CN113929695A

CN113929695A - Sulfenimide psoralen derivatives, and preparation method and application thereof

Info

Publication number: CN113929695A
Application number: CN202111351115.1A
Authority: CN
Inventors: 范志金; 董静月; 洪泽宇; 李坤; 陈蕾; 高卫; 唐良富; 王志宏
Original assignee: Nankai University
Current assignee: Nankai University
Priority date: 2021-11-16
Filing date: 2021-11-16
Publication date: 2022-01-14
Anticipated expiration: 2041-11-16
Also published as: CN113929695B

Abstract

The invention provides a sulfinyl imine psoralen derivative, a preparation method and application thereof, and particularly relates to a sulfinyl imine psoralen derivative, wherein the chemical structure general formula of the sulfinyl imine psoralen derivative is shown as formula I:

Description

Sulfenimide psoralen derivatives, and preparation method and application thereof

Technical Field

The technical scheme of the invention belongs to the field of pesticides, and particularly relates to sulfenimide psoralen compounds and a preparation method and application thereof.

Background

Psoralen is derived from furan type coumarin compounds in fructus psoraleae, widely exists in traditional Chinese medicines such as radix glehniae, radix saposhnikoviae, radix angelicae pubescentis and the like, and has multiple physiological and pharmacological activities (Yuan sea dragon and other Chinese herbal medicines, 2021, 52 (01): 289) -298 ℃ and the like) of relaxing tracheal smooth muscle, preventing and treating osteoporosis, stopping bleeding, inhibiting bacteria, killing insects, resisting cancers, resisting HIV, resisting inflammation, resisting oxidation and the like. Psoralen is used as a bactericide in agriculture, has a wide antibacterial spectrum and a long lasting period, and is an ideal bactericide in agriculture. Compared with the conventional pesticide, the psoralen has the effects of contact poisoning and stomach poisoning on pests, and has obvious effect; psoralen is also an important botanical drug intermediate, has the characteristics of low toxicity, no residue, no pollution and no public nuisance on various grain, melon and fruit, vegetables and other commercial crops, and is more favorable for environmental protection.

Sulfenimide compounds are hexavalent sulfur compounds containing one oxygen atom, one nitrogen atom and two carbon substituents, and are molecular fragments which have biological activity and are widely present in bioactive molecules such as pesticides and medicines. Sulfenimide is a very potential bioisostere in pharmaceutical chemistry, and the stereochemistry of the sulfur atom has a great influence on the biological activity of the compound. The sulfinyl imine is taken as an isostere of sulfone, a nitrogen atom provides a modifiable site, and the sulfenyl imine also becomes a key point of medicine development attention, and the structural fragment is introduced into a medicine molecule, so that the water solubility of the medicine can be improved, and the physicochemical property of the compound can be improved, thereby improving the activity of the compound. Meanwhile, the sulfinyl imine can also be used as a chiral auxiliary group, an asymmetric catalytic ligand and a hydrocarbon activated guide group (Zhang hong et al, Nature science edition, 2016, 25 (6): 491-.

In order to search and discover pesticide lead and candidate compounds which are more efficient, broad-spectrum, low-toxicity, low-ecological risk and free of cross resistance, the invention introduces a sulfenimide structure into a psoralen lead structure, designs and synthesizes sulfenimide psoralen derivatives, and screens and evaluates the biological activity of a system.

Disclosure of Invention

The technical problem to be solved by the invention is as follows: provides a synthesis method of a novel sulfinylimine psoralen derivative, provides a method for regulating and controlling the biological activity of agricultural, horticultural and sanitary and forestry plant pests and plant pathogens by using the compound and a determination method thereof, and also provides application of the compound in the agricultural field, the horticultural field, the forestry field and the sanitary field.

The technical scheme adopted by the invention for solving the technical problem is as follows: the chemical structural general formula of the sulfinyl imine psoralen compound with insecticidal, acaricidal, bactericidal, anti-plant virus and plant disease-resistant activities in the agricultural field, the horticultural field and the forestry field is shown as I:

wherein R is¹Selected from: hydrogen, 4-fluoro, 4-chloro; r²Selected from: cyclopropanesulfonyl, 4-trifluoromethoxybenzenesulfonyl, 4-nitrobenzenesulfonyl, 4-methylbenzenesulfonyl, 2, 4-dichlorobenzenesulfonyl, 4-methoxybenzenesulfonyl, 4-fluorobenzenesulfonyl, 4-chlorobenzenesulfonyl, benzenesulfonyl, 4-tert-butylbenzenesulfonyl, methanesulfonyl, trifluoromethanesulfonyl, 4-iodobenzenesulfonyl, 4-bromobenzenesulfonyl, 4-ethylbenzenesulfonyl, 3, 4-difluorobenzenesulfonyl, 2-naphthalenesulfonyl, 4-tert-butylbenzoyl, hydrogen, 4-trifluoromethylbenzoyl, 3-bromobenzoyl, 3-trifluoromethoxybenzoyl, 4-methylbenzoyl, 4-fluorobenzoyl, acetyl, 1-naphthoyl, (3, 5-dichlorophenyl) carbamoyl, (4-trifluoromethoxyphenyl) carbamoyl, (4-fluorophenyl) carbamoyl, (3-methylphenyl) aminomethylAcyl, 3, 4-dichloroisothiazole-5-formyl, 3- (difluoromethyl) -1-methyl-1H-pyrazole-4-formyl, 2-furoyl, cyclopentanecarboxyl, 2, 4-difluorobenzoyl, 2-chlorobenzoyl.

The synthesis route of the sulfinyl imine psoralen derivative I and the intermediate thereof is as follows:

the synthesis method of the sulfinyl imine psoralen derivative I comprises the following steps:

A. preparation of compound 3:

putting the compound 1 into a reaction bottle, adding the compound 2, then slowly dropwise adding 98% concentrated sulfuric acid while stirring, and stirring at room temperature; after the reaction is finished, adding a proper amount of methanol, then pouring the methanol into ice water to generate a large amount of white solid, and performing suction filtration and drying to obtain a compound 3;

B. preparation of compound 5:

putting the compound 3 into a reaction bottle, adding a proper amount of anhydrous acetonitrile, then sequentially adding potassium carbonate, potassium iodide and the compound 4 while stirring, and heating and refluxing; after the reaction is finished, removing most of acetonitrile under reduced pressure, adding water and ethyl acetate for extraction, washing an organic phase by using a saturated sodium chloride solution, drying anhydrous sodium sulfate, carrying out suction filtration under reduced pressure, concentrating a filtrate to remove a solvent, and carrying out column chromatography purification to obtain a compound 5;

C. preparation of compound 6:

adding a compound 5 into a reaction bottle, adding a proper amount of isopropanol, slowly dropwise adding 1 mol/L sodium hydroxide solution while stirring, and heating and refluxing; after the reaction is finished, removing most of isopropanol under reduced pressure, adjusting the pH of the system to be 1-2 by using 1 mol/L hydrochloric acid solution, and performing suction filtration and drying on the generated solid to obtain a compound 6;

D. preparation of compound 7:

adding a proper amount of N, N-dimethylformamide into the compound 6 in a reaction bottle, then sequentially adding 1H-benzotriazole-1-yloxytripyrrolidinyl hexafluorophosphate, N-diisopropylethylamine and 4-aminothioanisole under stirring, and stirring at room temperature; after the reaction is finished, adding water and ethyl acetate for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, carrying out vacuum filtration, concentrating a filtrate to remove a solvent, and carrying out column chromatography purification to obtain a compound 7;

E. preparation of Compound I-a:

putting the compound 7 into a reaction bottle, adding a proper amount of anhydrous methanol, sequentially adding iodobenzene diacetic acid and ammonium carbonate while stirring, and stirring at room temperature; after the reaction is finished, removing most of methanol under reduced pressure, adding water and ethyl acetate for extraction, washing an organic phase by using a saturated sodium chloride solution, drying anhydrous sodium sulfate, carrying out suction filtration under reduced pressure, concentrating a filtrate to remove a solvent, and carrying out column chromatography purification to obtain a compound I-a;

F. preparation of Compound I-b:

taking the compound I-a, adding a proper amount of anhydrous pyridine into a reaction bottle, then adding substituted sulfonyl chloride, and stirring at room temperature; after the reaction is finished, adding water and ethyl acetate for extraction, washing an organic phase by using a 1 mol/L hydrochloric acid solution and a saturated sodium chloride solution in sequence, drying the organic phase by using anhydrous sodium sulfate, performing suction filtration under reduced pressure, concentrating the filtrate to remove the solvent, and performing column chromatography purification to obtain a compound I-b;

G. preparation of Compounds I-c:

taking the compound I-a, adding a proper amount of anhydrous pyridine into a reaction bottle, then adding substituted acyl chloride, and stirring at room temperature; after the reaction is finished, adding water and ethyl acetate for extraction, washing an organic phase by using a 1 mol/L hydrochloric acid solution, a saturated sodium bicarbonate solution and a saturated sodium chloride solution in sequence, drying by using anhydrous sodium sulfate, carrying out vacuum filtration, concentrating a filtrate to remove a solvent, and carrying out column chromatography purification to obtain a compound I-c;

H. preparation of Compounds I-d:

taking the compound I-a, adding a proper amount of N, N-dimethylformamide into a reaction bottle, then sequentially adding cuprous chloride and substituted isocyanate, and stirring at room temperature; after the reaction is finished, adding water and ethyl acetate for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, carrying out vacuum filtration, concentrating a filtrate to remove a solvent, and carrying out column chromatography purification to obtain the compounds I-d.

As a preferred embodiment, the synthesis method of the sulfinyl imine psoralen derivative of the invention is divided into the following steps:

A. preparation of compound 3:

a100 ml round-bottom flask was charged with 18.2 mmol of resorcinol and 18.2 mmol of dimethyl acetylsuccinate, followed by slowly dropping 2.73 ml of 98% concentrated sulfuric acid under stirring, and after the dropping was completed, the reaction system was stirred at room temperature overnight. Monitoring by TLC, adding 30 ml of anhydrous methanol after the reaction is finished, pouring the anhydrous methanol into ice water to generate a large amount of white solid, performing suction filtration on the obtained solid, washing the crude product with diethyl ether, and recrystallizing with ethanol-water to obtain a compound 3; the amount of compound 3 produced and the volume of the reaction vessel are scaled up or down accordingly.

B. Preparation of compound 5:

in a 100 ml round-bottom flask were charged 4.03 mmol of compound 3 and 30 ml of anhydrous acetonitrile, and 4.836 mmol of compound 4, 16.12 mmol of anhydrous potassium carbonate and 0.403 mmol of potassium iodide were sequentially added under stirring at room temperature, followed by heating and refluxing the reaction system for 5 hours. Monitoring by TLC, standing and cooling to room temperature after the reaction is finished, removing most of solvent under reduced pressure, adding 30 ml of water into the residue, extracting for three times (15 ml. times.3) by ethyl acetate, washing the organic phase for three times (15 ml. times.3) by saturated sodium chloride solution, and drying the combined organic layers by anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with petroleum ether/ethyl acetate (3: 1, volume/volume) eluent column chromatography to obtain compound 5; the amount of compound 5 produced and the volume of the reaction vessel are scaled up or down accordingly.

C. Preparation of compound 6:

1 g of compound 5 and 30 ml of isopropanol are added into a 100 ml round-bottom flask, 30 ml of 1 mol/l sodium hydroxide solution is slowly added dropwise under stirring at room temperature, and the reaction system is heated and refluxed for 4 hours after the dropwise addition. Monitoring by TLC, standing the system after the reaction is finished, cooling to room temperature, removing most isopropanol under reduced pressure, adding 1 mol/L hydrochloric acid solution into the residue to adjust the pH of the system to 1, precipitating a large amount of solid, performing suction filtration, and drying to obtain a compound 6; the amount of compound 6 produced and the volume of the reaction vessel are scaled up or down accordingly.

D. Preparation of compound 7:

a100 ml round-bottomed flask was charged with 1 mmol of Compound 6 and 15 ml of N, N-dimethylformamide, and 1.1 mmol of 1H-benzotriazol-1-yloxytripyrrolidinyl hexafluorophosphate, 2.5 mmol of N, N-diisopropylethylamine and 1.1 mmol of 4-aminoanisole were sequentially added thereto with stirring, followed by stirring at room temperature for 6 hours. TLC, 30 ml of water was added after the reaction was complete, extracted three times with ethyl acetate (15 ml × 3), the separated organic phase was washed three times with saturated sodium chloride solution (15 ml × 3), and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with petroleum ether/ethyl acetate (3: 1, volume/volume) eluent column chromatography to obtain compound 7; the amount of compound 7 produced and the volume of the reaction vessel are scaled up or down accordingly.

E. Preparation of Compound I-a:

a100 ml round-bottom flask was charged with 1 mmol of Compound 7 and 30 ml of anhydrous methanol, and 2.3 mmol of iodobenzene diacetic acid and 1.5 mmol of ammonium carbonate were sequentially added thereto with stirring, and stirred at room temperature for 8 hours. TLC, after the reaction was complete most of the methanol was removed under reduced pressure, 30 ml of water was added to the residue, extracted three times with ethyl acetate (15 ml × 3), the organic phase was separated and washed three times with saturated sodium chloride solution (15 ml × 3), and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with dichloromethane/methanol (20: 1, volume/volume) eluent column chromatography to obtain compound I-a; the amount of compound I-a prepared and the volume of the reaction vessel are scaled up or down accordingly.

F. Preparation of Compound I-b:

a100 ml round-bottom flask was charged with 1 mmol of Compound I-a and 15 ml of anhydrous pyridine, and 1 mmol of substituted sulfonyl chloride was added with stirring and stirred at room temperature for 8 hours. TLC, 30 ml of water was added after the reaction was complete, extracted three times with ethyl acetate (15 ml × 3), the organic phase was separated and washed three times with 1 mol/l hydrochloric acid solution (15 ml × 3) and saturated sodium chloride solution (15 ml × 3) in sequence, and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with dichloromethane/methanol (100: 1, volume/volume) eluent column chromatography to obtain compound I-b; the amount of compound I-b prepared and the volume of the reaction vessel are scaled up or down accordingly.

G. Preparation of Compounds I-c:

a100 ml round-bottom flask was charged with 1 mmol of Compound I-a and 15 ml of anhydrous pyridine, and 1 mmol of substituted acid chloride was added with stirring and stirred at room temperature for 8 hours. TLC, 30 ml of water was added after the reaction was complete, extracted three times with ethyl acetate (15 ml × 3), the organic phase was separated and washed three times with 1 mol/l hydrochloric acid solution (15 ml × 3), saturated sodium bicarbonate solution (15 ml × 3), saturated sodium chloride solution (15 ml × 3) in sequence, and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with dichloromethane/methanol (100: 1, volume/volume) eluent column chromatography to obtain compound I-c; the amount of compound I-c prepared and the volume of the reaction vessel are scaled up or down accordingly.

H. Preparation of Compounds I-d:

a100 ml round-bottom flask was charged with 1 mmol of Compound I-a and 30 ml of N, N-dimethylformamide, and 0.1 mmol of cuprous chloride and 1 mmol of substituted isocyanate were sequentially added thereto under stirring, followed by stirring at room temperature for 8 hours. TLC, 30 ml of water was added after the reaction was complete, extracted three times with ethyl acetate (15 ml × 3), the separated organic phase was washed three times with saturated sodium chloride solution (15 ml × 3), and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with dichloromethane/methanol (100: 1, volume/volume) eluent column chromatography to obtain compound I-d; the amount of the compounds I-d prepared and the volume of the reaction vessel are scaled up or down accordingly.

Wherein, the substituent R¹、R²As defined above; r¹Selected from: hydrogen, 4-fluoro, 4-chloro; r²Selected from: cyclopropanesulfonyl, 4-trifluoromethoxybenzenesulfonyl, 4-nitrobenzenesulfonyl, 4-methylbenzenesulfonyl, 2, 4-dichlorobenzenesulfonyl, 4-methoxybenzenesulfonyl, 4-fluorobenzenesulfonyl, 4-chlorobenzenesulfonyl, benzenesulfonyl, 4-tert-butylbenzenesulfonyl, methanesulfonyl, trifluoromethanesulfonyl, 4-iodobenzenesulfonyl, 4-bromobenzenesulfonyl, 4-ethylbenzenesulfonyl, 3, 4-difluorobenzenesulfonyl, 2-naphthalenesulfonyl, 4-tert-butylbenzoyl, hydrogen, 4-trifluoromethylbenzoyl, 3-bromobenzoyl, 3-trifluoromethoxybenzoyl, 4-methylbenzoyl, 4-fluorobenzoyl, acetyl, 1-naphthoyl, (3, 5-dichlorophenyl) carbamoyl, (4-trifluoromethoxyphenyl) carbamoyl, (4-fluorophenyl) carbamoyl, (3-methylphenyl) carbamoyl, 3, 4-dichloroisothiazole-5-formyl, 3- (difluoromethyl) -1-methyl-1H-pyrazole-4-formyl, 2-furoyl, cyclopentanecarboxyl, 2, 4-difluorobenzoyl, 2-chlorobenzoyl.

The invention provides application of the sulfinyl imine psoralen derivative I in preparing a fungicide.

The invention provides application of the sulfinyl imine psoralen derivative I in preparing an anti-tobacco mosaic virus agent.

The invention provides application of the sulfinyl imine psoralen derivative I in preparing a plant activator for inducing tobacco to resist tobacco mosaic virus.

The invention provides application of the sulfinyl imine psoralen derivative I in preventing and treating agricultural and forestry and horticultural plant insect pests.

Co-administering the sulfinyl imido psoralen derivative I and an agricultural chemical; the agrochemical is selected from: one or more of insecticide, bactericide, plant virus resisting agent and acaricide.

The sulfinyl imine psoralen derivative I and any one or two of the pesticides are combined to form a pesticide composition for preventing and treating agricultural and forestry and horticultural plant insect pests;

the insecticide is selected from: methoprene, diazinon, acetamiprid, emamectin benzoate, milbemectin, abamectin, pleocidin, metaflumethrin, meperfluthrin, cyfluthrin, beta-cypermethrin, lambda-cyhalothrin, permethrin, allethrin, bifenthrin, permethrin, flumethrin, cyfluthrin, imidacloprid, nitenpyram, imidaclothianidin, thiacloprid, thiamethoxam, clothianidin, dinotefuran, cotinine, dinotefuran, diflubenzuron, chlorbenzuron, tefluazuron, flufenoxuron, lufenuron, chlorflufenoxuron, fluazuron, diflubenzuron, fluazuron, tezine, fluazuron, tezine, teflufenozide, tebufenozide, tezine, flufenozide, tebufenozide, tezine, tebufenozide, tezine, tebufenozide, tezine, tebufalin, tezine, tebenflumetsulbenflumetsulbens, tezine, tebenil, tezine, tebenil, tebenflumetsulbens, tebenil, tebens, tezine, tebens, and tebens, and the like, Methoxyfenozide, chromafenozide, dichlorvos, quinalphos, pyridaphenthion, cicada powder, carbaryl, pirimicarb, metolcarb, isoprocarb, cartap, fenobucarb, tetrafenozide, fenitrothion, hexythiazox, carbaryl, fenisobromolate, hexythiazox, pyridate, clofentezine, spirodiclofen, spirotetramat, azocyclobutazine, buprofezin, monosultap, dimehypo, chlorantraniliprole, tetrachlorantranilide, flubendiamide, cyantraniliprole, butenenitrile, tolfenpyrad, chlorfenapyr, pyrazofos, pyrazinone, etoxazole, tebufenpyrad, pyridaben, emamectin, and pentapyraflufen;

the content of the sulfinyl imine psoralen derivative I in the insecticidal composition is 1-90% by mass; preferably, the ratio of the sulfinyl imine psoralen derivative I to the pesticide is 1 percent to 99 percent to 1 percent in percentage by mass;

the insecticide composition is processed into a dosage form selected from the group consisting of: seed treatment emulsions, aqueous emulsions, microemulsions, suspoemulsions, capsule suspensions, water soluble granules, fine granules, soluble concentrates, venoms, block baits, granular baits, tablet baits, concentrated baits, sustained release blocks, electrostatic sprays, oil-in-water emulsions, aerosol cans, aerosol candles, aerosol cartridges, aerosol sticks, aerosol tablets, aerosol pellets, gas generants, ointments, hot fogging formulations, cold fogging formulations, aerosols, solid/liquid mixtures, liquid/liquid mixtures, solid/solid mixtures, lacquers, microgranules, chasing powders, oil suspensions, oil dispersible powders, concentrated gels, pour-on formulations, seed coatings, paints, film-forming oils, ultra-low volume liquids, vapor release agents;

the plant insect pests controlled by the insecticidal composition are selected from: meadow spodoptera, red spider, east Asian migratory locust, spruce-bug, Chinese rice locust, japanese yellow-back locust, single-prick mole cricket, oriental mole cricket, rice thrips, thrips tabaci, green house thrips, rice straw thistle, wheat simple pipe thrips, green house whitefly, bemisia tabaci, black tail hopper, big leaf hopper, cotton leafhopper, lesser leafhopper, brown plant hopper, white back plant hopper, gray plant hopper, sugarcane flat leaf planthopper, cotton aphid, binary wheat aphid, wheat straw aphid, peach aphid, sorghum aphid, radish aphid, mealybug, lybug, stinkbug, arrowhead bug, round scale, white insect, red wax insect, red worm, mealybug, pear net, banana net bug, tiny flower bug, laceleaf fly, green fly, rice moth, black armyworm, black fly, black rice moth, black armyworm, black rice moth, black rice plant, black rice plant, black rice plant, green plant, rice plant, black rice plant, green plant, rice plant, green plant, rice plant, pink bollworm, sweet potato wheat moth, diamond back moth, peach fruit borer, soybean pod borer, peach fruit borer, apple tip leaf roller moth, brown banded leaf roller moth, pardos leaf roller moth, striped rice borer, pod borer, corn borer, yellow rice borer, cabbage moth, rice leaf roller borer, striped rice borer, cotton leaf borer, peach borer, armyworm, prodenia litura, rice bollworm, cotton small bridgehead moth, beet armyworm, sesamia inferen, cotton bollworm, Dinodon diamond-back moth, agrotis, yellow cutworm, robber venom moth, gypsy moth, sweet potato hawkmoth, bean hawkmoth, straight grain rice skipper, cryptophyte butterfly, caeruleuca, caeruleuciscus nigra, yellow mealyratus caeruleucade, yellow meadowrue, yellow rice beetle, yellow tiger, red ramie yellow vanne, yellow rice borer, yellow rice, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice, yellow rice borer, yellow rice borer, yellow rice, yellow rice borer, yellow rice, Tribolium castaneum, verdigris, black tortoise, branchia palustris, longicorn beetle, pink neck longicorn beetle, ape leaf worm, yellow melon, flea beetle, mung bean weevil, pea weevil, broad bean weevil, corn weevil, rice weevil, wheat leaf bee, pear fruit bee, yellow stripe wasp, armyworm white star ichneumonid, sandfly bractenoconid, cotton bollworm tooth-lipped ichneumonid, borer black spot wart, mosquito, fly, horsefly, red mud fly, yellow leaf sucking serous, rice gall mosquito fly, citrus fruit fly, melon fruit fly, wheat leaf gray fly, American fly, black stalk black fly, wheat stem fly, seed fly, onion fly, radish skirt, eupatorium, corn borer, and armyworm;

the plants controlled by the insecticidal composition are selected from the following plants: rice, wheat, barley, oats, corn, sorghum, sweet potato, cassava, soybean, sweet broad bean, pea, mung bean, small bean, cotton, silkworm, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili, radish, cucumber, cabbage, celery, tuber mustard, sugar beet, rape, shallot, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

The sulfinyl imine psoralen derivative I and any one or two of the bactericides are combined to form a bactericidal composition for preventing and treating agricultural and forestry and horticultural plant diseases;

the bactericide is selected from: benzothiadiazole, tiadinil, thianamide, methicillin, 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid, 4-methyl-1, 2, 3-thiadiazole-5-sodium formate, 4-methyl-1, 2, 3-thiadiazole-5-ethyl formate, DL-beta-aminobutyric acid, isotianil, 3, 4-dichloroisothiazole-5-carboxylic acid, 3, 4-dichloroisothiazole-5-sodium formate, 3, 4-dichloroisothiazole-5-ethyl formate, ribavirin, antofine, ningnanmycin or salicylic acid, cyanamide, thiram, ziram, mancozeb, fosetyl, thiophanate-methyl, chlorothalonil, chlormadinone, procymidone, fenpropidium rust, Thiophanate methyl, thiophanate, metalaxyl-M, flumorph, dimethomorph, metalaxyl-M, benalaxyl-M, diclocyanamide, sulfentram, sulfsulfamide, thifluzamide, folpet, cyprodinil, cyhalodiamide, silthiopham, carboxin, oxim-methyl, mefuram, fenazamide, flutolanil, furametpyr, thifluzamide, boscalid, penthiopyrad, isopyrazamide, bixafen, fluopyram, fluxastrobin, fluxapyroxad, flufenapyr, benconazole, iprovalicarb, flutriafolan, flufenpyrazamide, flufenacetmid, fluoxastrobin, fenhexamid, iprodione, trifloxystrobin, kresoximtrobin, trifloxystrobin, fenstrobin, fenstrobilurin, fenpyraclostrobin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluopicolide, fluopicolinate, fluopicolide, fluopicolinate, fluopicolide, fluopicolinate, fluo, Enestroburin, dimethomorph, difenoconazole, bromhexine, epoxiconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole, difenoconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimenol, triticonazole, bitertanol, thiabendazole, imazalil, prochloraz, triflumizole, cyazofamid, fenamidone, imidazole, pefurazoate, famoxadone, pyridinozole, prodiamine, ethaboxam, hymexazol, penoxsulam, fenthion, fenpropimorph, tridemorph, fenpyroxanil, fluazinam, fenpropiconazole, fenpyrazamide, fluazinam, cyprodinil, flufenamidone, fenpyrad, fenpyroxim, fenpyroxapyroxapyroxad, fenpyroxad-methyl, fenpyroxad-a, Mepanipyrim, pyrimethanil, fenarimol, fluoropyrimidinol, mefenamate, dithianon, ethoxyquin, hydroxyquinoline, propoxymine, phenoxyquinoline, diethofencarb, iprovalicarb, benthiavalicarb, propamocarb, sulbencarb, edifenphos, iprobenfos, pyrazofos, tolclofos-methyl, blasticidin, kasugamycin, polyoxin, validamycin, streptomycin, metalaxyl, furalaxyl, benomyl, thiophanate-methyl, triadimefon, bupirimate, dimethirimol, ethirimol, captan, folpet, vinclozolin, fluocinolone, dimethachlon, chlorothalonil, isoprothiolane, pefurazone, bismerzole, quintozene, propineb, fosetyl, sulfur, polidocusate, cuprous oxide, cupric chloride, cupric oxide, cupric hydroxide, Metrafenone, pencycuron, pyridaben, tetrachlorophthalide, pyroquilon, spiroxamine, tricyclazole, azinam, dodine, diguanidinium salt, diguanidinium, niclosamide, bentiamine, tolfenpyrad, indole ester, sodium disulfate, quinconazole, probenazole, bronopol, methyl iodide, metam, dichloline ester, dazomet, dichloroisopropyl ether, fosthiazate, fosfenthion, fenamiphos, thiothifenthion, methiocarb, sulfuryl fluoride, dichloropropylene, dichloroisonicotinic acid, allylisothiazole;

the total mass percentage of the sulfinyl imine psoralen derivatives I in the bactericidal composition is 1% -90%; the ratio of the sulfinyl imine psoralen derivative I to the bactericide is 1 percent to 99 percent to 1 percent by mass percent;

the bactericidal composition is processed into a dosage form selected from the group consisting of: seed treatment emulsions, aqueous emulsions, microemulsions, suspoemulsions, capsule suspensions, water soluble granules, fine granules, soluble concentrates, venoms, block baits, granular baits, tablet baits, concentrated baits, sustained release blocks, electrostatic sprays, oil-in-water emulsions, aerosol cans, aerosol candles, aerosol cartridges, aerosol sticks, aerosol tablets, aerosol pellets, gas generants, ointments, hot fogging formulations, cold fogging formulations, aerosols, solid/liquid mixtures, liquid/liquid mixtures, solid/solid mixtures, lacquers, microgranules, chasing powders, oil suspensions, oil dispersible powders, concentrated gels, pour-on formulations, seed coatings, paints, film-forming oils, ultra-low volume liquids, vapor release agents;

the plant diseases controlled by the bactericidal composition are selected from: rice seedling blight, tomato root rot, potato late blight, tobacco black shank, millet powdery mildew, grape downy mildew, lettuce downy mildew, cucumber anthracnose;

the plants suitable for the bactericidal composition are selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, cassava, soybean, sweet broad bean, pea, mung bean, small bean, cotton, silkworm, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili, radish, cucumber, cabbage, celery, tuber mustard, sugar beet, rape, shallot, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

The sulfinyl imine psoralen derivative I and any one or two of the antiviral medicaments are combined to form an antiviral composition for preventing and treating virus diseases of agricultural, forestry and horticultural plants;

the antiviral agent is selected from: benzothiadiazole, tiadinil, isotianil, 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid, 4-methyl-1, 2, 3-thiadiazole-5-sodium formate, 4-methyl-1, 2, 3-thiadiazole-5-ethyl formate, 3, 4-dichloroisothiazole-5-carboxylic acid, 3, 4-dichloroisothiazole-5-sodium formate, 3, 4-dichloroisothiazole-5-ethyl formate, DL-beta-aminobutyric acid, 2, 6-dichloroisonicotinic acid, N-cyanomethyl-2-chloroisonicotinamide, probenazole, virazole, antofine, ningnanmycin, thiamide, methiothiamide or salicylic acid, pyriminomycin, Dichloroisonicotinic acid, probenazole, validamycin, moroxydine hydrochloride;

the sulfinyl imine psoralen derivative I accounts for 1-90% of the antiviral composition in total mass percentage; preferably, the ratio of the sulfinyl imine psoralen derivative I to the anti-plant virus agent is 1 to 99 to 1 percent by mass percent;

the antiviral composition is processed into a dosage form selected from: seed treatment emulsions, aqueous emulsions, microemulsions, suspoemulsions, capsule suspensions, water soluble granules, fine granules, soluble concentrates, venoms, block baits, granular baits, tablet baits, concentrated baits, sustained release blocks, electrostatic sprays, oil-in-water emulsions, aerosol cans, aerosol candles, aerosol cartridges, aerosol sticks, aerosol tablets, aerosol pellets, gas generants, ointments, hot fogging formulations, cold fogging formulations, aerosols, solid/liquid mixtures, liquid/liquid mixtures, solid/solid mixtures, lacquers, microgranules, chasing powders, oil suspensions, oil dispersible powders, concentrated gels, pour-on formulations, seed coatings, paints, film-forming oils, ultra-low volume liquids, vapor release agents;

the antiviral composition can be used for preventing and treating viral diseases selected from: rice dwarf, yellow dwarf, stripe disease, tomato fern leaf virus, pepper mosaic virus, tobacco vein necrosis virus, maize dwarf mosaic, cauliflower mosaic, citrus virus, cymbidium mosaic, cymbidium ringspot virus;

the plants for preventing and treating the antiviral composition are selected from the following plants: rice, wheat, barley, oats, corn, sorghum, sweet potato, cassava, soybean, sweet broad bean, pea, mung bean, small bean, cotton, silkworm, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili, radish, cucumber, cabbage, celery, tuber mustard, sugar beet, rape, shallot, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

The sulfinyl imine psoralen derivative I and any one or two of the acaricides form an acaricide composition for preventing and controlling mite damage of agricultural, forestry and horticultural plants;

the acaricide is selected from: dichlorvos, heptenophos, metofos, monocrotophos, phosphorus dibromide, pyrimidophos, chloromethylthion, ethion, chlorfenvinphos, vofenthion, pirimiphos, phoxim, isocarbophos, amicarbazone, chlormephos, fluthrin, bifenthrin, cyhalothrin, lambda-cyhalothrin, fenpropathrin, flumethrin, fluvalinate, bifenthrin, bifenazate, fenobucarb, butoxycarb, carbofuran, monocarb, benomyl, cloxacarb, butathiocarb, lufenuron, benzyl benzoate, bromopropylate, cyflumetofen, dimethrin, flufenpyr, fluazuron, bleomycin, chlortetracycline, abamectin, avermectin, lium, lividin, doramectin, epothidin, ivermectin, simethiofen, dimethofos, dimethrin, dimethoxim, fosetyl, chlorfenapyr, isofos, chlorfenapyr, dimethoxim, fluazurin, isomycin, chlorfenacin, avermectin, chlorfenacin, chlorfenapyr, chlorpyrifos, chlorpyri, Nicotine, matrine, azadirachtin, rotenone, tebufenpyrad, pyridaben, fenpyroximate, clofentezine, propargite, hexythiazox, spirodiclofen, fluacrypyrim, propargite and pyridaben;

the total mass percentage of the sulfinyl imine psoralen derivatives I in the acaricidal composition is 1% -90%; the ratio of the sulfinyl imine psoralen derivative I to the acaricide is 1 percent to 99 percent to 1 percent by mass percentage;

the acaricidal composition is processed into a dosage form selected from the following: seed treatment emulsions, aqueous emulsions, microemulsions, suspoemulsions, capsule suspensions, water soluble granules, fine granules, soluble concentrates, venoms, block baits, granular baits, tablet baits, concentrated baits, sustained release blocks, electrostatic sprays, oil-in-water emulsions, aerosol cans, aerosol candles, aerosol cartridges, aerosol sticks, aerosol tablets, aerosol pellets, gas generants, ointments, hot fogging formulations, cold fogging formulations, aerosols, solid/liquid mixtures, liquid/liquid mixtures, solid/solid mixtures, lacquers, microgranules, chasing powders, oil suspensions, oil dispersible powders, concentrated gels, pour-on formulations, seed coatings, paints, film-forming oils, ultra-low volume liquids, vapor release agents;

the mite damage controlled by the mite-killing composition is selected from the following groups: the mite is selected from spider mite family, furaciidae, gall mite family, Tetranychus genus, and pest mites of gall mite family, which are world agricultural pest mites, forestry pest mites, horticultural pest mites, and health pest mites;

the plant for controlling the acaricidal composition is selected from the following plants: rice, wheat, barley, oats, corn, sorghum, sweet potato, cassava, soybean, sweet broad bean, pea, mung bean, small bean, cotton, silkworm, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili, radish, cucumber, cabbage, celery, tuber mustard, sugar beet, rape, shallot, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

The biological activity of the sulfinyl imine psoralen derivative I is measured as follows:

I. the bactericidal activity of the sulfinyl imine psoralen derivative I is determined as follows:

the bactericidal or bacteriostatic activity of the psoralen derivative I containing sulfinyl imine adopts a thallus growth rate measuring method, and the method comprises the following specific steps: dissolving 1.8 mg of sample in 2 drops of N, N-dimethylformamide, diluting with a water solution containing a certain amount of Tween 20 emulsifier to 500 micrograms/ml of medicament, sucking 1 ml of the medicament to be tested in a culture dish under an aseptic condition, adding 9 ml of PDA culture medium, shaking uniformly to prepare a medicament-containing flat plate with the concentration of 50 micrograms/ml, taking the flat plate added with 1 ml of sterile water as a blank control, cutting a bacterial disc by a puncher with the diameter of 4 mm along the outer edge of hypha, moving the bacterial disc to the medicament-containing flat plate, placing the bacterial disc in an equilateral triangle, repeating the treatment for 3 times, placing the culture dish in a constant temperature incubator with the temperature of 24 +/-1 ℃ for culture, investigating the expansion diameter of each treated bacterial disc after the diameter of the control bacterial colony is expanded to 2-3 cm, calculating the relative bacteriostasis rate by comparing with the blank control, wherein the strain is the species of most typical plant pathogenic bacteria actually occurring in the agricultural production of China, the code numbers and names are as follows: AS: tomato early blight, its latin name is: alternaria solani, BC: the cucumber botrytis cinerea with the latin name as follows: botrytis cinerea, CA: peanut brown spot pathogen, its latin name is: cercospora arachidicola, GZ: wheat scab, its latin name is: gibberella zeae, PP: apple ring rot, its latin name is: physiosporia piricola, PS: rhizoctonia solani, the Latin name of which is: pellicularia sasakii, SS: sclerotinia sclerotiorum, its latin name is: sclerotina sclerotiorum.

The invention has the beneficial effects that: the sulfinyl imine psoralen derivatives I are subjected to lead optimization, and the sulfinyl imine psoralen derivatives are subjected to antibacterial activity screening.

The present invention further specifically illustrates the synthesis, biological activity and application of sulfinyl imine psoralen derivatives I through specific preparation and biological activity determination examples, which are only used for specifically illustrating the present invention and not for limiting the present invention, and particularly, the biological activity is only illustrated and not for limiting the patent, and the specific embodiments are as follows:

example 1: preparation of compound 3:

a100 ml round-bottom flask was charged with 18.2 mmol of resorcinol and 18.2 mmol of dimethyl acetylsuccinate, followed by slowly dropping 2.73 ml of 98% concentrated sulfuric acid under stirring, and after the dropping was completed, the reaction system was stirred at room temperature overnight. Monitoring by TLC, adding 30 ml of anhydrous methanol after the reaction is finished, pouring the anhydrous methanol into ice water to generate a large amount of white solid, performing suction filtration on the obtained solid, washing the crude product with diethyl ether, and recrystallizing with ethanol-water to obtain a compound 3; the yield is 81%; the nuclear magnetic data are as follows:¹h NMR (400MHz, DMSO) δ 10.50(s, 1H), 7.59(d, J ═ 8.8Hz, 1H), 6.79(dd, J ═ 8.7, 2.1Hz, 1H), 6.69(d, J ═ 2.1Hz, 1H), 3.61(s, 2H), 3.57(s, 3H), 2.30(s, 3H). The amount of compound 3 produced and the volume of the reaction vessel are scaled up or down accordingly.

Example 2: preparation of compound 5:

a100 ml round-bottom flask was charged with 1 mmol of Compound 3 and 30 ml of anhydrous acetonitrile, and 1.2 mmol of Compound 4, 4 mmol of anhydrous potassium carbonate and 0.1 mmol of potassium iodide were sequentially added under stirring at room temperature, followed by heating and refluxing the reaction system for 5 hours. TLC was monitored and the reaction was completeThen standing and cooling to room temperature, removing most of acetonitrile under reduced pressure, adding 30 ml of water into the residue, extracting for three times (15 ml × 3) by using ethyl acetate, washing an organic phase for three times (15 ml × 3) by using a saturated sodium chloride solution, and drying combined organic layers by using anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with petroleum ether/ethyl acetate (3: 1, volume/volume) eluent column chromatography to obtain compound 5; the yield is 65%; the nuclear magnetic data are as follows:¹h NMR (400MHz, DMSO) δ 8.12(s, 2H), 7.74(d, J ═ 8.8Hz, 1H), 7.42(t, J ═ 8.5Hz, 2H), 7.10(s, 1H), 7.04(d, J ═ 8.7Hz, 1H), 5.73(s, 2H), 3.67(s, 2H), 3.62(s, 3H), 2.38(s, 3H). The amount of compound 5 produced and the volume of the reaction vessel are scaled up or down accordingly.

Example 3: preparation of compound 6:

2 g of compound 5 and 30 ml of isopropanol are added to a 100 ml round-bottom flask, 60 ml of 1 mol/l sodium hydroxide solution is slowly added dropwise with stirring at room temperature, and the reaction system is heated and refluxed for 4 hours after the dropwise addition. Monitoring by TLC, standing the system after the reaction is finished, cooling to room temperature, removing most isopropanol under reduced pressure, adding 1 mol/L hydrochloric acid solution into the residue to adjust the pH of the system to 1, precipitating a large amount of solid, performing suction filtration, and drying to obtain a compound 6; the yield thereof was found to be 61%; the nuclear magnetic data are as follows:¹h NMR (400MHz, DMSO). delta.12.29 (s, 1H), 8.30(s, 1H), 7.98(s, 1H), 7.70(s, 1H), 7.61(s, 1H), 7.22(s, 2H), 3.49(s, 2H), 2.36(s, 3H). The amount of compound 6 produced and the volume of the reaction vessel are scaled up or down accordingly.

Example 4: preparation of compound 7:

a100 ml round-bottom flask was charged with 0.3 g of Compound 6 and 15 ml of N, N-dimethylformamide under stirring0.49 g of 1H-benzotriazol-1-yloxytripyrrolidinyl hexafluorophosphate, 0.275 g of N, N-diisopropylethylamine and 0.13 g of 4-aminoanisole sulfide were added in a lump, and the mixture was stirred at room temperature for 6 hours. TLC, 30 ml of water was added after the reaction was complete, extracted three times with ethyl acetate (15 ml × 3), the separated organic phase was washed three times with saturated sodium chloride solution (15 ml × 3), and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with petroleum ether/ethyl acetate (3: 1, volume/volume) eluent column chromatography to obtain compound 7; the yield is 82 percent; the nuclear magnetic data are as follows:¹h NMR (400MHz, DMSO) δ 10.24(s, 1H), 8.41(s, 1H), 8.09(s, 1H), 7.84(s, 2H), 7.70(s, 1H), 7.61(d, J ═ 7.6Hz, 2H), 7.37(t, J ═ 7.9Hz, 2H), 7.24(d, J ═ 7.5Hz, 2H), 3.82(s, 2H), 2.55(s, 3H), 2.45(s, 3H). The amount of compound 7 produced and the volume of the reaction vessel are scaled up or down accordingly.

Example 5: preparation of Compound I-a:

a100 ml round-bottom flask was charged with 0.15 g of Compound 7 and 10 ml of anhydrous methanol, followed by addition of 0.235 g of iodophenylenediacetic acid and 0.046 g of ammonium carbonate with stirring, and stirring at room temperature for 8 hours. TLC, after the reaction was complete most of the methanol was removed under reduced pressure, 30 ml of water was added to the residue, extracted three times with ethyl acetate (15 ml × 3), the organic phase was separated and washed three times with saturated sodium chloride solution (15 ml × 3), and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with dichloromethane/methanol (20: 1, volume/volume) eluent column chromatography to obtain compound I-a; the yield is 74-83%; when R is¹Is 4-fluorophenyl, R²The nuclear magnetic data for compound I-a-1, when hydrogen, are as follows: the nuclear magnetic data are as follows:¹H NMR(400MHz，DMSO)δ10.56(s，1H)，8.46(s，1H)，8.18(s，1H)，7.89-7.84(m，4H)，7.79(d，J＝8.2Hz，3H)，7.37(t，J＝8.7Hz，2H)，4.07(s，1H)，3.85(s，2H)，3.02(s，3H)，258(s, 3H). The preparation amount of the compound I-a-1 and the volume of a reaction vessel are enlarged or reduced according to corresponding proportion; the physicochemical and structural parameters of compound I-a are shown in Table 1.

Example 6: preparation of Compound I-b:

a100 ml round-bottomed flask was charged with 0.1 g of Compound I-a-1 and 5 ml of anhydrous pyridine, and 0.04 g of p-toluenesulfonyl chloride was added with stirring and stirred at room temperature for 8 hours. TLC, 30 ml of water was added after the reaction was complete, extracted three times with ethyl acetate (15 ml × 3), the organic phase was separated and washed three times with 1 mol/l hydrochloric acid solution (15 ml × 3) and saturated sodium chloride solution (15 ml × 3) in sequence, and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with dichloromethane/methanol (100: 1, volume/volume) eluent column chromatography to obtain compound I-b; the yield is 64-94%; when R is¹Is 4-fluorophenyl, R²For 4-methylbenzenesulfonyl, the nuclear magnetic data for compound I-b-1 are as follows:¹h NMR (400MHz, DMSO) δ 10.73(s, 1H), 8.48(s, 1H), 8.21(s, 1H), 7.91-7.81(m, 7H), 7.61(d, J ═ 8.1Hz, 2H), 7.39(t, J ═ 8.8Hz, 2H), 7.29(d, J ═ 8.1Hz, 2H), 3.88(s, 2H), 3.55(s, 3H), 2.60(s, 3H), 2.35(s, 3H). The preparation amount of the compound I-b-1 and the volume of a reaction vessel are enlarged or reduced according to corresponding proportion; the physicochemical and structural parameters of the compounds I-b are shown in Table 1.

Example 7: preparation of Compounds I-c:

a100 ml round-bottomed flask was charged with 0.05 g of Compound I-a-1 and 15 ml of anhydrous pyridine, and 0.01 g of acetyl chloride was added with stirring and stirred at room temperature for 8 hours. TLC was monitored, 30 ml of water were added after the reaction was complete, extraction was carried out three times with ethyl acetate (15 ml. times.3), the organic phase was separated and used successively1 mol/l hydrochloric acid solution (15 ml. times.3), saturated sodium bicarbonate solution (15 ml. times.3), saturated sodium chloride solution were washed three times (15 ml. times.3), and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with dichloromethane/methanol (100: 1, volume/volume) eluent column chromatography to obtain compound I-c; the yield is 67-94%; when R is¹Is 4-fluorophenyl, R²For acetyl, the nuclear magnetic data for compound I-c-1 are as follows:¹h NMR (400MHz, DMSO) δ 10.66(s, 1H), 8.47(s, 1H), 8.20(s, 1H), 7.90-7.81(m, 7H), 7.38(t, J ═ 8.7Hz, 2H), 3.87(s, 2H), 3.39(s, 3H), 2.59(s, 3H), 1.97(s, 3H). The preparation amount of the compound I-c-1 and the volume of a reaction vessel are enlarged or reduced according to corresponding proportion; the physicochemical and structural parameters of the compounds I-c are shown in Table 1.

Example 8: preparation of Compounds I-d:

a100 ml round-bottomed flask was charged with 0.1 g of compound I-a-1 and 20 ml of N, N-dimethylformamide, and 0.004 g of cuprous chloride and 0.027 g of p-fluorophenyl isocyanate were successively added thereto with stirring, and stirred at room temperature for 8 hours. TLC, 30 ml of water was added after the reaction was complete, extracted three times with ethyl acetate (15 ml × 3), the separated organic phase was washed three times with saturated sodium chloride solution (15 ml × 3), and the combined organic layers were dried over anhydrous sodium sulfate; vacuum filtering, concentrating the filtrate to remove solvent, and purifying with dichloromethane/methanol (100: 1, volume/volume) eluent column chromatography to obtain compound I-d; the yield is 72-91%; when R is¹Is 4-fluorophenyl, R²In the case of the (4-fluorophenyl) carbamoyl group, the nuclear magnetic data of the compound I-d-1 are as follows:¹h NMR (400MHz, DMSO) δ 10.66(s, 1H), 9.39(s, 1H), 8.47(s, 1H), 8.20(s, 1H), 8.06(d, J ═ 8.1Hz, 1H), 7.93(d, J ═ 8.3Hz, 2H), 7.87(s, 3H), 7.82(s, 1H), 7.51(d, J ═ 4.8Hz, 2H), 7.38(t, J ═ 8.3Hz, 2H), 7.03(t, J ═ 8.5Hz, 2H), 3.87(s, 2H), 3.45(s, 3H), 2.59(s, 3H). Amounts of Compound I-d-1 prepared andthe volume of the reaction vessel is enlarged or reduced according to the corresponding proportion; the physicochemical and structural parameters of the compounds I-d are shown in Table 1.

Example 9: the result of the antibacterial activity determination of the sulfinyl imine psoralen derivative I of the invention is as follows:

the codes and names of the common plant pathogenic fungi tested by the invention are as follows: a.s: tomato early blight, its latin name is: alternaria solani, b.c: the cucumber botrytis cinerea with the latin name as follows: botrytis cinerea, C.a: peanut brown spot pathogen, its latin name is: cercospora arachidicola, G.z: wheat scab, its latin name is: gibberella zeae, P.p: apple ring rot, its latin name is: physiosporia piricola, P.s: rhizoctonia solani, the Latin name of which is: pellicularia sasakii, S.s: sclerotinia sclerotiorum, its latin name is: the strains have good representativeness and can represent the species of most pathogenic bacteria in the field in agricultural production.

The results of the cell growth rate method are shown in Table 2, and Table 2 shows that all the compounds synthesized by the invention have bactericidal activity of different degrees at 50 micrograms/ml. For the tomato early blight bacteria, the compounds DJY-1-189, DJY-2-1, DJY-2-11, DJY-1-198, DJY-2-30, DJY-2-50, DJY-1-168, DJY-2-74, DJY-2-24, DJY-1-191, DJY-1-179, DJY-2-189, DJY-2-187, DJY-2-201, DJY-1-196, DJY-2-60-2, DJY-3-2 and DJY-2-77 have the inhibition rate of more than 50 percent, are equal to or higher than that of control medicaments such as bone lipid supplement medicaments and YZK-22, wherein the compounds DJY-2-1, DJY-2-11, DJY-11, The inhibition rates of DJY-1-191 and DJY-2-189 are more than 65 percent, which is nearly 10 percent higher than that of the control medicament for supplementing the bone lipoprotein and YZK-C22; for botrytis cinerea, the inhibition rates of compounds DJY-2-44, DJY-2-74, DJY-1-191, DJY-2-61, DJY-2-186, DJY-2-187, DJY-1-196 and DJY-3-2 are more than 60 percent and more than 10 percent higher than that of a control medicament for supplementing the ossein, wherein the inhibition rates of the compounds DJY-2-186 and DJY-3-2 are more than 90 percent and are all more than that of the control medicament YZK-C2220 percent, and particularly the bactericidal activity of the compounds DJY-2-186 is the highest and reaches 93 percent; for peanut brown spot pathogen, the inhibition rate of the compounds DKY-2-1, DKY-2-13, DKY-2-66 and DKY-2-24 is more than 65%, and the inhibition rate is equivalent to or higher than that of control medicaments such as bone lipoid and YZK-C22, wherein the bactericidal activity of the compound DKY-2-13 is the highest and reaches 88%, and is more than 20% higher than that of the control medicaments such as bone lipoid; for apple ring rot pathogen, the inhibition rate of the compounds DKY-1-192, DKY-2-29 and DKY-2-186 is above 60%, which is higher than that of the control drug for supplementing bone lipid by about 20%, wherein the bactericidal activity of the compound DKY-2-186 is the highest and reaches 72%; for rhizoctonia solani, the inhibition rate of the compounds DKY-2-66, DKY-2-67 and DKY-2-24 is more than 70 percent, and is higher than that of the control drug for supplementing the bone lipoprotein by nearly 20 percent; for Sclerotinia sclerotiorum, the inhibition rates of the compounds DJY-2-66, DJY-2-24, DJY-1-191, DJY-2-189, DJY-2-186, DJY-2-187, DJY-2-201 and DJY-3-2 are more than 50%, and are equivalent to or higher than that of control medicaments such as the bone lipoprotein and YZK-C22, wherein the inhibition rates of the compounds DJY-2-24 and DJY-1-191 are more than 90%, and are both more than 0% higher than that of the control medicaments such as the bone lipoprotein and YZK-C2230%, especially the bactericidal activity of the compounds DJY-1-191 is the highest and reaches 96%.

Example 10: the application of the sulfinyl imine psoralen derivative I in preparing the pesticide composition comprises the following steps:

the sulfinyl imine psoralen derivative I is used for preparing pesticide compositions, the composition contains the sulfinyl imine psoralen derivative I and an intermediate thereof as active ingredients, and the content of the active ingredients is 0.1 to 99.9 percent by weight, 99.9 to 0.1 percent by weight of solid or liquid auxiliary agents and optionally 0 to 50 percent by weight of surfactant.

Example 11: the application of the sulfinyl imine psoralen derivative I in preparing the pesticide compound composition comprises the following steps:

the sulfinyl imine psoralen derivative I and the intermediate thereof can be used for preparing other commercial pesticides, namely insecticide, acaricide, bactericide, antiviral agent or plant activator, to prepare the pesticide compound composition, the compound composition comprises the sulfinyl imine psoralen derivative I and the intermediate thereof and other commercial pesticides, namely an insecticide, an acaricide, a bactericide, an antiviral agent or a plant activator as active ingredients, the sulfinyl imine psoralen derivative I and the intermediate thereof and other commercial pesticides, the proportion of the insecticide, acaricide, bactericide, antiviral agent or plant activator is 1 percent to 99 percent to 1 percent by mass, the content of the active ingredient is 0.1 percent to 99.9 percent by weight, 99.9 percent to 0.1 percent by weight of solid or liquid auxiliary agent and optional 0 percent to 50 percent by weight of surfactant.

Example 12: the sulfenamide psoralen derivative I is combined with a pesticide to be applied to prevention and treatment of agricultural, forestry and horticultural plant insect pests:

the sulfenimide psoralen derivative I is combined with any one or two of commercial insecticides to form an insecticidal composition for preventing and treating agricultural and forestry and horticultural plant insect pests, wherein the commercial insecticides are selected from the following: methoprene, diazinon, acetamiprid, emamectin benzoate, milbemectin, abamectin, pleocidin, metaflumethrin, meperfluthrin, cyfluthrin, beta-cypermethrin, lambda-cyhalothrin, permethrin, allethrin, bifenthrin, permethrin, flumethrin, cyfluthrin, imidacloprid, nitenpyram, imidaclothianidin, thiacloprid, thiamethoxam, clothianidin, dinotefuran, cotinine, dinotefuran, diflubenzuron, chlorbenzuron, tefluazuron, flufenoxuron, lufenuron, chlorflufenoxuron, fluazuron, diflubenzuron, fluazuron, tezine, fluazuron, tezine, teflufenozide, tebufenozide, tezine, flufenozide, tebufenozide, tezine, tebufenozide, tezine, tebufenozide, tezine, tebufalin, tezine, tebenflumetsulbenflumetsulbens, tezine, tebenil, tezine, tebenil, tebenflumetsulbens, tebenil, tebens, tezine, tebens, and tebens, and the like, Methoxyfenozide, chromafenozide, dichlorvos, quinalphos, pyridaphenthion, cicada powder, carbaryl, pirimicarb, metolcarb, isoprocarb, cartap, fenobucarb, tetrafenozide, fenitrothion, hexythiazox, carbaryl, fenisobromolate, hexythiazox, pyridate, clofentezine, spirodiclofen, spirotetramat, azocyclobutazine, buprofezin, monosultap, dimehypo, chlorantraniliprole, tetrachlorantranilide, flubendiamide, cyantraniliprole, butenenitrile, tolfenpyrad, chlorfenapyr, pyrazofos, pyrazinone, etoxazole, tebufenpyrad, pyridaben, emamectin, and pentapyraflufen; the mass percentage of the sulfinyl imine psoralen derivative I in the insecticidal composition is 1-90%, and the mass percentage of the sulfinyl imine psoralen derivative I and the commercial insecticide is 1% to 99% to 1%; the insecticide composition is processed into a dosage form selected from the group consisting of: seed treatment emulsions, aqueous emulsions, microemulsions, suspoemulsions, capsule suspensions, water soluble granules, fine granules, soluble concentrates, venoms, block baits, granular baits, tablet baits, concentrated baits, sustained release blocks, electrostatic sprays, oil-in-water emulsions, aerosol cans, aerosol candles, aerosol cartridges, aerosol sticks, aerosol tablets, aerosol pellets, gas generants, ointments, hot fogging formulations, cold fogging formulations, aerosols, solid/liquid mixtures, liquid/liquid mixtures, solid/solid mixtures, lacquers, microgranules, chasing powders, oil suspensions, oil dispersible powders, concentrated gels, pour-on formulations, seed coatings, paints, film-forming oils, ultra-low volume liquids, vapor release agents; the plant insect pests controlled by the insecticidal composition are selected from: meadow spodoptera, red spider, east Asian migratory locust, spruce-bug, Chinese rice locust, japanese yellow-back locust, single-prick mole cricket, oriental mole cricket, rice thrips, thrips tabaci, green house thrips, rice straw thistle, wheat simple pipe thrips, green house whitefly, bemisia tabaci, black tail hopper, big leaf hopper, cotton leafhopper, lesser leafhopper, brown plant hopper, white back plant hopper, gray plant hopper, sugarcane flat leaf planthopper, cotton aphid, binary wheat aphid, wheat straw aphid, peach aphid, sorghum aphid, radish aphid, mealybug, lybug, stinkbug, arrowhead bug, round scale, white insect, red wax insect, red worm, mealybug, pear net, banana net bug, tiny flower bug, laceleaf fly, green fly, rice moth, black armyworm, black fly, black rice moth, black armyworm, black rice moth, black rice plant, black rice plant, black rice plant, green plant, rice plant, black rice plant, green plant, rice plant, green plant, rice plant, pink bollworm, sweet potato wheat moth, diamond back moth, peach fruit borer, soybean pod borer, peach fruit borer, apple tip leaf roller moth, brown banded leaf roller moth, pardos leaf roller moth, striped rice borer, pod borer, corn borer, yellow rice borer, cabbage moth, rice leaf roller borer, striped rice borer, cotton leaf borer, peach borer, armyworm, prodenia litura, rice bollworm, cotton small bridgehead moth, beet armyworm, sesamia inferen, cotton bollworm, Dinodon diamond-back moth, agrotis, yellow cutworm, robber venom moth, gypsy moth, sweet potato hawkmoth, bean hawkmoth, straight grain rice skipper, cryptophyte butterfly, caeruleuca, caeruleuciscus nigra, yellow mealyratus caeruleucade, yellow meadowrue, yellow rice beetle, yellow tiger, red ramie yellow vanne, yellow rice borer, yellow rice, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice, yellow rice borer, yellow rice borer, yellow rice borer, yellow rice, yellow rice borer, yellow rice borer, yellow rice, yellow rice borer, yellow rice, Tribolium castaneum, verdigris, black tortoise, branchia palustris, longicorn beetle, pink neck longicorn beetle, ape leaf worm, yellow melon, flea beetle, mung bean weevil, pea weevil, broad bean weevil, corn weevil, rice weevil, wheat leaf bee, pear fruit bee, yellow stripe wasp, armyworm white star ichneumonid, sandfly bractenoconid, cotton bollworm tooth-lipped ichneumonid, borer black spot wart, mosquito, fly, horsefly, red mud fly, yellow leaf sucking serous, rice gall mosquito fly, citrus fruit fly, melon fruit fly, wheat leaf gray fly, American fly, black stalk black fly, wheat stem fly, seed fly, onion fly, radish skirt, eupatorium, corn borer, and armyworm; the plants controlled by the insecticidal composition are selected from the following plants: rice, wheat, barley, oats, corn, sorghum, sweet potato, cassava, soybean, sweet broad bean, pea, mung bean, small bean, cotton, silkworm, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili, radish, cucumber, cabbage, celery, tuber mustard, sugar beet, rape, shallot, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

Example 13: the sulfinyl imine psoralen derivative I and the bactericide are combined to be applied to preventing and treating diseases of agricultural, forestry and horticultural plants:

the sulfinyl imine psoralen derivative I and any one or two of commercial bactericides form a bactericidal composition for preventing and treating agricultural and forestry and horticultural plant diseases, wherein the commercial bactericides are selected from the following components: benzothiadiazole, tiadinil, thianamide, methicillin, 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid, 4-methyl-1, 2, 3-thiadiazole-5-sodium formate, 4-methyl-1, 2, 3-thiadiazole-5-ethyl formate, DL-beta-aminobutyric acid, isotianil, 3, 4-dichloroisothiazole-5-carboxylic acid, 3, 4-dichloroisothiazole-5-sodium formate, 3, 4-dichloroisothiazole-5-ethyl formate, ribavirin, antofine, ningnanmycin or salicylic acid, cyanamide, thiram, ziram, mancozeb, fosetyl, thiophanate-methyl, chlorothalonil, chlormadinone, procymidone, fenpropidium rust, Thiophanate methyl, thiophanate, metalaxyl-M, flumorph, dimethomorph, metalaxyl-M, benalaxyl-M, diclocyanamide, sulfentram, sulfsulfamide, thifluzamide, folpet, cyprodinil, cyhalodiamide, silthiopham, carboxin, oxim-methyl, mefuram, fenazamide, flutolanil, furametpyr, thifluzamide, boscalid, penthiopyrad, isopyrazamide, bixafen, fluopyram, fluxastrobin, fluxapyroxad, flufenapyr, benconazole, iprovalicarb, flutriafolan, flufenpyrazamide, flufenacetmid, fluoxastrobin, fenhexamid, iprodione, trifloxystrobin, kresoximtrobin, trifloxystrobin, fenstrobin, fenstrobilurin, fenpyraclostrobin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluoxastrobilurin, fluoxastrobin, fluopicolide, fluopicolinate, fluopicolide, fluopicolinate, fluopicolide, fluopicolinate, fluo, Enestroburin, dimethomorph, difenoconazole, bromhexine, epoxiconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole, difenoconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimenol, triticonazole, bitertanol, thiabendazole, imazalil, prochloraz, triflumizole, cyazofamid, fenamidone, imidazole, pefurazoate, famoxadone, pyridinozole, prodiamine, ethaboxam, hymexazol, penoxsulam, fenthion, fenpropimorph, tridemorph, fenpyroxanil, fluazinam, fenpropiconazole, fenpyrazamide, fluazinam, cyprodinil, flufenamidone, fenpyrad, fenpyroxim, fenpyroxapyroxapyroxad, fenpyroxad-methyl, fenpyroxad-a, Mepanipyrim, pyrimethanil, fenarimol, fluoropyrimidinol, mefenamate, dithianon, ethoxyquin, hydroxyquinoline, propoxymine, phenoxyquinoline, diethofencarb, iprovalicarb, benthiavalicarb, propamocarb, sulbencarb, edifenphos, iprobenfos, pyrazofos, tolclofos-methyl, blasticidin, kasugamycin, polyoxin, validamycin, streptomycin, metalaxyl, furalaxyl, benomyl, thiophanate-methyl, triadimefon, bupirimate, dimethirimol, ethirimol, captan, folpet, vinclozolin, fluocinolone, dimethachlon, chlorothalonil, isoprothiolane, pefurazone, bismerzole, quintozene, propineb, fosetyl, sulfur, polidocusate, cuprous oxide, cupric chloride, cupric oxide, cupric hydroxide, Metrafenone, pencycuron, pyridaben, tetrachlorophthalide, pyroquilon, spiroxamine, tricyclazole, azinam, dodine, diguanidinium salt, diguanidinium, niclosamide, bentiamine, tolfenpyrad, indole ester, sodium disulfate, quinconazole, probenazole, bronopol, methyl iodide, metam, dichloline ester, dazomet, dichloroisopropyl ether, fosthiazate, fosfenthion, fenamiphos, thiothifenthion, methiocarb, sulfuryl fluoride, dichloropropylene, dichloroisonicotinic acid, allylisothiazole; the total mass percentage of the sulfinyl imine psoralen derivative I in the sterilization composition is 1-90%, and the mass percentage of the sulfinyl imine psoralen derivative I and the commercial bactericide is 1% to 99% to 1%; the bactericidal composition is processed into a dosage form selected from the group consisting of: seed treatment emulsions, aqueous emulsions, microemulsions, suspoemulsions, capsule suspensions, water soluble granules, fine granules, soluble concentrates, venoms, block baits, granular baits, tablet baits, concentrated baits, sustained release blocks, electrostatic sprays, oil-in-water emulsions, aerosol cans, aerosol candles, aerosol cartridges, aerosol sticks, aerosol tablets, aerosol pellets, gas generants, ointments, hot fogging formulations, cold fogging formulations, aerosols, solid/liquid mixtures, liquid/liquid mixtures, solid/solid mixtures, lacquers, microgranules, chasing powders, oil suspensions, oil dispersible powders, concentrated gels, pour-on formulations, seed coatings, paints, film-forming oils, ultra-low volume liquids, vapor release agents; the plant diseases controlled by the bactericidal composition are selected from: rice seedling blight, tomato root rot, potato late blight, tobacco black shank, millet powdery mildew, grape downy mildew, lettuce downy mildew, cucumber anthracnose; the plants suitable for the bactericidal composition are selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, cassava, soybean, sweet broad bean, pea, mung bean, small bean, cotton, silkworm, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili, radish, cucumber, cabbage, celery, tuber mustard, sugar beet, rape, shallot, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

Example 14: the sulfinyl imine psoralen derivative I and the plant virus resisting agent are combined to be applied to preventing and treating virus diseases of agricultural, forestry and horticultural plants:

the sulfinyl imine psoralen derivative I and any one or two of commercial antiviral medicaments form an antiviral composition for preventing and treating virus diseases of agricultural, forestry and horticultural plants, wherein the commercial antiviral medicaments are selected from: benzothiadiazole, tiadinil, isotianil, 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid, 4-methyl-1, 2, 3-thiadiazole-5-sodium formate, 4-methyl-1, 2, 3-thiadiazole-5-ethyl formate, 3, 4-dichloroisothiazole-5-carboxylic acid, 3, 4-dichloroisothiazole-5-sodium formate, 3, 4-dichloroisothiazole-5-ethyl formate, DL-beta-aminobutyric acid, ribavirin, antofine, ningnanmycin, thiaamide, mehtothiazolamide or salicylic acid, pyriminomycin, dichloroisonicotinic acid, probenazole, validamycin hydrochloride; the total mass percentage of the sulfinyl imine psoralen derivative I in the antiviral composition is 1-90%, and the mass percentage of the sulfinyl imine psoralen derivative I and the commercial anti-plant virus agent is 1: 99-99: 1%; the antiviral composition is processed into a dosage form selected from: seed treatment emulsions, aqueous emulsions, microemulsions, suspoemulsions, capsule suspensions, water soluble granules, fine granules, soluble concentrates, venoms, block baits, granular baits, tablet baits, concentrated baits, sustained release blocks, electrostatic sprays, oil-in-water emulsions, aerosol cans, aerosol candles, aerosol cartridges, aerosol sticks, aerosol tablets, aerosol pellets, gas generants, ointments, hot fogging formulations, cold fogging formulations, aerosols, solid/liquid mixtures, liquid/liquid mixtures, solid/solid mixtures, lacquers, microgranules, chasing powders, oil suspensions, oil dispersible powders, concentrated gels, pour-on formulations, seed coatings, paints, film-forming oils, ultra-low volume liquids, vapor release agents; the antiviral composition can be used for preventing and treating viral diseases selected from: rice dwarf, yellow dwarf, stripe disease, tomato fern leaf virus, pepper mosaic virus, tobacco vein necrosis virus, maize dwarf mosaic, cauliflower mosaic, citrus virus, cymbidium mosaic, cymbidium ringspot virus; the plants for preventing and treating the antiviral composition are selected from the following plants: rice, wheat, barley, oats, corn, sorghum, sweet potato, cassava, soybean, sweet broad bean, pea, mung bean, small bean, cotton, silkworm, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili, radish, cucumber, cabbage, celery, tuber mustard, sugar beet, rape, shallot, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

Example 15: the sulfenamide psoralen derivative I and the acaricide are combined to be applied to preventing and treating the mite damage of agricultural, forestry and horticultural plants:

the sulfinyl imine psoralen derivative I and any one or two of commercial acaricides form an acaricidal composition for preventing and controlling acarid damage of agricultural and forestry and horticultural plants, wherein the commercial acaricides are selected from the following groups: dichlorvos, heptenophos, metofos, monocrotophos, phosphorus dibromide, pyrimidophos, chloromethylthion, ethion, chlorfenvinphos, vofenthion, pirimiphos, phoxim, isocarbophos, amicarbazone, chlormephos, fluthrin, bifenthrin, cyhalothrin, lambda-cyhalothrin, fenpropathrin, flumethrin, fluvalinate, bifenthrin, bifenazate, fenobucarb, butoxycarb, carbofuran, monocarb, benomyl, cloxacarb, butathiocarb, lufenuron, benzyl benzoate, bromopropylate, cyflumetofen, dimethrin, flufenpyr, fluazuron, bleomycin, chlortetracycline, abamectin, avermectin, lium, lividin, doramectin, epothidin, ivermectin, simethiofen, dimethofos, dimethrin, dimethoxim, fosetyl, chlorfenapyr, isofos, chlorfenapyr, dimethoxim, fluazurin, isomycin, chlorfenacin, avermectin, chlorfenacin, chlorfenapyr, chlorpyrifos, chlorpyri, Nicotine, matrine, azadirachtin, rotenone, tebufenpyrad, pyridaben, fenpyroximate, clofentezine, propargite, hexythiazox, spirodiclofen, fluacrypyrim, propargite and pyridaben; the total mass percentage of the sulfinyl imine psoralen derivative I in the acaricidal composition is 1-90%, and the mass percentage of the sulfinyl imine psoralen derivative I and the commercial acaricide is 1% to 99% to 1%; the acaricidal composition is processed into a dosage form selected from the following: seed treatment emulsions, aqueous emulsions, microemulsions, suspoemulsions, capsule suspensions, water soluble granules, fine granules, soluble concentrates, venoms, block baits, granular baits, tablet baits, concentrated baits, sustained release blocks, electrostatic sprays, oil-in-water emulsions, aerosol cans, aerosol candles, aerosol cartridges, aerosol sticks, aerosol tablets, aerosol pellets, gas generants, ointments, hot fogging formulations, cold fogging formulations, aerosols, solid/liquid mixtures, liquid/liquid mixtures, solid/solid mixtures, lacquers, microgranules, chasing powders, oil suspensions, oil dispersible powders, concentrated gels, pour-on formulations, seed coatings, paints, film-forming oils, ultra-low volume liquids, vapor release agents; the mite damage controlled by the mite-killing composition is selected from the following groups: the mite is selected from spider mite family, furaciidae, goiter family, Tetranychus genus, and pest mites of the goiter family, which are world agricultural pest mites, forestry pest mites, horticultural pest mites, and health pest mites; the plant for controlling the acaricidal composition is selected from the following plants: rice, wheat, barley, oats, corn, sorghum, sweet potato, cassava, soybean, sweet broad bean, pea, mung bean, small bean, cotton, silkworm, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili, radish, cucumber, cabbage, celery, tuber mustard, sugar beet, rape, shallot, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

Industrial applicability

The invention provides a sulfinyl imine psoralen derivative; the derivative can regulate and control the biological activity of agricultural, horticultural and sanitary pests and plant pathogens of forestry plants, can be used for killing insects, killing mites, sterilizing, resisting plant viruses and inducing plants to generate disease resistance in the agricultural field, the horticultural field and the forestry field, and has better economic value and application prospect.

TABLE 2 bacteriostatic activity of sulfinyl imido psoralen derivatives I of the present invention (inhibition rate of 50. mu.g/ml/%)

Serial number	Compound (I)	A.s	B.c	C.a	G.z	P.p	P.s	S.s
									1	DJY-1-200	39	33	29	18	20	15	8
2	DJY-1-199	49	29	37	14	33	26	17
									3	DJY-1-189	55	24	38	14	20	19	11
4	DJY-1-183	40	33	46	13	17	15	24
									5	DJY-2-1	70	40	66	19	50	25	33
6	DJY-2-5	46	24	37	9	15	24	14
									7	DJY-2-11	67	48	48	15	39	14	25
8	DJY-2-13	49	30	88	19	14	25	13
									9	DJY-2-10	36	36	31	18	32	11	10
10	DJY-1-192	38	29	53	11	64	12	42
									11	DJY-1-188	23	31	27	35	27	18	26
12	DJY-1-198	63	42	37	11	17	18	13
									13	DJY-2-20	39	34	41	14	33	35	19
14	DJY-2-23	43	30	40	11	29	16	18
									15	DJY-2-29	28	51	54	16	63	22	25
16	DJY-2-30	63	26	38	20	38	19	9
									17	DJY-2-44	42	68	40	16	17	11	13
18	DJY-2-50	53	39	38	11	14	24	16
									19	DJY-2-47	43	28	28	42	20	9	8
20	DJY-2-66	41	46	67	40	44	73	62
									21	DJY-2-42	37	41	36	13	26	23	19
22	DJY-1-170	47	38	43	17	29	21	22
									23	DJY-1-168	65	43	50	20	33	27	14
24	DJY-2-67	27	44	61	32	42	70	38
									25	DJY-2-74	57	63	27	29	28	38	25
26	DJY-2-72	46	39	32	22	29	44	21
									27	DJY-2-24	61	34	65	32	34	73	92
28	DJY-1-191	67	78	32	13	9	22	96
									29	DJY-1-179	51	57	32	24	14	19	26
30	DJY-2-61	38	72	59	18	40	56	35
									31	DJY-2-189	70	32	53	24	34	37	54
32	DJY-2-186	23	93	64	37	72	39	55
									33	DJY-2-187	57	76	55	43	52	21	56
34	DJY-2-201	58	44	52	21	33	53	53
									35	DJY-1-196	56	61	41	20	27	26	16
36	DJY-2-60-2	55	20	47	29	25	23	33
									37	DJY-3-2	53	92	61	38	23	51	58
38	DJY-2-58	39	38	39	22	21	18	24
									39	DJY-2-77	52	58	38	25	20	41	19
40	DJY-2-70	35	20	31	20	23	34	24
									41	Psoralen	56	50	65	63	44	52	58
42	YZK-C22	58	72	74	75	57	81	61

A.s: tomato early blight, its latin name is: alternaria solani, b.c: the cucumber botrytis cinerea with the latin name as follows: botrytis cinerea, C.a: peanut brown spot pathogen, its latin name is: cercospora arachidicola, G.z: wheat scab, its latin name is: gibberella zeae, P.p: apple ring rot, its latin name is: physiosporia piricola, P.s: rhizoctonia solani, the Latin name of which is: pellicularia sasakii, S.s: sclerotinia sclerotiorum, its latin name is: sclerotina sclerotomalis.

Claims

1. The sulfinyl imine psoralen derivative is characterized by simultaneously containing sulfinyl imine and psoralen structures and has a structural general formula shown in a formula I:

wherein R is¹Selected from: hydrogen, 4-fluoro, 4-chloro; r²Selected from: cyclopropanesulfonyl, 4-trifluoromethoxybenzenesulfonyl, 4-nitrobenzenesulfonyl, 4-methylbenzenesulfonyl, 2, 4-dichlorobenzenesulfonyl, 4-methoxybenzenesulfonyl, 4-fluorobenzenesulfonyl, 4-chlorobenzenesulfonyl, benzenesulfonyl, 4-tert-butylbenzenesulfonyl, methanesulfonyl, trifluoromethanesulfonyl, 4-iodobenzenesulfonyl, 4-bromobenzenesulfonyl, 4-ethylbenzenesulfonyl, 3, 4-difluorobenzenesulfonyl, 2-naphthalenesulfonyl, 4-tert-butylbenzoyl, hydrogen, 4-trifluoromethylbenzoyl, 3-bromobenzoyl, 3-trifluoromethoxybenzoyl, 4-methylbenzoyl, 4-fluorobenzoyl, acetyl, 1-naphthoyl, (3, 5-dichlorophenyl) carbamoyl, (4-trifluoromethoxyphenyl) carbamoyl, (4-fluorophenyl) carbamoyl, (3-methylphenyl) carbamoyl, 3, 4-dichloroisothiazole-5-formyl, 3- (difluoromethyl) -1-methyl-1H-pyrazole-4-formyl, 2-furoyl, cyclopentanecarboxyl, 2, 4-difluorobenzoyl, 2-chlorobenzoyl.

2. The specific synthetic route and method of the sulfonyl hydrazide psoralen derivative I as claimed in claim 1 are as follows:

A：

B：

C：

D：

the definition of the substituent is as defined in claim 1, and the specific synthetic method comprises the following steps:

A. preparation of compound 3:

B. preparation of compound 5:

C. preparation of compound 6:

D. preparation of compound 7:

E. preparation of Compound I-a:

F. preparation of Compound I-b:

G. preparation of Compounds I-c:

H. preparation of Compounds I-d:

3. Use of the sulfinyliminopsoralen derivative I as claimed in claim 1 for preparing agricultural fungicides.

4. An agricultural fungicidal composition comprising the sulfinyl imine psoralen derivative I of claim 1 and an intermediate, wherein the composition comprises the sulfinyl imine psoralen derivative I of claim 1 as an active ingredient, and the active ingredient is in the range of 0.1 to 99.9% by weight, 99.9 to 0.1% by weight of a solid or liquid adjuvant, and optionally 0 to 25% by weight of a surfactant.

5. An agricultural sterilization compound composition, which comprises the sulfinyl imine psoralen derivative I and other commercial bactericides which are compounded to be used as active ingredients, wherein the ratio of the sulfinyl imine psoralen derivative I to the other commercial bactericides is 1 percent to 99 percent to 1 percent, the content of the active ingredients is 1 to 99 percent by weight, and the solid or liquid auxiliary agent is 99 to 1 percent by weight.

6. An agricultural insecticidal and acaricidal compound composition, which comprises the sulfinyl imine psoralen derivative I as claimed in claim 1 and other commercial insecticidal and acaricidal agents as active ingredients, wherein the insecticidal and acaricidal ratio of the sulfinyl imine psoralen derivative I to other commercial products is 1% to 99% to 1%, the content of the active ingredients is 1 to 99% by weight, and the content of the solid or liquid auxiliary agents is 99 to 1% by weight.

7. A compound composition of anti-plant virus agents, which comprises the sulfinyl imine psoralen derivatives I and other commercial anti-plant virus agents in the claim 1 to be compounded as active ingredients, wherein the ratio of the sulfinyl imine psoralen derivatives I to the other commercial anti-plant virus agents is 1 percent to 99 percent to 1 percent, the content of the active ingredients is 1 to 99 percent by weight, and the content of the solid or liquid auxiliary agents is 99 to 1 percent by weight.