A class of diarylmethylselenoether derivatives and their agriculturally acceptable salts, preparation methods and applications

Abstract

This invention discloses a class of diarylmethylselenoether derivatives, their agriculturally acceptable salts, preparation methods, and applications. The structures of the diarylmethylselenoether derivatives are shown in general formula (I). The preparation method of the compound of general formula (I) is simple, the raw materials are readily available, and the cost is low. It can effectively inhibit weeds and harmful plants in agriculture, forestry, and other fields, and promote the growth and development of various crops in agricultural production. The compound of general formula (I) has good toxic and growth-inhibiting effects on agricultural weeds and harmful plants such as barnyard grass, artichoke, and mitochondritis, and good growth-promoting effects on crops such as rice and Chinese cabbage. The compound of general formula (I) of this invention can be applied to plants in the range of 0.1 mg / L-100 mg / L through irrigation, spraying, and hydroponics, and has strong applicability.

Description

Technical Field

[0001] This invention belongs to the field of agricultural herbicides and plant growth regulators, specifically relating to a class of diarylmethylselenoether derivatives (including diarylmethylmonoselenide derivatives and diarylmethyldiselenoether derivatives) and their agriculturally acceptable salts, preparation methods and applications. Background Technology

[0002] Chinese patent (ZL202011222204.1) creatively developed a series of fluoxetine selenourea-based artificial organic selenium defense agents, their preparation methods, and applications. Studies have shown that fluoxetine selenourea compounds possess good insecticidal activity, particularly N-difluoromethyl oxetine selenourea, which exhibits excellent insecticidal activity. Chinese patent application (patent application number: 202110783471.4) discloses multifunctional fluoxetine selenourea pesticides with insecticidal, fungicidal, and herbicidal functions, significantly improving the insecticidal and fungicidal properties of novel fluoxetine selenourea compounds while also possessing excellent herbicidal capabilities. Chinese patent application (patent application number: 202210330025.2) discloses N-difluoromethyl diazahexacyclic selenourea compounds with insecticidal, antibacterial, herbicidal, and anticancer effects, enabling these novel N-difluoromethyl diazahexacyclic selenourea compounds to have therapeutic and preventative effects on human cancer, building upon existing technologies. Chinese patent application (patent application number: 202211434442.8) discloses that azole selenurea functional reagents can simultaneously promote crop growth and increase the content of soluble protein, soluble sugar, total phenols, flavonoids, glucosinolates, chlorophyll, carotenoids, anthocyanins, free amino acids, minerals, and functional organic selenium in crops.

[0003] Currently, there are no publicly available diarylmethyl monoselenoethers and diselenoether derivatives that can control and eliminate various agricultural and forestry weeds and promote crop growth and development. Summary of the Invention

[0004] In order to overcome the shortcomings and deficiencies of the prior art, the primary objective of this invention is to provide a class of diarylmethyl monoselenoethers and diselenoether derivatives that can control and eliminate a variety of agricultural and forestry weeds and promote crop growth and development.

[0005] Another object of the present invention is to provide a method for preparing the above-mentioned diarylmethyl monoselenoether and diselenoether derivatives.

[0006] Another object of the present invention is to provide the use of the above-mentioned diarylmethyl monoselenoether and diselenoether derivatives.

[0007] The objective of this invention is achieved through the following technical solution:

[0008] A class of diarylmethyl monoselenoethers and diselenoether derivatives that can be used to treat a variety of agricultural and forestry weeds and harmful plants as well as to promote the growth and development of a variety of crops, with the structure shown in general formula (I);

[0009]

[0010] In the technical solution of the present invention: R in general formula (I) is selected from phenyl containing a substituent, or from heteroaryl containing a substituent, or from other heterocycles containing a substituent; the heterocycle may be 1,3-dioxolane, tetrahydrofuran, 1,3-dithiofenenyl, tetrahydrothiophene, 1,4-dioxane, tetrahydropyran, or other heterocycles containing one or more heteroatoms such as oxygen, sulfur, and nitrogen;

[0011] The substituents may be independently selected from fluorine, chlorine, bromine, iodine, hydroxyl, cyano, carboxyl, amino, nitro, difluoromethyl, dichloromethyl, dibromomethyl, trifluoromethyl, trichloromethyl, tribromomethyl, ethyl fluoroacetate, C1-C12 alkyl, halogenated C1-C12 alkyl, C1-C12 alkoxy, halogenated C1-C12 alkoxy, C3-C12 cycloalkyl, halogenated C3-C12 cycloalkyl, C2-C12 alkenyl, C2-C12 alkynyl, C2-C12 alkenyloxy, halogenated C2-C12 alkenyloxy, C2-C12 alkynyloxy, halogenated C2-C12 alkynyloxy, C1-C12 alkylthio, halogenated C1-C12 alkyl, C1-C12 alkoxy-C1-C12 alkyl, halogenated C1-C12 alkoxy-C1-C12 alkyl. C1-C12 alkylthioC1-C12 alkyl, halo-C1-C12 alkylthioC1-C12 alkyl, C1-C12 alkyl containing sulfinyl, C1-C12 alkyl containing halo and sulfinyl, C1-C12 alkyl containing sulfonyl, C1-C12 alkyl containing halo and sulfonyl, C1-C12 alkyl containing amino, halo-C1-C12 alkyl containing amino, C1-C12 alkoxycarbonyl, CONH2, C1-C12 alkylaminocarbonyl, di(C1-C12 alkyl)aminocarbonyl, cyanoC1-C12 alkoxy, C1-C12 alkoxycarbonylC1-C12 alkyl, C1-C12 alkylaminocarbonylC1-C12 alkyl, di(C1-C12 alkyl)aminocarbonylC1-C12 alkyl, phenyl or heteroaryl;

[0012] The aforementioned heteroaryl groups can be pyridyl, pyrimidinyl, thiazolyl, thiophene, furanyl, pyrazolyl, pyrroleyl, indolyl, or other heteroaryl groups containing one or more heteroatoms such as oxygen, sulfur, or nitrogen.

[0013] A preferred embodiment of the present invention is as follows: the substituents can be independently selected from fluorine, chlorine, bromine, iodine, hydroxyl, cyano, carboxyl, amino, nitro, difluoromethyl, dichloromethyl, dibromomethyl, trifluoromethyl, trichloromethyl, tribromomethyl, ethyl fluoroacetate, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenoxy, halogenated C2-C6 alkenoxy, C2-C6 alkynoxy, halogenated C2-C6 alkynoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 alkoxy-C1-C6 alkyl, halogenated C1-C6 alkoxy-C1-C6 alkyl, C1- C6 alkylthio-C1-C6 alkyl, halo-C1-C6 alkylthio-C1-C6 alkyl, C1-C6 alkyl containing sulfinyl, C1-C6 alkyl containing both halo and sulfinyl, C1-C6 alkyl containing sulfonyl, C1-C6 alkyl containing both halo and sulfonyl, amino-C1-C6 alkyl, amino-containing halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, CONH2, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, cyano-C1-C6 alkoxy, C1-C6 alkoxycarbonyl-C1-C6 alkyl, C1-C6 alkylaminocarbonyl-C1-C6 alkyl, di(C1-C6 alkyl)aminocarbonyl-C1-C6 alkyl, phenyl or heteroaryl;

[0014] The heteroaryl group can be pyridyl, pyrimidinyl, thiazolyl, thiophene, furanyl, pyrazolyl, pyrroleyl, indolyl, or other heteroaryl groups containing one or more heteroatoms such as oxygen, sulfur, or nitrogen.

[0015] A further preferred embodiment of the present invention is that the substituents can be independently selected from fluorine, chlorine, bromine, iodine, hydroxyl, cyano, carboxyl, amino, nitro, difluoromethyl, dichloromethyl, dibromomethyl, trifluoromethyl, trichloromethyl, tribromomethyl, ethyl fluoroacetate, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, halogenated C3-C4 cycloalkyl, C2-C4 alkenoxy, halogenated C2-C4 alkenoxy, C2-C4 alkynoxy, halogenated C2-C4 alkynoxy, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkoxy-C1-C4 alkyl, halogenated C1-C4 alkoxy-C1-C4 alkyl, C1- C4 alkylthio-C1-C4 alkyl, halo-C1-C4 alkylthio-C1-C4 alkyl, C1-C4 alkyl containing sulfinyl, C1-C4 alkyl containing both halo and sulfinyl, C1-C4 alkyl containing sulfonyl, C1-C4 alkyl containing both halo and sulfonyl, amino-C1-C4 alkyl, amino-containing halo-C1-C4 alkyl, C1-C4 alkoxycarbonyl, CONH2, C1-C4 alkylaminocarbonyl, di(C1-C4 alkyl)aminocarbonyl, cyano-C1-C4 alkoxy, C1-C4 alkoxycarbonyl-C1-C4 alkyl, C1-C4 alkylaminocarbonyl-C1-C4 alkyl, di(C1-C4 alkyl)aminocarbonyl-C1-C4 alkyl, phenyl or heteroaryl;

[0016] The heteroaryl group can be pyridyl, pyrimidinyl, thiazolyl, thiophene, furanyl, pyrazolyl, pyrroleyl, indolyl, or other heteroaryl groups containing one or more heteroatoms such as oxygen, sulfur, or nitrogen.

[0017] The present invention uses the following specific compounds of general formula (I) as examples, but the present invention is not limited to these compounds:

[0018]

[0019]

[0020] The preparation routes of the compounds of general formula (I) of this invention are shown in formula (1), (2) or (3).

[0021] The preparation methods of compounds A-1 to A-12 are shown in reaction path (1); the preparation methods of compounds A-13 to A-27 are shown in reaction path (2) or (3).

[0022]

[0023] In reaction (1):

[0024] R is defined as described above, where "X" represents Cl, Br, I, etc.

[0025] The reaction is carried out in an atmosphere of air, nitrogen, or argon; preferably in an atmosphere of nitrogen or argon.

[0026] The alkali includes, but is not limited to, at least one of sodium borohydride, potassium borohydride, sodium hydride, and sodium hydroxide, preferably sodium borohydride dissolved in a 5% sodium hydroxide solution; the amount of alkali is 1-3 equivalents, preferably 2 equivalents;

[0027] The reaction solvent includes, but is not limited to, at least one of ethanol, anhydrous ethanol, N,N-dimethylformamide, N,N-dimethylacetamide, and acetonitrile; more preferably, anhydrous ethanol.

[0028] The preferred reaction conditions are: stirring reaction in an oil bath at 0-25℃, more preferably: stirring reaction in an oil bath at 0℃; the preferred reaction time is: 2-30 min for the first step and 2-12 h for the second step, more preferably: 5 min for the first step and 3-4 h for the second step.

[0029] In the post-processing, the preferred extraction reagent is ethyl acetate; the preferred drying reagent is anhydrous Na2SO4; the preferred purification method is column chromatography; when using column chromatography for purification, the preferred eluent is petroleum ether, ethyl acetate, and methanol.

[0030]

[0031] In reaction (2):

[0032] R is defined as described above, where "X" represents Cl, Br, I, etc.

[0033] The reaction is carried out in an atmosphere of air, nitrogen, or argon; preferably in an atmosphere of nitrogen or argon.

[0034] The reaction solvent is water, and the amount of KSeCN used is 1-3 equivalents, preferably 2 equivalents;

[0035] The alkali includes, but is not limited to, at least one of potassium phosphate, potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, and triethylamine, with potassium phosphate being preferred; the amount of alkali is 2-10 equivalents, preferably 5 equivalents;

[0036] The preferred reaction conditions are: stirring in an oil bath at 45-120°C, more preferably: stirring in an oil bath at 65°C; the preferred reaction time is: 10-300 min for the first step and 10-300 min for the second step, more preferably: 45 min for the first step and 45 min for the second step.

[0037] In the post-processing, the preferred extraction reagent is ethyl acetate; the preferred drying reagent is anhydrous Na2SO4; the preferred purification method is column chromatography; when using column chromatography for purification, the preferred eluent is petroleum ether, ethyl acetate, and methanol.

[0038]

[0039] In reaction (3):

[0040] R is as defined above in this article;

[0041] The reaction is carried out in an atmosphere of air, nitrogen, or argon; preferably in an atmosphere of nitrogen or argon.

[0042] The reaction solvent includes, but is not limited to, at least one of ethanol, anhydrous ethanol, N,N-dimethylformamide, N,N-dimethylacetamide, and acetonitrile; more preferably, anhydrous ethanol.

[0043] Base 1 includes, but is not limited to, at least one of sodium borohydride, potassium borohydride, sodium hydride and sodium hydroxide, preferably sodium borohydride; the amount of base 1 is 1-3 equivalents, preferably 2 equivalents;

[0044] Base 2 includes, but is not limited to, at least one of piperidine, piperidine hydrochloride, pyridine, tetrahydropyrrole, and pyrrole, preferably piperidine hydrochloride, and the amount of base 2 is 1-3 equivalents, preferably 2 equivalents;

[0045] The preferred reaction conditions are: first step, stirring reaction in an oil bath at 0-45℃; second step, stirring reaction in an oil bath at 45-120℃; more preferably, stirring reaction in an oil bath at 0℃ in the first step; and reflux heating and stirring reaction in an oil bath in the second step. The preferred reaction time is: 30-60 min for the first step and 45-180 min for the second step; more preferably, 45 min for the first step and 60 min for the second step.

[0046] In the post-processing, the preferred extraction reagent is ethyl acetate; the preferred drying reagent is anhydrous Na2SO4; the preferred purification method is column chromatography; when using column chromatography for purification, the preferred eluent is petroleum ether, ethyl acetate, and methanol.

[0047] The diarylmethylselenoether derivatives (including diarylmethylselenoether and diselenoether derivatives) and their agriculturally acceptable salts of the present invention can be widely used to control and eliminate various agricultural and forestry weeds and harmful plants, and to promote the growth and development of various crops (including crops, vegetables, fruits, etc.). Therefore, they can be used to prepare herbicides and plant growth regulators. The agriculturally acceptable salts of the diarylmethylselenoether derivatives (including diarylmethylselenoether and diselenoether derivatives) are formed by reacting the diarylmethylselenoether derivatives (including diarylmethylselenoether and diselenoether derivatives) with an acid, wherein the acid includes at least one of hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid, and citric acid. The weeds and harmful plants refer to broadleaf weeds, arborescent weeds, and sedges; the plant growth regulators are used to regulate crop growth and development, and the crops refer to food crops, oil crops, vegetable crops, fruits, and medicinal crops, etc.

[0048] In this instruction manual, "herbicide" and "plant growth regulator" are collective terms for substances that control all the weeds and harmful plants mentioned above and promote the growth and development of various crops. Examples of weeds and harmful plants include, but are not limited to: *Ageratum conyzoides* L., *Bidens pilosa* L., *Mikania micrantha* Kunth, *Praxelis clematidea* (Griseb.) RMKing et H. Rob., *Echinochloa crus-galli*, *Digitaria sanguinalis*, *Setaria viridis*, *Eleusine indica* L., *Avena fatua* L., *Sorghum halepense*, *Agropyron repens*, *Brachiaria plantaginea*, *Panicum purpurascen*, *Leptochloa chinensis*, and *Leptochloa chinensis*. panicea); plants of the genus *Cyperaceae* such as *Cyperus iria* L. and *Cyperus rotundus* L.), including *Scirpus juncoides*, *Cyperus serotinus*, *Cyperus difformis*, *Eleocharis acicularis*, and *Eleochariskuroguwai*; *Sagittaria* pygmaea, *Sagittaria trifolia*, and *Aisma canaliculatum*; *Monochoria* vaginalis and *Monochoria korsakowii*; *Lindernia pyxidaria* and *Dopatrium junceum*; *Lythraceae* rotala indica and *Ammannia multiflora*; and broadleaf plants such as *Amaranthus*. The following are some of the plant species mentioned: *Retroflexus*, *Abutilontheophrasti*, *Ipcmoea hederacea*, *Chenopodium album*, *Sidaspinosa L.*, *Portulaca oleracea L.*, *Amaranthus viridis L.*, *Cassia obtusifolia*, *Solanum nigrum L.*, *Polygonum lapathifolium L.*, *Stellaria media L.*, *Xanthium strumarium L.*, *Cardamine flexuosa WITH.*, *Lamium amplexicaule L.*, and *Acalypha australis L.*.

[0049] Examples of crops include, but are not limited to, wheat, rice, corn, sweet potatoes, potatoes, soybeans, broad beans, peas, and mung beans. Vegetables include, but are not limited to, radishes, turnips, cabbage, kale, bok choy, mustard greens, celery, tomatoes, eggplants, peppers, cucumbers, zucchini, and pumpkins. Fruits include, but are not limited to, apples, pears, hawthorns, oranges, pomelos, peaches, longans, grapes, lychees, strawberries, pineapples, mangoes, apricots, and plums. The methods for promoting crop growth and development (improving plant quality) include, but are not limited to: increasing root length, increasing fresh weight, improving germination rate, and improving seedling emergence rate.

[0050] The present invention also provides a weed control and plant growth regulator composition containing an active ingredient (a compound of general formula (I)) and an agriculturally acceptable carrier, wherein the active ingredient comprises 0.01–99.99% by weight.

[0051] The composition is prepared as defined above by mixing a compound of general formula (I) with a support. The active component in this composition may contain a single compound or a mixture of several compounds of the present invention.

[0052] The above compositions can be applied in formulation form. Compounds of general formula (I) are dissolved or dispersed in a carrier or formulated as active ingredients for easier dispersion when used as herbicides and plant growth regulators; for example, these chemical formulations can be made into powders, wettable powders, emulsifiable concentrates, concentrated emulsions and microemulsions, suspensions, granules, oils and ultra-low volume sprays, smoke formulations, slow-release formulations, and other pesticide formulations. At least one liquid or solid carrier is incorporated into these compositions, and a suitable surfactant may be added when necessary.

[0053] The carrier in the composition of this invention is a substance that, after being formulated with the active ingredients, is easily applied to the site to be treated, which may be a plant, seed, or soil; or is conducive to storage, transportation, or handling. The carrier may be solid or liquid, including substances that are typically gaseous but have been compressed into a liquid, and any carrier commonly used in the formulation of herbicide compositions may be used.

[0054] The above-mentioned agricultural composition can be used for controlling and killing or preventing agricultural weeds and harmful plants or for regulating the growth and development of various crops.

[0055] The specific method of the above application is as follows: the herbicide is applied to the medium in which weeds or harmful plants grow, and the plant growth regulator is applied to the medium in which the crop grows.

[0056] For certain applications, such as in agriculture, one or more other types of herbicides, plant growth regulators, insecticides, nematicides, acaricides, fungicides, or fertilizers may be added to the herbicide and plant growth regulator compositions of the present invention, thereby producing additional advantages and effects.

[0057] This invention also provides the use of diarylmethylselenoether derivatives (including diarylmethylselenoether derivatives and diarylmethyldiselenoether derivatives) as described in general formula (I) or their agronomically acceptable salts in the preparation of herbicides and plant growth regulators, wherein the herbicides are used to remove weeds and harmful plants, wherein the weeds and harmful plants refer to broadleaf weeds, tree weeds and sedges, specifically including barnyard grass, artichoke, and mitochondritis; and the plant growth regulators are used to regulate crop growth and development, wherein the crops refer to grain crops, oil crops, vegetable crops, fruits and medicinal crops, specifically including rice and Chinese cabbage.

[0058] It should be clearly stated that various modifications and alterations can be made within the scope defined by the claims of this invention.

[0059] Compared with the prior art, the present invention has the following advantages and beneficial effects:

[0060] The preparation method of the general formula (I) diarylmethylselenoether derivatives (including diarylmethylselenoether and diselenoether derivatives) compounds of this invention is simple, the raw materials are readily available, and the cost is low. They can effectively inhibit weeds and harmful plants in agriculture, forestry, and other fields, and promote the growth and development of various crops in agricultural production. The general formula (I) compounds have good toxic and growth-inhibiting effects on agricultural weeds and harmful plants such as barnyard grass, artichoke, and mitochondritis, and good growth-promoting effects on crops such as rice and Chinese cabbage. The general formula (I) diarylmethylselenoether derivatives (including diarylmethylselenoether and diselenoether derivatives) compounds of this invention can be applied to plants by irrigation or foliar spraying within the concentration range of 0.1 mg / L-100 mg / L, demonstrating strong applicability. Detailed Implementation

[0061] The present invention will be further described in detail below with reference to embodiments, but the embodiments of the present invention are not limited thereto. All raw materials involved in the present invention can be purchased directly from the market. For process parameters not specifically specified, conventional techniques can be referred to.

[0062] Compound Synthesis Examples

[0063] Synthesis Example 1: Preparation of Compound A-6

[0064]

[0065] Under N2 protection, Se (0.0395 g, 0.5 mmol) was added to 10 mL of anhydrous ethanol and stirred for 5 min in an ice bath. NaBH4 (0.0378 g, 1.0 mmol) was dissolved in 3 mL of 5% sodium hydroxide solution, and then the dissolved NaBH4 solution was added dropwise to the Se suspension and stirred. When the solution became colorless and transparent due to the formation of Na2Se, the ice bath was removed. Compound a (1.0 mmol) was dissolved and the solution was added dropwise to the colorless solution under vigorous stirring. The solution was stirred at room temperature for 3-4 h, then poured into ice water and extracted with ethyl acetate. The organic phase solution was filtered with diatomaceous earth, dried with anhydrous Na2SO4, and the dried solution was developed by TLC and then purified by column chromatography using petroleum ether, ethyl acetate, and methanol as eluents. Compounds A-1 to A-6 were prepared using the above method.

[0066]

[0067] Structures of compounds A-1 to A-6

[0068] Synthesis Example 2: Preparation of Compound A-8

[0069]

[0070] Under N2 protection, Se (0.0395 g, 0.5 mmol) and NaBH4 (0.0378 g, 1.0 mmol) were added to 2 mL of anhydrous ethanol, and after stirring for 2 min, anhydrous DMF (9 mL) was added. The mixture was stirred at 20 °C for 1.5 h. Stirring was stopped when the initial reddish-brown mixture turned into a colorless solution. Compound b (1.0 mmol) was then dissolved in 3 mL of anhydrous ethanol, and this solution was added dropwise to the colorless solution while stirring vigorously. The solution was further stirred at room temperature for 2–4 h, then poured into ice water and extracted with ethyl acetate. The organic phase solution was filtered through diatomaceous earth, dried over anhydrous Na2SO4, and the dried solution was developed by TLC and then purified by column chromatography using petroleum ether, ethyl acetate, and methanol as eluents. Compounds A-7 to A-12 were prepared using the above method.

[0071]

[0072] Structures of compounds A-7 to A-12

[0073] Synthesis Example 3: Preparation of Compound A-17

[0074]

[0075] Compound c (0.5 mmol) and KSeCN (0.0865 g, 0.6 mmol) were added to a 15 mL reaction tube, followed by 5 mL of distilled water. The reaction mixture was vigorously stirred at 65 °C for 45–60 min. Then, K3PO4 (0.5307 g, 2.5 mmol) was added to the mixture while stirring, and the mixture was stirred at 65 °C for 45–60 min. After the reaction was complete, the mixture was cooled, and the solution was poured into water and extracted with ethyl acetate. The organic phase was filtered through diatomaceous earth, dried over anhydrous Na2SO4, and the dried solution was developed by TLC. The solution was then purified by column chromatography using petroleum ether, ethyl acetate, and methanol as eluents. Compounds A-13 to A-17 were prepared using the above method.

[0076]

[0077] Structures of compounds A-13 to A-17

[0078] Synthesis Example 4: Preparation of Compound A-23

[0079]

[0080] Under N2 protection, Se (0.0395 g, 0.5 mmol) was added to 10 mL of anhydrous ethanol and stirred in an ice bath for 5 min. NaBH4 (0.0378 g, 1.0 mmol) was added to the vigorously stirred Se suspension, and stirring was continued for 45 min. When the solution became colorless and transparent due to the reaction to form NaHSe, the ice bath was removed. Piperidine hydrochloride (0.1216 g, 1.0 mmol) was then added to the colorless NaHSe solution, followed by 0.5 mmol of compound d. The reaction mixture was heated under reflux for 1 h and cooled to room temperature to obtain a brown solution. The addition of a small dose of sodium borohydride caused a vigorous reaction in the brown solution, changing the color from brown to yellow-orange. The yellow-orange solution was then poured into water and extracted with ethyl acetate. The organic phase solution was filtered through diatomaceous earth, dried over anhydrous Na2SO4, and the dried solution was developed by TLC and then purified by column chromatography using petroleum ether, ethyl acetate, and methanol as eluents. Compounds A-18 to A-27 were all prepared using the method described above.

[0081]

[0082] Structures of compounds A-18 to A-27

[0083] NMR data of compounds (unless otherwise specified, for all other compounds:) 1H NMR, 500MHz; 13 C NMR, 126MHz, internal standard TMS, solvent: CDCl3) as follows:

[0084] Compound A-1: ​​white solid. 1 H NMR (500MHz, CDCl3) δ7.39–7.18(m,10H),3.78–3.71(m,4H). 13 C NMR (126MHz, CDCl3) δ139.23,129.01,128.51,126.72,27.61.

[0085] Compound A-2: white solid. 1 H NMR (600MHz, CDCl3) δ7.29 (d, J = 8.4Hz, 4H), 7.14 (d, J = 8.4Hz, 4H), 3.82 (s, 4H). 13 C NMR (151MHz, CDCl3) δ137.60,133.11,130.40,128.74,31.78.

[0086] Compound A-3: pale yellow oil. 1 H NMR (500MHz, CDCl3) δ8.52(d,J=4.3Hz,2H),7.60(td,J=7.7,1.6Hz,2H),7.32(d,J=7.8Hz,2H),7.12(dd,J=6.9,5.3Hz,2H),3.92(s,4H). 13 CNMR (126MHz, CDCl3) δ159.77,149.42,136.76,123.31,121.72,29.11.

[0087] Compound A-4: pale yellow solid. 1 H NMR (500MHz, CDCl3) δ8.49(dd,J=4.7,1.4Hz,2H),8.42(d,J=1.9Hz,2H),7.51(d,J=7.8Hz,2H),7.23(dd,J=7.7,4.9Hz,2H),3.79–3.72(m,4H). 13 CNMR (126MHz, CDCl3) δ149.90,148.23,136.33,134.48,123.43,24.32.

[0088] Compound A-5: pale yellow solid. 1H NMR (500MHz, CDCl3) δ8.44 (d, J = 6.0 Hz, 4H), 7.08 (d, J = 5.9 Hz, 4H), 3.57 (s, 4H). 13 C NMR (126MHz, CDCl3) δ149.92,147.60,123.91,26.12.

[0089] Compound A-6: Yellow solid. 1 H NMR (500MHz, CDCl3) δ8.86–8.39(m,4H),7.15(t,J=4.9Hz,2H),4.29–4.01(m,4H). 13 C NMR (126MHz, CDCl3) δ169.94,157.54,118.92,30.09.

[0090] Compound A-7: white solid. 1 H NMR (500MHz, CDCl3) δ8.25(d,J=2.2Hz,2H),7.57(dd,J=8.2,2.4Hz,2H),7.30–7.24(m,2H),3.69(s,4H). 13 C NMR (126MHz, CDCl3) δ150.13149.58,139.32,133.42,124.36,23.63.

[0091] Compound A-8: pale yellow oil. 1 H NMR (500MHz, CDCl3) δ5.08 (t, J = 4.6 Hz, 2H), 3.99–3.95 (m, 4H), 3.89–3.82 (m, 4H), 2.81 (d, J = 4.6 Hz, 4H). 13 C NMR (126MHz, CDCl3) δ104.34, 65.31, 27.36.

[0092] Compound A-9: Black oil. 1 H NMR(500MHz,D2O)δ8.52(d,J=4.3Hz,2H),7.60(td,J=7.7,1.6Hz,2H),7.32(d,J=7.8Hz,2H),7.12(dd,J=6.9,5.3Hz,2H),,4.36(s,6H),3.92(s,4H). 13 CNMR (126MHz, CDCl3) δ159.77,149.42,136.76,123.31,121.72,48.76,29.11.

[0093] Compound A-10: Yellow-brown oily substance. 1 H NMR (500MHz, D2O) δ8.68 (d, J = 4.7Hz, 4H), 7.99 (s, 4H), 4.36 (s, 6H), 4.12 (s, 4H). 13 C NMR (126MHz, D2O) δ159.4,144.86,127.97,47.76,25.74.

[0094] Compound A-11: Black oil. 1 H NMR(500MHz,D2O)δ8.52(d,J=4.3Hz,2H),7.60(td,J=7.7,1.6Hz,2H),7.32(d,J=7.8 Hz,2H),7.12(dd,J=6.9,5.3Hz,2H),4.36(s,6H),3.92(s,4H),1.60(t,J=7.4Hz,6H). 13 C NMR (126MHz, CDCl3) δ159.77,149.42,136.76,123.31,121.72,56.33,48.76,29.11.

[0095] Compound A-12: Yellow-brown oily substance. 1 H NMR (500MHz, D2O) δ8.64(d,J=6.4Hz,4H),7.85(d,J=6.0Hz,4H),4.56(q,J=7.3Hz,4H),2.63(s,6H),1.60(t,J=7.4Hz,6H). 13 C NMR (126MHz, D2O) δ159.77,142.74,128.60,56.33,21.21,15.54.

[0096] Compound A-13: Yellow-orange solid. 1 H NMR (600MHz, CDCl3) δ7.51–7.02 (m, 10H), 3.85 (s, 4H). 13 C NMR (151MHz, CDCl3) δ139.15,129.16,128.58,127.23,32.76.

[0097] Compound A-14: white solid. 1 H NMR (600MHz, CDCl3) δ7.34 (d, J = 8.5 Hz, 4H), 7.30 (d, J = 8.6 Hz, 4H), 4.24 (s, 4H). 13C NMR (151MHz, CDCl3) δ134.74,134.24,130.39,129.41,31.92.

[0098] Compound A-15: Brown oily substance. 1 H NMR (500MHz, CDCl3) δ8.50(d,J=4.3Hz,2H),7.56(td,J=7.7,1.8Hz,2H),7.13(d,J=7.8Hz,2H),7.12–7.08(m,2H),4.20–3.86(m,4H). 13 C NMR (126MHz, CDCl3) δ158.78,149.67,136.40,123.12,121.91,34.80.

[0099] Compound A-16: pale yellow solid. 1 H NMR (500MHz, CDCl3) δ8.47(dd,J=4.8,1.4Hz,2H),8.41(d,J=1.9Hz,2H),7.51–7.48(m,2H),7.22(dd,J=7.7,4.8Hz,2H),3.79–3.70(m,4H). 13 C NMR (126MHz, CDCl3) δ149.87,148.41,136.26,134.65,123.37,28.82.

[0100] Compound A-17: Yellow solid. 1 H NMR (500MHz, CDCl3) δ8.51 (d, J = 5.8 Hz, 4H), 7.08 (d, J = 5.8 Hz, 4H), 3.75 (s, 4H). 13 C NMR (126MHz, CDCl3) δ149.89,147.81,123.90,30.65.

[0101] Compound A-18: Yellow solid. 1 H NMR (600MHz, CDCl3) δ8.18(d,J=2.4Hz,2H),7.49(dd,J=8.2,2.5Hz,2H),7.32–7.17(m,2H),3.78(s,4H). 13 C NMR (151MHz, CDCl3) δ150.34,149.51,139.12,133.68,124.26,27.84.

[0102] Compound A-19: pale yellow solid. 1H NMR (500MHz, CDCl3) δ8.32(d,J=5.1Hz,2H),7.26(s,2H),7.14(s,2H),7.04(dd,J=5.0,2.0Hz,2H).3.78(s,4H). 13 C NMR (126MHz, CDCl3) δ151.74,151.04,149.83,124.15,122.62,29.88.

[0103] Compound A-20: pale yellow solid. 1 H NMR (500MHz, CDCl3) δ7.47 (t, J = 7.7Hz, 2H), 7.32 (d, J = 7.8Hz, 2H), 7.13 (d, J = 7.5Hz, 2H), 3.99 (s, 4H). 13 C NMR (126MHz, CDCl3) δ160.15,141.78,138.80,126.44,122.09,33.79.

[0104] Compound A-21: pale yellow oil. 1 H NMR (500MHz, CDCl3) δ7.55(t,J=7.7Hz,2H),6.80(d,J=7.2Hz,2H),6.63(d,J=8.2Hz,2H),4.67(s,4H),3.95(s,6H). 13 C NMR (126MHz, CDCl3) δ163.65,156.78,139.28,112.69,109.09,63.86,53.38.

[0105] Compound A-22: white solid. 1 H NMR (500MHz, CDCl3) δ8.63 (s, 4H), 4.95 (s, 4H). 13 C NMR (126MHz, CDCl3) δ151.12,146.39,123.44,64.19.

[0106] Compound A-23: pale yellow oil. 1 H NMR (500MHz, CDCl3) δ6.24 (d, J = 3.2 Hz, 2H), 6.19 (d, J = 3.2 Hz, 2H), 3.91 (s, 4H). 13 C NMR (126MHz, CDCl3) δ153.94,121.2,112.63,110.90,23.90.

[0107] Compound A-24: Yellow-brown oily substance.1 H NMR (500MHz, CDCl3) δ7.44–7.30(m,2H),6.33(dd,J=3.0,1.9Hz,2H),6.21(d,J=3.1Hz,2H),3.93(s,4H). 13 C NMR (126MHz, CDCl3) δ151.96,142.35,110.98,108.15,24.25.

[0108] Compound A-25: a reddish-yellow solid. 1 H NMR (500MHz, CDCl3) δ8.09(s,2H),7.45(s,2H),7.28(t,J=6.9Hz,2H),7.22–7.14(m,2H),7.09(dd,J=8.3,1.4Hz,2H),6.55(s,2H),4.01(s,4H). 13 CNMR (126MHz, CDCl3) δ135.13,130.38,128.07,124.73,123.59,121.22,111.22,102.87,34.07.

[0109] Compound A-26: a dark red solid. 1 H NMR (600MHz, CDCl3) δ6.76 (d, J = 1.6 Hz, 2H), 6.17 (d, J = 3.0 Hz, 2H), 6.14 (dd, J = 1.6, 0.8 Hz, 2H), 3.90 (s, 4H). 13 C NMR (151MHz, CDCl3) δ128.95,118.40,108.87,108.39,24.72.

[0110] Compound A-27: white solid. 1 H NMR (600MHz, CDCl3) δ8.52(s,2H),8.08(s,2H),7.65(d,J=8.4Hz,4H),7.50(d,J=8.3Hz,4H),4.76(s,4H). 13 C NMR (151MHz, CDCl3) δ152.65,141.44,140.96,136.32,128.27,120.28,64.45.

[0111] Bioactivity Assay Examples

[0112] The compounds of this invention exhibit excellent activity against a variety of weeds in the agricultural field. The results of the herbicidal activity assays are shown in the following examples.

[0113] Example 5: Evaluation of the herbicidal activity of some compounds against barnyard grass

[0114] Pre-germination treatment: Soak weed seeds in 15% sodium hypochlorite solution for 15 minutes, rinse several times with tap water, and then wash 2-3 times with distilled water. Next, soak barnyard grass seeds in a 200 mg / L gibberellin solution for 24 hours. After 24 hours, remove the seeds and wash them 2-3 times with distilled water. Place 9.0 cm diameter qualitative filter paper in the culture dish and evenly moisten the filter paper with 3 mL of distilled water. Evenly place 40-50 barnyard grass seeds in each culture dish (the number varies depending on the seed size), add distilled water again until the seeds no longer float, and cover with plastic wrap with small holes to ensure ventilation and prevent moisture evaporation. Place in a light incubator at 25±2℃ for 16h / 8h (L / D) with a relative humidity of 80%. After 2-3 days, pick the seeds that have just sprouted white seeds for later use.

[0115] Experimental treatment: Each test compound was dissolved in an appropriate amount of acetone, diluted with water (containing 0.1% Tween 80) to a concentration of 10 g / L, and then diluted with acetone + water + Tween 80 to 50 mg / L. Plastic cups with a diameter of approximately 5 cm and a height of 7 cm were used as containers. Three to four layers of glass beads with a diameter of approximately 0.4 cm were added to each cup, which was then covered with perforated plastic wrap to prevent moisture loss and maintain ventilation. Ten to fifteen newly sprouted barnyard grass seeds were placed in each cup. The control group was treated with an equal volume of acetone-distilled water (generally, the organic solvent content was less than 1%). Each treatment was repeated three times. The treatment environment was a light incubator at 25±2℃, 16h / 8h (L / D), and a relative humidity of 80%. After 7 days, root growth and the overall condition of the plants were observed and photographed. Fresh weight was measured, and root length was measured using Image-Pro Plus 6.0 software. Root length and fresh weight inhibition rate were calculated. Root length inhibition rate (%) = (control root length – treatment root length) / control root length × 100%; Fresh weight inhibition rate (%) = (control fresh weight – treatment fresh weight) / control fresh weight × 100%. The experimental results are shown in Tables 1 and 2.

[0116] Example 6: Evaluation of the herbicidal activity of some compounds against Artemisia annua

[0117] Pre-germination treatment: Soak weed seeds in 15% sodium hypochlorite solution for 15 minutes, rinse several times with tap water, and then wash 2-3 times with distilled water. Next, soak *Ageratum conyzoides* seeds in a 200 mg / L gibberellin solution for 24 hours. Remove the seeds and wash 2-3 times with distilled water. Place 9.0 cm diameter qualitative filter paper in the culture dish and evenly moisten the filter paper with 3 mL of distilled water. Evenly place 40-50 *Ageratum conyzoides* seeds in each culture dish (the number varies depending on the seed size), add distilled water again until the seeds no longer float, and cover with plastic wrap with small holes to ensure ventilation and prevent moisture evaporation. Place in a light incubator at 25±2℃ for 16h / 8h (L / D) with a relative humidity of 80%. After 2-3 days, pick the seeds that have just sprouted white seeds for later use.

[0118] Experimental treatment: Each test compound was dissolved in an appropriate amount of acetone, diluted with water (containing 0.1% Tween 80) to a concentration of 10 g / L, and then diluted with acetone + water + Tween 80 to 50 mg / L. Plastic cups with a diameter of approximately 5 cm and a height of 7 cm were used as containers. Three to four layers of glass beads with a diameter of approximately 0.4 cm were added to each cup, which was then covered with perforated plastic wrap to prevent moisture loss and maintain ventilation. Ten to fifteen budding *Ageratum oryzae* seeds were placed in each cup. The control group was treated with an equal volume of acetone-distilled water (generally, the organic solvent content was less than 1%). Each treatment was repeated three times. The treatment environment was a light incubator at 25±2℃, 16h / 8h (L / D), and a relative humidity of 80%. After 7 days, root growth and the overall condition of the plants were observed and photographed. Fresh weight was measured, and root length was measured using Image-Pro Plus 6.0 software. Root length and fresh weight inhibition rate were calculated. Root length inhibition rate (%) = (control root length – treatment root length) / control root length × 100%; Fresh weight inhibition rate (%) = (control fresh weight – treatment fresh weight) / control fresh weight × 100%. The experimental results are shown in Tables 1 and 2.

[0119] Example 7: Evaluation of the herbicidal activity of some compounds against Mikania micrantha

[0120] Pre-germination treatment: Soak weed seeds in 15% sodium hypochlorite solution for 15 minutes, rinse several times with tap water, and then wash 2-3 times with distilled water. Next, soak Mikania micrantha seeds in a 200 mg / L gibberellin solution for 24 hours. Remove the seeds and wash 2-3 times with distilled water. Place 9.0 cm diameter qualitative filter paper in the culture medium and evenly moisten the filter paper with 3 mL of distilled water. Evenly place 40-50 Mikania micrantha seeds in each culture dish (the number varies depending on the seed size), add distilled water again until the seeds no longer float, and cover with plastic wrap with small holes to ensure ventilation and prevent moisture evaporation. Place in a light incubator at 25±2℃ for 16h / 8h (L / D) with a relative humidity of 80%. After 2-3 days, select the seeds that have just sprouted white seeds for later use.

[0121] Experimental treatment: Each test compound was dissolved in an appropriate amount of acetone, diluted with water (containing 0.1% Tween 80) to a concentration of 10 g / L, and then diluted with acetone + water + Tween 80 to 50 mg / L. Plastic cups with a diameter of approximately 5 cm and a height of 7 cm were used as containers. Three to four layers of glass beads with a diameter of approximately 0.4 cm were added to each cup, which was then covered with perforated plastic wrap to prevent moisture loss and maintain ventilation. Ten to fifteen budding Mikania seeds were placed in each cup. The control group was treated with an equal volume of acetone-distilled water (generally, the organic solvent content was less than 1%). Each treatment was repeated three times. The treatment environment was a light incubator at 25±2℃, 16h / 8h (L / D), and a relative humidity of 80%. After 7 days, root growth and the overall condition of the plants were observed and photographed. Fresh weight was measured, and root length was measured using Image-Pro Plus 6.0 software. Root length and fresh weight inhibition rate were calculated. Root length inhibition rate (%) = (control root length – treatment root length) / control root length × 100%; Fresh weight inhibition rate (%) = (control fresh weight – treatment fresh weight) / control fresh weight × 100%. The experimental results are shown in Tables 1 and 2.

[0122] Table 1. Root length inhibition rate test of some compounds of the present invention on three weeds.

[0123]

[0124]

[0125] Table 2. Test results of the fresh weight inhibition rate of some compounds of the present invention on three weeds.

[0126]

[0127]

[0128] The compounds of this invention exhibit excellent promoting activity against a variety of crops in the agricultural field. The results of crop-promoting activity assays are shown in the following examples.

[0129] Example 8: Evaluation of the rice-promoting activity of some compounds

[0130] Accurately weigh 5 mg of the test compound using a 0.01 g / L balance, add 0.5 mL of dimethyl sulfoxide (DMSO), and shake to completely dissolve the compound, preparing a stock solution with a concentration of 10,000 mg / L. Then, take a certain volume of the stock solution as needed, add a certain amount of DMSO solvent, and dilute the stock solution with Tween 80 at a concentration of 0.5‰-1.0‰ to obtain solutions of varying concentrations for testing.

[0131] Select rice seeds of uniform size and plumpness. Disinfect the selected seeds and then soak them in a 50 mg / L aqueous solution of a compound for 12 hours. After soaking, blot the surface moisture with filter paper. Sow the treated rice seeds into 9 cm diameter petri dishes, placing two layers of qualitative filter paper moistened with distilled water in each dish. Place 20 rice seeds in each dish. Incubate the petri dishes in a constant temperature incubator at 25 ± 1℃ in the dark. After 5 days of incubation, measure the root length of the rice seeds. Root length growth rate (%) = (Root length of treatment group / Root length of control group) × 100%. The experimental results are shown in Table 3.

[0132] Example 9: Evaluation of the promoting activity of some compounds on Chinese cabbage.

[0133] Accurately weigh 5 mg of the test compound using a 0.01 g / L balance, add 0.5 mL of dimethyl sulfoxide (DMSO), and shake to completely dissolve the compound, preparing a stock solution with a concentration of 10,000 mg / L. Then, take a certain volume of the stock solution as needed, add a certain amount of DMSO solvent, and dilute the stock solution with Tween 80 at a concentration of 0.5‰-1.0‰ to obtain solutions of varying concentrations for testing.

[0134] Select uniformly sized and plump rice seeds. Disinfect the selected Chinese cabbage seeds and then soak them in a 50 mg / L aqueous solution of a compound for 12 hours. After soaking, blot the surface moisture with filter paper. Sow the treated rice seeds into 9 cm diameter petri dishes, placing two layers of qualitative filter paper moistened with distilled water in each dish. Place 20 Chinese cabbage seeds in each dish. Incubate the petri dishes in a constant temperature incubator at 25 ± 1℃ in the dark. After 5 days of incubation, measure the root length of the Chinese cabbage seeds. Root length growth rate (%) = (Root length of treatment group / Root length of control group) × 100%. The experimental results are shown in Table 3.

[0135] Table 3. Promotion activity tests of some compounds of the present invention on two crops.

[0136]

[0137] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the present invention shall be considered equivalent substitutions and shall be included within the protection scope of the present invention.

Claims

1. A class of diarylmethylselenide derivatives, characterized in that, Its structural formula is as follows: 。 2. A class of diarylmethylselenide derivatives, characterized in that, Its structural formula is as follows: 。 3. The method for preparing a class of diarylmethylselenoether derivatives according to claim 1 or 2, characterized in that, The preparation route of the compound according to claim 1 or 2 is shown in formula (1), (2) or (3): In reaction (1): R is selected from the following structure ， Where "X" represents Cl; The reaction is carried out in an atmosphere of air, nitrogen, or argon; The base includes at least one of sodium borohydride, potassium borohydride, sodium hydride, and sodium hydroxide; the amount of the base is 1-3 equivalents; The reaction solvent includes at least one of ethanol, anhydrous ethanol, N,N-dimethylformamide, N,N-dimethylacetamide, and acetonitrile; The reaction conditions are: stirring reaction in an oil bath at 0-25℃; the reaction time is: 2-30 min for the first step and 2-12 h for the second step. In reaction (2): R is selected from the following structure ， Where "X" represents Cl or Br; The reaction is carried out in an atmosphere of air, nitrogen, or argon; The reaction solvent is water, and the amount of KSeCN used is 1-3 equivalents; The base includes at least one of potassium phosphate, potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, and triethylamine; the amount of base is 2-10 equivalents; The reaction conditions are: stirring reaction in an oil bath at 45-120℃; the reaction time is: 10-300 min for the first step and 10-300 min for the second step. In reaction (3): R is selected from the following structure ； The reaction is carried out in an atmosphere of air, nitrogen, or argon; The reaction solvent includes at least one of ethanol, anhydrous ethanol, N,N-dimethylformamide, N,N-dimethylacetamide, and acetonitrile; Base 1 includes at least one of sodium borohydride, potassium borohydride, sodium hydride, and sodium hydroxide; the amount of base 1 is 1-3 equivalents; Base 2 includes at least one of piperidine, piperidine hydrochloride, pyridine, tetrahydropyrrole, and pyrrole, and the amount of base 2 is 1-3 equivalents; The reaction conditions are as follows: the first step is to react with stirring in an oil bath at 0-45℃, and the second step is to react with stirring in an oil bath at 45-120℃; the reaction time is as follows: 30-60 min for the first step and 45-180 min for the second step. In the post-processing of reaction formulas (1)-(3), the extraction reagent is ethyl acetate; the drying reagent is anhydrous Na2SO4; the purification is carried out by column chromatography; when purifying by column chromatography, the eluent used is petroleum ether, ethyl acetate and methanol.

4. An agriculturally acceptable salt of a class of diarylmethylselenoether derivatives, characterized in that, The agriculturally acceptable salt of the diarylmethylselenoether derivative is formed by reacting the diarylmethylselenoether derivative of claim 1 or 2 with an acid, said acid including at least one selected from hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, fumaric acid, sorbic acid, malic acid, and citric acid.

5. Use of the diaryl methyl selenide derivative of claim 1 or an agriculturally acceptable salt thereof in the preparation of herbicides and plant growth regulators.

6. The use according to claim 5, characterized in that, The herbicide is used to control and eliminate weeds and harmful plants, which refer to broadleaf weeds, tree weeds, and sedges; the plant growth regulator is used to regulate crop growth and development, which refers to food crops, oil crops, vegetable crops, fruits, and medicinal crops.

7. The use according to claim 6, characterized in that, The weeds and harmful plants mentioned refer to barnyard grass, artichoke, and mikanea; the crops mentioned refer to rice and Chinese cabbage.

8. Use of a class of diarylmethyl selenide derivatives of claim 2 or an agriculturally acceptable salt thereof in the preparation of herbicides.

9. The use according to claim 8, characterized in that, The herbicide is used to control and eliminate weeds and harmful plants, which refer to broadleaf weeds, tree weeds, and sedges.

10. The use according to claim 8, characterized in that, The weeds and harmful plants mentioned refer to barnyard grass, artichoke, and mikanella.

11. A herbicide and plant growth regulator composition, characterized in that, The composition contains an active component and an agriculturally acceptable carrier. The active component is a diarylmethyl selenide derivative as described in claim 1 or an agriculturally acceptable salt thereof. The weight percentage of the active component in the composition is 0.01–99.99%.

12. A herbicidal composition, characterized in that, The composition contains an active component and an agriculturally acceptable carrier. The active component is a diarylmethyl selenide derivative as described in claim 2 or an agriculturally acceptable salt thereof. The weight percentage of the active component in the composition is 0.01–99.99%.

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