CN104430343B - Application of substituted ether and thioether compound as plant virus resisting agent - Google Patents

Application of substituted ether and thioether compound as plant virus resisting agent Download PDF

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CN104430343B
CN104430343B CN201310439077.4A CN201310439077A CN104430343B CN 104430343 B CN104430343 B CN 104430343B CN 201310439077 A CN201310439077 A CN 201310439077A CN 104430343 B CN104430343 B CN 104430343B
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alkyl
halo
compound
alkylthio group
alkoxy
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CN104430343A (en
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迟会伟
李慧超
李淼
范志金
刘长令
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Abstract

The invention discloses application of a substituted ether and thioether compound, represented by a general formula I shown in specifications, as a plant virus resisting agent. In the formula, all substituents are as defined in the specifications. The compound represented by the general formula I has very good plant virus resisting activity and can be used for preventing and treating virus diseases of a variety of crops, such as tobacco, vegetables, fruit trees, legumes, cereals and potatoes.

Description

Substituent ether and thio-ether type compounds are as the application of anti-plant virus agent
Technical field
The invention belongs to agricultural uses antivirotic field and in particular to substituent ether and thio-ether type compounds are as anti-phytopathy The application of toxic agent.
Background technology
The compounds of this invention disclosed in patent CN101119961, CN101205187, EP253213, US4829085, There is sterilization and insecticidal activity, but then there is no any report as antivirotic and application.
Content of the invention
It is an object of the invention to provide substituent ether as shown in formula I for the structure and thio-ether type compounds are as anti-plant The application of viral agent.
Technical scheme is as follows：
Substituent ether and thio-ether type compounds as the application of anti-plant virus agent, including orysastrobin, 2-cyano-3-amino-3-phenylancryic acetate and Structure compound as shown in formula I：
Q represents one of following group：
R1Selected from halogen, nitro, cyano group, C1-C12Alkyl, C3-C12Cycloalkyl, halo C1-C12Alkyl, C1-C12Alkoxyl, Halo C1-C12Alkoxyl, C1-C12Alkoxy C1-C12Alkyl, halo C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group, halogen For C1-C12Alkylthio group, C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphonyl, halo C1- C12Alkyl sulphonyl；Unsubstituted or by 1-5 R3The following radicals replacing：Aryl, aryloxy group, aryl C1-C12Alkyl, aryl C1-C12Alkoxyl, fragrant amino, heteroaryl, heteroaryl epoxide, heteroaryl C1-C12Alkyl or heteroaryl C1-C12Alkoxyl；
R2Selected from hydrogen, halogen, cyano group, C1-C12Alkyl, C3-C12Cycloalkyl, halo C1-C12Alkyl, C1-C12Alkoxyl, halogen For C1-C12Alkoxyl, C1-C12Alkoxy C1-C12Alkyl, halo C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group, halo C1-C12Alkylthio group, C1-C12Alkyl sulphinyl, halo C1-C12Alkyl sulphinyl, C1-C12Alkyl sulphonyl, halo C1-C12 Alkyl sulphonyl；Unsubstituted or by 1-5 R3The following radicals replacing：Aryl, aryloxy group, aryl C1-C12Alkyl, aryl C1- C12Alkoxyl, fragrant amino, heteroaryl, heteroaryl epoxide, heteroaryl C1-C12Alkyl or heteroaryl C1-C12Alkoxyl；
R3Selected from halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6Alcoxyl Base, C1-C6Alkylthio group, C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl, C2-C6Thiazolinyl, halo C2-C6Thiazolinyl, C3-C6Alkenyloxy group, Halo C3-C6Alkenyloxy group, C2-C6Alkynyl, halo C2-C6Alkynyl, C3-C6Alkynyloxy group, halo C3-C6Alkynyloxy group, halo C1-C6Alkane sulphur Base, halo C1-C6Alkyl-carbonyl, C1-C6Alkyl amino, halo C1-C6Alkyl amino, C2-C8Dialkyl amido, C1-C6Alkyl oxycarbonyl Base amino, halo C1-C6Alkyl-carbonyl-amino, C1-C6Alkyl amino-carbonyl or halo C1-C6Alkyl amino-carbonyl；
The integer of n=0-4；P=0 or 1；X=O or S；A=O, S or NH.
When applying as antivirotic in orysastrobin, 2-cyano-3-amino-3-phenylancryic acetate and compound of Formula I, more preferably compound is：
Q is selected from Q1、Q2、Q3、Q4、Q5、Q6、Q7、Q8、Q9、Q19、Q20、Q21Or Q22；
Ar is selected from Ar-1, Ar-2 or Ar-3；
R1Selected from halogen, nitro, cyano group, C1-C6Alkyl, C3-C6Cycloalkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halogen For C1-C6Alkoxyl, C1-C6Alkoxy C1-C6Alkyl, halo C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group, halo C1-C6 Alkylthio group, C1-C6Alkyl sulphinyl, halo C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halo C1-C6Alkyl sulfonyl Base；Unsubstituted or by 1-3 R3The following radicals replacing：Phenyl, phenoxy group, phenyl C1-C6Alkyl, phenyl C1-C3Alkoxyl, Pyridine radicals, pyridine radicals epoxide, pyridine radicals C1-C6Alkyl or pyridine radicals C1-C3Alkoxyl；
R2Selected from hydrogen, halogen, cyano group, C1-C6Alkyl, C3-C6Cycloalkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6Alkoxyl, C1-C6Alkoxy C1-C6Alkyl, halo C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group, halo C1-C6Alkane Sulfenyl, C1-C6Alkyl sulphinyl, halo C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halo C1-C6Alkyl sulfonyl Base；Unsubstituted or by 1-3 R3The following radicals replacing：Phenyl, phenoxy group, phenyl C1-C6Alkyl, phenyl C1-C3Alkoxyl, Pyridine radicals, pyridine radicals epoxide, pyridine radicals C1-C6Alkyl or pyridine radicals C1-C3Alkoxyl；
R3Selected from halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6Alcoxyl Base, C1-C6Alkylthio group, C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl, halo C1-C6Alkylthio group, halo C1-C6Alkyl-carbonyl, C1-C6Alkyl amino, halo C1-C6Alkyl amino, C2-C8Dialkyl amido, C1-C6Alkyl-carbonyl-amino, halo C1-C6Alkyl Carbonylamino, C1-C6Alkyl amino-carbonyl or halo C1-C6Alkyl amino-carbonyl；
N=0,1,2 or 3；P=0 or 1；X=O or S；A=O, S or NH.
Further preferred compound when applying as antivirotic in orysastrobin, 2-cyano-3-amino-3-phenylancryic acetate and compound of Formula I For：
Q is selected from Q1、Q2、Q3、Q4、Q5、Q6、Q7、Q8、Q9、Q19、Q20、Q21Or Q22；
Ar is selected from Ar-1, Ar-2 or Ar-3；
R1Selected from halogen, nitro, cyano group, C1-C6Alkyl, C3-C6Cycloalkyl, halo C1-C6Alkyl, C1-C6Alkoxy C1-C6 Alkyl, C1-C6Alkylthio group, halo C1-C6Alkylthio group, C1-C6Alkyl sulphinyl, halo C1-C6Alkyl sulphinyl, C1-C6Alkane Base sulfonyl, halo C1-C6Alkyl sulphonyl；Unsubstituted or by 1-3 R3The following radicals replacing：Phenyl, phenyl C1-C3Alkane Base, pyridine radicals or pyridine radicals C1-C3Alkyl；
R2Selected from hydrogen, halogen, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6Alkoxyl, C1-C6Alkoxy C1-C6Alkyl, halo C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group, halo C1-C6Alkylthio group, C1-C6Alkane Base sulfinyl, halo C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halo C1-C6Alkyl sulphonyl；Unsubstituted or By 1-3 R3The following radicals replacing：Phenyl, phenyl C1-C3Alkyl, pyridine radicals or pyridine radicals C1-C3Alkyl；
R3Selected from halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6Alcoxyl Base, C1-C6Alkylthio group, C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl or halo C1-C6Alkylthio group；
N=0,1,2 or 3；P=0 or 1；X=O or S；A=O, S or NH.
Chemical combination still more preferably when applying as antivirotic in orysastrobin, 2-cyano-3-amino-3-phenylancryic acetate and compound of Formula I Thing is：
Q is selected from Q1、Q2、Q3、Q4、Q5、Q6、Q7、Q8、Q19、Q20、Q21Or Q22；
Ar is selected from Ar-1, Ar-2 or Ar-3；
R1Selected from F, Cl, Br, I, nitro, cyano group, C1-C6Alkyl, C3-C6Cycloalkyl, halo C1-C6Alkyl, C1-C6Alcoxyl Base C1-C6Alkyl, C1-C6Alkylthio group, halo C1-C6Alkylthio group, C1-C6Alkyl sulphinyl, halo C1-C6Alkyl sulphinyl, C1-C6Alkyl sulphonyl, halo C1-C6Alkyl sulphonyl；Unsubstituted or by 1-3 R3The following radicals replacing：Phenyl or pyrrole Piperidinyl；
R2Selected from hydrogen, F, Cl, Br, I, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6Alkane Epoxide, C1-C6Alkylthio group, halo C1-C6Alkylthio group, C1-C6Alkyl sulphinyl, halo C1-C6Alkyl sulphinyl, C1-C6Alkane Base sulfonyl, halo C1-C6Alkyl sulphonyl；Unsubstituted or by 1-3 R3The following radicals replacing：Phenyl, phenyl C1-C3Alkane Base, pyridine radicals or pyridine radicals C1-C3Alkyl；
R3Selected from F, Cl, Br, I, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6 Alkoxyl, C1-C6Alkylthio group or halo C1-C6Alkylthio group；
N=0,1,2 or 3；P=0 or 1；X=O or S；A=O, S or NH.
In the definition of compound of Formula I given above, collect term used and be typically defined as follows：
Halogen：Refer to fluorine, chlorine, bromine or iodine.
Alkyl：Straight or branched alkyl, such as methyl, ethyl, propyl group, isopropyl, normal-butyl or the tert-butyl group.
Cycloalkyl：Substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopenta or cyclohexyl.Substituent such as methyl, Halogen etc..
Haloalkyl：Straight or branched alkyl, the hydrogen atom on these alkyl can partly or entirely be taken by halogen atom Generation, for example, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl etc..
Alkoxyl：Straight or branched alkyl, is bonded through oxygen atom and is connected in structure.
Halogenated alkoxy：Straight or branched alkoxyl, the hydrogen atom on these alkoxyls can be partly or entirely former by halogen Son is replaced.For example, chloromethane epoxide, dichloro methoxyl group, trichloromethoxy, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, Chlorine fluorine methoxyl group, trifluoro ethoxy etc..
Alkoxyalkyl：Alkoxyl is connected in structure through alkyl.As-CH2OCH3,-CH2OCH2CH3.
Halogenated alkoxy alkyl：Hydrogen atom on the alkyl of alkoxyalkyl can partly or entirely be replaced by halogen atom. As-CH2OCH2CH2Cl.
Alkoxy carbonyl：Alkoxyl is connected in structure through carbonyl.As-COOCH3,-COOCH2CH3.
Alkylthio group：Straight or branched alkyl, is bonded through sulphur atom and is connected in structure.
Halogenated alkylthio：Straight or branched alkylthio group, the hydrogen atom on these alkyl can be partly or entirely by halogen atom Replaced.For example, chloromethane sulfenyl, dichloro methyl mercapto, trichloro-methylthio, fluorine methyl mercapto, difluoro methyl mercapto, trifluoromethylthio, chlorine Fluorine methyl mercapto etc..
Alkyl amino：Straight or branched alkyl, is bonded through nitrogen-atoms and is connected in structure.
Haloalkylamino：Straight or branched alkyl amino, the hydrogen atom on these alkyl can be partly or entirely by halogen Atom is replaced.
Thiazolinyl：Straight or branched alkenes, such as vinyl, 1- acrylic, 2- acrylic and different cyclobutenyls, pentenyl And hexenyl isomers.Thiazolinyl also includes many alkenes, such as 1,2- allene base and 2,4- hexadienyl.
Haloalkenyl group：Straight or branched alkenes, the hydrogen atom on these thiazolinyls can partly or entirely be taken by halogen atom Generation.
Alkynyl：Straight or branched acetylenic, such as acetenyl, 1- propinyl, 2-propynyl and different butynyl, pentynyl And hexynyl isomers.Alkynyl also includes the group being made up of multiple three keys, such as 2,5- adipic alkynyl.
Halo alkynyl：Straight or branched acetylenic, the hydrogen atom on these alkynyls can partly or entirely be taken by halogen atom Generation.
Alkenyloxy group：Straight or branched alkenes, are bonded through oxygen atom and are connected in structure.
Halo alkenyloxy group：Straight or branched alkenyloxy group, the hydrogen atom in these alkenyloxy groups can be partly or entirely former by halogen Son is replaced.
Alkynyloxy group：Straight or branched acetylenic, is bonded through oxygen atom and is connected in structure.
Halo alkynyloxy group：Straight or branched alkynyloxy group, the hydrogen atom on these alkynyloxy groups can be partly or entirely former by halogen Son is replaced.
Alkyl-carbonyl：Straight or branched alkyl is through carbonyl（-CO-）It is connected in structure, such as acetyl group.
Halogenated alkyl carbonyl：Straight or branched alkyl carbonyl, the hydrogen atom on its alkyl can be partly or entirely by halogen atom Replaced, such as trifluoroacetyl group.
Alkyl sulphinyl：Straight or branched alkyl is through sulfinyl（-SO-）It is connected in structure, such as methylsulfinyl Base.
Alkylsulfinyl：Straight or branched alkyl sulfinyl, the hydrogen atom on its alkyl can be part or all of Replaced by halogen atom.
Alkyl sulphonyl：Straight or branched alkyl is through sulfonyl（-SO2-）It is connected in structure, such as methyl sulphonyl.
Halogenated alkyl sulfonyl：Straight or branched alkyl sulfonyl, the hydrogen atom on its alkyl can be partly or entirely by halogen Atom is replaced.
Alkyl-carbonyl-amino：As-NHCOCH3,-NHCOC (CH3)3.
Alkyl amino-carbonyl：As-C (=O) NHCH3,-C (=O) N (CH3)2.
Aryl moiety in aryl and aryl alkyl, aryloxy group, alkoxy aryl and fragrant amino etc. includes phenyl or naphthalene Base etc..
Heteroaryl moieties in heteroaryl and heteroaryl alkyl, heteroaryl epoxide and heteroarylalkoxy etc. refer to containing 1 The heteroatomic five-membered ring of individual or multiple N, O, S or hexatomic ring.Such as furyl, pyrazolyl, thiazolyl, pyridine radicals, pyrimidine radicals, pyrrole Piperazine base, pyridazinyl, triazine radical, quinolyl, benzoxazolyl, indyl etc..
Table 1 to table 26 lists the compound of formula I representative respectively, but compound of Formula I is not limited only to this.
It is selected from O when Ar is selected from Ar-1, X, Q is selected from Q1When, representation compound 1-30 is shown in Table 1.
Table 1
Compound (R1)n Compound (R1)n
1 H 16 2,5-2CH3
2 2-CH3 17 2,4-2Cl
3 2-Cl 18 2,4-2CH3
4 2-CN 19 2-Cl-4-CH3
5 2-CF3 20 2-Cl-4-CF3
6 3-CF3 21 2-Cl-4-OCF3
7 3-CN 22 3,5-2Cl
8 3-NO2 23 3,5-2CH3
9 4-CF3 24 2,6-2Cl-4-CF3
10 4-OCHF2 25 2-Cl-4-CN
11 4-OCF3 26 2-Cl-4-NO2
12 4-Cl 27 2,4,6-3Cl
13 4-CN 28 2-Cl-4-F
14 4-NO2 29 2-CH3-5-CN
15 2,5-2Cl 30 2,6-2Cl
Table 2：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q2When, other substituents of representation compound 31-60 and table 1 are changed Compound 1-30 is consistent；
Table 3：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q3When, other substituents of representation compound 61-90 and table 1 are changed Compound 1-30 is consistent；
Table 4：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q4When, other substituents of representation compound 91-120 and table 1 are changed Compound 1-30 is consistent；
Table 5：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q5When, other substituents of representation compound 121-150 and table 1 Compound 1-30 is consistent；
Table 6：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q6When, other substituents of representation compound 151-180 and table 1 Compound 1-30 is consistent；
Table 7：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q7When, other substituents of representation compound 181-210 and table 1 Compound 1-30 is consistent；
Table 8：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q8When, other substituents of representation compound 211-240 and table 1 Compound 1-30 is consistent；
Table 9：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q9When, other substituents of representation compound 241-270 and table 1 Compound 1-30 is consistent；
Table 10：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q19When, other substituents of representation compound 271-300 and table 1 Compound 1-30 is consistent；
Table 11：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q20When, other substituents of representation compound 301-330 and table 1 Compound 1-30 is consistent；
Table 12：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q21When, other substituents of representation compound 331-360 and table 1 Compound 1-30 is consistent；
Table 13：It is selected from O, Q when Ar is selected from Ar-1, X selected from Q22When, other substituents of representation compound 361-390 and table 1 Compound 1-30 is consistent；
Table 14：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q1、R2Selected from CH3, p=0 when, representation compound 391-420 its Its substituent is consistent with table 1 compound 1-30；
Table 15：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q2、R2Selected from CH3, p=0 when, representation compound 421-450 its Its substituent is consistent with table 1 compound 1-30；
Table 16：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q3、R2Selected from CH3, p=0 when, representation compound 451-480 its Its substituent is consistent with table 1 compound 1-30；
Table 17：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q4、R2Selected from CH3, p=0 when, representation compound 481-510 its Its substituent is consistent with table 1 compound 1-30；
Table 18：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q5、R2Selected from CH3, p=0 when, representation compound 511-540 its Its substituent is consistent with table 1 compound 1-30；
Table 19：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q6、R2Selected from CH3, p=0 when, representation compound 541-570 its Its substituent is consistent with table 1 compound 1-30；
Table 20：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q7、R2Selected from CH3, p=0 when, representation compound 571-600 its Its substituent is consistent with table 1 compound 1-30；
Table 21：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q8、R2Selected from CH3, p=0 when, representation compound 601-630 its Its substituent is consistent with table 1 compound 1-30；
Table 22：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q1、R2Selected from SCH3, p=0 when, representation compound 631-660's Other substituents are consistent with table 1 compound 1-30；
Table 23：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q1、R2Selected from OCH3, p=0 when, representation compound 661-690's Other substituents are consistent with table 1 compound 1-30；
Table 24：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q1、R2Selected from H, p=0 when, other of representation compound 691-720 Substituent is consistent with table 1 compound 1-30；
Table 25：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q1、R2Selected from CH3, p=1 when, representation compound 721-750 its Its substituent is consistent with table 1 compound 1-30；
Table 26：It is selected from O, Q when Ar is selected from Ar-2, X selected from Q3、R2Selected from CH3, p=1 when, representation compound 751-780 its Its substituent is consistent with table 1 compound 1-30；
Compound 781：It is selected from O, Q when Ar is selected from Ar-3, X selected from Q1、R1It is selected from O selected from H, A；
Compound 782：It is selected from O, Q when Ar is selected from Ar-3, X selected from Q1、R1It is selected from S selected from H, A；
Compound 783：It is selected from O, Q when Ar is selected from Ar-3, X selected from Q1、R1It is selected from NH selected from H, A；
Compound 784：It is selected from O, Q when Ar is selected from Ar-3, X selected from Q2、R1It is selected from O selected from H, A；
Compound 785：It is selected from O, Q when Ar is selected from Ar-3, X selected from Q3、R1It is selected from O selected from H, A；
Compound 786：It is selected from S, Q when Ar is selected from Ar-3, X selected from Q1、R1It is selected from O selected from H, A；
Compound 787：It is selected from S, Q when Ar is selected from Ar-3, X selected from Q1、R1It is selected from S selected from H, A；
Compound 788：It is selected from S, Q when Ar is selected from Ar-3, X selected from Q1、R1It is selected from NH selected from H, A；
Compound 789：It is selected from S, Q when Ar is selected from Ar-3, X selected from Q1、(R1) n be selected from 5-CH3, A be selected from O；
Compound 790：It is selected from S, Q when Ar is selected from Ar-3, X selected from Q1、(R1) n be selected from 5-OCH3, A be selected from S；
Compound 791：It is selected from S, Q when Ar is selected from Ar-3, X selected from Q1、(R1) n be selected from 5-CF3, A be selected from NH；
Compound 792：Orysastrobin（orysastrobin）.
Compound 793：2-cyano-3-amino-3-phenylancryic acetate.
The compounds of this invention according to patent CN101119961, CN101205187, EP253213, US4829085, Method preparation disclosed in CN101268780 etc., or prepare with reference to method known to other.
In present invention, the purposes of the compounds of this invention is as plant virus inhibitor, wherein main crop bag Include cereal crops（Paddy rice, wheat, barley, oat, corn, millet, Chinese sorghum etc.）, tuber crops（Sweet potato, potato, cassava Deng）, legume crop（Soybean, broad bean, pea, mung bean, red bean, garden pea etc.）And fibre crops（Cotton, crudefiber crop, silkworm and mulberry etc.）、 Oil crops（Peanut, rape, sesame, soybean, sunflower etc.）, sugar crop（Beet, sugarcane etc.）, beverage crops（Tealeaves, coffee Coffee, cocoa etc.）, hobby crop（Tobacco etc.）, medicinal crop（Ginseng, bulb of fritillary etc.）, tropical crops（Rubber, coconut, oil palm, sword Fiber crops etc.）, melon（Watermelon, muskmelon, "Hami" melon, pawpaw etc.）, and fruit, silkworm and mulberry, vegetables（Tomato, capsicum, radish, cucumber, white Dish, celery, hot pickled mustard tube, green onion, garlic, various wild vegetables etc.）, bamboo shoots, flowers（As orchid etc.）, potted landscape and ornamental plant etc.；Also include Fruit tree（Apple, banana, citrus, peach, papaya）, hops, pepper, seedling and other garden crops.Main virus bag Include tobacco mosaic virus (TMV), Tobacco rattle virus, tobacco leaf curl virus, nepovirus, marmor erodens, sweet potato pinniform spot Refute virus, marmor upsilon, corium solani, potato virus X, potato virus S, marmor solani, potato Spindle tuber viroid, corn mosaic virus, sugarcane streak mosaic virus, cucumber mosaic virus, melon mosaic virus, pumpkin flower Mosaic virus, tomato spotted wilf virus, tomato aspermy virus, BCTV, alfalfa mosaic virus, abaca bunchy top virus, banana Streak virus, citrus tristeza virus, WYMV, wheat soil-borne mosaic poison, Wheat ecological regions, barley Yellow dwarf virus, wheat mosaic poison, fractilinea oryzae, Rice Gall Dwarf In Guangdong Province, Rice bunchy stunt virus, black streaked dwarf virus of rice Poison, Rice Ragged Stunt Virus, oryza virus 3, rice hoja blanca virus, rice grassy stunt virus, rice leaf yellowing virus, Paddy rice yellow virus, Rice tungro spherical virus, rice yellow mottle poison, rice stripe necrosis virus, paddy rice Dong Gelu bar Shape virus, necrosis mosaic disease poison etc..
The compounds of this invention has excellent anti-phytoviral activity, can effectively prevent and treat tobacco, vegetables（Capsicum, tomato, melon Dish etc.）, fruit tree, beans, cereal, the virosis of the various crop such as potato class, be particularly suitable for preventing and treating tobacco mosaic disease, vegetables（Peppery Green pepper, tomato, melon dish, Chinese cabbage etc.）Virosis, Virus Diseases of Rice（Including rice dwarf virus disease, black streak dwarf, BYDV, striped leaf Rot etc.）, potato virus disease etc..
Specific embodiment
With resisting tobacco mosaic virus（Tobacco Mosaic Virus,TMV）As a example activity, but do not limit the present invention and resist The application of other viruses.The mensuration program of compound of Formula I activity of resisting tobacco mosaic virus of the present invention is as follows：
The preparation of compound solution：Designed according to test dose, accurately weigh test sample in volumetric flask, add ethanol 200 microlitres make it fully dissolve, and with the redistilled water containing 1%Tween20, are made into the solution of desired concn compound.
The assay method of compound of Formula I activity of resisting tobacco mosaic virus of the present invention（With reference to CN101891710B）As follows：
Directly the mensure of antiviral activity is carried out using half leaf withered spot method in vitro.The assay method of live body induced activity be by The consistent common cigarette of seedling age, 3 basins are one group, and respectively at the tobacco seedlings of inoculation pre-treatment in 7 days, processing mode includes：Spray for examination Compound solution 2 to 3 times, 10 milliliters every time, or soil treatment, 10 milliliters every time, rub on the tobacco leaf newly growing within the 7th day and connect Plant TMV, tobacco seedlings are placed in after cultivating 3 days under its growth preference temperature and illumination, check incidence, comprehensive scab number is pressed Formula calculates the induction antiviral effect to TMV for the test compound, and each process sets 3 repetitions.Referring concurrently to document Fan Z.J.;et al.J.Agric.Food Chem.,2010,58(5):2630-2636 and Zuo X.;et al.J.Agric.Food Chem.,2010,58(5):The method of 2755-2762 description carry out compound to the protection of tobacco mosaic virus (TMV), passivation, treat Direct antiviral activity in vitro.
R=(CK-I)/CK×100
Wherein：R is the effect of noval chemical compound TMV anti-to tobacco, and unit is %；
CK compares the average withered spot number of blade for clear water, and unit is individual；
I is the average withered spot number of chemicals treatment rear blade, and unit is individual.
The direct in vitro antiviral activity of part the compounds of this invention the results are shown in Table 27, and live body induced activity the results are shown in Table 28, live body protection activity the results are shown in Table 29, and live body passivation Activity Results are shown in Table 30, and live body therapeutic activity the results are shown in Table 31.
Table 27 direct antiviral activity result in vitro
Table 28 live body induced activity result
Table 29 live body protection activity result
Table 30 live body is passivated Activity Results
Table 31 live body therapeutic activity result

Claims (6)

1. substituent ether and thio-ether type compounds as the application of anti-plant virus agent it is characterised in that structure is as shown in formula I Compound：
In formula：
Q is selected from one of following group：
Ar is selected from following Ar-1：
R1Selected from halogen, C1-C12Alkyl, C3-C12Cycloalkyl, halo C1-C12Alkyl, C1-C12Alkoxyl, halo C1-C12Alcoxyl Base, C1-C12Alkoxy C1-C12Alkyl, halo C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkylthio group, halo C1-C12Alkylthio group；
The integer of n=0-4；X=O or S.
2. application according to claim 1 is it is characterised in that structure compound as shown in formula I, wherein
Q is selected from Q1、Q2、Q3Or Q4；
Ar is selected from Ar-1；
R1Selected from halogen, C1-C6Alkyl, C3-C6Cycloalkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6Alkoxyl, C1-C6Alkoxy C1-C6Alkyl, halo C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkylthio group, halo C1-C6Alkylthio group
N=0,1,2 or 3；X=O or S.
3. application according to claim 2 is it is characterised in that structure compound as shown in formula I, wherein
Q is selected from Q1、Q2、Q3Or Q4；
Ar is selected from Ar-1；
R1Selected from halogen, C1-C6Alkyl, C3-C6Cycloalkyl, halo C1-C6Alkyl, C1-C6Alkoxy C1-C6Alkyl, C1-C6Alkane sulphur Base, halo C1-C6Alkylthio group, n=0,1,2 or 3；X=O or S.
4. application according to claim 3 is it is characterised in that structure compound as shown in formula I, wherein
Q is selected from Q1、Q2、Q3Or Q4；
Ar is selected from Ar-1；
R1Selected from F, Cl, Br, I, C1-C6Alkyl, C3-C6Cycloalkyl, halo C1-C6Alkyl, C1-C6Alkoxy C1-C6Alkyl, C1-C6 Alkylthio group, halo C1-C6Alkylthio group；
N=0,1,2 or 3；X=O or S.
5. according to claim 1 application it is characterised in that：Described substituent ether and thio-ether type compounds are as being used for preventing Control the anti-plant of the virosis that tobacco, vegetables, fruit tree, legume crop, cereal crops or tuber crops are caused by tobacco mosaic virus (TMV) Thing viral agent.
6. according to claim 5 application it is characterised in that：Described substituent ether and thio-ether type compounds are as being used for preventing Control the anti-plant virus agent of the virosis that tobacco, vegetables, paddy rice or potato are caused by tobacco mosaic virus (TMV).
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