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Anthranilic diamides

Anthranilic diamide insecticides are derivatives of anthranil. Chlorantraniliprole (Rynaxy-pyr ) is the only member of this new class. It is very effective in controlling lepidopterous insects on pome fruit, stone fruit, tree nuts, grapes, cotton, potato, brassicaceous and fruiting vegetables, and cucurbits. Its oral LD30 in rats is 5000 mg/kg. [Pg.77]

3-Bromo-N-[4-chloro-2-methyl-6-[(methylamino)Carbonyl]Phenyl]-l-(3-chloro-2-pyridinyl)-1H- pyrazole-5-carboxamide [Pg.77]


DuPont has also introduced a new class of insecticides, the anthranilic diamides, such as DP-23 [205], which, like flubendiamide, also act by activating the ryanodine receptor [206],... [Pg.164]

Knight, A.L. and Flexner, L., Disruption of mating in codling moth (Lepidoptera Tortricidae) by chlorantranilipole, an anthranilic diamide insecticide, Pest Manag. Sci., 63,180, 2007. [Pg.141]

Rynaxypyr A New Anthranilic Diamide Insecticide Acting at the Ryanodine Receptor... [Pg.111]

Figure 2 illustrates the synthesis of several anthranilic diamides prepared in our early discovery program. Our initial targets consisted of derivatives including those of formula D1-D3. These were prepared by coupling of anthranilamide 2 with substituted benzoyl chlorides 3 in the presence of base. The anthranilamide intermediates 2 could be prepared from isatoic anhydrides by treatment with isopropylamine. [Pg.112]

Table I. Insecticidal potency of anthranilic diamides against three species of Lepidoptera. ... Table I. Insecticidal potency of anthranilic diamides against three species of Lepidoptera. ...
The first analog from this set, the unsubstituted phenyl pyrazole D9, showed activity similar to pyrazoles D6-D7, and somewhat less than the isopropyl pyrazole D8 especially on Hv. In contrast, however, the ortho-Cl-phenyl analog DIO showed a remarkable improvement in activity, spanning two orders of magnitude against all three species of Lepidoptera. This discovery was the key structural breakthrough in the anthranilic diamide area and provided the framework for a large scope... [Pg.113]

Based on the high levels of activity obtained for DIO, a series of N-pyridyl analogs were explored. We also wished to study the effect of substituents R4 on the aryl portion of the anthranilic diamide. Figures 4-6 illustrate the routes by which these compounds were prepared [2]. The method presented in Figure 4 was used to prepare the 3-trifluoromethyl-5-pyrazolecarboxylic acid 26. This method involves regioselective lithiation of 3-trifluoromethylpyrazole 25 followed by reaction with carbon dioxide, to afford the pyrazole carboxylic acid 26 in good yield. [Pg.115]

Anthranilic diamides, D11-D17, were prepared in good yield by the reaction of an amine, R5NH2, with benzoxazinones 35 as shown in Figure 6. Synthesis of the benzoxazinones was accomplished by sequential treatment of 34 with one equivalent of triethylamine and methanesulfonyl chloride, followed by the anthranilic acid 33, and then followed by a second equivalent of triethylamine and methanesulfonyl chloride. The intermediate 4-chloro-6-mefhyl-anthranilic acid 33 = Cl) was prepared by chlorination of 6-methylanfhranilic acid with... [Pg.116]

Table II. Insecticidal potency and CMT values of anthranilic diamides D11-Dl 7. Table II. Insecticidal potency and CMT values of anthranilic diamides D11-Dl 7.
To assess activity at the insect ryanodine receptor, pyridyl pyrazoles of Table II were tested in a calcium mobilization assay, using neurons from the American cockroach, Periplaneta americana. These studies have confirmed the mode of action to be RyR activation. Compounds D11-D17 showed exceptional potency in this assay with activity in the range of0.03-0.30 pM. The data shows the ability of anthranilic diamides to release internal calcium stores while failing to activate voltage-gated calcium channels. Furthermore, calcium mobilization induced by anthranilic diamides is blocked following treatment with 1 pM ryanodine, consistent with action at the ryanodine receptor. [Pg.118]

Figure 7 shows the relationship between insecticidal activity on Plutella xylostella and data from the Ca mobilization assay for a diverse structural set of anthranilic diamides. [Pg.118]

Figure 7. Anthranilic diamide LC50 values for Piutella xylostella plotted against CMT values. Figure 7. Anthranilic diamide LC50 values for Piutella xylostella plotted against CMT values.
Lepidopteran larvae exposed to anthranilic diamides exhibit rapid feeding cessation, general lethargy, constrictive muscle paralysis, and regurgitation. One of the earliest symptoms observed was reduction in heart rate. Manduca sexta larvae showed greater than a 50% decrease in heart beat frequency ten minutes following injection with Rynaxypyr (30 ng). Among anthranilic diamides evaluated, similar rank potency was found for this cardio-inhibitory effect and lepidopteran toxicity. [Pg.121]

Figure 1. Cif mobilization dose response for P. americana neurons challenged with anthranilic diamides shown in (a). Figure 1. Cif mobilization dose response for P. americana neurons challenged with anthranilic diamides shown in (a).
The RyR is a tetrameric channel protein, which regulates release of stored intracellular Ca (Figure 2). The name was derived from the natural plant product, ryanodine, which binds at the channel pore and alters the channel conductance state. Anthranilic diamides failed to displace or enhance H-ryanodine binding to P. americana membranes, indicating that this chemistry binds to a distinct site. [Pg.123]

A radiolabeled anthranilic diamide, H-D18, was prepared and found to exhibit specific, saturable binding to muscle membranes. Interestingly, under conditions of high CaCl2 (500 pM), ryanodine enhances H-D18 binding up to 8-fold, with a = 44 nM and B, = 9690 fmol/mg [6]. In this preparation, Rynaxypyr potently displaces H-D18 with an IC5Q value of 4 nM. As was observed with lepidopteran toxicity, a linear relationship was revealed between Ca mobilization and the ability of anthranilic diamides to displace H-D18. [Pg.123]

Western blot analysis of P. americana membranes and photo-affinity studies using a tritiated azido-anthranilic diamide revealed that Rynaxypyr and related analogs bind directly to the ryanodine receptor rather than to an accessory protein. [Pg.123]

Novel Arylpyrazole and Arylpyrimidine Anthranilic Diamide Insecticides... [Pg.141]

The preparation of aryl pyrazole anthranilic diamides with designated Isomer A regiochemistry is outlined in Figure 3. Esters 8 imderwent base hydrolysis to the acids 10 that were converted to the acid chlorides with oxalyl chloride and coupled with anthranilic amides 11 to afford the anthranilic diamide products of formula 12 in moderate yield. [Pg.142]

Table I shows that arylpyrazole anthranilic diamides of formula 12 (Isomer A regiochemistry) gave varying levels of plant protection against Lepidoptera at concentrations between 50 and 0.4 ppm. Plutella xylostella was generally the most sensitive insect species where some analogs (where Rj is isopropyl or t-butyl, Rj is trifluoroethyl or bromodifluoromethyl, Rj is chlorine and X is N) provided excellent plant protection at 0.4 ppm. These analogs required higher concentrations for comparable control of Heliothis virescens and Spodopterafru perda. Table I shows that arylpyrazole anthranilic diamides of formula 12 (Isomer A regiochemistry) gave varying levels of plant protection against Lepidoptera at concentrations between 50 and 0.4 ppm. Plutella xylostella was generally the most sensitive insect species where some analogs (where Rj is isopropyl or t-butyl, Rj is trifluoroethyl or bromodifluoromethyl, Rj is chlorine and X is N) provided excellent plant protection at 0.4 ppm. These analogs required higher concentrations for comparable control of Heliothis virescens and Spodopterafru perda.

See other pages where Anthranilic diamides is mentioned: [Pg.77]    [Pg.122]    [Pg.140]    [Pg.111]    [Pg.112]    [Pg.112]    [Pg.112]    [Pg.114]    [Pg.118]    [Pg.121]    [Pg.122]    [Pg.125]    [Pg.141]    [Pg.142]    [Pg.142]    [Pg.143]    [Pg.143]    [Pg.143]    [Pg.144]   
See also in sourсe #XX -- [ Pg.77 ]

See also in sourсe #XX -- [ Pg.1124 , Pg.1135 , Pg.1212 ]




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Anthranilate

Anthranilic diamide

Anthranilic diamide

Anthranillate

Anthranils

Arylpyrazole anthranilic diamide

Arylpyrimidine anthranilic diamide

Diamid

Diamide

Diamides

Diamids

Mode anthranilic diamides

Rynaxypyr A New Anthranilic Diamide Insecticide Acting at the Ryanodine Receptor

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