-2-¹⁴C]metsulfuron-methyl were used. The soil was treated with [¹⁴C]metsulfuron-methyl (0.1 mg kg⁻¹) and incubated in flow-through systems for one year. The degradation rate constants, DT₅₀, and DT₉₀ were obtained based on the first-order and biphasic models. The DT₅₀ (time required for 50% of applied chemical to degrade) for metsulfuron-methyl, estimated using a biphasic model, was approximately 10 days (9–11 days, 95% confidence limits) in the non-sterile soil and 20 days (12–32 days, 95% confidence limits) in the sterile soil. One-year cumulative carbon dioxide accounted for approximately 48% and 23% of the applied radioactivity in the [phenyl-U-¹⁴C] and [triazine-2-¹⁴C]metsulfuron-methyl systems, respectively. Seven metabolites were identified by HPLC or LC/MS with synthetic standards. The degradation pathways included O-demethylation, cleavage of the sulfonylurea bridge, and triazine ring opening. The triazine ring-opened products were methyl 2-[[[[[[[(acetylamino)carbohyl]amino]carbonyl]amino] carbonyl]-amino]sulfonyl]benzoate in the sterile soil and methyl 2-[[[[[amino[(aminocarbonyl)imino]methyl] amino]carbonyl]amino]sulfonyl]benzoate in the non-sterile soil, indicating that different pathways were operable. © 1999 Society of Chemical Industry     

Degradation of primisulfuron-methyl and metsulfuron-methyl in soil

A newly developed chemical assay was used to determine the degradation in soil of two sulfonylurea herbicides, primisulfuron-methyl and metsulfuron-methyl, under both controlled and field conditions. The results from the chemical assay were compared with those from traditional bio-assays for determination of persistence in the field. Phytotoxic effects of these herbicides were not observed after 6 weeks following application to an acidic (pH 5.7) soil with high organic matter content (7.3% o.c). Half-lives of 13 to 29 days were measured for primisulfuron-methyl at different soil-water contents and temperatures while those for metsulfuron-methyl ranged from 8 to 36 days. The rate of degradation of metsulfuron-methyl was more sensitive to temperature than that of primisulfuron-methyl. Persistence in the field was shorter than expected considering the results from the controlled environment studies. However, determination of the persistence by both chemical assay and bioassay methods produced very similar results.     

安全剂R-28725保护玉米免受绿磺隆药害的机理

在盆栽和田间小区模拟条件下，测定了安全剂R-28725对玉米的株高和株鲜重的影响，确定了玉米体内GSH及其支链氨基酸的变化。结果发现：当绿磺隆的使用量为2．5、5、10g/hm^2时，R-28725能够明显提高玉米株高、株鲜重，混喷的效果显著高于其它处理。在绿磺隆的使用量为5g/hm^2时，使用R-28725混喷处理，玉米的产量为对照的101．68％。R-28725能够直接提高玉米幼苗中体内谷胱甘肽(GSH)含量，在绿磺隆浓度为1μg／kg，使用R-28725浸种处理，玉米幼苗中体内GSH含量增加27．83％，说明R-28725能够诱导绿磺隆与谷胱甘肽的轭合，从而达到解毒的目的。     

Kinetics of hydrolysis of atrazine in aqueous fulvic acid solution

The hydrolysis of atrazine in aqueous fulvic acid solution followed first-order kinetics with respect to the herbicide concentration. The half-life of atrazine, calculated from first-order plots, was lowest at low pH and increased as the pH of the reaction mixture increased. Increase in fulvic acid concentration resulted in a higher hydrolysis rate constant and a shortened half-life but had no effect on the activation energy. However, the latter increased with increase in pH of the reaction mixture. The only product identified after hydrolysis in fulvic acid solution was 2-ethylamino-4-hydroxy-6-isopropylamino-1,3,5-triazine.     

Synergistic joint action of MCPA ester and metsulfuron-methyl

MCPA is antagonistic to a range of herbicides but there is limited research on its compatibility with other broad-leaved weed herbicides. In this study we assessed the joint action of MCPA ester and metsulfuron-methyl on Brassica napus L. using the additive dose model (ADM). The fresh weight responses for selected ratios of the mixture were plotted on the ADM and compared to the predicted mixture response at three assessment levels - 50, 75 and 90% control. The mixture demonstrated increasing synergism as the response level increased from 50 to 90%. This result for MCPA ester is in marked contrast to that of the MCPA amine formulation, which was shown in previous studies to be antagonistic towards sulfonylurea herbicides. Formulation is the major deciding factor in determining the compatability of phenoxy herbicides with other herbicides.     

Metabolism of chlorsulfuron by tolerant broadleaves

The ability of flax and black nightshade to metabolize chlorsulfuron was studied to determine if metabolism contributes to tolerance and to identify any metabolites produced. Plant leaves were treated with [¹⁴C]chlorsulfuron for a 24-hr period. The metabolites were extracted, separated by HPLC, and characterized. Mass spectral analysis and independent synthesis confirmed a major metabolite (B-1) as 2-chloro-N-{[4-(hydroxymethyl)-6-methoxy-1,3,5-triazin-2-yl]amino-carbonyl}benzenesulfonamide. A second major metabolite (B) was determined to be a carbohydrate conjugate of B-1. Plants were more tolerant to B-1 applications than to chlorsulfuron. These results suggest that metabolism may be the basis of selectivity to chlorsulfuron for tolerant broadleaf plants as well as for grasses.     

Variability of bioassays with metsulfuron-methyl in soil

A total of 74 independently run bioassays with soil incorporated metsulfuron-methyl from 12 different laboratories was analysed by a logistic dose-response curve to assess the precision of regression parameters and relate ED₅₀ to soil properties. The potency in terms of ED₅₀ of metsulfuron-methyl in Brassica rapa L., which was used by all laboratories, varied between 0.05 and 3.9 g a.i. ha^-1. ED₅₀ was negatively correlated with pH and positively correlated with organic matter. The majority of laboratories had ED₅₀ within the interval 0.1-1.0 g a.i. ha^-1. At one laboratory using three test species, the most sensitive species was Beta vulgaris L. followed by Brassica rapa L. and Lepidium sativum L. The coefficients of variation were smallest for the ED₅₀ and ED₉₀ response levels and largest for the ED₁₀. The slope of the response curves had considerably lower coefficients of variation than the EDs. The results are discussed in relation to a previous collaborative bioassay study. Finally it is suggested that standardization of bioassays with herbicides could be achieved in the same way as standardization of chemical analyses.     

Acetolactate synthase activity and chlorsulfuron sensitivity of wheat cultivars

Differences were observed in the sensitivity of three wheat (Triticum aestivum L.) cultivars to chlorsulfuron. Shoot dry weight was reduced by foliar applications of chlorsulfuron to a greater extent in cv. Rongotea than in cvs Lancer and Kotare. There was no difference between these cultivars in the specific activity of acetolactate synthase (ALS) enzyme extracted from leaves or roots. Moreover, chlorsulfuron inhibited ALS from the wheat cultivars to the same extent in?vitro. ALS measurement in vivo showed that after 15 h of incubating excised leaf tissues with chlorsulfuron, there was a greater reduction in ALS enzyme activity in Rongotea than in the other cultivars. Furthermore, 1 day after a foliar application of chlorsulfuron, in vitro ALS activity in leaves was reduced more in Rongotea than in Lancer or Kotare. Recovery of the enzyme activity following chlorsulfuron application was quicker in Kotare than in Lancer or Rongotea. It is concluded that differences in sensitivity of these wheat cultivars to chlorsulfuron are not due to differential ALS sensitivity or level, but may be due to differential rates of herbicide metabolism.     

Phytotoxicity and persistence of chlorsulfuron as affected by activated charcoal

Two bioassay procedures, using petri-dishes and pots, based on the root growth of pregerminated maize were used to study the residual phytotoxicity of chlorsulfuron under field conditions. Both bioassay procedures appeared to be equally reproducible and sensitive with residues of chlorsulfuron being detectable from 0·25 to 10·0 ng g^-1. The results indicated that persistence, movement and phytotoxicity increased with increasing rate of chlorsulfuron, but persistence of the herbicide was shorter in wet compared to dry field conditions. As little as 1 g a.i. ha^-1 of incorporated chlorsulfuron under warm and dry field conditions caused a stunting effect on maize plants (Hybrid F₁, Damon) and reduced yield by 53% compared to untreated control plants; while 5·0 and 10·0 g a.i. ha^-1 of incorporated chlorsulfuron killed all maize plants. However, under wetter field conditions, incorporated chlorsulfuron at 1·25, 2·5 and 5·0 g a.i. ha^-1 caused a stunting effect on maize plants (Hybrid F₁, ARIS) and decreased yield by 16, 57 and 92%, respectively, compared to untreated control. Incorporation of 50 kg ha^-1 of activated charcoal inactivated completely chlorsulfuron incorporated at 1·25 and 2·5 g a.i. ha^-1 and did not affect yield of maize compared to untreated control. Higher rates of activated charcoal such as 100 and 200 kg ha^-1 also inactivated chlorsulfuron applied at 1·25–5·0 g a.i. ha^-1 and did not affect grain yield of maize. Phytotoxicité et persistance du chlorsulfuron Deux méthodes d'essais biologiques, à savoir en boîte de Petri ou en pot, Basées sur la croissance des racines de maïs prégermé ont été utilisées pour étudier la phytotoxicité résiduelle du chlorsulfuron en conditions de plein champ. Les deux méthodes sont également reproductibles et sensibles à des niveaux de détection pour les résidus de chlorsulfuron de 0,25 à 10 ng g^-1. Les résultats montrent que la persistance et la phytotoxicité augmentent avec des doses croissantes de chlorsulfuron, mais la persistance est plus courte dans des conditions de plein champ humides que séches. Une dose aussi faible que 1 g de matiére active ha^-1 de chtorsulfuron incorporé en conditions chaudes et séches a causé un effet retard sur les plants de maïs (hybride F₁, Damon) et a réduit de 53% le rendement par rapport au témoin non traité; des doses de 5 à 10 g de matiére active ha^-1 de chlorsulfuron incorporé ont tué tous les pieds de maïs. Cependant, en conditions plus humides, le chlorsulfuron incorporéà 1,25, 2,5 et 5 g de matiére active ha^-1 a causé un effet retard sur le maïs (hybride F₁ ARIS) et a réduit le rendement par rapport au témoin non traité respectivement de 16, 57 et 92%. L'incorporation de 50 kg ha^-1 de charbon actif a complément inactive le chlorsulfuron incorporéà 1,25 et 2,5 g de matiére active ha^-1 et n'a pas eu de répercussion sur le rendement par rapport au témoin non traité. Des doses plus élevées de charbon actif comme 100 et 200 kg ha^-1 ont inactivé le chlorsulfuron appliquéà 1,25–5 g matiére active ha^-1et n'ont pas affecté le poids en grain du maïs. Ueber die Beeinflussung von Phytotoxizität und Wirkungsdauer von Chlorsulfuron durch Aklivkohle Zum Studium der Residualwirkung von Chlorsulfuron unter Feldbedingungen wurden zwei Bioassaymethoden, eine in Petrischalen, die andere in Töpfen, eingesetzt. Beide Methoden basierten auf dem Wurzelwachstum von vorgekeimtem Mais. Es zeigte sich, dass beide Versuchsverfahren in gleichem Masse reproduzierbar und empfindlich und in der Lage sind Rückstände von 0,25–10,0 ng g^-1 nachzuweisen. Mit steigender Chlorsulfurondosis wurde eine zunehmende Phytotoxizität, Persistenz und Mobilität des Herbizids festgestellt. Die Persistenz war unter feuchten Feldbedingungen kürzer als bei Trockenheit. Bis zu einer unteren Grenze von 1,0 g a.i. ha^-1 verursachte inkorporiertes Chlorsulfuron, unter trockenen und warmen Feldbedingungen an Mais (Hybride F₁, Damon) Wachstumshemmungen und Erntereduktionen von 53%, verglichen mit unbehandelten Kontrollpflanzen. Unter feuchteren Bedingungen, jedoch, hatten 1,25, 2,5 and 5,0 g a.i. ha^-1 eingearbeitetes Chlorsulfuron an Mais (Hybride F₁ ARIS) Wachstumshemmungen und Ernteverluste von 16, 57 und 92% zur Folge. Die Einarbeitung von 50 kg ha^-1 Aktivkohle inaktivierte 1,25 g und 2,5 g ha^-1 inkorporierles Chlorsulfuron vollständig und hatte keinerlei negative Auswirkungen auf die Maisernte, im Vergleich zu unbehandelten Kontrollen. Höhere Mengen von Aktivkohle, wie 100 und 200 kg ha^-1, inaktivierten auch Chlorsulfuronmengen von 1,25–5 g ha^-1 und hatten keinen Einfluss auf den Kömerertrag.     

Rates of chlorsulfuron degradation in three Brazilian oxisols

The degradation of chlorsulfuron was studied in laboratory experiments in three oxisols from south and south–east Brazil. Three soil profiles were sampled by horizon, and classified according to USDA soil taxonomy and the Brazilian system. Degradation assays were made to evaluate the influence of temperature, humidity and liming on chlorsulfuron decomposition. Further experiments were set up to study enhanced biodegradation. Abiotic degradation was also studied in sterile soils, to evaluate, by comparison with non–sterile soils, the role of microorganisms in degradation. The degradation always followed first–order kinetics and was generally faster in samples from A than B horizons. An increase in temperature (from 25 to 40°C) increased chlorsulfuron degradation. Further, an increase in moisture content increased chlorsulfuron degradation in samples from the A horizons of all soils, whereas for two out of three soils, degradation in samples from the B horizon was greater at lower water content. The biotic contribution to degradation was significant only for the soil with higher fertility. Soil liming significantly increased chlorsulfuron half–life in all samples. Significant enhancement of degradation (decrease in half–life on reapplication) was observed only in soil from A horizons, where a higher microbial activity was likely.     

Kinetics and products of the hydrolysis of 3,4-dihydroprecocene I 3,4-epoxide in aqueous organic solvents

The hydrolysis of 3, 4-dihydroprecocene I 3, 4-epoxide (3, 4-dihydro-7-methoxy-2, 2-dimethyl-3, 4-epoxy-2H-benzo[b]pyran), the putative ultimate cytotoxin of the insect growth regulator precocene I (7-methoxy-2, 2-dimethyl-2H-benzo[b]pyran), has been studied and found to exhibit first-order kinetics [k = 0.17 s^?1 in 10 mm-phosphate buffer pH 7.0, containing 1, 4-dioxane (1 + 1 by volume), ionic strength 0.1]. Plots of log k versus pH, and k versus buffer concentration, suggest that the reaction is subject to both specific and general acid catalysis. High-performance liquid chromatography showed the reaction products to be predominantly the corresponding stereoisomeric diols (3, 4-dihydro-7-methoxy-2, 2-dimethyl-2H-benzo[b]pyran-3, 4-diol), the trans : cis ratio of which varied from 1.8: 1 to 2.2: 1 but was constant over the pH range 6-8, at a given buffer concentration. The results indicate that acid-catalysed hydration of 3, 4-dihydroprecocene I 3, 4-epoxide is an S_N1 reaction, involving a trigonally hybridised carbocation at C4, even at physiological pH. Similar studies on 3, 4-dihydroiso-precocene I 3, 4-epoxide (3, 4-dihydro-6-methoxy-2, 2-dimethyl-3, 4-epoxy-2H-benzo-[b]pyran), a biologically inactive isomer of 3, 4-dihydroprecocene I 3, 4-epoxide suggest that an S_NI mechanism also contributes to its hydrolysis, but the rate constant is 4000 times lower than that for 3, 4-dihydroprecocene I 3, 4-epoxide. Knowledge of the reactivity and mechanism of reaction of such compounds forms an important part of the basis for rational prediction of biological activity in precocene analogues, and hence their possible use as pest control agents.