US20040142821A1 - Pesticide composition comprising malononitrile compounds - Google Patents
Pesticide composition comprising malononitrile compounds Download PDFInfo
- Publication number
- US20040142821A1 US20040142821A1 US10/476,979 US47697903A US2004142821A1 US 20040142821 A1 US20040142821 A1 US 20040142821A1 US 47697903 A US47697903 A US 47697903A US 2004142821 A1 US2004142821 A1 US 2004142821A1
- Authority
- US
- United States
- Prior art keywords
- halo
- malononitrile
- production example
- compound
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 92
- 239000000575 pesticide Substances 0.000 title claims abstract description 20
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical class N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 title abstract description 133
- 125000005843 halogen group Chemical group 0.000 claims abstract description 211
- -1 methylenedioxy Chemical group 0.000 claims abstract description 102
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 48
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 45
- 239000001257 hydrogen Substances 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 38
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 27
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 22
- 239000004480 active ingredient Substances 0.000 claims abstract description 19
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 19
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 13
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 8
- 241000238631 Hexapoda Species 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 150
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 125000006017 1-propenyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 141
- 241000244206 Nematoda Species 0.000 abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 336
- 238000004519 manufacturing process Methods 0.000 description 274
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 162
- 239000003921 oil Substances 0.000 description 110
- 235000019198 oils Nutrition 0.000 description 110
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 107
- 239000012312 sodium hydride Substances 0.000 description 107
- 229910000104 sodium hydride Inorganic materials 0.000 description 107
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
- 238000005160 1H NMR spectroscopy Methods 0.000 description 82
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- 238000009472 formulation Methods 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 239000000460 chlorine Substances 0.000 description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
- 238000003756 stirring Methods 0.000 description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 35
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
- 238000012360 testing method Methods 0.000 description 32
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 31
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 24
- 125000001309 chloro group Chemical group Cl* 0.000 description 23
- YKLCNJXWEFTBLY-UHFFFAOYSA-N 2-prop-2-enylpropanedinitrile Chemical compound C=CCC(C#N)C#N YKLCNJXWEFTBLY-UHFFFAOYSA-N 0.000 description 20
- 238000010898 silica gel chromatography Methods 0.000 description 20
- 239000004698 Polyethylene Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 229920000573 polyethylene Polymers 0.000 description 18
- SLNGZEZYPUSGBF-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]methyl]propanedinitrile Chemical compound FC(F)(F)C1=CC=C(CC(C#N)C#N)C=C1 SLNGZEZYPUSGBF-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 17
- 241001556089 Nilaparvata lugens Species 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- 240000007594 Oryza sativa Species 0.000 description 15
- 239000011780 sodium chloride Substances 0.000 description 15
- KZVZSAZGEKLWOJ-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]propanedinitrile Chemical compound ClC1=CC=C(CC(C#N)C#N)C=C1 KZVZSAZGEKLWOJ-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 0 CC.[1*]C([2*])(C1=CC=C([6*])C=C1)C(C#N)(C#N)C([3*])[4*] Chemical compound CC.[1*]C([2*])(C1=CC=C([6*])C=C1)C(C#N)(C#N)C([3*])[4*] 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 12
- FQBSVBZEJVVQSA-UHFFFAOYSA-N 2-[[4-(trifluoromethoxy)phenyl]methylidene]propanedinitrile Chemical compound FC(F)(F)OC1=CC=C(C=C(C#N)C#N)C=C1 FQBSVBZEJVVQSA-UHFFFAOYSA-N 0.000 description 11
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 11
- 239000012279 sodium borohydride Substances 0.000 description 11
- 229910000033 sodium borohydride Inorganic materials 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- AMWSRKJCOXETOT-UHFFFAOYSA-N 2-[[4-(trifluoromethoxy)phenyl]methyl]propanedinitrile Chemical compound FC(F)(F)OC1=CC=C(CC(C#N)C#N)C=C1 AMWSRKJCOXETOT-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- TVEMURJMVJRQFV-UHFFFAOYSA-N 2-but-3-enyl-2-[(4-hydroxyphenyl)methyl]propanedinitrile Chemical compound OC1=CC=C(CC(CCC=C)(C#N)C#N)C=C1 TVEMURJMVJRQFV-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000443 aerosol Substances 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- DVEBNMQXAHOZDV-UHFFFAOYSA-N 2-[[4-(trifluoromethylsulfanyl)phenyl]methyl]propanedinitrile Chemical compound FC(F)(F)SC1=CC=C(CC(C#N)C#N)C=C1 DVEBNMQXAHOZDV-UHFFFAOYSA-N 0.000 description 7
- XWYYZNRSHJHRQL-UHFFFAOYSA-N 2-but-3-enylpropanedinitrile Chemical compound C=CCCC(C#N)C#N XWYYZNRSHJHRQL-UHFFFAOYSA-N 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 230000000361 pesticidal effect Effects 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- UIUWJEYTDAZVFC-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)ethyl]propanedinitrile Chemical compound N#CC(C#N)C(C)C1=CC=C(Cl)C=C1 UIUWJEYTDAZVFC-UHFFFAOYSA-N 0.000 description 6
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000003071 parasitic effect Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- XLOPRKKSAJMMEW-SFYZADRCSA-M (R,R)-chrysanthemate Chemical compound CC(C)=C[C@@H]1[C@@H](C([O-])=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-M 0.000 description 5
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
- ZSJYICBBLIRRJB-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-2-methylpropyl]propanedinitrile Chemical compound N#CC(C#N)C(C(C)C)C1=CC=C(Cl)C=C1 ZSJYICBBLIRRJB-UHFFFAOYSA-N 0.000 description 5
- HXNDTPWSVQTUHS-UHFFFAOYSA-N 2-[1-[4-(trifluoromethoxy)phenyl]prop-2-enyl]propanedinitrile Chemical compound FC(F)(F)OC1=CC=C(C(C=C)C(C#N)C#N)C=C1 HXNDTPWSVQTUHS-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 5
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- YHLVIDQQTOMBGN-UHFFFAOYSA-N methyl prop-2-enyl carbonate Chemical compound COC(=O)OCC=C YHLVIDQQTOMBGN-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- BNBTZMHFJCIQJA-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)propanedinitrile Chemical compound CC(C)(C)CC(C#N)C#N BNBTZMHFJCIQJA-UHFFFAOYSA-N 0.000 description 4
- AMDMWNFTQDILEK-UHFFFAOYSA-N 2-[(2,3,4,5,6-pentafluorophenyl)methyl]propanedinitrile Chemical compound FC1=C(F)C(F)=C(CC(C#N)C#N)C(F)=C1F AMDMWNFTQDILEK-UHFFFAOYSA-N 0.000 description 4
- FGWGVZPDTCOPPK-UHFFFAOYSA-N 2-[(2,3-dichlorophenyl)methyl]propanedinitrile Chemical compound ClC1=CC=CC(CC(C#N)C#N)=C1Cl FGWGVZPDTCOPPK-UHFFFAOYSA-N 0.000 description 4
- XBROKFPGLALJQE-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methyl]propanedinitrile Chemical compound ClC1=CC=C(CC(C#N)C#N)C(Cl)=C1 XBROKFPGLALJQE-UHFFFAOYSA-N 0.000 description 4
- KDBNCZVVZHRCGK-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methyl]propanedinitrile Chemical compound ClC1=CC=CC(Cl)=C1CC(C#N)C#N KDBNCZVVZHRCGK-UHFFFAOYSA-N 0.000 description 4
- PNZADRODFKQPHL-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl]propanedinitrile Chemical compound COC1=CC=CC=C1CC(C#N)C#N PNZADRODFKQPHL-UHFFFAOYSA-N 0.000 description 4
- ONTUBZPGRNHELJ-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]propanedinitrile Chemical compound ClC1=CC=C(CC(C#N)C#N)C=C1Cl ONTUBZPGRNHELJ-UHFFFAOYSA-N 0.000 description 4
- VLHZCEGBKCZADN-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl]propanedinitrile Chemical compound N#CC(C#N)CC1=CC=C(C#N)C=C1 VLHZCEGBKCZADN-UHFFFAOYSA-N 0.000 description 4
- LYNBGUNDPXJMCW-UHFFFAOYSA-N 2-[(4-ethoxyphenyl)methyl]propanedinitrile Chemical compound CCOC1=CC=C(CC(C#N)C#N)C=C1 LYNBGUNDPXJMCW-UHFFFAOYSA-N 0.000 description 4
- LGHKJZGOYCCNRY-UHFFFAOYSA-N 2-[(4-methylphenyl)methyl]propanedinitrile Chemical compound CC1=CC=C(CC(C#N)C#N)C=C1 LGHKJZGOYCCNRY-UHFFFAOYSA-N 0.000 description 4
- QQIJAWNEEZUMBJ-UHFFFAOYSA-N 2-[1-[4-(trifluoromethoxy)phenyl]ethyl]propanedinitrile Chemical compound N#CC(C#N)C(C)C1=CC=C(OC(F)(F)F)C=C1 QQIJAWNEEZUMBJ-UHFFFAOYSA-N 0.000 description 4
- JGYHMHDVUHVBFO-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)propan-2-yl]propanedinitrile Chemical compound N#CC(C#N)C(C)(C)C1=CC=CC=C1Cl JGYHMHDVUHVBFO-UHFFFAOYSA-N 0.000 description 4
- CFWKBZWCLAAPML-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)propan-2-yl]propanedinitrile Chemical compound N#CC(C#N)C(C)(C)C1=CC=CC(Cl)=C1 CFWKBZWCLAAPML-UHFFFAOYSA-N 0.000 description 4
- SJGHHBVSUUNNIH-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]propanedinitrile Chemical compound N#CC(C#N)C(C)(C)C1=CC=C(Cl)C=C1 SJGHHBVSUUNNIH-UHFFFAOYSA-N 0.000 description 4
- DEVXXHPPRRTHKC-UHFFFAOYSA-N 2-[[3-(trifluoromethoxy)phenyl]methyl]propanedinitrile Chemical compound FC(F)(F)OC1=CC=CC(CC(C#N)C#N)=C1 DEVXXHPPRRTHKC-UHFFFAOYSA-N 0.000 description 4
- KXLZPFIRUHMMHU-UHFFFAOYSA-N 2-[[4-(trifluoromethylsulfanyl)phenyl]methylidene]propanedinitrile Chemical compound FC(F)(F)SC1=CC=C(C=C(C#N)C#N)C=C1 KXLZPFIRUHMMHU-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- LPNANKDXVBMDKE-UHFFFAOYSA-N 5-bromopent-1-ene Chemical compound BrCCCC=C LPNANKDXVBMDKE-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
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- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000003380 propellant Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
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- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
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- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
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- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- DFQMKYUSAALDDY-MQEBUAKTSA-N trinactin Chemical compound C[C@@H]([C@@H]1CC[C@@H](O1)C[C@H](OC(=O)[C@H](C)[C@H]1CC[C@H](O1)C[C@H](CC)OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@@H](CC)OC(=O)[C@@H]1C)CC)C(=O)O[C@@H](C)C[C@@H]2CC[C@H]1O2 DFQMKYUSAALDDY-MQEBUAKTSA-N 0.000 description 1
- DFQMKYUSAALDDY-UHFFFAOYSA-N trinactin Natural products CC1C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(C)CC2CCC1O2 DFQMKYUSAALDDY-UHFFFAOYSA-N 0.000 description 1
- UOHFCPXBKJPCAD-UHFFFAOYSA-N tyrphostin 1 Chemical compound COC1=CC=C(C=C(C#N)C#N)C=C1 UOHFCPXBKJPCAD-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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Definitions
- the present invention relates to pesticide compositions comprising the malononitrile compounds as active ingredients and to use of certain malononitrile compounds as pesticides.
- the present inventors have extensively studied to find compounds having excellent pest controlling activity. As a result, they have found that the malononitrile compounds of formula (X) as depicted below have excellent controlling activity against pests such as insect pests, acarine pests, and nematode pests, thereby reaching the present invention.
- the present invention provides a pesticide composition comprising malononitrile compounds of formula (X):
- R 1 and R 2 are the same or different and independently C 1 -C 5 (halo)alkyl, C 1 -C 5 (halo)alkyloxy, C 2 -C 5 (halo)alkenyl, C 2 -C 5 (halo)alkynyl, hydrogen, or cyano;
- R 3 and R 4 are the same or different and independently C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, or hydrogen, or R 3 and R 4 are taken together to form C 2 -C 6 (halo)alkylene or C 4 -C 6 (halo)alkenylene;
- R 5 is halogen, cyano, nitro, C 1 -C 4 (halo)alkyl, C 2 -C 4 (halo)alkenyl, C 2 -C 4 (halo)alkynyl, C 1 -C 4 (halo)alkyloxy, C 1 -C 4 (halo)alkylthio, C 1 -C 4 (halo)alkylsulfinyl, C 1 -C 4 (halo)alkylsulfonyl, C 1 -C 4 (halo)alkylcarbonyl, C 1 -C 4 (halo)alkyloxycarbonyl, C 1 -C 4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C 1 -C 3 alkyl;
- n is an integer of 0 to 4.
- R 6 is hydrogen, halogen, cyano, nitro, C 1 -C 4 (halo)alkyl, C 2 -C 4 (halo)alkenyl, C 2 -C 4 (halo)alkynyl, C 1 -C 4 (halo)alkyloxy, C 1 -C 4 (halo)alkylthio, C 1 -C 4 (halo)alkylsulfinyl, C 1 -C 4 (halo)alkylsulfonyl, C 1 -C 4 (halo)alkylcarbonyl, C 1 -C 4 (halo)alkyloxycarbonyl, C 1 -C 4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C 1 -C 3 alkyl;
- R 5 and R 6 are taken together to form methylenedioxy; with the provisos that when R 6 is hydrogen, then n is an integer of 1 to 4 and that when n is 2 or more, then R 5 's are the same or different from each other; as an active ingredient.
- the present invention also provides use of compounds (X) as active ingredients and pest controlling methods by applying compounds (X) to pests or habitats of pests.
- the (halo)alkyl group refers to alkyl optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkyloxy group refers to alkyloxy optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkenyl group refers to alkenyl optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkynyl group refers to alkynyl optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkylene group refers to alkylene optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkenylene group refers to alkenylene optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkylthio group refers to alkylthio optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkylsulfinyl group refers to alkylsulfinyl optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkylsulfonyl group refers to alkylsulfonyl optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkylcarbonyl group refers to alkylcarbonyl optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkyloxycarbonyl group refers to alkyloxycarbonyl optionally substituted with halogen for one or more than one hydrogen atoms.
- the (halo)alkylcarbonyloxy group refers to alkylcarbonyloxy optionally substituted with halogen for one or more than one hydrogen atoms.
- C 1 -C 10 refers to the number of carbon atoms constituting the alkyl, alkenyl, or alkynyl group in each substituent.
- C 1 -C 4 (halo)alkylcarbonyl means alkylcarbonyl optionally substituted with halogen for one or more hydrogen atoms wherein the alkyl part is constituted by C 1 -C 4 carbon atoms.
- each group includes specific ones as listed below:
- the C 1 -C 5 (halo)alkyl group represented by R 1 or R 2 may include methyl, ethyl, propyl, 1-methylethyl, 1,1-dimethylethyl, 2,2-dimethylpropyl, chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, and 1,1,2,2-tetrafluoroethyl.
- the C 1 -C 5 (halo)alkyloxy group represented by R 1 or R 2 may include methoxy, ethoxy, 1-methylethoxy, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, and 1,1,2,2-tetrafluoroethoxy.
- the C 2 -C 5 (halo)alkenyl group represented by R 1 or R 2 may include vinyl, 1-propenyl, 2-propenyl, 2,2-difluorovinyl, and 1,2,2-trifluorovinyl.
- the C 2 -C 5 (halo)alkynyl group represented by R 1 or R 2 may include ethynyl, 1-propynyl, 2-propynyl and 3,3,3-trifluoro-1-propynyl.
- the C 1 -C 10 alkyl group represented by R 3 or R 4 may include methyl, ethyl, 1-methylethyl, propyl, 2-methylpropyl, 2,2-dimethylpropyl, butyl, 3-methylbutyl, and 3,3-dimethylbutyl.
- the C 2 -C 10 alkenyl group represented by R 3 or R 4 may include vinyl, allyl, 1-propenyl, 3-butenyl, 2-methyl-1-propenyl, 3-methyl-2-butenyl, 3-pentenyl, 4-pentenyl, 3-methyl-3-butenyl, and 4-methyl-3-pentenyl.
- the C 2 -C 10 alkynyl group represented by R 3 or R 4 may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 3-methyl-1-butynyl, and 3,3-dimethyl-1-butynyl.
- the C 2 -C 6 (halo)alkylene group represented by R 3 and R 4 taken together may include ethylene, propylene, trimethylene, tetramethylene, and 3,3-dimethyltrimethylene.
- the C 4 -C 6 (halo)alkenylene group represented by R 3 and R 4 taken together may include 2-butenylene and 2-pentenylene.
- the halogen atom represented by R 5 or R 6 may include fluorine, chlorine, bromine, and iodine.
- the C 1 -C 4 (halo)alkyl group represented by R 5 or R 6 may include methyl, ethyl, propyl, 1-methylethyl, 1,1-dimethylethyl, trifluoromethyl, pentafluoroethyl, 3,3,3-trifluoroethyl, and 1,1,2,2-tetrafluoroethyl.
- the C 2 -C 4 (halo)alkenyl group represented by R 5 or R 6 may include vinyl, 1-propenyl, 2-propenyl and 2,2-difluorovinyl.
- the C 2 -C 4 (halo)alkynyl group represented by R 5 or R 6 may include ethynyl, 1-propynyl, 2-propynyl and 3,3,3-trifluoro-1-propynyl.
- the C 1 -C 4 (halo)alkyloxy group represented by R 5 or R 6 may include methoxy, ethoxy, propoxy, trifluoromethoxy, bromodifluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, and 1,1,2,2-tetrafluoroethoxy.
- the C 1 -C 4 (halo)alkylthio group represented by R 5 or R 6 may include methylthio, trifluoromethylthio, 2,2,2-trifluoroethylthio, and 1,1,2,2-tetrafluoroethylthio.
- the C 1 -C 4 (halo)alkylsulfinyl group represented by R 5 or R 6 may include methylsulfinyl and trifluoromethylsulfinyl.
- the C 1 -C 4 (halo)alkylsulfonyl group represented by R 5 or R 6 may include methylsulfonyl and trifluoromethylsulfonyl.
- the C 1 -C 4 (halo)alkylcarbonyl group represented by R 5 or R 6 may include acetyl, propionyl, and trifluoroacetyl.
- the C 1 -C 4 (halo)alkyloxycarbonyl group represented by R 5 or R 6 may include methoxycarbonyl and 2,2,2-trifluoroethoxycarbonyl.
- the C 1 -C 4 (halo)alkylcarbonyloxy group represented by R 5 or R 6 may include acetyloxy, propionyloxy, and trifluoroacetyloxy.
- the phenyloxy optionally substituted with halogen or C 1 -C 3 alkyl, which is represented by R 5 or R 6 , may include phenoxy, p-methylphenoxy, m-methylphenoxy, and p-chlorophenoxy.
- the phenylthio group optionally substituted with halogen or C 1 -C 3 alkyl, which is represented by R 5 or R 6 , may include phenylthio, p-methylphenylthio, m-methylphenylthio, and p-chlorophenylthio.
- compositions (X) may include the following compounds:
- R 1 is hydrogen
- R 2 is C 1 -C 5 (halo)alkyl, C 2 -C 5 (halo)alkenyl, or hydrogen
- R 3 is hydrogen
- R 4 is C 1 -C 10 alkyl, C 2 -C 10 alkenyl, or C 2 -C 10 alkynyl
- R 5 is halogen
- n is an integer of 0 to 2
- R 6 is halogen, cyano, nitro, C 1 -C 4 (halo)alkyl, C 1 -C 4 (halo)alkyloxy, or C 1 -C 4 (halo)alkylthio
- R 1 is hydrogen
- R 2 is C 1 -C 5 (halo)alkyl, C 2 -C 5 (halo)alkenyl, or hydrogen
- R 3 is hydrogen
- R 4 is C 1 -C 10 alkyl, C 2 -C 10 alkenyl, or C 2 -C 10 alkynyl
- the preferred compounds among compound (X) are the compounds wherein R 6 is halogen, cyano, nitro, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkyloxy or C 1 -C 4 haloalkylthio; the compounds wherein R 3 and R 4 are the same or different and independently C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, or hydrogen, or R 3 and R 4 are taken together to form C 2 -C 6 (halo)alkylene; or the compounds wherein n is 1 to 3 and at least one of R 5 is halogen, cyano, nitro, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkyloxy or C 1 -C 4 (halo)alkylthio.
- More preferred compounds are the compounds wherein R 6 is halogen, cyano, nitro, C 1 -C 4 fluoroalkyl, C 1 -C 4 fluoroalkyloxy or C 1 -C 4 fluoroalkylthio; or the compounds wherein n is 1 to 3 and at least one of R 5 is halogen, cyano, nitro, C 1 -C 4 fluoroalkyl, C 1 -C 4 fluoroalkyloxy or C 1 -C 4 fluoroalkylthio.
- the compounds (X) can be produced by, for example, the following (Production Process 1) to (Production Process 5).
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and n are as defined above, and Z is halogen, methanesulfonyl, trifluoromethanesulfonyl, or toluenesulfonyl.
- the reaction is usually carried out in a solvent.
- the solvent which can be used in the reaction may include acid amides such as dimethylformamide; ethers such as diethyl ether and tetrahydrofuran; organic sulfur compounds such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene; aromatic hydrocarbons such as toluene and xylene; water; and mixtures thereof.
- the base which can be used in the reaction may include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, and potassium carbonate; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; alkali metal amides such as lithium diisopropylamide; and organic bases such as 4-dimethylaminopyridine, 1,4-diazabicyclo[2.2.2]octane, and 1,8-diazabicylco[5.4.0]-7-undecene.
- the amount of base used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).
- the reaction temperature is usually in the range of ⁇ 20° C. to 100° C.
- the reaction time is usually in the range of 1 to 24 hours.
- the amount of compound (b) used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).
- reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- R 1 , R 2 , R 8 , R 4 , R 5 , R 6 , n, and Z are as defined above.
- the reaction is usually carried out in a solvent.
- the solvent which can be used in the reaction may include acid amides such as dimethylformamide; ethers such as diethyl ether and tetrahydrofuran; organic sulfur compounds such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene; aromatic hydrocarbons such as toluene and xylene; water; and mixtures thereof.
- the base which can be used in the reaction may include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, and potassium carbonate; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; alkali metal amides such as lithium diisopropylamide; and organic bases such as 4-dimethylaminopyridine, 1,4-diazabicyclo[2.2.2]octane, and 1,8-diazabicylco[5.4.0]-7-undecene.
- the amount of base used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).
- the reaction temperature is usually in the range of ⁇ 20° C. to 100° C.
- the reaction time is usually in the range of 1 to 24 hours.
- the amount of compound (b) used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).
- reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- the compound (a) can be produced through a route, for example, as shown in the following scheme.
- R 1 , R 2 , R 5 , R 6 , and n are as defined above.
- the compound (f) can be produced by reacting compound (e) with malononitrile.
- the reaction is usually carried out in a solvent and in the presence of a base.
- the solvent which can be used in the reaction may include acid amides such as N,N-dimethylformamide; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, and chlorobenzene; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, and isopropanol; and mixtures thereof.
- the base which can be used in the reaction may include tetrabutylammonium hydroxide.
- the amount of base used in the reaction is usually in a ratio of 0.01 to 0.5 mole relative to 1 mole of compound (e).
- the amount of malononitrile used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (e).
- the reaction temperature is usually in the range of ⁇ 20° C. to 200° C.
- the reaction time is usually in the range of 1 to 24 hours.
- the reaction may be carried out, while removing, if necessary, water which is generated by the reaction, from the reaction system.
- reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- the compound (a) can be produced by reacting compound (f) with an organometallic compound.
- reaction is usually carried out in a solvent and, if necessary, in the presence of a copper salt.
- the solvent which can be used in the reaction may include ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as toluene and xylene; and mixtures thereof.
- the organometallic compound which can be used in the reaction may include organic magnesium compounds such as methyl magnesium iodide, ethyl magnesium bromide, isopropyl magnesium bromide, vinyl magnesium bromide, ethynyl magnesium bromide, and dimethyl magnesium; organic lithium compounds such as methyl lithium; organic zinc compounds such as diethyl zinc; and organic copper compounds such as trifluoromethyl copper.
- the amount of organometallic compound used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (f).
- the copper salt which can be used in the reaction may include copper (I) iodide and copper (I) bromide.
- the amount of copper salt used in the reaction is usually not greater than 1 mole relative to 1 mole of compound (f).
- the reaction temperature is usually in the range of ⁇ 20° C. to 100° C.
- the reaction time is usually in the range of 1 to 24 hours.
- reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- the compound (a) can be produced by subjecting compound (f) to reduction.
- the reduction is usually carried out in a solvent.
- the solvent which can be used in the reaction may include ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, and propanol; water; and mixtures thereof.
- ethers such as diethyl ether and tetrahydrofuran
- aromatic hydrocarbons such as toluene and xylene
- alcohols such as methanol, ethanol, and propanol
- water and mixtures thereof.
- the reducing agent which can be used in the reaction may include sodium borohydride.
- the amount of reducing agent used in the reaction is usually in a ratio of 0.25 to 2 moles relative to 1 mole of compound (f).
- the reaction time is usually in the range of a moment to 24 hours.
- the reaction temperature is usually in the range of 0° C. to 50° C.
- reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- the compound (a) can be produced by reacting compound (f) with a cyanide.
- the solvent which can be used in the reaction may include ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as toluene and xylene; and mixtures thereof.
- the cyanide which can be used in the reaction may include tetrabutylammonium cyanide.
- the amount of cyanide used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (f).
- the reaction temperature is usually in the range of ⁇ 20° C. to 100° C.
- reaction time is usually in the range of 1 to 24 hours.
- reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- R 1 is C 1 -C 5 (halo)alkyl
- R 2 and R 3 are both hydrogen
- R 4 is CH 2 ⁇ CH
- R 5 , R 6 , and n are as defined above, R 11 is C 1 -C 5 (halo)alkyl, Bu is butyl, and AIBN is azobisisobutyronitrile.
- reaction can be carried out according to the process as described in J. Am. Chem. Soc., 110, 1289 (1988).
- R 5 , R 6 , and n are as defined above, dba is dibenzylideneacetone, and dppf is 1,1′-bis(diphenylphosphino)ferrocene.
- reaction can be carried out according to the conditions as described in Tetrahedron Lett., 41, 2911 (2000).
- R 1 is C 1 -C 5 (halo)alkyloxy
- R 2 and R 3 are both hydrogen
- R 4 is CH 2 ⁇ CH
- R 5 , R 6 , and n are as defined above, R 12 is C 1 -C 5 (halo)alkyloxy, Ph is phenyl, and THF is tetrahydrofuran.
- reaction can be carried out according to the conditions as described in J. Am. Chem. Soc., 120, 6838 (1998).
- the pests against which compounds (X) exhibit controlling activity may include insect pests, acarine pests, and nematode pests, specific examples which are as follows:
- Delphacidae such as Laodelphax striatellus, Nilaparvata lugens , and Sogatella furcifera;
- Deltocephalidae such as Nephotettix cincticeps and Nephotettix virescens
- Aphididae such as Aphis gossypii and Myzus persicae
- Pentatomidae such as Nezara antennata, Riptortus clavetus Eysarcoris lewisi, Eysarcoris parvus, Plautia stali and Halyomorpha misia;
- Aleyrodidae such as Trialeurodes vaporariorum and Bemisia argentifolii;
- Coccidae such as Aonidiella aurantii, Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens , and Icerya purchasi;
- Noctuidae such as Spodoptera litura, Pseudaletia separata , Thoricopiusia spp., Heliothis spp., and Helicoverpa spp.;
- Pieridae such as Pieris rapae
- Tortricidae such as Adoxophyes spp., Grapholita molesta , and Cydia pomonella;
- Carposinidae such as Carposina niponensis
- Lymantriidae such as Lyamantria spp. and Euproctis spp.
- Gelechiidae such as Pectinophora gossypiella
- Arctiidae such as Hyphantria cunea
- Tineidae such as Tinea translucens and Tineola bisselliella
- Calicidae such as Culex pipiens pallens, Culex tritaeniorhynchus , and Culex quinquefasciatus;
- Aedes spp. such as Aedes aegypti and Aedes albopictus
- Anopheles spp. such as Anopheles sinensis
- Muscidae such as Musca domestica and Muscina stabulans
- Anthomyiidae such as Delia platura and Delia antiqua
- Diabrotica spp. such as Diabrotica virgifera and Diabrotica undecimpunctata howardi;
- Curculionidae such as Sitophilus zeamais, Lissorhoptrus oryzophilus , and Callosobruchuys Kunststoffensis;
- Tenebrionidae such as Tenebrio molitor and Trbolium castaneum
- Chrysomelidae such as Oulema oryzae, Aulacophora femoralis, Phyllotreta striolata , and Leptinotarsa decemlineata;
- Epilachna spp. such as Epilachna vigintioctopunctata
- Dictyoptera [0251] Dictyoptera:
- Thysanoptera [0253] Thysanoptera:
- Thrips palmi Thrips tabaci, Frankliniella occidentalis, Frankliniella intonsa;
- Hymenoptera [0255] Hymenoptera:
- Tenthredinidae such as Athalia japonica
- Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, and Oligonychus spp.;
- Eriophyidae such as Aculops pelekassi and Aculus Lupendali;
- Tarsonemidae such as Polyphagotarsonem us latus
- Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, and Boophilus microplus;
- Epidermoptidae such as Dermatophagoides farinae and Dermatophagoides ptrenyssn us;
- Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, and Cheyletus moorei;
- Gastropoda [0288] Gastropoda:
- Pratylenchus coffeae Pratylenchus fallax
- Heterodera glycines Heterodera glycines
- Globodera rostochiensis Meloidogyne hapla
- Meloidogyne incognita Meloidogyne incognita
- compounds (X) When compounds (X) are used as the active ingredients of pesticide compositions, they may be used as such without addition of any other ingredients. However, they are usually used in admixture with solid carriers, liquid carriers and/or gaseous carriers, and if necessary, by addition of adjuvants such as surfactants, followed by formulation into various forms such emulsifiable concentrates, oil formulations, flowables, dusts, wettable powders, granules, paste formulations, microcapsule formulations, foams, aerosol formulations, carbon dioxide gas formulations, tablets, or resin formulations. These formulations may be used by processing into poison baits, shampoo, mosquito coils, electric mosquito mats, smokes, fumigants, or sheets.
- adjuvants such as surfactants
- compounds (X) are usually contained each in an amount of 0.1% to 95% by weight.
- the solid carrier which can be used in the formulation may include the following materials in fine powder or granular form: clays (e.g., kaolin clay, diatomaceous earth, bentonite, Fubasami clay, acid clay); talc, ceramic, and other inorganic minerals (e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica); and chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea).
- clays e.g., kaolin clay, diatomaceous earth, bentonite, Fubasami clay, acid clay
- talc e.g., talc, ceramic, and other inorganic minerals (e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica)
- chemical fertilizers e.g., ammonium sulfate, ammonium phosphate, ammonium
- the liquid carrier may include aromatic or aliphatic hydrocarbons (e.g., xylene, toluene, alkylnaphthalene, phenylxylylethane, kerosine, light oils, hexane, cyclohexane); halogenated hydrocarbons (e.g., chlorobenzene, dichloromethane, dichloroethane, trichloroethane); alcohols (e.g., methanol, ethanol, isopropyl alcohol, butanol, hexanol, ethylene glycol); ethers (e.g., diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, dioxane); esters (e.g., ethyl acetate, butyl acetate); ketones (e.g
- the gaseous carrier may include butane gas, Freon gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide.
- the surfactant may include alkyl sulfate salts; alkylsulfonic acid salts; alkylarylsulfonic acid salts; alkyl aryl ethers and their polyoxyethylene derivatives; polyethylene glycol ethers; polyol esters; and sugar alcohol derivatives.
- the other adjuvants may include binders, dispersants, and stabilizers, specific examples of which are casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid), PAP (isopropyl acid phosphate), BHT (2,6-di-t-butyl-4-methylphenol), BHA (mixtures of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids, and fatty acid esters.
- binders e.g., starch, gum arabic, cellulose derivatives, alginic acid
- lignin derivatives entonite
- sugars e.g., synthetic water-soluble polymers (e.g., poly
- the base material for resin formulations may include vinyl chloride polymers and polyurethanes. These base materials may contain, if necessary, plasticizers such as phthalic acid esters (e.g., dimethyl phthalate, dioctyl phthalate), adipic acid esters, and stearic acid.
- the resin formulations can be obtained by kneading the compounds into the base materials with an ordinary kneader and subsequent forming such as injection molding, extrusion, or pressing. They can be processed, if necessary, though further forming and cutting into resin formulations in various shapes such as plates, films, tapes, nets, or strings. These resin formulations are processed as, for example, collars for animals, ear tags for animals, sheet formulations, attractive strings, or poles for horticultural use.
- the base material for poison baits may include grain powders, vegetable oils, sugars, and crystalline cellulose. If necessary, additional agents may be added, including antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; agents for preventing children and pets from erroneously eating, such as hot pepper powder; and pest-attractive flavors such as cheese flavor, onion flavor, and peanut oil.
- antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid
- preservatives such as dehydroacetic acid
- agents for preventing children and pets from erroneously eating such as hot pepper powder
- pest-attractive flavors such as cheese flavor, onion flavor, and peanut oil.
- the pesticide compositions of the present invention may be used by, for example, direct application to pests and/or application to the habitats of pests (e.g., plant bodies, animal bodies, soil).
- pests e.g., plant bodies, animal bodies, soil.
- the pesticide compositions of the present invention are used for the control of pests in agriculture and forestry, their application amounts are usually 1 to 10,000 g/ha, preferably 10 to 500 g/ha.
- Formulations such as emulsifiable concentrates, wettable powders, flowables, and microcapsule formulations are usually used after dilution with water to have an active ingredient concentration of 1 to 1000 ppm, while formulations such as dusts and granules are usually used as such. These formulations may be directly applied to plants to be protected from pests. These formulations can also be incorporated into soil for the control of pests inhabiting the soil, or can also be applied to beds before planting or applied to planting holes or plant bottoms in the planting. Further, the pesticide compositions of the present invention in the form of sheet formulations can be applied by the methods in which the sheet formulations are wound around plants, disposed in the vicinity of plants, or laid on the soil surface at the plant bottoms.
- the pesticide compositions of the present invention are used for the prevention of epidemics, their application amounts as active ingredient amounts are usually 0.001 to 10 mg/m 3 for spatial application or 0.001 to 100 mg/m 2 for planar application.
- Formulations such as emulsifiable concentrates, wettable powders, and flowables are usually applied after dilution with water to have an active ingredient concentration of 0.01 to 10,000 ppm, while formulations such as oil formulations, aerosols, smokes, or poison baits are usually applied as such.
- the pesticide compositions of the present invention are used for the control of external parasites on domestic animals such as cattle, sheep, goat, and fowl or small animals such as dogs, cats, rats, and mice, they can be used by the veterinarily well-known methods.
- administration is achieved by, for example, tablets, feed incorporation, suppositories, or injections (e.g., intramuscular, subcutaneous, intravenous, intraperitoneal) for systemic control, or by, for example, spraying, pour-on treatment, or spot-on treatment with an oil formulation or an aqueous solution, washing animals with a shampoo formulation, or attachment of a collar or ear tag prepared from a resin formulation to animals for non-systemic control.
- the amounts of compounds (X) when administered to animal bodies are usually in the range of 0.1 to 1000 mg per 1 kg weight of each animal.
- the pesticide compositions of the present invention can also be used in admixture or combination with other insecticides, nematocides, acaricides, bactericides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, and the like.
- insecticides and acaricides include organophosphorus compounds such as fenitrothion[O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate], fenthion[O,O-dimethyl O-(3-methyl-4-(methythio)phenyl) phosphorothioate], diazinon[O,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate], chlorpyrifos[O,O-diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate], DDVP[2,2-dichlorovinyl dimethyl phosphate], cyanophos[O-4-cyanophenyl O,O-dimethyl phosphorothioate], dimethoate[O,O-dimethyl S-(N-methylcarbamoylmethyl)dithi
- synergists include bis-(2,3,3,3-tetrachloropropyl)ether (S-421), N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide (MGK-264) and ⁇ -[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene(piperonyl butoxide).
- n D 23.5 1.5354.
- n D 22.5 1.5272.
- n D 24.5 1.4682.
- n D 24.5 1.5028.
- n D 22.0 1.5244.
- n D 24.5 1.4707.
- n D 22.0 1.5252.
- n D 23.5 1.5398.
- n D 23.5 1.5448.
- n D 23.5 1.5483.
- n D 22.5 1.5518.
- a bundle of 3 to 4 of cotyledons (height of 3 to 5 cm) of rice was immersed in the test liquid, which had been prepared as described above, for 1 minute. After the test liquid treated the rice plants was dried, a filter paper moistened with 1 ml of water was place on a bottom of polyethylene cup and then the bundle of cotyledons of rice was placed on it. Thirty first-instar larvae of Nilaparvata lugens (brown planthoppers) were set free in the polyethylene cup, which was then kept covered and left in a greenhouse at 25° C. On the 6th day after the release of larvae of Nilaparvata lugens , the number of parasitic Nilaparvata lugens on the rice plants was examined.
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Abstract
wherein R1 and R2 are the same or different and independently C1-C5 (halo)-alkyl, C1-C5 (halo)alkyloxy, C2-C5 (halo)alkenyl, C2-C5 (halo)alkynyl, hydrogen, or cyano; R3 and R4 are the same or different and independently C1-C10 alkyl, C2-C10alkenyl, C2-C10alkynyl, or hydrogen, or R3 and R4 are taken together to form C2-C6 (halo)alkylene or C4-C6 (halo)alkenylene; R5 is halogen, cyano, nitro, C1-C4 (halo)alkyl, or the like; n is an integer of 0 to 4; R6 is halogen, cyano, nitro, C1-C4 (halo)alkyl, or the like; or R5 and R6 are taken together to form methylenedioxy; with the provisos that when R6 is hydrogen, then n is an integer of 1 to 4 and that when n is 2 or more, then R5's are different from each other; as pesticides, and to pesticide compositions containing these compounds as active ingredients. The present invention makes it possible to effectively control pests such as insect pests, acarine pests, and nematode pests.
Description
- The present invention relates to pesticide compositions comprising the malononitrile compounds as active ingredients and to use of certain malononitrile compounds as pesticides.
- Against pests such as insect pests, acarine pests, and nematode pests, various pesticide compositions have been used so far for their control. The conditions of pesticide compositions required have drastically been changed, including the care of their effects on the environment and the acquisition of drug resistance by pests to be controlled. Under such circumstances, there have been great demands for the development of new pesticide compositions.
- The present inventors have extensively studied to find compounds having excellent pest controlling activity. As a result, they have found that the malononitrile compounds of formula (X) as depicted below have excellent controlling activity against pests such as insect pests, acarine pests, and nematode pests, thereby reaching the present invention.
-
- (hereinafter referred to as compound(s) (X))
- wherein R1 and R2 are the same or different and independently C1-C5 (halo)alkyl, C1-C5 (halo)alkyloxy, C2-C5 (halo)alkenyl, C2-C5 (halo)alkynyl, hydrogen, or cyano;
- R3 and R4 are the same or different and independently C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, or hydrogen, or R3 and R4 are taken together to form C2-C6 (halo)alkylene or C4-C6 (halo)alkenylene;
- R5 is halogen, cyano, nitro, C1-C4 (halo)alkyl, C2-C4 (halo)alkenyl, C2-C4 (halo)alkynyl, C1-C4 (halo)alkyloxy, C1-C4 (halo)alkylthio, C1-C4 (halo)alkylsulfinyl, C1-C4 (halo)alkylsulfonyl, C1-C4 (halo)alkylcarbonyl, C1-C4 (halo)alkyloxycarbonyl, C1-C4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C1-C3 alkyl;
- n is an integer of 0 to 4;
- R6 is hydrogen, halogen, cyano, nitro, C1-C4 (halo)alkyl, C2-C4 (halo)alkenyl, C2-C4 (halo)alkynyl, C1-C4 (halo)alkyloxy, C1-C4 (halo)alkylthio, C1-C4 (halo)alkylsulfinyl, C1-C4 (halo)alkylsulfonyl, C1-C4 (halo)alkylcarbonyl, C1-C4 (halo)alkyloxycarbonyl, C1-C4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C1-C3 alkyl;
- or R5 and R6 are taken together to form methylenedioxy; with the provisos that when R6 is hydrogen, then n is an integer of 1 to 4 and that when n is 2 or more, then R5's are the same or different from each other; as an active ingredient.
- The present invention also provides use of compounds (X) as active ingredients and pest controlling methods by applying compounds (X) to pests or habitats of pests.
- In the definition of substituents as used herein, each group has the following meaning:
- The (halo)alkyl group refers to alkyl optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkyloxy group refers to alkyloxy optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkenyl group refers to alkenyl optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkynyl group refers to alkynyl optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkylene group refers to alkylene optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkenylene group refers to alkenylene optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkylthio group refers to alkylthio optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkylsulfinyl group refers to alkylsulfinyl optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkylsulfonyl group refers to alkylsulfonyl optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkylcarbonyl group refers to alkylcarbonyl optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkyloxycarbonyl group refers to alkyloxycarbonyl optionally substituted with halogen for one or more than one hydrogen atoms.
- The (halo)alkylcarbonyloxy group refers to alkylcarbonyloxy optionally substituted with halogen for one or more than one hydrogen atoms.
- The term “C1-C10” or the like refers to the number of carbon atoms constituting the alkyl, alkenyl, or alkynyl group in each substituent. For example, C1-C4 (halo)alkylcarbonyl means alkylcarbonyl optionally substituted with halogen for one or more hydrogen atoms wherein the alkyl part is constituted by C1-C4 carbon atoms.
- In compounds (X), each group includes specific ones as listed below:
- The C1-C5 (halo)alkyl group represented by R1 or R2 may include methyl, ethyl, propyl, 1-methylethyl, 1,1-dimethylethyl, 2,2-dimethylpropyl, chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, and 1,1,2,2-tetrafluoroethyl.
- The C1-C5 (halo)alkyloxy group represented by R1 or R2 may include methoxy, ethoxy, 1-methylethoxy, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, and 1,1,2,2-tetrafluoroethoxy.
- The C2-C5 (halo)alkenyl group represented by R1 or R2 may include vinyl, 1-propenyl, 2-propenyl, 2,2-difluorovinyl, and 1,2,2-trifluorovinyl.
- The C2-C5 (halo)alkynyl group represented by R1 or R2 may include ethynyl, 1-propynyl, 2-propynyl and 3,3,3-trifluoro-1-propynyl.
- The C1-C10 alkyl group represented by R3 or R4 may include methyl, ethyl, 1-methylethyl, propyl, 2-methylpropyl, 2,2-dimethylpropyl, butyl, 3-methylbutyl, and 3,3-dimethylbutyl.
- The C2-C10 alkenyl group represented by R3 or R4 may include vinyl, allyl, 1-propenyl, 3-butenyl, 2-methyl-1-propenyl, 3-methyl-2-butenyl, 3-pentenyl, 4-pentenyl, 3-methyl-3-butenyl, and 4-methyl-3-pentenyl.
- The C2-C10 alkynyl group represented by R3 or R4 may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 3-methyl-1-butynyl, and 3,3-dimethyl-1-butynyl.
- The C2-C6 (halo)alkylene group represented by R3 and R4 taken together may include ethylene, propylene, trimethylene, tetramethylene, and 3,3-dimethyltrimethylene.
- The C4-C6 (halo)alkenylene group represented by R3 and R4 taken together may include 2-butenylene and 2-pentenylene.
- The halogen atom represented by R5 or R6 may include fluorine, chlorine, bromine, and iodine.
- The C1-C4 (halo)alkyl group represented by R5 or R6 may include methyl, ethyl, propyl, 1-methylethyl, 1,1-dimethylethyl, trifluoromethyl, pentafluoroethyl, 3,3,3-trifluoroethyl, and 1,1,2,2-tetrafluoroethyl.
- The C2-C4 (halo)alkenyl group represented by R5 or R6 may include vinyl, 1-propenyl, 2-propenyl and 2,2-difluorovinyl.
- The C2-C4 (halo)alkynyl group represented by R5 or R6 may include ethynyl, 1-propynyl, 2-propynyl and 3,3,3-trifluoro-1-propynyl.
- The C1-C4 (halo)alkyloxy group represented by R5 or R6 may include methoxy, ethoxy, propoxy, trifluoromethoxy, bromodifluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, and 1,1,2,2-tetrafluoroethoxy.
- The C1-C4 (halo)alkylthio group represented by R5 or R6 may include methylthio, trifluoromethylthio, 2,2,2-trifluoroethylthio, and 1,1,2,2-tetrafluoroethylthio.
- The C1-C4 (halo)alkylsulfinyl group represented by R5 or R6 may include methylsulfinyl and trifluoromethylsulfinyl.
- The C1-C4 (halo)alkylsulfonyl group represented by R5 or R6 may include methylsulfonyl and trifluoromethylsulfonyl.
- The C1-C4 (halo)alkylcarbonyl group represented by R5 or R6 may include acetyl, propionyl, and trifluoroacetyl.
- The C1-C4 (halo)alkyloxycarbonyl group represented by R5 or R6 may include methoxycarbonyl and 2,2,2-trifluoroethoxycarbonyl.
- The C1-C4 (halo)alkylcarbonyloxy group represented by R5 or R6 may include acetyloxy, propionyloxy, and trifluoroacetyloxy.
- The phenyloxy optionally substituted with halogen or C1-C3 alkyl, which is represented by R5 or R6, may include phenoxy, p-methylphenoxy, m-methylphenoxy, and p-chlorophenoxy.
- The phenylthio group optionally substituted with halogen or C1-C3 alkyl, which is represented by R5 or R6, may include phenylthio, p-methylphenylthio, m-methylphenylthio, and p-chlorophenylthio.
- The embodiments of compounds (X) may include the following compounds:
- The malononitrile compounds of formula (X) wherein R1 is hydrogen, and R2 is C1-C5 (halo)alkyl, C2-C5 (halo)alkenyl, or hydrogen;
- The malononitrile compounds of formula (X) wherein R1 and R2 are both hydrogen;
- The malononitrile compounds of formula (X) wherein R3 is C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, or hydrogen; R4 is C1-C10 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl;
- The malononitrile compounds of formula (X) wherein R3 is hydrogen and R4 is C1-C10 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl;
- The malononitrile compounds of formula (X) wherein R3 is hydrogen and R4 is C1-C10 alkyl or C2-C10 alkenyl;
- The malononitrile compounds of formula (X) wherein R3 is hydrogen and R4 is C1-C10 alkyl;
- The malononitrile compounds of formula (X) wherein R5 is halogen, n is an integer of 0 to 2;
- The malononitrile compounds of formula (X) wherein R6 is halogen, cyano, nitro, C1-C4 haloalkyl, C1-C4 haloalkyloxy, or C1-C4 haloalkylthio;
- The malononitrile compounds of formula (X) wherein R5 is halogen, n is an integer of 0 to 2, and R6 is halogen, cyano, nitro, C1-C4 (halo)alkyl, C1-C4 (halo)alkyloxy, or C1-C4 (halo)alkylthio;
- The malononitrile compounds of formula (X) wherein R3 is hydrogen; R4 is C1-C10 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl, R5 is halogen, n is an integer of 0 to 2, and R6 is halogen, cyano, nitro, C1-C4 (halo)alkyl, C1-C4 (halo)alkyloxy, or C1-C4 (halo)alkylthio;
- The malononitrile compounds of formula (X) wherein R1 is hydrogen, R2 is C1-C5 (halo)alkyl, C2-C5 (halo)alkenyl, or hydrogen, R3 is hydrogen; R4 is C1-C10 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl, R5 is halogen, n is an integer of 0 to 2, and R6 is halogen, cyano, nitro, C1-C4 (halo)alkyl, C1-C4 (halo)alkyloxy, or C1-C4 (halo)alkylthio;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is trifluoromethyl;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is difluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is trifluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is trifluoromethylthio;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is 1,1,2,2-tetrafluoroethoxy;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is chlorine;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is bromine;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is fluorine;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is cyano;
- The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is nitro;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is trifluoromethyl;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is difluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is trifluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is trifluoromethylthio;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is 1,1,2,2-tetrafluoroethoxy;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is chlorine;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is bromine;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is fluorine;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is cyano;
- The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is nitro;
- The malononitrile compounds of formula (X) wherein R4 is ethyl and R6 is trifluoromethyl;
- The malononitrile compounds of formula (X) wherein R4 is ethyl and R6 is trifluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is ethyl and R6 is trifluoromethylthio;
- The malononitrile compounds of formula (X) wherein R4 is ethyl and R6 is chlorine;
- The malononitrile compounds of formula (X) wherein R4 is ethyl and R6 is cyano;
- The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R6 is trifluoromethyl;
- The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R6 is trifluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R6 is trifluoromethylthio;
- The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R6 is chlorine;
- The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R6 is cyano;
- The malononitrile compounds of formula (X) wherein R4 is 2-methyl-1-propenyl and R6 is trifluoromethyl;
- The malononitrile compounds of formula (X) wherein R4 is 2-methyl-1-propenyl and R6 is trifluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 2-methyl-1-propenyl and R6 is trifluoromethylthio;
- The malononitrile compounds of formula (X) wherein R4 is 2-methyl-1-propenyl and R6 is chlorine;
- The malononitrile compounds of formula (X) wherein R4 is 2-methyl-1-propenyl and R6 is cyano;
- The malononitrile compounds of formula (X) wherein R4 is 1-propenyl and R6 is trifluoromethyl;
- The malononitrile compounds of formula (X) wherein R4 is 1-propenyl and R6 is trifluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 1-propenyl and R6 is trifluoromethylthio;
- The malononitrile compounds of formula (X) wherein R4 is 1-propenyl and R6 is chlorine;
- The malononitrile compounds of formula (X) wherein R4 is 1-propenyl and R6 is cyano;
- The malononitrile compounds of formula (X) wherein R4 is 2-methylpropyl and R6 is trifluoromethyl;
- The malononitrile compounds of formula (X) wherein R4 is 2-methylpropyl and R6 is difluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 2-methylpropyl and R6 is trifluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 2-methylpropyl and R6 is trifluoromethylthio;
- The malononitrile compounds of formula (X) wherein R4 is 2-methylpropyl and R6 is 1,1,2,2-tetrafluoroethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 2-methylpropyl and R6 is chlorine;
- The malononitrile compounds of formula (X) wherein R4 is 2-methylpropyl and R6 is bromine;
- The malononitrile compounds of formula (X) wherein R4 is 2-methylpropyl and R6 is fluorine;
- The malononitrile compounds of formula (X) wherein R4 is 2-methylpropyl and R6 is cyano;
- The malononitrile compounds of formula (X) wherein R4 is −2-methylpropyl and R6 is nitro;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is trifluoromethyl;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is difluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is trifluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is trifluoromethylthio;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is 1,1,2,2-tetrafluoroethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is chlorine;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is bromine;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is fluorine;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is cyano;
- The malononitrile compounds of formula (X) wherein R4 is 2,2-dimethylpropyl and R6 is nitro;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is trifluoromethyl;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is difluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is trifluoromethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is trifluoromethylthio;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is 1,1,2,2-tetrafluoroethoxy;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is chlorine;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is bromine;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is fluorine;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is cyano;
- The malononitrile compounds of formula (X) wherein R4 is 1-methylethyl and R6 is nitro.
- The preferred compounds among compound (X) are the compounds wherein R6 is halogen, cyano, nitro, C1-C4 haloalkyl, C1-C4 haloalkyloxy or C1-C4 haloalkylthio; the compounds wherein R3 and R4 are the same or different and independently C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, or hydrogen, or R3 and R4 are taken together to form C2-C6 (halo)alkylene; or the compounds wherein n is 1 to 3 and at least one of R5 is halogen, cyano, nitro, C1-C4 haloalkyl, C1-C4 haloalkyloxy or C1-C4 (halo)alkylthio. More preferred compounds are the compounds wherein R6 is halogen, cyano, nitro, C1-C4 fluoroalkyl, C1-C4 fluoroalkyloxy or C1-C4 fluoroalkylthio; or the compounds wherein n is 1 to 3 and at least one of R5 is halogen, cyano, nitro, C1-C4 fluoroalkyl, C1-C4 fluoroalkyloxy or C1-C4 fluoroalkylthio.
- The following will describe the production processes for compounds (X).
- The compounds (X) can be produced by, for example, the following (Production Process 1) to (Production Process 5).
- (Production Process 1)
-
- wherein R1, R2, R3, R4, R5, R6, and n are as defined above, and Z is halogen, methanesulfonyl, trifluoromethanesulfonyl, or toluenesulfonyl.
- The reaction is usually carried out in a solvent. The solvent which can be used in the reaction may include acid amides such as dimethylformamide; ethers such as diethyl ether and tetrahydrofuran; organic sulfur compounds such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene; aromatic hydrocarbons such as toluene and xylene; water; and mixtures thereof. The base which can be used in the reaction may include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, and potassium carbonate; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; alkali metal amides such as lithium diisopropylamide; and organic bases such as 4-dimethylaminopyridine, 1,4-diazabicyclo[2.2.2]octane, and 1,8-diazabicylco[5.4.0]-7-undecene. The amount of base used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).
- The reaction temperature is usually in the range of −20° C. to 100° C.
- The reaction time is usually in the range of 1 to 24 hours.
- The amount of compound (b) used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).
- After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- (Production Process 2)
-
- wherein R1, R2, R8, R4, R5, R6, n, and Z are as defined above.
- The reaction is usually carried out in a solvent. The solvent which can be used in the reaction may include acid amides such as dimethylformamide; ethers such as diethyl ether and tetrahydrofuran; organic sulfur compounds such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene; aromatic hydrocarbons such as toluene and xylene; water; and mixtures thereof.
- The base which can be used in the reaction may include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, and potassium carbonate; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; alkali metal amides such as lithium diisopropylamide; and organic bases such as 4-dimethylaminopyridine, 1,4-diazabicyclo[2.2.2]octane, and 1,8-diazabicylco[5.4.0]-7-undecene. The amount of base used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).
- The reaction temperature is usually in the range of −20° C. to 100° C.
- The reaction time is usually in the range of 1 to 24 hours.
- The amount of compound (b) used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).
- After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
-
- wherein R1, R2, R5, R6, and n are as defined above.
- (Step 1)
- The compound (f) can be produced by reacting compound (e) with malononitrile.
- The reaction is usually carried out in a solvent and in the presence of a base. The solvent which can be used in the reaction may include acid amides such as N,N-dimethylformamide; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, and chlorobenzene; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, and isopropanol; and mixtures thereof.
- The base which can be used in the reaction may include tetrabutylammonium hydroxide. The amount of base used in the reaction is usually in a ratio of 0.01 to 0.5 mole relative to 1 mole of compound (e).
- The amount of malononitrile used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (e).
- The reaction temperature is usually in the range of −20° C. to 200° C.
- The reaction time is usually in the range of 1 to 24 hours.
- The reaction may be carried out, while removing, if necessary, water which is generated by the reaction, from the reaction system.
- After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- (Step 2)
- (1) The case where R2 is a substituent other than hydrogen and cyano:
- The compound (a) can be produced by reacting compound (f) with an organometallic compound.
- The reaction is usually carried out in a solvent and, if necessary, in the presence of a copper salt.
- The solvent which can be used in the reaction may include ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as toluene and xylene; and mixtures thereof.
- The organometallic compound which can be used in the reaction may include organic magnesium compounds such as methyl magnesium iodide, ethyl magnesium bromide, isopropyl magnesium bromide, vinyl magnesium bromide, ethynyl magnesium bromide, and dimethyl magnesium; organic lithium compounds such as methyl lithium; organic zinc compounds such as diethyl zinc; and organic copper compounds such as trifluoromethyl copper. The amount of organometallic compound used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (f).
- The copper salt which can be used in the reaction may include copper (I) iodide and copper (I) bromide. The amount of copper salt used in the reaction is usually not greater than 1 mole relative to 1 mole of compound (f).
- The reaction temperature is usually in the range of −20° C. to 100° C.
- The reaction time is usually in the range of 1 to 24 hours.
- After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- (2) The case where R2 is hydrogen:
- The compound (a) can be produced by subjecting compound (f) to reduction.
- The reduction is usually carried out in a solvent.
- The solvent which can be used in the reaction may include ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, and propanol; water; and mixtures thereof.
- The reducing agent which can be used in the reaction may include sodium borohydride. The amount of reducing agent used in the reaction is usually in a ratio of 0.25 to 2 moles relative to 1 mole of compound (f).
- The reaction time is usually in the range of a moment to 24 hours.
- The reaction temperature is usually in the range of 0° C. to 50° C.
- After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- (3) The case where R2 is cyano:
- The compound (a) can be produced by reacting compound (f) with a cyanide.
- The solvent which can be used in the reaction may include ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as toluene and xylene; and mixtures thereof.
- The cyanide which can be used in the reaction may include tetrabutylammonium cyanide. The amount of cyanide used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (f).
- The reaction temperature is usually in the range of −20° C. to 100° C.
- The reaction time is usually in the range of 1 to 24 hours.
- After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.
- (Production Process 3)
-
- wherein R5, R6, and n are as defined above, R11 is C1-C5 (halo)alkyl, Bu is butyl, and AIBN is azobisisobutyronitrile.
- The reaction can be carried out according to the process as described in J. Am. Chem. Soc., 110, 1289 (1988).
- (Production Process 4)
-
- wherein R5, R6, and n are as defined above, dba is dibenzylideneacetone, and dppf is 1,1′-bis(diphenylphosphino)ferrocene.
- The reaction can be carried out according to the conditions as described in Tetrahedron Lett., 41, 2911 (2000).
- (Production Process 5)
-
- wherein R5, R6, and n are as defined above, R12 is C1-C5 (halo)alkyloxy, Ph is phenyl, and THF is tetrahydrofuran.
- The reaction can be carried out according to the conditions as described in J. Am. Chem. Soc., 120, 6838 (1998).
- The pests against which compounds (X) exhibit controlling activity may include insect pests, acarine pests, and nematode pests, specific examples which are as follows:
- Hemiptera:
- Delphacidae such asLaodelphax striatellus, Nilaparvata lugens, and Sogatella furcifera;
- Deltocephalidae such asNephotettix cincticeps and Nephotettix virescens;
- Aphididae such asAphis gossypii and Myzus persicae;
- Pentatomidae such asNezara antennata, Riptortus clavetus Eysarcoris lewisi, Eysarcoris parvus, Plautia stali and Halyomorpha misia;
- Aleyrodidae such asTrialeurodes vaporariorum and Bemisia argentifolii;
- Coccidae such asAonidiella aurantii, Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, and Icerya purchasi;
- Tingidae;
- Psyllidae;
- Lepidoptera:
- Pyralidae such asChilo suppressalis, Cnaphalocrocis medinalis, Notarcha derogata, and Plodia interpunctella;
- Noctuidae such asSpodoptera litura, Pseudaletia separata, Thoricopiusia spp., Heliothis spp., and Helicoverpa spp.;
- Pieridae such asPieris rapae;
- Tortricidae such as Adoxophyes spp.,Grapholita molesta, and Cydia pomonella;
- Carposinidae such asCarposina niponensis;
- Lyonetiidae such as Lyonetia spp.;
- Lymantriidae such as Lyamantria spp. and Euproctis spp.;
- Yponomentidae such asPlutella xylostella;
- Gelechiidae such asPectinophora gossypiella;
- Arctiidae such asHyphantria cunea;
- Tineidae such asTinea translucens and Tineola bisselliella;
- Diptera:
- Calicidae such asCulex pipiens pallens, Culex tritaeniorhynchus, and Culex quinquefasciatus;
- Aedes spp. such asAedes aegypti and Aedes albopictus;
- Anopheles spp. such asAnopheles sinensis;
- Chironomidae;
- Muscidae such asMusca domestica and Muscina stabulans;
- Calliphoridae;
- Sarcophagidae;
- Fanniidae;
- Anthomyiidae such asDelia platura and Delia antiqua;
- Tephritidae;
- Drosophilidae;
- Psychodidae;
- Simuliidae;
- Tabanidae;
- Stomoxyidae;
- Agromyzidae;
- Coleoptera:
- Diabrotica spp. such asDiabrotica virgifera and Diabrotica undecimpunctata howardi;
- Scarabaeidae such asAnomala cuprea and Anomala rufocuprea;
- Curculionidae such asSitophilus zeamais, Lissorhoptrus oryzophilus, and Callosobruchuys chienensis;
- Tenebrionidae such asTenebrio molitor and Trbolium castaneum;
- Chrysomelidae such asOulema oryzae, Aulacophora femoralis, Phyllotreta striolata, and Leptinotarsa decemlineata;
- Anobiidae;
- Epilachna spp. such asEpilachna vigintioctopunctata;
- Lyctidae;
- Bostrychidae;
- Cerambycidae;
- Paederus fuscipes;
- Dictyoptera:
-
- Thysanoptera:
-
- Hymenoptera:
- Formicidae;
- Vespidae;
- Bethylidae;
- Tenthredinidae such asAthalia japonica;
- Orthoptera:
- Gryllotalpidae;
- Acrididae;
- Siphonaptera:
-
- Anoplura:
-
- Isoptera:
- Reticulitermes speratus and Coptotermes formosanus;
- Acarina:
- Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, and Oligonychus spp.;
- Eriophyidae such as Aculops pelekassi and Aculus schlechtendali;
- Tarsonemidae such as Polyphagotarsonem us latus;
- Tenuipalpidae;
- Tuckerellidae;
- Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, and Boophilus microplus;
- Acaridae such as Tophagus putrescentiae;
- Epidermoptidae such as Dermatophagoides farinae and Dermatophagoides ptrenyssn us;
- Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, and Cheyletus moorei;
- Dermanyssidae;
- Arachnida:
- Chiracanthium japonicum and Latrodectus hasseltii;
- Chilopoda:
- Thereuonema hilgendorfliand Scolopendra suhspinipes;
- Diplopoda:
- Oxidus gracilis and Nedyopus tambanus;
- Isopoda:
- Armadillidium vulgare;
- Gastropoda:
- Limax marginatus and Limax flavus;
- Nematoda:
- Pratylenchus coffeae, Pratylenchus fallax, Heterodera glycines, Globodera rostochiensis, Meloidogyne hapla, and Meloidogyne incognita.
- When compounds (X) are used as the active ingredients of pesticide compositions, they may be used as such without addition of any other ingredients. However, they are usually used in admixture with solid carriers, liquid carriers and/or gaseous carriers, and if necessary, by addition of adjuvants such as surfactants, followed by formulation into various forms such emulsifiable concentrates, oil formulations, flowables, dusts, wettable powders, granules, paste formulations, microcapsule formulations, foams, aerosol formulations, carbon dioxide gas formulations, tablets, or resin formulations. These formulations may be used by processing into poison baits, shampoo, mosquito coils, electric mosquito mats, smokes, fumigants, or sheets.
- In these formulations, compounds (X) are usually contained each in an amount of 0.1% to 95% by weight.
- The solid carrier which can be used in the formulation may include the following materials in fine powder or granular form: clays (e.g., kaolin clay, diatomaceous earth, bentonite, Fubasami clay, acid clay); talc, ceramic, and other inorganic minerals (e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica); and chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea).
- The liquid carrier may include aromatic or aliphatic hydrocarbons (e.g., xylene, toluene, alkylnaphthalene, phenylxylylethane, kerosine, light oils, hexane, cyclohexane); halogenated hydrocarbons (e.g., chlorobenzene, dichloromethane, dichloroethane, trichloroethane); alcohols (e.g., methanol, ethanol, isopropyl alcohol, butanol, hexanol, ethylene glycol); ethers (e.g., diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, dioxane); esters (e.g., ethyl acetate, butyl acetate); ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone); nitriles (acetonitrile, isobutyronitrile); sulfoxides (e.g., dimethylsulfoxide); acid amides (e.g., N,N-dimethylformamide, N,N-dimethylacetamide); vegetable oils (e.g., soy bean oil and cotton seed oil); plant essential oils (e.g., orange oil, hyssop oil, lemon oil); and water.
- The gaseous carrier may include butane gas, Freon gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide.
- The surfactant may include alkyl sulfate salts; alkylsulfonic acid salts; alkylarylsulfonic acid salts; alkyl aryl ethers and their polyoxyethylene derivatives; polyethylene glycol ethers; polyol esters; and sugar alcohol derivatives.
- The other adjuvants may include binders, dispersants, and stabilizers, specific examples of which are casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid), PAP (isopropyl acid phosphate), BHT (2,6-di-t-butyl-4-methylphenol), BHA (mixtures of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids, and fatty acid esters.
- The base material for resin formulations may include vinyl chloride polymers and polyurethanes. These base materials may contain, if necessary, plasticizers such as phthalic acid esters (e.g., dimethyl phthalate, dioctyl phthalate), adipic acid esters, and stearic acid. The resin formulations can be obtained by kneading the compounds into the base materials with an ordinary kneader and subsequent forming such as injection molding, extrusion, or pressing. They can be processed, if necessary, though further forming and cutting into resin formulations in various shapes such as plates, films, tapes, nets, or strings. These resin formulations are processed as, for example, collars for animals, ear tags for animals, sheet formulations, attractive strings, or poles for horticultural use.
- The base material for poison baits may include grain powders, vegetable oils, sugars, and crystalline cellulose. If necessary, additional agents may be added, including antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; agents for preventing children and pets from erroneously eating, such as hot pepper powder; and pest-attractive flavors such as cheese flavor, onion flavor, and peanut oil.
- The pesticide compositions of the present invention may be used by, for example, direct application to pests and/or application to the habitats of pests (e.g., plant bodies, animal bodies, soil).
- When the pesticide compositions of the present invention are used for the control of pests in agriculture and forestry, their application amounts are usually 1 to 10,000 g/ha, preferably 10 to 500 g/ha. Formulations such as emulsifiable concentrates, wettable powders, flowables, and microcapsule formulations are usually used after dilution with water to have an active ingredient concentration of 1 to 1000 ppm, while formulations such as dusts and granules are usually used as such. These formulations may be directly applied to plants to be protected from pests. These formulations can also be incorporated into soil for the control of pests inhabiting the soil, or can also be applied to beds before planting or applied to planting holes or plant bottoms in the planting. Further, the pesticide compositions of the present invention in the form of sheet formulations can be applied by the methods in which the sheet formulations are wound around plants, disposed in the vicinity of plants, or laid on the soil surface at the plant bottoms.
- When the pesticide compositions of the present invention are used for the prevention of epidemics, their application amounts as active ingredient amounts are usually 0.001 to 10 mg/m3 for spatial application or 0.001 to 100 mg/m2 for planar application. Formulations such as emulsifiable concentrates, wettable powders, and flowables are usually applied after dilution with water to have an active ingredient concentration of 0.01 to 10,000 ppm, while formulations such as oil formulations, aerosols, smokes, or poison baits are usually applied as such.
- When the pesticide compositions of the present invention are used for the control of external parasites on domestic animals such as cattle, sheep, goat, and fowl or small animals such as dogs, cats, rats, and mice, they can be used by the veterinarily well-known methods. As the specific methods of use, administration is achieved by, for example, tablets, feed incorporation, suppositories, or injections (e.g., intramuscular, subcutaneous, intravenous, intraperitoneal) for systemic control, or by, for example, spraying, pour-on treatment, or spot-on treatment with an oil formulation or an aqueous solution, washing animals with a shampoo formulation, or attachment of a collar or ear tag prepared from a resin formulation to animals for non-systemic control. The amounts of compounds (X) when administered to animal bodies are usually in the range of 0.1 to 1000 mg per 1 kg weight of each animal.
- The pesticide compositions of the present invention can also be used in admixture or combination with other insecticides, nematocides, acaricides, bactericides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, and the like.
- Examples of the insecticides and acaricides include organophosphorus compounds such as fenitrothion[O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate], fenthion[O,O-dimethyl O-(3-methyl-4-(methythio)phenyl) phosphorothioate], diazinon[O,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate], chlorpyrifos[O,O-diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate], DDVP[2,2-dichlorovinyl dimethyl phosphate], cyanophos[O-4-cyanophenyl O,O-dimethyl phosphorothioate], dimethoate[O,O-dimethyl S-(N-methylcarbamoylmethyl)dithiophosphate], phenthoate[ethyl 2-dimethoxyphosphinothioylthio(phenyl)acetate], malathion[diethyl(dimethoxyphosphinothioylthio)succinate], and azinphosmethyl[S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O,O-dimethyl phosphorodithioate]; carbamate compounds such as BPMC (2-sec-butyl-phenyl methylcarbamate), benfracarb[ethyl N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-p-alaninate], propoxur[2-isopropoxyphenyl N-methylcarbamate] and carbaryl[1-naphthyl N-methylcarbamate]; pyrethroid compounds such as etofenprox[2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether], fenvalerate[(RS)-α-cyano-3-phenoxybenzyl(RS)-2-(4-chlorophenyl)-3-methyl-butyrate], esfenvalerate[(S)-α-cyano-3-phenoxybenzyl(S)-2-(4-chlorophenyl)-3-methylbutyrate], fenpropathrin[(RS)-α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], cypermethrin[(RS)-α-cyano-3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], permethrin[3-phenoxybenzyl(1RS)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], cyhalothrin[(RS)-α-cyano-3-phenoxybenzyl(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], deltamethrin[(S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-carboxylate], cycloprothrin[(RS)-α-cyano-3-phenoxybenzyl(RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate], fluvalinate[α-cyano-3-phenoxybenzyl N-(2-chloro-α,α,α-trifluoro-p-tolyl)-D-valinate], bifenthrin[2-methylbiphenyl-3-ylmethyl(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], 2-methyl-2-(4-bromodifluoro-methoxyphenyl)propyl 3-phenoxybenzyl ether, tralomethrin[(S)-α-cyano-3-phenoxybenzyl (1R-cis)-3-{(1RS)(1,2,2,2-tetrabromoethyl)}-2,2-dimethyl-cyclopropanecarboxylate], silafluofen[(4-ethoxyphenyl){3-(4-fluoro-3-phenoxyphenyl)propyl}-dimethylsilane], d-phenothrin[3-phenoxybenzyl(1R-cis,trans)-chrysanthemate], cyphenothrin[(RS)-α-cyano-3-phenoxybenzyl(1R-cis,trans)-chrysanthemate], d-resmethrin[5-benzyl-3-furylmethyl(1R-cis,trans)-chrysanthemate], acrinathrin[(S)-α-cyano-3-phenoxybenzyl(1R,cis(Z))-2,2-dimethyl-3-{3-oxo-3-(1,1,1,3,3,3-hexafluoropropyloxy)propenyl}cyclopropanecarboxylate], cyfluthrin[(RS)-α-cyano-4-fluoro-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], tefluthrin[2,3,5,6-tetrafluoro-4-methylbenzyl(RS-cis(Z))-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], transfluthrin[2,3,5,6-tetrafluorobenzyl (1R-trans)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], tetramethrin [3,4,5,6-tetrahydrophthalimidomethyl(1RS)-cis,trans-chrysanthemate], allethrin[(RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl(1RS)cis,trans-chrysanthemate], prallethrin[(S)-2-methyl-4-oxo-3-(2-propynyl) cyclopent-2-enyl(1R)-cis,trans-chrysanthemate], empenthrin[(RS)-1-ethynyl-2-methyl-2-pentenyl(1R)-cis,trans-chrysanthemate], imiprothrin[2,5-dioxo-3-(prop-2-ynyl)imidazolidin-1-ylmethyl(1R)-cis,trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate], d-furamethrin[5-(2-propynyl) furfuryl(1R)-cis,trans-chrysanthemate] and 5-(2-propynyl)furfuryl 2,2,3,3-tetramethylcyclopropanecarboxylate; neonicotinoid derivatives such as N-cyano-N′-methyl-N′-(6-chloro-3-pyridylmethyl)acetamidine; nitenpyram[N-(6-chloro-3-pyridylmethyl)-N-ethyl-N′-methyl-2-nitrovynylidenediamine]; thiacloprid[1-(2-chloro-5-pyridylmethyl)-2-cyanoiminothiazoline]; thiamethoxam[3-((2-chloro-5-thiazolyl)methyl)-5-methyl-4-nitroiminotetrahydro-1,3,5-oxadiazine], 1-methyl-2-nitro-3-((3-tetrahydrofuryl)methyl)guanidine and 1-(2-chloro-5-thiazolyl)methyl-3-methyl-2-nitroguanidine; nitroiminohexahydro-1,3,5-triazine derivatives; chlorinated hydrocarbons such as endosulfan[6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepine oxide], γ-BHC [1,2,3,4,5,6-hexachlorocyclohexane] and 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol; benzoylphenylurea compounds such as chlorfluazuron[1-(3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridyn-2-yloxy)phenyl)-3-(2,6-difluorobenzoyl)urea], teflubenzuron[1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea] and flufenoxuron[1-(4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)-3-(2,6-difluorobenzoyl)urea]; juvenile hormone like compounds such as pyriproxyfen[4-phenoxyphenyl 2-(2-pyridyloxy)propyl ether], methoprene[isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate] and hydroprene[ethyl(2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate]; thiourea derivatives such as diafenthiuron[N-(2,6-diisopropyl-4-phenoxyphenyl)-N′-tert-butylcarbodiimide]; phenylpyrazole compounds; 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrol-3-carbonitrile[chlorfenapil]; metoxadiazone[5-methoxy-3-(2-methoxyphenyl)-1,3,4-oxadiazol-2(3H)-one], bromopropylate[isopropyl 4,4′-dibromobenzilate], tetradifon[4-chlorophenyl 2,4,5-trichlorophenyl sulfone], chinomethionat[S,S-6-methylquinoxaline-2,3-diyldithiocarbonate], pyridaben[2-tert-butyl-5-(4-tertbutylbenzylthio)-4-chloropyridazin-3(2H)-one], fenpyroximate [tert-butyl (E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl]benzoate], tebufenpyrad[N-(4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide], polynactins complex[tetranactin, dinactin and trinactin], pyrimidifen [5-chloro-N-[2-{4-(2-ethoxyethyl)-2,3-dimethylphenoxy}ethyl]-6-ethylpyrimidin-4-amine], milbemectin, abamectin, ivermectin and azadirachtin[AZAD]. Examples of the synergists include bis-(2,3,3,3-tetrachloropropyl)ether (S-421), N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide (MGK-264) and α-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene(piperonyl butoxide).
- The present invention will further be illustrated by the following production examples, formulation examples, and test examples; however, the present invention is not limited only to these examples. In the formulation examples, the compound numbers are those shown in Table 1 below.
- The following will describe some production examples for compounds (X).
- First, 0.20 g of (4-chlorobenzyl)malononitrile was dissolved in 5 ml of N,N-dimethylformamide, to which 46 mg of sodium hydride (60% in oil) was added, while stirring under ice cooling. After the evolution of hydrogen gas ceased, while stirring under ice cooling, 0.44 ml of allyl bromide was added dropwise, followed by further stirring at room temperature overnight. Then, 10% hydrochloric acid was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.13 g of 2-allyl-2-(4-chlorobenzyl)malononitrile (compound 1).
- Yield: 54%;
- nD 22.0: 1.5326.
- Using 0.60 g of (1-(4-chlorophenyl)-1-methylethyl)malononitrile, 10 ml of N,N-dimethylformamide, 121 mg of sodium hydride (60% in oil), and 1.20 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.60 g of 2-allyl-2-(1-(4-chlorophenyl)-1-methylethyl)malononitrile (compound 2).
- Yield: 85%;
- nD 23.5: 1.5354.
- Using 0.36 g of (1-(4-chlorophenyl)-2-methylpropyl)malononitrile, 5 ml of N,N-dimethylformamide, 75 mg of sodium hydride (60% in oil), and 0.20 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.29 g of 2-allyl-2-(1-(4-chlorophenyl)-2-methylpropyl)malononitrile (compound 3).
- Yield: 69%;
- nD 22.5: 1.5272.
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 126 mg of sodium hydride (60% in oil), and 0.40 ml of 4-bromo-1-butene, and according to the process described in the Production Example 1, there was obtained 0.46 g of 2-(3-butenyl)-2-(4-chlorobenzyl)malononitrile (compound 4).
- Yield: 72%;
- m.p.: 63.7° C.
- Using 1.12 g of (4-(trifluoromethyl)benzyl)malononitrile, 10 ml of N,N-dimethylformamide, 0.24 g of sodium hydride (60% in oil), and 0.63 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.58 g of 2-allyl-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 5).
- Yield: 44%;
- m.p.: 80.2° C.
- Using 0.50 g of (4-cyanobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 132 mg of sodium hydride (60% in oil), and 0.42 ml of 4-bromo-1-butene, and according to the process described in the Production Example 1, there was obtained 0.19 g of 2-(3-butenyl)-2-(4-cyanobenzyl)malononitrile (compound 6).
- Yield: 29%;
- m.p.: 109.4° C.
- Using 0.50 g of (4-cyanobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 132 mg of sodium hydride (60% in oil), and 0.49 ml of 5-bromo-1-pentene, and according to the process described in the Production Example 1, there was obtained 0.12 g of 2-(4-cyanobenzyl)-2-(4-pentenyl)malononitrile (compound 7).
- Yield: 17%;
- m.p.: 91.5° C.
- Using 0.20 g of (2-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 46 mg of sodium hydride (60% in oil), and 0.44 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.18 g of 2-allyl-2-(2-chlorobenzyl)malononitrile (compound 8).
- Yield: 74%;
- nD 20.5: 1.5329.
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 160 mg of sodium hydride (60% in oil), and 0.68 ml of cyclohexyl iodide, and according to the process described in the Production Example 1, there was obtained 0.20 g of 2-(4-chlorobenzyl)-2-cyclohexylmalononitrile (compound 9).
- Yield: 28%;
- m.p.: 107.9° C.
- Using 0.56 g of (1-(4-chlorophenyl)ethyl)malononitrile, 5 ml of N,N-dimethylformamide, 160 mg of sodium hydride (60% in oil), and 0.56 ml of 4-bromo-1-butene, and according to the process described in the Production Example 1, there was obtained 0.23 g of 2-(3-butenyl)-2-(1-(4-chlorophenyl)ethyl)malononitrile (compound 10).
- Yield: 32%;
- nD 25.5: 1.5259.
- Using 0.50 g of (4-(trifluoromethoxy)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 123 mg of sodium hydride, and 0.35 ml of ally bromide, and according to the process described in the Production Example 1, there was obtained 0.26 g of 2-allyl-2-(4-(trifluoromethoxy)benzyl)malononitrile (compound 11).
- Yield: 45%;
- nD 24.5: 1.4682.
- Using 0.77 g of (1-(4-(trifluoromethoxy)phenyl-2-methylpropyl)malononitrile, 5 ml of N,N-dimethylformamide, 160 mg of sodium hydride (60% in oil), and 0.55 ml of 4-bromo-1-butene, and according to the process described in the Production Example 1, there was obtained 0.30 g of 2-(3-butenyl)-2-(1-(4-(trifluoromethoxyphenyl)-2-methylpropyl)malononitrile (compound 12).
- Yield: 33%;
- nD 25.5: 1.4686.
- Using 2.35 g of (4-bromobenzyl)malononitrile, 50 ml of N,N-dimethylformamide, 0.44 g of sodium hydride (60% in oil), and 4.23 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 2.33 g of 2-allyl-2-(4-bromobenzyl)malononitrile (compound 13).
- Yield: 85%;
- m.p.: 61.7° C.
- Using 1.81 g of (4-cyanobenzyl)malononitrile, 50 ml of N,N-dimethylformamide, 0.44 g of sodium hydride (60% in oil), and 4.23 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.04 g of 2-allyl-2-(4-cyanobenzyl)malononitrile (compound 14).
- Yield: 47%;
- m.p.: 81.9° C.
- Using 0.23 g of (4-(trifluoromethoxy)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 60 mg of sodium hydride (60% in oil), and 0.20 ml of 4-bromo-1-butene, and according to the process described in the Production Example 1, there was obtained 0.16 g of 2-(3-butenyl)-2-(4-(trifluoromethoxy)benzyl)malononitrile (compound 15).
- Yield: 54%;
- nD 25.5: 1.4657.
- Using 0.76 g of (1-(4-(trifluoromethoxy)phenyl)ethyl)malononitrile, 5 ml of N,N-dimethylformamide, 180 mg of sodium hydride (60% in oil), and 0.61 ml of 4-bromo-1-butene, and according to the process described in the Production Example 1, there was obtained 0.36 g of 2-(3-butenyl)-2-(1-(4-(trifluoromethoxy)phenyl)ethyl)malononitrile (compound 16).
- Yield: 39%;
- nD 25.5: 1.4673.
- Using 0.20 g of (3-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 46 mg of sodium hydride (60% in oil), and 0.44 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.11 g of 2-allyl-2-(3-chlorobenzyl)malononitrile (compound 17).
- Yield: 45%;
- nD 21.5: 1.5302.
- Using 1.74 g of (4-fluorobenzyl)malononitrile, 50 ml of N,N-dimethylformamide, 0.44 g of sodium hydride (60% in oil), and 4.23 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 2.00 g of 2-allyl-2-(4-fluorobenzyl)malononitrile (compound 18).
- Yield: 93%;
- nD 24.5: 1.5028.
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.12 g of sodium hydride (60% in oil), and 0.33 ml of isobutyl iodide, and according to the process described in the Production Example 1, there was obtained 0.42 g of 2-(4-chlorobenzyl)-2-isobutylmalononitrile (compound 19).
- Yield: 65%;
- m.p.: 73.2° C.
- Using 0.50 g of (2-methoxybenzyl)malononitrile, 10 ml of N,N-dimethylformamide, 0.12 g of sodium hydride (60% in oil), and 1.1 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.50 g of 2-allyl-2-(2-methoxybenzyl)malononitrile (compound 20).
- Yield: 83%;
- nD 18.5: 1.5231.
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.126 g of sodium hydride (60% in oil), and 0.47 ml of 5-bromo-1-pentene, and according to the process described in the Production Example 1, there was obtained 0.49 g of 2-(4-chlorobenzyl)-2-(4-pentenyl)malononitrile (compound 21).
- Yield: 72%;
- nD 22.0: 1.5244.
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.126 g of sodium hydride (60% in oil), and 0.40 g of 3-chloro-1-butene, and according to the process described in the Production Example 1, there was obtained 0.35 g of 2-(4-chlorobenzyl)-2-(1-methyl-2-propenyl)malononitrile (compound 22).
- Yield: 55%;
- nD 22.5: 1.5284.
- Using 2.25 g of (3,4-dichlorobenzyl)malononitrile, 50 ml of N,N-dimethylformamide, 0.48 g of sodium hydride (60% in oil), and 1.30 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.96 g of 2-allyl-2-(3,4-dichlorobenzyl)malononitrile (compound 23).
- Yield: 74%;
- m.p.: 71.8° C.
- Using 1.13 g of (2,4-dichlorobenzyl)malononitrile, 20 ml of N,N-dimethylformamide, 0.24 g of sodium hydride (60% in oil), and 0.63 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.78 g of 2-allyl-2-(2,4-dichlorobenzyl)malononitrile (compound 24).
- Yield: 59%;
- nD 24.5: 1.5447
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.16 g of sodium hydride (60% in oil), and 0.60 ml of 1-bromo-3-methyl-2-butene, and according to the process described in the Production Example 1, there was obtained 0.52 g of 2-(4-chlorobenzyl)-2-(3-methyl-2-butenyl)malononitrile (compound 25).
- Yield: 77%;
- nD 25.5: 1.5263.
- Using 0.80 g of (1-(4-chlorophenyl)-2-methylpropyl)malononitrile, 10 ml of N,N-dimethylformamide, 0.21 g of sodium hydride (60% in oil), and 0.70 ml of 4-bromo-1-butene, and according to the process described in Production Example 1, there was obtained 0.32 g of 2-(3-butenyl)-2-(1-(4-chlorophenyl)-2-methylpropyl)malononitrile (compound 26).
- Yield: 32%;
- nD 25.5: 1.5217.
- Using 0.20 g of (4-(trifluoromethoxy)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 50 mg of sodium hydride (60% in oil), and 0.19 ml of 1-bromo-3-methyl-2-butene, and according to the process described in Production Example 1, there was obtained 0.19 g of 2-(3-methyl-2-butenyl)-2-(4-(trifluoromethoxy)benzyl)malononitrile (compound 27).
- Yield: 74%;
- nD 24.5: 1.4707.
- Using 0.50 g of (3-methoxybenzyl)malononitrile, 10 ml of N,N-dimethylformamide, 0.12 g of sodium hydride (60% in oil), and 1.1 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.45 g of 2-allyl-2-(3-methoxybenzyl)malononitrile (compound 28).
- Yield: 74%;
- nD 22.0: 1.5238.
- Using 0.50 g of (4-methoxybenzyl)malononitrile, 10 ml of N,N-dimethylformamide, 0.12 g of sodium hydride (60% in oil), and 1.1 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.50 g of 2-allyl-2-(4-methoxybenzyl)malononitrile (compound 29).
- Yield: 83%;
- nD 22.0: 1.5252.
- First, 0.24 g of (4-(trifluoromethoxy)benzylidene)malononitrile, 0.66 g of allyltributyltin, and 0.71 g of methyl iodide were dissolved in 10 ml of benzene, and the solution was heated to the reflux temperature. Then, 40 mg of azobis(isobutyronitrile) was added, and the mixture was stirred for 13 hours, while heating under reflux. The reaction mixture is poured into a mixture of 40 ml of hexane and 40 ml of acetonitrile, followed by phase separation. The acetonitrile layer was concentrated, and the resulting residue was subjected to silica gel thin layer chromatography to give 0.19 g of 2-allyl-2-(1-(4-(trifluoromethoxy)phenyl)ethyl)malononitrile (compound 30).
- Yield: 65%;
-
- Using 0.24 g of (4-(trifluoromethoxy)benzylidene)malononitrile, 10 ml of benzene, 0.66 g of allyltributyltin, 0.89 g of chloroiodomethane, and 66 mg of azobis(isobutyronitrile), and according to the process described in Production Example 30, there was obtained 0.20 g of 2-allyl-2-(1-(4-(trifluoromethoxy)phenyl)-2-chloroethyl)malononitrile (compound 31).
- Yield: 61%;
-
- Using 0.50 g of (1-(4-(trifluoromethoxy)phenyl)-2-propenyl)malononitrile, 4 ml of N,N-dimethylformamide, 83 mg of sodium hydride (60% in oil), and 0.51 g of 4-bromo-1-butene, and according to the process described in Production Example 1, there was obtained 0.56 g of 2-(3-butenyl)-2-(1-(4-(trifluoromethoxy)phenyl)-2-propenyl)malononitrile (compound 32).
- Yield: 93%;
-
- Using 0.25 g of (1-(4-(trifluoromethoxy)phenyl)-2-propenyl)malononitrile, 2 ml of N,N-dimethylformamide, 42 mg of sodium hydride (60% in oil), and 0.45 g of allyl bromide, and according to the process described in Production Example 1, there was obtained 0.25 g of 2-allyl-2-(1-(4-(trifluoromethoxy)phenyl)-2-propenyl)malononitrile (compound 33).
- Yield: 87%;
-
- Using 0.62 g of (1-(4-(trifluoromethoxy)phenyl)-2-propenyl)malononitrile, 5 ml of N,N-dimethylformamide, 103 mg of sodium hydride (60% in oil), and 0.56 g of 3-bromo-1-propyne, and according to the process described in Production Example 1, there was obtained 0.59 g of 2-(2-propynyl)-2-(1-(4-(trifluoromethoxy)phenyl)-2-propenyl)malononitrile (compound 34).
- Yield: 83%;
-
- First, 0.41 g of 2-(3-butenyl)-2-(4-hydroxybenzyl)malononitrile and 0.76 g of dibromodifluoromethane was dissolved in 5 ml of N,N-dimethylformamide, and while stirring under ice-cooling, 80 mg of sodium hydride (60% in oil) was added, and the mixture was heated to 80° C., followed by stirred for 5 hours. Then, a saturated ammonium chloride aqueous solution was added to the reaction mixture, which was extracted diethyl ether. The organic layer was successively washed with water, a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.16 g of 2-(3-butenyl)-2-(4-(bromodifluoromethoxy)benzyl)malononitrile (compound 35) as a low-polar compound.
- Yield: 25%;
- m.p.: 50.2° C.
- Also given was 58 mg of 2-(3-butenyl)-2-(4-(difluoromethoxy)benzyl)malononitrile (compound 36) as a high-polar compound.
- Yield: 12%;
-
- Using 0.43 g of (3,4-(methylenedioxy)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 100 mg of sodium hydride (60% in oil), and 0.36 g of 4-bromo-1-butene, and according to the process described in Production Example 1, there was obtained 0.42 g of 2-(3-butenyl)-2-(3,4-(methylenedioxy)benzyl)malononitrile (compound 37).
- Yield: 76%;
-
- First, 0.30 g of 2-(3-butenyl)-2-(4-hydroxybenzyl)malononitrile and 0.19 g of allyl bromide was dissolved in 5 ml of N,N-dimethylformamide, and 0.22 g of potassium carbonate was added, followed by stirred overnight at room temperature. Then, water was added to the reaction mixture, which was extracted diethyl ether. The organic layer was successively washed with water, a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.34 g of 2-(3-butenyl)-2-(4-(2-propenyloxy)benzyl)malononitrile (compound 38).
- Yield: 96%;
- m.p.: 77.7° C.
- First, 0.48 g of 4-(trifluoromethoxy)benzylidenemalononitrile, 0.10 g of tetrakis(triphenylphosphine)palladium, and 0.26 g of allylmethyl carbonate were dissolved in 20 ml of tetrahydrofuran, and the solution was stirred at room temperature for 10 hours. Then, the residue obtained by concentration under reduced pressure was subjected to silica gel chromatography to give 0.56 g of 2-allyl-2-(4-(trifluoromethoxy)-α-methoxybenzyl)malononitrile (compound 39).
- Yield: 89%;
-
- Using 0.50 g of (4-(trifluoromethylthio)benzyl)malononitrile, 6 ml of N,N-dimethylformamide, 90 mg of sodium hydride (60% in oil), and 0.29 g of allyl bromide, and according to the process described in Production Example 1, there was obtained 0.49 g of 2-allyl-2-(4-(trifluoromethylthio)benzyl)malononitrile (compound 41).
- Yield: 84%;
-
- Using 0.50 g of (4-(trifluoromethylthio)benzyl)malononitrile, 6 ml of N,N-dimethylformamide, 90 mg of sodium hydride (60% in oil), and 0.32 g of 4-bromo-1-butene, and according to the process described in Production Example 1, there was obtained 0.26 g of 2-(3-butenyl)-2-(4-(trifluoromethylthio)benzyl)malononitrile (compound 42).
- Yield: 44%;
-
- Using 0.51 g of 4-(trifluoromethylthio)benzylidenemalononitrile, 0.10 g of tetrakis(triphenylphosphine)palladium, 0.26 g of allylmethyl carbonate, and 20 ml of tetrahydrofuran, and according to the process described in Production Example 38, there was obtained 0.49 g of 2-allyl-2-(4-(trifluoromethylthio)-α-methoxybenzyl)malononitrile (compound 43).
- Yield: 75%;
-
- Using 1.76 g of (4-ethoxybenzyl)malononitrile, 30 ml of N,N-dimethylformamide, 0.40 g of sodium hydride (60% in oil), and 4.2 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.30 g of 2-allyl-2-(4-ethoxybenzyl)malononitrile (compound 44).
- Yield: 54%;
- m.p.: 84.3° C.
- Using 0.50 g of (4-(trifluoromethoxy)benzyl)malononitrile, 6 ml of N,N-dimethylformamide, 95 mg of sodium hydride (60% in oil), and 0.47 g of isopentyl bromide, and according to the process described in Production Example 1, there was obtained 0.42 g of 2-(3-methylbutyl)-2-(4-(trifluoromethoxy)benzyl)malononitrile (compound 45).
- Yield: 65%;
-
- Using 0.50 g of (4-(trifluoromethylthio)benzyl)malononitrile, 6 ml of N,N-dimethylformamide, 90 mg of sodium hydride (60% in oil), and 0.21 g of 1-chloro-2-butene, and according to the process described in Production Example 1, there was obtained 0.40 g of 2-(2-butenyl)-2-(4-(trifluoromethylthio)benzyl)malononitrile (compound 46).
- Yield: 66%;
-
- Using 0.50 g of (4-(trifluoromethylthio)benzyl)malononitrile, 6 ml of N,N-dimethylformamide, 90 mg of sodium hydride (60% in oil), and 0.21 g of 3-chloro-1-butene, and according to the process described in Production Example 1, there was obtained 0.14 g of 2-(1-methyl-2-propenyl)-2-(4-(trifluoromethylthio)benzyl)malononitrile (compound 47).
- Yield: 24%;
-
- Using 1.93 g of (1-(3-chlorophenyl)-1-methylethyl)malononitrile, 30 ml of N,N-dimethylformamide, 0.39 g of sodium hydride (60% in oil), and 3.70 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.14 g of 2-allyl-2-(1-(3-chlorophenyl)-1-methylethyl)malononitrile (compound 48).
- Yield: 50%;
- m.p.: 84.3° C.
- Using 0.60 g of (1-(2-chlorophenyl)-1-methylethyl)malononitrile, 10 ml of N,N-dimethylformamide, 0.12 g of sodium hydride (60% in oil), and 1.2 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.60 g of 2-allyl-2-(1-(2-chlorophenyl)-1-methylethyl)malononitrile (compound 49).
- Yield: 71%;
- nD 23.5: 1.5398.
- Using 2.01 g of (4-nitrobenzyl)malononitrile, 50 ml of N,N-dimethylformamide, 0.44 g of sodium hydride (60% in oil), and 4.23 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.13 g of 2-allyl-2-(4-nitrobenzyl)malononitrile (compound 50).
- Yield: 47%;
- m.p.: 94.2° C.
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.12 g of sodium hydride (60% in oil), and 0.27 ml of isopropyl iodide, and according to the process described in the Production Example 1, there was obtained 0.19 g of 2-(4-chlorobenzyl)-2-isopropylmalononitrile (compound 51).
- Yield: 31%;
- nD 22.5: 1.5229.
- Using 0.50 g of (4-(trifluoromethyl)benzyl)malononitrile, 21 ml of N,N-dimethylformamide, 100 mg of sodium hydride (60% in oil), and 0.45 g of 4-bromo-1-butene, and according to the process described in Production Example 1, there was obtained 0.25 g of 2-(3-butenyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 52).
- Yield: 20%;
-
- Using 2.25 g of (2,3-dichlorobenzyl)malononitrile, 20 ml of N,N-dimethylformamide, 0.48 g of sodium hydride (60% in oil), and 1.30 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.72 g of 2-allyl-2-(2,3-dichlorobenzyl)malononitrile (compound 53).
- Yield: 65%;
- nD 23.5: 1.5448.
- Using 2.25 g of (2,6-dichlorobenzyl)malononitrile, 20 ml of N,N-dimethylformamide, 0.48 g of sodium hydride (60% in oil), and 1.30 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 2.00 g of 2-allyl-2-(2,6-dichlorobenzyl)malononitrile (compound 54).
- Yield: 75%;
- nD 23.5: 1.5483.
- First, 0.50 g of 4-(trifluoromethylthio)benzylidenemalononitrile, 60 mg of tris(dibenzylideneacetone)dipalladium-chloroform complex, and 0.11 g of 1,1′-bis(diphenylphosphino)ferrocene were added to 10 ml of tetrahydrofuran, and 0.30 g of allyl chloride and 0.39 g of trimethylsilyl cyanide were further added under an atmosphere of nitrogen, followed by stirring at 75° C. for a day. The reaction mixture was then filtered through silica gel and the filtrate was concentrated. The residue was subjected to silica gel chromatography to give 0.42 g of 2-allyl-2-(4-(trifluoromethylthio)-α-cyanobenzyl)malononitrile (compound 56).
- Yield: 67%;
-
- Using 0.47 g of 4-(trifluoromethoxy)benzylidenemalononitrile, 60 mg of tris(dibenzylideneacetone)dipalladium-chloroform complex, 0.11 g of 1,1′-bis(diphenylphosphino)ferrocene, 10 ml of tetrahydrofuran, 0.30 g of allyl chloride, and 0.39 g of trimethylsilyl cyanide, and according to the process described in Production Example 53, there was obtained 0.42 g of 2-allyl-2-(4-(trifluoromethoxy)-α-cyanobenzyl)malononitrile (compound 55).
- Yield: 70%;
-
- Using 0.30 g of allylmalononitrile, 4 ml of N,N-dimethylformamide, 130 mg of sodium hydride (60% in oil), and 0.99 g of 2,4-bis(trifluoromethyl)benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.70 g of 2-allyl-2-(2,4-bis(trifluoromethyl)benzyl)malononitrile (compound 57).
- Yield: 72%;
-
- Using 0.30 g of allylmalononitrile, 4 ml of N,N-dimethylformamide, 125 mg of sodium hydride (60% in oil), and 0.85 g. of 2-chloro-4-(trifluoromethyl)benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.40 g of 2-allyl-2-(2-chloro-4-(trifluoromethyl)benzyl)malononitrile (compound 58).
- Yield: 47%;
-
- Using 0.50 g of (4-(trifluoromethoxy)benzyl)malononitrile, 3 ml of N,N-dimethylformamide, 93 mg of sodium hydride (60% in oil), and 0.42 g of 1-bromo-2-butyne, and according to the process described in Production Example 1, there was obtained 0.47 g of 2-(2-butynyl)-2-(4-(trifluoromethoxy)benzyl)malononitrile (compound 59).
- Yield: 70%;
-
- Using 0.30 g of (3-butenyl)malononitrile, 5 ml of N,N-dimethylformamide, 110 mg of sodium hydride (60% in oil), and 0.75 g of 2-chloro-4-(trifluoromethyl)benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.30 g of 2-(3-butenyl)-2-(2-chloro-4-(trifluoromethyl)benzyl)malononitrile (compound 60).
- Yield: 39%;
-
- Using 0.60 g of allylmalononitrile, 8 ml of N,N-dimethylformamide, 255 mg of sodium hydride (60% in oil), and 1.55 g of 4-(methylsulfonyl)benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.64 g of 2-allyl-2-(4-(methylsulfonyl)benzyl)malononitrile (compound 61).
- Yield: 41%;
-
- Using 1.23 g of (2,3,4,5,6-pentafluorobenzyl)malononitrile, 20 ml of N,N-dimethylformamide, 0.24 g of sodium hydride (60% in oil), and 0.63 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.98 g of 2-allyl-2-(2,3,4,5,6-pentafluorobenzyl)malononitrile (compound 62).
- Yield: 68%;
- m.p.: 78.2° C.
- Using 0.15 g of allylmalononitrile, 5 ml of N,N-dimethylformamide, 62 mg of sodium hydride (60% in oil), and 0.43 g of 2-nitro-4-(trifluoromethyl)benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.32 g of 2-allyl-2-(2-nitro-4-(trifluoromethyl)benzyl)malononitrile (compound 63).
- Yield: 70%;
-
- Using 0.15 g of allylmalononitrile, 5 ml of N,N-dimethylformamide, 62 mg of sodium hydride (60% in oil), and 0.44 g of 2,6-dichloro-4-(trifluoromethyl)benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.20 g of 2-allyl-2-(2,6-dichloro-4-(trifluoromethyl)benzyl)malononitrile (compound 64).
- Yield: 43%;
-
- Using 0.15 g of (3-butenyl)malononitrile, 5 ml of N,N-dimethylformamide, 55 mg of sodium hydride (60% in oil), and 0.39 g of 2,6-dichloro-4-(trifluoromethyl)benzyl bromide, and according to the process described in Production Example 1, there was obtained 95 mg of 2-(3-butenyl)-2-(2,6-dichloro-4-(trifluoromethyl)benzyl)malononitrile (compound 65).
- Yield: 22%;
-
- Using 0.41 g of (1-(3-chlorophenyl)-2-methylpropyl)malononitrile, 5 ml of N,N-dimethylformamide, 85 mg of sodium hydride (60% in oil), and 0.22 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.35 g of 2-allyl-2-(1-(3-chlorophenyl)-2-methylpropyl)malononitrile (compound 66).
- Yield: 73%;
- nD 23.0: 1.5267.
- Using 97 mg of (3-butenyl)malononitrile, 5 ml of N,N-dimethylformamide, 37 mg of sodium hydride (60% in oil), and 0.25 g of 2-nitro-4-(trifluoromethyl)benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.12 g of 2-(3-butenyl)-2-(2-nitro-4-(trifluoromethyl)benzyl)malononitrile (compound 67).
- Yield: 43%;
-
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.16 g of sodium hydride (60% in oil), and 0.33 ml of methyl iodide, and according to the process described in the Production Example 1, there was obtained 0.23 g of 2-(4-chlorobenzyl)-2-methylmalononitrile (compound 68).
- Yield: 43%;
- m.p.: 91.1° C.
- Using 0.30 g of allylmalononitrile, 4 ml of N,N-dimethylformamide, 124 mg of sodium hydride (60% in oil), and 0.80 g of 3-fluoro-4-(trifluoromethyl)benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.37 g of 2-allyl-2-(3-fluoro-4-(trifluoromethyl)benzyl)malononitrile (compound 69).
- Yield: 46%;
-
- Using 0.30 g of allylmalononitrile, 6 ml of N,N-dimethylformamide, 124 mg of sodium hydride (60% in oil), and 0.68 g of 4-(methylthio)benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.42 g of 2-allyl-2-(4-(methylthio)benzyl)malononitrile (compound 70).
- Yield: 62%;
-
- Using 0.50 g of (4-(trifluoromethyl)benzyl)malononitrile, 6 ml of N,N-dimethylformamide, 98 mg of sodium hydride (60% in oil), and 0.41 g of 1-iodopropane, and according to the process described in Production Example 1, there was obtained 0.21 g of 2-propyl-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 71).
- Yield: 41%;
-
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.16 g of sodium hydride (60% in oil), and 0.39 ml of ethyl bromide, and according to the process described in the Production Example 1, there was obtained 0.20 g of 2-(4-chlorobenzyl)-2-ethylmalononitrile (compound 72).
- Yield: 35%;
- m.p.: 70.9° C.
- Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.16 g of sodium hydride (60% in oil), and 0.85 g of (Z)-1-bromo-3-hexene, and according to the process described in the Production Example 1, there was obtained 0.22 g of 2-(4-chlorobenzyl)-2-((Z)-3-hexenyl)malononitrile (compound 73).
- Yield: 31%;
- m.p.: 44.8° C.
- Using 0.56 g of (1-(4-chlorophenyl)ethyl)malononitrile, 5 ml of N,N-dimethylformamide, 160 mg of sodium hydride (60% in oil), and 0.46 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.29 g of 2-allyl-2-(1-(4-chlorophenyl)ethyl)malononitrile (compound 74).
- Yield: 43%;
- nD 25.5: 1.5294.
- Using 0.50 g of (4-(trifluoromethyl)benzyl)malononitrile, 6 ml of N,N-dimethylformamide, 98 mg of sodium hydride (60% in oil), and 0.27 g of bromoethane, and according to the process described in Production Example 1, there was obtained 0.33 g of 2-ethyl-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 75).
- Yield: 58%;
-
- Using 0.56 g of (1-(4-chlorophenyl)ethyl)malononitrile, 5 ml of N,N-dimethylformamide, 160 mg of sodium hydride (60% in oil), and 0.65 ml of 1-bromo-4-pentene, and according to the process described in the Production Example 1, there was obtained 0.25 g of 2-(1-(4-chlorophenyl)ethyl)-2-(4-pentenyl)malononitrile (compound 76).
- Yield: 33%;
- nD 25.5: 1.5204.
- Using 0.50 g of (4-methylbenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.18 g of sodium hydride (60% in oil), and 0.50 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.37 g of 2-allyl-2-(4-methylbenzyl)malononitrile (compound 77).
- Yield: 60%;
- m.p.: 74.5° C.
- First, 0.40 g of 2-(3-butenyl)-2-(4-hydroxybenzyl)malononitrile and 0.22 g of acetic anhydride was dissolved in 5 ml of toluene, to which 0.23 g of triethylamine was added, followed by stirring overnight at room temperature. Then, water was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was successively washed with a saturated ammonium chloride aqueous solution, a saturated sodium bicarbonate aqueous solution, a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.45 g of 2-(3-butenyl)-2-(4-(acetyloxy)benzyl)malononitrile (compound 78).
- Yield: 95%;
- m.p.: 80.2° C.
- Using 0.50 g of (4-(trifluoromethyl)benzyl)malononitrile, 10 ml of N,N-dimethylformamide, 89 mg of sodium hydride (60% in oil), and 0.33 g of 5-bromo-1-pentene, and according to the process described in Production Example 1, there was obtained 0.16 g of 2-(4-pentenyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 79).
- Yield: 25%;
-
- First, 0.40 g of 2-(3-butenyl)-2-(4-hydroxybenzyl)malononitrile was dissolved in 5 ml of N,N-dimethylformamide, to which 75 mg of sodium hydride (60% in oil) was added, while stirring under ice cooling. After the evolution of hydrogen gas ceased, while stirring under ice cooling, 0.49 g of 1,1,2,2-tetrafluoro-1-iodoethane was added dropwise, followed by further stirring at room temperature overnight. Then, a saturated ammonium chloride aqueous solution was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was successively washed with water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 82 mg of 2-(3-butenyl)-2-(4-(1,1,2,2-tetrafluoroethoxy)benzyl)malononitrile (compound 80).
- Yield: 14%;
- m.p.: 60.5° C.
- Using 0.40 g of 2-(3-butenyl)-2-(4-hydroxybenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 75 mg of sodium hydride (60% in oil), and 0.45 g of 2,2,2-trifluoro-1-iodoethane, and according to the process described in the Production Example 78, there was obtained 70 mg of 2-(3-butenyl)-2-(4-(2,2,2-trifluoroethoxy)benzyl)malononitrile (compound 81).
- Yield: 13%;
- m.p.: 58.0° C.
- First, 0.48 g of (4-(trifluoromethoxy)benzyliden)malononitrile and 1.0 g of ethanol was dissolved in 20 ml of tetrahydrofuran, to which 0.10 g of tetrakis(triphenylphosphine)palladium and 0.26 g of allyl methyl carbonate was added, followed by further stirring for 10 hours at room temperature. Then, the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.65 g of 2-allyl-2-(4-(trifluoromethoxy)-α-ethoxybenzyl)malononitrile (compound 82).
- Yield: 99%;
-
- Using 0.36 g of (4-cyanobenzyliden)malononitrile, 0.10 g of tetrakis(triphenylphosphine)palladium, and 0.26 g of allyl methyl carbonate, and 20 ml of tetrahydrofuran, and according to the process described in the Production Example 38, there was obtained 0.11 g of 2-allyl-2-(4-cyano-α-methoxybenzyl)malononitrile (compound 83).
- Yield: 22%;
-
- Using 0.38 g of (4-chlorobenzyliden)malononitrile, 0.10 g of tetrakis(triphenylphosphine)palladium, and 0.26 g of allyl methyl carbonate, and 20 ml of tetrahydrofuran, and according to the process described in the Production Example 38, there was obtained 0.44 g of 2-allyl-2-(4-chloro-α-methoxybenzyl)malononitrile (compound 84).
- Yield: 84%;
-
- Using 0.41 g of (2,2-dimethylpropyl)malononitrile, 7 ml of N,N-dimethylformamide, 0.13 g of sodium hydride (60% in oil), and 0.92 g of 4-(trifluoromethyl)benzyl bromide, and according to the process described in the Production Example 1, there was obtained 0.59 g of 2-(2,2-dimethylpropyl)-2-(4-(trifluoromethoxy)benzyl)malononitrile (compound 85).
- Yield: 63%;
-
- Using 1.36 g of (2,2-dimethylpropyl)malononitrile, 20 ml of N,N-dimethylformamide, 0.43 g of sodium hydride (60% in oil), and 3.00 g of 4-bromobenzyl bromide, and according to the process described in the Production Example 1, there was obtained 2.74 g of 2-(4-bromobenzyl)-2-(2,2-dimethylpropyl)malononitrile (compound 86).
- Yield: 90%;
-
- Using 0.50 g of (4-(trifluoromethoxy)benzyl)malononitrile, 8 ml of N,N-dimethylformamide, 96 mg of sodium hydride (60% in oil), and 0.57 g of isobytyl bromide, and according to the process described in the Production Example 1, there was obtained 0.31 g of 2-isobutyl-2-(4-(trifluoromethoxy)benzyl)malononitrile (compound 87).
- Yield: 51%;
-
- Using 0.50 g of (4-(trifluoromethoxy)benzyl)malononitrile, 8 ml of N,N-dimethylformamide, 96 mg of sodium hydride (60% in oil), and 0.63 g of pentyl bromide, and according to the process described in the Production Example 1, there was obtained 0.45 g of 2-pentyl-2-(4-(trifluoromethoxy)benzyl)malononitrile (compound 88).
- Yield: 70%;
-
- Using 0.50 g of (3-(trifluoromethoxy)benzyl)malononitrile, 20 ml of N,N-dimethylformamide, 92 mg of sodium hydride (60% in oil), and 0.38 g of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.54 g of 2-allyl-2-(3-(trifluoromethoxy)benzyl)malononitrile (compound 89).
- Yield: 93%;
-
- Using 0.50 g of (3-(trifluoromethoxy)benzyl)malononitrile, 20 ml of N,N-dimethylformamide, 92 mg of sodium hydride (60% in oil), and 420 mg of 4-bromo-1-butene, and according to the process described in the Production Example 1, there was obtained 0.28 g of 2-(3-butenyl)-2-(3-(trifluoromethoxy)benzyl)malononitrile (compound 90).
- Yield: 46%;
-
- First, 1.0 g of (4-methoxybenzylidene)malononitrile was dissolved in 30 ml of tetrahydrofuran, to which 0.57 g of trimethylsilyl cyanide was added at room temperature under a atmosphere of nitrogen, followed by stirred for 30 minutes. Then, 5.5 ml of tetrabutylammonium fluoride (1.0 M solution of tetrahydrofuran) was added dropwise to the mixture under ice-cooling, followed by stirred for 4 hours keeping ice-cooling. Then, 0.98 g of allyl bromide was added dropwise followed by stirring overnight at room temperature. Then, a saturated ammonium chloride aqueous solution was added to the reaction mixture, which was extracted diethyl ether. The organic layer was successively washed with water, a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.0 g of 2-allyl-2-(4-methoxy-α-cyanobenzyl)malononitrile (compound 91).
- Yield: 76%;
-
- Using 1.0 g of (4-methylbenzyliden)malononitrile, 30 ml of tetrahydrofuran, 0.62 g of trimethylsilyl cyanide, 6.0 ml of tetrabutylammonium fluoride (1.0 M solution of tetrahydrofuran), and 1.08 g of allyl bromide, and according to the process described in the Production Example 89, there was obtained 1.0 g of 2-allyl-2-(4-methyl-α-cyanobenzyl)malononitrile (compound 92).
- Yield: 76%;
-
- Using 0.50 g of (4-(methoxycarbonyl)benzylidene)malononitrile, 70 mg of tris(dibenzylideneacetone)dipalladium-chloroform complex, 0.14 g of 1,1′-bis(diphenylphosphino)ferrocene, 12 ml of tetrahydrofuran, and 0.37 g of allyl chloride, and according to the process described in the Production Example 53, there was obtained 0.31 g of 2-allyl-2-(4-(methoxycarbonyl)-α-cyanobenzyl)malononitrile (compound 93).
- Yield: 48%;
-
- Using 0.3 g of (3-butenyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.72 g of 3,5-bis(trifluoromethyl)benzyl bromide, and according to the process described in the Production Example 1, there was obtained 0.12 g of 2-(3,5-bis(trifluoromethyl)benzyl)-2-(3-butenyl)malononitrile (compound 94).
- Yield: 14%;
-
- First, 0.72 g of 2,3-dimethoxybenzyl bromide was dissolved in 3 ml of N,N-dimethylformamide, to which a suspension 0.05 g of sodium hydride (60% in oil) and 0.3 g of allylmalononitrile in 2 ml of N,N-dimethylformamide was added dropwise, while stirring under ice cooling, followed by further stirring at 0° C. for 4 hours. Then, 10% hydrochloric acid was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was successively washed with water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.34 g of 2-allyl-2-(2,3-dimethoxybenzyl)malononitrile (compound 95).
- Yield: 46%;
-
- Using 0.47 g of 4-vinylbenzyl chloride, 5 ml of N,N-dimethylformamide, 0.13 g of sodium hydride (60% in oil), and 0.3 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.22 g of 2-allyl-2-(4-vinylbenzyl)malononitrile (compound 96).
- Yield: 35%;
-
- Using 0.40 g of 4-acetylbenzyl chloride, 5 ml of N,N-dimethylformamide, 0.08 g of sodium hydride (60% in oil), and 0.2 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.25 g of 2-(4-acetylbenzyl)-2-allylmalononitrile (compound 97).
- Yield: 56%;
-
- Using 0.3.0 g of 2-(3-butenyl)-2-(4-hydroxybenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 60 mg of sodium hydride (60% in oil), and 0.18 g of ethyl bromide, and according to the process described in the Production Example 78, there was obtained 255 mg of 2-(3-butenyl)-2-(4-ethoxybenzyl)malononitrile (compound 98).
- Yield: 75%;
-
- Using 0.30 g of 2-(3-butenyl)-2-(4-hydroxybenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 60 mg of sodium hydride (60% in oil), and 0.28 g of propyl iodide, and according to the process described in the Production Example 78, there was obtained 215 mg of 2-(3-butenyl)-2-(4-propoxybenzyl)malononitrile (compound 99).
- Yield: 60%;
-
- Using 0.30 g of 2-(3-butenyl)-2-(4-hydoroxybenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 60 mg of sodium hydride (60% in oil), and 0.21 g of isopropyl bromide, and according to the process described in the Production Example 78, there was obtained 227 mg of 2-(3-butenyl)-2-(4-isopropoxybenzyl)malononitrile (compound 100).
- Yield: 64%;
-
- Using 0.72 g of 4-ethylbenzyl chloride, 5 ml of N,N-dimethylformamide, 0.19 g of sodium hydride (60% in oil), and 0.5 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.48 g of 2-allyl-2-(4-ethylbenzyl)malononitrile (compound 101).
- Yield: 57%;
-
- Using 0.79 g of 4-isopropylbenzyl chloride, 5 ml of N,N-dimethylformamide, 0.19 g of sodium hydride (60% in oil), and 0.5 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.57 g of 2-allyl-2-(4-isopropylbenzyl)malononitrile (compound 102).
- Yield: 62%;
-
- Using 0.72 g of (4-(trifluoromethoxy)benzyliden)malononitrile, 20 ml of benzene, 1.99 g of allyl tributyl tin, 0.20 g of azobis(isobutyronitrile) and 2.76 g of 1,1-dimethylethyl iodide, and according to the process described in the Production Example 30, there was obtained 0.20 g of 2-allyl-2-(1-(4-(trifluoromethoxy)phenyl)-2,2-dimethylpropyl)malononitrile (compound 103).
- Yield: 61%;
- nD 20.5: 1.4762.
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of 1-bromopentane, and according to the process described in the Production Example 1, there was obtained 0.12 g of 2-pentyl-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 104).
- Yield: 46%;
-
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of 1-bromo-3-methylbutane, and according to the process described in the Production Example 1, there was obtained 0.14 g of 2-(3-methylbutyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 105).
- Yield: 54%;
-
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of 1-bromo-3-methyl-2-butene, and according to the process described in the Production Example 1, there was obtained 0.18 g of 2-(3-methyl-2-butenyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 106).
- Yield: 68%;
-
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.14 g of 1-bromo-2-butene, and according to the process described in the Production Example 1, there was obtained 0.18 g of 2-(2-butenyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 107).
- Yield: 74%;
-
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.14 g of 3-bromo-2-methylpropen, and according to the process described in the Production Example 1, there was obtained 0.20 g of 2-(2-methyl-2-propenyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 108).
- Yield: 71%;
-
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.14 g of 1-bromobutane, and according to the process described in the Production Example 1, there was obtained 0.16 g of 2-butyl-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 109).
- Yield: 57%;
-
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.14 g of 1-bromo-2-methylpropane, and according to the process described in the Production Example 1, there was obtained 0.13 g of 2-(2-methylpropyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 110).
- Yield: 46%;
-
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of 2-bromobutane, and according to the process described in the Production Example 1, there was obtained 0.07 g of 2-(1-methylpropyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 111).
- Yield: 25%;
-
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of 2-bromopentane, and according to the process described in the Production Example 1, there was obtained 0.09 g of 2-(1-methylbutyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 112).
- Yield: 30%;
-
- Using 0.23 g of (4-(trifluoromethyl)benzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.17 g of 2-bromohexane, and according to the process described in the Production Example 1, there was obtained 0.07 g of 2-(1-methylpentyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (compound 113).
- Yield: 21%;
-
- Using 0.54 g of 2,3-difluorobenzyl bromide, 5 ml of N,N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.28 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.31 g of 2-allyl-2-(2,3-difluorobenzyl)malononitrile (compound 114).
- Yield: 52%;
-
- Using 0.69 g of (4-(2-butyloxy))benzyl bromide, 5 ml of N,N-dimethylformamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.31 g of 2-allyl-2-(4-(2-butyloxy)benzyl)malononitrile (compound 115).
- Yield: 40%;
-
- Using 0.80 g of 4-fluoro-3-phenoxybenzyl bromide, 5 ml of N,N-dimethylformamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.32 g of 2-allyl-2-(4-fluoro-3-phenoxybenzyl)malononitrile (compound 116).
- Yield: 37%;
-
- Using 0.70 g of 4-(p-tolylthio)benzyl chloride, 5 ml of N,N-dimethylformamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.38 g of 2-allyl-2-(4-(p-tolylthio)benzyl)malononitrile (compound 117).
- Yield: 37%;
-
- Using 0.74 g of 3-phenoxybenzyl bromide, 5 ml of N,N-dimethylformamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.54 g of 2-allyl-2-(3-phenoxybenzyl)malononitrile (compound 118).
- Yield: 67%;
-
- Using 0.66 g of 4-(m-tolyloxy)benzyl bromide, 5 ml of N,N-dimethylformamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.38 g of 2-allyl-2-(4-(m-tolyloxy)benzyl)malononitrile (compound 119).
- Yield: 45%;
-
- Using 0.30 g of (2,4,6-trifluorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.06 g of sodium hydride (60% in oil), and 0.17 g of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.21 g of 2-allyl-2-(2,4,6-trifluorobenzyl)malononitrile (compound 120).
- Yield: 59%;
-
- Using 0.84 g of 4-(4-chlorophenoxy)benzyl bromide, 5 ml of N,N-dimethylformamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.50 g of 2-allyl-2-(4-(p-chlorophenoxy)benzyl)malononitrile (compound 121).
- Yield: 55%;
-
- The following will describe some production examples for intermediate compounds as reference production examples.
-
- was dissolved in 20 ml of diethyl ether, to which a catalytic amount of copper (I) iodide was added, and while stirring under ice cooling, a solution of methyl magnesium iodide in diethyl ether (prepared from 0.30 g of magnesium, 10 ml of diethyl ether, and 0.86 ml of methyl iodide) was added dropwise, followed by stirring for 30 minutes under ice cooling. Then, 10% hydrochloric acid was added to the reaction mixture, which was extracted with ethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.74 g of (1-(4-chlorophenyl)-1-methylethyl)malononitrile (the intermediate (2)).
- Yield: 69%. REFERENCE PRODUCTION EXAMPLE 2
- First, 1.02 g of (4-chlorobenzylidene)malononitrile was dissolved in 20 ml of tetrahydrofuran, to which a catalytic amount of copper (I) iodide was added, and while stirring under ice cooling, a solution of isopropyl magnesium bromide in tetrahydrofuran (prepared from 0.34 g of magnesium, 10 ml of tetrahydrofuran, and 1.46 ml of isopropyl bromide) was added dropwise, followed by stirring for 30 minutes under ice cooling. Then, 10% hydrochloric acid was added to the reaction mixture, which became acidic and was extracted with ethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.66 g of (1-(4-chlorophenyl)-2-methylpropyl)malononitrile (the intermediate (3)).
- Yield: 52%.
- First, 4.44 g of (4-(trifluoromethyl)benzylidene)malononitrile was dissolved in 20 ml of ethanol, and while stirring at room temperature, a suspension of 0.19 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room-temperature for 30 minutes. Then, 10% hydrochloride acid was added to the reaction mixture, which became acidic and was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.30 g of (4-(trifluoromethyl)benzyl)malononitrile (the intermediate (4)).
- Yield: 51%.
- First, 3.00 g of (4-chloro-α-methylbenzylidene)malononitrile was dissolved in 20 ml of ethanol, and while stirring at room temperature, a suspension of 0.15 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloride acid was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.70 g of (1-(4-chlorophenyl)ethyl)malononitrile (the intermediate (6)).
- Yield: 56%.
- First, 10.0 g of 4-(trifluoromethoxy)benzaldehyde and 3.50 g of malononitrile were dissolved in 60 ml of 70% (w/w) aqueous ethanol, to which a catalytic amount of benzyltrimethylammonium hydroxide was added, and the mixture was stirred at room temperature overnight. Then, a saturated aqueous sodium chloride solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from t-butyl methyl ether and hexane to give 9.24 g of (4-(trifluoromethoxy)benzylidene)malononitrile.
- Yield: 74%;
-
- Then, 2.61 g of (4-(trifluoromethoxy)benzylidene)malononitrile was dissolved in 20 ml of tetrahydrofuran, and while stirring at room temperature, a suspension of 0.11 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloric acid was added, and the mixture was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.20 g of (4-(trifluoromethoxy)benzyl)malononitrile (the intermediate (7)).
- Yield: 83%.
- Using 1.19 g of (4-(trifluoromethoxy)benzylidene)malononitrile, 20 ml of tetrahydrofuran, a catalytic amount of copper (I) iodide, and a solution of isopropyl magnesium bromide in tetrahydrofuran (prepared from 0.39 g of magnesium, 10 ml of tetrahydrofuran, and 2.36 g of isopropyl bromide), and according to the process described in Reference Production Example 2, there was obtained 0.77 g of (1-(4-(trifluoromethoxy)phenyl)-2-methylpropyl)malononitrile (the intermediate (8)).
- Yield: 55%.
- Using 1.19 g of (4-(trifluoromethoxy)benzylidene)malononitrile, 20 ml of tetrahydrofuran, a catalytic amount of copper (I) iodide, and 12.5 ml of a solution of methyl magnesium bromide in tetrahydrofuran (about 1 M, available from Tokyo Kasei Kogyo Co., Ltd), and according to the process described in Reference Production Example 2, there was obtained 0.76 g of (1-(4-(trifluoromethoxy)phenyl)ethyl)malononitrile (the intermediate (10)).
- Yield: 60%.
- First, 4.46 g of (3,4-dichlorobenzylidene)malononitrile was dissolved in 20 ml of tetrahydrofuran, and while stirring at room temperature, a suspension of 0.19 g of sodium borohydride in 5 ml of ethanol was added drop-wise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloride acid was added and the mixture was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 3.15 g of (3,4-dichlorobenzyl)malononitrile (the intermediate (12)).
- Yield: 70%.
- Using 4.46 g of (2,4-dichlorobenzylidene)malononitrile, 20 ml of tetrahydrofuran, and a suspension of 0.19 g of sodium borohydride in 5 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 3.10 g of (2,4-dichlorobenzyl)malononitrile (the intermediate (13)).
- Yield: 69%.
- First, 10.0 g of 4-(trifluoromethylthio)benzaldehyde and 2.92 g of malononitrile were dissolved in 50 ml of 70% (w/w) aqueous ethanol, to which a catalytic amount of benzyltrimethylammonium hydroxide was added, and the mixture was stirred at room temperature overnight. Then, a saturated aqueous sodium chloride solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized with a solvent system consisting of t-butyl methyl ether and hexane to give 10.5 g of (4-(trifluoromethylthio)benzylidene)malononitrile.
- Yield: 85%;
-
- Then, 8.00 g of (4-(trifluoromethylthio)benzylidene)malononitrile and 3.35 g of benzaldehyde were dissolved in 320 ml of ethanol, and while stirring at room temperature, 3.41g of phenylenediamine was slowly added, and the mixture was stirred at room temperature for 5 hours. Then, the reaction mixture was concentrated, 300 ml of t-butyl methyl ether was added, and insoluble matters were filtered. The filtrate was concentrated and the resulting residue was subjected to silica gel chromatography to give 6.22 g of (4-(trifluoromethylthio)benzyl)malononitrile (the intermediate (14)).
- Yield: 77%.
- First, 9.78 g of malononitrile, 954 mg of tetrabutylammonium bromide, and 10.0 g of 4-bromo-1-butene were mixed, and while stirring at 0° C. under an atmosphere of nitrogen, 8.3 g of potassium t-butoxide was slowly added. The mixture was further stirred at room temperature for 12 hours. Then, the reaction mixture was poured into water, followed by extraction with t-butyl methyl ether. The organic layer was washed with water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.31 g of (3-butenyl)malononitrile (the intermediate (16)).
- Yield: 26%.
- Using 4.00 g of (4-(trifluoromethoxy)benzylidene)malononitrile, 30 ml of tetrahydrofuran, 175 mg of copper (I) bromide dimethyl sulfide complex, and 26 ml of a solution (0.98 M) of vinyl magnesium bromide in tetrahydrofuran, and according to the process described in Reference Production Example 2, there was obtained 1.60 g of (1-(4-trifluoromethoxyphenyl))-2-propenylmalononitrile (the intermediate (18)).
- Using 5.00 g of (2-methoxybenzylidene)malononitrile, 40 ml of tetrahydrofuran, and a suspension of 0.31 g of sodium borohydride in 10 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 3.56 g of (2-methoxybenzyl)malononitrile (the intermediate (20)).
- Yield: 70%.
- First, 9.18 g of (4-hydroxybenzyl)malononitrile was dissolved in 90 ml of N,N-dimethylformamide, to which 2.56 g of sodium hydride (60% in oil) was added, while stirring under ice cooling. After the evolution of hydrogen gas ceased, while stirring under ice cooling, 7.21 g of 4-bromo-1-betene was added dropwise, followed by further stirring at room temperature overnight. Then, a saturated aqueous ammonium chloride solution was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was successively washed with water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 10.3 g of 2-(3-butenyl)-2-(4-hydroxybenzyl)malononitrile (the intermediate (23)).
- Yield: 86%.
- Using 5.23 g of (4-ethoxybenzylidene)malononitrile, 40 ml of tetrahydrofuran, and a suspension of 0.35 g of sodium borohydride in 10 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 2.76 g of (4-ethoxybenzyl)malononitrile (the intermediate (25)).
- Yield: 52%.
-
- 60 ml of diethyl ether, a catalytic amount of copper (I) iodide, and methyl magnesium iodide in diethyl ether (prepared from 0.90 g of magnesium, 30 ml of diethyl ether, and 2.58 ml of methyl iodide), and according to the process described in Reference Production Example 1, there was obtained 2.33 g of (1-(3-chlorophenyl)-1-methylethyl)malononitrile (the intermediate (26)).
- Yield: 73%.
-
- 60 ml of diethyl ether, a catalytic amount of copper (I) iodide, and methyl magnesium iodide in diethyl ether (prepared from 0.90 g of magnesium, 30 ml of diethyl ether, and 2.58 ml of methyl iodide), and according to the process described in Reference Production Example 1, there was obtained 1.16 g of (1-(2-chlorophenyl)-1-methylethyl)malononitrile (the intermediate (27)).
- Yield: 36%.
- Using 4.46 g of (2,3-dichlorobenzylidene)malononitrile, 20 ml of tetrahydrofuran, and a suspension of 0.21 g of sodium borohydride in 5 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 3.07 g of (2,3-dichlorobenzyl)malononitrile (the intermediate (29)).
- Yield: 68%.
- Using 4.46 g of (2,6-dichlorobenzylidene)malononitrile, 20 ml of tetrahydrofuran, and a suspension of 0.21 g of sodium borohydride in 5 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 2.73 g of (2,6-dichlorobenzyl)malononitrile (the intermediate (30)).
- Yield: 61%.
- Using 4.88 g of (2,3,4,5,6-pentafluorobenzylidene)malononitrile, 20 ml of tetrahydrofuran, and a suspension of 0.21 g of sodium borohydride in 5 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 2.20 g of (2,3,4,5,6-pentafluorobenzyl)malononitrile (the intermediate (31)).
- Yield: 45%.
- Using 1.02 g of (3-chlorobenzylidene)malononitrile, 20 ml of tetrahydrofuran, a catalytic amount of copper (I) iodide, and 10 ml of isopropyl magnesium bromide in tetrahydrofuran (1.4 M), and according to the process described in Reference Production Example 2, there was obtained 0.71 g of (1-(3-chlorophenyl)-2-methylpropyl)malononitrile (the intermediate (32)).
- Yield: 56%.
- First, 13.2 g of (2,2-dimethylpropylidene)malononitrile and 10.5 g of benzaldehyde was dissolved in 800 ml of ethanol, to which 10.6 g of 1,2-phenylenediamine was added slowly while stirring, followed by stirring overnight at room temperature. Then, the reaction mixture was concentrated under reduced pressure. Then, 300 ml of chloroform was added to the residue, the precipitate was filtered off, the filtrate was concentrated. And the same operation was repeated once more. The residue was subjected to silica gel column chromatography to give 8.50 g of (2,2-dimethylpropyl)malononitrile (the intermediate (34)).
- Yield: 64%.
- The intermediate compounds used in the production of the compounds are shown below with the compound numbers and physical data.
- Intermediate (1)
-
- m.p.: 96.9° C.
- Intermediate (2)
-
- nD 22.0: 1.5372.
- Intermediate (3)
-
- nD 21.5: 1.5289.
- Intermediate (4)
-
- m.p.: 79.1° C.
- Intermediate (5)
-
- m.p.: 118.7° C.
- Intermediate (6)
-
- nD 24.5: 1.5349.
- Intermediate (7)
-
- m.p.: 88.3° C.
- Intermediate (8)
-
-
- Intermediate (9)
-
- m.p.: 97.7° C.
- Intermediate (10)
-
-
- Intermediate (11)
-
- m.p.: 117.2° C.
- Intermediate (12)
-
- m.p.: 83.3° C.
- Intermediate (13)
-
- m.p.: 62.5° C.
- Intermediate (14)
-
-
- Intermediate (15)
-
-
- Intermediate (16)
-
-
- Intermediate (17)
-
- nD 19.5: 1.5384.
- Intermediate (18)
-
-
- Intermediate (19)
-
- nD 19.5:1.5403.
- Intermediate (20)
-
- nD 19.5: 1.5248.
- Intermediate (21)
-
- m.p.: 55.5° C.
- Intermediate (22)
-
- m.p.: 89.6° C.
- Intermediate (23)
-
-
- Intermediate (24)
-
-
- Intermediate (25)
-
- m.p.: 118.0° C.
- Intermediate (26)
-
- nD 22.5: 1.5376.
- Intermediate (27)
-
- m.p.: 90.2° C.
- Intermediate (28)
-
- m.p.: 155.7° C.
- Intermediate (29)
-
- nD 22.5: 1.5518.
- Intermediate (30)
-
- m.p.: 87.7° C.
- Intermediate (31)
-
- m.p.: 96.3° C.
- Intermediate (32)
-
- nD 21.5: 1.5268.
- Intermediate (33)
-
- m.p.: 83.7° C.
- Intermediate (34)
-
-
- Intermediate (35)
-
-
- Specific examples of the compounds (X) are shown in Table 1 with their compound numbers.
TABLE 1 The compounds of formula (X): (X) No. R1 R2 R3 R4 (R5)m R6 1 H H H CH═CH2 — Cl 2 CH3 CH3 H CH═CH2 — Cl 3 H CH(CH3)2 H CH═CH2 — Cl 4 H H H CH2CH═CH2 — Cl 5 H H H CH═CH2 — CF3 6 H H H CH2CH═CH2 — CN 7 H H H (CH2)2CH═CH2 — CN 8 H H H CH═CH2 2-Cl H 9 H H CH2CH2CH2CH2CH2 — Cl 10 H CH3 H CH2CH═CH2 — Cl 11 H H H CH═CH2 — OCF3 12 H CH(CH3)2 H CH2CH═CH2 — OCF3 13 H H H CHCH2 — Br 14 H H H CH═CH2 — CN 15 H H H CH2CH═CH2 — OCF3 16 H CH3 H CH2CH═CH2 — OCF3 17 H H H CH═CH2 3-Cl H 18 H H H CH═CH2 — F 19 H H H CH(CH3)2 — Cl 20 H H H CH═CH2 2-OCH3 H 21 H H H (CH2)2CH═CH2 — Cl 22 H H CH3 CH═CH2 — Cl 23 H H H CH═CH2 3-Cl Cl 24 H H H CH═CH2 2-Cl Cl 25 H H H CH═C(CH3)2 — Cl 26 H CH(CH3)2 H CH2CH═CH2 — Cl 27 H H H CH═C(CH3)2 — OCF3 28 H H H CH═CH2 3-OCH3 H 29 H H H CH═CH2 — OCH3 30 H CH3 H CH═CH2 — OCF3 31 H CH2Cl H CH═CH2 — OCF3 32 H CH═CH2 H CH2CH═CH2 — OCF3 33 H CH═CH2 H CH═CH2 — OCF3 34 H CH═CH2 H C≡CH — OCF3 35 H H H CH2CHCH2 — OCBrF2 36 H H H CH2CH═CH2 — OCHF2 37 H H H CH2CH═CH2 — 3,4-OCH2O 38 H H H CH2CH═CH2 — OCH2CH═CH2 39 H OCH3 H CH═CH2 — OCF3 40 H OCH2CF3 H CH═CH2 — OCF3 41 H H H CH═CH2 — SCF3 42 H H H CH2CH═CH2 — SCF3 43 H OCH3 H CH═CH2 — SCF3 44 H H H CH═CH2 — OCH2CH3 45 H H H CH2CH(CH3)2 — OCF3 46 H H H CH═CHCH3 — SCF3 47 H H CH3 CH═CH2 — SCF3 48 CH3 CH3 H CH═CH2 3-Cl H 49 CH3 CH3 H CH═CH2 2-Cl H 50 H H H CH═CH2 — NO2 51 H H CH3 CH3 — Cl 52 H H H CH2CH═CH2 — CF3 53 H H H CH═CH2 2,3-Cl2 — 54 H H H CH═CH2 2,6-Cl2 55 H CN H CH═CH2 — OCF3 56 H CN H CH═CH2 — SCF3 57 H H H CH═CH2 2-CF3 CF3 58 H H H CH═CH2 2-Cl CF3 59 H H H C≡CCH3 — OCF3 60 H H H CH2CH-CH2 2-Cl CF3 61 H H H CH═CH2 — S(O)2CH3 62 H H H CH═CH2 2,3,5,6-F4 F 63 H H H CH═CH2 2-NO2 CF3 64 H H H CH═CH2 2,6-Cl2 CF3 65 H H H CH2CH═CH2 2,6-Cl2 CF3 66 H CH(CH3)2 H CH═CH2 3-Cl H 67 H H H CH2CH═CH2 2-NO2 CF3 68 H H H H — Cl 69 H H H CH═CH2 3-F CF3 70 H H H CH═CH2 — SCH3 71 H H H C2H5 — CF3 72 H H H CH3 — Cl 73 H H H (Z)-CH2CH═CHCH2CH3 — Cl 74 H CH3 H CH═CH2 — Cl 75 H H H CH3 — CF3 76 H CH3 H CH2CH2CH═CH2 — Cl 77 H H H CH═CH2 — — CH3 78 H H H CH2CH═CH2 — OC(═O)CH3 79 H H H (CH2)2CH═CH2 — CF3 80 H H H CH2CH═CH2 — OCF2CF2H 81 H H H CH2CH═CH2 — OCH2CF3 82 H OCH2CH3 H CH═CH2 — OCF3 83 H OCH3 H CH═CH2 — CN 84 H OCH3 H CH═CH2 — Cl 85 H H H C(CH3)3 — OCF3 86 H H H C(CH3)3 — Br 87 H H H CH(CH3)2 — OCF3 88 H H H CH2CH2CH2CH3 — OCF3 89 H H H CH═CH2 3-OCF3 H 90 H H H CH2CH═CH2 3-OCF3 H 91 H CN H CH═CH2 — OCH3 92 H CN H CH═CH2 — CH3 93 H CN H CH═CH2 — C(═O)OCH3 94 H H H CH2CH═CH2 3,5-(CF3)2 H 95 H H H CH═CH2 2,3-(OCH3)2 H 96 H H H CH═CH2 — CH═CH2 97 H H H CH═CH2 — C(═O)CH3 98 H H H CH2CH═CH2 — OCH2CH3 99 H H H CH2CH═CH2 OCH2CH2CH3 100 H H H CH2CH═CH2 — OCH(CH3)2 101 H H H CH═CH2 — CH2CH3 102 H H H CH═CH2 — CH(CH3)2 103 H C(CH3)3 H CH═CH2 — OCF3 104 H H H CH2CH2CH2CH3 — CF3 105 H H H CH2CH(CH3)2 — CF3 106 H H H CH═C(CH3)2 — CF3 107 H H H CH═CHCH3 — CF3 108 H H H C(CH3)═CH2 — CF3 109 H H H CH2CH2CH3 — CF3 110 H H H CH(CH3)2 — CF3 111 H H CH3 CH2CH3 — CF3 112 H H CH3 CH2CH2CH3 — CF3 113 H H CH3 CH2CH2CH2CH3 — CF3 114 H H H CH═CH2 2,3-F2 H 115 H H H CH═CH2 — OCH(CH3)CH2CH3 116 H H H CH═CH2 3-OPh F 117 H H H CH═CH2 — S(p-CH3Ph) 118 H H H CH═CH2 3-OPh H 119 H H H CH═CH2 — O(m-CH3Ph) 120 H H H CH═CH2 2,6-F2 F 121 H H H CH═CH2 — O(p-ClPh) 122 H H H CH2CH(CH3)2 3-Cl Cl 123 H H H CH2CH(CH3)2 — Cl 124 H H H CH2CH(CH3)2 — CN 125 H H H CH2CH(CH3)2 — NO2 126 H H H CH2CH(CH3)2 3-F CF3 127 H H H CH2CH(CH3)2 3-Cl CN 128 H CH3 H CH2CH(CH3)2 — CF3 129 H CH3 H CH2CH(CH3)2 — Cl 130 H CH3 H CH2CH(CH3)2 — CN 131 H CH(CH3)2 H CH2CH(CH3)2 — CF3 132 H H H CH2CH(CH3)2 3-CF3 H 133 H H H CH2CH(CH3)2 — CF3 134 CH3 CH3 H CH2CH(CH3)2 — CN 135 CH3 CH3 H CH2CH(CH3)2 3-Cl Cl 136 H H H CH2C(CH3)3 — CF3 137 H H H CH2C(CH3)3 — Cl 138 H H H CH2C(CH3)3 — CN 139 H H H CH2C(CH3)3 — NO2 140 H H H CH2C(CH3)3 3-Cl CF3 141 H H H CH2C(CH3)3 3-F CN 142 H CH3 H CH2C(CH3)3 — CF3 143 H CH3 H CH2C(CH3)3 3-F CF3 144 H CH(CH3)2 H CH2C(CH3)3 3-F CF3 145 H CH(CH3)2 H CH2C(CH3)3 — CF3 146 H H H CH2C(CH3)3 3-F Cl 147 H H H CH2C(CH3)3 3-Cl F 148 H H H CH═CH2 3-Cl CF3 149 H CH3 H CH═CH2 3-F CF3 150 H H H CH═CH2 3-CF3 H 151 H H H CH═CH2 3-Cl CN 152 H H H CH2CH═CH2 3-Cl CF3 153 H H H CH2CH═CH2 3-F CF3 154 H H H CH2CH═CH2 3-F CN 155 H H H CH2CH═CH2 3-Cl F 156 H CH3 H CH2CH═CH2 3-F Cl 157 H CH3 H CH═C(CH3)2 3-F Cl 158 H H H CH═C(CH3)2 3-Cl CF3 159 H H H CH═C(CH3)2 3-F CF3 160 H CH(CH3)2 H CH═C(CH3)2 — CF3 161 H H H CH═C(CH3)2 3-CF3 H 162 H H H CH2CH═C(CH3)2 — CF3 163 H H H CH2CH═C(CH3)2 — CN 164 H H H CH2CH═C(CH3)2 — NO2 165 H H H CH2CH3 3-F CF3 166 H H H CH2CH3 — CN 167 H H H CH2CH3 — Cl 168 H H H CH2CH3 — NO2 169 H CH3 H CH2CH3 — CF3 170 H CH3 H CH2CH3 — CN 171 H H H CH2CH2CH3 3-F Cl 172 H H H CH2CH2CH3 3-Cl F 173 H H H CH2CH2CH3 3-F CF3 174 H CH3 H CH2CH2CH3 3-CF3 H 175 H H H CH2CH3 3-CF3 H 176 H H H CH2CH2CH3 3-CF3 H 177 H CH2F H CH2CH═CH2 — CF3 178 H H H CH2CH2CH3 — SCF3 179 H H H CH2CH3 — OCF3 180 H CF3 H CH2CH3 3-F CF3 - The following will describe some formulation examples wherein parts represent parts by weight. The compounds (X) are designated by their compound numbers shown in Table 1.
- Nine (9) parts of each of compounds 1 to 120 is dissolved in 37.5 parts of xylene and 37.5 parts of dimethylformamide, and 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added thereto, followed by well stirring and mixing, to give an emulsifiable concentrate for each compound.
- To 40 parts of each of compounds 1 to 120 is added 5 parts of Sorpol® 5060 (Toho Chemical Industry Co., Ltd.), followed by well mixing, and 32 parts of Carplex® #80 (synthetic hydrated silicone oxide fine powder; Shionogi & Co., Ltd.) and 23 parts of 300 mesh diatomaceous earth are added, which is mixed with a mixer to give a wettable powder for each compound.
- To 3 parts of each of compounds 1 to 120 are added 5 parts of synthetic hydrated silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite, and 57 parts of clay, followed by well stirring and mixing, and an appropriate amount of water is added to this mixture, followed by further stirring, granulation with a granulator, and air drying, to give a granule for each compound.
- First, 4.5 parts of each of compounds 1 to 120, 1 part of synthetic hydrated silicon oxide fine powder, 1 part of Doriresu B (Sankyo Co., Ltd.) as a flocculant, and 7 parts of clay are well mixed with a mortar, followed by stirring and mixing with a mixer. To the resulting mixture is added 86.5 parts of cut clay, followed by well stirring and mixing, to give a dust for each compound.
- Ten parts of each of compounds 1 to 120, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water are mixed and pulverized by the wet grinding method to give a formulation for each compound.
- First, 0.5 parts of each of compounds 1 to 120 is dissolved in 10 parts of dichloromethane, which is mixed with 89.5 parts of ISOPAR® M (isoparaffin; Exxon Chemical Co.) to give an oil formulation for each compound.
- First, 0.1 parts of compounds 1 to 120 and 49.9 parts of NEO-CHIOZOL (Chuo Kasei K. K.) are put into an aerosol can, to which an aerosol valve is attached. Then, 25 parts of dimethyl ether and 25 parts of LPG are filled in the aerosol can, followed by shaking and attachment of an actuator, to give an oil-based aerosol.
- First, 0.6 parts of each of compounds 1 to 120, 0.01 parts of BHT, 5 parts of xylene, 3.39 parts of deodorized kerosine, and 1 part of an emulsifier (Atmos 300; Atmos Chemical Co.) are mixed to become a solution. Then, this solution and 50 parts of distilled water are filled in an aerosol can, to which a valve part is attached, and 40 parts of a propellant (LPG) is filled under pressure through the valve in the aerosol can to give a water-based aerosol.
- The following test example will demonstrate that the compounds (X) are useful as the active ingredients of pesticide compositions. The compounds (X) are designated by their compound numbers shown in Table 1.
- Each formulation of the compound 11, 12, 16, 27, 30, 31, 32, 33, 34, 37, 40, 41, 42, 47, 49, 52, 56, 58, 59, 60, 63, 64, 65, 67, 69, 71, 75, 79, 87, 88, 89, 90, 98, 100, 102, 105, 106, 108, 109, 110, 114, 115, 116, 117, 118 and 119 obtained according to Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.
- Fifty grams of molding Bonsoru 2 (available from Sumitomo Chemical Co., Ltd.) was put into a polyethylene cup, and 10 to 15 seeds of rice were planted in the polyethylene cup. Then rice plants were grown until the second foliage leaves developed and then cut into the same height of 5 cm. The test liquid, which had been prepared as described above, was sprayed at the rate of 20 ml/cup onto these rice plants. After the test liquid sprayed onto the rice plants were dried, the polyethylene cup with the rice plants was placed in a large polyethylene cup and 30 first-instar larvae ofNilaparvata lugens (brown planthopper) were set free in the large polyethylene cup, which was then kept covered and left in a greenhouse at 25° C. On the 6th day after the release of larvae of Nilaparvata lugens, the number of parasitic Nilaparvata lugens on the rice plants was examined.
- As a result, in the treatment with each of the compounds described above, the number of parasitic pests on the 6th day after the treatment was not greater than 3.
- Each formulation of the compound 11, 12, 16, 41, 45, 47, 49, 52, 54, 58, 68, 69, 71, 75, 87, 90, 105, 106, 108, 109 and 110 obtained according to Formulation Example 5 was diluted with water so that the active ingredient concentration came to 45.5 ppm to prepare a test liquid for each compound.
- Fifty grams of molding Bonsoru 2 (available from Sumitomo Chemical Co., Ltd.) was put into a polyethylene cup having five holes of 5 mm, and 10 to 15 seeds of rice were planted in the polyethylene cup. Then rice plants were grown until the second foliage leaves developed and the polyethylene cup with the rice plants was placed in a large polyethylene cup containing 55 ml of the test liquid, which had been prepared as described above. The rice plants were left in a greenhouse at 25° C. for 6 days and then cut into the same height of 5 cm. Thirty first-instar larvae ofNilaparvata lugens (brown planthoppers) were set free in the large polyethylene cup, which was then kept covered and left in a greenhouse at 25° C. On the 6th day after the release of larvae of Nilaparvata lugens, the number of parasitic Nilaparvata lugens on the rice plants was examined.
- As a result, in the treatment with each of the compounds described above, the number of parasitic pests on the 6th day after the treatment was not greater than 3.
- Each formulation of the compound 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 25, 26, 27, 29, 44, 48, 49, 51, 62, 66, 73, 74, 76 and 77 obtained according to Formulation Example 1 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.
- A bundle of 3 to 4 of cotyledons (height of 3 to 5 cm) of rice was immersed in the test liquid, which had been prepared as described above, for 1 minute. After the test liquid treated the rice plants was dried, a filter paper moistened with 1 ml of water was place on a bottom of polyethylene cup and then the bundle of cotyledons of rice was placed on it. Thirty first-instar larvae ofNilaparvata lugens (brown planthoppers) were set free in the polyethylene cup, which was then kept covered and left in a greenhouse at 25° C. On the 6th day after the release of larvae of Nilaparvata lugens, the number of parasitic Nilaparvata lugens on the rice plants was examined.
- As a result, in the treatment with each of the compounds described above, the number of parasitic pests on the 6th day after the treatment was not greater than 3.
- Each formulation of the compound 1, 2, 3, 4, 5, 9, 10, 11, 12, 16, 19, 21, 22, 23, 24, 26, 66, 74 and 76 obtained according to Formulation Example 1 was diluted with water so that the active ingredient concentration came to 50 ppm to prepare a test liquid for each compound.
- On the bottom of a polyethylene cup of 5 cm in diameter was placed a filter paper, to which the test liquid had been prepared as described above, was added dropwise in an amount of 1 ml. One germinated seed of corn and 30 to 50 eggs ofDiabrotica undecimpunctata (southern-corn rootworm) was placed on the filter paper in the polyethylene cup, which was then kept covered and left in a room at 25° C. On the 6th day after, the number of surviving larvae of Diabrotica undecimpunctata was examined.
- As a result, in the treatment with each of the compounds described above, the number of surviving pests on the 6th day after was 0.
- Each formulation of the compound 1, 3, 4, 10, 11, 15, 17, 22, 24, 30, 31, 32, 33, 34, 35, 36, 37, 39, 40, 41, 42, 43, 45, 46, 47, 52, 55, 56, 57, 58, 59, 60, 64, 65, 66, 67, 68, 69, 71, 74, 75, 79, 82, 84, 89, 90, 92, 101, 102, 105, 107, 108, 109, 110, 111, 114, 115 and 120 obtained according to Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.
- On the bottom of a polyethylene cup of 5.5 cm in diameter was placed a filter paper on the same size, to which the test liquid had been prepared as described above, was added dropwise in an amount of 0.7 ml, and 30 mg of sucrose as a bait was placed on it. Ten female adults ofMusca domestics (house fly) were set free in the polyethylene cup, which was then kept covered. After 24 hours, their survival was examined to determine the mortality.
- As a result, in the treatment with each of the compounds described above, it was exhibited the mortality of 100%.
- Each formulation of the compound 1, 2, 3, 4, 5, 9, 10, 11, 12, 15, 16, 17, 23, 30, 31, 32, 33, 36, 39, 40, 41, 42, 43, 46, 47, 52, 55, 56, 57, 58, 59, 60, 64, 68, 69, 74, 79, 84, 89, 102, 109, 110, 114, 119, 120 and 121 obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.
- On the bottom of a polyethylene cup of 5.5 cm in diameter was placed a filter paper on the same size, to which the test liquid had been prepared as described above, was added dropwise in an amount of 0.7 ml, and 30 mg of sucrose as a bait was placed on it. Two male adults of German cockroach (Blattalla germanica) were set free in the polyethylene cup, which was then kept covered. After 6 days, their survival was examined to determine the mortality.
- As a result, in the treatment with each of the compounds described above, it was exhibited the mortality of 100%.
- Each formulation of the compound 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 15, 16, 17, 19, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 52, 54, 55, 56, 57, 58, 59, 60, 61, 63, 64, 65, 66, 67, 68, 69, 70, 71, 74, 75, 76, 78, 79, 80, 81, 82, 83, 84, 89, 91, 92, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 115, 116, 118 and 121 obtained according to Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.
- In 100 ml of ion-exchanged water, the test liquid had been prepared as described above, was added dropwise in an amount of 0.7 ml (the concentration of active ingredient was 3.5 ppm). Twenty final-instar larvae ofCullex pipiens pallens (common mosquito) were set free in the solution. After 1 days, their survival was examined to determine the mortality. As a result, in the treatment with each of the compounds described above, it was exhibited the mortality of 100%.
- The present invention makes it possible to effectively control pests such as insect pests, acarine pests, and nematode pests.
Claims (10)
1. A pesticide composition comprising a malononitrile compound of formula (X):
wherein R1 and R2 are the same or different and independently C1-C5 (halo)alkyl, C1-C5 (halo)alkyloxy, C2-C5 (halo)alkenyl, C2-C5 (halo)alkynyl, hydrogen, or cyano;
R3 and R4 are the same or different and independently C1-C10 alkyl, C2-C1 alkenyl, C2-C10 alkynyl, or hydrogen, or R3 and R4 are taken together to form C2-C6 (halo)alkylene or C4-C6 (halo)alkenylene;
R5 is halogen, cyano, nitro, C1-C4 (halo)alkyl, C2-C4 (halo)alkenyl, C2-C4 (halo)alkynyl, C1-C4 (halo)alkyloxy, C1-C4 (halo)alkylthio, C1-C4 (halo)alkylsulfinyl, C1-C4 (halo)alkylsulfonyl, C1-C4 (halo)alkylcarbonyl, C1-C4 (halo)alkyloxycarbonyl, C1-C4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C1-C3 alkyl;
n is an integer of 0 to 4;
R6 is hydrogen, halogen, cyano, nitro, C1-C4-(halo)alkyl, C2-C4 (halo)alkenyl, C2-C4 (halo)alkynyl, C1-C4 (halo)alkyloxy, C1-C4 (halo)alkylthio, C1-C4 (halo)alkylsulfinyl, C1-C4 (halo)alkylsulfonyl, C1-C4 (halo)alkylcarbonyl, C1-C4 (halo)alkyloxycarbonyl, C1-C4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C1-C3 alkyl;
or R5 and R6 are taken together to form methylenedioxy;
with the provisos that when R6 is hydrogen, then n is an integer of 1 to 4 and that when n is 2 or more, then R5's are the same or different from each other; as an active ingredient, and a carrier.
2. The pesticide composition according to claim 1 , wherein a containing amount of the malononitrile compound is 0.1% to 95% by weight.
3. A pest controlling method comprising applying an pesticidally effective amount of a malononitrile compound of formula (X):
wherein R1 and R2 are the same or different and independently C1-C5 (halo)-alkyl, C1-C5 (halo)alkyloxy, C2-C5 (halo)alkenyl, C2-C5 (halo)alkynyl, hydrogen, or cyano;
R3 and R4 are the same or different and independently C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, or hydrogen, or R1 and R4 are taken together to form C2-C6 (halo)alkylene or C4-C6 (halo)alkenylene;
R5 is halogen, cyano, nitro, C1-C4 (halo)alkyl, C2-C4 (halo)alkenyl, C2-C4 (halo)alkynyl, C1-C4 (halo)alkyloxy, C1-C4 (halo)alkylthio, C1-C4 (halo)alkylsulfinyl, C1-C4 (halo)alkylsulfonyl, C1-C4 (halo)alkylcarbonyl, C1-C4 (halo)alkyloxycarbonyl, C1-C4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C1-C3 alkyl;
n is an integer of 0 to 4;
R6 is hydrogen, halogen, cyano, nitro, C1-C4 (halo)alkyl, C2-C4 (halo)alkenyl, C2-C4 (halo)alkynyl, C1-C4 (halo)alkyloxy, C1-C4 (halo)alkylthio, C1-C4 (halo)alkylsulfinyl, C1-C4 (halo)alkylsulfonyl, C1-C4 (halo)alkylcarbonyl, C1-C4 (halo)alkyloxycarbonyl, C1-C4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C1-C3 alkyl;
or R5 and R6 are taken together to form methylenedioxy;
with the provisos that when R6 is hydrogen, then n is an integer of 1 to 4 and that when n is 2 or more, then R5's are the same or different from each other; to pests or habitats of pests.
4. The pest controlling method according to claim 3 , wherein R6 is halogen, cyano, nitro, C1-C4 haloalkyl, C1-C4 haloalkyloxy or C1-C4 haloalkylthio.
5. The pest controlling method according to claim 3 , wherein R3 and R4 are the same or different and independently C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, or hydrogen, or R3 and R4 are taken together to form C2-C6 (halo)alkylene.
6. The pest controlling method according to claim 3 , wherein R1 and R2 are both hydrogen.
7. The pest controlling method according to claim 3 , wherein R1 and R2 are the same or different and independently C1-C3 (halo)alkyl, C1-C3 (halo)alkyloxy, C2-C4 (halo)alkenyl, C2-C4 (halo)alkynyl, hydrogen, or cyano; R5 and R6 are the same or different and independently halogen, cyano, nitro, C1-C3 haloalkyl, C1-C8 haloalkyloxy, C1-C3 (halo)alkylthio, C1-C3 (halo)alkylsulfinyl, C1-C3 (halo)alkylsulfonyl, C1-C3 (halo)alkylcarbonyl, or C1-C3 haloalkyloxycarbonyl.
8. The pest controlling method according to claim 7 , wherein R3 is hydrogen and R4 are vinyl, allyl, ethyl, 3-butenyl and 1-propenyl.
9. The pest controlling method according to claim 3 , wherein the pests are insect pests.
10. Use of a malononitrile compound of formula (X):
wherein R1 and R2 are the same or different and independently C1-C5 (halo)alkyl, C1-C5 (halo)alkyloxy, C2-C5 (halo)alkenyl, C2-C5 (halo)alkynyl, hydrogen, or cyano;
R3 and R4 are the same or different and independently C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, or hydrogen, or R3 and R4 are taken together to form C2-C6 (halo)alkylene or C4-C6 (halo)alkenylene;
R5 is halogen, cyano, nitro, C1-C4 (halo)alkyl, C2-C4 (halo)alkenyl, C2-C4 (halo)alkynyl, C1-C4 (halo)alkyloxy, C1-C4 (halo)alkylthio, C1-C4 (halo)alkylsulfinyl, C1-C4 (halo)alkylsulfonyl, C1-C4 (halo)alkylcarbonyl, C1-C4 (halo)alkyloxycarbonyl, C1-C4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C1-C3 alkyl;
n is an integer of 0 to 4;
R6 is hydrogen, halogen, cyano, nitro, C1-C4 (halo)alkyl, C2-C4 (halo)alkenyl, C2-C4 (halo)alkynyl, C1-C4 (halo)alkyloxy, C1-C4 (halo)alkylthio, C1-C4 (halo)alkylsulfinyl, C1-C4 (halo)alkylsulfonyl, C1-C4 (halo)alkylcarbonyl, C1-C4 (halo)alkyloxycarbonyl, C1-C4 (halo)alkylcarbonyloxy, phenyloxy, or phenylthio, in which the phenyloxy and phenylthio groups may optionally be substituted with halogen or C1-C3 alkyl;
or R5 and R6 are taken together to form methylenedioxy;
with the provisos that when R6 is hydrogen, then n is an integer of 1 to 4 and that when n is 2 or more, then R5's are the same or different from each other; as an active ingredient of a pesticide composition.
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US10/476,979 Abandoned US20040142821A1 (en) | 2001-05-09 | 2002-05-08 | Pesticide composition comprising malononitrile compounds |
US11/107,853 Expired - Fee Related US7402691B2 (en) | 2001-05-09 | 2005-04-18 | Malononitrile compounds and their use as pesticides |
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US10/477,120 Abandoned US20040143007A1 (en) | 2001-05-09 | 2002-05-08 | Malononitrile compounds and their use as pesticides |
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EP (3) | EP1385817B1 (en) |
JP (3) | JP4269574B2 (en) |
KR (3) | KR100858268B1 (en) |
CN (4) | CN100584823C (en) |
AR (3) | AR034427A1 (en) |
AU (1) | AU2002255313B2 (en) |
BR (3) | BR0209532B1 (en) |
CA (1) | CA2446006A1 (en) |
DE (1) | DE60230131D1 (en) |
ES (1) | ES2316557T3 (en) |
HU (1) | HUP0400033A3 (en) |
IL (3) | IL158499A0 (en) |
MY (1) | MY134029A (en) |
RU (3) | RU2003135637A (en) |
SA (2) | SA02230096B1 (en) |
TW (1) | TWI223979B (en) |
WO (3) | WO2002090320A2 (en) |
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Cited By (10)
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US20040138065A1 (en) * | 2001-05-09 | 2004-07-15 | Ken Otaka | Malononitrile compounds and their use as pesticides |
US20040143007A1 (en) * | 2001-05-09 | 2004-07-22 | Ken Otaka | Malononitrile compounds and their use as pesticides |
US20050209323A1 (en) * | 2001-05-09 | 2005-09-22 | Ken Otaka | Malononitrile compounds and their use as pesticides |
US7011838B2 (en) * | 2001-05-09 | 2006-03-14 | Sumitomo Chemical Company, Limited | Malononitrile compounds and their use as pesticides |
US7402691B2 (en) | 2001-05-09 | 2008-07-22 | Sumitomo Chemical Company, Limited | Malononitrile compounds and their use as pesticides |
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US7541374B2 (en) | 2004-01-16 | 2009-06-02 | Sumitomo Chemical Company, Limited | Malononitrile compounds and use thereof |
US20090149425A1 (en) * | 2004-01-16 | 2009-06-11 | Hiromasa Mitsudera | Malononitrile compound as pesticides |
US7846956B2 (en) | 2004-01-16 | 2010-12-07 | Sumitomo Chemical Company, Limited | Malononitrile compound as pesticides |
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Owner name: SUMITOMO CHEMICAL COMPANY, LIMITED, JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:OTAKA, KEN;SUZUKI, MASAYA;OOHIRA, DAISUKE;REEL/FRAME:015131/0691;SIGNING DATES FROM 20031014 TO 20031015 |
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