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WO2010139271A1 - 含取代苯胺基嘧啶基团的e-型苯基丙烯酸酯类化合物及其应用 - Google Patents

含取代苯胺基嘧啶基团的e-型苯基丙烯酸酯类化合物及其应用 Download PDF

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Publication number
WO2010139271A1
WO2010139271A1 PCT/CN2010/073484 CN2010073484W WO2010139271A1 WO 2010139271 A1 WO2010139271 A1 WO 2010139271A1 CN 2010073484 W CN2010073484 W CN 2010073484W WO 2010139271 A1 WO2010139271 A1 WO 2010139271A1
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WO
WIPO (PCT)
Prior art keywords
chloro
compound
fluoro
methyl
dichloro
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Application number
PCT/CN2010/073484
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English (en)
French (fr)
Inventor
刘长令
李慧超
张弘
柴宝山
罗艳梅
何晓敏
黄光�
刘少武
孙宝祥
Original Assignee
中国中化股份有限公司
沈阳化工研究院有限公司
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Application filed by 中国中化股份有限公司, 沈阳化工研究院有限公司 filed Critical 中国中化股份有限公司
Priority to CN201080016379.5A priority Critical patent/CN102395569B/zh
Priority to ES10782975.6T priority patent/ES2439052T3/es
Priority to JP2012513463A priority patent/JP5416838B2/ja
Priority to US13/265,379 priority patent/US8609667B2/en
Priority to BRPI1010756-8A priority patent/BRPI1010756B1/pt
Priority to EP10782975.6A priority patent/EP2439199B1/en
Publication of WO2010139271A1 publication Critical patent/WO2010139271A1/zh

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4

Definitions

  • the invention belongs to the field of agricultural, civil and animal technology insecticidal and acaricidal agents. Specifically, it relates to an E-type phenyl acrylate compound containing a substituted anilinopyrimidine group and uses thereof. Background technique
  • the natural product methoxy acrylate compound is a known biologically active compound.
  • the methoxy acrylate compounds as insecticidal and acaricidal agents have been reported in the following documents: EP242081, EP299694, EP335519, US2006235075 and the like.
  • Patent US 5,106,852 relates to the following compounds of the general formula as insecticides:
  • alkyl selected from alkyl, cycloalkyl, haloalkyl, alkoxy, alkylthio or substituted and unsubstituted aryl.
  • Patent US5378711 relates to the following compounds as fungicides:
  • Patent US 5,935,965 relates to the following compounds of the general formula as a killing and bactericide:
  • Patent US6114342 relates to the following compounds of the general formula as insecticidal and fungicides:
  • the applicant of the present invention has disclosed a compound of the following formula as a bactericidal and bactericidal agent in the patent application of WO2008145052A1 or CN101311170A:
  • the object of the present invention is to provide an E-type phenyl acrylate compound containing a substituted anilinopyrimidine group which can be used for controlling pests in agriculture, civil and animal technology at a small dose.
  • the inventors of the present invention obtained the obtained compounds of the present invention not only have good killing activity, but also have excellent ovicidal activity.
  • the technical solution of the present invention is as follows:
  • the present invention provides an E-type phenyl acrylate compound having a substituted anilinopyrimidine group, as shown in Formula I:
  • Ri is selected from halogenated CC 3 alkyl
  • R 2 is selected from hydrogen, halo, cyano, nitro, dC 12 alkyl, ⁇ alkoxy, halo C12 alkoxy, alkylthio or dC 12 12 alkylsulfonyl;
  • R 2 and a pyrimidine ring constitute a cyclopentanepyrimidine or a cyclohexane-pyrimidine;
  • R 3 is selected from the group consisting of hydrogen, cyano, dC 12 alkyl, halo dC 12 alkyl, C 3 -C 6 cycloalkyl, 12 alkoxy, halo 12 alkoxy, dC 12 ⁇ thio, dC 12 Alkylsulfonyl, dC 12 alkylcarbonyl, 12 alkoxy dC 12 alkyl, dC 12 alkoxycarbonyl, dC 12 alkoxycarbonyl C r C 12 alkyl, unsubstituted or 1-5 independent
  • R 2 is selected from the group consisting of hydrogen, chlorine or methyl
  • R 2 and a pyrimidine ring constitute a cyclopentanepyrimidine or a cyclohexane-pyrimidine;
  • R 3 is selected from hydrogen, C r C 4 alkyl, C r C 4 alkylsulfonyl or C r C 4 alkylcarbonyl;
  • Rn is selected from 2,3-difluoro, 2, 4-Difluoro, 2,4-dichloro, 2-fluoro-3-chloro, 2-chloro-3-fluoro, 2-fluoro-4-chloro, 2-chloro-4-fluoro, 2,3,4- Trifluoro, 2,3,4-trichloro, 2,4-difluoro-3-methyl, 2,4-dichloro-3-methyl, 2-fluoro-3,4-dichloro or 2-chloro -3,4-difluoro;
  • Rn is selected from the group consisting of hydrogen, 2-chloro, 4-chloro, 2,3-difluoro, 2,4-difluoro, 2,3-dichloro, 2,4-di Chlorine, 2-fluoro-3-chloro, 2-chloro-3-fluoro, 2-fluoro-4-chloro, 2-chloro-4-fluoro, 2,3,4-trifluoro, 2,3,4-tri Chlorine, 2,4-difluoro-3-methyl, 2,4-dichloro-3-methyl, 2-fluoro-3,4-dichloro or 2-chloro-3,4-difluoro;
  • R 2 and the pyrimidine ring constitute a cyclopentadepyrimidine or a cyclohexane pyrimidine
  • Ri is selected from trifluoromethyl
  • R 2 is selected from the group consisting of hydrogen, chlorine or methyl
  • R 2 and a pyrimidine ring constitute a cyclopentanepyrimidine or a cyclohexane-pyrimidine;
  • R 3 is selected from hydrogen
  • Rn is selected from the group consisting of 2,4-difluoro, 2,4-dichloro, 2-fluoro-4-chloro, 2-chloro-4-fluoro, 2,3,4-trifluoro, 2,3,4-trichloro or 2,4-dichloro-3-methyl;
  • Rn is selected from the group consisting of hydrogen, 2-chloro, 4-chloro, 2,4-difluoro, 2,3-dichloro, 2,4-dichloro, 2-fluoro-4 -chloro, 2-chloro-4-fluoro, 2,3,4-trifluoro, 2,3,4-trichloro or 2,4-dichloro-3-methyl;
  • R 2 and the pyrimidine ring constitute a cyclopentanepyrimidine or a cyclohexane pyrimidine
  • Halogen means fluorine, chlorine, bromine or iodine.
  • Alkyl a linear or branched alkyl group such as methyl, ethyl, propyl, isopropyl or t-butyl.
  • Cycloalkyl a substituted or unsubstituted cyclic alkyl group such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen and the like.
  • Haloalkyl a linear or branched alkyl group in which a hydrogen atom may be partially or completely substituted by a compound such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, Fluoromethyl, trifluoromethyl, and the like.
  • Alkoxy A linear or branched alkyl group bonded to a structure via an oxygen atom.
  • Haloalkoxy a linear or branched alkoxy group, and a hydrogen atom on these alkoxy groups may be partially or completely substituted by a halogen.
  • a halogen for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, and the like.
  • Alkylthio a linear or branched alkyl group bonded to a structure via a sulfur atom bond.
  • the compound represented by the formula I is obtained by reacting a hydroxyl group-containing pyrimidine compound represented by the formula III with benzyl chloride IV under an alkali injection condition:
  • Benzyl chloride IV can be obtained by a known method, as described in detail in US5663370 and the like.
  • a suitable solvent may be selected from, for example, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide, dimethyl sulfoxide, acetone or methyl ethyl ketone.
  • Suitable bases may be selected from, for example, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium t-butoxide or sodium t-butoxide.
  • the reaction temperature may be between room temperature and the boiling point of the solvent, and is usually from 20 to 100 °C.
  • the reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
  • the present invention also includes a salt of the compound of the formula I, that is, a salt formed from the 2-position amine of the pyrimidine group and the corresponding acid, which can be obtained by a conventional method from the compound of the formula I and the corresponding acid.
  • the salt of the compound of the formula I may be an inorganic salt such as a hydrochloride or a phosphate; or an organic salt such as an acetate, a benzenesulfonate or an oxalate.
  • the intermediate III can be obtained by condensation of the intermediate II with a ⁇ -ketoester compound (e.g., ethyl trifluoroacetoacetate, etc.) according to a known method.
  • a ⁇ -ketoester compound e.g., ethyl trifluoroacetoacetate, etc.
  • the intermediate II can be purchased or prepared by known methods, as described in detail in EP310550, EP0655441 and the like. Some specific intermediates III are shown in Table 4
  • the compound of the formula I is active against important species of the following families: Aphididae (two-spotted spider mites, cinnabar leaf mites, apple whole-clawed scorpion, citrus full-clawed scorpion, etc.), Aphididae, Aphididae, and the like.
  • the compounds of formula I are less toxic to many beneficial insects and aphids, mammals, fish, birds, and are not phytotoxic.
  • the above compounds are advantageously used to protect crops, livestock and stocks important in agriculture and horticulture, as well as the environment in which humans are often exposed to harmful aphids and harmful insects.
  • the amount of the compound varies depending on various factors such as the compound used, the pre-protected crop, the type of the pest, the degree of infection, the climatic conditions, the method of application, and the dosage form employed.
  • a dose of 10 grams to 5 kilograms of compound per hectare provides adequate control.
  • a further object of the invention also relates to a method for controlling pests and/or phytopathogenic fungi in agricultural and horticulturally important crops and/or livestock and breeding stocks and/or environments frequented by humans by administering the compounds of formula I .
  • the amount of the compound varies from 10 g to 5 kg per hectare.
  • Another embodiment of the present invention further comprises an insecticidal and acaricidal composition
  • an insecticidal and acaricidal composition comprising as an active ingredient a compound of the formula I and an agriculturally acceptable carrier, wherein the active ingredient is present in an amount of 0.5 by weight. -90%.
  • the technical solution of the present invention also includes the use of the above composition for controlling pests in agriculture and other fields.
  • composition comprising one or more compounds of formula I.
  • the form of use (formulation type) of the composition may be dry powder, wettable powder, emulsifiable concentrate, microemulsion, paste, Granules, solutions, suspensions, and the like.
  • the choice of the form of use of the composition will depend on the particular application.
  • composition is prepared in a known manner, for example by diluting or dissolving the active substance with a solvent medium and/or a solid diluent, optionally in the presence of a surfactant.
  • Useful solid diluents or carriers are, for example: silica, kaolin, bentonite, talc, diatomaceous earth, dolomite, calcium carbonate, magnesium oxide, chalk, clay, synthetic silicate, attapulgite, sepiolite.
  • useful liquid diluents are, for example, aromatic organic solvents (mixtures of xylene or alkylbenzenes, chlorobenzene, etc.), paraffin (petroleum fractions), alcohols (methanol, propanol, butanol, octanol, Glycerin), esters (ethyl acetate, isobutyl acetate, etc.), ketones (cyclohexanone, acetone, acetophenone, isophorone, ethyl amyl ketone, etc.), amides (N, N- Dimethylformamide, N-methylpyrrolidone, etc.).
  • aromatic organic solvents mixture of xylene or alkylbenzenes, chlorobenzene, etc.
  • paraffin paraffin
  • alcohols methanol, propanol, butanol, octanol, Glycerin
  • esters ethyl acetate, isobutyl
  • Usable surfactants are sodium, calcium, triethylamine, such as alkyl sulfonates, alkyl aryl sulfonates, polyoxyethylene alkyl phenols, polyoxyethylene esters of sorbitol, lignosulfonates, and the like. Or triethanolamine salt.
  • composition may also contain special additives for specific purposes such as binders such as gum arabic, polyvinyl alcohol, polyvinylpyrrolidone and the like.
  • binders such as gum arabic, polyvinyl alcohol, polyvinylpyrrolidone and the like.
  • the concentration of the active ingredient in the above composition may vary widely depending on the active ingredient, its intended use, environmental conditions, and the type of preparation employed. Generally, the concentration of the active ingredient ranges from 1 to 90%, preferably from 5 to 50%.
  • compositions may be added to the compositions, such as other acaricides/insecticides, fungicides, plant growth regulators, antibiotics, herbicides, fertilizers.
  • suspending agent The active ingredient content in the commonly used formula is 5%-35%.
  • the water is used as a medium, and the original drug, the dispersing agent, the suspending agent and the antifreezing agent are added to a sand mill to be ground to prepare a suspension.
  • Preparation of wettable powder According to the formulation requirements, the original drug, various surfactants and solid diluents are thoroughly mixed and pulverized by an ultrafine pulverizer to obtain a wettable property of a predetermined content (for example, 10% to 40%). Powder products.
  • the compounds of the invention may be admixed with finely divided solid powders such as clays, inorganic silicates, carbonates, and wetting agents, binders and/or dispersing agents.
  • Preparation of water-dispersible granules Mix and pulverize the original drug with powdered solid diluent, wetting spreader and binder, add water and knead, and add granulator with 10 to 100 mesh screen Granulation is carried out, followed by drying and sieving (by sieve range).
  • the original drug, dispersing agent, disintegrating agent and wetting agent and solid diluent may also be added to a sand mill, ground with water as a suspending agent, and then spray-dried and granulated, usually in a content of 20%. — 30% granulated product.
  • Compound 8 Melting point 105-107. C. S (ppm): 3.70 (s, 3H), 3. 80 (s, 3H), 5.31 (s, 2H), 6.54 (s, 1H), 6.90 (m, 2H), 7.20 (m, 1H), 7.28 (m, 1H), 7.36 (m, 2H), 7.48 (m, 1H), 7.59 (s, 1H), 8.28 (m, 1H).
  • Compound 96 Melting point 106-108. C. 5 (ppm): 2.08 (m, 2H), 2.77 (t, 2H), 2.85 (t, 2H), 3.69 (s, 3H), 3.77 (s, 3H), 5.32 (s, 2H), 6.84 (m , 2H), 7.04 (m, 1H), 7.19 (m, 1H), 7.34 (m, 2H), 7.51 (m, 1H), 7.58 (s, 1H), 8.35 (m, 1H).
  • Compound 138 Melting point 170-171.
  • Example 4 30% Compound 9 Wettable Powder
  • Example 5 60% Compound 88 Water-dispersible granules
  • Kaolin is made up to 100%
  • the compound 88 and other components are mixed and pulverized, and then kneaded by water, and then granulated by adding into a granulator of a 10-100 mesh sieve, and then dried and sieved (by a sieve range) to obtain 60%. Water-dispersible granules.
  • Biological activity assay
  • Example 6 Determination of indoor acaricidal activity
  • the indoor activity assay of the sorghum, scorpion and scorpion eggs of the cinnabarinus sinensis was carried out using the compound of the present invention.
  • the method of determination is as follows:
  • Determination of the activity of the cockroach indoors After the compound was weighed, the mother liquor was made of acetone, and the serial concentration was diluted according to the experimental design with static tap water containing 0.1% Tween 80. Two true leafy bean sprouts were inoculated, inoculated with cinnabar leaf mites and investigated for base number, and then sprayed with a hand-held sprayer (DeVilbiss Atomizer M163), three times per treatment, placed in a standard observation room after treatment, and the number of survival sputum was investigated after 72 hours. Calculate the mortality rate.
  • ⁇ For indoor activity determination of ⁇ :: Take two slices of true leaf potted bean sprouts, then connect the healthy cinnabar leaf mites to the leaves and connect them to the leaves. After 24 hours, the mites are removed and the eggs continue to be cultured. After 7-10 days, they enter. After the investigation, the base was sprayed, and each treatment was repeated three times. After treatment, it was placed in a standard observation room. After 72 hours, the number of survival was investigated and the mortality was calculated.
  • Determination of indoor ovicidal activity Take a pot of bean sprouts to retain a true leaf, then connect the healthy cinnabar to the head of the scorpion, and then remove it into the leaves. After 24 hours, remove the mites, investigate the number of eggs, and then spray, treat and spray. The method is the same as the sputum test. After 5 days, all the blank control eggs were hatched, and the number of unhatched eggs in each treatment was investigated to calculate the hatching inhibition rate.
  • the lethal rates of 82, 83, 84, 85, 88, etc. for cinnabar mites are 100%; compounds 7, 129, etc. for cinnabar
  • the mortality rate of Ye Yucheng is higher than 90%.
  • the concentration of the drug solution is 40 mg/L
  • the lethal rates of compounds 2, 6, 8, 9, 12, 15, 16, 17, 18, 79, 80, 88, etc. for cinnabarin are 100%; compound 13, 82
  • the mortality rate of 84, etc. on the cinnabar leaf mites is above 95%.
  • the concentration of the chemical solution is 10 mg/L
  • the lethal rates of compounds 2, 8, 9, 12, 15, 16, 17, 79, etc. for the cinnabar mites are 100%, and the compounds 13, 80, 82, 84, 88, etc.
  • the mortality rate of cinnabarinus sinensis is higher than 80%.
  • the lethal rates of the compounds 8, 9, 12, 15, 16, 17 and so on for the cinnabar are 100%.
  • the mortality rate of 9 and so on to the cinnabar leaf mites is above 85%.
  • the concentration of the drug solution is 0.31 mg/L
  • the lethal rate of compound 15 and the like on the cinnabar is higher than 75%.
  • the concentration of the drug solution was 2.5 mg/L
  • the lethal rate of the compound 9 and 15 to the cinnabar was 100%
  • the lethal rate of the compound 8 to the cinnabar was higher than 95%.
  • the concentration of the chemical solution is 0.63 mg/L
  • the lethal rate of compound 15 and the like on the cinnabar leaf is 100%
  • the lethal rate of the compound 9 on the cinnabar leaf is higher than 95%
  • the compound 8 is on the cinnabar leaf. If the mortality rate of cockroaches is higher than 75%.
  • Control A Control B Control C The commercial product pyridoxine (commercially available from Tiandeng, 30% suspension, manufactured by Soda, Japan) and snail ester (commercially endangered, 24% suspension, manufactured by Bayer) were used.
  • a control compound an activity comparison test was carried out with the compound of the present invention. The measurement method is the same as described above.
  • the test was carried out in a 2-year-old succulent citrus orchard in Chaotian Township, Lingchuan County, Guilin City.
  • the rootstock was ⁇
  • the plant spacing was 1. 5 X 2. 5 meters
  • the average plant height was 1.45 meters
  • the crown width was 1.30 meters. 2 trees per plot, repeated 4 times, arranged in random blocks.
  • Compound 9 (15% suspension) was given in two doses of 100 mg/L and 25 mg/L, and spironolactone (24% suspension) was given at a dose of 48 mg/L; using "MATABI" super green 16-type knapsack sprayer ( Matabi Supergreen) 16 Knapsack Sprayer 16 Litre ) Evenly sprayed with a spray volume of about 2L per plant.
  • citrus red spiders were found to be sputum, young scorpion, and scorpion eggs, and the ratio of scorpion eggs was 1: 1. 27.
  • the weather was fine on the day of application, the average temperature was 23 °C, and the weather was fine for 3 days after application.
  • the number of insect populations was investigated before application, and each of them was investigated once, 3 days, 10 days, 15 days, 20 days, and 30 days after application.
  • 2 trees were surveyed per plot. According to the east, west, south, north and middle directions of the canopy, the number of active states on 5 leaves was investigated in each direction. 50 leaves were investigated in each plot, and the mouth was calculated according to the following formula.
  • Mouth reduction rate (%) [(the average number of leaves before application - the average number of leaves after application) / the number of leaves before application]
  • X 100 control effect (%) [ (treatment area diverted Rate - untreated area mouthwash rate) / (100-untreated area mouthwash rate)]
  • X lOOo Compound 9 test results of citrus red spider field trial (Guilin, Guangxi) are shown in Table 9: Table 9

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Description

含取代苯胺基嘧啶基团的 E-型苯基丙烯酸酯类化合物及其应用 技术领域
本发明属农业、 民用和动物技术杀虫杀螨剂领域。 具体地涉及一种含取代苯胺基 嘧啶基团的 E-型苯基丙烯酸酯类化合物及其应用。 背景技术
天然产物甲氧基丙烯酸酯化合物是已知的具有生物活性的化合物。如下文献曾报 道过作为杀虫杀螨剂的甲氧基丙烯酸酯化合物： EP242081、 EP299694、 EP335519、 US2006235075等。
另外， 嘧啶甲氧基丙烯酸酯类化合物也有报道作为杀虫、 杀螨或杀菌剂的： 专利 US5106852中涉及以下通式化合物作为杀虫剂：
Figure imgf000002_0001
其中： 选自烷基、 环烷基、 卤代烷基、 烷氧基、 烷硫基或取代的和非取代的芳 基。
专利 US5378711中涉及以下化合物作为杀菌剂:
Figure imgf000002_0002
专利 US5935965中涉及以下通式化合物作为杀螨、 杀菌剂:
Figure imgf000002_0003
专利 US6114342中涉及以下通式化合物作为杀虫、 杀菌剂:
Figure imgf000002_0004
本发明的申请人在 W02008145052A1或 CN101311170A专利申请中曾公开如下通式 化合物作为杀螨、 杀菌剂：
Figure imgf000003_0001
尽管已有类似专利， 但仍需要不断研发出效果更佳的杀虫杀螨化合物以控制农 业、 民用和动物技术领域中有害的螨虫和昆虫。 发明内容
本发明的目的在于提供一种在很小的剂量下就可以应用于农业、民用和动物技术 领域中控制害虫害螨的一种含取代苯胺基嘧啶基团的 E-型苯基丙烯酸酯类化合物，本 发明人通过详尽研究， 得到的本发明化合物不仅具有很好的杀成螨、 若螨活性， 而且 具有更优的杀卵活性。 本发明的技术方案如下：
本发明提供一种含取代苯胺基嘧啶基团的 E-型苯基丙烯酸酯类化合物， 如通式 I 所示：
Figure imgf000003_0002
式中：
Ri选自卤代 C C3烷基；
R2选自氢、 卤素、氰基、 硝基、 d-C12烷基、 ^烷氧基、 卤代 12烷氧基、 12烷硫基或 d-C12烷基磺酰基；
或者 、 R2与嘧啶环组成环戊烷并嘧啶或环己烷并嘧啶；
R3选自氢、 氰基、 d-C12烷基、 卤代 d-C12烷基、 C3-C6环烷基、 12烷氧基、 卤代 12烷氧基、 d-C12 ^硫基、 d-C12烷基磺酰基、 d-C12烷基羰基、 12烷 氧基 d-C12烷基、 d-C12烷氧基羰基、 d-C12烷氧基羰基 CrC12烷基、 未取代的或被 1-5个独立选自以下基团取代的苯基、 苄基、 苯基羰基、 苄基羰基、 苯基磺酰基或苄 基磺酰基： 卤素、硝基、氰基、 d-C4烷基、 卤代 d-C4烷基、 d-C4烷氧基、 卤代 d-C4 烷氧基或 d-C4烷硫基；
R选自卤素、 氰基、 硝基、 d-C4烷基或卤代 CrC3烷基， n=0-5;
或其盐。 本发明较优选的化合物为： 通式 I 中
选自三氯甲基、 一氯二氟甲基、 二氯一氟甲基、 三氟甲基或 2，2，2-三氟乙基；
R2选自氢、 氯或甲基；
或者 、 R2与嘧啶环组成环戊烷并嘧啶或环己烷并嘧啶； R3选自氢、 CrC4烷基、 CrC4烷基磺酰基或 CrC4烷基羰基； 当 R2选自氢时， Rn选自 2,3-二氟、 2,4-二氟、 2,4-二氯、 2-氟 -3-氯、 2-氯 -3-氟、 2-氟 -4-氯、 2-氯 -4-氟、 2，3，4-三氟、 2，3，4-三氯、 2,4-二氟 -3-甲基、 2,4-二氯 -3-甲基、 2- 氟 -3,4-二氯或 2-氯 -3,4-二氟；
当 R2选自氯或甲基时， Rn选自氢、 2-氯、 4-氯、 2,3-二氟、 2,4-二氟、 2,3-二氯、 2,4-二氯、 2-氟 -3-氯、 2-氯 -3-氟、 2-氟 -4-氯、 2-氯 -4-氟、 2，3，4-三氟、 2，3，4-三氯、 2,4- 二氟 -3-甲基、 2，4-二氯 -3-甲基、 2-氟 -3,4-二氯或 2-氯 -3,4-二氟；
当 、 R2与嘧啶环组成环戊烷并嘧啶或环己烷并嘧啶时， R选自卤素、 氰基、 硝基、 C C4烷基或卤代 d-C3烷基， n=0-4。
或其盐酸盐、 磷酸盐、 醋酸盐、 苯磺酸盐或草酸盐。 进一步优选的化合物为： 通式 I 中
Ri选自三氟甲基；
R2选自氢、 氯或甲基；
或者 、 R2与嘧啶环组成环戊烷并嘧啶或环己烷并嘧啶；
R3选自氢；
当 R2选自氢时， Rn选自 2,4-二氟、 2,4-二氯、 2-氟 -4-氯、 2-氯 -4-氟、 2，3，4-三氟、 2，3，4-三氯或 2,4-二氯 -3-甲基；
当 R2选自氯或甲基时， Rn选自氢、 2-氯、 4-氯、 2,4-二氟、 2,3-二氯、 2,4-二氯、 2-氟 -4-氯、 2-氯 -4-氟、 2，3，4-三氟、 2，3，4-三氯或 2,4-二氯 -3-甲基；
当 、 R2与嘧啶环组成环戊烷并嘧啶或环己烷并嘧啶时， R选自氯、 溴、 氟、 C C4烷基或卤代 d-C3烷基， n=0-3 ;
或其盐酸盐、 磷酸盐、 醋酸盐、 苯磺酸盐或草酸盐。 上面给出的通式 I化合物的定义中， 汇集所用术语一般代表如下取代基： 卤素： 指氟、 氯、 溴或碘。
烷基： 直链或支链烷基， 例如甲基、 乙基、 丙基、 异丙基或叔丁基。
环烷基： 取代或未取代的环状烷基， 例如环丙基、 环戊基或环己基。 取代基如甲 基、 卤素等。
卤代烷基：直链或支链烷基，在这些烷基上的氢原子可部分或全部被 ^素所取代， 例如， 氯甲基、 二氯甲基、 三氯甲基、 氟甲基、 二氟甲基、 三氟甲基等。
烷氧基： 直链或支链烷基， 经氧原子键连接到结构上。
卤代烷氧基： 直链或支链烷氧基， 在这些烷氧基上的氢原子可部分或全部被卤素 所取代。 例如， 氯甲氧基、 二氯甲氧基、 三氯甲氧基、 氟甲氧基、 二氟甲氧基、 三氟 甲氧基、 氯氟甲氧基、 三氟乙氧基等。
烷硫基： 直链或支链烷基， 经硫原子键连接到结构上。
下面表 1一表 3中列出的具体化合物可以用来说明本发明， 但并不限定本发明， 其中通式 I中苯环取代基 Rn用 、 R5、 、 R7表示。 表 1 ( 为 CF3)
Figure imgf000005_0001
Figure imgf000005_0002
Figure imgf000006_0001
74 CI H F F F H
75 Br H CI H CI H
76 Br H F H F H
77 Br H F F F H
78 CH3 H CI H CI H
79 CH3 H F H F H
80 CH3 H F F F H
81 CH3 H CI CI H H
82 CH3 H CI H H H
83 CH3 H H H CI H
84 CH3 H H H H H
85 CI H H H H H
86 CI H CI CI H H
87 CI H CI CH3 CI H 表 2 ( R 、 R2与嘧啶环组成环戊烷并嘧啶）
Figure imgf000007_0001
Figure imgf000007_0002
Figure imgf000008_0001
表 3 (Ri R2与嘧啶环组成环己烷并嘧啶）
Figure imgf000008_0002
表 3中化合物 129- 169各取代基分别依次同于表 2中化合物 88- 128的取代基 ; 本发明的通式 I 化合物可按照以下方法制备：
通式 I所代表的化合物由通式 III 所示的含羟基的嘧啶类化合物与苄氯 IV在碱 注条件下反应制得：
Figure imgf000009_0001
苄氯 IV可以由已知方法制得， 具体参见 US5663370等。
反应在适宜的溶剂中进行， 适宜的溶剂可选自如四氢呋喃、 乙腈、 甲苯、二甲苯、 苯、 N，N-二甲基甲酰胺、 二甲亚砜、 丙酮或丁酮等。
适宜的碱可选自如氢氧化钾、 氢氧化钠、 碳酸钠、 碳酸钾、 碳酸氢钠、 三乙胺、 吡啶、 甲醇钠、 乙醇钠、 氢化钠、 叔丁醇钾或叔丁醇钠等。
反应温度可在室温至溶剂沸点温度之间， 通常为 20〜100°C。
反应时间为 30分钟至 20小时， 通常 1〜10小时。
本发明还包括通式 I化合物的盐， 即由其嘧啶基团 2-位胺与相应的酸生成的盐， 可由通式 I化合物与对应的酸按常规方法制得。 通式 I化合物的盐可以为无机盐如盐 酸盐或磷酸盐等； 也可以是有机盐如醋酸盐、 苯磺酸盐或草酸盐等。
中间体 III 可由中间体 II与 β-酮酸酯类化合物 （例如三氟乙酰乙酸乙酯等） 按照 已知的方法縮合得到， 具体参见 GB1388402、 US4000138、 CH395385等。
Figure imgf000009_0002
中间体 II可以购得或通过已知方法制备， 具体参见 EP310550、 EP0655441等。 部分具体中间体 III见表 4-
Figure imgf000009_0003
编号 R3 4 R5 Re R7 熔点 （°c )
III- 1 H H H H CN H 242-245
III-2 H H F H H H 232-234
III-3 H H Br H H H
III-4 H H CN H H H
III-5 H H N02 H H H
III-6 H H H CH3 H H 196-198
III-7 H H H CF3 H H 180-182 ΠΙ-8 H H F H F H 243-244
ΠΙ-9 H H CI H CI H 253-254
III- 10 H H H CI CI H 234-238
III- 11 H H N02 H N02 H 254-256
III- 12 H H F H CI H 257-259
III- 13 H H H CI F H 195-196
III- 14 H H H F H CI
III- 15 H H F F F H 210-212
III- 16 H H CI CI CI H 278-279
III- 17 H H CI CH3 CI H 269-271
III- 18 H H CI H H CI 196-197
III- 19 H H H CI H F
111-20 H CH3 F H F H
111-21 H CH3 CI H CI H
111-22 H CH3 F H CI H
111-23 H CH3 F F F H
111-24 H CH3 CI CI CI H
111-25 H CH3 CI CH3 CI H
111-26 H CH (CH3)2 F H F H
111-27 H CH (CH3)2 CI H CI H
111-28 H CH (CH3)2 F H CI H
111-29 H CH (CH3)2 F F F H
111-30 H CH (CH3)2 CI CI CI H
111-31 H CH (CH3)2 CI CH3 CI H
111-32 CH3 H CI H CI H 267°C分解
111-33 CH3 H F H F H 205-207
111-34 CH3 H F F F H 190-192
111-35 CH3 H CI CI H H >280°C
111-36 CH3 H CI H H H 240°C分解
111-37 CH3 H H H CI H 210-212
111-38 CH3 H H H H H 152-155
111-39 CI H H H H H
111-40 CI H CI CI H H
111-41 CI H CI H CI H
111-42 CI H F H F H
111-43 CI H F F F H 表 4中部分中间体核磁数据 C1HNMR, 300MHz, 内标 TMS，溶剂 DMSO， 5(ppm)) 如下：
中间体 111-32： 2.00 (d， 3H), 7.35 (m， 1H), 7.55 (d, 1H), 8.25 (m， 1H), 8.80 (s, 1H)。 中间体 m-33 2.00 (d， 3H), 7.00 (m， 1H), 7.18 (m， 1H), 8.20 (m， 1H), 8.72 (s, lH 中间体 m-34 2.01 (t， 3H), 7.18 (m， 1H)， 7.95 (d, 1H)， 8.91 (s, 1H)。
中间体 m-35 2.01 (d, 3H), 7.29 (m， 2H), 8.24 (m， 1H), 8.90 (s, 1H)。
中间体 m-36 2.00 (d， 3H), 7.06 (t， 1H), 7.28 (t， 1H), 7.41 (d， 1H), 8.34 (d， 1H)。 中间体 m-37 2.01 (d, 3H), 7.29 (m， 2H), 7.63 (d， 2H), 9.07 (s, 1H)。
中间体 m-38 2.00 (d， 3H), 7.03 (t， 1H), 7.29 (t， 2H), 7.60 (d， 2H), 8.96 (s, 1H)。 表 5
Figure imgf000011_0001
Figure imgf000011_0003
表 5中部分中间体核磁数据 (^HNMR, 300MHz, 内标 TMS，溶剂 DMSO， 5(ppm)) 如下：
中间体 111-51 : 1.95 (m， 2H), 2.56 (t， 2H), 2.65 (t， 2H), 7.19 (m， 1H), 7.94 (s， 1H)。 中间体 111-53: 2.08 (m， 2H), 2.60 (s, 3H), 2.71 (t， 2H), 2.83 (t， 2H), 7.32 (d， 1H), 7.63 (s， 1H), 7.80 (s, 1H)。
Figure imgf000011_0002
Figure imgf000011_0004
ΠΙ-57 Η C1 Η Η
ΙΠ-58 Η F Η F 242-244
ΠΙ-59 Η C1 Η C1 226-228
ΠΙ-60 Η F Η C1
ΙΠ-61 Η C1 Η F
ΠΙ-62 Η F F F 276-278
ΠΙ-63 Η C1 C1 C1
ΠΙ-64 Η C1 CH3 C1 280°C分解
ΠΙ-65 Η C1 C1 Η >280°C 表 6中部分中间体核磁数据 (^HNMR, 300MHz, 内标 TMS，溶剂 DMSO， 5(ppm)) 如下：
中间体 111-55: 1.69 (m， 4H)， 2.28 (t， 2H), 2.47 (m， 2H), 6.94 (t， 1H), 7.24 (t， 2H), 7.59 (d， 2H), 8.40 (s， 1H), 10.45(s, 1H)。
中间体 ΙΠ-58: 1.69 (m， 4H)， 2.27 (t， 2H), 2.50 (t， 2H), 6.92 (t， 1H)， 7.09 (t， 1H)， 8.39 (m， lH
中间体 m-62 1.67 (m， 4H)， 2.26 (t， 2H), 2.41 (t， 2H), 7.16 (m， 2H), 8.05 (d， 1H)。 中间体 m-64 1.69 (m， 4H)， 2.27 (t， 2H), 2.44 (d， 5H)， 7.29 (d， 1H), 8.30 (d， 1H)。 中间体 m-65 1.69 (m， 4H)， 2.27 (t， 2H), 2.43 (t， 2H), 7.21 (m， 2H), 8.41 (d， 1H)。 通式 I 化合物对农业、 民用和动物技术领域中有害的螨虫和昆虫的成虫、幼虫和 卵都显示出高杀虫活性。
因此，本发明的另一技术方案涉及通式 I 化合物在农业和其他领域中防治害虫害 螨的用途。 尤其是， 通式 I 化合物对下列科的重要品种有活性： 叶螨科 （二斑叶螨、 朱砂叶螨、 苹果全爪螨、 柑橘全爪螨等）， 瘿螨科， 跗线螨科等。
同时， 通式 I 化合物对许多有益的昆虫和螨虫、 哺乳动物、 鱼、 鸟具有低毒性， 而且没有植物毒性。
由于其积极的特性， 上述化合物可有利地用于保护农业和园艺业重要的作物、家 畜和种畜， 以及人类常去的环境免于有害螨虫和有害昆虫的伤害。
为获得理想效果， 化合物的用量因各种因素而改变， 例如所用化合物、 预保护的 作物、 有害生物的类型、 感染程度、 气候条件、 施药方法、 采用的剂型。
每公顷 10克一 5公斤的化合物剂量能提供充分的防治。
本发明的另一目的还涉及通过施用通式 I 化合物，防治农业和园艺业重要的作物 和 /或家畜和种畜和 /或人类常去的环境中的害虫和 /或植物致病性真菌的方法。 尤其 是， 化合物的用量在每公顷 10克一 5公斤内变化。
本发明的另外一种技术方案还包括一种杀虫杀螨组合物，含有作为活性组分的通 式 I 化合物和农业上可接受的载体， 组合物中活性组分的重量百分含量为 0.5-90%。
因此，本发明的技术方案还包括上述组合物在农业和其他领域中防治害虫害螨的 用途。
为了实际应用于农业， 使用含一种或多种通式 I 化合物的组合物通常是有益的。 组合物的使用形式（制剂类型）可以是干粉、可湿性粉剂、 乳油、微乳剂、糊剂、 颗粒剂、 溶液、 悬浮剂等。 组合物使用形式的选择取决于具体的应用。
组合物是以已知方式制备的， 例如任选在表面活性剂的存在下， 通过用溶剂介质 和 /或固体稀释剂稀释或溶解活性物质。
可用的固体稀释剂或载体是例如： 二氧化硅、 高岭土、 膨润土、 滑石、 硅藻土、 白云石、 碳酸钙、 氧化镁、 白垩、 粘土、 合成硅酸盐、 硅镁土、 海泡石。
除水以外， 可用的液体稀释剂是例如芳族有机溶剂 （二甲苯或烷基苯的混合物、 氯苯等）， 石蜡 （石油馏分）， 醇类 （甲醇、 丙醇、 丁醇、 辛醇、 甘油）， 酯类 （乙酸 乙酯、 乙酸异丁酯等）， 酮类 （环己酮、 丙酮、 苯乙酮、 异佛尔酮、 乙基戊基酮等）， 酰胺类 （N，N-二甲基甲酰胺、 N-甲基吡咯烷酮等）。
可用的表面活性剂是烷基磺酸盐、 烷基芳基磺酸盐、 聚氧乙烯烷基酚、 山梨醇的 聚氧乙烯酯、 木质素磺酸盐等的钠、 钙、 三乙基胺或三乙醇胺盐。
组合物还可含特殊的添加剂用于特定的目的，例如粘合剂如阿拉伯胶、聚乙烯醇、 聚乙烯吡咯烷酮等。
上述组合物中活性成分的浓度可根据活性成分、其使用目的、环境条件和采用的 制剂类型而在宽范围内改变。 通常， 活性成分的浓度范围是 1-90%， 优选 5-50 %。
如果需要， 可以向组合物中添加能与通式 I 化合物兼容的其他活性成分， 例如其 他杀螨剂 /杀虫剂、 杀真菌剂、 植物生长调节剂、 抗生素、 除草剂、 肥料。
几种剂型的配制方法举例如下：
悬浮剂的配制： 常用配方中活性组分含量为 5%-35%。 以水为介质， 将原药、 分 散剂、 助悬剂和抗冻剂等加入砂磨机中， 进行研磨， 制成悬浮剂。
可湿性粉剂的配制： 按配方要求， 将原药、 各种表面活性剂及固体稀释剂等充分 混合， 经超细粉碎机粉碎后， 即得到预定含量 （例如 10%-40%) 的可湿性粉剂产品。 为制备适于喷洒用的可湿性粉剂， 本发明的化合物可以和研细的固体粉末如粘土、无 机硅酸盐、 碳酸盐以及润湿剂、 粘合剂和 /或分散剂组成混合物。
水分散性粒剂的配制： 将原药和粉状固体稀释剂、润湿展着剂及粘合剂等进行混 合粉碎， 再加水捏合后， 加入装有 10至 100 目筛网的造粒机中进行造粒， 然后再经 干燥、 筛分 (按筛网范围）。 也可将原药、 分散剂、 崩解剂和润湿剂及固体稀释剂加入 砂磨机中， 以水为介质研磨， 制成悬浮剂， 然后进行喷雾干燥造粒， 通常配制含量为 20%— 30%颗粒状产品。 具体实施方式
以下具体实施例用来进一步说明本发明， 但本发明绝非限于这些例子。
合成实施例 实例 1 : 化合物 9的制备
Figure imgf000014_0001
化合物 9 ΠΙ-9
1 ) 1-(2，4-二氯苯氨基)胍 Π-9的制备
将 2克浓盐酸滴入盛有 3.28克 2，4-二氯苯胺的反应瓶中，保持 pH值在 2-3之间， 升温至 85 °C， 固体全部溶解后向其中滴加 2.02克 50%的单氰胺水溶液， 85 °C下保温 反应 5小时， pH值升高至 7左右， 降温至 60°C， 滴入 10.6克 10%的碳酸钠水溶液， 滴完继续搅拌 10分钟， 冷却， 过滤固体， 用少量水洗， 干燥， 得乳白色固体 3.95克。
2) 中间体 ΠΙ-9的制备
将 2.35克 1-(2，4-二氯苯氨基)胍 Π-9和 30毫升甲苯加入到装有回流分水装置的
100毫升反应瓶中， 升温至 100°C左右， 待固体全部溶解且不再有气泡放出后， 缓慢 滴入 2.02克三氟乙酰乙酸乙酯，滴毕升温至回流，到冷凝管滴下的液体中不再有水时 反应完成， 继续回流半小时， 冷却， 过滤析出的固体， 滤饼用少量甲苯洗涤， 得白色 絮状固体 2.96克， 熔点 253-254°C。
3 ) 化合物 9的制备
将 0.65克中间体 ΠΙ-9溶于 15毫升 DMF中， 加入 0.55克碳酸钾， 室温搅拌半小时， 加入 0.44克中间体 IV (参照 US5663370制备）， 80°C下反应 8小时。 TLC监测反应完毕后， 将反应液倒入 30毫升饱和食盐水中， 乙酸乙酯萃取， 萃取液用无水硫酸镁干燥减压脱 溶， 柱层析 (洗脱剂为乙酸乙酯与石油醚 （沸程 60-90°C)， 体积比为 1 : 10)纯化得浅黄 色固体， 将此固体中加入 10毫升石油醚， 过滤， 得到化合物 9的乳白色固体 0.71克， 熔点 120-121°C。
1H-NMR (300MHz,内标 TMS，溶剂 CDC13) 5(ppm): 3.68 (s, 3H), 3. 79 (s, 3H), 5.34 (s, 2H), 6.56 (s, 1H)， 7.20 (m， 1H)， 7.25 (m， 1H)， 7.36 (m， 2H), 7.41 (m， 1H)， 7.50 (m， 1H)， 7.57 (s, 1H)， 7.60 (s, 1H)， 8.40 (d, 1H)。 实例 2: 化合物 88的制备
Figure imgf000015_0001
化合物 88 将 0.48克中间体 111-44 (；参照实例 1方法制备)溶于 10毫升 DMF中， 加入 0.55 克碳酸钾， 室温搅拌半小时， 加入 0.44克中间体 IV， 80°C下反应 8小时。 TLC监测 反应完毕后， 将反应液倒入 30毫升饱和食盐水中， 乙酸乙酯萃取， 萃取液用无水硫 酸镁干燥减压脱溶， 柱层析 (洗脱剂为乙酸乙酯与石油醚 （沸程 60-90°C)， 体积比为 1: 10) 纯化得浅黄色固体， 将此固体中加入 10毫升石油醚， 过滤， 得到化合物 88的 乳白色固体 0.50克， 熔点 161-163°C。
1H-NMR (300MHz,内标 TMS，溶剂 CDC13) 5(ppm): 2.07 (m， 2H), 2.77 (t, 2H), 2.85
(t， 2H), 3.68 (s， 3H), 3.75 (s， 3H), 5.35 (s， 2H), 6.98 (m， 1H), 7.19 (m， 1H), 7.34 (m， 4H)， 7.55 (m， 1H)， 7.57 (s, 1H)， 7.63 (m， 2H)。
参照以上实例可以制备本发明通式 I中其他化合物。 部分通式 I化合物的物性数据及核磁数据 (^HNMR, 300MHz, 内标 TMS， 溶剂
CDC13)如下：
化合物 1 : 熔点 151-154。C。 S(ppm): 3.77 (s, 3H), 3.84 (s, 3H), 5.30 (s, 2H), 6.60 (s， 1H), 7.20 (m， 1H)， 7.34 (m， 2H), 7.46 (m， 1H)， 7.58 (m， 2H), 7.64 (s, 1H)， 7.82 (m， 2H), 7.92 (m, 1H)。
化合物 2:熔点 89-91。C。 5(ppm): 3.69(s, 3H), 3.78 (s, 3H), 5.35(s, 2H), 6.53 (s, 1H)，
7.00(m, 1H), 7.18(m, 4H)， 7.35 (m， 2H), 7.49(m, 2H), 7.57 (s， 1H)。
化合物 6:熔点 98-100。C。S(ppm): 2.34 (s,lH),3.69 (s, 3H), 3.76 (s, 3H), 5.32 (s, 2H), 6.46 (s， 1H), 6.88(m，lH)， 7.22(m, 2H), 7.36(m, 4H)， 7.49 (m， 2H), 7.57 (s， 1H)。
化合物 7:熔点 108-110。C。S(ppm): 3.73(s, 3H), 3.80 (s, 3H), 5.30 (s, 2H), 6.53(s, 1H): 7.20(m, 1H), 7.34(m, 3H), 7.42 (m， 2H), 7.60(s, 1H), 7.81(d, 2H), 8.06(s， 1H)
化合物 8: 熔点 105-107。C。 S(ppm): 3.70 (s, 3H), 3. 80 (s, 3H), 5.31 (s, 2H), 6.54 (s， 1H), 6.90 (m， 2H), 7.20 (m， 1H)， 7.28 (m， 1H)， 7.36 (m， 2H), 7.48 (m， 1H)， 7.59 (s, 1H)， 8.28 (m, 1H)。
化合物 10:熔点 188-190。S(ppm): 3.74 (s, 3H), 3.81 (s, 3H), 5.30 (s, 2H), 6.52 (s, 1H): 7.20 (m， 1H)， 7.33 (m， 3H), 7.48 (m， 2H), 7.61 (m， 2H), 7.90 (m， 1H)。
化合物 11 :熔点 165-168。C。 5(ppm): 3.67 (s, 3H), 3. 83 (s, 3H), 5.42 (s, 2H), 6.77 (s， 1H), 7.20 (m， 1H)， 7.38 (m， 2H), 7.51 (m， 1H)， 7.61 (s, 1H)， 8.48 (m， 1H)， 9.20 (m， 2H), 10.85 (s, 1H)。
化合物 12:熔点 118-120。C。 S(ppm): 3.70 (s, 3H), 3.80 (s, 3H), 5.33 (s, 2H), 6.56 (s， 1H), 7.12 (m， 1H), 7.15 (m， 1H), 7.20 (m， 1H), 7.37 (m， 3H), 7.50 (m， 1H), 7.59 (s， 1H)， 8.37 (m, 1H)。
化合物 13:熔点 135-137。C。 S(ppm): 3.73 (s, 3H), 3.82 (s, 3H), 5.28 (s, 2H), 6.51 (s， 1H), 7.09 (m， 1H), 7.20 (m， 1H), 7.34 (m， 2H), 7.47 (m， 2H), 7.61 (s， 1H), 7.82 (m， 1H)。
化合物 15:熔点 129-130。C。 5(ppm): 3.71 (s, 3H), 3. 80 (s, 3H), 5.31 (s, 2H), 6.57 (s， 1H)， 6.98 (m， 1H)， 7.20 (m， 1H)， 7.30 (m， 1H)， 7.36 (m， 2H), 7.48 (m， 1H)， 7.59 (s, 1H)， 8.06 (s, 1H)。
化合物 16： 5(ppm): 3.69 (s, 3H), 3. 80 (s, 3H), 5.34 (s, 2H), 6.59 (s, 1H), 7.21 (m， 1H):
7.38 (m， 3H), 7.50 (m， 1H), 7.59 (s， 1H), 7.68 (m， 1H), 8.40 (d， 1H)。
化合物 17: 熔点 115-117。C。 S(ppm): 2.52 (s, 3H), 3.68 (s, 3H), 3.78 (s, 3H), 5.34 (s， 2H), 6.55 (s， 1H), 7.19 (m， 1H), 7.29 (d， 1H), 7.37 (m， 2H), 7.49 (m， 1H), 7.57 (s， 1H), 7.74 (s, 1H)， 8.24 (d， 1H)。
化合物 18: 熔点 115-117。C。 S(ppm): 3.67 (s, 3H), 3.79 (s, 3H), 5.37 (s, 2H), 6.57 (s， 1H), 6.99 (m， 1H), 7.19 (m， 1H), 7.37 (m， 3H), 7.52 (m， 1H), 7.58 (s， 1H), 7.63 (m， 1H)， 8.65 (d, 1H)。
化合物 78：熔点 160-162°C o 5(ppm): 2.19 (d， 3H), 3.69 (s, 3H), 3.80 (s, 3H), 5.34 (s，
2H), 7.23 (m， 2H), 7.38 (m， 3H), 7.50 (m， 2H), 7.58 (s， 1H), 8.49 (d， 1H)。
化合物 79：熔点 129-131°C o 5(ppm): 2.19 (d， 3H), 3.68 (s, 3H), 3.80 (s, 3H), 5.32 (s， 2H), 6.89 (m， 2H), 7.13 (m， 1H)， 7.20 (m， 1H)， 7.37 (m， 2H), 7.51 (m， 1H)， 7.60 (s, 1H)， 8.19 (m, 1H)。
化合物 80:熔点 156-158。C。 S(ppm): 2.20 (d， 3H), 3.71 (s, 3H), 3.82 (s, 3H), 5.32 (s,
2H), 6.97 (m， 1H)， 7.15 (m， 1H)， 7.21 (m， 1H)， 7.37(m, 2H), 7.5 l(m, 1H)， 7.60(s, 1H)， 8.19 (m, 1H)。
化合物 81 :熔点 160-162。C。 S(ppm): 2.19 (d， 3H), 3.68 (s, 3H), 3.80 (s, 3H), 5.35 (s, 2H), 7.14 (m， 1H)， 7.22 (m， 2H), 7.38 (m， 2H), 7.54 (m， 1H)， 7.58 (s, 1H)， 7.63 (s, 1H)， 8.50 (d, lH) o
化合物 82：熔点 142-144°C o 5(ppm): 2.18 (d， 3H), 3.68 (s, 3H), 3.77 (s, 3H), 5.36 (s， 2H), 6.97 (m， 1H)， 7.21 (m， 1H)， 7.29 (m， 1H)， 7.38 (m， 3H), 7.54 (m， 2H), 7.58 (s, 1H)， 8.52 (d,lH) o
化合物 83:熔点 167-170。C。 S(ppm): 2.19 (d， 3H), 3.72 (s, 3H), 3.81 (s, 3H), 5.26 (s, 2H), 7.21 (m， 1H)， 7.34 (m， 4H)， 7.49 (m， 1H)， 7.58 (m， 1H)， 7.61 (s， 2H)。
化合 if 84：熔点 150-152。C。 S(ppm): 2.18 (d， 3H), 3.70 (s, 3H), 3.78 (s, 3H), 5.27 (s， 2H), 7.03 (m， 1H)， 7.20 (m， 1H)， 7.36 (m， 4H)， 7.52 (m， 2H), 7.59 (s, 1H)， 7.63 (s, 1H)， 7.65(s, 1H)。
化合物 85: 熔点 141-143。C。 S(ppm): 3.70 (s, 3H), 3.79 (s, 3H), 5.38 (s, 2H), 7.07 (t， 1H), 7.20 (m， 1H), 7.35 (m， 3H), 7.44 (s， 1H), 7.54 (m， 1H), 7.63 (m， 3H)。
化合物 96:熔点 106-108。C。 5(ppm): 2.08 (m， 2H), 2.77 (t， 2H), 2.85 (t， 2H), 3.69 (s， 3H), 3.77 (s, 3H), 5.32 (s, 2H), 6.84 (m， 2H), 7.04 (m， 1H), 7.19 (m， 1H), 7.34 (m， 2H), 7.51 (m， 1H), 7.58 (s， 1H), 8.35 (m， 1H)。
化合物 97:熔点 150-151。C。 5(ppm): 2.05 (m， 2H), 2.78 (t， 2H), 2.87 (t， 2H), 3.68 (s， 3H), 3.77 (s， 3H), 5.34 (s， 2H), 7.20 (m， 2H), 7.35 (m， 3H), 7.40 (s， 1H), 7.52 (m， 1H), 7.57 (s, 1H)， 8.44 (d， 1H)。 化合物 103:熔点 118-120。C。S(ppm): 2.09 (m， 2H), 2.78 (t， 2H), 2.85 (t， 2H), 3.69 (s， 3H), 3.78 (s， 3H), 5.31 (s， 2H), 6.92 (m， 1H), 7.18 (s， 1H), 7.20 (m， 1H), 7.34 (m， 2H), 7.51 (m， 1H), 7.58 (s， 1H), 8.09 (m， 1H)。
化合物 105:熔点 150-151°C。S(ppm): 2.09 (m， 2H), 2.49 (s, 3H), 2.78 (t， 2H), 2.87 (t， 2H), 3.68 (s， 3H), 3.77 (s， 3H), 5.34 (s， 2H), 7.24 (m， 2H), 7.35 (m， 2H), 7.53 (m， 2H), 7.57 (s， 1H), 8.32 (d， 1H)。
化合物 128:熔点 132-134。C。S(ppm): 2.08 (m， 2H), 2.78 (t， 2H), 2.88 (t， 2H), 3.66 (s， 3H), 3.77 (s, 3H), 5.35 (s, 2H), 7.07 (m， 1H)， 7.18 (m， 2H), 7.36 (m， 2H), 7.54 (m， 2H), 7.57 (s， 1H), 8.49 (d， 1H)。
化合物 129:熔点 136-138。C。S(ppm): 1.81 (m， 4H)， 2.55 (t， 2H), 2.70 (t， 2H), 3.71 (s，
3H), 3.78 (s， 3H), 5.37 (s， 2H), 6.98 (m， 1H), 7.22 (m， 1H), 7.38 (m， 4H)， 7.58 (m， 1H)， 7.61 (s, 1H), 7.66 (m, 2H)。
化合物 137:熔点 118-120。C。S(ppm): 1.80 (m， 4H)， 2.52 (t， 2H), 2.68 (t， 2H), 3.69 (s， 3H), 3.78 (s， 3H), 5.29 (s， 2H), 6.86 (m， 3H), 7.19 (m， 1H), 7.37 (m， 2H), 7.54 (m， 1H)， 7.58 (s， 1H)， 8.38 (m， 1H)。
化合物 138:熔点 170-171。C。S(ppm): 1.80 (m， 4H)， 2.52 (t， 2H), 2.69 (t， 2H), 3.68 (s， 3H), 3.78 (s， 3H), 5.30 (s， 2H), 7.19 (m， 2H), 7.28 (s， 1H), 7.35 (m， 3H), 7.54 (m， 1H), 7.58 (s, 1H)， 8.48 (d， 1H)。
化合物 144:熔点 142-144。C。 5(ppm): 1.80 (m， 4H)， 2.52(t, 2H), 2.68 (t， 2H), 3.70 (s， 3H), 3.79 (s, 3H), 5.28 (s, 2H), 6.91 (m， 2H), 7.19 (m， 1H)， 7.35 (m， 2H), 7.53 (m， 1H)， 7.59 (s， 1H), 8.16 (m, 1H)。
化合物 146: 熔点 170-172。C。 S(ppm): 1.80(m， 4H)， 2.49(s, 3H), 2.52(t, 2H), 2.69 (t， 2H), 3.69 (s, 3H), 3.78 (s, 3H), 5.30 (s, 2H), 7.20 (m， 2H), 7.35 (m， 3H), 7.54 (m， 1H)， 7.58 (s, lH)，8.16 (m， 1H)。
化合物 169:熔点 150-152°C。 5(ppm): 1.80 (m， 4H)， 2.53 (t， 2H), 2.70(t, 2H), 3.68(s,
3H), 3.78 (s， 3H), 5.32 (s， 2H), 7.06 (m， 1H), 7.18 (m， 2H), 7.36 (m， 2H), 7.46 (s， 1H), 7.56 (m， 1H), 7.58 (s, 1H)。 制剂实施例 （各组分加入量均为重量百分含量， 活性化合物折百后计量加入） 实施例 3: 15%化合物 9悬浮剂
化合物 15 15 %
乙二醇 4%
壬基苯酚聚乙二醇醚 3 %
木质素磺酸钠 4%
羧甲基纤维素 1 %
75 %硅油水乳液 0.8 %
水 补足至 100%
化合物 9及其他组分充分混合， 由此得到的悬浮剂， 用水稀释所得悬浮剂可得到 所需浓度的稀释液。 实施例 4: 30%化合物 9可湿性粉剂
化合物 9 30%
十二烷基硫酸钠 2%
木质素磺酸钠 3%
萘磺酸甲醛縮合物 5 %
轻质碳酸钙 补足至 100%
将化合物 9及其他组分充分混合， 经超细粉碎机粉碎后， 即得到 30%的可湿性粉 剂产 t 实施例 5: 60%化合物 88水分散性粒剂
化合物 88 60%
萘磺酸钠甲醛縮合物 12%
甲基 油酰基-牛磺酸钠 8%
聚乙烯吡咯烷酮 2%
羧甲基纤维素 2%
高岭土 补足至 100%
将化合物 88及其他组分混合粉碎， 再加水捏合后， 加入 10-100目筛网的造粒机 中进行造粒， 然后再经干燥、 筛分 (按筛网范围)， 即得到 60%的水分散性粒剂。 生物活性测定
实例 6: 室内杀螨活性测定
用本发明化合物对朱砂叶螨的成螨、若螨和螨卵进行室内活性测定试验。测定方 法如下：
对成螨室内活性测定： 化合物称量后用丙酮制成母液， 按试验设计用含有 0. 1% 吐温 80的静置自来水稀释系列浓度。 取两片真叶菜豆苗， 接种朱砂叶螨成螨并调查 基数后， 用手持喷雾器 (DeVilbiss Atomizer M163)喷雾处理， 每处理 3次重复， 处理 后置于标准观察室， 72小时后调查存活螨数， 计算死亡率。
对若螨室内活性测定： 取两片真叶盆栽菜豆苗， 然后将健康朱砂叶螨雌成螨 10头 接到叶片上， 24 小时后去除成螨， 卵继续进行培养， 7-10天后进入若螨期调查基数 后进行喷雾处理，每处理 3次重复，处理后置于标准观察室， 72 小时后调查存活螨数， 计算死亡率。
室内杀卵活性测定： 取盆栽菜豆苗保留一片真叶， 然后将健康朱砂叶螨雌成螨 10 头接到叶片上， 24 小时后去除成螨， 调查卵数后进行喷雾处理， 药剂处理与喷雾方 法与成螨试验相同。 5天后待空白对照卵全部孵化， 调查各处理未孵化卵数， 计算孵 化抑制率。 部分测试结果如下：
药液浓度为 100mg/L时， 化合物 2、 6、 8、 9、 12、 13、 15、 16、 17、 18、 79、 80、
82、 83、 84、 85、 88等对朱砂叶螨成螨的致死率均为 100%; 化合物 7、 129等对朱砂 叶螨成螨的致死率均高于 90%。
药液浓度为 40mg/L时， 化合物 2、 6、 8、 9、 12、 15、 16、 17、 18、 79、 80、 88 等对朱砂叶螨成螨的致死率均为 100%; 化合物 13、 82、 84等对朱砂叶螨成螨的致死 率均在 95%以上。
药液浓度为 10mg/L时， 化合物 2、 8、 9、 12、 15、 16、 17、 79等对朱砂叶螨成螨 的致死率均为 100%， 化合物 13、 80、 82、 84、 88等对朱砂叶螨成螨的致死率均高于 80%。
药液浓度为 5mg/L时， 化合物 8、 9、 12、 15、 16、 17等对朱砂叶螨成螨的致死率 均为 100%。
药液浓度为 0.625mg/L时，化合物 15等对朱砂叶螨成螨的致死率为 95%;化合物 8、
9等对朱砂叶螨成螨的致死率在 85%以上。
药液浓度为 0.31mg/L时， 化合物 15等对朱砂叶螨成螨的致死率高于 75%。
药液浓度为 2.5mg/L时， 化合物 9、 15等对朱砂叶螨若螨的致死率均为 100%， 化合 物 8等对朱砂叶螨若螨的致死率高于 95%。
药液浓度为 0.63mg/L时， 化合物 15等对朱砂叶螨若螨的致死率为 100%， 化合物 9 等对朱砂叶螨若螨的致死率高于 95%， 化合物 8等对朱砂叶螨若螨的致死率高于 75%。
药液浓度为 0.16mg/L时， 化合物 9、 15等对朱砂叶螨若螨的致死率均在 60%以上。 药液浓度为 10mg/L时， 化合物 8、 9、 15、 16对朱砂叶螨卵孵化抑制率为 100%。 药液浓度为 2.5mg/L时，化合物 8、 9、 15、 16对朱砂叶螨卵孵化抑制率为 90%或 90% 以上。 将 WO2008145052A1中的化合物 20(对照 A)、 680 (对照 B ) 和 694(对照 C)作为对 照化合物，与本发明中的化合物进行活性比较试验。三个对照化合物的结构如下所示:
Figure imgf000019_0001
对照 A 对照 B 对照 C 同时选用商品化产品嘧螨酯 （市售天达农、 30%悬浮剂， 日本曹达生产)和螺螨酯 (市售螨危、 24%悬浮剂， 拜耳公司生产)作为对照化合物， 与本发明中的化合物进行 活性比较试验。 测定方法同前所述。
防治朱砂叶螨成螨活性结果见表 7; 抑制朱砂叶螨螨卵活性结果见表 8。 表 7
仆 A物 朱砂叶螨成螨的致死率 （％)
VL π
40mg/L 10mg/L 5mg/L 2.5mg/L 1.25mg/L 0.625mg/L 化合物 8 100 100 100 100 98 86 化合物 9 100 100 100 98 90 88 化合物 12 100 100 100 92 86 60 化合物 15 100 100 100 100 100 95 化合物 16 100 100 100 98 78 60 化合物 17 100 100 100 98 70 60 对照 A 100 90 60 30 10 0 对照 B 0 0 - - - - 嘧螨酯 100 100 95 65 30 0 注： "-"表示未测药效。 表 8
螨卵孵化抑制率 （°
化合物
10 mg/L 2.5 mg/L 0.625 mg/L
化合物 8 100 90 25
化合物 9 100 100 20
对照 A 100 10 0
对照 C 100 10 0
嘧螨酯 95 10 0
螺螨酯 100 70 0
实例 7 : 田间小区验证试验
防治柑桔红蜘蛛田间小区试验 （中国广西桂林）
试验设在桂林市灵川县潮田乡 2年生沙糖柑桔园进行， 砧木为枳， 株行距 1. 5 X 2. 5米， 平均株高 1. 45米， 冠幅 1. 30米。 每小区 2株树， 重复 4次， 随机区组排列。 化合物 9 ( 15%悬浮剂）设 100mg/L、 25mg/L两个剂量，螺螨酯（24%悬浮剂）设 48mg/L 一个剂量； 采用 "MATABI "超绿 16型背负式喷雾器 ( Matabi Supergreen 16 Knapsack Sprayer 16 Litre )均匀喷雾， 喷液量每株约 2L。 于 2009年 10月 30日施药 1次， 此时 柑桔红蜘蛛成螨、 幼若螨、 螨卵均存在， 螨卵比为 1 : 1. 27。 施药当天天气晴好， 平 均气温 23°C， 施药后 3天均为晴好天气。 施药前调查虫口基数， 施药后 1天、 3天、 10天、 15天、 20天和 30天各调查一次。 调查时每小区调查 2株树， 按树冠东、 西、 南、 北、 中五个方位， 各个方位调查 5张叶片上的活动态螨数， 每小区调查 50张叶 片， 根据下式计算螨口减退率及校正防效： 螨口减退率 （％) = [ (施药前叶均螨数 -施药后叶均螨数) /施药前叶均螨数] X 100 防治效果 （％) = [ (处理区螨口减退率-未处理区螨口减退率） / ( 100-未处理区螨 口减退率） ] X lOOo 化合物 9防治柑桔红蜘蛛田间小区试验 （广西桂林） 的试验结果见表 9: 表 9
防效 (%)
化合物 mg/L 药后 1天 药后 3天 药后 10天 药后 15天 药后 20天 药后 30天
100 92 96 96 95 97 94 化合物 9
25 90 92 83 91 92 91 螺螨酯 48 59 72 75 76 83 82

Claims

权 利 要 求 书
1、 一种含取代苯胺基嘧啶基团的 E-型苯基丙烯酸酯类化合物， 如通式 I 所示:
Figure imgf000022_0001
式中：
选自三氯甲基、 一氯二氟甲基、 二氯一氟甲基、 三氟甲基或 2，2，2-三氟乙基； R2选自氢、 氯或甲基；
或者 、 R2与嘧啶环组成环戊烷并嘧啶或环己烷并嘧啶；
R3选自氢、 d-C4烷基、 d-C4烷基磺酰基或 d-C4烷基羰基；
当 R2选自氢时， Rn选自 2,3-二氟、 2,4-二氟、 2,4-二氯、 2-氟 -3-氯、 2-氯 -3-氟、
2-氟 -4-氯、 2-氯 -4-氟、 2，3，4-三氟、 2，3，4-三氯、 2,4-二氟 -3-甲基、 2,4-二氯 -3-甲基、 2- 氟 -3,4-二氯或 2-氯 -3,4-二氟；
当 R2选自氯或甲基时， Rn选自氢、 2-氯、 4-氯、 2,3-二氟、 2,4-二氟、 2,3-二氯、 2,4-二氯、 2-氟 -3-氯、 2-氯 -3-氟、 2-氟 -4-氯、 2-氯 -4-氟、 2，3，4-三氟、 2，3，4-三氯、 2,4- 二氟 -3-甲基、 2,4-二氯 -3-甲基、 2-氟 -3,4-二氯或 2-氯 -3,4-二氟；
当 、 R2与嘧啶环组成环戊烷并嘧啶或环己烷并嘧啶时， R选自卤素、 氰基、 硝基、 C C4烷基或卤代 d-C3烷基， n=0-4。
或其盐酸盐、 磷酸盐、 醋酸盐、 苯磺酸盐或草酸盐。
2、 根据权利要求 1所述的化合物， 其特征在于： 通式 I 中
选自三氟甲基；
R2选自氢、 氯或甲基；
或者 、 R2与嘧啶环组成环戊烷并嘧啶或环己烷并嘧啶；
R3选自氢；
当 R2选自氢时， Rn选自 2,4-二氟、 2,4-二氯、 2-氟 -4-氯、 2-氯 -4-氟、 2，3，4-三氟、 2，3，4-三氯或 2,4-二氯 -3-甲基；
当 R2选自氯或甲基时， Rn选自氢、 2-氯、 4-氯、 2,4-二氟、 2,3-二氯、 2,4-二氯、 2-氟 -4-氯、 2-氯 -4-氟、 2，3，4-三氟、 2，3，4-三氯或 2,4-二氯 -3-甲基；
当 、 R2与嘧啶环组成环戊烷并嘧啶或环己烷并嘧啶时， R选自氯、 溴、 氟、 C C4烷基或卤代 d-C3烷基， n=0-3 ;
或其盐酸盐、 磷酸盐、 醋酸盐、 苯磺酸盐或草酸盐。
3、 一种按照权利要求 1所述的通式 I 化合物在农业和其他领域中防治害虫害螨 的用途。
4、 一种杀虫杀螨组合物， 其特征在于： 含有作为活性组分的权利要求 1所述通 式 I 化合物和农业上可接受的载体， 组合物中活性组分的重量百分含量为 0.5-90%。
5、一种按照权利要求 4所述的组合物在农业和其他领域中防治害虫害螨的用途。
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