CN101628881B - Substituted cyanoacetate compound and application thereof - Google Patents

Substituted cyanoacetate compound and application thereof Download PDF

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CN101628881B
CN101628881B CN2008101167622A CN200810116762A CN101628881B CN 101628881 B CN101628881 B CN 101628881B CN 2008101167622 A CN2008101167622 A CN 2008101167622A CN 200810116762 A CN200810116762 A CN 200810116762A CN 101628881 B CN101628881 B CN 101628881B
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trifluoromethyl
base
phenyl
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methyl
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CN101628881A (en
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刘长令
李洋
张弘
周银平
王军锋
刘远雄
罗艳梅
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Research Institute of Chemical Industry Co Ltd
Sinochem Corp
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Abstract

The invention relates to a substituted cyanoacetate compound as shown in the general formula (I). In the general formula (I), all groups are defined as in the specification. The compound and the composition thereof can be used for preventing and controlling harmful mites and eggs of the harmful mites, and also can be used for preventing and controlling pests.

Description

Substituted cyanoacetate compound and application thereof
Technical field:
The invention belongs to agricultural insecticidal, miticide field; Comprise that one type of new substituted cyanoacetate compound is used for agricultural and goes up control arthropod (insect and mite); And the purposes of worm (comprising nematode), specifically kind of cyanic acetate compounds and application thereof.
Background technology
Because the agrochemicals of a new generation must satisfy many-sided demand; For example relate to application dose, drug effect phase, activity profile, Application Areas, toxicity, with the combination of other active substance, with processing aid combine or synthetic and because resistance that possibly occur or the like; And existing chemistry of pesticide article can not be all satisfactory in all Application Areass, and therefore the exploitation to novel pesticide never finishes.People exist higher demand to new compound, and performance at least in some aspects is better than known compound.
The acyl group cyanide compound that contains phenyl ring with acaricidal activity is disclosed in the prior art.For example U.S. Pat 200320808 discloses the compound of following general formula (II):
Figure G200810116762201D00011
Japanese Patent JP2003286265, the disclosed general formula of JP2004115399 (III) compound is that the part of the B in the above-mentioned general formula (II) is become pyrazolyl by phenyl ring, structure is following:
Figure G200810116762201D00012
Still keeping A partly to be the common structure characteristic of phenyl ring on this two compounds structure.The B ring portion is divided into phenyl ring and pyrazoles ring.
In recent years, some acarids are for having used miticide for many years to produce resistance, and this is difficult to prevent and kill off them with traditional miticide with regard to making.Therefore, need develop the novel miticide that to prevent and kill off acarid admirably.
Summary of the invention
One of the object of the invention provides a kind of even when lower concentration uses, also can demonstrate the cyanoacetate compound that good acarid is prevented and kill off effect.Another object of the present invention provides one type of cyanoacetate compound control arthropod, and the purposes of worm.The object of the invention also comprises provides a kind of to long novel pesticide of mite class lasting period and provide a kind of mite class that traditional miticide is produced resistance still to have the novel pesticide of excellent activity.
These purposes can possess simultaneously or part possesses.
Technical scheme of the present invention is following:
A kind of cyanoacetate compound, shown in general formula (I):
In the formula:
R 1Be selected from C 1-C 6Alkyl, C 1-C 6Haloalkyl, the substituted C of phenyl 1-C 6Alkyl, C 2-C 6Thiazolinyl, C 2-C 6Haloalkenyl group, C 2-C 6Alkynyl, C 2-C 6Halo alkynyl, C 3-C 7Naphthenic base, C 3-C 7Halogenated cycloalkyl, vinyl halides base
Figure G200810116762201D00022
C 3-C 7Naphthenic base, R 6Or R 7
R 2Be selected from R 8Or R 9
R 3, R 4, R 5Independently be selected from CN, halogen or R separately 17
R 6Be selected from not replacement or substituted phenyl, described substituting group is selected from 1-5 following radicals: halogen, C 1-C 6-alkyl, C 1-C 6Haloalkyl, C 1-C 6Alkoxyl group, C 1-C 6Halogenated alkoxy, CN, NO 2, SO nR 17, COR 17, COOR 17, CONR 17R 18, SO 2NR 17R 18Or OR 17
R 7Be selected from not replacement or substituted fragrant heterocyclic radical, described substituting group is selected from one or more following radicals: halogen, C 1-C 6Alkyl, C 1-C 6Haloalkyl, C 1-C 6Alkoxyl group, C 1-C 6Halogenated alkoxy, CN, NO 2, SO nR 16, COR 16, COOR 17, CONR 17R 18, SO 2NR 17R 18, OR 17Or halogenophenyl; Described fragrant heterocyclic radical is selected from pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl group 、 oxazolyl 、 isoxazolyl, furyl, pyrryl, pyrazolyl, imidazolyl, triazolyl or 1,4-oxygen thiapyran;
R 8Be selected from R 6, R 7, R 10, R 11, R 12Or R 13
R 9Be selected from CHR 14R 15
R 10Be selected from and have the substituted R of following groups 16: R 6Or R 7
R 11Be selected from and have the substituted R of following groups 16: XR 6Or XR 7
R 12Be selected from and have the substituted R of following groups 16: COOR 6, COOR 7, CONR 6R 12, CONR 7R 17, SO 2NR 6R 17, SO 2NR 7R 17, NHSO 2R 6Or NHSO 2R 7
R 13Be selected from:
Figure G200810116762201D00023
R 14Be selected from CN or R 17
R 15Be selected from CN, COOR 17, CONR 17R 18, CH 2CH 2OCH 3, nonaromatic heterocycles base or by the substituted C of following groups 1-C 6Alkyl: CN, COOR 17, CONR 17R 18, NR 17R 18, R 19, OCH 2CN, OCH 2COOR 16, OCH 2CONR 17R 18, OCH 2CF 3, C 3-C 6Cycloalkyl oxy, C 3-C 6Cycloalkenyl oxy, C 3-C 6Nonaromatic heterocycles alkyl oxy, C 3-C 6Nonaromatic heterocycles thiazolinyl oxygen base, C 3-C 6Naphthenic base sulfenyl, C 3-C 6Cycloalkenyl group sulfenyl, C 3-C 6Nonaromatic heterocycles alkyl sulfenyl or C 3-C 6Nonaromatic heterocycles thiazolinyl sulfenyl; Described nonaromatic heterocycles base is selected from THF, THTP, Pyrrolidine, thiazolidine, tetrahydro-pyrazole, imidazolidine, tetrahydrochysene triazole, hexahydropyridine or six hydrogen pyrans;
R 16Be selected from C 1-C 6Alkyl, C 1-C 6Haloalkyl, C 2-C 6Thiazolinyl, C 2-C 6Haloalkenyl group, C 2-C 6Alkynyl, C 2-C 6Halo alkynyl or C 3-C 6-naphthenic base;
R 17, R 18Independently be selected from hydrogen or R separately 16
R 19P shown in being selected from down 1-P 28In any group:
Figure G200810116762201D00031
X is selected from O, S or NR 17
N is the integer of 0-2.
The comparatively preferred compound of the present invention is: in the general formula (I)
R 1Be selected from C 3-C 7Halogenated cycloalkyl, vinyl halides base C 3-C 7Naphthenic base, R 6Or R 7
R 2Be selected from R 8Or R 9
R 3, R 4, R 5Independently be selected from CN, halogen or R separately 17
R 6Be selected from not replacement or substituted phenyl, described substituting group is selected from 1-5 following radicals: halogen, C 1-C 4-alkyl, C 1-C 4Haloalkyl, C 1-C 4Alkoxyl group, C 1-C 4Halogenated alkoxy, CN, NO 2, SO nR 17, COR 17, COOR 17, CONR 17R 18, SO 2NR 17R 18Or OR 17
R 7Be selected from not replacement or substituted fragrant heterocyclic radical, described substituting group is selected from 1-3 following radicals: halogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl, C 1-C 4Alkoxyl group, C 1-C 4Halogenated alkoxy, CN, NO 2, SO nR 16, COR 16, COOR 17, CONR 17R 18, SO 2NR 17R 18, OR 17Or halogenophenyl; Described fragrant heterocyclic radical is selected from pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl group 、 oxazolyl 、 isoxazolyl, furyl, pyrryl, pyrazolyl, imidazolyl, triazolyl or 1,4-oxygen thiapyran;
R 8Be selected from R 6, R 7, R 10, R 11, R 12Or R 13
R 9Be selected from CHR 14R 15
R 10Be selected from and have the substituted R of following groups 16: R 6Or R 7
R 11Be selected from and have the substituted R of following groups 16: XR 6Or XR 7
R 12Be selected from and have the substituted R of following groups 16: COOR 6, COOR 7, CONR 6R 12, CONR 7R 17, SO 2NR 6R 17, SO 2NR 7R 17, NHSO 2R 6Or NHSO 2R 7
R 13Be selected from:
Figure G200810116762201D00041
R 14Be selected from CN or R 17
R 15Be selected from CN, COOR 17, CONR 17R 18, CH 2CH 2OCH 3, nonaromatic heterocycles base or by the substituted C of following groups 1-C 4Alkyl: CN, COOR 17, CONR 17R 18, NR 17R 18, R 19, OCH 2CN, OCH 2COOR 16, OCH 2CONR 17R 18, OCH 2CF 3, C 3-C 6Cycloalkyl oxy, C 3-C 6Cycloalkenyl oxy, C 3-C 6Nonaromatic heterocycles alkyl oxy, C 3-C 6Nonaromatic heterocycles thiazolinyl oxygen base, C 3-C 6Naphthenic base sulfenyl, C 3-C 6Cycloalkenyl group sulfenyl, C 3-C 6Nonaromatic heterocycles alkyl sulfenyl, C 3-C 6Nonaromatic heterocycles thiazolinyl sulfenyl.Described nonaromatic heterocycles base is selected from THF, THTP, Pyrrolidine, thiazolidine, tetrahydro-pyrazole, imidazolidine, tetrahydrochysene triazole, hexahydropyridine or six hydrogen pyrans;
R 16Be selected from C 1-C 4Alkyl, C 1-C 4Haloalkyl, C 2-C 4Thiazolinyl, C 2-C 4Haloalkenyl group, C 2-C 4Alkynyl, C 2-C 4Halo alkynyl or C 3-C 6-naphthenic base;
R 17, R 18Independently be selected from hydrogen or R separately 16
R 19Be selected from following groups: P 1, P 2, P 3, P 5, P 7, P 8, P 9, P 12, P 13, P 14, P 15, P 16, P 17, P 19, P 20, P 21, P 22, P 23, P 24, P 25, P 26, P 27Or P 28
X is selected from O, S or NR 17
N is the integer of 0-2.
The further preferred compound of the present invention is: in the general formula (I)
R 1Be selected from R 6Or R 7
R 2Be selected from R 8Or R 9
R 3, R 4, R 5Independently be selected from CN, halogen or R separately 17
R 6Be selected from not replacement or substituted phenyl, described substituting group is selected from 1-5 following radicals: halogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl, NO 2Or SO nR 9
R 7Be selected from not replacement or substituted fragrant heterocyclic radical, described substituting group is selected from 1-3 following radicals: halogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl, NO 2, SO nR 9, described fragrant heterocyclic radical is selected from pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl group 、 oxazolyl 、 isoxazolyl, furyl, pyrryl, pyrazolyl, imidazolyl, triazolyl or 1,4-oxygen thiapyran;
R 8Be selected from R 6, R 7, R 10, R 11, R 12Or R 13
R 9Be selected from CHR 14R 15
R 10Be selected from and have the substituted R of following groups 16: R 6Or R 7
R 11Be selected from and have the substituted R of following groups 16: XR 6Or XR 7
R 12Be selected from and have the substituted R of following groups 16: COOR 6, COOR 7, CONR 6R 12, CONR 7R 17, SO 2NR 6R 17, SO 2NR 7R 17, NHSO 2R 6Or NHSO 2R 7
R 13Be selected from:
Figure G200810116762201D00051
R 14Be selected from CN or R 17
R 15Be selected from CN, COOR 17, CONR 17R 18, CH 2CH 2OCH 3, nonaromatic heterocycles base or by the substituted C of following groups 1-C 4Alkyl: CN, COOR 17, CONR 17R 18, NR 17R 18, R 19, OCH 2CN, OCH 2COOR 16, OCH 2CONR 17R 18, OCH 2CF 3, C 3-C 6Cycloalkyl oxy, C 3-C 6Cycloalkenyl oxy, C 3-C 6Nonaromatic heterocycles alkyl oxy, C 3-C 6Nonaromatic heterocycles thiazolinyl oxygen base, C 3-C 6Naphthenic base sulfenyl, C 3-C 6Cycloalkenyl group sulfenyl, C 3-C 6Nonaromatic heterocycles alkyl sulfenyl, C 3-C 6Nonaromatic heterocycles thiazolinyl sulfenyl; Described nonaromatic heterocycles base is selected from THF, THTP, Pyrrolidine, thiazolidine, tetrahydro-pyrazole, imidazolidine, tetrahydrochysene triazole, hexahydropyridine or six hydrogen pyrans.
R 16Be selected from C 1-C 4Alkyl;
R 17, R 18Independently be selected from hydrogen or C separately 1-C 4Alkyl;
R 19Be selected from following groups: P 1, P 2, P 3, P 5, P 7, P 8, P 9, P 12, P 13, P 14, P 15, P 16, P 17, P 19, P 20, P 21, P 22, P 23, P 24, P 25, P 26, P 27Or P 28
X is selected from O, S or NR 17
N is the integer of 0-2.
The further preferred again compound of the present invention is: in the general formula (I)
R 1Be selected from R 6Or R 7
R 2Be selected from R 8Or R 9
R 3, R 4, R 5Independently be selected from CN, halogen or R separately 17
R 6Be selected from not replacement or substituted phenyl, described substituting group is selected from 1-5 following radicals: halogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl;
R 7Be selected from not replacement or substituted fragrant heterocyclic radical, described substituting group is selected from 1-3 following radicals: halogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl; Described fragrant heterocyclic radical is selected from pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl group 、 oxazolyl 、 isoxazolyl, furyl, pyrryl, pyrazolyl, imidazolyl, triazolyl or 1,4-oxygen thiapyran;
R 8Be selected from R 6, R 7, R 10, R 11, R 12Or R 13
R 9Be selected from CHR 14R 15
R 10Be selected from and have the substituted R of following groups 16: R 6Or R 7
R 11Be selected from and have the substituted R of following groups 16: XR 6Or XR 7
R 12Be selected from and have the substituted R of following groups 16: COOR 6, COOR 7, CONR 6R 12, CONR 7R 17, SO 2NR 6R 17, SO 2NR 7R 17, NHSO 2R 6Or NHSO 2R 7
R 13Be selected from:
Figure G200810116762201D00061
R 14Be selected from CN or R 17
R 15Be selected from CN, COOR 17, CONR 17R 18, CH 2CH 2OCH 3, the nonaromatic heterocycles base, or by the substituted C of following groups 1-C 4Alkyl: CN, COOR 17, CONR 17R 18, NR 17R 18, R 19, OCH 2CN, OCH 2COOR 16, OCH 2CONR 17R 18, OCH 2CF 3, C 3-C 6Cycloalkyl oxy, C 3-C 6Cycloalkenyl oxy, C 3-C 6Nonaromatic heterocycles alkyl oxy, C 3-C 6Nonaromatic heterocycles thiazolinyl oxygen base.Described nonaromatic heterocycles is selected from THF, THTP, Pyrrolidine, thiazolidine, tetrahydro-pyrazole, imidazolidine, tetrahydrochysene triazole, hexahydropyridine or six hydrogen pyrans
R 16Be selected from C 1-C 4Alkyl;
R 17, R 18Independently be selected from hydrogen or C separately 1-C 4Alkyl;
R 19Be selected from following groups: P 1, P 2, P 3, P 5, P 7, P 8, P 12, P 14, P 17, P 19, P 20, P 21, P 22, P 23, P 24, P 25, P 26, P 27Or P 28
X is selected from O, S or NR 17
N is the integer of 0-2.
The further preferred compound of the present invention is: in the general formula (I)
R 1Be selected from R 6
R 2Be selected from R 8Or R 9
R 3, R 4, R 5Independently be selected from CN, halogen or R separately 17
R 6Be selected from not replacement or substituted phenyl, described substituting group is selected from 1-5 following radicals: halogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl;
R 7Be selected from not replacement or substituted fragrant heterocyclic radical, described substituting group is selected from 1-3 following radicals: halogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl; Described fragrant heterocyclic radical is selected from pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl group 、 oxazolyl 、 isoxazolyl, furyl, pyrryl, pyrazolyl, imidazolyl, triazolyl or 1,4-oxygen thiapyran;
R 8Be selected from R 6, R 7, R 10, R 11, R 12Or R 13
R 9Be selected from CHR 14R 15
R 10Be selected from and have the substituted R of following groups 16: R 6Or R 7
R 11Be selected from and have the substituted R of following groups 16: XR 6Or XR 7
R 12Be selected from and have the substituted R of following groups 16: COOR 6, COOR 7, CONR 6R 12, CONR 7R 17, SO 2NR 6R 17, SO 2NR 7R 17, NHSO 2R 6Or NHSO 2R 7
R 13Be selected from:
R 14Be selected from CN or R 17
R 15Be selected from CN, CH 2CH 2OCH 3, nonaromatic heterocycles base or by the substituted C of following groups 1-C 4Alkyl: CN, NR 17R 18, OCH 2CN, OCH 2CF 3, C 3-C 6Cycloalkyl oxy, C 3-C 6Cycloalkenyl oxy, C 3-C 6Nonaromatic heterocycles alkyl oxy, C 3-C 6Nonaromatic heterocycles thiazolinyl oxygen base; Described nonaromatic heterocycles base is selected from THF, THTP, Pyrrolidine, thiazolidine, tetrahydro-pyrazole, imidazolidine, tetrahydrochysene triazole, hexahydropyridine or six hydrogen pyrans;
R 16Be selected from C 1-C 4Alkyl;
R 17, R 18Independently be selected from hydrogen or C separately 1-C 4Alkyl;
X is selected from O.
Substituting group described in general formula of the present invention (I) compound has following implication:
Halogen is represented fluorine, chlorine, bromine or iodine.
The term " halo " that occurs in the group front representes that this group is part or all of halo, that is to say, is replaced by F, Cl, Br or I with the mode of arbitrary combination, is preferably replaced by F or Cl.
An alkyl and its part (except as otherwise noted) can be straight or brancheds.
Expression formula " C 1-C 6Alkyl " be appreciated that the straight or branched alkyl that has 1 to 6 carbon atom for expression, as, for example methyl, ethyl, propyl group, sec.-propyl, 1-butyl, 2-butyl, 2-methyl-propyl or the tertiary butyl.
Alkyl in alkyl and the combination group except as otherwise noted, preferably has 1-4 carbon atom.
" C 1-C 6Haloalkyl " mean expression formula " C 1-C 6Alkyl " described in alkyl, wherein one or more Wasserstoffatomss are by the identical or different halogen atoms replacements of same quantity, like a haloalkyl, whole haloalkyl, CF 3, CHF 2, CH 2F, CHFCH 3, CF 3CF 2, CHF 2CF 2, CH 2FCHCl, CH 2Cl, CCl 3, CHCl 2Or CH 2CH 2Cl.
" C 1-C 6Alkoxyl group " carbochain that means in the alkoxyl group has at expression formula " C 1-C 6Alkyl " expression has the straight or branched alkyl of 1 to 6 carbon atom, for example methyl, ethyl, propyl group, sec.-propyl, 1-butyl, 2-butyl, 2-methyl-propyl or the tertiary butyl.
" C 2-C 6Thiazolinyl " expression has and contains at least one with the non-annularity carbochain of the straight or branched of the corresponding carbonatoms of said scope and this carbochain and can be positioned two keys of the optional position of unsaturated group separately.Therefore " C 2-C 12Thiazolinyl " typical example such as vinyl, allyl group, 2-methyl-2-propenyl, crotyl, pentenyl, 2-methylpent thiazolinyl or hexenyl etc.
" C 2-C 6Alkynyl " expression has and contains one with the non-annularity carbochain of the straight or branched of the corresponding carbonatoms of said scope and this carbochain and can be positioned the triple bond of the optional position of unsaturated group separately.Therefore " C 2-C 6Alkynyl " typical example such as propargyl, 1-methyl-2-propynyl, 2-butyne base or 3-butynyl etc.
During preferably encircling, naphthenic base has 3-7 carbon atom and optional by halogen or alkyl replacement.
General formula of the present invention (I) compound can referenced patent US200320808, the method that provides in the documents such as JP2003286265 preparation.
General formula of the present invention (I) compound includes but not limited to the compound in the following compound tabulation 1 and 2.
Compound tabulation 1 (R wherein 2Be R 8)
Figure G200810116762201D00071
Numbering R 1 R 8 R 3 R 4 R 5
I-1 The 4-chloro-phenyl- Ph H H Bu t
I-2 The 2-trifluoromethyl Ph H H Bu t
I-3 3-(4-5-flumethiazine base) Ph H H Bu t
I-4 5-(1-methyl-3-ethyl pyrazolyl) Ph H H Bu t
I-5 The 4-chloro-phenyl- Q 1 H H Bu t
I-6 The 2-trifluoromethyl Q 1 H H Bu t
I-7 3-(4-5-flumethiazine base) Q 1 H H Bu t
I-8 5-(1-methyl-3-ethyl pyrazolyl) Q 1 H H Bu t
I-9 The 4-chloro-phenyl- Q 2 H H Bu t
[0129]
I-10 The 2-trifluoromethyl Q 2 H H Bu t
I-11 3-(4-5-flumethiazine base) Q 2 H H Bu t
I-12 5-(1-methyl-3-ethyl pyrazolyl) Q 2 H H Bu t
I-13 The 4-chloro-phenyl- Q 3 H H Bu t
I-14 The 2-trifluoromethyl Q 3 H H Bu t
I-15 3-(4-5-flumethiazine base) Q 3 H H Bu t
I-16 5-(1-methyl-3-ethyl pyrazolyl) Q 3 H H Bu t
I-17 The 4-chloro-phenyl- Q 4 H H Bu t
I-18 The 2-trifluoromethyl Q 4 H H Bu t
I-19 3-(4-5-flumethiazine base) Q 4 H H Bu t
I-20 5-(1-methyl-3-ethyl pyrazolyl) Q 4 H H Bu t
I-21 The 2-trifluoromethyl Q 5 H H Bu t
I-22 The 2-trifluoromethyl Q 6 H H Bu t
I-23 2, the 6-difluorophenyl CH 2CH 2Ph H H Bu t
I-24 The 4-chloro-phenyl- CH 2CH 2Ph H H Bu t
I-25 The 2-trifluoromethyl CH 2CH 2Ph H H Bu t
I-26 1-(4-chloro-phenyl-)-isobutyl- CH 2CH 2Ph H H Bu t
I-27 3-(4-5-flumethiazine base) CH 2CH 2Ph H H Bu t
I-28 3-(6-chloropyridine base) CH 2CH 2Ph H H Bu t
I-29 2-(6-(3-trifluoromethyl) pyridyl) CH 2CH 2Ph H H Bu t
I-30 5-(4-trifluoromethyl pyrimidine base) CH 2CH 2Ph H H Bu t
I-31 4-(2-chlorine thiazolyl) CH 2CH 2Ph H H Bu t
I-32 5-(4-trifluoromethyl thiazole base) CH 2CH 2Ph H H Bu t
I-33 5-(2-methyl-4-trifluoromethyl thiazole base) CH 2CH 2Ph H H Bu t
I-34 5-(2-chloro-4-trifluoromethyl thiazole base) CH 2CH 2Ph H H Bu t
I-35 5-(1-methyl-3-trifluoromethyl pyrazol base) CH 2CH 2Ph H H Bu t
I-36 5-(1-methyl-3-ethyl pyrazolyl) CH 2CH 2Ph H H Bu t
I-37 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CH 2CH 2Ph H H Bu t
I-38 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) CH 2CH 2Ph H H Bu t
I-39 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base CH 2CH 2Ph H H Bu t
I-40 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CH 2CH 2Ph H H Bu t
I-41 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CH 2CH 2Ph H H Bu t
I-42 The 2-trifluoromethyl Q 7 H H Bu t
I-43 The 2-trifluoromethyl Q 8 H H Bu t
I-44 The 2-trifluoromethyl Q 9 H H Bu t
I-45 2, the 6-difluorophenyl (CH 2) 3Ph H H Bu t
I-46 The 4-chloro-phenyl- (CH 2) 3Ph H H Bu t
I-47 The 2-trifluoromethyl (CH 2) 3Ph H H Bu t
I-48 1-(4-chloro-phenyl-)-isobutyl- (CH 2) 3Ph H H Bu t
I-49 3-(4-5-flumethiazine base) (CH 2) 3Ph H H Bu t
I-50 3-(6-chloropyridine base) (CH 2) 3Ph H H Bu t
I-51 2-(6-(3-trifluoromethyl) pyridyl) (CH 2) 3Ph H H Bu t
I-52 5-(4-trifluoromethyl pyrimidine base) (CH 2) 3Ph H H Bu t
[0130]
I-53 4-(2-chlorine thiazolyl) (CH 2) 3Ph H H Bu t
I-54 5-(4-trifluoromethyl thiazole base) (CH 2) 3Ph H H Bu t
I-55 5-(2-methyl-4-trifluoromethyl thiazole base) (CH 2) 3Ph H H Bu t
I-56 5-(2-chloro-4-trifluoromethyl thiazole base) (CH 2) 3Ph H H Bu t
I-57 5-(1-methyl-3-trifluoromethyl pyrazol base) (CH 2) 3Ph H H Bu t
I-58 5-(1-methyl-3-ethyl pyrazolyl) (CH 2) 3Ph H H Bu t
I-59 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) (CH 2) 3Ph H H Bu t
I-60 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) (CH 2) 3Ph H H Bu t
I-61 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base (CH 2) 3Ph H H Bu t
I-62 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) (CH 2) 3Ph H H Bu t
I-63 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) (CH 2) 3Ph H H Bu t
I-64 The 4-chloro-phenyl- (CH 2) 4Ph H H Bu t
I-65 The 2-trifluoromethyl (CH 2) 4Ph H H Bu t
I-66 3-(4-5-flumethiazine base) (CH 2) 4Ph H H Bu t
I-67 5-(1-methyl-3-ethyl pyrazolyl) (CH 2) 4Ph H H Bu t
I-68 The 2-trifluoromethyl Q 10 H H Bu t
I-69 The 2-trifluoromethyl Q 11 H H Bu t
I-70 The 2-trifluoromethyl Q 12 H H Bu t
I-71 The 4-chloro-phenyl- Q 13 H H Bu t
I-72 The 2-trifluoromethyl Q 13 H H Bu t
I-73 3-(4-5-flumethiazine base) Q 13 H H Bu t
I-74 5-(1-methyl-3-ethyl pyrazolyl) Q 13 H H Bu t
I-75 2, the 6-difluorophenyl Q 14 H H Bu t
I-76 The 4-chloro-phenyl- Q 14 H H Bu t
I-77 The 2-trifluoromethyl Q 14 H H Bu t
I-78 1-(4-chloro-phenyl-)-isobutyl- Q 14 H H Bu t
I-79 3-(4-5-flumethiazine base) Q 14 H H Bu t
I-80 3-(6-chloropyridine base) Q 14 H H Bu t
I-81 2-(6-(3-trifluoromethyl) pyridyl) Q 14 H H Bu t
I-82 5-(4-trifluoromethyl pyrimidine base) Q 14 H H Bu t
I-83 4-(2-chlorine thiazolyl) Q 14 H H Bu t
I-84 5-(4-trifluoromethyl thiazole base) Q 14 H H Bu t
I-85 5-(2-methyl-4-trifluoromethyl thiazole base) Q 14 H H Bu t
I-86 5-(2-chloro-4-trifluoromethyl thiazole base) Q 14 H H Bu t
I-87 5-(1-methyl-3-trifluoromethyl pyrazol base) Q 14 H H Bu t
I-88 5-(1-methyl-3-ethyl pyrazolyl) Q 14 H H Bu t
I-89 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) Q 14 H H Bu t
I-90 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) Q 14 H H Bu t
I-91 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base Q 14 H H Bu t
I-92 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) Q 14 H H Bu t
I-93 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) Q 14 H H Bu t
I-94 The 4-chloro-phenyl- Q 15 H H Bu t
I-95 The 2-trifluoromethyl Q 15 H H Bu t
[0131]
I-96 3-(4-5-flumethiazine base) Q 15 H H Bu t
I-97 5-(1-methyl-3-ethyl pyrazolyl) Q 15 H H Bu t
I-98 2, the 6-difluorophenyl Q 16 H H Bu t
I-99 The 4-chloro-phenyl- Q 16 H H Bu t
I-100 The 2-trifluoromethyl Q 16 H H Bu t
I-101 1-(4-chloro-phenyl-)-isobutyl- Q 16 H H Bu t
I-102 3-(4-5-flumethiazine base) Q 16 H H Bu t
I-103 3-(6-chloropyridine base) Q 16 H H Bu t
I-104 2-(6-(3-trifluoromethyl) pyridyl) Q 16 H H Bu t
I-105 5-(4-trifluoromethyl pyrimidine base) Q 16 H H Bu t
I-106 4-(2-chlorine thiazolyl) Q 16 H H Bu t
I-107 5-(4-trifluoromethyl thiazole base) Q 16 H H Bu t
I-108 5-(2-methyl-4-trifluoromethyl thiazole base) Q 16 H H Bu t
I-109 5-(2-chloro-4-trifluoromethyl thiazole base) Q 16 H H Bu t
I-110 5-(1-methyl-3-trifluoromethyl pyrazol base) Q 16 H H Bu t
I-111 5-(1-methyl-3-ethyl pyrazolyl) Q 16 H H Bu t
I-112 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) Q 16 H H Bu t
I-113 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) Q 16 H H Bu t
I-114 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base Q 16 H H Bu t
I-115 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) Q 16 H H Bu t
I-116 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) Q 16 H H Bu t
I-117 2, the 6-difluorophenyl Q 17 H H Bu t
I-118 The 4-chloro-phenyl- Q 17 H H Bu t
I-119 The 2-trifluoromethyl Q 17 H H Bu t
I-120 1-(4-chloro-phenyl-)-isobutyl- Q 17 H H Bu t
I-121 3-(4-5-flumethiazine base) Q 17 H H Bu t
I-122 3-(6-chloropyridine base) Q 17 H H Bu t
I-123 2-(6-(3-trifluoromethyl) pyridyl) Q 17 H H Bu t
I-124 5-(4-trifluoromethyl pyrimidine base) Q 17 H H Bu t
I-125 4-(2-chlorine thiazolyl) Q 17 H H Bu t
I-126 5-(4-trifluoromethyl thiazole base) Q 17 H H Bu t
I-127 5-(2-methyl-4-trifluoromethyl thiazole base) Q 17 H H Bu t
I-128 5-(2-chloro-4-trifluoromethyl thiazole base) Q 17 H H Bu t
I-129 5-(1-methyl-3-trifluoromethyl pyrazol base) Q 17 H H Bu t
I-130 5-(1-methyl-3-ethyl pyrazolyl) Q 17 H H Bu t
I-131 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) Q 17 H H Bu t
I-132 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) Q 17 H H Bu t
I-133 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base Q 17 H H Bu t
I-134 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) Q 17 H H Bu t
I-135 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) Q 17 H H Bu t
I-136 2, the 6-difluorophenyl Q 18 H H Bu t
I-137 The 4-chloro-phenyl- Q 18 H H Bu t
I-138 The 2-trifluoromethyl Q 18 H H Bu t
[0132]
I-139 1-(4-chloro-phenyl-)-isobutyl- Q 18 H H Bu t
I-140 3-(4-5-flumethiazine base) Q 18 H H Bu t
I-141 3-(6-chloropyridine base) Q 18 H H Bu t
I-142 2-(6-(3-trifluoromethyl) pyridyl) Q 18 H H Bu t
I-143 5-(4-trifluoromethyl pyrimidine base) Q 18 H H Bu t
I-144 4-(2-chlorine thiazolyl) Q 18 H H Bu t
I-145 5-(4-trifluoromethyl thiazole base) Q 18 H H Bu t
I-146 5-(2-methyl-4-trifluoromethyl thiazole base) Q 18 H H Bu t
I-147 5-(2-chloro-4-trifluoromethyl thiazole base) Q 18 H H Bu t
I-148 5-(1-methyl-3-trifluoromethyl pyrazol base) Q 18 H H Bu t
I-149 5-(1-methyl-3-ethyl pyrazolyl) Q 18 H H Bu t
I-150 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) Q 18 H H Bu t
I-151 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) Q 18 H H Bu t
I-152 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base Q 18 H H Bu t
I-153 5-(4-Trifluoromethyl-1,2,3 thiadiazoles Q 18 H H Bu t
I-154 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) Q 18 H H Bu t
I-155 The 4-chloro-phenyl- Q 19 H H Bu t
I-156 The 2-trifluoromethyl Q 19 H H Bu t
I-157 3-(4-5-flumethiazine base) Q 19 H H Bu t
I-158 5-(1-methyl-3-ethyl pyrazolyl) Q 19 H H Bu t
I-159 The 4-chloro-phenyl- Q 20 H H Bu t
I-160 The 2-trifluoromethyl Q 20 H H Bu t
I-161 3-(4-5-flumethiazine base) Q 20 H H Bu t
I-162 5-(1-methyl-3-ethyl pyrazolyl) Q 20 H H Bu t
I-163 The 4-chloro-phenyl- Q 21 H H Bu t
I-164 The 2-trifluoromethyl Q 21 H H Bu t
I-165 3-(4-5-flumethiazine base) Q 21 H H Bu t
I-166 5-(1-methyl-3-ethyl pyrazolyl) Q 21 H H Bu t
I-167 2, the 6-difluorophenyl Q 22 H H Bu t
I-168 The 4-chloro-phenyl- Q 22 H H Bu t
I-169 The 2-trifluoromethyl Q 22 H H Bu t
I-170 1-(4-chloro-phenyl-)-isobutyl- Q 22 H H Bu t
I-171 3-(4-5-flumethiazine base) Q 23 H H Bu t
I-172 3-(6-chloropyridine base) Q 23 H H Bu t
I-173 2-(6-(3-trifluoromethyl) pyridyl) Q 23 H H Bu t
I-174 5-(4-trifluoromethyl pyrimidine base) Q 23 H H Bu t
I-175 4-(2-chlorine thiazolyl) Q 23 H H Bu t
I-176 5-(4-trifluoromethyl thiazole base) Q 23 H H Bu t
I-177 5-(2-methyl-4-trifluoromethyl thiazole base) Q 23 H H Bu t
I-178 5-(2-chloro-4-trifluoromethyl thiazole base) Q 23 H H Bu t
I-179 5-(1-methyl-3-trifluoromethyl pyrazol base) Q 23 H H Bu t
I-180 5-(1-methyl-3-ethyl pyrazolyl) Q 23 H H Bu t
I-181 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) Q 23 H H Bu t
[0133]
I-182 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) Q 23 H H Bu t
I-183 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base Q 23 H H Bu t
I-184 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) Q 23 H H Bu t
I-185 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) Q 23 H H Bu t
I-186 The 4-chloro-phenyl- Q 24 H H Bu t
I-187 The 2-trifluoromethyl Q 24 H H Bu t
I-188 3-(4-5-flumethiazine base) Q 24 H H Bu t
I-189 5-(1-methyl-3-ethyl pyrazolyl) Q 24 H H Bu t
I-190 The 4-chloro-phenyl- Q 25 H H Bu t
I-191 The 2-trifluoromethyl Q 25 H H Bu t
I-192 3-(4-5-flumethiazine base) Q 25 H H Bu t
I-193 5-(1-methyl-3-ethyl pyrazolyl) Q 25 H H Bu t
I-194 The 4-chloro-phenyl- Q 26 H H Bu t
I-195 The 2-trifluoromethyl Q 26 H H Bu t
I-196 3-(4-5-flumethiazine base) Q 26 H H Bu t
I-197 5-(1-methyl-3-ethyl pyrazolyl) Q 26 H H Bu t
I-198 2, the 6-difluorophenyl CH 2CH 2OPh H H Bu t
I-199 The 4-chloro-phenyl- CH 2CH 2OPh H H Bu t
I-200 The 2-trifluoromethyl CH 2CH 2OPh H H Bu t
I-201 1-(4-chloro-phenyl-)-isobutyl- CH 2CH 2OPh H H Bu t
I-202 3-(4-5-flumethiazine base) CH 2CH 2OPh H H Bu t
I-203 3-(6-chloropyridine base) CH 2CH 2OPh H H Bu t
I-204 2-(6-(3-trifluoromethyl) pyridyl) CH 2CH 2OPh H H Bu t
I-205 5-(4-trifluoromethyl pyrimidine base) CH 2CH 2OPh H H Bu t
I-206 4-(2-chlorine thiazolyl) CH 2CH 2OPh H H Bu t
I-207 5-(4-trifluoromethyl thiazole base) CH 2CH 2OPh H H Bu t
I-208 5-(2-methyl-4-trifluoromethyl thiazole base) CH 2CH 2OPh H H Bu t
I-209 5-(2-chloro-4-trifluoromethyl thiazole base) CH 2CH 2OPh H H Bu t
I-210 5-(1-methyl-3-trifluoromethyl pyrazol base) CH 2CH 2OPh H H Bu t
I-211 5-(1-methyl-3-ethyl pyrazolyl) CH 2CH 2OPh H H Bu t
I-212 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CH 2CH 2OPh H H Bu t
I-213 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) CH 2CH 2OPh H H Bu t
I-214 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base CH 2CH 2OPh H H Bu t
I-215 5-(4-Trifluoromethyl-1,2,3 thiadiazoles CH 2CH 2OPh H H Bu t
I-216 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CH 2CH 2OPh H H Bu t
I-217 The 2-trifluoromethyl Q 27 H H Bu t
I-218 The 2-trifluoromethyl Q 28 H H Bu t
I-219 The 2-trifluoromethyl Q 29 H H Bu t
I-220 The 2-trifluoromethyl Q 30 H H Bu t
I-221 The 2-trifluoromethyl Q 31 H H Bu t
I-222 The 2-trifluoromethyl Q 32 H H Bu t
I-223 The 2-trifluoromethyl Q 33 H H Bu t
I-224 The 2-trifluoromethyl Q 34 H H Bu t
[0134]
I-225 The 2-trifluoromethyl Q 35 H H Bu t
I-226 The 2-trifluoromethyl Q 36 H H Bu t
I-227 The 2-trifluoromethyl Q 37 H H Bu t
I-228 The 2-trifluoromethyl Q 38 H H Bu t
I-229 The 2-trifluoromethyl Q 39 H H Bu t
I-230 The 2-trifluoromethyl Q 40 H H Bu t
I-231 The 2-trifluoromethyl Q 41 H H Bu t
I-232 The 2-trifluoromethyl Q 42 H H Bu t
I-233 The 4-chloro-phenyl- (CH 2) 3OPh H H Bu t
I-234 The 2-trifluoromethyl (CH 2) 3OPh H H Bu t
I-235 3-(4-5-flumethiazine base) (CH 2) 3OPh H H Bu t
I-236 5-(1-methyl-3-ethyl pyrazolyl) (CH 2) 3OPh H H Bu t
I-237 The 2-trifluoromethyl Q 43 H H Bu t
I-238 The 2-trifluoromethyl Q 44 H H Bu t
I-239 The 2-trifluoromethyl Q 45 H H Bu t
I-240 The 2-trifluoromethyl Q 46 H H Bu t
I-241 2, the 6-difluorophenyl Q 47 H H Bu t
I-242 The 4-chloro-phenyl- Q 47 H H Bu t
I-243 The 2-trifluoromethyl Q 47 H H Bu t
I-244 1-(4-chloro-phenyl-)-isobutyl- Q 47 H H Bu t
I-245 3-(4-5-flumethiazine base) Q 47 H H Bu t
I-246 3-(6-chloropyridine base) Q 47 H H Bu t
I-247 2-(6-(3-trifluoromethyl) pyridyl) Q 47 H H Bu t
I-248 5-(4-trifluoromethyl pyrimidine base) Q 47 H H Bu t
I-249 4-(2-chlorine thiazolyl) Q 47 H H Bu t
I-250 5-(4-trifluoromethyl thiazole base) Q 47 H H Bu t
I-251 5-(2-methyl-4-trifluoromethyl thiazole base) Q 47 H H Bu t
I-252 5-(2-chloro-4-trifluoromethyl thiazole base) Q 47 H H Bu t
I-253 5-(1-methyl-3-trifluoromethyl pyrazol base) Q 47 H H Bu t
I-254 5-(1-methyl-3-ethyl pyrazolyl) Q 47 H H Bu t
I-255 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) Q 47 H H Bu t
I-256 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) Q 47 H H Bu t
I-257 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base Q 47 H H Bu t
I-258 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) Q 47 H H Bu t
I-259 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) Q 47 H H Bu t
I-260 The 4-chloro-phenyl- Q 48 H H Bu t
I-261 The 2-trifluoromethyl Q 48 H H Bu t
I-262 3-(4-5-flumethiazine base) Q 48 H H Bu t
I-263 5-(1-methyl-3-ethyl pyrazolyl) Q 48 H H Bu t
I-264 2, the 6-difluorophenyl Q 49 H H Bu t
I-265 The 4-chloro-phenyl- Q 49 H H Bu t
I-266 The 2-trifluoromethyl Q 49 H H Bu t
I-267 1-(4-chloro-phenyl-)-isobutyl- Q 49 H H Bu t
[0135]
I-268 3-(4-5-flumethiazine base) Q 49 H H Bu t
I-269 3-(6-chloropyridine base) Q 49 H H Bu t
I-270 2-(6-(3-trifluoromethyl) pyridyl) Q 49 H H Bu t
I-271 5-(4-trifluoromethyl pyrimidine base) Q 49 H H Bu t
I-272 4-(2-chlorine thiazolyl) Q 49 H H Bu t
I-273 5-(4-trifluoromethyl thiazole base) Q 49 H H Bu t
I-274 5-(2-methyl-4-trifluoromethyl thiazole base) Q 49 H H Bu t
I-275 5-(2-chloro-4-trifluoromethyl thiazole base) Q 49 H H Bu t
I-276 5-(1-methyl-3-trifluoromethyl pyrazol base) Q 49 H H Bu t
I-277 5-(1-methyl-3-ethyl pyrazolyl) Q 49 H H Bu t
I-278 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) Q 49 H H Bu t
I-279 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) Q 49 H H Bu t
I-280 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base Q 49 H H Bu t
I-281 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) Q 49 H H Bu t
I-282 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) Q 49 H H Bu t
I-283 The 4-chloro-phenyl- Q 50 H H Bu t
I-284 The 2-trifluoromethyl Q 50 H H Bu t
I-285 2, the 6-difluorophenyl Q 51 H H Bu t
I-286 The 4-chloro-phenyl- Q 51 H H Bu t
I-287 The 2-trifluoromethyl Q 51 H H Bu t
I-288 1-(4-chloro-phenyl-)-isobutyl- Q 51 H H Bu t
I-289 3-(4-5-flumethiazine base) Q 51 H H Bu t
I-290 3-(6-chloropyridine base) Q 51 H H Bu t
I-291 2-(6-(3-trifluoromethyl) pyridyl) Q 51 H H Bu t
I-292 5-(4-trifluoromethyl pyrimidine base) Q 51 H H Bu t
I-293 4-(2-chlorine thiazolyl) Q 51 H H Bu t
I-294 5-(4-trifluoromethyl thiazole base) Q 51 H H Bu t
I-295 5-(2-methyl-4-trifluoromethyl thiazole base) Q 51 H H Bu t
I-296 5-(2-chloro-4-trifluoromethyl thiazole base) Q 51 H H Bu t
I-297 5-(1-methyl-3-trifluoromethyl pyrazol base) Q 51 H H Bu t
I-298 5-(1-methyl-3-ethyl pyrazolyl) Q 51 H H Bu t
I-299 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) Q 51 H H Bu t
I-300 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) Q 51 H H Bu t
I-301 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base Q 51 H H Bu t
I-302 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) Q 51 H H Bu t
I-303 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) Q 51 H H Bu t
I-304 The 4-chloro-phenyl- Q 52 H H Bu t
I-305 The 2-trifluoromethyl Q 52 H H Bu t
I-306 3-(4-5-flumethiazine base) Q 52 H H Bu t
I-307 5-(1-methyl-3-ethyl pyrazolyl) Q 52 H H Bu t
I-308 2, the 6-difluorophenyl Q 52 H H Bu t
I-309 The 4-chloro-phenyl- Q 52 H H Bu t
I-310 The 2-trifluoromethyl Q 52 H H Bu t
[0136]
I-311 1-(4-chloro-phenyl-)-isobutyl- Q 52 H H Bu t
I-312 3-(4-5-flumethiazine base) Q 52 H H Bu t
I-313 3-(6-chloropyridine base) Q 52 H H Bu t
I-314 2-(6-(3-trifluoromethyl) pyridyl) Q 52 H H Bu t
I-315 5-(4-trifluoromethyl pyrimidine base) Q 52 H H Bu t
I-316 4-(2-chlorine thiazolyl) Q 52 H H Bu t
I-317 5-(4-trifluoromethyl thiazole base) Q 52 H H Bu t
I-318 5-(2-chloro-4-trifluoromethyl thiazole base) Q 52 H H Bu t
I-319 5-(1-methyl-3-ethyl pyrazolyl) Q 52 H H Bu t
I-320 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) Q 52 H H Bu t
I-321 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) Q 52 H H Bu t
I-322 3-(2, the 2-dichloroethylene)-2,2-dimethylcyclopropane base Q 52 H H Bu t
I-323 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) Q 52 H H Bu t
I-324 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) Q 52 H H Bu t
I-325 The 4-chloro-phenyl- Q 53 H H Bu t
I-326 The 2-trifluoromethyl Q 53 H H Bu t
I-327 The 4-chloro-phenyl- Q 54 H H Bu t
I-328 The 2-trifluoromethyl Q 54 H H Bu t
I-329 The 4-chloro-phenyl- Q 55 H H Bu t
I-330 The 2-trifluoromethyl Q 55 H H Bu t
I-331 The 4-chloro-phenyl- Q 56 H H Bu t
I-332 The 2-trifluoromethyl Q 56 H H Bu t
I-333 The 4-chloro-phenyl- Q 57 H H Bu t
I-334 The 2-trifluoromethyl Q 57 H H Bu t
I-335 The 4-chloro-phenyl- Q 58 H H Bu t
I-336 The 2-trifluoromethyl Q 58 H H Bu t
I-337 The 4-chloro-phenyl- Q 59 H H Bu t
I-338 The 2-trifluoromethyl Q 59 H H Bu t
I-339 The 4-chloro-phenyl- Q 60 H H Bu t
I-340 The 2-trifluoromethyl Q 60 H H Bu t
I-341 The 4-chloro-phenyl- Q 61 H H Bu t
I-342 The 2-trifluoromethyl Q 61 H H Bu t
I-343 The 2-trifluoromethyl Q 62 H H Bu t
I-344 The 2-trifluoromethyl Q 63 H H Bu t
I-345 The 2-trifluoromethyl Q 64 H H Bu t
I-346 The 2-trifluoromethyl Q 65 H H Bu t
I-347 The 2-trifluoromethyl Q 66 H H Bu t
I-348 The 2-trifluoromethyl Q 67 H H Bu t
I-349 The 2-trifluoromethyl Q 68 H H Bu t
I-350 The 2-trifluoromethyl Q 69 H H Bu t
I-351 The 2-trifluoromethyl Q 70 H H Bu t
I-352 The 2-trifluoromethyl Q 71 H H Bu t
I-353 The 2-trifluoromethyl Q 72 H H Bu t
[0137]
I-354 The 2-trifluoromethyl Q 73 H H Bu t
I-355 The 2-trifluoromethyl Q 74 H H Bu t
I-356 The 2-trifluoromethyl Q 75 H H Bu t
I-357 The 2-trifluoromethyl Q 76 H H Bu t
I-358 The 2-trifluoromethyl Q 77 H H Bu t
I-359 The 2-trifluoromethyl Q 78 H H Bu t
I-360 The 2-trifluoromethyl Q 79 H H Bu t
I-361 The 2-trifluoromethyl Q 80 H H Bu t
I-362 The 2-trifluoromethyl Q 81 H H Bu t
I-363 The 2-trifluoromethyl Q 82 H H Bu t
I-364 The 2-trifluoromethyl Q 83 H H Bu t
I-365 The 2-trifluoromethyl Q 84 H H Bu t
I-366 The 2-trifluoromethyl Q 85 H H Bu t
I-367 The 2-trifluoromethyl Q 86 H H Bu t
I-368 The 2-trifluoromethyl Q 87 H H Bu t
I-369 The 2-trifluoromethyl CH 2CH 2Ph H H Cl
I-370 The 2-trifluoromethyl CH 2CH 2Ph H H CH 3
I-371 The 2-trifluoromethyl CH 2CH 2Ph H H Ph
I-372 The 2-trifluoromethyl CH 2CH 2Ph Cl H Bu t
I-373 The 2-trifluoromethyl CH 2CH 2OPh H H Cl
I-374 The 2-trifluoromethyl CH 2CH 2OPh H H CH 3
I-375 The 2-trifluoromethyl CH 2CH 2OPh H H Ph
I-376 The 2-trifluoromethyl CH 2CH 2OPh Cl H Bu t
I-377 The 2-trifluoromethyl (CH 2CH 2) 3Ph Cl H Bu t
I-378 The 2-trifluoromethyl Q 88 H H Bu t
I-379 The 2-trifluoromethyl Q 89 H H Bu t
I-380 The 2-trifluoromethyl Q 90 H H Bu t
I-381 The 2-trifluoromethyl Q 91 H H Bu t
I-382 The 2-trifluoromethyl Q 92 H H Bu t
I-383 The 2-trifluoromethyl Q 93 H H Bu t
I-384 The 2-trifluoromethyl Q 94 H H Bu t
I-385 The 2-trifluoromethyl Q 95 H H Bu t
I-386 The 2-trifluoromethyl Q 96 H H Bu t
I-387 The 2-trifluoromethyl Q 97 H H Bu t
I-388 The 2-trifluoromethyl Q 98 H H Bu t
I-389 The 2-trifluoromethyl Q 99 H H Bu t
I-390 The 2-trifluoromethyl Q 100 H H Bu t
I-391 The 2-trifluoromethyl Q 101 H H Bu t
I-392 The 2-trifluoromethyl Q 102 H H Bu t
I-393 The 2-trifluoromethyl Q 103 H H Bu t
I-394 The 2-trifluoromethyl Q 104 H H Bu t
I-395 The 2-trifluoromethyl Q 105 H H Bu t
I-396 The 2-trifluoromethyl Q 106 H H Bu t
[0138]
I-397 The 2-trifluoromethyl Q 107 H H Bu t
I-398 The 2-trifluoromethyl Q 108 H H Bu t
I-399 The 2-trifluoromethyl Q 109 H H Bu t
I-400 The 2-trifluoromethyl Q 110 H H Bu t
I-401 The 2-trifluoromethyl Q 111 H H Bu t
I-402 The 2-trifluoromethyl Q 112 H H Cl
I-403 The 4-chloro-phenyl- Q 113 H H Cl
I-404 The 4-chloro-phenyl- Q 114 H H Bu t
In the last table: Ph represents phenyl, Bu tRepresent the tertiary butyl, Q 1-Q 114Represent following structure, wherein wavy line representes that other part links to each other in this key and the general formula (I).
Figure G200810116762201D00171
Figure G200810116762201D00181
Figure G200810116762201D00201
Compound tabulation 2 (R wherein 2Be CHR 14R 15)
Figure G200810116762201D00202
Numbering R 1 R 15 R 14 R 3 R 5 R 4
II-1 2, the 6-difluorophenyl (CH 2) 2OCH 3 H H Bu t H
II-2 The 4-chloro-phenyl- (CH 2) 2OCH 3 H H Bu t H
[0147]
II-3 The 2-trifluoromethyl (CH 2) 2OCH 3 H H Bu t H
II-4 3-(4-5-flumethiazine base) (CH 2) 2OCH 3 H H Bu t H
II-5 3-(6-chloropyridine base) (CH 2) 2OCH 3 H H Bu t H
II-6 5-(4-trifluoromethyl pyrimidine base) (CH 2) 2OCH 3 H H Bu t H
II-7 4-(2-chlorine thiazolyl) (CH 2) 2OCH 3 H H Bu t H
II-8 5-(4-trifluoromethyl thiazole base) (CH 2) 2OCH 3 H H Bu t H
II-9 5-(2-methyl-4-trifluoromethyl thiazole base) (CH 2) 2OCH 3 H H Bu t H
II-10 5-(2-chloro-4-trifluoromethyl thiazole base) (CH 2) 2OCH 3 H H Bu t H
II-11 5-(1-methyl-3-trifluoromethyl pyrazol base) (CH 2) 2OCH 3 H H Bu t H
II-12 5-(1-methyl-3-ethyl pyrazolyl) (CH 2) 2OCH 3 H H Bu t H
II-13 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) (CH 2) 2OCH 3 H H Bu t H
II-14 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) (CH 2) 2OCH 3 H H Bu t H
II-15 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) (CH 2) 2OCH 3 H H Bu t H
II-16 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) (CH 2) 2OCH 3 H H Bu t H
II-17 The 4-chloro-phenyl- CH 2OCH 2CF 3 H H Bu t H
II-18 The 2-trifluoromethyl CH 2OCH 2CF 3 H H Bu t H
II-19 3-(4-5-flumethiazine base) CH 2OCH 2CF 3 H H Bu t H
II-20 3-(6-chloropyridine base) CH 2OCH 2CF 3 H H Bu t H
II-21 5-(4-trifluoromethyl pyrimidine base) CH 2OCH 2CF 3 H H Bu t H
II-22 4-(2-chlorine thiazolyl) CH 2OCH 2CF 3 H H Bu t H
II-23 5-(4-trifluoromethyl thiazole base) CH 2OCH 2CF 3 H H Bu t H
II-24 5-(1-methyl-3-ethyl pyrazolyl) CH 2OCH 2CF 3 H H Bu t H
II-25 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CH 2OCH 2CF 3 H H Bu t H
II-26 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CH 2OCH 2CF 3 H H Bu t H
II-27 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CH 2OCH 2CF 3 H H Bu t H
II-28 The 4-chloro-phenyl- CH 2OCH 2CN H H Bu t H
II-29 The 2-trifluoromethyl CH 2OCH 2CN H H Bu t H
II-30 3-(4-5-flumethiazine base) CH 2OCH 2CN H H Bu t H
II-31 3-(6-chloropyridine base) CH 2OCH 2CN H H Bu t H
II-32 5-(4-trifluoromethyl pyrimidine base) CH 2OCH 2CN H H Bu t H
II-33 4-(2-chlorine thiazolyl) CH 2OCH 2CN H H Bu t H
II-34 5-(4-trifluoromethyl thiazole base) CH 2OCH 2CN H H Bu t H
II-35 5-(1-methyl-3-ethyl pyrazolyl) CH 2OCH 2CN H H Bu t H
II-36 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CH 2OCH 2CN H H Bu t H
II-37 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CH 2OCH 2CN H H Bu t H
II-38 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CH 2OCH 2CN H H Bu t H
II-39 The 4-chloro-phenyl- CH 2OCH 2CO 2CH 3 H H Bu t H
II-40 The 2-trifluoromethyl CH 2OCH 2CO 2CH 3 H H Bu t H
II-41 3-(4-5-flumethiazine base) CH 2OCH 2CO 2CH 3 H H Bu t H
II-42 3-(6-chloropyridine base) CH 2OCH 2CO 2CH 3 H H Bu t H
II-43 5-(4-trifluoromethyl pyrimidine base) CH 2OCH 2CO 2CH 3 H H Bu t H
II-44 4-(2-chlorine thiazolyl) CH 2OCH 2CO 2CH 3 H H Bu t H
II-45 5-(4-trifluoromethyl thiazole base) CH 2OCH 2CO 2CH 3 H H Bu t H
[0148]
II-46 5-(1-methyl-3-ethyl pyrazolyl) CH 2OCH 2CO 2CH 3 H H Bu t H
II-47 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CH 2OCH 2CO 2CH 3 H H Bu t H
II-48 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CH 2OCH 2CO 2CH 3 H H Bu t H
II-49 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CH 2OCH 2CO 2CH 3 H H Bu t H
II-50 The 4-chloro-phenyl- CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-51 The 2-trifluoromethyl CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-52 3-(4-5-flumethiazine base) CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-53 3-(6-chloropyridine base) CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-54 5-(4-trifluoromethyl pyrimidine base) CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-55 4-(2-chlorine thiazolyl) CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-56 5-(4-trifluoromethyl thiazole base) CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-57 5-(1-methyl-3-ethyl pyrazolyl) CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-58 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-59 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-60 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CH 2OCH 2CON(CH 3) 2 H H Bu t H
II-61 The 4-chloro-phenyl- CH 2OCH 2CONHCH 3 H H Bu t H
II-62 The 2-trifluoromethyl CH 2OCH 2CONHCH 3 H H Bu t H
II-63 3-(4-5-flumethiazine base) CH 2OCH 2CONHCH 3 H H Bu t H
II-64 3-(6-chloropyridine base) CH 2OCH 2CONHCH 3 H H Bu t H
II-65 5-(4-trifluoromethyl pyrimidine base) CH 2OCH 2CONHCH 3 H H Bu t H
II-66 4-(2-chlorine thiazolyl) CH 2OCH 2CONHCH 3 H H Bu t H
II-67 5-(4-trifluoromethyl thiazole base) CH 2OCH 2CONHCH 3 H H Bu t H
II-68 5-(1-methyl-3-ethyl pyrazolyl) CH 2OCH 2CONHCH 3 H H Bu t H
II-69 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CH 2OCH 2CONHCH 3 H H Bu t H
II-70 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CH 2OCH 2CONHCH 3 H H Bu t H
II-71 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CH 2OCH 2CONHCH 3 H H Bu t H
II-72 The 4-chloro-phenyl- CON(CH 3) 2 H H Bu t H
II-73 The 2-trifluoromethyl CON(CH 3) 2 H H Bu t H
II-74 3-(4-5-flumethiazine base) CON(CH 3) 2 H H Bu t H
II-75 3-(6-chloropyridine base) CON(CH 3) 2 H H Bu t H
II-76 5-(4-trifluoromethyl pyrimidine base) CON(CH 3) 2 H H Bu t H
II-77 4-(2-chlorine thiazolyl) CON(CH 3) 2 H H Bu t H
II-78 5-(4-trifluoromethyl thiazole base) CON(CH 3) 2 H H Bu t H
II-79 5-(1-methyl-3-ethyl pyrazolyl) CON(CH 3) 2 H H Bu t H
II-80 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CON(CH 3) 2 H H Bu t H
II-81 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CON(CH 3) 2 H H Bu t H
II-82 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CON(CH 3) 2 H H Bu t H
II-83 The 4-chloro-phenyl- CONHCH 3 H H Bu t H
II-84 The 2-trifluoromethyl CONHCH 3 H H Bu t H
II-85 3-(4-5-flumethiazine base) CONHCH 3 H H Bu t H
II-86 3-(6-chloropyridine base) CONHCH 3 H H Bu t H
II-87 5-(4-trifluoromethyl pyrimidine base) CONHCH 3 H H Bu t H
II-88 4-(2-chlorine thiazolyl) CONHCH 3 H H Bu t H
[0149]
II-89 5-(4-trifluoromethyl thiazole base) CONHCH 3 H H Bu t H
II-90 5-(1-methyl-3-ethyl pyrazolyl) CONHCH 3 H H Bu t H
II-91 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CONHCH 3 H H Bu t H
II-92 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CONHCH 3 H H Bu t H
II-93 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CONHCH 3 H H Bu t H
II-94 The 4-chloro-phenyl- CONHCH 3 H H Bu t H
II-95 The 2-trifluoromethyl CONHCH 3 H H Bu t H
II-96 3-(4-5-flumethiazine base) CONHCH 3 H H Bu t H
II-97 3-(6-chloropyridine base) CONHCH 3 H H Bu t H
II-98 5-(4-trifluoromethyl pyrimidine base) CONHCH 3 H H Bu t H
II-99 4-(2-chlorine thiazolyl) CONHCH 3 H H Bu t H
II-100 5-(4-trifluoromethyl thiazole base) CONHCH 3 H H Bu t H
II-101 5-(1-methyl-3-ethyl pyrazolyl) CONHCH 3 H H Bu t H
II-102 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CONHCH 3 H H Bu t H
II-103 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CONHCH 3 H H Bu t H
II-104 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CONHCH 3 H H Bu t H
II-105 The 4-chloro-phenyl- CO 2CH 3 H H Bu t H
II-106 The 2-trifluoromethyl CO 2CH 3 H H Bu t H
II-107 3-(4-5-flumethiazine base) CO 2CH 3 H H Bu t H
II-108 3-(6-chloropyridine base) CO 2CH 3 H H Bu t H
II-109 5-(4-trifluoromethyl pyrimidine base) CO 2CH 3 H H Bu t H
II-110 4-(2-chlorine thiazolyl) CO 2CH 3 H H Bu t H
II-111 5-(4-trifluoromethyl thiazole base) CO 2CH 3 H H Bu t H
II-112 5-(1-methyl-3-ethyl pyrazolyl) CO 2CH 3 H H Bu t H
II-113 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CO 2CH 3 H H Bu t H
II-114 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CO 2CH 3 H H Bu t H
II-115 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CO 2CH 3 H H Bu t H
II-116 The 4-chloro-phenyl- CO 2CH 3 H H Bu t H
II-117 The 2-trifluoromethyl CO 2CH 3 H H Bu t H
II-118 3-(4-5-flumethiazine base) CO 2CH 3 H H Bu t H
II-119 3-(6-chloropyridine base) CO 2CH 3 H H Bu t H
II-120 5-(4-trifluoromethyl pyrimidine base) CO 2CH 3 H H Bu t H
II-121 4-(2-chlorine thiazolyl) CO 2CH 3 H H Bu t H
II-122 5-(4-trifluoromethyl thiazole base) CO 2CH 3 H H Bu t H
II-123 5-(1-methyl-3-ethyl pyrazolyl) CO 2CH 3 H H Bu t H
II-124 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CO 2CH 3 H H Bu t H
II-125 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CO 2CH 3 H H Bu t H
II-126 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CO 2CH 3 H H Bu t H
II-127 The 4-chloro-phenyl- CH 2N(CH 3) 2 H H Bu t H
II-128 The 2-trifluoromethyl CH 2N(CH 3) 2 H H Bu t H
II-129 3-(4-5-flumethiazine base) CH 2N(CH 3) 2 H H Bu t H
II-130 3-(6-chloropyridine base) CH 2N(CH 3) 2 H H Bu t H
II-131 5-(4-trifluoromethyl pyrimidine base) CH 2N(CH 3) 2 H H Bu t H
[0150]
II-132 4-(2-chlorine thiazolyl) CH 2N(CH 3) 2 H H Bu t H
II-133 5-(4-trifluoromethyl thiazole base) CH 2N(CH 3) 2 H H Bu t H
II-134 5-(1-methyl-3-ethyl pyrazolyl) CH 2N(CH 3) 2 H H Bu t H
II-135 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) CH 2N(CH 3) 2 H H Bu t H
II-136 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) CH 2N(CH 3) 2 H H Bu t H
II-137 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) CH 2N(CH 3) 2 H H Bu t H
II-138 Phenyl P 29 H H Bu t H
II-139 The 2-trifluoromethyl P 29 H H Bu t H
II-140 The 2-aminomethyl phenyl P 29 H H Bu t H
II-141 The 3-chloro-phenyl- P 29 H H Bu t H
II-142 The 2-chloro-phenyl- P 29 H H Bu t H
II-143 The 4-chloro-phenyl- P 29 H H Bu t H
II-144 The 4-bromophenyl P 29 H H Bu t H
II-145 The 4-iodophenyl P 29 H H Bu t H
II-146 The 4-nitrophenyl P 29 H H Bu t H
II-147 The 4-aminomethyl phenyl P 29 H H Bu t H
II-148 The 4-tert-butyl-phenyl P 29 H H Bu t H
II-149 The 4-trifluoromethyl P 29 H H Bu t H
II-150 The 3-trifluoromethyl P 29 H H Bu t H
II-151 2-chloro-4-methyl sulphonyl P 29 H H Bu t H
II-152 2-nitro-4-methyl alkylsulfonyl P 29 H H Bu t H
II-153 2-trifluoromethyl-4-fluorophenyl P 29 H H Bu t H
II-154 2-trifluoromethyl-4-methyl sulphonyl phenyl P 29 H H Bu t H
II-155 2, the 6-difluorophenyl P 29 H H Bu t H
II-156 The 2-fluorophenyl P 29 H H Bu t H
II-157 The 4-fluorophenyl P 29 H H Bu t H
II-158 The 2-p-methoxy-phenyl P 29 H H Bu t H
II-159 The 4-p-methoxy-phenyl P 29 H H Bu t H
II-160 The 4-Trifluoromethoxyphen-l P 29 H H Bu t H
II-161 3, the 4-Dimethoxyphenyl P 29 H H Bu t H
II-162 The 2-phenyl P 29 H H Bu t H
II-163 The 2-ethylphenyl P 29 H H Bu t H
II-164 The 2-isopropyl phenyl P 29 H H Bu t H
II-165 The 2-tert-butyl-phenyl P 29 H H Bu t H
II-166 (4-chloro-phenyl-) methyl P 29 H H Bu t H
II-167 (4-chloro-phenyl-)-isopropyl-methyl P 29 H H Bu t H
II-168 2,2-3,3-tetramethyl-ring propyl P 29 H H Bu t H
II-169 2-(5-nitrofuran base) P 29 H H Bu t H
II-170 2-(5-chlorine furyl) P 29 H H Bu t H
II-171 2-(3-trifluoromethyl furyl) P 29 H H Bu t H
II-172 2-(3-chlorine furyl) P 29 H H Bu t H
II-173 3-(2-trifluoromethyl furyl) P 29 H H Bu t H
II-174 3-(2-chlorine furyl) P 29 H H Bu t H
[0151]
II-175 2-(3-chlorothiophene base) P 29 H H Bu t H
II-176 2-(3 methyl thiophene base) P 29 H H Bu t H
II-177 3-(2-iodothiophen base) P 29 H H Bu t H
II-178 3-(2-thiotolene base) P 29 H H Bu t H
II-179 3-(4-trifluoromethyl pyrpole base) P 29 H H Bu t H
II-180 3-(1-methyl-4-trifluoromethyl pyrpole base) P 29 H H Bu t H
II-181 2-(1-methylpyrrole base) P 29 H H Bu t H
II-182 4-(5-San Fu Jia Ji oxazolyl) P 29 H H Bu t H
II-183 4-(2-methyl-5-San Fu Jia Ji oxazolyl) P 29 H H Bu t H
II-184 4-(2-chlorine thiazolyl) P 29 H H Bu t H
II-185 4-(5-trifluoromethyl thiazole base) P 29 H H Bu t H
II-186 4-(2-methyl-5-trifluoromethyl thiazole base) P 29 H H Bu t H
II-187 5-(2-chloro-4-trifluoromethyl thiazole base) P 29 H H Bu t H
II-188 5-(2-cyanic acid-4-trifluoromethyl thiazole base) P 29 H H Bu t H
II-189 5-(2-methoxyl group-4-trifluoromethyl thiazole base) P 29 H H Bu t H
II-190 5-(2-methylthio group-4-trifluoromethyl thiazole base) P 29 H H Bu t H
II-191 5-(2-methyl sulphonyl-4-trifluoromethyl thiazole base) P 29 H H Bu t H
II-192 5-(4-trifluoromethyl thiazole base) P 29 H H Bu t H
II-193 5-(2-methyl-4-trifluoromethyl thiazole base) P 29 H H Bu t H
II-194 5-(2,4-two trifluoromethyl thiazole bases) P 29 H H Bu t H
II-195 5-(1-phenylpyrazole base) P 29 H H Bu t H
II-196 5-(1-phenyl-3-methylpyrazole base) P 29 H H Bu t H
II-197 5-(1,3-dimethyl pyrazole base) P 29 H H Bu t H
II-198 5-(1,3,4-trimethylammonium pyrazolyl) P 29 H H Bu t H
II-199 5-(1-methyl-3-ethyl-4-chlorine pyrazolyl) P 29 H H Bu t H
II-200 5-(1-methyl-3-ethyl pyrazolyl) P 29 H H Bu t H
II-201 5-(1,3-dimethyl--4-chlorine pyrazolyl) P 29 H H Bu t H
II-202 5-(1-phenyl-3-trifluoromethyl pyrazol base) P 29 H H Bu t H
II-203 5-(1-methyl-3-trifluoromethyl pyrazol base) P 29 H H Bu t H
II-204 5-(1-methyl-3-trifluoromethyl-4-chlorine pyrazolyl) P 29 H H Bu t H
II-205 5-(1-phenyl-3-chlorine pyrazolyl) P 29 H H Bu t H
II-206 5-(1-(2-pyridyl)-3-chlorine pyrazolyl) P 29 H H Bu t H
II-207 5-(1-(2-pyridyl)-3-bromine pyrazolyl) P 29 H H Bu t H
II-208 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) P 29 H H Bu t H
II-209 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) P 29 H H Bu t H
II-210 5-(1-(2-(3-chloropyridine base))-3-trifluoromethyl pyrazol base) P 29 H H Bu t H
II-211 4-(1-phenyl-3-trifluoromethyl pyrazol base) P 29 H H Bu t H
II-212 4-(1-methyl-3-trifluoromethyl pyrazol base) P 29 H H Bu t H
II-213 4-(1-methyl-3-trifluoromethyl-5 chlorine pyrazolyl) P 29 H H Bu t H
II-214 4-(1-methyl-5-trifluoromethyl pyrazol base) P 29 H H Bu t H
II-215 3-(5-methyl-isoxazole base) P 29 H H Bu t H
II-216 3-(5-trifluoromethyl isoxazolyl) P 29 H H Bu t H
II-217 4-(3-trifluoromethyl isoxazolyl) P 29 H H Bu t H
[0152]
II-218 4-(5-Trifluoromethyl-1,2,3 triazolyls) P 29 H H Bu t H
II-219 5-(4-methyl isophthalic acid, 2,3 thiadiazolyl groups) P 29 H H Bu t H
II-220 5-(4-Trifluoromethyl-1,2,3 thiadiazolyl groups) P 29 H H Bu t H
II-221 3-(2-chloropyridine base) P 29 H H Bu t H
II-222 3-(2-fluorine pyridyl) P 29 H H Bu t H
II-223 3-(2-5-flumethiazine base) P 29 H H Bu t H
II-224 3-(2-is cyanopyridine-based) P 29 H H Bu t H
II-225 3-(2-methoxypyridine base) P 29 H H Bu t H
II-226 3-(2-phenoxypyridines base) P 29 H H Bu t H
II-227 3-(2-methylthio group pyridyl) P 29 H H Bu t H
II-228 3-(2-methyl sulphonyl pyridyl) P 29 H H Bu t H
II-229 3-(4-5-flumethiazine base) P 29 H H Bu t H
II-230 3-(6-chloropyridine base) P 29 H H Bu t H
II-231 3-(6-fluorine pyridyl) P 29 H H Bu t H
II-232 3-(6-5-flumethiazine base) P 29 H H Bu t H
II-233 3-(6-is cyanopyridine-based) P 29 H H Bu t H
II-234 3-(6-methoxypyridine base) P 29 H H Bu t H
II-235 3-(6-methyl sulphonyl pyridyl) P 29 H H Bu t H
II-236 3-(2,6-two chloro-4-picolyls) P 29 H H Bu t H
II-237 3-(2,6-dichlor-4-trifluoromethyl pyridyl) P 29 H H Bu t H
II-238 The 4-pyridyl P 29 H H Bu t H
II-239 5-(4-trifluoromethyl pyrimidine base) P 29 H H Bu t H
II-240 5-(2-chloro-4-trifluoromethyl pyrimidine base) P 29 H H Bu t H
II-241 5-(2-methyl-4-trifluoromethyl pyrimidine base) P 29 H H Bu t H
II-242 3-(5,6-dihydro-2-methyl isophthalic acid, 4-oxygen thiapyran base) P 29 H H Bu t H
II-243 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) P 29 H H Bu t H
II-244 The 4-chloro-phenyl- P 30 H H Bu t H
II-245 The 2-trifluoromethyl P 30 H H Bu t H
II-246 3-(4-5-flumethiazine base) P 30 H H Bu t H
II-247 3-(6-chloropyridine base) P 30 H H Bu t H
II-248 5-(4-trifluoromethyl pyrimidine base) P 30 H H Bu t H
II-249 4-(2-chlorine thiazolyl) P 30 H H Bu t H
II-250 5-(4-trifluoromethyl thiazole base) P 30 H H Bu t H
II-251 5-(1-methyl-3-ethyl pyrazolyl) P 30 H H Bu t H
II-252 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) P 30 H H Bu t H
II-253 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) P 30 H H Bu t H
II-254 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) P 30 H H Bu t H
II-255 The 4-chloro-phenyl- P 31 H H Bu t H
II-256 The 2-trifluoromethyl P 31 H H Bu t H
II-257 3-(4-5-flumethiazine base) P 31 H H Bu t H
II-258 5-(1-methyl-3-ethyl pyrazolyl) P 31 H H Bu t H
II-259 The 4-chloro-phenyl- P 33 H H Bu t H
II-260 The 2-trifluoromethyl P 33 H H Bu t H
[0153]
II-261 3-(4-5-flumethiazine base) P 33 H H Bu t H
II-262 5-(1-methyl-3-ethyl pyrazolyl) P 33 H H Bu t H
II-263 The 4-chloro-phenyl- P 32 H H Bu t H
II-264 The 2-trifluoromethyl P 32 H H Bu t H
II-265 3-(4-5-flumethiazine base) P 32 H H Bu t H
II-266 5-(1-methyl-3-ethyl pyrazolyl) P 32 H H Bu t H
II-267 The 4-chloro-phenyl- P 34 H H Bu t H
II-268 The 2-trifluoromethyl P 34 H H Bu t H
II-269 3-(4-5-flumethiazine base) P 34 H H Bu t H
II-270 5-(1-methyl-3-ethyl pyrazolyl) P 34 H H Bu t H
II-271 2, the 6-difluorophenyl P 1 H H Bu t H
II-272 The 4-chloro-phenyl- P 1 H H Bu t H
II-273 The 2-trifluoromethyl P 1 H H Bu t H
II-274 3-(4-5-flumethiazine base) P 1 H H Bu t H
II-275 3-(6-chloropyridine base) P 1 H H Bu t H
II-276 2-(6-(3-trifluoromethyl) pyridyl) P 1 H H Bu t H
II-277 5-(4-trifluoromethyl pyrimidine base) P 1 H H Bu t H
II-278 4-(2-chlorine thiazolyl) P 1 H H Bu t H
II-279 5-(4-trifluoromethyl thiazole base) P 1 H H Bu t H
II-280 5-(2-methyl-4-trifluoromethyl thiazole base) P 1 H H Bu t H
II-281 5-(2-chloro-4-trifluoromethyl thiazole base) P 1 H H Bu t H
II-282 5-(1-methyl-3-trifluoromethyl pyrazol base) P 1 H H Bu t H
II-283 5-(1-methyl-3-ethyl pyrazolyl) P 1 H H Bu t H
II-284 5-(1-(2-(3-chloropyridine base))-3-chlorine pyrazolyl) P 1 H H Bu t H
II-285 5-(1-(2-(3-chloropyridine base))-3-bromine pyrazolyl) P 1 H H Bu t H
II-286 5-(4-Trifluoromethyl-1,2,3 thiadiazoles) P 1 H H Bu t H
II-287 3-(5,6-dihydro-2-Trifluoromethyl-1,4-oxygen thiapyran base) P 1 H H Bu t H
II-288 The 2-trifluoromethyl P 2 H H Bu t H
II-289 The 2-trifluoromethyl P 3 H H Bu t H
II-290 The 2-trifluoromethyl P 5 H H Bu t H
II-291 The 2-trifluoromethyl P 6 H H Bu t H
II-292 The 2-trifluoromethyl P 7 H H Bu t H
II-293 The 2-trifluoromethyl P 8 H H Bu t H
II-294 The 2-trifluoromethyl P 9 H H Bu t H
II-295 The 2-trifluoromethyl P 10 H H Bu t H
II-296 The 2-trifluoromethyl P 11 H H Bu t H
II-297 The 2-trifluoromethyl P 12 H H Bu t H
II-298 The 2-trifluoromethyl P 13 H H Bu t H
II-299 The 2-trifluoromethyl P 14 H H Bu t H
II-300 The 2-trifluoromethyl P 15 H H Bu t H
II-301 The 2-trifluoromethyl P 16 H H Bu t H
II-302 The 2-trifluoromethyl P 17 H H Bu t H
II-303 The 2-trifluoromethyl P 18 H H Bu t H
[0154]
II-304 The 2-trifluoromethyl P 4 H H Bu t H
II-305 The 2-trifluoromethyl P 19 H H Bu t H
II-306 The 2-trifluoromethyl P 20 H H Bu t H
II-307 The 2-trifluoromethyl P 21 H H Bu t H
II-308 The 2-trifluoromethyl P 22 H H Bu t H
II-309 The 2-trifluoromethyl P 23 H H Bu t H
II-310 The 2-trifluoromethyl P 24 H H Bu t H
II-311 The 2-trifluoromethyl P 25 H H Bu t H
II-312 The 2-trifluoromethyl P 26 H H Bu t H
II-313 The 2-trifluoromethyl (CH 2) 2OCH 3 H Cl Bu t H
II-314 The 2-trifluoromethyl (CH 2) 2OCH 3 H F Bu t H
II-315 The 2-trifluoromethyl (CH 2) 2OCH 3 H Br Bu t H
II-316 The 2-trifluoromethyl (CH 2) 2OCH 3 H I Bu t H
II-317 The 2-trifluoromethyl (CH 2) 2OCH 3 H CH 3 Bu t H
II-318 The 2-trifluoromethyl (CH 2) 2OCH 3 CH 3 H Bu t H
II-319 The 2-trifluoromethyl (CH 2) 2OCH 3 CN H Bu t H
II-320 The 2-trifluoromethyl (CH 2) 2OCH 3 H Cl Bu t Cl
II-321 The 2-trifluoromethyl CH 2OCH 2CF 3 H Cl Bu t H
II-322 The 2-trifluoromethyl CH 2OCH 2CF 3 H F Bu t H
II-323 The 2-trifluoromethyl CH 2OCH 2CF 3 H Br Bu t H
II-324 The 2-trifluoromethyl CH 2OCH 2CF 3 H I Bu t H
II-325 The 2-trifluoromethyl CH 2OCH 2CF 3 H CH 3 Bu t H
II-326 The 2-trifluoromethyl CH 2OCH 2CF 3 CH 3 H Bu t H
II-327 The 2-trifluoromethyl CH 2OCH 2CF 3 CN H Bu t H
II-328 The 2-trifluoromethyl CH 2OCH 2CF 3 H Cl Bu t Cl
II-329 The 2-trifluoromethyl CH 2OCH 2CN H Cl Bu t H
II-330 The 2-trifluoromethyl CH 2OCH 2CN H F Bu t H
II-331 The 2-trifluoromethyl CH 2OCH 2CN H Br Bu t H
II-332 The 2-trifluoromethyl CH 2OCH 2CN H I Bu t H
II-333 The 2-trifluoromethyl CH 2OCH 2CN H CH 3 Bu t H
II-334 The 2-trifluoromethyl CH 2OCH 2CN CH 3 H Bu t H
II-335 The 2-trifluoromethyl CH 2OCH 2CN CN H Bu t H
II-336 The 2-trifluoromethyl CH 2OCH 2CN H Cl Bu t Cl
II-337 The 2-trifluoromethyl CH 2OCH 2CO 2CH 3 H Cl Bu t H
II-338 The 2-trifluoromethyl CH 2OCH 2CO 2CH 3 H F Bu t H
II-339 The 2-trifluoromethyl CH 2OCH 2CO 2CH 3 H Br Bu t H
II-340 The 2-trifluoromethyl CH 2OCH 2CO 2CH 3 H I Bu t H
II-341 The 2-trifluoromethyl CH 2OCH 2CON(CH 3) 2 H Cl Bu t H
II-342 The 2-trifluoromethyl CH 2OCH 2CON(CH 3) 2 H F Bu t H
II-343 The 2-trifluoromethyl CH 2OCH 2CON(CH 3) 2 H Br Bu t H
II-344 The 2-trifluoromethyl CH 2OCH 2CON(CH 3) 2 H I Bu t H
II-345 The 2-trifluoromethyl CH 2OCH 2CON(CH 3) 2 H CH 3 Bu t H
II-346 The 2-trifluoromethyl CH 2OCH 2CON(CH 3) 2 CH 3 H Bu t H
[0155]
II-347 The 2-trifluoromethyl CH 2OCH 2CON(CH 3) 2 CN H Bu t H
II-348 The 2-trifluoromethyl CH 2OCH 2CON(CH 3) 2 H Cl Bu t Cl
II-349 The 2-trifluoromethyl CH 2OCH 2CONHCH 3 H Cl Bu t H
II-350 The 2-trifluoromethyl CH 2OCH 2CONHCH 3 H F Bu t H
II-351 The 2-trifluoromethyl CH 2OCH 2CONHCH 3 H CH 3 Bu t H
II-352 The 2-trifluoromethyl CH 2OCH 2CONHCH 3 CH 3 H Bu t H
II-353 The 2-trifluoromethyl CH 2OCH 2CONHCH 3 CN H Bu t H
II-354 The 2-trifluoromethyl CH 2OCH 2CONHCH 3 H Cl Bu t Cl
II-355 The 2-trifluoromethyl CON(CH 3) 2 CN H Bu t H
II-356 The 2-trifluoromethyl CON(CH 3) 2 H Cl Bu t Cl
II-357 The 2-trifluoromethyl CON(CH 3) 2 H Cl Bu t H
II-358 The 2-trifluoromethyl CON(CH 3) 2 H F Bu t H
II-359 The 2-trifluoromethyl CON(CH 3) 2 H CH 3 Bu t H
II-360 The 2-trifluoromethyl CON(CH 3) 2 CH 3 H Bu t H
II-361 The 2-trifluoromethyl CON(CH 3) 2 CN H Bu t H
II-362 The 2-trifluoromethyl CON(CH 3) 2 H Cl Bu t Cl
II-363 The 2-trifluoromethyl CONHCH 3 H Cl Bu t H
II-364 The 2-trifluoromethyl CONHCH 3 CN H Bu t H
II-365 The 2-trifluoromethyl CONHCH 3 CH 3 H Bu t H
II-366 The 2-trifluoromethyl CONHCH 3 H CH 3 Bu t Cl
II-367 The 2-trifluoromethyl CO 2CH 3 H Cl Bu t H
II-368 The 2-trifluoromethyl CO 2CH 3 H F Bu t H
II-369 The 2-trifluoromethyl CO 2CH 3 H Br Bu t H
II-370 The 2-trifluoromethyl CO 2CH 3 H I Bu t H
II-371 The 2-trifluoromethyl CO 2CH 3 H CH 3 Bu t H
II-372 The 2-trifluoromethyl CO 2CH 3 CH 3 H Bu t H
II-373 The 2-trifluoromethyl CO 2CH 3 CN H Bu t H
II-374 The 2-trifluoromethyl CO 2CH 3 H Cl Bu t Cl
II-375 The 2-trifluoromethyl P 29 H Cl Bu t H
II-376 The 2-trifluoromethyl P 29 H F Bu t H
II-377 The 2-trifluoromethyl P 29 H Br Bu t H
II-378 The 2-trifluoromethyl P 29 H I Bu t H
II-379 The 2-trifluoromethyl P 29 H CH 3 Bu t H
II-380 The 2-trifluoromethyl P 29 CH 3 H Bu t H
II-381 The 2-trifluoromethyl P 29 CN H Bu t H
II-382 The 2-trifluoromethyl P 29 H Cl Bu t Cl
II-383 The 2-trifluoromethyl P 1 H F Bu t H
II-384 The 2-trifluoromethyl P 1 CN H Bu t H
II-385 The 2-trifluoromethyl P 1 CH 3 H Bu t H
II-386 The 2-trifluoromethyl P 1 H CH 3 Bu t Cl
II-387 The 2-trifluoromethyl P 1 H Cl Bu t H
II-388 The 2-trifluoromethyl P 1 H Cl Bu t Cl
II-389 The 2-trifluoromethyl P 19 H Cl Bu t H
[0156]?
Figure G200810116762201D00301
Figure G200810116762201D00311
Ph represents phenyl, Bu in the last table tRepresent the tertiary butyl, wavy line is represented in this key and the general formula (I) other part P that links to each other 1-P 28Structure the same, P 29-P 34Represent following structure:
The acarid that substituted cyanoacetate compound shown in the general formula of the present invention (I) can effectively be directed against is a garden pest, like cotton spider mites, carmine spider mite (Carmine spider mite), the full pawl of citrus full (citrus red mite), refreshing Ze Shi leaf (kanzawa spidermite), mite apple tetranychus (fruit tree red) (European red mite), tea half tarsonemid mite (broad mite), citrus rust full (pink citrusrust), Rhizoglyphus hyacinthi (bulb mite) etc.
Substituted cyanoacetate compound shown in the general formula of the present invention (I) also can effectively be directed against indoor acarid, like flour mite, wheat food mite, tarsonemid mite etc.
Even when using with lower concentration, substituted cyanoacetate compound of the present invention also demonstrates good acarid for various acarids and prevents and kill off effect.Each stage (like ovum, larva, adult) that the term " acarid is prevented and kill off " that the present invention uses means in the acarid life cycle has acaricidal activity.
Substituted cyanoacetate compound of the present invention demonstrates good acarid and prevents and kill off effect in 14-40 days long-time.
Even for those traditional miticide has been produced drug-fast acarid, substituted cyanoacetate compound of the present invention also demonstrates good acarid and prevents and kill off effect.
About the security aspect; Substituted cyanoacetate compound of the present invention is satisfactory; They do not influence plant, honeybee, trichogramma evanescens (Trichogramma evanescens), Encarsia formosa (Enscarsia formosa), little dark-coloured flower stinkbug (minutepirate bug) useful insects such as (minute pirate bugs (Orius spp)), the mite that Chilean little phytoseiid mite (Phytoseiulus persimilis) etc. are useful etc.
When the cyanoacetate compound shown in the general formula of the present invention (I) was used for agricultural use, amount of application was/1000 square metres of 0.1-500 grams usually ,/1000 square metres of preferred 0.5-200 grams.When the compsn dilute with water of the present invention with forms such as emulsifiable concentrate, wettable powder, flowing agents used, the application concentration of active ingredient was generally 1-1000ppm, is preferably 1-500ppm.When the miticide that contains general formula of the present invention (I) compound uses with forms such as granula, pulvis, can not dilute directly and use.
Although more than listed amount and the concentration used, according to different situations such as the kind of preparation, time of application, place to use, application process, pest species, degree of damage, amount of using and concentration can suitably increase or reduce.
Compound of the present invention itself can be used as miticide and sterilant.But preferably it is mixed with solid-state carrier, liquid carrier or gaseous carrier (sprays), add tensio-active agent and other auxiliary agent in case of necessity; According to known compound method, can it be mixed with various forms, like oil solution, emulsifiable concentrate, wettable powder, flowing agent, pulvis, smoke substance or fumigant etc.Cyanoacetate compound of the present invention is usually with 0.01-99% weight, and the ratio of preferred 0.1-50% weight is included in these preparations.Therefore the present invention also comprises a kind of insecticide acaricide composition, contains general formula (I) compound as active ingredient, and carrier and/or tensio-active agent, and the weight content of active ingredient is 0.01-99% in the compsn.
Carrier and/or tensio-active agent commonly used in known miticide and the sterilant all can be used in the compsn of the present invention.Can also contain other auxiliary agents for example sticking agent, dispersion agent, stablizer etc. in case of necessity in the compsn.
The compounds of this invention can be mixed together use with other active substance such as sterilant, attractive substance, sterilizing agent, miticide, nematocides, mycocide, growth regulator or weedicide etc.
Embodiment
Below will be described in more detail the present invention with reference to preparation example, formulation example and biological activity test example, but these embodiment and unrestricted scope of the present invention.
The preparation of instance 1 compound I-25
(1), to the preparation of tert.-butylbenzene acetonitrile
Figure G200810116762201D00321
Take by weighing 20 gram sodium cyanides and be dissolved in 30 milliliters the water, stir and make it to dissolve fully, add in 100 milliliters the ethanol.Be warming up to 75 ℃, slowly drip 68 gram 4 tert butylbenzyl chlorides, reacted 8 hours down at 75-80 ℃.Thin-layer chromatography shows that raw material reaction is complete, adds 30 gram Anhydrous potassium carbonates, transfers reacting liquid pH value to 8～9.Pressure reducing and steaming ethanol adds 100 ml waters.With ethyl acetate extraction (100ml * 2); Merge organic layer; And with washing (20ml * 2); Saturated common salt washing (20ml * 2), anhydrous magnesium sulfate drying.Column chromatography obtains 42 gram products.
(2), the preparation of 2-(4-tert-butyl-phenyl)-ethyl cyanacetate
Figure G200810116762201D00323
Take by weighing in the round-bottomed flask of 500 milliliters of sodium hydride 3.5 gram (60% content) addings, add 120 milliliters of exsiccant THFs, the tert.-butylbenzene acetonitrile is added drop-wise in the reaction solution being dissolved in the gram of 15 in 10 milliliters of THFs.Dropping temperature is 0-5 ℃, finishes, and rises to room temperature gradually in about 20 minutes.Again to wherein slowly dripping the 12 gram diethyl carbonate solution that are dissolved in 100 milliliters of THFs.Dropwise, reflux 4 hours, thin-layer chromatography shows that raw material reaction is complete.Solvent evaporated adds little water, and it is about 2 that Hydrogen chloride is regulated pH.Ethyl acetate extraction (200ml * 2) merges organic layer, organic layer washing (30ml * 2), saturated common salt washing (30ml * 2), anhydrous magnesium sulfate drying.Column chromatography obtains yellow oil 2.8 grams.
Nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3), δ ppm:1.32 (9H, s), 1.27-1.30 (3H, t), 4.23-4.25 (2H, q), 4.60 (1H, s), 7.40 (2H, d), 7.42 (2H, d).
(3), the preparation of 2-(4-tert-butyl-phenyl)-cyanoacetic acid 2-(phenyl) ethyl ester
Figure G200810116762201D00324
Take by weighing 5 gram 2-(4-tert-butyl-phenyl)-ethyl cyanacetates, 6 and restrain in the round-bottomed flask of 100 milliliters of 2-phenylethyl alcohols addings, add a tetrabutyl titanate, be warming up to 100 ℃, reacted 12 hours.Thin-layer chromatography shows that raw material reaction is complete.In reaction solution, add little water,, merge organic layer with ethyl acetate extraction (100ml * 3).Organic layer washing (20ml * 2), saturated common salt washing (20ml * 2), anhydrous magnesium sulfate drying.Column chromatography obtains white solid 4.0 grams, fusing point: 56-58 ℃.
Nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3), δ ppm:1.32 (9H, s), 2.92-2.97 (2H, t), 4.37-4.41 (2H, t), 4.66 (1H, s), 7.11-7.12 (1H, d), 7.13-7.33 (4H, m), 7.37-7.45 (4H, m).
(4), the preparation of compound I-25
0.3 gram sodium hydride (60% content) and 10 milliliters of THFs add in 125 milliliters of round-bottomed flasks; In 0-5 ℃ of scope, will be dissolved in the gram of 1.6 in 10 milliliters of THFs 2-(4-tert-butyl-phenyl)-cyanoacetic acid 2-(phenyl) ethyl ester is added drop-wise in the reaction solution; React after 30 minutes, will be dissolved in the gram of 3.6 in 10 milliliters of THFs 2-(trifluoromethyl)-Benzoyl chloride 99min. again and slowly be added drop-wise in the reaction solution, dropwise; Be warming up to room temperature gradually, reacted 4 hours.THF is removed in decompression, adds little water, and it is about 2 that Hydrogen chloride is regulated pH.Ethyl acetate extraction (30ml * 2) merges organic phase, and with washing (20ml * 2), saturated common salt washing (20ml * 2), anhydrous magnesium sulfate drying.Column chromatography obtains 2.3 grams, fusing point: 92-94 ℃.
Nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3), δ ppm:1.32 (9H, s), 2.98-3.03 (4H, t), 4.43-4.54 (2H, m), 7.00-7.03 (1H, d), 7.19-7.31 (4H, m), 7.41-7.56 (7H, m), 7.76-7.79 (1H, d).
The preparation of instance 2 compound I I-139
(1), the preparation of 2-(4-tert-butyl-phenyl)-cyanoacetic acid (2-tetrahydrofuran base) methyl ester
Figure G200810116762201D00332
Take by weighing 5 gram 2-(4-tert-butyl-phenyl)-ethyl cyanacetates, 6 and restrain in the round-bottomed flask of 100 milliliters of tetrahydrofurfuryl alcohols addings, add a tetrabutyl titanate, be warming up to 100 ℃, reacted 12 hours.Thin-layer chromatography shows that raw material reaction is complete.In reaction solution, add little water,, merge organic layer with ethyl acetate extraction (100ml * 3).Organic layer washing (20ml * 2), saturated common salt washing (20ml * 2), anhydrous magnesium sulfate drying.Column chromatography obtains oily matter 7.6 grams.
Nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3), δ ppm:1.32 (9H, s), 1.48-1.68 (1H, m), 1.85-1.90 (3H, m), 3.77-3.80 (2H, m), 4.12-4.15 (2H, m), 4.22-4.25 (1H, m), 4.77 (1H, s), 7.37-7.50 (4H, m).
(2), the preparation of compound I I-139
Figure G200810116762201D00333
0.53 gram sodium hydride (60% content) and 10 milliliters of THFs add in 125 milliliters of round-bottomed flasks; 3 gram 2-(4-tert-butyl-phenyl)-cyanoacetic acid (2-tetrahydrofuran base) methyl ester that in 0-5 ℃ of scope, will be dissolved in 10 milliliters of THFs are added drop-wise in the reaction solution; React after 30 minutes, will be dissolved in again 10 milliliters of THFs 1.9 the gram 2-(trifluoromethyl)-Benzoyl chloride 99min.s slowly be added drop-wise in the reaction solution, add finish after; Be warming up to room temperature gradually, reacted 4 hours.THF is removed in decompression, adds little water, and it is about 2 that Hydrogen chloride is regulated pH.Ethyl acetate extraction (20ml * 2) merges organic phase, and with washing (20ml * 2), saturated common salt washing (20ml * 2), anhydrous magnesium sulfate drying.Column chromatography obtains 2.0 gram oily maters.
Nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3), δ ppm:1.31 (9H, s), 1.63-2.45 (4H, m), 3.65-3.68 (2H, m), 4.32-4.34 (3H, m), 7.31-4.15 (2H, m), 7.48-7.51 (4H, m), 7.56-7.59 (4H, m).
The fusing point of compound I-47: 84-86 ℃, nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3), δ ppm:1.34 (9H, s), 2.00-2.05 (4H, m), 2.67-2.72 (4H, t), 4.26-4.34 (2H, m), 7.04-7.05 (1H, d), 7.15-7.29 (4H, m), 7.46-7.61 (7H, m), 7.78 (1H, d).
Formulation examples
The embodiment of following series preparation is for example clear to be used to prevent and treat the pest mite class, the compsn of Plant nematode or insect, and these compsns comprise the The compounds of this invention as activeconstituents, as preparing those compounds described in the embodiment.Compsn described in the embodiment can be diluted to the concentration that is suitable for using in the field separately and obtain Sprayable composition.The general chemical descriptor of each composition that uses in the following listed examples (following all percentage ratios that relate to all are weight percentage, and umber is parts by weight) is as follows:
Formulation example 1 (missible oil)
10 parts of each compounds of the present invention are dissolved in 45 parts of peaceful newborn 34# and 45 parts of N, in the dinethylformamide, these compositions are mixed, obtain 10% emulsifiable concentrate.
Formulation example 2 (wettable powder)
20 parts of each compounds of the present invention are joined in the mixture of 2 parts of Sodium Lauryl Sulphate BP/USPs, 4 parts of sodium lignosulfonates, 20 parts of oxidizing aqueous silicon finess of synthetic and 54 parts of clays; Through whisking appliance these compositions are mixed, obtain 20% wettable powder.
Formulation example 3 (granula)
5 parts of each compounds of the present invention are mixed with 2 parts of X 2073es, 10 parts of wilkinites and 83 parts of clays, fully stir afterwards.Add an amount of water, stir the mixture once more.Through the tablets press granulation and with its dry air, obtain 5% granula.
Formulation example 4 (pulvis)
1 part of each compound of the present invention is dissolved in an amount of acetone, in this solution, adds 5 parts of oxidizing aqueous silicon finess of synthetic, 0.3 part of tributyl phosphate and 93.7 parts of clays, mix through whisking appliance afterwards.Therefrom remove acetone through evaporation, obtain 1% pulvis.
The biological activity determination instance
Indoor acaricidal activity method for measuring is following:
After the mixed solvent dissolving of testing compound with acetone/methanol (1: 1), be diluted to required concentration with the water that contains 0.1% tween 80.(Tetranychus cinnabarinus) is target with carmine spider mite, adopts the airbrush spray method to carry out acaricidal activity and measures, and the pressure that the airbrush spraying is handled is that 10psi (is roughly equal to 0.7kg/cm 2), spouting liquid is 0.5 milliliter.Handle the mortality ratio that 2-3 day is investigated target in the back.
Active result is following for part of compounds:
Under the 40ppm dosage, mite mortality ratio such as compound I-25, II-139 are 100%, and I-47 mite mortality ratio is greater than 65%.
Under the 10ppm dosage, compound I-25 pair mite mortality ratio is greater than 95%, compound I I-139 to the mite mortality ratio greater than 85%.
2.5ppm under the dosage, compound I-25 mite mortality ratio is greater than 70%, compound I I-139 mite mortality ratio is greater than 60%.
The field test method is following:
Carry out with reference to miticide field test national standard method, subjects is citrus red mite (Panonychus citri).Behind the former medicinal acetone solution of new compound, use the water dilution that contains 0.1% tween 80 to be a series of concentration.Adopt the engine-driven atomiser spraying to handle, spouting liquid is 1000L/hm 2, each is handled 3 times and repeats, and whenever repeats to be not less than 2 branches, radix profusely at least 20 of the investigation before every re-treatment is handled back 3d, 7d, 14d, each investigation of the 21d mite number of once surviving, according to following formula calculate the mite mouth go down rate with proofread and correct preventive effect:
Figure G200810116762201D00341
Figure G200810116762201D00342
The result that the field acaricidal activity is measured is following:
The field miticidal effect of compound
Figure G200810116762201D00351

Claims (3)

1. substituted cyanoacetate compound, structure is as follows:
Figure FSB00000890436400011
2. a compound as claimed in claim 1 is in the purposes of agricultural, lawn or indoor control pest mite class and ovum thereof.
3. a miticide composition contains compound as claimed in claim 1 as active ingredient, and carrier and/or tensio-active agent, and the weight content of active ingredient is 0.01-99% in the compsn.
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Patentee before: Sinochem Corporation

Patentee before: Shenyang Research Institute of Chemical Industry