A composition containing a thiazolidone acaricide and use thereof
By combining trifluoroethyl phenyl sulfide thiazolidinone acaricides with other insecticides, acaricides, or fungicides to create a synergistic effect, the problems of poor control efficacy and pest resistance in existing technologies are solved, achieving efficient and environmentally friendly pest control.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2025-12-08
- Publication Date
- 2026-03-27
AI Technical Summary
Existing insecticide and acaricide compositions are difficult to achieve efficient control and delay the development of pesticide resistance in pests, resulting in decreased control effectiveness, increased pesticide dosage, and environmental pollution problems.
When trifluoroethyl phenyl sulfide thiazolidinone acaricides are used in combination with insecticides, acaricides or fungicides in specific proportions, a synergistic effect is formed, which improves the control effect and delays the development of pesticide resistance in pests.
It significantly improves the control of pests, mites and diseases, reduces the cost of use, reduces environmental pollution, and delays the development of pesticide resistance in pests.
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Abstract
Description
TECHNICAL FIELD
[0001] The present application relates to the field of pesticide compositions, in particular to a thiazolidinone acaricide composition containing a trifluoroethyl phenyl sulfide and application thereof. BACKGROUND
[0002] The compound of formula (I) and its preparation method have been disclosed in patent CN119528843A, which belongs to a novel trifluoroalkyl sulfide (sulfoxide) thiazolidinone acaricide, has the characteristics of novel structure and excellent acaricidal activity, and shows good control effect on each growth stage of the pest mites, and has broad market application prospect.
[0003] In pest control practice, long-term use of insecticides with a single active ingredient can easily lead to pest resistance, resulting in decreased control effect, increased pesticide use, and other problems, which not only increases the control cost and environmental pollution, but also significantly increases the risk of pesticide residues in agricultural products. By compounding two active ingredients in a specific ratio into a mixed insecticide and acaricide, the control effect can usually be improved, the amount of active ingredients can be reduced, the cost can be reduced, and the development of pest resistance can be delayed. However, the compounding of two substances is not arbitrary, and whether it can achieve synergism and expand the control spectrum is highly uncertain. If the combination can improve the control effect, reduce the cost, and improve the efficiency, it has excellent market prospect, so such synergistic combination has always been the goal of the industry.
[0004] The insecticide and acaricide compositions disclosed in the prior art have different emphases and are difficult to achieve efficient control. Therefore, there is an urgent need to develop new active compound compositions with synergistic properties. SUMMARY
[0005] The purpose of the present application is to overcome the technical problem of low pest / mite control efficiency in the prior art, and to provide a thiazolidinone acaricide composition containing a trifluoroethyl phenyl sulfide, which has the advantages of improving the control effect, expanding the control spectrum, and effectively delaying pest resistance.
[0006] The compound of formula (I) can be used to control various pests, especially agricultural mites, and has good control effect on various mites and pests such as Tetranychus cinnabarinus, Panonychus citri, Citrus rust mite, Tetranychus urticae, Comstock mealybug, apple leaf mite, eriophyid mite, powdery mite, and nematode.
[0007] The inventors of the present application have unexpectedly found that when the compound of formula (I) and the active compound of group (II) are used in combination, especially in a certain ratio, they have more excellent effect in the control of pests, mites, or diseases, thereby providing the present application.
[0008] The present application provides in a first aspect a composition comprising a compound of formula (I) and an active compound of group (II),
[0009] wherein the compound of formula (I) is selected from ,
[0010] the active compound of group (II) is selected from the group of insecticides (IRAC mode of action classification group) (3), (6), (10), (12), (13), (20), (21), (23) or (25),
[0011] the weight ratio between the compound of formula (I) and the active compound of group (II) is in the range of 1 :99 to 99:1.
[0012] According to some embodiments of the present application, the weight ratio between the compound of formula (I) and the active compound of group (II) is in the range of 1 :99 to 99:1, such as 1 :1, 1 :2, 1 :2.5, 1 :4, 1 :5, 1 :6, 1 :8, 1 :10, 1 :20, 1 :30, 1 :40, 1 :50, 1 :60, 1 :70, 1 :80, 1 :90, 1 :99, 99:1, 90:1, 85:1, 80:1, 70:1, 60:1, 50:1, 40:1, 30:1, 20:1, 10:1, 8:1, 6:1, 5:1, 4:1, 2.5:1, 2:1 or any value in between the aforementioned values.
[0013] Further, the composition of the present application preferably comprises a synergistically effective amount of the compound of formula (I) and the compound of group (II). Group (II) consists of:
[0014] Insecticide group (IRAC (Insecticide Resistance Action Committee) mode of action classification group; also referred to as "IRAC classification group"): (3), (6), (10), (12), (13), (20), (21), (23) or (25). Further defined as follows:
[0015] (3) Sodium channel modulators, preferably pyrethroids selected from the group consisting of bifenthrin, cyhalothrin, fenpropathrin, acrinathrin, brofluthrinate, wherein the mentioned compounds are preferred;
[0016] (6) glutamate-gated chloride channel (GluCl) allosteric modulators selected from the group consisting of abamectin, ivermectin, emamectin benzoate, lepimectin, milbemycin oxime, milbemycins, ivermectin, emamectin benzoate, wherein the mentioned compounds are preferred;
[0017] (10) mite growth inhibitors selected from the group consisting of clofentezine, diflovidazin, etoxazole, hexythiazox, wherein the mentioned compounds are preferred;
[0018] (12) inhibitors of the mitochondrial ATPase, such as ATP disruptors, for example diafenthiuron or organotin compounds, such as azocyclotin, fenbutatin oxide, cyhexatin, triphorustine, propargite, propargite, tetradifon or tetradifon, wherein the mentioned compounds are preferred;
[0019] (13) uncouplers that interfere with the proton gradient influencing oxidative phosphorylation selected from the group consisting of chlorfenapyr, meptyldinocap, binapacryl, sulphluramid, wherein the mentioned compounds are preferred;
[0020] (20) inhibitors of the mitochondrial electron transport complex (III) selected from the group consisting of fluacrypyrim, flufenoxystrobin, pyriminostrobin, fluopyram, bifenazate, acequinocyl, wherein the mentioned compounds are preferred;
[0021] (21 ) Mitochondrial complex I electron transport inhibitors, for example MET I acaricides, such as tebufenpyrad, tolfenpyrad, fenazaquin, fenpyroximate, pyridaben, pyrimidifen, or rotenone, wherein the mentioned compounds are preferred;
[0022] (23) Acetyl CoA carboxylase inhibitors, for example tetronic acid and tetramic acid derivatives, selected from spirodiclofen, spiromesifen, spirotetramat, spidoxamat, spiropidion, spirobudifen, spirodiclofen, spirodichlorid, wherein the mentioned compounds are preferred;
[0023] (25) Mitochondrial complex II electron transport inhibitors, for example beta-ketonitrile derivatives, selected from cyflumetofen, cyenopyrafen, cyetpyrafen, pyflubumide, wherein the mentioned compounds are preferred.
[0024] The composition according to the present application more preferably comprises a synergistically effective amount of a compound of formula (I) and a compound of group (II). Group II consists of:
[0025] (3) Sodium channel modulators selected from (II-1 ) bifenthrin, (II-3) fenpropathrin;
[0026] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators selected from (II-6) abamectin, (II-7) ivermectin, (II-8) emamectin benzoate;
[0027] (10) Mite growth inhibitors selected from (II-15) etoxazole;
[0028] (12) Inhibitors of mitochondrial ATP synthase selected from the group consisting of (II-16) diafenthiuron, (II-17) azocyclotin, (II-18) fenbutatin oxide, (II-21) propargite;
[0029] (20) Inhibitors of mitochondrial electron transport complex (III) selected from the group consisting of (II-33) bifenazate, (II-34) acequinocyl;
[0030] (21) Inhibitors of mitochondrial complex I electron transport selected from the group consisting of (II-37) fenazaquin, (II-39) pyridaben;
[0031] (23) Acetyl CoA carboxylase inhibitors selected from the group consisting of (II-42) spirodiclofen, (II-44) spirotetramat;
[0032] (25) Inhibitors of mitochondrial complex II electron transport selected from the group consisting of (II-51) cyflumetofen, (II-52) cyenopyrafen, (II-53) cyetpyrafen.
[0033] The synergistic effect is particularly pronounced when the active compounds in the compositions according to the application are present in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can vary within relatively wide ranges. In general, the compositions according to the application comprise the active compounds (I) and the active compounds of group (II) selected from the compounds of groups (3), (6), (10), (12), (20), (21), (23) or (25) in the following preferred, more preferred mixing ratios.
[0034] Preferred mixing ratios: 99: 1 to 1 : 99, such as 50: 1 to 1 : 50, or 20: 1 to 1 : 20.
[0035] More preferred mixing ratios: 50: 1 to 1 : 50, such as 50: 1 to 1 : 15, or 1 : 15 to 50: 1, or 20: 1 to 1 : 15, or 15: 1 to 1 : 20, or 15: 1 to 1 : 15, or 10: 1 to 1 : 10, or 5: 1 to 1 : 5.
[0036] Table 1 provides particularly preferred mixing ratios for some specific compositions of the compounds of formula (I) and the compounds of group (II). Thus, each individual active compound combination of the compounds of formula (I) and the indicated group (II) in the respective indicated mixing ratio is a preferred embodiment of the present application.
[0037] Table 1
[0038]
[0039]
[0040] The mixing ratios are based on weight ratios. The ratio is to be understood as meaning active compound of formula (I) : active compound of group (II).
[0041] the weight parts ratio of the compound of formula (I) to (II-1) bifenthrin, (II-7) ivermectin, (II-39) pyridaben or (II-42) spirodiclofen is from 20:1 to 1 :20;
[0042] the weight parts ratio of the compound of formula (I) to (II-15) etoxazole is from 20:1 to 1 :5;
[0043] the weight parts ratio of the compound of formula (I) to (II-3) fenpropathrin, (II-6) abamectin, (II-16) diafenthiuron, (II-18) fenbutatin oxide, (II-21) propargite or (II-33) bifenazate is from 10:1 to 1 :20;
[0044] the weight parts ratio of the compound of formula (I) to (II-8) emamectin benzoate or (II-37) quimacryd thiin is from 5:1 to 1 :20;
[0045] the weight parts ratio of the compound of formula (I) to (II-17) azocyclotin is from 20:1 to 1 :10;
[0046] the weight parts ratio of the compound of formula (I) to (II-34) milbactin, (II-44) spirotetramat, (II-51) cyflumetofen or (II-52) cymiazole is from 10:1 to 1 :10;
[0047] the weight parts ratio of the compound of formula (I) to (II-53) ethyl (Z)-3-ethoxy-3-(2,4-dioxo-3-(prop-2-yn-1 -yl)imidazolidin-1 -yl)prop-2- enoate is from 10:1 to 1 :5.
[0048] According to some preferred embodiments of the present application, the compound of formula (I) is a compound of the structure shown in formula I-332.
[0049]
[0050] Surprisingly, the insecticidal and / or arachnicidal / acaricidal and / or nematicidal and / or antimicrobial and / or fungicidal and / or plant enhancing and / or yield enhancing efficacy of the active compound combinations according to the invention is significantly higher than the sum of the efficacies of the individual active ingredients. There is a real, unanticipated synergistic effect, rather than merely a complementary / additive effect.
[0051] The second aspect of the present invention provides the use of the composition according to the first aspect in the control of pests, especially acarid pests, or diseases. The pests and diseases are as described above.
[0052] In the present invention, the combination of the active compounds (I) and the listed compounds of the active compounds of group (II) in the composition is suitable for controlling a variety of important agricultural and forestry pests, acarid pests; the combination of the active compounds (I) and the listed compounds of the active compounds of group (II) in the composition is suitable for controlling a variety of harmful fungi, especially a variety of fungal diseases, bacterial diseases, nematode diseases, viral diseases of cereals, vegetables, fruit trees, ornamental plants, lawns and tropical crops, and a variety of storage diseases.
[0053] Specifically suitable for controlling a variety of important agricultural pests such as armyworm, beet armyworm, cotton bollworm, cutworm, cabbage armyworm, codling moth, rice leaf roller, corn borer, rice borer, diamondback moth, cabbage looper, gypsy moth, fall armyworm, subterranean pests, leaf-roller moth, leafminer, aphid, leafhopper, scale insect, potato beetle, flea beetle, thrips, stink bug, two-spotted spider mite, hawthorn spider mite, citrus red mite, apple spider mite, two-spotted spider mite, gall mite, acaruspis, etc., urban pests such as termites, cockroaches, ants, flies, mosquitoes, etc. For fruit trees such as apples, pears, citrus, lychee, etc., cereals such as wheat, rice, etc., legumes such as soybeans, beans, etc., cotton, vegetables such as cabbage, cauliflower, Chinese cabbage, rape, tomato, pepper, and flowers. When used for controlling urban pests, it can be used in homes, various public places, office places, and trees, embankments, etc. damaged by termites.
[0054] According to some embodiments of the present invention, the composition is applied in a manner to control pests, acarid pests or diseases in an amount of 10-5000 grams per hectare.
[0055] In the present invention, the direct or indirect manner is not particularly limited as long as the purpose of controlling pests, acarid pests or diseases can be achieved, for example, the direct manner can include directly contacting the composition of the present invention with pests, acarid pests or fungi; the indirect manner can include treating the habitat or food chain of pests, acarid pests or fungi with the composition of the present invention.
[0056] The composition of the present application can be provided in the form of a finished formulation. For example, emulsifiable concentrate, suspension concentrate, water dispersible granule, aqueous emulsion, microemulsion, soluble liquid, wettable powder, oil miscible flowable concentrate, etc. can be prepared as needed.
[0057] The composition of the present application contains active ingredients I and II in a cumulative amount of 0.5 to 95% by weight, preferably in a cumulative amount of 1 to 85% by weight.
[0058] The content of the active ingredients in the composition of the present application depends on the application rate when used alone, and also on the mixing ratio and the degree of synergistic effect. The optimal range of the content of the active ingredients can vary depending on the type of the composition.
[0059] The formulation of the composition of the present application can be prepared by conventional processing methods, for example, by mixing the active ingredients with a liquid carrier (solvent) or a solid carrier, and adding one or more auxiliary agents (for example, emulsifiers, dispersants, wetting agents, binders, stabilizers, and antifoaming agents, etc.). In the present application, preferably, the composition contains at least one carrier and at least one surfactant. Preferably, in each of the above cases, it is ensured that the active ingredients of the composition of the present application are uniformly distributed.
[0060] In the present application, the emulsifiable concentrate generally contains 10 to 75% of the active ingredients, 2 to 20% of the emulsifier, 0 to 20% of other additives (for example, stabilizers, penetrants, corrosion inhibitors, etc.), and a solvent, and, if necessary, a co-solvent, by weight.
[0061] In the present application, the suspension concentrate generally requires sand milling to obtain a stable non-deposited flowable product. The suspension concentrate generally contains 5 to 50% of the active ingredients, 5 to 15% of the dispersant, 0.1 to 10% of the wetting agent, 4 to 10% of the antifreezing agent, 0 to 10% of other additives (for example, antifoaming agents, preservatives, stabilizers, penetrants, and thickening agents), and the balance of the liquid carrier, by weight.
[0062] In the present application, the water dispersible granule is generally prepared as 10 to 100 mesh (1.676 to 0.152 mm) granules, and can be prepared by extrusion, impregnation, or spray granulation. The water dispersible granule generally contains 0.5 to 80% of the active ingredients and 5 to 20% of the auxiliary agents (for example, dispersants, wetting agents, disintegrants, and binders), and the balance of the inert carrier, by weight.
[0063] In the present application, the wettable powder generally contains 10 to 85% of the active ingredients, 3 to 10% of the dispersant, and, in addition to the solid inert carrier, 0 to 10% of the wetting agent and / or other additives (for example, penetrants or stabilizers), by weight.
[0064] In the present application, the emulsion in water is formed by mixing the raw drug, organic solvent and surfactant to form an oil phase; mixing water and antifreezing agent together to form a homogeneous transparent water phase. The oil phase is sheared by a high shear emulsifier, and the water phase is slowly added into the oil phase. The emulsion in water usually contains 1-60% of active ingredient, 5-20% of surfactant, 2-10% of antifreezing agent and the rest of water.
[0065] In the present application, the microemulsion is formed by mixing the raw drug, organic solvent, emulsifier and water together to form a homogeneous transparent liquid. The microemulsion usually contains 1-50% of active ingredient, 10-40% of emulsifier, 40-60% of organic solvent and the rest of water.
[0066] In the present application, the soluble liquid is formed by mixing the active ingredient, organic solvent and surfactant together to form a homogeneous transparent liquid. The soluble liquid usually contains 1-50% of active ingredient, 6-20% of surfactant and the rest of organic solvent.
[0067] In the present application, the oil suspension is formed by adding the active ingredient, surfactant and oil-based carrier into a sand mill for sand milling until the particle size is qualified. The oil suspension usually contains 2-60% of active ingredient, 6-20% of surfactant and the rest of oil-based carrier.
[0068] In the present application, the aqueous dispersion and emulsion (such as the composition obtained by diluting the emulsion, wettable powder or concentrate of the present application with water) are also within the scope of the present application. The above-mentioned emulsion (including the various forms mentioned above) can be water-in-oil type or oil-in-water type, and can have thick slurry consistency.
[0069] Compared with the prior art, the present application has the following remarkable advantages:
[0070] 1. Significant synergistic effect: the active compound combination of the present application has a significantly higher insecticidal and miticidal effect within a certain ratio range than the sum of the effects of each single active ingredient compound, showing obvious synergistic effect, which can effectively improve the control effect on pests and better cope with the problem of pest control.
[0071] 2. Reducing the use cost and environmental impact: due to the synergistic effect of the composition, the use dose in actual application is significantly lower than that of each single compound, which not only reduces the use cost of pesticides and the economic burden of farmers, but also reduces the pollution of pesticides to soil, water, air and other environments, reduces the risk of pesticide residues in agricultural products, and is conducive to the protection of ecological environment and the improvement of agricultural product quality and safety.
[0072] 3. Delaying the development of pest resistance: the effective components in the composition of the present application act on different mechanisms of insecticidal and miticidal action, and there is no cross-resistance problem. When used for pest control, it can kill pests from different target points, effectively delay the development of pest resistance, prolong the service life of pesticides, and provide protection for long-term and effective pest control. DETAILED DESCRIPTION
[0073] The endpoints of the ranges and any values in the ranges disclosed herein are not limited to the precise values or the exact range, and the ranges should be interpreted as approximately between the stated values or endpoints. For ranges of values, the endpoints of the ranges are included in the ranges, and the endpoints and individual points within the ranges can be combined to form new ranges, which are also contemplated within the scope of the present disclosure.
[0074] In vitro bioactivity assay
[0075] Example 1 In vitro bioactivity assay of the composition containing compound I on Tetranychus cinnabarinus female adult mites
[0076] Test basis: the test refers to the Agricultural Industry Standard NY / T 1154.6-2006 "Pesticide In vitro Bioassay Test Guidelines. Insecticides. Part 6: Insecticidal Activity Test. Immersion Test".
[0077] Test object: Tetranychus cinnabarinus female adult mites.
[0078] 1.1 Test method of Tetranychus cinnabarinus female adult mites
[0079] Select Vicia faba seedlings with uniform growth, and grow thick and tender leaves. Cut them into two leaves and one stem shape, and then cut one leaf into one leaf and one stem shape, and insert them into 5 mL sample bottles filled with water. About 30 female adult mites are selected for each leaf. Accurately weigh each test agent, dissolve it with a small amount of DMSO, and prepare a 10000 mg / L stock solution. The test solution is prepared by gradient dilution of the test solution stock solution. After the test insects are stable on the leaves, immerse them in the prepared solution for 5-10 s, absorb the excess solution with filter paper, and air dry. Each treatment is repeated 3 times, and a blank control group is set up. The immersion solution used in the blank control group is a DMSO and Tween water solution with the same proportion. Then, place the experimental target in an artificial climate chamber (24-26 ℃, L:D=16h:8h, RH 60%) for culture. After 72 h, check and record the death of female adult mites.
[0080] 1.2 Test design
[0081] Table 2 Test design of mixing bifenthrin with formula I-332 (female adult mites)
[0082]
[0083] Table 3 Formulation I-332 mixed with fenpropathrin test design (female adult mites)
[0084]
[0085] Table 4 Formulation I-332 mixed with abamectin test design (female adult mites)
[0086]
[0087] Table 5 Formulation I-332 mixed with ivermectin test design (female adult mites)
[0088]
[0089] Table 6 Formulation I-332 mixed with emamectin benzoate test design (female adult mites)
[0090]
[0091] Table 7 Formulation I-332 mixed with triazamate test design (female adult mites)
[0092]
[0093] Table 8 Formulation I-332 mixed with fenbutatin oxide test design (female adult mites)
[0094]
[0095] Table 9 Formulation I-332 mixed with diafenthiuron test design (female adult mites)
[0096]
[0097] Table 10 Formulation I-332 mixed with bifenazate test design (female adult mites)
[0098]
[0099] Table 11 Formulation I-332 mixed with chinomethionat test design (female adult mites)
[0100]
[0101] Table 12 Formulation I-332 mixed with pyridaben test design (female adult mites)
[0102]
[0103] Table 13 Formulation I-332 mixed with quimacox test design (female adult mites)
[0104]
[0105] Table 14 shows the experimental design for mixing Formula I-332 with fenpropathrin (adult female mites).
[0106]
[0107] Table 15 Experimental design for mixing Formula I-332 with cypermethrin (adult female mites)
[0108]
[0109] Table 16 Experimental Design for Mixing Formula I-332 with Ethoxamer (Adult Female Mites)
[0110]
[0111] 1.3 Data Statistics and Analysis
[0112] The number of live insects and the total number of insects in each treatment were counted, and the mortality rate and corrected mortality rate for each treatment were calculated.
[0113] Mortality rate (%) = [(Insect population before treatment - Number of surviving insects after treatment) / Insect population before treatment] × 100%;
[0114] Corrected mortality rate (%) = [(treatment mortality rate - control mortality rate) / (1 - control mortality rate)] × 100%.
[0115] If the mortality rate in the blank control group is less than 5%, no adjustment is required.
[0116] Use formulas edited in Excel to perform data analysis and statistics to calculate LC. 50 The toxicity index was calculated using the Sun Yunpei method (Sun et al., 1960), and the co-toxicity coefficient was also calculated.
[0117] The co-toxicity coefficient (CTC) calculation method of Sun Yunpei (Sun et al., 1960) is used to evaluate the effect of drug mixtures. A CTC ≥ 120 indicates synergistic effects, a CTC ≤ 80 indicates antagonism, and 80 < CTC < 120 indicates additive effects. The co-toxicity coefficient (CTC) is calculated using formulas (1), (2), and (3):
[0118] ┈┈┈┈┈┈┈┈┈┈┈┈┈(1;
[0119] In the formula:
[0120] ATI – The measured toxicity index of the mixture;
[0121] S-----EC50 of the standard reagent, in milligrams per liter (mg / L);
[0122] M ----- EC50 of the mixture, in mg / L.
[0123] ┈┈┈┈┈┈┈┈┈┈┈┈ (2);
[0124] wherein:
[0125] TTI ----- Theoretical Toxicity Index of the mixture;
[0126] TIA ----- Toxicity Index of A agent;
[0127] PA ----- Percentage of A agent in the mixture, in %;
[0128] TIB ----- Toxicity Index of B agent;
[0129] PB ----- Percentage of B agent in the mixture, in %.
[0130] ┈┈┈┈┈┈┈┈┈┈ (3);
[0131] wherein:
[0132] CTC ----- Co-Toxicity Coefficient;
[0133] ATI ----- Actual Toxicity Index of the mixture;
[0134] TTI ----- Theoretical Toxicity Index of the mixture.
[0135] 1.4 Test Results
[0136] Table 17 Results of indoor activity determination of compound I-332 and bifenthrin against T. c. (female adult)
[0137]
[0138] The results of joint toxicity determination of compound I-332 and bifenthrin in different proportions against T. c. (female adult) showed that the LC 50 value of I-332 against T. c. (female adult) was 0.2039 mg / L, the LC 50 value of bifenthrin against T. c. (female adult) was 3.0846 mg / L, and I-332 and bifenthrin had synergistic effect against T. c. (female adult) in the range of 20:1 to 1:20 (Table 17).
[0139] Table 18 Results of indoor activity determination of compound I-332 and fenpropathrin against T. c. (female adult)
[0140]
[0141] The joint toxicity test results of compound I-332 and fenpropathrin in different proportions on T. cinnabarinus (female adult) showed that the LC50 value of I-332 on T. cinnabarinus (female adult) was 0.2807 mg / L, the LC50 value of fenpropathrin on T. cinnabarinus (female adult) was 23.8399 mg / L, and I-332 and fenpropathrin had a synergistic effect on T. cinnabarinus (female adult) in the range of 10:1 to 1:20 (Table 18). 50 50
[0142] Table 19 Indoor activity test results of compound I-332 and abamectin on T. cinnabarinus (female adult)
[0143]
[0144] The joint toxicity test results of compound I-332 and abamectin in different proportions on T. cinnabarinus (female adult) showed that the LC50 value of I-332 on T. cinnabarinus (female adult) was 0.1905 mg / L, the LC50 value of abamectin on T. cinnabarinus (female adult) was 0.003511 mg / L, and I-332 and abamectin had a synergistic effect on T. cinnabarinus (female adult) in the range of 10:1 to 1:20 (Table 19). 50 50
[0145] Table 20 Indoor activity test results of compound I-332 and ivermectin on T. cinnabarinus (female adult)
[0146]
[0147] The joint toxicity test results of compound I-332 and ivermectin in different proportions on T. cinnabarinus (female adult) showed that the LC50 value of I-332 on T. cinnabarinus (female adult) was 0.1875 mg / L, the LC50 value of ivermectin on T. cinnabarinus (female adult) was 0.01138 mg / L, and I-332 and ivermectin had a synergistic effect on T. cinnabarinus (female adult) in the range of 20:1 to 1:20 (Table 20). 50 50
[0148] Table 21 Indoor activity test results of compound I-332 and emamectin benzoate on T. cinnabarinus (female adult)
[0149]
[0150] The joint toxicity test results of compound I-332 and emamectin benzoate in different proportions on T. cinnabarinus (female adult) showed that the LC50 value of I-332 on T. cinnabarinus (female adult) was 0.1905 mg / L, the LC50 value of emamectin benzoate on T. cinnabarinus (female adult) was 0.003511 mg / L, and I-332 and emamectin benzoate had a synergistic effect on T. cinnabarinus (female adult) in the range of 10:1 to 1:20 (Table 19). 50 The LC value of I-332 against T. c. adults is 0.1940 mg / L, and the LC value of emamectin benzoate against T. c. adults is 0.2108 mg / L. 50 The I-332 and emamectin benzoate in the range of 5:1 to 1:20 have synergistic effect on T. c. adults (Table 21).
[0151] Table 22 The results of indoor activity determination of I-332 and azocyclotin against T. c. (adults)
[0152]
[0153] The results of joint toxicity determination of I-332 and azocyclotin in different ratios against T. c. (adults) show that the LC value of I-332 against T. c. adults is 0.2108 mg / L, and the LC value of azocyclotin against T. c. adults is 3.6431 mg / L. 50 The LC value of I-332 against T. c. adults is 0.2108 mg / L, and the LC value of azocyclotin against T. c. adults is 3.6431 mg / L. 50 The I-332 and azocyclotin in the range of 20:1 to 1:10 have synergistic effect on T. c. adults (Table 22).
[0154] Table 23 The results of indoor activity determination of I-332 and fenbutatin-oxide against T. c. (adults)
[0155]
[0156] The results of joint toxicity determination of I-332 and fenbutatin-oxide in different ratios against T. c. (adults) show that the LC value of I-332 against T. c. adults is 0.2186 mg / L, and the LC value of fenbutatin-oxide against T. c. adults is 4.9870 mg / L. 50 The LC value of I-332 against T. c. adults is 0.2186 mg / L, and the LC value of fenbutatin-oxide against T. c. adults is 4.9870 mg / L. 50 The I-332 and fenbutatin-oxide in the range of 10:1 to 1:20 have synergistic effect on T. c. adults (Table 23).
[0157] Table 24 The results of indoor activity determination of I-332 and diafenthiuron against T. c. (adults)
[0158]
[0159] The results of joint toxicity determination of I-332 and diafenthiuron in different ratios against T. c. (adults) show that the LC value of I-332 against T. c. adults is 0.2181 mg / L, and the LC value of diafenthiuron against T. c. adults is 6.7479 mg / L. 50 The LC value of I-332 against T. c. adults is 0.2181 mg / L, and the LC value of diafenthiuron against T. c. adults is 6.7479 mg / L. 50 The I-332 and diafenthiuron in the range of 10:1 to 1:20 have synergistic effect on T. c. adults (Table 24).
[0160] Table 25 The results of laboratory activity determination of compound I-332 and bifen- pyr against T. c. (adult female)
[0161]
[0162] The results of joint toxicity determination of compound I-332 and bifen- pyr in different proportions against T. c. (adult female) showed that the LC50 value of I-332 against T. c. (adult female) was 0.1679 mg / L, the LC50 value of bifen- pyr against T. c. (adult female) was 1.6120 mg / L, and I-332 and bifen- pyr had synergistic effect against T. c. (adult female) in the range of 10:1-1:20 (Table 25). 50 50
[0163] Table 26 The results of laboratory activity determination of compound I-332 and acequinocyl against T. c. (adult female)
[0164]
[0165] The results of joint toxicity determination of compound I-332 and acequinocyl in different proportions against T. c. (adult female) showed that the LC50 value of I-332 against T. c. (adult female) was 0.2525 mg / L, the LC50 value of acequinocyl against T. c. (adult female) was 1.0985 mg / L, and I-332 and acequinocyl had synergistic effect against T. c. (adult female) in the range of 10:1-1:10 (Table 26). 50 50
[0166] Table 27 The results of laboratory activity determination of compound I-332 and quinofen- phos against T. c. (adult female)
[0167]
[0168] The results of joint toxicity determination of compound I-332 and quinofen- phos in different proportions against T. c. (adult female) showed that the LC50 value of I-332 against T. c. (adult female) was 0.2628 mg / L, the LC50 value of quinofen- phos against T. c. (adult female) was 11.1655 mg / L, and I-332 and quinofen- phos had synergistic effect against T. c. (adult female) in the range of 5:1-1:20 (Table 27). 50 50
[0169] Table 28 The results of laboratory activity determination of compound I-332 and pyrid- azine against T. c. (adult female)
[0170]
[0171] The results of joint toxicity determination of compound I-332 and pyrid- azine in different proportions against T. c. (adult female) showed that the LC50 value of I-332 against T. c. (adult female) was 0.2628 mg / L, the LC50 value of pyrid- azine against T. c. (adult female) was 11.1655 mg / L, and I-332 and pyrid- azine had synergistic effect against T. c. (adult female) in the range of 5:1-1:20 (Table 28).50 The LC50 value of pyridaben against T. c. adults was 0.2284 mg / L, and the LC50 value of I-332 against T. c. adults was 0.1952 mg / L. 50 The LC50 value of I-332 against T. c. adults was 0.3389 mg / L, and the LC50 value of I-332 against T. c. adults was 0.8468 mg / L.
[0172] Table 29 Results of indoor activity determination of I-332 and cyflumetofen in different proportions against T. c. (female adults)
[0173]
[0174] The results of joint toxicity determination of compound I-332 and cyflumetofen in different proportions against T. c. (female adults) showed that the LC50 value of I-332 against T. c. adults was 0.3389 mg / L, and the LC50 value of I-332 against T. c. adults was 0.8468 mg / L. 50 The LC50 value of pyridaben against T. c. adults was 0.2284 mg / L, and the LC50 value of I-332 against T. c. adults was 0.1952 mg / L. 50 The LC50 value of I-332 against T. c. adults was 0.3389 mg / L, and the LC50 value of I-332 against T. c. adults was 0.8468 mg / L.
[0175] Table 30 Results of indoor activity determination of I-332 and fonicamid in different proportions against T. c. (female adults)
[0176]
[0177] The results of joint toxicity determination of compound I-332 and fonicamid in different proportions against T. c. (female adults) showed that the LC50 value of I-332 against T. c. adults was 0.3389 mg / L, and the LC50 value of I-332 against T. c. adults was 0.8468 mg / L. 50 The LC50 value of pyridaben against T. c. adults was 0.2284 mg / L, and the LC50 value of I-332 against T. c. adults was 0.1952 mg / L. 50 The LC50 value of I-332 against T. c. adults was 0.3389 mg / L, and the LC50 value of I-332 against T. c. adults was 0.8468 mg / L.
[0178] Table 31 Results of indoor activity determination of I-332 and ethyl acetate in different proportions against T. c. (female adults)
[0179]
[0180] The results of joint toxicity determination of compound I-332 and ethyl acetate in different proportions against T. c. (female adults) showed that the LC50 value of I-332 against T. c. adults was 0.3389 mg / L, and the LC50 value of I-332 against T. c. adults was 0.8468 mg / L. 50 The LC50 value of pyridaben against T. c. adults was 0.2284 mg / L, and the LC50 value of I-332 against T. c. adults was 0.1952 mg / L. 50 The LC50 value of I-332 against T. c. adults was 0.3389 mg / L, and the LC50 value of I-332 against T. c. adults was 0.8468 mg / L.
[0181] Example 2 Laboratory bioassay of compositions containing Compound I against Tetranychus cinnabarinus nymphs
[0182] Test basis: The test refers to the Agricultural Industry Standard NY / T 1154.6-2006 “Guidelines for Laboratory Bioassay of Pesticides. Insecticides. Part 6: Insecticidal Activity Test. Immersion Method”.
[0183] Test object: Tetranychus cinnabarinus nymphs.
[0184] 2.1 Test method for Tetranychus cinnabarinus nymphs
[0185] Select Vicia faba seedlings with uniform growth, and cut the thick and tender leaves into two-leaf-and-stem shapes. Then cut one leaf from each two-leaf-and-stem shape into a one-leaf-and-stem shape. Introduce 5 female adult mites to each one-leaf-and-stem shape to lay eggs. After 1 day, remove the female adult mites. After 3 days of hatching of the nymphs, cut the Vicia faba branches and insert them into 5 mL sample bottles filled with water. Keep about 30 nymphs on each leaf. Accurately weigh each test agent, dissolve it in a small amount of DMSO, and prepare a 10,000 mg / L stock solution. Dilute the test solution stock solution to obtain the test solution. Dip the leaf with the mites in the prepared test solution for 5-10 s, absorb the excess test solution with filter paper, and air dry. Repeat each treatment 3 times, and set up a blank control group. The dipping solution used in the blank control group is a DMSO and Tween water solution with the same proportion. Then place the experimental targets in an artificial climate chamber (24-26 °C, L:D = 16 h:8 h, RH 60%) for cultivation. After 72 h, check and record the number of dead nymphs.
[0186] Table 32 Test design for mixing Formula I-332 with etoxazole (nymphs)
[0187]
[0188] Table 33 Test design for mixing Formula I-332 with propargite (nymphs)
[0189]
[0190] Table 34 Test design for mixing Formula I-332 with spirotetramat (nymphs)
[0191]
[0192] Table 35 Test design for mixing Formula I-332 with spirodiclofen (nymphs)
[0193]
[0194] 2.3 Data statistics and analysis Refer to the data statistics and analysis in 1.3 of Reference Example 1.
[0195] 2.4 Test results
[0196] Table 36 The results of the indoor activity determination of compound I-332 and etoxazole against T. c. (nymphs)
[0197]
[0198] The joint toxicity determination results of compound I-332 and etoxazole in different proportions against T. c. (nymphs) showed that the LC50 value of I-332 against T. c. (nymphs) was 0.07598 mg / L, the LC50 value of etoxazole against T. c. (nymphs) was 0.04247 mg / L, and I-332 and etoxazole had a synergistic effect against T. c. (nymphs) in the range of 20:1 to 1:5 (Table 36). 50 50
[0199] Table 37 The results of the indoor activity determination of compound I-332 and propargite against T. c. (nymphs)
[0200]
[0201] The joint toxicity determination results of compound I-332 and propargite in different proportions against T. c. (nymphs) showed that the LC50 value of I-332 against T. c. (nymphs) was 0.08311 mg / L, the LC50 value of propargite against T. c. (nymphs) was 10.4488 mg / L, and I-332 and propargite had a synergistic effect against T. c. (nymphs) in the range of 10:1 to 1:20 (Table 37). 50 50
[0202] Table 38 The results of the indoor activity determination of compound I-332 and spirodiclofen against T. c. (nymphs)
[0203]
[0204] The joint toxicity determination results of compound I-332 and spirodiclofen in different proportions against T. c. (nymphs) showed that the LC50 value of I-332 against T. c. (nymphs) was 0.09321 mg / L, the LC50 value of spirodiclofen against T. c. (nymphs) was 1.3083 mg / L, and I-332 and spirodiclofen had a synergistic effect against T. c. (nymphs) in the range of 20:1 to 1:20 (Table 38). 50 50
[0205] Table 39 The results of the indoor activity determination of compound I-332 and spirotetramat against T. c. (nymphs)
[0206]
[0207] The results of the combined toxicity assay of compound I-332 and spirotetramat against *Tetranychus carmine* nymphs at different ratios showed that I-332 had the following LC50-95% toxicity against *Tetranychus carmine* nymphs: 50 The LC50 value for spirotetramat against Tetranychus cinnabarin nymphs was 0.07595 mg / L. 50 The value was 2.3672 mg / L. I-332 and spirotetramat had a synergistic effect on Tetranychus cinnabarinus nymphs in the range of 10:1 to 1:10 (Table 39).
[0208] The results of the above indoor tests clearly show that the compound of Formula I, when combined with dicofol, pyridaben, quinfenoxam, dicofol, difenoconazole, fenbutatin, triazophos, emamectin benzoate, ivermectin, cypermethrin, bifenthrin, etoxazole, cypermethrin, etoxazole, fenpyroximate, pyridaben, propargite, spirotetramat, or spirotetramat at appropriate mass ratios, exhibits excellent control effects against common crop mites, with a significant synergistic effect. Future field applications can reduce pesticide usage and slow the development of mite resistance. This composition can address the problems of high resistance, poor efficacy, and high dosage in the acaricide market, and has significant market application prospects.
[0209] The composition provided by this invention has the advantages of synergistic effect and broadened control spectrum. It can be used to control a variety of pests (especially mites) and plant diseases caused by a variety of fungi, bacteria, nematodes and viruses. It is particularly used to control plant diseases caused by plant mites such as carmine spider mite, citrus spider mite, two-spotted spider mite, apple spider mite, and broad mite.
[0210] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.
Claims
1. A composition comprising a thiazolidine acaricide, characterized in that, A composition comprising a compound of formula (I) and a group (II) of active compounds, wherein the compound of formula (I) is selected from , The active compounds of Group (II) are selected from (II-1) bifenthrin, (II-3) fenpropathrin, (II-6) abamectin, (II-7) ivermectin, (II-8) emamectin benzoate, (II-15) etoxazole, (II-16) diafenthiuron, (II-17) triazemate, (II-18) fenbutatin oxide, (II-21) propargite, (II-33) bifenazate, (II-34) acequinocyl, (II-37) quimacryl, (II-39) pyridaben, (II-42) spirodiclofen, (II-44) spiromesifen, (II-51) cyflumetofen, (II-52) cyenopyrafen, (II-53) ethyl (2-chloro-5-(thiazol-2-yl)phenyl) acetate; The weight ratio of the compound of formula (I) to (II-1) bifenthrin, (II-7) ivermectin, (II-39) pyridaben or (II-42) spirodiclofen is 20:1 to 1:20; The weight ratio of the compound of formula (I) to (II-15) etoxazole is 20:1 to 1:5; The weight ratio of the compound of formula (I) to (II-3) fenpropathrin, (II-6) abamectin, (II-16) diafenthiuron, (II-18) fenbutatin oxide, (II-21) propargite or (II-33) bifenazate is 10:1 to 1:20; The weight ratio of the compound of formula (I) to (II-8) emamectin benzoate or (II-37) quimacryl is 5:1 to 1:20; The weight ratio of the compound of formula (I) to (II-17) triazemate is 20:1 to 1:10; The weight ratio of the compound of formula (I) to (II-34) acequinocyl, (II-44) spiromesifen, (II-51) cyflumetofen or (II-52) cyenopyrafen is 10:1 to 1:10; The weight ratio of the compound of formula (I) to (II-53) ethyl (2-chloro-5-(thiazol-2-yl)phenyl) acetate is 10:1 to 1:
5.
2. Use of a composition according to claim 1, characterized in that, The use of the composition for preparing an insecticide or acaricide for controlling agricultural pests or urban hygiene pests.
3. Use of a composition according to claim 2, characterized in that, The composition is applied to pests to be controlled or the medium where pests grow in an effective dose of 100-1000 g per hectare.
4. An insecticidal and miticidal preparation, characterized by comprising: The composition of claim 1 is used as an active ingredient mixed with a carrier and any auxiliary agent to prepare a preparation.
Citation Information
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