CN1071419A - 取代4-烷氧基嘧啶,其制造方法,含有该化合物的制剂以及其作为病虫害防治剂的应用 - Google Patents
取代4-烷氧基嘧啶,其制造方法,含有该化合物的制剂以及其作为病虫害防治剂的应用 Download PDFInfo
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- CN1071419A CN1071419A CN92111089A CN92111089A CN1071419A CN 1071419 A CN1071419 A CN 1071419A CN 92111089 A CN92111089 A CN 92111089A CN 92111089 A CN92111089 A CN 92111089A CN 1071419 A CN1071419 A CN 1071419A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 title claims description 96
- 238000000034 method Methods 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 201000010099 disease Diseases 0.000 title abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract description 8
- -1 4Be hydrogen Chemical class 0.000 claims abstract description 130
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 55
- 239000001257 hydrogen Substances 0.000 claims abstract description 55
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 29
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 25
- 150000001721 carbon Chemical group 0.000 claims abstract description 21
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000005864 Sulphur Substances 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 230000031709 bromination Effects 0.000 claims description 8
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
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- 230000003647 oxidation Effects 0.000 claims description 6
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
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- 125000005843 halogen group Chemical group 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- QISSZCLKRJOYQS-UHFFFAOYSA-N phenoxyperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOOC1=CC=CC=C1 QISSZCLKRJOYQS-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
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- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 10
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229960003536 phenothrin Drugs 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
- 229950001664 phoxim Drugs 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 229940108410 resmethrin Drugs 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical class [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 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
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- ZDPPRKDPNPMSCU-UHFFFAOYSA-N tetratriacontyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCOP(O)(O)=O ZDPPRKDPNPMSCU-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
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Abstract
本发明涉及上式取代4-烷氧基嘧啶,式中R1为
氢,卤素,烷基或环烷基,R2为氢,必要时取代的烷基
或烷氧基或烷硫基,烷氨基或二烷氨基,R3为氢,烷
基,烷氧基,卤代烷氧基,卤素,烷硫基,氨基,烷氨基
或二烷氨基,R4为氢,烷基,环烷基或卤代烷基且R2
和R3可与碳原子成环,而Q如说明书所述。本发明
还涉及其制备方法,及其作病虫害防治剂的应用。
Description
本发明涉及取代4-烷氧基嘧啶,其制造方法,以及其作为病虫害防治剂,特别是作为杀昆虫剂,杀螨剂,杀线虫剂和杀其菌剂的应用。
已知某些取代4-烷氧基喹唑啉具有良好的杀真菌,杀螨和杀虫效果(EP326328和EP326329)。但在低用量和浓度低时,这些化合物的生物活性并不是在所有情况下均令人满意。
本发明目的是式Ⅰ取代4-烷氧基嘧啶
其中
R1为氢,卤素,(C1-C4)烷基或(C3-C6)环烷基
R2为氢,(C1-C4)烷基,卤素,(C1-C4)卤代烷基,(C1-C10)烷氧基,苯基-(C1-C4)烷氧基,(C1-C10)烷氧基-(C1-C10)烷氧基,苄氧基-(C1-C10)烷氧基,(C1-C10)卤代烷氧基,(C1-C10)烷氧基-(C1-C10)烷基,(C1-C10)烷硫基(C1-C10)烷硫基-(C1-C10)烷基,(C1-C10)烷氨基或二(C1-C10)烷氨基,其中上述基团中的苯基必要时可用(C1-C6)烷基,(C1-C6)烷氧基或卤素取代,
R3为氢,(C1-C4)烷基,(C1-C4)烷氧基,(C1-C4)卤代烷氧基,卤素,(C1-C4)烷硫基,氨基,(C1-C4)二烷氨基,(C1-C4)烷氨基或
R2和R3与其连接的碳原子一起构成不饱和5圆环,其中含氧或硫并且必要时由烷基或卤素取代或
R2和R3与其连接的碳原子一起构成饱和5,6或7圆环,其中含氧或硫并且必要时由烷基取代,
R4为氢,(C1-C4)烷基,(C3-C6)环烷基或(C1-C4)卤代烷基,如CF3,
Q为Q1定义,
Q1为(C1-C15)烷基,其中可有至多3个不饱和键并且必要时可被取代,其取代基可为一,二或三个卤原子,(C3-C8)环烷基,(C1-C15)烷氧基,(C1-C15)烷氧基-(C1-C15)烷氧基,(C1-C15)烷硫基,(C1-C15)烷亚磺酰基,(C1-C15)烷磺酰基,(C1-C15)烷酰基,(C4-C8)环烷基烷氧基,(C4-C8)环烷基烷硫基,苄氧基或苯氧苄氧基或
Q为Q2定义
Q2为式Ⅱa-Ⅱj基团
其中
n为0,1或2,
A为氧,-O-CH2-,硫,亚磺酰或磺酰基,
A′为氧或硫,
D为直接键或(C1-C6)亚烷基,
E为直接键并在D烷基时为氧或亚氨基,
R5,R6和R6′相同或不同,各为氢,卤素,(C1-C8)烷基,(C2-C8)烯基,(C2-C8)炔基,(C3-C6)环烷基,(C1-C8)卤烷基,(C1-C8)烷氧基,(C1-C8)烷硫基,(C1-C8)烷亚磺酰基,(C1-C8)烷磺酰基,(C1-C4)二烷基氨基或硝基,而且在R5,R6和R6′均为烷基时,也可成环,
R7为R5,R6和R6′的定义,而且在E为直接键时,(C1-C4)烷氧基-(C1-C4)烷基,(C1-C4)烷氧羰基,(C1-C8)烷酰基或式Ⅲ基团,
其中X和Y相同或不同,各为硫或氧,
R8为氢或(C1-C4)烷基或
Q为Q3定义,
Q3在不被上述式Ⅱd包括时,为式Ⅳ基团,
其中R5和R6为上述定义,
U为直接键,氧,硫,亚磺酰基,磺酰基或亚甲基,
R9为苯基或杂环基,其中均可不被取代或由一或二个取代基取代,这些取代基相同或不同,各为卤素,(C1-C4)烷基,三氟甲基,硝基,(C1-C4)烷氧基,(C1-C4)烷硫基,(C1-C4)烷亚磺酰基,(C1-C4)烷磺酰基,(C1-C4)烷氧基-(C1-C4)烷基,苯基,苯氧基,(C1-C4)烷氧苯氧基,卤代苯氧基或(C1-C4)烷基苯氧基,
R9在U为氧时还可为(C1-C4)卤代烷基或式Ⅴ基团
其中
W为氮或CR10,
R10为氢,氟,氰基,甲酰基,乙酰基,硝基,甲基,甲氧基或1,3-二氧戊环-2-基,
R11,R12和R13相同或不同,各为(C1-C15)烷基必要时可由一或多个卤素取代或
其中
R6和R6′为上述定义。
优选式Ⅰ化合物中
R1为氢,氯或甲基,
R2为(C1-C4)烷基,氯,三氟甲基,甲氧基,乙氧基或甲氧甲基,
R3为氢,(C1-C3)烷基,甲氧基,乙氧基或卤素或
R2和R3与其连接的碳原子一起构成不饱和5圆环,其中可含氧或硫或R2和R3与其连接的碳原子一起构成饱和5或6圆环,其中可含硫,
R4为氢,甲基,乙基,三氟甲基或环丙基,
Q为Q1,Q2或Q3。
更优选的式Ⅰ化合物中
R1为氢或甲基,
R2为甲基,乙基,三氟甲基,甲氧基,乙氧基或甲氧甲基,
R3为甲基,乙基,甲氧基,氯或溴或
R2和R3与其连接的碳原子一起构成饱和5或6圆环,
R4为氢,甲基,乙基,三氟甲基或环丙基,
Q为Q1,Q2或Q3。
更优选的式Ⅰ化合物中
R1为氢,
R2为甲基,乙基或甲氧甲基,
R3为氯,溴或甲氧基或
R2和R3与其连接的碳原子一起构成饱和6圆环,
R4为氢,甲基或乙基,
Q为Q1,Q2或Q3。
特别优选的式Ⅰ化合物中
R1为氢,
R2为甲氧甲基且R3为甲氧基或
R2为甲基或乙基且R3为氯或溴或
R2和R3与其连接的碳原子一起构成饱和6圆环,
R4为氢,甲基或乙基,
Q为Q1,Q2或Q3。
最优选的水Ⅰ化合物中
R1为氢,
R2为甲氧甲基且R3为甲氧基或
R2为乙基而R3为氯或
R2和R3与其连接的碳原子一起构成饱和6圆环,
R4为氢或甲基,
Q1为(C4-C10)烷基或(C1-C3)烷基,可由环己基,(C4-C8)环烷基烷氧基或(C4-C8)环烷基烷硫基取代。
最为优选的式Ⅰ化合物中
R1为氢,
R2为甲氧甲基且R3为甲氧基或
R2为乙基而R3为氯或
R2和R3与其连接碳原子一起构成饱和6圆环;
R4为氢或甲基,
Q2为式Ⅱa-Ⅱj,如Ⅱa,Ⅱb,Ⅱc,ⅡdⅡf,Ⅱi,Ⅱj,特别是Ⅱa,Ⅱi,Ⅱj的基团,其中D为亚甲基,E为直接键,R5,R6和R6′为氢,(C1-C8)烷基,(C1-C4)烷氧基,环己基或三氟甲基,
R7为甲氧基或乙氧乙基。
最为优选的式Ⅰ化合物中
R1为氢,
R2为甲氧甲基且R3为甲氧基或
R2为乙基和R3为氯或
R2和R3与其连接的碳原子一起构成饱和6圆环,
R4为甲基,乙基或环丙基,
Q为Q3,
R5和R6为氢,
U为氧
R9为苯基或杂环,其中均可未被取代或被一或二个取代基取代这些取代基相同或不同,各为卤素,(C1-C4)烷基,三氟甲基硝基,(C1-C4)烷氧基,(C1-C4)烷硫基或(C1-C4)烷氧基-(C1-C4)烷基。
式Ⅰ中“卤素”为氟,氯,溴或碘,优选氯或溴。“(C1-C4)烷基”指1-4碳直链或支链烷基,如甲基,乙基,丙基,1-甲基乙基,2-甲基丙基或1,1-二甲基乙基。“(C1-C8)烷基”指上述基团以及戊基,2-甲基丁基或2,2-二甲基丙基,己基,庚基或辛基等。
“(C1-C15)烷基”指1-15碳直链或支链烷基,如“(C1-C4)烷基”所述基团和戊基,己基,庚基,辛基,1-壬基,1-癸基,2-癸基,1-十一烷基,2-十一烷基,十二烷基,十三烷基,十四烷基或十五烷基。
“(C3-C6)环烷基”指环丙基,环丁基,环戊基或环己基等。
“(C1-C4)烷氧基”指烷基部分如“(C1-C4)烷基”所述的基团。
“(C1-C15)烷氧基指烷基部分如“(C1-C15)烷基”所述的基团。
“(C1-C4)烷硫基”指烷基部分如“(C1-C4)烷基所述的基团。
“(C1-C15)烷硫基”指烷基部分如“(C1-C15)烷基”所述的基团。
“(C1-C4)烷氧羰基”指烷氧基部分如“(C1-C4)烷氧基”所述的羧酸酯等。
“(C1-C4)卤代烷基”指其中一或多个氢原子由上述卤原子,优选氯或氟取代的“(C1-C4)烷基,如三氟甲基,2,2,2-三氟乙基,氯甲基或氟甲基。
“(C1-C4)卤代烷氧基”指其卤代烃基部分如“(C1-C4)卤代烷基”所述的基团。
“(C1-C4)烷氧基-(C1-C4)烷基”例如为1-甲氧乙基,2-甲氧乙基,2-乙氧乙基,甲氧甲基或乙氧乙基,3-甲氧丙基或4-丁氧丁基。
“(C1-C4)烷硫基-(C1-C4)烷基”例如为甲硫甲基,丙硫甲基,2-甲硫乙基,2-乙硫乙基或3-甲硫丙基。
“(C1-C4)烷氨基”指其烃基部分如“(C1-C4)烷基”所述的基团,优选乙或甲氨基。
“(C1-C4)二烷基氨基”指其烃基部分如“(C1-C4)烷基”所述的基团,优选二甲基或二乙基氨基。
“(C1-C15)烷亚磺酰基”指其烃基部分如“(C1-C15)烷基”所述的基团。
“(C1-C15)烷磺酰基”指其烃基部分如“(C1-C15)烷基”所述的基团。
“(C4-C8)环烷基烷氧基”如环丙基甲氧基,环丙基乙氧基,环丁基甲氧基,环戊基甲氧基,环己基甲氧基或环己基乙氧基,
“(C4-C8)环烷基烷硫基”如环丙基甲硫基,环丙基乙硫基,环丁基甲硫基,环戊基甲硫基,环己基甲硫基或环己基乙硫基,
“(C1-C6)亚烷基”指1-6碳直链或支链亚烷基,如亚甲基,亚乙基,三亚甲基,四亚甲基,-CH(CH3)-,
“(C1-C8)烷酰基”指1-8碳直链或支链烷酰基,如甲酰基,乙酰基,丙酰基,2-甲基丙酰基,丁酰基,新戊酰基,戊酰基,己酰基,庚酰基或辛酰基。
“杂环基”优选为最多10碳杂芳基或由此衍生的部分或完全饱和基,最多10碳的杂芳基可举出例如单,二或三环(C6-C14)芳基,如苯基,萘基或蒽基,其中至少一个CH由N代替和/或其中至少二个相邻CH基由NH,O和/或S代替。这些基团例子为噻吩基,苯并噻吩基,呋喃基,苯并呋喃基,吡咯基,咪唑基,吡啶基,吡嗪基,嘧啶基,哒嗪基,吲哚基,噁唑基,异噁唑基,噻唑基,异噻唑基,苯并噁唑基,苯并噻唑基,异吲啶基,吲唑基,Indalizonyl,Chinolizinyl,喹啉基,异喹啉基,2,3-二氮杂萘酮基,Chinoxalonyl,喹唑啉基,噌啉基,咔唑基,吖啶基,吩嗪基,吩噁嗪基和四唑基,吡唑基。
其碳数偏离上述这些基团或从这些基团衍生的个别基团并不适用于此。
上述说明适用于同系物。
本发明涉及游离碱或其酸加成盐态式Ⅰ化合物,成盐酸可为无机酸,如盐酸,氢溴酸,硝酸,硫酸,磷酸或有机酸,如甲酸,乙酸,丙酸,丙二酸,草酸,富马酸,己二酸,硬脂酸,油酸,甲磺酸,苯磺酸或甲苯磺酸。
式Ⅰ化合物部分具有一或多个非对称碳原子,因此可以外消旋体和非对映体出现。本发明包括异构体混合物。非对映体混合物可按常见方法,如用适用溶剂选择性结晶或经色谱分成各成分。外消旋体可按常见方法分成对映体,如用旋光酸成盐,分出非对映体盐并用碱释放出纯对映体。当然,本发明也包括纯异构体。
本发明还包括式Ⅰ化合物制造方法,其特征是将式Ⅵ化合物
其中R1,R2和R3为式Ⅰ定义,Z为离去基,如卤素,烷硫基,烷磺酰氧基或芳磺酰氧基,烷磺酰基或芳磺酰基,与式Ⅶ醇反应,
其中R4和Q为式Ⅰ定义,必要时在硫醚侧链的硫上将所得式Ⅰ化合物氧化或在嘧啶的C5上氯化或溴化,并必要时将所得化合物成盐。
上述取代反应原则上已知。离去基团可在广泛范围内选择,例如卤原子,如氟,氯,溴或碘或烷硫基,如甲或乙硫基,或烷磺酰氧基如甲,三氟甲或乙磺酰氧基或芳磺酰氧基,如苯或甲苯磺酰氧基或烷磺酰基如甲或乙磺酰基或芳磺酰基,如苯或甲苯磺酰基。
上述反应温度20-150℃,可在碱存在下进行,必要时在惰性有机溶剂中进行,如用N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,二甲亚砜,N-甲基吡咯烷-2-酮,二噁烷,四氢呋喃,4-甲基-2-戊酮,甲醇,乙醇,丁醇,乙二醇,乙二醇二甲醚,甲苯,氯苯或二甲苯,也可用上述溶剂混合物。
适宜碱例如为碱或碱土金属碳酸盐,碳酸氢盐,氨基化合物或氢化合物,如碳酸钠,碳酸氢钠,碳酸钾,氨基化钠或氢化钠,有机锂化合物,如正丁基锂。
本发明还包括式Ⅰ′化合物制备方法,
其中R1,R3,R4和Q为式Ⅰ定义,R2为(C1-C10)烷氧基,(C1-C10)卤代烷氧基,(C1-C10)烷硫基,(C1-C10)烷氨基或(C1-C10)二烷基氨基,其特征是将式Ⅷ化合物
其中Z和Z′相同或不同,为离去基,例如卤素,烷硫基,烷磺酰氧基,芳磺酰氧基,烷磺酰基或磺酰基,而R1和R3为式Ⅰ′定义与式Ⅶ化合物反应,
其中R4和Q为式Ⅰ′定义,得式Ⅸ化合物,
其中R1,R3,R4,Q和Z为上述定义,第二步再将式Ⅷ化合物与式Ⅹ化合物反应,
其中R2′为上述定义,必要时在硫醚侧链的硫上将所得水Ⅰ′化合物氧化必要时或在R3为氢时氯化或溴化,并必要时将所得化合物成盐。
为制得式Ⅰ′化合物,可完全同于上述制造式Ⅰ化合物的方法,即与将式Ⅵ化合物与式Ⅶ化合物反应时同样进行反应。
第二阶段的离去基Z′定义同于上述离去基Z。至于反应条件,第二阶段可采用与用式Ⅵ和Ⅶ化合物制造上述式Ⅰ化合物时相同的溶剂,碱助剂和反应温度。两步反应中可不经处理,而在第一步反应后连续进行反应。
本发明还涉及式Ⅰ′化合物制造方法,其特征是将上述式Ⅷ化合物与式Ⅹ化合物反应而得式Ⅺ化合物
其中R1和R3为式Ⅰ′的定义,R2′为(C1-C4)烷氧基,(C1-C4)卤代烷氧基,(C1-C4)烷硫基,(C1-C4烷氨基或(C1-C4)二烷基氨基,而Z为式Ⅵ定义,再将式Ⅺ化合物与式Ⅶ醇反应,必要时在硫醚侧链的硫上将所得式Ⅰ′化合物氧化或在R3为氢时氯化或溴化。
关于反应条件,可采用与用上述式Ⅵ和Ⅶ化合物制造式Ⅰ化合物时相同的溶剂,碱助剂和反应温度。
两步反应间不进行处理而在第一步反应后连续进行反应。
式Ⅵ初始化合物可类似于已知方法制得,其中原料可用乙酸酯衍生物,经相应的羟基嘧啶而转为卤代嘧啶:
式Ⅶ初始化合物可类似于已知方法用丙二酸酯衍生物制得:
作为原料的式Ⅶ醇也可按已知方法制得:
R3为卤素的式Ⅴ化合物可按已知的方法卤化:
在5-氯衍生物情况下,可引入例如元素氯,次氯酸钠,硫酰氯或N-氯琥珀酰亚胺,溴化特别宜用元素溴或N-溴琥珀酰亚胺,其中溶剂为例如二氯甲烷,氯仿或冰醋酸。
这些有效物质与植物的相容性很好,宜于防治有害动物,特别是昆虫,蛛形纲,蠕虫和软疣,特别宜于防治昆虫和蛛形纲,主要用于农业,畜牧业,林业,仓储业和物资业以及公共卫生领域。
这些有效物质由植物茎和叶吸收性优异并且经basipetalen传送过程而送至根部,因此可有效用于线虫防治。
这些有效物质对具有正常知觉性和抗性的物种以及其全部或个别发育阶段均有防治效果。上述害虫包括:
属于等足目:例如潮虫(球鼠妇),鼠妇(Armadillidium Vulgare),porcellio scaber。
属于倍员目:例如Blaniulus guttulatus。
属于唇足亚纲,例如地蜈蚣(Geophilus carpophagus)蚰蜒(Scutigera spec。)
属于综合纲,例如庭园么蚰。
属于缨尾目,例如西洋衣鱼。
属于弹尾目,例如刺跳虫(Onychiurus armatus)。
属于革翅目,例如欧洲球螋。
属于等翅目,例如散白蚁属。
属于虱目,例如葡萄根瘤蚜,瘿绵蚜属,体虱,盲虱属,长鄂虱属。
属于食毛目,例如羽虱属,畜虱属。
属于缨翅目,例如温室条篱蓟马,烟蓟马。
属于异翅亚目,例如扁盾蝽属,红蝽(Dysdercus intermedius),方背皮蝽,温带臭虫,长江猪蝽,猪蝽属。
属于同翅目,例如甘兰粉虱,木薯粉虱,温室粉虱,棉蚜,甘蓝蚜,茶
隐瘤蚜,敌伏蚜,敌普蚜,苹果绵蚜,梅大尾蚜,麦长管蚜,瘤额蚜属,忽布疣蚜,缢管属,小叶蝉,诱贝蚜,艾辛蚜,水木竖蚧,乌盔蚧,灰飞虱,褐飞虱,红肾圆盾蚧,常春藤圆盾蚧,粉蚧属,木虱属。
属于鳞翅目,例如:红玲麦蛾,松尺蠖,Cheimatobiabrumata蛾,苹细蛾,苹果巢蛾,菜蛾,黄褐天幕毛虫,黄毒蛾,毒蛾,棉潜蛾,桔潜蛾,夜蛾属,切根虫属,地虎属,埃及金刚钻,夜蛾属,甜菜夜蛾,甘蓝夜蛾,松夜蛾,斜纹夜蛾,夜蛾属,粉纹夜蛾,苹果小卷蛾,菜粉蝶属,螟类,玉米螟,地中海粉斑螟,六蜡螟,幕谷蛾,褐织蛾,亚麻黄卷蛾,烟卷蛾,枞色卷蛾,葡萄果蠹蛾,茶长卷蛾,栎绿卷蛾,袋谷蛾。
属于鞘翅目,例如:家具窃蠹,谷蠹,菜锥胸豆象,北美家天牛,杨树萤叶甲,马玲薯叶甲,辣根猿叶,叶甲属,油菜金头跳甲,大豆瓢虫,锯谷盗,花象属,谷象属,黑葡萄耳象,香蕉根颈象,白菜籽龟象,紫苜蓿叶象,皮蠹属,斑皮蠹属,圆皮蠹属,毛皮蠹属,粉蠹属,菜花露尾甲,蛛甲属,黄蛛甲,裸蛛甲,拟谷盗属,黄粉虫,叩头中属,宽胸叩头虫属,西方五月鳃鱼角金龟,马玲薯鳃角金龟,褐新西兰肋翅鳃角金龟。
属于膜翅目,例如:据角叶蜂属,叶蜂属,地蚁属,法老蚁,胡蜂属。
属于双翅目,例如,伊蚊属,按蚊属,库蚊属,黑尾果蝇,象蝇属,厕蝇属,红头丽蝇,绿蝇属,金蝇属,疽蝇科,胃蝇属,赭虱属厩螯蝇属,狂蝇属,皮蝇属,虻属,螗蜩属,毛蚊属,瑞典麦杆蝇,草种蝇属,甜菜泉蝇,地中海蜡实蝇,橄榄大实蝇,欧洲大蚊。
属于蚤目,例如:印鼠客蚤,角叶蚤属。
属于蝽科,例如:蝎蛉,黑寡妇球腹蛛。
属于蜱螨目,例如:粗脚粉螨,锐绿蜱属,纯缘蜱属,鸡皮刺螨,茶
瘿螨,桔芸锈螨,牛蜱属,扁头蜱属,花蜱属,卉乐蜱属,硬啤属,痒螨属,皮痒螨属,疥螨属,跗线螨属,苜蓿苔螨属,全爪螨属,叶螨属,Eotetranychus spp.,Oligonychus spp.,Eutetranychus spp.,
属于蠕虫纲,例如:Haemonchus,Trichostrongulus Ostertagia,Cooperia,Chabertia,Strongyloides Oesophagostomum,Hyostrongulus,Ancylostoma,Ascaris和Heterakis以及Fasciola,还有危害植物的线虫,如防治根结线虫属,狭布叩头虫,茎线虫,内侵线虫,球线虫,草地垫刃线虫属,长囊线虫,剑尾线虫。
Gastropoda 纲,如Deroceras spp.,Arion spp.,Limnaea spp.Galba spp.,Succinea spp.,Biophalaria spp.,Bulirus spp.,Oncomelania spp.。
Bivalva 纲,如Dreissena spp.。
本发明还涉及除适宜配方助剂外还含式Ⅰ化合物的杀虫剂和杀螨剂。
本发明制剂一般含1-95wt%式Ⅰ有效物质。
这些化合物可制成各种制剂,其中通过生物和/或化学物理参数确定,制剂类型可包括可湿性粉剂(WP),乳油(EC),水溶液(SC),油或水乳液,可喷溶液,分散液(SC),悬浮乳液(SC),粉剂(DP),拌种剂,微粒剂,喷粒剂,沉降粒剂和吸附粒剂,可水分散粒剂(WG),ULV制剂,微胶囊,涂蜡剂或诱饵。
这些配方原则上已知,例如已见于:
Winna,cker-Kuechler,“ChemischeTechnologie”,Band 7,C.Hauser Verlag,Muenchen,4.Aufl,1986;Van Falkenberg,“Pesticides Formulations”,Marcel Dekker,N.Y.,2nd Ed.,1972-73;K.Martens,“Spray Drying Handbook”,3rd Ed.1979,G.GoodWin Ltd.,London。
必须的配方助剂,如惰性材料,表面活性剂,溶剂和其它添加剂同样已知并已见于例如:Watkins,“Handbook of Insecticide Dust Diluents and Carriers”,2nd Ed.,Darland Books,Caldwell N.J.;HH.V.Olphen,“Introduction to Clay Colloid Chemistry”,2nd Ed.,J.Wiley & Sons,N.Y.;Marschen,“Solvents Guide”,2nd Ed.,Interscience,N.Y.1950;McCutcheon′s,“Detergents and Emulsifiers Annual”,MC Publ.Corp.,Ridgewood,N.J.;Sisley and Wood,“Encyclopedia of Surface Active Agents”,Chem.Publ.Co.Inc.,N.Y.,1964;Schoenfeldt,“Grenzflaechenaktive Aethylenoxidaddukte”,Wiss.Verlagsgesell.,Stuttgart,1976;Winnacker-Kuechler,“Chemische Techwologie”,Band 7,C.Hauser Verlag,Muenchen,4,Aufl.,1986。
可将矿物油涂到载体物质,如砂,高岭土或造粒惰性物料上。而且适宜的有效物质可按常用于制造肥料颗粒的方式(必要时与肥料混合)造粒。
在可湿性粉剂中有效物质浓度例如约10-90wt%,达到100wt%的其余部分由常见配方成分组成。在乳油中,有效物质浓度约5-80wt%。粉剂含至少5-20wt%有效物质,可喷溶液含约2-20wt%。在粒剂中,有效物质含量部分取决于有效化合物以液态或固态存在和应用哪些选粒助剂,填料等。
除此之外,上述有效物质配方必要时还含有各种常见缓释剂,润湿剂,分散剂,乳化剂,穿透剂,溶剂,填料或载体。
应用时,以常见形式存在的浓缩物必要时可按常规方式稀释,如在可湿性粉剂,乳油,分散液以及有时在微粒剂情况下,可用水稀释。粉剂和粒剂以及可喷溶液在应用前不再用惰性物料稀释。
用量还随外部条件,如温度,湿度等变化,可在宽范围内选择,如选为0.005-10.0kg/ha或用更多的活性物质,但优选0.01-5kg/ha。
本发明活性物质可按其常见商品配方或以这些配方与其它活性物质,如杀虫剂,诱饵,杀菌剂,杀线虫剂,杀真菌剂,生长调节剂或除草剂混合而配制成的其它应用剂型存在。
病虫害防治剂可举出例如磷酸酯,氨基甲酸酯,羧酸酯,甲脒,锡化合物,由微生物制得的物料等。
优选混合组分包括
1.磷化合物
高灭磷,azamethiphos,乙基谷硫磷,甲基谷硫磷,溴硫磷,乙基溴硫磷,毒虫畏,氯甲磷,氯蜱硫磷,甲基氯蜱硫磷,内吸磷,S-甲基内吸磷,S-甲基内吸磷砜,Dialifos,二嗪农,敌敌畏,百治磷,0,0-1,2,2,2-四氯乙基硫代磷酸酯(SD 208 304),乐果,乙拌磷,EPN,乙硫磷,灭克磷,乙嘧硫磷,氨磺磷,Fenamiphos,杀螟松,丰索磷,倍硫磷,地虫磷,安果,庚烯磷,Isozophos,叶蚜磷,异噁唑磷,马拉松,Methacrifos,甲胺磷,杀扑磷,杀抗松,速灭磷,久效磷,二溴磷,氧化乐果,砜吸磷,对硫磷,甲基对硫磷,稻丰散,甲拌磷,伏杀硫磷,棉安磷,Phosmet,磷胺,Phoxim,乙基虫螨磷,甲基虫螨磷,朴吩磷,丙虫磷,Proetamphos,低毒硫磷,田乐磷,Pyridapenthion,喹噁磷,硫普磷,Temephos,Terbufos,杀虫畏,甲基乙拌磷,三唑磷,敌百虫,蚜灭多。
2.氨基甲酸酯
涕灭威,2-仲丁基苯基甲基氨基甲酸酯(BPMC),西维因,虫螨威,硫泛威,氯乙威,氯草胺,杀虫丹,furathiocarb,甲基乙基苯酚甲基氨基甲酸酯,灭多虫,5-甲基-间枯烯基丁酰基(甲基)氨基甲酸酯,草氨酰,抗蚜威,残杀威,Thiodicarb,Thiofanox,4,6,9-三氮杂-4-苄基-6,10-二甲基-8-氧杂-7-氧-5,11-二硫代-9-十二碳烯酸乙酯(OK 135),1-甲硫基(亚乙氨基)-N-甲基-N-(吗啉代硫代)氨基甲酸酯(UC 51717);
3.羧酸酯
丙烯菊酯,α型甲除虫菊,5-苄基-3-呋喃甲基-(E)-(1R)-顺式-2,2-二甲基-3-(2-氧硫亚戊环-3-二基甲基)环丙烷羧酸酯,右旋反丙烯菊酯,右旋反丙烯菊酯((S)-环戊基异构体),右旋反苄呋菊酯,Biphenate,(RS)-1-氰基-1-(6-苯氧基-2-吡啶基)甲基-(IRS)-反式-3-(4-叔丁基苯基)-2,2-二甲基环丙烷羧酸酯(NCI 85193),环丙除虫菊,环氟除虫菊,环卤除虫菊,腈二氯苯醚菊酯,cyphenothrin,δ型甲除虫菊,Empenthrin,Esfenvalerate,伐氟除虫菊,伐丙除虫菊,腈氯苯苯醚菊酯,氟氰除虫菊酯,氟甲除虫菊,氟缬氨酸酯(D-异构体),全甲除虫菊,Pheothrin((R)-异构体),d-Pralethrin,除虫菊酯(天然产物),苄呋喃酯,Tefluthrin,似虫菊,Tralo型甲除虫菊;
4.脒
氨山氮螨,杀虫脒基;
5.锡化合物
三环锡,螨完锡;
6.其它
Abamectin,苏云金杆菌,苄硫丹,乐杀螨,溴螨酯,布洛菲辛,Camphechlor,巴丹,乙酯杀螨醇,Chlorfluazuron,2-(4-(氯苯基)-4,5-二苯基硫酚(UBI-T 930),Chlorfentezine,环丙烷羧酸-(2-萘甲基)酯(R012-0470),曲洛麦芹,N-(3,5-二氯-4-(1,1,2,3,3,3-六氟-1-丙氧基)苯基)氨基甲酰基)-2-氯苄酰亚氨酸乙酯,DDI,开乐散,N-(N-(3,5-二氯-4-(1,1,2,2-四氟乙氧基)苯氨基)羰基)-2,6-二氟苯甲酰胺(XRD 473),Diflubenzuron,N-(2,3-二氢-3-甲基-1,3-噻唑-2-二基)-2,4-二甲苯胺,敌螨通,敌螨普,硫丹,乙氧丙氧芬,(4-乙氧苯基)(二甲基)(3-(3-苯氧苯基)丙基)硅烷,(4-乙氧基苯基)(3-(4-氟-3-苯氧苯基)丙基)二甲基硅烷,伐氧威,2-氟-5-(4-(4-乙氧苯基)-4-甲基-1-戊基)二苯醚(MTI 800),克拉灵和开朴敌,Fenthiocarb,Flubenzimine,Flucycloxuron,Flufenoxuron,r.-HCH,六噻斯,Hydramethylnon(AC 217300)Ivermectin,2-硝基甲基-4,5-二氢-6H-噻嗪(SD52618),2-硝基甲基-3,4-二氢噻唑(SD 35651),2-硝基亚甲基-1,2-噻嗪烷-2-基氨基甲醛(WL 108-77),克满特,Teflubenzuron,四氯杀螨砜,杀螨好,Thiocyclam,Triflumuron。
用市售商品配方制成的应用剂型中有效物质量可为0.00000000.00000001-100wt%,优选0.00001-1wt%。
可按宜于应用剂型的常见式进行应用。
本发明化合物还宜于在兽医或动物饲养上防治内和外寄生虫。
以这些配方为基础,还可混入其它农药有效物质,肥料和/或生长调节剂而制成混合制剂,如以预制配方或以Tankmix形式制成。可湿性粉剂为在水中均匀分散的制剂,其中除活性物质,稀释剂或惰性物质而外,还可含润湿剂,如聚氧乙基化烷基酚,聚氧乙基化脂肪醇,烷基或烷基酚-磺酸酯和分散剂,如木素磺酸钠,2,2′-二萘基甲烷-6,6′-二磺酸钠,二丁基萘磺酸钠或油酰甲基牛磺酸钠。可通过将有效物质溶于有机溶剂,如丁醇,环己酮,二甲基甲酰胺,二甲苯或高沸点芳烃或烃中并加入-或多种乳化剂而制成乳油。乳化剂可用例如:烷芳基磺酸钙盐,如十二烷基苯磺酸钙或非离子乳化剂,如脂肪酸聚二醇酯,烷芳基聚二醇醚,脂肪醇聚二醇醚,环氧丙烷-环氧乙烷缩合产物,烷基聚醚,脱水山梨糖醇脂肪酸酯,聚氧乙烯脱水山梨糖醇脂肪酸酯或聚氧乙烯山梨醇酯。
粉剂可通过将有效物质与固体细粉,如滑石,天然陶土,如高岭土,膨润土,Pyrophillit或硅藻土混合而制成。将有效物质喷到有吸附能力的惰性物料上或用粘结剂,如聚乙烯醇,聚丙烯酸钠或其它适宜粘结剂使有效物质浓缩物成粒而制成粒剂。
使用本发明提出的生物活性物质时可采用通常的使用方式,例如采用片剂,胶囊,饮料及粒剂等口服形式,也可用经皮肤使用的方式,例如浸泡(浸渍),喷射(喷洒),喷淋(浇灌和喷淋)和撒粉以及采用肠胃外应用的形式,如注射。
因此,本发明式Ⅰ新化合物也特别适宜于家畜(如牛,羊,猪和家禽,如鸡,鹅等)。在本发明优选实施方案中,新化合物,必要时以合适的配方(如上述)并且必要时与饮用水或饲料混合给动物口服。由于可以有效方式在粪便中排泄,所以按此方式可极简单地使病虫在动物粪便中的生长受到抑制。适宜的剂量和配方与施用动物的种类和发育阶段以及病害程度关系很大,这可很容易地按常规方法确定。这些新化合物用于牛时,剂量如为0.01-1mg/kg体重。
本发明式Ⅰ化合物还是有惊人的杀真菌作用,可成功地防治了浸入植物组织中的真菌病原体。这一点非常重要,并且可有效地用于防治吸入感染后用常用杀真菌剂不能有效防治的病害。本发明化合物的效用中心包括许多不同的具有经济意义的植物病原菌,如稻梨孢,苹果黑星菌,菾菜生尾孢,echte Mehltauarten,镰孢菌属,葡萄生单轴霉,各种Rostpilze和Pseudocercoporella herpotrichoides。
除此之外,本发明化合物还适用于各工业领域,如作为森林防护剂,在涂料中或在金属加工用冷却润滑剂中作防腐剂,还可在钻孔或切割用油中作防腐剂。
本发明还涉及杀真菌剂,其中除适宜的配方助剂外,还含式Ⅰ化合物。本发明制剂含式Ⅰ有效物质一般为1-95wt%。
这些化合物可制成各种制剂,其中通过生物和/或化学物理参数确定,制剂类型可包括可湿性粉剂(WP),乳油(EC),油或水分散液(SC),悬浮乳液(SC),粉剂(DP),拌种剂,可水分散粒剂(WG),ULV制剂,微胶囊,涂蜡剂或诱饵。
这些配方原则上已知,例如已见于:
Winnacker-Kuechler,“Chemiche Technologie”,Band 7,C.Hauser Verlag,Muenchen,4.Aufl.1986;van Falkenberg,“Pesticides Formulations”,Marcel Dekker,N.Y.,2nd Ed.,1972-73;K.Martens,“Spray Drying Handbook”,3rd Ed.1979,G.Goodwin Ltd.,London。
必须的配方助剂,如惰性材料,表面活性剂,溶剂和其它添加剂同样已知并已见于例如:Watkins,“Handbook ofInsecticide Dust Diluents and Carriers”,2nd Ed.,Darland Books,Caldwell N.J.;H.V.Olphen,“Introduction to Clay Colloid Chemistry”,2nd Ed.,J.Wiley & Sons,N.Y.;Marschen,“Solvents Guide”,2nd Ed.,Interscience,N.Y.1950;McCutcheon′s“Detergents and Emulsifiers Annual”,MC Publ.Corp.,Ridgewood,N.J.;Sisley and Wood,“Encyclopedia of Surface Active Agents”,Chem.Publ.Co.Inc.,N,Y.,1964;Schoenfeldt,“Grenzflaechenaktive Aethylenoxidaddukte,Wiss.Verlagsgesell.,Stuttgart,1976;Winnacker-Kuechler,“Chemische Technologie”,Band 7,C.Hauser Verlag,Muenchen,4.Aufl.,1986。
以这些配方为基础,还可混入其它农药有效物质,肥料和/或生长调节剂而制成混合制剂,如以预制配方或以Tankmix形式制成。
可湿性粉剂为在水中可均匀分散的制剂,其中除活性物质,稀释剂或惰性物质而外,还可含润湿剂,如聚氧乙基化烷基酚,聚氧乙基化脂肪醇,烷基或烷基酚磺酸盐和分散剂,如木素磺酸钠,2,2′-二萘基甲烷-6,6′-二磺酸钠,二丁基萘磺酸钠或油酰甲基牛磺酸钠。可通过将有效物质溶于有机溶剂,如丁醇,环己酮,二甲基甲酰胺,二甲苯或高沸点芳烃或烃中并加一或多种乳化剂而制得乳油。乳化剂可采用例如:烷芳基磺酸钙盐,如十二烷基苯磺酸钙或非离子乳化剂,如脂肪酸聚二醇酯,烷芳基聚二醇醚,脂肪醇聚二醇醚环氧丙烷-环氧乙烷-脱水山梨糖醇脂肪酸酯,聚氧乙烯脱水山梨糖醇脂肪酸酯或聚氧乙烯山梨糖醇酯。
可将有效物质与固体物料细粉,如滑石,天然陶土,如高岭土,膨润土,Poryphillit或硅藻土组合而得粉剂。粒剂制造方法是将有效物质喷到有吸附能力的惰性物料颗粒上或将有效物质浓缩物用粘合剂,如聚乙烯醇,聚丙烯酸钠或矿物油涂到载体,如砂,高岭土或粒状惰性物料的表面上。而且,适宜的有效物质可按常用于制造颗粒的方式(必要时与肥料混合)造粒。
在可湿性粉剂中有效物质浓度例如约10-90wt%,达到100wt%的其余部分由常见配方成分组成。在乳油中,有效物质浓度约5-80wt%。粉剂含至少5-20wt%有效物质,可喷溶液含约2-20wt%。在粒剂中,有效物质含量部分取决于有效化合物以液态或固态存在和应用哪些选粒助剂,填料等。
除此之外,上述有效物质配方必要时还含有各别常见缓释剂,润湿剂,分散剂,乳化剂,穿透剂,溶剂,填料或载体。
应用时,以常见形式存在的浓缩物必要时可按常规方式稀释,如在可湿性载体,乳油,分散液以及有时在微粒剂情况下,可用水稀释。
粉剂和粒剂以及可喷溶液在应用前不再用惰性物料稀释。
用量还随外部条件,如温度,湿度等变化,可在宽范围内选择,如选为0.005-10.0kg/ha或用更多的活性物质,但优选0.01-5kg/ha。
本发明有效物质可以其市售商品配方单独或与文献中已知的其它杀真菌剂并用。
作为文献中已知并可与本发明的式Ⅰ化合物并用的杀真菌剂,可举出:
敌菌灵,Benalaxyl,麦锈灵,苯菌灵,乐杀螨,Bitertanol,Buthiobat,Captafol,克菌丹,多菌灵,萎锈灵,CGD-94240F,Chlobenzthiazone,百菌清,Cymoxam′l,Cyproconazole,Cyprofuram,抑菌灵,Dichlomezin,Diclobutrazol,Diethofencarb,Difluconazole,甲菌定,Dimethomorph,Diniconazole敌满普,二嗪农,吗菌灵,多果定,尺瘟散,乙菌定,Etridiazol,Fenarimol,甲基苯基呋喃羧酰胺,Fenpiclonil,Fenpropidin,Fenpropomorph,薯瘟锡,毒菌锡,Fluaziram,Fluobenzimine,Fluorimide,Flusinazole,Flutolanil,Flutriafol,灭菌丹,Fosetylaluminium,麦穗宁,Furalaxyl,Farmecyclox,双胍盐,Hexaconazole,Imazalil,Iprobenfos,二氯苯基甲乙基三氧咪唑烷羧酰胺,富士一号,铜化合物。如氧氯化铜,吡喃铜,氧化铜,Mancozeb,代森锰,Mepromil,Metalaxyl,Methasulfocarb,三甲基苯基呋喃羧酰胺,Myclobuttanil,代森钠,Nitrothalidopropyl,Nuarimol,Ofurace,Oxadixyl,萎锈散,Penconazol,Pencycuron,pp969,苯菌灵,Probineb,Prochloraz,Procymidon,Propamocarb,Propiconazole,胺丙威,比锈灵,Pyrofenox,Pyroquilon,Rabenzazole,硫,Tebuconazole,涕必灵,Thiofanatemethyl,福美双,Tolclofos-methyl,对甲抑菌灵,Triadimefon,氯苯氧基二甲乙基三唑乙醇,Tricyclazole,克啉菌,Triflumizol,嗪氨灵,Vinchlozolin,代森锌,十二烷基苯磺酸钠,十二烷基硫酸钠,C13/C15醇醚磺酸钠,鲸蜡基硬脂酰磷酸酯钠盐,二辛基磺酰琥珀酸钠,异丙基萘磺酸钠,亚甲双萘磺酸钠,鲸蜡基三甲基氯化铵,长链伯,仲或叔胺盐,烷基亚丙基胺,月桂基溴化嘧啶鎓,乙氧基化脂肪季铵,烷基二甲基苄基氯化铵和1-羟乙基-2-烷基咪唑啉。
上述混合组分为已知活性物质,大部分已见于C.R.Worthing,S.B.Walker,The pesticide Manual,7.Auflage(1983),Britis Corp Protection Council。
因此,本发明活性物质,特别是下述实施例的化合物可以其市售商品配方或以用这些配方制成的应用剂型与其它活性物质。如杀虫剂,消毒剂,杀菌剂,杀螨剂,杀线虫剂,杀真菌剂,生长调节剂或除草剂混合的形式存在。
各应用剂型的市售商品配方中活性物质含量可在很宽范围内变化,应用剂型的活性物质浓度0.0001-100wt%,优选0.001-1wt%。
应用按其宜于所用剂型的常见方式进行。
用下述实例对本发明加以说明。
A.配方实施例
a)粉剂由10份(重量)生物活性物质和90份(重量)滑石作为惰性材料进行混合而制得,并经锤磨机粉碎。
b)易在水中分散的可湿性粉剂由25份(重量)生物活性物质,65份(重量)含高岭土的石英作为惰性材料,10份(重量)木质素磺酸钾1份(重量)油酰甲牛磺酸钠作为润湿剂和分散剂进行混合而制得,并经棒磨机研磨。
c)易分散于水中的分散体浓缩物由40份(重量)生物活性物质与7份(重量)磺酰琥珀酸半酯,2份(重量)木素磺酸钠和51份(重量)水混合制成,并经球磨机研磨至粒度低于5μm。
d)乳油由15份(重量)生物活性物质,75份(重量)环己酮作为溶剂以及10份(重量)氧乙基化壬基苯酚(10 Aeo)作为乳化剂而制得。
e)颗粒剂由2至15份(重量)生物活性物质及惰性粒状载体材料,如绿坂缕石,浮石粒料及/或石英砂而制得。可有效地应用固体物质含量30%的例b)的可湿性粉剂悬浮液,其中将该液喷到绿坂缕石颗粒表面上,干燥并混合均匀。可湿性粉剂重量占固体颗粒的约约5%,而惰性载体重量占固体颗粒的约95%。
B)化学实施例
实施例A
向1.2g(0.03mol)氢化钠(油中60%分散体)的50ml无水DMF(二甲基甲酰胺)悬浮液中50℃滴加5.4g(0.03mol)2-(4-叔丁苯基)乙醇并搅拌至生成水的反应结束。冷至0℃后加入4.7g(0.025mol)4-氯-5-甲氧基-6-甲氧甲基嘧啶(Coll.Czechoslov.Chem.Commun.33,2266(1968)。室温搅拌1h后100℃搅拌2h。用二氯甲烷/水分出溶剂,有机相干燥并浓缩。粗产物用硅胶柱色谱(乙酸乙酯)分离得3.8g(理论值的46%)黄色油状4-〔2-(4-叔丁苯基)乙氧基〕-5-甲氧基-6-甲氧基甲基嘧啶。
实施例B
向1.2g(0.03mol)氢化钠(油中60%分散体)和5.7g(0.03mol)4-氯-5-甲氧基-6-甲氧甲基嘧啶在50ml无水DMF中的混合物中10-20℃滴加入5.8g(0.03mol)3-(4-叔丁苯基)丙醇的20ml无水DMF溶液。室温搅拌1h后100℃搅拌2h。类似实施例A处理和色谱提纯后得2.5g(24%)黄色油状4-〔3-(4-叔丁苯基)丙氧基〕-5-甲氧基-6-甲氧甲基嘧啶。
实施例C
向680mg(22.7mmol)氢化钠(油中80%悬浮液)的40ml无水THF(四氢呋喃)悬浮液中40℃滴加22.40g(15.2mmol)2-(4-氯苯基)乙醇并搅拌至生成水的反应结束。然后冷至室温并分批加2.7g(15.2mmol)4,6-二氯-5-甲氧嘧啶(Monatshefte Chem.96,1661(1965))。室温搅拌1h后40℃搅拌4h处理时将反应混合物倒入饱和氯化铵溶液中并用二乙醚提取。组合的有机相硫酸镁干燥并真空浓缩,剩余物用硅胶柱色谱(正庚烷/乙酸乙酯:4/1)提纯而得4.0g(理论值的88%)粘性4-〔2-(4-氯苯基)乙氧基〕-5-甲氧基-6-氯嘧啶,干燥时缓慢结晶(熔点70-71℃)。
实施例D
向650mg(21.6mmol)氢化钠(油中86%悬浮液)的60ml无水DMF悬浮液中50℃滴加2.7g(17.0mmol)2-十二烷醇并搅拌至生成水的反应结束。冷至室温后分批加3.0g(15.9mmol)4-氯-5-甲氧基-6-乙氧基嘧啶(类似于实施例C制造)。30分钟后将反应温度提高到50℃并再搅拌12h。反应混合物倒入氯化铵溶液中并用二乙醚萃取。组合有机相用水洗涤,硫酸镁干燥后真空浓缩。剩余物用硅胶柱色谱(正庚烷/乙酸乙酯:4/1)提纯而得1.4g(理论值的28%)黄色油状4-(2-癸氧基)-5-甲氧基-6-乙氧基嘧啶。
实施例E
向700mg(23.3mmol)氢化钠(油中80%悬浮液)的50ml无水THF悬浮液中加入3.8g(17.8mmol)2-〔4-(苯氧基)苯基〕乙醇并50℃搅拌至生成水的反应结束。冷至室温后加3.0g(17.8mmol)4-氯-5,6,7,8-四氢喹唑啉,然后5h加热到40℃。将反应混合物倒入饱和氯化铵溶液中并用二乙醚提取。组合有机相用硫酸钠干燥并真空浓缩。剩余物用硅胶柱色谱(正庚烷/乙酸乙酯:2/1)提纯而得3.2g粘性黄色油状4-〔2-(4-(苯氧)苯基)乙氧基〕-5,6,7,8-四氢喹唑啉。
其它实施例见表1,表中所列基团R1至R对应于式Ⅰ中的符号:
C)生物实施例
实施例1
大麦植物3叶期由粉霉病孢子(Erysiphe graminisf.sp.hordei)大量接种并移入20℃和90-95%的空气相对湿度下的温室中。接种后24小时,用表Ⅳ所列给定活性物质浓度的化合物均匀润湿植物。保留10天后观察感染大麦粉霉病的植物。感染程度计为感染面积%表示,以未处理感染对照植物(=100%感染)计,结果列在表Ⅳ中。
表Ⅳ
化合物对应实施例 大麦感染粉霉病叶面积%
(mg活性物质/1喷洒液)
500 250
4 0 0
34 0 0
40 0 0
43 0 0
45 0 0
46 0 0
65 0 3
66 0 5
72 0 0
73 0 0
74 0 0
75 0 0
76 0 5
77 0 0
78 0 0
未处理感染植物 100
实施例2
“Jubilar”种小麦植物2叶期用表Ⅴ所列制剂的水悬浮液喷淋处理。
喷洒液膜放干后,植物用Leptosphaeria nodorum的Pykno孢子水悬浮液接种并移入100%空气相对湿度的温室中培养数小时。开始出现症状后将植物移入约90%空气相对湿度的温室中进一步培养。
感染程度用与未处理感染对照植物比较的%感染叶面积计,结果列于表Ⅴ。
表Ⅴ
化合物对应实施例 感染Leptosphaeria nodorum叶面积%
(mg活性物质/l喷洒液)
500 250 125
5 0 3 5
41 0 0 0
61 0 3 -
64 0 0 3
72 0 0 -
74 0 0 0
75 0 0 0
76 0 0 0
78 0 0 5
83 0 5 -
100 0 5 -
未处理感染植物 100
实施例3
“Igri”种大麦植物2叶期用要求的化合物水悬浮液喷洒处理。
喷洒液膜放干后,植物用圆核腔菌孢子水悬浮液接种并移入100%空气相对湿度下的温室中培养。然后将感染植物移入25℃和80%空气相对湿度下的温室中再培养。
接种后约1星期评价感染,其中感染程度计为与未处理感染对照植长比较的%感染叶面积,结果也列在表Ⅵ中。
表Ⅵ
化合物对应实施例 感染圆核腔菌叶面积%
(mg活性物质/1喷洒液)
500 250 125
3 0 0 -
4 0 0 5
5 0 0 0
15 0 0 0
34 0 0 0
42 0 0 -
66 0 0 0
67 0 0 3
74 0 0 0
75 0 0 0
76 0 0 0
77 0 0 0
81 0 0 5
82 0 0 0
98 0 0 0
未处理感染植物 100
实施例4
“Julibar”种小麦2叶期用要求化合物水悬浮液喷洒处理。
喷洒液膜放干后,植物用隐柄锈菌孢子水悬浮液接种。植物湿淋地放入20℃和约100%相对空气湿度下的温室中培养约16小时。然后将感染植物再移入22-25℃和50-70%相对湿度下的温室中再培养。
约2星期培养后,真菌在整未处理对照植物叶表面上形成孢子,这样就可进行感染程度评价,其中感染程度计为与未处理感染对照植物比较的感染叶表面积%,结果列在表Ⅶ中。
表Ⅶ
化合物对应实施例 隐 柄锈菌感染叶表面%
(mg安性物质/1喷洒液)
500 250 125
1 0 0 -
4 0 0 -
5 0 0 0
8 0 0 -
16 0 0 -
31 0 0 -
61 0 0 5
63 0 5 10
64 0 - -
65 0 0 0
77 0 0
78 0 0
99 0 0
实施例5
放有大量菜豆(Tetranychus urticae,Vollpopulaton)的菜豆植物(Phaseolus V.)用均含250ppm的喷粉浓缩物水稀释液喷洒。7天后检查死亡率,结果发现达到100%死亡率的化合物为实施例4,5,14,23,42,43,46,47,49,50,51,65,69,73,74,75,82,90,92,95,100,102和840的化合物。
实施例6
大量放有黑菜豆蚜虫(Aphis fabae)的大田菜豆(Vicia faba)用活性物质含量为250ppm的喷粉浓缩物稀释液喷洒,直到落下液滴为止。3天后确定蚜虫死亡率,达到100%死亡率的化合物有实施例4,5,42,46,49,65,66,73,74,75,77,87和102的化合物。
实施例7
在玻璃盘盖和底盘内侧,将各1ml的试验配方乳化,均匀分散在水中并在液膜放干后各加入10只苍蝇成虫(Musca domestica)。锁上盘后室温下保存并在3小时后确定试验动物死亡率。在250ppm(以活性物质计)下,实施例4,15,16,46,49,59,63,72,73,77,78,79,98,99和841的化合物制剂对苍蝇具有很好的效用(100%死亡)。
实施例8
呈椭圆形放有棉花虫(Oncopeltus fasciatus)滤纸盘用0.5ml试验配方的水稀释液处理。液膜放干后盖上盘并使室内保持最高空气湿度。室温保存7天后确定ovizide作用。在250ppm活性物质含量下,实施例1,2,4,5,14,15,16,30,33,34,35,40,41,43,45-50,53,58,59,61,64,65,66,72,73,74,76,77,83,84,87,89,90,95,102,839和841的化合物达到100%的死亡率。
Claims (19)
1、式Ⅰ化合物及其盐和立体异构体制备方法
其中
R1为氢,卤素,(C1-C4)烷基或(C3-C6)环烷基,
R2为氢,(C1-C4)烷基,卤素,(C1-C4)卤代烷基,(C1-C10)烷氧基,苯基-(C1-C4)烷氧基,(C1-C10)烷氧基-(C1-C10)烷氧基,苄氧基-(C1-C10)烷氧基,(C1-C10)卤代烷氧基,(C1-C10)烷氧基-(C1-C10)烷基,(C1-C10)烷硫基,(C1-C10)烷硫基-(C1-C10)烷基,(C1-C10)烷氨基或二(C1-C10)烷氨基,其中上述基团中的苯基必要时可用(C1-C6)烷基,(C1-C6)烷氧基或卤素单取代,
R3为氢,(C1-C4)烷基,(C1-C4)烷氧基,(C1-C4)卤代烷氧基,卤素,(C1-C4)烷硫基,氨基,(C1-C4)烷氨基,(C1-C4)二烷氨基或
R2和R3与其连接的碳原子一起构成不饱和5圆环,其中含氧或硫并且必要时由烷基或卤素取代或
R2和R3与其连接的碳原子一起构成饱和5,6或7圆环,其中含氧或硫并且必要时由烷基取代,
R4为氢,(C1-C4)烷基,(C3-C6)环烷基或(C1-C4)卤代烷基,如CF3,
Q为Q1定义,
Q1为(C1-C15)烷基,其中可有至多3个不饱和键并且必要时可被取代,其取代基可为一,二或三个卤原子,(C3-C8)环烷基,(C1-C15)烷氧基,(C1-C15)烷氧基-(C1-C15)烷氧基,(C1-C15)烷硫基,(C1-C15)烷亚磺酰基,(C1-C15)烷磺酰基,(C1-C15)烷酰基,(C4-C8)环烷基烷氧基,(C1-C8)环烷基烷硫基,苄氧基或苯氧苄氧基或
Q为Q2定义
Q2为式Ⅱa-Ⅱj基团
其中
n为0,1或2,
A为氧,-O-CH2-,硫,亚磺酰或磺酰基,
A1为氧或硫,
D为直接键或(C1-C6)烷基,
E为直接键并在D为烷基时为氧或亚氨基,
R5,R6和R6′相同或不同,各为氢,卤素,(C1-C8)烷基,(C2-C8)烯基,(C2-C8)炔基,(C2-C6)环烷基,(C1-C8)卤烷基,(C1-C8)烷氧基,(C1-C8)烷硫基,(C1-C8)烷亚磺酰基,(C1-C8)烷磺酰基,(C1-C4)二烷基氨基或硝基,而且在R5,R6和R6′均为烷基时,也可成环,
R7为R5,R6和R6′的定义,而且在E为直接键时,为(C1-C4)烷氧基-(C1-C4)烷基,(C1-C4)烷氧羰基,(C1-C8)烷酰基或式Ⅲ基团,
其中X和Y相同或不同,各为硫或氧,
R8为氢或(C1-C4)烷基或
Q为Q3定义,
Q3为不被上述式Ⅱd包括时,为式Ⅳ基团,
其中R5和R6为上述定义,
U为直接键,氧,硫,亚磺酰基,磺酰基或亚甲基,
R9为苯基或杂环基,其中均可不被取代或由一或二个取代基取代,这些取代基相同或不同,各为卤素,(C1-C4)烷基,三氟甲基,硝基,(C1-C4)烷氧基,(C1-C4)烷硫基,(C1-C4)烷亚磺酰基,(C1-C4)烷磺酰基,(C1-C4)烷氧基-(C1-C4)烷基,苯基,苯氧基,(C1-C4)烷氧苯氧基,卤代苯氧基或(C1-C4)烷基苯氧基,
R9在U为氧时还可为(C1-C4)卤代烷基或式Ⅴ基团
其中
W为氮或CR10,
R10为氢,氟,氰基,甲酰基,乙酰基,硝基,甲基,甲氧基或1,3-二氧戊环-2-基,
R11,R12和R13相同或不同,各为(C1-C15)烷基,必要时可由一或多个卤素取代或
其中
R6和R6′为上述定义。
其特征是将式Ⅵ化合物
其中R1,R2和R3为式Ⅰ定义,Z为离去基,如卤素,烷硫基,烷磺酰氧基或芳磺酰氧基,烷磺酰基或芳磺酰基,与式Ⅶ醇反应,
其中R4和Q为式Ⅰ定义,必要时在硫醚侧链的硫上将所得式Ⅰ化合物氧化或在嘧啶的C5上氯化或溴化,并必要时将所得化合物成盐。
2、权利要求1的方法,其特征是式Ⅰ中
R1为氢,氯或甲基,
R2为(C1-C4)烷基,氯,三氟甲基,甲氧基,乙氧基或甲氧甲基,
R3为氢,(C1-C4)烷基,甲氧基,乙氧基或卤素或
R2和R3与其连接的碳原子一起构成不饱和5圆环,其中可含氧或硫或R2和R3与其连接的碳原子一起构成饱和5或6圆环,其中可含硫,
R4为氢,甲基,乙基,三氟甲基或环丙基,
Q为Q1,Q2或Q3。
3、权利要求1的方法,其特征是式Ⅰ中
R1为氢或甲基,
R2为甲基,乙基,三氟甲基,甲氧基,乙氧基或甲氧甲基,
R3为甲基,乙基,甲氧基,氯或溴或
R2和R3与其连接的碳原子一起构成饱和5或6圆环,
R4为氢,甲基,乙基,三氟甲基或环丙基,
Q为Q1,Q2或Q3。
4、权利要求1的方法,其特征是式Ⅰ中
R1为氢,
R2为甲基,乙基或甲氧甲基,
R3为氯,溴或甲氧基或
R2和R3与其连接的碳原子一起构成饱和6圆环,
R4为氢,甲基或乙基,
Q为Q1,Q2或Q3。
5、权利要求1的方法,其特征是式Ⅰ中
R1为氢
R2为甲氧甲基且R3为甲氧基或
R2为甲基或乙基且R3为氯或溴或
R2和R3与其连接的碳原子一起构成饱和6圆环,
R4为氢,甲基或乙基,
Q为Q1,Q2或Q3。
6、权利要求1的方法,其特征是式Ⅰ中
R1为氢,
R2为甲氧甲基且R3为甲氧基或
R2为乙基而R3为氯或
R2和R3与其连接的碳原子一起构成饱和6圆环,
R4为氢或甲基,
Q1为(C4-C10)烷基或(C1-C3)烷基,可由环烷基,(C4-C8)环烷基烷氧基或(C4-C8)环烷基烷硫基取代。
7、权利要求1的方法,其特征是式Ⅰ中
R1为氢,
R2为甲氧甲基且R3为甲氧基或
R2为乙基而R3为氯或
R2和R3与其连接碳原子一起构成饱和6圆环,
R4为氢或甲基,
Q2为式Ⅱa-Ⅱj,如Ⅱa,Ⅱb,Ⅱc,ⅡdⅡf,Ⅱi,Ⅱj,特别是Ⅱa,Ⅱi,Ⅱj的基团,其中D为亚甲基,E为直接键,R5,R6和R6′为氢,(C1-C8)烷基,(C1-C4)烷氧基,环己基或三氟甲基,
R7为甲氧乙基或乙氧乙基。
8、权利要求1的方法,其特征是式Ⅰ中
R1为氢,
R2为甲氧甲基且R3为甲氧基或
R2为乙基和R3为氯或
R2和R3与其连接的碳原子一起构成饱和6圆环
R4为甲基,乙基或环丙基,
Q为Q3,
R5和R6为氢,
U为氧
R9为苯基或杂环,其中均可未被取代或被一或二个取代基取代这些取代基相同或不同,各为卤素,(C1-C4)烷基,三氟甲基硝基,(C1-C4)烷氧基,(C1-C4)烷硫基或(C1-C4)烷氧基-(C1-C4)烷基。
9、式Ⅰ′化合物制备方法
其中R1,R3,R4和Q为式Ⅰ定义,R2为(C1-C10)烷氧基,(C1-C10)卤代烷氧基,(C1-C10)烷硫基,(C1-C10)烷氨基或(C1-C4)二烷基氨基,其特征是将式Ⅷ化合物
其中Z和Z′相同或不同,为离去基,例如卤素,烷硫基,烷磺酰氧基,芳磺酰氧基,烷磺酰基或其磺酰基,而R1和R3为式Ⅰ′定义与式Ⅶ化合物反应,
其中R4和Q为式Ⅰ′定义,得式Ⅸ化合物,
其中R1,R3,R4,Q和乙为上述定义,第二步再将式Ⅷ化合物与式X化合物反应,
其中R2′为上述定义,必要时在硫醚侧链的硫上将所得式Ⅰ′化合物氧化或必要时或在R3为氢时氯化或溴化,并必要时将所得化合物成盐。
10、权利要求9的式Ⅰ′化合物制备方法,其特征是将上述式Ⅷ化合物与式Ⅹ化合物反应而得式Ⅺ化合物,
其中R1和R3为式Ⅰ′的定义,R2′为(C1-C4)烷氧基,(C1-C4)卤代烷氧基,(C1-C4)烷硫基,(C1-C4)烷氨基或(C1-C4)二烷基氨基,而Z为式Ⅳ定义,再将式Ⅸ化合物与式Ⅶ醇反应,必要时在硫醚侧链的硫上将所得式Ⅰ′化合物氧化或在R3为氢时氯化或溴化。
11、杀虫剂或杀螨剂,其特征是其中含有效量权利要求1所得式Ⅰ化合物。
12、杀真菌剂,其特征是其中含有效量权利要求1所得式Ⅰ化合物。
13、杀线虫剂,其特征是其中含有效量权利要求1所得式Ⅰ化合物。
14、应用权利要求1所述的式Ⅰ化合物防治害虫和。
15、应用权利要求1所述的式Ⅰ化合物防治有害真菌。
16、应用权利要求1所述的式Ⅰ化合物防治线虫。
17、害虫和螨防治方法,其特征是将有效量权利要求1所得式Ⅰ化合物喷酒到害虫和螨上或其所在的植物,叶或根基上。
18、有害真菌防治方法,其特征是将有效量权利要求1所得式Ⅰ化合物喷酒到真菌上或其所在的植物,叶或根基上。
19、线虫防治方法,其特征是将有效量权利要求1所得式Ⅰ化合物喷酒到线虫上或其所在的植物,叶或根基上。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4131924A DE4131924A1 (de) | 1991-09-25 | 1991-09-25 | Substituierte 4-alkoxypyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
DEP4131924.9 | 1991-09-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1071419A true CN1071419A (zh) | 1993-04-28 |
Family
ID=6441469
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN92111089A Pending CN1071419A (zh) | 1991-09-25 | 1992-09-25 | 取代4-烷氧基嘧啶,其制造方法,含有该化合物的制剂以及其作为病虫害防治剂的应用 |
Country Status (11)
Country | Link |
---|---|
US (1) | US5859020A (zh) |
EP (2) | EP0605552A1 (zh) |
JP (1) | JPH06510993A (zh) |
CN (1) | CN1071419A (zh) |
AU (1) | AU2595392A (zh) |
DE (1) | DE4131924A1 (zh) |
IL (1) | IL103282A0 (zh) |
MA (1) | MA22650A1 (zh) |
MX (1) | MX9205443A (zh) |
WO (1) | WO1993006091A1 (zh) |
ZA (1) | ZA927305B (zh) |
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-
1991
- 1991-09-25 DE DE4131924A patent/DE4131924A1/de not_active Withdrawn
-
1992
- 1992-09-21 JP JP5505794A patent/JPH06510993A/ja active Pending
- 1992-09-21 WO PCT/EP1992/002181 patent/WO1993006091A1/de not_active Application Discontinuation
- 1992-09-21 EP EP92920155A patent/EP0605552A1/de not_active Withdrawn
- 1992-09-21 AU AU25953/92A patent/AU2595392A/en not_active Abandoned
- 1992-09-21 MA MA22941A patent/MA22650A1/fr unknown
- 1992-09-21 EP EP92116108A patent/EP0534341A1/de active Pending
- 1992-09-24 MX MX9205443A patent/MX9205443A/es unknown
- 1992-09-24 IL IL103282A patent/IL103282A0/xx unknown
- 1992-09-24 ZA ZA927305A patent/ZA927305B/xx unknown
- 1992-09-25 CN CN92111089A patent/CN1071419A/zh active Pending
-
1997
- 1997-01-15 US US08/783,072 patent/US5859020A/en not_active Expired - Fee Related
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1062559C (zh) * | 1995-09-26 | 2001-02-28 | 南开大学 | 4-芳基肟醚基喹唑啉类化合物及其合成方法和应用 |
CN103339114A (zh) * | 2010-12-24 | 2013-10-02 | 日本农药株式会社 | 苄氧基嘧啶衍生物,包含该衍生物的农业/园艺用杀虫剂及其使用方法 |
CN104185628A (zh) * | 2012-02-01 | 2014-12-03 | 日本农药株式会社 | 芳基烷氧基嘧啶衍生物、含有芳基烷氧基嘧啶衍生物作为活性成分的农业和园艺用杀虫剂、以及它们的用途 |
TWI566701B (zh) * | 2012-02-01 | 2017-01-21 | 日本農藥股份有限公司 | 芳烷氧基嘧啶衍生物及包含該衍生物作為有效成分的農園藝用殺蟲劑及其使用方法 |
CN104185628B (zh) * | 2012-02-01 | 2017-03-08 | 日本农药株式会社 | 芳基烷氧基嘧啶衍生物、含有芳基烷氧基嘧啶衍生物作为活性成分的农业和园艺用杀虫剂、以及它们的用途 |
US9750252B2 (en) | 2012-02-01 | 2017-09-05 | Nihon Nohyaku., Ltd. | Arylalkyloxy pyrimidine derivative, pesticide for agricultural and horticultural use containing arylalkyloxy pyrimidine derivative as active ingredient, and use of same |
Also Published As
Publication number | Publication date |
---|---|
US5859020A (en) | 1999-01-12 |
DE4131924A1 (de) | 1993-07-08 |
WO1993006091A1 (de) | 1993-04-01 |
JPH06510993A (ja) | 1994-12-08 |
MX9205443A (es) | 1993-03-01 |
ZA927305B (en) | 1993-03-29 |
IL103282A0 (en) | 1993-02-21 |
MA22650A1 (fr) | 1993-04-01 |
EP0605552A1 (de) | 1994-07-13 |
AU2595392A (en) | 1993-04-27 |
EP0534341A1 (de) | 1993-03-31 |
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