CN1280767A - Heterocycle substituted isoxazoline compounds used as disinfectant - Google Patents

Heterocycle substituted isoxazoline compounds used as disinfectant Download PDF

Info

Publication number
CN1280767A
CN1280767A CN 99113093 CN99113093A CN1280767A CN 1280767 A CN1280767 A CN 1280767A CN 99113093 CN99113093 CN 99113093 CN 99113093 A CN99113093 A CN 99113093A CN 1280767 A CN1280767 A CN 1280767A
Authority
CN
China
Prior art keywords
alkyl
chlorphenyl
halogen
cycloalkyl
fluorophenyl
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.)
Granted
Application number
CN 99113093
Other languages
Chinese (zh)
Other versions
CN1091444C (en
Inventor
张立新
史蒂芬H·塞伯
爱德华M·斯采佩斯
詹姆斯·奎恩
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.)
Shenyang Sinochem Agrochemicals R&D Co Ltd
Original Assignee
Shenyang Research Institute of Chemical Industry Co Ltd
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 Shenyang Research Institute of Chemical Industry Co Ltd filed Critical Shenyang Research Institute of Chemical Industry Co Ltd
Priority to CN99113093A priority Critical patent/CN1091444C/en
Publication of CN1280767A publication Critical patent/CN1280767A/en
Application granted granted Critical
Publication of CN1091444C publication Critical patent/CN1091444C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Landscapes

  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The heterocycle substituted isoxazoline compounds used as disinfectant and its stereoisomer are disclosed, and they can be used individually or in conjunction with other active components.

Description

Heterocyclic substituted De isoxazoline compounds as bactericide
The invention belongs to the disinfectant use in agriculture field.
U.S. Pat had once been reported some 2-aryl-3-in P.4066770, and (3-pyridine radicals) isoxazoline compounds can be used as bactericide.
In order to satisfy the requirement on the agricultural, the invention provides novel 3,3 '-two replace, contain 3-pyridine radicals or 5-pyrimidine radicals and non-hydrogen substituting group, at least one carbon containing substituted radical De isoxazoline compounds, their preparation method are arranged on the C-5 position and contain these compound compositions, and the method for preventing and treating fungies (particularly fungi infecting plant) with these compounds.
The invention provides the have general formula compound of (I) and enantiomer thereof, stereoisomer:
Figure 9911309300041
X is N or CH in the formula;
R is (C 1-C 12) alkyl, halogen (C 1-C 12) alkyl, (C 2-C 8) thiazolinyl, halogen (C 2-C 8) thiazolinyl, (C 2-C 8) alkynyl, halogen (C 2-C 8) alkynyl, (C 1-C 12) alcoxyl (C 1-C 12) alkyl, (C 3-C 7) cycloalkyl, halogen (C 3-C 7) cycloalkyl, (C 3-C 7) cycloalkyl (C 1-C 4) alkyl, aryl alkyl, aryloxy group (C 1-C 4) alkyl, heterocyclic radical;
R 1Be aryl, heterocyclic radical or C (R 6R 7R 8);
R 2And R 3Each is hydrogen, (C naturally 1-C 12) alkyl, halogen (C 1-C 12) alkyl, (C 1-C 12) alkoxyl, halogen (C 1-C 12) alkoxyl, (C 3-C 7) cycloalkyl, (C 3-C 7) cycloalkyl (C 1-C 4) alkyl, aryl, aryl alkyl, heterocyclic radical; Cyano group or (C 1-C 4) alkoxy carbonyl;
R 4And R 5Each is hydrogen, (C naturally 1-C 12) alkyl, halogen (C 1-C 12) alkyl, (C 2-C 8) thiazolinyl, halogen (C 2-C 8) thiazolinyl, (C 2-C 8) alkynyl, halogen (C 2-C 8) alkynyl, (C 3-C 7) cycloalkyl, halogen (C 3-C 7) cycloalkyl, (C 3-C 7) cycloalkyl (C 1-C 4) alkyl, aryl, aryloxy group (C 1-C 4) alkyl, aryl alkyl, heterocyclic radical, cyano group or (C 1-C 4) alkoxy carbonyl; But R 4And R 5Be not hydrogen simultaneously;
R 6, R 7And R 8Each is hydrogen, (C naturally 1-C 12) alkyl, (C 2-C 8) thiazolinyl, (C 2-C 8) alkynyl, (C 1-C 12) alcoxyl (C 1-C 12) alkyl, (C 3-C 7) cycloalkyl, (C 3-C 7) cycloalkyl (C 1-C 4) alkyl, aryl, aralkyl, heterocycle (C 1-C 4) alkyl;
So-called (C 1-C 12) alkyl, (C 2-C 8) thiazolinyl, (C 2-C 8) alkynyl, (C 3-C 7) cycloalkyl can selectively single, double or three replacements by nitro, trihalomethyl or cyano group etc.
So-called alkyl is meant and contains 1 to 12 carbon atom, comprise the straight or branched form, for example methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, positive decyl etc.Alkylhalide group is meant that alkyl is replaced by 1 to 3 halogen atom.
So-called thiazolinyl is meant the unsaturated hydrocarbon that contains 2 to 8 carbon atoms, comprises the straight or branched form, has 1 to 2 carbon-carbon double bond.
Haloalkenyl group is meant the thiazolinyl that is replaced by 1 to 3 halogen atom.
So-called alkynyl is meant and contains the unsaturated hydrocarbon that 2 to 8 carbon atoms comprise the straight or branched form, 1 to 2 carbon carbon triple bond can be arranged.
So-called cycloalkyl is meant the saturated rings that contains 3 to 7 carbon atoms.
So-called aryl comprises phenyl and naphthyl, and they can be replaced by 3 following radicals of as many as: halogen, cyano group, nitro, trihalomethyl, phenyl, phenoxy group, (C 1-C 4) alkyl, alkylthio group, alkyl sulphonyl or alkylhalide group and (C 1-C 6) alkoxyl.
Typical aryl substituent includes but not limited to as 4-chlorphenyl, 4-fluorophenyl, 4-bromophenyl, 2-tolyl, 3-tolyl, 4-tolyl, 2-anisyl, 4-methoxyphenyl, 2,4-Dimethoxyphenyl, 2,4-dibromo phenyl, 3,5-difluorophenyl, 2,4,6-trichlorophenyl, 4-trifluoromethyl, 2-iodo-4-aminomethyl phenyl, 2-chloronaphthyl, methylnaphthyl etc.
So-called heterocyclic radical is meant and replaces or unsubstitutedly contain 1 to 3 heteroatomic unsaturated five or hexatomic ring.Unsaturated and the ring that particularly contains ten atoms of as many as of 1 to 2 nitrogen, oxygen, sulphur atom and nitrogenous, oxygen, sulphur atom.For example but be not limited to: the 2-pyrrole is than pyridine base, 3-pyridine radicals, 4-pyridine radicals, piperidyl, 2-pyrimidine radicals, 4-pyrimidine radicals, 5-pyrimidine radicals, pyrazinyl, triazolyl, imidazole radicals, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, pyrrole radicals, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazole base, thiadiazolyl group, quinolyl, isoquinolyl, and these heterocycles can be by 1 to 2 (C 1-C 4) alkyl, halogen, cyano group, nitro or trihalomethyl replace.
So-called aryl alkyl is meant the alkyl chain that contains 1 to 10 carbon atom, and these alkyl chains can be the straight or branched forms, but straight chain preferably is connected on the chain as top defined aryl moiety.For example benzyl, phenethyl, phenylpropyl, benzene butyl.Typical benzyl such as 2-benzyl chloride base, 3-benzyl chloride base, 4-benzyl chloride base, 2-luorobenzyl, 3-luorobenzyl, 4-luorobenzyl, 4-trifluoromethyl benzyl, 2,4-dichloro benzyl, 2,4-dibromo-benzyl, 2-methyl-benzyl, 3-methyl-benzyl, 4-methyl-benzyl.Typical phenethyl such as 2-(2-chlorphenyl) ethyl, 2-(3-chlorphenyl) ethyl, 2-(4-chlorphenyl) ethyl, 2-(2-fluorophenyl) ethyl, 2-(3-fluorophenyl) ethyl, 2-(4-fluorophenyl) ethyl, 2-(2-aminomethyl phenyl) ethyl, 2-(3-aminomethyl phenyl) ethyl, 2-(4-aminomethyl phenyl) ethyl, 2-(4-trifluoromethyl) ethyl, 2-(2-methoxyphenyl) ethyl, 2-(3-methoxyphenyl) ethyl, 2-(4-methoxyphenyl) ethyl, 2-(2, the 4-dichlorophenyl) ethyl, 2-(3, the 5-Dimethoxyphenyl) ethyl.Typical phenylpropyl such as 3-phenylpropyl, 3-(2-chlorphenyl) propyl group, 3-(3-chlorphenyl) propyl group, 3-(4-chlorphenyl) propyl group, 3-(2, the 4-dichlorophenyl) propyl group, 3-(2-fluorophenyl) propyl group, 3-(3-fluorophenyl) propyl group, 3-(4-fluorophenyl) propyl group, 3-(2-aminomethyl phenyl) propyl group, 3-(3-aminomethyl phenyl) propyl group, 3-(4-aminomethyl phenyl) propyl group, 3-(2-methoxyphenyl) propyl group, 3-(3-methoxyphenyl) propyl group, 3-(4-methoxyphenyl) propyl group, 3-(4-trifluoromethyl) propyl group, 3-(2, the 4-dichlorophenyl) propyl group, 3-(3, the 5-Dimethoxyphenyl) propyl group.Typical benzene butyl such as 4-benzene butyl, 4-(2-chlorphenyl) butyl, 4-(3-chlorphenyl) butyl, 4-(4-chlorphenyl) butyl, 4-(2,4 dichloro benzene base) butyl, 4-(2-fluorophenyl) butyl, 4-(3-fluorophenyl) butyl, 4-(4-fluorophenyl) butyl, 4-(2-aminomethyl phenyl) butyl, 4-(3-aminomethyl phenyl) butyl, 4-(4-aminomethyl phenyl) butyl, 4-(2-methoxyphenyl) butyl, 4-(3-methoxyphenyl) butyl, 4-(4-methoxyphenyl) butyl.
So-called halogen is meant fluorine, chlorine, bromine, iodine.
R 2, R 3And R 4, R 5For heterocycle cis-trans-isomer can be arranged.These isomer can separate with conventional method.These isomer and composition thereof, with and bactericidal activity constituted the present invention.
Among the present invention than compound and isomer, salt and the composition of suitable compound shown in general formula (I '):
Compare with general formula (I), wherein X is N or CH;
R is (C 1-C 12) alkyl; R 1Be aryl or C (R 6R 7R 8);
R 2, R 3And R 5Each is hydrogen naturally;
R 4Be aryl, aryloxy group (C 1-C 4) alkyl, aryl alkyl, heterocyclic radical, cyano group or (C 1-C 4) alkoxy carbonyl.
Compound and isomer, salt and the composition of compound shown in general formula (I ") more suitably among the present invention:
Figure 9911309300061
Compare with general formula (I '), wherein X is CH; R is a methyl; R 1Be C (R 6R 7R 8), R wherein 6, R 7And R 8Be H.
The compound of general formula (I) can be prepared by reaction equation A.These 3-heterocyclic radicals-3,4, the 5-substituted isoxazolines can be prepared by nitrous ketone (V) and the alkene (VI) that replaces reaction.1 of nitrous ketone and alkene, 3-Dipolar Cycloaddition had description in following document: Advanced in Heterocyclic Chemistry, Vol.21,207-251,1977; AngewandteChem.Int.Ed, Vol.2,565-598,1963; Synthesis, 205-221,1975; J.Org.Chemistry, Vol.49,276-281,1984 and appended list of references.Cycloaddition reaction can produce two kinds of isomer.A kind of isomer as shown in reaction equation A, R in the structure I 4, R 5The carbon adjacent with oxygen links to each other; R 2, R 3The carbon adjacent with the oxygen another kind of isoxazoline isomer that obtains that links to each other also is a part of the present invention.Thin layer or column chromatography with routine can be with above-mentioned isomer separation.Formula V or V ' shown in N-replace-3, the reaction that 3-two replaces the nitrous ketone can be carried out in suitable reaction medium such as benzene, toluene or chlorobenzene, suitable reaction temperature is 50 ℃ of reflux temperatures to solvent.Temperature preferably is in reflux in toluene.Alkene can be four substituted olefines (VI) shown in reaction equation A, α more usually, α-disubstituted olefin (VI, wherein R 2, R 3Be H) and single substituted olefine (VI ', R wherein 4Be H) as substituted phenylethylene, allyl ether, esters of acrylic acid.The product of reaction can exist with isomeric forms.When for example being starting material with mono-substituted alkene, H and R 5Can be for the heterocycle that contains three carbon atoms with cis or trans the existence.Cis or transisomer can by the column chromatography technical point from.Thin layer chromatography Rf value is big when separating is considered as isomer A.
Reaction equation A
Work as R 1Be C (R 6, R 7, R 8), R 2=R 3During=H,
Formula V or V ' shown in nitrous ketone can prepare by reaction equation B.N-among the present invention replaces-3, and it is on 3 non-hydrogen substituting group to be arranged that 3-two replaces nitrous ketone.The preparation of nitrous ketone and reaction are referring to Chem.Reviews, Vol.64,473-495,1964.Nitrous ketone among the present invention can be by as the defined R of preamble 1Replace ketone, react in the presence of sodium acetate as heterocyclic radical ketone such as 3-pyridyl ketone, 5-pyrimidine radicals ketone and R-NHOH such as N-methyl hydroxylamine hydrochloride and make.Reaction can be at suitable protonic solvent for example methyl alcohol, ethanol, and solvent preferably is to carry out in the ethanol.Suitable reaction temperature is the reflux temperature that room temperature arrives solvent, and temperature preferably is a room temperature.Remove the back of desolvating and add carrene, cross and filter out insoluble matter, evaporate to dryness filtrate gets nitrous ketone.This nitrous ketone can be directly used in the ring-closure reaction among the reaction equation A
Reaction equation B
Work as R 1Be C (R 6R 7R 8) time,
Formula VII or VII ' shown in 3-pyridyl ketone, 5-pyrimidine radicals ketone can prepare by usual method.The 3-acetylpyridine has commodity selling.Advanced Organic Chemistry, 4th Ed, p.963-965 and narrated in the appended list of references by nitrile compounds and Grignard reagent alkyl magnesium bromide or lithium alkylide addition and make above-mentioned ketone compounds.Organic Synthesis; Vol.37,1957 have narrated by Fu Shi acylation reaction system pyridyl ketone, Tetrahedron Vol.48; p.9233-9236; 1992 have narrated the method for magnesium catalytic reaction system acetylpyridine, JACS, Vol.69; 119; narrated by the method for pyridyl ester compounds in 1947 and Vol.76,5452,1954 through Claisen condensation system pyridyl ketone.When thick nitrous ketone (V or V ') during, obtain the mixture of (I) and (VII) with substituted olefine (VI or VI ') reaction.With this mixture and R-NHOH in the presence of sodium acetate in alcohols solvent stirring at room can remove unreacted (VII) or (VII ').Remove and desolvate, residue is dissolved in organic solvent, and the washing organic facies can be removed water miscible nitrous ketone, is pure object in the organic facies.
Below listed the part typical compound of general formula of the present invention (I) in three tables, but do not limit the present invention.
Listed a part of compound of the present invention in the table 1, X is CH in its general formula (I), R 2, R 3Be H, R 1Be C (R 6, R 7, R 8), shown in general formula (II), wherein R, R 4, R 5, R 6, R 7, R 8Definition see Table 1.
Figure 9911309300073
Table 1
Numbering ????R ????R 4 R 5 ?R 6 ?R 7 Rerum natura
1.1 ????CH 3 ????Ph ?H ?H ?H ?H Grease
1.2 ????CH 3 ????2-Cl-Ph ?H ?H ?H ?H Grease
1.3 ????CH 3 ????3-Cl-Ph ?H ?H ?H ?H Grease
1.4 ????CH 3 ????4-Cl-Ph ?H ?H ?H ?H Grease
1.4A ????CH 3 ????4-Cl-Ph ?H ?H ?H ?H Grease isomer A/B=9/1
?1.4B ????CH 3 ????4-Cl-Ph ?H ?H ?H ?H Isomer B/A=6/1 fusing point: 75-80 ℃
1.5 ????CH 3 ????2-FPh ?H ?H ?H ?H Grease
1.6 ????CH 3 ????3-FPh ?H ?H ?H ?H Grease
1.7 ????CH 3 ????4-FPh ?H ?H ?H ?H Grease
1.8 ????CH 3 ????2-BrPh ?H ?H ?H ?H
1.9 ????CH 3 ????3-BrPh ?H ?H ?H ?H Grease
1.10 ????CH 3 ????4-BrPh ?H ?H ?H ?H Grease
1.11 ????CH 3 ????2-CF 3Ph ?H ?H ?H ?H
1.12 ????CH 3 ????3-CF 3Ph ?H ?H ?H ?H
1.13 ????CH 3 ????4-CF 3Ph ?H ?H ?H ?H Grease
1.14 ????CH 3 ????2-MePh ?H ?H ?H ?H
1.15 ????CH 3 ????3-MePh ?H ?H ?H ?H Grease
1.16 ????CH 3 ????4-MePh ?H ?H ?H ?H
1.17 ????CH 3 ????2-OMePh ?H ?H ?H ?H
1.18 ????CH 3 ????3-OMePh ?H ?H ?H ?H
1.19 ????CH 3 ????4-OMePh ?H ?H ?H ?H
1.20 ????CH 3 ????1-Naphthyl ?H ?H ?H ?H
1.21 ????CH 3 ????2，4-Cl 2Ph ?H ?H ?H ?H
1.22 ????CH 3 ????3，4-Cl 2Ph ?H ?H ?H ?H
1.23 ????CH 3 ????2，4-Me 2Ph ?H ?H ?H ?H Grease
1.23 ?A ????CH 3 ????2，4-Me 2Ph ?H ?H ?H ?H The grease isomer
1.24 ????CH 3 The 2-pyridine radicals ?H ?H ?H ?H
1.25 ????CH 3 The 3-pyridine radicals ?H ?H ?H ?H
1.26 ????CH 3 The 4-pyridine radicals ?H ?H ?H ?H
1.27 ????CH 3 ????-CH 2-O-Ph ?H ?H ?H ?H
1.28 ????CH 3 ????-CH 2-O-Ph(2Cl) ?H ?H ?H ?H
1.29 ????CH 3 ????-CH 2-O-Ph(3Cl) ?H ?H ?H ?H
1.30 ????CH 3 ????-CH 2-O-Ph(4Cl) ?H ?H ?H ?H
1.31 ????CH 3 ????-CH 2-O-Ph(2F) ?H ?H ?H ?H
?1.32 ????CH 3 ????-CH 2-O-Ph(3F) ?H ?H ?H ?H
?1.33 ????CH 3 ????-CH 2-O-Ph(4F) ?H ?H ?H ?H
?1.34 ????CH 3 ????-CH 2-O-Ph(3CF 3) ?H ?H ?H ?H
?1.35 ????CH 3 ????-CH 2-O-Ph(4CF 3) ?H ?H ?H ?H
?1.36 ????C 2H 5 ????Ph ?H ?H ?H ?H
?1.37 ????C 2H 5 ????2Cl-Ph ?H ?H ?H ?H
?1.38 ????C 2H 5 ????3Cl-Ph ?H ?H ?H ?H
?1.39 ????C 2H 5 ????4Cl-Ph ?H ?H ?H ?H Grease
?1.40 ????C 2H 5 ????2，4-Cl 2-Ph ?H ?H ?H ?H
?1.41 ????C 2H 5 ????3，4-Cl 2-Ph ?H ?H ?H ?H
?1.42 ????C 2H 5 The 2-pyridine radicals ?H ?H ?H ?H
?1.43 ????C 2H 5 The 3-pyridine radicals ?H ?H ?H ?H
?1.44 ????C 2H 5 The 4-pyridine radicals ?H ?H ?H ?H
?1.45 ????C 2H 5 ????-CH 2-O-Ph ?H ?H ?H ?H
?1.46 ????C 2H 5 ????-CH 2-O-Ph(4Cl) ?H ?H ?H ?H
?1.47 ????C 2H 5 ????-CH 2-O-Ph(4CF 3) ?H ?H ?H ?H
?1.48 ?iso-C 3H 7 ????Ph ?H ?H ?H ?H
?1.49 ?iso-C 3H 7 ????2Cl-Ph ?H ?H ?H ?H
?1.50 ?iso-C 3H 7 ????3Cl-Ph ?H ?H ?H ?H
?1.51 ?iso-C 3H 7 ????4Cl-Ph ?H ?H ?H ?H Grease
?1.52 ?iso-C 3H 7 ????2，4-Cl 2-Ph ?H ?H ?H ?H
?1.53 ?iso-C 3H 7 ????3，4-Cl 2-Ph ?H ?H ?H ?H
?1.54 ?iso-C 3H 7 The 2-pyridine radicals ?H ?H ?H ?H
?1.55 ?iso-C 3H 7 The 3-pyridine radicals ?H ?H ?H ?H
?1.56 ?iso-C 3H 7 The 4-pyridine radicals ?H ?H ?H ?H
?1.57 ?iso-C 3H 7 ????-CH 2-O-Ph ?H ?H ?H ?H
?1.58 ?iso-C 3H 7 ????-CH 2-O-Ph(4Cl) ?H ?H ?H ?H
?1.59 ?iso-C 3H 7 ????-CH 2-O-Ph(4CF 3) ?H ?H ?H ?H
?1.60 ?c-C 6H 11 ????Ph ?H ?H ?H ?H
?1.61 ?c-C 6H 11 ????2Cl-Ph ?H ?H ?H ?H
?1.62 ?c-C 6H 11 ????3Cl-Ph ?H ?H ?H ?H
?1.63 ?c-C 6H 11 ????4Cl-Ph ?H ?H ?H ?H Grease
?1.64 ?c-C 6H 11 ????2，4-Cl 2-Ph ?H ?H ?H ?H
?1.65 ?c-C 6H 11 ????3，4-Cl 2Ph ?H ?H ?H ?H
?1.66 ?c-C 6H 11 The 2-pyridine radicals ?H ?H ?H ?H
?1.67 ?c-C 6H 11 The 3-pyridine radicals ?H ?H ?H ?H
?1.68 ?c-C 6H 11 The 4-pyridine radicals ?H ?H ?H ?H
?1.69 ?c-C 6H 11 ????-CH 2-O-Ph ?H ?H ?H ?H
?1.70 ?c-C 6H 11 ????-CH 2-O-Ph(4Cl) ?H ?H ?H ?H
?1.71 ?c-C 6H 11 ????-CH 2-O-Ph(4CF 3) ?H ?H ?H ?H
?1.72 ????CH 3 ????Ph ?H ?CH 3 ?H ?H
?1.73 ????CH 3 ????2Cl-Ph ?H ?CH 3 ?H ?H
?1.74 ????CH 3 ????3Cl-Ph ?H ?CH 3 ?H ?H
?1.75 ????CH 3 ????4Cl-Ph ?H ?CH 3 ?H ?H
?1.76 ????CH 3 ????2，4-Cl 2-Ph ?H ?CH 3 ?H ?H
?1.77 ????CH 3 ????3，4-Cl 2-Ph ?H ?CH 3 ?H ?H
?1.78 ????CH 3 The 2-pyridine radicals ?H ?CH 3 ?H ?H
?1.79 ????CH 3 The 3-pyridine radicals ?H ?CH 3 ?H ?H
?1.80 ????CH 3 The 4-pyridine radicals ?H ?CH 3 ?H ?H
?1.81 ????CH 3 ????-CH 2-O-Ph ?H ?CH 3 ?H ?H
?1.82 ????CH 3 ????-CH 2-O-Ph(2Cl) ?H ?CH 3 ?H ?H
?1.83 ????CH 3 ????-CH 2-O-Ph(3Cl) ?H ?CH 3 ?H ?H
?1.84 ????CH 3 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?H ?H
?1.85 ????CH 3 ????-CH 2-O-Ph(2F) ?H ?CH 3 ?H ?H
?1.86 ????CH 3 ????-CH 2-O-Ph(3F) ?H ?CH 3 ?H ?H
?1.87 ????CH 3 ????-CH 2-O-Ph(4F) ?H ?CH 3 ?H ?H
?1.88 ????C 2H 5 ????Ph ?H ?CH 3 ?H ?H
?1.89 ????C 2H 5 ????2Cl-Ph ?H ?CH 3 ?H ?H
?1.90 ????C 2H 5 ????3Cl-Ph ?H ?CH 3 ?H ?H
?1.91 ????C 2H 5 ????4Cl-Ph ?H ?CH 3 ?H ?H
?1.92 ????C 2H 5 ????2，4-Cl 2-Ph ?H ?CH 3 ?H ?H
?1.93 ????C 2H 5 ????3，4-Cl 2-Ph ?H ?CH 3 ?H ?H
?1.94 ????C 2H 5 The 2-pyridine radicals ?H ?CH 3 ?H ?H
?1.95 ????C 2H 5 The 3-pyridine radicals ?H ?CH 3 ?H ?H
?1.96 ????C 2H 5 The 4-pyridine radicals ?H ?CH 3 ?H ?H
?1.97 ????C 2H 5 ????-CH 2-O-Ph ?H ?CH 3 ?H ?H
?1.98 ????C 2H 5 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?H ?H
?1.99 ????C 2H 5 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?H ?H
?1.100 ?iso-C 3H 7 ????Ph ?H ?CH 3 ?H ?H
?1.101 ?iso-C 3H 7 ????2Cl-Ph ?H ?CH 3 ?H ?H
?1.102 ?iso-C 3H 7 ????3Cl-Ph ?H ?CH 3 ?H ?H
?1.103 ?iso-C 3H 7 ????4Cl-Ph ?H ?CH 3 ?H ?H
?1.104 ?iso-C 3H 7 ????2，4-Cl 2-Ph ?H ?CH 3 ?H ?H
?1.105 ?iso-C 3H 7 ????3，4-Cl 2Ph ?H ?CH 3 ?H ?H
?1.106 ?iso-C 3H 7 The 2-pyridine radicals ?H ?CH 3 ?H ?H
?1.107 ?iso-C 3H 7 The 3-pyridine radicals ?H ?CH 3 ?H ?H
?1.108 ?iso-C 3H 7 The 4-pyridine radicals ?H ?CH 3 ?H ?H
?1.109 ?iso-C 3H 7 ????-CH 2-O-Ph ?H ?CH 3 ?H ?H
?1.110 ?iso-C 3H 7 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?H ?H
?1.111 ?iso-C 3H 7 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?H ?H
?1.112 ?c-C 6H 11 ????Ph ?H ?CH 3 ?H ?H
?1.113 ?c-C 6H 11 ????2Cl-Ph ?H ?CH 3 ?H ?H
?1.114 ?c-C 6H 11 ????3Cl-Ph ?H ?CH 3 ?H ?H
?1.115 ?c-C 6H 11 ????4Cl-Ph ?H ?CH 3 ?H ?H
?1.116 ?c-C 6H 11 ????2，4-Cl 2-Ph ?H ?CH 3 ?H ?H
?1.117 ?c-C 6H 11 ????3，4-Cl 2-Ph ?H ?CH 3 ?H ?H
?1.118 ?c-C 6H 11 The 2-pyridine radicals ?H ?CH 3 ?H ?H
?1.119 ?c-C 6H 11 The 3-pyridine radicals ?H ?CH 3 ?H ?H
?1.120 ?c-C 6H 11 The 4-pyridine radicals ?H ?CH 3 ?H ?H
?1.121 ?c-C 6H 11 ????-CH 2-O-Ph ?H ?CH 3 ?H ?H
?1.122 ?c-C 6H 11 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?H ?H
?1.123 ?c-C 6H 11 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?H ?H
?1.124 ????CH 3 ????Ph ?H ?CH 3 ?CH 3 ?H
?1.125 ????CH 3 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.126 ????CH 3 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.127 ????CH 3 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.128 ????CH 3 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
?1.129 ????CH 3 ????3，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
?1.130 ????CH 3 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.131 ????CH 3 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.132 ????CH 3 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.133 ????CH 3 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?H
?1.134 ????CH 3 ????-CH 2-O-Ph(2Cl) ?H ?CH 3 ?CH 3 ?H
?1.135 ????CH 3 ????-CH 2-O-Ph(3Cl) ?H ?CH 3 ?CH 3 ?H
?1.136 ????CH 3 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?H
?1.137 ????CH 3 ????-CH 2-O-Ph(2F) ?H ?CH 3 ?CH 3 ?H
?1.138 ????CH 3 ????-CH 2-O-Ph(3F) ?H ?CH 3 ?CH 3 ?H
?1.139 ????CH 3 ????-CH 2-O-Ph(4F) ?H ?CH 3 ?CH 3 ?H
?1.140 ????CH 3 ????-CH 2-O-Ph(3CF 3) ?H ?CH 3 ?CH 3 ?H
?1.141 ????CH 3 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?H
?1.142 ????C 2H 5 ????Ph ?H ?CH 3 ?CH 3 ?H
?1.143 ????C 2H 5 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.144 ????C 2H 5 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.145 ????C 2H 5 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.146 ????C 2H 5 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
?1.147 ????C 2H 5 ????3，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
?1.148 ????C 2H 5 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.149 ????C 2H 5 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.150 ????C 2H 5 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.151 ????C 2H 5 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?H
?1.152 ????C 2H 5 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?H
?1.153 ????C 2H 5 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?H
?1.154 ?iso-C 3H 7 ????Ph ?H ?CH 3 ?CH 3 ?H
?1.155 ?iso-C 3H 7 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.156 ?iso-C 3H 7 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.157 ?iso-C 3H 7 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.158 ?iso-C 3H 7 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
?1.159 ?iso-C 3H 7 ????3，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
?1.160 ?iso-C 3H 7 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.161 ?iso-C 3H 7 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.162 ?iso-C 3H 7 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.163 ?iso-C 3H 7 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?H
?1.164 ?iso-C 3H 7 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?H
?1.165 ?iso-C 3H 7 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?H
?1.166 ?c-C 6H 11 ????Ph ?H ?CH 3 ?CH 3 ?H
?1.167 ?c-C 6H 11 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.168 ?c-C 6H 11 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.169 ?c-C 6H 11 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?H
?1.170 ?c-C 6H 11 ????2，4-Cl2-Ph ?H ?CH 3 ?CH 3 ?H
?1.171 ?c-C 6H 11 ????3，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
?1.172 ?c-C 6H 11 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.173 ?c-C 6H 11 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.174 ?c-C 6H 11 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?H
?1.175 ?c-C 6H 11 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?H
?1.176 ?c-C 6H 11 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?H
?1.177 ?c-C 6H 11 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?H
?1.178 ????CH 3 ????Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.179 ????CH 3 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.180 ????CH 3 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.181 ????CH 3 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.182 ????CH 3 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.183 ????CH 3 ????3，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.184 ????CH 3 The 2-pyridine radicals ?CH 3 ?CH 3 ?CH 3
?1.185 ????CH 3 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?1.186 ????CH 3 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?1.187 ????CH 3 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.188 ????CH 3 ????-CH 2-O-Ph(2Cl) ?H ?CH 3 ?CH 3 ?CH 3
?1.189 ????CH 3 ????-CH 2-O-Ph(3Cl) ?H ?CH 3 ?CH 3 ?CH 3
?1.190 ????CH 3 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?CH 3
?1.191 ????CH 3 ????-CH 2-O-Ph(2F) ?H ?CH 3 ?CH 3 ?CH 3
?1.192 ????CH 3 ????-CH 2-O-Ph(3F) ?H ?CH 3 ?CH 3 ?CH 3
?1.193 ????CH 3 ????-CH 2-O-Ph(4F) ?H ?CH 3 ?CH 3 ?CH 3
?1.194 ????CH 3 ????-CH 2-O-Ph(2CF 3) ?H ?CH 3 ?CH 3 ?CH 3
?1.195 ????CH 3 ????-CH 2-O-Ph(3CF 3) ?H ?CH 3 ?CH 3 ?CH 3
?1.196 ????CH 3 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?CH 3
?1.197 ????C 2H 5 ????Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.198 ????C 2H 5 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.199 ????C 2H 5 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.200 ????C 2H 5 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.201 ????C 2H 5 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.202 ????C 2H 5 ????3，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
?1.203 ????C 2H 5 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
1.204 ????C 2H 5 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
1.205 ????C 2H 5 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
1.206 ????C 2H 5 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.207 ????C 2H 5 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?CH 3
1.208 ????C 2H 5 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?CH 3
1.209 ?iso-C 3H 7 ????Ph ?H ?CH 3 ?CH 3 ?CH 3
1.210 ?iso-C 3H 7 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.211 ?iso-C 3H 7 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.212 ?iso-C 3H 7 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.213 ?iso-C 3H 7 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.214 ?iso-C 3H 7 ????3，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.21?5 ?iso-C 3H 7 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
1.216 ?iso-C 3H 7 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
1.217 ?iso-C 3H 7 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
1.218 ?iso-C 3H 7 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.219 ?iso-C 3H 7 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?CH 3
1.220 ?iso-C 3H 7 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?CH 3
1.221 ?c-C 6H 11 ????Ph ?H ?CH 3 ?CH 3 ?CH 3
1.222 ?c-C 6H 11 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.223 ?c-C 6H 11 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.224 ?c-C 6H 11 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.225 ?c-C 6H 11 ????2．4-Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.226 ?c-C 6H 11 ????3．4-ClPh ?H ?CH 3 ?CH 3 ?CH 3
1.227 ?c-C 6H 11 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
1.228 ?c-C 6H 11 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
1.229 ?c-C 6H 11 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
1.230 ?c-C 6H 11 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?CH 3
1.231 ?c-C 6H 11 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?CH 3
1.232 ?c-C 6H 11 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?CH 3
1.233 ????CH 3 ????CN ?H ?H ?H ?H
1.234 ????CH 3 ????CO 2CH 3 ?H ?H ?H ?H
1.235 ????CH 3 ????CN ?H ?CH 3 ?H ?H
1.236 ????CH 3 ????CO 2CH 3 ?H ?CH 3 ?H ?H
1.237 ????CH 3 ????CN ?H ?CH 3 ?CH 3 ?H
1.238 ????CH 3 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?H
1.239 ????C 2H 5 ????CN ?H ?H ?H ?H
1.240 ????C 2H 5 ????CO 2CH 3 ?H ?H ?H ?H
1.241 ????C 2H 5 ????CN ?H ?CH 3 ?H ?H
1.242 ????C 2H 5 ????CO 2CH 3 ?H ?CH 3 ?H ?H
1.243 ????C 2H 5 ????CN ?H ?CH 3 ?CH 3 ?H
1.244 ????C 2H 5 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?H
1.245 ???i-C 3H 7 ????CN ?H ?H ?H ?H
1.246 ???i-C 3H 7 ????CO 2CH 3 ?H ?H ?H ?H
1.247 ????i-C 3H 7 ????CN ?H ?CH 3 ?H ?H
1.248 ????i-C 3H 7 ????CO 2CH 3 ?H ?CH 3 ?H ?H
1.249 ????i-C 3H 7 ????CN ?H ?CH 3 ?CH 3 ?H
1.250 ????i-C 3H 7 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?H
1.251 ????c-C 6H 11 ????CN ?H ?CH 3 ?CH 3 ?H
1.252 ????c-C 6H 11 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?H
1.253 ????CH 3 ????CN ????H ?CH 3 ?CH 3 ?CH 3
1.254 ????CH 3 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?CH 3
1.255 ????C 2H 5 ????CN ?H ?CH 3 ?CH 3 ?CH 3
1.256 ????C 2H 5 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?CH 3
1.257 ????i-C 3H 7 ????CN ?H ?CH 3 ?CH 3 ?CH 3
1.258 ????i-C 3H 7 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?CH 3
1.259 ????c-C 6H 11 ????CN ?H ?CH 3 ?CH 3 ?CH 3
1.260 ????c-C 6H 11 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?CH 3
Listed in the table 2 of the present invention in addition-part of compounds, the X in its general formula (I) is N, R 2And R 3Be H, R 1Be C (R 6R 7R 8), shown in general formula (III), wherein R, R 4, R 5, R 6, R 7, R 8Definition see Table 2.
Figure 9911309300141
Table 2
Numbering ????R ????R 4 ?R 5 ?R 6 ?R 7 ?R 8 Rerum natura
2.1 ????CH 3 ????Ph ?H ?H ?H ?H Grease
2.2 ????CH 3 ????2-ClPh ?H ?H ?H ?H Grease
2.3 ????CH 3 ????3-ClPh ?H ?H ?H ?H Grease
2.4 ????CH 3 ????4-Cl-Ph ?H ?H ?H ?H Grease,
2.5 ????CH 3 ????2-FPh ?H ?H ?H ?H Grease
2.6 ????CH 3 ????3-FPh ?H ?H ?H ?H Grease
2.7 ????CH 3 ????4-FPh ?H ?H ?H ?H Grease
2.8 ????CH 3 ????2-BrPh ?H ?H ?H ?H
2.9 ????CH 3 ????3-BrPh ?H ?H ?H ?H Grease
2.10 ????CH 3 ????4-BrPh ?H ?H ?H ?H Grease
2.11 ????CH 3 ????2-CF 3Ph ?H ?H ?H ?H
2.12 ????CH 3 ????3-CF 3Ph ?H ?H ?H
2.13 ????CH 3 ????4-CF 3Ph ?H ?H ?H ?H Grease
2.14 ????CH 3 ????2-MePh ?H ?H ?H ?H
?2.15 ????CH 3 ????3-MePh ?H ?H ?H ?H Grease
?2.16 ????CH 3 ????4-MePh ?H ?H ?H ?H
?2.17 ????CH 3 ????2-OMePh ?H ?H ?H ?H
?2.18 ????CH 3 ????3-OMePh ?H ?H ?H ?H
?2.19 ????CH 3 ????4-OMePh ?H ?H ?H ?H
?2.20 ????CH 3 ????1-Naphthyl ?H ?H ?H ?H
?2.21 ????CH 3 ????2-Naphthyl ?H ?H ?H ?H
?2.22 ????CH 3 ????2，4-Cl 2Ph ?H ?H ?H ?H
?2.23 ????CH 3 ????3，4-Cl 2Ph ?H ?H ?H ?H
?2.24 ????CH 3 ????3，5-Cl 2Ph ?H ?H ?H ?H
?2.25 ????CH 3 The 2-pyridine radicals ?H ?H ?H ?H
?2.26 ????CH 3 The 3-pyridine radicals ?H ?H ?H ?H
?2.27 ????CH 3 The 4-pyridine radicals ?H ?H ?H ?H
?2.28 ????CH 3 ????-CH 2-O-Ph ?H ?H ?H ?H
?2.29 ????CH 3 ????-CH 2-O-Ph(2Cl) ?H ?H ?H ?H
?2.30 ????CH 3 ????-CH 2-O-Ph(3Cl) ?H ?H ?H ?H
?2.31 ????CH 3 ????-CH 2-O-Ph(4C1) ?H ?H ?H
?2.32 ????CH 3 ????-CH 2-O-Ph(2F) ?H ?H ?H ?H
?2.33 ????CH 3 ????-CH 2-O-Ph(3F) ?H ?H ?H ?H
?2.34 ????CH 3 ????-CH 2-O-Ph(4F) ?H ?H ?H ?H
?2.35 ????CH 3 ????-CH 2-O-Ph(3CF 3) ?H ?H ?H ?H
?2.36 ????CH 3 ????-CH 2-O-Ph(4CF 3) ?H ?H ?H ?H
?2.37 ????C 2H 5 ????Ph ?H ?H ?H ?H
?2.38 ????C 2H 5 ????2Cl-Ph ?H ?H ?H ?H
?2.39 ????C 2H 5 ????3Cl-Ph ?H ?H ?H ?H
?2.40 ????C 2H 5 ????4Cl-Ph ?H ?H ?H ?H
?2.41 ????C 2H 5 ????2，4-Cl 2-Ph ?H ?H ?H ?H
?2.42 ????C 2H 5 ????3，4-Cl 2Ph ?H ?H ?H ?H
?2.43 ????C 2H 5 The 2-pyridine radicals ?H ?H ?H ?H
?2.44 ????C 2H 5 The 3-pyridine radicals ?H ?H ?H ?H
?2.45 ????C 2H 5 The 4-pyridine radicals ?H ?H ?H ?H
?2.46 ????C 2H 5 ????-CH 2-O-Ph ?H ?H ?H ?H
?2.47 ????C 2H 5 ????-CH 2-O-Ph(4Cl) ?H ?H ?H ?H
?2.48 ????C 2H 5 ????-CH 2-O-Ph(4CF 3) ?H ?H ?H ?H
?2.49 ?iso-C 3H 7 ????Ph ?H ?H ?H ?H
?2.50 ?iso-C 3H 7 ????2Cl-Ph ?H ?H ?H ?H
?2.51 ?iso-C 3H 7 ????3Cl-Ph ?H ?H ?H ?H
?2.52 ?iso-C 3H 7 ????4Cl-Ph ?H ?H ?H ?H
?2.53 ?iso-C 3H 7 ????2，4-Cl 2-Ph ?H ?H ?H ?H
?2.54 ?iso-C 3H 7 ????3，4-Cl 2Ph ?H ?H ?H ?H
?2.55 ?iso-C 3H 7 The 2-pyridine radicals ?H ?H ?H ?H
?2.56 ?iso-C 3H 7 The 3-pyridine radicals ?H ?H ?H ?H
?2.57 ?iso-C 3H 7 The 4-pyridine radicals ?H ?H ?H ?H
?2.58 ?iso-C 3H 7 ????-CH 2-O-Ph ?H ?H ?H ?H
?2.59 ?iso-C 3H 7 ????-CH 2-O-Ph(4Cl) ?H ?H ?H ?H
?2.60 ?iso-C 3H 7 ????-CH 2-O-Ph(4CF 3) ?H ?H ?H ?H
?2.61 ?c-C 6H 11 ????Ph ?H ?H ?H ?H
?2.62 ?c-C 6H 11 ????2Cl-Ph ?H ?H ?H ?H
?2.63 ?c-C 6H 11 ????3Cl-Ph ?H ?H ?H ?H
?2.64 ?c-C 6H 11 ????4Cl-Ph ?H ?H ?H ?H
?2.65 ?c-C 6H 11 ????2，4-Cl 2-Ph ?H ?H ?H ?H
?2.66 ?c-C 6H 11 ????3，4-Cl 2Ph ?H ?H ?H ?H
?2.67 ?c-C 6H 11 The 2-pyridine radicals ?H ?H ?H ?H
?2.68 ?c-C 6H 11 The 3-pyridine radicals ?H ?H ?H ?H
?2.69 ?c-C 6H 11 The 4-pyridine radicals ?H ?H ?H ?H
?2.70 ?c-C 6H 11 ????-CH 2-O-Ph ?H ?H ?H ?H
?2.71 ????c-C 6H 11 ????-CH 2-O-Ph(4Cl) ?H ?H ?H ?H
?2.72 ?c-C 6H 11 ????-CH 2-O-Ph(4CF 3) ?H ?H ?H ?H
?2.73 ????CH 3 ????Ph ?H ?CH 3 ?H ?H
?2.74 ????CH 3 ????2Cl-Ph ?H ?CH 3 ?H ?H
?2.75 ????CH 3 ????3Cl-Ph ?H ?CH 3 ?H ?H
?2.76 ????CH 3 ????4Cl-Ph ?H ?CH 3 ?H ?H
?2.77 ????CH 3 ????2，4-Cl 2-Ph ?H ?CH 3 ?H ?H
?2.78 ????CH 3 ????3，4-Cl 2Ph ?H ?CH 3 ?H ?H
?2.79 ????CH 3 The 2-pyridine radicals ?H ?CH 3 ?H ?H
?2.80 ????CH 3 The 3-pyridine radicals ?H ?CH 3 ?H ?H
?2.81 ????CH 3 The 4-pyridine radicals ?H ?CH 3 ?H ?H
?2.82 ????CH 3 ????-CH 2-O-Ph ?H ?CH 3 ?H ?H
?2.83 ????CH 3 ????-CH 2-O-Ph(2Cl) ?H ?CH 3 ?H ?H
?2.84 ????CH 3 ????-CH 2-O-Ph(3Cl) ?H ?CH 3 ?H ?H
?2.85 ????CH 3 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?H ?H
?2.86 ????CH 3 ????-CH 2-O-Ph(2F) ?H ?CH 3 ?H ?H
?2.87 ????CH 3 ????-CH 2-O-Ph(3F) ?H ?CH 3 ?H ?H
?2.88 ????CH 3 ????-CH 2-O-Ph(4F) ?H ?CH 3 ?H ?H
?2.89 ????CH 3 ????-CH 2-O-Ph(2CF 3) ?H ?CH 3 ?H ?H
?2.90 ????CH 3 ????-CH 2-O-Ph(3CF 3) ?H ?CH 3 ?H ?H
?2.91 ????CH 3 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?H ?H
?2.92 ????C 2H 5 ????Ph ?H ?CH 3 ?H ?H
?2.93 ????C 2H 5 ????2Cl-Ph ?H ?CH 3 ?H ?H
?2.94 ????C 2H 5 ????3Cl-Ph ?H ?CH 3 ?H ?H
?2.95 ????C 2H 5 ????4Cl-Ph ?H ?CH 3 ?H ?H
?2.96 ????C 2H 5 ????2，4-Cl 2-Ph ?H ?CH 3 ?H ?H
?2.97 ????C 2H 5 ????3，4-Cl 2Ph ?H ?CH 3 ?H ?H
?2.98 ????C 2H 5 The 2-pyridine radicals ?H ?CH 3 ?H ?H
?2.99 ????C 2H 5 The 3-pyridine radicals ?H ?CH 3 ?H ?H
?2.100 ????C 2H 5 The 4-pyridine radicals ?H ?CH 3 ?H ?H
2.101 ????C 2H 5 ????-CH 2-O-Ph ?H ?CH 3 ?H ?H
2.102 ????C 2H 5 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?H ?H
2.103 ????C 2H 5 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?H ?H
2.104 ?iso-C 3H 7 ????Ph ?H ?CH 3 ?H ?H
2.105 ?iso-C 3H 7 ????2Cl-Ph ?H ?CH 3 ?H ?H
2.106 ?iso-C 3H 7 ????3Cl-Ph ?H ?CH 3 ?H ?H
2.107 ?iso-C 3H 7 ????4Cl-Ph ?H ?CH 3 ?H ?H
2.108 ?iso-C 3H 7 ????2，4-Cl 2-Ph ?H ?CH 3 ?H ?H
2.109 ?iso-C 3H 7 ????3，4-Cl 2Ph ?H ?CH 3 ?H ?H
2.110 ?iso-C 3H 7 The 2-pyridine radicals ?H ?CH 3 ?H ?H
2.111 ?iso-C 3H 7 The 3-pyridine radicals ?H ?CH 3 ?H ?H
2.112 ?iso-C 3H 7 The 4-pyridine radicals ?H ?CH 3 ?H ?H
2.113 ?iso-C 3H 7 ????-CH 2-O-Ph ?H ?CH 3 ?H ?H
2.114 ?iso-C 3H 7 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?H ?H
2.115 ?iso-C 3H 7 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?H ?H
2.116 ?c-C 6H 11 ????Ph ?CH 3 ?H ?H
2.117 ?c-C 6H 11 ????2Cl-Ph ?H ?CH 3 ?H ?H
2.118 ?c-C 6H 11 ????3Cl-Ph ?H ?CH 3 ?H ?H
2.119 ?c-C 6H 11 ????4Cl-Ph ?H ?CH 3 ?H ?H
2.120 ?c-C 6H 11 ????2，4-Cl 2-Ph ?H ?CH 3 ?H ?H
2.121 ?c-C 6H 11 ????3，4-Cl 2Ph ?H ?CH 3 ?H ?H
2.122 ?c-C 6H 11 The 2-pyridine radicals ?H ?CH 3 ?H ?H
2.123 ?c-C 6H 11 The 3-pyridine radicals ?H ?CH 3 ?H ?H
2.124 ?c-C 6H 11 The 4-pyridine radicals ?H ?CH 3 ?H ?H
2.125 ?c-C 6H 11 ????-CH 2-O-Ph ?H ?CH 3 ?H ?H
2.126 ?c-C 6H 11 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?H ?H
2.127 ?c-C 6H 11 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?H ?H
2.128 ????CH 3 ????Ph ?H ?CH 3 ?CH 3 ?H
2.129 ????CH 3 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.130 ????CH 3 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.131 ????CH 3 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.132 ????CH 3 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
2.133 ????CH 3 ????3，4-Cl 2Ph ?H ?CH 3 ?CH 3 ?H
2.134 ????CH 3 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.135 ????CH 3 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.136 ????CH 3 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.137 ????CH 3 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?H
2.138 ????CH 3 ????-CH 2-O-Ph(2Cl) ?H ?CH 3 ?CH 3 ?H
2.139 ????CH 3 ????-CH 2-O-Ph(3Cl) ?H ?CH 3 ?CH 3 ?H
2.140 ????CH 3 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?H
2.141 ????CH 3 ????-CH 2-O-Ph(2F) ?H ?CH 3 ?CH 3 ?H
2.142 ????CH 3 ????-CH 2-O-Ph(3F) ?H ?CH 3 ?CH 3 ?H
2.143 ????CH 3 ????-CH 2-O-Ph(4F) ?H ?CH 3 ?CH 3 ?H
2.144 ????CH 3 ????-CH 2-O-Ph(3CF 3) ?H ?CH 3 ?CH 3 ?H
2.145 ????CH 3 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?H
2.146 ????C 2H 5 ????Ph ?H ?CH 3 ?CH 3 ?H
2.147 ????C 2H 5 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.148 ????C 2H 5 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.149 ????C 2H 5 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.150 ????C 2H 5 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
2.151 ????C 2H 5 ????3，4-Cl 2Ph ?H ?CH 3 ?CH 3 ?H
2.152 ????C 2H 5 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.153 ????C 2H 5 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.154 ????C 2H 5 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.155 ????C 2H 5 ????CH 2-O-Ph ?H ?CH 3 ?CH 3 ?H
2.156 ????C 2H 5 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?H
2.157 ????C 2H 5 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?H
2.158 ?iso-C 3H 7 ????Ph ?H ?CH 3 ?CH 3 ?H
2.159 ?iso-C 3H 7 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.160 ?iso-C 3H 7 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.161 ?iso-C 3H 7 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.162 ?iso-C 3H 7 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
2.163 ?iso-C 3H 7 ????3，4-Cl 2Ph ?H ?CH 3 ?CH 3 ?H
2.164 ?iso-C 3H 7 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.165 ?iso-C 3H 7 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.166 ?iso-C 3H 7 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.167 ?iso-C 3H 7 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?H
2.168 ?iso-C 3H 7 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?H
2.169 ?iso-C 3H 7 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?H
2.170 ?c-C 6H 11 ????Ph ?H ?CH 3 ?CH 3 ?H
2.171 ?c-C 6H 11 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.172 ?c-C 6H 11 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.173 ?c-C 6H 11 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?H
2.174 ?c-C 6H 11 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?H
2.175 ?c-C 6H 11 ????3，4-Cl 2Ph ?H ?CH 3 ?CH 3 ?H
2.176 ?c-C 6H 11 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.177 ?c-C 6H 11 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.178 ?c-C 6H 11 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?H
2.179 ?c-C 6H 11 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?H
2.180 ?c-C 6H 11 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?H
2.181 ?c-C 6H 11 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?H
2.182 ????CH 3 ????Ph ?H ?CH 3 ?CH 3 ?CH 3
2.183 ????CH 3 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
2.184 ????CH 3 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
2.185 ????CH 3 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
2.186 ????CH 3 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.187 ????CH 3 ????3，4-Cl 2Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.188 ????CH 3 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.189 ????CH 3 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.190 ????CH 3 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.191 ????CH 3 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.192 ????CH 3 ????-CH 2-O-Ph(2Cl) ?H ?CH 3 ?CH 3 ?CH 3
?2.193 ????CH 3 ????-CH 2-O-Ph(3Cl) ?H ?CH 3 ?CH 3 ?CH 3
?2.194 ????CH 3 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?CH 3
?2.195 ????CH 3 ????-CH 2-O-Ph(2F) ?H ?CH 3 ?CH 3 ?CH 3
?2.196 ????CH 3 ????-CH 2-O-Ph(3F) ?H ?CH 3 ?CH 3 ?CH 3
?2.197 ????CH 3 ????-CH 2-O-Ph(4F) ?H ?CH 3 ?CH 3 ?CH 3
?2.198 ????CH 3 ????-CH 2-O-Ph(3CF 3) ?H ?CH 3 ?CH 3 ?CH 3
?2.199 ????CH 3 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?CH 3
?2.200 ????C 2H 5 ????Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.201 ????C 2H 5 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.202 ????C 2H 5 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.203 ????C 2H 5 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.204 ????C 2H 5 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.205 ????C 2H 5 ????3，4-Cl 2Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.206 ????C 2H 5 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.207 ????C 2H 5 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.208 ????C 2H 5 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.209 ????C 2H 5 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.210 ????C 2H 5 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?CH 3
?2.211 ????C 2H 5 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?CH 3
?2.212 ?iso-C 3H 7 ????Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.213 ?iso-C 3H 7 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.214 ?iso-C 3H 7 ????3Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.215 ?iso-C 3H 7 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.216 ?iso-C 3H 7 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.217 ?iso-C 3H 7 ????3，4-Cl 2Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.218 ?iso-C 3H 7 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.219 ?iso-C 3H 7 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.220 ?iso-C 3H 7 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.221 ?iso-C 3H 7 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.222 ?iso-C 3H 7 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?CH 3
?2.223 ?iso-C 3H 7 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?CH 3
?2.224 ?c-C 6H 11 ????Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.225 ?c-C 6H 11 ????2Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.226 ?c-C 6H 11 ????3C1-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.227 ?c-C 6H 11 ????4Cl-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.228 ?c-C 6H 11 ????2，4-Cl 2-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.229 ?c-C 6H 11 ????3，4-Cl 2Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.230 ?c-C 6H 11 The 2-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.231 ?c-C 6H 11 The 3-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.232 ?c-C 6H 11 The 4-pyridine radicals ?H ?CH 3 ?CH 3 ?CH 3
?2.233 ?c-C 6H 11 ????-CH 2-O-Ph ?H ?CH 3 ?CH 3 ?CH 3
?2.234 ?c-C 6H 11 ????-CH 2-O-Ph(4Cl) ?H ?CH 3 ?CH 3 ?CH 3
?2.235 ?c-C 6H 11 ????-CH 2-O-Ph(4CF 3) ?H ?CH 3 ?CH 3 ?CH 3
?2.236 ????CH 3 ????CN ?H ?H ?H ?H
?2.237 ????CH 3 ????CO 2CH 3 ?H ?H ?H ?H
?2.238 ????CH 3 ????CN ?H ?CH 3 ?H ?H
?2.239 ????CH 3 ????CO 2CH 3 ?H ?CH 3 ?H ?H
?2.240 ????CH 3 ????CN ?H ?CH 3 ?CH 3 ?H
?2.241 ????CH 3 ????CO2CH 3 ?H ?CH 3 ?CH 3 ?H
?2.242 ????C 2H 5 ????CN ?H ?H ?H ?H
?2.243 ????C 2H 5 ????CO 2CH 3 ?H ?H ?H ?H
?2.244 ????C 2H 5 ????CN ?H ?CH 3 ?H ?H
?2.245 ????C 2H 5 ????CO 2CH 3 ?H ?CH 3 ?H ?H
?2.246 ????C 2H 5 ????CN ?H ?CH 3 ?CH 3 ?H
?2.247 ????C 2H 5 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?H
?2.248 ?i-C 3H 7 ????CN ?H ?H ?H ?H
?2.249 ?i-C 3H 7 ????CO 2CH 3 ?H ?H ?H ?H
?2.250 ?i-C 3H 7 ????CN ?H ?CH 3 ?H ?H
?2.251 ?i-C 3H 7 ????CO 2CH 3 ?H ?CH 3 ?H ?H
?2.252 ?i-C 3H 7 ????CN ?H ?CH 3 ?CH 3 ?H
?2.253 ?i-C 3H 7 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?H
?2.254 ?c-C 6H 11 ????CN ?H ?CH 3 ?CH 3 ?H
?2.255 ?c-C 6H 11 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?H
?2.256 ????CH 3 ????CN ?H ?CH 3 ?CH 3 ?CH 3
?2.257 ????CH 3 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?CH 3
?2.258 ????C 2H 5 ????CN ?H ?CH 3 ?CH 3 ?CH 3
?2.259 ????C 2H 5 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?CH 3
?2.260 ?i-C 3H 7 ????CN ?H ?CH 3 ?CH 3 ?CH 3
?2.261 ?i-C 3H 7 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?CH 3
?2.262 ?c-C 6H 11 ????CN ?H ?CH 3 ?CH 3 ?CH 3
?2.263 ?c-C 6H 11 ????CO 2CH 3 ?H ?CH 3 ?CH 3 ?CH 3
The third part typical compound of formula of of the present invention (I) shown in general formula (IV), wherein R, R 1, R 4See Table 3 with the definition of X.
Figure 9911309300201
Table 3
Numbering ????R ?X ????R 1 Rerum natura
3.1. ?CH 3 ?CH ????Ph ????Ph
3.2. ?CH 3 ?CH ????2-ClPh ????Ph
3.3. ?CH 3 ?CH ????3-ClPh ????Ph
3.4. ?CH 3 ?CH ????4-ClPh ????Ph
3.5. ?CH 3 ?CH ????2-FPh ????Ph
3.6. ?CH 3 ?CH ????3-FPh ????Ph
3.7. ?CH 3 ?CH ????4-FPh ????Ph
3.8. ?CH 3 ?CH ????2-BrPh ????Ph
3.9. ?CH 3 ?CH ????3-BrPh ????Ph
3.10. ?CH 3 ?CH ????4-BrPh ????Ph
3.11. ?CH 3 ?CH ????2-CF 3Ph ????Ph
3.12. ?CH 3 ?CH ????3-CF 3Ph ????Ph
3.13. ?CH 3 ?CH ????4-CF 3Ph ????Ph
3.14. ?CH 3 ?CH ????4-MePh ????Ph
3.15. ?CH 3 ?CH ????1-Naphthyl ????Ph
3.16. ?CH 3 ?CH ????2，4-Cl 2Ph ????Ph
3.17. ?CH 3 ?CH ????3，4-Cl 2Ph ????Ph
3.18. ?CH 3 ?CH ????3，5-Cl 2Ph ????Ph
3.19. ?CH 3 ?CH ????2-Pyridyl ????Ph
3.20. ?CH 3 ?CH ????3-Pyridyl ????Ph
3.21. ?CH 3 ?CH ????4-Pyridyl ????Ph
3.22 ?A ?CH 3 ?CH ????-CH 2-O-Ph ????Ph 145-147 ℃, isomer A
3.22 ?B ?CH 3 ?CH ????-CH 2-O-Ph ????Ph Grease, isomer B
3.23 ?CH 3 ?CH ????-CH 2-O-Ph(4Cl) ????Ph
3.24 ?CH 3 ?CH ????Ph ????4Cl-Ph
3.25 ?CH 3 ?CH ????2-ClPh ????4Cl-Ph
3.26 ?CH 3 ?CH ????3-ClPh ????4Cl-Ph
3.27 ?CH 3 ?CH ????4-ClPh ????4Cl-Ph
3.28 ?CH 3 ?CH ????2-FPh ????4Cl-Ph
3.29 ?CH 3 ?CH ????3-FPh ????4Cl-Ph
3.30 ?CH 3 ?CH ????4-FPh ????4Cl-Ph
3.31 ?CH 3 ?CH ????2-BrPh ????4Cl-Ph
3.32 ?CH 3 ?CH ????3-BrPh ????4Cl-Ph
3.33 ?CH 3 ?CH ????4-BrPh ????4Cl-Ph
3.34 ?CH 3 ?CH ????2-CF 3Ph ????4Cl-Ph
3.35 ?CH 3 ?CH ????3-CF 3Ph ????4Cl-Ph
3.36 ?CH 3 ?CH ????4-CF 3Ph ????4Cl-Ph
?3.37 ?CH 3 ?CH ????4-MePh ????4Cl-Ph
?3.38 ?CH 3 ?CH ????1-Naphthyl ????4Cl-Ph
?3.39 ?CH 3 ?CH ????2，4-Cl 2Ph ????4Cl-Ph
?3.40 ?CH 3 ?CH ????3，4-Cl 2Ph ????4Cl-Ph
?3.41 ?CH 3 ?CH ????3，5-Cl 2Ph ????4Cl-Ph
?3.42 ?CH 3 ?CH ????2-Pyridyl ????4Cl-Ph
?3.43 ?CH 3 ?CH ????3-Pyridyl ????4Cl-Ph
?3.44 ?CH 3 ?CH ????4-Pyridyl ????4Cl-Ph
?3.45 ?CH 3 ?CH ????-CH 2-O-Ph ????4Cl-Ph
?3.46 ?CH 3 ?CH ???-CH 2-O-Ph(4-Cl) ????4Cl-Ph
?3.47 ?CH 3 ?CH ????Ph ????4CF 3-Ph
?3.48 ?CH 3 ?CH ????2-ClPh ????4CF 3-Ph
?3.49 ?CH 3 ?CH ????3-ClPh ????4CF 3-Ph
?3.50 ?CH 3 ?CH ????4-ClPh ????4CF 3-Ph
?3.51 ?CH 3 ?CH ????2-FPh ????4CF 3-Ph
?3.52 ?CH 3 ?CH ????3-FPh ????4CF 3-Ph
?3.53 ?CH 3 ?CH ????4-FPh ????4CF 3-Ph
?3.54 ?CH 3 ?CH ????2-BrPh ????4CF 3-Ph
?3.55 ?CH 3 ?CH ????3-BrPh ????4CF 3-Ph
?3.56 ?CH 3 ?CH ????4-BrPh ????4CF 3-Ph
?3.57 ?CH 3 ?CH ????2-CF 3Ph ????4CF 3-Ph
?3.58 ?CH 3 ?CH ????3-CF 3Ph ????4CF 3-Ph
?3.59 ?CH 3 ?CH ????4-CF 3Ph ????4CF 3-Ph
?3.60 ?CH 3 ?CH ????4-MePh ????4CF 3-Ph
?3.61 ?CH 3 ?CH ????1-Naphthyl ????4CF 3-Ph
?3.62 ?CH 3 ?CH ????2，4-Cl 2Ph ????4CF 3-Ph
?3.63 ?CH 3 ?CH ????3，4-Cl 2Ph ????4CF 3-Ph
?3.64 ?CH 3 ?CH ????3，5-Cl 2Ph ????4CF 3-Ph
?3.65 ?C 2H 5 ?CH ????Ph ????Ph
?3.66 ?C 2H 5 ?CH ????2-ClPh ????Ph
?3.67 ?C 2H 5 ?CH ????3-ClPh ????Ph
?3.68 ?C 2H 5 ?CH ????4-ClPh ????Ph
?3.69 ?C 2H 5 ?CH ????2-FPh ????Ph
?3.70 ?C 2H 5 ?CH ????3-FPh ????Ph
?3.71 ?C 2H 5 ?CH ????4-FPh ????Ph
?3.72 ?C 2H 5 ?CH ????Ph ????4Cl-Ph
?3.73 ?C 2H 5 ?CH ????2-CF 3Ph ????4Cl-Ph
?3.74 ?C 2H 5 ?CH ????3-CF 3Ph ????4Cl-Ph
?3.75 ?C 2H 5 ?CH ????4-CF 3Ph ????4Cl-Ph
?3.76 ?C 2H 5 ?CH ????4-MePh ????4Cl-Ph
?3.77 ?C 2H 5 ?CH ????l-Naphthyl ????4Cl-Ph
?3.78 ?C 2H 5 ?CH ????2，4-Cl 2Ph ????4Cl-Ph
?3.79 ?C 2H 5 ?CH ????3，4-Cl 2Ph ????4Cl-Ph
?3.80 ?C 2H 5 ?CH ????3，5-Cl 2Ph ????4Cl-Ph
?3.81 ?C 2H 5 ?CH ????2-Pyridyl ????4Cl-Ph
?3.82 ?C 2H 5 ?CH ????3-Pyridyl ????4Cl-Ph
?3.83 ?C 2H 5 ?CH ????4-Pyridyl ????4Cl-Ph
?3.84 ?C 2H 5 ?CH ????-CH 2-O-Ph ????4Cl-Ph
?3.85 ?C 2H 5 ?CH ????-CH 2-O-Ph(4Cl) ????4Cl-Ph
?3.86 ?CH 3 ?CH ????Ph ????2-Pyridyl
?3.87 ?CH 3 ?CH ????Ph ????3-Pyridyl
?3.88 ?CH 3 ?CH ????Ph ????4-Pyridyl
?3.89 ?CH 3 ?CH ????2-Cl-Ph ????2-Pyridyl
?3.90 ?CH 3 ?CH ????3-Cl-Ph ????3-Pyridyl
?3.91 ?CH 3 ?CH ????4-Cl-Ph ????4-Pyridyl
?3.92 ?C 2H 5 ?CH ????-CH 2-O-Ph ????3-Pyridyl
?3.93 ?C 2H 5 ?CH ????-CH 2-O-Ph(4Cl) ????4-Pyridyl
?3.94 ?CH 3 ?CH ????CN ????Ph
?3.95 ?CH 3 ?CH ????CO 2CH 3 ????Ph
?3.96 ?C 2H 5 ?CH ????CN ????Ph
?3.97 ?C 2H 5 ?CH ????CO 2Cl 3 ????Ph
?3.98 ?CH 3 ?CH ????CN ????4-ClPh
?3.99 ?CH 3 ?CH ????CO 2CH 3 ????4-ClPh
3.100 ?C 2H 5 ?CH ????CN ????4-ClPh
3.101 ?C 2H 5 ?CH ????CO 2CH 3 ????4-ClPh
3.102 ?CH 3 ?N ????Ph ????Ph
3.103 ?CH 3 ?N ????2-ClPh ????Ph
3.104 ?CH 3 ?N ????3-ClPh ????Ph
3.105 ?CH 3 ?N ????4-ClPh ????Ph
3.106 ?CH 3 ?N ????2-FPh ????Ph
3.107 ?CH 3 ?N ????3-FPh ????Ph
3.108 ?CH 3 ?N ????4-FPh ????Ph
3.109 ?CH 3 ?N ????2-BrPh ????Ph
3.110 ?CH 3 ?N ????3-BrPh ????Ph
3.111 ?CH 3 ?N ????4-BrPh ????Ph
3.112 ?CH 3 ?N ????2-CF 3Ph ????Ph
3.113 ?CH 3 ?N ????3-CF 3Ph ????Ph
3.114 ?CH 3 ?N ????4-CF 3Ph ????Ph
3.115 ?CH 3 ?N ????4-MePh ????Ph
3.116 ?CH 3 ?N ????1-Naphthyl ????Ph
3.117 ?CH 3 ?N ????2，4-Cl 2Ph ????Ph
3.118 ?CH 3 ?N ????3，4-Cl 2Ph ????Ph
3.119 ?CH 3 ?N ????3，5-Cl 2Ph ????Ph
3.120 ?CH 3 ?N ????2-Pyridyl ????Ph
3.121 ?CH 3 ?N ????3-Pyridyl ????Ph
3.122 ?CH 3 ?N ????4-Pyridyl ????Ph
3.123 ?CH 3 ?N ????-CH 2-O-Ph ????Ph
3.124 ?CH 3 ?N ????-CH 2-O-Ph(4Cl) ????Ph
3.125 ?CH 3 ?N ????Ph ????4Cl-Ph
3.126 ?CH 3 ?N ????2-ClPh ????4Cl-Ph
3.127 ?CH 3 ?N ????3-ClPh ????4Cl-Ph
3.128 ?CH 3 ?N ????4-ClPh ????4Cl-Ph
3.129 ?CH 3 ?N ????2-FPh ????4Cl-Ph
3.130 ?CH 3 ?N ????3-FPh ????4Cl-Ph
3.131 ?CH 3 ?N ????4-FPh ????4Cl-Ph
3.132 ?CH 3 ?N ????2-BrPh ????4Cl-Ph
3.133 ?CH 3 ?N ????3-BrPh ????4Cl-Ph
3.134 ?CH 3 ?N ????4-BrPh ????4Cl-Ph
3.135 ?CH 3 ?N ????2-CF 3Ph ????4Cl-Ph
3.136 ?CH 3 ?N ????3-CF 3Ph ????4Cl-Ph
3.137 ?CH 3 ?N ????4-CF 3Ph ????4Cl-Ph
3.138 ?CH 3 ?N ????4-MePh ????4Cl-Ph
3.139 ?CH 3 ?N ????1-Naphthyl ????4Cl-Ph
3.140 ?CH 3 ?N ????2，4-Cl 2Ph ????4Cl-Ph
3.141 ?CH 3 ?N ????3，4-Cl 2Ph ????4Cl-Ph
3.142 ?CH 3 ?N ????3，5-Cl 2Ph ????4Cl-Ph
3.143 ?CH 3 ?N ????2-Pyridyl ????4Cl-Ph
3.144 ?CH 3 ?N ????3-Pyridyl ????4Cl-lPh
3.145 ?CH 3 ?N ????4-Pyridyl ????4Cl-Ph
3.146 ?CH 3 ?N ????-CH 2-O-ph ????4Cl-Ph
3.147 ?CH 3 ?N ????-CH 2-O-Ph(4-Cl) ????4Cl-Ph
3.148 ?CH 3 ?N ????Ph ????4CF 3-Ph
3.149 ?CH 3 ?N ????2-ClPh ????4CF 3-Ph
3.150 ?CH 3 ?N ????3-ClPh ????4CF 3-Ph
3.151 ?CH 3 ?N ????4-ClPh ????4CF 3-Ph
3.152 ?CH 3 ?N ????2-FPh ????4CF 3-Ph
3.153 ?CH 3 ?N ????3-FPh ????4CF 3-Ph
3.154 ?CH 3 ?N ????4-FPh ????4CF 3-Ph
3.155 ?CH 3 ?N ????2-BrPh ????4CF 3-Ph
3.156 ?CH 3 ?N ????3-BrPh ????4CF 3-Ph
3.157 ?CH 3 ?N ????4-BrPh ????4CF 3-Ph
3.158 ?CH 3 ?N ????2-CF 3Ph ????4CF 3-PH
3.159 ?CH 3 ?N ????3-CF 3Ph ????4CF 3-Ph
3.160 ?CH 3 ?N ????4-CF 3Ph ????4CF 3-Ph
3.161 ?CH 3 ?N ????4-MePh ????4CF 3-Ph
3.162 ?CH 3 ?N ????1-Naphthyl ????4CF 3-Ph
3.163 ?CH 3 ?N ????2，4-Cl 2Ph ????4CF 3-Ph
3.164 ?CH 3 ?N ????3，4-Cl 2Ph ????4CF 3-Ph
3.165 ?CH 3 ?N ????3，5-Cl 2Ph ????4CF 3-Ph
3.166 ?C 2H 5 ?N ????Ph ????Ph
3.167 ?C 2H 5 ?N ????2-ClPh ????Ph
3.168 ?C 2H 5 ?N ????3-ClPh ????Ph
3.169 ?C 2H 5 ?N ????4-ClPh ????Ph
3.170 ?C 2H 5 ?N ????2-FPh ????Ph
3.171 ?C 2H 5 ?N ????3-FPh ????Ph
3.172 ?C 2H 5 ?N ????4-FPh ????Ph
3.173 ?C 2H 5 ?N ????Ph ????4Cl-Ph
3.174 ?C 2H 5 ?N ????2-CF 3Ph ????4Cl-Ph
3.175 ?C 2H 5 ?N ????3-CF 3Ph ????4Cl-Ph
3.176 ?C 2H 5 ?N ????4-CF 3Ph ????4Cl-Ph
3.177 ?C 2H 5 ?N ????4-MePh ????4Cl-Ph
3.178 ?C 2H 5 ?N ????1-Naphthyl ????4Cl-Ph
3.l79 ?C 2H 5 ?N ????2，4-Cl 2Ph ????4Cl-Ph
3.180 ?C 2H 5 ?N ????3，4-Cl 2Ph ????4Cl-Ph
3.181 ?C 2H 5 ?N ????3，5-Cl 2Ph ????4Cl-Ph
3.1?82 ?C 2H 5 ?N ????2-Pyridyl ????4Cl-Ph
3.183 ?C 2H 5 ?N ????3-Pyridyl ????4Cl-Ph
3.184 ?C 2H 5 ?N ????4-Pyridyl ????4Cl-Ph
3.185 ?C 2H 5 ?N ????-CH 2-O-Ph ????4Cl-Ph
3.186 ?C 2H 5 ?N ????-CH 2-O-Ph(4Cl) ????4Cl-Ph
3.187 ?CH 3 ?N ????Ph ????2-Pyridyl
3.188 ?CH 3 ?N ????Ph ????3-Pyridyl
3.189 ?CH 3 ?N ????Ph ????4-Pyridyl
3.190 ?CH 3 ?N ????2-Cl-Ph ????2-Pyridyl
3.19l ?CH 3 ?N ????3-Cl-Phl ????3-Pyridyl
3.192 ?CH 3 ?N ????4-Cl-Phl ????4-Pyridyl
3.193 ?C 2H 5 ?N ????-CH 2-O-Ph ????3-Pyridyl
3.194 ?C 2H 5 ????-CH 2-O-Ph(4Cl) ????4-Pyridyl
3.195 ?CH 3 ?N ????CN ????Ph
3.196 ?CH 3 ?N ????CO 2CH 3 ????Ph
3.197 ?C 2H 5 ?N ????CN ????Ph
3.198 ?C 2H 5 ?N ????CO 2CH 3 ????Ph
3.199 ?CH 3 ?N ????CN ????4-ClPh
3.200 ?CH 3 ?N ????CO 2CH 3 ????4-ClPh
3.201 ?C 2H 5 ?N ????CN ????4-ClPh
3.202 ?C 2H 5 ?N ????CO 2CH 3 ????4-ClPh
To table 3, Ph represents phenyl ring at table 1.
Compound of the present invention shows the bactericidal activity of wide spectrum, can prevent and treat following disease:
The long Cercospora disease of corn and barley.
Wheat and barley powdery mildew
Wheat leaf rust and black rust, wheat glume blight
Big wheat yellow rust, leaf rust of barley
Target, potato late blight
Leaf spot of peanut
Grape powdery mildew, black rot of vine grape
Apple scab, apple mildew
Powdery mildew of cucumber, cucumber anthracnose
The fruit brown rot
Gray mold
The beans powdery mildew
Rice sheath blight disease, rice blast.
Therefore compound of the present invention can be used for the storage of cereal, can be used as bactericide and is applied to wheat, barley, paddy rice, peanut, beans, grape, fruit, nut, vegetables field and lawn.
Compound of the present invention can be used with different processing modes, as seed treatment, soil treatment or leaf surface treatment.
Compound of the present invention can be used with conventional method.For example with high power capacity hydraulic atomizing, low-gallonage spraying, utmost point low-gallonage spraying, pneumatics spraying, aerial spraying, dusting etc.Its diluted concentration depends on applied equipment, application process, pending crop and the disease of desire control.Common compound application dose of the present invention is about 0.005 to 50 kilogram of per hectare.Application dose preferably is 0.025 to 25 kilogram of a per hectare.
As seed protectant, the active matter that is wrapped in the surface of the seed is generally 0.05 to 20 kilogram in per hundred kilograms of seeds, and suitable consumption is 0.05 to 4 kilogram in per hundred kilograms of seeds, and consumption preferably is 0.1 to 1 kilogram in per hundred kilograms of seeds.Can mix with soil as processing soil treatment agent and to be in the same place, consumption is 0.02 to 20 kilogram of a per hectare usually, and suitable consumption is 0.05 to 10 kilogram of a per hectare, and consumption preferably is 0.1 to 5 kilogram of a per hectare.Be sprayed at as the blade face bactericide and be generally 0.01 to 10 kilogram of per hectare on the crop, suitable consumption is 0.02 to 5 kilogram of a per hectare, and consumption preferably is 0.25 to 1 kilogram of a per hectare.
Compound of the present invention both can use separately also can be mixed together use with other known insecticide, bactericide, weed killer herbicide, plant growth regulator or fertilizer etc.
Compound of the present invention and other known biocides are used with and can be enlarged fungicidal spectrum.Suitable bactericide comprises (but not being limited) dimethomorph, frost urea cyanogen (cymoxanil), thifluzamide (thifluzamide), furalaxyl (furalaxyl), ofurace (ofurace), M 9834 (benalaxyl), Wakil (oxadixyl), Propamocarb (propamocarb), cyprofuram (cyprofuram), fenpiclonil (fenpiclonil), fludioxonil (fludioxonil), phonetic mould amine (pyrimethanil), cyprodinil (cyprodinil), triticonazole (triticonazole), Fluquinconazole (fluquinconazole), metconazole (metconazole), volution bacterium amine (spiroxamine), ring propionamide (carpropamid), cough up bacterium ester (azoxystrobin), SSF 126 (metominostrobin), kresoxim-methyl, and trifloxystrobin.
Compound of the present invention can exist with the form of composition or preparation.Preparation preparation or composition adopt conventional method.So-called preparation is meant thinner or the solid carrier of dispersant and the mixture of liquid-carrier that active component and agrotechnique are suitable for.Carrier is meant to have emulsification, peptizaiton and diluting effect, do not damage the active component effect and soil, equipment, crop and agricultural environment are not had the composition of influence, also need add auxiliary agent such as surfactant, stabilizing agent, defoamer or antisettling agent sometimes.
So-called composition or formulation example such as the aqueous solution or aqueous dispersions, oil solution or oily dispersion liquid, paste, pulvis, wetting powder, emulsifiable concentrate, granule, attractant, aerosol etc.Wetting powder, emulsifiable concentrate, paste are prepared also dilute with water before use with high concentration.In these preparations, can contain the liquid or solid carrier and can add surfactant if necessary.When the preparation attractant, need add the composition of food or attraction insect and comprise a compound of the present invention less.
When preparation foliage spray preparation, for example wetting agent, spreader-sticker, dispersant, adhesive or thickener improve result of use to need to add auxiliary agent usually.Auxiliary agent and using method commonly used all have description in many documents.For example " washing agent and emulsifier handbook.
In composition of the present invention, the weight percentage of active component is between 0.0001 (1: 999,999)-99 (99: 1) %.For the suitable weight percentage of the convenience of transporting and preserving between 0.5 (1: 199)-90 (9: 1) %, weight percentage preferably is between 1 (1: 99)-75 (3: 1) %.The weight percentage of active component was at 0.0001 (1: 999 in the composition that is suitable for using in the field, 999)-95 between (19: 1) %, suitable weight percentage was at 0.0005 (1: 199,999)-90 between (9: 1) %, weight percentage preferably is between 0.001 (1: 99,999)-75 (3: 1) %.Composition also can compound and the ratio mode of carrier explain.For example the weight ratio between reactive compound and the carrier can change between 1: 99 (1%) to 4: 1 (80%) among the present invention, and is preferably between 1: 10 (9.1%) to 3: 1 (75%).
Be preparation emulsion, compound of the present invention can be dissolved in for example dilute with water again in acetone, methyl alcohol, ethanol, dimethyl formamide, pyridine or the dimethyl sulfoxide (DMSO) of specific solvent earlier, and its concentration can be 1% to 90% variation, and preferably is 5% to 50%.
Be the preparation emulsifiable concentrate, compound of the present invention is dissolvable in water a kind of or several mixed solvents, adds emulsifier again and strengthens the dispersion effect of compound in water.Active component is usually between 10% to 90% in the emulsifiable concentrate.Active component can reach 75% in the emulsifiable concentrate that can flow.
Be the wetting powder that preparation is suitable for spraying, compound of the present invention can with pressed powder such as clay, inorganic silicate, carbonate and wetting agent, adhesive and/or the dispersant composition mixture of porphyrize.Active component is usually between 20% to 99%, and is preferably between 45% to 75%.For example typical 50% wetting powder is 50 parts of compounds of the present invention, 45 parts of silicate and 5 parts of lignin sodium sulphate.
The preparation of pulvis is the inert solid powder by compound of the present invention and porphyrize.Suitable pressed powder such as plant powder, silicate, carbonate or clay.One easily method be with the dilution of the pressed powder of porphyrize with wetting powder.Active component is generally between 20% to 80% in the pulvis, is diluted to 1% to 10% working concentration subsequently.
In addition, can also add other compositions in compound of the present invention or the composition.But for example lubricating oil can be added in the preparation such as wet-milling: add and to improve the adhesion property of medicament on protected crop such as adhesives such as polypropylene alcohols.
Following examples describe the present invention in detail.Embodiment 1
5-(4-chlorphenyl)-2,3-dimethyl-3-(3-pyridine radicals) isoxazoline (compound 1.4,1.4A and 1.4B.See Table 1) preparation
Add 35 gram nitrous ketone (0.233 mole) and 32.3 grams in 500 milliliters of there-necked flasks to chlorostyrene (0.233 mole) and 200 milliliters of toluene, add hot reflux (110 ℃) 5 hours, thin layer chromatography (TLC) monitoring reaction (n-hexane/ethyl acetate=1: 1).Chlorostyrene disappearance afterreaction thing is chilled to room temperature.Toluene is used 300 milliliter of 10% hydrochloric acid, 100 milliliter of 10% hcl as extraction agent twice mutually, and the acid layer is used 100 milliliters of toluene wash again.With 10% sodium hydroxide acid being transferred to pH mutually is 6.Water with 200 milliliters of ethyl acetate extractions for several times.The washing of organic facies water, salt, remove behind the anhydrous sodium sulfate drying desolvate 32 gram orange, contain 3-acetylpyridine and object.
This thick product can be purified by the following step:
32 gram orange, 10 gram N-methyl hydroxylamine hydrochlorides, 20 gram sodium acetates and 100 milliliters of ethanol join in 500 milliliters of there-necked flasks stirred overnight at room temperature.Remove and to desolvate, residue is dissolved in 150 milliliters of ethyl acetate, washes with 2x100 ml water, 100 mL of saline, removes behind the anhydrous sodium sulfate drying and desolvates to such an extent that 15.6 restrain orange. 1HNMR (200MHz) analyzes and to be that title compound, the ratio of isomer A (the last higher Rf value of TLC) and isomer B are 2: 1 (on the TLC lower Rf value).
NMR ( 1H, 200MHz): compound 1.4:1.6-1.7 (2s, 3H), 2.6 (2s, 3H), 2.3-2.9 (m, 2H), 4.9-5.4 (2dd, 1H), 7.0-7.4 (m, 5H), 7.8-8.0 (2dd, 1H), 8.5-8.6 (2dd, 1H), 8.75 and 8.85 (2dd, 1H).
Get 8 gram crude mixtures and separate with column chromatography (leacheate be n-hexane/ethyl acetate=1: 1), obtain 1.2 and restrain 9: 1 A: the B isomer is transparent grease; 0.4 restrain 4: 1 A: the B isomer is transparent grease; 0.2 restrain 1: 6 A:B isomer, be white solid, mp.75 ℃-80 ℃ and 4: 5 A of 2.0 grams: the B isomer is solidliquid mixture (rate of recovery is 52.5%).
NMR ( 1H, 200MHz): 9: 1 A: the B isomer, compound 1.4A:1.6 (s, 3H), 2.6 (s, 3H), 2.5-2.9 (m, 2H), 5.2-5.4 (dd, 1H), 7.0-7.4 (m, 5H), 7.8-7.9 (d, 1H), 8.5 (d, 1H), 8.75 (d, 1H).
NMR ( 1H, 200MHz): 1: 5 A: the B isomer, compound 1.4B:1.55 (s, 3H), 2.6 (s, 3H), 2.3-2.9 (m, 2H), 4.85-5.0 (t, 1H), 7.0-7.4 (m, 5H), 7.9-8.0 (d, 1H), 8.6 (dd, 1H), 8.75 (d, 1H).Synthetic nitrous ketone: 3-pyridine radicals-N-methyl-ethyleneimine nitrogen oxide
80 gram 3-acetylpyridine (0.661 mole), 84 gram N-methyl hydroxylamine hydrochlorides (1.108 moles) and 164.8 gram sodium acetates (2.01 moles) join in 450 milliliters of absolute ethyl alcohols, stir under the room temperature and spend the night.The TLC monitoring reaction carries out.Treat raw material 3-acetylpyridine complete obiteration and after a dot generation is arranged at the bottom, steam 400 milliliters of carrene of adding in residue except that ethanol.Remove by filter insoluble matter, filtrate concentrates to such an extent that light yellow oil 94 restrains yield 95% behind anhydrous sodium sulfate drying.Embodiment 2
5-Phenoxymethyl-3-phenyl-3-(3-pyridine radicals)-2-methyl isoxazoline (compound 3.22A and 3.22B see Table 3)
Add 2.1 gram (10 mM) 3-pyridine radicals-N-methyl-benzyl imines nitrogen oxide and 25 milliliters of toluene in 300 milliliters of there-necked flasks, add 4.0 gram phenyl allyl ether (30 mM) and 25 milliliters of toluene again, add hot reflux (110 ℃) 1 day, add following starting material again: 1.05 gram (5 mM) nitrogen oxide, 2.0 gram ethers (15 mM).Add hot reflux (110 ℃) 6 days, 50 ℃ of following concentration of reaction solution provide 6.6 gram solids.N-hexane/ethyl acetate is washed, filter 1.8 the gram isomer A (the last higher Rf of TLC (0.59) value, n-hexane/ethyl acetate=1: 1), mp.145 ℃-147 ℃.
NMR ( 1H, 200MHz): compound 3.22A:2.5 (s, 3H), 3.0 (s, 1H), 3.3 (s, 1H), 3.7-4.1 (m, 2H), 4.65 (s, 1H), 6.8-7.4 (m, 11H), 7.85 (d, 1H), 8.5 (dd, 1H), 8.65 (d, 1H).
After filtrate concentrates 4.5 grams, separate with column chromatography (leacheate be n-hexane/ethyl acetate=1: 1), obtain 0.7 and restrain isomer B (Rf=0.59, n-hexane/ethyl acetate=1: 1), be yellow oil.
NMR ( 1H, 200MHz): compound 3.22B:2.5 (s, 3H), 3.1 (s, 1H), 4.1 (s, 1H), 6.85-7.4 (m, 11H), 7.9 (s, 1H), 8.5 (dd, 1H), 8.65 (d, 1H).
Synthetic 3-pyridine radicals-N-methyl-benzyl imines nitrogen oxide
Add 9.15 gram 3-benzoyl pyridine (0.050 mole) and 50 milliliters of absolute ethanol in 300 milliliters of there-necked flasks, 5.0 gram N-methyl hydroxylamine hydrochlorides (0.060 mole) and 9.84 gram sodium acetates (0.12 mole).Stirred 88 hours under the room temperature, add hot reflux (78 ℃) 20 hours.Potash transfers to pH=8, removes by filter insoluble matter, filtrate concentrate orange/yellow solid.Wash residue with carrene, remove by filter insoluble matter, filtrate concentrates to such an extent that light yellow oil 11.3 restrains orange/yellow solid behind anhydrous magnesium sulfate drying, and it is 60% product and 40% starting ketone that GC analyzes.Wash orange/yellow solid with ethyl acetate, filter and collect to such an extent that white solid 2.4 restrains mp.143 ℃-146 ℃.Filtrate concentrates to such an extent that second batch of solid 1.5 restrains, and is total to such an extent that product 3.9 restrains yield 36.8%.
NMR( 1H，200MHz)：3.8(s，3H)，7.2-7.6(m，6H)，8.6(d，1H)，8.8(dd，1H)，8.9(d，1H)。Embodiment 3
Provided in the table 4 representative compound in table 1, the table 2 nuclear magnetic resoance spectrum ( 1H, 200MHz) data.Table 4
Compound number NMR data (chemical shift, interior mark TMS)
1.4A ?1.6(s,3H),2.6(s,3H),2.5-2.9(m,2H),5.2-5.4(dd,1H),7.0-7.4(m,5H), ?7.8-7.9(d,1H),8.5(d,1H),8.75(d,1H)
1.4 ?1.6-1.7(2s,3H),2.6(2s,3H),2.3-2.9(m,2H),4.9-5.4(2dd,1H), ?7.0-7.4(m,5H),7.8-8.0(2dd,1H),8.5-8.6(2dd,1H),8.75,8.85(2dd,1H)
1.4B ?1.55(s,3H),2.6(s,3H),2.3-2.9(m,2H),4.85-5.0(t,1H), ?7.0-7.4(m,5H),7.9-8.0(d,1H),8.6(d,1H),8.85(d,1H).
3.22A ?2.5(s,3H);3.0(s,1H);3.3(s,1H);3.7-4.1(m,2H);4.65(s,1H); ?6.8-7.4(m,11H);7.85(d,1H);8.5(dd,1H);8.65(d,1H).
3.22B ?2.5(s,3H);3.1(s,2H);4.1(s,2H);4.4(s,1H);6.85-7.4(m,11H); ?7.9(s,1H);8.5(dd,1H);8.65(d,1H).
1.6 ?1.6(s,3H),2.6(d,3H),2.6-2.9(m,2H),5.2-5.3(dd,1H), ?6.9-7.4(m,5H),7.9(dd,1H),8.5(d,1H),8.8(d,1H).
1.23A ?1.6(s,3H),2.2(d,6H),2.6(d,3H),2.3-2.9(m,2H),5.5(dd,1H), ?6.9-7.5(m,4H),7.8(dd,1H),8.5(d,1H),8.85(s,1H).
1.23 ?1.6(2s,3H),2.2(d,6H),2.6(d,3H),2.3-2.9(m,2H),5.2-5.4(2m,1H), ?6.9-7.5(m,4H),7.8-7.9(2m,1H),8.4-8.5(2d,1H),8.7-8.9(2s,1H).
1.2 ?1.5-1.6(2s,3H),2.6(br.s,3H),2.3-2.9(m,2H),5.25-5.3,5.4-5.5(br.m,dd,1H), ?7.0-7.4(m,4H),7.7-7.8(2d,1H),8.4-8.5(2d,1H),8.7-8.9(2s,1H).
1.3 ?1.5-1.6(2s,3H),2.6(br.s,3H),2.3-2.9(m,2H),5.0-5.1,5.2-5.3(br.m,dd,1H), ?7.0-7.4(m,5H),7.8-7.9(2d,1H),8.4-8.5(2d,1H),8.7-8.85(2s,1H).
1.7 ?1.59-1.60(2s,3H),2.63(br.s,3H),2.3-2.9(m,2H),5.0-5.1,5.2-5.3(br.m,dd, ?1H),6.9-7.4(m,5H),7.8-8.0(2d,1H),8.5-8.6(2d,1H),8.74-8.85(2s,1H).
1.1 ?1.60-1.62(2s,3H),2.62,2.65(2s,3H),2.3-2.9(m,2H),5.0-5.1,5.2-5.3 ?(brm,dd,1H),7.1-7.4(m,6H),7.85-8.0(2d,1H),8.5-8.6(2d,1H), ?8.74-8.85(2s,1H).
1.5 ?1.56-1.62(2s,3H),2.62,2.65(2s,3H),2.3-2.9(2dd,2H),5.0-5.1,5.2-5.3 ?(brm,dd,1H),6.9-7.65(m,5H),7.85-7.95(2d,1H),8.45-8.55(2d,1H), ?8.7-8.85(2s,1H).
1.15 ?1.60-1.62(2s,3H),2.09,2.17(2s,3H),2.64-2.67(br.d,3H),2.3-2.9(2dd,2H), ?5.0-5.1,5.2-5.3(br.m,dd,1H),6.9-7.35(m,5H),7.85-7.95(2d,1H), ?8.5-8.55(2d,1H),8.7-8.85(2s,1H).
1.10 ?1.57-1.60(2s,3H),2.61-2.63(2s,3H),2.3-2.9(2dd,2H),4.9-5.1,5.2-5.3 ?(brm,dd,1H),7.1-7.65(m,5H),7.85-7.95(2d,1H),8.58.55(2d,1H), ?8.72-8.8(2s,1H).
1.13 ?1.57-1.62(2s,3H),2.61-2.63(2s,3H),2.3-2.9(2dd,2H),5.0-5.1,5.2-5.3 ?(brm,dd,1H),7.3-7.65(m,5H),7.85-7.95(2d,1H),8.5-8.55(2d,1H), ?8.7-8.8(2s,1H).
?1.9 ?1.58-1.62(2s,3H),2.6-2.63(2s,3H),2.3-2.9(2dd,2H),5.0-5.1,5.2-5.3 ?(brm,dd,1H),7.1-7.5(m,5H),7.85-7.95(2d,1H),8.5-8.55(2d,1H), ?8.7-8.8(2s,1H).
1.39 ?1.23-1.30(m,6H,NCH 2CH 3,C-3CH 3),2.2-2.6(m,2H),2.7-3.0(m,2H, ?NCH 2CH 3),5.0-5.1,5.2-5.3(br.m,dd,1H),7.1-7.5(m,5H), ?7.85-7.95(2d,1H),8.5-8.6(2d,1H),8.7-8.8(2s,1H).
1.51 ?1.23-1.30(m,9H),2.2-2.6(m,2H),2.9-3.0(m,1H),5.0-5.1,5.2-5.3 ?(br.m,dd,1H),7.1-7.5(m,4H),7.8-8.0(4d,1H),8.5-8.6(2d,1H), ?8.7-8.8(2s,1H).
1.63 ?1.1-1.9(m,13H),2.1-2.6(2dd,2H),2.7-2.9(m,1H),4.9-5.0,5.1-5.2 ?(br..m,m,1H),7.2-7.5(m,5H),7.85-7.95(2d,1H),8.6(d,1H),8.9(s,1H).
Solvent is deuterochloroform.Each alphabetical implication in the nuclear magnetic resoance spectrum data:
S: unimodal d: bimodal t: triplet m: multiplet br: broad peak
Embodiment 4
Chemical compound lot among the present invention has been carried out the bactericidal activity test.Method is as follows: testing compound is dissolved in 1: 1 acetone and carbinol mixture or N, in the dinethylformamide, again with 2: 1: 1 water, acetone and carbinol mixture (volume ratio) be diluted to desired concn.This solution is sprayed onto to be treated to dry on the measuring plants 2 hours, carried out the germ inoculation then.Make blank with used solvent.In the protection activity test, chemicals treatment is carried out the germ inoculation after 1 day.To provide compound activity to various germs under 300 gram/hectare dosage below.Activity in percentage, is controlled to be 100% with respect to blank fully, and invalid fully is 0%.
Active classification: A:90-100%B:70-89%C:50-9%D:＜50%.
Wheat glume blight
Dispenser was inoculated after one day.Spore concentration is 3.0 * 10 6/ ml.The examination material is placed in climatic cabinate and is moved into 2 days " Invest, Then Investigate "s in the greenhouse after 7 days.
Wheat powdery mildew
Dispenser was inoculated after one day.7 days " Invest, Then Investigate "s are placed in the inoculation back in the greenhouse.
Powdery mildew of cucumber
Dispenser was inoculated after one day.Spore concentration is 1.0 * 10 6/ ml.7 days " Invest, Then Investigate "s are placed in the inoculation back in the greenhouse.
Rice blast
Dispenser was inoculated after one day.Spore concentration is 5.0 * 10 5/ ml.Preserving moisture in humidistat and be beneficial to infect in 36 hours in the inoculation back, moves into the greenhouse, 7 days " Invest, Then Investigate "s.
Gray mold of cucumber
Dispenser was inoculated after one day.The examination material is placed 4 days " Invest, Then Investigate "s in climatic cabinate.
Cucumber downy mildew
Dispenser was inoculated after one day.The examination material is placed 5 days " Invest, Then Investigate "s in climatic cabinate.
Under 300 gram/hectare dosage, wheat glume blight compound 1.7 has been shown B level activity.
To wheat powdery mildew compound 1.4A, 1.10,1.51 have shown A level activity under 300 gram/hectare dosage.Compound 1.7,1.13,1.63 have shown B level activity.
Under 300 gram/hectare dosage, powdery mildew of cucumber compound 1.4 has been shown A level activity.Compound 1.23 has shown B level activity.
Under 300 gram/hectare dosage, rice blast compound 1.4,1.10,1.39,1.51 has been shown A level activity.
To gray mold of cucumber compound 1.4A, 1.9,1.10 have shown A level activity under 300 gram/hectare dosage.Compound 1.13,1.39,1.51 have shown B level activity.
To cucumber downy mildew compound 1.4A, 1.15,1.51 have shown A level activity under 300 gram/hectare dosage.

Claims (9)

1, as the heterocyclic substituted De isoxazoline compounds of bactericide, it is characterized in that: the present invention has the compound of general formula (I):
Figure 9911309300021
X is N or CH in the formula;
R is (C 1-C 12) alkyl, halogen (C 1-C 12) alkyl, (C 2-C 8) thiazolinyl, halogen (C 2-C 8) thiazolinyl, (C 2-C 8) alkynyl, halogen (C 2-C 8) alkynyl, (C 1-C 12) alcoxyl (C 1-C 12) alkyl, (C 3-C 7) cycloalkyl, halogen (C 3-C 7) cycloalkyl, (C 3-C 7) cycloalkyl (C 1-C 4) alkyl, aryl alkyl, aryloxy group (C 1-C 4) alkyl, heterocyclic radical;
R 1Be aryl, heterocyclic radical or C (R 6R 7R 8);
R 2And R 3Each is hydrogen, (C naturally 1-C 12) alkyl, halogen (C 1-C 12) alkyl, (C 1-C 12) alkoxyl, halogen (C 1-C 12) alkoxyl, (C 3-C 7) cycloalkyl, (C 3-C 7) cycloalkyl (C 1-C 4) alkyl, aryl, aryl alkyl, heterocyclic radical; Cyano group or (C 1-C 4) alkoxy carbonyl;
R 4And R 5Each is hydrogen, (C naturally 1-C 12) alkyl, halogen (C 1-C 12) alkyl, (C 2-C 8) thiazolinyl, halogen (C 2-C 8) thiazolinyl, (C 2-C 8) alkynyl, halogen (C 2-C 8) alkynyl, (C 3-C 7) cycloalkyl, halogen (C 3-C 7) cycloalkyl, (C 3-C 7) cycloalkyl (C 1-C 4) alkyl, aryl, aryloxy group (C 1-C 4) alkyl, aryl alkyl, heterocyclic radical, cyano group or (C 1-C 4) alkoxy carbonyl; But R 4And R 5Be not hydrogen simultaneously;
R 6, R 7And R 8Each is hydrogen, (C naturally 1-C 12) alkyl, (C 2-C 8) thiazolinyl, (C 2-C 8) alkynyl, (C 1-G 12) alcoxyl (C 1-C 12) alkyl, (C 3-C 7) cycloalkyl, (C 3-C 7) cycloalkyl (C 1-C 4) alkyl, aryl, aralkyl, heterocycle (C 1-C 4) alkyl;
And enantiomer, stereoisomer and agricultural go up acceptable salt.
2, according to the described compound of claim 1, it is characterized in that: wherein R is (C 1-C 12) alkyl or halogen (C 1-C 12) alkyl; R 1Be aryl or C (R 6R 7R 8); R 4Be the phenyl of trihalomethyl replacement or the phenyl of halogen replacement.
3, according to the described compound of claim 2, it is characterized in that; Wherein R is (C 1-C 4) alkyl; R 1Be phenyl or the C (R that phenyl, halogen replace 6R 7R 8); R 4Be 2-chlorphenyl, 2-fluorophenyl, 2-trifluoromethyl, 3-chlorphenyl, 3-fluorophenyl, 3-trifluoromethyl, 4-chlorphenyl, 4-fluorophenyl, 4-trifluoromethyl or 2,4 dichloro benzene base.
4, according to the described compound of claim 2, it is characterized in that; Wherein R is (C 1-C 4) alkyl; R 4Be 2-chlorphenyl, 2-fluorophenyl, 2-trifluoromethyl, 3-chlorphenyl, 3-fluorophenyl, 3-trifluoromethyl, 4-chlorphenyl, 4-fluorophenyl, 4-trifluoromethyl or 2,4 dichloro benzene base; R 6, R 7And R 8Be respectively hydrogen or (C 1-C 4) alkyl.
5, according to the described compound of claim 3, it is characterized in that: wherein R is a methyl; R 1Be phenyl, 2-chlorphenyl, 3-chlorphenyl, 4-chlorphenyl; R 4Be 4-chlorphenyl, 4-fluorophenyl, 4-trifluoromethyl or 2,4 dichloro benzene base.
6, according to the described compound of claim 4, it is characterized in that: wherein R is a methyl; R 4Be 4-chlorphenyl, 4-fluorophenyl, 4-trifluoromethyl or 2,4 dichloro benzene base; R 6, R 7And R 8Be hydrogen.
7, according to the described compound of claim 5, it is characterized in that: R wherein 1Be phenyl or 4-chlorphenyl; R 4Be 4-chlorphenyl or 4-fluorophenyl.
8, according to the described compound of claim 6, it is characterized in that: R 4Be the 4-chlorphenyl, this compound is 5-(4-chlorphenyl)-2,3-dimethyl-3-(3-pyridine radicals) isoxazoline.
9, a kind of bactericidal composition that is used for the controlling plant disease is characterized in that: the compound and the agricultural that wherein contain in the claim 1 go up the carrier that is fit to, and the ratio among the present invention between reactive compound and the carrier can change between 1: 99 to 4: 1.10, compound of the present invention can be used for preventing and treating the disease in wheat, barley, paddy rice, peanut, beans, fruit, nut, vegetables field and the lawn, be specially adapted to prevent and treat wheat glume blight, powdery mildew, powdery mildew of cucumber, gray mold, downy mildew, rice blast; Application method is the difference according to crop and disease, adopts foliar spray, seed treatment, agent, soil treatment method.
CN99113093A 1999-07-14 1999-07-14 Heterocycle substituted isoxazoline compounds used as disinfectant Expired - Lifetime CN1091444C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN99113093A CN1091444C (en) 1999-07-14 1999-07-14 Heterocycle substituted isoxazoline compounds used as disinfectant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN99113093A CN1091444C (en) 1999-07-14 1999-07-14 Heterocycle substituted isoxazoline compounds used as disinfectant

Publications (2)

Publication Number Publication Date
CN1280767A true CN1280767A (en) 2001-01-24
CN1091444C CN1091444C (en) 2002-09-25

Family

ID=5276325

Family Applications (1)

Application Number Title Priority Date Filing Date
CN99113093A Expired - Lifetime CN1091444C (en) 1999-07-14 1999-07-14 Heterocycle substituted isoxazoline compounds used as disinfectant

Country Status (1)

Country Link
CN (1) CN1091444C (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100389110C (en) * 2005-04-15 2008-05-21 沈阳化工研究院 Process of preparing aromatic ring substituted ixooxazoline compound
US8124565B2 (en) 2006-02-09 2012-02-28 Syngenta Crop Protection, Inc. Method of protecting a plant propagation material, a plant, and/or plant organs
CN103314955A (en) * 2013-07-17 2013-09-25 中国中化股份有限公司 Water emulsion composition containing SYP-Z048 bactericide
CN104798791A (en) * 2015-05-13 2015-07-29 深圳诺普信农化股份有限公司 Sterilization composition containing isopyrazam and application of sterilization composition
CN104817549A (en) * 2015-04-16 2015-08-05 河南师范大学 Oxazole compound with anti-fungal activity, preparation method of oxazole compound and application of oxazole compound
CN104823985A (en) * 2015-05-07 2015-08-12 深圳诺普信农化股份有限公司 Bactericidal composition containing SYP-Z048 and applications thereof
CN105061304A (en) * 2015-06-05 2015-11-18 沈阳科创化学品有限公司 Method for preparing isoxazoline compound and intermediate thereof
CN105085502A (en) * 2015-06-05 2015-11-25 沈阳科创化学品有限公司 Compound with high biological activity, preparation method therefore and pesticide composition
CN105815324A (en) * 2015-01-09 2016-08-03 中化农化有限公司 Bactericidal composition containing SYP-Z048 and JS399-19
CN111848597A (en) * 2019-04-28 2020-10-30 沈阳科创化学品有限公司 Isoxazoline compound isomer and preparation method thereof
CN114685471A (en) * 2020-12-31 2022-07-01 沈阳科创化学品有限公司 Preparation method of isoxazoline compound

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1540580A (en) * 1975-09-02 1979-02-14 Shell Int Research Fungicidal isoxazolidines
US4239889A (en) * 1978-06-27 1980-12-16 Shell Oil Company 3-(N-Heterocyclyl)isoxazolidine fungicides

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100389110C (en) * 2005-04-15 2008-05-21 沈阳化工研究院 Process of preparing aromatic ring substituted ixooxazoline compound
US8124565B2 (en) 2006-02-09 2012-02-28 Syngenta Crop Protection, Inc. Method of protecting a plant propagation material, a plant, and/or plant organs
CN103314955A (en) * 2013-07-17 2013-09-25 中国中化股份有限公司 Water emulsion composition containing SYP-Z048 bactericide
CN103314955B (en) * 2013-07-17 2015-06-17 中国中化股份有限公司 Water emulsion composition containing SYP-Z048 bactericide
CN105815324A (en) * 2015-01-09 2016-08-03 中化农化有限公司 Bactericidal composition containing SYP-Z048 and JS399-19
CN105815324B (en) * 2015-01-09 2018-08-21 中化农化有限公司 Bactericidal composition containing oxazole and 2-cyano-3-amino-3-phenylancryic acetate
CN104817549A (en) * 2015-04-16 2015-08-05 河南师范大学 Oxazole compound with anti-fungal activity, preparation method of oxazole compound and application of oxazole compound
CN104817549B (en) * 2015-04-16 2017-08-11 河南师范大学 Evil azole compounds with antifungal activity and its preparation method and application
CN104823985A (en) * 2015-05-07 2015-08-12 深圳诺普信农化股份有限公司 Bactericidal composition containing SYP-Z048 and applications thereof
CN104823985B (en) * 2015-05-07 2016-07-06 深圳诺普信农化股份有限公司 A kind of bactericidal composition containing pyridine bacterium azoles and application thereof
CN104798791A (en) * 2015-05-13 2015-07-29 深圳诺普信农化股份有限公司 Sterilization composition containing isopyrazam and application of sterilization composition
CN105085502A (en) * 2015-06-05 2015-11-25 沈阳科创化学品有限公司 Compound with high biological activity, preparation method therefore and pesticide composition
CN105061304A (en) * 2015-06-05 2015-11-18 沈阳科创化学品有限公司 Method for preparing isoxazoline compound and intermediate thereof
CN111848597A (en) * 2019-04-28 2020-10-30 沈阳科创化学品有限公司 Isoxazoline compound isomer and preparation method thereof
WO2020220925A1 (en) * 2019-04-28 2020-11-05 沈阳科创化学品有限公司 Isoxazoline compound isomer and preparation method therefor
CN114685471A (en) * 2020-12-31 2022-07-01 沈阳科创化学品有限公司 Preparation method of isoxazoline compound
CN114685471B (en) * 2020-12-31 2024-02-06 沈阳科创化学品有限公司 Preparation method of isoxazoline compound

Also Published As

Publication number Publication date
CN1091444C (en) 2002-09-25

Similar Documents

Publication Publication Date Title
RU2319697C2 (en) Difluoromethylthiazolyl carboxanilides
EP1035122B1 (en) Heterocyclic subsituted isoxazolidines and their use as fungicides
DK169161B1 (en) Microbicidal agents containing 3- (2,2-difluorobenzodioxol-4-yl) -4-cyanopyrrole derivatives, process for their preparation, process for controlling or preventing attacks on culture plants by phytopathogenic microorganisms, and using the 4-cyanopyrrole derivatives for control and / or preventive prevention of microorganism infestations on vegetable or stockpile products
EP1852428B1 (en) 4-cyclopropyl-1,2,3-thiadiazole compound, agrohorticultural plant disease controlling agent and method of using the same
EP0694529A1 (en) Aromatic compounds
CN1091444C (en) Heterocycle substituted isoxazoline compounds used as disinfectant
CN1121399C (en) Isothiazolcarboxylic acid derivatives
CZ289778B6 (en) Amides of N-sulfonyl- and N-sulfinylamino acids, process of their preparation, microbicidal preparations in which the amides are comprised and use thereof
BRPI0620079A2 (en) aromatic heterocyclic compounds substituted as fungicides
WO1996005170A1 (en) 4-trifluoromethylbenzamides and their use as pesticides in plant and materials protection
CN1197373A (en) Compsns. of control harmful fungus, and its method
JPS5978162A (en) Bactericidal composition containing ethene derivatives
CN1306506A (en) Phenyl-methoxyimino-acetic acid derivatives as pesticides
JP2022517031A (en) 3-substituted phenylamidine compound, its manufacture and use
CN1356988A (en) Phenoxy fluoropyrimidines
EA001313B1 (en) Pesticides
OA10106A (en) (Hetero) -aryl-alkyl-cetoxim-o-ethers substituted insecticidal acaricides and nematocides process for their preparation agents containing them and their use as pest control agents
CN1856249A (en) Pyridyl pyrimidines for use as pesticides
CN1662489A (en) N-sulphonylaminoacetonitriles having pesticidal properties
CN1226242A (en) Dihydrofuran carboxamides
CN1310926C (en) Phthali acid diamide, method for prodn. thereof and use of same as pesticide
JPH0215049A (en) Sterilizable compound, its production and sterilizing composition containing the same
JPS63185958A (en) Acrylic acid derivative compound, manufacture and bactericidal composition
EP0172031B1 (en) Novel sulfenylated acylhydrazones, compositions containing them, methods of making them and their use
JPH0331277A (en) Microbial extermination compound

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
ASS Succession or assignment of patent right

Owner name: CHINA PETROCHEMICAL CORPORATION; SHENYANG CHEMICA

Free format text: FORMER OWNER: SHENYANG CHEMICAL ENGINEERING INST.

Effective date: 20080718

C41 Transfer of patent application or patent right or utility model
TR01 Transfer of patent right

Effective date of registration: 20080718

Address after: F6 - F12 layer, middle block of Kai Chen World Trade Centre, 28 Fuxing Man Street, Xicheng District, Beijing, zip code: 100031

Co-patentee after: Shenyang Research Institute of Chemical Industry

Patentee after: Sinopec Group

Address before: No eight, Shen Liaodong Road, Tiexi District, Liaoning, Shenyang: 110021

Patentee before: Shenyang Research Institute of Chemical Industry

ASS Succession or assignment of patent right

Owner name: CHINA CHEMISTRY CO., LTD.

Free format text: FORMER OWNER: SINOCHEM CORPORATION

Effective date: 20091120

C41 Transfer of patent application or patent right or utility model
C56 Change in the name or address of the patentee
CP03 Change of name, title or address

Address after: F6 - F12 layer, middle block of Kai Chen World Trade Centre, 28 Fuxing Man Street, Xicheng District, Beijing, zip code: 100031

Co-patentee after: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd.

Patentee after: Sinochem Corp.

Address before: F6 - F12 layer, middle block of Kai Chen World Trade Centre, 28 Fuxing Man Street, Xicheng District, Beijing, zip code: 100031

Co-patentee before: Shenyang Research Institute of Chemical Industry

Patentee before: Sinochem Corp.

TR01 Transfer of patent right

Effective date of registration: 20091120

Address after: 28, Fuxing Man Street, Xicheng District, Beijing, zip code: 100031

Co-patentee after: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd.

Patentee after: SINOCHEM Corp.

Address before: F6 - F12 layer, middle block of Kai Chen World Trade Centre, 28 Fuxing Man Street, Xicheng District, Beijing, zip code: 100031

Co-patentee before: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd.

Patentee before: Sinochem Corp.

C41 Transfer of patent application or patent right or utility model
TR01 Transfer of patent right

Effective date of registration: 20160121

Address after: 110021 Liaodong Road, Tiexi District, Liaoning, No. 8-1, No.

Patentee after: SHENYANG SINOCHEM AGROCHEMICALS R&D Co.,Ltd.

Address before: 100031 Beijing, Xicheng District, the door of the revitalization of the main street, No. 28

Patentee before: SINOCHEM Corp.

Patentee before: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd.

CX01 Expiry of patent term

Granted publication date: 20020925

CX01 Expiry of patent term