Deuterated bisamides insecticides, process for their preparation and use thereof

Abstract

The application discloses a kind of deuterated bisamide insecticides, belong to the technical field of insecticide;The deuterated bisamide insecticide of the application has the chemical structure as described in compound (1), the preparation method and application of the above-mentioned insecticide are also disclosed;The present application takes bromofenoxim as a lead compound, and deuterates the special position, which significantly improves the insecticidal effect of bromofenoxim, and can be widely used for killing Lepidoptera, Coleoptera, Thysanoptera pests, termites and mosquitoes and flies, solving the problem of drug resistance and persistence of existing pesticides.

Description

Technical Field

[0001] This invention relates to the field of insecticides, and more particularly to a deuterated diamide insecticide, its preparation method, and its application. Background Technology

[0002] Broflanilide is a novel diamide insecticide belonging to the class of γ-aminobutyric acid (GABA)-gated chloride ion channel negative allosteric modulators. It is currently mainly used to control lepidopteran and coleopteran pests, and also has good insecticidal activity against termites and mosquitoes.

[0003] The beet armyworm (Spodoptera exigua (Hübner, 1808)), also known as the fall armyworm, cabbage brown armyworm, or corn armyworm, belongs to the order Lepidoptera and the family Noctuidae. It is characterized by its wide distribution, numerous hosts, strong migratory and dispersal capabilities, preference for warm temperatures, and tolerance to high temperatures. This insect is a polyphagous, with 170 known host species involving 35 families and 108 genera. It mainly damages vegetables, cotton, tobacco, corn, peanuts, beets, and flowers. Beet armyworms mate immediately after emergence, with females mating an average of about two times in their lifetime, and up to five to six times in some cases. They lay eggs rapidly after mating, resulting in a relatively short pre-oviposition period, generally around two days. In greenhouse crops such as chrysanthemums and tomatoes, beet armyworm eggs are mostly laid on the undersides of leaves 10 cm above the soil surface; in chrysanthemums, more eggs are laid on young plants than on older plants. Beet armyworm larvae are generally in the fifth instar, with a few reaching the sixth instar. The first instar larvae of the beet armyworm exhibit positive phototaxis, while the second instar larvae show weak negative phototaxis. The distribution of the third and fourth instar larvae is unaffected by light intensity, while the fifth instar larvae exhibit strong negative phototaxis. Newly hatched beet armyworm larvae mainly congregate and spin webs to cause damage. After the third instar, they disperse. The larvae feed mostly at night, and their consumption increases significantly after the fourth instar. The fourth and fifth instar larvae consume approximately 80-90% of their total food intake during their larval stage, making this a period of voracious feeding. They may also pupate on the soil surface.

[0004] Currently, the control of the beet armyworm mainly relies on chemical control. Previously commonly used pesticides included 12% abamectin-chlorfenapyr, 15% acetamiprid, and 5.7% abamectin. However, with prolonged use, the efficacy of these pesticides has significantly decreased. Now, 100 g / L brofenoxam suspension concentrate is the main control agent, and its efficacy has improved to some extent. However, the market still needs more effective alternative insecticides to address the beet armyworm's resistance problem.

[0005] The diamondback moth (Plutella xylostella (Linnaeus)) belongs to the family Plutellaeidae in the order Lepidoptera. The number of generations per year varies geographically, with two peak infestation periods: spring (May-June) and autumn (late August-early September), with spring generally being more severe than autumn. In northwestern Hebei, this insect has 3-4 generations per year, overwintering as pupae, with overwintering adults found in the field in April of the following year. The first generation of larvae appears in early May and matures by early June. This generation primarily lives on cruciferous vegetables such as cabbage. Subsequent generations overlap, resulting in mixed developmental stages. In northern regions, two peak infestation periods occur: April-June and August-September, with spring being the dominant period. The diamondback moth is highly specialized, primarily feeding on cruciferous vegetables, and is a common and high-incidence pest. It has developed high resistance to commonly used pesticides, limiting the range of pesticides that can be effectively controlled, making it one of the typical pests that are difficult to manage with chemical pesticides in current agricultural production. During peak pest seasons, farmers typically use methods such as increasing pesticide concentration, increasing the frequency of application, and using highly toxic pesticides for control. As a result, they kill off a large number of natural enemies, disrupt the ecological balance of the vegetable garden, and cause pests to proliferate.

[0006] Current control of the diamondback moth primarily relies on chemical control. Previously commonly used pesticides included 12% abamectin + chlorfenapyr, 5% lufenuron EC, 9.1% abamectin EC, and 20% chlorfenapyr. However, their effectiveness has significantly declined, and alternative insecticides are urgently needed to address the problem of diamondback moth resistance.

[0007] The striped flea beetle (Phyllotreta striolata (Fabricius)) belongs to the order Coleoptera and the family Chrysomelidae. Also known as the cabbage flea, soil flea, yellow flea, dog lice, and yellow striped vegetable beetle, it is a global pest. It occurs throughout my country, but is most severely affected in the southern provinces (autonomous regions). This insect primarily feeds on cruciferous vegetables such as cabbage, cauliflower, Chinese cabbage, radish, mustard greens, rapeseed, and turnip, but it also feeds on fruits, melons, and legumes.

[0008] Current methods for controlling the striped flea beetle mainly rely on chemical control. Commonly used pesticides include dinotefuran, pyridaben, acetamiprid, and cartap, but their effectiveness has significantly declined. There is an urgent need for alternative insecticides to address the problem of pesticide resistance in the striped flea beetle.

[0009] Palm thrips (Thrips palmi Karny) belong to the order Thysanoptera and family Thripidae. They are a major pest of vegetables such as melons, flowers, solanaceous fruits, and legumes. Adults and nymphs scavenge the epidermal tissue of tender shoots, leaves, flowers, and young fruits of their hosts to suck sap. Damaged shoots and leaves harden and shrink, with the hairs turning grayish-brown or dark brown. Plant growth slows, internodes shorten, and young fruits harden, leading to fruit drop. In eggplants, damaged leaves wrinkle, and the underside of leaves develops silvery-gray patches. Later, these patches lose their green color, turning into yellow necrotic spots, and the veins turn dark brown. Damaged young fruits develop scars and may even become deformed, severely impacting eggplant yield and quality. In Kunming, palm thrips can have up to 17-18 generations per year, with overlapping generations. They reproduce year-round, capable of both parthenogenesis and sexual reproduction, exhibiting high reproductive capacity and extremely rapid population growth in the field.

[0010] In recent years, the damage caused by this insect in Yunnan's flower-growing areas has become increasingly serious. For example, in Kunyang Street and Yiliang, the infestation rate of flower plants has reached 100%. Control of palm thrips mainly relies on chemical agents. However, due to the insect's tiny size, it often infests hidden places such as tender buds and flower clusters in the early stages, making it difficult to notice. Often, it is only discovered and controlled when the population in the field has grown large and caused significant damage, resulting in unsatisfactory control effects. To improve control efficacy, people often use unreasonable application methods such as increasing the frequency or dosage of pesticides, leading to the insect developing resistance to most commonly used insecticides. Summary of the Invention

[0011] One of the objectives of this invention is to provide a deuterated diamide insecticide to solve the above-mentioned problems.

[0012] To achieve the above objectives, the technical solution adopted by the present invention is as follows: a deuterated diamide insecticide having the chemical structure shown in the following compound (1):

[0013]

[0014] This invention uses brofenoxam as a lead compound and, through extensive experiments, deuterates specific positions of it, achieving a significant improvement in the insecticidal effect of brofenoxam.

[0015] The second objective of this invention is to provide a method for preparing the above-mentioned deuterated diamide insecticide, the technical solution of which includes the following steps:

[0016] (1) Synthesis of compound (3):

[0017] Using compound (2) as the raw material and tetrahydrofuran as the reaction solvent, the temperature was lowered to -5℃~5℃ under an inert atmosphere, sodium hydride was added, the reaction was stirred for 30 minutes, then deuterated iodomethyl was added dropwise, after which the reaction was stirred for 1 hour, ammonium chloride was added to quench the reaction, the mixture was extracted, and the solvent was evaporated to obtain compound (3).

[0018] (2) Synthesis of compound 4:

[0019] Add tetrahydrofuran, methanol and water to compound (3) obtained in step (1), then add sodium hydroxide, heat to 40°C, keep the temperature for 80 minutes, extract and evaporate the solvent after the reaction is complete to obtain compound (4);

[0020] (3) Synthesis of compound (5):

[0021] Add thionyl chloride to compound 4, heat to 80°C and react for 2 hours, then evaporate the solvent to obtain compound (5);

[0022] (4) Synthesis of compound 7:

[0023] Compound 5 (5) was placed in a reaction vessel, compound (6) was added, and toluene was added. The temperature was raised to 100°C, and the reaction was stirred for 2 hours. The solvent was evaporated and the mixture was subjected to column chromatography to obtain compound (7).

[0024] (5) Synthesis of compound (1):

[0025] Compound (7) was dissolved in dichloromethane and denoted as system A; sodium hydroxide, sodium bromide and water were mixed and denoted as system B; system B was added to system A, the temperature was raised to 40°C, sodium hypochlorite was added dropwise, and the reaction was stirred for 5 hours. After the reaction was completed, the mixture was separated and purified to obtain the final product compound (1).

[0026] The compounds (1)-(7) and the reaction formulas are shown below:

[0027]

[0028] The third objective of this invention is to provide the application of the aforementioned deuterated diamide insecticide for the control of Lepidoptera, Coleoptera, Thysanoptera pests, as well as the killing of termites and mosquitoes.

[0029] As a preferred technical solution: the lepidopteran pests are beet armyworm and diamondback moth; the coleopteran pests are striped flea beetles; and the tsunamipteran pests are palm thrips.

[0030] Compared with the prior art, the advantages of the present invention are as follows: The present invention uses bromfenac as a lead compound and deuterates its specific position, thereby significantly improving the insecticidal effect of bromfenac. It can be widely used to kill lepidopteran, coleopteran, and tsanoptera pests, as well as termites and mosquitoes. It solves the problems of drug resistance and persistence of existing pesticides, and has high biological safety. Attached Figure Description

[0031] Figure 1The 1H NMR spectrum of compound 1 obtained in Example 1 of this invention;

[0032] Figure 2 This is the mass spectrum of compound 1 obtained in Example 1 of the present invention. Detailed Implementation

[0033] The invention will now be further described with reference to the accompanying drawings.

[0034] Example 1:

[0035] A deuterated diamide insecticide having the chemical structure shown in compound 1 below:

[0036]

[0037] Its preparation method includes the following steps:

[0038] (1) Synthesis of compound 3:

[0039] Compound 2 (25 g) was placed in a three-necked flask, 150 mL of tetrahydrofuran was added, the mixture was purged with argon three times, the temperature was lowered to about 0 °C, 4.3 g of sodium hydride was added, the mixture was stirred for 30 minutes, 6.66 mL of deuterated iodomethyl ether was added dropwise, the mixture was stirred for 1 hour, ammonium chloride was added to quench the reaction, ethyl acetate was used for extraction, the organic phases were combined, and 24.43 g of compound 3 was obtained, with a yield of 92%.

[0040] (2) Synthesis of compound 4:

[0041] Compound 3 (24.43 g) was placed in a three-necked flask, and 50 mL of tetrahydrofuran, 50 mL of methanol, and 50 mL of water were added. 13.46 g of sodium hydroxide was added, and the temperature was raised to 40 °C. The reaction was maintained at this temperature for 80 minutes. The reaction was monitored by TLC. After the reaction was completed, the reaction system was adjusted to acidity, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give compound 4 (18.06 g), with a yield of 80%.

[0042] (3) Synthesis of compound 5:

[0043] Compound 4 was added to the reaction system, along with 20 mL of thionyl chloride. The mixture was heated to 80°C and reacted for 2 hours. The solution was then evaporated under reduced pressure for the next step.

[0044] (4) Synthesis of compound 7:

[0045] Compound 5 was placed in a three-necked flask, compound 6 was added, 30 mL of toluene was added, the temperature was raised to 100 °C, the reaction was stirred for 2 hours, the solvent was evaporated under reduced pressure, and column chromatography was performed to give product 7 (30.23 g), yield 79%.

[0046] (5) Synthesis of Compound 1:

[0047] Compound 7 (13 g) was dissolved in 52 mL of dichloromethane, denoted as system A; 0.442 g of sodium hydroxide, 3.41 g of sodium bromide, and 13 mL of water were mixed, denoted as system B; system B was added to system A, the mixture was heated to 40 °C, and 52 mL of sodium hypochlorite was added dropwise. The mixture was stirred for 5 hours, and the reaction was monitored by TLC. After the reaction was complete, the mixture was extracted with dichloromethane, washed with saturated sodium sulfite, evaporated under reduced pressure, and then subjected to column chromatography to give the final product, compound 1 (14 g), with a yield of 94.9%. NMR and mass spectrometry results are as follows: Figure 1 , Figure 2 Place.

[0048] The proton NMR data are as follows:

[0049] 1 H NMR (400MHz, DMSO) δ 10.68 (s, 1H), 8.42 (s, 1H), 7.96 (s, 1H), 7.59 (d, J = 24.2Hz, 2H), 7.31 (d, J = 7.7Hz, 6H).

[0050] Effect test

[0051] The following tests were conducted on the control of pests such as beet armyworm, diamondback moth, yellow striped flea beetle, and palm thrips using compound 1 prepared in Example 1.

[0052] The test reagents used in the following experimental examples include:

[0053] A. Control reagent: 100 g / L bromfenac suspension concentrate manufactured and sold by BASF Europe, i.e., 100 g bromfenac per L of suspension concentrate. The dosage of this suspension concentrate was 5 ml / 667 ml. 2 10ml / 667m 2 20ml / 667m 2 That is, the effective ingredient dosage is 0.5g / 667m 2 1g / 667m 2 2g / 667m 2 The following are referred to as Comparative Example 1, Comparative Example 2, and Comparative Example 3;

[0054] B. Test reagents: Compound 1 obtained in Example 1 above was prepared into a suspension formulation with a concentration of 3g / 100ml using conventional methods. Six active ingredient dosage groups were set up for the experiment, with dosages of 0.5g / 667ml. 2 1g / 667m 2 2g / 667m 2 Hereinafter referred to as "Experimental Example 1", "Experimental Example 2", and "Experimental Example 3" respectively.

[0055] In the following control experiment, when evaluating the control effect, the insect mortality rate (%) = (number of live insects before treatment - number of live insects after treatment) / number of live insects before treatment × 100.

[0056] The following control experiment used EXCEL office software to calculate the control effect and DPS data processing system to statistically analyze the significant differences in control efficacy between treatments.

[0057] Beet armyworm control experiment

[0058] 1. Test site and conditions

[0059] The experiment was conducted on Shanghai bok choy in Zhengjiaying Village, Xinjie Town, Jinning District, Kunming City, Yunnan Province. The soil organic matter content was 1.5%, the pH value was 5.7, the irrigation conditions were good, and the water and fertilizer management was above average. The growth period of Shanghai bok choy was 32 days at the time of pesticide application.

[0060] 2. Test subjects and crops

[0061] Experimental subject: Beet armyworm (Shanghai bok choy);

[0062] Experimental crop: Shanghai bok choy;

[0063] 3. Experimental Design

[0064] The experiment consisted of six treatments: “Control Example 1”, “Control Example 2”, “Control Example 3”, “Experimental Example 1”, “Experimental Example 2”, and “Experimental Example 3”, as mentioned above. Each treatment was repeated four times, with each plot measuring 30m. 2 A total of 24 plots were constructed, arranged in a randomized block design. One application of pesticide was made during the peak emergence period of the beet armyworm (1st-3rd instar), when the insect population was relatively large. The application date was September 27, 2021. Each pesticide was diluted with water to the designed dosage to form a uniform solution, which was then sprayed evenly onto the Shanghai bok choy. A backpack-mounted, automatically adjustable electric sprayer with a single conical nozzle was used. No other insecticides were used during the experiment.

[0065] 4. Drug efficacy survey

[0066] Before applying pesticides, the initial insect population was surveyed. After pesticide application, surveys were conducted again at 1, 3, 10, and 25 days, for a total of 4 surveys. Five samples were taken from each plot, with 5 adjacent plants sampled from each sample. The number of live beet armyworms on the leaves of 25 Shanghai bok choy plants was then investigated, and the mortality rate of the insect population was calculated.

[0067] 5. Results and Analysis

[0068] 5.1 Safety observation of test reagents

[0069] Under the experimental conditions, the pesticides used in "Experimental Example 1", "Experimental Example 2" and "Experimental Example 3" were safe for Shanghai bok choy. No phytotoxicity was observed after the pesticides were applied, and the Shanghai bok choy grew normally.

[0070] 5.2 Control effect on beet armyworm in Shanghai bok choy

[0071] The experimental results, as shown in Table 1, indicate that the control efficacy of Experiment 3 was not significantly different from that of Experiment 2, and was relatively close, but superior to that of Experiment 1. One day after application, the control efficacy of Control Example 1 was 69.0%, while Experiment 3 showed the highest control efficacy, reaching 93.6%. Three and ten days after application, the control efficacies of Experiment 2 and Experiment 3 reached 93.0% and 95.3%, and 91.4% and 95.7%, respectively. With increased dosage, the effects of Experiment 2 and Experiment 3 were significantly better than those of Control Examples 2 and 3. Twenty-five days after application, the mortality rate of Experiment 3 was significantly better than that of Control Example 3, indicating that the residual effect of the compound of this invention is significantly longer than that of bromufenoxam.

[0072] Table 1. Field trial effects of different pesticides on controlling the Shanghai cabbage looper.

[0073]

[0074] Note: (1) The data in the table are all averages of 4 repetitions; the insect population statistics in the table include 1st to 5th instar insects.

[0075] 6. Conclusion:

[0076] The beet armyworm is a relatively difficult pest to control in cruciferous vegetables. The test sample used in this experiment showed good rapid and sustained efficacy against the beet armyworm in Shanghai bok choy, with an effective period of more than 25 days. It is safe for Shanghai bok choy and is an ideal pesticide for controlling the beet armyworm. It can be used as a commonly used or rotating pesticide for controlling the beet armyworm in vegetable production areas of Yunnan.

[0077] Diamondback moth control experiment:

[0078] 1. Test site and conditions

[0079] The experiment was conducted in a cabbage field in Sijie Town, Tonghai County, Yuxi City, Yunnan Province. The soil organic matter content was 2.7%, the pH value was 6.5, irrigation conditions were good, and water and fertilizer management was above average. The pesticide was applied during the early heading stage of the cabbage growth.

[0080] 2. Experimental subjects and crops

[0081] Experimental subject: Diamondback moth of cabbage;

[0082] Experimental crop: Cabbage;

[0083] 3. Experimental Design

[0084] The experiment consisted of six treatments: “Control Example 1,” “Control Example 2,” “Control Example 3,” “Experimental Example 1,” “Experimental Example 2,” and “Experimental Example 3,” with each treatment replicated four times. Each plot was 40 square meters, for a total of 24 plots arranged in a randomized block design. The pesticide was applied once during the peak emergence period of the diamondback moth (1st to 3rd instar), when the initial insect population was relatively large. The application date was August 13, 2021. Each pesticide was diluted with water to the designed dosage to form a uniform solution, which was then sprayed evenly onto the Shanghai bok choy. A backpack-mounted, automatically adjustable electric sprayer with a single conical nozzle was used. No other insecticides were used during the experiment.

[0085] 4. Drug efficacy survey

[0086] The initial insect population was surveyed before pesticide application, and then again at 1, 3, 10, and 25 days after application, for a total of four surveys. Five samples were taken from each plot, with five adjacent plants sampled from each point. The number of live diamondback moths on the leaves of 25 cabbage plants was then investigated, and the mortality rate of the insect population was calculated.

[0087] 5. Results and Analysis

[0088] 5.1 Safety observation of test reagents

[0089] Under the experimental conditions, the pesticides used in "Experimental Example 1", "Experimental Example 2" and "Experimental Example 3" were safe for cabbage. No phytotoxicity was observed after the pesticides were applied, and the cabbage grew normally.

[0090] 5.2 Control effect on diamondback moth of cabbage

[0091] The experimental results, as shown in Table 2, indicate that 1 day after application, the control efficacy of Experiment 3 was not significantly different from that of Experiment 2, but significantly different from that of Experiment 1. 1 day after application, the control efficacy of Experiment 1 and Control Example 1 was 80.8% and 83.3%, respectively, with Experiment 3 showing the highest efficacy at 95.9%. 3 and 10 days after application, the control efficacy of Experiment 2 and Experiment 3 reached 94.8% and 97.1%, and 97.3% and 98.5%, respectively, showing significantly better efficacy than Control Example 2 and Control Example 3 after increasing the effective dosage. 25 days after application, the mortality rate of Experiment 1, Experiment 2, and Experiment 3 was significantly better than that of Control Example 1, Control Example 2, and Control Example 3, and the duration of efficacy was significantly longer than that of the control example (brombutamide).

[0092] Table 2. Field trial effects of different pesticides on control of diamondback moth in cabbage.

[0093]

[0094] Note: All data in the table are averages of four replicates; the insect population statistics in the table include 1st to 5th instar insects; 2.3 Conclusion

[0095] This study demonstrates that the pesticides used in the three control examples and the three experimental examples were all effective in controlling the diamondback moth and safe for head cabbage. The pesticides used in the three experimental examples showed significantly longer-lasting effects than those used in the control examples, providing prolonged and highly effective control of the diamondback moth.

[0096] Yellow-striped flea beetle control experiment

[0097] 1. Test site and conditions

[0098] The experiment was conducted on Shanghai bok choy in Tianjiaba Village, Xinjie Town, Jinning District, Kunming City, Yunnan Province. The soil organic matter content was 2.1%, the pH value was 5.9, irrigation conditions were good, and water and fertilizer management was above average. The Shanghai bok choy was 22 days old when the pesticide was applied.

[0099] 2. Test subjects and crops

[0100] Test subject: Shanghai green flea beetle;

[0101] Experimental crop: Shanghai bok choy;

[0102] 3. Experimental Design

[0103] The experiment consisted of four treatments: “Control Example 1”, “Control Example 2”, “Control Example 3”, “Experimental Example 1”, “Experimental Example 2”, and “Experimental Example 3”, with each treatment replicated four times. Each plot was 20 square meters, for a total of 24 plots arranged in a randomized block design. The pesticide was applied once during the peak emergence period of the beet armyworm (1st to 3rd instar), when the initial insect population was relatively large. The application date was September 27, 2021. Each pesticide was diluted with water to the designed dosage to form a uniform solution, which was then sprayed evenly onto the Shanghai bok choy. A backpack-mounted, automatically adjustable electric sprayer with a single conical nozzle was used. No other insecticides were used during the experiment.

[0104] 4. Drug efficacy survey

[0105] Before applying pesticides, the initial insect population was surveyed. After pesticide application, surveys were conducted again at 1, 3, 10, and 25 days, for a total of 4 surveys. Five samples were taken from each plot, with 5 adjacent plants sampled from each sample. The number of live flea beetles on the leaves of 25 Shanghai bok choy plants was then investigated, and the mortality rate of the insect population was calculated.

[0106] 5. Results and Analysis

[0107] 5.1 Safety observation of test reagents

[0108] Under the experimental conditions, the pesticides in the three experimental cases were safe for Shanghai bok choy, and no phytotoxicity was observed after application. The Shanghai bok choy grew normally.

[0109] 5.2 Control effect on Shanghai green flea beetle

[0110] The experimental results, as shown in Table 3, indicate that 1 day after application, the control efficacy of Experimental Example 3 was not significantly different from that of Experimental Example 2, and was quite similar. Experimental Example 3 was significantly better than both Control Example 3 and Control Example 2, but showed a significant difference in control efficacy compared to Experimental Example 1. The control efficacy of Control Example 1 was 64.9% 1 day after application and 80.3% 10 days after application, showing a significant difference compared to Experimental Example 2.

[0111] Table 3. Field trial effects of different pesticides on the control of Shanghai green flea beetle.

[0112]

[0113] Note: (1) The data in the table are the average of 4 repetitions; (2) The population statistics in the table include 1st to 5th instar larvae.

[0114] 6. Conclusion

[0115] This study demonstrates that the formulations in Experiment 2 and Experiment 3 have good control effects against Shanghai flea beetles and exhibit good rapid-acting properties, significantly better than Controls 2 and 3. Furthermore, after 25 days, their effective duration is superior to that of the control formulation, bromuconazole suspension, at the same effective dosage.

[0116] Palm thrips control trial data

[0117] 1. Test site and conditions

[0118] The experiment was conducted at the home of farmer Wu Gang in Yujiahai, Kunyang Street, Jinning District, Kunming City, Yunnan Province. The soil organic matter content was 1.5%, the pH value was 6.7, the irrigation conditions were good, and the water and fertilizer management was above average. The rose plants used at the time of pesticide application were 5-year-old plants.

[0119] 2. Test subjects and crops

[0120] Test subject: Rose palm thrips;

[0121] Experimental crop: Rose, variety: Plateau Red

[0122] 3. Experimental Design

[0123] The experiment consisted of four treatments: Control Example 2, Control Example 3, Experimental Example 2, and Experimental Example 3, as described above. Each treatment was replicated four times, with each plot measuring 30 square meters, for a total of 16 plots arranged in a randomized block design. The pesticide was applied once during the peak emergence period of palm thrips (1st to 3rd instar), when the insect population was relatively large. The application date was May 18, 2021. Each pesticide was diluted with water to the designed dosage to form a uniform solution, which was then sprayed evenly onto the rose bushes. A backpack-mounted, automatically adjustable electric sprayer with a single conical nozzle was used. No other insecticides were used during the experiment.

[0124] 4. Drug efficacy survey

[0125] Before applying pesticides, the initial insect population was surveyed. After pesticide application, surveys were conducted again at 1 day, 3 days, and 10 days, for a total of 4 surveys. Five samples were taken from each plot, with 5 adjacent plants sampled from each sample. The number of live insects on the flowers of 25 rose bushes was then investigated, and the insect mortality rate was calculated.

[0126] 5. Results and Analysis

[0127] 5.1 Safety observation of test reagents

[0128] Under the experimental conditions, the pesticide samples in both cases were safe for roses, and no phytotoxicity was observed after application; the roses grew normally.

[0129] 5.2 Control effect on rose palm thrips

[0130] The experimental results, as shown in Table 4, indicate that one day after application, the control efficacy of Experimental Example 2 and Experimental Example 3 were 92.6% and 97.7%, respectively, significantly better than those of Control Example 2 and Control Example 3. The control efficacy of Control Example 2 was 28.6% one day after application, but only 16.7% ten days later, showing a significant difference from that of Experimental Example 2.

[0131] Table 4. Field trial effects of different pesticides on controlling thrips on rose and palm trees.

[0132]

[0133] Note: (1) The data in the table are the average of 4 repetitions; (2) The population statistics in the table include 1st to 4th instar larvae.

[0134] 6. Conclusion

[0135] This study demonstrates that the sample formulations of Experiment 2 and Experiment 3 have good control effects on rose palm thrips, and exhibit good rapid-acting properties with a residual effect of more than 10 days. They are significantly better than the control in terms of residual effect and mortality rate.

[0136] 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, and improvements made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A deuterated bisamide insecticide characterized by: It has a chemical structure as shown in the following compound 1: 。 2. The process for the preparation of deuterated bisamide insecticides as claimed in claim 1, wherein, Comprise the following steps: (1) Synthesis of compound 3: Take compound 2 as raw material, tetrahydrofuran as reaction solvent, under inert atmosphere, cool to-5℃~5℃, add sodium hydride, stir for 30 minutes, then drop deuterated methyl iodide, after adding, stir for 1 hour, add ammonium chloride to quench the reaction, extract, spin dry solvent to obtain compound 3; (2) Synthesis of compound 4: To the compound 3 obtained in step (1), add tetrahydrofuran, methanol and water, then add sodium hydroxide, heat to 40℃, keep reaction for 80 minutes, after reaction is completed, extract, spin dry solvent to obtain compound 4; (3) Synthesis of compound 5: To compound 4, add dichlorosulfoxide, heat to 80℃ for 2 hours, spin dry solvent to obtain compound 5; (4) Synthesis of compound 7: Put compound 5 into reaction container, add compound 6 and toluene, heat to 100℃, stir for 2 hours, spin dry solvent, column chromatography to obtain compound 7; (5) Synthesis of compound 1: Dissolve compound 7 in dichloromethane, as system A; Take sodium hydroxide, sodium bromide, water, mix as system B, add system B to system A, heat to 40℃, drop sodium hypochlorite, stir for 5 hours, after reaction is completed, separate and purify to obtain final product compound 1; The compounds 1-7, and reaction formula are as follows: 。 3. Use of a deuterated bisamide insecticide according to claim 1, characterized in that: For controlling lepidoptera, coleoptera, and thysanoptera pests.

4. Use according to claim 3, characterized in that: The lepidoptera pests are Spodoptera exigua and Plutella xylostella; the coleoptera pest is Phyllotreta striolata; the thysanoptera pest is Odontothrips palustris.

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