CN100390140C

CN100390140C - Nitrile compound and its pest control use

Info

Publication number: CN100390140C
Application number: CNB200480039069XA
Authority: CN
Inventors: 大平大辅; 大高健
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2003-12-26
Filing date: 2004-12-22
Publication date: 2008-05-28
Anticipated expiration: 2024-12-22
Also published as: CN1898200A; ZA200604415B

Abstract

The present invention provides a nitrile compound represented by the formula (I): wherein R represents C1-C4 fluoroalkyl, Q represents halogen, C1-C11 alkyl optionally substituted with halogen, C2-C6 alkenyl group optionally substituted with halogen, C2-C6 alkynyl optionally substituted with halogen, C3-C7 cycloalkyl optionally substituted with halogen or (C3-C7 cycloalkyl optionally substituted with halogen)C1-C4 alkyl, which has excellent control effect against pests.

Description

Nitrile compound and the purposes in insect control thereof

Technical field

The present invention relates to comprise the nitrile compound and the purposes in insect control thereof of fluoroalkyl.

Background technology

Provide some to be used for the Pest Control for example compound of insect, mite and nematode and the insect control method of using described compound so far.But these compounds effect in some cases are good inadequately.

JP-A 4-21652 and JP-A 6-116200 disclose some nitrile compound that comprises fluoroalkyl and have been used to prepare the activeconstituents of town's epilepsy agent as intermediate.

Disclosure of the Invention

A target of the present invention is for providing a kind of compound and the purposes of described compound in insect control that insect is had good control effect.

In order to seek the compound with good insect control effect, the inventor has carried out deep research.As a result, the nitrile compound that the inventor finds following formula (I) expression to insect for example arthropods (for example insect, mite) and nematode have the good control activity, thereby finished the present invention.

That is to say that the invention provides the nitrile compound of a kind of formula (I) expression, this compound is called The compounds of this invention hereinafter:

Wherein R represents the C1-C4 fluoroalkyl, and Q represents halogen, optional C1-C11 alkyl, optional C2-C6 thiazolinyl, optional C2-C6 alkynyl, optional C3-C7 cycloalkyl or (the optional C3-C7 cycloalkyl that is replaced by one or more halogens) C1-C4 alkyl that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens; The present invention also provides and has comprised the insect-killing composition of The compounds of this invention as activeconstituents, the present invention has also supplied a kind of method of Pest Control, and described method comprises that the The compounds of this invention with significant quantity is applied to described insect or is applied to the habitat of described insect.

The accompanying drawing summary

Fig. 1 is the top view that is used for the solid carrier of example of formulations 9.

Fig. 2 is the skeleton view that is used for the solid carrier of example of formulations 9.

Fig. 3 represents to be used for the paper with folding structure of example of formulations 13.As axle the folding the highest expansion of paper (a) is reached 180 ° with a plane institution movement, thus the form that for example can obtain using (b), and this form comprises tubular structure.

Fig. 4 represents to be used for the paper with folding structure of example of formulations 14.Draw back relative plane and make up folding paper (a) expansion, thus the form that obtains using (b), and this form comprises tubular structure.

Fig. 5 is the skeleton view that is used for the plastic cylinder of example of formulations 21, and the height of this cylinder is 7cm, and diameter is 8.3cm and in the bottom electric fan is housed.Each numeral is as follows, and 1: electric motor; 2: fan; 3: the flow direction of air.

Fig. 6 represents to be used for the insect device extremely of experimental example 26.Each numeral is as follows, and 4: the insecticide liquid that is used for heated volatile; 5: heating unit; 6: wicking liquid; 7: the container that insecticide liquid is housed.

Implement mode of the present invention

In the present invention, halogen is represented fluorine, chlorine or bromine.Term " C1-C6-alkyl " expression the total number of carbon atoms is the alkyl of 1-6.Term " C1-C4 fluoroalkyl " expression the total number of carbon atoms is the alkyl of 1-4, and wherein one or more hydrogen atoms are replaced by fluorine atom." C3-C7 " in the term " C3-C7 cycloalkyl " is meant the 3-7 that adds up to of carbon atom that constitutes ring structure and the carbon atom of the alkyl that is connected with the carbon atom of the described ring structure of formation.

The C1-C4 fluoroalkyl that R represents comprises C1-C2 fluoroalkyl such as trifluoromethyl, 1-one fluoro ethyl, 2-one fluoro ethyl, 1,1-two fluoro ethyls, 2,2-two fluoro ethyls, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoro ethyl, 1,2,2,2-tetrafluoro ethyl or 1,1,2,2, the 2-pentafluoroethyl group; C3 fluoroalkyl such as 2-fluoropropyl, 3-fluoropropyl, 1,1-two fluoropropyls, 2,2-two fluoropropyls, 2,3-two fluoropropyls, 3,3-two fluoropropyls, 1,2,2-trifluoro propyl, 2,2,3-trifluoro propyl, 3,3,3-trifluoro propyl, 1,1,2,2-tetrafluoro propyl group, 2,2,3,3-tetrafluoro propyl group, 2,3,3,3-tetrafluoro propyl group, 2,2,3,3,3-five fluoropropyls, 1,1,2,3,3,3-hexafluoro propyl group or 1,1,2,2,3,3,3-seven fluoropropyls; With C4 fluoroalkyl such as 1-fluorine butyl, 2-fluorine butyl, 3-fluorine butyl, 4-fluorine butyl, 1,1-difluoro butyl, 2,2-difluoro butyl, 2,3-difluoro butyl, 2,4-difluoro butyl, 3,3-difluoro butyl, 4,4-difluoro butyl, 1,2,2-trifluoro butyl, 2,2,3-trifluoro butyl, 3,3,4-trifluoro butyl, 3,4,4-trifluoro butyl, 4,4,4-trifluoro butyl, 1,1,2,2-tetrafluoro butyl, 2,2,3,3-tetrafluoro butyl, 3,3,4,4-tetrafluoro butyl, 3,4,4,4-tetrafluoro butyl, 3,3,4,4,4-five fluorine butyl, 2,2,3,3,4,4-hexafluoro butyl, 1,1,2,2,3,3-hexafluoro butyl, 1,1,2,2,3,3,4,4-octafluoro butyl or 1,1,2,2,3,3,4,4,4-nine fluorine butyl.

The halogen that Q represents comprises fluorine, chlorine and bromine.

The optional C1-C11 alkyl that is replaced by one or more halogens that Q represents comprises methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the 2-methyl-propyl, 1, the 1-dimethyl ethyl, amyl group, isopentyl, neo-pentyl, hexyl, isohexyl, 3, the 3-dimethylbutyl, heptyl, octyl group, nonyl, decyl, one methyl fluoride, difluoromethyl, trifluoromethyl, one chloromethyl, dichloromethyl, trichloromethyl, one brooethyl, 1-one fluoro ethyl, 2-one fluoro ethyl, 1-one chloroethyl, 2-one chloroethyl, 1-one bromotrifluoromethane, 2-one bromotrifluoromethane, 1,1-two fluoro ethyls, 2,2-two fluoro ethyls, 1,2, the 2-trifluoroethyl, 2,2, the 2-trifluoroethyl, 1,1,2,2-tetrafluoro ethyl, 1,1,2,2, the 2-pentafluoroethyl group, 2-chloro-1-methylethyl, the 1-fluoropropyl, the 2-fluoropropyl, the 3-fluoropropyl, the 3-chloropropyl, the 3-bromopropyl, 1,1-two fluoropropyls, 2,2-two fluoropropyls, 3,3-two fluoropropyls, 2,3, the 3-trifluoro propyl, 3,3, the 3-trifluoro propyl, 3-chloro-3,3-two fluoropropyls, 3,3-two chloro-3-fluoropropyls, 2,2,3,3-tetrafluoro propyl group, 2,2,3,3,3-five fluoropropyls, 1,1,2,3,3,3-hexafluoro propyl group, 1,1,2,2,3,3,3-seven fluoropropyls, 2-chloro-3-bromo-2,3, the 3-trifluoro propyl, 3-bromo-2,2,3,3-tetrafluoro propyl group, 2-(trifluoromethyl)-2,3,3,3-tetrafluoro propyl group, 4-fluorine butyl, the 4-chlorobutyl, the 4-brombutyl, 2-fluorine butyl, 2,2-difluoro butyl, 3-fluorine butyl, 3,3-difluoro butyl, 4,4-difluoro butyl, 2,2,3-trifluoro butyl, 2,2,3,3-tetrafluoro butyl, 2,2,3,4-tetrafluoro butyl, 3,3,4,4-tetrafluoro butyl, 3-chloro-3,4,4-trifluoro butyl, 4-bromo-3-chloro-3,4,4-trifluoro butyl, 3,4-two chloro-3,4,4-trifluoro butyl, 2,2,3,4,4-five fluorine butyl, 2,2,3,4,4,4-hexafluoro butyl, 2,2,3,3,4,4-hexafluoro butyl, 3-(trifluoromethyl)-2,2,3,3,4,4,4-seven fluorine butyl, 3,4,4,4-tetrafluoro butyl, 1,1,2,2,3,3,4,4-octafluoro butyl, 1,1,2,2,3,3,4,4,4-nine fluorine butyl, 5-fluorine amyl group, 5-chlorine amyl group, 5-bromine amyl group, 2-fluorine amyl group, 2-chlorine amyl group, 2,2-difluoro amyl group, 2,3-difluoro amyl group, 2,2-dichloro amyl group, 2,3-dichloro amyl group, 3,4-difluoro amyl group, 3,4-dichloro amyl group, 2,2,3-trifluoro amyl group, 2,2,3,3-tetrafluoro amyl group, 2,2,3,3,4-five fluorine amyl groups (pentafluorofloropentyl), 2,2,3,3,4,4-hexafluoro amyl group, 2,2,3,3,4,4,5-seven fluorine amyl groups, 2,2,3,3,4,4,5,5-octafluoro amyl group, 2,2,3,3,4,4,5,5,5-nine fluorine amyl groups, 3-fluorine amyl group, 3-chlorine amyl group, 3,3-difluoro amyl group, 3,3-dichloro amyl group, 3,3,4-trifluoro amyl group, 3,3,4,4-tetrafluoro amyl group, 3,3,4,4,5-five fluorine amyl groups, 3,4,5,5,5-five fluorine amyl groups, 3,4,4,5,5-five fluorine amyl groups, 3,3,4,4,5,5-hexafluoro amyl group, 3,3,4,4,5,5,5-seven fluorine amyl groups, 4-fluorine amyl group, 4,4-difluoro amyl group, 4,4,5-trifluoro amyl group, 4,4,5,5-tetrafluoro amyl group, 4,4,5,5,5-five fluorine amyl groups, 5,5-difluoro amyl group, 5,5,5-trifluoro amyl group, 6-fluorine hexyl, 6-chlorine hexyl, 6-bromine hexyl, 2,2-difluoro hexyl, 3-fluorine hexyl, 3,3-difluoro hexyl, 4-fluorine hexyl, 4,4-difluoro hexyl, 5,5-difluoro hexyl, 2,2,3-trifluoro hexyl, 2,2,3,3-hexafluoro hexyl (hexaflurohexyl), 2,2,3,3,4-five fluorine hexyls, 2,2,3,3,4,4-hexafluoro hexyl, 2,2,3,3,4,4,5-seven fluorine hexyls, 2,2,3,3,4,4,5,5-octafluoro hexyl, 2,2,3,3,4,4,5,5,6-nine fluorine hexyls, 2,2,3,3,4,4,5,5,6,6-ten fluorine hexyls, 2,2,3,3,4,4,5,5,6,6,6-11 fluorine hexyls, 3-fluorine hexyl, 1,1,2,2,3,3,4,4,5,5,6,6-ten difluoro hexyls, 3,3-difluoro hexyl, 3,3,4-trifluoro hexyl, 3,3,4,4-hexafluoro hexyl, 3,3,4,4,5-five fluorine hexyls, 3,3,4,4,5,5-hexafluoro hexyl, 3,3,4,4,5,5,6-seven fluorine hexyls, 4-fluorine hexyl, 4,4-difluoro hexyl, 4,4,5-trifluoro hexyl, 4,4,5,5-hexafluoro hexyl, 4,4,5,5,6-five fluorine hexyls, 4,4,5,5,6,6-hexafluoro hexyl, 4,4,5,5,6,6,6-seven fluorine hexyls, 5-fluorine hexyl, 5,5-difluoro hexyl, 5,5,6-trifluoro hexyl, 5,5,6,6-hexafluoro hexyl, 5,5,6,6,6-five fluorine hexyls, 6,6-difluoro hexyl and 6,6,6-trifluoro hexyl.

The optional C2-C6 thiazolinyl that is replaced by one or more halogens that Q represents comprises vinyl, allyl group, the 1-propenyl, 2-methyl isophthalic acid-propenyl, 2-methyl-2-propenyl, the 3-butenyl, crotyl, the 1-butylene base, 3-methyl-2-butene base, the 4-pentenyl, the 3-pentenyl, pentenyl, the 1-pentenyl, 4-methyl-3-pentenyl, the 5-hexenyl, the 4-hexenyl, the 3-hexenyl, the 2-hexenyl, the 1-hexenyl, 1-is fluoride-based, 2-is fluoride-based, the 1-chlorovinyl, the 2-chlorovinyl, 2,2-difluoroethylene base, 2, the 2-dichloroethylene, 2, the 2-dibromo vinyl, 2,3,3-three fluoro-2-propenyl, 3,3,3-three fluoro-1-propenyl, 4,4-two bromo-3-butenyls, 3,4,4-three fluoro-3-butenyls, 4,4,4-three fluoro-crotyl, 5,5-two fluoro-4-pentenyls, 4,5,5-three fluoro-4-pentenyls, 5,5,5-three fluoro-3-pentenyls, 6,6-two fluoro-5-hexenyls, 5,6,6-three fluoro-5-hexenyls and 6,6,6-three fluoro-4-hexenyls.

The optional C2-C6 alkynyl that is replaced by one or more halogens that Q represents comprises ethynyl, 1-proyl, 2-propynyl, ethyl acetylene base, 2-butyne base, 3-butynyl, 1-pentynyl, valerylene base, 3-pentynyl, 4-pentynyl, 1-hexin base, 2-hexin base, 3-hexin base, 4-hexin base, 5-hexin base, 4,4,4-three fluoro-2-butyne bases and 3-chloro-2-propynyl.

The optional C3-C7 cycloalkyl that is replaced by one or more halogens that Q represents comprises cyclopropyl, 1-methyl cyclopropyl, 2-methyl cyclopropyl, 2,2-dimethyl cyclopropyl, 2,3-dimethyl cyclopropyl, 2,2,3-trimethylammonium cyclopropyl, 2,2,3,3-tetramethyl-ring propyl group, cyclobutyl, cyclopentyl, cyclohexyl, suberyl, 1-fluorine cyclopropyl, 2-fluorine cyclopropyl, 2,2-difluoro cyclopropyl, 2,2,3-trifluoro cyclopropyl, 2,2,3,3-ptfe ring propyl group, 2,2-dichloro cyclopropyl, 4-(trifluoromethyl) cyclohexyl, 3-(methyl fluoride) cyclohexyl and 2,2,3,3-tetrachloro cyclopropyl.

(the optional C3-C7 cycloalkyl that is replaced by one or more halogens) C1-C4 alkyl that Q represents comprises the cyclopropyl methyl, 2-(cyclopropyl) ethyl, 3-(cyclopropyl) propyl group, (1-methyl cyclopropyl) methyl, 2-(1-methyl cyclopropyl) ethyl, 3-(1-methyl cyclopropyl) propyl group, cyclobutylmethyl, 2-(cyclobutyl) ethyl, 3-(cyclobutyl) propyl group, (2-fluorine cyclopropyl) methyl, 1-(2-fluorine cyclopropyl) ethyl, 2-(1-fluorine cyclopropyl) ethyl, 2-(2-fluorine cyclopropyl) ethyl, (2,2-difluoro cyclopropyl) methyl, 2-(2,2-difluoro cyclopropyl) ethyl, 1-(2,2-difluoro cyclopropyl) ethyl, (2,2,3,3-ptfe ring propyl group) methyl, (2,2-dichloro cyclopropyl) methyl, 2-(2,2-dichloro cyclopropyl) ethyl, cyclopentyl-methyl, cyclohexyl methyl, 1-(2,2,3-trifluoro cyclopropyl) ethyl, 1-(2,2,3,3-ptfe ring propyl group) ethyl, 4-(cyclopropyl) butyl, 3-(cyclopropyl) butyl, 2-(cyclopropyl) butyl, 4-(1-fluorine cyclopropyl) butyl, 4-(2-fluorine cyclopropyl) butyl, 4-(2,2-difluoro cyclopropyl) butyl, 4-(2,2,3-trifluoro cyclopropyl) butyl and 4-(2,2,3,3-ptfe ring propyl group) butyl.

The compounds of this invention for example comprises following compound:

The nitrile compound of formula (I), wherein Q is halogen, optional C1-C6-alkyl, optional C2-C6 thiazolinyl, optional C2-C6 alkynyl, optional C3-C7 cycloalkyl or (the optional C3-C7 cycloalkyl that is replaced by one or more halogens) C1-C4 alkyl that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens.

The nitrile compound of formula (I), wherein R is 2,2, the 2-trifluoroethyl;

The nitrile compound of formula (I), wherein R is 1,1,2,2-tetrafluoro ethyl;

The nitrile compound of formula (I), wherein R is 1,1,2,2,3,3-hexafluoro propyl group;

The nitrile compound of formula (I), wherein R is 1,1,2,2,3,3,4,4-octafluoro butyl;

The nitrile compound of formula (I), wherein R is 2,3,3,3-tetrafluoro-2-(trifluoromethyl) propyl group;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl with 3-5 fluorine atom;

The nitrile compound of formula (I), wherein R is the C3-C4 fluoroalkyl with 6-8 fluorine atom;

The nitrile compound of formula (I), wherein R is a trifluoromethyl;

The nitrile compound of formula (I), wherein R is the C2 fluoroalkyl;

The nitrile compound of formula (I), wherein R is the 2-fluoro ethyl;

The nitrile compound of formula (I), wherein R is 2,2-two fluoro ethyls;

The nitrile compound of formula (I), wherein R is 1,2,2,2-tetrafluoro ethyl;

The nitrile compound of formula (I), wherein R is 1,1,2,2, the 2-pentafluoroethyl group;

The nitrile compound of formula (I), wherein R is the C3 fluoroalkyl;

The nitrile compound of formula (I), wherein R is 2,2-two fluoropropyls;

The nitrile compound of formula (I), wherein R is 3,3, the 3-trifluoro propyl;

The nitrile compound of formula (I), wherein R is 1,1,2,2-tetrafluoro propyl group;

The nitrile compound of formula (I), wherein R is 2,2,3,3-tetrafluoro propyl group;

The nitrile compound of formula (I), wherein R is 2,2,3,3,3-five fluoropropyls;

The nitrile compound of formula (I), wherein R is the C4 fluoroalkyl;

The nitrile compound of formula (I), wherein R is 2,2-difluoro butyl;

The nitrile compound of formula (I), wherein R is 1,2,2-trifluoro butyl;

The nitrile compound of formula (I), wherein R is 2,2,3-trifluoro butyl;

The nitrile compound of formula (I), wherein R is 1,1,2,2-tetrafluoro butyl;

The nitrile compound of formula (I), wherein R is 2,2,3,3-tetrafluoro butyl;

The nitrile compound of formula (I), wherein R is 3,3,4,4,4-five fluorine butyl;

The nitrile compound of formula (I), wherein R is 2,2,3,3,4,4-hexafluoro butyl;

The nitrile compound of formula (I), wherein R is 1,1,2,2,3,3-hexafluoro butyl;

The nitrile compound of formula (I), wherein R is 1,1,2,2,3,3,4,4,4-nine fluorine butyl;

The nitrile compound of formula (I), wherein Q is a halogen;

The nitrile compound of formula (I), wherein Q is a bromine;

The nitrile compound of formula (I), wherein Q is a chlorine;

The nitrile compound of formula (I), wherein Q is a fluorine;

The nitrile compound of formula (I), wherein Q is the optional C1-C6 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is the optional C1 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is a methyl;

The nitrile compound of formula (I), wherein Q is a methyl fluoride;

The nitrile compound of formula (I), wherein Q is a difluoromethyl;

The nitrile compound of formula (I), wherein Q is a trifluoromethyl;

The nitrile compound of formula (I), wherein Q is a chloromethyl;

The nitrile compound of formula (I), wherein Q is a dichloromethyl;

The nitrile compound of formula (I), wherein Q is a brooethyl;

The nitrile compound of formula (I), wherein Q is the optional C2 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is an ethyl;

The nitrile compound of formula (I), wherein Q is a 2-chloro-1-methylethyl;

The nitrile compound of formula (I), wherein Q is a 1-bromo-2,2, the 2-trifluoroethyl;

The nitrile compound of formula (I), wherein Q is a 1-chloro-2,2, the 2-trifluoroethyl;

The nitrile compound of formula (I), wherein Q is 1, the 1-dimethyl ethyl;

The nitrile compound of formula (I), wherein Q is 1-one chloroethyl;

The nitrile compound of formula (I), wherein Q is 2-one chloroethyl;

The nitrile compound of formula (I), wherein Q is 2-one bromotrifluoromethane;

The nitrile compound of formula (I), wherein Q is 2-one fluoro ethyl;

The nitrile compound of formula (I), wherein Q is 2,2-two fluoro ethyls;

The nitrile compound of formula (I), wherein Q is 2,2, the 2-trifluoroethyl;

The nitrile compound of formula (I), wherein Q is 1,1,2,2-tetrafluoro ethyl;

The nitrile compound of formula (I), wherein Q is 1,1,2,2, the 2-pentafluoroethyl group;

The nitrile compound of formula (I), wherein Q is the optional C3 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is a propyl group;

The nitrile compound of formula (I), wherein Q is a sec.-propyl;

The nitrile compound of formula (I), wherein Q is the 3-chloropropyl;

The nitrile compound of formula (I), wherein Q is a 3-chloro-2-propyl group;

The nitrile compound of formula (I), wherein Q is the 3-fluoropropyl;

The nitrile compound of formula (I), wherein Q is the 3-bromopropyl;

The nitrile compound of formula (I), wherein Q is the 2-bromopropyl;

The nitrile compound of formula (I), wherein Q is 2,3-two chloropropyls;

The nitrile compound of formula (I), wherein Q is 2,2-two fluoropropyls;

The nitrile compound of formula (I), wherein Q is 3,3, the 3-trifluoro propyl;

The nitrile compound of formula (I), wherein Q is 2,2,3,3-tetrafluoro propyl group;

The nitrile compound of formula (I), wherein Q is 2,2,3,3,3-five fluoropropyls;

The nitrile compound of formula (I), wherein Q is 1,1,2,3,3,3-hexafluoro propyl group;

The nitrile compound of formula (I), wherein Q is 1,1,2,2,3,3,3-seven fluoropropyls;

The nitrile compound of formula (I), wherein Q is 2,3-two chloro-2,3,3-trifluoro propyl;

The nitrile compound of formula (I), wherein Q is a 2-chloro-3-bromo-2,3, the 3-trifluoro propyl;

The nitrile compound of formula (I), wherein Q is a 3-bromo-2,2,3,3-tetrafluoro propyl group;

The nitrile compound of formula (I), wherein Q is 2-(trifluoromethyl)-2,3,3,3-tetrafluoro propyl group;

The nitrile compound of formula (I), wherein Q is the optional C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is a butyl;

The nitrile compound of formula (I), wherein Q is a sec.-propyl;

The nitrile compound of formula (I), wherein Q is a 4-fluorine butyl;

The nitrile compound of formula (I), wherein Q is the 4-chlorobutyl;

The nitrile compound of formula (I), wherein Q is 2,2-difluoro butyl;

The nitrile compound of formula (I), wherein Q is 4,4-difluoro butyl;

The nitrile compound of formula (I), wherein Q is 4,4,4-trifluoro butyl;

The nitrile compound of formula (I), wherein Q is a 4-bromo-3-chloro-3,4,4-trifluoro butyl;

The nitrile compound of formula (I), wherein Q is a 4-bromo-3,3,4,4-tetrafluoro butyl;

The nitrile compound of formula (I), wherein Q is 3-(trifluoromethyl)-3,4,4,4-tetrafluoro butyl;

The nitrile compound of formula (I), wherein Q is 2,2,3,4,4,4-hexafluoro butyl;

The nitrile compound of formula (I), wherein Q is 3,3,4,4,4-five fluorine butyl;

The nitrile compound of formula (I), wherein Q is 2,2,3,3,4,4,4-seven fluorine butyl;

The nitrile compound of formula (I), wherein Q is 1,1,2,2,3,3,4,4-octafluoro butyl;

The nitrile compound of formula (I), wherein Q is 1,1,2,2,3,3,4,4,4-nine fluorine butyl;

The nitrile compound of formula (I), wherein Q is the optional C5 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is an amyl group;

The nitrile compound of formula (I), wherein Q is an isopentyl;

The nitrile compound of formula (I), wherein Q is 5,5,5-trifluoro amyl group;

The nitrile compound of formula (I), wherein Q is 3,3,4,4,5,5,5-seven fluorine amyl groups;

The nitrile compound of formula (I), wherein Q is 2,2,3,3,4,4,5,5-octafluoro amyl group;

The nitrile compound of formula (I), wherein Q is 2,2,3,3,4,4,5,5,5-nine fluorine amyl groups;

The nitrile compound of formula (I), wherein Q is the optional C6 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is a hexyl;

The nitrile compound of formula (I), wherein Q is an isohexyl;

The nitrile compound of formula (I), wherein Q is 6,6,6-trifluoro hexyl;

The nitrile compound of formula (I), wherein Q is 5,5,6,6,6-five fluorine hexyls;

The nitrile compound of formula (I), wherein Q is 4,4,5,5,6,6,6-seven fluorine hexyls;

The nitrile compound of formula (I), wherein Q is 3,3,4,4,5,5,6,6-octafluoro hexyl;

The nitrile compound of formula (I), wherein Q is 3,3,4,4,5,5,6,6,6-nine fluorine hexyls;

The nitrile compound of formula (I), wherein Q is 1,1,2,2,3,3,4,4,5,5,6,6-ten difluoro hexyls;

The nitrile compound of formula (I), wherein Q is the optional C2-C6 thiazolinyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is the optional vinyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is a vinyl;

The nitrile compound of formula (I), wherein Q is the 1-methyl ethylene;

The nitrile compound of formula (I), wherein Q is the 1-propenyl;

The nitrile compound of formula (I), wherein Q is the 2-propenyl;

The nitrile compound of formula (I), wherein Q is 2,3,3-three fluoro-2-propenyl;

The nitrile compound of formula (I), wherein Q is the 1-butylene base;

The nitrile compound of formula (I), wherein Q is a crotyl;

The nitrile compound of formula (I), wherein Q is a 3-methyl-2-butene base;

The nitrile compound of formula (I), wherein Q is 4,4,4-three fluoro-crotyl;

The nitrile compound of formula (I), wherein Q is the 3-butenyl;

The nitrile compound of formula (I), wherein Q is 3,4,4-three fluoro-3-butenyls;

The nitrile compound of formula (I), wherein Q is the optional C2-C6 alkynyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is an ethynyl;

The nitrile compound of formula (I), wherein Q is the 1-proyl;

The nitrile compound of formula (I), wherein Q is 2-methyl isophthalic acid-proyl;

The nitrile compound of formula (I), wherein Q is 3,3,3-three fluoro-1-proyls;

The nitrile compound of formula (I), wherein Q is a 2-propynyl;

The nitrile compound of formula (I), wherein Q is the optional C3-C7 cycloalkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is the optional cyclopropyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is a cyclopropyl;

The nitrile compound of formula (I), wherein Q is 2,2-dichloro cyclopropyl;

The nitrile compound of formula (I), wherein Q is the optional cyclobutyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is a cyclobutyl;

The nitrile compound of formula (I), wherein Q is the optional cyclopentyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is a cyclopentyl;

The nitrile compound of formula (I), wherein Q is the optional cyclohexyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is a cyclohexyl;

The nitrile compound of formula (I), wherein Q is 4,4-difluoro cyclohexyl;

The nitrile compound of formula (I), wherein Q is (the optional C3-C7 cycloalkyl that is replaced by one or more halogens) C1-C4 alkyl;

The nitrile compound of formula (I), wherein Q is the optional C4-C6 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is the cyclopropyl methyl;

The nitrile compound of formula (I), wherein Q is a cyclopentyl-methyl;

The nitrile compound of formula (I), wherein Q is 2,2-difluoro cyclopropyl methyl;

The nitrile compound of formula (I), wherein Q is 3,3-difluoro cyclopentyl-methyl;

The nitrile compound of formula (I), wherein Q is the optional C4-C6 alkyl that is replaced by one or more fluorine;

The nitrile compound of formula (I), wherein Q is the C4-C6 alkyl with 6-8 fluorine atom;

The nitrile compound of formula (I), wherein Q is the optional C3-C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein Q is the optional C3-C4 alkyl that is replaced by one or more fluorine;

The nitrile compound of formula (I), wherein Q is the C3-C4 alkyl with 6-8 fluorine atom;

The nitrile compound of formula (I), wherein Q is the optional C4 alkyl that is replaced by one or more fluorine;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl with 3-5 fluorine atom, Q is the optional C4-C6 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is the C3-C4 fluoroalkyl with 6-8 fluorine atom, Q is the optional C4-C6 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl with 3-5 fluorine atom, Q is the optional C4-C6 alkyl that is replaced by one or more fluorine atoms;

The nitrile compound of formula (I), wherein R is the C3-C4 fluoroalkyl with 6-8 fluorine atom, Q is the optional C4-C6 alkyl that is replaced by one or more fluorine atoms;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl with 3-5 fluorine atom, Q is the C4-C6 alkyl with 6-8 fluorine atom;

The nitrile compound of formula (I), wherein R is the C3-C4 fluoroalkyl with 6-8 fluorine atom, Q is the C4-C6 alkyl with 6-8 fluorine atom;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl with 3-5 fluorine atom, Q is the optional C3-C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is the C3-C4 fluoroalkyl with 6-8 fluorine atom, Q is the optional C3-C4 alkyl that is replaced by one or more fluorine atoms;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl with 3-5 fluorine atom, Q is the C3-C4 alkyl with 6-8 fluorine atom;

The nitrile compound of formula (I), wherein R is the C3-C4 fluoroalkyl with 6-8 fluorine atom, Q is the optional C3-C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl with 3-5 fluorine atom, Q is the optional C3-C4 alkyl that is replaced by one or more fluorine atoms;

The nitrile compound of formula (I), wherein R is the C3-C4 fluoroalkyl with 6-8 fluorine atom, Q is the C3-C4 alkyl with 6-8 fluorine atom;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl, Q is the optional C1-C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is the C2 fluoroalkyl, Q is the optional C1-C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is 2,2, the 2-trifluoroethyl, Q is the optional C1-C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl, Q is the optional C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is the C2-C3 fluoroalkyl that at least two fluorine atoms of 2 quilts replace, Q is (C3-C5 fluorine cycloalkyl) methyl;

The nitrile compound of formula (I), wherein R is the C2-C3 fluoroalkyl that at least 2 quilts replace more than two fluorine atoms, Q is 4,4-difluoro cyclohexyl;

The nitrile compound of formula (I), wherein R is that at least two fluorine atoms of 1 quilt replace and 3 C3-C4 fluoroalkyls that replaced by at least one fluorine atom, Q is the C2-C3 alkyl that at least two fluorine atoms of 2 quilts replace;

The nitrile compound of formula (I), wherein R be 1 replaced by two fluorine atoms and 3 replaced the C3-C4 fluoroalkyl by one or two fluorine atom, Q is the C2-C3 alkyl that at least two fluorine atoms of 2 quilts replace;

The nitrile compound of formula (I), wherein R is the C2-C3 fluoroalkyl that at least two fluorine atoms of 2 quilts replace, Q is the optional C3-C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is 2 C2-C3 fluoroalkyls that replaced by two fluorine atoms, Q is the optional C3 fluoroalkyl that is replaced by chlorine or bromine;

The nitrile compound of formula (I), wherein R is 2 C2-C3 fluoroalkyls that replaced by two fluorine atoms, Q is the C3 fluoroalkyl;

The nitrile compound of formula (I), wherein R is 2 C2-C3 fluoroalkyls that replaced by two fluorine atoms, Q is the C4 fluoroalkyl;

The nitrile compound of formula (I), wherein R is the C2-C3 fluoroalkyl that at least two fluorine atoms of 2 quilts replace, Q be 1 replaced by two fluorine atoms and 3 by one or two fluorine atom replace the C4 fluoroalkyl;

The nitrile compound of formula (I), wherein R is the C2-C3 fluoroalkyl, Q is 1,1,2,2,3,3,4,4-octafluoro butyl;

The nitrile compound of formula (I), wherein R is the C2-C3 fluoroalkyl that at least two fluorine atoms of at least 2 quilts replace, Q is 1,1,2,2,3,3,4,4-octafluoro butyl;

The nitrile compound of formula (I), wherein R is the C2-C4 fluoroalkyl, Q is 1,1,2,2,3,3,4,4-octafluoro butyl;

The nitrile compound of formula (I), wherein R is the C3 fluoroalkyl, Q is 1,1,2,2,3,3,4,4-octafluoro butyl;

The nitrile compound of formula (I), wherein R is 2,2,2-trifluoroethyl, Q are 1,1,2,2,3,3,4,4-octafluoro butyl;

The nitrile compound of formula (I), wherein R is 2,2,3,3,3-five fluoropropyls, Q are 1,1,2,2,3,3,4,4-octafluoro butyl;

The nitrile compound of formula (I), wherein R is the C2 fluoroalkyl, Q is the optional C4 alkyl that is replaced by one or more halogens;

The nitrile compound of formula (I), wherein R is the C2 fluoroalkyl, Q is 1,1,2,2,3,3,4,4-octafluoro butyl; With

The nitrile compound of formula (I), wherein R is the C4 fluoroalkyl, Q is 1,1,2,2,3,3,4,4-octafluoro butyl.

Subsequently the method for preparing The compounds of this invention will be described.

The compounds of this invention for example can adopt any preparation to the method 5 of following method 1.

Method 1

The compounds of this invention can pass through compound (a) and compound (b) prepared in reaction:

Wherein R represents the C1-C4 fluoroalkyl, Q represents halogen, optional C1-C11 alkyl, optional C2-C6 thiazolinyl, optional C2-C6 alkynyl, optional C3-C7 cycloalkyl or (the optional C3-C7 cycloalkyl that is replaced by one or more halogens) C1-C4 alkyl that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens, X ¹Expression bromine, iodine, mesyloxy, tosyloxy or trifluoro-methanesulfonyl oxy.

Usually this is reflected under the alkali existence and carries out in solvent.

The solvent that is used for this reaction comprises aliphatic hydrocrbon such as hexane, heptane, octane or hexanaphthene; Aromatic hydrocarbons such as toluene, dimethylbenzene or mesitylene; Ether such as ether, methyl tertiary butyl ether, tetrahydrofuran (THF) or 1, the 4-dioxane; Acid amides such as N, dinethylformamide; Dialkyl sulphoxide such as methyl-sulphoxide; And composition thereof.

The alkali that is used for this reaction comprises carbonate such as yellow soda ash or salt of wormwood; Alkalimetal hydride such as sodium hydride; Tertiary amine such as triethylamine or diisopropylethylamine.

Usually every mole compound (b) uses 1-10 mole compound (a) in this reaction.

Usually every mole compound (b) uses the 1-10 mol alkali in this reaction.

Temperature of reaction is generally-20 to 100 ℃.Reaction times is generally 0.1-24 hour.

After reaction is finished, can carry out aftertreatment, for example this reaction mixture be added in the water, use organic solvent extraction, concentrate extract etc., separate The compounds of this invention reaction mixture.If desired, can carry out purifying to the The compounds of this invention after separating by methods such as chromatography, recrystallizations.

Method 2

The compounds of this invention can pass through compound (c) and compound (d) prepared in reaction:

Wherein R and Q as above define, X ²Expression bromine, iodine, mesyloxy, tosyloxy or trifluoro-methanesulfonyl oxy.

Usually every mole compound (c) uses 1-10 mole compound (d) in this reaction.

Usually every mole compound (c) uses the 1-10 mol alkali in this reaction.

Method 3

In The compounds of this invention, wherein Q and R are that the compound (II) of identical C1-C4 fluoroalkyl also can be by with compound (e) and propane dinitrile prepared in reaction:

R wherein ¹And Q ¹Represent identical C1-C4 fluoroalkyl, X ³Expression chlorine, bromine, iodine, mesyloxy, tosyloxy or trifluoro-methanesulfonyl oxy.

Usually every mole compound (e) uses 0.3-1 mole propane dinitrile in this reaction.Usually every mole compound (e) uses the 0.6-5 mol alkali in this reaction.

Temperature of reaction is generally-20 to 100 ℃.Reaction times is generally 0.1-36 hour.

After reaction is finished, can carry out aftertreatment, for example this reaction mixture be added in the water, use organic solvent extraction, concentrate extract etc., separate The compounds of this invention reaction mixture.If desired, can carry out purifying to the compound (II) after separating by methods such as chromatography, recrystallizations.

Method 4

In The compounds of this invention, compound (III) also can pass through compound (c) and compound (f) prepared in reaction:

Wherein R as above defines, X ⁴Expression C1-C10 perfluoroalkyl, X ⁵The expression halogen.

The alkali that is used for this reaction comprises carbonate such as yellow soda ash or salt of wormwood; Fluorochemical is Potassium monofluoride and tetrabutylammonium for example; Alkalimetal hydride such as sodium hydride; Tertiary amine such as triethylamine or diisopropylethylamine.

Usually every mole compound (c) uses 1-10 mole compound (f) in this reaction.Usually every mole compound (c) uses the 0.1-5 mol alkali in this reaction, preferably uses the 0.6-5 mol alkali.

After reaction is finished, can carry out aftertreatment, for example this reaction mixture be added in the water, use organic solvent extraction, concentrate extract etc., separate The compounds of this invention reaction mixture.If desired, can carry out purifying to the compound (III) after separating by methods such as chromatography, recrystallizations.

Method 5

In The compounds of this invention, compound (IV) also can pass through compound (g) and fluorizating agent prepared in reaction:

Wherein R as above defines, X ⁶Expression oxo C1-C11 alkyl, hydroxyl C1-C11 alkyl, oxo C3-C6 thiazolinyl, hydroxyl C3-C6 thiazolinyl, oxo C4-C6 alkynyl, hydroxyl C4-C6 alkynyl, oxo C3-C7 cycloalkyl, hydroxyl C3-C7 cycloalkyl, oxo (C3-C7 cycloalkyl) C1-C4 alkyl or hydroxyl (C3-C7 cycloalkyl) C1-C4 alkyl, X ⁷Expression fluorine C1-C11 alkyl, fluorine C3-C6 thiazolinyl, fluorine C4-C6 alkynyl, fluorine C3-C7 alkyl or fluorine (C3-C7 cycloalkyl) C1-C4 alkyl.

This has been reflected under solvent or the solvent-free existence and has carried out.

The solvent that is used for this reaction comprises aliphatic hydrocrbon such as hexane, heptane, octane or hexanaphthene; Halohydrocarbon such as tetracol phenixin, chloroform or methylene dichloride; And composition thereof.

The fluorizating agent that is used for this reaction comprises diethylaminosulfurtrifluoride and 2-chloro-1,1,2-trifluoroethyl-diethylamine.

Usually every mole compound (g) uses 1-10 mole fluorizating agent in this reaction.

After reaction is finished, can be with in the reaction mixture impouring water and use organic solvent extraction.Can carry out aftertreatment to organic layer, for example dry and concentrated with separating compound (IV).If desired, can carry out purifying to the compound (IV) after separating by methods such as chromatography, recrystallizations.

Then, explanation is used to prepare the intermediates preparation of The compounds of this invention.

Compound (b) for example can pass through compound (d) and propane dinitrile prepared in reaction:

Wherein Q and X ²As above definition.

The solvent that is used for this reaction comprises aliphatic hydrocrbon such as hexane, heptane, octane or hexanaphthene; Aromatic hydrocarbons such as toluene, dimethylbenzene or mesitylene; Ether such as ether, methyl tertiary butyl ether, tetrahydrofuran (THF) or 1, the 4-dioxane; Acid amides such as N, dinethylformamide; And composition thereof.

Usually every mole compound (d) uses 0.5-10 mole propane dinitrile in this reaction, preferably uses 0.5-1 mole propane dinitrile.Usually every mole compound (d) uses the 0.5-5 mol alkali in this reaction.

After reaction is finished, can carry out aftertreatment, for example this reaction mixture be added in the water, use organic solvent extraction, concentrate extract etc., separate The compounds of this invention reaction mixture.If desired, can carry out purifying to the compound (b) after separating by methods such as chromatography, recrystallizations.

Compound (c) for example can pass through compound (a) and propane dinitrile prepared in reaction:

Wherein R and X ¹As above definition.

Usually every mole compound (a) uses 0.5-10 mole propane dinitrile in this reaction, preferably uses 0.5-1 mole propane dinitrile.Usually every mole compound (a) uses the 0.5-5 mol alkali in this reaction.

After reaction is finished, can carry out aftertreatment, for example this reaction mixture be added in the water, use organic solvent extraction, concentrate extract etc., separate The compounds of this invention reaction mixture.If desired, can carry out purifying to the compound (c) after separating by methods such as chromatography, recrystallizations.

Perhaps, compound (c) also can pass through J.Chem.Soc.Perkin Trans.1, the method preparation of describing among the 2589-2592 (1991).

The compounds of this invention has the insect of control action kou to comprise deleterious arthropods (as insect, acarid) and deleterious nematode to it, and specific examples is as follows:

Hemiptera (Hemiptera):

Delphacidae (Delphacidae), for example small brown rice planthopper (Laodelphax striatellus), brown paddy plant hopper (Nilaparvata lugens), white backed planthopper (Sogatella furcifera) etc.,

Angle top Cicadidae (Deltocephalidae), for example rice green leafhopper (Nephotettixcincticeps), nephotettix bipunctatus (Nephotettix virescens) etc.,

Aphidiadae (Aphididae), for example cotten aphid (Aphis gossypii), black peach aphid (Myzus persicae) etc.,

Pentatomiddae (Pentatomidae) and Alydidae (Alydidae), for example spend the green stinkbug in angle (Nezaraantennata), excellent honeybee coried (Riptortus clavetus), Japanese two star stinkbugs (Eysarcorislewisi), wedge angle two star stinkbugs (Eysarcoris parvus), Plautia stali and Halyomorphamista etc.

Aleyrodidae (Aleyrodidae), for example greenhouse whitefly (Trialeurodes vaporariorum), Bemisia argentifolii (Bemisia argentifolii) etc.,

A red-spotted lizard section (Coccidae), Coccidae and Margarodidae, for example red kidney Aspidiotus (Aonidiella aurantii), Sheng Qiongsikang armored scale (Comstockaspis perniciosa), citrus point armored scale (Unaspis citri), red ceroplastes floridensis (Ceroplastes rubens), Australia icerya purchasi (Icerya purchasi) etc.

Tingidae (Tingidae),

Cimicidae is as Cimex lectularius etc.

Psyllidae (Psyllidae) etc.;

Lepidopteran (Lepidoptera):

Pyralidae (Pyralidae), the for example wild snout moth's larva (Notarcha derogata) of striped rice borer (Chilo suppressalis), cnaphalocrocis medinalls guenee (Cnaphalocrocis medinalis), lap leaf, India paddy phycitid (Plodia interpunctella) etc.

Noctuidae (Noctuidae), for example prodenia litura (Spodoptera litura), mythimna separata (Pseudaletia separata), Thoricoplusia spp., real noctuid (Heliothis spp.), noctuid (Helicoverpa spp.) etc.,

Sulfur butterfly (Pieridae), small white (Pieris rapae) etc. for example,

Tortricidae (Tortricidae) is for example rolled up moth (Adoxophyes spp.), oriental fruit months (Grapholita molesta), Pericarpium Mali pumilae steinernema (Cydia pomonella) etc.,

Moth fruit moth section (Carposinidae), peach fruit moth (Carposina niponensis) etc. for example,

Lyonetid section (Lyonetiidae), lyonetid (Lyonetia spp.) etc. for example,

Lymantriidae (Lymantriidae), for example poison moth (Lymantria spp.), pornography and drug moth (Euproctis spp.) etc.,

Yponomeutidae (Yponomeutidae), small cabbage moth (Plutella xylostella) etc. for example,

Gelechidae (Gelechiidae), Pectinophora gossypiella (Pectinophora gossypiella) etc. for example,

Arctiidae (Arctiidae), fall webworms (Hyphantria cunea) etc. for example,

Rain moth section (Tineidae), for example Tinea translucens, curtain rain moth (Tineolabisselliella) etc.;

Diptera (Diptera):

Calicedae, for example culex pipiens pollens (culex pipiens pollens (Culex pipiens pallens)), Culex tritaeniorhynchus (Culex tritaeniorhynchus), Culex quinquefasciatus (Culex quinquefasciatus) etc.,

Yellow-fever mosquito (Aedes spp.), for example Aedes aegypti (Aedes aegypti), text of an annotated book yellow-fever mosquito (Aedesalbopictus) etc.,

Anopheles (Anopheles), Anopheles sinensis (Anopheles sinensis) etc. for example,

Chironomidae (Chironomidae),

Nuscidae (Muscidae), for example housefly (housefly (Musca domestica)), false stable fly (Muscina stabulans) etc.,

Calliphoridae (Calliphoridae),

Flesh flies (Sarcophagidae),

Latrine fly section (Fanniidae),

Anthomyiidae (Anthomyiidae), for example fly (Delia antigua) etc. is planted on delia platura (Delia platura), green onion ground,

Tephritidae (Tephritidae),

Drosophilidae (Drosophilidae),

Phoridae (Phoridae) is Megaselia spiracularis etc. for example.

Moth files (Psychodidae), for example Clogmia albipunctata etc.

Simulidae (Simuliidae),

Tabanidae (Tabanidae),

The Nuscidae of stinging (Stomoxyidae),

Agromyzidae (Agromyzidae) etc.;

Coleoptera (Coleoptera):

Corn root leaf A section (corn rootworms), for example corn root leaf A (Diabroticavirgifera), Diabrotica undecimpunctata howardi etc.,

Scarabaeidae (Scarabaeidae), for example bronze different beetle (Anomala cuprea), polychrome different beetle (Anomala rufocuprea) etc.,

Rhynchophoridae, Curculionidae (Culculionidae) and Bruchidae (Bruchidae), Curculionidae (Curculionidae), for example sitophilus zea-mais (Sitophilus zeamais), rice water resemble (Lissorhoptrus oryzophilus), Callosobruchus chinensis (Callosobruchus chinesis) etc.

TRenebrionidae (Tenebrionidae), for example bloom first (Tenebrio molitor), red flour beetle (Tribolium castaneum) etc.,

Chrysomelidae (Chrysomelidae), for example rice leaf beetles (oulema oryzae), aulacophora femoralis (Aulacophora femoralis), Phyllotreta striolata (Phyllotreta striolata), colorado potato beetles (Leptinotarsa decemlineata) etc.

Dermestidae (Dermestidae), as white glues khapra beetle (Dermestes maculates) etc.,

Anobiidae (Anobiidae),

Ladybug (Epilachna spp.), potato ladybug (Epilachnavigintioctopunctata) etc. for example,

Lyctidae (Lyctidae),

Bostrichidae (Bostrychidae),

Ptinidae (Ptinidae)

Cerambycidae (Cerambycidae),

Paederus fuscipes Curtis (Paederus fuscipes) etc.;

Blattodea (Blattodea):

Groton bug (Groton bug (Blattella germanica)), Peroplaneta fluligginosa (Periplanetafuliginosa), periplaneta americana (Periplaneta americana), the big Lian of foxiness (Periplanetabrunnea), oriental cockroach (Blatta orientalis) etc.;

Thysanoptera (Thysanoptera):

Palm thrips (Thrips palmi), onion thrips (Thrips tabaci), Frankliniella occidentalis (Frankliniella occidentalis), flower thrips (Frankliniella intonsa) etc.;

Hymenoptera (Hymenoptera):

Formicidae (Formicidae), for example MonomoriumMayr (Monomorium pharaonis), the brown woods ant of mercerising (Formica fusca japonica), Ochetellus glaber, crosspointer ant (Pristomyrmexpungens), Pheidole noda etc.,

Vespidae (Vespidae),

Bethylidae (bethylididae),

Tenthredinidae (Tenthredinidae), for example Japanese cabbage sawfly (Athaliajaponica) etc.;

Orthoptera (Orthoptera):

Gryllotalpidae (Gryllotalpidae), sword angle locust section (Acrididae) etc.;

Siphonaptera (Aphaniptera):

Cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), Pulex irritans (Pulex irritans), mouse flea (Xenopsylla cheopis);

Anoplura (Anoplura)

Head louse (Pediculus humanus capitis), crab louse (Phthirus pubis), haematopinus eurysternus (Haematopinus eurysternus), Dalmalinia ovis etc.;

Isoptera (Isoptera):

Coptotermes formosanus Shtrari (Subterranean termites), as the northern reticulitermes flavipe (Reticulitermessperatus) that dwells, Coptotermes formosanus Shtrari (Coptotermes formosanus), North America reticulitermes flavipe (Reticulitermesflavipes), western U.S. reticulitermes flavipe (Reticulitermes hesperus), U.S. little black reticulitermes flavipe (Reticulitermes virginicus), U.S. black shin reticulitermes flavipe (Reticulitermes tibialis), golden yellow different termite (Heterotermes aureus) etc.

Dry-wood termite (dry wood termites) is as little principal columns of a hall termite (Incisitermes minor) etc.,

Damp-wood termite (damp wood termites) is as the ancient termite (Zootermopsisnevadensis) in Nevada;

Acarina (Acarina):

Tetranychidae (Tetranychidae), for example Tetranychus urticae (Tetranychus urticae), kamisawa tetranychus (Tetranychus kanzawai), citrus red mite (crm) (Panonychus citri), panonychus ulmi (Panonychus ulmi), unguiculus mite (Oligonychus spp.) etc.

Eriophyidae (Eriophyidae), for example tangerine peronium goitre mite (Aculops pelekassi), Si Shi sting goitre mite (Aculus achlechtendali) etc.,

Tarsonemidae (Tarsonemidae), Polyphagotarsonemus latus Banks (Polyphagotarsonemus latus) etc. for example,

Tenuipalpidae (Tenuipalpidae),

Du Ke mite section (Tuckerellidae),

Hard tick section (Ixodidae), for example haemaphysalis longicornis (Haemaphysalis longicornis), haemaphysalis flava (Haemaphysalis flava), Dermacentor variabilis (Dermacentor variabilis), ixodes ovatus (Ixodes ovatus), ixodes scapularis (Ixodes scapularis), boophilus microplus (Boophilus microplus), amblyomma americanum (amblyomma americanum), brown dog tick (Rhipicephalus sanguineus) etc.

Tyroglyphidae (Acaridae), tyrophagus putrescentiae (Trophagus putrescentiae) etc. for example,

Epidermis mite section (Epidermoptidae), for example dust mite (Dermatophagoidesfarinae), dermatophagoides pteronyssinus (Dermatophagoides ptrenyssnus) etc.,

Cheyletidae (Cheyletidae), for example common cheyletid mite (Cheyletus eruditus), Malacca cheyletid mite (Cheyletus malaccensis), Cheyletus moorei etc.,

Dermanyssidae (Dermanyssidae) is as Dermanyssus gallinae (Dermanyssus gallinae) etc.

Illness dirt mite section (Trombiculidae), as trombicula deliensis (Leptotrombidium akamushi) etc.,

Araneae: Japanese red chela spider (Chiracanthium japonicum), Latrodectushasseltii etc.;

Spider type guiding principle (Chilopoda):

Thereuonema hilgendorfi, few sour jujube centipede (Scolopendra subspinipes) etc.;

Diplopoda (Diplopoda):

Oxidus gracilis, Nedyopus tambanus etc.;

Deng order guiding principle (Isopoda):

Tide worm (Armadillidium vulgare) etc.;

Gastropoda (Gastropoda):

Limax marginatus, yellow slug (Limax flavus) etc.;

Nematode (Nematodes):

Coffee pratylenchus (Pratylenchus coffeae), Pratylenchus fallax, soy bean cyst roundworm (Heterodera glycines), Globadera rostochiensis, northern root knot nematode (Meloidogyne hapla), Meloidogyne incognita (Meloidogyne incognita) etc.

Although the form that insect-killing composition of the present invention can The compounds of this invention itself exists, usually itself and solid carrier, liquid vehicle and/or carrier gas are hybridly prepared into preparation, and if desired, adding tensio-active agent or other preparation used additives.That is to say that insect-killing composition of the present invention comprises The compounds of this invention usually and comprises inert support.But this class preparation comprises emulsion, finish, shampoo agent flowing agent, pulvis, wettable dose, granule, paste, microcapsule, foaming agent, aerosol, carbon dioxide gas body preparation, tablet, resin formulation, made of paper dose, nonwoven fabric preparation and braiding or textile fabric preparation.These preparations can poison bait, the form of desinsection volume fragrant (pesticide coil), electric pesticide tablet (pesticide mat), the preparation of being fuming, fumigant or sheet is used.

The preparation of insect-killing composition of the present invention comprises the compound of the present invention of 0.01-98% weight usually.

The solid carrier that is used for preparation comprises well as clay fines or particle (for example kaolin, diatomite, wilkinite, Fubasami soil, acid clay etc.); Synthetic hydrated silicon oxide; Talcum powder; Potter's clay; Other inorganic materials (as sericite, quartz, sulphur, gac, lime carbonate and hydrated SiO 2 etc.); Or chemical fertilizer (ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride and urea etc.); It under normal temps the material (for example 2,4,6-triisopropyl-1,3,5-trioxane, naphthalene, santochlor, camphor and diamantane etc.) of solid form; Wool; Silk; Cotton; Hemp; Paper pulp; Synthetic resins is (as polyvinyl resin such as new LDPE (film grade), straight-chain low density polyethylene and high density polyethylene(HDPE); Ethylene-vinyl ester copolymer such as ethylene-vinyl acetate copolymer; Ethylene-methyl acrylate multipolymer such as ethylene-methyl methacrylate methyl terpolymer and ethylene-methyl methacrylate ethyl ester multipolymer; Ethylene-acrylate copolymer such as ethylene-methyl acrylate copolymer and ethylene-ethyl acrylate copolymer; Vinyl-vinyl polymers of carboxylic acid such as ethylene-acrylic acid copolymer; Ethene-tetracyclododecane (tetracyclododecene) multipolymer; Acrylic resin such as alfon and propylene-ethylene copolymers; Poly-(4-methyl-1-pentene), poly-(1-butylene), polyhutadiene, polystyrene; Acrylonitrile styrene resin (AS); Styrenic elastomer such as acrylonitrile-butadiene-styrene resin, vinylbenzene-conjugated diene block copolymer and vinylbenzene-conjugated diene block copolymer hydride; Fluoro-resin; Acrylic resin is as poly-(methyl methacrylate); Polyamide resin such as nylon 6 and nylon 66; Vibrin such as polyethylene terephthalate, PEN, polybutylene terephthalate and poly terephthalic acid hexamethylene two methylene esters; Polycarbonate, polyacetal, polypropylene aldehyde radical sulfone (polyacrylsulfones), polyarylate, hydroxy-benzoic acid polyester, polyimide, polyestercarbonate (polyester carbonates), poly (phenylene ether) resin, polyvinyl chloride, polyvinylidene dichloride, urethane and porous resin such as polyurathamc, expanded polypropylene or foaming ethene etc.), glass, metal, pottery, fiber, cloth, cloth, sheet material, paper, yarn, foam, porous material and multifilament.

Liquid vehicle comprises that aromatics or aliphatic hydrocrbon are (as dimethylbenzene, toluene, alkylnaphthalene, phenyl xylyl ethane, kerosene, gasoline, hexane, hexanaphthene etc.), halohydrocarbon is (as chlorobenzene, methylene dichloride, ethylene dichloride, trichloroethane etc.), alcohol is (as methyl alcohol, ethanol, Virahol, butanols, hexanol, benzylalcohol, ethylene glycol etc.), ether is (as ether, glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran (THF) diox etc.), ester is (as ethyl acetate, butylacetate etc.), ketone is (as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), pimelinketone etc.), nitrile is (as acetonitrile, isopropyl cyanide etc.), sulfoxide (as dimethyl sulfoxide (DMSO) etc.), acid amides is (as N, dinethylformamide, N,N-dimethylacetamide, N-Methyl pyrrolidone etc.), alkylene carbonate (as Texacar PC etc.), vegetables oil is (as soybean oil, the cottonseed wet goods), plants essential oil is (as orange oil, Hyssop oil, the lemon wet goods) and water.

Gaseous carrier comprises butane gas, chlorofluorocarbon gas, liquefied petroleum gas (LPG) (LPG), methyl ether and carbon dioxide.

Tensio-active agent comprises alkyl sulfuric ester salt, alkylsulfonate, alkylaryl sulfonate, alkyl aryl ether and their polyoxyethylene thing, polyglycol ether, polyol ester and sugar alcohol derivant.

Other auxiliary agents that are used for preparation comprise tackiness agent, dispersion agent and stablizer etc., particularly, as casein, gelatin, polysaccharide is (as starch, gum arabic, derivatived cellulose, Lalgine etc.), lignin derivative, wilkinite, sugar, synthesizing water-solubility polymer (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid etc.), PAP (acid phosphatase isopropyl ester), BHT (2,6 di tert butyl 4 methyl phenol), BHA (mixture of the 2-tertiary butyl-4-methoxyphenol and the 3-tertiary butyl-4-methoxyphenol), vegetables oil, mineral oil, lipid acid and fatty acid ester.

The base mateiral that is used for resin formulation comprises polyvinyl resin such as new LDPE (film grade), straight-chain low density polyethylene and high density polyethylene(HDPE); Ethylene-vinyl ester copolymer such as ethylene-vinyl acetate copolymer; Ethylene-methyl acrylate multipolymer such as ethylene-methyl methacrylate methyl terpolymer and ethylene-methyl methacrylate ethyl ester multipolymer; Ethylene-acrylate copolymer such as ethylene-methyl acrylate copolymer and ethylene-propylene acetoacetic ester; Vinyl-vinyl polymers of carboxylic acid such as ethylene-acrylic acid copolymer; Ethene-tetracyclododecane multipolymer; Acrylic resin such as propylene copolymer and propylene-ethylene copolymers; Poly-(4-methyl-1-pentene), poly-1-butylene, polyhutadiene, polystyrene, acrylonitrile styrene resin (AS); Styrenic elastomer such as acrylonitrile-butadiene-styrene resin, vinylbenzene-conjugated diene copolymer, vinylbenzene-conjugated diene block copolymer hydride; Fluoro-resin; Acrylic resin is as poly-(methyl methacrylate); Polyamide resin such as nylon 6 and nylon 66; Vibrin such as polyethylene terephthalate, PEN, poly-fourth dioctyl phthalate butanediol ester (polybutylene butalate) and poly terephthalic acid hexamethylene two methylene esters; Polycarbonate, polyacetal, polypropylene aldehyde radical sulfone, polyarylate, hydroxy-benzoic acid polyester, polyimide, polyestercarbonate, poly (phenylene ether) resin, polyvinyl chloride, polyvinylidene dichloride and urethane.Can use a kind of in this class base mateiral or use two or more mixture.If desired, can in these base mateirals, add softening agent such as phthalic ester (as dimethyl phthalate, dioctyl phthalate (DOP) etc.), fatty acid ester or stearic acid.

Can with post moulding such as injection moulding, extrusion molding or compression moulding, obtain resin formulation by The compounds of this invention is kneaded in base mateiral.If desired, can the resin formulation that obtain be made shapes such as plate, film, band, net, rope by methods such as further molding, cuttings.These resin formulation can collar for animal (collar), animal ear board (ear tag), Formulation, tubulose (lead) or gardening label (horticultural post) form are used.

The base mateiral of poison bait comprises farm crop powder, vegetables oil, sugar and Microcrystalline Cellulose.In case of necessity, in poison bait, add antioxidant such as butylated hydroxytoluene or nordihydroguaiaretic acid, sanitas such as dehydro-acetic acid prevent material such as red chilly powder that children or pet accident are eaten, attract perfume compound such as cheese spices, onion spice or the peanut oil of insect.

Can directly be applied to insect and/or insect habitat (as plant, animal, soil etc.) by The compounds of this invention The compounds of this invention is used for insect control significant quantity.

When insect-killing composition of the present invention was used for Pest Control in agricultural and forestry, the consumption of The compounds of this invention was generally 1-100, and 000g/ha is preferably 10-1,000g/ha.When insect-killing composition of the present invention is emulsion, wetting agent, in the time of can flowing preparation or microencapsulation form, uses behind the dilute with water usually, make that the concentration of activeconstituents is 0.01-1,000ppm.When insect-killing composition of the present invention was oily matter, powder or particulate matter form, former state was used usually.Can same as before these preparations be sprayed on the plant to prevent insect pest, perhaps dilutable water is sprayed on the plant then to prevent insect pest.Available these preparations processing soil are controlled and are lived in insect pest in soil.Also these preparations can be used for planting rice shoot, in plantation, handle implantation hole and undesirable root with the pre-treatment seedbed.Formulation that also can insect-killing composition of the present invention is wrapped on the plant, be dispersed in around the plant, place undesirable root soil surface etc.

When insect-killing composition of the present invention was used to control popular insect pest, The compounds of this invention was usually with 0.001-100mg/m ³Amount be applied to the space, and The compounds of this invention is usually with 0.001-1,000mg/m ²Amount be applied to the plane.But use behind the common dilute with water of insect-killing composition of emulsion, wetting agent or flowing agent form, make to comprise 0.001-100 usually, 000ppm, preferred 0.01-1, the The compounds of this invention of 000ppm.The insect-killing composition of oily matter, aerosol, be fuming preparation or poison bait form uses with the form of itself usually.Desinsection volume insect-killing composition fragrant or electric pesticide tablet form itself gives out activeconstituents by heating.The insect-killing composition of resin formulation, papery composition, sheet, nonwoven fabric, braiding or textile fabric preparation or Formulation form for example uses by said preparation being placed inflate in a certain space and with said preparation.Use insect-killing composition of the present invention with the space that prevents popular insect pest comprise between case, Japanese molding box (Japanese-style closet), Japanese type cabinet (Japanese-style chest), cupboard, lavatory, bathroom, refuse, living room, dining room, warehouse and Che Nei.Also can use insect-killing composition in the space of outdoor opening.

When insect-killing composition of the present invention is used for the parasite of the livestock (as milk cow, horse, pig, sheep, goat or chicken or animalcule such as dog, cat, rat or mouse) outside the watch-keeping cubicle, can use the veterinary applications known method to be used for described animal.More particularly, when being used for whole body when control, for example with tablet, give with mixture, suppository or the injection of feed (as intramuscular, subcutaneous, intravenously, intraperitoneal etc.) form as described in insect-killing composition.When being used for the control of non-whole body, use the method for the present composition to comprise spraying, inclining with the insect-killing composition of ointment or liquid, aqueous form is coated with or spot printing processing, the necklace that animal is cleaned and will be made by the insect-killing composition of resin formulation form with the insect-killing composition of shampoo formulation form or ear board hang on one's body the animal.When giving animal, the amount of The compounds of this invention is generally every kilogram of the weight of animals 0.01-1,000mg.

Insect-killing composition of the present invention can mixture form use, perhaps can be used in combination with other worm agent, nematocides, miticide, mycocide, weedicide, plant-growth regulator, synergistic agent, fertilizer, soil redeposition, animal-feed etc.

This insecticides or acaricidal activeconstituents comprise pyrethroids compound such as Pynamin, Tetramethrin, prallethrin, phenothrin, Chryson, cyphenothrin, permethrin, Cypermethrin, α-Cypermethrin, ξ-Cypermethrin, δ-chrysanthemum ester, tralomethrin, cyhalofop-butyl, β-cyhalofop-butyl, cyhalothrin, λ-cyhalothrin, flumethrin, miaow alkynes chrysanthemum ester, ether chrysanthemum ester, fenvalerate, fenvalerate, Fenvalerate, deinsectization silicon ether, bifenthrin, transfluthrin, flucythrinate, fluorine amine fenvalerate, fluorine ester chrysanthemum ester, tefluthrin, acetonitrile chrysanthemum ester, (EZ)-(1RS, 3RS; 1RS, 3SR)-2,2-dimethyl-3-third-1-thiazolinyl cyclopropane-carboxylic acid 2,3,5,6-tetrafluoro-4-(methoxymethyl) benzyl ester, (EZ)-(1RS, 3RS; 1RS, 3SR)-2,2-dimethyl-3-third-1-thiazolinyl cyclopropane-carboxylic acid 2,3,5,6-tetrafluoro-4-methyl benzyl ester, tetrafluoro (dimefluthrin) and Prallethrin; Organo phosphorous compounds such as SD-1750, fenitrothion 95, cynock, Profenofos, sulprofos, Tsidial, different hungry azoles phosphorus, tetrachlorvinphos, Tiguvon, Chlorpyrifos 94, diazinon, Ortho 12420, uncle's fourth phosphorus, phorate, isofenphos (chlorethoxyfos), colophonate, ethoprop, gram line pellet and Thiamazole; Amino formate compounds such as Propoxur, carbaryl, hungry worm ketone, fenobucarb, methomyl, thiodicarb, alanycarb, benfuracarb, oxamyl, aldicarb and metmercapturon; Benzoyl phenyl carbamide compound such as octafluoro urea, UC 62644, fluorine bell urea, diflubenzuron, desinsection are grand, diflubenzuron, flufenoxuron, a N-Serve worm urea, napropamide (novaluron), triazuron and bistrifluoron; Immature hormone shape material (juvenile hormone-like substances) is as pyriproxyfen, methoprene, illiteracy 512 and Fenoxycarb 25WG; New class nicotine compound such as pyrrole worm are clear, the spirit of alkene worm, thiophene worm quinoline (thiacloprid), thiophene worm piperazine (thiamethoxam) and MTI-446 (dinotefuran); N-phenyl pyrazole compounds such as acetoprole and ethiprole; Benzoyl hydrazine compound such as RH-5992, ring worm hydrazides, methoxyl group fenozide and trimethylphenylmethane hydrazides; Methamidophos; Pyrrole first piperazine; Flonicamid (flonicamid); The azoles aphid becomes; Buprofezin; Spinosad; Emaricin (emamectinbenzoate); Fluorine azoles worm is clear; Indenes worm prestige MP; Pleocidin; Fly eradication amine; Azoles mite ester; Tebufenpyrad (tebufenpyrad); Azoles insect amide (tolfenpyrad); Pyridaben; The pyramine phenylate; Phonetic mite amine (fluacrypyrim); Second mite azoles (etoxazole); Fenazaquin; The mite quinone goes out; Hexythiazox; Four mite piperazines; Fenbutatin oxide; Kelthane, propargite; Ah crust's desinsection element; Milbemycin; Amitraz; Cartap; Bensultap; Thiocyclam; 5a,6,9,9a-hexahydro-6,9-methano-2,4; Spiral shell mite ester (spirodiclofen); Season ketone first mite ester (spiromesifen); Amidoflumet and Ai Zhading.

The activeconstituents of these sterilants comprises tetramethoxy esters of acrylic acid (strobilurin) compound such as nitrile Azoxystrobin (azoxystrobin); Organo phosphorous compounds such as tolclofosmethyl; Azole compounds such as metconazole (metconazole), own azoles alcohol, bacterium azoles (ipconazole), sipconazole, fluorine bacterium azoles, pefurazoate and hungry ether azoles; Iodine propargyl compound such as IPBC; Isothiazolone compounds such as OIT and MEC; Phthalide (fthalide); Fultolanil; Validamycin; Thiabendazole; Diclomezine; Pencycuron; Dazomet; Kasugamycin; IBP; Grass green pyridine (pyroquilon); Oxolinic acide (oxolinic acid); Tricyclazole; Ferimzone; Mebenil; EDDP; Isoprothiolane; Ring propionyl bacterium amine (carpropamid); Two chlorine zarilamids (diclocymet); Good fortune Lapie (furametpyr); Fludioxonil (fludioxonil); The sterilization profit; With the mould prestige of second.

Embodiment

The present invention will be described in more detail the present invention by following preparation embodiment, example of formulations and experimental example, but the present invention is not limited to these embodiment.

The preparation embodiment of The compounds of this invention at first will be described.

Preparation embodiment 1

(1) 0.5g sodium hydride (60% oil suspension) is suspended in 10mlN, in the dinethylformamide, at about 0 ℃ of 10mlN that adds down 1.6g (3,3, the 3-trifluoro propyl) propane dinitrile in this suspension, dinethylformamide solution.Allow this mixture rise to room temperature, toward wherein adding N, dinethylformamide to cumulative volume is 20ml (hereinafter the solution that will obtain like this is called solution A).

(2) 0.23g 1-bromo-3-chloropropane is dissolved in 1ml N, in the dinethylformamide, adds the 2ml solution A subsequently.After this mixture at room temperature stirs 4 hours, in this reaction mixture, add dilute hydrochloric acid, use ethyl acetate extraction subsequently.The organic layer of water and saturated sodium-chloride water solution washing subsequently, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 0.13g 2-(3-chloropropyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (1) hereinafter) through silica gel column chromatography.

The compounds of this invention (1):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.13-2.21(6H，m)，2.42-2.53(2H，m)，3.62(2H，t)。

Preparation embodiment 2

Adopt the method for preparing embodiment 1 (2) to prepare 0.11g 2-(3-chloro-2-methyl-propyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (2) hereinafter), difference are to use 0.17g 1-bromo-3-chloro-2-methylpropane to replace 1-bromo-3-chloropropane.

The compounds of this invention (2):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.26(3H，d)，1.84-1.92(1H，m)，2.21-2.38(4H，m)，2.43-2.57(2H，m)，3.43-3.68(2H，m)。

Preparation embodiment 3

Adopt the method for preparing embodiment 1 (2) to obtain 0.17g 2-(4-chlorobutyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (3) hereinafter), difference are to use 0.17g 1-bromo-4-chlorobutane to replace 1-bromo-3-chloropropane.

The compounds of this invention (3):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.82-1.94(4H，m)，1.96-2.06(2H，m)，2.13-2.21(2H，m)，2.41-2.53(2H，m)，2.54(2H，t)。

Preparation embodiment 4

Adopt the method for preparing embodiment 1 (2) to obtain 0.12g 2-(2,2-dichloro cyclopropyl methyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (4) hereinafter), difference is to use 0.21g 2-brooethyl-1, and 1-two Cyclopropanoyl Chlorides replace 1-bromo-3-chloropropane.

The compounds of this invention (4):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.42(1H，t)，1.81-1.96(2H，m)，2.08-2.12(1H，m)，2.22-2.29(2H，m)，2.43-2.58(3H，m)。

Preparation embodiment 5

With 2.00g propane dinitrile and 13.0g 1-bromo-3,3,3-trifluoro propane is dissolved in 10ml N, and dinethylformamide cools off in ice bath subsequently.After adding 8.4g salt of wormwood, mixture was at room temperature stirred 30 hours.In reaction mixture, add frozen water and ethyl acetate.Stir the mixture, subsequently layering.Use the ethyl acetate extraction water layer.Merge organic layer, water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 4.75g 2 through silica gel column chromatography, two (3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (5) hereinafter) of 2-.

The compounds of this invention (5):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.26-2.33(4H，m)，2.52-2.61(4H，m)。

Preparation embodiment 6

Adopt the method for preparing embodiment 1 (2) to obtain 0.03g 2-ethyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (6) hereinafter), difference is to use the 0.16g iodoethane to replace 1-bromo-3-chloropropane.

The compounds of this invention (6):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.32(3H，t)，2.06(2H，q)，2.14-2.22(2H，m)，2.42-2.57(2H，m)。

Preparation embodiment 7

Adopt the method for preparing embodiment 1 (2) to obtain 0.05g 2-propyl group-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (7) hereinafter), difference is to use the 0.17g propyl iodide to replace 1-bromo-3-chloropropane.

The compounds of this invention (7):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.08(3H，t)，1.68-1.77(2H，m)，1.91-1.96(2H，m)，2.13-2.21(2H，m)，2.43-2.57(2H，m)。

Preparation embodiment 8

Adopt the method for preparing embodiment 1 (2) to obtain 0.11g 2-butyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (8) hereinafter), difference is to use 0.18g 1-butyl iodide to replace 1-bromo-3-chloropropane.

The compounds of this invention (8):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.98(3H，t)，1.46(2H，q)，1.63-1.72(2H，m)，1.94-2.03(2H，m)，2.18-2.23(2H，m)，2.43-2.55(2H，m)。

Preparation embodiment 9

Adopt the method for preparing embodiment 1 (2) to obtain 0.10g 2-amyl group-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (9) hereinafter), difference is to use 0.20g 1-iodopentane to replace 1-bromo-3-chloropropane.

The compounds of this invention (9):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.91-1.02(3H，m)，1.38-1.45(4H，m)，1.61-1.74(2H，m)，1.93-2.07(2H，m)，2.13-2.24(2H，m)，2.47-2.54(2H，m)。

Preparation embodiment 10

Adopt the method for preparing embodiment 1 (2) to obtain 0.13g 2-hexyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (10) hereinafter), difference is to use the 0.21g 1-iodohexane to replace 1-bromo-3-chloropropane.

The compounds of this invention (10):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.87(3H，t)，1.28-1.43(6H，m)，1.63-1.72(2H，m)，1.91-2.01(2H，m)，2.13-2.19(2H，m)，2.42-2.51(2H，m)。

Preparation embodiment 11

Adopt the method for preparing embodiment 1 (2) to obtain 0.10g 2-heptyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (11) hereinafter), difference is to use 0.23g 1-iodine heptane to replace 1-bromo-3-chloropropane.

The compounds of this invention (11):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.90(3H，t)，2.21-2.42(8H，m)，2.59-2.68(2H，m)，1.91-2.02(2H，m)，2.12-2.28(2H，m)，2.41-2.53(2H，m)。

Preparation embodiment 12

Adopt the method for preparing embodiment 1 (2) to obtain 0.17g 2-octyl group-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (12) hereinafter), difference is to use the 0.24g 1-iodo-octane to replace 1-bromo-3-chloropropane.

The compounds of this invention (12):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.89(3H，t)，1.21-1.42(10H，m)，1.63-1.71(2H，m)，1.92-1.97(2H，m)，2.13-2.19(2H，m)，2.41-2.58(2H，m)。

Preparation embodiment 13

Adopt the method for preparing embodiment 1 (2) to obtain 0.19g 2-nonyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (13) hereinafter), difference is to use 0.21g 1-bromononane to replace 1-bromo-3-chloropropane.

The compounds of this invention (13):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.89(3H，t)，1.21-1.48(12H，m)，1.68-1.77(2H，m)，1.96-2.03(2H，m)，2.19-2.23(2H，m)，2.43-2.61(2H，m)。

Preparation embodiment 14

Adopt the method for preparing embodiment 1 (2) to obtain 0.15g 2-decyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (14) hereinafter), difference is to use 0.22g 1-bromo-decane to replace 1-bromo-3-chloropropane.

The compounds of this invention (14):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.89(3H，t)，1.22-1.48(14H，m)，1.68-1.74(2H，m)，1.97-2.01(2H，m)，2.18-2.22(2H，m)，2.48-2.63(2H，m)。

Preparation embodiment 15

Adopt the method for preparing embodiment 1 (2) to obtain 0.12g 2-allyl group-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (15) hereinafter), difference is to use the 0.12g allyl bromide 98 to replace 1-bromo-3-chloropropane.

The compounds of this invention (15):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.12-2.21(2H，m)，2.43-2.58(2H，m)，2.75(2H，d)，5.43-5.51(2H，m)，5.84-5.95(1H，m)。

Preparation embodiment 16

Adopt the method for preparing embodiment 1 (2) to obtain 0.13g 2-(3-butenyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (16) hereinafter), difference is to use 0.14g 1-bromo-3-butylene to replace 1-bromo-3-chloropropane.

The compounds of this invention (16):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.06-2.10(2H，m)，2.21-2.24(2H，m)，2.45-2.58(4H，m)，5.14-5.23(2H，m)，5.81-5.85(1H，m)。

Preparation embodiment 17

Adopt the method for preparing embodiment 1 (2) to obtain 0.19g 2-(3,3,4-three fluoro-3-butenyls)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (17) hereinafter), difference is to use 0.19g 1-bromo-3,4, and 4-three fluoro-3-butylene replace 1-bromo-3-chloropropane.

The compounds of this invention (17):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.23-2.27(4H，m)，2.52-2.61(2H，m)，2.69-2.80(2H，m)。

Preparation embodiment 18

0.4g 2-(3,3, the 3-trifluoro propyl) propane dinitrile and 0.5g cyclopropyl monobromomethane are dissolved in the 5ml methyl-sulphoxide, and add 0.41g salt of wormwood.Mixture at room temperature stirred 5 hours.Subsequently, in this reaction mixture, add dilute hydrochloric acid, use ethyl acetate extraction subsequently.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 0.34g 2-cyclopropyl methyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (18) hereinafter) through silica gel column chromatography.

The compounds of this invention (18):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.40(2H，dd)，0.72(2H，dd)，0.91-0.98(1H，m)，1.95(2H，d)2.16-2.23(2H，m)，2.43-2.52(2H，m)。

Preparation embodiment 19

Adopt the method for preparing embodiment 18 to obtain 0.34g 2-cyclobutylmethyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (19) hereinafter), difference is with 0.44g cyclobutylmethyl bromo for the cyclopropyl monobromomethane.

The compounds of this invention (19):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.81-1.92(2H，m)，1.93-2.01(2H，m)，2.06(2H，d)，2.11-2.19(2H，m)，2.22-2.27(2H，m)，2.41-2.52(2H，m)，2.61-2.69(1H，m)。

Preparation embodiment 20

Adopt the method for preparing embodiment 18 to obtain 0.34g 2-(2,2,3,3-tetrafluoro propyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (20) hereinafter), difference is with 0.44g trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro propyl ester replaces the cyclopropyl monobromomethane.

The compounds of this invention (20):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.34-2.41(2H，m)，2.55-2.63(2H，m)，2.74(2H，t)，5.88(1H，tt)。

Preparation embodiment 21

Adopt the method for preparing embodiment 18 to obtain 0.2g 2-(2,2, the 2-trifluoroethyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (21) hereinafter), difference is with 1.2g trifluoromethanesulfonic acid 2,2, the 2-trifluoro ethyl ester replaces the cyclopropyl monobromomethane.

The compounds of this invention (21):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.30-2.38(2H，m)，2.51-2.69(2H，m)，2.87(2H，q)。

Preparation embodiment 22

Adopt the method for preparing embodiment 18 to obtain 0.2g 2-(2,2,3,3,3-five fluoropropyls)-and 2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (22) hereinafter), difference is with 1.3g trifluoromethanesulfonic acid 2,2,3,3,3-five fluorine propyl ester replace the cyclopropyl monobromomethane.

The compounds of this invention (22):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.35-2.41(2H，m)，2.57-2.67(2H，m)，2.81(2H，t)。

Preparation embodiment 23

Adopt the method for preparing embodiment 18 to obtain 0.34g 2-(2,2,3,4,4,4-hexafluoro butyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (23) hereinafter), difference are with 2.4

g trifluoromethanesulfonic acid

2,2,3,4,4,4-hexafluoro butyl ester replaces the cyclopropyl monobromomethane.

The compounds of this invention (23):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.36-2.40(2H，m)，2.57-2.68(2H，m)，2.81-2.91(2H，m)，4.85-5.03(1H，m)。

Preparation embodiment 24

Adopt the method for preparing embodiment 18 to obtain 2.0g 2-(2,2,3,3,4,4,4-seven fluorine butyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (24) hereinafter), difference is with

15g trifluoromethanesulfonic acid

2,2,3,3,4,4,4-seven fluorine butyl esters replace the cyclopropyl monobromomethane.

The compounds of this invention (24):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.37-2,41(2H，m)，2.58-2.80(2H，m)，2.86(2H，t)。

Preparation embodiment 25

Adopt the method for preparing embodiment 18 to obtain 0.4g 2-(2-fluoro ethyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (25) hereinafter), difference is to replace the cyclopropyl monobromomethane with 2.2g toluenesulphonic acids 2-fluorine ethyl ester.

The compounds of this invention (25):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.29-2.34(2H，m)，2.40-2.42(2H，m)，2.46-2.59(2H，m)，4.82(2H，dt)。

Preparation embodiment 26

Adopt the method for preparing embodiment 18 to obtain 0.6g 2-((2-perfluoro hexyl) ethyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (26) hereinafter), difference are to replace the cyclopropyl monobromomethane with 4.7g (2-perfluoro hexyl) iodoethane.

The compounds of this invention (26):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.27-2.35(4H，m)，2.47-2.61(4H，m)。

Preparation embodiment 27

Adopt the method for preparing embodiment 18 to obtain 0.94g 2-(3,3, the 3-trifluoro propyl)-2-(2-propynyl) propane dinitrile (being called The compounds of this invention (27) hereinafter), difference is to replace the cyclopropyl monobromomethane with 1.2g3-bromo-1-propine.

The compounds of this invention (27):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.34-2.39(2H，m)，2.44-2.57(3H，m)，3.00(2H，s)。

Preparation embodiment 28

Adopt the method for preparing embodiment 18 to obtain 0.64g 2-cyclohexyl methyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (28) hereinafter), difference is to replace the cyclopropyl monobromomethane with 1.8g (brooethyl) hexanaphthene.

The compounds of this invention (28):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.14-1.71(5H，m)，1.80-1.98(8H，m)，2.06-2.11(2H，m)，2.21-2.28(2H，m)。

Preparation embodiment 29

Adopt the method for preparing embodiment 18 to obtain 1.8g 2-(3,3,4,4,4-five fluorine butyl)-and 2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (29) hereinafter), difference is with 2.8

g

3,3,4,4,4-five fluorine butyl iodides replace the cyclopropyl monobromomethane.

The compounds of this invention (29):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.12-2.20(4H，m)，2.23-2.59(4H，m)。

Preparation embodiment 30

Adopt the method for preparing embodiment 18 to obtain 0.89g 2-(4-bromo-3-chloro-3,4,4-trifluoro butyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (30) hereinafter), difference is that 2-trifluoro butane replaces the cyclopropyl monobromomethane with 2.8g 1-bromo-2-chloro-4-iodo-1,1.

The compounds of this invention (30):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：230-2.65(7H，m)，2.74-2.83(1H，m)。

Preparation embodiment 31

Adopt the method for preparing embodiment 18 to obtain 0.54g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (31) hereinafter), difference are with 1.6

g trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5-octafluoro pentyl ester replaces the cyclopropyl monobromomethane.

The compounds of this invention (31):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.36-2.41(2H，m)，2.57-2.65(2H，m)，2.84(2H，t)，6.07(1H，tt)。

Preparation embodiment 31-2

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.2g 1-bromo-3,3,3-trifluoro propane is dissolved in the 10ml glycol dimethyl ether, adds 0.97g salt of wormwood, and mixture was at room temperature stirred 10 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively.Through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 0.74g The compounds of this invention (31) through silica gel column chromatography.

Preparation embodiment 32

Adopt the method for preparing embodiment 18 to obtain 0.70g 2-(2,2,3,3,4,4,5,5,6,6,7,7-ten difluoro heptyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (32) hereinafter), difference is with 1.6g trifluoromethanesulfonic acid (2,2,3,3,4,4,5,5,6,6,7,7-ten difluoro heptyl esters) replacement cyclopropyl monobromomethane.

The compounds of this invention (32):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.36-2.41(2H，m)，2.58-2.65(2H，m)，2.84(2H，t)，6.06(1H，tt)。

Preparation embodiment 33

Adopt the method for preparing embodiment 18 to obtain 2.0g 2-((2-perfluor decyl) ethyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (33) hereinafter), difference are to replace the cyclopropyl monobromomethane with 3.2g 2-(perfluor decyl) iodoethane.

The compounds of this invention (33):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.66-2.80(4H，m)，3.23-3.29(4H，m)。

Preparation embodiment 34

Adopt the method for preparing embodiment 18 to obtain 0.1g 2-((2-perfluoro capryl) ethyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (34) hereinafter), difference are to replace the cyclopropyl monobromomethane with 2.4g 2-(perfluoro capryl) iodoethane.

The compounds of this invention (34):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.27-2.35(4H，m)，2.45-2.58(4H，m)。

Preparation embodiment 35

Adopt the method for preparing embodiment 18 to obtain 0.53g 2-(4-bromo-3,3,4,4-tetrafluoro butyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (35) hereinafter), difference is with 1.7g 1-bromo-4-iodo-1,1,2,2-tetrafluoro butane replaces the cyclopropyl monobromomethane.

The compounds of this invention (35):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.26-2.36(4H，m)，2.47-2.61(4H，m)。

Preparation embodiment 36

Adopt the method for preparing embodiment 18 to obtain 0.53g 2-(3,4,4,4-tetrafluoro-3-(trifluoromethyl) butyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (36) hereinafter), difference is with 1.7g 4-iodo-1,1,1,2-tetrafluoro-2-(trifluoromethyl) butane replaces the cyclopropyl monobromomethane.

The compounds of this invention (36):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.23-2.32(4H，m)，2.47-2.61(4H，m)。

Preparation embodiment 37

Adopt the method for preparing embodiment 18 to obtain 0.23g 2-(3,3,4,4,5,5,5-seven fluorine amyl groups)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (37) hereinafter), difference is with 1.6g 5-iodo-1,1,1,2,2,3,3-seven amyl fluorides replace the cyclopropyl monobromomethane.

The compounds of this invention (37):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.28-2.35(4H，m)，2.48-2.61(4H，m)。

Preparation embodiment 38

Adopt the method for preparing embodiment 18 to obtain 0.64g 2-(3,3,4,4,5,5,6,6,6-nine fluorine hexyls)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (38) hereinafter), difference is with 2.1

g

3,3,4,4,5,5,6,6,6-nine fluorine hexyl iodides replace the cyclopropyl monobromomethane.

The compounds of this invention (38):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.26-2.35(4H，m)，2.50-2.62(4H，m)。

Preparation embodiment 39

Adopt the method for preparing embodiment 18 to obtain 0.62g 2-(3-fluoropropyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (39) hereinafter), difference is with 1.4g3-fluoropropyl bromo for the cyclopropyl monobromomethane.

The compounds of this invention (39):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.05-2.11(2H，m)，2.13-2.19(2H，m)，2.20-2.28(2H，m)，3.49-2.59(2H，m)，4.57(2H，dt)。

Preparation embodiment 40

Adopt the method for preparing embodiment 18 to obtain 2.3g 2-(2-bromotrifluoromethane)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (40) hereinafter), difference is to use 5.6g1, and the 2-ethylene dibromide replaces the cyclopropyl monobromomethane.

The compounds of this invention (40):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.23-2.30(2H，m)，2.49-2.58(4H，m)，3.59(2H，t)。

Preparation embodiment 41

Adopt the method for preparing embodiment 18 to obtain 2.3g 2-(3-bromopropyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (41) hereinafter), difference is to use 5.6g1, and the 3-dibromopropane replaces the cyclopropyl monobromomethane.

The compounds of this invention (41):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.16-2.30(6H，m)，2.47-2.59(2H，m)，3.51(2H，t)。

Preparation embodiment 42

Adopt the method for preparing embodiment 18 to obtain 6.0g 2-(4-pentenyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (42) hereinafter), difference is to replace the cyclopropyl monobromomethane with 7.2g5-bromo-1-amylene.

The compounds of this invention (42):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.78-1.85(2H，m)，1.97-2.01(2H，m)，2.18-2.23(4H，m)，2.46-2.57(2H，m)，5.06-5.12(2H，m)，5.72-5.82(1H，m)。

Preparation embodiment 43

400mg 2-(2, the 2-dimethyl propyl) propane dinitrile is dissolved in 5ml N, and dinethylformamide cools off in ice bath subsequently.Toward wherein adding 120mg sodium hydride (60% oil suspension).After stopping to produce hydrogen, drip 750mg 1-bromo-3,3,3-trifluoro propane also at room temperature stirred mixture 12 hours.Subsequently frozen water and ethyl acetate are added in the reaction mixture.Stir the mixture, subsequently layering.Use the ethyl acetate extraction water layer.Merge organic layer, water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 437mg 2-(2, the 2-dimethyl propyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (43) hereinafter) through silica gel column chromatography.

The compounds of this invention (43):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.21(9H，s)，1.92(2H，s)，2.19-2.23(2H，m)，2.49-2.61(2H，m)。

Preparation embodiment 44

Adopt the method for preparing embodiment 1 (2) to obtain 0.20g 2-(2-methyl-2-propenyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (44) hereinafter), difference are to use 0.12g 3-bromo-methacrylic to replace 1-bromo-3-chloropropane.

The compounds of this invention (44):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.97(3H，s)，2.19-2.24(2H，m)，2.48-2.60(2H，m)，2.71(2H，s)，5.16(2H，d)。

Preparation embodiment 45

Adopt the method for preparing embodiment 1 (2) to obtain 0.16g 2-(2-methyl-propyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (45) hereinafter), difference are to use 0.14g 1-bromo-2-methylpropane to replace 1-bromo-3-chloropropane.

The compounds of this invention (45):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.17(6H，d)，1.89(2H，d)，2.08-2.18(1H，m)，2.19-2.23(2H，m)，2.47-2.62(2H，m)。

Preparation embodiment 46

With 1.2g 2-(2,2,3,4,4,4-hexafluoro butyl) propane dinitrile and 1.5g 2-chloro-1,4-two bromo-1,1,2-trifluoro butane is dissolved in the 10ml dimethyl sulfoxide (DMSO), adds 0.7g salt of wormwood, and mixture was at room temperature stirred 5 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, use ethyl acetate extraction subsequently.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 0.14g 2-(4-bromo-3-chloro-3,4,4-trifluoro butyl)-2-(2,2,3,4,4,4-hexafluoro butyl) propane dinitrile (being called The compounds of this invention (46) hereinafter) through silica gel column chromatography.

The compounds of this invention (46):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.39-2.93(6H，m)，4.86-5.02(1H，m)。

Preparation embodiment 47

0.56g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 0.30g allyl bromide 98 are dissolved in the 5ml dimethyl sulfoxide (DMSO), add 0.28g salt of wormwood, and mixture was at room temperature stirred 5 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, use ethyl acetate extraction subsequently.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 0.15g 2-(allyl group)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (47) hereinafter) through silica gel column chromatography.

The compounds of this invention (47):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.75(2H，t)，2.87(2H，d)，5.47-5.72(2H，m)，5.86-6.21(2H，m)。

Preparation embodiment 48

Adopt the method for preparing embodiment 18 to obtain 1.0g 2-(4,4,4-trifluoro butyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (48) hereinafter), difference is with 1.2g 1-iodo-4,4,4-trifluoro butane replaces the cyclopropyl monobromomethane.

The compounds of this invention (48):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.00-2.11(4H，m)，2.21-2.32(4H，m)，2.48-2.59(2H，m)。

Preparation embodiment 49

With 14.6

g trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5-octafluoro pentyl ester is dissolved in the 30ml dimethyl sulfoxide (DMSO), adds 5.5g salt of wormwood.In addition, drip the 2.6g propane dinitrile that is dissolved in the 10ml dimethyl sulfoxide (DMSO), mixture was at room temperature stirred 3 hours.In addition, add 7.0

g trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5-octafluoro pentyl ester and 2.7g salt of wormwood.Mixture stirred 1 hour.In this reaction mixture, add dilute hydrochloric acid subsequently, use ethyl acetate extraction subsequently.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates is through silica gel column chromatography.With the partial concentration that obtains and with the chloroform washing, obtain 0.13g 2, two (2,2,3,3,4,4,5, the 5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (49) hereinafter) of 2-.

The compounds of this invention (49):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：3.00(4H，t)，6.07(2H，tt)。

Preparation embodiment 50

The 7.5g propane dinitrile is dissolved in 50ml N, and dinethylformamide also adds 10.4g salt of wormwood.Mixture at room temperature stirred 1 hour, and drip and be dissolved in 20ml N, the 10.0g trifluoromethanesulfonic acid 2,2,3 in the dinethylformamide, 3-tetrafluoro propyl ester spends the night the mixture stirring.Subsequently with in the reaction mixture impouring water and use extracted with diethyl ether.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates is through silica gel column chromatography.The part that obtains is washed with chloroform, obtains 0.08g 2, two (2,2,3, the 3-tetrafluoro propyl group) propane dinitrile (being called The compounds of this invention (50) hereinafter) of 2-.

The compounds of this invention (50):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.89(4H，t)，5.88(2H，tt)。

Preparation embodiment 51

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.0g iodopentane are dissolved in the 10ml dimethyl sulfoxide (DMSO), add 0.70g salt of wormwood, mixture was at room temperature stirred 3 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, use ethyl acetate extraction subsequently.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 0.90g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-amyl group propane dinitrile (being called The compounds of this invention (51) hereinafter) through silica gel column chromatography.

The compounds of this invention (51):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.94(3H，t)，1.37-1.45(4H，m)，1.71-1.79(2H，m)，2.07-2.11(2H，m)，2.76(2H，t)，6.06(1H，tt)。

Preparation embodiment 52

3.2g 2-(3,3, the 3-trifluoro propyl) propane dinitrile, 7.0g methylene bromide and 5.5g salt of wormwood are added the 40ml dimethyl sulfoxide (DMSO), mixture was at room temperature stirred 18 hours.Extracted with diethyl ether will also be used subsequently subsequently in the reaction mixture impouring water.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous sodium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 3.4g 2-brooethyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (52) hereinafter) through silica gel column chromatography.

The compounds of this invention (52):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.32-2.38(2H，m)，2.50-2.59(2H，m)，3.72(2H，s)。

Preparation embodiment 53

With 2.0g 2-(3,3, the 3-trifluoro propyl) propane dinitrile and 4.7

g trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5,5-nine fluorine pentyl esters are dissolved in 10ml N, and dinethylformamide adds 2.0g salt of wormwood, and mixture stirred 4 hours down at 60 ℃.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.87g 2-(2,2,3,3,4,4,5,5,5-nine fluorine amyl groups)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (53) hereinafter) through silica gel column chromatography.

The compounds of this invention (53):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.36-2.41(2H，m)，2.56-2.67(2H，m)，2.84(2H，t)。

Preparation embodiment 54

1.6g 2-(3,3, the 3-trifluoro propyl) propane dinitrile and 3.1g 1,2-two chloro-4-iodo-1,1,2-trifluoro butane is dissolved in the 5ml dimethyl sulfoxide (DMSO), adds 1.4g salt of wormwood, and mixture was at room temperature stirred 6 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 1.9g 2-(3,4-two chloro-3,4,4-trifluoro butyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (54) hereinafter) through silica gel column chromatography.

The compounds of this invention (54):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.28-2.61(7H，m)，2.71-2.80(1H，m)。

Preparation embodiment 55

0.29g diethylaminosulfurtrifluoride is dissolved in the 5ml chloroform, at 0 ℃ of past down 0.40g 2-(5-hydroxyl amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile solution in the 3ml chloroform that wherein drips.Mixture at room temperature stirred 9 hours.In reaction mixture, add entry subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.12g 2-(5-fluorine amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (55) hereinafter) through silica gel column chromatography.

The compounds of this invention (55):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.54-1.61(2H，m)，1.70-1.84(4H，m)，1.99-2.03(2H，m)，2.19-2.23(2H，m)，2.46-2.58(2H，m)，4.48(2H，dt)。

Preparation embodiment 56

With 0.66g propane dinitrile and 9.7g 1-iodo-3,4,4,4-tetrafluoro-3-trifluoromethyl butane is dissolved in the 10ml glycol dimethyl ether, adds 4.1g salt of wormwood, and mixture was at room temperature stirred 15 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.04g 2 through silica gel column chromatography, two (3,4,4, the 4-tetrafluoro-3-trifluoromethyl butyl) propane dinitrile (being called The compounds of this invention (56) hereinafter) of 2-.

The compounds of this invention (56):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.27-2.31(4H，m)，2.47-2.57(4H，m)。

Preparation embodiment 57

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile is dissolved in the tetrahydrofuran solution (1mol/L) of 6ml tetrabutylammonium, is cooled to 0 ℃ subsequently.Toward wherein dripping 1.1g 2-bromo-3,3, the 3ml tetrahydrofuran solution of 3-trifluoro propene at room temperature stirred mixture 8 hours, stirred 5 hours down at 60 ℃ subsequently.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.02g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(2-bromo-3,3,3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (57) hereinafter) through silica gel column chromatography.

The compounds of this invention (57):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.71-2.98(4H，m)，4.33-4.46(1H，m)，6.03(1H，tt)。

Preparation embodiment 58

1.6g 2-(3,3, the 3-trifluoro propyl) propane dinitrile is dissolved in the tetrahydrofuran solution (1mol/L) of 20ml tetrabutylammonium, toward wherein adding 5ml 2-chloro-3,3, the 3-trifluoro propene at room temperature stirred mixture 3 hours under 0 ℃.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.22g 2-(2-chloro-3,3,3-trifluoro propyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (58) hereinafter) through silica gel column chromatography.

The compounds of this invention (58):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.31-2.40(2H，m)，2.54-2.66(4H，m)，4.47-4.52(1H，m)。

Preparation embodiment 59

0.15g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(3-oxo butyl) propane dinitrile is added in the 2ml diethylaminosulfurtrifluoride that is cooled to 0 ℃, mixture was at room temperature stirred 8 hours.Subsequently reaction mixture is added in the entry and also extract with methyl tertiary butyl ether subsequently.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.12g2-(3,3-difluoro butyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (59) hereinafter) through silica gel column chromatography.

The compounds of this invention (59):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.72(3H，t)，2.21-2.36(4H，m)，2.80(2H，t)，6.03(1H，tt)。

Preparation embodiment 60

The 1.1g diethylaminosulfurtrifluoride is dissolved in the 3ml chloroform, at 0 ℃ of past down 3ml chloroformic solution that wherein drips 0.80g 2-(5-oxo amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile.Mixture at room temperature stirred 7 hours.Subsequently reaction mixture is added in the entry and with methyl tert-butyl ether and extract.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.45g 2-(5,5-difluoro amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (60) hereinafter) through silica gel column chromatography.

The compounds of this invention (60):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.58-1.66(2H，m)，1.75-1.83(2H，m)，1.85-1.98(2H，m)，1.99-2.04(2H，m)，2.19-2.23(2H，m)，2.46-2.58(2H，m)，5.85(1H，tt)。

Preparation embodiment 61

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 4.0g trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro propyl ester is dissolved in the 10ml glycol dimethyl ether, adds 1.4g salt of wormwood, and mixture was at room temperature stirred 8 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.36g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(2,2,3,3-tetrafluoro propyl group) propane dinitrile (being called The compounds of this invention (61) hereinafter) through silica gel column chromatography.

The compounds of this invention (61):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.91(2H，t)，2.99(2H，t)，5.89(1H，tt)，6.06(1H，tt)。

Preparation embodiment 62

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 2.2g 1, the 3-dibromobutane is dissolved in the 10ml dimethyl sulfoxide (DMSO), adds 0.83g salt of wormwood, and mixture was at room temperature stirred 4 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 1.2g 2-(3-brombutyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (62) hereinafter) through silica gel column chromatography.

The compounds of this invention (62):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.81(3H，d)，2.14-2.47(4H，m)，2.83(2H，t)，4.13-4.18(1H，m)，6.07(1H，tt)。

Preparation embodiment 63

With 3.3g 2-(3,3, the 3-trifluoro propyl) propane dinitrile and 8.6g 1, the 4-dibromobutane is dissolved in the 20ml dimethyl sulfoxide (DMSO), adds 3.0g salt of wormwood, and mixture was at room temperature stirred 2 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and sodium chloride aqueous solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 3.2g 2-(4-brombutyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (63) hereinafter) through silica gel column chromatography.

The compounds of this invention (63):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.85-1.93(2H，m)，1.95-2.04(4H，m)，2.18-2.23(2H，m)，2.42-2.55(2H，m)，3.41(2H，t)。

Preparation embodiment 64

1.2g 2-(3-oxo butyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile is added in the 1.6g diethylaminosulfurtrifluoride that is cooled to 0 ℃.Mixture is adjusted to room temperature and stirred 3 hours.Subsequently reaction mixture is added in the entry and with methyl tert-butyl ether and extract.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.85g 2-(3,3-difluoro butyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (64) hereinafter) through silica gel column chromatography.

The compounds of this invention (64):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.68(3H，m)，2.18-2.27(6H，m)，2.43-2.56(2H，m)。

Preparation embodiment 65

With 3.2g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 8.6g 1, the 3-dibromopropane is dissolved in the 20ml dimethyl sulfoxide (DMSO), adds 3.0g salt of wormwood, and mixture was at room temperature stirred 2 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 3.2g 2-(3-bromopropyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (65) hereinafter) through silica gel column chromatography.

The compounds of this invention (65):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.30(4H，m)，2.78(2H，t)，3.52(2H，t)，6.02(1H，tt)。

Preparation embodiment 66

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.2g 1-iodo-4,4,4-trifluoro butane is dissolved in the 5ml dimethyl sulfoxide (DMSO), adds 0.83g salt of wormwood, and mixture was at room temperature stirred 5 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.35g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(4,4,4-trifluoro butyl) propane dinitrile (being called The compounds of this invention (66) hereinafter) through silica gel column chromatography.

The compounds of this invention (66):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.01-2.13(2H，m)，2.16-2.32(4H，m)，2.78(2H，t)，6.02(1H，tt)。

Preparation embodiment 67

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.5g 1,2-two chloro-4-iodo-1,1,2-trifluoro butane is dissolved in the 5ml dimethyl sulfoxide (DMSO), adds 0.83g salt of wormwood, and mixture was at room temperature stirred 9 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.05g 2-(3,4-two chloro-3,4,4-trifluoro butyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (67) hereinafter) through silica gel column chromatography.

The compounds of this invention (67):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.42-2.49(2H，m)，2.54-2.70(2H，m)，2.87(2H，t)，6.07(1H，tt)。

Preparation embodiment 68

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.4g 1-iodo-3,3,4,4, the 4-3-pentafluorobutane is dissolved in the 5ml dimethyl sulfoxide (DMSO), adds 0.83g salt of wormwood, and mixture was at room temperature stirred 7 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.45g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(3,3,4,4,4-five fluorine butyl) propane dinitrile (being called The compounds of this invention (68) hereinafter) through silica gel column chromatography.

The compounds of this invention (68):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.40-2.60(4H，m)，2.87(2H，t)，6.07(1H，tt)。

Preparation embodiment 69

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile is dissolved in the tetrahydrofuran solution (1mol/L) of 10ml tetrabutylammonium, at 0 ℃ of past down 5ml 2-chloro-3,3,3-trifluoro propene of wherein adding.This mixture at room temperature stirred 3 days subsequently.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.03g 2-(2-chloro-3,3,3-trifluoro propyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (69) hereinafter) through silica gel column chromatography.

The compounds of this invention (69):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.67-2.80(2H，m)，2.86-3.06(2H，m)，4.50-4.58(1H，m)，6.07(1H，tt)。

Preparation embodiment 70

1.2g 2-(3-oxo amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile is added in the 1.6g diethylaminosulfurtrifluoride that is cooled to 0 ℃, mixture was at room temperature stirred 5 hours.Subsequently reaction mixture is added in the entry and with methyl tert-butyl ether and extract.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.15g 2-(3,3-difluoro amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (70) hereinafter) through silica gel column chromatography.

The compounds of this invention (70):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.07(3H，t)，1.87-2.01(2H，m)，2.16-2，2.28(6H，m)，2.48-2.60(2H，m)。

Preparation embodiment 71

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.6g 1-iodo-3,3,4,4,5,5,5-seven amyl fluorides are dissolved in the 5ml glycol dimethyl ether, add 0.83g salt of wormwood, and mixture was at room temperature stirred 8 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.75g 2-(3,3,4,4,5,5,5-seven fluorine amyl groups)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (71) hereinafter) through silica gel column chromatography.

The compounds of this invention (71):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.41-2.45(2H，m)，2.50-2.64(2H，m)，2.87(2H，t)，6.07(1H，tt)。

Preparation embodiment 72

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.4g brooethyl cyclopropane are dissolved in the 10ml dimethyl sulfoxide (DMSO), add 1.4g salt of wormwood, mixture was at room temperature stirred 2 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.35g 2-cyclopropyl methyl-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (72) hereinafter) through silica gel column chromatography.

The compounds of this invention (72):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.43(2H，dd)，0.78(2H，dd)，1.06-1.13(1H，m)，2.09(2H，d)，2.81(2H，t)，6.06(1H，tt)。

Preparation embodiment 73

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.4g 4-bromo-1-butylene are dissolved in the 10ml dimethyl sulfoxide (DMSO), add 1.4g salt of wormwood, mixture was at room temperature stirred 5 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.09g 2-(3-butenyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (73) hereinafter) through silica gel column chromatography.

The compounds of this invention (73):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.18-2.22(2H，m)，21.50-2.55(2H，m)，2.79(2H，t)，5.15(2H，m)，5.78-5.87(1H，m)，6.07(1H，tt)。

Preparation embodiment 74

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.0g 1-bromo-3-fluoro-propane are dissolved in the 10ml glycol dimethyl ether, add 0.97g salt of wormwood, mixture was at room temperature stirred 10 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.67g 2-(3-fluoropropyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (74) hereinafter) through silica gel column chromatography.

The compounds of this invention (74):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.10-2.23(2H，m)，2.27-2.31(2H，m)，2.81(2H，t)，4.58(2H，dt)，6.07(1H，tt)。

Preparation embodiment 75

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.3g 1-bromo-3,4,4-three fluoro-3-butylene are dissolved in the 10ml glycol dimethyl ether, add 0.97g salt of wormwood, and mixture was at room temperature stirred 10 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.45g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(3,4,4-three fluoro-3-butenyls) propane dinitrile (being called The compounds of this invention (75) hereinafter) through silica gel column chromatography.

The compounds of this invention (75):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.35-2.39(2H，m)，2.74-2.87(4H，m)，6.06(1H，tt)。

Preparation embodiment 76

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 0.83g 1-bromo-2-propine are dissolved in the 10ml glycol dimethyl ether, add 0.97g salt of wormwood, mixture was at room temperature stirred 4 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.65g 2-(2-propynyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (76) hereinafter) through silica gel column chromatography.

The compounds of this invention (76):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.52(1H，t)，2.94(2H，t)，3.14(2H，d)，6.07(1H，tt)。

Preparation embodiment 77

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.1g 1-bromo-3-methylbutane are dissolved in the 10ml glycol dimethyl ether, add 0.97g salt of wormwood, mixture was at room temperature stirred 5 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.15g 2-(3-methyl butyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (77) hereinafter) through silica gel column chromatography.

The compounds of this invention (77):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.98(6H，d)，1.58-1.74(3H，m)，2.08-2.12(2H，m)，2.77(2H，t)，6.06(1H，tt)。

Preparation embodiment 78

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.1g 1-bromo-3-methyl-2-butene are dissolved in the 10ml glycol dimethyl ether, add 0.97g salt of wormwood, mixture was at room temperature stirred 7 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.50g 2-(3-methyl-2-butene base)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (78) hereinafter) through silica gel column chromatography.

The compounds of this invention (78):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.76(3H，s)，1.86(3H，s)，2.73(2H，t)，2.85(2H，d)，5.30(1H，t)，6.07(1H，tt)。

Preparation embodiment 79

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 3.3

g trifluoromethanesulfonic acid

2,2,3,3,4,4,4-seven fluorine butyl esters are dissolved in the 10ml glycol dimethyl ether, add 0.97g salt of wormwood, and mixture was at room temperature stirred 7 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.07g 2-(2,2,3,3,4,4,4-seven fluorine butyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (79) hereinafter) through silica gel column chromatography.

The compounds of this invention (79):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：3.01(4H，t)，6.07(1H，tt)。

Preparation embodiment 80

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.3g 1-butyl iodide are dissolved in the 10ml glycol dimethyl ether, add 0.97g salt of wormwood, mixture was at room temperature stirred 7 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 1.1g2-butyl-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (80) hereinafter) through silica gel column chromatography.

The compounds of this invention (80):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.00(3H，t)，1.43-1.53(2H，m)，1.69-1.77(2H，m)，2.07-2.12(2H，m)，2.72(2H，t)，6.06(1H，tt)。

Preparation embodiment 81

With 1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 3.1

g trifluoromethanesulfonic acid

2,2,3,4,4,4-hexafluoro butyl ester is dissolved in the 10ml glycol dimethyl ether, adds 0.97g salt of wormwood, and mixture was at room temperature stirred 7 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.06g 2-(2,2,3,4,4,4-hexafluoro butyl)-2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile (being called The compounds of this invention (81) hereinafter) through silica gel column chromatography.

The compounds of this invention (81):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.89-3.04(4H，m)，4.89-5.02(1H，m)，6.07(1H，tt)。

Preparation embodiment 82

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 1.3g propyl iodide are dissolved in the 10ml glycol dimethyl ether, add 0.97g salt of wormwood, mixture was at room temperature stirred 10 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 1.1g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-propyl group propane dinitrile (being called The compounds of this invention (82) hereinafter) through silica gel column chromatography.

The compounds of this invention (82):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.10(3H，t)，1.75-1.85(2H，m)，2.06-2.10(2H，m)，2.77(2H，t)，6.07(1H，tt)。

Preparation embodiment 83

With 1.2g 2-(3,3, the 3-trifluoro propyl) propane dinitrile and 0.76g 4-brooethyl-1,1-difluoro hexanaphthene is dissolved in 10ml N, and dinethylformamide adds 0.99g salt of wormwood, and mixture at room temperature stirs and spends the night.In reaction mixture, add entry subsequently, use the ethyl acetate extraction mixture.Organic layer is successively with the washing of dilute hydrochloric acid and saturated nacl aqueous solution, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.51g 2-(4,4-difluoro cyclohexyl) methyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (83) hereinafter) through silica gel column chromatography.

The compounds of this invention (83):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.42-1.56(2H，m)，1.71-1.96(5H，m)，1.99-2.08(2H，m)，2.10-2.25(4H，m)，2.46-2.60(2H，m)。

Preparation embodiment 84

Adopt the method for preparing embodiment 83 to obtain 56mg 2-[2-(3,3-difluoro cyclopentyl) ethyl]-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (84) hereinafter), difference is with 0.17g 3-(2-bromotrifluoromethane)-1,1-difluoro pentamethylene replaces 4-brooethyl-1,1-difluoro hexanaphthene.

The compounds of this invention (84):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.47(1H，m)，1.63-1.85(3H，m)，1.92-2.61(11H，m)。

Preparation embodiment 85

Adopt the method for preparing embodiment 83 to obtain 0.26g 2-(4-trifluoromethyl cyclohexyl) methyl]-2-(3,3, the 3-trifluoro propyl) propane dinitrile (suitable/inverse proportion=5/1) (being called The compounds of this invention (85) hereinafter), difference is to replace 4-brooethyl-1,1-difluoro hexanaphthene with 0.20g 1-brooethyl-4-trifluoromethyl hexanaphthene.

The compounds of this invention (85):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.10-1.22(0.33H，m)，1.36-1.49(0.33H，m)，1.51-1.85(6.34H，m)，1.90(0.33H，d)，2.00(1.67H，d)，2.24-2.40(5H，m)，2.43-2.61(2H，m)。

Preparation embodiment 86

Adopt the method for preparing embodiment 83 to obtain 0.35g 2-(4-methylcyclohexyl) methyl-2-(3,3, the 3-trifluoro propyl) propane dinitrile (suitable/inverse proportion=2/1) (being called The compounds of this invention (86) hereinafter), difference is to replace 4-brooethyl-1,1-difluoro hexanaphthene with 0.29g 1-brooethyl-4-methylcyclohexane.

The compounds of this invention (86):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.90(1H，d)，0.93(2H，d)，0.97-1.29(3H，m)，1.48-1.78(6H，m)，1.87(0.67H，d)，1.91-2.00(2.33H，m)，2.16-2.24(2H，m)，2.45-2.59(2H，m)。

Preparation embodiment 87

Adopt the method for preparing embodiment 60 to obtain 0.10g cis 2-(3-difluoromethyl cyclohexyl) methyl]-2-(3; 3; the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (87) hereinafter); difference is methyl-2-(3 with 0.18g cis 2-(3-formyl radical cyclohexyl); 3; the 3-trifluoro propyl) propane dinitrile replaces 2-(5-oxo amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile.

The compounds of this invention (87):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.97-1.49(4H，m)，1.78-2.13(8H，m)，2.19-2.29(2H，m)，2.47-2.62(2H，m)，5.58(1H，dt)。

Preparation embodiment 88

Adopt the method for preparing embodiment 55 to obtain 0.12g cis 2-(3-methyl fluoride cyclohexyl) methyl]-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (88) hereinafter), difference is methyl-2-(3 with 0.32g cis 2-(3-hydroxymethyl cyclohexyl), 3, the 3-trifluoro propyl) propane dinitrile replaces 2-(5-hydroxyl amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile.

The compounds of this invention (88):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.86-1.13(3H，m)，1.38(1H，m)，1.74-2.09(8H，m)，2.16-2.26(2H，m)，2.46-2.60(2H，m)，4.17-4.37(2H，m)。

Preparation embodiment 89

Under 0 ℃, the 18.6g trifluoromethanesulfanhydride anhydride is added drop-wise to 10.7

g

4,4,5,5, in the 5-Pentafluorobenzyl pentanol.Mixture at room temperature stirred 1 hour, stirred 2 hours down at 80 ℃ subsequently.To also extract with t-butyl methyl ether subsequently in the reaction mixture impouring frozen water subsequently.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, and through anhydrous magnesium sulfate drying, concentrating under reduced pressure obtains 6.2

g trifluoromethanesulfonic acid

4,4,5,5 subsequently, 5-five fluorine pentyl esters.

Add 6.2

g trifluoromethanesulfonic acid

4,4,5,5 in the 10ml glycol dimethyl ether, 5-five fluorine pentyl esters, 1.6g 2-(3,3, the 3-trifluoro propyl) propane dinitrile and 1.4g salt of wormwood at room temperature stirred mixture 5 hours.In reaction mixture, add dilute hydrochloric acid and extract mixture subsequently with t-butyl methyl ether.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.65g 2-(4,4,5,5,5-five fluorine amyl groups)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (89) hereinafter) through silica gel column chromatography.

The compounds of this invention (89):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.05-2.26(8H，m)，2.48-2.60(2H，m)。

Preparation embodiment 90

Add 1.4g 2-(4-oxo amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile in 0 ℃ the 2ml diethylaminosulfurtrifluoride toward being cooled to, mixture was at room temperature stirred 5 hours.To also extract with t-butyl methyl ether subsequently in the reaction mixture impouring water subsequently.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.37g 2-(4,4-difluoro amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile (being called The compounds of this invention (90) hereinafter) through silica gel column chromatography.

The compounds of this invention (90):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.65(3H，t)，1.86-2.89(6H，m)，2.20-2.24(2H，m)，2.47-2.59(2H，m)。

Preparation embodiment 91

With 2.8g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 4.5g trifluoromethanesulfonic acid 2,2,3,3,3-five fluorine propyl ester are dissolved in 20ml acetone, add 2.2g salt of wormwood, and mixture was at room temperature stirred 8 hours.In reaction mixture, add dilute hydrochloric acid and extract mixture subsequently with t-butyl methyl ether.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.10g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(2,2,3,3,3-five fluoropropyls) propane dinitrile (being called The compounds of this invention (91) hereinafter) through silica gel column chromatography.

The compounds of this invention (91):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.96(2H，t)，3.00(2H，t)，6.07(1H，tt)。

Preparation embodiment 92

With 2.1g 2-(2,2,3,3,3-five fluoropropyls) propane dinitrile and 4.5g trifluoromethanesulfonic acid 2,2,3,3,3-five fluorine propyl ester are dissolved in 20ml acetone, add 2.2g salt of wormwood, and mixture was at room temperature stirred 10 hours.In reaction mixture, add dilute hydrochloric acid and extract mixture subsequently with t-butyl methyl ether.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.05g 2 through silica gel column chromatography, two (2,2,3,3, the 3-five fluoropropyls) propane dinitrile (being called The compounds of this invention (93) hereinafter) of 2-.

The compounds of this invention (93):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.96(4H，t)。

Preparation embodiment 93

With 2.0g 2-(2,2,3,4,4,4-hexafluoro butyl) propane dinitrile and 5.3

g trifluoromethanesulfonic acid

2,2,3,4,4,4-hexafluoro butyl ester is dissolved in 50ml acetone, adds 1.9g salt of wormwood, and mixture was at room temperature stirred 10 hours.In reaction mixture, add dilute hydrochloric acid and extract mixture subsequently with t-butyl methyl ether.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.05g 2 through silica gel column chromatography, two (2,2,3,4,4, the 4-hexafluoro butyl) propane dinitrile (being called The compounds of this invention (95) hereinafter) of 2-.

The compounds of this invention (95):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.84-3.06(4H，m)，4.85-5.05(2H，m)。

Preparation embodiment 94

3.2g 2-(2,2,3,3,3-five fluoropropyls) propane dinitrile and 7.2g 5-iodo-1,1,1,2,2,3,3-seven amyl fluorides are dissolved in 50ml acetone, add 3.2g salt of wormwood, and mixture was at room temperature stirred 10 hours.In reaction mixture, add dilute hydrochloric acid and extract mixture subsequently with t-butyl methyl ether.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.05g 2-(3,3,4,4,5,5,5-seven fluorine amyl groups)-2-(2,2,3,3,3-five fluoropropyls) propane dinitrile (being called The compounds of this invention (96) hereinafter) through silica gel column chromatography:

The compounds of this invention (96):

¹H-MR(CDCl ₃，TMS)δ(ppm)：2.41-2.45(2H，m)，2.50-2.64(2H，m)，2.82(2H，t)。

Below will specifically list compound of the present invention, but the invention is not restricted to this.

The compound of formula (I) expression:

The combination of R and Q sees the following form 1 to table 4 in the formula.

Table 1

Table 2

Table 3

Table 4

In order to prepare the intermediate of The compounds of this invention, subsequently to being described with reference to preparation embodiment.

With reference to preparation embodiment 1

The 27.6g propane dinitrile is dissolved in 50ml N, and dinethylformamide adds salt of wormwood 27.6g, and mixture was at room temperature stirred 1 hour.Subsequently toward wherein adding 17.7g 1-bromo-3,3,3-trifluoro propane and 20ml N, the mixture of dinethylformamide continues mixture to stir 1 hour.Extracted with diethyl ether will also be used subsequently subsequently in the reaction mixture impouring water.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 11.3g 2-(3,3, the 3-trifluoro propyl) propane dinitrile through silica gel column chromatography.

2-(3,3, the 3-trifluoro propyl) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.32-2.42(2H，m)，2.43-2.52(2H，m)，3.91(1H，t)。

With reference to preparation embodiment 2

Under 0 ℃, the 100ml trifluoromethanesulfanhydride anhydride is dropped to 79.2g 2,2,3, in the 3-C3-Fluoroalcohol.Subsequently, mixture was at room temperature stirred 1 hour, stirred 3 hours down at 60 ℃ subsequently.Subsequently reaction mixture impouring frozen water is also used extracted with diethyl ether subsequently.Organic layer is water and saturated sodium-chloride water solution washing successively, and through anhydrous magnesium sulfate drying, concentrating under reduced pressure obtains 100g trifluoromethanesulfonic acid 2,2,3 subsequently, 3-tetrafluoro propyl ester.

Trifluoromethanesulfonic acid 2,2,3,3-tetrafluoro propyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：4.73(2H，t)，5.97(1H，tt)。

With reference to preparation embodiment 3

Adopt with reference to the method for preparing embodiment 2 and obtain 1.2g trifluoromethanesulfonic acid 2,2, the 2-trifluoro ethyl ester, difference is to replace 2,2,3 with the 2.0g 2,2,2 tfifluoroethyl alcohol, the 3-C3-Fluoroalcohol.

Trifluoromethanesulfonic acid 2,2, the 2-trifluoro ethyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：4.71(2H，q)。

With reference to preparation embodiment 4

Adopt with reference to the method for preparing embodiment 2 and obtain 4.1g trifluoromethanesulfonic acid 2,2,3,3,3-five fluorine propyl ester, difference is that with 4.8g 2,2,3,3,3-five fluorine propyl alcohol replace 2,2,3, the 3-C3-Fluoroalcohol.

Trifluoromethanesulfonic acid 2,2,3,3,3-five fluorine propyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：4.72(2H，t)。

With reference to preparation embodiment 5

Adopt with reference to the method for preparing embodiment 2 and obtain 16.5

g trifluoromethanesulfonic acid

2,2,3,4,4,4-hexafluoro butyl ester, difference is that with 14.1

g

2,2,3,4,4,4-hexafluoro butanols replaces 2,2,3, the 3-C3-Fluoroalcohol.

Trifluoromethanesulfonic acid

2,2,3,4,4,4-hexafluoro butyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：4.71-4.79(2H，m)，4.92-5.11(1H，m)。

With reference to preparation embodiment 6

Adopt with reference to the method for preparing embodiment 2 and obtain 10g trifluoromethanesulfonic

acid

2,2,3,3,4,4,4-seven fluorine butyl esters, difference is that with 8.0

g

2,2,3,3,4,4,4-seven fluoro butanols replace 2,2,3, the 3-C3-Fluoroalcohol.

Trifluoromethanesulfonic acid

2,2,3,3,4,4,4-seven fluorine butyl esters:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：4.80(2H，t)。

With reference to preparation embodiment 7

Adopt with reference to the method for preparing embodiment 2 and obtain

187g trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5-octafluoro pentyl ester, difference is that with

139g

2,2,3,3,4,4,5, the 5-octafluoropentanol replaces 2,2,3, the 3-C3-Fluoroalcohol.

Trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5-octafluoro pentyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：4.82(2H，m)，6.04(1H，tt)。

With reference to preparation embodiment 8

Adopt with reference to the method for preparing embodiment 2 and obtain 20.5

g trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5,6,6,7,7-ten difluoro heptyl esters, difference is to use 16.6g2, and 2,3,3,4,4,5,5,6,6,7,7-ten difluoro enanthol replace 2,2,3, the 3-C3-Fluoroalcohol.

Trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5,6,6,7,7-ten difluoro heptyl esters:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：4.83(2H，t)，6.07(1H，tt)。

With reference to preparation embodiment 9

With 14.6

g trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5,6,6,7,7-ten difluoro heptyl esters are dissolved in the 20ml dimethyl sulfoxide (DMSO), add 5.5g salt of wormwood.10ml dimethyl sulphoxide solution toward wherein dripping the 2.6g propane dinitrile at room temperature stirred mixture 3 hours.Extracted with diethyl ether will also be used in the reaction mixture impouring water subsequently.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 2.0g 2-(2,2,3,3,4,4,5,5,6,6,7,7-ten difluoro heptyl) propane dinitrile through silica gel column chromatography.

2-(2,2,3,3,4,4,5,5,6,6,7,7-ten difluoro heptyl) propane dinitrile

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.91(2H，dt)，4.14(1H，t)，6.05(1H，tt)。

With reference to preparation embodiment 10

With 8.0

g trifluoromethanesulfonic acid

2,2,3,4,4,4-hexafluoro butyl ester is dissolved in the 15ml dimethyl sulfoxide (DMSO), adds 6.9g salt of wormwood.The past wherein 15ml dimethyl sulphoxide solution of Dropwise 5 .0g propane dinitrile at room temperature stirred mixture 3 hours.Extracted with diethyl ether will also be used in the reaction mixture impouring water subsequently.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 2.0g 2-(2,2,3,4,4,4-hexafluoro butyl) propane dinitrile through silica gel column chromatography.

2-(2,2,3,4,4,4-hexafluoro butyl) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.79-2.91(2H，m)，4.15(1H，t)，4.84-5.04(1H，m)。

With reference to preparation embodiment 11

Under 0 ℃, the 6.8g trifluoromethanesulfanhydride anhydride is dropped to 5.0

g

2,2,3,3,4,4,5,5, in the 5-nine fluorine amylalcohols, mixture was at room temperature stirred 5 hours, stirred 3 hours down at 100 ℃ subsequently.Subsequently with reaction mixture impouring frozen water and methyl tertiary butyl ether extraction subsequently.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, and through anhydrous magnesium sulfate drying, concentrating under reduced pressure obtains 4.7

g trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5 subsequently, 5-nine fluorine pentyl esters.

Trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5,5-nine fluorine pentyl esters:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：4.82(2H，t)。

With reference to preparation embodiment 12

With

15g trifluoromethanesulfonic acid

2,2,3,3,4,4,5,5-octafluoro pentyl ester and 2.6g propane dinitrile are dissolved in the 20ml dimethyl sulfoxide (DMSO), add 5.5g salt of wormwood, with mixture stirred in water bath 3 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 2.0g2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile through silica gel column chromatography.

2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.90(2H，dt)，4.15(1H，t)，6.06(1H，tt)。

With reference to preparation embodiment 13

PhH ₂C-O-CH ₂CH ₂CH ₂CH ₂CH ₂OH+CBr ₄

→PhH ₂C-O-CH ₂CH ₂CH ₂CH ₂CH ₂Br

7.0g 5-hydroxyl amyl group benzylic ether and 10.6g triphenylphosphine are added in the 50ml methyl tertiary butyl ether, be cooled to 0 ℃ subsequently.In addition, add the 13.2g carbon tetrabromide, mixture was at room temperature stirred 3 hours.Add the 100ml hexane subsequently, the concentrating under reduced pressure mixture.Resistates obtains 5.5g 5-bromine amyl group benzylic ether through silica gel column chromatography.

5-bromine amyl group benzylic ether:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.49-1.57(2H，m)，1.61-1.68(2H，m)，1.85-1，92(2H，m)，3.41(2H，t)，2.48(2H，t)，4.50(2H，s)，7.26-7.37(5H，m)。

With reference to preparation embodiment 14

3.5g 2-(3,3, the 3-trifluoro propyl) propane dinitrile, 5.5g 5-bromine amyl group benzylic ether and 0.70g potassiumiodide are dissolved in the 20ml dimethyl sulfoxide (DMSO), add 3.3g salt of wormwood, mixture was at room temperature stirred 9 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 5.9g 2-(5-benzyloxy amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile through silica gel column chromatography.

2-(5-benzyloxy amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.48-1.57(2H，m)，1.64-1.76(4H，m)，1.95-2.00(2H，m)，2.20-2.44(2H，m)，2.44-2.56(2H，m)，3.49(2H，t)，4.50(2H，s)，7.28-7.35(5H，m)。

With reference to preparation embodiment 15

1.8g 2-(5-benzyloxy amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile is added in the 20ml acetonitrile that is cooled to 0 ℃.In this mixture, add the 1.6g sodium iodide, drip the 1.3g trifluoroboranes-etherate that is dissolved in the 5ml acetonitrile subsequently.This mixture stirred 1 hour down at 0 ℃, at room temperature stirred 6 hours.In reaction mixture, add entry subsequently, use chloroform extraction subsequently.Organic layer water and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 0.40g 2-(5-hydroxyl amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile through silica gel column chromatography.

2-(5-hydroxyl amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.26(1H，br)，1.51-1.57(2H，m)，1.61-1.66(2H，m)，1.72-1.79(2H，m)，1.98-2.02(2H，m)，2.18-2.23(2H，m)，2.48-2.55(2H，m)，3.69(2H，t)。

With reference to preparation embodiment 16

1.4g 2-(2,2,3,3,4,4,5,5-octafluoro amyl group) propane dinitrile and 0.70g methyl vinyl ketone are dissolved in 15ml acetone, add 0.83g salt of wormwood, mixture was at room temperature stirred 4 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.5g2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(3-oxo butyl) propane dinitrile through silica gel column chromatography.

2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(3-oxo butyl) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.26(3H，s)，2.39(2H，t)，2.80(2H，t)，2.94(2H，t)，6.07(1H，tt)。

With reference to preparation embodiment 17

The Dess-Martin of 20ml15% is crossed iodine alkane (periodinane)=1,1,1-three (acetoxyl group)-1,1-dihydro-1, the dichloromethane solution of 2-benzo iodine heterocycle pentanone (benziodoxol)-3-(1H)-ketone drops to 1.5g 2-(5-hydroxyl amyl group)-2-(3,3,3-trifluoro propyl) in the propane dinitrile, mixture was at room temperature stirred 5 hours.Subsequently reaction mixture is added to dilute sodium hydroxide aqueous solution and use chloroform extraction subsequently.Organic layer water and sodium chloride aqueous solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 1.0g 2-(5-oxo amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile through silica gel column chromatography.

2-(5-oxo amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.73-1.78(4H，m)，1.99-2.03(2H，m)，2.19-2.23(2H，m)，2.46-2.59(4H，m)，9.81(1H，t)。

With reference to preparation embodiment 18

3.2g 2-(3,3, the 3-trifluoro propyl) propane dinitrile and 2.1g methyl vinyl ketone are dissolved in 30ml acetone, add 3.3g salt of wormwood, mixture was at room temperature stirred 4 hours.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.7g 2-(3,3, the 3-trifluoro propyl)-2-(3-oxo butyl) propane dinitrile through silica gel column chromatography.

2-(3,3, the 3-trifluoro propyl)-2-(3-oxo butyl) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.19-2.30(7H，m)，2.46-2.55(2H，m)，2.84-2.91(2H，m)。

With reference to preparation embodiment 19

3.2g 2-(3,3, the 3-trifluoro propyl) propane dinitrile and 1.7g ethyl vinyl ketone are dissolved in 30ml acetone, add 3.3g salt of wormwood, mixture was at room temperature stirred 1 hour.In this reaction mixture, add dilute hydrochloric acid subsequently, extract with methyl tertiary butyl ether again.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 1.3g 2-(3,3, the 3-trifluoro propyl)-2-(3-oxo amyl group) propane dinitrile through silica gel column chromatography.

2-(3,3, the 3-trifluoro propyl)-2-(3-oxo amyl group) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.11(3H，t)，2.22-2.26(2H，m)，2.31(2H，t)，2.46-2.58(4H，m)，2.84(2H，t)。

With reference to preparation embodiment 20

Adopt the method for preparing embodiment 60 to obtain 2.5g 4,4-difluoro naphthenic acid ethyl ester, difference is to replace 2-(5-oxo amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile with 5.0g 4-oxo naphthenic acid ethyl ester.

4,4-difluoro naphthenic acid ethyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.26(3H，t)，1.69-2.16(8H，m)，2.39(1H，m)，4.15(2H，q)。

With reference to preparation embodiment 21

(1) under nitrogen atmosphere, with 2.3g 4,4-difluoro naphthenic acid ethyl ester is dissolved in the 50ml tetrahydrofuran (THF).Toward wherein adding the 0.46g lithium aluminum hydride, mixture was 0 ℃ little stirring 1 hour under 0 ℃.Add the 1N aqueous sodium hydroxide solution subsequently in reaction mixture, the solid that leaches formation also washs with ethyl acetate subsequently.Merging filtrate and washing soln, through anhydrous magnesium sulfate drying, concentrating under reduced pressure obtains (4,4-difluoro cyclohexyl) methyl alcohol.

(2) with above-mentioned (4,4-difluoro cyclohexyl) dissolve with methanol in the 5ml pyridine.Toward wherein adding the 2.2g Tosyl chloride, mixture at room temperature stirs and spends the night under 0 ℃.Concentrating under reduced pressure reaction mixture subsequently.Resistates is dissolved in ethyl acetate, water, dilute hydrochloric acid and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, concentrating under reduced pressure subsequently.Resistates obtains 3.1g tosic acid 4 through silica gel column chromatography, 4-difluoro cyclohexyl methyl esters.

Tosic acid 4,4-difluoro cyclohexyl methyl esters:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.18-1.37(2H，m)，1.56-1.86(5H，m)，2.00-2.17(2H，br)，2.46(3H，s)，3.86(2H，d)，7.35(2H，d)，7.78(2H，d)。

With reference to preparation embodiment 22

With 1.5g tosic acid 4,4-difluoro cyclohexyl methyl esters is dissolved in 15ml acetone.Toward wherein adding 1.6g lithiumbromide monohydrate, mixture heating up was refluxed 8 hours.After reaction mixture is cooled to room temperature, add entry, extract mixture with t-butyl methyl ether.Organic layer washs with saturated sodium-chloride water solution, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.76g 4-brooethyl-1 through silica gel column chromatography, 1-difluoro hexanaphthene.

4-brooethyl-1,1-difluoro hexanaphthene:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.33-1.48(2H，m)，1.64-1.84(3H，m)，1.90-2.00(2H，m)，2.14-2.20(2H，m)，3.31(2H，d)。

With reference to preparation embodiment 23

Adopt the method for preparing embodiment 60 to obtain 0.9g (3,3-difluoro cyclopentyl) methyl acetate, difference is to replace 2-(5-oxo amyl group)-2-(3,3, the 3-trifluoro propyl) propane dinitrile with 1.8g (3-oxocyclopentyl) methyl acetate.

(3,3-difluoro cyclopentyl) methyl acetate:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.46(1H，m)，1.75(1H，m)，1.98-2.25(3H，m)，2.29-2.44(3H，m)，2.53(1H，m)，3.68(3H，s)。

With reference to preparation embodiment 24

Adopt with reference to the method for preparing embodiment 21 and obtain 0.68g tosic acid 2-(3,3-difluoro cyclopentyl) ethyl ester, difference is to replace 4 with 0.50g (3,3-difluoro cyclopentyl) methyl acetate, 4-difluoro naphthenic acid ethyl ester.

Tosic acid 2-(3,3-difluoro cyclopentyl) ethyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.35(1H，m)，1.59(1H，m)，1.70-1.76(2H，m)，1.85-2.24(5H，m)，2.46(3H，s)，3.98-4.08(2H，m)，7.36(2H，d)，7.79(2H，d)。

With reference to preparation embodiment 25

Adopt with reference to the method for preparing embodiment 22 and obtain 0.17g 3-(2-bromotrifluoromethane)-1,1-difluoro pentamethylene, difference is to replace tosic acid 4,4-difluoro cyclohexyl methyl esters with 0.33g tosic acid 2-(3,3-difluoro cyclopentyl) ethyl ester.

3-(2-bromotrifluoromethane)-1,1-difluoro pentamethylene:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.42(1H，m)，1.69(1H，m)，1.92-2.39(7H，m)，3.39(2H，t)。

With reference to preparation embodiment 26

1.0g 4-trifluoromethyl naphthenic acid is dissolved in 25ml methyl alcohol.Toward wherein adding the 50mg concentrated hydrochloric acid, mixture heating up was refluxed 10 hours.After reaction mixture is cooled to room temperature,, extract mixture with t-butyl methyl ether toward wherein adding entry.Organic layer washs with saturated sodium-chloride water solution, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 0.83g4-trifluoromethyl naphthenic acid methyl esters (suitable/inverse proportion=7/1) through silica gel column chromatography.

4-trifluoromethyl naphthenic acid methyl esters (suitable/inverse proportion=7/1):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.23-1.59(3H，m)，1.73-1.84(2H，m)，1.94-2.28(4H，m)，2.66(1H，m)，3.68(0.37H，s)，3.71(2.63H，s)。

With reference to preparation embodiment 27

Adopt with reference to the method for preparing embodiment 21 and obtain 1.2g tosic acid 4-trifluoromethyl cyclohexyl methyl esters (cis/trans=12/1), difference is to replace 4,4-difluoro naphthenic acid ethyl ester with 0.83g 4-trifluoromethyl naphthenic acid methyl esters.

Tosic acid 4-trifluoromethyl cyclohexyl methyl esters (cis/trans=12/1):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.91-1.68(7H，m)，1.80-2.11(3H，m)，2.47(3H，s)，3.84(0.15H，d)，3.96(1.85H，d)，7.36(2H，d)，7.76-7.84(2H，m)。

With reference to preparation embodiment 28

Adopt with reference to the method for preparing embodiment 22 and obtain 0.31g 1-brooethyl-4-trifluoromethyl hexanaphthene (cis/trans=10/1), difference is to replace tosic acid 4,4-difluoro cyclohexyl methyl esters with 1.2g tosic acid 4-trifluoromethyl cyclohexyl methyl esters.

1-brooethyl-4-trifluoromethyl hexanaphthene (cis/trans=10/1):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.01-1.82(7H，m)，1.95-2.18(3H，m)，3.30(0.18H，d)，3.41(1.82H，d)。

With reference to preparation embodiment 29

Adopt with reference to the method for preparing embodiment 21 (2) and obtain 1.6g tosic acid 4-methylcyclohexyl methyl esters (cis/trans=5/2), difference is to use 0.85g (4-methylcyclohexyl) methyl alcohol to replace (4,4-difluoro cyclohexyl) methyl alcohol.

Tosic acid 4-methylcyclohexyl methyl esters (cis/trans=5/2):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.85(0.86H，d)，0.86(2.14H，d)，0.91(1H，m)，1.09-1.21(2H，m)，1.32-1.51(4H，m)，1.56-1.75(2H，m)，1.85(1H，m)，2.36(0.86H，s)，2.45(2.14H，s)，3.81(0.57H，d)，3.92(1.43H，d)，7.34(2H，d)，7.74-7.83(2H，m)。

With reference to preparation embodiment 30

Adopt with reference to the method for preparing embodiment 22 and obtain 0.29g 1-brooethyl-4-methylcyclohexane (cis/trans=5/2), difference is to replace tosic acid 4,4-difluoro cyclohexyl methyl esters with 1.6g tosic acid 4-methylcyclohexyl methyl esters.

1-brooethyl-4-methylcyclohexane (cis/trans=5/2):

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.86-1.09(4H，m)，1.22-1.37(2H，m)，1.43-1.92(7H，m)，3.28(0.57H，d)，3.38(1.43H，d)。

With reference to preparation embodiment 31

Adopt with reference to the method for preparing embodiment 22 obtain 1.9g cis-3-brooethyl naphthenic acid ethyl ester and 0.41g trans-3-brooethyl naphthenic acid ethyl ester, difference is to replace tosic acid 4,4-difluoro cyclohexyl methyl esters with 3.8g 3-(toluene-4-sulfonyloxy methyl) naphthenic acid ethyl ester.

Cis-3-brooethyl naphthenic acid ethyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.92-1.37(7H，m)，1.69(1H，m)，1.82-2.00(3H，m)，2.11(1H，br)，2.33(1H，m)，330(2H，d)，4.13(2H，q)。

Trans-3-brooethyl naphthenic acid ethyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.15-1.64(8H，m)，1.77(1H，m)，1.90-2.01(2H，m)，2.13(1H，m)，2.66(1H，m)，3.33(2H，d)，4.15(2H，q)。

With reference to preparation embodiment 32

Adopt the method for preparing embodiment 84 to obtain 1.1g cis 3-(2,2-dicyano-5,5,5-trifluoro amyl group) naphthenic acid ethyl ester, difference is to replace 4-brooethyl-1,1-difluoro hexanaphthene with 1.1g cis 3-brooethyl naphthenic acid ethyl ester.

Cis 3-(2,2-dicyano-5,5,5-trifluoro amyl group) naphthenic acid ethyl ester:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.08(1H，m)，1.21-1.45(7H，m)，1.82(1H，m)，1.91(2H，d)，1.99-2.08(2H，br)，2.11-2.24(3H，m)，2.38(1H，m)，2.46-2.60(2H，m)，4.13(2H，q)。

With reference to preparation embodiment 33

Under nitrogen atmosphere, 1.1g cis 3-(2,2-dicyano-5,5,5-trifluoro amyl group) naphthenic acid ethyl ester is dissolved in the 10ml tetrahydrofuran (THF).At-78 ℃ of past down hexane solutions (0.93mol/L) that wherein drip the 7.0ml diisobutylaluminium hydride, mixture stirred 2 hours at-78 ℃.In reaction mixture impouring saturated sodium-chloride water solution, extract with t-butyl methyl ether subsequently.Organic layer is through anhydrous sodium sulfate drying, subsequently concentrating under reduced pressure.Resistates obtains 0.18g cis 2-(3-formyl radical cyclohexyl methyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile and 0.32g cis 2-(3-hydroxymethyl cyclohexyl methyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile through silica gel column chromatography.

Cis 2-(3-formyl radical cyclohexyl methyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.00-2.10(10H，m)，2.15-2.27(3H，m)，2.34-2.61(3H，m)，9.64(1H，s)。

Cis 2-(3-methylol cyclohexyl methyl)-2-(3,3, the 3-trifluoro propyl) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：0.78-1.45(4H，m)，1.61(1H，m)，1.77-1.92(5H，m)，1.97-2.08(2H，br)，2.17-2.27(2H，m)，2.46-2.60(2H，m)，3.45-3.56(2H，br)。

With reference to preparation embodiment 34

With 2.7g 2-(3,3, the 3-trifluoro propyl) propane dinitrile and 3.5g 2-(3-bromopropyl)-2-methyl isophthalic acid, the 3-dioxolane is dissolved in 30ml acetone.Toward wherein adding 2.3g salt of wormwood, mixture was at room temperature stirred 5 hours.Add reaction mixture in the dilute hydrochloric acid subsequently and stirred 1 hour.With t-butyl methyl ether extractive reaction mixture.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains the compound that the 1.4g following formula is represented through silica gel column chromatography:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：1.91-1.99(2H，m)，2.01-2.06(2H，m)，2.18(3H，s)，2.20-2.24(2H，m)，2.46-2.57(2H，m)，2.62(2H，t)。

With reference to preparation embodiment 35

With 8.4g trifluoromethanesulfonic acid 2,2,3,3,3-five fluorine propyl ester and 5.9g propane dinitrile are dissolved in the 30ml glycol dimethyl ether.Toward wherein adding 12.3g salt of wormwood, mixture was at room temperature stirred 8 hours.In reaction mixture, add dilute hydrochloric acid and extract mixture subsequently with t-butyl methyl ether.Organic layer is water, saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution washing successively, through anhydrous magnesium sulfate drying, and concentrating under reduced pressure subsequently.Resistates obtains 2.1g 2-(2,2,3,3,3-five fluoropropyls) propane dinitrile through silica gel column chromatography.

2-(2,2,3,3,3-five fluoropropyls) propane dinitrile:

¹H-NMR(CDCl ₃，TMS)δ(ppm)：2.86(2H，dt)，4.14(1H，t)。

" part " represents weight part then will to describe example of formulations, term.In addition, The compounds of this invention will refer to above-mentioned compound number.

Example of formulations 1

9 parts of any The compounds of this invention (1)-(96) are dissolved in 37.5 parts of dimethylbenzene and 37.5 parts of N, dinethylformamide.Toward wherein adding 10 parts of polyoxyethylene styryl phenyl ethers and 6 parts of calcium dodecylbenzene sulphonates, thoroughly mix and obtain emulsion.

Example of formulations 2

Add 5 parts of SORPOL 5060 (TOHO Chemical Industry Co., the registrar name of an article of LTD.) in 40 parts of any The compounds of this invention (1)-(96) and mix.Subsequently, toward wherein adding 32 parts of CARPLEX #80 (Shionogi ﹠amp; Co., the registrar name of an article of Ltd., synthetic dry oxidation silica fine powder) and 23 part of 300 order diatomite, use the fruit juice mixing tank to mix, obtain wettable preparation.

Example of formulations 3

3 parts of any The compounds of this invention (1)-(96), 5 parts of oxidizing aqueous silica fine powders of synthetic, 5 parts of Sodium dodecylbenzene sulfonatees, 30 parts of wilkinites and 57 parts of clays are thoroughly mixed.In this mixture, add an amount of water.Further stir this compound, use the tablets press granulation, the air-dry subsequently particle that obtains.

Example of formulations 4

With mortar with 4.5 parts of any The compounds of this invention (1)-(96), 1 part of oxidizing aqueous silica fine powder of synthetic, 1 part of Dorires B (Sankyo manufacturing) as flocculation agent and 7 parts of clay uniform mixing, stir with the fruit juice mixing tank subsequently.In the mixture that obtains, add 86.5 parts of engravings (cut) clay, mix, obtain powder.

Example of formulations 5

10 parts of any The compounds of this invention (1)-(96), 35 parts of white carbon black and 55 parts of water that contain 50 parts of Voranol EP 2001 ammonium sulfates mix, and make its fine dispersion by wet milling process subsequently, obtain preparation.

Example of formulations 6

0.5 part any The compounds of this invention (1)-(96) are dissolved in 10 parts of methylene dichloride.This solution and 89.5 parts of Isopar M (isoparaffin: the registrar name of an article of Exxon Chemical) mix, obtain oily matter.

Example of formulations 7

(Chuo Kasei Co. Ltd.) places aerosol container with 0.1 part of any The compounds of this invention (1)-(96) and 49.9 parts of NEO-THIOZOL.On jar aerosol valves is housed, 25 parts of methyl ethers and 25 parts of LPG subsequently pack in jar.This jar of jolting is loaded onto driving mechanism (actuator) on this jar, obtain the oily aerosol.

Example of formulations 8

In aerosol container, pack into mixture and 50 parts of distilled water of 0.6 part of any The compounds of this invention (1)-(96), 0.01 part of BHT, 5 parts of dimethylbenzene, 3.39 parts of deodorized kerosines and 1 part of emulsifying agent [Atmos 300 (the registrar name of an article of AtmosChemical Ltd.)].On this container, load onto valve part, the 40 parts of propelling agents (LPG) of in container, packing into subsequently, the pressurization back obtains water-borne aerosol by valve.

Example of formulations 9

To have honey comb structure and thickness is that 0.5cm, length are that 69cm, width are that 0.2cm paper container (paperware) is reeled from an end of paper, and making diameter is that 5.5cm, width are the carrier of 0.2cm (seeing Fig. 1 and Fig. 2).5 parts of any The compounds of this invention (1)-(96) are dissolved in 95 parts of acetone.An amount of gained solution evenly is applied to described carrier, subsequently with the air-dry preparation that obtains of acetone.

Example of formulations 10

(Asahi KaseiFibers Corporation makes, thickness: 4.3mm, weight: 321 g/m for trade(brand)name: Fusion, model: AKE69440 from the 3 D weaving fabric ², make by polymeric amide) and cut out the circle that diameter is 5cm.5 parts of any The compounds of this invention (1)-(96) are dissolved in 95 parts of acetone.With an amount of solution be applied to equably described 3 D weaving fabric around, subsequently with the air-dry preparation that obtains of acetone.

Example of formulations 11

(content of methyl methacrylate is 10% weight with 98 parts by weight of ethylene-methylmethacrylate copolymer, MFR=2[g/10 minute]) and any The compounds of this invention of 2 weight parts (1)-(96) fusion and mediate with the biaxial extruders in the same way of 45mm φ down at 130 ℃, mediate with 40mm φ forcing machine down at 150 ℃ subsequently, be extruded into sheet material by T pattern head, with the cooling roller cooling, obtain resin formulation subsequently.

Example of formulations 12

(vinyl acetate content is 10% weight with 98 parts by weight of ethylene-vinyl acetate copolymer, MFR=2[g/10 minute]) and any The compounds of this invention of 2 weight parts (1)-(96) fusion and mediate with the biaxial extruders in the same way of 45mm φ down at 130 ℃, mediate with 40mm φ forcing machine down at 150 ℃ subsequently, be extruded into sheet material by T pattern head, with the cooling roller cooling, obtain resin formulation subsequently.

Example of formulations 13

5 parts of any The compounds of this invention (1)-(96) are dissolved in 95 parts of acetone.This an amount of solution is applied to the paper (2000cm with folding structure shown in Figure 3 ²) on, acetone is air-dry, obtain preparation.

Example of formulations 14

5 parts of any The compounds of this invention (1)-(96) are dissolved in 95 parts of acetone.This an amount of solution is applied to the paper (2000cm with folding structure shown in Figure 4 ²) on, acetone is air-dry, obtain preparation.

Example of formulations 15

3.6 parts of any The compounds of this invention (1)-(96) and 14.3 parts of acetone mixing are obtained solution.Subsequently 0.2 part of zinc oxide, 1.0 parts of Alpha-starch and 42.8 parts of Cellmic C 121s are added in this solution, add 38.1 parts of water subsequently.With forcing machine this mixture of kneading, be molded as particulate matter, subsequent drying.The top of the container that the particle centering part that will contain The compounds of this invention is separated by the aluminium spacer places the bottom of this container, (smoking) preparation of being fuming with the 50g calcium oxide.

Example of formulations 16

0.5 part of zinc oxide, 2 parts of Alpha-starch and 97.5 parts of Cellmic C 121s are mixed, in this mixture, add entry.With forcing machine this mixture of kneading, be molded as particulate matter, subsequent drying obtains particle.Evenly flood this particulate matter of 2g with the acetone soln that comprises any The compounds of this invention of 0.58g (1)-(96), subsequent drying obtains containing the particle of any The compounds of this invention (1)-(96).The top of the container that the particle centering part that will contain The compounds of this invention is separated by the aluminium spacer places the bottom of this container with the 50g calcium oxide, obtains the preparation of being fuming.

Example of formulations 17

Any The compounds of this invention of 0.5g (1)-(96) are dissolved in 20ml acetone, mix with 99.4g coiled mosquito-repellent incense carrier [tabu powdered mixture (Machilus thunbergii powder): medicinal (dregs) powder (other powder parts outside the pyrethrum activeconstituents): wood powder is 4: 3: 3, weight ratio] and 0.3g veridian subsequently.In mixture, add 120ml water.This mixture is mediated evenly, and molded, subsequent drying obtains coiled mosquito-repellent incense.

Example of formulations 18

10 parts of any The compounds of this invention (1)-(96), 40 parts of tributyl acetylcitrates, 40 parts of hexanodioic acid esters in the different ninth of the ten Heavenly Stems, 5 parts of blue pigmentss and 5 parts of spices mixing obtain solution.The even infiltration of this solution to the base mateiral that is used for electric mosquito eradication tablet (electric mosquito mat) (fibril of the mixture by sclerosis cotton linter and paper pulp obtains) is obtained electric mosquito eradication tablet, this base mateiral is of a size of 3.4cm * 2.1cm, and thickness is 0.22cm.

Example of formulations 19

0.1 part of any The compounds of this invention (1)-(96) are dissolved in 99.9 parts of deodorized kerosines, subsequently this solution are placed polyvinyl chloride container.Insert its top in this container and can obtain the part of imbibition core pattern heated volatile desinsection product with the wick (inorganic powder and tackiness agent sintering are obtained) of heater heats.

Example of formulations 20

(Chuo Kasei Co. Ltd.) places aerosol container, loads onto aerosol valve on jar with 0.2 part of any The compounds of this invention (1)-(96) and 49.8 parts of NEO-THIOZOL.In jar, pack into subsequently 25 parts of dme and 25 parts of LPG, joltings subsequently.On jar, load onto the driving mechanism that is used for full dose ejection-type aerosol, obtain aerosol.

Example of formulations 21

99.8 parts of diethylene glycol monoethyl ethers are added in 0.2 part of any The compounds of this invention (1)-(96), mix, obtain the spot printing preparation.

Example of formulations 22

With the solution of 3.3 parts of any The compounds of this invention of 1mL (1)-(96) and 96.7 parts of acetone evenly be applied to dish (diameter: 3cm, thickness: 3mm) subsequent drying obtains Formulation, this dish is with 4000mg 2,4,6-triisopropyl-1,3, (4 tons/cm of 5-trioxane compactings ²) form.

Example of formulations 23

With any The compounds of this invention of 200mg (1)-(96) and 4000mg 2,4,6-triisopropyl-1,3, (4 tons/cm of the uniform mixture compactings of 5-trioxane ²) one-tenth dish (diameter: 3cm, thickness: 3mm), obtain Formulation.

Example of formulations 24

With any The compounds of this invention of 200mg (1)-(96) and 4000mg 2,4,6-triisopropyl-1,3,5-trioxane place 50mL spiral tube (screw tube), and heating and melting is cooled to room temperature subsequently, obtains Formulation.

Then, will illustrate that The compounds of this invention is the effective active composition of insect-killing composition by experimental example.The compounds of this invention will refer to above-mentioned compound number.

Experimental example 1

The The compounds of this invention (1) that the method that adopts example of formulations 5 is obtained, (2), (3), (4), (5), (22), (23), (24), (28), (29), (30), (31), (32), (35), (36), (37), (38), (39), (46), (48), (49), (51), (53), (54), (56), (58), (59), (60), (61), (64), (66), (67), (68), (69), (70), (71), (72), (73), (74), (75), (76), (77), (78), (79), (80), (81), (82), (83), (85), (86), (87), (88) and the preparation of (89) dilution, make that activity component concentration is that 500ppm is with preparation test insecticide solution.

The molded Bonsoru 2 of 50g (Sumitomo Chemical Co., Ltd. makes) is placed the polyethylene cup, 10-15 grain rice paddy seed is planted in the polyethylene cup.Paddy growth all is cut into the height of 5cm then to growing second trophophyll.To sparge on these rice plants as the amount of above-mentioned prepared test insecticide liquid with the 20ml/ cup.After waiting to sparge the insecticidal solution soma on the paddy rice, rice plant is put into plastic cup to prevent to test the insect escape.The first-instar young of 30 Nilaparvata lugen (brown planthopper)s (Nilaparvata lugens) is put to plastic cup, seal this cup, be positioned over then in 25 ℃ of greenhouses.Put into the 6th day behind Nilaparvata lugen (brown planthopper) (Nilaparvata lugens) larva, detect Nilaparvata lugen (brown planthopper) (Nilaparvata lugens) number parasitic on the rice plant.

The result is using The compounds of this invention (1), (2), (3), (4), (5), (22), (23), (24), (28), (29), (30), (31), (32), (35), (36), (37), (38), (39), (46), (48), (49), (51), (53), (54), (56), (58), (59), (60), (61), (64), (66), (67), (68), (69), (70), (71), (72), (73), (74), (75), (76), (77), (78), (79), (80), (81), (82), (83), (85), (86), (87), (88) and on (89) plant of handling, the number of parasitic insect is 3 or still less.

Experimental example 2

The The compounds of this invention (1) that the method that adopts example of formulations 5 is obtained, (2), (3), (4), (5), (9), (10), (11), (15), (16), (17), (20), (21), (22), (23), (24), (25), (27), (29), (30), (31), (32), (35), (36), (37), (38), (39), (46), (47), (48), (49), (50), (51), (52), (53), (54), (55), (56), (58), (59), (60), (61), (62), (64), (66), (67), (68), (69), (70), (71), (73), (74), (75), (76), (77), (78), (79), (80), (81), (82), (83), (85), (86), (87) and the preparation dilute with water of (89), make that activity component concentration is that 500ppm is with preparation test insecticide solution.

With diameter is that the filter paper of 5.5cm is layered on the bottom that diameter is the polyethylene cup of 5.5cm, drips 0.7ml test insecticide solution on filter paper.To evenly place on the filter paper as the 30mg sucrose of bait.In the polyethylene cup, put into 10 female houseflies (Musca domestica) adult, use the cap covers cup.After 24 hours, detect housefly (Musca domestica) number of survival, calculate the mortality ratio of insect.

The result is through The compounds of this invention (1), (2), (3), (4), (5), (9), (10), (11), (15), (16), (17), (20), (21), (22), (23), (24), (25), (27), (29), (30), (31), (32), (35), (36), (37), (38), (39), (46), (47), (48), (49), (50), (51), (52), (53), (54), (55), (56), (58), (59), (60), (61), (62), (64), (66), (67), (68), (69), (70), (71), (73), (74), (75), (76), (77), (78), (79), (80), (81), (82), (83), (85), (86), (87) and (89) mortality ratio of handling the back insect be 90% or higher.

Experimental example 3

The The compounds of this invention (3) that the method that adopts example of formulations 5 is obtained, (4), (5), (9), (10), (17), (20), (21), (22), (23), (24), (25), (27), (29), (30), (31), (32), (35), (36), (37), (38), (46), (47), (48), (50), (52), (53), (54), (55), (56), (58), (59), (60), (61), (64), (66), (67), (68), (69), (71), (72), (73), (74), (75), (78), (79), (80), (81), (82), (83), (87), (88), (89) and the preparation dilute with water of (93), make that activity component concentration is that 500ppm is with preparation test insecticide solution.

With diameter is that the filter paper of 5.5cm is layered on the bottom that diameter is the polyethylene cup of 5.5cm, drips 0.7ml test insecticide solution on filter paper.To evenly place on the filter paper as the 30mg sucrose of bait.In the polyethylene cup, put into 2 Groton bugs (Blattella germanica) adult, use the cap covers cup.After 6 days, detect Groton bug (Blattella germanica) number of survival, calculate the mortality ratio of insect.

The result is through The compounds of this invention (3), (4), (5), (9), (10), (17), (20), (21), (22), (23), (24), (25), (27), (29), (30), (31), (32), (35), (36), (37), (38), (46), (47), (48), (50), (52), (53), (54), (55), (56), (58), (59), (60), (61), (64), (66), (67), (68), (69), (71), (72), (73), (74), (75), (78), (79), (80), (81), (82), (83), (87), (88), (89) and (93) mortality ratio of handling the back insect be 100%.

Experimental example 4

The The compounds of this invention (1) that the method that adopts example of formulations 5 is obtained, (3), (4), (8), (9), (10), (11), (12), (17), (20), (21), (22), (23), (28), (29), (30), (31), (32), (35), (36), (37), (38), (39), (43), (46), (47), (48), (49), (51), (53), (54), (55), (56), (58), (59), (60), (61), (62), (63), (65), (66), (67), (68), (69), (70), (71), (72), (73), (74), (75), (76), (77), (78), (79), (80), (81), (82), (83), (85), (87), (89) and the preparation dilute with water of (93), make that activity component concentration is that 500ppm is with preparation test insecticide solution.

The 0.7ml test is added (activity component concentration: 3.5ppm) in the 100mL ion exchanged water with insecticide solution.Put into the whole instar larvae of 20 culex pipiens pollens (Culex pipiens pallens) in this solution.After one day, detect the number of survival, calculate the mortality ratio of insect.

The result is through The compounds of this invention (1), (3), (4), (8), (9), (10), (11), (12), (17), (20), (21), (22), (23), (28), (29), (30), (31), (32), (35), (36), (37), (38), (39), (43), (46), (47), (48), (49), (51), (53), (54), (55), (56), (58), (59), (60), (61), (62), (63), (65), (66), (67), (68), (69), (70), (71), (72), (73), (74), (75), (76), (77), (78), (79), (80), (81), (82), (83), (85), (87), (89) and (93) mortality ratio of handling the back insect be 90% or higher.

Experimental example 5

Preparation contains The compounds of this invention (20), (23), (24), (30), (31) of 0.057% (weight/volume), the acetone soln of (35) and (37).Be evenly to drip 0.2ml solution and air-dry (be equivalent to every square metre handle with the 100mg The compounds of this invention) on the filter paper of 3.8cm at diameter.About 20 ctenocephalides felises (Ctenocephalised felis) adult is put into the 200mL vial.Be placed with the cap covers bottle of filter paper with inner face.After 24 hours, detect the number of ctenocephalides felis (Ctenocephalised felis) survival of survival, calculate the mortality ratio of insect.

The mortality ratio that the result handles the back insect through The compounds of this invention (20), (23), (24), (30), (31), (35) and (37) is 80% or higher.

Experimental example 6

The spot printing preparation for preparing The compounds of this invention (23), (24), (30) and (31) according to the method for example of formulations 21.Back line skin at the female mice (the about 30g of body weight) of growing up drips 0.1ml spot printing preparation.Place the mesh bag that is a bit larger tham its stature that it is unable to stir any more this mouse.Place the bottom to be covered with the 900mL vial of filter paper this mouse, (Ctenocephalised felis adult is put into vial with 20 ctenocephalides felises subsequently.The upside of vial is coated with nylon wire.After 24 hours, detect the number of ctenocephalides felis (Ctenocephalised felis) survival of survival, calculate the mortality ratio of insect.

The mortality ratio that the result handles the back insect through The compounds of this invention (23), (24), (30) and (31) is 95% or higher.

Experimental example 7

The methanol solution of the The compounds of this invention (31) of preparation 0.25% (weight/volume).Evenly drip upward this solution of 0.22ml (not being coated with within the poly-wide place of film edge 5mm) in a side of polypropylene film (high 5.7cm * wide 16.5cm), air-dry subsequently.Subsequently that film is folding with the half-width direction, the one side that contains The compounds of this invention inwardly.Subsequently, pocket is made in two of folding film long limit (every hem width 5mm) heat-sealings.The young mite of 10 haemaphysalis longicornises (Haemaphysalislongicornis) is put into the polypropylene screen pocket.The opening portion of polypropylene screen pocket is sealed with clip.After 48 hours, detect the quantity of the haemaphysalis longicornis (Haemaphysalis longicornis) of survival, and calculate the mortality ratio of insect.

The mortality ratio that the result handles the back insect through The compounds of this invention (31) is 100%.

Experimental example 8

The acetone soln of the The compounds of this invention (31) of preparation 2% (weight/volume).On the filter paper of 10cm * 12.5cm, evenly drip this solution of 2.5ml and air-dry.The top board center suspension of this filter paper from the glass box of 70cm (wide) * 70cm (deeply) * 70cm (height) got off, in glass box, put into 20 different eye flys in East Asia (Megaselia spiracularis) adult.After 2 hours, collect the insect of all tests, put into plastic cup, place down at 25 ℃ subsequently with the absorbent tampons that is soaked with 5% syrup.After 24 hours, detect the quantity of the different eye fly in East Asia (Megaseliaspiracularis) of survival, and calculate the mortality ratio of insect.

Experimental example 9

The acetone soln of the The compounds of this invention (31) of preparation 2% (weight/volume).On the filter paper of 10cm * 12.5cm, evenly drip this solution of 2.5ml and air-dry.The top board center suspension of this filter paper from the glass box of 70cm (wide) * 70cm (deeply) * 70cm (height) got off, in glass box, put into 20 hickie moth buffalo gnats (Clogmia albipunctata) adult.After 2 hours, collect the insect of all tests, put into plastic cup, place down at 25 ℃ subsequently with the absorbent tampons that is soaked with 5% syrup.After 24 hours, detect the quantity of the hickie moth buffalo gnat (Clogmia albipunctata) of survival, and calculate the mortality ratio (repeating twice) of insect.

The mortality ratio that the result handles the back insect through The compounds of this invention (31) is 83%.

Experimental example 10

The acetone soln of the The compounds of this invention (31) of preparation 1% (weight/volume).Evenly this solution of Dropwise 5 ml is also air-dry on the filter paper of 10cm * 25cm.The top board center suspension of this filter paper from the Peet-Grady case of 1.8m (wide) * 1.8m (deeply) * 1.8m (height) got off, in this case, put into about 50 culex pipiens pollens (Culex pipiens pallens) female insect.After 1 hour, collect the insect of all tests, put into plastic cup, place down at 25 ℃ subsequently with the absorbent tampons that is soaked with 5% syrup.After 24 hours, detect the quantity of the culex pipiens pollens (Culex pipienspallens) of survival, and calculate mortality ratio.

The mortality ratio that the result handles the back insect through The compounds of this invention (31) is 86%.

Experimental example 11

The acetone soln of the The compounds of this invention (31) of preparation 1% (weight/volume).Evenly this solution of Dropwise 5 ml is also air-dry on the filter paper of 10cm * 25cm.The top board center suspension of this filter paper from the Peet-Grady case of 1.8m (wide) * 1.8m (deeply) * 1.8m (height) got off, in this case, put into about 50 houseflies (Musca domestica) adult.After 1 hour, collect the insect of all tests, put into plastic cup, place down at 25 ℃ subsequently with the absorbent tampons that is soaked with 5% syrup.After 24 hours, detect the quantity of the housefly (Musca domestica) of survival, and calculate mortality ratio.

The mortality ratio that the result handles the back insect through The compounds of this invention (31) is 92%.

Experimental example 12

The compounds of this invention (31) is dissolved in the acetone soln of the sudan red 7B of 0.05% (weight/volume), makes that the concentration of The compounds of this invention is 0.005% (weight/volume), make the test insecticide solution.Abdomen back the worker ant of Coptotermes formosanus Shtrari (Coptotermes formosanus) drips 0.2 this test solution of μ l.After handling one day, detect survival insect quantity and calculate the mortality ratio of insect.

Experimental example 13

7.5mg The compounds of this invention (31) is dissolved in the mixture of the 90 weight part IsoparM (isoparaffin, the registrar name of an article of Exxon Chemical) of 30mL and 10 weight part methylene dichloride the oily matter of preparation 0.025% (weight/volume).10 Groton bugs (Blattella germanica) adult is housed, and (5 male, 5 are female) plastic containers (diameter: 9.5cm, highly: 4cm, the bottom is 16 purpose silk screens) place the CSMA case (wide: 46cm, deeply: 46cm, highly: bottom 70cm).

From the top of CSMA case 1.5ml oily matter is sprayed directly on on the cockroach of test.After having sprayed 30 seconds, remove the container that cockroach is housed.All cockroaches are transferred in the plastic containers (200mL) of another cleaning, and under 25 ℃, subsist and water.After 3 days, detect survival Groton bug (Blattella germanica) number and calculate the mortality ratio of insect.

Experimental example 14

The acetone soln of the The compounds of this invention (4) of preparation 1% (weight/volume), (20), (22), (23), (24), (29), (30), (31), (35), (36), (37), (38), (46), (53), (54), (56), (57), (59), (61), (66), (67), (68), (69), (70), (71), (79), (81), (83), (84), (89) and (90).Chest (sternum of the thorax) at Groton bug (Blattella germanica) female insect drips 1 this acetone soln of μ l.Adult is transferred to diameter for about 9cm, highly in the plastic cup of about 4.5cm, and under 25 ℃, subsists and water.After 7 days, detect survival Groton bug (Blattella germanica) number and calculate the mortality ratio of insect.10 Groton bugs (Blattella germanica) adult is put into cup, and carry out revision test three times.

The mortality ratio that the result handles the back insect through The compounds of this invention (4), (20), (22), (23), (24), (29), (30), (31), (35), (36), (37), (38), (46), (53), (54), (56), (57), (59), (61), (66), (67), (68), (69), (70), (71), (79), (81), (83), (84), (89) and (90) is 100%.

Experimental example 15

The The compounds of this invention (23) of preparation 2.5% (weight/volume), the acetone soln of (24) and (31).This drips of solution of 0.1ml is added on the filter paper of 2cm * 2cm and air-dry.Filter paper is pasted on the center of the carton inner bottom part of 10cm (wide) * 2cm (height) * 7cm (deeply) with double faced adhesive tape.Open the hole of wide 5mm, high 2cm in a side of this box.This box is placed in the plastic tank of 25cm * 20cm * 8cm (height), put into 10 female and 10 male Groton bugs (Blattellagermanica).The inwall that is used for the plastic tank of this test scribbles talcum powder and runs away to prevent cockroach.Food and water are housed in the plastic tank and place under 25 ℃ the condition.After 7 days, observe Groton bug (Blattella germanica) and calculate the mortality ratio of insect.Should test and repeat twice.

The mortality ratio that the result handles the back insect through The compounds of this invention (23) is 97.5%, and the mortality ratio of handling the back insect through The compounds of this invention (24) and (31) is 100%.

Experimental example 16

The The compounds of this invention (23) of preparation 5% (weight/volume), the acetone soln of (24) and (31).This drips of solution of 0.1ml is added on the filter paper of 2cm * 2cm and air-dry subsequently.Filter paper is pasted on the center of the carton inner bottom part of 10cm (wide) * 2cm (height) * 7cm (deeply) with double faced adhesive tape.Open the hole of wide 2mm, high 2cm in a side of this box.This box is placed in the plastic tank of 25cm * 20cm * 8cm (height), put into 3 female and 3 male smoke Perilpaneta americanas (Periplaneta fuliginosa).The inwall that is used for the plastic tank of this test scribbles talcum powder and runs away to prevent cockroach.Food and water are housed in the plastic tank and place 25 ℃.After 7 days, observe smoke Perilpaneta americana (Periplaneta fuliginosa) and calculate the mortality ratio of insect.Should test and repeat twice.

The mortality ratio that the result handles the back insect through The compounds of this invention (23) is 91.7%, and the mortality ratio of handling the back insect through The compounds of this invention (24) and (31) is 100%.

Experimental example 17

The acetone soln of the The compounds of this invention (31) of preparation 5% (weight/volume).This drips of solution of 0.1ml is added on the filter paper of 2cm * 2cm and air-dry subsequently.Filter paper is pasted on the center of the carton inner bottom part of 10cm (wide) * 2cm (height) * 7cm (deeply) with double faced adhesive tape.Open the hole of wide 2mm, high 2cm in a side of this box.This box is placed in the plastic tank of 25cm * 20cm * 8cm (height), put into 3 female and 3 male periplaneta americanaes (Periplanetaamerican).The inwall that is used for the plastic tank of this test scribbles talcum powder and runs away to prevent cockroach.Food and water are housed in the plastic tank and place 25 ℃.After 7 days, observe periplaneta americana (Periplanetaamericana) and calculate the mortality ratio of insect.Should test and repeat twice.

The mortality ratio of insect after the result handles through The compounds of this invention (31) is 100%.

Experimental example 18

Plastic cup (the diameter 12.5cm of 10 (5 male and 5 female) Groton bug (Blattella germanica) adults will be housed, highly: 8cm) place two corners of the Peet-Grady case of 1.8m (wide) * 1.8m (deeply) * 1.8m (height), the plastic containers that will contain water place the Peet-Grady case the bottom the center and will place this plastic cup according to the preparation of being fuming of the The compounds of this invention (31) of example of formulations 16 preparations.After 2 hours, collect Groton bug (Blattella germanica), be transferred in the 200mL plastic cup, and under 25 ℃, subsist and water.After 72 hours, detect survival Groton bug (Blattella germanica) number and calculate the mortality ratio of insect.

Experimental example 19

18.8mg The compounds of this invention (31) is dissolved in the mixed solvent of the 90 weight part IsoparM (isoparaffin, the registrar name of an article of Exxon Chemical) of 30mL and 10 weight part methylene dichloride the oily matter of preparation 0.0625% (weight/volume).The plastic cup (200mL) that 10 brown ants of Japan (Formica fusca japonica) adult will be housed place the CSMA case (wide: 46cm, dark: 46cm, highly: bottom 70cm).From the top of CSMA case 0.4ml oily matter is sprayed directly on on the Japanese brown ant of test (Formica fusca japonica).After having sprayed 10 seconds, remove Japanese brown ant (Formica fusca japonica) container is housed.The brown ant of Japan (Formica fusca japonica) is transferred to another plastic containers (200mL) and under 25 ℃, subsists and water.Biological proofing intact after 72 hours, observe Japanese brown ant (Formica fusca japonica) and calculate the mortality ratio of insect.

Experimental example 20

The acetone soln of the The compounds of this invention (31) of 1ml 0.1% weight is dripped at the commercially available unpurified Icing Sugar of 1g, and uniform mixing is also air-dry subsequently, obtains poison bait.Cotton balls is under water, will place at the 0.5g poison bait on the aluminium dish 10 the brown ant of Japan (Formica fuscajaponica) adult plastic cups (860mL) will be housed.After 48 hours, observe survival Japanese brown ant (Formica fusca japonica) number and calculate the mortality ratio of insect.

The mortality ratio of result Japanese brown ant (Formica fusca japonica) in this test is 100%.

Experimental example 21

The acetone soln of the The compounds of this invention (31) of 3ml 0.5% weight is dropped in the 3g animal powder feed, mix the air-dry subsequently poison bait that obtains.Place the aluminium dish also this dish to be placed in the plastic cup (860mL) that 20 Groton bugs (Blattella germanica) adult (10 male, and 10 female) is housed in this poison bait of 1g.Give the insect supplied water and remain on 25 ℃.After 7 days, detect survival Groton bug (Blattella germanica) number and obtain the activity of this poison bait.The poison bait that contains The compounds of this invention (31) has enough insecticidal effects to Groton bug (Blattellagermanica).

Experimental example 22

The acetone soln of the The compounds of this invention (31) of preparation 10% (weight/volume).This solution of 10mL is evenly dropped on the filter paper of 10cm * 25cm and air-dry subsequently.The case top center suspension of this filter paper from 70cm (wide) * 70cm (deeply) * 70cm (height) got off.Put into 20 Groton bugs (Blattella germanica) adult (10 male, and 10 female), close upper chamber door.Be placed with food and water in the glass box.After 72 hours, detect the number of the Groton bug (Blattellagermanica) of survival, confirmed insecticidal effect Groton bug (Blattella germanica).

Experimental example 23

The acetone soln of the The compounds of this invention (31) of preparation 5% (weight/volume).This solution of 0.1ml is evenly dropped on the filter paper of 2cm * 2cm and air-dry subsequently.In the plastic cup of the high 8cm of diameter 12.5cm, put into 10 brown ants of Japan (Formica fusca japonica) adult.After in cup, putting into food and water, use the cap covers cup.Above-mentioned filter paper with pesticide treatments is attached to the inner face of lid.In addition, the inwall of cup scribbles talcum powder to prevent the ant climbing.Cup places under 25 ℃.After 7 days, observe the Japanese brown ant (Formica fuscajapontca) of survival, confirmed insecticidal effect the brown ant of Japan (Formica fusca japonica).

Experimental example 24

1.5g The compounds of this invention (31) is dissolved in 30mL by 90 weight part Isopar M (isoparaffins; The Exxon Chemical registrar name of an article) and prepare the oily matter of 5% (weight/volume) in the mixed solvent formed of 10 weight part methylene dichloride.With nylon wire (mesh is wide: 2mm) cover the plastic cup (860mL) of 10 blind curling up of brown (Halyomorpha mista) adult be housed, subsequently plastic cup is placed the CSMA case (wide: 46cm, dark: 46cm, highly: bottom 70cm).From the top of CSMA case the described oily matter of 0.4ml is sprayed directly on to test brown is blind and curl up on (Halyomorpha mista).After having sprayed 10 minutes, remove the cup that is equipped with that brown is blind and curls up (Halyomorpha mista), in cup, put into food and water.Biological proofing intact after 72 hours, observe that brown is blind curls up (Halyomorpha mista), the insecticidal effect of confirmed to curl up (Halyomorpha mista) to brown is blind.

Experimental example 25

To place on the electric mosquito sheet well heater according to the electric mosquito eradication tablet of the The compounds of this invention (31) of example of formulations 18 preparation, with the central authorities that are placed on bottom 70cm (wide) * 70cm (deeply) * 70cm (height) case.Begin about 20 culex pipiens pollens (Culexpipiens pallens) female insect to be put into case with behind the heater heats electricity mosquito eradication tablet.After 20 minutes, collect all test insects, place plastic cup with the absorbent tampons of having soaked 5% syrup, with being placed under 25 ℃.After 24 hours, detect the number of the culex pipiens pollens (Culex pipiens pallens) of survival, thereby confirmed insecticidal effect culex pipiens pollens (Culex pipiens pallens).

Experimental example 26

To be placed on the well heater that is used for imbibition core pattern heated volatile desinsection product according to the imbibition core pattern heated volatile desinsection product component of the The compounds of this invention (31) of example of formulations 19 preparation, be placed on the bottom center of 70cm (wide) * 70cm (deeply) * 70cm (height) case subsequently.Begin about 20 culex pipiens pollens (Culexpipiens pallens) female insect to be put into case with after the heater heats volatilization desinsection product component.After 20 minutes, collect all test insects, place plastic cup with the absorbent tampons of having soaked 5% syrup, with being placed under 25 ℃.After 24 hours, detect the number of the culex pipiens pollens (Culex pipiens pallens) of survival, thereby confirmed insecticidal effect culex pipiens pollens (Culex pipiens pallens).

Experimental example 27

To place the top of electric fan shown in Figure 5 according to the preparation of the The compounds of this invention (31) of example of formulations 10 preparation, with the bottom center that is placed on 70cm (wide) * 70cm (deeply) * 70cm (height) case.After starting electric fan and making said preparation volatilization, about 20 culex pipiens pollens (Culexpipiens pallens) female insect is put into case.After 20 minutes, collect all test insects, place plastic cup with the absorbent tampons of having soaked 5% syrup, with being placed under 25 ℃.After 24 hours, detect the number of the culex pipiens pollens (Culex pipiens pallens) of survival, thereby confirmed insecticidal effect culex pipiens pollens (Culex pipiens pallens).

Industrial applicability

The present invention is Control pests such as insect, mite and nematode effectively.

Claims

1. the nitrile compound of a formula (I) expression:

Wherein R represents the C1-C4 fluoroalkyl,

Q represents halogen, optional C1-C11 alkyl, optional C2-C6 thiazolinyl, optional C2-C6 alkynyl, optional C3-C7 cycloalkyl or (the optional C3-C7 cycloalkyl that is replaced by one or more halogens) C1-C4 alkyl that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens

Described halogen is represented fluorine, chlorine or bromine.

2. the nitrile compound of claim 1, wherein Q is halogen, optional C1-C6 alkyl, optional C2-C6 thiazolinyl, optional C2-C6 alkynyl, optional C3-C7 cycloalkyl or (the optional C3-C7 cycloalkyl that is replaced by one or more halogens) C1-C4 alkyl that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens that is replaced by one or more halogens.

3. the nitrile compound of claim 1, wherein R is the C2-C4 fluoroalkyl with 3-5 fluorine atom.

4. the nitrile compound of claim 1, wherein R is the C3-C4 fluoroalkyl with 6-8 fluorine atom.

5. the nitrile compound of claim 1, wherein R is the C2 fluoroalkyl.

6. the nitrile compound of claim 1, wherein R is 2,2, the 2-trifluoroethyl.

7. each nitrile compound among the claim 1-6, wherein Q is the optional C4-C6 alkyl that is replaced by one or more halogens.

8. each nitrile compound among the claim 1-6, wherein Q is the optional C3-C4 alkyl that is replaced by one or more halogens.

9. each nitrile compound among the claim 1-6, wherein Q is the optional C4 alkyl that is replaced by one or more halogens.

10. each nitrile compound among the claim 1-6, wherein Q is 1,1,2,2,3,3,4,4-octafluoro butyl.

11. an insect-killing composition, described composition comprise the nitrile compound and the inert support of claim 1.

12. the method for a Pest Control, described method comprise that the nitrile compound with the claim 1 of significant quantity is applied to described insect or described insect habitat.

13. the nitrile compound of claim 1 is used for the purposes of insect control.