Insecticidal compositions comprising pyridylpyrazole insecticides

Abstract

The present invention relates to an insecticidal composition comprising a pyridylpyrazole insecticide, which is highly effective for controlling animal pests. The insecticidal composition comprising a pyridylpyrazole insecticide contains an active ingredient of a compound of Formula I and a chlorfenapyr. The insecticidal composition is used for the purpose of preventing or controlling Plutellidae, Aleyrodidae, Eriophyidae, Thripidae, Aphididae, Pentatomidae pests and their larvae and eggs. The method for protecting plants from pests includes contacting the plants with the insecticidal composition.

Description

TECHNICAL FIELD

[0001] The present invention relates to an insecticidal composition comprising a pyridyl pyrazole insecticide, which is highly effective for controlling animal pests. BACKGROUND

[0002] The active ingredient of formula I is known from WO2013162716. The agent is useful for controlling cotton mealybug, rhynchophorus palmarum.

[0003]

[0004] The repeated and exclusive use of a single insecticidal active ingredient leads in many cases to a rapid selection of pests which develop natural or adapted resistance to the active ingredient in question.

[0005] It is an object of the present invention to provide an insecticidal composition comprising a pyridyl pyrazole insecticide which solves at least one problem such as improving biological properties, providing synergistic properties, reducing dosage rates, broadening the activity spectrum, combining knockdown activity and long lasting effect, resistance management to delay resistance. SUMMARY

[0006] It is an object of the present invention to provide an insecticidal composition comprising a pyridyl pyrazole insecticide which is a mixture (synergistic mixture) having improved activity against animal pests and a reduced total amount of active compounds applied, to reduce the application rates and to improve the activity spectrum of the compound of formula I, lufenuron.

[0007] Surprisingly, it has been found that simultaneous (i.e. combined or separate) application of the active compounds, the compound of formula I and lufenuron or sequential application of the compound of formula I and lufenuron results in an enhanced pest control effect compared to the control rates possible with the individual compounds applied alone, which unexpected effect is a true synergism and not just an additive effect of the activities.

[0008] The presence of a synergistic effect was determined using the method described in Colby S.R., "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations," Weeds, 1967, 15, 20-22.

[0009] The insecticidal composition comprising a pyridyl pyrazole insecticide according to the present invention can comprise a combination of the compound of formula I and lufenuron in synergistically effective amounts, the weight ratio of the compound of formula I to lufenuron can be from about 50:1 to 1:50, preferably from 20:1 to 1:20, preferably from 15:1 to 1:15, more preferably from 10:1 to 1:10, even more preferably from 5:1 to 1:5.

[0010] Use of the insecticidal composition comprising the pyridyl pyrazole insecticide for preventing or controlling Plutellidae, Aleyrodidae, Eriophyidae, Thripidae, Aphididae, Pentatomidae, and larvae and eggs thereof.

[0011] Use of the insecticidal composition comprising the pyridyl pyrazole insecticide for preventing or controlling Myzus persicae, Aphis gossypii, Eriosoma lanigerum, Plutella xylostella, Spodoptera exigua, Bemisia tabaci,

[0012] Use of the insecticidal composition comprising the pyridyl pyrazole insecticide for preventing or controlling Plutella xylostella, Thripidae, Aphis gossypii, Bemisia tabaci, Cantharis, and larvae and eggs thereof.

[0013] Use of the insecticidal composition comprising the pyridyl pyrazole insecticide for preventing or controlling Plutella xylostella, Thripidae, and larvae and eggs thereof.

[0014] A method for protecting a plant from pests, comprising contacting the plant with the insecticidal composition comprising the pyridyl pyrazole insecticide.

[0015] A method for preventing or controlling pests, and larvae and eggs thereof, comprising applying the insecticidal composition comprising the pyridyl pyrazole insecticide to target pests, seeds of plants, plants, or fruits of plants, or soil where plants grow or soil suitable for plants to grow.

[0016] The insecticidal composition comprising the pyridyl pyrazole insecticide, further comprises other fungicides, bactericides, attractants, insecticides, acaricides, nematicides, growth regulators, herbicides, safeners, fertilizers, or semiochemicals.

[0017] The insecticidal composition of the present application can be prepared in a form suitable for application as a combination of the active ingredient compounds, or as a combination of commercially available formulations in an appropriate dose.

[0018] The insecticidal composition of the present application can be in the form of a solid preparation or a liquid preparation. The solid preparation includes a powder, a dust, or a granular preparation; the liquid preparation includes a dispersion, a suspension, an emulsion, or a solution in an appropriate liquid carrier.

[0019] The total amount of the active ingredient in the insecticidal composition of the present application can be selected according to specific factors to achieve the desired effect. The factors include, for example, the dosage form, the object to be applied, the method of application, and the like.

[0020] The present application provides a method for protecting a plant from pests, comprising contacting the plant with the insecticidal composition of the present application.

[0021] The insecticidal composition of the present application can be applied to target pests, seeds, plants, or fruits of plants, or soil where plants grow or soil suitable for plants to grow.

[0022] Methods of treating target pests, seeds, plants, or the fruit of plants or soil with the insecticidal composition of the present invention include, for example, spreading treatment, soil treatment, surface treatment, and fumigation treatment. Spreading treatment includes, for example, spreading, spraying, misting, atomizing, and granular application. Soil treatment includes, for example, soil irrigation and soil mixing. Surface treatment includes, for example, coating and covering. Fumigation treatment includes, for example, covering the soil with a polyethylene film after injection. Direct foliar application is preferred.

[0023] Applicants typically use the insecticidal compositions of the present invention in backpack sprayers, spray cans, spray aircraft, or irrigation systems. The insecticidal compositions of the present invention are usually formulated with water, buffers, and / or other adjuvants to the desired application concentration to obtain a ready-to-use spray.

[0024] The insecticidal composition of this invention is particularly suitable for controlling animal pests of the classes Insecta and Arachnida. For example:

[0025] Lepidoptera pests: Noctuidae (e.g., *Trichoplusiani*, *Mamestra brassicae*, *Spodopterae xigua*, *Spodopteralitura*, *Helicoverpa armigera*, *Pseudaletia separate*, *Agrotis ipsilon*); Plutellidae (e.g., *Plutellaxylotella*); Tortricidae (e.g., *Adoxophyes oranafasciata*, *Archips fuscocureanus*, *Homona magnanima*); Gelechiidae (e.g., *Pectinophoragos sypiella*, *Pinkbellaria*). Bollworms; Pyralidae, such as the rice stem borer (chilosuppressalis (walker), rice leaf roller (Tryporyzaincertulas (walker)), rice leaf roller (cnaphalocrocismedinalis Guenee), Chinese cabbage leaf roller (hellullaundalis), peach borer (conogethespunctiferlis); Pieridae, such as the cabbage white butterfly (Pieris rapae), citrus swallowtail (papilioxuthus), white-skinned butterfly (pierisrapaecrucivora), and straight-striped rice skipper (parnaraguttata); Arctiidae, such as the fall webworm (hyphantriacunea);

[0026] Thysanopteran pests, such as palm thrips, western flower thrips (Frankliniella occidentalis), tobacco thrips (Thrips alliorum (Priesner)), yellow-breasted thrips (Thrips hawaiiensis (Morgan), yellow tea thrips (Scirtothrips dorsalis Hood), and flower thrips (Frankliniella intonsa (Trybom)).

[0027] Orthoptera (Orthoptera) pests, such as Acrididae (Grasshoppers); stink bugs (megacoptapunctatissimum), cabbage bugs (eurydemarugosum), large-spined white-spotted bugs (eysarcorislewisi), white-spotted bugs (eysarcorisparvus), rice green bugs (nezaraviridula), Plautiastali, stink bugs (halymorphamista), rice thorny-edged bugs (cletuspunctiger), Chinese rice thorny-edged bugs (leptocorisachinensis), cuckoo lace bugs (stephantispyrioides), and red-bearded mirid bugs (trigonotyluscoelestialium), etc.

[0028] Hemiptera pests, such as those from the families Aphididae, Adelgidae, or Phylloxaceridae, including the tobacco aphid (Myzus persicae), cotton aphid (Aphis gossypii), black bean aphid (Aphis fabae), corn aphid (Aphis maidis) (corn leaf aphid), pea aphid (Acyrthosiphon pisum), eggplant webless aphid (Aulacorthum solani), bean aphid (Aphis craccivora), euphorbiae macrosiphumeuphorbiae, wheat webless aphid (Macrosiphum avenae), wheat webless aphid (Metopolophium dirhodum), rice webless aphid (Rhopalosiphum padi), wheat two-forked aphid (Schizaphis graminum), cabbage aphid (Brevicoryne brassicae), turnip aphid (Lipaphis erysimi), and spirea aphid (Aphis). The species include: citricola, rose apple aphid (Rosy apple aphid), apple woolly aphid (Eriosoma lanigerum), citrus two-forked aphid (Toxoptera aurantii), and large citrus aphid (Toxoptera citricidus); Cicadidae, such as black-tailed leafhopper (Nephotettix cincticeps); Delphacidae, such as gray planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), and white-backed planthopper (Sogatella furcifera); Pentatomidae, such as white-spotted bug (Eysarcoris ventralis) and green rice bug (Nezara viridula); and Aleyrodidae, such as tobacco whitefly (Bemisia). The whitefly (Trialeurodesvaporariorum); Scale insects (Diaspididae, Margarodidae, Ortheziidae, Aclerdiae, Dactylopiidae, Kerridae, Pseudocoddidae); Coccidae; Eriococcidae; Asterolecaniidae; Lecanodiaspididae;Or family Cerococcidae, such as Pseudococcus comstocki and Planococcus citri Risso; family Psyllidae, such as pear psyllid (psyllapyrisuga) and citrus psyllid (diaphorinatabaci);

[0029] Coleoptera pests, such as: rice weevil (Sitophilus oryzaelinne), citrus leaf miner (Podagricomelanigricollis Che), corn weevil (S. zeamails), grain weevil (S. granarius), large ape leaf beetle (Cabbageleaf beetle), small ape leaf beetle (Daikon leaf beele), flea beetle (flea beetle), grape flea beetle (Altica chalybea), striped flea beetle (phyllotretastriolata), cucumber flea beetle (Epitrix cucumeris), tobacco flea beetle (Ehirtipennis), eggplant flea beetle (E. fuscula), cucumber beetle (Aula cophora ndica (Gemlin), mustard leaf beetle (Phaedon cochleariae), rice water weevil (Lissorhoptrus oryzophilus), Callosobruchuyschienensis, yellow mealworm (Tenebrio molitor), and corn root leaf beetle (Diabrotica). The species include *Vibriferavirgifera*, cucumber beetle (*Diabrotica undecimpunctata howardi*), green beetle (*Anomalacuprea*), red copper beetle (*Anomala rufocuprea*), yellow striped flea beetle (*Phyllotreta striolata*), cucumber beetle (*Aulacophora femoralis*), potato beetle (*Leptinotarsa ​​decemlineata*), rice leaf beetle (*Oulema oryzae*), bostrychidae, and longhorn beetles (*Cerambycidae*).

[0030] Pests belonging to the order Acari. Examples include: citrus leafminer (panonychuscitri), cinnabar mite (Tetranychuscinnabarinus), apple leafminer (panonychusulmi), two-spotted leafminer (tetranychusurticae), hawthorn leafminer (tetranychusviennensis), needle-leaved leafminer (oligonychusununguis), citrus leafminer (eotetranychuskankitus), purple short-haired mite (brevipalpusphoenicis), alfalfa moth (bryobiapraetiosa), wheat leafroller (aceriatulipae), grape gall mite (colomerusvitis), tea gall mite (calacaruscarinatus), and citrus rust mite (Phyllocoptesoleivora). Ashmead, broad yellow mite (polyphagotarsonemuslatus), long hairy root mite (rhizoglyphusrostochiensis), rough-legged flour mite (Acarussiro), citrus gall mite (Aceriasheldoni), Aculusschlechtendali, etc.

[0031] Diptera pests, such as: rice leafminer (Agromyza oryzae), barley water fly (Hydrilla agriseola), gerbera leafminer (Liriomyza trifolii), pea leafminer (Chromomaia horticola), tomato leafminer (Liriomyza bryoniae), gray field fly (Delia platura), onion field fly (Delia antiqua), Mediterranean fruit fly (Ceratis capiata wiedgman), apple fruit fly (Rhagoletis pomonella), cherry fruit fly (R. cingulata), etc.

[0032] Hymenoptera pests, such as the yellow-winged cabbage leaf bee (athaliarosaeruficornis), the rose leaf bee (argepagana), the black mountain ant (formica japonica), and the chestnut gall bee (dryocsmuskuriphilus);

[0033] Orthoptera pests, such as house crickets (Acheta domesticus), crickets (Gryllotalpa spp.), migratory locusts (Locustamigratoriamigratorioides), black locusts (Melanopluss pp.), and desert locusts (Schistocercagregaria);

[0034] Blattodea pests, such as the Oriental cockroach (Blatta orientalis), the American cockroach (Periplaneta americana), the Madeira cockroach (Leucophae amadea), and the German cockroach (Blattella germanica);

[0035] Dermaptera pests, such as the European ball cactus (Forficula auricularia);

[0036] Isoptera pests, such as species of the genus *Reticulitermes* spp.;

[0037] The order Anoplura (Phthiraptera) includes genera such as Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., and Trichodectes spp.;

[0038] Representative organisms of the class Nematoda include those selected from genera such as *Meloidogyne* spp., *Heterodera* spp., *Globodera* spp., *Radipoholus* spp., *Pratylenchus* spp., and *Longidorus* spp. Among these, the soybean cyst nematode *Heterodera*, the potato golden nematode *golboderarostochiensis*, and the southern root-knot nematode *meloidogyne incognita* are preferred.

[0039] The insecticidal composition of the present invention is particularly effective against Lepidoptera, Thysanoptera, Orthoptera, Hemiptera, and Acari pests.

[0040] In particular, the insecticidal composition of the present invention is especially effective against the following pests; specifically including the following pests:

[0041] Plutellidae family, such as the diamondback moth (Plutellaxylotella);

[0042] Whiteflies include species such as the cabbage whitefly (Aleurodes brassicae), the tobacco whitefly (Bemisia tabaci), and the greenhouse whitefly (Trialeurodes vaporariorum);

[0043] Aphids include species such as the tobacco aphid (Myzus persicae), the cotton aphid (Aphis gossypii), the cabbage aphid (Brevicoryne brassicae), and the rice constrictor aphid (Rhopalosiphum padi);

[0044] Thripidae includes species such as palm thrips, western flower thrips (Frankliniella occidentalis), tobacco thrips (Thrips alliorum (Priesner)), yellow-breasted thrips (Thrips hawaiiensis (Morgan), yellow tea thrips (Scirtothrips dorsalis Hood), and flower thrips (Frankliniella intonsa (Trybom)).

[0045] The family Pentatomidae (stinkbugs) includes species such as the stink bug (megacoptapunctatissimum), the cabbage bug (eurydemarugosum), the large-spined white-spotted bug (eysarcoris lewisi), the white-spotted bug (eysarcoris parvus), the green rice bug (nezaraviridula), the plautiastali, the stink bug (halymorphamista), the rice thorny-edged bug (cletuspunctiger), the Chinese rice thorny-edged bug (leptocorisa chinensis), the cuckoo lace bug (stephantis pyrioides), and the red-bearded blind bug (trigonotylus coelestialium).

[0046] Eriophyidae includes species such as the grape gall mite (colomerusvitis), the tea gall mite (calacaruscarinatus), the citrus rust mite (Phyllocoptes oleivora Ashmead), the citrus gall mite (Aceriasheldoni), and the Aculusschlechtendali.

[0047] In particular, the insecticidal composition of the present invention exhibits a surprising "synergistic" effect on the prevention or control of pests of the families Diamondback Mothidae, Whiteflyidae, Gallidae, Thripsidae, and Aphididae, as well as their larvae and eggs.

[0048] The insecticidal composition of the present invention has excellent control efficacy against diamondback moths, whiteflies, gall midges, thrips, aphids and their larvae and eggs at low doses.

[0049] In particular, the insecticidal composition of the present invention has excellent control efficacy against tobacco aphids, cotton aphids, peach aphids, diamondback moths, beet armyworms, whiteflies, citrus rust mites, thrips, stink bugs and their larvae and eggs at low doses.

[0050] The insecticidal composition of the present invention is particularly important for controlling animal pests in various crops such as citrus, pineapple, banana, plantain, pear (especially apple and pear), grape, almond, coffee, tea, vegetables (especially tomato, lettuce, cucumber, carrot, onion, garlic and potato), cotton, soybean, coffee, tea, corn (corn) and rice.

[0051] The mixtures of the present invention are active against both generally susceptible and resistant species, and exhibit excellent activity against all or individual developmental stages. Therefore, the insecticidal compositions of the present invention can be applied to any and all developmental stages of pests, such as eggs, larvae, pupae, and adults.

[0052] The insecticidal composition of the present invention can also be used in combination with other active ingredients, such as fungicides, bactericides, attractants, insecticides, acaricides, nematicides, growth regulators, herbicides, safeners, fertilizers, or chemical pheromones.

[0053] The insecticidal compositions of the present invention include not only ready-to-use compositions that can be applied to plants or plant propagation materials using suitable devices, but also commercially available concentrates that must be diluted with water before application.

[0054] The insecticidal composition of the present invention exhibits high synergistic pest control effects, reduces the effective dose rate, increases environmental safety, and reduces the incidence of pest resistance.

[0055] The invention relates to an insecticidal composition comprising a pyridylpyrazole insecticide that can address at least one problem such as improving biological properties, providing synergistic properties, reducing dosage rate, broadening the activity spectrum, combining knockdown activity and long-lasting effects, and managing resistance to delay resistance. Detailed Implementation

[0056] The present invention will be further described below with reference to embodiments.

[0057] Biological test cases

[0058] The expected effect of a specific combination of two active components can be calculated using the so-called "Colby formula" (see SRColby, "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 1967, 15, 20-22):

[0059]

[0060] X represents the control effect when the active ingredient of compound I is used at a dosage of mg / ha or a concentration of m ppm, expressed as a percentage of the untreated control.

[0061] Y represents the control efficacy when the active ingredient, lufenuron, is applied at a dosage of ng / ha or a concentration of n ppm, expressed as a percentage of the untreated control.

[0062] E represents the control efficacy when using active ingredient compound of formula I and lufenuron at dosages of m and ng / ha or concentrations of m and n ppm, expressed as a percentage of the untreated control.

[0063] If the actual control effect exceeds the calculated value, the lethal effect of the composition is superadditive, that is, there is a synergistic effect.

[0064] Experimental Example 1: Diamondback Moth Experiment

[0065] Preparation of the solution: Prepare a stock solution of compound I and lufenuron with acetone, and then dilute it with 0.1% Tween-80 aqueous solution to the required concentration.

[0066] Select second-instar diamondback moth larvae that have been continuously reared indoors and are in the same physiological state. Select cabbage leaves of uniform growth to make suitable leaf saucers.

[0067] Immerse the leaf discs in the test solution for 10 seconds, then remove and air dry them before placing them in a petri dish containing moisturizing filter paper. Inoculate with test insects. Approximately 10 test insects are inoculated into each group of experiments. Each treatment is replicated 4 times. A blank control is provided for the treatment without the test solution (containing organic solvents and emulsifiers).

[0068] The treated test insects were covered and placed in a container at 25±1°C. o They were raised and observed in a constant temperature incubator with a relative humidity of 60%-80% and a light cycle of L:D=(16:8)h.

[0069] The results were checked after 72 hours in the incubator. The criterion for determining death was: the insect was considered dead if it did not react at all or could not react normally when gently touched with a needle.

[0070] Calculation method:

[0071] Mortality rate (%) = (Number of live worms before treatment - Number of live worms after treatment) / Number of live worms before treatment × 100

[0072] Prevention and control efficacy % = ((mortality rate of treatment group - mortality rate of control group) / (100 - mortality rate of control group)) × 100

[0073] Table 1. Effects of Formula I compound and lufenuron on diamondback moth.

[0074]

[0075] Experimental Example 2: Experiment with Western Flower Thrips

[0076] Preparation of the solution: Prepare a stock solution by disoproxil fumarate and compound of formula I with acetone, and then dilute it with 0.1% Tween-80 aqueous solution to the required concentration.

[0077] The green bean soaking feeding method was used. Fresh green bean pods were immersed in the drug solution for 5 seconds, then removed, excess solution was absorbed with absorbent paper, and the pods were allowed to air dry. They were then placed in disposable plastic cups, inoculated with newly emerged western flower thrips, sealed with Parafilm, and placed in an incubator at a temperature of 25 ± 0.5℃, relative humidity of 50 ± 5%, and a photoperiod of 14 L:10D. Water (containing solvent and Tween) was used as a control. Each plastic cup contained 20 western flower thrips, and each treatment was repeated three times. After 48 hours, the number of live thrips was counted (thrips that did not move when lightly touched with a brush were considered dead).

[0078] Calculation method:

[0079] Mortality rate (%) = (Number of dead test insects / Number of test insects before drug administration) × 100

[0080] Efficacy % = ((mortality rate in treatment group - mortality rate in control group) / (100 - mortality rate in control group)) × 100

[0081] Table 2. Control efficacy of the combination of Formula I compound and lufenuron against western flower thrips.

[0082]

[0083] The experimental results in Tables 1-2 show that the combination of compound I and lufenuron has a synergistic effect on the control of diamondback moth and thrips.

Claims

1. An insecticidal composition comprising a pyridylpyrazole insecticide, characterized in that, The active ingredient consists of a compound of formula I and lufenuron, wherein the weight ratio of the compound of formula I to lufenuron is 50:1 to 1:

5. 。 2. The insecticidal composition according to claim 1, characterized in that, The weight ratio of the compound of Formula I to lufenuron is 20:1 to 1:

5.

3. The insecticidal composition according to claim 1, characterized in that, The weight ratio of the compound of Formula I to lufenuron is 10:1 to 1:

1.

4. The insecticidal composition according to claim 1, characterized in that, The weight ratio of the compound of Formula I to lufenuron is 5:1 to 1:

1.

5. The use of the insecticidal composition of claim 1 for the prevention or control of diamondback moths, thrips, and their larvae and eggs.

6. Use of the insecticidal composition of claim 1 for the prevention or control of diamondback moth, thrips and their larvae and eggs.

7. A method for protecting plants from pests, characterized in that, The insecticidal composition of claim 1 is brought into contact with the plant, wherein the pest is selected from the Prunella vulgaris and Thripsidae families.

8. A method for preventing or controlling pests and their larvae and eggs, characterized in that, The insecticidal composition of claim 1 is applied to a target pest, plant seed, plant or plant fruit or soil in which the plant grows or soil suitable for plant growth, wherein the pest is selected from the Pyrenidae family or Thrips family.

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