CN1159290C - Method for preparing biocide alkyl-substituted (hetero)-aryl-ketoxime-o-ether and its intermediate ketone or oxime compounds - Google Patents

Method for preparing biocide alkyl-substituted (hetero)-aryl-ketoxime-o-ether and its intermediate ketone or oxime compounds Download PDF

Info

Publication number
CN1159290C
CN1159290C CNB991155572A CN99115557A CN1159290C CN 1159290 C CN1159290 C CN 1159290C CN B991155572 A CNB991155572 A CN B991155572A CN 99115557 A CN99115557 A CN 99115557A CN 1159290 C CN1159290 C CN 1159290C
Authority
CN
China
Prior art keywords
alkyl
heteroaryl
aryl
group
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CNB991155572A
Other languages
Chinese (zh)
Other versions
CN1288002A (en
Inventor
柳爱平
龙胜佑
欧晓明
于正英
黄明智
徐建兵
刘曙东
王永江
侯仲轲
任训和
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hunan Research Institute of Chemical Industry
Original Assignee
Hunan Research Institute of Chemical Industry
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hunan Research Institute of Chemical Industry filed Critical Hunan Research Institute of Chemical Industry
Priority to CNB991155572A priority Critical patent/CN1159290C/en
Publication of CN1288002A publication Critical patent/CN1288002A/en
Application granted granted Critical
Publication of CN1159290C publication Critical patent/CN1159290C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Landscapes

  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention discloses a series of compounds of alkyl group-substituted (hetero)-aryl group-ketoxime-O-ether showed by general formula (I), a series of compounds of intermediate body of ketone and oximate showed by general formula (II) and general formula (III), a preparation method thereof and a bioactivity thereof. The definition of each symbol in general formulas (I), (II) and (III) is disclosed in the specification. The compound showed in general formula (I) has an excellent bioactivity, particularly has a better bioactivity in preventing and curing pests in agriculture, gardening, flower, sanitation, etc. The compound showed in general formula (I) kills insects continuously and quickly with no damage to crops. Some of the compounds showed in general formula (II) and general formula (III) used as intermediate bodies also have a preferable bioactivity.

Description

Biocidal alkyl-replacement (mixing)-aryl-ketoxime-O-ether and intermediate ketone, oxime compounds and preparation method thereof
The present invention relates to a series of biocidal alkyl-replacement (mixing)-aryl-ketoxime-O-ether and intermediate ketone, oxime compounds and preparation method thereof.
Relevant alkyl-replacement (mixing)-aryl-ketoxime-O-ether compound all has the lot of documents report both at home and abroad as the research and the application of agricultural chemicals, also has commercially available agricultural chemical to come out simultaneously, relevant document and patent are as Bull, M.J., Davics, J.H., Searle, J.G., Henry, A.G., Pestic.Sci., II, 249 (1980); Paul, JillHelaine et al., Eur.Pat.Appl.4,754, US Appl.891,991; Jpn.Kokai Tokkyo Koho80,115,864; B. storehouse grace, G. Sa Bake etc., CN 1077709A (DE P4213149.9); CN1059515A; DE 4442730A; DE 2806664A; Xi Gangmin heros etc. are openly speciallyyed permit communique, 55-17323, and the 54-13852. commercially available agricultural chemical is as oxime ether chrysanthemum ester (CA registration number 69043-27-2) etc.Alkyl-replacement (mixing)-aryl-ketoxime-O-ether compound has good biocidal activity.It not only has characteristics such as wide spectrum, efficient and low toxicity, and the biological activity characteristics that also have pyrethroid pesticides such as knocking down fast that have.Alkyl-replacement (mixing)-aryl-ketoxime-O-ether compound obtains developing more widely and using as a class novel agrochemical.For finding new alkyl-replacement (mixing)-aryl-ketoxime-O-ethers pesticide species, Hunan Chemical Research Institute has carried out extensive research to this compounds, and with regard to some bioactive new compound application is arranged Chinese invention patent (application number is: 98 112665.0), by further work, have found that a series of fabulous agricultural chemicals character that have, particularly new alkyl-replacement (the mixing)-aryl-ketoxime-O-ether compound of insecticidal properties.
The present invention is shown in the general formula (I)-serial alkyl-replacement (mixing)-aryl-ketoxime-O-ether and general formula (II) and a series of intermediate ketones, the oxime compounds shown in the general formula (III):
Figure C9911555700091
General formula (I), (II) and (III) in:
I.Ar 1And Ar 2Be identical or different, and representative
(a) (C 6-C 12The heteroaryl of)-aryl or 1O carbon atom of band as many as, or
(b) as at I.a) in determined implication, be selected from case of necessity following in 5 identical or different substituting groups of as many as replace:
Halogen, nitro, cyano group, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, cyano group-(C 1-C 6)
-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkylthio-(C 1-C 6)
-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)
-halogenated alkoxy, (C 1-C 6)-halogenated alkoxy alkyl, (C 1-C 6)-alkylthio, (C 1-C 6)
-halogenated alkylthio, (C 1-C 6)-alkyl sulphonyl, (C 1-C 6)-alkyl sulphinyl, (C 1-C 6)
-alkoxy carbonyl, (C 1-C 6)-alkylamino, two-(C 1-C 6)-alkylamino, (C 2-C 6)
-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-alkenyl oxy alkyl, (C 2-C 6)
-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-halogenated alkenyl oxy
Alkyl, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl,
(C 2-C 6)-halo alkynyloxy base, (C 3-C 8)-cycloalkyl, (C 3-C 8)-cycloalkyl oxy,
(C 3-C 8)-cycloalkyl amino, (C 6-C 12)-aryl, (C 6-C 12)-aryloxy, (C 6-C 12)
-artyl sulfo, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-aryloxy carbonyl
Base, (C 6-C 12)-aryl sulfonyl, (C 6-C 12)-aryl sulfonyl kia, (C 6-C 12)-aryl
Amino, heteroaryl, heteroaryl oxygen base, heteroaryl-(C 1-C 4)-alkyl, the heteroaryl sulfenyl,
Heteroaryl oxygen base carbonyl, heteroarylsulfonyl, the heteroaryl sulfinyl, and
When substituting group is aryl or heteroaryl 1) I.b), sometimes can be by-individual or a plurality of (C that are selected from 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-haloalkyl, (C 1-C 6The identical or different group of)-halogenated alkoxy and halogen replaces, and heteroaryl is the heteroaryl of 10 carbon atoms of band as many as,
2) cycloalkyl I.b) can be selected from halogen, (C by 5 of as many as sometimes 1-C 4The identical or different group of)-alkyl replaces,
3) represent methylenedioxy group or ethylenedioxy for substituent 2 I.b), methylenedioxy group or ethylenedioxy sometimes with 1 or 2 identical or different be selected from halogen and (C 1-C 6The substituting group of)-alkyl,
I.a) and determined the aryl and the partly or entirely hydrogenation of heteroaryl of implication, wherein 1 or 2 CH I.b) 4) 2Group can be replaced by CO,
II.R 1And R 2Be identical or different, and representative
Hydrogen, halogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, cyano group-(C 1-C 6)-alkyl, (C 1-C 6)
-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkylthio-(C 1-C 6)-alkyl, (C 1-C 6)-alkane
Oxygen base-(C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkylthio, (C 1-C 6)-alkane
The base alkylsulfonyl, (C 1-C 6)-alkyl sulphinyl, (C 1-C 6)-alkoxy carbonyl, (C 1-C 6)-alkyl
Amino, two-(C 1-C 6)-alkylamino, (C 1-C 6)-halogenated alkoxy, (C 2-C 6)-alkenyl,
(C 2-C 6)-alkenyl oxy, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy,
(C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl, (C 2-C 6)-halo
The alkynyloxy base, (C 3-C 8)-cycloalkyl, (C 3-C 8)-cycloalkyl oxy, (C 3-C 8)-cycloalkyl
Amino, (C 6-C 12)-aryl, (C 6-C 12)-aryloxy, (C 6-C 12)-aryl-(C 1-C 4)-alkane
Base, (C 6-C 12)-artyl sulfo, (C 6-C 12)-aryloxy carbonyl, (C 6-C 12)-aryl sulfonyl,
(C 6-C 12)-aryl sulfonyl kia, (C 6-C 12)-arylamino, heteroaryl, heteroaryl oxygen base, assorted
Aryl-(C 1-C 4)-alkyl, the heteroaryl sulfenyl, heteroaryl oxygen base carbonyl, heteroarylsulfonyl,
The heteroaryl sulfinyl,
III.R 3Representative
(a) hydrogen,
(b) (C 1-C 6)-alkyl, (C 6-C 12)-aryl, the heteroaryl of 10 carbon atoms of band as many as, (C 2-C 6)-alkenyl, (C 2-C 6)-alkynyl, (C 1-C 4)-acyl group
III.b) group described in can be selected from halogen, (C sometimes 1-C 4)-alkyl, (C 1-C 4)-alkoxyl group, (C 1-C 4)-haloalkyl, (C 1-C 4)-alkylthio, (C 1-C 4Identical or the different groups of)-halogenated alkoxy replace,
IV.X represents O, S, SO, SO 2, NH, NR a[R aBe (C 1-C 4)-alkyl],
V.Y represents hydrogen, cyano group, halogen, (C 1-C 4)-alkyl, (C 1-C 4)-alkoxyl group,
VI.M be hydrogen or-alkali metal atom,
VII.m or n represent 0,1, and 2 or 3.
All abovementioned alkyls, alkenyl and alkynyl can be straight chain also can be side chain, also be applicable to simultaneously, as by alkyl derivative group alkoxyl group, alkoxy carbonyl, alkylthio, haloalkyl and arylalkyl by they derivative groups.
Haloalkyl, halogenated alkenyl and halo alkynyl are meant wherein 1, the alkyl that a plurality of or all hydrogen atoms are replaced by halogen, alkenyl and alkynyl.Also be applicable to by they derivative groups simultaneously halogenated alkoxy is arranged, halogenated alkylthio, halo alkoxy carbonyl and aryl halide substituted alkyl as the group that derives from by haloalkyl.
Halogen is meant fluorine, chlorine, bromine or iodine, preferred fluorine, chlorine or bromine.
(C 6-C 12The preferred phenyl of)-aryl and by its derivative group, as naphthyl, xenyl etc.
The heteroaryl preferred one or the aryl bicyclic of 10 carbon atoms of band as many as have 1 N at least, O and/or S in the formula, as thienyl, benzothienyl, furyl, benzofuryl, pyrryl, indyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, oxazolyl, isoxazolyl, thiazolyl and isothiazolyl.
(C 6-C 12The partly or entirely hydrogenation of heteroaryl of)-aryl and 10 carbon atoms of band as many as, wherein 1 or 2 CH 2-Ji is replaced by CO, as cyclohexenyl, and cyclohexanedione base etc.
At general formula (I), (II) and (III) in, At 1Preferred following groups:
Z is O, S or NR 5, R 5Be hydrogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkylthio-(C 1-C 6)-alkyl, cyano group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxy carbonyl, (C 2-C 6)-alkenyl, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-alkynyl, (C 2-C 6)-halo alkynyl, (C 3-C 8)-cycloalkyl, and cycloalkyl can be selected from halogen or (C by 5 of as many as sometimes 1-C 4The identical or different group of)-alkyl replaces (C 6-C 12)-aryl, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-aryloxycarbonyl, the heteroaryl of 10 carbon atoms of band as many as, heteroaryl oxygen base carbonyl, heteroaryl-(C 1-C 4)-alkyl,
P is one 0 to 5 a integer,
R 4Be identical or different, and represent hydrogen, halogen, nitro, cyano group, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, cyano group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkylthio-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)-halogenated alkoxy, (C 1-C 6)-halogenated alkoxy alkyl, (C 1-C 6)-alkylthio, (C 1-C 6)-halogenated alkylthio, (C 1-C 6)-alkyl sulphonyl, (C 1-C 6)-alkyl sulphinyl, (C 1-C 6)-alkoxy carbonyl, (C 1-C 6)-alkylamino, two-(C 1-C 6)-alkylamino, (C 2-C 6)-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-alkenyl oxy alkyl, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-halogenated alkenyl oxy alkyl, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl, (C 2-C 6)-halo alkynyloxy base, (C 3-C 8)-cycloalkyl, (C 3-C 8)-cycloalkyl oxy, (C 3-C 8)-cycloalkyl amino, (C 6-C 12)-aryl, (C 6-C 12)-aryloxy, (C 6-C 12)-artyl sulfo, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-aryloxy carbonyl, (C 6-C 12)-aryl sulfonyl, (C 6-C 12)-aryl sulfonyl kia, (C 6-C 12)-arylamino, heteroaryl, heteroaryl oxygen base, heteroaryl-(C 1-C 4)-alkyl, the heteroaryl sulfenyl, heteroaryl oxygen base carbonyl, heteroarylsulfonyl, the heteroaryl sulfinyl,
R 4Preferred group is a hydrogen, halogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)-halogenated alkoxy, (C 1-C 6)-alkyl sulphonyl, (C 2-C 6)-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl, (C 2-C 6)-halo alkynyloxy base, (C 3-C 8)-cycloalkyl, (C 3-C 8)-cycloalkyl oxy, (C 3-C 8)-halogenated cycloalkyl, (C 6-C 12)-aryl, (C 6-C 12)-aryloxy, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-artyl sulfo, the heteroaryl of 10 carbon atoms of band as many as, heteroaryl oxygen base, heteroaryl-(C 1-C 4)-alkyl.And
1) R 4Described in substituting group when being aryl or heteroaryl, sometimes can be by-individual or a plurality of (C that are selected from 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-haloalkyl, (C 1-C 6The identical or different group of)-halogenated alkoxy and halogen replaces, and heteroaryl is the heteroaryl of 10 carbon atoms of band as many as,
2) R 4Described in cycloalkyl can be selected from halogen, (C by 5 of as many as sometimes 1-C 4The identical or different group of)-alkyl replaces,
3) R 4Described in substituent 2 represent methylenedioxy group or ethylenedioxy, methylenedioxy group or ethylenedioxy sometimes with 1 or 2 identical or different be selected from halogen and (C 1-C 6The substituting group of)-alkyl,
At general formula (I), (II) and (III) in, Ar 1Preferred especially following groups:
Figure C9911555700121
Figure C9911555700131
Z is O in the formula, S or NR 5, R 5Be hydrogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxy carbonyl, (C 2-C 6)-alkenyl, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-alkynyl, (C 2-C 6)-halo alkynyl.
R 4Be hydrogen, halogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)-halogenated alkoxy, (C 1-C 6)-alkyl sulphonyl, (C 2-C 6)-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl, (C 2-C 6)-halo alkynyloxy base, (C 3-C 8)-cycloalkyl, (C 3-C 8)-halogenated cycloalkyl.
R 4Represent methylenedioxy group for substituent 2, methylenedioxy group sometimes with 1 or 2 identical or different be selected from halogen and (C 1-C 6The substituting group of)-alkyl.
At general formula (I), (II) and (III) in, R 1And R 2Be identical or different, and preferred hydrogen, halogen, (C 1-C 4)-alkyl, (C 1-C 4)-alkoxyl group, (C 1-C 4)-haloalkyl, (C 1-C 4)-alkylthio, (C 1-C 4)-alkenyl, (C 1-C 4)-alkynyl, (C 1-C 4)-halogenated alkenyl, (C 1-C 4)-halo alkynyl, (C 1-C 4)-alkyl sulphonyl, (C 1-C 4)-alkyl sulphinyl, (C 1-C 4)-alkylamino,
At general formula (I), (II) and (III) in, R 3Preferred hydrogen, (C 1-C 4)-alkyl, (C 1-C 4)-haloalkyl, (C 1-C 4)-alkenyl, (C 1-C 4)-alkynyl, (C 1-C 4)-halogenated alkenyl, (C 1-C 4)-halo alkynyl, (C 6-C 12)-aryl,
At general formula (I), (II) and (III) in, m is preferred 0, n preferred 1.
At general formula (I), (II) and (III) in, Ar 2Preferably:
R represents N or CH, and q is O, S, NH or CH 2, preferred O or CH 2, R 6Be hydrogen, halogen, allyl group oxygen base, propargyloxy,
Figure C9911555700141
F represents fluorine,
T is identical or different with g, represents 0,1,2,3 or 4, and t and g and be not more than 5,
R 7Be identical or different, and represent hydrogen, halogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)-halogenated alkoxy, (C 1-C 6)-alkyl sulphonyl, (C 2-C 6)-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl, (C 2-C 6)-halo alkynyloxy base, (C 3-C 8)-cycloalkyl, (C 3-C 8)-cycloalkyl oxy, (C 3-C 8)-halogenated cycloalkyl, (C 6-C 12)-aryl, (C 6-C 12)-aryloxy, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-artyl sulfo, the heteroaryl of 10 carbon atoms of band as many as, heteroaryl oxygen base, heteroaryl-(C 1-C 4)-alkyl.
W is 1,2 or 3 in the formula,
Z is O, S or NR 5, R 5Be hydrogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkylthio-(C 1-C 6)-alkyl, cyano group (C 1-C 6)-alkyl, (C 1-C 6)-alkoxy carbonyl, (C 2-C 6)-alkenyl, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-alkynyl, (C 2-C 6)-halo alkynyl, (C 3-C 8)-cycloalkyl, and cycloalkyl can be selected from halogen or (C by 5 of as many as sometimes 1-C 4The identical or different group of)-alkyl replaces (C 6-C 12)-aryl, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-aryloxycarbonyl, the heteroaryl of 10 carbon atoms of band as many as, heteroaryl carbonyl, heteroaryl-(C 1-C 4)-alkyl,
R 8Be identical or different, and represent hydrogen, halogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)-halogenated alkoxy, (C 2-C 6)-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl, (C 2-C 6)-halo alkynyloxy base, (C 6-C 12)-aryloxy, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-artyl sulfo, the heteroaryloxy of 10 carbon atoms of band as many as, heteroaryl sulfenyl, heteroaryl-(C 1-C 4)-alkyl, and R 8In aryl or heteroaryl, can be selected from (C sometimes 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-haloalkyl, (C 1-C 6The identical or different group of)-halogenated alkoxy and halogen replaces,
R 8Preferred especially benzyl, phenoxy group, propenyl, proyl, methyl or trifluoromethyl,
Figure C9911555700151
F represents fluorine,
R 9Be hydrogen, fluorine or methyl,
P is 0,1 or 2,
R is (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, preferable methyl,
A is an oxygen, sulphur or NH,
B is nitrogen or CH,
At general formula (I), (II) and (III) in, particularly preferred Ar 2Be:
Figure C9911555700153
R 6Be hydrogen, 3-fluorine, 4-fluorine, 4-chlorine.
S is O, S, NH or CH 2, preferred O or CH 2
Figure C9911555700154
R 7Be (C 1-C 6)-alkyl, preferred especially CH 3, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-halogenated alkoxy.
R 7Be H, CH 3Or OCH 3
Figure C9911555700162
A=CH 2Or O, Z=O, S.
F is a fluorine,
R 9Be hydrogen, fluorine or methyl,
P is 0,1 or 2.
Figure C9911555700164
R is a methyl,
A is an oxygen, sulphur or NH,
B is nitrogen or CH,
Particularly preferred formula (I), formula (II), and the compound of formula (III) is: Ar 1Be to replace or unsubstituted aryl or heteroaryl Ar 2Be above-mentioned particularly preferred Ar 2, R 1And R 2Be hydrogen, methyl or ethyl, R 3Be methyl, m is 0, and n is 1, and X is S, O, SO 2
Compound shown in formula (I) and the formula (III) can two kinds of geometrical isomer forms occur: " cis " (Z formula) and " trans " (E formula) form, " cis " (Z formula) is oxime-oxygen and aryl or heteroaryl Ar 1Be in the two key homonymies of C=N, " trans " (E formula) is oxime-oxygen and aryl or heteroaryl Ar 1Be in the two key heteropleurals of C=N, during the oxime alkylation, do not change its rotamerism, i.e. " cis " (Z formula) (III) obtains (I) formula oxime ether of corresponding " cis " (Z formula) during the alkylation of formula oxime, and " trans " (E formula) (III) obtains (I) formula oxime ether of corresponding " trans " (E formula) during the alkylation of formula oxime.
Figure C9911555700171
" cis " (Z formula)
" trans " (E formula)
In addition, alkyl-replacement (mixing)-aryl-ketoxime-O-ether shown in the general formula (I) and general formula (II) and (III) shown in intermediate ketone, oxime compound, as have one or more unsymmetrical carbons, it can be a racemic modification, diastereomer or pure optical isomer
Intermediate oxime compound shown in alkyl-replacement (mixing)-aryl-ketoxime-O-ether shown in the general formula (I) and the general formula (III) not only relates to cis (Z formula), also relates to trans (E formula) and both mixtures,
Alkyl-replacement (mixing)-aryl-ketoxime-O-ether shown in the general formula (I) and general formula (II) and (III) shown in intermediate ketone, oxime compound, not only relate to racemic modification, diastereomer also relates to pure optical isomer,
Alkyl-replacement (mixing)-aryl-ketoxime-O-ether shown in the general formula (I) and general formula (II) and (III) shown in intermediate ketone, oxime compound, not only relate to pure isomer, also relate to various mixture of isomers.
Alkyl-replacement (mixing)-aryl-ketoxime-O-ether shown in the segment bounds provided by the invention (I) and general formula (II) and (III) shown in intermediate ketone, oxime compound, see Table 1, in the table 1, group Ar 2Simplify and use G K(K=1-35) abbreviation expression.G kSee Table 2.But formula (I), the compound of formula (II) and formula (III) is not limited only to the compound shown in the table 1.
The present invention also provide alkyl-replacement (the mixing)-aryl-ketoxime-O-ether shown in the formula (I) and general formula (II) and (III) shown in intermediate ketone, the preparation method of oxime compound, the preparation method of formula (I) compound is:
A) compound shown in compound shown in the employing formula (III) and the formula (IV)
In the formula (IV), L representative-individual leavings group is if M is a hydrogen in the formula (III), at an appropriate base such as alkali metal hydroxide, alkaline carbonate, alkali metal hydrocarbonate, alkali metal alcoholates, basic metal, alkalimetal hydride, pyridine, tertiary amine exists down, adds suitable solvent such as suitable solvent and be to be selected from the following solvents one or both: water, tetrahydrofuran (THF), toluene, benzene, acetonitrile, dimethyl sulfoxide (DMSO) etc., add phase-transfer catalyst PTC such as tetrabutylammonium iodide again, Tetrabutyl amonium bromide, tetraethylammonium bromide, hexaoxacyclooctadecane-6-6, in normal pressure, reaction is 1-20 hour and get under the 0-120 ℃ of condition.
During the M=alkali metal atom, the alkylated reaction of its oximate carries out under identical conditions, does not need the existence of appropriate base in the formula (III).Or
B) compound shown in the formula (II), in case of necessity in the presence of an appropriate base with the compound shown in the formula V or with their reactant salt
The preparation method of formula provided by the invention (III) compound is:
Compound shown in the formula (II) and hydroxylamine hydrochloride or hydroxylamine sulfate, in normal pressure, 0-100 ℃ of reaction and getting in a suitable solvent preferably water and/or alcohol, also need add alkali metal hydroxide, alkaline carbonate, alkali metal hydrocarbonate in case of necessity, appropriate base such as pyridine are synthesized
The preparation method of formula provided by the invention (II) compound is: the general formula of different structure (II) compound need select proper raw material and corresponding synthetic method to carry out the synthetic of (II).In general formula (II) compound, when X=S, the compound shown in the available formula (VI)
Figure C9911555700182
Ar in the formula 1And R 1, R 2, X, R 3, n, definition in m such as the claim 1, with the sodium salt of corresponding mercaptan in water solvent, in normal pressure, 30-100 ℃ of reaction 2-10 hour and getting.
Alkyl provided by the invention-replacement (mixing)-aryl-ketoxime-O-ether and intermediate ketone, oxime compounds, biologically active and the compound that has have fabulous biological activity.Particularly showing high reactivity aspect the preventing and treating of insects such as agricultural, gardening, flowers and health, and damage to crops not, all is being gratifying aspect desinsection and lasting insecticidal effect fast.Harmful organism described here include but not limited to this:
Harmful insect: Orthoptera such as blattaria, Thysanoptera such as cotton thrips, rice thrips, melon thrips, Homoptera such as leafhopper, plant hopper, aphid, lepidopteran such as oriental armyworm, prodenia litura, small cabbage moth, cabbage caterpillar, Hymenoptera such as sawfly larva, Diptera such as yellow-fever mosquito, culex, fly, acarina such as tangerine gold melon mite, cotton spider mites;
Harmful pathogenic bacteria: the phytophthora kind, white powder belongs to kind, Gibberella kind, Venturia kind, species of Monilinia fructicola, Rhizoctonia kind, Staphlosporonites kind, Pyricularia Sacc. kind, fusarium kind;
Injurious weed: gramineous weeds such as barnyard grass, amur foxtail, brooklet astilbe root or herb, broad leaved weeds such as lamb's-quarters, bitter cress.
With alkyl provided by the invention-replacement (mixing)-aryl-ketoxime-O-ether or intermediate ketone, oxime compounds, Agrotechnical formulation as effective ingredient, can make desirable any-kind of formulation such as missible oil, wettable powder, suspension agent, granula, suitable auxiliary agent comprises carrier (thinner) and other auxiliary such as spreader-sticker, emulsifying agent, wetting agent, dispersion agent, tackiness agent and decomposition agent.
Agrotechnical formulation prepares embodiment:
Preparation missible oil: with 20 parts (by weight) alkyl provided by the invention-replacement (mixing)-aryl-ketoxime-O-ether compound or intermediate ketone, oxime compound, 73 parts of thinners such as dimethylbenzene and 7 parts of suitable auxiliary agent uniform mixing can prepare missible oil, and dilute with water can be used.
Preparation wettable powder: with 20 parts (by weight) alkyl provided by the invention-replacement (mixing)-aryl-ketoxime-O-ether compound or intermediate ketone, oxime compound, 53 parts of clays, 20 parts of white carbon blacks, 5 parts of lignin silicate and 2 parts of polyoxy ethyl alkyl oxide mixing are worn into fine powder and can be made wettable powder.
Below in conjunction with embodiment the present invention is done into-goes on foot explanation.
Embodiment 1:1-(4-chloro-phenyl-)-2-methylthio group-O-[(3-phenoxy phenyl) methyl] synthetic [No. 30 general formula (I) compound in the table 1] (systhesis of 1-propanone, 1-(4-chlorophenyl)-2-methylthio-O-[(3-phenoxyphenyl) methyl] oxime) of acetoxime ether
Take by weighing 1-(4-chloro-phenyl-)-2-methylthio group acetoxime { 1-propanone, 1-(4-chlorophenyl)-2-methylthio) oxime} (mixture of Z and E isomer, content 90%) 1.7 grams (0.007 mole) are in 18 milliliters of anhydrous acetonitriles that are dissolved with 0.20 gram sodium Metal 99.5,30~40 ℃ the reaction 2~3 hours between after, add 0.3 gram tetrabutylammonium iodide, the back drips m-phenoxy benzyl chloride (content 90%) 1.91 grams (0.008 mole), after dropwising, slowly be warming up to 60~65 ℃ of reactions 8~9 hours.After the processing oily crude product 2.85 gram (mixture of Z and E isomer), purify with the petroleum ether-ethyl acetate column chromatography for separation that reduces pressure, can get Z and E pure isomer, product is faint yellow viscous liquid, Z and E pure isomer weigh 1.49 grams altogether.Purity Z body: 92%E body 93% (gas spectrum), yield 47%.
Hydrogen spectrum δ CDCl3 TMS:
E isomer: 1.26 (d, 3H, CH 3), 2.05 (s, 3H, SCH 3), 4.76 (q, 1H ,-CH-S-), 5.15 (s, 2H, C=N-O-CH 2-), 6.96-7.66 (m, 13H, hydrogen on the phenyl ring).
Z isomer: 1.27 (d, 3H, CH 3), 1.93 (s, 3H, SCH 3), 3.60 (q, 1H ,-CH-S-), 5.02 (s, 2H, C=N-O-CH 2-), 6.88-7.38 (m, 13H, hydrogen on the phenyl ring).
Results of elemental analyses: (measured value/theoretical value): C% 67.41/67.07 H% 5.06/5.35
N% 3.32/3.40 S% 7.25/7.77
Mass spectrum: molecular ion peak M +(411).
Embodiment 2. 1-(4-chloro-phenyl-)-2-methylthio group-O-[(3-phenoxy phenyl) methyl] synthetic [No. 5 general formula (I) compound in the table 1] (synthesis of ethanone, 1-(4-chlorophenyl)-2-methylthio-O-[(3-phenoxyphenyl) methyl] oxime) of second ketoxime ether
Take by weighing 1-(4-chloro-phenyl-)-2-methylmercaptan ethyl ketoxime { ethanone, 1-(4-chlorophenyl)-2-methylthio) oxime} (E isomer, content 90%) 1.7 grams (O.007 mole), m-phenoxy benzyl chloride (content 90%) 1.76 grams (0.007 mole), 0.3 gram tetrabutylammonium iodide, 4 milliliters of toluene add the solution that is made into by 4 ml waters and 0.63 gram sodium hydroxide in batches under stirring in reaction flask, slowly be warming up to 58~60 ℃ of reactions 7~8 hours.After the processing oily crude product 2.67 gram (E isomer), purify with the petroleum ether-ethyl acetate column chromatography for separation that reduces pressure, faint yellow viscous liquid 1.39 grams (E body).Purity 94% (gas spectrum), yield 44%.
Hydrogen spectrum δ CDCl3 TMS: 1.98 (s, 3H, SCH 3), 3.72 (s, 2H ,-CH 2-S-), 5.19 (s, 2H, C=N-O-CH 2-), 6.89-7.66 (m, 13H, hydrogen on the phenyl ring).
Results of elemental analyses: (measured value/theoretical value): C% 66.41/66.08 H% 5.06/4.88
N% 3.52/3.50 S% 8.05/8.54
Mass spectrum: molecular ion peak M +(397).
Synthetic (synthesis of ethanone, 1-(4-chlorophenyl)-2-methylthio oxime) [No. 5 general formula (III) compound in the table 1] of embodiment 3. 1-(4-chloro-phenyl-)-2-methylmercaptan ethyl ketoxime
To reflux condensing tube is housed, thermometer, add 1-(4-chloro-phenyl-)-2-methylthio group ethyl ketone 27.0 grams (0.13 mole) in 250 milliliters of there-necked flasks of stirring magneton, 35 milliliters of ethanol, 14 milliliters in water, oxammonium hydrochloride 12.80 grams (0.18 mole), add solid sodium hydroxide 16.0 grams (0.4 mole) under stirring in batches, finish, keep room temperature (about 25 ℃) reaction 15~20 minutes, after slowly be warming up to 45 ℃ of reactions 45 minutes, reheat was to reflux temperature reaction 5~6 hours.Cooling gets canescence needle-like crystal 29 grams (mixture of Z body and E body) after aftertreatment,, purity 90% (gas spectrum), yield 90%, fusing point: 93.6~96.6 ℃.
Results of elemental analyses: (measured value/theoretical value) C%:50.42/50.11 H%:4.83/4.64
N%:6.47/6.49 S%:13.82/14.80
Mass spectrum: molecular ion peak M +(215).
Synthetic (the synthesis of ethanone of embodiment 4. 1-(4-chloro-phenyl-)-2-methylthio group ethyl ketone (or claiming 4-chloro-2-methylthio group-methyl phenyl ketone), 1-(4-chlorophenyl)-2-methylthio or title acetophenone, 4 '-chloro-2-methylthio) [No. 5 general formula (H) compound in the table 1]
To reflux condensing tube is housed, thermometer, add the sodium methyl mercaptide aqueous solution (content 37%) 41.0 grams (0.217 mole) in 250 milliliters of there-necked flasks of stirring magneton, add 1-(4-chloro-phenyl-)-2-chloroethene ketone (content 95%) 24.75 grams (0.124 mole) under the room temperature, reacted 3~5 hours under 60~80 ℃ of conditions in normal pressure the back in batches, cooling, after aftertreatment, get oily liquids product 27 grams, purity 90% (gas spectrum), yield 97%.
Results of elemental analyses: (measured value/theoretical value) C%:53.80/53.86 H%:4.30/4.52
S%:15.28/15.97
Mass spectrum: molecular ion peak M +(200).
The synthetic synthesis of ethanone of embodiment 5. 1-(4-chloro-phenyl-)-2-chloroethene ketone (or claim 4 '-chloro-2-chloro-methyl phenyl ketone), 1-(4-chlorophenyl)-2-chloro (or 4 '-chloro-2-chloro)-acetophenone
To the reflux condensing tube (drying tube links to each other with the alkali absorption liquid) that band Calcium Chloride Powder Anhydrous drying tube is housed, thermometer, dropping funnel, add chlorobenzene 135 grams (1.2 moles) in 500 milliliters of there-necked flasks of stirring magneton, aluminum trichloride (anhydrous) 88.8 grams (0.667 mole), in slowly dripping after chloroacetyl chloride 69.5 gram (0.615 mole) dropwises from the water clock bucket under 5~15 ℃, slowly be warming up to and react about 70 ℃ to emission-free emitting, cooling, get 118 gram white needle-like crystals through aftertreatment, purity 90% (gas spectrum), yield 91%, fusing point: 97.9~99.0 ℃ (literature value: 98~100 ℃).
Results of elemental analyses: (measured value/theoretical value) C%:50.38/50.82 H%:3.02/3.19
Mass spectrum: molecular ion peak M+ (188).
All formulas (I), the compound of formula (II) and formula (III) can be synthetic with similar approach, and institute's synthetic compound is all through the hydrogen spectrum, and is infrared, and mass spectrum is or/and the ultimate analysis conclusive evidence.
(the Z body is different with the biological activity of E body, and the biological activity of general E body is better than the Z body, and its activity data is generally the activity data of E body or Z and E mixture for biological activity determination embodiment.)
The biological activity test of 6 pairs of mythimna separatas of embodiment (Mythimne separata)
Will be by the missible oil or the wettable powder of alkyl provided by the invention-replacement (the mixing)-aryl-ketoxime-O-ether of above-mentioned Agrotechnical formulation embodiment method preparation or intermediate ketone, oxime active compound, dilute with water is made into the pesticidal solutions of predetermined concentration, choosing 10 mythimna separatas and 5 one cun long maize leafs is put in the culture dish and quantitatively sprays, dry the back and move into normal raising the in the greenhouse, statistics survival and death toll after 24 hours.Experiment repeats 3 times, results averaged.Discovery is numbered 5,6, and 7,8,9,10,11,12,21,22,23,30,31,32,33,34,35,36,37,46,47,48,213,216,229,230,231,238,254,629, a series of general formulas (I) compound mortality ratio when 500ppm (in effective component content) such as 632,645,646,647,654,657 reach 100%.Be numbered 5,8,30 general formula such as grade (I) compounds in compound that has such as the table 1 and under lower concentration, still can make mythimna separata 100% death.
The activity experiment of 7 pairs of bean aphids of embodiment (Aphis fabae)
Will be by the missible oil or the wettable powder of alkyl provided by the invention-replacement (the mixing)-aryl-ketoxime-O-ether of above-mentioned Agrotechnical formulation embodiment method preparation or intermediate ketone, oxime active compound, dilute with water is made into the pesticidal solutions of predetermined concentration, bean aphid is connected on the bean seedlings that just have been unearthed, every strain connects more than 15, then bean seedlings are dipped in the soup together with the examination worm, take out after 5 seconds, unnecessary soup is removed in suction, insert in the sponge of suction, cover with glass-tube, check survival and dead borer population after 24 hours.Repeat results averaged 3 times.Found that to be numbered 5,8 that a series of general formulas (I) compound lethality rates to bean aphid when 250ppm (in effective component content) such as 21,22,23,30,33,46,47,48 reach 100%.Be numbered 5,8,30 general formula such as grade (I) compounds etc. in compound that has such as the table 1 and under lower concentration, still can make bean aphid 100% death.
The insecticidal test of 8 pairs of rice green leafhoppers of embodiment (Nephotetlix cimeticeps)
Will be by the missible oil or the wettable powder of alkyl provided by the invention-(the mixing)-aryl-ketoxime-O-ether of above-mentioned Agrotechnical formulation embodiment method preparation or intermediate ketone, oxime active compound, dilute with water is made into the pesticidal solutions of predetermined concentration, choosing two core rice seedlings immerses in the soup, take out after 5 seconds and dry, place Boiling tube, 20 rice green leafhopper nymphs in 5 age are introduced in every pipe 20 strains then, the mouth of pipe is placed under the greenhouse experiment with white gauze wrapping, checks survival and dead borer population after 24 hours.Experiment repeats 3 times.Found that to be numbered 5,6,7,8,9,10,, a series of general formulas (I) compound lethality rates to leafhopper when 250ppm (in effective component content) such as 11,12,21,22,23,30,31,32,33,34,36,37,46,47,48,188 reach 100%., No. 8, wait general formula (I) compound etc. under lower concentration, still can make leafhopper 100% death 30,33, No. 188 in compound that has such as the table 1 No. 5.
Institute's synthetic compound also has advantages of high activity to other insect:
The biological activity of No. 5 general formula (I) compound in the table 1: beet armyworm E body LC 50(ppm)<5 cabbage looper E body LC 50(ppm)<5 U.S. state tobacco budworm E body LC 50(ppm)<10 black peach aphid E body LC 50(ppm)>100.
The biological activity of No. 30 general formula (I) compound in the table 1: beet armyworm E body LC 50(ppm)<5 Z body LC 50(ppm)>150 cabbage looper E body LC 50(ppm)<1.5 Z body LC 50(ppm)>150 U.S. state tobacco budworm E body LC 50(ppm)<5 Z body LC 50(ppm)>150 black peach aphid E body LC 50(ppm)<15 Z body LC 50(ppm)>150.
Embodiment 9 stripped fungicidal activity determination tests
Alkyl provided by the invention-replacement (mixing)-aryl-ketoxime-O-ether or intermediate ketone, oxime active compound are made into the mother liquor of predetermined concentration with suitable thinner (as acetone), get 1 milliliter of soup in 50 milliliters of PDA substratum that dissolve with transfer pipet, after fully shaking up, pour into respectively in 2 culture dish and repeat as 2 times, cooling back is that 4 millimeters bacterium cake places culture dish central authorities with inoculating needle picking diameter, establishes thinner simultaneously for contrasting.Put into the incubator of optimal temperature after inoculation finishes, measure the mycelial growth diameter after 72 hours, calculate mycelial growth inhibition rate.Found that being numbered 5,7 etc.-serial general formula (III) compound reaches more than 90% one or more crop pathogens mycelial growth inhibition rates when 100ppm (in effective component content).
The experiment of embodiment 10 weeding activity
Will be by alkyl provided by the invention-replacement (the mixing)-aryl-ketoxime-O-ether or the intermediate ketone of above-mentioned Agrotechnical formulation embodiment method preparation, the missible oil of oxime active compound or wettable powder, dilute with water is made into the mother liquor of predetermined concentration, choosing that behind presoaking and germinating bud is about is that 0.3 centimetre even seed is (as barnyard grass, amaranth) placing the diameter that is lined with filter paper in advance is in 9 centimetres the culture dish, and then covering one deck filter paper, add in the ware with a certain amount of soup of pipette, extract, loam cake is placed in the illumination box of optimal temperature, it is long to measure root after 3-4 days, long and the fresh weight of bud calculates inhibiting rate.Found that the growth to one or more unifacial leaves or broadleaf weed when 100ppm (in effective component content) of some compound has restraining effect or growth promoting function.
Group Ar in the formula (I) 2Simplify and use G K(K=1-35) abbreviation expression, then available general formula (VII) expression general formula (I) compound in table 1.
Segment bounds (VII) is that the compound of formula (I), formula (II) and formula (III) shows as table 1, but formula (I), the compound of formula (II) and formula (III) is not limited only to the compound shown in the table 1.
Figure C9911555700241
Table 1
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1 4-Cl H Ethyl CH 3 phenyl S 0 1 G 1 H
2 4-OCH 2CH 3 G 1
3 4-CH 3 G 1
4 3,4-Cl 2 G 1
5 4-Cl H G 1
6 4-F G 1
7 4-Br G 1
8 4-CH 3 G 1
9 4-OCH 3 G 1
10 4-CH 2CH 3 G 1
11 4-OCH 2CH 3 G 1
12 4-CH(CH 3) 2 G 1
13 4-SCH 3 G 1
14 4-C(CH 3) 3 G 1
15 4-CH 2CH 2CH 3 G 1
16 4-OCH(CH 3) 2 G 1
17 4-OCH 2CH 2CH 3 G 1
18 4-SOCH 3 G 1
19 3,4-O-CH 2-O G 1
20 The 4-phenoxy group G 1
21 3,4-Cl 2 G 1
22 3,4-(CH 3) 2 G 1
23 3-Cl,4-CH 3 G 1
24 4-CF 3 G 1
25 4-OCF 3 G 1
26 4-CF 2H G 1
27 4-OCH 2CF 3 G 1
28 3-Br,4-F G 1
29 4-CH 2OCH 3 G 1
No R R 1 R 2 R 3 Ar 1 X m n G K Y
30 4-Cl H CH 3 CH 3 phenyl S 0 1 G 1 H
31 4-F G 1
32 4-Br G 1
33 4-CH 3 G 1
34 4-OCH 3 G 1
35 4-CH 2CH 3 G 1
36 4-OCH 2CH 3 G 1
37 4-CH(CH 3) 2 G 1
38 4-SCH 3 G 1
39 4-C(CH 3) 3 G 1
40 4-CH 2CH 2CH 3 G 1
41 4-OCH(CH 3) 2 G 1
42 4-OCH 2CH 2CH 3 G 1
43 4-SOCH 3 G 1
44 3,4-O-CH 2-O G 1
45 The 4-phenoxy group G 1
46 3,4-Cl 2 G 1
47 3,4-(CH 3) 2 G 1
48 3-Cl,4-CH 3 G 1
49 4-CF 3 G 1
50 4-OCF 3 G 1
51 4-CF 2H G 1
52 4-OCH 2CF 3 G 1
53 3-Br,4-F G 1
54 4-CH 2OCH 3 G 1
55 4-OCF 2CF 2H H G 1
56 4-OCF 2H G 1
57 4-OCH 2CCl=CH 2 G 1
58 4-ethoxy oxyethyl group G 1
59 4-OCH 2CH 2Cl G 1
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
60 3,4,5-Trifluoro H H CH 3 phenyl S 0 1 G 1 H
61 4-allyl oxygen methyl G 1
62 4-CH 2Cl G 1
63 4-NO 2 G 1
64 3-NO 2 G 1
65 4-OCF 2CF 2H CH 3 G 1
66 4-OCF 2H G 1
67 4-OCH 2CCl=CH 2 G 1
68 4-ethoxy oxyethyl group G 1
69 4-OCH 2CH 2Cl G 1
70 3,4,5-Trifluoro G 1
71 4-allyl oxygen methyl G 1
72 4-CH 2Cl G 1
73 4-Cl H 3 G 1
74 4-CH 3 3 G 1
75 2-Cl 1 G 1
76 3-Cl G 1
77 3-CF 3 G 1
78 The 3-phenoxy group G 1
79 2-CH 3 G 1
80 2-Cl CH 3 G 1
81 3-Cl G 1
82 3-CF 3 G 1
83 The 3-phenoxy group G 1
84 2-CH 3 G 1
85 4-Cl CH 3 G 1
86 4-F G 1
87 4-Br G 1
88 4-CH 3 G 1
No. R R 1 R 2 R 3 Ar 1 X m n G K
89 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 0 1 G 1 H
90 4-CH 2CH 3 G 1
91 4-OCH 2CH 3 G 1
92 4-Cl H SCH 3 G 1
93 4-F G 1
94 4-Br G 1
95 4-CH 3 G 1
96 4-OCH 3 G 1
97 4-CH 2CH 3 G 1
98 4-OCH 2CH 3 G 1
99 4-Cl H Ethyl G 1
100 4-F G 1
101 4-Br G 1
102 4-CH 3 G 1
103 4-OCH 2CH 3 G 1
104 4-Cl Sec.-propyl G 1
105 4-F G 1
106 4-OCH 3 G 1
107 4-CH 3 G 1
108 4-OCH 2CH 3 G 1
109 4-Cl N-propyl G 1
110 4-F G 1
111 4-OCH 3 G 1
112 4-OCH 2CH 3 G 1
113 4-Cl Phenyl G 1
114 4-F G 1
115 4-CH 3 G 1
116 4-OCH 2CH 3 G 1
117 H CH 3 2-pyridyl G 1
118 6-Cl G 1
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
119 H H H CH 3 4-pyridyl S 0 1 G 1 H
120 6-H 3-pyridyl G 1
121 6-Cl G 1
122 6-OCH 2CH 3 G 1
123 6-OCH 2CF 3 G 1
124 6-CH 3 G 1
125 6-OCH 3 G 1
126 2-H The 5-pyrimidyl G 1
127 2-Cl G 1
128 2-OCH 2CH 3 G 1
129 H The 2-furyl G 1
130 5-Cl G 1
131 H The 2-thienyl G 1
132 5-Cl G 1
133 H The 2-pyrryl G 1
134 5-Cl G 1
135 H The 2-naphthyl G 1
136 H The 2-benzofuryl G 1
137 H The 2-benzothienyl G 1
138 4-Cl phenyl 1 G 1
139 4-F G 1
140 4-Br G 1
141 4-CH 3 G 1
142 4-OCH 3 G 1
143 4-CH 2CH 3 G 1
144 4-OCH 2CF 3 G 1
145 4-Cl CH 3 CH 3 G 1
146 4-F G 1
147 4-Br G 1
148 4-CH 3 G 1
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
149 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 1 1 G 1 H
150 4-OCH 2CF 3 G 1
151 4-Cl H H O 0 1 G 1
152 4-F G 1
153 4-Br G 1
154 4-CH 3 G 1
155 4-OCH 3 G 1
156 4-CH 2CH 3 G 1
157 4-OCH 2CF 3 G 1
158 4-C1 CH 3 O G 1
159 4-F G 1
160 4-Br G 1
161 4-CH 3 G 1
162 4-OCH 3 G 1
163 4-CH 2CH 3 G 1
164 H H The 2-furyl G 1
165 H The 2-thienyl G 1
166 H 2-pyridyl G 1
167 4-Cl Phenyl SO 2 G 1
168 4-F G 1
169 4-Br G 1
170 4-CH 3 G 1
171 4-OCH 3 G 1
172 4-CH 2CH 3 G 1
173 4-OCH 2CF 3 G 1
174 4-Cl CH 3 G 1
175 4-F G 1
176 4-Br G 1
177 4-CH 3 G 1
178 4-OCH 3 G 1
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
179 4-OCH 2CF 3 H CH 3 CH 3 Phenyl SO 2 0 1 G 1 H
180 4-CH 2CH 3 G 1
181 4-Cl H SO G 1
182 4-F G 1
183 4-Br G 1
184 4-CH 3 G 1
185 4-OCH 3 G 1
186 4-OCH 2CH 3 G 1
187 4-OCH 3 S 3 G 1
188 H CH 3 1 G 1
189 CH 3 G 1
190 4-OCH 2CH 3 H H 1 G 1
191 H CH 3 G 1
192 CH 3 G 1
193 H H SO 2 0 G 1
194 SO G 1
195 H S 3 G 1
196 4-F G 1
197 4-OCH 2CH 3 G 1
198 H 2 G 1
199 SCH 3 1 G 1
200 CH 3 G 1
201 H Chlorine G 1
202 Ethyl G 1
203 F G 1
204 Chlorine Chlorine G 1
205 H N-propyl G 1
206 2,4, the 5-trichlorine H G 1
207 2,4, the 5-trichlorine CH 3 G 1
208 4-SO 2CH 3 H G 1
No R R 1 R 2 R 3 Ar 1 X m n G K Y
209 4-Cl H Ethyl CH 3 phenyl S 0 1 G 8 H
210 4-OCH 2CH 3 G 8
211 4-CH 3 G 8
212 3,4-Cl 2 G 8
213 4-Cl H G 8
214 4-F G 8
215 4-Br G 8
216 4-CH 3 G 8
217 4-OCH 3 G 8
218 4-CH 2CH 3 G 8
219 4-OCH 2CH 3 G 8
220 4-CH(CH 3) 2 G 8
221 4-SCH 3 G 8
222 4-C(CH 3) 3 G 8
223 4-CH 2CH 2CH 3 G 8
224 4-OCH(CH 3) 2 G 8
225 4-OCH 2CH 2CH 3 G 8
226 4-SOCH 3 G 8
227 3,4-O-CH 2-O G 8
228 The 4-phenoxy group G 8
229 3,4-Cl 2 G 8
230 3,4-(CH 3) 2 G 8
231 3-Cl,4-CH 3 G 8
232 4-CF 3 G 8
233 4-OCF 3 G 8
234 4-CF 2H G 8
235 4-OCH 2CF 3 G 8
236 3-Br,4-F G 8
237 4-CH 2OCH 3 G 8
No R R 1 R 2 R 3 Ar 1 X m n G K Y
238 4-Cl H CH 3 CH 3 phenyl S 0 1 G 8 H
239 4-F G 8
240 4-Br G 8
241 4-CH 3 G 8
242 4-OCH 3 G 8
243 4-CH 2CH 3 G 8
244 4-OCH 2CH 3 G 8
245 4-CH(CH 3) 2 G 8
246 4-SCH 3 G 8
247 4-C(CH 3) 3 G 8
248 4-CH 2CH 2CH 3 G 8
249 4-OCH(CH 3) 2 G 8
250 4-OCH 2CH 2CH 3 G 8
251 4-SOCH 3 G 8
252 3,4-O-CH 2-O G 8
253 The 4-phenoxy group G 8
254 3,4-Cl 2 G 8
255 3,4-(CH 3) 2 G 8
256 3-Cl,4-CH 3 G 8
257 4-CF 3 G 8
258 4-OCF 3 G 8
259 4-CF 2H G 8
260 4-OCH 2CF 3 G 8
261 3-Br,4-F G 8
262 4-CH 2OCH 3 G 8
263 4-OCF 2CF 2H H G 8
264 4-OCF 2H G 8
265 4-OCH 2CCl=CH 2 G 8
266 4-ethoxy oxyethyl group G 8
267 4-OCH 2CH 2Cl G 8
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
268 3,4,5-Trifluoro H H CH 3 phenyl S 0 1 G 8 H
269 4-allyl oxygen methyl G 8
270 4-CH 2Cl G 8
271 4-NO 2 G 8
272 3-NO 2 G 8
273 4-OCF 2CF 2H CH 3 G 8
274 4-OCF 2H G 8
275 4-OCH 2CCl=CH 2 G 8
276 4-ethoxy oxyethyl group G 8
277 4-OCH 2CH 2Cl G 8
278 3,4,5-Trifluoro G 8
279 4-allyl oxygen methyl G 8
280 4-CH 2Cl G 8
281 4-Cl H 3 G 1
282 4-CH 3 3 G 1
283 2-Cl 1 G 1
284 3-Cl G 8
285 3-CF 3 G 8
286 The 3-phenoxy group G 8
287 2-CH 3 G 8
288 2-Cl CH 3 G 8
289 3-Cl G 8
290 3-CF 3 G 8
291 The 3-phenoxy group G 8
292 2-CH 3 G 8
293 4-Cl CH 3 G 8
294 4-F G 8
295 4-Br G 8
296 4-CH 3 G 8
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
297 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 0 1 G 8 H
298 4-CH 2CH 3 G 8
299 4-OCH 2CH 3 G 8
300 4-Cl H SCH 3 G 8
301 4-F G 8
302 4-Br G 8
303 4-CH 3 G 8
304 4-OCH 3 G 8
305 4-CH 2CH 3 G 8
306 4-OCH 2CH 3 G 8
307 4-Cl H Ethyl G 8
308 4-F G 8
309 4-Br G 8
310 4-CH 3 G 8
311 4-OCH 2CH 3 G 8
312 4-Cl Sec.-propyl G 8
313 4-F G 8
314 4-OCH 3 G 8
315 4-CH 3 G 8
316 4-OCH 2CH 3 G 8
317 4-Cl N-propyl G 8
318 4-F G 8
319 4-OCH 3 G 8
320 4-OCH 2CH 3 G 8
321 4-Cl Phenyl G 8
322 4-F G 8
323 4-CH 3 G 8
324 4-OCH 2CH 3 G 8
325 H CH 3 2-pyridyl G 8
326 6-Cl G 8
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
327 H H H CH 3 4-pyridyl S 0 1 G 8 H
328 6-H 3-pyridyl G 8
329 6-Cl G 8
330 6-OCH 2CH 3 G 8
331 6-OCH 2CF 3 G 8
332 6-CH 3 G 8
333 6-OCH 3 G 8
334 2-H The 5-pyrimidyl G 8
335 2-Cl G 8
336 2-OCH 2CH 3 G 8
337 H The 2-furyl G 8
338 5-Cl G 8
339 H The 2-thienyl G 8
340 5-Cl G 8
341 H The 2-pyrryl G 8
342 5-Cl G 8
343 H The 2-naphthyl G 8
344 H The 2-benzofuryl G 8
345 H The 2-benzothienyl G 8
346 4-Cl phenyl 1 G 8
347 4-F G 8
348 4-Br G 8
349 4-CH 3 G 8
350 4-OCH 3 G 8
351 4-CH 2CH 3 G 8
352 4-OCH 2CF 3 G 8
353 4-Cl CH 3 CH 3 G 8
354 4-F G 8
355 4-Br G 8
356 4-CH 3 G 8
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
357 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 1 1 G 8 H
358 4-OCH 2CF 3 G 8
359 4-Cl H H O 0 1 G 8
360 4-F G 8
361 4-Br G 8
362 4-CH 3 G 8
363 4-OCH 3 G 8
364 4-CH 2CH 3 G 8
365 4-OCH 2CF 3 G 8
366 4-Cl CH 3 O G 8
367 4-F G 8
368 4-Br G 8
369 4-CH 3 G 8
370 4-OCH 3 G 8
371 4-CH 2CH 3 G 8
372 H H The 2-furyl G 8
373 H The 2-thienyl G 8
374 H 2-pyridyl G 8
375 4-Cl Phenyl SO 2 G 8
376 4-F G 8
377 4-Br G 8
378 4-CH 3 G 8
379 4-OCH 3 G 8
380 4-CH 2CH 3 G 8
381 4-OCH 2CF 3 G 8
382 4-Cl CH 3 G 8
383 4-F G 8
384 4-Br G 8
385 4-CH 3 G 8
386 4-OCH 3 G 8
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
387 4-OCH 2CF 3 H CH 3 CH 3 Phenyl SO 2 0 1 G 8 H
388 4-CH 2CH 3 G 8
389 4-Cl H SO G 8
390 4-F G 8
391 4-Br G 8
392 4-CH 3 G 8
393 4-OCH 3 G 8
394 4-OCH 2CH 3 G 8
395 4-OCH 3 S 3 G 8
396 H CH 3 1 G 8
397 CH 3 G 8
398 4-OCH 2CH 3 H H 1 G 8
399 H CH 3 G 8
400 CH 3 G 8
401 H H SO 2 0 G 8
402 SO G 8
403 H S 3 G 8
404 4-F G 8
405 4-OCH 2CH 3 G 8
406 H 2 G 8
407 SCH 3 1 G 8
408 CH 3 G 8
409 H Chlorine G 8
410 Ethyl G 8
411 F G 8
412 Chlorine Chlorine G 8
413 H N-propyl G 8
414 2,4, the 5-trichlorine H G 8
415 2,4, the 5-trichlorine CH 3 G 8
416 4-SO 2CH 3 H G 8
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
417 4-Cl H Ethyl CH 3 phenyl S 0 1 G 15 H
418 4-OCH 2CH 3 G 15
419 4-CH 3 G 15
420 3,4-Cl 2 G 15
421 4-Cl H G 15
422 4-F G 15
423 4-Br G 15
424 4-CH 3 G 15
425 4-OCH 3 G 15
426 4-CH 2CH 3 G 15
427 4-OCH 2CH 3 G 15
428 4-CH(CH 3) 2 G 15
429 4-SCH 3 G 15
430 4-C(CH 3) 3 G 15
431 4-CH 2CH 2CH 3 G 15
432 4-OCH(CH 3) 2 G 15
433 4-OCH 2CH 2CH 3 G 15
434 4-SOCH 3 G 15
435 3,4-O-CH 2-O G 15
436 The 4-phenoxy group G 15
437 3,4-Cl 2 G 15
438 3,4-(CH 3) 2 G 15
439 3-Cl,4-CH 3 G 15
440 4-CF 3 G 15
441 4-OCF 3 G 15
442 4-CF 2H G 15
443 4-OCH 2CF 3 G 15
444 3-Br,4-F G 15
445 4-CH 2OCH 3 G 15
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
446 4-Cl H CH 3 CH 3 phenyl S 0 1 G 15 H
447 4-F G 15
448 4-Br G 15
449 4-CH 3 G 15
450 4-OCH 3 G 15
451 4-CH 2CH 3 G 15
452 4-OCH 2CH 3 G 15
453 4-CH(CH 3) 2 G 15
454 4-SCH 3 G 15
455 4-C(CH 3) 3 G 15
456 4-CH 2CH 2CH 3 G 15
457 4-OCH(CH 3) 2 G 15
458 4-OCH 2CH 2CH 3 G 15
459 4-SOCH 3 G 15
460 3,4-O-CH 2-O G 15
461 The 4-phenoxy group G 15
462 3,4-Cl 2 G 15
463 3,4-(CH 3) 2 G 15
464 3-Cl,4-CH 3 G 15
465 4-CF 3 G 15
466 4-OCF 3 G 15
467 4-CF 2H G 15
468 4-OCH 2CF 3 G 15
469 3-Br,4-F G 15
470 4-CH 2OCH 3 G 15
471 4-OCF 2CF 2H H G 15
472 4-OCF 2H G 15
473 4-OCH 2CCl=CH 2 G 15
474 4-ethoxy oxyethyl group G 15
475 4-OCH 2CH 2Cl G 15
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
476 3,4,5-Trifluoro H H CH 3 phenyl S 0 1 G 15 H
477 4-allyl oxygen methyl G 15
478 4-CH 2Cl G 15
479 4-NO 2 G 15
480 3-NO 2 G 15
481 4-OCF 2CF 2H CH 3 G 15
482 4-OCF 2H G 15
483 4-OCH 2CCl=CH 2 G 15
484 4-ethoxy oxyethyl group G 15
485 4-OCH 2CH 2Cl G 15
486 3,4,5-Trifluoro G 15
487 4-allyl oxygen methyl G 15
488 4-CH 2Cl G 15
489 4-Cl H 3 G 15
490 4-CH 3 3 G 15
491 2-Cl 1 G 15
492 3-Cl G 15
493 3-CF 3 G 15
494 The 3-phenoxy group G 15
495 2-CH 3 G 15
496 2-Cl CH 3 G 15
497 3-Cl G 15
498 3-CF 3 G 15
499 The 3-phenoxy group G 15
500 2-CH 3 G 15
501 4-Cl CH 3 G 15
502 4-F G 15
503 4-Br G 15
504 4-CH 3 G 15
No. R R 1 R 2 R 3 Ar 1 X m n G K
505 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 0 1 G 15 H
506 4-CH 2CH 3 G 15
507 4-OCH 2CH 3 G 15
508 4-Cl H SCH 3 G 15
509 4-F G 15
510 4-Br G 15
511 4-CH 3 G 15
512 4-OCH 3 G 15
513 4-CH 2CH 3 G 15
514 4-OCH 2CH 3 G 15
515 4-Cl H Ethyl G 15
516 4-F G 15
517 4-Br G 15
518 4-CH 3 G 15
519 4-OCH 2CH 3 G 15
520 4-Cl Sec.-propyl G 15
521 4-F G 15
522 4-OCH 3 G 15
523 4-CH 3 G 15
524 4-OCH 2CH 3 G 15
525 4-Cl N-propyl G 15
526 4-F G 15
527 4-OCH 3 G 15
528 4-OCH 2CH 3 G 15
529 4-Cl Phenyl G 15
530 4-F G 15
531 4-CH 3 G 15
532 4-OCH 2CH 3 G 15
533 H CH 3 2-pyridyl G 15
534 6-Cl : G 15
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
535 H H H CH 3 4-pyridyl S 0 1 G 15 H
536 6-H 3-pyridyl G 15
537 6-Cl G 15
538 6-OCH 2CH 3 G 15
539 6-OCH 2CF 3 G 15
540 6-CH 3 G 15
541 6-OCH 3 G 15
542 2-H The 5-pyrimidyl G 15
543 2-Cl G 15
544 2-OCH 2CH 3 G 15
545 H The 2-furyl G 15
546 5-Cl G 15
547 H The 2-thienyl G 15
548 5-Cl G 15
549 H The 2-pyrryl G 15
550 5-Cl G 15
551 H The 2-naphthyl G 15
552 H The 2-benzofuryl G 15
553 H The 2-benzothienyl G 15
554 4-Cl phenyl 1 G 15
555 4-F G 15
556 4-Br G 15
557 4-CH 3 G 15
558 4-OCH 3 G 15
559 4-CH 2CH 3 G 15
560 4-OCH 2CF 3 G 15
561 4-Cl CH 3 CH 3 G 15
562 4-F G 15
563 4-Br G 15
564 4-CH 3 G 15
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
565 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 1 1 G 15 H
566 4-OCH 2CF 3 G 15
567 4-Cl H H O 0 1 G 15
568 4-F G 15
569 4-Br G 15
570 4-CH 3 G 15
571 4-OCH 3 G 15
572 4-CH 2CH 3 G 15
573 4-OCH 2CF 3 G 15
574 4-Cl CH 3 O G 15
575 4-F G 15
576 4-Br G 15
577 4-CH 3 G 15
578 4-OCH 3 G 15
579 4-CH 2CH 3 G 15
580 H H The 2-furyl G 15
581 H The 2-thienyl G 15
582 H 2-pyridyl G 15
583 4-Cl Phenyl SO 2 G 15
584 4-F G 15
585 4-Br G 15
586 4-CH 3 G 15
587 4-OCH 3 G 15
588 4-CH 2CH 3 G 15
589 4-OCH 2CF 3 G 15
590 4-Cl CH 3 G 15
591 4-F G 15
592 4-Br G 15
593 4-CH 3 G 15
594 4-OCH 3 G 15
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
595 4-OCH 2CF 3 H CH 3 CH 3 Phenyl SO 2 0 1 G 15 H
596 4-CH 2CH 3 G 15
597 4-Cl H SO G 15
598 4-F G 15
599 4-Br G 15
600 4-CH 3 G 15
601 4-OCH 3 G 15
602 4-OCH 2CH 3 G 15
603 4-OCH 3 S 3 G 15
604 H CH 3 1 G 15
605 CH 3 G 15
606 4-OCH 2CH 3 H H 1 G 15
607 H CH 3 G 15
608 CH 3 G 15
609 H H SO 2 0 G 15
610 SO G 15
611 H S 3 G 15
612 4-F G 15
613 4-OCH 2CH 3 G 15
614 H 2 G 15
615 SCH 3 1 G 15
616 CH 3 G 15
617 H Chlorine G 15
618 Ethyl G 15
619 F G 15
620 Chlorine Chlorine G 15
621 H N-propyl G 15
622 2,4, the 5-trichlorine H G 15
623 2,4, the 5-trichlorine CH 3 G 15
624 4-SO 2CH 3 H G 15
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
625 4-Cl H Ethyl CH 3 phenyl S 0 1 G 11 H
626 4-OCH 2CH 3 G 11
627 4-CH 3 G 11
628 3,4-Cl 2 G 11
629 4-Cl H G 11
630 4-F G 11
631 4-Br G 11
632 4-CH 3 G 11
633 4-OCH 3 G 11
634 4-CH 2CH 3 G 11
635 4-OCH 2CH 3 G 11
636 4-CH(CH 3) 2 G 11
637 4-SCH 3 G 11
638 4-C(CH 3) 3 G 11
639 4-CH 2CH 2CH 3 G 11
640 4-OCH(CH 3) 2 G 11
641 4-OCH 2CH 2CH 3 G 11
642 4-SOCH 3 G 11
643 3,4-OCH 2-O G 11
644 The 4-phenoxy group G 11
645 3,4-Cl 2 G 11
646 3,4-(CH 3) 2 G 11
647 3-Cl,4-CH 3 G 11
648 4-CF 3 G 11
649 4-OCF 3 G 11
650 4-CF 2H G 11
651 4-OCH 2CF 3 G 11
652 3-Br,4-F G 11
653 4-CH 2OCH 3 G 11
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
654 4-Cl H CH 3 CH 3 phenyl S 0 1 G 11 H
655 4-F G 11
656 4-Br G 11
657 4-CH 3 G 11
658 4-OCH 3 G 11
659 4-CH 2CH 3 G 11
660 4-OCH 2CH 3 G 11
661 4-CH(CH 3) 2 G 11
662 4-SCH 3 G 11
663 4-C(CH 3) 3 G 11
664 4-CH 2CH 2CH 3 G 11
665 4-OCH(CH 3) 2 G 11
666 4-OCH 2CH 2CH 3 G 11
667 4-SOCH 3 G 11
668 3,4-O-CH 2-O G 11
669 The 4-phenoxy group G 11
670 3,4-Cl 2 G 11
671 3,4-(CH 3) 2 G 11
672 3-Cl,4-CH 3 G 11
673 4-CF 3 G 11
674 4-OCF 3 G 11
675 4-CF 2H G 11
676 4-OCH 2CF 3 G 11
677 3-Br,4-F G 11
678 4-CH 2OCH 3 G 11
679 4-OCF 2CF 2H H G 11
680 4-OCF 2H G 11
681 4-OCH 2CCl=CH 2 G 11
682 4-ethoxy oxyethyl group G 11
683 4-OCH 2CH 2Cl G 11
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
684 3,4,5-Trifluoro H H CH 3 phenyl S 0 1 G 11 H
685 4-allyl oxygen methyl G 11
686 4-CH 2Cl G 11
687 4-NO 2 G 11
688 3-NO 2 G 11
689 4-OCF 2CF 2H CH 3 G 11
690 4-OCF 2H G 11
691 4-OCH 2CCl=CH 2 G 11
692 4-ethoxy oxyethyl group G 11
693 4-OCH 2CH 2Cl G 11
694 3,4,5-Trifluoro G 11
695 4-allyl oxygen methyl G 11
696 4-CH 2Cl G 11
697 4-Cl H 3 G 11
698 4-CH 3 3 G 11
699 2-Cl 1 G 11
700 3-Cl G 11
701 3-CF 3 G 11
702 The 3-phenoxy group G 11
703 2-CH 3 G 11
704 2-Cl CH 3 G 11
705 3-Cl G 11
706 3-CF 3 G 11
707 The 3-phenoxy group G 11
708 2-CH 3 G 11
709 4-Cl CH 3 G 11
710 4-F G 11
711 4-Br G 11
712 4-CH 3 G 11
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
713 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 0 1 G 11 H
714 4-CH 2CH 3 G 11
715 4-OCH 2CH 3 G 11
716 4-Cl H SCH 3 G 11
717 4-F G 11
718 4-Br G 11
719 4-CH 3 G 11
720 4-OCH 3 G 11
721 4-CH 2CH 3 G 11
722 4-OCH 2CH 3 G 11
723 4-Cl H Ethyl G 11
724 4-F G 11
725 4-Br G 11
726 4-CH 3 G 11
727 4-OCH 2CH 3 G 11
728 4-Cl Sec.-propyl G 11
729 4-F G 11
730 4-OCH 3 G 11
731 4-CH 3 G 11
732 4-OCH 2CH 3 G 11
733 4-Cl N-propyl G 11
734 4-F G 11
735 4-OCH 3 G 11
736 4-OCH 2CH 3 G 11
737 4-Cl Phenyl G 11
738 4-F G 11
739 4-CH 3 G 11
740 4-OCH 2CH 3 G 11
741 H CH 3 2-pyridyl G 11
742 6-Cl G 11
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
743 H H H CH 3 4-pyridyl S 0 1 G 11 H
744 6-H 3-pyridyl G 11
745 6-Cl G 11
746 6-OCH 2CH 3 G 11
747 6-OCH 2CF 3 G 11
748 6-CH 3 G 11
749 6-OCH 3 G 11
750 2-H The 5-pyrimidyl G 11
751 2-Cl G 11
752 2-OCH 2CH 3 G 11
753 H The 2-furyl G 11
754 5-Cl G 11
755 H The 2-thienyl G 11
756 5-Cl G 11
757 H The 2-pyrryl G 11
758 5-Cl G 11
759 H The 2-naphthyl G 11
760 H The 2-benzofuryl G 11
761 H The 2-benzothienyl G 11
762 4-Cl phenyl 1 G 11
763 4-F G 11
764 4-Br G 11
765 4-CH 3 G 11
766 4-OCH 3 G 11
767 4-CH 2CH 3 G 11
768 4-OCH 2CF 3 G 11
769 4-Cl CH 3 CH 3 G 11
770 4-F G 11
771 4-Br G 11
772 4-CH 3 G 11
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
773 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 1 1 G 11 H
774 4-OCH 2CF 3 G 11
775 4-Cl H H O 0 1 G 11
776 4-F G 11
777 4-Br G 11
778 4-CH 3 G 11
779 4-OCH 3 G 11
780 4-CH 2CH 3 G 11
781 4-OCH 2CF 3 G 11
782 4-Cl CH 3 O G 11
783 4-F G 11
784 4-Br G 11
785 4-CH 3 G 11
786 4-OCH 3 G 11
787 4-CH 2CH 3 G 11
788 H H The 2-furyl G 11
789 H The 2-thienyl G 11
790 H 2-pyriyl G 11
791 4-Cl Phenyl SO 2 G 11
792 4-F G 11
793 4-Br G 11
794 4-CH 3 G 11
795 4-OCH 3 G 11
796 4-CH 2CH 3 G 11
797 4-O CH 2CF 3 G 11
798 4-Cl CH 3 G 11
799 4-F G 11
800 4-Br G 11
801 4-CH 3 G 11
802 4-OCH 3 G 11
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
803 4-OCH 2CF 3 H CH 3 CH 3 Phenyl SO 2 0 1 G 11 H
804 4-CH 2CH 3 G 11
805 4-Cl H SO G 11
806 4-F G 11
807 4-Br G 11
808 4-CH 3 G 11
809 4-OCH 3 G 11
810 4-OCH 2CH 3 G 11
811 4-OCH 3 S 3 G 11
812 H CH 3 1 G 11
813 CH 3 G 11
814 4-OCH 2CH 3 H H 1 G 11
815 H CH 3 G 11
816 CH 3 G 11
817 H H SO 2 0 G 11
818 SO G 11
819 H S 3 G 11
820 4-F G 11
821 4-OCH 2CH 3 G 11
822 H 2 G 11
823 SCH 3 1 G 11
824 CH 3 G 11
825 H Chlorine G 11
826 Ethyl G 11
827 F G 11
828 Nitrogen Chlorine G 11
829 H N-propyl G 11
830 2,4, the 5-trichlorine H G 11
831 2,4, the 5-trichlorine CH 3 G 11
832 4-SO 2CH 3 H G 11
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
833 4-Cl H Ethyl CH 3 phenyl S 0 1 G 24 H
834 4-OCH 2CH 3 G 24
835 4-CH 3 G 24
836 3,4-Cl 2 G 24
837 4-Cl H G 24
838 4-F G 24
839 4-Br G 24
840 4-CH 3 G 24
841 4-OCH 3 G 24
842 4-CH 2CH 3 G 24
843 4-OCH 2CH 3 G 24
844 4-CH(CH 3) 2 G 24
845 4-SCH 3 G 24
846 4-C(CH 3) 3 G 24
847 4-CH 2CH 2CH 3 G 24
848 4-OCH(CH 3) 2 G 24
849 4-OCH 2CH 2CH 3 G 24
850 4-SOCH 3 G 24
851 3,4-O-CH 2-O G 24
852 The 4-phenoxy group G 24
853 3,4-Cl 2 G 24
854 3,4-(CH 3) 2 G 24
855 3-Cl,4-CH 3 G 24
856 4-CF 3 G 24
857 4-OCF 3 G 24
858 4-CF 2H G 24
859 4-OCH 2CF 3 G 24
860 3-Br,4-F G 24
861 4-CH 2OCH 3 G 24
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
862 4-Cl H CH 3 CH 3 phenyl S 0 1 G 24 H
863 4-F G 24
864 4-Br G 24
865 4-CH 3 G 24
866 4-OCH 3 G 24
867 4-CH 2CH 3 G 24
868 4-OCH 2CH 3 G 24
869 4-CH(CH 3) 2 G 24
870 4-SCH 3 G 24
871 4-C(CH 3) 3 G 24
872 4-CH 2CH 2CH 3 G 24
873 4-OCH(CH 3) 2 G 24
874 4-OCH 2CH 2CH 3 G 24
875 4-SOCH 3 G 24
876 3,4-O-CH 2-O G 24
877 The 4-phenoxy group G 24
878 3,4-Cl 2 G 24
879 3,4-(CH 3) 2 G 24
880 3-Cl,4-CH 3 G 24
881 4-CF 3 G 24
882 4-OCF 3 G 24
883 4-CF 2H G 24
884 4-OCH 2CF 3 G 24
885 3-Br,4-F G 24
886 4-CH 2OCH 3 G 24
887 4-OCF 2CF 2H H G 24
888 4-OCF 2H G 24
889 4-OCH 2CCl=CH 2 G 24
890 4-ethoxy oxyethyl group G 24
891 4-OCH 2CH 2Cl G 24
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
892 3,4,5-Trifluoro H H CH 3 phenyl S 0 1 G 24 H
893 4-allyl oxygen methyl G 24
894 4-CH 2Cl G 24
895 4-NO 2 G 24
896 3-NO 2 G 24
897 4-OCF 2CF 2H CH 3 G 24
898 4-OCF 2H G 24
899 4-OCH 2CCl=CH 2 G 24
900 4-ethoxy oxyethyl group G 24
901 4-OCH 2CH 2Cl G 24
902 3,4,5-Trifluoro G 24
903 4-allyl oxygen methyl G 24
904 4-CH 2Cl G 24
905 4-Cl H 3 G 24
906 4-CH 3 3 G 24
907 2-Cl 1 G 24
908 3-Cl G 24
909 3-CF 3 G 24
910 The 3-phenoxy group G 24
911 2-CH 3 G 24
912 2-Cl SCH 3 G 24
913 3-Cl G 24
914 3-CF 3 G 24
915 The 3-phenoxy group G 24
916 2-CH 3 G 24
917 4-Cl CH 3 G 24
918 4-F G 24
919 4-Br G 24
920 4-CH 3 G 24
No. R R 1 R 2 R 3 Ar 1 X m n G K
921 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 0 1 G 24 H
922 4-CH 2CH 3 G 24
923 4-OCH 2CH 3 G 24
924 4-Cl H SCH 3 G 24
925 4-F G 24
926 4-Br G 24
927 4-CH 3 G 24
928 4-OCH 3 G 24
929 4-CH 2CH 3 G 24
930 4-OCH 2CH 3 G 24
931 4-Cl H Ethyl G 24
932 4-F G 24
933 4-Br G 24
934 4-CH 3 G 24
935 4-OCH 2CH 3 G 24
936 4-Cl Sec.-propyl G 24
937 4-F G 24
938 4-OCH 3 G 24
939 4-CH 3 G 24
940 4-OCH 2CH 3 G 24
941 4-Cl N-propyl G 24
942 4-F G 24
943 4-OCH 3 G 24
944 4-OCH 2CH 3 G 24
945 4-Cl Phenyl G 24
946 4-F G 24
947 4-CH 3 G 24
948 4-OCH 2CH 3 G 24
949 H CH 3 2-pyridyl G 24
950 6-Cl G 24
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
951 H H H CH 3 4-pyridyl S 0 1 G 24 H
952 6-H 3-pyridyl G 24
953 6-Cl G 24
954 6-OCH 2CH 3 G 24
955 6-OCH 2CF 3 G 24
956 6-CH 3 G 24
957 6-OCH 3 G 24
958 2-H The 5-pyrimidyl G 24
959 2-Cl G 24
960 2-OCH 2CH 3 G 24
961 H The 2-furyl G 24
962 5-Cl G 24
963 H The 2-thienyl G 24
964 5-Cl G 24
965 H The 2-pyrryl G 24
966 5-Cl G 24
967 H The 2-naphthyl G 24
968 H The 2-benzofuryl G 24
969 H The 2-benzothienyl G 24
970 4-Cl phenyl 1 1 G 24
971 4-F G 24
972 4-Br G 24
973 4-CH 3 G 24
974 4-OCH 3 G 24
975 4-CH 2CH 3 G 24
976 4-O CH 2CF 3 G 24
977 4-Cl CH 3 CH 3 G 24
978 4-F G 24
979 4-Br G 24
980 4-CH 3 G 24
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
981 4-OCH 3 CH 3 CH 3 CH 3 Phenyl S 1 1 G 24 H
982 4-O CH 2CF 3 G 24
983 4-Cl H H O 0 1 G 24
984 4-F G 24
985 4-Br G 24
986 4-CH 3 G 24
987 4-OCH 3 G 24
988 4-CH 2CH 3 G 24
989 4-O CH 2CF 3 G 24
990 4-Cl CH 3 O G 24
991 4-F G 24
992 4-Br G 24
993 4-CH 3 G 24
994 4-OCH 3 G 24
995 4-CH 2CH 3 G 24
996 H H The 2-furyl G 24
997 H The 2-thienyl G 24
998 H 2-pyridyl G 24
999 4-Cl Phenyl SO 2 G 24
1000 4-F G 24
1001 4-Br G 24
1002 4-CH 3 G 24
1003 4-OCH 3 G 24
1004 4-CH 2CH 3 G 24
1005 4-O CH 2CF 3 G 24
1006 4-Cl CH 3 G 24
1007 4-F G 24
1008 4-Br G 24
1009 4-CH 3 G 24
1010 4-OCH 3 G 24
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1011 4-OCH 2CF 3 H CH 3 CH 3 Phenyl SO 2 0 1 G 24 H
1012 4-CH 2CH 3 G 24
1013 4-Cl H SO G 24
1014 4-F G 24
1015 4-Br G 24
1016 4-CH 3 G 24
1017 4-OCH 3 G 24
1018 4-OCH 2CH 3 G 24
1019 4-OCH 3 S 3 G 24
1020 H CH 3 1 G 24
1021 CH 3 G 24
1022 4-Cl H H 1 G 24
1023 H CH 3 G 24
1024 CH 3 G 24
1025 H H SO 2 0 G 24
1026 SO G 24
1027 H S 3 G 24
1028 4-F G 24
1029 4-OCH 2CH 3 G 24
1030 H 2 G 24
1031 SCH 3 1 G 24
1032 CH 3 G 24
1033 H Chlorine G 24
1034 Ethyl G 24
1035 F G 24
1036 Chlorine Chlorine G 24
1037 H N-propyl G 24
1038 2,4, the 5-trichlorine H G 24
1039 2,4, the 5-trichlorine CH 3 G 24
1040 4-SO 2CH 3 H G 24
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1041 4-Cl H Ethyl CH 3 phenyl S 0 1 G 2 H
1042 H SO G 2
1043 SO 2 G 2
1044 O G 2
1045 4-Cl S G 2
1046 4-F G 2
1047 4-Br G 2
1048 4-CH 3 G 2
1049 4-OCH 3 G 2
1050 4-OCH 2CH 3 G 2
1051 4-OCH 2CF 3 G 2
1052 3,4-Cl 2 G 2
1053 4-CF 3 G 2
1054 3-Cl,4-CH 3 G 2
1055 3,4-(CH 3) 2 G 2
1056 3,4-O-CH 2-O G 2
1057 3,4-Cl 2 CH 3 G 2
1058 4-Cl G 2
1059 4-CH 3 G 2
1060 4-OCH 2CH 3 G 2
1061 3,4-(CH 3) 2 G 2
1062 4-Br G 2
1063 4-OCH 2CF 3 G 2
1064 3-Cl,4-CH 3 G 2
1065 4-F G 2
1066 4-CF 3 G 2
1067 6-OCH 2CF 3 3-pyridyl G 2
1068 6-Cl G 2
1069 H G 2
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1070 4-Cl H Ethyl CH 3 phenyl S 0 1 G 9 H
1071 H SO G 9
1072 SO 2 G 9
1073 O G 9
1074 4-Cl S G 9
1075 4-F G 9
1076 4-Br G 9
1077 4-CH 3 G 9
1078 4-OCH 3 G 9
1079 4-OCH 2CH 3 G 9
1080 4-OCH 2CF 3 G 9
1081 3,4-Cl 2 G 9
1082 4-CF 3 G 9
1083 3-Cl,4-CH 3 G 9
1084 3,4-(CH 3) 2 G 9
1085 3,4-O-CH 2-O G 9
1086 3,4-Cl 2 CH 3 G 9
1087 4-Cl G 9
1088 4-CH 3 G 9
1089 4-OCH 2CH 3 G 9
1090 3,4-(CH 3) 2 G 9
1091 4-Br G 9
1092 4-OCH 2CF 3 G 9
1093 3-Cl,4-CH 3 G 9
1094 4-F G 9
1095 4-CF 3 G 9
1096 6-OCH 2CF 3 3-pyridyl G 9
1097 6-Cl G 9
1098 H G 9
1099 6-CH 3 G 9
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1100 4-Cl H Ethyl CH 3 phenyl S 0 1 G 4 H
1101 H SO G 4
1102 SO 2 G 4
1103 O G 4
1104 4-Cl S G 4
1105 4-F G 4
1106 4-Br G 4
1107 4-CH 3 G 4
1108 4-OCH 3 G 4
1109 4-OCH 2CH 3 G 4
1110 4-OCH 2CF 3 G 4
1111 3,4-Cl 2 G 4
1112 4-CF 3 G 4
1113 3-Cl,4-CH 3 G 4
1114 3,4-(CH 3) 2 G 4
1115 3,4-O-CH 2-O G 4
1116 3,4-Cl 2 CH 3 G 4
1117 4-Cl G 4
1118 4-CH 3 G 4
1119 4-OCH 2CH 3 G 4
1120 3,4-(CH 3) 2 G 4
1121 4-Br G 4
1122 4-OCH 2CF 3 G 4
1123 3-Cl,4-CH 3 G 4
1124 4-F G 4
1125 4-CF 3 G 4
1126 6-OCH 2CF 3 3-pyridyl G 4
1127 6-Cl G 4
1128 H G 4
No. R R 1 R 2 R 3 Ar 1 X G K
1129 4-Cl H Ethyl CH 3 phenyl S G 10 H
1130 H SO G 10
1131 SO 2 G 10
1132 O G 10
1133 4-Cl S G 10
1134 4-F G 10
1135 4-Br G 10
1136 4-CH 3 G 10
1137 4-OCH 3 G 10
1138 4-OCH 2CH 3 G 10
1139 4-OCH 2CF 3 G 10
1140 3,4-Cl 2 G 10
1141 4-CF 3 G 10
1142 3-Cl,4-CH 3 G 10
1143 3,4-(CH 3) 2 G 10
1144 3,4-O-CH 2-O G 10
1145 3,4-Cl 2 CH G 10
1146 4-Cl G 10
1147 4-CH 3 G 10
1148 4-OCH 2CH 3 G 10
1149 3,4-(CH 3) 2 G 10
1150 4-Br G 10
1151 4-OCH 2CF 3 G 10
1152 3-Cl,4-CH 3 G 10
1153 4-F G 10
1154 4-CF 3 G 10
1155 6-OCH 2CF 3 3-pyridyl G 10
1156 6-Cl G 10
1157 H G 10
1158 6-CH 3 G 10
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1159 4-Cl H Ethyl CH 3 phenyl S 0 1 G 12 H
1160 H SO G 12
1161 SO 2 G 12
1162 O G 12
1163 4-Cl S G 12
1164 4-F G 12
1165 4-Br G 12
1166 4-CH 3 G 12
1167 4-OCH 3 G 12
1168 4-OCH 2CH 3 G 12
1169 4-OCH 2CF 3 G 12
1170 3,4-Cl 2 G 12
1171 4-CF 3 G 12
1172 3-Cl,4-CH 3 G 12
1173 3,4-(CH 3) 2 G 12
1174 3,4-O-CH 2-O G 12
1175 3,4-Cl 2 CH 3 G 12
1176 4-Cl G 12
1177 4-CH 3 G 12
1178 4-OCH 2CH 3 G 12
1179 3,4-(CH 3) 2 G 12
1180 4-Br G 12
1181 4-OCH 2CF 3 G 12
1182 3-Cl,4-CH 3 G 12
1183 4-F G 12
1184 4-CF 3 G 12
1185 6-OCH 2CF 3 3-pyridyl G 12
1186 6-Cl G 12
1187 H G 12
1188 6-CH 3 G 12
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1189 4-Cl H Ethyl CH 3 phenyl S 0 1 G 16 H
1190 H SO G 16
1191 SO 2 G 16
1192 O G 16
1193 4-Cl S G 16
1194 4-F G 16
1195 4-Br G 16
1196 4-CH 3 G 16
1197 4-OCH 3 G 16
1198 4-OCH 2CH 3 G 16
1199 4-OCH 2CF 3 G 16
1200 3,4-Cl 2 G 16
1201 4-CF 3 G 16
1202 3-Cl,4-CH 3 G 16
1203 3,4-(CH 3) 2 G 16
1204 3,4-O-CH 2-O G 16
1205 3,4-Cl 2 CH 3 G 16
1206 4-Cl G 16
1207 4-CH 3 G 16
1208 4-OCH 2CH 3 G 16
1209 3,4-(CH 3) 2 G 16
1210 4-Br G 16
1211 4-OCH 2CF 3 G 16
1212 3-Cl,4-CH 3 G 16
1213 4-F G 16
1214 4-CF 3 G 16
1215 6-OCH 2CF 3 3-pyridyl G 16
1216 6-Cl G 16
1217 H G 16
1218 6-CH 3 G 16
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1219 4-Cl H Ethyl CH 3 phenyl S 0 1 G 22 H
1220 H SO G 22
1221 SO 2 G 22
1222 O G 22
1223 4-Cl S G 22
1224 4-F G 22
1225 4-Br G 22
1226 4-CH 3 G 22
1227 4-OCH 3 G 22
1228 4-OCH 2CH 3 G 22
1229 4-OCH 2CF 3 G 22
1230 3,4-Cl 2 G 22
1231 4-CF 3 G 22
1232 3-Cl,4-CH 3 G 22
1233 3,4-(CH 3) 2 G 22
1234 3,4-O-CH 2-O G 22
1235 3,4-Cl 2 CH 3 G 22
1236 4-Cl G 22
1237 4-CH 3 G 22
1238 4-OCH 2CH 3 G 22
1239 3,4-(CH 3) 2 G 22
1240 4-Br G 22
1241 4-OCH 2CF 3 G 22
1242 3-Cl,4-CH 3 G 22
1243 4-F G 22
1244 4-CF 3 G 22
1245 6-OCH 2CF 3 3-pyridyl G 22
1256 6-Cl G 22
1247 H G 22
1248 6-CH 3 G 22
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1249 4-Cl H Ethyl CH 3 phenyl S 0 1 G 28 H
1250 H SO G 28
1251 SO 2 G 28
1252 O G 28
1253 4-Cl S G 28
1254 4-F G 28
1255 4-Br G 28
1256 4-CH 3 G 28
1257 4-OCH 3 G 28
1258 4-OCH 2CH 3 G 28
1259 4-OCH 2CF 3 G 28
1260 3,4-Cl 2 G 28
1261 4-CF 3 G 28
1262 3-Cl,4-CH 3 G 28
1263 3,4-(CH 3) 2 G 28
1264 3,4-O-CH 2-O G 28
1265 3,4-Cl 2 CH 3 G 28
1266 4-Cl G 28
1267 4-CH 3 G 28
1268 4-OCH 2CH 3 G 28
1269 3,4-(CH 3) 2 G 28
1270 4-Br G 28
1271 4-OCH 2CF 3 G 28
1272 3-Cl,4-CH 3 G 28
1273 4-F G 28
1274 4-CF 3 G 28
1275 6-OCH 2CF 3 3-pyridyl G 28
1276 6-Cl G 28
1277 H G 28
1278 6-CH 3 G 28
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1279 4-Cl H Ethyl CH 3 phenyl S 0 1 G 29 H
1280 H SO G 29
1281 SO 2 G 29
1282 O G 29
1283 4-Cl S G 29
1284 4-F G 29
1285 4-CH 2CH 3 G 29
1286 4-CH 3 G 29
1287 4-OCH 3 G 29
1288 4-OCH 2CH 3 G 29
1289 4-OCH 2CF 3 G 29
1290 3,4-Cl 2 G 29
1291 4-CF 3 G 29
1292 3-Cl,4-CH 3 G 29
1293 3,4-(CH 3) 2 G 29
1294 3,4-O-CH 2-O G 29
1295 3,4-Cl 2 CH 3 G 29
1296 4-Cl G 29
1297 4-CH 3 G 29
1298 4-OCH 2CH 3 G 29
1299 3,4-(CH 3) 2 G 29
1300 4-Br G 29
1301 4-OCH 2CF 3 G 29
1302 3-Cl,4-CH 3 G 29
1303 4-F G 29
1304 4-CF 3 G 29
1305 6-OCH 2CF 3 3-pyridyl G 29
1306 6-Cl G 29
1307 H G 29
1308 6-CH 3 G 29
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1309 4-OCH 2CH 3 H H CH 3 phenyl S 0 1 G 3 H
1310 4-Cl G 3
1311 4-CH 3 G 3
1312 4-OCH 2CH 3 CH 3 G 3
1313 4-Cl G 3
1314 H 3-pyridyl G 3
1315 6-Cl G 3
1316 4-Cl phenyl O G 3
1317 4-Cl SO 2 G 3
1318 4-Cl SO G 3
1319 4-OCH 2CH 3 H H CH 3 phenyl S G 5 H
1320 4-Cl G 5
1321 4-CH 3 G 5
1322 4-CH 3 CH 3 G 5
1323 4-Cl G 5
1324 H 3-pyridyl G 5
1325 6-Cl G 5
1326 4-Cl phenyl O G 5
1327 4-Cl SO 2 G 5
1328 4-Cl SO G 5
1329 4-OCH 2CH 3 H H CH 3 phenyl S G 6 H
1330 4-Cl G 6
1331 4-CH 3 G 6
1332 4-OCH 3 CH 3 G 6
1333 4-Cl G 6
1334 H 3-pyridyl G 6
1335 6-Cl G 6
1336 4-Cl phenyl O G 6
1337 4-Cl SO 2 G 6
1338 4-Cl SO G 6
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1339 4-OCH 2CH 3 H H CH 3 phenyl S 0 1 G 7 H
1340 4-Cl G 7
1341 4-CH 3 G 7
1342 4-CH 3 CH 3 G 7
1343 4-Cl G 7
1344 H 3-pyridyl G 7
1345 6-Cl G 7
1346 4-Cl phenyl O G 7
1347 4-Cl SO 2 G 7
1348 4-Cl SO G 7
1349 4-OCH 2CH 3 H H CH 3 phenyl S G 13 H
1350 4-Cl G 13
1351 4-CH 3 G 13
1352 4-CH 3 CH 3 G 13
1353 4-Cl G 13
1354 H 3-pyridyl G 13
1355 6-Cl G 13
1356 4-Cl phenyl O G 13
1357 4-Cl SO 2 G 13
1358 4-Cl SO G 13
1359 4-OCH 2CH 3 H H CH 3 phenyl S G 14 H
1360 4-Cl G 14
1361 4-CH 3 G 14
1362 4-CH 3 CH 3 G 14
1363 4-Cl G 14
1364 H 3-pyridyl G 14
1365 6-Cl G 14
1366 4-Cl phenyl O G 14
1367 4-Cl SO 2 G 14
1368 4-Cl SO G 14
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1369 4-OCH 2CH 3 H H CH 3 phenyl S 0 1 G 17 H
1370 4-Cl G 17
1371 4-CH 3 G 17
1372 4-CH 3 CH 3 G 17
1373 4-Cl G 17
1374 H 3-pyridyl G 17
1375 6-Cl G 17
1376 4-Cl phenyl O G 17
1377 4-Cl SO 2 G 17
1378 4-Cl SO G 17
1379 4-OCH 2CH 3 H H CH 3 phenyl S G 18 H
1380 4-Cl G 18
1381 4-CH 3 G 18
1382 4-CH 3 CH 3 G 18
1383 4-Cl G 18
1384 H 3-pyridyl G 18
1385 6-Cl G 18
1386 4-Cl phenyl O G 18
1387 4-Cl SO 2 G 18
1388 4-Cl SO G 18
1389 4-OCH 2CH 3 H H CH 3 phenyl S G 19 H
1390 4-Cl G 19
1391 4-CH 3 G 19
1392 4-CH 3 CH 3 G 19
1393 4-Cl G 19
1394 H 3-pyridyl G 19
1395 6-Cl G 19
1396 4-Cl phenyl O G 19
1397 4-Cl SO 2 G 19
1398 4-Cl SO G 19
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1399 4-OCH 2CH 3 H H CH 3 phenyl S 0 1 G 20 H
1400 4-Cl G 20
1401 4-CH 3 G 20
1402 4-CH 3 CH 3 G 20
1403 4-Cl G 20
1404 H 3-pyridyl G 20
1405 6-Cl G 20
1406 4-Cl phenyl O G 20
1407 4-Cl SO 2 G 20
1408 4-Cl SO G 20
1409 4-OCH 2CH 3 H H CH 3 phenyl S G 21 H
1410 4-Cl G 21
1411 4-CH 3 G 21
1412 4-CH 3 CH 3 G 21
1413 4-Cl G 21
1414 H 3-pyridyl G 21
1415 6-Cl G 21
1416 4-Cl phenyl O G 21
1417 4-Cl SO 2 G 21
1418 4-Cl SO G 21
1419 4-OCH 2CH 3 H H CH 3 phenyl S G 23 H
1420 4-Cl G 23
1421 4-CH 3 G 23
1422 4-CH 3 CH 3 G 23
1423 4-Cl G 23
1424 H 3-pyridyl G 23
1425 6-Cl G 23
1426 4-Cl phenyl O G 23
1427 4-Cl SO 2 G 23
1428 4-Cl SO G 23
No R R 1 R 2 R 3 Ar 1 X m n G K Y
1429 4-OCH 2CH 3 H H CH 3 phenyl S 0 1 G 25 H
1430 4-Cl G 25
1431 4-CH 3 G 25
1432 4-CH 3 CH 3 G 25
1433 4-Cl G 25
1434 H 3-pyridyl G 25
1435 6-Cl G 25
1436 4-Cl phenyl O G 25
1437 4-Cl SO 2 G 25
1438 4-Cl SO G 25
1439 4-OCH 2CH 3 H H CH 3 phenyl S G 26 H
1440 4-Cl G 26
1441 4-CH 3 G 26
1442 4-CH 3 CH 3 G 26
1443 4-Cl G 26
1444 H 3-pyridyl G 26
1445 6-Cl G 26
1446 4-Cl phenyl O G 26
1447 4-Cl SO 2 G 26
1448 4-Cl SO G 26
1449 4-OCH 3 H H CH 3 phenyl S G 27 H
1450 4-Cl G 27
1451 4-CH 3 G 27
1452 4-CH 3 CH 3 G 27
1453 4-Cl G 27
1454 H 3-pyridyl G 27
1455 6-Cl G 27
1456 4-Cl phenyl O G 27
1457 4-Cl SO 2 G 27
1458 4-Cl SO G 27
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1459 4-Cl H Ethyl CH 3 phenyl S 0 1 G 1 Cyano group
1460 H SO G 1
1461 SO 2 G 1
1462 O G 1
1463 4-Cl S G 1
1464 4-F G 1
1465 4-Br G 1
1466 4-CH 3 G 1
1467 4-OCH 3 G 1
1468 4-OCH 2CH 3 G 1
1469 4-OCH 2CF 3 G 1
1470 3,4-Cl 2 G 1
1471 4-CF 3 G 1
1472 3-Cl,4-CH 3 G 1
1473 3,4-(CH 3) 2 G 1
1474 3,4-O-CH 2-O G 1
1475 3,4-Cl 2 CH 3 G 1
1476 4-Cl G 1
1477 4-CH 3 G 1
1478 4-OCH 2CH 3 G 1
1479 3,4-(CH 3) 2 G 1
1480 4-Br G 1
1481 4-OCH 2CF 3 G 1
1482 3-Cl,4-CH 3 G 1
1483 4-F G 1
1484 4-CF 3 G 1
1485 6-OCH 2CF 3 3-pyridyl G 1
1486 6-Cl G 1
1487 H G 1
1488 6-CH 3 G 1
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1489 4-Cl H Ethyl CH 3 phenyl S 0 1 G 1 Chlorine
1490 H SO G 1
1491 SO 2 G 1
1492 O G 1
1493 4-Cl S G 1
1494 4-F G 1
1495 4-Br G 1
1496 4-CH 3 G 1
1497 4-OCH 3 G 1
1498 4-OCH 2CH 3 G 1
1499 4-OCH 2CF 3 G 1
1500 3,4-Cl 2 G 1
1501 4-CF 3 G 1
1502 3-Cl,4-CH 3 G 1
1503 3,4-(CH 3) 2 G 1
1504 3,4-O-CH 2-O G 1
1505 3,4-Cl 2 CH 3 G 1
1506 4-Cl G 1
1507 4-CH 3 G 1
1508 4-OCH 2CH 3 G 1
1509 3,4-(CH 3) 2 G 1
1510 4-Br G 1
1511 4-OCH 2CF 3 G 1
1512 3-Cl,4-CH 3 G 1
1513 4-F G 1
1514 4-CF 3 G 1
1515 6-OCH 2CF 3 3-pyridyl G 1
1516 6-Cl G 1
1517 H G 1
1518 6-CH 3 G 1
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1519 4-Cl H Ethyl CH 3 phenyl S 0 1 G 1 CH 3
1520 H SO G 1
1521 SO 2 G 1
1522 O G 1
1523 4-Cl S G 1
1524 4-F G 1
1525 4-Br G 1
1526 4-CH 3 G 1
1527 4-OCH 3 G 1
1528 4-OCH 2CH 3 G 1
1529 4-OCH 2CF 3 G 1
1530 3,4-Cl 2 G 1
1531 4-CF 3 G 1
1532 3-Cl,4-CH 3 G 1
1533 3,4-(CH 3) 2 G 1
1534 3,4-O-CH 2-O G 1
1535 3,4-Cl 2 CH 3 G 1
1536 4-Cl G 1
1537 4-CH 3 G 1
1538 4-OCH 2CH 3 G 1
1539 3,4-(CH 3) 2 G 1
1540 4-Br G 1
1541 4-OCH 2CF 3 G 1
1542 3-Cl,4-CH 3 G 1
1543 4-F G 1
1544 4-CF 3 G 1
1545 6-OCH 2CF 3 3-pyridyl G 1
1546 6-Cl G 1
1547 H G 1
1548 6-CH 3 G 1
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1549 4-Cl H Ethyl CH 3 phenyl S 0 1 G 1 OCH 3
1550 H SO G 1
1551 SO 2 G 1
1552 O G 1
1553 4-Cl S G 1
1554 4-F G 1
1555 4-Br G 1
1556 4-CH 3 G 1
1557 4-OCH 3 G 1
1558 4-OCH 2CH 3 G 1
1559 4-OCH 2CF 3 G 1
1560 3,4-Cl 2 G 1
1561 4-CF 3 G 1
1562 3-Cl,4-CH 3 G 1
1563 3,4-(CH 3) 2 G 1
1564 3,4-O-CH 2-O G 1
1565 3,4-Cl 2 CH 3 G 1
1566 4-Cl G 1
1567 4-CH 3 G 1
1 568 4-OCH 2CH 3 G 1
1569 3,4-(CH 3) 2 G 1
1570 4-Br G 1
1571 4-OCH 2CF 3 G 1
1572 3-Cl,4-CH 3 G 1
1573 4-F G 1
1574 4-CF 3 G 1
1575 6-OCH 2CF 3 3-pyridyl G 1
1576 6-Cl G 1
1577 H G 1
1578 6-CH 3 G 1
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1579 H H H CH 3 phenyl NH 0 1 G 1 H
1580 4-Cl
1581 4-CH 3
1582 4-OCH 3
1583 H CH 3
1584 4-Cl
1585 4-CH 3
1586 4-OCH 3
1587 4-OCH 2CH 3 / / CH 3 S 0 0
1588 4-Cl / /
1589 4-CH 3 / /
1590 4-OCH 3 / /
1591 4-OCH 2CH 3 / / Ethyl S 0 0
1592 4-Cl / /
1593 4-CH 3 / /
1594 4-OCH 3 / /
1595 4-OCH 2CH 3 / / Sec.-propyl S 0 0
1596 4-Cl / /
1597 4-CH 3 / /
1598 4-OCH 3 / /
1599 4-OCH 2CH 3 / / N-propyl S 0 0
1600 4-Cl / /
1601 4-CH 3 / /
1602 4-OCH 3 / /
1603 4-OCH 2CH 3 / / Phenyl S 0 0
1604 4-Cl / /
1605 4-CH 3 / /
1666 4-OCH 3 / /
1607 4-Cl / / Methyl O 0 0
1608 4-Cl / / H NH 0 0
No. R R 1 R 2 R 3 Ar 1 X m n G K Y
1609 4-OCH 3 H H CH 3 phenyl S 0 1 G 32 H
1610 4-Cl G 32
1611 4-CH 3 G 32
1612 4-CH 3 CH 3 G 32
1613 4-Cl G 32
1614 6-CH 3 3-pyridyl G 32
1615 6-Cl G 32
1616 4-OCH 3 H H CH 3 phenyl S 0 1 G 33 H
1617 4-Cl G 33
1618 4-CH 3 G 33
1619 4-CH 3 CH 3 G 33
1620 4-Cl G 33
1621 6-CH 3 3-pyridyl G 33
1622 6-Cl G 33
1623 4-OCH 3 H H CH 3 phenyl S 0 1 G 34 H
1624 4-Cl G 34
1625 4-CH 3 G 34
1626 4-CH 3 CH 3 G 34
1627 4-Cl G 34
1628 6-CH 3 3-pyridyl G 34
1629 6-Cl G 34
1630 4-OCH 3 H H CH 3 phenyl S 0 1 G 35 H
1631 4-Cl G 35
1632 4-CH 3 G 35
1633 4-CH 3 CH 3 G 35
1634 4-Cl G 35
1635 6-CH 3 3-pyridyl G 35
1636 6-Cl G 35
1637 4-Cl SO 2 G 32
1638 4-Cl SO G 33
Group Ar in table 2 table 1 2Simplify and use G K(K=1-35) abbreviation expression.
Figure C9911555700801
Figure C9911555700811

Claims (15)

1. biocidal alkyl-aryl or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds is characterized in that: a series of alkyl-aryl shown in the general formula (I) or alkyl-heteroaryl-ketoxime-O-ether compound and general formula (II) and a series of intermediate ketones, the oxime compounds shown in the general formula (III) are provided:
Figure C9911555700021
General formula (I), (II) and (III) in:
I.Ar1 is identical or different with Ar2, and representative
(a) (C 6-C 12The heteroaryl of)-aryl or 10 carbon atoms of band as many as; Or
(b) as at I.a) in determined implication, be selected from following in 5 identical or different substituting groups of as many as replace:
Halogen, nitro, cyano group, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, cyano group-(C 1-C 6)
-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkylthio-(C 1-C 6)
-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)
-halogenated alkoxy, (C 1-C 6)-halogenated alkoxy alkyl, (C 1-C 6)-alkylthio, (C 1-C 6)
-halogenated alkylthio, (C 1-C 6)-alkyl sulphonyl, (C 1-C 6)-alkyl sulphinyl, (C 1-C 6)
-alkoxy carbonyl, (C 1-C 6)-alkylamino, two-(C 1-C 6)-alkylamino, (C 2-C 6)
-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-alkenyl oxy alkyl, (C 2-C 6)
-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-halogenated alkenyl oxy
Alkyl, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl,
(C 2-C 6)-halo alkynyloxy base, (C 3-C 8)-cycloalkyl, (C 3-C 8)-cycloalkyl oxy,
(C 3-C 8)-cycloalkyl amino, (C 6-C 12)-aryl, (C 6-C 12)-aryloxy, (C 6-C 12)
-artyl sulfo, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-aryloxy carbonyl
Base, (C 6-C 12)-aryl sulfonyl, (C 6-C 12)-aryl sulfonyl kia, (C 6-C 12)-aryl
Amino, heteroaryl, heteroaryl oxygen base, heteroaryl-(C 1-C 4)-alkyl, the heteroaryl sulfenyl,
Heteroaryl oxygen base carbonyl, heteroarylsulfonyl, heteroaryl sulfinyl; And
When substituting group is aryl or heteroaryl 1) I.b), can be by one or more (C that are selected from 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-haloalkyl, (C 1-C 6The identical or different group of)-halogenated alkoxy and halogen replaces, and heteroaryl is the heteroaryl of 10 carbon atoms of band as many as;
2) cycloalkyl I.b) can be selected from halogen, (C by 5 of as many as 1-C 4The identical or different group of)-alkyl replaces;
3) represent methylenedioxy group or ethylenedioxy for substituent 2 I.b), methylenedioxy group or ethylenedioxy can with 1 or 2 identical or different be selected from halogen and (C 1-C 6The substituting group of)-alkyl;
I.a) and determined the aryl and the partly or entirely hydrogenation of heteroaryl of implication, wherein 1 or 2 CH I.b) 4) 2Group can be replaced by CO;
II.R 1And R 2Be identical or different, and representative
Hydrogen, halogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkylthio, (C 2-C 6)-alkenyl, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-alkynyl, (C 2-C 6)-halo alkynyl, (C 3-C 8)-cycloalkyl;
III.R 3Representative
(a) hydrogen;
(b) (C 1-C 6)-alkyl, (C 6-C 12)-aryl, (C 2-C 6)-alkenyl, (C 2-C 6)-alkynyl,
And group III.b) can be selected from halogen, (C 1-C 4Identical or the different groups of)-alkylthio replace;
IV.X represents S, SO and SO 2
V.Y represents hydrogen, cyano group, halogen, (C 1-C 4)-alkyl, (C 1-C 4)-alkoxyl group;
VI.M be hydrogen or-alkali metal atom;
VII.m represents 0 or 1;
VIII.n represents 1,2 or 3;
All abovementioned alkyls, alkenyl and alkynyl can be straight chain also can be side chain;
Haloalkyl, halogenated alkenyl and halo alkynyl are meant wherein 1, the alkyl that a plurality of or all hydrogen atoms are replaced by halogen, alkenyl and alkynyl;
Halogen is meant fluorine, chlorine, bromine or iodine;
(C 6-C 12)-aryl refers to phenyl, naphthyl or xenyl;
The heteroaryl of 10 carbon atoms of band as many as is meant thienyl, benzothienyl, furyl, benzofuryl, pyrryl, indyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, oxazolyl, isoxazolyl, thiazolyl or isothiazolyl;
(C 6-C 12The partly or entirely hydrogenation of heteroaryl of)-aryl and 10 carbon atoms of band as many as, wherein 1 or 2 CH 2-Ji is replaced by CO.
2. alkyl-aryl according to claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds is characterized in that general formula (I), (II) and (III) in Ar1 be meant a group as follows:
Shown in above-mentioned in the group:
Z is O, S or NR 5, R 5Be hydrogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkylthio-(C 1-C 6)-alkyl, cyano group (C 1-C 6)-alkyl, (C 1-C 6)-alkoxy carbonyl, (C 2-C 6)-alkenyl, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-alkynyl, (C 2-C 6)-halo alkynyl, (C 3-C 8)-cycloalkyl, and cycloalkyl can be selected from halogen or (C by 5 of as many as sometimes 1-C 4The identical or different group of)-alkyl replaces (C 6-C 12)-aryl, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-aryloxycarbonyl, the heteroaryl of 10 carbon atoms of band as many as, heteroaryl oxygen base carbonyl, heteroaryl-(C 1-C 4)-alkyl;
P is one 0 to 5 a integer;
R 4Be identical or different, and represent hydrogen, halogen, nitro, cyano group, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, cyano group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkylthio-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)-halogenated alkoxy, (C 1-C 6)-halogenated alkoxy alkyl, (C 1-C 6)-alkylthio, (C 1-C 6)-halogenated alkylthio, (C 1-C 6)-alkyl sulphonyl, (C 1-C 6)-alkyl sulphinyl, (C 1-C 6)-alkoxy carbonyl, (C 1-C 6)-alkylamino, two-(C 1-C 6)-alkylamino, (C 2-C 6)-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-alkenyl oxy alkyl, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-halogenated alkenyl oxy alkyl, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl, (C 2-C 6)-halo alkynyloxy base, (C 3-C 8)-cycloalkyl, (C 3-C 8)-cycloalkyl oxy, (C 3-C 8)-cycloalkyl amino, (C 6-C 12)-aryl, (C 6-C 12)-aryloxy, (C 6-C 12)-artyl sulfo, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-aryloxy carbonyl, (C 6-C 12)-aryl sulfonyl, (C 6-C 12)-aryl sulfonyl kia, (C 6-C 12)-arylamino, heteroaryl, heteroaryl oxygen base, heteroaryl-(C 1-C 4)-alkyl, the heteroaryl sulfenyl, heteroaryl oxygen base carbonyl, heteroarylsulfonyl, the heteroaryl sulfinyl, and
1) R 4Described in substituting group when being aryl or heteroaryl, can be by one or more (C that are selected from 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-haloalkyl, (C 1-C 6The identical or different group of)-halogenated alkoxy and halogen replaces, and heteroaryl is the heteroaryl of 10 carbon atoms of band as many as;
2) R 4Described in cycloalkyl can be selected from halogen, (C by 5 of as many as 1-C 4The identical or different group of)-alkyl replaces;
3) R 4Described in substituent 2 represent methylenedioxy group or ethylenedioxy, methylenedioxy group or ethylenedioxy can with 1 or 2 identical or different be selected from halogen and (C 1-C 6The substituting group of)-alkyl.
3. alkyl-aryl according to claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds is characterized in that general formula (I), (II) and (III) in Ar1 be preferably as follows especially shown in a group:
Figure C9911555700051
Z and R 4As determined implication in the claim 2.
4. alkyl-aryl according to claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds is characterized in that general formula (I), (II) and (III) in, R 1And R 2Be identical or different, and represent hydrogen, halogen, (C 1-C 4)-alkyl, (C 1-C 4)-haloalkyl, (C 1-C 4)-alkylthio.
5. according to the described alkyl-aryl of claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds, it is characterized in that general formula (I), R (II) and (III) 3Represent hydrogen, (C 1-C 4)-alkyl, (C 1-C 4)-haloalkyl.
6. according to the described alkyl-aryl of claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds, it is characterized in that Ar2 representative in the general formula (I):
R represents N or CH; Q is O, S, NH or CH 2R 6Be hydrogen, halogen, allyl group oxygen base, propargyloxy;
Figure C9911555700053
F represents fluorine;
T is identical or different with g, represents 0,1,2,3 or 4, and t and g sum are not more than 5;
R 7Be identical or different, and represent hydrogen, halogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)-halogenated alkoxy, (C 1-C 6)-alkyl sulphonyl, (C 2-C 6)-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-alkenyl oxy alkyl, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-halogenated alkenyl oxy alkyl, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl, (C 2-C 6)-halo alkynyloxy base, (C 3-C 8)-cycloalkyl, (C 3-C 8)-cycloalkyl oxy, (C 3-C 8)-halogenated cycloalkyl, (C 6-C 12)-aryl, (C 6-C 12)-aryloxy, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-artyl sulfo, the heteroaryl of 10 carbon atoms of band as many as, heteroaryl oxygen base, heteroaryl-(C 1-C 4)-alkyl;
C.1) 2)
Z is O, S or NR 5, R 5As R in the claim 2 5Definition; W is 0,1,2 or 3;
R 8Be identical or different, and represent hydrogen, halogen, (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group-(C 1-C 6)-alkoxyl group, (C 1-C 6)-halogenated alkoxy, (C 2-C 6)-alkenyl, (C 2-C 6)-alkenyl oxy, (C 2-C 6)-halogenated alkenyl, (C 2-C 6)-halogenated alkenyl oxy, (C 2-C 6)-alkynyl, (C 2-C 6)-alkynyloxy base, (C 2-C 6)-halo alkynyl, (C 2-C 6)-halo alkynyloxy base, (C 6-C 12)-aryloxy, (C 6-C 12)-aryl-(C 1-C 4)-alkyl, (C 6-C 12)-artyl sulfo, the heteroaryl oxygen base of 10 carbon atoms of band as many as, heteroaryl sulfenyl, heteroaryl-(C 1-C 4)-alkyl, and R 8In aryl or heteroaryl, can be selected from (C 1-C 6)-alkyl, (C 1-C 6)-alkoxyl group, (C 1-C 6)-haloalkyl, (C 1-C 6The identical or different group of)-halogenated alkoxy and halogen replaces;
Figure C9911555700062
F represents fluorine;
R 9Be hydrogen, fluorine or methyl;
P is 0,1 or 2;
Figure C9911555700063
R is (C 1-C 6)-alkyl, (C 1-C 6)-haloalkyl;
A is an oxygen, sulphur or NH;
B is nitrogen or CH.
7. according to the preparation method of the described alkyl-aryl of claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds general formula (I) compound, it is characterized in that:
A) with a compound shown in the formula (III)
Make with the compound reaction shown in the formula (IV),
Figure C9911555700071
Definition in Ar2 and Y such as the claim 1 in the formula (IV), L represents a leavings group, if M is a hydrogen in the formula (III), then in the presence of an appropriate base, add suitable solvent, add phase-transfer catalyst again, in normal pressure, reaction is 1-20 hour and get under the 0-120 ℃ of condition, if M is alkali metal atom such as sodium in the formula (III), then in a suitable solvent, add phase-transfer catalyst, in normal pressure, reaction is 1-20 hour and get under the 0-120 ℃ of condition; Or
B) with the compound shown in the formula (II)
In case of necessity in the presence of an appropriate base with the compound shown in the formula V or with their reactant salt
Figure C9911555700072
Definition in Y and Ar2 such as the claim 1 in the formula.
8. according to the preparation method of the described alkyl-aryl of claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds general formula (III) compound, it is characterized in that:
With compound shown in the formula (II) and hydroxylamine hydrochloride or hydroxylamine sulfate, in normal pressure, 0-100 ℃, at water and/or alcohol and metal hydroxides, alkaline carbonate, reaction in alkali metal hydrocarbonate or the pyridine and getting.
9. according to the preparation method of the described alkyl-aryl of claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds general formula (II) compound, in the general formula (II), the preparation method of X=S compound is characterized in that:
With the compound shown in the formula (VI)
Figure C9911555700073
Ar1 and R in the formula 1, R 2, n, definition in m such as the claim 1, with the sodium salt of corresponding mercaptan in the aqueous solution, in normal pressure, 30-100 ℃ of reaction 2-10 hour and getting.
10. according to the preparation method of the described alkyl-aryl of claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds formula (I) compound, it is characterized in that preparing the used appropriate base of oxime ether compound is alkali metal hydroxide, alkaline carbonate, alkali metal hydrocarbonate, alkali metal alcoholates, basic metal, alkalimetal hydride, pyridine, tertiary amine; Phase-transfer catalyst is a tetrabutylammonium iodide, Tetrabutyl amonium bromide, tetraethylammonium bromide, hexaoxacyclooctadecane-6-6; Suitable solvent is to be selected from the following solvents one or both: water, and tetrahydrofuran (THF), toluene, benzene, acetonitrile, dimethyl sulfoxide (DMSO), suitable leavings group is a chlorine, bromine or OSO 2
11. according to the described alkyl-aryl of claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds, it is characterized in that: the compound shown in formula (I) and the formula (III) can two kinds of geometrical isomer forms occur: Z formula and E formula, the Z formula is that oxime-oxygen and aryl or heteroaryl Ar1 are in the two key homonymies of C=N, and the E formula is that oxime-oxygen is in C=N pair of key heteropleurals with aryl or heteroaryl Ar1;
Figure C9911555700081
Described alkyl-the aryl of claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds, as have one or more unsymmetrical carbons, it can be a racemic modification, diastereomer or pure optical isomer;
Described alkyl-the aryl of claim 1 or alkyl-heteroaryl-ketoxime-O-ether and intermediate ketone, oxime compounds not only relate to pure isomer, also relate to various mixture of isomers.
12. contain at least one according to the additive of compound in the claim 1 and routine and the harmful organism medicament extremely of auxiliary material.
13. contain at least one purposes on insect, evil mite, pathogenic bacteria and weeds of harmful organism medicament extremely according to the additive and the auxiliary material of compound in the claim 1 and routine.
14. contain at least one compound and the additive of routine and purposes on insect, evil mite, pathogenic bacteria and weeds of harmful organism medicament extremely of auxiliary material according to claim 1 to 6 Chinese style (II) and formula (III).
15. be used as the intermediate for preparing general formula (I) active substance according to described formula of claim 1 to 6 (II) and formula (III) compound.
CNB991155572A 1999-09-10 1999-09-10 Method for preparing biocide alkyl-substituted (hetero)-aryl-ketoxime-o-ether and its intermediate ketone or oxime compounds Expired - Lifetime CN1159290C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CNB991155572A CN1159290C (en) 1999-09-10 1999-09-10 Method for preparing biocide alkyl-substituted (hetero)-aryl-ketoxime-o-ether and its intermediate ketone or oxime compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CNB991155572A CN1159290C (en) 1999-09-10 1999-09-10 Method for preparing biocide alkyl-substituted (hetero)-aryl-ketoxime-o-ether and its intermediate ketone or oxime compounds

Publications (2)

Publication Number Publication Date
CN1288002A CN1288002A (en) 2001-03-21
CN1159290C true CN1159290C (en) 2004-07-28

Family

ID=5278499

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB991155572A Expired - Lifetime CN1159290C (en) 1999-09-10 1999-09-10 Method for preparing biocide alkyl-substituted (hetero)-aryl-ketoxime-o-ether and its intermediate ketone or oxime compounds

Country Status (1)

Country Link
CN (1) CN1159290C (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100579956C (en) * 2003-12-12 2010-01-13 湖南化工研究院 Insecticidal antibacterial sulphur, oxygen and oxime-containing ether compounds
CN102030680B (en) * 2010-10-20 2014-03-26 湖北省生物农药工程研究中心 Novel oxime ether or ester derivatives with insecticidal activity
CN102228044B (en) * 2011-05-11 2013-04-24 海利尔药业集团股份有限公司 Insecticidal composition containing sufluoxime
CN102239875A (en) * 2011-05-17 2011-11-16 海利尔药业集团股份有限公司 Insecticidal composition containing 1-(3-fluoro-4-chlorphenyl)-2-methylthioethanone-O-(2-hydroxymethyl-3-methyl)aether and partial nicotine compounds
CN102246778A (en) * 2011-05-18 2011-11-23 海利尔药业集团股份有限公司 Efficiency enhanced insecticidal composition, and application thereof
CN102228028A (en) * 2011-05-30 2011-11-02 青岛海利尔药业有限公司 Pesticide composition containing sulfur-fluorine oxime ether and part of amide pesticides
CN102911093B (en) * 2012-10-25 2014-08-13 湖南化工研究院 Preparation method for sulfur fluorine oxime ether
CN103734180B (en) * 2013-12-30 2015-12-30 刘一平 A kind of Fungicidal insecticidal composition containing sufluoxime
MX2018004516A (en) * 2015-10-13 2018-08-01 Nihon Nohyaku Co Ltd Oxime group-containing condensed heterocyclic compound or salts thereof and agricultural and horticultural insecticide containing said compound, and method for using same.
CN112661732B (en) * 2020-12-23 2023-08-04 湖南化研院检测技术有限公司 Furanol derivative and preparation method and application thereof

Also Published As

Publication number Publication date
CN1288002A (en) 2001-03-21

Similar Documents

Publication Publication Date Title
CN1035539C (en) Hydrazine derivative and pesticidal composition comprising said derivative as an effective ingredient
CN1059672C (en) 1,2,4-oxadiazole derivatives and their use as parasiticides for animals
CN1141032A (en) Pesticides
CN1427823A (en) Pyrrolecarboxamides and pyrrolethioamides as fungicides
CN1159290C (en) Method for preparing biocide alkyl-substituted (hetero)-aryl-ketoxime-o-ether and its intermediate ketone or oxime compounds
WO2013097518A1 (en) Thiazole methylamino pyridine compounds and preparation method therefor
CN1131945A (en) Arthropodicidal oxazolines and thiazolines
CN1217903C (en) Substituted biphenyl oxazoline
CN1117071C (en) Pesticides
CN1293083C (en) Siliconated phenyl amides derivatives useful as microbiocide
CN1100761C (en) Benzyloxy substituted aromatics and their use as fungicides and insecticides
CN1670016A (en) Aryl pyrrole compounds with insecticidal, miticidal and fungicidal bioactivities and process for preparing same
CN1546462A (en) Insecticidal antibacterial sulphur , oxygen and oxime-containing ether compounds
CN1511142A (en) Pyrazolecarboxamide derivative, intermediate therefor, and pest control agent containing same as active ingredient
CN1333761A (en) Isothiazolecarboxylic acid derivatives
CN1063281A (en) 2-aryl-5-(trifluoromethyl)-2-pyrrolinium compound and method for producing insecticide, 2-aryl-1-(alkoxyl-methyl)-4-halo-5-(trifluoromethyl) pyrroles
CN1071322C (en) Process for producing 5,6-dihydro-1,3-oxazines
CN1027448C (en) Heterocyclic neophenan alogue, process of preparation and used as insecticide thereof
CN1079462A (en) New 7-ethynyl-α-(methoxyl group methylene radical)-1-naphthylacetic acid derivant and preparation method thereof and as sterilant
CN1323784A (en) Amidine compound and usage as insecticide
CN1105023A (en) Substituted benzoyl cyclic enone, process for preparation, and herbicide
CN1121510A (en) Substituted phenoxymethylphenyl derivatives, their preparation and their use for controlling pests and fungi
CN1146203A (en) Pyrimidinyl aryl ketone oximes
CN1059671C (en) 3-aryl akenyl-1,2,4-oxadiazole derivatives and their use as parasiticides for animals
CN1091423A (en) The pesticide composition that contains derivative of diene amide

Legal Events

Date Code Title Description
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C06 Publication
PB01 Publication
C14 Grant of patent or utility model
GR01 Patent grant
CX01 Expiry of patent term

Granted publication date: 20040728

CX01 Expiry of patent term