A possible mechanism for the selective herbicidal activity of iodide in relation to thiocyanate content

In an in vivo study, the rate of iodide oxidation by horseradish peroxidase was found to be reduced by the addition of ammonium thiocyanate to the system. The seleetive herbicidal activity of sodium iodide towards dwarf bean, pea, kale and cabbage was tested while the poicnlial ihioeyanale conteni of these platits was measured, A good relationship between inereasmg thiocyanale content and inereasing resistance to iodide was observed.     

Rational herbicide design by synthesis of inhibitors for the peroxidase catalysed oxidation of indolyl-3-acetic acid

An attempt has been made to design a herbicide by synthesising active site directed irreversible inhibitors for the peroxidase-catalysed oxidation of indolyl-3-acetic acid (IAA). A variety of substituted indoles were prepared and found to bind reversibly to the enzyme, but none produced any progressive inhibition, nor showed any herbicidal activity. This may be related to the fact that the inhibitors can be degraded by peroxidase in vitro since, if this occurred in the plant, the compounds could not then interfere with IAA oxidation.     

Synthesis and insecticidal activity of lipophilic amides. Part 4: The effect of substituents on the phenyl group of 6-phenylhexa-2,4-dienamides

Substituted phenylacetaldehydes, made by homologation of the benzaldehydes by Wittig condensation with a methoxymethylene ylid, were condensed under Wadsworth-Emmons conditions to give the substituted N-(2-methylpropyl)-6-phenylhexa-2,4-dienamides. Electron withdrawing substituents favoured the formation of the unwanted 3,5-diene isomer. Insecticidal activity was lowered by most substituents examined, but was retained or even enhanced by halogen atoms at the m- or p-positions. At the m-position, activity decreased as size of halogen increased.     

Effect of indole-acetic acid (IAA) on the development of symptoms caused by <Emphasis Type="Italic">Pythium ultimum</Emphasis> on tomato plants

The effect of indole-acetic acid (IAA) on the development of symptoms caused by Pythium ultimum on tomato plants was investigated using different bioassays. Application of IAA (5 μg ml⁻¹) on tomato seedlings inoculated with P. ultimum did not affect their emergence suggesting that IAA did not affect the severity of Pythium damping-off. However, IAA was shown to influence the development of P. ultimum symptoms on tomato plantlets. Low concentrations of IAA (0–0.1 μg ml⁻¹) within the rhizosphere of plantlets increased the severity of the symptoms caused by P. ultimum, while higher concentrations (10 μg ml⁻¹), applied either by drenching to the growing medium or by spraying on the shoot, reduced the symptoms caused by this pathogen. In addition, the study demonstrated that P. ultimum produces IAA in liquid culture amended with L-tryptophan, tryptamine or tryptophol (200 μg ml⁻¹) and in unamended culture.     

Shifts in disease resistance induced by growth regulators

Experiments on the effect of various compounds with plant growth regulating activity led to the hypothesis that conditions inhibitory to indoleacetic acid (IAA) action or leading to a decrease in the IAA level in cucumber seedlings would be unfavourable for the development of cucumber scab, caused byCladosporium cucumerinum. Susceptibility decreased as the result of treatment with growth retardants, which cause an increase in IAA-oxidase activity in the plants, whereas application of indoleacetic acid or compounds expected to decrease the rate of oxidative breakdown of IAA in the seedlings resulted in an increase of susceptibility. Growing the plants under various periods of illumination also influenced both the susceptibility of the plants and the IAA-oxidase activity in the hypocotyl tissue.To obtain further information about the relation between the increase in resistance and the increase in the rate of IAA oxidation, the effect of one compound, viz. L-threo-β-phenylserine (abbr. phenylserine) was studied in more detail. The rate of oxidative breakdown of IAA was increased in extracts of hypocotyls and cotyledons of plants treated with phenylserine as compared with extracts of tissue of untreated plants. Extracts of phenylserine-treated plants were found to contain a higher cofactor and/or a lower inhibitor content than those of control plants. The substances involved were not identified, but this result may indicate a shift in the concentrations of various phenols in the tissue.The question must remain open whether a shift in the concentration of phenols some-how effected by phenylserine treatment determines both degree of susceptibility and rate of IAA oxidation independently, or whether the rate of IAA breakdown and the resulting change in IAA content in the plants is directly related to the degree of susceptibility.     

Indole derivatives enhance resistance against the rice blast fungus <Emphasis Type="Italic">Magnaporthe oryzae</Emphasis>

In leaves pretreated with an indole derivative [indole-3-acetic acid (IAA) tryptamine, or tryptophan], blast lesion formation was suppressed compared to those treated with distilled water (DW) as a control. Phenylalanine ammonia-lyase (PAL) activity and PAL expression were significantly enhanced in the IAA- or tryptophan-pretreated leaves, but not in tryptamine-pretreated leaves. This induction of resistance was inhibited by pretreatment with a PAL inhibitor, α-aminooxyacetic acid, in IAA- and in tryptophan-treated leaves, but not in tryptamine-treated leaves. This study strongly shows that the indole derivatives IAA tryptamine and tryptophan can enhance a disease resistance mechanism that is supported by different metabolic pathways.     

Synthesis and insecticidal activity of lipophilic amides. Part 7. Alternative aromatic groups for phenyl in 6-phenylhexa-2,4-dienamides

Synthesis of a wide range of analogues of the lead compound, N-2-methylpropyl-6-phenylhexa-2,4-dienamide, in which phenyl was replaced by other aromatic systems is reported. In cases where rearrangement rendered the N-2-methylpropyl compound less accessible, N-2,2-dimethylpropyl substitution was used, because rearrangement was then suppressed. Several of the groups examined, for instance 2-naphthyl, enhanced insecticidal activity, and when appropriately substituted, particularly with halogen, led to the most active compounds discovered in this series.     

Mode of action of thiocyanates and iodides in aminotriazole formulations

Ammonium thiocyanate ( I ) was shown to inhibit the oxidation of aminotriazole (3-amino-1,2,4-triazole) in two free-radical generating systems: (a) riboflavin photo-sensitised oxidation; and (b) oxidation by hydroxyl radicals. Evidence from in-vitro studies is presented to show that I could enhance aminotriazole performance by being preferentially oxidised within the leaf, thereby preventing aminotriazole free-radical formation and subsequent conjugation with amino acids and other compounds. This opens up the possibility of a whole new range of additives which could enhance translocation by inhibiting free-radical reactions. A comparison of possible inhibitors revealed that cyanides, iodides and perhaps bromides may be of use in this respect. In addition to inhibiting free-radical reactions, I and potassium iodide ( II ) were shown to have a considerable effect on the uptake of aminotriazole by bean leaves (Phaseolus vulgaris var. Canadian Wonder). In the absence of additives, uptake of aminotriazole was negligible (1.8%); in the presence of a 1:1 molar ratio of I or II , uptake of aminotriazole was increased to 36.6% and 54.2% respectively. At a 3:1 molar ratio of additive:aminotriazole, the respective figures were 63.5% and 81.0%. II appeared to be the more efficient of the two additives at higher humidity. However, the results and observations indicated that the situation may be reversed under low-humidity conditions.     

The colonization processes of Myrtus communis by strains of Pseudomonas savastanoi with a differential ability to produce phytohormones

The ability to produce indole-3-acetic acid (IAA) through the indole-3-acetamide (IAM) pathway as well as cytokinins is a common trait of Pseudomonas savastanoi populations causing disease on oleander and olive. These phytohormones are required for the induction and development of an outgrowth of plant cell tissue termed a knot. However, in myrtle orchards of Sardinia (Italy), strains of P. savastanoi unable to produce cytokinins were found coexisting with cytokinin-producing strains. Data presented here show that the ability to produce IAA through the IAM pathway is also a variable trait within this population, raising questions on the exact role of these plant growth substances in the disease process on myrtle. Three P. savastanoi strains were selected based on their differential ability to produce phytohormones in vitro, and their interaction with the host was investigated over a period of 8 months using histological methods. All strains successfully invaded the infected twigs, moving systemically (unhalted by host defences) upward and downward from the inoculation point, both by completely degrading the cell walls and by taking advantage of the xylem vessels and intercellular spaces. Moreover, all strains induced the development of cankers, which slowly evolved into typical knots only on the twigs inoculated with the phytohormone-producing strains. This study further demonstrates that cytokinins and IAA are essential for knot development; moreover, it ascertains that bacterial production of cytokinins is not necessary for host colonization and for the expression of pathogenicity (i.e. the ability to cause disease) of P. savastanoi on myrtle.     

Bioregulatory Effects of the Fungicidal Strobilurin Kresoxim-methyl in Wheat (Triticum aestivum)

Apart from its fungicidal effect, the strobilurin kresoxim-methyl (BAS 490 F) was found to induce physiological and developmental alterations in wheat (Triticum aestivum L.) which are seen in connection with improved yield. In a series of biotests including heterotrophic maize and photoautotrophic algal cell suspensions, duckweed, isolated mustard shoots and germinating cress seeds, kresoxim-methyl showed a similar response pattern to standard auxins (e.g. indol-3-ylacetic acid, IAA; 2-(1-naphthyl)acetic acid, α-NAA). Auxin-like activity of kresoxim-methyl was also found when stem explants of tobacco were cultured on a hormone-free medium. Kresoxim-methyl stimulated shoot formation, particularly at 10^-7 M . The same effect was induced by 10^-8 M IAA. The determination of phytohormone-like substances in shoots of wheat plants foliar-treated with 7×10^-4 M kresoxim-methyl revealed only slightly changed levels of endogenous IAA, gibberellins and abscisic acid. In contrast, the contents of dihydrozeatin riboside-type cytokinins increased to 160% of the control, while trans-zeatin riboside- and isopentenyladenosine-type cytokinins remained nearly unchanged. The most remarkable alterations were the reductions in 1-aminocyclopropane-1-carboxylic acid (ACC) levels and ethylene formation which were demonstrated in intact plants, leaf discs and the shoots of wheat subjected to drought stress. Kresoxim-methyl affected the induction of ACC synthase activity which converts S-adenosyl-methionine to ACC in ethylene biosynthesis. In shoots from foliar-treated wheat plants, 10^-4 M kresoxim-methyl inhibited stress-induced increases in endogenous ACC synthase activity, ACC levels and ethylene formation by approximately 50%. Reductions in ACC synthase activity and ACC levels of 30% were also obtained at low concentrations of α-NAA (10^-6 M ). In contrast, ACC synthase activity in vitro was not influenced by adding the compounds. In wheat leaf discs, the inhibiting effect of kresoxim-methyl, α-NAA and IAA on ethylene formation was accompanied by delayed leaf senescence, characterized by reduced chlorophyll loss. However, in contrast to kresoxim-methyl which showed only inhibitory activity on ethylene synthesis over a wide range of concentrations applied, the auxins stimulated ethylene production at high concentrations of about 10^-4 M . The inhibition of ethylene biosynthesis by kresoxim-methyl, together with an increase in endogenous cytokinins could explain the retardation of senescence and the intensified green leaf pigmentation in wheat exposed to this strobilurin. © 1997 SCI.     

Indol-3-ylacetic acid- and calmodulin-regulated Ca2+-ATPase: A target for the phytotoxic action of hexachlorocyclohexane

In rice seedlings, the organochlorine insecticide hexachlorocyclohexane (HCH) and its four major isomers—α,β, γ, and δ—have been shown to elicit their phytotoxic action by interacting with indol-3-ylacetic acid (IAA)-regulated growth and Ca²⁺-ATPase activity. When rice seedlings were grown in the presence of 0.34 mM HCH, seedling vigour was reduced to 33% of the control. A similar effect was observed when seedlings were grown in the presence of the γ and δ isomers, but not with the α and δ isomers of HCH. This reduced vigour could be restored by treating the seedlings with 100 nM IAA, suggesting that HCH and its isomers (γ and δ) limit either IAA synthesis or action or both. In a microsomal fraction from rice seedlings grown in the presence of either HCH or its isomers, the calmodulin-regulated Ca²⁺-ATPase activity was inhibited as follows: technical HCH = 46%, α isomer = 80%, β isomer = 72%, γ isomer = 65% and δ isomer = 62% of the control value, respectively. TLC analysis suggested that the various isomers of HCH are metabolised by the plant, except for the δ isotner, which accumulated. This isomer, along with the degraded products of other isomers, may be responsible for the phytotoxic action of HCH.     

Efficacy of methyl iodide and synergy with chloropicrin for control of fungi

Efficacy of soil fumigation with methyl bromide and methyl iodide against Botrytis cinerea, Colletotrichum gloeosporioides, Fusarium oxysporum, Gliocladium virens, Phytophthora citricola, Phytophthora citrophthora, Pythium ultimum, Rhizoctonia solani and Verticillium dahliae was determined in laboratory experiments in closed fumigation chambers. Pythium ultimum was the most sensitive fungal species with EC₅₀ values for methyl bromide and methyl iodide of 15.5 and 8.6 µM , respectively. R solani was the least sensitive with EC₅₀ values of 253.4 and 161.4 µM for methyl bromide and methyl iodide, respectively. Relative potency ([methyl bromide]/[methyl iodide]) values ranged from 5.2 for P citricola to 1.5 for F oxysporum. Methyl iodide was 2.7 more efficacious than methyl bromide averaged over all fungal species. Methyl bromide/chloropicrin and methyl iodide/chloropicrin applied jointly were 2.2 and 2.8 times more efficacious, respectively, against F oxysporum than when the compounds were applied singly. Combining methyl bromide and methyl iodide with chloropicrin resulted in a significant synergistic increase in activity against F oxysporum. © 2000 Society of Chemical Industry     

钾肥与吲哚-3-乙酸共同作用对小麦-麦长管蚜-短翅蚜小蜂三级营养关系的影响

为明确钾肥和吲哚-3-乙酸(IAA)的相互作用对调控小麦-麦长管蚜-短翅蚜小蜂载体植物系统内3个营养级生长发育的影响,通过外源浇灌含223.5、447和894 mg/L KCl的Hoagland营养液和喷施0、50、150和250 mg/L IAA溶液的组合,研究了其对小麦叶片各生理指标、麦长管蚜体重差及体内代谢酶活力、短翅蚜小蜂体长及体内代谢酶活力的影响。结果表明,不同KCl和IAA组合对3个营养级的影响差异显著。447 mg/L KCl与150 mg/L IAA处理下的小麦叶面积最大,为9.57±0.16 cm²;223.5 mg/L KCl与50、250 mg/L IAA处理组的叶片含水量最高,达89.69%;叶绿素和类胡萝卜素含量最高的处理组是447 mg/L KCl与250 mg/L IAA;麦长管蚜体重增长最多及短翅蚜小蜂体长最长的处理组均为447 mg/L KCl与50 mg/L IAA;各处理组对3个营养级酶活水平的影响程度不同。KCl和IAA在多个指标中表现出交互效应,表明选用合适的组合不仅能饲养出优异的适宜繁殖寄生蜂的替代寄主,还可最大限度地培养优秀蜂源。     

Synthesis and insecticidal activity of 3-(haloalkyl-1,3-dienyl)-2,2-dimethylcyclopropanecarboxylates

New 2,2-dimethylcyclopropanecarboxylic acids bearing halogenated 1,3-alkadienyl substituents at position 3 of the cyclopropane ring were synthesised and the insecticidial activities of their 3-phenoxybenzyl and α-cyano-3-phenoxybenzyl esters against housefly (Musca domestica), Colorado potato beetle (Leptinotarsa decemlineata) and Egyptian cotton leafworm (Spodoptera littoralis) were determined. The activity of these compounds varied according to the relative position of the halogen substituents on the diene chain. The observed changes of activity with the structure of the side chain are discussed in terms of the coplanarity of the conjugated double bonds.     

Evaluation of regulatory influence of four plant growth regulators on the reproductive potential and longevity of melon fruit fly (Bactrocera cucurbitae)

The topical treatment given to freshly emerged (0–1-day-old) male and female adults ofBactrocera cucurbitae (Coquillett), a serious pest of cucurbit crops in tropical countries, with 25, 125, 625 and 3125 ppm concentrations of gibberellic acid (GA₃), indole-3-acetic acid (IAA), kinetin and coumarin showed a significant adverse influence on the reproductive potential of this fruit fly. The assessment for reproductive potential was made on the basis of reduction in fecundity and fertility of laid eggs and measured as sterility in females and shortening of the longevity,i.e. ovipositional phase. The strongest influence was with kinetin, followed closely by coumarin, then GA₃ and lastly with IAA treatments. It was concluded that although these compounds demonstrate their activities differently in plants and might be following a different mode of action in insects, they ultimately influence the reproductive potential of this insect.     

Effect of soil physical factors on methyl iodide and methyl bromide

Production and importation of methyl bromide is scheduled to be banned by 2001. Methyl iodide was evaluated as a possible replacement soil fumigant. The effects of soil moisture, temperature, soil texture and fumigation time on the efficacy of methyl iodide for the control of two common weeds, Abutilon theophrasti and Lolium multiflorum, were characterized and compared with those of methyl bromide. The optimal soil moisture for methyl iodide to kill both weed species in sandy soils was 14% water content (w/w). Greater efficacy was obtained when the temperature during fumigation was above 20°C. Compared to methyl bromide, the efficacy of methyl iodide was more consistent in different soils. Time to 100% mortality of weeds was 24 h for methyl iodide fumigation and 36 h for methyl bromide when 200 μM of fumigant was used. On a molar basis methyl iodide was consistently more effective than methyl bromide across the range of environmental factors tested. In terms of application technology and spectrum of activity, methyl bromide can be directly replaced by methyl iodide. © 1998 SCI     

A comparative review of the mammalian toxicity of Bacillus thuringiensis-based pesticides

The extensive mammalian toxicity studies performed to support the safety of Bacillus thuringiensis-containing pesticides clearly demonstrate that the tested isolates are not toxic or pathogenic. Toxicity studies submitted to the US Environmental Protection Agency to support the registration of B. thuringiensis subspecies have failed to show any significant adverse effects in body weight gain, clinical observations, or upon necropsy. Infectivity/pathogenicity studies have shown that the intact rodent immune system responds as expected to eliminate B. thuringiensis gradually from the body after oral, pulmonary or intravenous challenge. Similar clearance patterns were observed with B. subtilis and B. sphaericus, which also were non-toxic to test animals. The results also indicate that the currently used protocols for toxicity/pathogenicity evaluations of micro-organisms in laboratory animals have provided useful and necessary information for risk assessment. The study results raise the issue, however, of whether some reduced set of toxicily/pathogenicity studies could be required for new B. thuringiensis isolates of already registered subspecies, and whether this reduced data set would also apply to subspecies not yet registered as pesticidal active ingredients.     

The pyrethrins and related compounds. Part XXIX: Haloallylbenzyl esters

Synthesis and bioassay of a series of esters based on pyrethroidal acids established that the activity of halosubstituted allylbenzyl esters depends on the position and stereochemistry of substitution in the allyl side-chain, on the substitution pattern on benzyl, on the esterifying acid, and, to a lesser extent, on the nature of the halogen substituent itself. The most powerful combination of the first four parameters for activity against houseflies is in (Z)-3-haloallylbenzyl esters of the (1R)-cis 3-(2,2-dibromovinyl) acid. Other combinations have moderate to low activity. Some aspects of the variation conform to previously recognised patterns, others define more precisely the requirements for the side-chain to confer activity. The pattern of response of activity to cyano-substitution at the α-position, noted earlier, persists in the current compounds, and is here analysed quantitatively.     

The Use of Confined Colonies of Wild Mice (Mus musculus L.) in the Evaluation of Rodenticides1

Experimental studies have been conducted using penned families of wild house mice (Mus musculus L.) treated with different rodenticides and subjected to various poisoning regimes. The results showed that such investigations on rodents can provide valuable post-laboratory information on the relative merits and the best mode of application of rodenticides prior to their examination under field conditions. Pen population studies also permit closer study of feeding activity, bait acceptance, social behaviour and other factors that can affect rodenticidal efficacy.     

Inhibitors of choline acetyltransferase as potential insecticides

Choline acetyltransferase (E.C.2.3.1.6) catalyses the synthesis of acetylcholine and is therefore a target for a new insecticide. We have prepared a variety of compounds, mainly choline analogues, as inhibitors of this enzyme. One of these, 2-isothiocyanatoethyltrimethylammonium iodide, has a K_i of 0.06 μM (K_m for choline is 150 μM ) and is apparently the most powerful inhibitor known for this enzyme. Although some of our compounds are insecticidal we believe, on the basis of electrophysiological studies, that they act, not on choline acetyltransferase, but on the acetylcholine receptor of the insect.