WO2017129113A1 - Bromohexahydroindanone compounds, preparation method for same, and uses thereof - Google Patents

Abstract

Provided in the present invention are halogenated hexahydroindanone compounds, a preparation method for same, and uses thereof. The present invention relates to bromohexahydroindanone compounds, which have a chemical structural formula as represent by I. Disclosed are the structural formula of the compounds, a synthesis method for same, and uses thereof as pesticides, fungicides, antiviral agents for plants, uses of and a preparation method for the compounds being used in conjunction with agriculturally acceptable excipients or synergists and with commercialized pesticides, fungicides, antiviral agents for plants, and acaricides in prevention and treatment of pests, diseases, viral diseases of plants in agriculture, forestry, and gardening.

Description

一类溴代六氢茚酮类化合物及其制备方法和用途Brominated hexahydroindanone compound, preparation method and use thereof 技术领域Technical field

本发明的技术方案涉及含卤素原子的六氢茚酮类化合物，具体涉及溴代六氢茚酮类化合物。The technical solution of the present invention relates to a hexahydroinone compound containing a halogen atom, and more particularly to a hexahydroindanone compound.

背景技术Background technique

卤素具有独特的理化性质，因此，带来含卤素的化合物具有独特的生物活性，不同卤素原子之间由于其原子半径和电负性的差异，不同的卤化物也具有不同的理化性质以及生物活性。在农药品种中，氯代物和溴代物以及碘代物均具有不同的生物活性，例如，将烯酰吗啉中的Cl原子用F原子取代后的氟吗啉的两个异构体均具有很好的杀菌活性，而烯酰吗啉则只有一个异构体具有杀菌活性。本课题组将具有诱导抗病活性的4-甲基-1,2,3-噻二唑-5-甲酸乙酯中的甲基H用Br原子取代后生成的4-溴甲基-1,2,3-噻二唑-5-甲酸乙酯则具有很好的杀菌活性。Halogen has unique physicochemical properties, so the halogen-containing compounds have unique biological activities. Different halides have different physical and chemical properties and biological activities due to differences in atomic radius and electronegativity. . Among the pesticide varieties, the chlorinated and brominated substances and the iodomorph have different biological activities. For example, the two isomers of the fluoromorpholine in which the Cl atom in the dimethomorph is substituted with the F atom has a good The bactericidal activity, while the dimethomorph has only one isomer having bactericidal activity. Our group will have 4-bromomethyl-1 formed by substituting the methyl group H of 4-methyl-1,2,3-thiadiazole-5-carboxylate in the induction of disease resistance with Br atom. 2,3-thiadiazol-5-carboxylic acid ethyl ester has good bactericidal activity.

茚酮类化合物是有机合成的重要中间体，例如2-乙酰氧基二氢茚酮可用于有机合成，而茚酮的结构广泛存在与天然产物和药物以及农药等生物活性分子中，其在有机发光和光致变色以及燃料中也是重要的结构单元。Anthrones are important intermediates in organic synthesis. For example, 2-acetoxyindanone can be used in organic synthesis, and the structure of anthrone is widely distributed in biologically active molecules such as natural products and drugs as well as pesticides. Luminescence and photochromism as well as fuel are also important structural units.

本发明利用农药分子设计的原理，将卤素原子引入六氢茚酮先导结构中设计合成了一类卤代六氢茚酮类化合物，并进行了***的生物活性筛选，以期为新农药的创制提供更多高效的侯选化合物。The invention utilizes the principle of pesticide molecular design, introduces a halogen atom into the hexahydrofluorenone lead structure, designs and synthesizes a class of halogenated hexahydroindolone compounds, and carries out systematic biological activity screening, in order to provide for the creation of new pesticides. More efficient candidate compounds.

发明内容Summary of the invention

本发明所要解决的技术问题是：提供新的溴代六氢茚酮类化合物的合成方法，提供这类化合物调控农业、园艺和卫生以及林业植物害虫和植物病原物的生物活性及其测定方法，同时提供这些化合物在农业领域、园艺领域、林业领域以及卫生领域的中应用。The technical problem to be solved by the present invention is to provide a novel method for synthesizing brominated hexahydroindolone compounds, and to provide such compounds for regulating biological activities of agricultural, horticultural and sanitary and forestry plant pests and plant pathogens, and methods for determining the same, At the same time, these compounds are provided for use in the agricultural, horticultural, forestry, and sanitary fields.

本发明解决该技术问题所采用的技术方案是：具有农业领域、园艺领域、林业以及卫生领域杀虫活性、杀菌活性、抗植物病毒活性的溴代六氢茚酮类化合物的结构通式为I：The technical solution adopted by the present invention to solve the technical problem is that the structural formula of the brominated hexahydroinone compound having insecticidal activity, bactericidal activity, and anti-plant virus activity in the agricultural field, the horticultural field, the forestry, and the sanitary field is I. :

其中，R¹选自苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-氟苯基、3-氟苯基、4-氟苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-硝基苯基、3-硝基苯基、4-硝基苯基、4-乙基苯基、4-甲基-1,2,3-噻二唑基、2-呋喃基、2-甲基-2-(4-氯苯基)-1-丙基、三氯甲基、菊酰基、二氯菊酰基、4-氟苯乙基、2,6-二氯苯基、甲基、丙基、庚基、3,5-二氯苯基、3,5-二甲基、3-(2-氯苯基)-5-甲基异噁唑-4-基、2,4-二甲基-1-苯基吡唑-3-基、环己基、2-氟苯乙基、3,6-二氯吡啶-2-基、5-乙基-1-甲基吡唑-3-基、2-氟苯乙基的基团、4-甲基-1,2,3-噻二唑-5-基、5-甲基-1,2,3-噻二唑-4-基、3,4-二氯异噻唑-5-基；X¹选自F、Cl、Br、I；X²选自F、Cl、Br、I。Wherein, R ¹ is selected from phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl Phenylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-trifluoromethylphenyl, 3 -trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-ethylphenyl, 4-methyl- 1,2,3-thiadiazolyl, 2-furyl, 2-methyl-2-(4-chlorophenyl)-1-propyl, trichloromethyl, cholanyl, dichloro chrysanyl, 4 -fluorophenethyl, 2,6-dichlorophenyl, methyl, propyl, heptyl, 3,5-dichlorophenyl, 3,5-dimethyl, 3-(2-chlorophenyl) -5-methylisoxazol-4-yl, 2,4-dimethyl-1-phenylpyrazol-3-yl, cyclohexyl, 2-fluorophenethyl, 3,6-dichloropyridine- a group of 2-yl, 5-ethyl-1-methylpyrazol-3-yl, 2-fluorophenethyl, 4-methyl-1,2,3-thiadiazol-5-yl, 5 -Methyl-1,2,3-thiadiazol-4-yl, 3,4-dichloroisothiazol-5-yl; X ^{1 is} selected from F, Cl, Br, I; X ^{2 is} selected from F, Cl , Br, I.

本发明的溴代六氢茚酮类化合物I的合成方法如下：The synthesis method of the brominated hexahydroindolone compound I of the present invention is as follows:

其中，R¹选自苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-氟苯基、3-氟苯基、4-氟苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-硝基苯基、3-硝基苯基、4-硝基苯基、4-乙基苯基、4-甲基-1,2,3-噻二唑基、2-呋喃基、2-甲基-2-(4-氯苯基)-1-丙基、三氯甲基、菊酰基、二氯菊酰基、4-氟苯乙基、2,6-二氯苯基、甲基、丙基、庚基、3,5-二氯苯基、3,5-二甲基、3-(2-氯苯基)-5-甲基异噁唑-4-基、2,4-二甲基-1-苯基吡唑-3-基、环己基、2-氟苯乙基、3,6-二氯吡啶-2-基、5-乙基-1-甲基吡唑-3-基、2-氟苯乙基的基团、4-甲基-1,2,3-噻二唑-5-基、5-甲基-1,2,3-噻二唑-4-基、3,4-二氯异噻唑-5-基；X选自F、Cl、Br、I；X¹选自F、Cl、Br、I；X²选自F、Cl、Br、I；NXS选自N-溴代丁二酰亚胺、N-氯代丁二酰亚胺。Wherein, R ¹ is selected from phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl Phenylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-trifluoromethylphenyl, 3 -trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-ethylphenyl, 4-methyl- 1,2,3-thiadiazolyl, 2-furyl, 2-methyl-2-(4-chlorophenyl)-1-propyl, trichloromethyl, cholanyl, dichloro chrysanyl, 4 -fluorophenethyl, 2,6-dichlorophenyl, methyl, propyl, heptyl, 3,5-dichlorophenyl, 3,5-dimethyl, 3-(2-chlorophenyl) -5-methylisoxazol-4-yl, 2,4-dimethyl-1-phenylpyrazol-3-yl, cyclohexyl, 2-fluorophenethyl, 3,6-dichloropyridine- a group of 2-yl, 5-ethyl-1-methylpyrazol-3-yl, 2-fluorophenethyl, 4-methyl-1,2,3-thiadiazol-5-yl, 5 -Methyl-1,2,3-thiadiazol-4-yl, 3,4-dichloroisothiazol-5-yl; X is selected from the group consisting of F, Cl, Br, I; X ^{1 is} selected from the group consisting of F, Cl, br, I; X ² is selected from F, Cl, br, I; NXS selected from N- bromosuccinimide, N- chlorosuccinimide acid Amine.

优选地，所述的溴代六氢茚酮类化合物的合成方法分为以下步骤：Preferably, the method for synthesizing the brominated hexahydroindanone compound is divided into the following steps:

A.化合物III的制备：A. Preparation of Compound III:

将化合物II加入反应瓶中，抽真空，注入氮气保护，然后加入干燥的四氢呋喃溶液，冰盐浴下向反应瓶中缓慢滴加乙烯基溴化镁，滴加完毕后，分别在冰盐浴中和室温下搅拌，反应完全后，反应液加入饱和碳酸氢钠溶液淬灭，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物III； Add compound II to the reaction flask, vacuum, inject nitrogen to protect, then add dry tetrahydrofuran solution, slowly add vinyl magnesium bromide to the reaction flask under ice salt bath, and add the mixture to the ice salt bath. After stirring at room temperature, the reaction mixture was quenched with saturated sodium hydrogen sulfate solution and extracted with ethyl acetate. The ethyl acetate layer was separated and washed with saturated sodium hydrogen carbonate and saturated sodium chloride. Drying over anhydrous magnesium sulfate, suction filtration, concentration, solvent was evaporated under reduced pressure, and the residue was purified to give compound III;

B.化合物IV的制备：B. Preparation of Compound IV:

将步骤A制得的化合物III溶于四氢呋喃溶液中，然后加入硼氢化钠，冰浴下缓慢滴加三氟化硼***的四氢呋喃溶液，滴加完毕后，分别在冰浴中和室温下搅拌，反应完全后，在冰浴下向反应瓶中缓慢滴加Jones试剂，滴加完毕后在室温继续搅拌，反应完全后，加入水，然后用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物IV；The compound III obtained in the step A was dissolved in a tetrahydrofuran solution, and then sodium borohydride was added thereto, and a solution of boron trifluoride diethyl ether in tetrahydrofuran was slowly added dropwise thereto in an ice bath. After the dropwise addition, the mixture was stirred in an ice bath and at room temperature. After the reaction was completed, the Jones reagent was slowly added dropwise to the reaction flask under ice bath. After the completion of the dropwise addition, stirring was continued at room temperature. After the reaction was completed, water was added, and then extracted with ethyl acetate to separate the ethyl acetate layer. The ester phase is washed with saturated sodium hydrogen carbonate and saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, filtered, evaporated

C.化合物V的制备：C. Preparation of Compound V:

将步骤B制得的化合物IV溶于四氢呋喃与水的混合溶液中，冰浴下向反应液中加入硼氢化钠，加入完毕后，撤去冰浴，室温搅拌，反应完全后加入饱和碳酸氢钠淬灭，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物V；The compound IV obtained in the step B is dissolved in a mixed solution of tetrahydrofuran and water, and sodium borohydride is added to the reaction solution under ice bath. After the addition, the ice bath is removed, stirred at room temperature, and the reaction is completed, and then saturated with sodium hydrogencarbonate is added. The mixture was extracted with EtOAc. EtOAc EtOAc. Purification, preparation of compound V;

D.化合物VI的制备：D. Preparation of Compound VI:

将步骤C制得的化合物V溶于二氯甲烷中，抽真空，注入氮气保护，冰浴下向反应瓶中加入三乙胺，然后缓慢滴加酰氯R¹COCl，滴加完毕后，撤去冰浴，室温搅拌，反应完全后加入饱和碳酸氢钠溶液萃取，分出二氯甲烷层，二氯甲烷相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物VI；The compound V prepared in the step C was dissolved in dichloromethane, vacuumed, and protected with nitrogen. Triethylamine was added to the reaction flask under ice bath, and then the acid chloride R ¹ COCl was slowly added dropwise. After the addition was completed, the ice was removed. The mixture was stirred at room temperature. After the reaction was completed, the mixture was evaporated, evaporated, evaporated, evaporated, evaporated. , the solvent is removed under reduced pressure, the residue is purified to give the compound VI;

E.化合物VII的制备：E. Preparation of Compound VII:

将步骤D制得的化合物VI溶于甲磺酸中，然后加入五氧化二磷在35-40摄氏度下反应，反应完全后加入水，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物VII；The compound VI obtained in the step D is dissolved in methanesulfonic acid, and then the phosphorus pentoxide is added to react at 35-40 degrees Celsius. After the reaction is completed, water is added, and the mixture is extracted with ethyl acetate to separate the ethyl acetate layer. The ester phase is washed with saturated sodium hydrogencarbonate and saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, filtered, evaporated,

F.化合物I的制备：F. Preparation of Compound I:

当R¹为Ph、X¹为Br、X²为H时，化合物I的制备方法如下：When R ¹ is Ph, X ¹ is Br, and X ² is H, the preparation method of Compound I is as follows:

将步骤E制得的化合物VII溶于干燥的四氯化碳中，然后依次加入N-溴代丁二酰亚胺和偶氮二异丁腈，在50摄氏度下反应，反应完全后，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物I；The compound VII obtained in the step E is dissolved in dry carbon tetrachloride, and then N-bromosuccinimide and azobisisobutyronitrile are sequentially added, and the reaction is carried out at 50 ° C. After the reaction is completed, the filtration is carried out. , concentrated, the solvent is removed under reduced pressure, the residue is purified to give the compound I;

当R¹为Ph、X¹为H、X²为Br时，化合物I的制备方法如下：When R ¹ is Ph, X ¹ is H, X ² is Br, compound I was prepared as follows:

将步骤E制得的化合物VII溶于干燥的乙腈中，然后依次加入N-溴代丁二酰亚胺和三氟甲磺酸三甲基硅酯，加入完毕后，室温搅拌，反应完全后加入饱和碳酸氢钠溶液萃取，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯 化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物I。The compound VII obtained in the step E is dissolved in dry acetonitrile, and then N-bromosuccinimide and trimethylsilyl trifluoromethanesulfonate are sequentially added. After the addition is completed, the mixture is stirred at room temperature, and the reaction is completed. Extracted with saturated sodium bicarbonate solution, extracted with ethyl acetate, and the ethyl acetate layer was separated, and ethyl acetate phase with saturated sodium hydrogen carbonate and saturated After washing with sodium chloride, dried over anhydrous magnesium sulfate, filtered, evaporated, evaporated,

作为本发明的一个优选的方法，所述的溴代六氢茚酮类化合物的合成方法分为以下步骤：As a preferred method of the present invention, the synthesis method of the brominated hexahydroinone compound is divided into the following steps:

A.化合物III的制备：A. Preparation of Compound III:

将3.2毫摩尔的化合物II加入100毫升两口瓶中，抽真空，注入氮气保护，然后加入25毫升干燥的四氢呋喃溶液，冰盐浴下向反应瓶中缓慢滴加3.5毫摩尔乙烯基溴化镁，滴加完毕后，冰盐浴搅拌20分钟，撤去冰浴，室温搅拌2小时，反应完全后，反应液加入20毫升饱和碳酸氢钠溶液淬灭，乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，残余物经200～300目硅胶柱层析纯化得化合物III，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝6:1的混合液；用所得纯品计算收率，收率70％；化合物III制备的量和反应容器的体积按相应比例扩大或缩小。3.2 mmol of Compound II was added to a 100 ml two-necked flask, vacuumed, and protected with nitrogen. Then, 25 ml of a dry tetrahydrofuran solution was added, and 3.5 mmol of vinylmagnesium bromide was slowly added dropwise to the reaction flask under ice salt bath. After the completion of the dropwise addition, the ice salt bath was stirred for 20 minutes, the ice bath was removed, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction mixture was quenched with 20 ml of saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The ethyl acetate phase was washed with saturated sodium bicarbonate and saturated sodium chloride, and dried over anhydrous magnesium sulfate, filtered, evaporated, evaporated, evaporated. III, the eluent is a mixture of petroleum ether = 6:1 in a volume ratio of ethyl acetate: 60-90 degrees Celsius; the yield is calculated from the obtained pure product, the yield is 70%; the amount of the compound III and the reaction container are prepared. The volume is enlarged or reduced according to the corresponding proportion.

B.化合物IV的制备：B. Preparation of Compound IV:

将0.76毫摩尔化合物III溶于20毫升干燥的四氢呋喃溶液中，然后加入2.27毫摩尔硼氢化钠，冰浴下缓慢滴加3.04毫摩尔三氟化硼***的四氢呋喃溶液，滴加完毕后，冰浴搅拌15分钟再撤去冰浴，然后室温搅拌2小时，停止反应后在冰浴下向反应瓶中缓慢滴加4.6毫摩尔的Jones试剂，滴加完毕后在室温继续搅拌2小时，反应完全后，加入20毫升水，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，乙酸乙酯相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物IV，洗脱剂体积比为乙酸乙酯:60～90摄氏度馏分的石油醚＝4:1的混合液；用所得纯品计算收率，收率45％；化合物IV制备的量和反应容器的体积按相应比例扩大或缩小。0.76 mmol of the compound III was dissolved in 20 ml of a dry tetrahydrofuran solution, then 2.27 mmol of sodium borohydride was added, and a solution of 3.04 mmol of boron trifluoride etherate in tetrahydrofuran was slowly added dropwise on an ice bath. After stirring for 15 minutes, the ice bath was removed, and then stirred at room temperature for 2 hours. After the reaction was stopped, 4.6 mmol of Jones reagent was slowly added dropwise to the reaction flask under ice bath. After the completion of the dropwise addition, stirring was continued for 2 hours at room temperature. After the reaction was completed, After adding 20 ml of water and extracting with ethyl acetate, the ethyl acetate layer was separated, and the ethyl acetate phase was washed again with saturated sodium hydrogen carbonate and saturated sodium chloride. After concentrating and removing the solvent under reduced pressure, the residue was purified by silica gel column chromatography from 200 to 300 mesh to obtain compound IV. The volume ratio of eluent to ethyl acetate: petroleum ether of 60 to 90 ° C = 4:1 mixture The yield was calculated from the obtained pure product in a yield of 45%; the amount of the compound IV prepared and the volume of the reaction vessel were expanded or reduced in a corresponding ratio.

C.化合物V的制备：C. Preparation of Compound V:

将1.9毫摩尔化合物IV溶于15毫升体积比为四氢呋喃与水为10:1的混合溶液中，冰浴下向反应液中分批加入2毫摩尔硼氢化钠，加入完毕后，撤去冰浴，室温搅拌1小时，反应完全后加入15毫升饱和碳酸氢钠淬灭，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，乙酸乙酯相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物V，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝3:1的混合液；用所得纯品计算收率，收率68％；化合物V制备的量和反应容器的体积按相应比例扩大或缩小。 1.9 mmol of the compound IV was dissolved in 15 ml of a mixed solution of tetrahydrofuran and water of 10:1, and 2 mmol of sodium borohydride was added portionwise to the reaction solution under ice bath. After the addition, the ice bath was removed. After stirring at room temperature for 1 hour, the reaction was completed, and then the mixture was evaporated to ethyl acetate. The ethyl acetate phase was dried over anhydrous magnesium sulfate, filtered, evaporated, evaporated, evaporated, evaporated. A mixture of petroleum ether = 3:1 of -90 ° C fraction; the yield was calculated by the obtained pure product, the yield was 68%; the amount of the compound V and the volume of the reaction vessel were expanded or reduced according to the corresponding ratio.

D.化合物VI的制备：D. Preparation of Compound VI:

将3.5毫摩尔化合物V溶于25毫升重蒸后的二氯甲烷中，抽真空，注入氮气保护，冰浴下向反应瓶中加入14毫摩尔的三乙胺，然后缓慢滴加酰氯R¹COCl，滴加完毕后，撤去冰浴，室温搅拌过夜，反应完全后加入20毫升饱和碳酸氢钠溶液萃取，分出二氯甲烷层，二氯甲烷相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，二氯甲烷相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物VI，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝8:1的混合液；用所得纯品计算收率，收率90％；化合物VI制备的量和反应容器的体积按相应比例扩大或缩小。3.5 mmol of compound V was dissolved in 25 ml of re-distilled dichloromethane, vacuumed, and protected with nitrogen. 14 mmol of triethylamine was added to the reaction flask under ice bath, and then acid chloride R ¹ COCl was slowly added dropwise. After the dropwise addition is completed, the ice bath is removed, and the mixture is stirred at room temperature overnight. After the reaction is completed, the mixture is extracted with 20 ml of saturated sodium hydrogencarbonate solution, and the dichloromethane layer is separated, and the dichloromethane phase is further saturated sodium bicarbonate and saturated sodium chloride. After washing once, the dichloromethane phase was dried over anhydrous magnesium sulfate, suction filtered, concentrated, and then evaporated to remove the solvent, and the residue was purified by silica gel column chromatography on 200-300 mesh to afford compound VI. Ester: a mixture of petroleum ether = 8:1 of a fraction of 60 to 90 degrees Celsius; the yield was calculated by the obtained pure product, and the yield was 90%; the amount of the compound VI and the volume of the reaction vessel were expanded or reduced according to the corresponding ratio.

E.化合物VII的制备：E. Preparation of Compound VII:

将0.7毫摩尔化合物VI溶于6毫升甲磺酸中，然后加入0.01毫摩尔五氧化二磷与35-40摄氏度加热反应6小时，反应完全后加入20毫升水，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，乙酸乙酯相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物VII，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝8:1的混合液；用所得纯品计算收率，收率60％；化合物VII制备的量和反应容器的体积按相应比例扩大或缩小。0.7 mmol of compound VI was dissolved in 6 ml of methanesulfonic acid, and then 0.01 mmol of phosphorus pentoxide was added and heated at 35-40 ° C for 6 hours. After the reaction was completed, 20 ml of water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer and the ethyl acetate phase were washed again with saturated sodium hydrogen sulfate and saturated sodium chloride, and the ethyl acetate phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The compound VII was purified by silica gel column chromatography on ~300 mesh, and the eluent was a mixture of petroleum ether = 8:1 in a volume ratio of ethyl acetate: 60-90 ° C; the yield was calculated from the obtained pure product, yield 60 %; the amount of the compound VII prepared and the volume of the reaction vessel are enlarged or reduced in a corresponding ratio.

F.化合物I的制备：F. Preparation of Compound I:

当R¹为Ph、X¹为Br、X²为H时，化合物I的制备方法如下：When R ¹ is Ph, X ¹ is Br, and X ² is H, the preparation method of Compound I is as follows:

将7毫摩尔化合物VII溶于干燥的四氯化碳中，然后依次加入7.7毫摩尔N-溴代丁二酰亚胺、0.07毫摩尔偶氮二异丁腈，于50摄氏度加热反应过夜，反应完全后，抽滤，浓缩，减压除去溶剂，残余物经200～300目硅胶柱层析纯化得化合物I，洗脱剂为体积比为乙酸乙酯:60～90摄氏度馏分的石油醚＝10:1的混合液；用所得纯品计算收率，收率50％；用N-氯代丁二酰亚胺替代N-溴代丁二酰亚胺可以制备相应的氯代物；化合物I制备的量和反应容器的体积按相应比例扩大或缩小。7 mmol of the compound VII was dissolved in dry carbon tetrachloride, and then 7.7 mmol of N-bromosuccinimide and 0.07 mmol of azobisisobutyronitrile were sequentially added, and the reaction was heated at 50 ° C overnight. After completion, the mixture was suction filtered, concentrated, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography from 200 to 300 mesh to afford compound I, eluent in a volume ratio of ethyl acetate: petroleum ether of 60-90 deg. a mixture of :1; the yield is calculated by the obtained pure product, the yield is 50%; the corresponding chloro compound can be prepared by substituting N-chlorosuccinimide for N-bromosuccinimide; The amount and volume of the reaction vessel are enlarged or reduced in proportion to the corresponding ratio.

当R¹为Ph、X¹为H、X²为Br时，化合物I的制备方法如下：When R ¹ is Ph, X ¹ is H, and X ² is Br, the preparation method of Compound I is as follows:

将0.4毫摩尔化合物VII溶于15毫升干燥的乙腈中，然后依次加入0.44毫摩尔N-溴代丁二酰亚胺，0.02毫摩三氟甲磺酸三甲基硅酯，加入完毕后，室温搅拌过夜，反应完全后加入20毫升饱和碳酸氢钠溶液萃取，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，乙酸乙酯相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物I，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝10:1的混合液；用所得纯品 计算收率，收率46％；用N-氯代丁二酰亚胺替代N-溴代丁二酰亚胺可以制备相应的氯代物；化合物I制备的量和反应容器的体积按相应比例扩大或缩小。0.4 mmol of compound VII was dissolved in 15 ml of dry acetonitrile, followed by the addition of 0.44 mmol of N-bromosuccinimide, 0.02 mmol of trimethylsilyl trifluoromethanesulfonate. After stirring overnight, the reaction was completed, and then extracted with 20 ml of saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was separated, and the ethyl acetate phase was washed again with saturated sodium hydrogen carbonate and saturated sodium chloride. The ester phase is dried over anhydrous magnesium sulfate, filtered, concentrated, and evaporated, evaporated, evaporated. a mixture of petroleum ether = 10:1 of Celsius fraction; Calculate the yield, yield 46%; replace the N-bromosuccinimide with N-chlorosuccinimide to prepare the corresponding chlorinated product; the amount of compound I prepared and the volume of the reaction vessel are expanded according to the corresponding proportion Or shrink.

本发明还提供了所述的溴代六氢茚酮类化合物I在制备杀菌剂、杀虫剂、抗植物病毒剂或植物激活剂中的用途。The invention also provides the use of the bromo hexahydroindanone compound I in the preparation of a bactericide, insecticide, plant virus agent or plant activator.

本发明还提供了所述的溴代六氢茚酮类化合物I与农业上可接受的助剂在制备杀虫剂、杀虫剂、抗植物病毒剂或植物激活剂中的用途。The invention also provides the use of the bromo hexahydroindanone compound I and an agriculturally acceptable adjuvant in the preparation of an insecticide, insecticide, plant virus agent or plant activator.

本发明还提供了所述的溴代六氢茚酮类化合物I在制备抗植物病毒剂中的用途。The invention also provides the use of the bromo hexahydroindanone compound I in the preparation of an anti-plant virus agent.

本发明还提供了所述的溴代六氢茚酮类化合物I在制备植物激活剂中的用途。The invention also provides the use of the bromo hexahydroindanone compound I in the preparation of a plant activator.

本发明还提供了所述的溴代六氢茚酮类化合物I在防治农业和林业以及园艺植物虫害中的用途。The invention also provides the use of the bromo hexahydroindanone compound I for controlling agricultural and forestry and horticultural plant pests.

优选地，所述溴代六氢茚酮类化合物I与农业化学品共同施用；更优选地，所述农业化学品选自：杀虫剂、杀菌剂、抗植物病毒剂、杀螨剂中的一种或几种。Preferably, the brominated hexahydroindanone compound I is co-administered with an agricultural chemical; more preferably, the agricultural chemical is selected from the group consisting of: an insecticide, a bactericide, an anti-plant virus agent, an acaricide One or several.

优选地，所述的溴代六氢茚酮类化合物I与所述杀虫剂中的任意一种或两种组合形成杀虫组合物用于防治农业和林业以及园艺植物虫害；Preferably, the hexahydroindanone compound I is combined with any one or both of the insecticides to form a pesticidal composition for controlling agricultural and forestry and horticultural plant pests;

其中，所述杀虫剂选自：毒死蜱、地亚哝、啶虫脒、甲氨基阿维菌素、弥拜菌素、阿维菌素、多杀菌素、氰戊菊酯、高效氰戊菊酯、氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、Beta-氟氯氰菊酯、Lambda-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、联苯菊酯、氯菊酯、醚菊酯、氟氯苯菊酯、氯氟胺氰戊菊酯、吡虫啉、烯啶虫胺、氯噻啉、噻虫啉、噻虫嗪、噻虫胺、呋虫胺、可尼丁、达特南、除虫脲、灭幼脲、伏虫隆、除虫隆、氟铃脲、氟虫脲、啶虫隆、虱螨脲、毒虫脲、氟幼脲、Noviflumuron即多氟脲，其CAS号为121451-02-3、氟螨脲、Novaluron即双苯氟脲、氟啶脲、Bay sir 6874即1-[(3.5-二氯-4)4-硝基苯氧基苯基3-3-(2-氯苯)-脲、Bay SIR-8514即1-(4-三氟甲氧基苯基)-3-(2-氯苯)-脲、嗪虫脲、Bistrifluron即双三氟虫脲、呋喃虫酰肼、虫酰肼、氯虫酰肼、甲氧虫酰肼、环虫酰肼、乐果、氧化乐果、敌敌畏、乙酰甲胺磷、***磷、喹硫磷、哒嗪硫磷、氯唑磷、叶蝉散、西维因、抗蚜威、速灭威、异丙威、杀螟丹、仲丁威、叶飞散、甲萘威、丙硫克百威、丁硫克百威、杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、丁烯氟虫腈、***锡、噻嗪酮、灭线磷、氟虫腈、杀虫单、杀虫双、氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、唑虫酰胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素；Wherein the insecticide is selected from the group consisting of: chlorpyrifos, scorpion scorpion, acetamiprid, emamectin, imipenem, avermectin, spinosad, fenvalerate, high-efficiency fenvalerate Ester, cypermethrin, beta-cypermethrin, cyhalothrin, deltamethrin, fenpropathrin, Beta-cyfluthrin, Lambda-cyhalothrin, permethrin, permethrin, methrin, biphenyl Pyrethroid, permethrin, etofenprox, flumethrin, flufenacetate, imidacloprid, nitenpyram, chlorothiazide, thiacloprid, thiamethoxam, clothianidin, furosemide Amine, cotinine, Dartnam, diflubenzuron, chlorbenzuron, flubenzuron, chlorfenapyr, hexaflumuron, flubenzuron, acetamiprid, guanidine, chlorfenapyr, fluorolactam, Noviflumuron That is, polyfluorourea, its CAS number is 121451-02-3, fluoroquinone urea, Novaluron, ie, diphenylfluorourea, chlorfluazuron, Bay sir 6874, 1-[(3.5-dichloro-4)4-nitrobenzene Oxyphenyl-3-3(2-chlorophenyl)-urea, Bay SIR-8514, 1-(4-trifluoromethoxyphenyl)-3-(2-chlorophenyl)-urea, oxazide , Bistrifluron, bistriazole, furanyl hydrazide, tebufenozide, chlorine Acylhydrazide, methoxyfenhydrazide, chlorfenapyr, dimethoate, omethoate, dichlorvos, acephate, triazophos, quetiapine, pyridazin, chlorpyrifos, arsenic, western Weiyin, Kangwei, Suweiwei, Weiweiwei, Zhidan, Zhongdingwei, Yefeisan, carbaryl, propylthiocarbamate, butyl thiocarb, chlorpyrifos, bromo oxime ester, Thiacinone, oxazolidine, anthrone, tetrazine, alkyne, dibutyl ether urea, pymetrozine, spirodecyl ester, spirotetramat, spirotetramat, butene fipronil, triazole tin , buprofezin, chlorpyrifos, fipronil, insecticidal, insecticidal, chlorantranil, flubendiamide, flufenamide, cyanamide, azole, chlorfenapyr, pyrazinone, Etoxazole, pyridoxamine, ketone, pyriproxyfen, emamectin;

所述的溴代六氢茚酮类化合物I在所述杀虫组合物中的质量百分含量是1％-90％；The mass percentage of the brominated hexahydroindanone compound I in the pesticidal composition is 1% to 90%;

所述的溴代六氢茚酮类化合物I与所述杀虫剂的比例为质量百分比1％∶99％到 99％∶1％；The ratio of the brominated hexahydroindanone compound I to the insecticide is 1% by mass to 99% by mass 99%: 1%;

所述杀虫组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；The dosage form processed by the pesticidal composition is selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble thickener, poisonous valley, block bait, granular Bait, flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, hot aerosol ,cold spray, aerosol, solid/liquid mixture, liquid/liquid mixture, solid/solid mixture, lacquer, granule, trace powder, oil suspension, oil dispersible powder, thick rubber Agent, pouring agent, seed coating agent, smear agent, film forming oil agent, ultra low volume liquid agent, steam release agent;

所述杀虫组合物防治的植物虫害选自：红蜘蛛、东亚飞蝗、云斑车蝗、中华稻蝗、日本黄脊蝗、单刺蝼蛄、东方蝼蛄、稻蓟马、烟蓟马、温室蓟马、稻管蓟马、麦简管蓟马、温室白粉虱、烟粉虱、黑尾叶蝉、大青叶蝉、棉叶蝉、斑衣蜡蝉、褐飞虱、白背飞虱、灰飞虱、甘蔗扁角飞虱、棉蚜、麦二叉蚜、麦长管蚜、桃蚜、高粱蚜、萝卜蚜、吹绵蚧、桑盾蚧、矢尖盾蚧、梨圆蚧、白蜡虫、红蜡蚧、朝鲜球坚蚧、梨网蝽、香蕉网蝽、细角花蝽、微小花蝽、针缘蝽、稻蛛缘蝽、稻褐蝽、稻黑蝽、稻绿蝽、绿盲蝽、苜蓿盲蝽、中黑盲蝽、大草蛉、丽草蛉、中华草蛉、谷蛾、衣蛾、黄刺蛾、褐刺蛾、扁刺蛾、麦蛾、棉红铃虫、甘薯麦蛾、小菜蛾、桃小食心虫、大豆食心虫、桃小食心虫、苹果顶梢卷叶蛾、褐带长卷叶蛾、拟小黄卷叶蛾、二化螟、豆荚螟、玉米螟、三化螟、菜螟、稻纵卷叶螟、条螟、棉卷叶野螟、桃蛀螟、黏虫、斜纹夜蛾、稻螟蛉、棉小造桥虫、甜菜夜蛾、大螟、棉铃虫、鼎点金刚钻、小地老虎、大地老虎、黄地老虎、盗毒蛾、舞毒蛾、甘薯天蛾、豆天蛾、直纹稻弄蝶、隐纹谷弄蝶、柑橘凤蝶、玉带凤蝶、菜粉蝶、苎麻赤蛱蝶、苎麻黄蛱蝶、豆芫菁、金星步甲、皱鞘步甲、麦穗步甲、沟金针虫、细胸金针虫、谷斑皮蠹、黑皮蠹、柑橘小吉丁虫、金缘吉丁虫、黄粉虫、黑粉虫、赤拟谷盗、杂拟谷盗、铜绿异丽金龟、暗黑金龟、华北大黑鳃金龟、桑天牛、星天牛、橘褐天牛、桃红颈天牛、大猿叶虫、小猿叶虫、黄守瓜、黄曲条跳甲、绿豆象、豌豆象、蚕豆象、玉米象、米象、小麦叶蜂、梨实蜂、黄带姬蜂、黏虫白星姬蜂、螟蛉悬茧姬蜂、棉铃虫齿唇姬蜂、螟黑点疣姬蜂、蚊、蝇、虻、麦红吸浆虫、麦黄吸浆虫、稻瘿蚊、柑橘大实蝇、瓜实蝇、麦叶灰潜蝇、美洲斑潜蝇、豆秆黑潜蝇、麦秆蝇、种蝇、葱蝇、萝卜蝇、伞裙追寄蝇、玉米螟厉寄蝇、黏虫；The plant pests controlled by the insecticidal composition are selected from the group consisting of: red spider, oriental locust, scorpion locust, Chinese rice blast, Japanese yellow ridge, single locust, oriental carp, rice locust, smoky horse, greenhouse Hummer, rice tube thrips, wheat tube horses, greenhouse whitefly, whitefly, black-tailed leafhopper, big green leafhopper, cotton leafhopper, spotted waxhopper, brown planthopper, white-backed planthopper, gray fly虱, sugarcane, flat-horned locust, cotton aphid, wheat birch, wheat long tube, peach aphid, sorghum, radish, blown mulberry, mulberry scorpion, yam shield, pear round, white wax insect, Red wax mites, Korean ball scorpion, pear net 蝽, banana net 蝽, fine-horned flower bud, tiny flower bud, needle-edge 蝽, rice spider 蝽, rice brown 蝽, rice black 蝽, rice green 蝽, green blind 蝽, 苜蓿 苜蓿 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Plutella xylostella, Peach Pythium, Soybean, Heartworm, Apple Leaf Roller, Brown Leaf Moth, Yellow Leaf Moth, Chilo suppressalis, Pea, Corn Borer Sanhua carp, rapeseed meal, rice leaf roller, bark, cotton leaf stalk, peach aphid, armyworm, Spodoptera litura, rice blast, cotton small bridge worm, beet armyworm, giant salamander, cotton bollworm Dingdian diamond, small tiger, earth tiger, yellow tiger, poisonous moth, gypsy moth, sweet potato hawk moth, bean hawk moth, straight grain rice butterfly, cryptic valley butterfly, citrus phoenix butterfly, jade belt butterfly, Cabbage butterfly, ramie red butterfly, ramie yellow butterfly, bean phthalocyanine, Venus carapace, wrinkle sheath, armor, wheat burdock, sphaerocephala, scutellaria, scutellaria, black scorpion, citrus Xiaojiding insect, Jinyuanjidin insect, Tenebrio molitor, black mealworm, red-grained pirate, miscellaneous grain thief, bronze green tortoise, dark golden tortoise, North China black scorpion tortoise, mulberry sinensis, star snail, orange Brown-bellied beetle, pink-necked beetle, big-leaf-leaf-leaf, small-leaf-leaf-leaf, yellow-sucking melon, yellow-striped beetle, mung bean, pea, broad bean, corn, rice, wheat leaf bee, pear bee, Yellow-banded bee, sticky insect white star cockroach, cockroach cockroach, cotton bollworm, larvae, cockroach, cockroach, cockroach, cockroach, cockroach Insect, wheat yellow sucking insect, rice gall midge, citrus fruit fly, melon flies, wheat leaf gray fly, Liriomyza sativae, stalk black fly, wheat straw fly, fly, onion fly, radish fly, umbrella The skirt is chasing the flies, the corn scorpion flies, and the sticky insects;

所述杀虫组合物防治的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、 番木瓜、兰花、盆景。The plant controlled by the pesticidal composition is selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, pea, broad bean, pea, mung bean, adzuki bean, cotton, sericulture, peanut, rapeseed, Sesame, sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, rape, onion, garlic , watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, Papaya, orchid, bonsai.

优选地，所述的溴代六氢茚酮类化合物I与所述杀菌剂中的任意一种或两种组合形成杀菌组合物用于防治农业和林业以及园艺植物病害，Preferably, the brominated hexahydroindanone compound I is combined with any one or both of the bactericides to form a bactericidal composition for controlling agricultural and forestry and horticultural plant diseases,

其中，所述杀菌剂选自：苯并噻二唑、噻酰菌胺，简写为TDL、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺，其英文通用名为：isotianil、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、氟酰胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、呋吡菌胺、吡噻菌胺、双炔酰菌胺、苯酰菌胺、甲呋酰胺、萎锈灵、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、***醇、灭菌唑、联苯***醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、灭锈胺、多菌灵、苯菌灵、甲基硫菌灵、***酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、硫线磷、丰索磷、虫线磷、苯线磷、灭线磷、除线磷、氯唑磷、丁硫环磷、杀线威、涕灭威、克百威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑； Wherein the bactericide is selected from the group consisting of: benzothiadiazole, thiazide, abbreviated as TDL, thiazamide, methyl thiazide, 4-methyl-1,2,3-thiadiazole-5-carboxylic acid , 4-methyl-1,2,3-thiadiazol-5-formate, 4-methyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester, DL-β-aminobutyric acid, different Thiamin, its common name in English is: isotianil, 3,4-dichloroisothiazol-5-carboxylic acid, 3,4-dichloroisothiazol-5-formate, 3,4-dichloroisothiazol-5-carboxylic acid Ethyl ester, ribavirin, antofin, nymidine or salicylic acid, cymoxanil, thiram, thiram, mancozeb, ethylphosphorus, thiophanate, chlorothalonil, enemies Pine, procymidone, benzopyridin, methyl thiophanate, thiophanate, refined metalaxyl, flumorph, enoylmorpholine, high-performance metalaxyl, high-efficiency benzoxanthin, chloramphenicol, fungicide Amine, mesalamide, thifluzamide, fluoroamide, leaf cumin, cyclopropionamide, cycloflufenamide, fenhexamidide, cyanamide, thiastrobin, flupirfen, pyr Thiamin, dipropionamide, benzilamide, mefenamide, wilting, etoxin, iprodione, azoxystrobin, fenfluramine, fluoxastrobin, Bacteriocin, phenoxystrobin, acesulfame, pyridoxate, pyraclostrobin, trifloxystrobin, enestrobin, enestrobin, oxoxazole, carbendazole, cyproconazole, Difenoconazole, diniconazole, high-efficiency diniconazole, epoxiconazole, nitrile azole, fluoroquinazole, flusilazole, fluconazole, hexaconazole, imidazole, inocastazole, mexazole , myclobutanil, penconazole, propiconazole, prothioconazole, silrazole, tebuconazole, tetrafluoroetherazole, triazole alcohol, sterilized azole, biphenyl triazole alcohol, thiabendazole, wheat Sui Ning, imazalil, high-efficiency imazalil, prochloraz, fluconazole, cyanoxazole, imidazolone, moxalimid, rice oxime ester, famoxadone, pyridine oxazole, carbendazim, evil Creaming, ethaboxam, carbendazim, octyl ketone, thiothiazide, dodecaline morpholine, butyl morpholine, thirteen morpholine, seed dressing, fluke nitrile, fluazinam, pyridine plaque肟, Cyclohexillin, boscalid, fluazirid, acesulfame, cyprodinil, fluzalazine, azoxystrobin, azoxystrobin, pyrimethanil, chlorpyrimidine, fluoride Pyrimidine alcohol, chlorpyrifos, dicyanoquinone, ethoxyquin, quinolin, propoxy Porphyrin, phenoxyquinoline, carbendazim, isopropylidene, phenothimethamine, propamocarb, sulfavir, enemies, diarrhea, pyridoxine, methyl chlorpyrifos, cockroach , chunleimycin, polymycin, polyoxomycin, tyrosin, jinggangmycin, streptomycin, metalaxyl, furosemide, benzoxanthin, furamide, rust-free amine, carbendazim , benomyl, thiophanate-methyl, triadimefon, acetaminophen sulfonate, dipyridol, acetem, propitan, captan, sterilized dan, vinyl nucleus, chlorofluoro Sclerotium, sclerotium, chlorothalonil, indigo, rice stalk, sulphate, pentachloronitrobenzene, zinc propyl, triethylphosphonate, sulphur, Bordeaux, copper sulphate, oxychloride Copper, cuprous oxide, copper hydroxide, benomyl, pentosan, chlorfenapyr, tetrachlorobenzoquinone, praziquantel, spiroxanthin, tricyclazole, pyrazinamide, polyglycoside, biguanide Octyl salt, bis-octylamine, chloramine, benzepamide, toluidine, oxime ester, sodium sulfonate, quinocodone, allyl benzothiazole, bronopol, iodomethane, Weibaimu, enemy Linear ester, cotton, dichloroisopropyl ether, thiazolyl, sulfur Line phosphorus, Fengsuo phosphorus, insect line phosphorus, benzene line phosphorus, phosphine, dephosphorization, chlorazol, sulphur cyclophosphine, chlorpyrifos, aldicarb, carbofuran, sulfuryl fluoride, dichloro Propylene, dichloroisonicotinic acid, allylic isothiazole;

所述的溴代六氢茚酮类化合物I在所述杀菌组合物中的总的质量百分含量是1％-90％；The total mass percentage of the brominated hexahydroindanone compound I in the germicidal composition is from 1% to 90%;

所述的溴代六氢茚酮类化合物I与所述杀菌剂的比例为质量百分比1％∶99％到99％∶1％；The ratio of the brominated hexahydroindanone compound I to the bactericide is 1% by mass: 99% to 99%: 1% by mass;

所述杀菌组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；The dosage form processed by the bactericidal composition is selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble thickener, poisonous valley, block bait, granular bait , flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, hot spray, Cold spray, aerosol, solid/liquid mixed charge, liquid/liquid mixed charge, solid/solid mixed charge, lacquer, microparticle, trace powder, oil suspension, oil dispersible powder, thickener , pouring agent, seed coating agent, smear agent, film forming oil agent, ultra low volume liquid agent, steam release agent;

所述杀菌组合物防治的植物病害选自：稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病；The plant diseases controlled by the bactericidal composition are selected from the group consisting of: rice seedling cotton rot, tomato root rot, potato late blight, tobacco black shank, millet powdery mildew, grape downy mildew, lettuce downy mildew, cucumber downy mildew Cucumber anthracnose;

所述杀菌组合物适用的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。The bactericidal composition is suitable for plants selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, pea, broad bean, pea, mung bean, adzuki bean, cotton, sericulture, peanut, rape, sesame , sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, rape, onion, garlic, Watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

优选地，所述的溴代六氢茚酮类化合物I与所述抗病毒药剂中的任意一种或两种组合形成抗病毒组合物用于防治农业和林业以及园艺植物病毒病害，Preferably, the bromo hexahydroindanone compound I is combined with any one or both of the antiviral agents to form an antiviral composition for controlling agricultural and forestry and horticultural plant virus diseases,

其中，所述商品抗病毒药剂选自：苯并噻二唑、噻酰菌胺，简写为TDL、异噻菌胺，其英文通用名为：isotianil、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、DL-β-氨基丁酸、病毒唑、安托芬、宁南霉素、噻酰胺、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈羟胺、井冈霉素；Wherein, the commercial antiviral agent is selected from the group consisting of: benzothiadiazole, thiazolamide, abbreviated as TDL, isothiazide, and its common name in English is: isotianil, 4-methyl-1,2,3- Thiadiazole-5-carboxylic acid, sodium 4-methyl-1,2,3-thiadiazole-5-carboxylate, ethyl 4-methyl-1,2,3-thiadiazole-5-carboxylate, 3, 4-Dichloroisothiazol-5-carboxylic acid, 3,4-dichloroisothiazol-5-formate, 3,4-dichloroisothiazol-5-carboxylic acid ethyl ester, DL-β-aminobutyric acid, ribavirin, Antofin, ningnanmycin, thiazamide, methyl thiazide or salicylic acid, glutathione, dichloroisonicotinic acid, allylisothiazole, Jinggang hydroxylamine, Jinggangmycin;

所述的溴代六氢茚酮类化合物I在所述抗病毒组合物中的总的质量百分含量是1％-90％；The total mass percentage of the brominated hexahydroindanone compound I in the antiviral composition is from 1% to 90%;

所述的溴代六氢茚酮类化合物I与所述抗植物病毒剂的比例为质量百分比1％∶99％到99％∶1％；The ratio of the brominated hexahydroindanone compound I to the anti-plant virus agent is 1% by mass: 99% to 99%: 1% by mass;

所述抗病毒组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状 毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；The antiviral composition processed dosage form is selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble thickener, poisonous valley, block bait, granular Poison, flake Poison bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, hot spray, cold spray , aerosol, solid/liquid mixed charge, liquid/liquid mixed charge, solid/solid mixed charge, lacquer, microparticle, trace powder, oil suspension, oil dispersible powder, thick glue, pouring Agent, seed coating agent, smear agent, film forming oil agent, ultra low volume liquid agent, steam release agent;

所述抗病毒组合物防治的病毒病害选自：水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒；The viral disease controlled by the antiviral composition is selected from the group consisting of rice dwarf disease, yellow dwarf disease, stripe leaf blight, tomato fern leaf virus disease, pepper mosaic virus disease, tobacco vein necrosis virus disease, corn dwarf mosaic disease , cauliflower mosaic virus, citrus virus disease, broccoli virus, Jianlan ring spot virus;

所述抗病毒组合物用于防治的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。The plant for controlling the antiviral composition is selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, tapioca, soybean, pea, broad bean, pea, mung bean, adzuki bean, cotton, sericulture, peanut, Rape, sesame, sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, rape, onion , garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

优选地，所述的溴代六氢茚酮类化合物I与所述杀螨剂中的任意一种或两种组合形成杀螨组合物用于防治农业和林业以及园艺植物螨害，Preferably, the hexahydroindanone compound I is combined with any one or both of the acaricides to form a acaricidal composition for controlling agricultural and forestry and horticultural plant damage,

其中所述杀螨剂选自：***锡、三环锡、苯丁锡、三磷锡、毒虫畏、甲基毒虫畏、巴毒磷、敌敌畏、庚烯磷、速灭磷、久效磷、二溴磷、毒死蜱、嘧啶磷、氯甲亚胺硫磷、氧乐果、敌杀磷、乙硫磷、马拉硫磷、虫螨畏、伏杀硫磷、辛硫磷、甲基嘧啶硫磷、喹硫磷、治螟磷、***磷、蚜灭多、水胺硫磷、甲胺磷、胺丙畏、氯亚胺硫磷、亚胺硫磷、氟丙菊酯、联苯菊酯、氯氟氰菊酯、精高效氯氟氰菊酯、甲氰菊酯、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯、溴氟菊酯、联苯肼酯、苯硫威、涕灭威、丁酮威、杀线威、抗虫威、久效威、苯菌灵、氯灭杀威、克百威、丁硫克百威、速灭威、蜱虱威、伐虫脒、单甲脒、杀螨脒、双甲脒、杀虫脒、苯甲酸苄酯、溴螨酯、丁氟螨酯、灭螨醌、氟蚜螨、氟虫脲、浏阳霉素、虫螨霉素、苏云金素、杀螨素、浏阳霉素、阿维菌素、多拉菌素、埃普利诺菌素、伊维菌素、赛拉菌素、莫西菌素、除虫菊素、烟碱、苦参碱、印楝素、鱼藤酮、吡螨胺、哒螨酮、唑螨酯、四螨嗪、炔螨特、噻螨酮、螺螨酯、嘧螨酯、杀螨酯、克螨特、哒螨灵；Wherein the acaricide is selected from the group consisting of: triazolyl tin, tricyclotin, phenbutyltin, triphosphorus, chlorpyrifos, methyl chlorpyrifos, cytotoxic phosphorus, dichlorvos, heptene phosphorus, quick-killing phosphorus, monocrotophos , dibromophosphorus, chlorpyrifos, pyrimidine, chloromethionine, omethoate, chlorpyrifos, ethion, malathion, chlorpyrifos, sulforaphane, phoxim, methylpyrimidine Phosphorus, quetiapine, strontium phosphate, triazophos, quenching, acesulfame, methamidophos, acesulfame, chloroimidate, imipenem, flumethrin, biphenyl Pyrethroid, cyhalothrin, cyhalothrin, fenpropathrin, fluvalerate, flumethrin, fluvalinate, bifenthrin, bifenyl ester, Phenylthiocarb, aldicarb, butanone, chlorpyrifos, anti-insect, long-acting, benomyl, chlorhexidine, carbofuran, butyl thiocarb, fast-breaking, converse , worms, monomethyl hydrazine, acaricidal, amitraz, chlorpyrifos, benzyl benzoate, bromo oxime ester, butyl fluoro ester, guanidine, fluoranthene, flubenzuron, liuyangmycin , echinomycin, sulphate, acaricidin, liuyangmycin, ar Bacteriocin, doramectin, eplenomycin, ivermectin, serramycin, moxidectin, pyrethrin, nicotine, matrine, azadirachtin, rotenone, pyridoxamine, Anthrone, oxazolidine, tetrazine, alkyne, thiazolone, spirodecyl ester, pyridoxine, acaricidal ester, ketone, hydrazine;

所述的溴代六氢茚酮类化合物I在所述杀螨组合物中的总的质量百分含量是1％-90％； The total mass percentage of the brominated hexahydroindanone compound I in the acaricidal composition is from 1% to 90%;

所述的溴代六氢茚酮类化合物I与所述商品杀螨剂的比例为质量百分比1％∶99％到99％∶1％；The ratio of the brominated hexahydroindanone compound I to the commercial acaricide is 1% by mass: 99% to 99%: 1% by mass;

所述杀螨组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；The dosage form processed by the acaricidal composition is selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble thickener, poisonous valley, block bait, granular Bait, flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, hot aerosol ,cold spray, aerosol, solid/liquid mixture, liquid/liquid mixture, solid/solid mixture, lacquer, granule, trace powder, oil suspension, oil dispersible powder, thick rubber Agent, pouring agent, seed coating agent, smear agent, film forming oil agent, ultra low volume liquid agent, steam release agent;

所述杀螨组合物防治的螨害选自：螨害选自叶螨科、细须螨科、呋线螨、瘿螨科、红叶螨属、瘿螨科的害螨，这些害螨是世界性农业害螨、林业害螨、园艺害螨和卫生害螨；The pest control of the acaricidal composition is selected from the group consisting of: the pest is selected from the group consisting of the leaf family, the genus, the genus, the genus, the genus, the genus, the cockroach, and the cockroach is the world agriculture. Hazards, forest pests, horticultural pests and health hazards;

所述杀螨组合物用于防治的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。The plant for controlling the acaricidal composition is selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, pea, broad bean, pea, mung bean, adzuki bean, cotton, sericulture, peanut, Rape, sesame, sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, rape, onion , garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

G.本发明的溴代六氢茚酮类化合物I的杀菌活性测定：G. Determination of bactericidal activity of the brominated hexahydroindanone compound I of the present invention:

本发明的溴代六氢茚酮类化合物I的杀菌或抑菌活性采用菌体生长率测定法，具体步骤为：取1.8毫克样品溶解在2滴N,N-二甲基甲酰胺中，即DMF中，然后用含有一定量吐温20乳化剂的水溶液稀释至500微克/毫升的药剂，将供试药剂在无菌条件下各吸取1毫升于培养皿内，再分别加入9毫升PDA培养基，摇匀后制成50微克/毫升含药平板，以添加1毫升灭菌水的平板做空白对照，用直径4毫米的打孔器沿菌丝外缘切取菌盘，移至含药平板上，呈等边三角形摆放，每处理重复3次，将培养皿放在24±1摄氏度恒温培养箱内培养，待对照菌落直径扩展到2-3厘米后调查各处理菌盘扩展直径，求平均值，与空白对照比较计算相对抑菌率，供试菌种为我国农业生产中田间实际发生的大部分典型植物病原菌的种属，其代号和名称如下：AS：番茄早疫病菌，其拉丁名为：Alternaria solani、BC：黄瓜灰霉病菌，其拉丁名为：Botrytis cinerea、CA：花生褐斑病菌，其拉丁名为：Cercospora arachidicola、GZ：小麦赤霉病菌，其拉丁名 为：Gibberella zeae、PI：马铃薯晚疫病菌，其拉丁名为：Phytophthora infestans(Mont.)de Bary、PP：苹果轮纹病菌，其拉丁名为：Physalospora piricola、PS：水稻纹枯病菌，其拉丁名为：Pellicularia sasakii、RC：禾谷丝核菌，其拉丁名为：Rhizoctonia cerealis、SS：油菜菌核病菌，其拉丁名为：Sclerotinia sclerotiorum。The bactericidal or bacteriostatic activity of the brominated hexahydroindanone compound I of the present invention is determined by a cell growth rate measurement method, and the specific procedure is as follows: a 1.8 mg sample is dissolved in 2 drops of N,N-dimethylformamide, that is, In DMF, then dilute to 500 μg/ml of the drug with an aqueous solution containing a certain amount of Tween 20 emulsifier, and absorb 1 ml of the test agent under sterile conditions into the culture dish, and then add 9 ml of PDA medium separately. Shake well to make a 50 μg/ml drug-containing plate, add 1 ml of sterilized water plate as a blank control, cut the fungus disc along the outer edge of the hyphae with a 4 mm diameter puncher, and transfer to the drug-containing plate. Placed in an equilateral triangle, repeating 3 times for each treatment, and cultivating the culture dish in a constant temperature incubator at 24±1 °C. After the diameter of the control colony is extended to 2-3 cm, investigate the expanded diameter of each treated disk and average The relative inhibition rate was calculated by comparison with the blank control. The tested strains were the species of most typical plant pathogens actually occurring in the field of agricultural production in China. The codes and names are as follows: AS: tomato early blight, its Latin name For: Alternaria solani, B C: Cucumber gray mold, its Latin name: Botrytis cinerea, CA: peanut brown spot disease, its Latin name: Cercospora arachidicola, GZ: wheat scab, its Latin name For: Gibberella zeae, PI: Phytophthora infestans, Latin name: Phytophthora infestans (Mont.) de Bary, PP: Apple ring rot, its Latin name: Physalospora piricola, PS: Rhizoctonia solani, its Latin name: Pellicularia sasakii, RC: Rhizoctonia cereal, its Latin name: Rhizoctonia cerealis, SS: Sclerotinia sclerotiorum, its Latin name: Sclerotinia sclerotiorum.

H.本发明的溴代六氢茚酮类化合物I对蚜虫毒杀活性的测定：H. Determination of the aphid toxicity activity of the bromo hexahydroindolone compound I of the present invention:

本发明的溴代六氢茚酮类化合物I对蚜虫毒杀活性的测定采用浸渍法，蚕豆蚜为室内饲养的正常种群，拉丁名为Aphis laburni Kaltenbach(ALK)；称取供试化合物2.5毫克于烧杯中，滴加1滴N,N-二甲基甲酰胺，即DMF，加5毫升丙酮振荡溶解样本，再加入有吐温80的水配成200微克/毫升的待测溶液；将带有至少30头蚕豆蚜的供试蚕豆植株从盆中剪下，在各待测药液中浸渍5秒钟，取出轻轻甩掉多余的药液，插在已经被水饱和的海绵上保湿，待药液自然风干后用玻璃罩罩上，玻璃罩上端的开口用纱布封口以防蚜虫逃逸，在培养室内饲养72小时后检查蚜虫死亡状况，标准为：以试虫能爬行或能站立或六条腿能剧烈运动视为活虫；以清水为对照计算校正死亡率。The brominated hexahydroindanone compound I of the present invention is used for the determination of aphid toxicity by using a dipping method, the broad bean meal is a normal population raised indoors, the Latin name is Aphis laburni Kaltenbach (ALK); the test compound is weighed 2.5 mg. In the beaker, add 1 drop of N,N-dimethylformamide, ie DMF, add 5 ml of acetone to dissolve the sample, then add water with Tween 80 to prepare 200 μg/ml of the solution to be tested; At least 30 tested broad bean plants were cut from the pots, immersed in each test solution for 5 seconds, removed and gently licked off the excess liquid, and immersed in a sponge that had been saturated with water, and hydrated. The liquid is naturally air-dried and covered with a glass cover. The opening at the upper end of the glass cover is sealed with gauze to prevent the mites from escaping. The locust death is checked after 72 hours in the culture room. The standard is: the test worm can crawl or stand or six legs. Strenuous exercise can be regarded as live insects; corrected water is used as a control to correct mortality.

I.本发明的溴代六氢茚酮类化合物I的诱导抗病活性测定：I. Determination of the induced disease resistance activity of the bromohexamidine compound I of the present invention:

本发明的溴代六氢茚酮类化合物I诱导烟草抗烟草花叶病毒活性的筛选方法如下，烟草花叶病毒简写为TMV：The screening method for inducing tobacco against tobacco mosaic virus activity by the bromo hexahydroindanone compound I of the present invention is as follows. The tobacco mosaic virus is abbreviated as TMV:

(1).阳性对照植物激活剂：选择质量纯度纯度大于99.5％的噻酰菌胺为阳性对照的植物激活剂；S-甲基苯并[1,2,3]噻二唑-7-硫代羧酸酯简写为BTH；(1). Positive control plant activator: select a plant activator with a purity purity greater than 99.5% of thiazide as a positive control; S-methylbenzo[1,2,3]thiadiazole-7-sulfur The carboxylic acid ester is abbreviated as BTH;

(2).溴代六氢茚酮类化合物I的诱导烟草抗TMV活性的筛选方法：离体直接抗病毒活性的测定采用半叶法进行；活体诱导是将苗龄一致的普通烟，3盆为一组，分别于接种前7d前处理过的烟苗，处理方式包括：喷施供试化合物溶液2到3次，每次10毫升，或土壤处理，每次10毫升，测定浓度为50微克/毫升，第7天于新长出的烟叶上摩擦接种TMV，将烟苗置于其生长适宜温度及光照下培养3天后，检查发病情况，综合病斑数目按下式计算出供试化合物对TMV的诱导抗病毒效果，每一处理设3次重复，空白对照和标准药剂对照分别选择水和BTH：(2) Screening method for inducing tobacco anti-TMV activity of bromo hexahydroindanone I: The determination of direct antiviral activity in vitro is carried out by the half-leaf method; the living induction is a common smoke with the same age of seedlings, 3 pots. For a group of tobacco seedlings treated before 7 days before inoculation, the treatment methods include: spraying the test compound solution 2 to 3 times, each time 10 ml, or soil treatment, 10 ml each time, the concentration is 50 μg. /ml, on the 7th day, the TMV was inoculated on the newly grown tobacco leaves, and the seedlings were placed in the growth temperature and light for 3 days. The disease was examined and the number of lesions was calculated according to the following formula. The antiviral effect of TMV was induced by three replicates per treatment, and the blank and standard drug controls were selected for water and BTH, respectively:

其中，R为供试化合物对烟草抗TMV的诱导效果，单位：％；CK为清水对照叶片的平均枯斑数，单位：个；I为经供试化合物诱导处理后叶片的平均枯斑数，单位：个；Wherein, R is the inducing effect of the test compound on tobacco anti-TMV, unit: %; CK is the average number of dead spots of the control leaves of clear water, unit: one; I is the average number of leaves of the leaves after induction treatment by the test compound, unit: PCS;

除了进行上述诱导活性的测定外，同时进行目标化合物I的抗TMV治疗活性、 钝化活性和保护活性的测定。In addition to performing the above assay for inducing activity, the anti-TMV therapeutic activity of the target compound I is simultaneously performed, Determination of passivation activity and protective activity.

本发明的有益效果是：对溴代六氢茚酮类化合物I进行了先导优化，并对合成的新化合物进行杀虫活性、抑菌活性、抗病毒活性的筛选。The invention has the beneficial effects that the brominated hexahydroindanone compound I is subjected to pilot optimization, and the synthetic new compound is screened for insecticidal activity, antibacterial activity and antiviral activity.

本发明通过特定制备和生物活性测定实施例更加具体说明溴代六氢茚酮类化合物I的合成与生物活性及应用，所述实施例仅用于具体说明本发明而非限制本发明，尤其是生物活性仅是举例说明，而非限制本专利，具体实施方式如下：The present invention more specifically illustrates the synthesis and biological activity and application of the bromo hexahydroindanone compound I by specific preparation and biological activity assay examples, which are intended to specifically illustrate the invention and not to limit the invention, especially Biological activity is merely illustrative and not limiting, and the specific embodiments are as follows:

实施例1Example 1

化合物III的制备：Preparation of Compound III:

将3.2毫摩尔的化合物II加入100毫升两口瓶中，抽真空，注入氮气保护，然后加入25毫升干燥的四氢呋喃溶液，冰盐浴下向反应瓶中缓慢滴加3.5毫摩尔乙烯基溴化镁，滴加完毕后，冰盐浴搅拌20分钟，撤去冰浴，室温搅拌2小时，反应完全后，反应液加入20毫升饱和碳酸氢钠溶液淬灭，乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，残余物经200～300目硅胶柱层析纯化得化合物III，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝6:1的混合液；用所得纯品计算收率，收率70％；化合物III的理化参数和结构参数见表1；化合物III制备的量和反应容器的体积按相应比例扩大或缩小。3.2 mmol of Compound II was added to a 100 ml two-necked flask, vacuumed, and protected with nitrogen. Then, 25 ml of a dry tetrahydrofuran solution was added, and 3.5 mmol of vinylmagnesium bromide was slowly added dropwise to the reaction flask under ice salt bath. After the completion of the dropwise addition, the ice salt bath was stirred for 20 minutes, the ice bath was removed, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction mixture was quenched with 20 ml of saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The ethyl acetate phase was washed with saturated sodium bicarbonate and saturated sodium chloride, and dried over anhydrous magnesium sulfate, filtered, evaporated, evaporated, evaporated. III, the eluent is a mixture of petroleum ether = 6:1 in a volume ratio of ethyl acetate: 60-90 degrees Celsius; the yield is calculated from the obtained pure product, the yield is 70%; the physical and chemical parameters and structural parameters of the compound III See Table 1; the amount of Compound III prepared and the volume of the reaction vessel are expanded or reduced in proportions.

实施例2Example 2

化合物IV的制备：Preparation of Compound IV:

将0.76毫摩尔化合物III溶于20毫升干燥的四氢呋喃溶液中，然后加入2.27毫摩尔硼氢化钠，冰浴下缓慢滴加3.04毫摩尔三氟化硼***的四氢呋喃溶液，滴加完毕后，冰浴搅拌15分钟再撤去冰浴，然后室温搅拌2小时，停止反应后在冰浴下向反应瓶中缓慢滴加4.6毫摩尔的Jones试剂，滴加完毕后在室温继续搅拌2小时，反应完全后，加入20毫升水，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，乙酸乙酯相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物IV，洗脱剂体积比为乙酸乙酯:60～90摄氏度馏分的石油醚＝4:1的混合液；用所得纯品计算收率，收率45％；化合物IV的理化参数和结构参数见表1；化合物IV制备的量和反应容器的体积按相应比例扩大或缩小。0.76 mmol of the compound III was dissolved in 20 ml of a dry tetrahydrofuran solution, then 2.27 mmol of sodium borohydride was added, and a solution of 3.04 mmol of boron trifluoride etherate in tetrahydrofuran was slowly added dropwise on an ice bath. After stirring for 15 minutes, the ice bath was removed, and then stirred at room temperature for 2 hours. After the reaction was stopped, 4.6 mmol of Jones reagent was slowly added dropwise to the reaction flask under ice bath. After the completion of the dropwise addition, stirring was continued for 2 hours at room temperature. After the reaction was completed, After adding 20 ml of water and extracting with ethyl acetate, the ethyl acetate layer was separated, and the ethyl acetate phase was washed again with saturated sodium hydrogen carbonate and saturated sodium chloride. After concentrating and removing the solvent under reduced pressure, the residue was purified by silica gel column chromatography from 200 to 300 mesh to obtain compound IV. The volume ratio of eluent to ethyl acetate: petroleum ether of 60 to 90 ° C = 4:1 mixture The yield was calculated by the obtained pure product, and the yield was 45%; the physical and chemical parameters and structural parameters of the compound IV are shown in Table 1; the amount of the compound IV and the volume of the reaction vessel were expanded or reduced according to the corresponding ratio.

实施例3Example 3

化合物V的制备：Preparation of Compound V:

将1.9毫摩尔化合物IV溶于15毫升体积比为四氢呋喃与水为10:1的混合溶液中， 冰浴下向反应液中分批加入2毫摩尔硼氢化钠，加入完毕后，撤去冰浴，室温搅拌1小时，反应完全后加入15毫升饱和碳酸氢钠淬灭，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，乙酸乙酯相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物V，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝3:1的混合液；用所得纯品计算收率，收率68％；化合物V的理化参数和结构参数见表1；化合物V制备的量和反应容器的体积按相应比例扩大或缩小。1.9 mmol of compound IV was dissolved in 15 ml of a mixed solution of tetrahydrofuran and water in a volume ratio of 10:1. 2 mM sodium borohydride was added portionwise to the reaction mixture under ice-cooling. After the addition was completed, the ice bath was removed, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the mixture was stirred and evaporated with ethyl acetate. The ethyl acetate layer was taken, and the ethyl acetate phase was washed again with saturated sodium bicarbonate and saturated sodium chloride, and the ethyl acetate phase was dried over anhydrous magnesium sulfate, filtered, evaporated and evaporated. The compound V is purified by silica gel column chromatography from 200 to 300 mesh, and the eluent is a mixture of petroleum ether = 3:1 in a volume ratio of ethyl acetate: 60-90 degrees Celsius; the yield is obtained by using the obtained pure product. 68%; physical and chemical parameters and structural parameters of compound V are shown in Table 1; the amount of compound V prepared and the volume of the reaction vessel are enlarged or reduced according to the corresponding ratio.

实施例4Example 4

化合物VI的制备：Preparation of Compound VI:

将3.5毫摩尔化合物V溶于25毫升重蒸后的二氯甲烷中，抽真空，注入氮气保护，冰浴下向反应瓶中加入14毫摩尔的三乙胺，然后缓慢滴加酰氯R¹COCl，滴加完毕后，撤去冰浴，室温搅拌过夜，反应完全后加入20毫升饱和碳酸氢钠溶液萃取，分出二氯甲烷层，二氯甲烷相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，二氯甲烷相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物VI，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝8:1的混合液；用所得纯品计算收率，收率90％；化合物VI的理化参数和结构参数见表1；化合物VI制备的量和反应容器的体积按相应比例扩大或缩小。3.5 mmol of compound V was dissolved in 25 ml of re-distilled dichloromethane, vacuumed, and protected with nitrogen. 14 mmol of triethylamine was added to the reaction flask under ice bath, and then acid chloride R ¹ COCl was slowly added dropwise. After the dropwise addition is completed, the ice bath is removed, and the mixture is stirred at room temperature overnight. After the reaction is completed, the mixture is extracted with 20 ml of saturated sodium hydrogencarbonate solution, and the dichloromethane layer is separated, and the dichloromethane phase is further saturated sodium bicarbonate and saturated sodium chloride. After washing once, the dichloromethane phase was dried over anhydrous magnesium sulfate, suction filtered, concentrated, and then evaporated to remove the solvent, and the residue was purified by silica gel column chromatography on 200-300 mesh to afford compound VI. Ester: a mixture of petroleum ether = 8:1 of 60-90 ° C; the yield is calculated by the obtained pure product, the yield is 90%; the physical and chemical parameters and structural parameters of the compound VI are shown in Table 1; the amount and reaction of the compound VI are prepared. The volume of the container is enlarged or reduced in proportion to the corresponding ratio.

实施例5Example 5

化合物VII的制备：Preparation of Compound VII:

将0.7毫摩尔化合物VI溶于6毫升甲磺酸中，然后加入0.01毫摩尔五氧化二磷与35-40摄氏度加热反应6小时，反应完全后加入20毫升水，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，乙酸乙酯相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物VII，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝8:1的混合液；用所得纯品计算收率，收率60％；化合物VII的理化参数和结构参数见表1；化合物VII制备的量和反应容器的体积按相应比例扩大或缩小。0.7 mmol of compound VI was dissolved in 6 ml of methanesulfonic acid, and then 0.01 mmol of phosphorus pentoxide was added and heated at 35-40 ° C for 6 hours. After the reaction was completed, 20 ml of water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer and the ethyl acetate phase were washed again with saturated sodium hydrogen sulfate and saturated sodium chloride, and the ethyl acetate phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The compound VII was purified by silica gel column chromatography on ~300 mesh, and the eluent was a mixture of petroleum ether = 8:1 in a volume ratio of ethyl acetate: 60-90 ° C; the yield was calculated from the obtained pure product, yield 60 %; physical and chemical parameters and structural parameters of compound VII are shown in Table 1; the amount of compound VII prepared and the volume of the reaction vessel are expanded or reduced in corresponding proportions.

实施例6Example 6

化合物I的制备：Preparation of Compound I:

当R¹为Ph、X¹为Br、X²为H时，化合物I的制备方法如下：When R ¹ is Ph, X ¹ is Br, and X ² is H, the preparation method of Compound I is as follows:

将7毫摩尔化合物VII溶于干燥的四氯化碳中，然后依次加入7.7毫摩尔N-溴代丁二酰亚胺、0.07毫摩尔偶氮二异丁腈，于50摄氏度加热反应过夜，反应完全后，抽滤，浓缩，减压除去溶剂，残余物经200～300目硅胶柱层析纯化得化合物I，洗脱剂 为体积比为乙酸乙酯:60～90摄氏度馏分的石油醚＝10:1的混合液；用所得纯品计算收率，收率50％；用N-氯代丁二酰亚胺替代N-溴代丁二酰亚胺可以制备相应的氯代物；化合物I的理化参数和结构参数见表1；化合物I制备的量和反应容器的体积按相应比例扩大或缩小。7 mmol of the compound VII was dissolved in dry carbon tetrachloride, and then 7.7 mmol of N-bromosuccinimide and 0.07 mmol of azobisisobutyronitrile were sequentially added, and the reaction was heated at 50 ° C overnight. After completion, suction filtration, concentration, solvent removal under reduced pressure, and the residue was purified by silica gel column chromatography from 200 to 300 mesh to afford compound I, eluent a mixture of petroleum ether = 10:1 in a volume ratio of ethyl acetate: 60-90 ° C; the yield is calculated by the obtained pure product, the yield is 50%; N-chlorosuccinimide is substituted for N- The corresponding chloroforms can be prepared from bromosuccinimide; the physical and chemical parameters and structural parameters of the compound I are shown in Table 1; the amount of the compound I prepared and the volume of the reaction vessel are enlarged or reduced according to the corresponding ratio.

当R¹为Ph、X¹为H、X²为Br时，化合物I的制备方法如下：When R ¹ is Ph, X ¹ is H, and X ² is Br, the preparation method of Compound I is as follows:

将0.4毫摩尔化合物VII溶于15毫升干燥的乙腈中，然后依次加入0.44毫摩尔N-溴代丁二酰亚胺，0.02毫摩三氟甲磺酸三甲基硅酯，加入完毕后，室温搅拌过夜，反应完全后加入20毫升饱和碳酸氢钠溶液萃取，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相再用饱和碳酸氢钠和饱和氯化钠各洗涤一遍，乙酸乙酯相经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂后，残余物经200～300目硅胶柱层析纯化得化合物I，洗脱剂为体积比是乙酸乙酯:60～90摄氏度馏分的石油醚＝10:1的混合液；用所得纯品计算收率，收率46％；用N-氯代丁二酰亚胺替代N-溴代丁二酰亚胺可以制备相应的氯代物；化合物I的理化参数和结构参数见表1；化合物I制备的量和反应容器的体积按相应比例扩大或缩小。0.4 mmol of compound VII was dissolved in 15 ml of dry acetonitrile, followed by the addition of 0.44 mmol of N-bromosuccinimide, 0.02 mmol of trimethylsilyl trifluoromethanesulfonate. After stirring overnight, the reaction was completed, and then extracted with 20 ml of saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was separated, and the ethyl acetate phase was washed again with saturated sodium hydrogen carbonate and saturated sodium chloride. The ester phase is dried over anhydrous magnesium sulfate, filtered, concentrated, and evaporated, evaporated, evaporated. a mixture of petroleum ether = 10:1 of Celsius fraction; the yield is calculated by the obtained pure product, the yield is 46%; and N-chlorosuccinimide can be substituted for N-bromosuccinimide to prepare corresponding Chlorinated compounds; physical and chemical parameters and structural parameters of compound I are shown in Table 1; the amount of compound I prepared and the volume of the reaction vessel are expanded or reduced in corresponding proportions.

实施例7Example 7

本发明的溴代六氢茚酮类化合物I的抑菌活性测定结果：The bacteriostatic activity of the bromohexahydroinone compound I of the present invention is measured:

本发明测试的常见植物病原真菌的代号和名称如下：AS：番茄早疫病菌，其拉丁名为：Alternaria solani、BC：黄瓜灰霉病菌，其拉丁名为：Botrytis cinerea、CA：花生褐斑病菌，其拉丁名为：Cercospora arachidicola、GZ：小麦赤霉病菌，其拉丁名为：Gibberella zeae、PI：马铃薯晚疫病菌，其拉丁名为：Phytophthora infestans(Mont.)de Bary、PP：苹果轮纹病菌，其拉丁名为：Physalospora piricola、PS：水稻纹枯病菌，其拉丁名为：Pellicularia sasakii、RC：禾谷丝核菌，其拉丁名为：Rhizoctonia cerealis、SS：油菜菌核病菌，其拉丁名为：Sclerotinia sclerotiorum，这些菌种具有很好的代表性，能够代表农业生产中田间发生的大部分病原菌的种属。The code and name of the common phytopathogenic fungi tested in the present invention are as follows: AS: tomato Phytophthora infestans, Latin name: Alternaria solani, BC: Botrytis cinerea, Latin name: Botrytis cinerea, CA: Peanut brown spot disease Its Latin name: Cercospora arachidicola, GZ: Fusarium graminearum, its Latin name: Gibberella zeae, PI: Phytophthora infestans, Latin name: Phytophthora infestans (Mont.) de Bary, PP: Apple wheel The pathogen, its Latin name: Physalospora piricola, PS: Rhizoctonia solani, its Latin name: Pellicularia sasakii, RC: Rhizoctonia cereal, its Latin name: Rhizoctonia cerealis, SS: Sclerotinia sclerotiorum, its The Latin name is: Sclerotinia sclerotiorum, which is well-represented and represents the species of most pathogens that occur in the field of agricultural production.

菌体生长率法测定结果见表2，表2表明，在50微克/毫升时，本发明合成的所有溴代六氢茚酮类化合物I均有不同程度的杀菌活性，本发明的大部分溴代六氢茚酮类化合物I具有较好的杀菌活性；对番茄早疫病菌而言，本发明的所有化合物的抑菌活性均在35％以上，其中化合物zyj05-186的抑菌活性最高，为28.00％。对黄瓜灰霉病菌而言，本发明的所有化合物的抑菌活性均在28％以上，其中化合物zyj05-172的抑菌活性最高，为61.85％。对花生褐斑病菌而言，本发明的所有化合物的抑菌活性均在30％以上，其中化合物zyj05-186的抑菌活性最高，为46.67％。对小麦赤霉病菌而言，本发明的所有化合物的抑菌活性均在30％以上，其中化合物zyj05-154的抑菌活性最高， 为58.49％。对马铃薯晚疫病菌而言，本发明的所有化合物的抑菌活性均在20％以上，其中化合物zyj05-171的抑菌活性最高，为39.18.00％。对苹果轮纹病菌而言，本发明的化合物zyj05-154、zyj05-155、zyj05-157、zyj05-171、zyj05-172的抑菌活性均在28％以上，其中化合物zyj05-157的抑菌活性最高，为39.15％。对水稻纹枯病菌而言，本发明的所有化合物的抑菌活性均在27％以上，其中化合物zyj05-172的抑菌活性最高，为40.29％。对禾谷丝核菌而言，本发明的所有化合物的抑菌活性均在20％以上，其中化合物zyj05-186的抑菌活性最高，为42.31％。对油菜菌核病菌而言，本发明的所有化合物的抑菌活性均在60％以上，其中化合物zyj05-186的抑菌活性最高，为86.96％。The results of the cell growth rate assay are shown in Table 2. Table 2 shows that at 50 μg/ml, all of the brominated hexahydroindolone compounds I synthesized in the present invention have different degrees of bactericidal activity, and most of the bromine of the present invention. The hexahydroindanone compound I has better bactericidal activity; for the tomato Phytophthora infestans, the antibacterial activity of all the compounds of the invention is above 35%, and the compound zyj05-186 has the highest antibacterial activity, 28.00%. For Cucumber gray mold, all the compounds of the present invention have an antibacterial activity of more than 28%, and the compound zyj05-172 has the highest antibacterial activity of 61.85%. For P. aureus, all the compounds of the present invention have an antibacterial activity of more than 30%, and the compound zyj05-186 has the highest antibacterial activity of 46.67%. For the Fusarium graminearum, the antibacterial activity of all the compounds of the present invention is above 30%, and the compound zyj05-154 has the highest antibacterial activity. It is 58.49%. For the Phytophthora infestans, all the compounds of the present invention have an antibacterial activity of more than 20%, and the compound zyj05-171 has the highest antibacterial activity of 39.18.00%. For the apple ring rot, the antibacterial activities of the compounds zyj05-154, zyj05-155, zyj05-157, zyj05-171 and zyj05-172 of the present invention are all above 28%, wherein the bacteriostatic activity of the compound zyj05-157 The highest is 39.15%. For the Rhizoctonia solani, all the compounds of the present invention have an antibacterial activity of more than 27%, and the compound zyj05-172 has the highest antibacterial activity of 40.29%. For Rhizoctonia cerealis, all the compounds of the present invention have an antibacterial activity of more than 20%, and the compound zyj05-186 has the highest antibacterial activity of 42.31%. For Sclerotinia sclerotiorum, all the compounds of the present invention have an antibacterial activity of more than 60%, and the compound zyj05-186 has the highest antibacterial activity of 86.96%.

实施例8Example 8

本发明的溴代六氢茚酮类化合物I杀虫活性：The insecticidal activity of the brominated hexahydroindanone compound I of the present invention:

溴代六氢茚酮类化合物I的杀虫活性测定结果见表3，表3可见：本发明的溴代六氢茚酮类化合物I具有较好的杀虫活性，在供试药剂浓度为100毫克/升时，观察作用72小时后，本发明的溴代六氢茚酮类化合物I对蚜虫有较好的毒杀作用，本发明的所有化合物的杀虫活性均在25％以上；其中化合物zyj05-176的杀虫活性最高，为46.4％。The results of the insecticidal activity determination of the bromo hexahydroindanone compound I are shown in Table 3. Table 3 shows that the brominated hexahydroindanone compound I of the present invention has good insecticidal activity, and the concentration of the test agent is 100. At mg/L, after 72 hours of observation, the bromo hexahydroindolone compound I of the present invention has a good toxic effect on aphids, and all the compounds of the present invention have an insecticidal activity of more than 25%; Zyj05-176 has the highest insecticidal activity of 46.4%.

本发明的氯代异噻唑新烟碱类化合物I还对直翅目、等翅目、半翅目、同翅目、缨翅目、鞘翅目、鳞翅目、脉翅目、双翅目、膜翅目和蜱螨目的农业和林业以及园艺植物害虫害螨具有很好的杀虫活性。The chloroisothiazole neonicotinoid compound I of the present invention is also directed to Orthoptera, Isoptera, Hemiptera, Homoptera, Thysanoptera, Coleoptera, Lepidoptera, Hymenoptera, Diptera, Hymenoptera and eye-catching agriculture and forestry as well as horticultural plant pests have good insecticidal activity.

实施例9Example 9

本发明的溴代六氢茚酮类化合物I的抗TMV活性：Anti-TMV activity of the bromo hexahydroindanone compound I of the present invention:

溴代六氢茚酮类化合物I抗TMV活性的测定结果见表4，表4表明，本发明的溴代六氢茚酮类化合物I具有较好的抗TMV活性。就保钝化性而言，本发明的所有化合物的钝化活性均高于30％，其中化合物zyj05-171的钝化活性最高，为49.90％。就诱导活性而言，本发明的所有化合物的钝化活性均高于20％，其中化合物zyj05-186的钝化活性最高，为59.99％。The results of the measurement of the anti-TMV activity of the bromo hexahydroindanone compound I are shown in Table 4. Table 4 shows that the bromo hexahydroindanone compound I of the present invention has a good anti-TMV activity. In terms of passivation, the passivation activity of all the compounds of the present invention was higher than 30%, and the compound zyj05-171 had the highest passivation activity of 49.90%. In terms of inducing activity, the passivation activity of all the compounds of the present invention was higher than 20%, and the compound zyj05-186 had the highest passivation activity of 59.99%.

本发明的所有溴代六氢茚酮类化合物I还对水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒病、建兰环斑病毒的农业和林业以及园艺植物病毒病害具有很好的抗病毒活性。All of the bromo hexahydroindolone compounds I of the present invention are also resistant to rice dwarf disease, yellow dwarf disease, stripe leaf blight, tomato fern leaf virus disease, pepper mosaic virus disease, tobacco vein necrosis virus disease, corn dwarf flower Leaf disease, cauliflower mosaic virus, citrus virus disease, broccoli virus disease, Jianlan ring spot virus agriculture and forestry, and horticultural plant virus disease have good antiviral activity.

实施例10Example 10

本发明的溴代六氢茚酮类化合物I与杀虫剂组合在防治农业和林业以及园艺植物虫害中的应用： The use of the brominated hexahydroindolone compound I of the present invention in combination with an insecticide for controlling agricultural and forestry and horticultural plant pests:

本发明的所有溴代六氢茚酮类化合物I与商品杀虫剂中的任意一种或两种组合形成杀虫组合物用于防治农业和林业以及园艺植物虫害，所述商品杀虫剂选自：毒死蜱、地亚哝、啶虫脒、甲氨基阿维菌素、弥拜菌素、阿维菌素、多杀菌素、氰戊菊酯、高效氰戊菊酯、氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、Beta-氟氯氰菊酯、Lambda-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、联苯菊酯、氯菊酯、醚菊酯、氟氯苯菊酯、氯氟胺氰戊菊酯、吡虫啉、烯啶虫胺、氯噻啉、噻虫啉、噻虫嗪、噻虫胺、呋虫胺、可尼丁、达特南、除虫脲、灭幼脲、伏虫隆、除虫隆、氟铃脲、氟虫脲、啶虫隆、虱螨脲、毒虫脲、氟幼脲、Noviflumuron即多氟脲，其CAS号为121451-02-3、氟螨脲、Novaluron即双苯氟脲、氟啶脲、Bay sir 6874即{1-[(3.5-二氯-4)4-硝基苯氧基苯基3-3-(2-氯苯)-脲}、Bay SIR-8514即[1-(4-三氟甲氧基苯基)-3-(2-氯苯)-脲]、嗪虫脲、Bistrifluron即双三氟虫脲、呋喃虫酰肼、虫酰肼、氯虫酰肼、甲氧虫酰肼、环虫酰肼、乐果、氧化乐果、敌敌畏、乙酰甲胺磷、***磷、喹硫磷、哒嗪硫磷、氯唑磷、叶蝉散、西维因、抗蚜威、速灭威、异丙威、杀螟丹、仲丁威、叶飞散、甲萘威、丙硫克百威、丁硫克百威、杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、丁烯氟虫腈、***锡、噻嗪酮、灭线磷、氟虫腈、杀虫单、杀虫双、氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、唑虫酰胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素；本发明的溴代六氢茚酮类化合物I在所述杀虫组合物中的质量百分含量是1％-90％，本发明的溴代六氢茚酮类化合物I与前述商品杀虫剂的比例为质量百分比1％∶99％到99％∶1％；所述杀虫组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；所述杀虫组合物防治的植物虫害选自：红蜘蛛、东亚飞蝗、云斑车蝗、中华稻蝗、日本黄脊蝗、单刺蝼蛄、东方蝼蛄、稻蓟马、烟蓟马、温室蓟马、稻管蓟马、麦简管蓟马、温室白粉虱、烟粉虱、黑尾叶蝉、大青叶蝉、棉叶蝉、斑衣蜡蝉、褐飞虱、白背飞虱、灰飞虱、甘蔗扁角飞虱、棉蚜、麦二叉蚜、麦长管蚜、桃蚜、高粱蚜、萝卜蚜、吹绵蚧、桑盾蚧、矢尖盾蚧、梨圆蚧、白蜡虫、红蜡蚧、朝鲜球坚蚧、梨网蝽、香蕉网蝽、细角花蝽、微小花蝽、针缘蝽、稻蛛缘蝽、稻褐蝽、稻黑蝽、稻绿蝽、绿盲蝽、苜蓿盲蝽、中黑盲蝽、大草蛉、丽草蛉、中华草蛉、谷蛾、衣蛾、黄刺蛾、褐 刺蛾、扁刺蛾、麦蛾、棉红铃虫、甘薯麦蛾、小菜蛾、桃小食心虫、大豆食心虫、桃小食心虫、苹果顶梢卷叶蛾、褐带长卷叶蛾、拟小黄卷叶蛾、二化螟、豆荚螟、玉米螟、三化螟、菜螟、稻纵卷叶螟、条螟、棉卷叶野螟、桃蛀螟、黏虫、斜纹夜蛾、稻螟蛉、棉小造桥虫、甜菜夜蛾、大螟、棉铃虫、鼎点金刚钻、小地老虎、大地老虎、黄地老虎、盗毒蛾、舞毒蛾、甘薯天蛾、豆天蛾、直纹稻弄蝶、隐纹谷弄蝶、柑橘凤蝶、玉带凤蝶、菜粉蝶、苎麻赤蛱蝶、苎麻黄蛱蝶、豆芫菁、金星步甲、皱鞘步甲、麦穗步甲、沟金针虫、细胸金针虫、谷斑皮蠹、黑皮蠹、柑橘小吉丁虫、金缘吉丁虫、黄粉虫、黑粉虫、赤拟谷盗、杂拟谷盗、铜绿异丽金龟、暗黑金龟、华北大黑鳃金龟、桑天牛、星天牛、橘褐天牛、桃红颈天牛、大猿叶虫、小猿叶虫、黄守瓜、黄曲条跳甲、绿豆象、豌豆象、蚕豆象、玉米象、米象、小麦叶蜂、梨实蜂、黄带姬蜂、黏虫白星姬蜂、螟蛉悬茧姬蜂、棉铃虫齿唇姬蜂、螟黑点疣姬蜂、蚊、蝇、虻、麦红吸浆虫、麦黄吸浆虫、稻瘿蚊、柑橘大实蝇、瓜实蝇、麦叶灰潜蝇、美洲斑潜蝇、豆秆黑潜蝇、麦秆蝇、种蝇、葱蝇、萝卜蝇、伞裙追寄蝇、玉米螟厉寄蝇、黏虫；所述杀虫组合物防治的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。All of the brominated hexahydroindanone compounds I of the present invention are combined with any one or both of the commercial insecticides to form a pesticidal composition for controlling agricultural and forestry and horticultural plant pests. From: chlorpyrifos, scorpion scorpion, acetamiprid, emamectin, milavirin, avermectin, spinosyn, fenvalerate, high-grade fenvalerate, cypermethrin, beta-cypermethrin, three Cyfluthrin, deltamethrin, fenpropathrin, Beta-cyfluthrin, Lambda-cyhalothrin, permethrin, permethrin, methrin, bifenthrin, permethrin, ether Pyrethroid, flumethrin, flufenacetate, imidacloprid, nitenpyram, chlorothiazol, thiacloprid, thiamethoxam, clothianidin, dinotefuran, cotinine, dart South, Diflubenzuron, Diflubenzuron, Fumaron, Buproron, Fluorochroma, Flufenuril, Azadron, Ureaplasma, Venom, Fluoride, Noviflumuron, Polyfluorourea, CAS No. Is 121451-02-3, fluoroquinone urea, Novaluron, ie, diphenylfluorourea, chlorfluazuron, Bay sir 6874, ie {1-[(3.5-dichloro-4) 4-nitrophenoxy Phenyl 3-3-(2-chlorophenyl)-urea}, Bay SIR-8514 is [1-(4-trifluoromethoxyphenyl)-3-(2-chlorophenyl)-urea], azine Insecture, Bistrifluron, ie, bistriazole, furanoyl hydrazide, tebufenozide, chlorfenapyr, methoxyfenhydrazide, chlorfenapyr, dimethoate, omethoate, dichlorvos, acephate, Triazophos, quetiapine, pyridazin, chlorpyrifos, scutellaria, carbaryl, carbaryl, acesulfame, isoprocarb, chlorpyrifos, zhongdingwei, yefeisan, methine Wei, propyl thiocarbamate, butyl thiocarbamate, chlorpyrifos, bromo oxime ester, thiazolone, oxazolidine, fluorenone, tetraoxazine, alkyne, butyl ether urea, pymetrozine, Spiroester, spirotetramat, spirotetramat, butene fipronil, triazole tin, buprofezin, phosphazone, fipronil, insecticidal, insecticidal, chlorantraniliprole, flubendiamide , fluocyanamide, cyanamide, oxazolamide, chlorfenapyr, pyrazinone, etoxazole, pyridoxamine, ketone, pyriproxyfen, emamectin; brominated hexahydrogen of the invention The mass percentage of the fluorenone compound I in the insecticidal composition is from 1% to 90%, and the brominated six of the present invention The ratio of the fluorenone compound I to the aforementioned commercial insecticide is 1% by mass: 99% to 99%: 1% by mass; the dosage form processed by the insecticidal composition is selected from the group consisting of a seed treatment emulsion, an aqueous emulsion, a microemulsion, Suspension emulsion, capsule suspension, water-soluble granule, fine granule, soluble concentrate, poisonous valley, block bait, granular bait, flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, Smoke cans, smoke candles, smoke tubes, smoke sticks, smoke sheets, smoke pills, gas generators, ointments, hot sprays, cold sprays, aerosols, solid/liquid mixed agents, liquid/liquid mixed agents , solid/solid mixed agent, lacquer, microgranule, trace powder, oil suspension, oil dispersible powder, thickener, pouring agent, seed coating agent, smear agent, film forming oil agent, ultra low volume liquid Agent and steam release agent; the plant pests controlled by the insecticidal composition are selected from the group consisting of: red spider, oriental fly, zebra, Chinese rice blast, Japanese yellow ridge, single locust, oriental carp, rice glutinous horse , smoky horses, greenhouse hummers, rice-tube hummers, wheat-striped hummers, greenhouse white meal, smoke虱, 黑尾叶蝉, 大青叶蝉, cotton leaf 蝉, spotted wax 蝉, brown planthopper, white-backed planthopper, gray planthopper, sugarcane striata, cotton aphid, wheat bifurcation, wheat long tube , peach aphid, sorghum, radish, sputum, sang shield, yam shield, pear scorpion, white wax insect, red wax scorpion, Korean ball scorpion, pear net 蝽, banana net 蝽, fine horn flower蝽, tiny flower buds, needle 蝽, rice spider 蝽, rice brown 蝽, rice black 蝽, rice green 蝽, green blind 蝽, 苜蓿 blind 蝽, middle black blind 大, big grass 蛉, 蛉草蛉, Chinese 蛉, moth, moth, yellow moth, brown Spiny moth, flat moth, wheat moth, cotton red bollworm, sweet potato moth, diamondback moth, peach small heartworm, soybean heartworm, peach small heartworm, apple top leaf curling moth, brown leaf curling moth, pseudo small yellow leaf moth, dichotomy螟, 豆, 螟, corn 螟, 三, 螟, rice leaf 螟, 螟, 棉 leaf wild 蛀螟, peach 蛀螟, sticky worm, Spodoptera litura, rice blast, cotton small bridge worm, beet Noctuidae, giant salamander, cotton bollworm, Dingdian diamond, small tiger, earth tiger, yellow tiger, poisonous moth, gypsy moth, sweet potato hawk moth, bean hawk moth, straight grain rice butterfly, cryptic valley butterfly, Citrus Swallowtail, Jade Butterfly, Cabbage Butterfly, Ramie Butterfly, Ramie Butterfly, Bean Phthalocyanine, Venus Carapace, Wrinkle-coating Armor, Wheat-Fly Armor, Ditch Golden Needle, Fine-necked Golden Needle, Grain Spot Pipi, black scorpion, citrus small jiding insect, Jinyuan jiding insect, yellow mealworm, black mealworm, red worm, snail, scorpion, scorpion, dark tortoise, black turtle, sang Tianniu, Xingtianniu, Orange-branched Beef, Peach-necked Beef, Big Leafhopper, Small Leafhopper, Yellow Stalk, Yellow Jumping armor, mung bean elephant, pea elephant, broad bean elephant, corn elephant, rice elephant, wheat leaf bee, pear bee, yellow belt wasp, sticky insect white star wasp, cockroach cockroach, cotton bollworm, larvae, Black spotted bee, mosquito, fly, cockroach, wheat red worm, wheat yellow worm, rice blast, citrus fruit fly, melon fly, larvae, larvae, larvae , wheat straw fly, fly, onion fly, radish fly, umbrella skirt chasing fly, corn scorpion fly, armyworm; the plant controlled by the insecticidal composition is selected from: rice, wheat, barley, oats, corn , sorghum, sweet potato, potato, cassava, soybean, pea, bean, pea, mung bean, adzuki bean, cotton, sericulture, peanut, rape, sesame, sunflower, sugar beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, Oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, rape, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables , bamboo shoots, hops, pepper, bananas, Papaya, orchids, bonsai.

实施例11Example 11

本发明的溴代六氢茚酮类化合物I与杀菌剂组合在防治农业和林业以及园艺植物病害中的应用：The use of the brominated hexahydroindolone compound I of the present invention in combination with a bactericide for controlling agricultural and forestry and horticultural plant diseases:

本发明的所有溴代六氢茚酮类化合物I与商品杀菌剂中的任意一种或两种组合形成杀菌组合物用于防治农业和林业以及园艺植物病害，所述商品杀菌剂选自：苯并噻二唑、噻酰菌胺，简写为TDL、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺，其英文通用名为：isotianil、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、氟酰胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、呋吡菌胺、吡噻菌胺、双炔酰菌胺、苯酰菌胺、甲呋酰 胺、萎锈灵、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、***醇、灭菌唑、联苯***醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、灭锈胺、多菌灵、苯菌灵、甲基硫菌灵、***酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、硫线磷、丰索磷、虫线磷、苯线磷、灭线磷、除线磷、氯唑磷、丁硫环磷、杀线威、涕灭威、克百威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑；本发明的溴代六氢茚酮类化合物I在所述杀菌组合物中的总的质量百分含量是1％-90％，本发明的溴代六氢茚酮类化合物I与前述商品杀菌剂的比例为质量百分比1％∶99％到99％∶1％；所述杀菌组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；所述杀菌组合物防治的植物病害选自：稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病；所述杀菌组合物适用的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、 蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。All of the brominated hexahydroindanone compounds I of the present invention are combined with any one or two of the commercial bactericides to form a bactericidal composition for controlling agricultural and forestry and horticultural plant diseases, the commercial bactericide selected from the group consisting of: benzene Thiadiazole, thiazide, abbreviated as TDL, thiazamide, methyl thiazide, 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 4-methyl-1,2, 3-thiadiazole-5-formate, 4-methyl-1,2,3-thiadiazol-5-carboxylic acid ethyl ester, DL-β-aminobutyric acid, isotianil, the English common name: Isotianil, 3,4-dichloroisothiazol-5-carboxylic acid, 3,4-dichloroisothiazol-5-formate, 3,4-dichloroisothiazol-5-carboxylic acid ethyl ester, ribavirin, antofin, Ningnanmycin or salicylic acid, cymoxanil, thiram, thiram, mancozeb, ethylphosphoric acid, thiophanate-methyl, chlorothalonil, diclofenac, procymidone, benzodiazepine, Methyl thiophanate, thiophanate, refined metalaxyl, flumorph, enoylmorpholine, high-performance metalaxyl, high-efficiency benzoxanthin, dicyandiamide, sulfamethoxazole, mesalamide, thiafluoxazole Amine, fluoroamide, leaf cumin, cyclopropionamide, cycloflufenamide, fenhexamid, cyanamide , thiastrobin, flupirfen, penthiopyramine, dipropionamide, fenhexamide, carbamoyl Amine, rust, chloramphenicol, iprodione, azoxystrobin, fenfluramine, fluoxastrobin, oxystrobin, phenoxystrobin, anthracycline, picoxystrobin, pyraclostrobin , trifloxystrobin, enestrobin, enestrobin, oxoxazole, carbendazole, cyproconazole, difenoconazole, diniconazole, high-efficiency diniconazole, epoxiconazole, nitrile azole , fluoroquinazole, flusilazole, fluconazole, hexaconazole, imidazole, inocastazole, meconazole, myclobutanil, penconazole, propiconazole, prothioconazole, silrazole, Tebuconazole, tetrafluoroetherazole, triazolol, sterilized azole, biphenyl triazole alcohol, thiabendazole, maisuin, imazalil, high-efficiency imazalil, prochloraz, fluconazole, cyanide cream Azole, imidazolone, mzoimidazole, rice oxime ester, famoxadone, pyridine oxazole, carbendazim, oxacillin, ethaboxam, carbendazim, octyl ketone, thiothiazide, twelve Cyclomorpholine, butylmorpholine, thirteen morpholine, seed dressing, fludioxonil, fluazinam, aglycone, Cyclohexamide, boscalid, fluazirid, aridin, Azoxystrobin, fluzalazine, azoxystrobin, azoxystrobin, pyrimethanil, chlorpyrimidine, Pyrimidine alcohol, chlorpyrifos, dicyanoquinone, ethoxyquin, quinolin, propoxyquinoline, phenoxyquinoline, carbendazim, isopropylidene, phenothiamine, propamocarb, Sulfapredil, enemies, diarrhea, pyridoxine, methyl chlorfen, quercetin, geranol, polymycin, polyoxymycin, tyrosin, jinggangmycin, chain Neomycin, metalaxyl, furosemide, benzathine, furfuramide, rust-eliminating amine, carbendazim, benomyl, thiophanate-methyl, triadimefon, acetaminophen sulfonate, Phenol, acetazol, diclofenac, captan, sterilized dan, vinyl nucleus, chlorhexidine nucleus, sclerotium net, chlorothalonil, indigo, rice glutinous rice, leaf azole, five Chloronitrobenzene, propidium zinc, aluminum triethylphosphinate, sulfur, Bordeaux solution, copper sulfate, copper oxychloride, cuprous oxide, copper hydroxide, benomyl, pentosan, chlorfenone, tetrachloro Benzoquinone, praziquantel, spiroxylamine, tricyclazole, pyridazinamide, polyglycosidine, biguanide salt, bis-octylamine, chloramine, benzepamide, toluidine, oxime ester, Sodium sulfonate, quinostrobin, allyl benzothiazole, bromine , iodomethane, Weibaimu, enemy ester, cotton, dichloroisopropyl ether, thiazophos, sulphur phosphorus, phosporin, insect phosphorus, benzene phosphorus, phosphine, phosphine, chlorazole Phosphorus, butylthiophosphorus, nematicide, aldicarb, carbofuran, sulfuryl fluoride, dichloropropene, dichloroisonicotinic acid, allylisothiazole; brominated hexahydroindolone compound I of the present invention The total mass percentage in the germicidal composition is from 1% to 90%, and the ratio of the brominated hexahydroindanone compound I of the present invention to the commercial fungicide is 1% by mass: 99% to 99% by mass. %: 1%; the dosage form processed by the bactericidal composition is selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble concentrate, poisonous valley, block Bait, granular bait, flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment , hot spray, cold spray, aerosol, solid/liquid mixed charge, liquid/liquid mixed charge, solid/solid mixed charge, lacquer, Microgranule, trace powder, oil suspension, oil dispersible powder, thickener, pouring agent, seed coating agent, spread agent, film forming oil agent, ultra low volume liquid agent, steam release agent; The plant diseases to be controlled are selected from the group consisting of: rice seedling cotton rot, tomato root rot, potato late blight, tobacco black shank, millet powdery mildew, grape downy mildew, lettuce downy mildew, cucumber downy mildew, cucumber anthracnose; The bactericidal composition is suitable for plants selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, pea, broad bean, pea, mung bean, adzuki bean, cotton, Silkworm, peanut, rapeseed, sesame, sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet , rapeseed, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

实施例12Example 12

本发明的溴代六氢茚酮类化合物I与抗植物病毒剂组合在防治农业和林业以及园艺植物病毒病害中的应用：The use of the brominated hexahydroindolone compound I of the present invention in combination with an anti-plant virus agent for controlling agricultural and forestry and horticultural plant virus diseases:

本发明的所有溴代六氢茚酮类化合物I与商品抗病毒药剂中的任意一种或两种组合形成抗病毒组合物用于防治农业和林业以及园艺植物病毒病害，所述商品抗病毒药剂选自：苯并噻二唑、噻酰菌胺，简写为TDL、异噻菌胺，其英文通用名为：isotianil、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、DL-β-氨基丁酸、病毒唑、安托芬、宁南霉素、噻酰胺、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈羟胺、井冈霉素；本发明的溴代六氢茚酮类化合物I在所述抗病毒组合物中的总的质量百分含量是1％-90％，本发明的溴代六氢茚酮类化合物I与前述商品抗植物病毒剂的比例为质量百分比1％∶99％到99％∶1％；所述抗病毒组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；所述抗病毒组合物防治的病毒病害选自：水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒；所述抗病毒组合物用于防治的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。All of the brominated hexahydroindolone compounds I of the present invention are combined with any one or both of the commercial antiviral agents to form an antiviral composition for controlling agricultural and forestry and horticultural plant virus diseases, the commercial antiviral agents Selected from: benzothiadiazole, thiazide, abbreviated as TDL, Isotianil, its common name in English is: isotianil, 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 4-methyl-1,2,3-thiadiazol-5-formate, 4-methyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester, 3,4-dichloroisothiazol-5 - formic acid, sodium 3,4-dichloroisothiazol-5-formate, ethyl 3,4-dichloroisothiazol-5-carboxylate, DL-β-aminobutyric acid, ribavirin, antofin, ningnanmycin , thiamidamide, methyl thiazide or salicylic acid, praline peptide, dichloroisonicotinic acid, allylisothiazole, Jinggang hydroxylamine, Jinggangmycin; the brominated hexahydroindolone compound I of the present invention The total mass percentage in the antiviral composition is from 1% to 90%, and the ratio of the brominated hexahydroindanone compound I of the present invention to the commercial anti-plant virus agent is 1% by mass to 99% by mass 99%: 1%; the antiviral composition plus The dosage form is selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble concentrate, poisonous valley, block bait, granular bait, flaky bait, Thick bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, hot spray, cold spray, gas Atomizing agent, solid/liquid mixing agent, liquid/liquid mixing agent, solid/solid mixing agent, lacquer, granule, tracking powder, oil suspension, oil dispersible powder, thick glue, pouring agent, Seed coating agent, smear agent, film forming oil agent, ultra low volume liquid agent, steam release agent; the virus disease controlled by the antiviral composition is selected from the group consisting of rice dwarf disease, yellow dwarf disease, stripe leaf blight, tomato Fern leaf virus disease, pepper mosaic virus disease, tobacco vein necrosis virus disease, corn dwarf mosaic disease, cauliflower mosaic virus, citrus virus disease, Jianlan leaf virus, Jianlan ring spot virus; the antiviral composition is used for Control plants are selected from: rice, wheat, barley, oats, jade , sorghum, sweet potato, potato, cassava, soybean, pea, bean, pea, mung bean, adzuki bean, cotton, sericulture, peanut, rape, sesame, sunflower, sugar beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, Oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, rape, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables , bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

实施例13：本发明的溴代六氢茚酮类化合物I与杀螨剂组合在防治农业和林业以及园艺植物螨害中的应用： Example 13: Application of the brominated hexahydroindolone compound I of the present invention in combination with an acaricide in controlling agricultural and forestry and horticultural plant damage:

本发明的所有溴代六氢茚酮类化合物I与商品杀螨剂中的任意一种或两种组合形成杀螨组合物用于防治农业和林业以及园艺植物螨害，所述商品杀螨剂选自：***锡、三环锡、苯丁锡、三磷锡、毒虫畏、甲基毒虫畏、巴毒磷、敌敌畏、庚烯磷、速灭磷、久效磷、二溴磷、毒死蜱、嘧啶磷、氯甲亚胺硫磷、氧乐果、敌杀磷、乙硫磷、马拉硫磷、虫螨畏、伏杀硫磷、辛硫磷、甲基嘧啶硫磷、喹硫磷、治螟磷、***磷、蚜灭多、水胺硫磷、甲胺磷、胺丙畏、氯亚胺硫磷、亚胺硫磷、氟丙菊酯、联苯菊酯、氯氟氰菊酯、精高效氯氟氰菊酯、甲氰菊酯、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯、溴氟菊酯、联苯肼酯、苯硫威、涕灭威、丁酮威、杀线威、抗虫威、久效威、苯菌灵、氯灭杀威、克百威、丁硫克百威、速灭威、蜱虱威、伐虫脒、单甲脒、杀螨脒、双甲脒、杀虫脒、苯甲酸苄酯、溴螨酯、丁氟螨酯、灭螨醌、氟蚜螨、氟虫脲、浏阳霉素、虫螨霉素、苏云金素、杀螨素、浏阳霉素、阿维菌素、多拉菌素、埃普利诺菌素、伊维菌素、赛拉菌素、莫西菌素、除虫菊素、烟碱、苦参碱、印楝素、鱼藤酮、吡螨胺、哒螨酮、唑螨酯、四螨嗪、炔螨特、噻螨酮、螺螨酯、嘧螨酯、杀螨酯、克螨特、哒螨灵；本发明的溴代六氢茚酮类化合物I在所述杀螨组合物中的总的质量百分含量是1％-90％，本发明的溴代六氢茚酮类化合物I与所述商品杀螨剂的比例为质量百分比1％∶99％到99％∶1％；所述杀螨组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；所述杀螨组合物防治的螨害选自：螨害选自叶螨科、细须螨科、呋线螨、瘿螨科、红叶螨属、瘿螨科的害螨，这些害螨是世界性农业害螨、林业害螨、园艺害螨和卫生害螨；所述杀螨组合物用于防治的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。 All of the brominated hexahydroindolone compounds I of the present invention are combined with any one or both of the commercial acaricides to form acaricidal compositions for controlling agricultural and forestry and horticultural plant mites, said commercial acaricides Selected from: triazolyl, tricyclotin, phenbutyltin, triphosphorus, chlorpyrifos, methyl chlorpyrifos, phytophos, dichlorvos, heptene phosphorus, fast-acting phosphorus, monocrotophos, dibromophosphorus, chlorpyrifos , pyrimidine phosphorus, chloromethionine, omethoate, chlorpyrifos, ethion, malathion, chlorpyrifos, sulforaphane, phoxim, methyl pyrithione, quetiapine , treatment of bismuth phosphorus, triazophos, annihilation, acesulfame, methamidophos, acesulfame, chloroimidate, imipenem, flumethrin, bifenthrin, chlorofluorocyanide Pyrethroid, cyhalothrin, fenvalerate, fluvalinate, flumethrin, fluvalinate, bifenthrin, bifenyl ester, phenylthiocarb, annihilation Wei, butanone, killing, anti-insect, long-acting, benomyl, chlorhexidine, carbofuran, butyl thiocarb, acesulfame, suiwei, worm, sputum, single Hyperthyroidism, killing, double armor脒, chlorpyrifos, benzyl benzoate, bromo oxime ester, butyl fluoro ester, guanidine, fluoroquinone, flubendiamide, liuyangmycin, echinomycin, sulphate, acaricidal, sulphate , avermectin, doramectin, eplenomycin, ivermectin, serramycin, moxidectin, pyrethrin, nicotine, matrine, azadirachtin, rotenone, Pyridoxamine, anthrone, oxazolidine, tetrazazine, alkyne , thiazolone , spirodecyl ester, pyridoxine , acaricidal ester , ketone, oxime ; The total mass percentage of the hydroquinone compound I in the acaricidal composition is from 1% to 90%, and the ratio of the brominated hexahydroindanone compound I of the present invention to the commercial acaricide is Percentage by mass: 1%: 99% to 99%: 1%; the dosage form processed by the acaricidal composition is selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule Agent, soluble concentrate, poisonous valley, block bait, granular bait, flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle Smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, hot spray, cold spray, aerosol, solid/liquid mixture, liquid/liquid mixture, solid/solid mixture Agent, lacquer, microgranule, trace powder, oil suspension, oil dispersible powder, thick glue, pouring agent, seed coating agent, spread agent, film forming oil agent, ultra low volume liquid agent, steam release agent; The pest control of the acaricidal composition is selected from the group consisting of: the pest is selected from the group consisting of the leaf family, the genus, the genus, the genus, the genus, the genus, the cockroach, and the cockroach is the world agriculture. Pests, forest pests, horticultural pests and health hazards; plants used for control of the acaricidal composition are selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, pea , broad beans, peas, mung beans, adzuki beans, cotton, sericulture, peanuts, rapeseed, sesame, sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, Radish, cucumber, cabbage, celery, mustard, beet, rape Onions, garlic, watermelon, melon, cantaloupe, papaya, apple, peach and citrus, tea, mountain vegetables, bamboo shoots, hops, pepper, banana, papaya, orchids, bonsai.

表1本发明的溴代六氢茚酮类化合物I的化学结构和理化参数Table 1 Chemical structure and physical and chemical parameters of the brominated hexahydroindolone compound I of the present invention

表2本发明的溴代六氢茚酮类化合物I的抑菌活性(50微克/毫升的抑制/％)Table 2 Antibacterial activity of the bromohexamidine compound I of the present invention (inhibition/% of 50 μg/ml)

序号Serial number	编号Numbering	ASAS	BCBC	CACA	GZGZ	PIPI	PPPP	PSPS	RCRC	SSSS
11	zyj05-154Zyj05-154	35.7235.72	47.3847.38	36.8736.87	58.4958.49	35.4635.46	29.0029.00	36.0836.08	28.9528.95	77.4377.43
22	zyj05-155Zyj05-155	36.2936.29	45.7645.76	40.5040.50	48.0248.02	32.7232.72	36.8836.88	27.5227.52	29.3329.33	68.1868.18
33	zyj05-157Zyj05-157	42.5242.52	61.4661.46	45.0045.00	49.5049.50	30.5630.56	39.1539.15	29.6729.67	38.1738.17	75.2975.29
44	zyj05-171Zyj05-171	45.5345.53	28.2828.28	35.6735.67	34.8834.88	39.1839.18	28.0028.00	27.0527.05	31.7631.76	70.0970.09
55	zyj05-172Zyj05-172	44.5644.56	61.8561.85	35.9935.99	51.0551.05	34.7234.72	30.0030.00	40.2940.29	25.4525.45	78.9978.99
66	zyj05-176Zyj05-176	42.3142.31	50.0050.00	33.3333.33	40.0040.00	22.2222.22	4.004.00	31.0331.03	23.0823.08	73.9173.91
77	zyj05-186Zyj05-186	50.0050.00	41.6741.67	46.6746.67	44.0044.00	29.6329.63	8.008.00	37.9337.93	42.3142.31	86.9686.96
88	异噻菌胺Isotianil	00	34.5034.50	13.3013.30	8.308.30	22.7022.70	32.0032.00	13.3013.30	34.8034.80	87.5087.50

表3本发明的溴代六氢茚酮类化合物I的杀蚜活性(死亡率，％，100毫克/毫升)Table 3 Acaricidal activity of bromohexamidine compound I of the present invention (mortality, %, 100 mg/ml)

序号Serial number	编号Numbering	死亡率/％mortality rate/%
11	zyj05-154Zyj05-154	25.025.0
22	zyj05-155Zyj05-155	32.632.6
33	zyj05-157Zyj05-157	28.328.3
44	zyj05-171Zyj05-171	45.945.9
55	zyj05-172Zyj05-172	39.739.7
66	zyj05-176Zyj05-176	46.446.4
77	zyj05-186Zyj05-186	40.940.9
88	噻虫啉Thiacloprid	51.4851.48

表4本发明的溴代六氢茚酮类化合物I的抗烟草花叶病毒活性(100微克/毫升的抑制率/％)Table 4 Anti-tobacco mosaic virus activity of the brominated hexahydroindanone compound I of the present invention (inhibition rate/% of 100 μg/ml)

序号Serial number	编号Numbering	钝化模式Passivation mode	诱导模式Induction mode
11	zyj05-154Zyj05-154	45.15±4.3545.15±4.35	28.38±5.1228.38±5.12
22	zyj05-155Zyj05-155	47.37±6.2847.37±6.28	49.89±3.5549.89±3.55
33	zyj05-157Zyj05-157	38.56±7.0038.56±7.00	56.66±5.0056.66±5.00
44	zyj05-171Zyj05-171	49.90±3.5549.90±3.55	35.55±4.4435.55±4.44
55	zyj05-172Zyj05-172	42.58±5.3842.58±5.38	37.90±5.6837.90±5.68
66	zyj05-176Zyj05-176	37.99±4.8137.99±4.81	57.62±6.9957.62±6.99
77	zyj05-186Zyj05-186	39.50±4.1939.50±4.19	59.99±4.2759.99±4.27
99	病毒唑Ribavirin	38.05±3.5038.05±3.50	--
3333	噻酰菌胺Thiabendamide	24.99±4.5824.99±4.58	46.58±6.1246.58±6.12

工业实用性Industrial applicability

本发明提供一类卤代六氢茚酮类化合物及其制备方法和用途。本发明提供的化合物能够调控农业、园艺和卫生以及林业植物害虫和植物病原物的生物活性，可用于农业领域、园艺领域、林业领域以及卫生领域杀虫、杀菌、抗植物病毒，具有较好的经济价值和应用前景。 The invention provides a class of halogenated hexahydroindolone compounds, a preparation method thereof and use thereof. The compound provided by the invention can regulate the biological activities of agricultural, horticultural and sanitary and forestry plant pests and plant pathogens, and can be used for agricultural, horticultural, forestry and sanitary fields, insecticidal, bactericidal, anti-plant virus, and has better Economic value and application prospects.

Claims (11)

1. 一类溴代六氢茚酮类化合物，其特征在于具有如式I所示的化学结构通式：A class of brominated hexahydroindolone compounds having the chemical structural formula as shown in Formula I:

   

   

   其中，R¹选自苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-氟苯基、3-氟苯基、4-氟苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-硝基苯基、3-硝基苯基、4-硝基苯基、4-乙基苯基、4-甲基-1,2,3-噻二唑基、2-呋喃基、2-甲基-2-(4-氯苯基)-1-丙基、三氯甲基、菊酰基、二氯菊酰基、4-氟苯乙基、2,6-二氯苯基、甲基、丙基、庚基、3,5-二氯苯基、3,5-二甲基、3-(2-氯苯基)-5-甲基异噁唑-4-基、2,4-二甲基-1-苯基吡唑-3-基、环己基、2-氟苯乙基、3,6-二氯吡啶-2-基、5-乙基-1-甲基吡唑-3-基、2-氟苯乙基的基团、4-甲基-1,2,3-噻二唑-5-基、5-甲基-1,2,3-噻二唑-4-基、3,4-二氯异噻唑-5-基；X¹选自F、Cl、Br、I；X²选自F、Cl、Br、I。Wherein R ^{1 is} selected from the group consisting of phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxy Phenylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-trifluoromethylphenyl, 3 -trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-ethylphenyl, 4-methyl- 1,2,3-thiadiazolyl, 2-furyl, 2-methyl-2-(4-chlorophenyl)-1-propyl, trichloromethyl, cholanyl, dichloro chrysanyl, 4 -fluorophenethyl, 2,6-dichlorophenyl, methyl, propyl, heptyl, 3,5-dichlorophenyl, 3,5-dimethyl, 3-(2-chlorophenyl) -5-methylisoxazol-4-yl, 2,4-dimethyl-1-phenylpyrazol-3-yl, cyclohexyl, 2-fluorophenethyl, 3,6-dichloropyridine- a group of 2-yl, 5-ethyl-1-methylpyrazol-3-yl, 2-fluorophenethyl, 4-methyl-1,2,3-thiadiazol-5-yl, 5 - methyl-1,2,3-thiadiazol-4-yl, 3,4-dichloro-5-yl; X ¹ is selected from F, Cl, Br, I; X 2 is selected from F, Cl , Br, I.
2. 权利要求1所述的溴代六氢茚酮类化合物I的合成方法，具体合成路线如下：The method for synthesizing the brominated hexahydroindolone compound I according to claim 1, wherein the specific synthetic route is as follows:

   

   

   其中，R¹选自苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-氟苯基、3-氟苯基、4-氟苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-硝基苯基、3-硝基苯基、4-硝基苯基、4-乙基苯基、4-甲基-1,2,3-噻二唑基、2-呋喃基、2-甲基-2-(4-氯苯基)-1-丙基、三氯甲基、菊酰基、二氯菊酰基、4-氟苯乙基、2,6-二氯苯基、甲基、丙基、庚基、3,5-二氯苯基、3,5-二甲基、3-(2-氯苯基)-5-甲基异噁唑-4-基、2,4-二甲基-1-苯基吡唑-3-基、环己基、2-氟苯乙基、3,6-二氯吡啶-2-基、5-乙基-1-甲基吡唑-3-基、2-氟苯乙基的基团、4-甲基-1,2,3-噻二唑-5-基、5-甲基-1,2,3-噻二唑-4-基、3,4-二氯异噻唑-5-基；X选自F、Cl、Br、I；X¹选自F、Cl、Br、I；X²选自F、Cl、Br、I；NXS选自N-溴代丁二酰亚胺、N-氯代丁二酰亚胺。Wherein R ^{1 is} selected from the group consisting of phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxy Phenylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-trifluoromethylphenyl, 3 -trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-ethylphenyl, 4-methyl- 1,2,3-thiadiazolyl, 2-furyl, 2-methyl-2-(4-chlorophenyl)-1-propyl, trichloromethyl, cholanyl, dichloro chrysanyl, 4 -fluorophenethyl, 2,6-dichlorophenyl, methyl, propyl, heptyl, 3,5-dichlorophenyl, 3,5-dimethyl, 3-(2-chlorophenyl) -5-methylisoxazol-4-yl, 2,4-dimethyl-1-phenylpyrazol-3-yl, cyclohexyl, 2-fluorophenethyl, 3,6-dichloropyridine- a group of 2-yl, 5-ethyl-1-methylpyrazol-3-yl, 2-fluorophenethyl, 4-methyl-1,2,3-thiadiazol-5-yl, 5 -Methyl-1,2,3-thiadiazol-4-yl, 3,4-dichloroisothiazol-5-yl; X is selected from the group consisting of F, Cl, Br, I; X ^{1 is} selected from the group consisting of F, Cl, br, I; X ² is selected from F, Cl, br, I; NXS selected from N- bromosuccinimide, N- chlorosuccinimide acid Amine.
3. 根据权利要求2所述的合成方法，其特征在于，所述的溴代六氢茚酮类化合物的合成方法分为以下步骤： The method according to claim 2, wherein the method for synthesizing the brominated hexahydroindanone compound is divided into the following steps:

   A.化合物III的制备：A. Preparation of Compound III:

   将化合物II加入反应瓶中，抽真空，注入氮气保护，然后加入干燥的四氢呋喃溶液，冰盐浴下向反应瓶中缓慢滴加乙烯基溴化镁，滴加完毕后，分别在冰盐浴中和室温下搅拌，反应完全后，反应液加入饱和碳酸氢钠溶液淬灭，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物III；Add compound II to the reaction flask, vacuum, inject nitrogen to protect, then add dry tetrahydrofuran solution, slowly add vinyl magnesium bromide to the reaction flask under ice salt bath, and add the mixture to the ice salt bath. After stirring at room temperature, the reaction mixture was quenched with saturated sodium hydrogen sulfate solution and extracted with ethyl acetate. The ethyl acetate layer was separated and washed with saturated sodium hydrogen carbonate and saturated sodium chloride. Drying over anhydrous magnesium sulfate, suction filtration, concentration, solvent was evaporated under reduced pressure, and the residue was purified to give compound III;

   B.化合物IV的制备：B. Preparation of Compound IV:

   将步骤A制得的化合物III溶于四氢呋喃溶液中，然后加入硼氢化钠，冰浴下缓慢滴加三氟化硼***的四氢呋喃溶液，滴加完毕后，分别在冰浴中和室温下搅拌，反应完全后，在冰浴下向反应瓶中缓慢滴加Jones试剂，滴加完毕后在室温继续搅拌，反应完全后，加入水，然后用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物IV；The compound III obtained in the step A was dissolved in a tetrahydrofuran solution, and then sodium borohydride was added thereto, and a solution of boron trifluoride diethyl ether in tetrahydrofuran was slowly added dropwise thereto in an ice bath. After the dropwise addition, the mixture was stirred in an ice bath and at room temperature. After the reaction was completed, the Jones reagent was slowly added dropwise to the reaction flask under ice bath. After the completion of the dropwise addition, stirring was continued at room temperature. After the reaction was completed, water was added, and then extracted with ethyl acetate to separate the ethyl acetate layer. The ester phase is washed with saturated sodium hydrogen carbonate and saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, filtered, evaporated

   C.化合物V的制备：C. Preparation of Compound V:

   将步骤B制得的化合物IV溶于四氢呋喃与水的混合溶液中，冰浴下向反应液中加入硼氢化钠，加入完毕后，撤去冰浴，室温搅拌，反应完全后加入饱和碳酸氢钠淬灭，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物V；The compound IV obtained in the step B is dissolved in a mixed solution of tetrahydrofuran and water, and sodium borohydride is added to the reaction solution under ice bath. After the addition, the ice bath is removed, stirred at room temperature, and the reaction is completed, and then saturated with sodium hydrogencarbonate is added. The mixture was extracted with EtOAc. EtOAc EtOAc. Purification, preparation of compound V;

   D.化合物VI的制备：D. Preparation of Compound VI:

   将步骤C制得的化合物V溶于二氯甲烷中，抽真空，注入氮气保护，冰浴下向反应瓶中加入三乙胺，然后缓慢滴加酰氯R¹COCl，滴加完毕后，撤去冰浴，室温搅拌，反应完全后加入饱和碳酸氢钠溶液萃取，分出二氯甲烷层，二氯甲烷相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物VI；The compound V prepared in the step C was dissolved in dichloromethane, vacuumed, and protected with nitrogen. Triethylamine was added to the reaction flask under ice bath, and then the acid chloride R ¹ COCl was slowly added dropwise. After the addition was completed, the ice was removed. The mixture was stirred at room temperature. After the reaction was completed, the mixture was evaporated, evaporated, evaporated, evaporated, evaporated. , the solvent is removed under reduced pressure, the residue is purified to give the compound VI;

   E.化合物VII的制备：E. Preparation of Compound VII:

   将步骤D制得的化合物VI溶于甲磺酸中，然后加入五氧化二磷在35-40摄氏度下反应，反应完全后加入水，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物VII；The compound VI obtained in the step D is dissolved in methanesulfonic acid, and then the phosphorus pentoxide is added to react at 35-40 degrees Celsius. After the reaction is completed, water is added, and the mixture is extracted with ethyl acetate to separate the ethyl acetate layer. The ester phase is washed with saturated sodium hydrogencarbonate and saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, filtered, evaporated,

   F.化合物I的制备：F. Preparation of Compound I:

   当R¹为Ph、X¹为Br、X²为H时，化合物I的制备方法如下：When R ¹ is Ph, X ¹ is Br, and X ² is H, the preparation method of Compound I is as follows:

   将步骤E制得的化合物VII溶于干燥的四氯化碳中，然后依次加入N-溴代丁二酰 亚胺和偶氮二异丁腈，在50摄氏度下反应，反应完全后，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物I；The compound VII obtained in the step E is dissolved in dry carbon tetrachloride, and then N-bromosuccinyl group is sequentially added. The imine and azobisisobutyronitrile, the reaction is carried out at 50 ° C, the reaction is completed, suction filtration, concentration, the solvent is removed under reduced pressure, the residue is purified to obtain the compound I;

   当R¹为Ph、X¹为H、X²为Br时，化合物I的制备方法如下：When R ¹ is Ph, X ¹ is H, and X ² is Br, the preparation method of Compound I is as follows:

   将步骤E制得的化合物VII溶于干燥的乙腈中，然后依次加入N-溴代丁二酰亚胺和三氟甲磺酸三甲基硅酯，加入完毕后，室温搅拌，反应完全后加入饱和碳酸氢钠溶液萃取，用乙酸乙酯萃取，分离出乙酸乙酯层，乙酸乙酯相用饱和碳酸氢钠和饱和氯化钠洗涤后经无水硫酸镁干燥，抽滤，浓缩，减压除去溶剂，将残余物纯化，制得化合物I。The compound VII obtained in the step E is dissolved in dry acetonitrile, and then N-bromosuccinimide and trimethylsilyl trifluoromethanesulfonate are sequentially added. After the addition is completed, the mixture is stirred at room temperature, and the reaction is completed. The mixture was extracted with EtOAc EtOAc (EtOAc m. The solvent was removed and the residue was purified to give Compound I.
4. 权利要求1所述的溴代六氢茚酮类化合物I在制备杀菌剂、杀虫剂、抗植物病毒剂或植物激活剂中的用途。Use of the bromohexamidine compound of claim 1 for the preparation of a bactericide, insecticide, plant virus or plant activator.
5. 根据权利要求4所述的用途，其特征在于，所述的溴代六氢茚酮类化合物I与农业上可接受的助剂在制备杀菌剂、杀虫剂、抗植物病毒剂或植物激活剂中的用途。The use according to claim 4, characterized in that the bromo hexahydroindanone compound I and an agriculturally acceptable auxiliaries are used in the preparation of bactericides, insecticides, plant virus agents or plant activators Use in.
6. 权利要求1所述的溴代六氢茚酮类化合物I在防治农业和林业以及园艺植物虫害中的用途。Use of the brominated hexahydroindanone compound I according to claim 1 for controlling agricultural and forestry and horticultural plant pests.
7. 根据权利要求6所述的用途，其特征在于，所述溴代六氢茚酮类化合物I与农业化学品共同施用；优选地，所述农业化学品选自：杀虫剂、杀菌剂、抗植物病毒剂、杀螨剂中的一种或几种。The use according to claim 6, wherein the brominated hexahydroindanone compound I is co-administered with an agricultural chemical; preferably, the agricultural chemical is selected from the group consisting of insecticides, fungicides, and antibiotics. One or more of a plant virus agent and an acaricide.
8. 根据权利要求6-7所述的用途，其特征在于，所述的溴代六氢茚酮类化合物I与所述杀虫剂中的任意一种或两种组合形成杀虫组合物用于防治农业和林业以及园艺植物虫害；The use according to claims 6-7, characterized in that the hexahydroindanone compound I is combined with any one or both of the insecticides to form an insecticidal composition for control Agriculture and forestry and horticultural plant pests;

   优选地，所述杀虫剂选自：毒死蜱、地亚哝、啶虫脒、甲氨基阿维菌素、弥拜菌素、阿维菌素、多杀菌素、氰戊菊酯、高效氰戊菊酯、氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、Beta-氟氯氰菊酯、Lambda-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、联苯菊酯、氯菊酯、醚菊酯、氟氯苯菊酯、氯氟胺氰戊菊酯、吡虫啉、烯啶虫胺、氯噻啉、噻虫啉、噻虫嗪、噻虫胺、呋虫胺、可尼丁、达特南、除虫脲、灭幼脲、伏虫隆、除虫隆、氟铃脲、氟虫脲、啶虫隆、虱螨脲、毒虫脲、氟幼脲、Noviflumuron即多氟脲，其CAS号为121451-02-3、氟螨脲、Novaluron即双苯氟脲、氟啶脲、Bay sir 6874即1-[(3.5-二氯-4)4-硝基苯氧基苯基3-3-(2-氯苯)-脲、Bay SIR-8514即1-(4-三氟甲氧基苯基)-3-(2-氯苯)-脲、嗪虫脲、Bistrifluron即双三氟虫脲、呋喃虫酰肼、虫酰肼、氯虫酰肼、甲氧虫酰肼、环虫酰肼、乐果、氧化乐果、敌敌畏、乙酰甲胺磷、***磷、喹硫磷、哒嗪硫磷、氯唑磷、叶蝉散、西维因、抗蚜威、速灭威、异丙威、杀螟丹、仲丁威、叶飞散、甲萘威、丙硫克百威、丁硫克百威、 杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、丁烯氟虫腈、***锡、噻嗪酮、灭线磷、氟虫腈、杀虫单、杀虫双、氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、唑虫酰胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素；Preferably, the insecticide is selected from the group consisting of: chlorpyrifos, scorpion guanidine, acetamiprid, emamectin, imipenem, avermectin, spinosyn, fenvalerate, high-efficiency acetonide Pyrethroid, cypermethrin, beta-cypermethrin, cyhalothrin, deltamethrin, fenpropathrin, Beta-cyfluthrin, Lambda-cyhalothrin, permethrin, permethrin, methrin, hydrazine Pyrethrin, permethrin, fenthrin, flumethrin, flufenacetate, imidacloprid, nitenpyram, chlorothiazide, thiacloprid, thiamethoxam, clothianidin, fur Nicotinamide, cotinine, Dartnam, diflubenzuron, chlorbenzuron, flubenzuron, chlorfenapyr, hexaflumuron, flubenzuron, acetamiprid, guanidine, chlorpyrifos, flubenzuron, Noviflumuron is a polyfluorourea with a CAS number of 121451-02-3, fluoroquinone urea, Novaluron, ie, diphenylfluorourea, chlorfluazuron, and Bay sir 6874, 1-[(3.5-dichloro-4)4-nitro Phenoxyphenyl 3-3-(2-chlorophenyl)-urea, Bay SIR-8514, 1-(4-trifluoromethoxyphenyl)-3-(2-chlorophenyl)-urea, oxazide Urea, Bistrifluron, bis-trifluoroidazolium, furanyl hydrazide, tebufenozide, Tebufenozide, methoxyfenhydrazide, chlorfenapyr, dimethoate, omethoate, dichlorvos, acephate, triazophos, quetiapine, pyridazin, chlorpyrifos, arsenic, Xiweiin, Kangwei, Kuweiwei, Weiweiwei, Qidan, Zhongdingwei, Yefeisan, Jia Naiwei, propyl thiocarb, thiocarb, Killing dan, bromo oxime ester, thiazolone, oxazolidine, fluorenone, tetrazine, acetylene, butyl ether urea, pymetrozine, spiro sterol, spirotetramat, spirotetramat, diced Iridazil, triazole tin, buprofezin, phosphazone, fipronil, insecticidal, insecticidal, chlorantraniliprole, flubendiamide, flufenamide, cyanamide, azole, Bromocarbonitrile, pyrazinone, etoxazole, pyridoxamine, ketone, pyriproxyfen, emamectin;

   优选地，所述的溴代六氢茚酮类化合物I在所述杀虫组合物中的质量百分含量是1％-90％；Preferably, the mass percentage of the brominated hexahydroindanone compound I in the pesticidal composition is from 1% to 90%;

   优选地，所述的溴代六氢茚酮类化合物I与所述杀虫剂的比例为质量百分比1％∶99％到99％∶1％；Preferably, the ratio of the brominated hexahydroindanone compound I to the insecticide is 1% by mass: 99% to 99%: 1% by mass;

   优选地，所述杀虫组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；Preferably, the dosage form processed by the pesticidal composition is selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble concentrate, poisonous valley, lumps Bait, granular bait, flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, Hot mist, cold spray, aerosol, solid/liquid mixed charge, liquid/liquid mixed charge, solid/solid mixed charge, lacquer, microparticle, trace powder, oil suspension, oil dispersible powder , thickener, pouring agent, seed coating agent, smear agent, film forming oil agent, ultra low volume liquid agent, steam release agent;

   优选地，所述杀虫组合物防治的植物虫害选自：红蜘蛛、东亚飞蝗、云斑车蝗、中华稻蝗、日本黄脊蝗、单刺蝼蛄、东方蝼蛄、稻蓟马、烟蓟马、温室蓟马、稻管蓟马、麦简管蓟马、温室白粉虱、烟粉虱、黑尾叶蝉、大青叶蝉、棉叶蝉、斑衣蜡蝉、褐飞虱、白背飞虱、灰飞虱、甘蔗扁角飞虱、棉蚜、麦二叉蚜、麦长管蚜、桃蚜、高粱蚜、萝卜蚜、吹绵蚧、桑盾蚧、矢尖盾蚧、梨圆蚧、白蜡虫、红蜡蚧、朝鲜球坚蚧、梨网蝽、香蕉网蝽、细角花蝽、微小花蝽、针缘蝽、稻蛛缘蝽、稻褐蝽、稻黑蝽、稻绿蝽、绿盲蝽、苜蓿盲蝽、中黑盲蝽、大草蛉、丽草蛉、中华草蛉、谷蛾、衣蛾、黄刺蛾、褐刺蛾、扁刺蛾、麦蛾、棉红铃虫、甘薯麦蛾、小菜蛾、桃小食心虫、大豆食心虫、桃小食心虫、苹果顶梢卷叶蛾、褐带长卷叶蛾、拟小黄卷叶蛾、二化螟、豆荚螟、玉米螟、三化螟、菜螟、稻纵卷叶螟、条螟、棉卷叶野螟、桃蛀螟、黏虫、斜纹夜蛾、稻螟蛉、棉小造桥虫、甜菜夜蛾、大螟、棉铃虫、鼎点金刚钻、小地老虎、大地老虎、黄地老虎、盗毒蛾、舞毒蛾、甘薯天蛾、豆天蛾、直纹稻弄蝶、隐纹谷弄蝶、柑橘凤蝶、玉带凤蝶、菜粉蝶、苎麻赤蛱蝶、苎麻黄蛱蝶、豆芫菁、金星步甲、皱鞘步甲、麦穗步甲、沟金针虫、细胸金针虫、谷斑皮蠹、黑皮蠹、柑橘小吉丁虫、金缘吉丁虫、黄粉虫、黑粉虫、赤拟谷盗、杂拟谷盗、铜绿异丽金龟、暗黑金龟、华北大黑鳃金龟、桑天牛、星天牛、橘褐天牛、桃红颈天牛、大猿叶虫、小猿叶虫、黄守瓜、黄曲条跳甲、绿豆象、豌豆象、蚕豆象、玉米象、米象、小麦叶蜂、梨实蜂、黄带姬蜂、黏虫白星姬蜂、螟蛉悬茧姬蜂、棉铃虫齿唇姬蜂、螟黑点疣姬蜂、蚊、蝇、虻、 麦红吸浆虫、麦黄吸浆虫、稻瘿蚊、柑橘大实蝇、瓜实蝇、麦叶灰潜蝇、美洲斑潜蝇、豆秆黑潜蝇、麦秆蝇、种蝇、葱蝇、萝卜蝇、伞裙追寄蝇、玉米螟厉寄蝇、黏虫；Preferably, the plant pests controlled by the insecticidal composition are selected from the group consisting of: red spider, oriental planthopper, cloud locust, Chinese rice blast, Japanese yellow ridge, single locust, oriental carp, rice locust, and tobacco Horse, greenhouse thrips, rice tube thrips, wheat tube horses, greenhouse whitefly, whitefly, black-tailed leafhopper, big green leafhopper, cotton leafhopper, spotted waxhopper, brown planthopper, white-backed planthopper , Laodelphax striatellus, sugarcane, flat-horned corn fly, cotton aphid, wheat bifurcation, wheat long tube, peach aphid, sorghum, radish, blown, sang shield, yam shield, pear round, White wax insects, red wax mites, Korean ball glutinous rice, pear net mites, banana net mites, fine-horned flower buds, tiny flower buds, needle-edge mites, rice spider mites, rice brown mites, rice black mites, rice green mites, Green-spotted scorpion, scorpion scorpion, black-spotted scorpion, large grass scorpion, cypress, Chinese grass scorpion, valley moth, clothing moth, yellow thorn moth, brown thorn moth, spur moth, wheat moth, cotton bollworm, Sweet potato moth, diamondback moth, peach small heartworm, soybean heartworm, peach small heartworm, apple tip leaf moth, brown leaf moth, pseudo-small leaf moth, stem borer, bean pod Corn borer, stem borer, rapeseed meal, rice leaf roller, barley, cotton leaf bark, peach aphid, armyworm, Spodoptera litura, rice bran, cotton small bridgeworm, beet armyworm, giant salamander , cotton bollworm, Ding Ding diamond, small tiger, earth tiger, yellow tiger, poisonous moth, gypsy moth, sweet potato hawk moth, bean hawk moth, straight grain rice butterfly, cryptic valley butterfly, citrus swallow butterfly, jade belt Swallowtail butterfly, cabbage butterfly, ramie red butterfly, ramie butterfly, bean phthalocyanine, Venus carapace, wrinkle sheath, armor, wheat burdock, echinoderma, scutellaria, variegata, black skin蠹, citrus small jiding insects, Jinyuan jiding insects, yellow mealworms, black mealworms, red worms, miscellaneous pirates, patina, golden tortoises, dark golden tortoises, North China black scorpion, sangtian cattle, star days Cow, Orange Brown Beech, Peach Red-necked Beef, Big Leafhopper, Small Leafhopper, Yellow Cucumber, Yellow-curved Flea, Green Bean, Pea, Broad Bean, Corn, Rice, Wheat Leaf, Pear Real bees, yellow-banded bees, sticky insects, white-spotted bee, stag beetle, cotton bollworm, beetle, bee, black-spotted bee, mosquito, fly, dragonfly Wheat red worm, wheat yellow worm, rice blast, citrus fruit fly, melon flies, larvae, larvae, stalk snail, stalk fly, fly, onion fly, radish fly , umbrella skirts to catch flies, corn scorpion flies, sticky insects;

   优选地，所述杀虫组合物防治的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。Preferably, the plant controlled by the pesticidal composition is selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, tapioca, soybean, pea, broad bean, pea, mung bean, adzuki bean, cotton, sericulture, peanut , rapeseed, sesame, sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, rape, Onions, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.
9. 根据权利要求6-7所述的用途，其特征在于，所述的溴代六氢茚酮类化合物I与所述杀菌剂中的任意一种或两种组合形成杀菌组合物用于防治农业和林业以及园艺植物病害；The use according to claims 6-7, characterized in that the brominated hexahydroindanone compound I is combined with any one or both of the bactericides to form a bactericidal composition for controlling agriculture and Forestry and horticultural plant diseases;

   优选地，，所述杀菌剂选自：苯并噻二唑、噻酰菌胺，简写为TDL、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺，其英文通用名为：isotianil、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、氟酰胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、呋吡菌胺、吡噻菌胺、双炔酰菌胺、苯酰菌胺、甲呋酰胺、萎锈灵、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、***醇、灭菌唑、联苯***醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、灭锈胺、多菌灵、苯菌灵、 甲基硫菌灵、***酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、硫线磷、丰索磷、虫线磷、苯线磷、灭线磷、除线磷、氯唑磷、丁硫环磷、杀线威、涕灭威、克百威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑；Preferably, the bactericide is selected from the group consisting of: benzothiadiazole, thiazide, abbreviated as TDL, thiazamide, methyl thiazide, 4-methyl-1,2,3-thiadiazole-5 - formic acid, sodium 4-methyl-1,2,3-thiadiazole-5-carboxylate, ethyl 4-methyl-1,2,3-thiadiazole-5-carboxylate, DL-β-aminobutyric acid Isotianil, its common name in English is: isotianil, 3,4-dichloroisothiazol-5-carboxylic acid, 3,4-dichloroisothiazol-5-formate, 3,4-dichloroisothiazol-5 - ethyl formate, ribavirin, antofin, nymidine or salicylic acid, cymoxanil, thiram, thiram, mancozeb, ethylaphosphonate, thiophanate, chlorothalonil, Enchkixone, procymidone, fenpropidin, methyl thiophanate, thiophanate, refined metalaxyl, flumorph, enoylmorpholine, high-performance metalaxyl, high-efficiency benzoxanthin, chloramphenicol, Sulfasamine, mesalamide, thifluzamide, fluamide, leaf cumin, cyclopropionamide, cycloflufenamide, cyclidamide, cyanamide, thiabendamide, flufenamide , penthiopyramine, dipropanoylamide, benzilamide, mefenamide, wilting, etoxin, iprodione, azoxystrobin, fenfluramine, fluz , ether oxystrobin, phenoxystrobin, anthracycline, picoxystrobin, pyraclostrobin, trifloxystrobin, enestrobin, enestrobin, oxycyclazole, carbendazole, cyclazole Alcohol, difenoconazole, diniconazole, high-efficiency diniconazole, epoxiconazole, nitrile azole, fluoroquinazole, flusilazole, fluconazole, hexaconazole, imidazole, inocastazole, leaf Pyrazole, myclobutanil, penconazole, propiconazole, prothioconazole, silrazole, tebuconazole, tetrafluoroetherazole, triazole alcohol, sterilized azole, biphenyl triazole alcohol, thiabendazole , Mai Sui Ning, imazalil, high-efficiency imazalil, prochloraz, fluconazole, cyanoxazole, imidacloprid, moxazole, rice sterol ester, famoxadone, pyridine oxazole, carbendazim , oxacillin, ethaboxam, carbendazim, octyl thiazolone, thiothiazide, dodecaline morpholine, butyl morpholine, thirteen morpholine, seed dressing, fluke nitrile, fluazinam, Pyridoxine, Cycloheximide, boscalid, fluaziram, acetazin, cyprodinil, fluzalazine, azoxystrobin, azoxystrobin, pyrimethanil, chlorpyrimidine , fluoropyrimidinol, chlorpyrifos, dicyanoquinone, ethoxyquin, quinolinol, Oxyquinoline, phenoxyquinoline, carbendazim, isopropylidene, phenothiamine, propamocarb, sulfavir, enemies, diarrhea, pyridoxine, methyl phos Quercetin, Chunleimycin, Polymycin, Polyoxomycin, Azadirachtin, Jinggangmycin, Streptomycin, Metalaxyl, Furosemide, Benzoicin, Furamide, Arsenicamine, Multi Fungi, benomyl, Methyl thiophanate, triadimefon, acetazol sulfonate, dipyridol, acesulfame, dipyridamole, captan, sterilized dan, vinyl nucleus, chlorofluorobacteria, bacteria Nuclear net, chlorothalonil, indigo, rice bran, leaf azole, pentachloronitrobenzene, propidium zinc, aluminum triethylphosphinate, sulfur, Bordeaux mixture, copper sulfate, copper oxychloride, oxidized Copper, copper hydroxide, benomyl, pentosan, chlorhexidine, tetrachlorophenyl hydrazine, praziquantel, spirocyclamamine, tricyclazole, pyrazinamide, polyglycoside, biguanide salt, diterpene Amine, chloramine, benzepamide, toluidine, oxime ester, sodium sulfonate, quinocodone, allyl benzothiazole, bronopol, methyl iodide, Weibaimu, enemy ester, cotton , dichloroisopropyl ether, thiazolyl, sulphur, phosphorus, folsa, phosphatidylcholine, phenylphosphorus, phosphine, phosphatidylcholine, chlorpyrifos, sulphur phosphine, chlorpyrifos, aldicarb , carbofuran, sulfuryl fluoride, dichloropropene, dichloroisonicotinic acid, allyl isothiazole;

   优选地，所述的溴代六氢茚酮类化合物I在所述杀菌组合物中的总的质量百分含量是1％-90％；Preferably, the total mass percentage of the brominated hexahydroindanone compound I in the germicidal composition is from 1% to 90%;

   优选地，所述的溴代六氢茚酮类化合物I与所述杀菌剂的比例为质量百分比1％∶99％到99％∶1％；Preferably, the ratio of the brominated hexahydroindanone compound I to the bactericide is 1% by mass: 99% to 99%: 1% by mass;

   优选地，所述杀菌组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；Preferably, the bactericidal composition is processed in a dosage form selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble concentrate, poisonous valley, block bait , granular bait, flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, heat Spray, cold spray, aerosol, solid/liquid mixed charge, liquid/liquid mixed charge, solid/solid mixed charge, lacquer, microparticle, trace powder, oil suspension, oil dispersible powder, Thickener, pouring agent, seed coating agent, smear agent, film forming oil agent, ultra low volume liquid agent, steam release agent;

   优选地，所述杀菌组合物防治的植物病害选自：稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病；Preferably, the plant disease controlled by the bactericidal composition is selected from the group consisting of: rice seedling cotton rot, tomato root rot, potato late blight, tobacco black shank, millet powdery mildew, grape downy mildew, lettuce downy mildew, cucumber Downy mildew, cucumber anthracnose;

   所述杀菌组合物适用的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。The bactericidal composition is suitable for plants selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, pea, broad bean, pea, mung bean, adzuki bean, cotton, sericulture, peanut, rape, sesame , sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, rape, onion, garlic, Watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.
10. 根据权利要求6-7所述的用途，其特征在于，所述的溴代六氢茚酮类化合物I与所述抗病毒药剂中的任意一种或两种组合形成抗病毒组合物用于防治农业和林业以及园艺植物病毒病害，The use according to claims 6-7, characterized in that the hexahydroindanone compound I is combined with any one or both of the antiviral agents to form an antiviral composition for control Agriculture and forestry and horticultural plant virus diseases,

    优选地，，所述商品抗病毒药剂选自：苯并噻二唑、噻酰菌胺，简写为TDL、异噻菌胺，其英文通用名为：isotianil、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5- 甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、DL-β-氨基丁酸、病毒唑、安托芬、宁南霉素、噻酰胺、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈羟胺、井冈霉素；Preferably, the commercial antiviral agent is selected from the group consisting of: benzothiadiazole, thiazide, abbreviated as TDL, isothiazide, and its common name in English is: isotianil, 4-methyl-1, 2, 3-thiadiazol-5-carboxylic acid, 4-methyl-1,2,3-thiadiazole-5- Sodium formate, ethyl 4-methyl-1,2,3-thiadiazole-5-carboxylate, 3,4-dichloroisothiazol-5-carboxylic acid, sodium 3,4-dichloroisothiazol-5-carboxylate, 3 , 4-Dichloroisothiazol-5-carboxylic acid ethyl ester, DL-β-aminobutyric acid, ribavirin, antofin, ningnanmycin, thiazamide, methyl thiazide or salicylic acid, pyrimycin , dichloroisonicotinic acid, allylisothiazole, Jinggang hydroxylamine, Jinggangmycin;

    优选地，所述的溴代六氢茚酮类化合物I在所述抗病毒组合物中的总的质量百分含量是1％-90％；Preferably, the total mass percentage of the brominated hexahydroindanone compound I in the antiviral composition is from 1% to 90%;

    优选地，所述的溴代六氢茚酮类化合物I与所述抗植物病毒剂的比例为质量百分比1％∶99％到99％∶1％；Preferably, the ratio of the brominated hexahydroindanone compound I to the anti-plant virus agent is 1% by mass: 99% to 99%: 1% by mass;

    优选地，所述抗病毒组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；Preferably, the antiviral composition is processed in a dosage form selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble concentrate, poisonous valley, lumps Bait, granular bait, flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, Hot mist, cold spray, aerosol, solid/liquid mixed charge, liquid/liquid mixed charge, solid/solid mixed charge, lacquer, microparticle, trace powder, oil suspension, oil dispersible powder , thickener, pouring agent, seed coating agent, smear agent, film forming oil agent, ultra low volume liquid agent, steam release agent;

    优选地，所述抗病毒组合物防治的病毒病害选自：水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒；Preferably, the viral disease controlled by the antiviral composition is selected from the group consisting of rice dwarf disease, yellow dwarf disease, stripe leaf blight, tomato fern leaf virus disease, pepper mosaic virus disease, tobacco vein necrosis virus disease, corn dwarf Mosaic disease, cauliflower mosaic virus, citrus virus disease, broccoli virus, Jianlan ring spot virus;

    优选地，所述抗病毒组合物用于防治的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。Preferably, the plant for controlling the antiviral composition is selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, tapioca, soybean, pea, broad bean, pea, mung bean, adzuki bean, cotton, sericulture , peanuts, rapeseed, sesame, sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, Rape, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.
11. 根据权利要求6-7所述的用途，其特征在于，所述的溴代六氢茚酮类化合物I与所述杀螨剂中的任意一种或两种组合形成杀螨组合物用于防治农业和林业以及园艺植物螨害，The use according to claims 6-7, characterized in that the hexahydroindanone compound I is combined with any one or both of the acaricides to form a acaricidal composition for controlling Agriculture and forestry, as well as horticultural plant damage,

    优选地，所述杀螨剂选自：***锡、三环锡、苯丁锡、三磷锡、毒虫畏、甲基毒虫畏、巴毒磷、敌敌畏、庚烯磷、速灭磷、久效磷、二溴磷、毒死蜱、嘧啶磷、氯甲亚胺硫磷、氧乐果、敌杀磷、乙硫磷、马拉硫磷、虫螨畏、伏杀硫磷、辛硫磷、甲基嘧啶硫磷、喹硫磷、治螟磷、***磷、蚜灭多、水胺硫磷、甲胺磷、胺丙畏、氯亚胺 硫磷、亚胺硫磷、氟丙菊酯、联苯菊酯、氯氟氰菊酯、精高效氯氟氰菊酯、甲氰菊酯、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯、溴氟菊酯、联苯肼酯、苯硫威、涕灭威、丁酮威、杀线威、抗虫威、久效威、苯菌灵、氯灭杀威、克百威、丁硫克百威、速灭威、蜱虱威、伐虫脒、单甲脒、杀螨脒、双甲脒、杀虫脒、苯甲酸苄酯、溴螨酯、丁氟螨酯、灭螨醌、氟蚜螨、氟虫脲、浏阳霉素、虫螨霉素、苏云金素、杀螨素、浏阳霉素、阿维菌素、多拉菌素、埃普利诺菌素、伊维菌素、赛拉菌素、莫西菌素、除虫菊素、烟碱、苦参碱、印楝素、鱼藤酮、吡螨胺、哒螨酮、唑螨酯、四螨嗪、炔螨特、噻螨酮、螺螨酯、嘧螨酯、杀螨酯、克螨特、哒螨灵；Preferably, the acaricide is selected from the group consisting of: triazole tin, tricyclotin, phenbutyltin, triphosphorus, chlorpyrifos, methyl chlorpyrifos, phytophos, dichlorvos, heptene phosphorus, quick-killing phosphorus, long time Phosphorus, dibromophosphorus, chlorpyrifos, pyrimidine, chloromethylimine, omethoate, chlorpyrifos, ethion, malathion, worm, phoxim, phoxim, Pyrithione, quetiapine, strontium phosphate, triazophos, quenching, heptaphos, methamidophos, aminoxime, chlorimimine Thiofos, imipenem, flumethrin, bifenthrin, cyhalothrin, cyhalothrin, fenpropathrin, fluvalerate, flumethrin, fluoride Cypermethrin, bifenthrin, bifenazate, phenylthiocarb, aldicarb, butanone, chlorpyrifos, anti-insect, long-acting, benomyl, chlorhexidine, kebai Wei, Ding Ke Ke Wei, Kui Wei Wei, Converse, Valerian, Monomethylhydrazine, Acaricide, Amitraz, Insecticidal, Benzoyl Benzoate, Bromodecyl Ester, Butyl Fluoride, Quercetin, fluoropterin, flubendiamide, liuyangmycin, echinomycin, sulphate, acaricidin, liuyangmycin, avermectin, doramectin, eplenomycin, y Vermicillin, serramycin, moxidectin, pyrethrin, nicotine, matrine, azadirachtin, rotenone, pyridoxamine, anthrone, oxazolidine, tetrazine, alkyne, Thiazolinone, spirodecyl ester, pyrimidin, acaricidal ester, ketone, hydrazine;

    优选地，所述的溴代六氢茚酮类化合物I在所述杀螨组合物中的总的质量百分含量是1％-90％；Preferably, the total mass percentage of the brominated hexahydroindanone compound I in the acaricidal composition is from 1% to 90%;

    优选地，所述的溴代六氢茚酮类化合物I与所述商品杀螨剂的比例为质量百分比1％∶99％到99％∶1％；Preferably, the ratio of the brominated hexahydroindanone compound I to the commercial acaricide is 1% by mass: 99% to 99%: 1% by mass;

    优选地，所述杀螨组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；Preferably, the dosage form processed by the acaricidal composition is selected from the group consisting of: seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble concentrate, poisonous valley, block Bait, granular bait, flake bait, concentrated bait, slow release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke tube, smoke stick, smoke sheet, smoke pill, gas generator, ointment, Hot mist, cold spray, aerosol, solid/liquid mixed charge, liquid/liquid mixed charge, solid/solid mixed charge, lacquer, microparticle, trace powder, oil suspension, oil dispersible powder , thickener, pouring agent, seed coating agent, smear agent, film forming oil agent, ultra low volume liquid agent, steam release agent;

    优选地，所述杀螨组合物防治的螨害选自：螨害选自叶螨科、细须螨科、呋线螨、瘿螨科、红叶螨属、瘿螨科的害螨，这些害螨是世界性农业害螨、林业害螨、园艺害螨和卫生害螨；Preferably, the cockroach damage controlled by the acaricidal composition is selected from the group consisting of: the mites are selected from the group consisting of the genus Aphididae, the genus Diptera, the eucalyptus, the genus Eucalyptus, the genus Eucalyptus, and the mites. World agricultural pests, forest pests, horticultural pests and health hazards;

    优选地，所述杀螨组合物用于防治的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。 Preferably, the plant for controlling the acaricidal composition is selected from the group consisting of: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, pea, broad bean, pea, mung bean, adzuki bean, cotton, sericulture , peanuts, rapeseed, sesame, sunflower, beet, sugar cane, coffee, cocoa, ginseng, fritillary, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard, beet, Rape, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus and peach, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.