Immobilization of the pesticide 2,4‐dichlorophenoxyacetic acid on a silica gel surface

A route for the immobilization of 2,4‐dichlorophenoxyacetic acid (2,4‐D) on silica gel has been developed. In the first step the precursor was prepared by reacting the silylating agent 3‐(trimethoxysilyl)propylamine with silica gel. Nitrogen analysis of this anchored compound showed the presence of 1.16 mmol of amine groups per gram of support. The herbicide was covalently bonded to the amine groups previously anchored onto silica gel. Infrared, [¹³C] and [²⁹Si] NMR spectra supported the reaction between the nitrogen of the amine group of the anchored silica with the carbon on the para‐position of the aromatic ring of 2,4‐D. The reaction yield, 90.3%, was confirmed through elemental analysis. © 2000 Society of Chemical Industry     

Evidence for 2,4‐D mineralisation in Mediterranean soils: impact of moisture content and temperature

BACKGROUND: The 2,4‐D degradation ability of the microbiota of three arable Mediterranean soils was estimated. The impact of soil moisture and temperature on 2,4‐D degradation was investigated. RESULTS: The microbiota of the three soils regularly exposed to 2,4‐D were able rapidly to mineralise this herbicide. The half‐life of 2,4‐D ranged from 8 to 30 days, and maximum mineralisation of ¹⁴C‐2,4‐D ranged from 57 to 71%. Extractable ¹⁴C‐2,4‐D and ¹⁴C‐bound residues accounted for less than 1 and 15% respectively of the ¹⁴C‐2,4‐D initially added. The highest amounts of ¹⁴C‐2,4‐D bound residues were recorded in the soil with the lowest 2,4‐D‐mineralising ability. Although all three soils were able to mineralise 2,4‐D, multivariate analysis revealed that performance of this degrading microbial activity was dependent on clay content and magnesium oxide. Soil temperature affected the global structure of soil microbial community, but it had only a moderate effect on 2,4‐D‐mineralising ability. 2,4‐D‐mineralising ability was positively correlated with soil moisture content. Negligible 2,4‐D mineralisation occurred in all three soils when incubated at 10 or 15% soil moisture content, i.e. within the range naturally occurring under the Mediterranean climate of Algeria. CONCLUSION: This study shows that, although soil microbiota can adapt to rapid mineralisation of 2,4‐D, this microbial activity is strongly dependent on climatic parameters. It suggests that only limited pesticide biodegradation occurs under Mediterranean climate, and that arable Mediterranean soils are therefore fragile and likely to accumulate pesticide residues. Copyright © 2009 Society of Chemical Industry     

Insecticidal activity and mode of action of 2,4‐diaminopyrimidines

Three 2,4‐diaminopyrimidines were tested against several insect species. They were active against lepidopteran pests with LC₅₀ values <3 mg liter⁻¹ for most species tested. They were also active against two‐spotted spider mite, Tetranychus urticae, (LC₅₀ 10–40 mg liter⁻¹). Folinate, but not hypoxanthine or thymidine was found to be an effective rescue agent, requiring a concentration of 100 mg liter⁻¹ diet to rescue half of the intoxicated larvae. The results confirm dihydrofolate reductase to be the site of action for these insecticides and are consistent with the mode of action of folinate rescue in mammals. © 2000 Society of Chemical Industry     

Awnless barley (Hordeum vulgare L.) response to hand weeding and 2,4‐D application at two growth stages under Mediterranean environment*

A field study was conducted to determine the response of two awnless barley genotypes (JF//Barsoy/Ri and VA 92‐42‐46) to hand weeding (practised monthly during the growing seasons) and 2,4‐D application at different growth stages during the rainy seasons of 1999 and 2000 at Houfa in northern Jordan. JF//Barsoy/Ri gave significantly higher grain yield than VA 92‐42‐46; 820 and 923 kg ha^?1 during 1999 and 2000, respectively. Differences in weed number and fresh weight were significant among various treatments in both seasons. In both growing seasons, yield reductions occurred when 2,4‐D was applied to barley at the stage 11–18 of BBCH scale (leaves 1 to 8 unfolded) and the stage 22–28 (2–8 tillers detectable). Hand weeding proved the best weed control and was more effective than 2,4‐D applications.     

Multiple resistance of Papaver rhoeas L. to 2,4‐D and acetolactate synthase inhibitors in four European countries

The issue of cross‐ or multiple resistance to acetolactate synthase (ALS) inhibitors and the auxinic herbicide 2,4‐D was investigated in Papaver rhoeas L., a common and troublesome weed in winter cereals, in a broad‐scale study across four European countries. A combination of herbicide sensitivity bioassays and molecular assays targeting mutations involved in resistance was conducted on 27 populations of P. rhoeas originating from Greece (9), Italy (5), France (10) and Spain (3). Plants resistant to the field rate of 2,4‐D were observed in 25 of the 27 populations assayed, in frequencies ranging from 5% to 85%. Plants resistant to ALS‐inhibiting herbicides (sulfonylureas) were present in 24 of the 27 populations, in frequencies ranging from 4% to 100%. Plants resistant to 2,4‐D co‐occurred with plants resistant to sulfonylureas in 23 populations. In four of these, the probability of presence of plants with cross‐ or multiple resistance to 2,4‐D and sulfonylureas was higher than 0.5. ALS genotyping of plants from the field populations or of their progenies, identified ALS alleles carrying a mutation at codon Pro197 or Trp574 in 2,4‐D‐sensitive and in 2,4‐D‐resistant plants. The latter case confirmed multiple resistance to 2,4‐D and ALS inhibitors at the level of individual plants in all four countries investigated. This study is the first to identify individual plants with multiple resistance in P. rhoeas, an attribute rarely assessed in other weed species, but one with significant implications in designing chemical control strategies.     

Callose and β‐1,3‐glucanase inhibit Phytophthora cinnamomi in a resistant avocado rootstock

Phytophthora root rot (PRR) of avocado, caused by Phytophthora cinnamomi, is a significant threat to sustainable production wherever the crop is grown. Resistant rootstocks in combination with phosphite applications are the most effective options for managing this disease. Recently, the mechanisms underpinning PRR resistance have been investigated by the avocado community. Here, biochemical assays and confocal and scanning electron microscopy were used to investigate early defence responses in PRR resistant and ‐susceptible avocado rootstocks. Zoospore germination and subsequent hyphal growth for the pathogen were significantly inhibited on the surface of resistant avocado roots. When penetration occurred in the resistant R0.06 rootstock, callose was deposited in the epidermal cells, parenchyma and cortex of roots. In addition, β‐1,3‐glucanase was released early (6 h post‐inoculation, hpi) in response to the pathogen, followed by a significant increase in catalase by 24 hpi. In contrast, susceptible R0.12 roots responded only with the deposition of lignin and phenolic compounds incapable of impeding pathogen colonization. In this study, PRR resistance was attributed to a timely multilayered response to infection by P. cinnamomi.