JP4403096B2 - 殺虫作用を有する新規アゾール類 - Google Patents
殺虫作用を有する新規アゾール類 Download PDFInfo
- Publication number
- JP4403096B2 JP4403096B2 JP2005111638A JP2005111638A JP4403096B2 JP 4403096 B2 JP4403096 B2 JP 4403096B2 JP 2005111638 A JP2005111638 A JP 2005111638A JP 2005111638 A JP2005111638 A JP 2005111638A JP 4403096 B2 JP4403096 B2 JP 4403096B2
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- Prior art keywords
- spp
- formula
- methyl
- 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.)
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- 230000000749 insecticidal effect Effects 0.000 title description 3
- 150000003851 azoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 140
- 239000000203 mixture Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 239000003085 diluting agent Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 230000000802 nitrating effect Effects 0.000 claims description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- XLTUPERVRFLGLJ-UHFFFAOYSA-N isothiocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=S XLTUPERVRFLGLJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
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- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
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- -1 C 1 -C 4 -alkyl Chemical group 0.000 description 101
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- 239000011230 binding agent Substances 0.000 description 11
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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- 239000003995 emulsifying agent Substances 0.000 description 8
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
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- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- BFIWQSSAMKDRRZ-UHFFFAOYSA-N 2,4-bis(4-phenoxyphenyl)-2,4-bis(sulfanylidene)-1,3,2$l^{5},4$l^{5}-dithiadiphosphetane Chemical compound S1P(=S)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)SP1(=S)C(C=C1)=CC=C1OC1=CC=CC=C1 BFIWQSSAMKDRRZ-UHFFFAOYSA-N 0.000 description 7
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- 150000003839 salts Chemical class 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
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- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- WHMZYGMQWIBNOC-UHFFFAOYSA-N propan-2-yl n-(3,4-dimethoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)C)C=C1OC WHMZYGMQWIBNOC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 210000003689 pubic bone Anatomy 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- WJSXSXUHWBSPEP-UHFFFAOYSA-N pyridine;triphenylborane Chemical compound C1=CC=NC=C1.C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 WJSXSXUHWBSPEP-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000010453 quartz Substances 0.000 description 1
- MRUMAIRJPMUAPZ-UHFFFAOYSA-N quinolin-8-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CN=C2C(O)=CC=CC2=C1 MRUMAIRJPMUAPZ-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004223 radioprotective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 description 1
- 229960002245 selamectin Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- KHDSWONFYIAAPE-UHFFFAOYSA-N silicon sulfide Chemical compound S=[Si]=S KHDSWONFYIAAPE-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SRCCECZAEZWOJX-UHFFFAOYSA-M sodium;2-[formyl(hydroxy)amino]propanoate Chemical compound [Na+].[O-]C(=O)C(C)N(O)C=O SRCCECZAEZWOJX-UHFFFAOYSA-M 0.000 description 1
- IYYIUOWKEMQYNV-UHFFFAOYSA-N sodium;ethoxy-oxido-oxophosphanium Chemical compound [Na+].CCO[P+]([O-])=O IYYIUOWKEMQYNV-UHFFFAOYSA-N 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CTIFGDZXFQEIHW-UHFFFAOYSA-N sulfanylmethyl methanimidothioate Chemical compound C(S)SC=N CTIFGDZXFQEIHW-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 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
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 229950004921 temefos Drugs 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- HOKKPVIRMVDYPB-UHFFFAOYSA-N thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=NC#N)SCC1 HOKKPVIRMVDYPB-UHFFFAOYSA-N 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
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
- KJLXVAPBVMFHOL-UHFFFAOYSA-N thiolane-2,4-dione Chemical compound O=C1CSC(=O)C1 KJLXVAPBVMFHOL-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- 230000009261 transgenic effect Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- WVZPYZMQQDNINJ-UHFFFAOYSA-N tributyl(butylstannyloxy)stannane Chemical compound CCCC[SnH](CCCC)O[SnH](CCCC)CCCC WVZPYZMQQDNINJ-UHFFFAOYSA-N 0.000 description 1
- YDUBPEZBWPRJJL-UHFFFAOYSA-M tributyl-(4-chloro-2-phenylphenoxy)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)OC1=CC=C(Cl)C=C1C1=CC=CC=C1 YDUBPEZBWPRJJL-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- HFFZSMFXOBHQLV-UHFFFAOYSA-M tributylstannyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)CCCC HFFZSMFXOBHQLV-UHFFFAOYSA-M 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- NBTHYJWPOYZDHL-UHFFFAOYSA-N tricyclohexyl(tricyclohexylstannylsulfanyl)stannane Chemical compound C1CCCCC1[Sn](C1CCCCC1)(C1CCCCC1)S[Sn](C1CCCCC1)(C1CCCCC1)C1CCCCC1 NBTHYJWPOYZDHL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 241000701451 unidentified granulovirus Species 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Aは、場合により置換されていてもよいアリール、場合により置換されていてもよいヘタリール(hetaryl)又は場合により置換されていてもよいヘテロシクリルを表し;
R1は、水素又はC1-C3-アルキルを表し;
R2は、水素又はC1-C3-アルキルを表し;
R3は、水素又はC1-C3-アルキルを表し;
R4は、水素又はC1-C3-アルキルを表し;
Xは、N又はCHを表し;
Yは、CN又はNO2を表し;
Zは、CH2、O、S、SO、SO2又はNR5を表し;
R5は、水素又はC1-C3-アルキルを表す]
で表される新規ヘテロ環式化合物を提供する。
のアミンを、例えばアセトニトリル、エタノール、ベンゼン、トルエン、クロロベンゼン、ブロモベンゼン、ニトロベンゼン又はキシレンなどの稀釈剤の存在下に、適切な場合には、例えばp-トルエンスルホン酸などの酸触媒の存在下に、式(VIII):
の化合物を、先ず、例えばエーテルなどの稀釈剤中で、トリメチルシリルイソチオシアネートと反応させ、次いで、形成した中間体を、例えばメタノールを用いて、可溶化し、次いで、形成した式(IIa):
の中間体を、先ず、アセトンなどの稀釈剤の存在下で、ハロゲン化アルキル、好ましくは、ヨウ化アルキル、特に、ヨウ化メチルと反応させ、次いで、アセトンなどの稀釈剤の存在下、炭酸ナトリウムなどの塩基を用いて、式(IIIa)の最終生成物を遊離させることにより得る。
の化合物と反応させることによっても得られる(cf. J. Chem. Soc., Perkin Trans. 1(5), 1201, 1991; Zh. Org. Khim., 27(3), 526, 1991)。
の化合物を、メタノールなどの稀釈剤の存在下、ナトリウムメトキシドなどの塩基の存在下に、クロロアセトニトリルと反応させることによっても得られる。
ディプロポーダ目(Diplopoda)の、例えば、ブラニウルス・グツラツス(Blaniulus guttulatus);
チロポーダ目(Chilopoda)の、例えば、ゲオフィルス・カルポファグス(Geophilus carpophagus)及びスクチゲラ spp.(Scutigera spp);
コムカデ目(Symphyla)の、例えば、スクチゲレラ・イマクラタ(Scutigerella immaculata);
シミ目(Thysanura)の、例えば、レピスマ・サッカリナ(Lepisma saccharina);
トビムシ目(Collembola)の、例えば、オニチウルス・アルマツス(Onychiurus armatus);
バッタ目(Orthoptera)の、例えば、アケタ・ドメスチクス(Acheta domesticus)、グリロタルパ spp.(Gryllotalpa spp.)、ロクスタ・ミグラトリア・ミグラトリオイデス(Locusta migratoria migratorioides)、メラノプルス spp.(Melanoplus spp.)、及び、シストセルカ・グレガリア(Schistocerca gregaria);
ゴキブリ目(Blattaria)の、例えば、ブラッタ・オリエンタリス(Blatta orientalis)、ペリプラネタ・アメリカナ(Periplaneta americana)、レウコファエア・マデラエ(Leucophaea maderae)、及び、ブラッテラ・ゲルマニカ(Blattella germanica);
ハサミムシ目(Dermaptera)の、例えば、フォルフィクラ・アウリクラリア(Forficula auricularia);
シロアリ目(Isoptera)の、例えば、レチクリテルメス spp.(Reticulitermes spp.);
フチラプテラ目(Phthiraptera)の、例えば、ペジクルス・フマヌス・コルポリス(Pediculus humanus corporis)、ハエマトピヌス spp.(Haematopinus spp.)、リノグナツス spp.(Linognathus spp.)、トリコデクテス spp.(Trichodectes spp.)、及び、ダマリニア spp.(Damalinia spp.);
アザミウマ目(Thysanoptera)の、例えば、ヘルシノトリプス・フェモラリス(Hercinothrips femoralis)、トリプス・タバシ(Thrips tabaci)、トリプス・パルミ(Thrips palmi)、及び、フランクリニエラ・アッシデンタリス((Frankliniella accidentalis);
ヘテロプテラ目(Heteroptera)の、例えば、エウリガステル spp.(Eurygaster spp.)、ジスデルクス・インテルメヂウス(Dysdercus intermedius)、ピエスマ・クアドラタ(Piesma quadrata)、シメキス・レクツラリウス(Cimex lectularius)、ロドニウス・プロリキス(Rhodnius prolixus)、及び、トリアトマ spp.(Triatoma spp.);
ホモプテラ目(Homoptera)の、例えば、アレウロデス・ブラシカエ(Aleurodes brassicae)、ベミシア・タバシ(Bemisia tabaci)、トリアレウロデス・バポラリオルム(Trialeurodes vaporariorum)、アフィス・ゴシピイ(Aphis gossypii)、ブレビコリネ・ブラシカエ(Brevicoryne brassicae)、クリプトミズス・リビス(Cryptomyzus ribis)、アフィス・ファバエ(Aphis fabae)、アフィス・ポミ(Aphis pomi)、エリオソマ・ラニゲルム(Eriosoma lanigerum)、ヒアロプテルス・アルンジニス(Hyalopterus arundinis)、フィロキセラ・バスタトリクス(Phylloxera vastatrix)、パムフィグス spp.(Pemphigus spp.)、マクロシフム・アベナエ(Macrosiphum avenae)、ミズス spp.(Myzus spp.)、フォロドン・フムリ(Phorodon humuli)、フォパロシフム・パジ(Rhopalosiphum padi)、エムポアスカ spp.(Empoasca spp.)、エウスセリス・ビロバツス(Euscelis bilobatus)、ネフォテッチキス・シンクチセプス(Nephotettix cincticeps)、レカニウム・コルニ(Lecanium corni)、サイセチア・オレアエ(Saissetia oleae)、ラオデルファキス・ストリアテルス(Laodelphax striatellus)、ニラパルバタ・ルゲンス(Nilaparvata lugens)、アオニジエラ・アウランチイ(Aonidiella aurantii)、アスピジオツス・ハデラエ(Aspidiotus hederae)、プセウデコックス spp.(Pseudococcus spp.)、及び、プシラ spp.(Psylla spp.);
チョウ目(Lepidoptera)の、例えば、ペクチノフォラ・ゴシピエラ(Pectinophora gossypiella)、ブパルス・ピニアリウス(Bupalus piniarius)、ケイマトビア・ブルマタ(Cheimatobia brumata)、リトコレチス・ブランカルデラ(Lithocolletis blancardella)、ヒポノメウタ・パデラ(Hyponomeuta padella)、プルテラ・キシロステラ(Plutella xylostella)、マラコソマ・ネウストリア(Malacosoma neustria)、エウプロクチス・クリソロエア(Euproctis chrysorrhoea)、リマントリア spp.(Lymantria spp.)、ブクラトリス・ツルベリエラ(Bucculatrix thurberiella)、フィロクニスチス・キトレラ(Phyllocnistis citrella)、アグロチス spp.(Agrotis spp.)、エウキソア spp.(Euxoa spp.)、フェルチア spp.(Feltia spp.)、エアリアス・インスラナ(Earias insulana)、ヘリオチス spp.(Heliothis spp.)、マメステラ・ブラシカエ(Mamestra brassicae)、パノリス・フラメア(Panolis flammea)、スポドプテラ spp.(Spodoptera spp.)、トリコプルシア・ニ(Trichoplusia ni)、カルポカプサ・ポモネラ(Carpocapsa pomonella)、ピエリス spp.(Pieris spp.)、キロ spp.(Chilo spp.)、ピラウスタ・ヌビラリス(Pyrausta nubilalis)、エフェスチア・クエニエラ(Ephestia kuehniella)、ガレリア・メロネラ(Galleria mellonella)、チネオラ・ビセリエラ(Tineola bisselliella)、チネア・ペリオネラ(Tinea pellionella)、ホフマノフィラ・プセウドスプレテラ(Hofmannophila pseudospretella)、カコエシア・ポダナ(Cacoecia podana)、カプア・レチクラナ(Capua reticulana)、コリストネウラ・フミフェラナ(Choristoneura fumiferana)、クリシア・アムビグエラ(Clysia ambiguella)、ホモナ・マグナニマ(Homona magnanima)、トルトリキス・ビリダナ(Tortrix viridana)、クナファロセルス spp.(Cnaphalocerus spp.)、及び、オウレマ・オリザエ(Oulema oryzae);
コウチュウ目(Coleoptera)の、例えば、アノビウム・プンクタツム(Anobium punctatum)、リゾペルタ・ドミニカ(Rhizopertha dominica)、ブルチジウス・オブテクツス(Bruchidius obtectus)、アカントセリデス・オブテクツス(Acanthoscelides obtectus)、ヒロトルペス・バジュルス(Hylotrupes bajulus)、アゲラスチカ・アルニ(Agelastica alni)、レプチノタルサ・デセムリネアタ(Leptinotarsa decemlineata)、ファエドン・コクレアリアエ(Phaedon cochleariae)、ジアブロチカ spp.(Diabrotica spp.)、プシリオデス・クリソセファラ(Psylliodes chrysocephala)、エピラクナ・バリベスチス(Epilachna varivestis)、アトマリア spp.(Atomaria spp.)、オリザエフィルス・スリナメンシス(Oryzaephilus surinamensis)、アントノムス spp.(Anthonomus spp.)、シトフィルス spp.(Sitophilus spp.)、オチオルヒンクス・スルカツス(Otiorrhynchus sulcatus)、コスモポリテス・ソルジズス(Cosmopolites sordidus)、セウトルヒンクス・アシミリス(Ceuthorrhynchus assimilis)、ヒペラ・ポスチカ(Hypera postica)、デルメステス spp.(Dermestes spp.)、トロゴデルマ spp.(Trogoderma spp.)、アントレヌス spp.(Anthrenus spp.)、アタゲヌス spp.(Attagenus spp.)、リクツス spp.(Lyctus spp.)、メリゲテス・アエネウス(Meligethes aeneus)、プチヌス spp.(Ptinus spp.)、ニプツス・ホロレウクス(Niptus hololeucus)、ギビウム・プシロイデス(Gibbium psylloides)、トリボリウム spp.(Tribolium spp.)、テネブリオ・モリトル(Tenebrio molitor)、アグリオテス spp.(Agriotes spp.)、コノデルス spp.(Conoderus spp.)、メロロンタ・メロロンタ(Melolontha melolontha)、アンフィマロン・ソルスチチアリス(Amphimallon solstitialis)、コステリトラ・ゼアランジカ(Costelytra zealandica)、及び、リソルホプトルス・オリゾフィルス(Lissorhoptrus oryzophilus);
ハチ目(Hymenoptera)の、例えば、ジプリオン spp.(Diprion spp.)、ホプロカンパ spp.(Hoplocampa spp.)、ラシウス spp.(Lasius spp.)、モノモリウム・ファラオニス(Monomorium pharaonis)、及び、ベスパ spp.(Vespa spp.);
ハエ目(Diptera)の、例えば、アエデス spp.(Aedes spp.)、アノフェレスspp.(Anopheles spp.)、クレキス spp.(Culex spp.)、ドロソフィラ・メラノガステル(Drosophila melanogaster)、ムスカ spp.(Musca spp.)、ファニア spp.(Fannia spp.)、カリフォラ・エリトロセファラ(Calliphora erythrocephala)、ルシリア spp.(Lucilia spp.)、クリソミイア spp.(Chrysomyia spp.)、クテレブラ spp.(Cuterebra spp.)、ガストロフィルス spp.(Gastrophilus spp.)、ヒポボスカ spp.(Hyppobosca spp.)、ストモキシス spp.(Stomoxys spp.)、オエストルス spp.(Oestrus spp.)、ヒポデルマ spp.(Hypoderma spp.)、タバヌス spp.(Tabanus spp.)、タニア spp.(Tannia spp.)、ビビオ・ホルツラヌス(Bibio hortulanus)、オシネラ・フリト(Oscinella frit)、フォルビア spp.(Phorbia spp.)、ペゴミイア・ヒオスシアミ(Pegomyia hyoscyami)、セラチチス・カピタタ(Ceratitis capitata)、ダクス・オレアエ(Dacus oleae)、チプラ・パルドサ(Tipula paludosa)、ヒレミイア spp.(Hylemyia spp.)、及び、リリオミザ spp.(Liriomyza spp.);
ノミ目(Siphonaptera)の、例えば、キセノプシラ・ケオピス(Xenopsylla cheopis)、及び、セラトフィルス spp.(Ceratophyllus spp.);
アラクニダ目(Arachnida)の、例えば、スコルピオ・マウルス(Scorpio maurus)、ラトロデクツス・マクタンス(Latrodectus mactans)、アカルス・シロ(Acarus siro)、アルガス spp.(Argas spp.)、オルニトドロス spp.(Ornithodoros spp.)、デルマニスス・ガリナエ(Dermanyssus gallinae)、エリオフィエス・リビス(Eriophyes ribis)、フィロコプトルタ・オレイボラ(Phyllocoptruta oleivora)、ボオフィルス spp.(Boophilus spp.)、リピセファルス spp.(Rhipicephalus spp.)、アンブリオンマ spp.(Amblyomma spp.)、ヒアロンマ spp.(Hyalomma spp.)、イクソデス spp.(Ixodes spp.)、プソロプテス spp.(Psoroptes spp.)、コリオプテス spp.(Chorioptes spp.)、サルコプテス spp.(Sarcoptes spp.)、タルソネムス spp.(Tarsonemus spp.)、ブリオビア・プラエチオサ(Bryobia praetiosa)、パノニクス spp.(Panonychus spp.)、テトラニクス spp.(Tetranychus spp.)、ヘミタルソネムス spp.(Hemitarsonemus spp.)、及び、ブレビパルプス spp.(Brevipalpus spp.);
植物寄生性線虫としては、例えば、以下のものを挙げることができる。
プラチレンクス spp.(Pratylenchus spp.)、ラドフォルス・シミリス(Radopholus similis)、ジチレンクス・ジプサシ(Ditylenchus dipsaci)、チレンクルス・セミペネトランス(Tylenchulus semipenetrans)、ヘテロデラ spp.(Heterodera spp.)、グロボデラ spp.(Globodera spp.)、メロイドギネ spp.(Meloidogyne spp.)、アフェレンコイデス spp.(Aphelenchoides spp.)、ロンギドルス spp.(Longidorus spp.)、キシフィネマ spp.(Xiphinema spp.)、トリコドルス spp.(Trichodorus spp.)、及び、ブルサフェレンクス spp.(Bursaphelenchus spp.)
本発明の式(I)の化合物は、特に、吸汁性昆虫(sucking insects)に対して活性を示す。 特定の濃度又は特定の施用量において、本発明の化合物は、適切であれば、除草剤及び殺微生物剤(microbicides)、例えば、殺菌剤(fungicides)、殺真菌剤(antimycotics)及び殺細菌剤としても使用することができる。本発明の式(I)の化合物は、適切な場合には、別の活性化合物を合成するための中間体又は前駆体としても使用することができる。
アルジモルフ、アンプロピルホス、アンプロピルホス-カリウム、アンドプリム(andoprim)、アニラジン、アザコナゾール、アゾキシストロビン、
ベナラキシル、ベノダニル、ベノミル、ベンザマクリル、ベンザマクリル-イソブチル、ビアラホス、ビナパクリル、ビフェニル、ビテルタノール、ブラストサイジン-S、ブロムコナゾール、ブピリメート、ブチオベート、
石灰硫黄(ポリ硫化カルシウム;calcium polysulphide)、カプシマイシン(capsimycin)、キャプタホール、キャプタン、カルベンダジム、カルボキシン、カルボン(carvon)、キノメチオネート、クロベンチアゾン、クロルフェナゾール、クロロネブ、クロロピクリン、クロロタロニル、クロゾリネート、クロジラコン(clozylacon)、クフラネブ、シモキサニル、シプロコナゾール、シプロジニル、シプロフラム、
デバカルブ(debacarb)、ジクロロフェン、ジクロブトラゾール、ジクロフルアニド、ジクロメジン、ジクロラン、ジエトフェンカルブ、ジフェノコナゾール、ジメチリモール、ジメトモルフ、ジニコナゾール、ジニコナゾール-M、ジノカップ、ジフェニルアミン、ジピリチオン、ジタリムホス、ジチアノン、ドデモルフ、ドジン、ドラゾクソロン、
エジフェンホス、エポキシコナゾール、エタコナゾール、エチリモール、エトリジアゾール、
ファモキサドン、フェナパニル、フェナリモール、フェンブコナゾール、フェンフラム、フェニトロパン、フェンピクロニル、フェンプロピジン、フェンプロピモルフ、酢酸トリフェニル錫、水酸化トリフェニル錫、ファーバム、フェリムゾン、フルアジナム、フルメトベル(flumetover)、フルオロイミド、フルキンコナゾール、フルルプリミドール、フルシラゾール、フルスルファミド、フルトラニル、フルトリアホール、ホルペット、ホセチル-アルミニウム、ホセチル-ナトリウム、フサライド、フベリダゾール、フララキシル、フラメトピル、フルカルボニル(furcarbonil)、フルコナゾール、フルコナゾール-シス、フルメシクロックス、
グアザチン、
ヘキサクロロベンゼン、ヘキサコナゾール、ヒメキサゾール、
イマザリル、イミベンコナゾール、イミノクタジン、イミノクタジンアルベシル酸塩、イミノクタジン三酢酸塩、ヨードカルブ、イプコナゾール、イプロベンホス(IBP)、イプロジオン、イルママイシン、イソプロチオラン、イソバレジオン、
カスガマイシン、クレソキシム-メチル、銅調製物、例えば、水酸化銅、ナフテン酸銅、オキシ塩化銅、硫酸銅、酸化銅、オキシン-銅及びボルドー液など、
マンカッパー(mancopper)、マンコゼブ、マンネブ、メフェリムゾン、メパニピリム、メプロニル、メタラキシル、メトコナゾール、メタスルホカルブ、メトフロキサム、メチラム、メトメクラム、メトスルホバックス(metsulfovax)、ミルディオマイシン、ミクロブタニル、ミクロゾリン、
ジメチルジチオカルバミン酸ニッケル、ニトロタル-イソプロピル、ヌアリモール、
オフラセ、オキサジキシル、オキサモカルブ(oxamocarb)、オキソリン酸、オキシカルボキシム、オキシフェンチイン(oxyfenthiin)、
パクロブトラゾール、ペフラゾエート、ペンコナゾール、ペンシクロン、ホスダイフェン、ピマリシン、ピペラリン(piperalin)、ポリオキシン、ポリオキソリム(polyoxorim)、プロベナゾール、プロクロラズ、プロシミドン、プロパモカルブ、プロパノシン-ナトリウム(propanosine-sodium)、プロピコナゾール、プロピネブ、ピラゾホス、ピリフェノックス、ピリメタニル、ピロキロン、ピロキシフル、
キノコナゾール(quinconazole)、キントゼン(PCNB)、
硫黄及び硫黄調製物、
テブコナゾール、テクロフタラム、テクナゼン、テトシクラシス、テトラコナゾール、チアベンダゾール、チシオフェン(thicyofen)、チフルザミド、チオファネート-メチル、チラム、チオキシミド、トルクロホス-メチル、トリルフルアニド、トリアジメホン、トリアジメノール、トリアズブチル、トリアゾキシド、トリクラミド、トリシクラゾール、トリデモルフ、トリフルミゾール、トリホリン、トリチコナゾール、
ウニコナゾール、
バリダマイシン-A、ビンクロゾリン、ビニコナゾール、
ザリラミド、ジネブ、ジラム
及び、さらに、
Dagger G、
OK-8705、
OK-8801、
α-(1,1-ジメチルエチル)-β-(2-フェノキシエチル)-1H-1,2,4-トリアゾール-1-エタノール、
α-(2,4-ジクロロフェニル)-β-フルオロ-β-プロピル-1H-1,2,4-トリアゾール-1-エタノール、
α-(2,4-ジクロロフェニル)-β-メトキシ-α-メチル-1H-1,2,4-トリアゾール-1-エタノール、
α-(5-メチル-1,3-ジオキサン-5-イル)-β-[[4-(トリフルオロメチル)-フェニル]-メチレン]-1H-1,2,4-トリアゾール-1-エタノール、
(5RS,6RS)-6-ヒドロキシ-2,2,7,7-テトラメチル-5-(1H-1,2,4-トリアゾール-1-イル)-3-オクタノン、
(E)-α-(メトキシイミノ)-N-メチル-2-フェノキシ-フェニルアセトアミド、
1-イソプロピル{2-メチル-1-[[[1-(4-メチルフェニル)-エチル]-アミノ]-カルボニル]-プロピル}-カルバメート、
1-(2,4-ジクロロフェニル)-2-(1H-1,2,4-トリアゾール-1-イル)-エタノン-O-(フェニルメチル)-オキシム、
1-(2-メチル-1-ナフタレニル)-1H-ピロール-2,5-ジオン、
1-(3,5-ジクロロフェニル)-3-(2-プロペニル)-2,5-ピロリジンジオン、
1-[(ジヨードメチル)-スルホニル]-4-メチル-ベンゼン、
1-[[2-(2,4-ジクロロフェニル)-1,3-ジオキソラン-2-イル]-メチル]-1H-イミダゾール、
1-[[2-(4-クロロフェニル)-3-フェニルオキシラニル]-メチル]-1H-1,2,4-トリアゾール、
1-[1-[2-[(2,4-ジクロロフェニル)-メトキシ]-フェニル]-エテニル]-1H-イミダゾール、
1-メチル-5-ノニル-2-(フェニルメチル)-3-ピロリジノール、
2',6'-ジブロモ-2-メチル-4'-トリフルオロメトキシ-4'-トリフルオロ-メチル-1,3-チアゾール-5-カルボキシアニリド、
2,2-ジクロロ-N-[1-(4-クロロフェニル)-エチル]-1-エチル-3-メチルシクロプロパンカルボキサミド、
2,6-ジクロロ-5-(メチルチオ)-4-ピリミジニル-チオシアネート、
2,6-ジクロロ-N-(4-トリフルオロメチルベンジル)-ベンズアミド、
2,6-ジクロロ-N-[[4-(トリフルオロメチル)-フェニル]-メチル]-ベンズアミド、
2-(2,3,3-トリヨード-2-プロペニル)-2H-テトラゾール、
2-[(1-メチルエチル)-スルフォニル]-5-(トリクロロメチル)-1,3,4-チアジアゾール、
2-[[6-デオキシ-4-O-(4-O-メチル-β-D-グリコピラノシル)-α-D-グルコピラノシル]-アミノ]-4-メトキシ-1H-ピロロ[2,3-d]ピリミジン-5-カルボニトリル、
2-アミノブタン、
2-ブロモ-2-(ブロモメチル)-ペンタンジニトリル、
2-クロロ-N-(2,3-ジヒドロ-1,1,3-トリメチル-1H-インデン-4-イル)-3-ピリジンカルボキサミド、
2-クロロ-N-(2,6-ジメチルフェニル)-N-(イソチオシアナトメチル)-アセトアミド、
2-フェニルフェノール(OPP)、
3,4-ジクロロ-1-[4-(ジフルオロメトキシ)-フェニル]-1H-ピロール-2,5-ジオン、
3,5-ジクロロ-N-[シアノ-[(1-メチル-2-プロピニル)-オキシ]-メチル]-ベンズアミド、
3-(1,1-ジメチルプロピル)-1-オキソ-1H-インデン-2-カルボニトリル、
3-[2-(4-クロロフェニル)-5-エトキシ-3-イソオキサゾリジニル]-ピリジン、
4-クロロ-2-シアノ-N,N-ジメチル-5-(4-メチルフェニル)-1H-イミダゾール-1-スルホンアミド、
4-メチル-テトラゾロ[1,5-a]キナゾリン-5(4H)-オン、
8-(1,1-ジメチルエチル)-N-エチル-N-プロピル-1,4-ジオキサスピロ[4.5]デカン-2-メタンアミン、
8-ヒドロキシキノリンスルフェート、
9H-キサンテン-2-[(フェニルアミノ)-カルボニル]-9-カルボン酸ヒドラジド、
ビス-(1-メチルエチル)-3-メチル-4-[(3-メチルベンゾイル)-オキシ]-2,5-チオフェンジカルボキシレート、
シス-1-(4-クロロフェニル)-2-(1H-1,2,4-トリアゾール-1-イル)-シクロヘプタノール、
シス-4-[3-[4-(1,1-ジメチルプロピル)-フェニル-2-メチルプロピル]-2,6-ジメチルモルホリン塩酸塩、
エチル [(4-クロロフェニル)-アゾ]-シアノアセテート、
炭酸水素カリウム、
メタンテトラチオールナトリウム塩、
メチル 1-(2,3-ジヒドロ-2,2-ジメチル-1H-インデン-1-イル)-1H-イミダゾール-5-カルボキシレート、
メチル N-(2,6-ジメチルフェニル)-N-(5-イソオキサゾリルカルボニル)-DL-アラニネート、
メチル N-(クロロアセチル)-N-(2,6-ジメチルフェニル)-DL-アラニネート、
N-(2,3-ジクロロ-4-ヒドロキシフェニル)-1-メチル-シクロヘキサンカルボキサミド、
N-(2,6-ジメチルフェニル)-2-メトキシ-N-(テトラヒドロ-2-オキソ-3-フラニル)-アセトアミド、
N-(2,6-ジメチルフェニル)-2-メトキシ-N-(テトラヒドロ-2-オキソ-3-チエニル)-アセトアミド、
N-(2-クロロ-4-ニトロフェニル)-4-メチル-3-ニトロ-ベンゼンスルホンアミド、
N-(4-シクロヘキシルフェニル)-1,4,5,6-テトラヒドロ-2-ピリミジンアミン、
N-(4-ヘキシルフェニル)-1,4,5,6-テトラヒドロ-2-ピリミジンアミン、
N-(5-クロロ-2-メチルフェニル)-2-メトキシ-N-(2-オキソ-3-オキサゾリジニル)-アセトアミド、
N-(6-メトキシ)-3-ピリジニル-シクロプロパンカルボキサミド、
N-[2,2,2-トリクロロ-1-[(クロロアセチル)-アミノ]-エチル]-ベンズアミド、
N-[3-クロロ-4,5-ビス-(2-プロピニルオキシ)-フェニル]-N'-メトキシ-メタンイミドアミド、
N-ホルミル-N-ヒドロキシ-DL-アラニンナトリウム塩、
O,O-ジエチル [2-(ジプロピルアミノ)-2-オキソエチル]-エチルホスホルアミドチオエート、
O-メチル S-フェニル フェニルプロピルホスホルアミドチオエート、
S-メチル 1,2,3-ベンゾチアジアゾール-7-カルボチオエート、
スピロ[2H]-1-ベンゾピラン-2,1'(3'H)-イソベンゾフラン-3'-オン。
ブロノポール、ジクロロフェン、ニトラピリン、ジメチルジチオカルバミン酸ニッケル、カスガマイシン、オクチリノン、フランカルボン酸、オキシテトラサイクリン、プロベナゾール、ストレプトマイシン、テクロフタラム、硫酸銅及び別の銅調製物。
アバメクチン、アセフェート、アセタミプリド、アクリナトリン、アラニカルブ、アルジカルブ、アルドキシカルブ、アルファシペルメトリン、アルファメトリン、アミトラズ、アベルメクチン、AZ 60541、アザディラクチン、アザメチホス、アジンホス-A、アジンホス-M、アゾシクロチン、
バシルス・ポピリアエ(Bacillus popilliae)、バシルス・スファエリクス(Bacillus sphaericus)、バシルス・スブチリス(Bacillus subtilis)、バシルス・ツリンギエンシス(Bacillus thuringiensis)、バキュロウイルス、ベアウベリア・バシアナ(Beauveria bassiana)、ベアウベリア・テネラ(Beauveria tenella)、ベンジオカルブ、ベンフラカルブ、ベンスルタップ、ベンゾキシメート、ベータシフルトリン、ビフェナゼート、ビフェントリン、ビオエタノメトリン(bioethanomethrin)、ビオペルメトリン、BPMC、ブロモホス-A、ブフェンカルブ、ブプロフェジン、ブタチオホス、ブトカルボキシム、ブチルピリダベン(butylpyridaben)、
カズサホス、カルバリル、カルボフラン、カルボフェノチオン、カルボスルファン、カルタップ、クロエトカルブ、クロルエトキシホス、クロルフェナピル、クロルフェンビンホス、クロルフルアズロン、クロルメホス、クロルピリホス、クロルピリホス-M、クロバポルトリン(chlovaporthrin)、シス-レスメトリン、シスペルメトリン、クロシトリン(clocythrin)、クロエトカルブ、クロフェンテジン、シアノホス、シクロプレン(cycloprene)、シクロプロトリン、シフルトリン、シハロトリン、シヘキサチン、シペルメトリン、シロマジン、
デルタメトリン、ジメトン-M、ジメトン-S、ジメトン-Sメチル、ジアフェンチウロン、ダイアジノン、ジクロルボス、ジフルベンズロン、ジメトエート、ジメチルビンホス、ジオフェノラン、ダイスルホトン、ドクサト-ナトリウム(docusat-sodium)、ドフェナピン(dofenapyn)、
エフルシラネート(eflusilanate)、エマメクチン、エムペントリン、エンドスルファン、エントモプトラ spp.(Entomopfthora spp.)、エプリノメクチン、エスフェンバレレート、エチオフェンカルブ、エチオン、エトプロホス、エトフェンプロックス、エトキサゾール、エトリムホス、
フェナミホス、フェナザキン、酸化フェンブタスズ、フェニトロチオン、フェノチオカルブ、フェノキサクリム、フェノキシカルブ、フェンプロパトリン、フェンピラド、フェンピリトリン、フェンピロキシメート、フェンバレレート、フィプロニル、フルアジナム、フルアズロン、フルブロシトリネート(flubrocythrinate)、フルシクロクスロン、フルシトリネート、フルフェノクスロン、フルテンジン(flutenzine)、フルバリネート、ホノホス、ホスメチラン、ホスチアゼート、フブフェンプロックス(fubfenprox)、フラチオカルブ、
グラニュローシスウイルス、
ハロフェンジド(halofenozide)、HCH、ヘプテノホス、ヘキサフルムロン、ヘキシチアゾクス、ハイドロプレン、
イミダクロプリド、イサゾホス、イソフェンホス、イソキサチオン、イベルメクチン、
核多角体病ウイルス、
ラムダ-シハロトリン、ルフェヌロン
マラチオン、メカルバム、メタアルデヒド、メタミドホス、メタリジウム・アニソプリアエ(Metharhizium anisopliae)、メタリジウム・フラボビリデ(Metharhizium flavoviride)、メチダチオン、メチオカルブ、メソミル、メトキシフェノジド、メトルカルブ、メトキサジアゾン、メビンホス、ミルベメクチン、モノクロトホス、
ナレド、ニテンピラム、ニチアジン、ノバルロン、
オメトエート、オキサミル、オキシジメトン-M、
パエシロマイセス・フモソロセウス(Paecilomyces fumosoroseus)、パラチオン-A、パラチオン-M、ペルメトリン、フェントエート、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミカーブ、ピリミホス-A、ピリミホス-M、プロフェノホス、プロメカルブ、プロポクスル、プロチオホス、プロトエート、ピメトロジン、ピラクロホス、ピレスメトリン、ピレトルム、ピリダベン、ピリダチオン(pyridathion)、ピリミジフェン、ピリプロキシフェン、
キナルホス、
リバビリン、
サリチオン、セブホス(sebufos)、セラメクチン、シラフルオフェン、スピノサド、スルホテップ、スルプロホス、
タウ-フルバリネート、テブフェノジド、テブフェンピラド、テブピリミホス(tebupirimiphos)、テフルベンズロン、テフルトリン、テメホス、テミビンホス、 テルブホス、テトラクロロビンホス、シータシペルメトリン(thetacypermethrin)、チアメトキサム、チアプロニル、チアトリホス(thiatriphos)、チオシクラムシュウ酸水素塩(thiocyclam hydrogen oxalate)、チオジカルブ、チオファノックス、チューリンギエンシン、トラロシトリン(tralocythrin)、 トラロメトリン、トリアラセン、トリアザメート、トリアゾホス、トリアズロン、トリクロフェニジン(trichlophenidine)、トリクロルホン、トリフルムロン、トリメタカルブ、
バミドチオン、バニリプロール(vaniliprole)、ベルチシリウム・レカニイ(Verticillium lecanii)、
YI 5302、
ゼータ-シペルメトリン(zeta-cypermethrin)、ゾラプロホス、
(1R-シス)-[5-(フェニルメチル)-3-フラニル]-メチル-3-[(ジヒドロ-2-オキソ-3(2H)-フラニリデン)-メチル]-2,2-ジメチルシクロプロパンカルボキシレート、
(3-フェノキシフェニル)-メチル-2,2,3,3-テトラメチルシクロプロパンカルボキシレート、
1-[(2-クロロ-5-チアゾリル)メチル]テトラヒドロ-3,5-ジメチル-N-ニトロ-1,3,5-トリアジン-2(1H)-イミン、
2-(2-クロロ-6-フルオロフェニル)-4-[4-(1,1-ジメチルエチル)フェニル]-4,5-ジヒドロ-オキサゾール、
2-(アセトキシ)-3-ドデシル-1,4-ナフタレンジオン、
2-クロロ-N-[[[4-(1-フェニルエトキシ)-フェニル]-アミノ]-カルボニル]-ベンズアミド、
2-クロロ-N-[[[4-(2,2-ジクロロ-1,1-ジフルオロエトキシ)-フェニル]-アミノ]-カルボニル]ベンズアミド、
3-メチルフェニル プロピルカルバメート、
4-[4-(4-エトキシフェニル)-4-メチルペンチル]-1-フルオロ-2-フェノキシ-ベンゼン、
4-クロロ-2-(1,1-ジメチルエチル)-5-[[2-(2,6-ジメチル-4-フェノキシフェノキシ)エチル]チオ]-3(2H)-ピリダジノン、
4-クロロ-2-(2-クロロ-2-メチルプロピル)-5-[(6-ヨード-3-ピリジニル)メトキシ]-3(2H)-ピリダジノン、
4-クロロ-5-[(6-クロロ-3-ピリジニル)メトキシ]-2-(3,4-ジクロロフェニル)-3(2H)-ピリダジノン、
バシルス・ツリンギエンシス(Bacillus thuringiensis)株EG-2348、
[2-ベンゾイル-1-(1,1-ジメチルエチル)-ヒドラジノ安息香酸、
2,2-ジメチル-3-(2,4-ジクロロフェニル)-2-オキソ-1-オキサスピロ[4.5]デカ-3-エン-4-イルブタン酸塩、
[3-[(6-クロロ-3-ピリジニル)メチル]-2-チアゾリジニリデン]-シアンアミド、
ジヒドロ-2-(ニトロメチレン)-2H-1,3-チアジン-3(4H)-カルボキシアルデヒド、
エチル [2-[[1,6-ジヒドロ-6-オキソ-1-(フェニルメチル)-4-ピリダジニル]オキシ]エチル]-カルバメート、
N-(3,4,4-トリフルオロ-1-オキソ-3-ブテニル)-グリシン、
N-(4-クロロフェニル)-3-[4-(ジフルオロメトキシ)フェニル]-4,5-ジヒドロ-4-フェニル-1H-ピラゾール-1-カルボキサミド、
N-[(2-クロロ-5-チアゾリル)メチル]-N'-メチル-N''-ニトロ-グアニジン、
N-メチル-N'-(1-メチル-2-プロペニル)-1,2-ヒドラジンジカルボチオアミド、
N-メチル-N'-2-プロペニル-1,2-ヒドラジンジカルボチオアミド、
O,O-ジエチル [2-(ジプロピルアミノ)-2-オキソエチル]-エチルホスホルアミドチオエート。
ハジラミ(Mallophagida)目及びマルツノハジラミ(Amblycerina)亜目とホソツノハジラミ(Ischnocerina)亜目の、例えば、トリメノポン spp.(Trimenopon spp.)、メノポン spp.(Menopon spp.)、トリノトン spp.(Trinoton spp.)、ボビコラ spp.(Bovicola spp.)、ウェルネツキエラ spp.(Werneckiella spp.)、レピケントロン spp.(Lepikentron spp.)、ダマリナ spp.(Damalina spp.)、トリコデクテス spp.(Trichodectes spp.)及びフェリコラ spp.(Felicola spp.)。
ノミ(Siphonapterida)目の、例えば、プレクス spp.(Pulex spp.)、クテノセファリデス spp.(Ctenocephalides spp.)、キセノプシラ spp.(Xenopsylla spp.)及びケラトフィルス spp.(Ceratophyllus spp.);
カメムシ(Heteropterida)目の、例えば、シメクス spp.(Cimex spp.)、トリアトマ spp.(Triatoma spp.)、ロドニウス spp.(Rhodnius spp.)及びパンストロンギルス spp.(Panstrongylus spp.);
ゴキブリ(Blattarida)目の、例えば、ブラッタ・オリエンタリス(Blatta orientalis)、ペリプラネタ・アメリカナ(Periplaneta americana)、ブラテラ・ゲルマニカ(Blattela germanica)及びスペラ spp.(Supella spp.);
アカリア(Acaria(Acarida)))亜綱及びメタスチグマタ(Metastigmata)目とメソスチグマタ(Mesostigmata)目の、例えば、アルガス spp.(Argas spp.)、オルニトドロス spp.(Ornithodorus spp.)、オトビウス spp.(Otobius spp.)、イクソデス spp.(Ixodes spp.)、アンブリオンマ spp.(Amblyomma spp.)、ボオフィルス spp.(Boophilus spp.)、デルマセントル spp.(Dermacentor spp.)、ハエモフィサリス spp.(Haemophysalis spp.)、ヒアロマ spp.(Hyalomma spp.)、リピセファルス spp.(Rhipicephalus spp.)、デルマニスス spp.(Dermanyssus spp.)、ライリエチア spp.(Raillietia spp.)、プネウモニスス spp.(Pneumonyssus spp.)、ステルノストマ spp.(Sternostoma spp.)及びバロア spp.(Varroa spp.);
アクチネジダ(Actinedida(Prostigmata))目及びアカリジダ(Acaridida(Astigmata))目の、例えば、アカラピス spp.(Acarapis spp.)、ケイレチエラ spp.(Cheyletiella spp.)、オルニトケイレチア spp.(Ornithocheyletia spp.)、ミオビア spp.(Myobia spp.)、プソレルガテス spp.(Psorergates spp.)、デモデクス spp.(Demodex spp.)、トロムビクラ spp.(Trombicula spp.)、リストロホルス spp.(Listrophorus spp.)、アカルス spp.(Acarus spp.)、チロファグス spp.(Tyrophagus spp.)、カログリフス spp.(Caloglyphus spp.)、ヒポデクテス spp.(Hypodectes spp.)、プテロリクス spp.(Pterolichus spp.)、プソロプテス spp.(Psoroptes spp.)、クオリオプテス spp.(Chorioptes spp.)、オトデクテス spp.(Otodectes spp.)、サルコプテス spp.(Sarcoptes spp.)、ノトエドレス spp.(Notoedres spp.)、クネミドコプテス spp.(Knemidocoptes spp.)、シトジテス spp.(Cytodites spp.)及びラミノシオプテス spp.(Laminosioptes spp.)。
シミ類、例えば、レピスマ・サッカリナ(Lepisma saccharina)。
殺菌剤、例えば、ベンゾ[b]チオフェンカルボン酸シクロヘキシルアミド S,S-ジオキシド、ジクロフルアニド、フルオロフォルペット、3-ヨード-2-プロピニル ブチルカルバメート、トリルフルアニド、及び、アゾール類、例えば、アザコナゾール、シプロコナゾール、エポキシコナゾール、ヘキサコナゾール、メトコナゾール、プロピコナゾール及びテブコナゾール;
軟体動物駆除剤、例えば、酢酸トリフェニルスズ、メタルデヒド、メチオカルブ、ニクロサミド、チオジカルブ及びトリメタカルブ;
又は、通常の汚れ止め活性化合物、例えば、4,5-ジクロロ-2-オクチル-4-イソチアゾリン-3-オン、ジヨードメチルパラトリルスルホン(diiodomethylparatryl sulphone)、2-(N,N-ジメチルチオカルバモイルチオ)-5-ニトロチアジル、2-ピリジンチオール1-オキシドのカリウム塩、銅塩、ナトリウム塩及び亜鉛塩、ピリジン-トリフェニルボラン、テトラブチルジスタンノキサン(tetrabutyldistannoxane)、2,3,5,6-テトラクロロ-4-(メチルスルホニル)-ピリジン、2,4,5,6-テトラクロロイソフタロニトリル、テトラメチルチウラム ジスルフィド、及び、2,4,6-トリクロロフェニルマレイミド。
アカリナ(Acarina)目の、例えば、アルガス・ペルシクス(Argas persicus)、アルガス・レフレクスス(Argas reflexus)、ブリオビア spp.(Bryobia ssp.)、デルマニススス・ガリナエ(Dermanyssus gallinae)、グリシファグス・ドメスチクス(Glyciphagus domesticus)、オルニトドルス・モウバト(Ornithodorus moubat)、リピセファルス・サングイネウス(Rhipicephalus sanguineus)、トロムビクラ・アルフレズゲシ(Trombicula alfreddugesi)、ネウトロムビクラ・アウツムナリス(Neutrombicula autumnalis)、デルマトファゴイデス・プテロニスシムス(Dermatophagoides pteronissimus)、デルマトファゴイデス・フォリナエ(Dermatophagoides forinae);
クモ(Araneae)目の、例えば、アビクラリイダエ(Aviculariidae)、アラネイダエ(Araneidae);
ザトウムシ(Opiliones)目の、例えば、プセウドスコルピオネス・ケリフェル(Pseudoscorpiones chelifer)、プセウドスコルピオネス・ケイリジウム(Pseudoscorpiones cheiridium)、オピリオネス・ファランギウム(Opiliones phalangium);
ワラジムシ(Isopoda)目の、例えば、オニスクス・アセルス(Oniscus asellus)、ポルセリオ・スカベル(Porcellio scaber);
ジプロポダ(Diplopoda)目の、例えば、ブラニウルス・グツラツス(Blaniulus guttulatus)、ポリデスムス spp.(Polydesmus spp.);
チロポダ(Chilopoda)目の、例えば、ゲオフィルス spp.(Geophilus spp.);
シミ(Zygentoma)目の、例えば、クテノレピスマ spp.(Ctenolepisma spp.)、レピスマ・サカリナ(Lepisma saccharina)、レピスモデス・インクイリヌス(Lepismodes inquilinus);
ゴキブリ(Blattaria)目の、例えば、ブラッタ・オリエンタリエス(Blatta orientalies)、ブラッテラ・ゲルマニカ(Blattella germanica)、ブラッテラ・アサヒナイ(Blattella asahinai)、レウコファエア・マデラエ(Leucophaea maderae)、パンクロラ spp.(Panchlora spp.)、パルコブラッタ spp.(Parcoblatta spp.)、ペリプラネタ・アウストララシアエ(Periplaneta australasiae)、ペリプラネタ・アメリカナ(Periplaneta americana)、ペリプラネタ・ブルネア(Periplaneta brunnea)、ペリプラネタ・フリギノサ(Periplaneta fuliginosa)、スペラ・ロンギパルパ(Supella longipalpa);
サルタトリア(Saltatoria)目の、例えば、アケタ・ドメスチクス(Acheta domesticus);
ハサミムシ(Dermaptera)目の、例えば、フォルフィクラ・アウリクラリア(Forficula auricularia);
シロアリ(Isoptera)目の、例えば、カロテルメス spp.(Kalotermes spp.)、レチクリテルメス spp.(Reticulitermes spp.);
チャタテムシ(Psocoptera)目の、例えば、レピナツス spp.(Lepinatus spp.)、リポセリス spp.(Liposcelis spp.);
コレプテラ(Coleptera)目の、例えば、アントレヌス spp.(Anthrenus spp.)、アタゲヌス spp.(Attagenus spp.)、デルメステス spp.(Dermestes spp.)、ラテチクス・オリザエ(Latheticus oryzae)、ネクロビア spp.(Necrobia spp.)、プチヌス spp.(Ptinus spp.)、リゾペルタ・ドミニカ(Rhizopertha dominica)、シトフィルス・グラナリウス(Sitophilus granarius)、シトフィルス・オリザエ(Sitophilus oryzae)、シトフィルス・ゼアマイス(Sitophilus zeamais)、ステゴビウム・パニセウム(Stegobium paniceum);
ハエ(Diptera)目の、例えば、アエデス・アエギプチ(Aedes aegypti)、アエデス・アルボピクツス(Aedes albopictus)、アエデス・タエニオリンクス(Aedes taeniorhynchus)、アノフェレス spp.(Anopheles spp.)、カリフォラ・エリトロセファラ(Calliphora erythrocephala)、クリソゾナ・プルビアリス(Chrysozona pluvialis)、クレクス・クインクエファシアツス(Culex quinquefasciatus)、クレクス・ピピエンス(Culex pipiens)、クレクス・タルサリス(Culex tarsalis)、ドロソフィラ spp.(Drosophila spp.)、ファニア・カニクラリス(Fannia canicularis)、ムスカ・ドメスチカア(Musca domestica)、ホレボトムス spp.(Phlebotomus spp.)、サルコファガ・カルナリア(Sarcophaga carnaria)、シムリウム spp.(Simulium spp.)、ストモキシス・カルシトランス(Stomoxys calcitrans)、チプラ・パルドサ(Tipula paludosa);
チョウ(Lepidoptera)目の、例えば、アクロイア・グリセラ(Achroia grisella)、ガレリア・メロネラ(Galleria mellonella)、プロジア・インテルプンクテラ(Plodia interpunctella)、チネア・クロアセラ(Tinea cloacella)、チネア・ペリオネラ(Tinea pellionella)、チネオラ・ビセリエラ(Tineola bisselliella);
シフォナプテラ(Siphonaptera)目の、例えば、クテノセファリデス・カニス(Ctenocephalides canis)、クテノセファリデス・フェリス(Ctenocephalides felis)、プレクス・イリタンス(Pulex irritans)、ツンガ・ペネトランス(Tunga penetrans)、キセノプシラ・ケオピス(Xenopsylla cheopis);
ハチ(Hymenoptera)目の、例えば、カムポノツス・ヘルクレアヌス(Camponotus herculeanus)、ラシウス・フリギノスス(Lasius fuliginosus)、ラシウス・ニゲル(Lasius niger)、ラシウス・ウムブラツス(Lasius umbratus)、モノモリウム・ファラオニス(Monomorium pharaonis)、パラベスプラ spp.(Paravespula spp.)、テトラモリウム・カエスピツム(Tetramorium caespitum);
シラミ(Anoplura)目の、例えば、ペジクルス・フマヌス・カピチス(Pediculus humanus capitis)、ペジクルス・フマヌス・コルポリス(Pediculus humanus corporis)、フチルス・プビス(Phthirus pubis);
ヘテロプテラ(Heteroptera)目の、例えば、シメクス・ヘミプテルス(Cimex hemipterus)、シメクス・レクツラリウス(Cimex lectularius)、ロジヌス・プロリクスス(Rhodinus prolixus)、トリアトマ・インフェスタンス(Triatoma infestans)。
実施例I-1
4-(N-(6-クロロ-3-ピリジルメチル)-N-メチル)アミノ-2-シアンイミノ-2,5-ジヒドロ-[1,3]-チアゾリン
収量:0.42g(理論値の15%) C11H10ClN5S(M = 279.75g/mol)
MS(FAB/NBA マトリックス)
m/z(%) = 283 (5), 282 (31), 281 (15), 280 (80) [M+1]+, 279 (7)
IR(KBr中の固体)
4-(N-(2-クロロチアゾール-5-イル)-N-エチル)アミノ-2-シアンイミノ-2,5-ジヒドロ-[1,3]-チアゾリン
C10H10ClN5S2 (M = 299.8g/mol)
LC-MS(ESI 正)(m/z, %) = 300 (MH+, 100)
Rt=3.54分(0.1%HCOOH/アセトニトリル)
HPLC (水/アセトニトリル) = 3.17分; λmax= 287.5nm。
5-シアンイミノ-2-(N-(2-クロロチアゾール-5-イル)-N-エチル)アミノピロリン
収量:1.4mg(理論値の0.05%) C11H12ClN5S(M = 281.7g/mol)
LC-MS(ESI 正)(m/z, %) = 282 (MH+, 100)
Rt = 2.93分(0.1%HCOOH/アセトニトリル)。
5-(N-(6-クロロ-3-ピリジルメチル)-N-メチルアミノ)-4,4-ジメチル-2-メチルスルファニル-4H-イミダゾール
収量:1.93g(理論値の81%) C13H17ClN4S(M = 296.82g/mol)
2-(N-(2-クロロチアゾール-5-イル)-N-エチル)アミノピロリン-5-チオン
収量:0.01g(理論値の1.8%) C10H12ClN3S2(M = 273.8g/mol)
LC-MS(ESI 正)(m/z, %) = 274 (MH+, 100)
Rt = 3.12分(0.1%HCOOH/アセトニトリル)。
4-(N-(6-クロロ-3-ピリジルメチル)-N-メチルアミノ)-5,5-ジメチル-2,5-ジヒドロ-1H-イミダゾール-2-チオン
収量:2.69g(理論値の95%) C12H15ClN4S(M = 282.80g/mol)
2-(N-(2-クロロピリド-5-イル)-N-メチル)アミノピロリン-5-オン
収量:4.6g(理論値の66.7%) C11H12ClN3O(M = 237.7 g/mol)
LC-MS(ESI 正)(m/z, %) = 238 (MH+, 100)
Rt = 1.08分(0.1%HCOOH/アセトニトリル)。
HPLC(0.05M NH4HCO3/アセトニトリル) = 1.41分;λmax = 238nm。
4-(N-(2-クロロチアゾール-5-イル)-N-メチル)アミノ-2(5H)-チオフェノン
収量:0.20g(理論値の6.4%) C9H9ClN2OS2(M = 260.7 g/mol)
LC-MS(ESI 正)(m/z, %) = 261 (MH+, 100)
Rt = 3.33分(0.1%HCOOH/アセトニトリル)。
6-クロロ-3-(N-(2,2-ジメチル-2H-アジリン-3-イル)-N-メチル)-アミノメチルピリジン
収量:1.92g(理論値の57%) C11H14ClN3(M = 223.71g/mol)
N-(6-クロロ-3-ピリジルメチル)-N-メチル-2-メチルプロパンチオアミド
m.p.:56℃
収量:5.16g(理論値の71%) C11H15ClN2S(M = 242.77g/mol)
(a) シアノイミドジチオ炭酸ジカリウム塩の調製
窒素雰囲気下、オーバーヘッド撹拌機、滴下漏斗、温度計及び還流冷却器が付いた500mL容の四つ口フラスコ内で、40mLのエタノール中の21.0g(0.50mol)のシアンアミドを0℃に冷却する。この温度で、41.9g(0.55mol)の二硫化炭素、次いで、180mLのエタノール中の56.1g(1.00mol)の水酸化カリウムを、内部温度が5℃を超えないように、連続して滴下して加える(約4時間)。二硫化炭素と水酸化カリウムの添加終了後、冷浴を除去し、得られた混合物を室温で一晩撹拌する。生じた固体を濾過し、エタノールで洗浄し、減圧下に乾燥させる。得られた塩は吸湿性であり、濾過中に、大気/大気湿度に長時間接触させるべきではない。前記塩は、次のステップにおいて粗生成物として使用する。収率は理論値の75%〜80%である。
77.7g(0.40mol)の上記粗生成物を、270mLのアセトンと300mLの水の混液に溶解させ、0℃に冷却する。この温度で、激しく撹拌しながら、150mLのアセトン中の56.8g(0.40mol)のヨウ化メチルを、ゆっくりと3時間かけて滴下して加える。ヨウ化メチルの添加終了後、得られた反応混合物を、0℃で1時間撹拌した後、室温でさらに3時間撹拌する。回転蒸発器を用いて、全ての溶媒を除去して、乾固させる。残渣を250mLの無水アセトンに取り込み、回転蒸発器を用いて、元の容積の半分になるまで濃縮する。生じたヨウ化カリウムを結晶化させるために、反応混合物を冷蔵庫内に一晩維持する。生じた固体を濾過し、濾液を、殆ど乾固するまでさらに濃縮する。冷所で、所望の生成物が析出する。最後のステップを繰り返してヨウ化カリウムを完全に除去することができる。収量は、理論値の75%〜80%である。分析データは、文献のデータと一致する。
実施例A
ネコブセンチュウ(Meloidogyne)試験
溶媒: 7重量部のジメチルホルムアミド
乳化剤: 2重量部のアルキルアリールポリグリコールエーテル
活性化合物の適切な調製物を製造するために、1重量部の活性化合物を上記量の溶媒及び乳化剤と混合する。得られた濃厚物を水で稀釈して所望の濃度とする。
試験動物: クテノセファリデス・フェリス(Ctenocephalides felis)の成虫
溶媒: ジメチルスルホキシド(DMSO)
適切な調製物を製造するために、20mgの活性化合物と1mLのDMSOから活性化合物の適切な溶液を調製する。この配合物の20μLを4mLのクエン酸処理した蓄牛の血液に加えて撹拌する。
Claims (2)
- 式(I):
Aは、場合により置換されていてもよいアリール、場合により置換されていてもよいヘタリール又は場合により置換されていてもよいヘテロシクリルを表し;
R1は、水素又はC1-C3-アルキルを表し;
R2は、水素又はC1-C3-アルキルを表し;
R3は、水素又はC1-C3-アルキルを表し;
R4は、水素又はC1-C3-アルキルを表し;
Xは、Nを表し;
Yは、CN又はNO2を表し;
Zは、NR5を表し;
R5は、水素を表す]
で表される化合物の製造方法であって、下記式(IX)
で表される化合物を稀釈剤中でトリメチルシリルイソチオシアネートと反応させて、式(IIa):
で表される中間体を形成し、これとハロゲン化アルキルとを稀釈剤の存在下で反応させ、次いで塩基を用いて、式(IIIa):
で表される化合物を得、さらにアンモニア/塩化アンモニウム混合物と反応させて式(II):
で表される化合物を得、さらにシアン化剤またはニトロ化剤を用いて式(I)の化合物に変換することを特徴とする、前記方法。 - 式(IX)で表される化合物。
R1、R2、R3及びR4は請求項1で定義されている通りである]
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DE102006015470A1 (de) * | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
DE102006015456A1 (de) * | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Bicyclische Enamino(thio)carbonylverbindungen |
DE102006015467A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
DE102006015468A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
DE102006046161A1 (de) * | 2006-09-29 | 2008-04-03 | Bayer Cropscience Ag | Neue kristalline Modifikation |
EP2107058A1 (de) * | 2008-03-31 | 2009-10-07 | Bayer CropScience AG | Substituierte Enaminothiocarbonylverbindungen |
US8663182B2 (en) * | 2009-06-02 | 2014-03-04 | The Procter & Gamble Company | Disposable absorbent article with absorbent waistcap or waistband and method for making the same |
EP2493881A1 (de) * | 2009-10-26 | 2012-09-05 | Bayer CropScience AG | Neue feste form von 4-[[(6-chlorpyridin-3-yl)methyl](2,2-difluorethyl)amino]furan-2(5h)-on |
BR112013028895A2 (pt) | 2011-05-10 | 2016-08-09 | Bayer Ip Gmbh | (tio)carbonilamidinas bicíclicas |
WO2013150115A1 (en) | 2012-04-05 | 2013-10-10 | Basf Se | N- substituted hetero - bicyclic compounds and derivatives for combating animal pests |
TWI603962B (zh) | 2016-09-10 | 2017-11-01 | 國立清華大學 | 含硫噁嗪化合物及其合成方法 |
CN108440519B (zh) * | 2018-04-03 | 2020-10-23 | 青岛科技大学 | 一种噁二唑邻苯乙氧基类化合物与用途 |
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US4098791A (en) | 1977-07-29 | 1978-07-04 | The Upjohn Company | Process for preparing 3-(cyanimino)-3-amino-propionitriles |
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DE2921683A1 (de) | 1979-05-29 | 1980-12-11 | Basf Ag | Verfahren zur herstellung von 2,4-diiminothiazolidin |
JPS60233054A (ja) * | 1984-05-02 | 1985-11-19 | Dainippon Pharmaceut Co Ltd | アジリン誘導体およびその製造法 |
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SU1392872A1 (ru) | 1986-01-28 | 1998-04-10 | Иркутский институт органической химии СО АН СССР | 2-имино-4-гидроксиэтиламино-5,5-диметил-2,5-дигидрофуран, обладающий противовоспалительной и анальгетической активностью |
ATE166051T1 (de) | 1987-08-01 | 1998-05-15 | Takeda Chemical Industries Ltd | Zwischenprodukte, ihre herstellung und verwendung zur herstellung alpha-ungesättigter amine |
IL99576A0 (en) * | 1990-10-05 | 1992-08-18 | Ciba Geigy Ag | Triazacyclohexane derivatives |
EP0547557B1 (en) | 1991-12-16 | 1994-07-27 | MITSUI TOATSU CHEMICALS, Inc. | N-vinylimidazolidine derivatives, preparation thereof, insecticides containing same as an effective ingredient and intermediates thereof |
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AU6845094A (en) | 1993-06-07 | 1995-01-03 | Bayer Aktiengesellschaft | Iodopropargyl carbamates and their use as biocides in the protection of plants and materials |
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DE10119423A1 (de) * | 2001-04-20 | 2002-10-24 | Bayer Ag | Neue insektizid wirkende Azole |
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CN1503788A (zh) | 2004-06-09 |
KR20030090699A (ko) | 2003-11-28 |
JP2004532226A (ja) | 2004-10-21 |
WO2002085870A1 (de) | 2002-10-31 |
CA2444592A1 (en) | 2002-10-31 |
AU2008202990B2 (en) | 2012-02-02 |
AU2008202990A1 (en) | 2008-07-31 |
MXPA03009481A (es) | 2004-02-12 |
CN1312138C (zh) | 2007-04-25 |
JP2009227688A (ja) | 2009-10-08 |
CN1250533C (zh) | 2006-04-12 |
NO20034664D0 (no) | 2003-10-17 |
KR100879717B1 (ko) | 2009-01-22 |
US7417150B2 (en) | 2008-08-26 |
BR0209430A (pt) | 2004-08-03 |
KR20080032263A (ko) | 2008-04-14 |
JP2005272472A (ja) | 2005-10-06 |
ES2280565T3 (es) | 2007-09-16 |
DE50209287D1 (de) | 2007-03-08 |
JP4516274B2 (ja) | 2010-08-04 |
AU2002308133B2 (en) | 2008-07-31 |
EP1383751A1 (de) | 2004-01-28 |
NO20034664L (no) | 2003-12-10 |
US20050009839A1 (en) | 2005-01-13 |
NZ528960A (en) | 2005-03-24 |
CN1690051A (zh) | 2005-11-02 |
DE10119423A1 (de) | 2002-10-24 |
ZA200308086B (en) | 2004-10-18 |
KR100845191B1 (ko) | 2008-07-10 |
EP1383751B1 (de) | 2007-01-17 |
BR0209430B1 (pt) | 2013-07-23 |
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