CN1257498A - 吡啶硫代-二噻唑二氧化物衍生物及其作为杀虫剂的应用 - Google Patents
吡啶硫代-二噻唑二氧化物衍生物及其作为杀虫剂的应用 Download PDFInfo
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- CN1257498A CN1257498A CN98805368A CN98805368A CN1257498A CN 1257498 A CN1257498 A CN 1257498A CN 98805368 A CN98805368 A CN 98805368A CN 98805368 A CN98805368 A CN 98805368A CN 1257498 A CN1257498 A CN 1257498A
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- JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-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
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229950000975 salicylanilide Drugs 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical class [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229950009390 symclosene Drugs 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- AJKIRUJIDFJUKJ-UHFFFAOYSA-N taurolidine Chemical compound C1NS(=O)(=O)CCN1CN1CNS(=O)(=O)CC1 AJKIRUJIDFJUKJ-UHFFFAOYSA-N 0.000 description 1
- 229960004267 taurolidine Drugs 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
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-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
- 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
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 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
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 229960004546 thiabendazole Drugs 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
- 235000010296 thiabendazole Nutrition 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- DTMHTVJOHYTUHE-UHFFFAOYSA-N thiocyanogen Chemical compound N#CSSC#N DTMHTVJOHYTUHE-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- PIZNQHDTOZMVBH-UHFFFAOYSA-N thionylimide Chemical class N=S=O PIZNQHDTOZMVBH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 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
- 108010067167 thuricin Proteins 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 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
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 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
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-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
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 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
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
-
- 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
- A01N43/82—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 three ring hetero atoms
-
- 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
- A01N43/88—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 six-membered rings with three ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
-
- 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
-
- 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
- C07D417/14—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 three or more hetero rings
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及式(Ⅰ)的化合物,其中pyr代表吡啶基,喹啉基及异喹啉基,其任选为单或多取代,n是1或2。其具有显著的抗微生物活性,可用于杀灭不期望的微生物,特别是真菌和细菌,用于保护植物和材料。
Description
本发明涉及一种新型S-吡啶基-二噻唑二氧化物、它们的制备方法、以及它们在植物或材料保护中的应用。
具有5元环的二噻唑已有文献报道,但其生物活性没有被提及(参看K.Dickore,Lieb.Ann.Chem.671(1964);US-PA 3345374)。S-芳基二噻唑二氧化物也已经公开,但它的活性范围没有达到所需的要求,尤其是杀细菌活性(参看DE 19545635)。在S位烷基取代的二噻嗪氧化物(6元环)也已经被公开,但其生物活性没有被提及(参看Nakahashi等Bull.Chem.Soc.Jpn.45,3217(1972);Hasegawa,K.等Bull Chem.Soc.Jpn.45,1567(1972))。
优选的通式(I)的化合物为:Pyr任意地被卤素、具有1-10个碳原子的烷基、具有1-8个碳原子和1-8个相同或不同卤素原子的卤代烷基、具有1-10个碳原子的烷氧基、具有1-8个碳原子和1-8个相同或不同卤素原子的卤代烷氧基、具有1-10个碳原子的烷硫基、具有1-8个碳原子和1-8个相同或不同卤素原子的卤代烷硫基、氨基、具有1-6个碳原子的直链或支链烷基基团的一烷基氨基、每个具有1-6个碳原子的相同或不同直链或支链烷基基团的二烷基氨基、具有1-6个碳原子的环烷基、亚甲二氧基、二氟亚甲二氧基、氯氟亚甲二氧基、二氯亚甲二氧基、硝基、氰基或如下基团单取代至五取代:
特别优选的通式(I)的化合物为:Pyr未被取代,或被氟、氯、溴、具有1-8个碳原子的烷基、优选甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷基、优选三氟甲基、三氟乙基、二氟氯甲基、具有1-8个碳原子的烷氧基、如优选甲氧基、乙氧基、u-丙氧基或异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷氧基、如优选二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三氟乙氧基、具有1-8个碳原子的烷硫基、具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷硫基、氨基、具有1-4个碳原子的烷基基团的一烷基氨基、具有相同或不同的烷基基团的二烷基氨基(其中每个烷基具有1-4个碳原子)、具有1-6个碳原子的环烷基、亚甲二氧基、二氟亚甲二氧基、氯氟亚甲二氧基、二氯亚甲二氧基、硝基、氰基或如下基团单取代至四取代,优选单取代至双取代:且n代表1或2。
在特定组合中、或优选组合中,基团的详细定义可用其他优选范围的基团的定义代替,如果需要,每一种情况的组合是独立的。
M代表碱金属离子或碱土金属离子,优选Na+、K+,与具有通式(III)的重氮盐反应获得,如果适宜,反应在催化剂存在的条件下进行。
Pyr-N≡NAθ (III)其中:
Pyr如上述定义,Aθ代表无机酸阴离子
向溶液(II)中优选加入一种碱,如果适宜,再加入催化剂,随后加入重氮盐溶液(III)。适用的碱优选碱金属氢氧化物,例如:氢氧化钾或氢氧化钠。适用催化剂为所有可促进重氮化官能团被含硫基团取代的催化剂。
催化剂优选使用Cu(I)盐或铜粉。加入重氮盐溶液时的温度可在一个很宽的范围内变化。一般而言,反应在-30℃-+60℃之间进行,优选在-20℃-+40℃之间进行。重氮盐溶液按现有技术中已知的方法由苯胺制备而成。
通式(II)的盐在一些情况下是公知的,也可按照现有技术(参见P1文献)中已知的方法类似地制备。通式(II)的盐可以是分离的固体形式也可是在原位制成的溶液。
其中:n代表1或2与通式(V)的硫代化合物反应获得,如果适宜,反应在碱或稀释剂存在的条件下进行,
Pyr-SH (V)
其中:Pyr如上述定义。
反应时,反应温度可在一个很大的范围内变化。通常,反应在在-30℃-100℃之间进行,优选在-10℃-+60℃之间进行。
如果适宜,反应在碱存在的条件下进行,所有的常规碱均适用于本发明目的。碱优选包括:叔胺如三乙胺和吡啶;碱金属氢氧化物如氢氧化钠或氢氧化钾;以及碱金属碳酸盐和碱金属碳酸氢盐如碳酸钾和碳酸氢钠。
合适的稀释剂可以为水,也可为所有惰性有机溶剂。稀释剂优选包括:烃类如甲苯、二甲苯或己烷,氯代烃类如氯苯和氯仿,酮类如丙酮,醚类如四氢呋喃、乙醚、甲基叔丁基醚和二噁烷,腈类如乙腈,以及DMSO、DMF和NMP。
R优选代表具有1-5个碳原子的烷基;特别优选甲基、乙基、丙基、异丙基、丁基、异丁基、或仲丁基。
反应时,反应温度可在一个基本的范围内变化。通常,反应在在-30℃-120℃之间进行,优选在-10℃-100℃之间进行。优选使用的稀释剂为氯代烃类,例如四氯化碳、氯仿、二氯甲烷或1,2-二氯乙烷。
通式(VI)的化合物是公知的,也可通过已知的方法(参见US-PA3345374)制备。
所有常规的卤化剂均可用于本发明。
优选的卤化剂为氯、溴、磺酰氯。
本发明的活性化合物具有强的杀微生物活性,且可以在植物保护和材料保护上用来防治有害微生物,优选防治真菌和细菌。
在本文中,工业材料是指已制备出的用于工业中的非生命材料。欲用本发明活性化合物保护而免受微生物改变或变质的工业材料的实例为:粘合剂、粘接剂、纸和卡片、织物、皮革、木材、涂料和塑料品、润滑冷却剂以及会受微生物侵害和破坏的其它材料。生产性工厂的部件,例如冷却水循环,也可能受到大量微生物的破坏,也在保护的材料范围之内。在本发明范围内提到的工业材料优选:粘合剂、粘接剂、纸和卡片、皮革、木材、涂料、润滑冷却剂和导热液体。
可以使工业材料变质或改变的微生物的实例为:细菌、真菌、酵母、藻类和粘菌。本发明活性化合物或组合物优选作用于真菌,特别是霉菌、以及粘菌和藻类。
下列属的微生物通过举例方式被提到:
链格孢属,如纤细链格孢,
曲霉属,如黑色曲霉,
毛壳霉属,如球毛壳霉,
粉孢革菌属,如单纯粉孢革菌,
香菇属,如虎皮香菇,
青霉属,如灰绿青霉,
多孔菌属,变色多孔菌,
短柄霉属,如出芽短柄霉,
Sclerophoma,如Sclerophoma.pityophila,
木霉属,如绿色木霉,
埃希氏杆菌属,如大肠杆菌,
假单胞菌属,如铜绿假单胞菌,
葡萄球菌属,如金黄色葡萄球菌。
杀真菌组合物可以用在作物保护中,用于防治根肿菌纲、卵菌纲、壶菌纲、接合菌纲、子囊菌纲、担子菌纲、半知菌纲。
上面以属名列出的病原真菌病害,可以提到的实例如下,但不限于这些:
腐霉属,如终极腐霉;
疫霉属,如蔓延疫霉;
假霜霉属,如律草假霜霉或古巴假霜霉;
单轴霉属,如葡萄生单轴霉;
霜霉属,如豌豆霜霉或芸苔霜霉;
白粉菌属,如禾白粉菌;
单丝壳菌属,如苍耳单丝壳菌;
柄球菌属,如苹果白粉病柄球菌;
黑星菌属,如苹果黑星菌;
核腔菌属,如圆核腔菌或麦类核腔菌(分生孢子形式:Drechslera,异名:长蠕孢属);
旋孢腔菌属,如禾旋孢腔菌(分生孢子形式:Drechslera,异名:长蠕孢属);
单孢锈菌属,如菜豆单孢锈菌;
柄锈菌属,如隐匿柄锈菌;
腥黑粉菌属,如小麦网腥黑粉菌;
黑粉菌属,如裸黑粉菌或燕麦黑粉菌;
薄膜革菌属,如佐佐木氏薄膜革菌;
梨孢菌属,如稻梨孢菌;
镰孢属,如大刀镰孢;
葡萄孢属,如灰色葡萄孢;
壳针孢属,如颖枯壳针孢;
小球腔菌属,如颖枯病小球腔菌;
尾孢属,如变灰尾孢菌;
链格孢属,如甘蓝黑斑病链格孢;
假小尾孢菌属,如柔毛假小尾孢菌。
在防治植物病害所需浓度下,本发明活性化合物被植物很好地耐受这一事实,使得活性化合物可以处理植物的地上部分、无性繁殖原种和种子,以及处理土壤。
根据其特定的物理和/或化学性能,通式(I)的活性化合物可以制成常规的剂型,如溶液、乳剂、悬浮剂、粉剂、泡沫剂、膏剂、颗粒剂、气雾剂和聚合物微胶囊剂。
这些型剂或组合物可以通过已知的方法生产,例如,将活性化合物与填充剂,即液体溶剂、加压的液化气、和/或固体载体混合,并任选使用表面活性剂,即乳化剂、和/或分散剂、和/或泡沫形成剂。在以水作填充剂的情况下,也可用有机溶剂作助溶剂。适合的液体溶剂主要有:芳族化合物,如二甲苯、甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡(例如石油馏份),醇类,如丁醇或乙二醇及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水;液化气填充剂或载体应理解为在室温常压下是气体的液体,例如气溶胶推进剂,如卤代烃类,或丁烷、丙烷、氮气和二氧化碳;适合的固体载体是:细的天然矿石,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,以及细的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;适用于颗粒剂的固体载体有:碾碎并分级的天然矿石如方解石、大理石、浮石、海泡石和白云石,或有机和无机粉末的合成颗粒,以及如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或泡沫形成剂为:非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐或蛋白水解产物;适合的分散剂为:木素亚硫酸盐废液和甲基纤维素。
制剂中可使用粘合剂,例如:羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,或天然磷脂(如脑磷脂和卵磷脂)和合成磷脂。其它的添加剂可以是矿物油和植物油。
制剂中也可使用着色剂,例如:无机颜料如氧化铁、二氧化钛和普鲁士蓝,有机染料如茜素染料、偶氮染料和金属酞菁染料,以及微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
通式(I)的活性化合物、组合物、前体、或由它们制成的制剂的效果和作用谱可以得到提高,当合适地加入其他抗微生物活性化合物、杀真菌剂、杀细菌剂、除草剂、杀虫剂、或其他活性化合物,从而扩大作用谱或获得特异的效果,例如可以同时杀灭昆虫。这些混合物与本发明混合物相比,具有一个较宽的作用谱。
在许多情况下,可产生协同效果,即混合物的效果超过单独组分的效果。混合物中特别有利的组分的实施例为下列化合物:
三唑类如:
氧环唑、三唑锡、联苯三唑醇、糠菌唑、环丙唑醇、苄氯三唑醇、苯醚甲环唑、烯唑醇、epoxyconazole、乙环唑、腈苯唑、解草唑、fenethanil、氟喹唑、氟唑硅、粉唑醇、呋菌唑、乙唑醇、亚胺唑、种菌唑、isozofos、腈菌唑、叶菌唑、多效唑、戊菌唑、丙环唑、(±)-顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇、2-(1-叔丁基)-1-(2-氯苯基)-3-(1,2,4-三唑-1-基)-丙烷-2-醇、戊唑醇、四氟醚唑、三唑酮、三唑醇、抑芽唑、氟菌唑、灭菌唑、烯效唑以及它们的金属盐和酸加合物。
咪唑类如:
克霉唑、bifonazole、咪唑酮、econazole、咪菌腈、抑霉唑、isoconazole、ketoconazole、lombazole、miconazole、稻瘟酯、咪鲜胺、氟菌唑、thiazolcar、1-咪唑基-1-(4’-氯苯氧基)-3,3-二甲基丁烷-2-酮、以及它们的金属盐和酸加合物。
吡啶类和嘧啶类如:
环嘧啶醇、丁硫啶、氯苯嘧啶醇、氟苯嘧啶醇、triamirol。
琥珀酸脱氢酶抑制剂如:
麦锈灵、萎锈灵、增效砜、环糠酰胺、甲呋酰苯胺、flutanil、furcarbanil、furmecyclox、邻酰胺、灭锈胺、呋菌胺、噻菌胺、pyrocarbolid、氧化萎锈灵、防霉胺、拌种灵。
萘衍生物如:
terbinafine、naftifine、butenafine、3-氯-7-(2-氮杂-2,7,7-三甲基-辛-3-烯-5-炔)。
亚磺酰胺类如:
抑菌灵、甲苯氟磺胺、灭菌丹、flurofolpet、克菌丹、captofol。
苯并咪唑类如:
多菌灵、苯菌灵、麦穗宁、噻菌灵、以及它们的盐。
吗啉衍生物类如:
aldimorph、烯酰吗啉、十二环吗啉、falimorph、苯锈啶、丁苯吗啉、十三吗啉、trimorphamid、以及它们的芳基磺酸盐,例如对-甲苯磺酸和对-十二烷基苯基-磺酸。
苯并噻唑类如:
2-巯基苯并噻唑。
苯并噻吩二氧化物如:
N-环己基-苯并[b]噻吩-S,S-二氧-甲酰胺。
苯甲酰胺类如:
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺、叶枯酞。
硼化合物如:
硼酸、硼酸酯、硼砂。
甲醛和甲醛释放化合物如:
苄醇单-(多)-半缩甲醛、正丁醇半缩甲醛、棉隆、乙二醇半缩甲醛、六氢-S-三嗪、六亚甲基四胺、N-羟甲基-N’-甲基硫脲、N-甲基醇氯乙酰胺、噁唑烷、多聚甲醛、taurolin、四氢-1,3-噁嗪、N-(2-羟丙基)-氨基-甲醇。
异噻唑啉酮类如:
N-甲基异噻唑啉-3-酮、5-氯-N-甲基异噻唑啉-3-酮、4,5-二氯-N-辛基异噻唑啉-3-酮、5-氯-N-辛基异噻唑啉酮、N-辛基-异噻唑啉-3-酮、4,5-三亚甲基-异噻唑啉酮、4,5-苯并异噻唑啉酮。
醛类如:
肉桂醛、甲醛、戊二醛、β-溴肉桂醛。
硫氰酸类如:
硫氰基甲硫基苯并噻唑、亚甲基二硫氰酸。
季铵化合物如:
苄菌胺、氯化苄基二甲基十四烷基铵、氯化苄基二甲基十二烷基铵、氯化二氯苯基二甲基烷基铵、氯化二癸基二甲基铵、氯化二辛基二甲基铵、氯化N-十六烷基三甲基铵、氯化1-十六烷基吡啶嗡。
碘衍生物如:
二碘甲基对甲苯基砜、3-碘-2-丙炔基醇、4-氯苯基-3-碘炔丙基缩甲醛、3-溴-2,3-二碘-2-丙烯基乙基氨基甲酸酯、2,3,3-三碘烯丙基醇、3-溴-2,3-二碘-2-丙烯基醇、3-碘-2-丙炔基正丁基氨基甲酸酯、3-碘-2-丙炔基正己基氨基甲酸酯、3-碘-2-丙炔基环己烷基氨基甲酸酯、3-碘-2-丙炔基苯基氨基甲酸酯。
酚类如:
三溴酚、四氯酚、3-甲基-4-氯酚、3,5-二甲基-4-氯酚、苯氧基乙醇、双氯酚、2-苄基-4-氯酚、5-氯-2-(2,4-二氯苯氧基)-酚、毒菌酚、对羟基苯甲酸盐、邻苯基酚、间苯基酚、对苯基酚、以及它们的碱金属盐和碱土金属盐。
具有活性卤素基团的杀微生物剂如:
溴硝丙二醇、bronidox、2-溴-2-硝基-1,3-丙二醇、2-溴-4’-羟基乙酰苯、1-溴-3-氯-4,4,5,5-四甲基-2-咪唑烷酮、β-溴-β-硝基苯乙烯、氯乙酰胺、氯胺、1,3-二溴-4,4,5,5-四甲基-2-咪唑烷酮、双氯胺、3,4-二氯-(3H)-1,2-二硫醇-3-酮、2,2-二溴-3-腈基丙酰胺、1,2-二溴-2,4-二氰基丁烷、halazone、卤胺宗、粘氯酸、苯基-(2-氯氰基-乙烯基)砜、苯基-(1,2-二氯-2-氰基乙烯基)砜、三氯异氰脲酸。
吡啶类如:
1-羟基-2-吡啶硫酮(以及它们的Na、Fe、Mn、Zn盐)、四氯-4-甲基磺酰基吡啶、pyrimethanol、噻菌胺、dipyrithion、1-羟基-4-甲基-6-(2,4,4-三甲基戊基)-2(1H)-吡啶。
甲氧基丙烯酸酯或类似物如:
(E)-甲氧基亚氨基-(α-(邻甲苯基氧基)邻甲苯基)乙酸甲酯、
(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧基苯基)乙酰胺、
(E)-2-{2-[6-(2-氰基苯氧基)嘧啶-4-基-氧基]苯基}-3-甲氧基丙烯酸酯、
2-[([3-甲氧基亚氨基-2-丁基)亚氨基]氧基)邻甲苯基]-2-甲氧基亚氨基亚氨逐乙酸-0-甲酯、
2-[[[[1-(2,5-二甲基苯基)亚乙基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-苯乙酰胺、
α-(甲氧基亚氨基)-N-甲基-2-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]-苯乙酰胺、
α-(甲氧基亚氨基)-2-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]-苯乙酸甲酯、
α-(甲氧基亚甲基)-2-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]-苯乙酸甲酯、
2-[[[5-氯-3-(三氟甲基)-2-吡啶基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-苯乙酰胺、
2-[[[环丙基[(4-乙氧基苯基)亚氨基]硫基]甲基]-α-(甲氧基亚氨基)-苯乙酸甲酯、
α-(甲氧基亚氨基)-N-甲基-2-(4-甲基-5-苯基-2,7-二氧杂-3,6-重氮辛-3,5-二烯-1-基)-苯乙酰胺、
α-(甲氧基亚甲基)-2-(4-甲基-5-苯基-2,7-二氧杂-3,6-重氮辛-3,5-二烯-1-基)-苯乙酸甲酯、
α-(甲氧基亚氨基)-N-甲基-2-[[[1-[3-(三氟甲基)苯基]乙氧基]亚氨基]甲基]-苯乙酰胺、
2-[[(3,5-二氯-2-吡啶基)氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-苯乙酰胺、
2-[4,5-二甲基-9-(4-吗啉基)-2,7-二氧杂-3,6-重氮壬-3,5-二烯-1-基)-α-(甲氧基亚甲基)-苯乙酸甲酯。
金属皂类如:
环烷酸锡、辛酸锡、2-乙基己酸锡、油酸锡、磷酸锡、苯甲酸锡、环烷酸铜、辛酸铜、2-乙基己酸铜、油酸铜、磷酸铜、苯甲酸铜、烷酸锌、辛酸锌、2-乙基己酸锌、油酸锌、磷酸锌、苯甲酸锌。
金属盐类如:
碳酸氢铜、二铬酸钠、二铬酸钾、铬酸钾、硫酸铜、氯化铜、硼酸铜、氟硅酸锌、氟硅酸铜。
氧化物如:
氧化三丁基锡、氧化亚铜、氧化铜、氧化锌。
二硫代氨基甲酸酯(盐)类如:
硫杂灵、福美铁、N-羟基甲基-N’-甲基-二硫代氨基甲酸钾、二甲基二硫代氨基甲酸钠、二甲基二硫代氨基甲酸钾、macozeb、代森锰、威百亩、代森联、福美双、代森锌、福美锌。
腈类如:
2,4,5,6-四氯异邻苯二甲腈、氰基-二硫代亚氨基氨基甲酸二钠。
喹啉类如:
8-羟基喹啉及其铜盐。
其他杀真菌剂和杀细菌剂如:
5-羟基-2(5H)-呋喃酮、4,5-苯并二噻唑啉酮、4,5-三亚甲基二噻唑啉酮、氯化N-(2-对氯苯甲酰基乙基)-己烷基铵、2-氧代-2-(4-羟基-苯基)乙酰基羟基肉桂酰氯、三-N-(环己基重氮二氧基)铝、N-(环己基重氮二氧基)-三丁基锡及其钾盐、双-N-(环己基重氮二氧基)铜;单独的含银、锌或铜的沸石或将其混入高聚物材料中。
特别优选是与如下组分混合:
氧环唑、糠菌唑、环丙唑醇、苄氯三唑醇、苯醚甲环唑、乙唑醇、叶菌唑、戊菌唑、丙环唑、戊唑醇、抑菌灵、甲苯氟磺胺、flurofolpet、呋菌胺、萎锈灵、苯并[b]噻吩-S,S-二氧-N-环己基甲酰胺、拌种咯、4-(2,2-二氟-1,3-苯并二桥氧-4-基)-1H-吡咯-3-腈、butenafine、抑霉唑、N-甲基-异噻唑啉-3-酮、5-氯-N-甲基异噻唑啉-3-酮、N-辛基异噻唑啉-3-酮、二氯-N-辛基异噻唑啉酮、巯基苯并噻唑、硫代氰酰基甲基硫代苯并噻唑、苯并异噻唑啉酮、N-(2-羟基丙基)-氨基-甲醇、苄醇(半)缩醛、N-甲基醇氯乙酰胺、N-(2-羟基丙基)-胺-甲醇、戊二醛、万亩定、二碳酸二甲酯、和/或3-碘-2-丙炔基-正丁基氨基甲酸酯。
除了上述杀真菌剂和杀细菌剂之外,混合物为获得好的防治效果,也可与如下其他活性化合物混合制剂:
杀虫剂/杀螨剂/杀线虫剂,如:
齐墩螨素、乙酰甲胺磷、啶虫脒、氟酯菊酯、棉铃威、涕灭威、涕灭砜威、艾氏剂、烯丙菊酯、甲体氯氰菊酯、双甲脒、除虫菌素、AZ 60541、苦楝素、乙基谷硫磷、谷硫磷、三唑锡、苏芸金杆菌、熏虫菊、4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)-H-吡咯-3-腈、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、生物苄呋菊酯、生物烯丙菊酯、乙基溴硫磷、溴硫磷、合杀威、噻嗪酮、butathiophos、丁酮威、丁酮砜威、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、灭螨猛、除线威、氯丹、氯氧磷、毒虫畏、定虫隆、氯甲硫磷、N-[(6-氯-3-吡啶基)-甲基]-N’-氰基-N-甲基-乙亚氨酰胺、氯化苦、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、cypophenothrin、四螨嗪、蝇毒磷、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷II、demeton-methyl、杀螨隆、氯亚胺硫磷、二嗪磷、1,2-二苯甲酰基-1-(1,1-二甲基)-肼、二硝甲酚、除线磷、敌敌畏、dicliphos、百治磷、除虫脲、乐果、二甲基-(苯基)-甲硅烷基-甲基-3-苯氧基苄基醚、二甲基-(4-乙氧基苯基)-甲硅烷基甲基-3-苯氧基苄基醚、甲基毒虫畏、敌噁磷、乙拌磷、克瘟散、emamectin、右旋烯炔菊酯、硫丹、苯硫磷、S-氰戊菊酯、乙硫苯威、乙硫磷、醚菊酯、乙嘧硫磷、克线磷、喹螨醚、螨完锡、五氟苯菊酯、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、丰索磷、倍硫磷、氰戊菊酯、氟虫腈、啶蜱脲、氟螨脲、氟氰戊菊酯、氟虫脲、氟氯苯菊酯、氟醚菊酯、氟胺氰菊酯、地虫硫磷、伐虫脒、安果、丁苯硫磷、噻唑磷、溴醚菊酯、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、伏蚁腙、烯虫乙酯、吡虫磷、碘硫磷、异稻瘟净、氯唑磷、异丙胺磷、异柳磷、异丙威、稻瘟磷、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、kadedrin、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxiectin、二溴磷、NC 184、NI 125、烟碱、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氟幼脲、氯菊酯、2-(4-苯氧基苯氧基)-乙基乙基氨基甲酸酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶磷、嘧啶磷、右旋炔丙菊酯、丙溴磷、猛杀威、丙虫磷、残杀威、低毒硫磷、发果、pymetrozin、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊酯、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、苄呋菊酯、RH-7998、鱼藤酮、水杨硫磷、硫线磷、氟硅菊酯、治螟磷、甲丙硫磷、氟胺氰菊酯、taroils、虫酰肼、吡螨胺、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁硫磷、杀虫畏、胺菊酯、tetramethacarb、thiafenox、噻丙腈、硫双灭多威、久效威、thiazophos、thiocyclam、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、三唑磷、唑蚜威、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、zetamethrin。
杀软体动物药剂,如:
薯瘟锡、四聚乙醛、灭虫威、miclosamide;
除草剂和其它杀藻剂,如:
乙草胺、三氟羧草醚、aclonifen、丙烯醛、甲草胺、禾草灭、莠灭净、amidosulfuron、杀草强、氨基磺酸铵、莎稗磷、磺草灵、莠去津、叠氮津、azimsulfuron、草除灵、乙丁氟灵、呋草黄、苄嘧黄隆、bensulphide、灭草松、benzofencap、吡草酮、甲羧除草醚、硼砂、除草定、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、抑草磷、仲丁灵、丁草敌、双丙氨磷、新燕灵、溴丁酰草胺、双酰草胺、甲氧除草醚、草灭畏、氯甲丹、氯草敏、氯嘧黄隆、草枯醚、氯乙酸、绿麦隆、枯草隆、氟苯胺灵、chorsulfuron、敌草索、氯硫酰草胺、环庚草醚、醚黄隆、烯草酮、异噁草酮、chlomeprop、二氟吡啶酸、氨腈、氰草津、灭草特、噻草酮、羟敌草腈、clodinafop-propargyl、cumyluron、CGA 248757、clometoxyfen、氰氟草酯、clopyrasuluron、cyclosulfamuron、2,4-滴丙酸、精2,4-滴丙酸、禾草灵、乙酰甲草胺、枯莠隆、野燕枯、吡氟酰草胺、噁唑隆、哌草丹、二甲草胺、噻节因、敌乐胺、地乐酚、地乐酯、特乐酚、双苯酰草胺、异丙净、敌草快、氟硫草定、敌草隆、二硝甲酚、甲胂钠、2,4-滴、daimuron、茅草枯、棉隆、2,4-滴丁酸、甜菜安、敌草净、麦草畏、敌草腈、二甲吩草胺、氟硫草丁、异戊乙净、eglinazine、菌多酸、菌草敌、戊草丹、乙丁烯氟灵、磺噻隆、乙氧呋草黄、乙氧苯草胺、ethoxyfen、吡草醚、胺苯磺隆、噁唑禾草灵、精噁唑禾草灵、非草隆、麦草氟、麦草氟甲酯、啶嘧黄隆、吡氟禾草灵、精吡氟禾草灵、fuenachlor、氯乙氟灵、伏草隆、乙羧氟草醚、氟除草醚、flupropanate、芴丁酸、flurochloridone、氯氟吡氧乙酸、氟黄胺草醚、fosamine、麦草氟异丙酯、强氟燕灵、氟烯草酸、flumipropyn、flumioxzim、flurtatone、flumioxzim、草甘膦、草铵膦、吡氟禾灵、环嗪酮、咪草酯、异丙隆、isoxaben、异噁草醚、咪唑烟酸、咪唑喹啉酸、咪唑乙烟酸、碘苯腈、异丙乐灵、咪吡嘧磺隆、KUH 911、KUH 920、乳氟禾草灵、环草定、利谷隆、磺草膦、2甲4氯、酚硫杀、2甲4氯丁酸、2甲4氯丙酸、精2甲4氯丙酸、苯噻酰草胺、氯磺酰草胺、威百亩、苯嗪草酮、吡草胺、甲基苯噻隆、灭草唑、methoroptryne、甲基杀草隆、异硫氰酸甲酯、溴谷隆、甲氧隆、嗪草酮、甲磺隆、草达灭、庚酰草胺、绿谷隆、甲胂一钠、异丙甲草胺、磺草唑胺、吡喃隆、萘丙胺、萘氧丙草胺、萘草胺、草不隆、烟嘧黄隆、达草灭、氯酸钠、噁草酮、乙氧氟草醚、坪草丹、安磺灵、二氯喹啉酸、氯甲喹啉酸、炔苯酰草胺、苄草丹、吡唑特、pyrazolsulfuron、苄草唑、稗草畏、哒草特、百草枯、克草敌、二甲戊灵、五氯酚、甲氯酰草胺、矿油、甜菜宁、落叶素、哌草磷、丙草胺、氟嘧黄隆、氨基丙氟灵、扑草净、毒草胺、敌稗、扑灭津、苯胺灵、嘧草硫醚、氯甲喹啉酸、灭藻醌、喹禾灵、精喹禾灵、噻嘧磺隆、稀禾定、sifuron、西玛津、西草净、甲嘧磺隆、甲磺草胺、磺草酮、sulfosate、重焦油、三氯醋酸(钠)、丁噻隆、特草定、特丁通、特丁津、特丁净、噻氟隆、噻吩磺隆、禾草丹、丁草威、三基苯草酮、野麦畏、醚苯黄隆、苯黄隆、绿草定、灭草环、氟乐灵、乙嗪草酮、thdiazimin、噻唑烟酸、氟胺黄隆、灭草敌。
在这些活性化合物组合物中各活性化合物的重量比例可在相当大的范围内变化。
活性化合物组合物优选含有0.1-99.9%,优选1-75%,最优选5-50%的活性化合物,由一种或多种上述混合物中的组分补足100%。
用于保护工业材料的杀微生物组合物或浓缩物包含0.01-95%(重量),优选0.1-60%的活性化合物或活性化合物组合物。
活性化合物或活性化合物组合物的使用浓度取决于欲防治的微生物的种类以及欲保护的材料的组成。最佳用药量可通过一系列试验确定。根据欲保护的材料,使用浓度通常在0.001-5%(重量),优选0.05-1%(重量)的范围内。
本发明的活性化合物或组合物中的现有杀微生物组分可被效果更好的组分代替,从而使得组合物更稳定且获得更宽的作用谱。
将5g(26mmol)的1,4,2-二噻唑-3-硫醇-1,1-二氧化物和7.71g乙酸钠加入到130ml丙酮/26ml水中,混合物冷却至0℃。将重氮盐溶液滴加入该混合物中,在0℃下搅拌1.5小时。在约10℃下用乙酸乙酯萃取,提取物用硫酸钠干燥并蒸发。
剩余物用硅胶色谱纯化(甲苯/乙酸乙酯=1∶1)。
产率为3.1g(理论值的48%);物理参数见表1。
重氮盐溶液:
将2.76g(26mmol)的3-氨基吡啶加入到7ml浓盐酸和52ml水的混合物中,用1.9g NaNO2溶于15.8ml水中形成的溶液在0℃下重氮化。在0℃下搅拌1小时,然后向溶液中加入3.73g脲和4.68g乙酸钠(Na-Acetone)。实施例9
将2g(11.6mmol)的3-氯-1,4,2-二噻唑-1,1-二氧化物加入到5ml DMF中,再在10℃下向其中滴加入1.38g(12.5mmol)和1.26g(12.5mmol)三乙胺溶于5ml DMF形成的溶液,在室温下搅拌24小时,将混合物倾入50ml冰水中,抽气过滤沉淀的晶体,并用少量水洗涤,在40℃下真空干燥。
表1中所列的实施例化合物根据实施例1和实施例9所述的方法类似制备。
将4.5g(24.5mmol)的1,4,2-二噻唑-3-甲硫基-l,1-二氧化物缓慢加入(10分钟)到17g(122mmol)的SO2Cl2中。将混合物加热至40℃,在该温度下搅拌24小时。真空蒸发除去过量的SO2Cl2后,混合物加入乙醚,搅拌,抽气过滤,并真空干燥。
产率:3.3g(理论值的78%)1H NMR(CDCl3)δ=4.67ppm。应用实施例A
为了证实防治真菌的效果,测定了本发明组合物的最低抑制浓度(MICs):
将本发明活性化合物以0.1g/l-5000mg/l的浓度加入到含有麦芽浸出液的琼脂中。琼脂凝固后,用表2所列试验微生物的纯菌种接种。使培养物维持在28℃、相对湿度60-70%的条件下2周,测定MIC值。MIC是指活性化合物使试验微生物种停止生长的最低浓度。结果列于表2。表2
本发明通式(I)化合物的最低抑制浓度(ppm)
应用实施例B
实施例编号 | 1 | 2 | 3 | 5 | 7 | 13 |
短茎青霉 | 20 | 200 | <40 | <40 | <40 | 20 |
球毛壳霉 | 20 | 200 | <40 | <40 | <40 | 10 |
黑色曲霉 | 20 | 400 | 100 | <40 | <40 | 100 |
疫霉病试验(蕃茄)/保护性
溶剂: 47重量份的丙酮
乳化剂: 3重量份的烷芳基聚乙二醇醚
制备活性化合物的合适制剂:将1重量份的活性化合物与上述重量的溶剂和乳化剂混合,并将该浓缩物用水稀释至所需浓度。
测定保护活性:用特定施用量的活性化合物制剂对幼苗进行喷雾。喷液干燥后,用蔓延疫霉的孢子水悬浮液接种植株。然后,将植株置于约20℃、相对湿度100%的培养箱中。
接种3天后检测结果。0%是指防效与对照相当,防效100%是指没有可观察到感染。
在100g/ha的用量下,本发明化合物1的防效为82%。应用实施例C
黑星病(苹果)/保护性
溶剂: 47重量份的丙酮
乳化剂: 3重量份的烷芳基聚乙二醇醚
制备活性化合物的合适制剂:将1重量份的活性化合物与上述重量的溶剂和乳化剂混合,并将该浓缩物用水稀释至所需浓度。
测定保护活性:用特定施用量的活性化合物制剂对幼苗进行喷雾。喷液干燥后,用苹果痂痕病原体苹果黑星菌的分生孢子水悬浮液接种植株。然后,将植株置于约20℃、相对温度100%的培养箱中1天。
随后将植株置于约21℃和相对湿度约为90%的温室中。
接种12天后检测结果。0%是指防效与对照相当,防效100%是指没有可观察到感染。
在100g/ha的用量下,本发明化合物1的防效为80%。
Claims (11)
3.权利要求1所述的通式(I)的化合物,其中Pyr未被取代,或被氟、氯、溴、具有1-8个碳原子的烷基、优选甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷基、如优选三氟甲基、三氟乙基、二氟氯甲基、具有1-8个碳原子的烷氧基、优选甲氧基、乙氧基、u-丙氧基或异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷氧基、如优选二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三氟乙氧基、具有1-8个碳原子的烷硫基、1-6个碳原子和1-6个氟和/或氯原子的卤代烷硫基、氨基、具有1-4个碳原子的烷基基团的一烷基氨基、具有相同或不同的烷基基团的二烷基氨基(其中每个烷基具有1-4个碳原子)、具有1-6个碳原子的环烷基、亚甲二氧基、二氟亚甲二氧基、氯氟亚甲二氧基、二氯甲烯二氧基、硝基、氰基或如下基团单取代至四取代,优选单取代至双取代:且n代表1或2。
5.组合物,其特征在于:它们含有至少一种权利要求1所述的通式(I)的化合物。
6.防治有害生物的方法,其特征在于:将权利要求1所述的通式(I)的化合物用于有害生物上或其所在的环境。
7.权利要求1至5所述的通式(I)的化合物或组合物用于防治有害生物的用途。
8.用于制备农药的方法,其特征在于:将权利要求1至4所述的通式(I)的化合物与填充剂和/或表面活性剂混合。
9.权利要求1所述通式(I)化合物的制备方法,其特征在于:在水溶液或碱性溶液中,通式(II)的盐:其中:n代表1或2,
M代表碱金属离子或碱土金属离子,优选Na+、K+,与具有通式(III)的重氮盐反应,如果适宜,反应在催化剂存在的条件下进行,
Pyr-N≡NAθ (III)其中:
Pyr定义同权利要求1,Aθ代表无机酸阴离子
11.通式(I)化合物的制备方法,其特征在于:通式(IV)的化合物:其中:n代表1或2与通式(V)的硫代化合物反应,如果适宜,反应在碱或稀释剂存在的条件下进行,
Pyr-SH (V)
其中:Pyr定义同权利要求1。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19721627A DE19721627A1 (de) | 1997-05-23 | 1997-05-23 | S-Pyridyl-dithiazoldioxide |
DE19721627.7 | 1997-05-23 |
Publications (1)
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CN1257498A true CN1257498A (zh) | 2000-06-21 |
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Application Number | Title | Priority Date | Filing Date |
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CN98805368A Pending CN1257498A (zh) | 1997-05-23 | 1998-05-12 | 吡啶硫代-二噻唑二氧化物衍生物及其作为杀虫剂的应用 |
Country Status (10)
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EP (1) | EP0984964A1 (zh) |
JP (1) | JP2001525834A (zh) |
KR (1) | KR20010020274A (zh) |
CN (1) | CN1257498A (zh) |
AU (1) | AU735796B2 (zh) |
BR (1) | BR9809659A (zh) |
CA (1) | CA2290790A1 (zh) |
DE (1) | DE19721627A1 (zh) |
PL (1) | PL336933A1 (zh) |
WO (1) | WO1998052945A1 (zh) |
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US6927214B1 (en) | 1999-01-15 | 2005-08-09 | Novo Nordisk A/S | Non-peptide GLP-1 agonists |
DE19918294A1 (de) * | 1999-04-22 | 2000-10-26 | Bayer Ag | O-Aryldithiazoldioxide |
DE19918297A1 (de) * | 1999-04-22 | 2000-10-26 | Bayer Ag | Hetarylsubstituierte Dithiazoldioxide |
DE10034133A1 (de) * | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (l) |
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DE2608488A1 (de) * | 1975-03-05 | 1976-09-16 | Ciba Geigy Ag | Iso(thio)harnstoffe |
DE3842970A1 (de) * | 1988-07-20 | 1990-01-25 | Bayer Ag | 4-halogen-5-nitrothiazol-derivate, verfahren zu ihrer herstellung, ihre verwendung als schaedlingsbekaempfungsmittel und neue zwischenprodukte |
DE19545635A1 (de) * | 1995-12-07 | 1997-06-12 | Bayer Ag | Dithiazoldioxide |
-
1997
- 1997-05-23 DE DE19721627A patent/DE19721627A1/de not_active Withdrawn
-
1998
- 1998-05-12 KR KR1019997009875A patent/KR20010020274A/ko not_active Application Discontinuation
- 1998-05-12 AU AU77639/98A patent/AU735796B2/en not_active Ceased
- 1998-05-12 BR BR9809659-1A patent/BR9809659A/pt not_active IP Right Cessation
- 1998-05-12 WO PCT/EP1998/002754 patent/WO1998052945A1/de not_active Application Discontinuation
- 1998-05-12 JP JP54989198A patent/JP2001525834A/ja active Pending
- 1998-05-12 CA CA002290790A patent/CA2290790A1/en not_active Abandoned
- 1998-05-12 PL PL98336933A patent/PL336933A1/xx unknown
- 1998-05-12 CN CN98805368A patent/CN1257498A/zh active Pending
- 1998-05-12 EP EP98925575A patent/EP0984964A1/de not_active Withdrawn
Also Published As
Publication number | Publication date |
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PL336933A1 (en) | 2000-07-17 |
WO1998052945A1 (de) | 1998-11-26 |
DE19721627A1 (de) | 1998-11-26 |
CA2290790A1 (en) | 1998-11-26 |
AU735796B2 (en) | 2001-07-12 |
JP2001525834A (ja) | 2001-12-11 |
BR9809659A (pt) | 2000-07-11 |
KR20010020274A (ko) | 2001-03-15 |
EP0984964A1 (de) | 2000-03-15 |
AU7763998A (en) | 1998-12-11 |
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