CN1558719A - 烟酸杂环酰胺及类似的嘧啶衍生物作为杀虫剂 - Google Patents
烟酸杂环酰胺及类似的嘧啶衍生物作为杀虫剂 Download PDFInfo
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- CN1558719A CN1558719A CNA028188977A CN02818897A CN1558719A CN 1558719 A CN1558719 A CN 1558719A CN A028188977 A CNA028188977 A CN A028188977A CN 02818897 A CN02818897 A CN 02818897A CN 1558719 A CN1558719 A CN 1558719A
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- alkyl
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- amino
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- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 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
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
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- 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
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 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
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 238000010572 single replacement reaction Methods 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- ZEVCJZRMCOYJSP-UHFFFAOYSA-N sodium;2-(dithiocarboxyamino)ethylcarbamodithioic acid Chemical compound [Na+].SC(=S)NCCNC(S)=S ZEVCJZRMCOYJSP-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 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
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 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
- 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
- OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
- 231100000027 toxicology Toxicity 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
- 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
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-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
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 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
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Abstract
本发明涉及式(I)的酰胺类及其盐类,X为CH或N;Y为O或S;n为0或1;R1为(C1-C4)-卤烷基;R2,R3彼此独立地为氢、(C1-C4)-烷基、(C1-C4)-卤烷基或卤素;R4为氢、(C1-C10)-烷基、(C3-C10)-环烷基、(C3-C10)-链烯基或(C3-C10)-炔基,其中所述烷基、环烷基、链烯基或炔基基团可以至多三个氢原子被卤素原子(优选为氟或氯)所取代,若被氟原子取代,则可被至多最大数目的氟原子取代。R5为脂族杂环,其含有至少一个氧、硫、氮和/或硅环原子,其为未经取代的杂环或被一至六个单价基团所取代,且其可为螺环、稠合环或双环系统的一部分。这些化合物可用来控制害虫。
Description
杂环酰胺、其制备方法,含有该杂环酰胺的组合物及其用途
本发明涉及杂环酰胺,其制备方法,含有该杂环酰胺的组合物及其在控制动物害虫,尤其是节肢动物,如昆虫、蜱螨和蠕虫上的用途。
由于昆虫例如通过撕食有用的植物、贮存食物、木材和纺织品或者通过将疾病传染给人类、饲养动物和有用的植物,会引起巨大的损害,因此,目前为止仍无法避免使用杀昆虫剂或驱虫剂。杀昆虫剂为综合性害虫控制中的一种重要部分,且其对全世界的收成产量和收成持续性而言具有决定性的贡献。
EP-A 0 580 374中揭示三氟甲基吡啶酰胺类作为杀虫剂。
然而,由于对现代杀昆虫剂在生态和经济方面的要求不断提高,例如涉及毒性、选择性、施用量、残质形成和简便的可制造性等方面,此外可能还出现例如抗药性等问题。因此,对于开发出比较现有技术中的杀昆虫剂至少部分具有优越性的新颖杀昆虫剂的任务一直存在。
现已发现,通式(I)的化合物,任选地也可为其盐类,在对抗动物害虫方面有良好的活性谱,且其同时有良好的植物耐受性,而对哺乳动物和水生动物而言具有适宜的毒物学性质。
因此,本发明提供式(I)的酰胺类及其盐类,
其中符号及标示的定义如下:
X为CH或N;
Y为O或S;
n为0或1;
R1为(C1-C4)-卤烷基;
R2,R3彼此独立地为氢、(C1-C4)-烷基、(C1-C4)-卤烷基或卤素;
R4为氢、(C1-C10)-烷基、(C3-C10)-环烷基、(C3-C10)-链烯基或(C3-C10)-炔基,其中所述烷基、环烷基、链烯基或炔基基团可以至多三个氢原子被卤素原子(优选为氟或氯)所取代,若被氟原子取代,则可被至多最大数目的氟原子取代;
R5为脂族杂环,其优选为四至八员环,并含有至少一个氧、硫、氮和/或硅环原子,且任选地可为螺环、稠合环或双环系统的一部分。
R5优选为含有一个氧环原子、一个硫环原子、一个氮环原子、一个硅环原子、二个氧环原子或二个硫环原子的四至八员的脂族杂环,其中该硫环原子以-S(O)p-的形式存在,且p为0、1或2。
特别优选的情况为,R5是式(II)的四至八员的杂脂基,
其中A和/或B为含有至少一个氧、硫、氮和/或硅环原子的单元,优选为-O-,-S(O)0,1,2-、-NR8-或-SiR9R10-,且该环可另外含有一或二个羰基,此一或二个羰基可与该杂单元一起形成内酯、内酰胺或酰亚胺单元;且其中,若A为氧且B为-NR8-,则这些单元可直接相邻,而在A和B为杂原子单元的所有其它情况中,这些单元必须以至少一个饱和的碳单元分开;
m为0或1至6,优选为0、1或2;
R6根据m,而为相同或相异,且各为杂环脂族环的单价取代基,例如未经取代或被一或多个相同或不同的基团所取代的(C1-C10)-烷基、(C2-C10)-链烯基、(C2-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基或(C8-C10)-环炔基,或为基团R7,其中
R7为卤素、氰基、硝基、羟基、硫基、氨基、(C1-C10)-烷酰基、(C3-C10)-烯酰基、(C3-C10)-炔酰基、(C3-C10)-环烷酰基、(C1-C10)-烷氧基、(C3-C10)-烯氧基、(C3-C10)-炔氧基、(C3-C10)-环烷氧基、(C4-C10)-环烯氧基、(C3-C8)-环烷基-(C1-C4)-烷氧基、(C4-C8)-环烯基-(C1-C4)-烷氧基、(C3-C8)-环烷基-(C3-C4)-烯氧基、(C4-C8)-环烯基-(C3-C4)-烯氧基、(C1-C4)-烷基-(C3-C8)-环烷氧基、(C2-C4)-链烯基-(C3-C8)-环烷氧基、(C2-C4)-炔基-(C3-C8)-环烷氧基、(C1-C4)-烷基-(C4-C8)-环烯氧基、(C2-C4)-链烯基-(C4-C8)-环烯氧基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、(C1-C4)-烷氧基-(C3-C4)-烯氧基、氨基甲酰基、(C1-C8)-一或-二烷基氨基甲酰基、(C3-C8)-一或-二环烷基氨基甲酰基、(C1-C8)-烷氧羰基、(C3-C8)-环烷氧羰基、(C1-C8)-烷酰氧基、(C3-C8)-环烷酰氧基、(C1-C8)-烷酰氨基、(C3-C8)-烯酰氨基、(C3-C8)-环烷酰氨基、(C3-C8)-环烷基-(C1-C4)-烷酰氨基、上述最后四种基团的N-(C1-C4)-烷氨基类似物、(C1-C10)-烷硫基、(C3-C10)-烯硫基、(C3-C10)-炔硫基、(C3-C8)-环烷硫基、(C4-C8)-环烯硫基、(C3-C8)-环烷基-(C1-C4)-烷硫基、(C4-C8)-环烯基-(C1-C4)-烷硫基、(C3-C8)-环烷基-(C3-C4)-烯硫基、(C4-C8)-环烯基-(C3-C4)-烯硫基、(C1-C4)-烷基-(C3-C8)-环烷硫基、(C2-C4)-链烯基-(C3-C8)-环烷硫基、(C2-C4)-炔基-(C3-C8)-环烷硫基、(C1-C8)-烷基-(C4-C8)-环烯硫基、(C2-C6)-链烯基-(C4-C8)-环烯硫基、(C1-C10)-烷基亚硫酰基、(C3-C4)-烯基亚硫酰基、(C3-C4)-炔基亚硫酰基、(C3-C10)-环烷基亚硫酰基、(C4-C10)-环烯基亚硫酰基、(C3-C8)-环烷基-(C1-C4)-烷基亚硫酰基、(C4-C8)-环烯基-(C1-C4)-烷基亚硫酰基、(C3-C8)-环烷基-(C3-C4)-烯基亚硫酰基、(C4-C8)-环烯基-(C3-C4)-烯基亚硫酰基、(C1-C4)-烷基-(C3-C8)-环烷基亚硫酰基、(C2-C4)-链烯基-(C3-C8)-环烷基亚硫酰基、(C2-C4)-炔基-(C3-C8)-环烷基亚硫酰基、(C1-C4)-烷基-(C4-C8)-环烯基亚硫酰基、(C2-C3)-链烯基-(C4-C8)-环烯基亚硫酰基、(C1-C10)-烷基磺酰基、(C3-C10)-烯基磺酰基、(C3-C10)-炔基磺酰基、(C3-C10)-环烷基磺酰基、(C4-C10)-环烯基磺酰基、(C3-C8)-环烷基-(C1-C4)-烷基磺酰基、(C4-C8)-环烯基-(C1-C4)-烷基磺酰基、(C3-C8)-环烷基-(C3-C4)-烯基磺酰基、(C4-C8)-环烯基-(C3-C4)-烯基磺酰基、(C1-C4)-烷基-(C3-C8)-环烷基磺酰基、(C2-C4)-链烯基-(C3-C8)-环烷基亚硫酰基、(C3-C6)-炔基-(C3-C8)-环烷基磺酰基、(C1-C4)-烷基-(C4-C8)-环烯基磺酰基、(C3-C4)-链烯基-(C4-C8)-环烯基磺酰基、(C1-C10)-烷氨基、(C3-C10)-烯氨基、(C3-C10)-炔氨基、(C3-C8)-环烷氨基、(C4-C8)-环烯氨基、(C3-C8)-环烷基-(C1-C4)-烷氨基、(C8-C8)-环烯基-(C1-C4)-烷氨基、(C3-C8)-环烷基-(C3-C4)-烯氨基、(C4-C8)-环烯基-(C3-C4)-烯氨基、(C1-C4)-烷基-(C3-C8)-环烷氨基、(C2-C4)-链烯基-(C3-C8)-环烷氨基、(C2-C4)-炔基-(C3-C8)-环烷氨基、(C1-C4)-烷基-(C4-C8)-环烯氨基、(C2-C4)-链烯基-(C4-C8)-环烯氨基、前述最后十四种基团的N-(C1-C4)-烷氨基类似物、(C1-C10)-三烷基甲硅烷基、芳基、芳酰基、杂环羰基、芳氧基、芳硫基、芳氨基、N-(C1-C4)-烷基-芳氨基、前述最后二种基团的N-(C1-C4)-烷氨基类似物、芳基-(C1-C4)-烷氧基、芳基-(C3-C4)-烯氧基、芳基-(C1-C4)-烷硫基、芳基-(C3-C4)-烯硫基、芳基-(C1-C4)-烷氨基、芳基-(C3-C4)-烯氨基、上述最后一种基团的N-(C1-C4)-烷氨基类似物、芳基-(C1-C8)-二烷基甲硅烷基、二芳基-(C1-C8)-烷基甲硅烷基、三芳基甲硅烷基、杂环基、杂环氧基、杂环硫基或杂环氨基,其中所述的芳基或杂环基的环形部分为未经取代或被一或多个选自下列组的基团所取代:卤素、氰基、硝基、氨基、羟基、硫基、(C1-C4)-烷基、(C1-C4)-卤烷基、(C3-C8)-环烷基、(C1-C4)-烷氧基、(C1-C4)-卤烷氧基、(C1-C4)-烷硫基、(C1-C4)-卤烷硫基、(C1-C4)-烷氨基、(C1-C4)-二烷氨基、三甲基甲硅烷基和(C1-C4)-烷酰基;
其中,任选地连接在相同碳原子上的二个烷基R6可与此碳原子一同形成螺环系统,或者任选地连接在不同碳原子上的二个烷基R6可与式(II)的脂族杂环一同形成稠合或双环系统,或再者,式(II)的杂脂环系统与另一芳基或杂芳基系统一起形成稠合环系统;
且其中,若R6为(C1-C10)-烷基、(C2-C10)-链烯基、(C2-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基或(C8-C10)-环炔基,则所述残基为未经取代或经单-或多取代的,优选为被R11所取代的,其中
R11具有上述R7的定义;
R8为氢、(C1-C10)-烷基、(C3-C10)-链烯基、(C3-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基、芳基、杂环基、(C1-C10)-烷酰基、(C3-C10)-烯酰基、(C3-C10)-炔酰基、(C4-C8)-环烷酰基、芳酰基、杂环羰基、氨基甲酰基、(C1-C6)-一或-二烷基氨基甲酰基、(C3-C10)-一或-二环烷基氨基甲酰基、(C1-C10)-烷氧羰基、(C3-C10)-环烷氧羰基、(C1-C10)-烷基磺酰基、(C3-C10)-烯基磺酰基、(C3-C6)-炔基磺酰基、(C3-C10)-环烷基磺酰基、(C4-C10)-环烯基磺酰基、(C3-C10)-环烷基-(C1-C10)-烷基磺酰基、(C4-C8)-环烯基-(C1-C4)-烷基磺酰基、(C3-C8)-环烷基-(C3-C4)-烯基磺酰基、(C4-C8)-环烯基-(C3-C4)-烯基磺酰基、(C1-C4)-烷基-(C3-C8)-环烷基磺酰基、(C2-C4)-链烯基-(C3-C8)-环烷基磺酰基、(C2-C4)-炔基-(C3-C8)-环烷基磺酰基、(C1-C4)-烷基-(C4-C8)-环烯基磺酰基、(C2-C4)-链烯基-(C4-C8)-环烯基磺酰基、羟基、(C1-C10)-烷氧基、(C3-C10)-烯氧基、(C3-C10)-炔氧基、(C3-C10)-环烷氧基、(C4-C10)-环烯氧基、(C3-C8)-环烷基-(C1-C4)-烷氧基、(C4-C8)-环烯基-(C1-C4)-烷氧基、(C3-C8)-环烷基-(C3-C4)-烯氧基、(C4-C8)-环烯基-(C3-C4)-烯氧基、(C1-C4)-烷基-(C3-C8)-环烷氧基、(C2-C4)-链烯基-(C3-C8)-环烷氧基、(C2-C4)-炔基-(C3-C8)-环烷氧基、(C1-C4)-烷基-(C4-C8)-环烯氧基、(C2-C4)-链烯基-(C4-C8)-环烯氧基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、(C1-C4)-烷氧基-(C3-C4)-烯氧基、芳氧基、芳基-(C1-C10)-烷氧基、芳基-(C3-C10)-烯氧基或芳基-(C3-C10)-炔氧基,
且上述为R8的基团是未经取代的基团或可被一或多个选自下列组的基团所取代:氰基、硝基、氨基、羟基、硫基、(C1-C4)-烷基、(C3-C10)-环烷基、(C1-C4)-烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷氨基和(C1-C4)-烷酰基;
R9和R10为(C1-C10)-烷基、(C2-C10)-链烯基、(C2-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基、(C8-C10)-环炔基、芳基、芳基-(C1-C4)-烷基或杂环基,优选甲基,
且其中,所有属于R5、R6、R7、R8、R9、R10和R11的所述基团中,与碳原子连接的氢未经取代或被一至三个卤素原子所取代,若被氟原子取代,则可被至多最大数目的氟原子取代。
式(I)中的符号和标示优选具有下述定义:
X优选为-CH-。
Y优选为-O-。
n优选为0。
R1优选为被F和/或Cl所单取代或多取代的(C1-C4)-烷基,特别优选为CF3、CHF2或CF2Cl,尤其特别优选CF3。
R2,R3优选为氢。
R4优选为氢或甲基,特别优选氢。
优选的还有如下的式(I)化合物,其中
R6为(C1-C10)-烷基、(C2-C10)-链烯基、(C2-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基或(C8-C10)-环炔基,其中所述基为未经取代的基团或可被R11所单取代或多取代,而R11具有上述定义之一;特别优选的是,R6为氢或(C1-C4)-烷基。
优选的还有如下的式(I)化合物,其中
R5优选为具有一或二个杂原子单元A和/或B的五至七员脂族杂环,特别优选的是具有一或二个杂原子单元的五至七员脂族杂环,此外,任选地环中的另一羰基与杂单元一起形成内酯或内酰胺单元。
优选的还有如下的式(I)化合物,其中
R7为芳基、芳酰基、杂环羰基、芳氧基、芳硫基、芳氨基、N-(C1-C4)-烷基-芳氨基、前述最后二种基团的N-(C1-C4)-烷氨基类似物、芳基-(C1-C4)-烷氧基、芳基-(C3-C4)-烯氧基、芳基-(C1-C4)-烷硫基、芳基-(C3-C4)-烯硫基、芳基-(C1-C4)-烷氨基、芳基-(C3-C4)-烯氨基、前述最后二种基团的N-(C1-C4)-烷氨基类似物、芳基-(C1-C8)-二烷基甲硅烷基、二芳基-(C1-C8)-烷基甲硅烷基、三芳基甲硅烷基、杂环基、杂环氧基、杂环硫基或杂环氨基,其中所述芳基或杂环基的环形部分为未经取代或被一或多个选自下列组的基团所取代:卤素、氰基、硝基、氨基、羟基、硫基、(C1-C4)-烷基、(C1-C4)-卤烷基、(C3-C8)-环烷基、(C1-C4)-烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷氨基或(C1-C4)-烷酰基。
优选的还有如下的式(I)化合物,其中
R8为(C1-C4)-烷基、(C1-C4)-烷酰基、(C1-C4)-烷氧羰基、(C1-C4)-烷基磺酰基或(C1-C4)-二烷基氨基甲酰基。
优选的还有如下的式(I)化合物,其中
A或B为氧、硫、SO、SO2、NR8,尤其是氧、硫、SO或SO2。
特别优选的还有如下的式(I)化合物,其中
R5为具有杂原子单元A或B的五或六员脂族杂环,其杂原子单元优选为氧、硫、S(O)或S(O)2,其若A或B为氧,且任选地环中带有另一个羰基,此羰基与氧原子一起形成内酯基团。
“卤素”包括氟、氯、溴或碘。
“(C1-C4)-烷基”是指具有1、2、3或4个碳原子的直链或分支的饱和的脂族烃基,例如甲基、乙基、丙基、异丙基、1-丁基、2-丁基、异丁基或叔丁基。
类似地,具有较大范围的碳原子数的烷基是指直链或分支的饱和的脂族烃基,其含有相应于所指定的范围的碳原子数。据此,“(C1-C10)-烷基”包含上述烷基,以及例如戊基、2-甲基丁基、1,1-二甲丙基、己基、庚基、辛基、叔辛基、壬基或癸基。
“(C1-C4)-卤烷基”是指“(C1-C4)-烷基”所表示的烷基中有一或多个氢原子被同样数目的相同或相异的卤素原子所取代,且优选被氯或氟所取代,例如三氟甲基、1-或2-氟乙基、2,2,2-三氟乙基、氯甲基、氟甲基、二氟甲基或1,1,2,2-四氟乙基。
具有给定碳原子数范围的“链烯基”或“炔基”是指具有相应于所指定范围的碳原子数的直链或分支的烃基,其含有至少一个多价键,此多价键可位于所述不饱和基的任何位置中。据此,“(C3-C10)-链烯基”是指,例如烯丙基、2-甲基丙烯基、1-或2-丁烯基、戊烯基、2-甲基戊烯基、己烯基、庚烯基、辛烯基、壬烯基或癸烯基。“(C2-C10)-链烯基”是指例如上述的基团和乙烯基。
“(C3-C10)-炔基”是指,例如丙炔、2-甲基丙炔基、2-丁炔基、戊炔基、2-甲基戊炔基、己炔、庚炔基、辛炔基、壬炔基或癸炔基。“(C2-C10)-炔基”是指,如上述的基团和乙炔基。
“(C3-C10)-环烷基”是指单环形且饱和的烷基,例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基或环癸基、双环形且饱和的烷基,例如降冰片烷基(norbornyl)或双环[2,2,2]辛基或为稠合且饱和的系统,例如十氢萘基。
“(C3-C10)-环烯基”对于单环,是指含有至少一个多价键的烷基,例如环丁烯基、环戊烯基、环己烯基、环庚烯基、环辛烯基或环癸烯基;对于双环,是指含有至少一个多价键的烷基,例如降冰片烯基或双环[2,2,2]辛烯基或为含有至少一个多价键的稠合系统,例如四-、六-或八氢萘基。
“(C8-C10)-环炔基”是指环辛炔基,环壬炔基或环癸炔基。
“(C1-C10)-烷酰基”是指,例如甲酰基、乙酰基、丙酰基、丁酰基、2-甲基丁酰基、三甲基乙酰基、辛酰基或癸酰基。
“(C3-C10)-烯酰基”是指,例如丙烯酰基、甲基丙烯酰基、巴豆酰基、二甲基丙烯酰基或辛烯酰基。
“(C3-C10)-炔酰基”是指,例如丙炔酰基、丁炔酰基、己炔酰基或辛炔酰基。
“(C3-C10)-环烷酰基”是指,例如环丙羰基、环丁羰基、环戊羰基、环己羰基或环辛羰基。
“(C1-C4)-烷氧基”及“(C1-C10)-烷氧基”是指其烃基各为“(C1-C4)-烷基”和“(C1-C10)-烷基”的烷氧基。
“(C3-C10)-烯氧基”、“(C3-C10)-炔氧基”、“(C3-C10)-环烷氧基”和“(C4-C10)-环烯氧基”是指其烃基各为“(C3-C10)-链烯基”、“(C3-C10)-炔基”、“(C3-C10)-环烷基”和“(C4-C10)-环烯基”的烷氧基。
“(C3-C8)-环烷基-(C1-C4)-烷氧基”是指,例如环丙基甲氧基、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)-环烯基-(C1-C4)-烷氧基”是指,例如环丁烯甲氧基、环戊烯甲氧基、环己烯甲氧基或环己烯乙氧基。
“(C3-C8)-环烷基-(C3-C4)-烯氧基”是指,例如环丙基烯丙氧基、环丁基烯丙氧基或环戊基烯丙氧基。
“(C4-C8)-环烯基-(C3-C4)-烯氧基”是指,例如环丁烯基烯丙氧基或环戊烯基烯丙氧基。
“(C1-C4)-烷基-(C3-C8)-环烷氧基”是指,例如甲基环戊氧、乙基环戊氧基、甲基环己氧基或乙基环己氧基。
“(C2-C4)-链烯基-(C3-C8)-环烷氧基”是指,例如乙烯环戊氧基、烯丙基环戊氧基、乙烯环己氧基或烯丙基环己氧基。
“(C2-C4)-炔基-(C3-C8)-环烷氧基”是指,例如乙炔环戊氧基、丙炔环戊氧基、乙炔环己氧基或丙炔环己氧基。
“(C1-C4)-烷基-(C4-C8)-环烯氧基”是指,例如甲基环戊烯氧基、乙基环戊烯氧基、甲基环己烯氧基或乙基环己烯氧基。
“(C2-C4)-链烯基-(C3-C8)-环烷氧基”是指,例如乙烯环戊氧基、烯丙基环戊氧基、乙烯环己氧基或烯丙基环己氧基。
“(C2-C4)-链烯基-(C3-C8)-环烯氧基”是指,例如乙烯环戊烯氧基、烯丙基环戊烯氧基、乙烯环己烯氧基或烯丙基环己烯氧基。
“(C1-C4)-烷氧基-(C1-C4)-烷氧基”是指被另一烷氧基取代的如上述定义的烷氧基,例如乙氧甲氧基、1-甲氧乙氧基、1-乙氧乙氧基或1-甲氧丙氧基。
“(C1-C4)-烷氧基-(C3-C4)-烯氧基”是指例如甲氧烯丙氧基或乙氧烯丙氧基。
“(C1-C8)-一或-二烷基氨基甲酰基”是指,例如甲基-、乙基-、丙基-、异丙基-、丁基-或叔丁基氨基甲酰基或二甲基-、二乙基-、甲基乙基-或二异丙基氨基甲酰基,但也指环形衍生物,例如吡咯烷基-或六氢吡啶烷氨基甲酰基。
“(C3-C8)-一或-二环烷基氨基甲酰基”是指,例如环丙基-、环丁基-、环戊基-或环己基氨基甲酰基或为二环丙基-、二环丁基-、二环戊基-或二环己基氨基甲酰基。
“(C1-C8)-烷氧羰基”是指,例如甲氧羰基、乙氧羰基、丙氧羰基、异丙氧羰基、丁氧羰基、异丁氧羰基、仲丁氧羰基或叔丁氧羰基。
“(C3-C8)-环烷氧羰基”是指,例如环丙氧羰基、环丁氧羰基、环戊氧羰基或环己氧羰基。
“(C1-C8)-烷酰氧基”是指,例如乙酰氧基、丙酰氧基、丁酰氧基或三甲基乙酰氧基。
“(C3-C8)-环烷酰氧基”是指,例如环丙羰氧基、环丁羰氧基、环戊羰氧基或环己羰氧基。
“(C1-C8)-烷酰氨基”是指,例如甲酰氨基、乙酰氨基、丙酰氨基、异丙酰氨基、丁酰氨基或三甲基乙酰氨基。
“(C3-C8)-烯酰氨基”是指,例如丙烯酰氨基、甲基丙烯酰氨基、二甲基丙烯酰氨基或巴豆酰氨基。
“(C3-C8)-环烷酰氨基”是指,例如环丙酰氨基、环丁酰氨基、环戊酰氨基或环己酰氨基。
“(C3-C8)-环烷基-(C1-C4)-烷酰氨基”是指,例如环丙基乙酰氨基或环戊基乙酰氨基。
“(C1-C10)-烷硫基”是指其烃基具有“(C1-C10)-烷基”所表示的意义的烷硫基。
“(C3-C10)-烯硫基”是指其烃基具有“(C3-C10)-链烯基”所表示的意义的烯硫基。
“(C3-C10)-炔硫基”是指其烃基具有“(C3-C10)-炔基”所表示的意义的炔硫基。
“(C3-C10)-环烷硫基”是指其烃基具有“(C3-C10)-环烷基”所表示的意义的环烷硫基。
“(C4-C10)-环烯硫基”是指其烃基具有“(C4-C10)-环烯基”所表示的意义的烯硫基。
“(C3-C8)-环烷基-(C1-C4)-烷硫基”是指,例如环丙基甲硫基、环丙基乙硫基、环戊基甲硫基或环己基甲硫基。
“(C4-C8)-环烯基-(C1-C4)-烷硫基”是指,例如环戊烯基甲硫基或环己烯基甲硫基。
“(C3-C8)-环烷基-(C3-C4)-烯硫基”是指,例如环丙基烯丙硫基、环戊基烯丙硫基或环己基烯丙硫基。
“(C4-C8)-环烯基-(C3-C4)-烯硫基”是指,例如环戊烯基烯丙硫基或环己烯基烯丙硫基。
“(C1-C4)-烷基-(C3-C8)-环烷硫基”是指,例如甲基环戊硫基或甲基环己硫基。
“(C1-C4)-烷基-(C4-C8)-环烯硫基”是指,例如甲基环戊烯硫基或甲基环己烯硫基。
“(C2-C4)-链烯基-(C3-C8)-环烷硫基”是指,例如乙烯基环戊硫基、烯丙基环戊硫基、乙烯基环己硫基或烯丙基环己硫基。
“(C2-C6)-炔基-(C3-C8)-环烷硫基”是指,例如乙炔基环戊硫基、丙炔基环戊硫基、乙炔基环己硫基或丙炔基环己硫基。
“(C2-C4)-链烯基-(C4-C8)-环烯硫基”是指,例如烯丙基环戊烯硫基或烯丙基环己烯硫基。
“(C1-C8)-烷基亚硫酰基”是指,例如甲基-、乙基-、丙基-、异丙基-、丁基-、异丁基-、仲丁基-、叔丁基-或辛基亚硫酰基。
“(C3-C8)-烯基亚硫酰基”是指,例如烯丙基-、甲基烯丙基-、丁烯基-或辛烯基亚硫酰基。
“(C3-C8)-炔基亚硫酰基”是指,例如丙炔基-、丁炔基-或辛炔基亚硫酰基。
“(C3-C10)-环烷基亚硫酰基”是指基烃基具有“(C3-C10)-环烷基”所表示的意义的环烷基亚硫酰基。
“(C4-C10)-环烯基亚硫酰基”是指其烃基具有“(C4-C10)-环烯基”所表示的意义的环烯基亚硫酰基。
“(C3-C8)-环烷基-(C1-C4)-烷基亚硫酰基”是指,例如环丙基甲基亚硫酰基、环丙基乙基亚硫酰基、环戊基甲基亚硫酰基或环己基甲基亚硫酰基。
“(C4-C8)-环烯基-(C1-C4)-烷基亚硫酰基”是指,例如环戊烯基甲基亚硫酰基或环己烯基甲基亚硫酰基。
“(C3-C8)-环烷基-(C3-C4)-烯基亚硫酰基”是指,例如环丙基烯丙基亚硫酰基、环戊基烯丙基亚硫酰基或环己基烯丙基亚硫酰基。
“(C4-C8)-环烯基-(C3-C4)-烯基亚硫酰基”是指,例如环戊烯基烯丙基亚硫酰基或环己烯基烯丙基亚硫酰基。
“(C1-C4)-烷基-(C3-C8)-环烷基亚硫酰基”是指,例如甲基环戊基亚硫酰基或甲基环己基亚硫酰基。
“(C1-C8)-烷基-(C4-C8)-环烯基亚硫酰基”是指,例如甲基环戊烯基亚硫酰基或甲基环己烯基亚硫酰基。
“(C2-C4)-链烯基-(C3-C8)-环烷基亚硫酰基”是指,例如乙烯环戊基亚硫酰基、烯丙基环戊基亚硫酰基、乙烯环己基亚硫酰基或烯丙基环己基亚硫酰基。
“(C2-C4)-炔基-(C3-C8)-环烷基亚硫酰基”是指,例如乙炔环戊基亚硫酰基、丙炔环戊基亚硫酰基、乙炔环己基亚硫酰基或丙炔环己基亚硫酰基。
“(C2-C4)-链烯基-(C4-C8)-环烯基亚硫酰基”是指,例如乙烯环戊烯基亚硫酰基、烯丙基环戊烯基亚硫酰基、乙烯环己烯基亚硫酰基或烯丙基环己烯基亚硫酰基。
“(C1-C10)-烷基磺酰基”是指,例如甲基-、乙基-、丙基-、异丙基-、丁基-、异丁基-、仲丁基-、叔丁基-或辛基磺酰基。
“(C3-C10)-烯基磺酰基”是指,例如烯丙基-、甲基烯丙基-、丁烯基-或辛烯基磺酰基。
“(C3-C10)-炔基磺酰基”是指,例如丙炔基-、丁炔基-或辛炔基磺酰基。
“(C3-C10)-环烷基磺酰基”是指其烃基具有“(C3-C10)-环烷基”所表示的意义的环烷基磺酰基。
“(C4-C10)-环烯基磺酰基”是指其烃基具有“(C4-C10)-环烯基”所表示的意义的环烯基磺酰基。
“(C3-C8)-环烷基-(C1-C4)-烷基磺酰基”是指,例如环丙基甲基磺酰基、环丙基乙基磺酰基、环戊基甲基磺酰基或环己基甲基磺酰基。
“(C4-C8)-环烯基-(C1-C4)-烷基磺酰基”是指,例如环戊烯基甲基磺酰基或环己烯基甲基磺酰基。
“(C3-C8)-环烷基-(C3-C4)-烯基磺酰基”是指,例如环丙基烯丙基磺酰基、环戊基烯丙基磺酰基或环己基烯丙基磺酰基。
“(C4-C8)-环烯基-(C3-C4)-烯基磺酰基”是指,例如环戊烯基烯丙基磺酰基或环己烯基烯丙基磺酰基。
“(C1-C4)-烷基-(C3-C8)-环烷基磺酰基”是指,例如甲基环戊基磺酰基或甲基环己基磺酰基。
“(C1-C4)-烷基-(C4-C8)-环烯基磺酰基”是指,例如甲基环戊烯基磺酰基或甲基环己烯基磺酰基。
“(C2-C4)-链烯基-(C3-C8)-环烷基磺酰基”是指,例如乙烯环戊基磺酰基、烯丙基环戊基磺酰基、乙烯环己基磺酰基或烯丙基环己基磺酰基。
“(C2-C4)-炔基-(C3-C8)-环烷基磺酰基”是指,例如乙炔环戊基磺酰基、丙炔环戊基磺酰基、乙炔环己基磺酰基或丙炔环己基磺酰基。
“(C2-C4)-链烯基-(C4-C8)-环烯基磺酰基”是指,例如乙烯环戊烯基磺酰基、烯丙基环戊烯基磺酰基、乙烯环己烯基磺酰基或烯丙基环己烯基磺酰基。
“(C1-C10)-烷氨基”是指有一氮原子被一或二个相同或相异的上述定义的烷基所取代。
“(C3-C10)-烯氨基”是指有一氮原子被一或二个相同或相异的上述定义的烯基所取代。
“(C3-C10)-炔氨基”是指有一氮原子被一或二个相同或相异的上述定义的炔基所取代。
“(C3-C8)-环烷氨基”是指有一氮原子被一或二个相同或相异的上述定义的环烷基所取代。
“(C3-C8)-环烷基-(C1-C4)-烷氨基”是指,例如环丙基甲氨基、环丙基乙氨基、环戊基甲氨基或环己基甲氨基。
“(C4-C8)-环烯基-(C1-C4)-烷氨基”是指,例如环戊烯基甲氨基或环己烯甲氨基。
“(C3-C8)-环烷基-(C3-C4)-烯氨基”是指,例如环丙基烯丙氨基、环戊基烯丙氨基或环己基烯丙氨基。
“(C4-C8)-环烯基-(C3-C4)-烯氨基”是指,例如环戊烯基烯丙氨基或环己烯基烯丙氨基。
“(C1-C4)-烷基-(C3-C8)-环烷氨基”是指,例如甲基环戊氨基或甲基环己氨基。
“(C1-C8)-烷基-(C4-C8)-环烯氨基”是指,例如甲基环戊烯氨基或甲基环己烯氨基。
“(C2-C4)-链烯基-(C3-C8)-环烷氨基”是指,例如乙烯环戊氨基、烯丙基环戊氨基、乙烯环己氨基或烯丙基环己氨基。
“(C2-C4)-炔基-(C3-C8)-环烷氨基”是指,例如乙炔环戊氨基、丙炔环戊氨基、乙炔环己氨基或丙炔环己氨基。
“(C2-C4)-链烯基-(C4-C8)-环烯氨基”是指,例如乙烯环戊烯氨基、烯丙基环戊烯氨基、乙烯环己烯氨基或烯丙基环己烯氨基。
除了经单-N取代的氨基外,本发明也包括相应的经N,N-二取代的衍生物,尤其是其中有一个氢被(C1-C4)-烷基所取代的衍生物。
“(C1-C10)-三烷基甲硅烷基”是指带有三个如上述定义的相同或相异的烷基的硅原子。类似地,“芳基-(C1-C6)-二烷基甲硅烷基”是指带有一个芳基及二个如上述定义的相同或相异的烷基的硅原子,“二芳基-(C1-C6)-烷基甲硅烷基”是指带有一个烷基及二个如上述定义的相同或相异的芳基的硅原子,而“三芳基甲硅烷基”是指带有三个如上述定义的相同或相异的芳基的硅原子。
“芳基”是指碳环的(即碳原子构造的)优选具有6至14个碳原子的芳族基,尤其优选具有6至12个碳原子,例如苯基、萘基或联苯基,优选为苯基。
据此,“芳酰基”是指经由羰基连接的如上述定义的芳基,例如苄酰基。
“含有至少一个氧、硫、氮和/或硅环原子的四至八员脂族杂环”是指可为完全饱和部分饱和,但非芳香族的环形基,且其被一或多个(优选为一或二个)来自氮、硫、氧和硅的组中相同或相异的原子所中断,然而其中二个氧原子不可以直接相邻。此杂环有四至八个环原子,除了上述的杂原子外,其余均为碳原子。
“杂环基”优选指可为完全饱和、部分饱和或完全不饱和的环形基,且其可被至少一或多个(优选为一至三个)来自氮、硫和氧的组中相同或相异的原子所中断,然而其中二个氧原子不可以直接相邻,且至少有一个碳原子存在于环中,例如噻吩、呋喃、吡咯、噻唑、噁唑、咪唑、异噻唑、异噁唑、吡唑、1,3,4-噁二唑、1,3,4-噻二唑、1,3,4-三唑、1,2,4-噁二唑、1,2,4-噻二唑、1,2,4-三唑、1,2,3-三唑、1,2,3,4-四唑、苯并[b]噻吩、苯并[b]呋喃、吲哚、苯并[c]噻吩、苯并[c]呋喃、异吲哚、苯并噁唑、苯并噻唑、苯并咪唑、苯并异噁唑、苯并异噻唑、苯并吡唑、苯并噻二唑、苯并三唑、二苯并呋喃、二苯并噻吩、咔唑、吡啶、吡嗪、嘧啶、哒嗪、1,3,5-三嗪、1,2,4-三嗪、1,2,4,5-四嗪、喹啉、异喹啉、喹喏啉(Chinoxalin)、喹唑啉、噌啉、1,8-萘啶、1,5萘啶、1,6-萘啶、1,7-萘啶、酞嗪、吡啶并嘧啶、嘌呤、喋啶、4H-喹嗪(4H-Chinolizin)、哌啶、吡咯烷、噁唑啉、四氢呋喃、四氢吡喃、异噁唑烷或噻唑烷的基团。“杂芳族的”为包含据此上述“杂环基”的定义的完全不饱和的芳族杂环化合物。
杂环基特别优选地是指具有3至6个环原子且1至4个选自O、S或N的杂原子的饱和、部分饱和或芳族的环系统,其环中至少有一个碳原子存在。
杂环基尤其特别优选地是指吡啶、嘧啶、1,2,4-噁二唑、1,3,4-噁二唑、吡咯、呋喃、噻吩、噁唑、噻唑、咪唑、吡唑、异噁唑、1,2,4-三唑、四唑、吡嗪、哒嗪、噁唑啉、噻唑啉、四氢呋喃、四氢吡喃、吗福啉、哌啶、哌嗪、吡咯啉、吡咯烷、噁唑烷、噻唑烷、环氧乙烷和环氧丙烷的基团。
“芳氧基”据此是指经由氧原子连接的如上述定义的芳基,例如苯氧基或萘氧基。
“芳硫基”据此是指经由硫原子连接的如上述定义的芳基,例如苯硫基或1-或2-萘硫基。
“芳氨基”是指经由氮原子连接的如上述定义的芳基,例如苯氨基或1-或2-萘氨基。
“N-(C1-C4)-烷基-芳氨基”是指,例如N-甲基-或N-乙基苯氨基。
“芳基-(C1-C4)-烷氧基”是指经由(C1-C4)-烷氧基连接的如上述定义的芳基,例如苄氧基、苯乙氧基、苯丁氧基或萘甲氧基。
“芳基-(C3-C4)-烯氧基”是指经由(C3-C4)-烯氧基连接的如上述定义的芳基,例如1-、2-或3-苯基烯丙氧基。
“芳基-(C1-C4)-烷硫基”是指经由烷硫基连接的如上述定义的芳基,例如苄硫基,萘甲硫基或1-或2-苯乙硫基。
“芳基-(C3-C4)-烯硫基”是指经由(C3-C4)-烯硫基连接的如上述定义的芳基,例如1-、2-或3-苯基烯丙硫基。
“芳基-(C3-C4)-烯氨基”是指经由(C3-C4)-烯氨基连接的如上述定义的芳基,例如1-、2-或3-苯基烯丙氨基。
“芳基-(C1-C8)-二烷基甲硅烷基”是指,例如苯基-或萘二甲基甲硅烷基。
“二芳基-(C3-C4)-烷基甲硅烷基”是指,例如二苯基-、苯基-萘基-或二萘甲基甲硅烷基。
“三芳基甲硅烷基”是指,例如三苯基-、二苯基-萘基-或三萘基甲硅烷基。
此外,“所有属于R5、R6、R7、R8、R9、R10和R11的所述基团中,与碳原子连接的氢未经取代或被一至三个卤素原子所取代,若被氟原子取代,则可被至多最大数目的氟原子取代”如包括下列基团:
卤烷基,例如1-或2-氟乙基、三氟甲基、2,2,2-三氟乙基、氯甲基,氟甲基、二氟甲基或1,1,2,2-四氟乙基;
卤烯基,例如1-、2-或3-氟烯丙基或1,1-二氟丙烯-3-基;
卤烷氧基,例如三氟甲氧基、2,2,2-三氟乙氧基;
卤烷硫基,例如三氟甲硫基;
卤烷基亚硫酰基,例如三氟甲基亚硫酰基;
卤烷基磺酰基,例如三氟甲基磺酰基;
卤环丙基,例如1,1-二氟环丙-2-基。
分别根据上述定义的取代基的类型,通式(I)化合物具有酸或碱的性质,并能形成盐类。如果通式(I)化合物带有例如羟基、羧基或其它可诱出酸性性质的基团时,这些化合物可与碱反应形成盐类。适宜的碱为,例如碱金属及碱土金属的氢氧化物、碳酸盐及碳酸氢盐,尤其是钠、钾、镁和钙的盐类,还有氨、具有(C1-C4)-烷基的伯胺、仲胺和叔胺以及(C1-C4)-烷醇的一-、二-和三烷醇胺。如果通式(I)化合物带有例如氨基、烷氨基或其它可诱出碱性性质的基团时,这些化合物可与酸反应形成盐类。适宜的酸为,例如矿物质酸,如盐酸、硫酸和磷酸,有机酸,如醋酸或草酸,和酸性盐类,如NaHSO4和KHSO4。以此方式可取得的盐类同样具有杀昆虫,杀蜱螨和杀螨虫性质。
通式(I)化合物可在双键上带有一或多个不对称碳原子或立体异构体。因此,其可有对映异构体或非对映异构体存在。本发明包含纯异构体及其混合物。非对映异构体的混合物可借助常用方法,例如从适宜的溶剂中选择性结晶或借助色谱法来分开异构体。外消旋物可借助常用方法分开对映异构体。
根据本发明的化合物的制备方法借助文献中已知的方法,例如有机合成中的标准操作,如Houben-Weyl,Mothoden der Organischen Chemie,Georg-Thieme-Verlag,Stuttgart中所描述。
此制备方法在已知且适宜所述反应的反应条件下进行。也可使用已知但本文未详述的变化方法。
按所希望的也可就地合成起始物质,并且以这样的方式,即不将其从反应混合物中分离,而是立即转化为式(I)化合物。
本发明也涉及制备通式(I)化合物的方法。
为了制备其中R1、R2、R3、R4、R5、A、Y和n具有上述式(I)中所给出的意义的通式(I)化合物,可例如将式(III)的羧酸,
其中X、R1、R2、R3、和n具有上述对于式(I)所给出的意义,以其活性衍生物形式,例如酸性卤化物、酯或酐,在碱的存在下,例如至少有一种胺(如三乙胺、二异丙基乙胺、吡啶、卢剔啶)、碱金属碳酸盐、碱金属碳酸氢盐或碱金属氢氧化物存在或有这些化合物的组合存在,与式(IV)的化合物反应,并任选地随即将R5基团进一步衍生化。
HNR4R5 (IV)
其中R4和R5具有上述对于式(I)所给出的意义,并任选地随即将R5基团进一步衍生化。
可借助上述方案合成的式(I)化合物集合库可以按类似的方式来制备,且其中可借助人工操作、以半自动或全自动的方式进行。在此例如可以将产物或中间体的反应操作、加工或纯化步骤自动化。在此的操作步骤整体上可例如通过S.H.DeWitt在“Annual Reports inCombinatorial Chemistry and Molecular Diversity:AutomatedSynthesis”,第1卷,Verlag Escom 1997,69-77页中的描述来理解。
用于类似的反应操作和加工中,可使用一系列商购可得的仪器,例如从下列公司提供的:Stem Corporation,Woodrolfe Road,Tollesbury,Essex,CM9 8SE,英国;或H+P Labortechnik GmbH,Bruckmannring28,85764 Oberschleiβheim,德国;或Radleys公司,Shirehill,SaffronWalden,Essex英国。用于通式(I)的化合物及在生产中出现的中间体的类似的纯化还可使用色谱法,例如ISCO公司,4700 Superior Street,Lincoln,NE 68504,美国。
前述的仪器可导致模块式的操作方式,其中各个处理步骤被自动化,但在各处理步骤之间则必须以手工操作。此点可通过使用半-整合或完全-整合的自动系统来避免,在这些系统中,各个自动化模块可例如通过自动机械来操作。此类自动系统可从如下述的公司取得:ZymarkCorporation公司,Zymark Center,Hopkinton,MA 01748,美国。
除了本文已描述的方法外,通式(I)化合物可借助固相-支持法来完全或部分制备。出于此目的,可将合成或适宜于合成的相应操作方式中的个别中间步骤或全部中间步骤与合成树脂结合。固相-支持合成法在专业文献中有足够的描述,例如Barry A.Bunin在“The CombinatiorialIndex”,Verlag Academic Press,1998。
使用固相-支持合成法可进行一系列文献已知的实验方案,其再次是可以人工或自动操作的。例如可以半自动化进行“茶袋法”(Houghten,US 4,631,211;Houghten等的,Proc.Natl.Acad.Sci,1985,82,5131-5135),且其中是使用来自IRORI公司(IRORI,11149 North TorreyPines Road,La Jolla,CA 92037,美国)的产品。自动化的固相-支持之类似合成法可借助来自下列公司的仪器成功进行:ArgonautTechnologies,Inc.,887 Industrial Road,San Carlos,CA 94070,美国,或MultiSynTech GmbH,Wullener Feld 4,58454 Witten,德国。
根据在此所描述的制备方法提供以物质集合形式的式(I)化合物,其被称为集合库。
本发明也涉及含有至少二种式(I)化合物的集合库。
式(I)化合物以良好的植物耐受性和适宜的温血动物毒性适用于控制动物害虫,尤其是昆虫、蜘蛛、蠕虫和软体动物,尤其特别优选于农业、于动物养殖、于森林、于储藏及材料保护及于卫生范畴中控制所发现的昆虫类及蜘蛛类。其对于一般敏感及具有抗性的种类具有活性,且对于所有或个别的发展阶段具有活性。所述害虫类属于:
蜱螨目分类,例如粗脚粉螨、脱缘蜱属、纯缘蜱属、鸡皮刺螨、茶瘿螨、桔皱叶刺瘿螨、牛蜱属、头蜱属(Rhipicephalus spp.)、花蜱属、璃眼蜱属、硬蜱属、瘙螨属、痒螨属、疥螨属、线螨属、苜蓿螨属、全爪螨属、叶螨属、始叶螨属、爪螨属、真叶螨属;
等足目分类,例如Oniscus aselus、Armadium vulgare、Porcellioscaber;
Diplopod马陆目分类,例如Blaniulus guttulatus;
唇足亚网分类,例如食土甜果螨(Geophilus carpophagus)、蚰蜒属(Scutigera spp.);
组合网分类,例如白松鼠(Scutigerella immaculat阿)
缨尾目分类,例如台湾衣鱼;
弹尾目分类,例如棘跳虫(Onychiurus armatus);
直翅目分类,例如东方蜚蠊、美洲大蠊、Leucophaea maderae、德国小蠊、居屋艾蟋、蝼蛄属(Gryllotalpa spp.)、非洲飞蝗、特异黑蝗、沙漠蝗;
等翅目分类,例如散白蚁属;
虱目分类,例如葡萄根瘤蚜(Phylloera vastatrix)、瘿绵蚜属、头虱(Pediculus humanus corporis)、血虱属、Linognathus spp.;
食毛目分类,例如嚼虱属、Damalinea spp.;
缨翅目分类,例如蔗苗网纹蓟马、烟蓟马(葱蓟马);
异翅亚目分类,例如扁盾蝽属、棉红蝽属(Dysdercus intermedius)、方背皮蝽、温带臭虫、长红猎蝽、椎猪蝽属;
同翅亚目分类,例如甘蓝粉虱、甘薯粉虱、温室粉虱、棉蚜、甘蓝蚜、茶 隐瘤蚜、Doralis fabae、苹果蚜、苹果绵蚜、桃大尾蚜、麦长管蚜、瘤蚜属、忽布疣蚜、禾谷缢管蚜、绿小叶蝉属、Euscelus bilobatus、黑尾叶蝉、欧果坚球蚧、榄珠蜡蚧、灰飞虱、褐飞虱、红肾圆盾蚧、常春藤圆盾蚧、粉蚧属、木虱属;
鳞翅目分类,例如红铃麦蛾,Bupalus piniarius、果园秋尺蛾(Cheimatobia brumata)、细潜蛾(Lithocolletis blancardella)、苹果巢蛾、菜蛾、黄褐天幕毛虫、黄毒蛾(棕尾毒蛾)、毒蛾属、棉药穿孔潜蛾(Bucculartix thurberiella)、柑桔叶潜蛾(柑桔潜叶蛾)、地虎属、切夜蛾属、褐夜蛾(Feltia spp.)、埃及钻夜蛾(埃及金钢钻)、实夜蛾属、贪夜蛾(甜菜夜蛾)、甘蓝夜峨、小眼夜蛾(panolis flammea)、斜纹夜蛾、灰翅夜蛾属、粉斑夜蛾(粉纹夜蛾)、苹果小卷蛾(苹果蠹蛾)、苹小卷叶蛾、粉蝶属、禾草螟属、玉米螟(玉米钻心虫)、Ephestiakuehniella、蜡螟(大蜡螟、绵虫)、黄尾卷叶蛾、Capua reticulana、云杉色卷蛾、葡萄果蠹蛾、茶长卷蛾,栎绿卷蛾;
鞘翅目分类,例如家俱窃蠹、谷蠹、豆象(Bruchidius obtectus)、菜豆象(Acanthoscelides obtectus)、家希天牛(家天牛)、杨树莹叶甲、马铃薯叶甲(马铃薯甲虫)、辣根猿叶甲、灯蛾属(Diabrotica spp.)、油菜壮Psylloides chrysocephala、Epilachna varivestis、Atomariaspp.、锯谷盗、花象属、米象属、葡萄黑耳喙象、香蕉根颈象、Ceuthorrynchus assimilis、紫苜蓿叶象、皮蠹属、斑皮蠹属、圆皮蠹属、毛皮蠹属、粉蠹属、Meligethes aeneus、蛛甲属、黄蛛甲、裸蛛甲、拟谷盗属、黄粉虫、叩头虫属、宽胸叩甲属、五月鳃金龟(五月金龟子)、双绺鳃金龟(马铃薯金龟子)、褐新西兰肋翅鳃角金龟(Costelytrazealandica);
膜翅目分类,例如松叶蜂属、实叶蜂属、毛蚁属、小家蚁、胡蜂属;
双翅目分类,例如伊蚊属、按蚊属、库蚊属、黑尾果蝇(醋蝇、黄猩猩果蝇)、家蝇属、厕蝇属、红头丽蝇(Calliphora erythrocephala)、绿蝇属、Hrysomyia spp.、疽蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、Hypobosca spp.、螯蝇属、狂蝇属、皮蝇属、虻属、Tannia spp.、花园毛蚊、欧洲麦杵绳、草种蝇属、菠菜蝇属(Pegomyiahyoscyami)、地中海实蝇、橘果实蝇、欧洲大蚊;
蚤目种分类,例如印属客蚤、角叶蚤属;
蛛形网分类,例如Scorpio maurus、红斑蛛;
蠕虫(Helminthen)分类,例如血矛线虫属(Haemonchus)、毛圆线虫(Trichostrongulus)、奥斯托线虫、古柏线虫、夏柏特线虫、圆线虫科、结节线虫、猪圆线虫、钩口线虫属、蛔虫属、异刺线虫及片形吸虫;
腹足纲动物分类,例如蛞蝓属(Deroceras spp.)、阿勇蛞蝓属、椎实螺属、土蜗属、琥珀螺属、双脐螺属、豆螺属(Bulinus spp.)、钉螺属;
双壳纲分类,例如饰贝属。
根据本发明控制寄生于植物的线虫类包括,例如,寄生于根部的土居型线虫类,如例如那些根结线虫属(根结线虫类,如南方根结线虫、北方根结线虫及爪蛙根结线虫)、异皮线虫属及球异皮线虫属(形成囊块的线虫如马铃薯金线虫,苍白球异皮线虫、三叶草异皮线虫、)与那些穿孔线虫属(如相似穿孔线虫)、短体线虫属(如疏忽短体线虫、穿刺短体线虫和草地垫刃线虫属(Pratylenchus curvitatus));
小垫刃线虫属如半穿刺线虫、矮化线虫属如不定矮化线虫及克莱顿矮化线虫、盘旋线虫属如强壮盘旋线虫、Heliocotylenchus如Haliocotylenchus multicinctus、Belonoaimus(如Belonoaimuslongicaudatus)、长针线虫属如逸去长针线虫、毛刺线虫属如原始毛刺线虫及剑线虫属如标准剑线虫。
此外根据本发明的化合物用于控制茎线虫属(茎部寄生虫如起绒草茎线虫、马铃薯茎线虫)、滑刃线虫属(叶部线虫类如菊叶芽滑刃线虫属ritzemabosi)及鳗线虫属(种子线虫类,如小麦粒瘿线虫)。
本发明还涉及组合物,例如植物保护组合物,优选杀虫的、杀螨的、杀蜱的、杀线虫的、杀软体动物的或杀真菌的组合,特别优选杀虫及杀螨组合物,其除了适宜的调配助剂之外包含一种或多种式(I)的化合物。
为了制备根据本发明的组合物,将活性物质与其它添加剂组合并调配成适宜的使用形式。
本发明也涉及含式(I)化合物以及适宜的配方佐剂的组合物,尤其是用于杀昆虫和杀螨虫的组合物。
根据本发明的组合物通常包含1至95重量%的式(I)的活性物质。它们可以不同的方式调配,分别是通过给出的生物和/或化学-物理参数而定。作为调配可能性因此例如考虑:
可湿性的粉剂(WP)、可乳化的浓缩剂(EC)、水溶液(SL)、乳液、可喷雾的溶液、基于油或水的分散液(SC)、悬浮乳液(SE)、喷粉剂(DP)、拌种剂(以微颗粒、喷雾颗粒、涂敷的颗粒及吸附颗粒形式的粒剂)、水分散性粒剂(WG)、ULV调配组合物、微胶囊、蜡或诱饵。
所述各种调配类型基本上是已知,并例如在:Winnacker-Kuechler,“化学技术(Chemische Technologie)”,第7册,C.Hanser VerlagMuenchen,第四版,1986;van Falkenberg,“农药调配(PesticidesFormulations)”,Marcel Dekker N.Y.,第二版,1972-73;K.Martens,“喷雾干燥手册(Spray Drying Handbook)”,第三版,1979,G.GoodwinLtd.London中有描述。
所述必要的调配辅剂,如惰性材料、表面活性剂、溶剂及其它的添加剂同样是已知的并例如在:Watkins,“(杀虫粉尘稀释液和载体手册)Handbook of Insecticide Dust Diluents and Carrier”,第二版,DarlandBooks,Caldwell N.J.;H.v.Olphen,“粘土胶体化学入门(Introductionto Clay Colloid Chemistry)”,第二版,J.Wiley&Sons,N.Y.;Marsden,“Solvents Guide”,第二版,Interscience,N.Y.1950;McCutcheon′s,“Detergents and Emulsifiers Annual”,MC Publ.Corp.,RidgewoodN.J.;Sisley and Wood,“表面活性剂百科全书(Encyclopedia ofSurface Active Agents)”,Chem.Publ.Co.Inc.,N.Y.1964;Schoenfeldt,“表面活性的环氧乙烷加成物(Grenzflchenaktivethylenoxid-addukte)”,Wiss Verlagsgesell.,Stuttgart 1967;Winnacker-Küchler,“化学技术”,第7册,C.Hanser Verlag Muenchen,第四版1986中有描述。
以所述调配为基础,也可以制备与其它杀虫活性物质、肥料和/或生长调节剂例如以调配好的形式的组合物或桶混组合物。可湿性的粉剂是均匀分散在水中的制品,在活性物质之外,除了稀释剂或惰性物质还有湿润剂(例如,聚氧乙基化烷基酚、聚氧乙基化脂肪醇、烷基磺酸酯或烷基酚基磺酸酯)及分散剂(例如,木素磺酸钠、2,2′-二萘甲烷-6,6′-二磺酸钠)。
可乳化的浓缩剂是通过将活性物质溶解在有机溶剂中(如丁醇、环己酮、二甲基甲酰胺、二甲苯或还有沸点较高的芳族或烃)并添加一种或多种乳化剂而制备的。作为乳化剂可以被使用的是例如:烷芳基磺酸的钙盐(如十二烷基苯-磺酸钙)或非离子性乳化剂(如脂肪酸聚乙二醇酯、烷芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷-环氧乙烷-稠合产物、烷基聚醚、失水山梨糖脂肪酸酯、聚氧乙烯山梨糖脂肪酸酯或聚氧乙烯山梨醇酯)。
喷粉剂是通过用细粒分布的固体物质(例如滑石粉、天然粘土(如高岭土、澎润土或叶蜡石)或硅藻土)研磨活性物质所得。粒剂或以活性物质喷洒在吸附性、粒化惰性物质上,或以结合剂的方式(例如,聚乙烯醇、聚丙烯酸钠或还有矿物油)将活性物质浓缩物覆盖在载体表面上(如沙、高岭石或粒化惰性物质)制备。也可将适宜的活性物质以用于生产肥料颗粒的惯用方式,任选地在与肥料的混合物中粒化。
可湿性的粉剂中的活性物质浓度通常约10-90重量%,其余的100重量%是由惯用的调配组份所组成。就可乳化的浓缩液而论,活性物质浓度可以是约5-80重量%。喷粉剂形式的调配组合物通常包含至少5至20重量%的活性物质,可喷洒的溶液约2-20重量%。就粒剂而论,活性物质的含量部分取决于活性物质是以液体还是固体形式存在并且由所使用的粒化助剂、填料等而定。
此外,所提及的活性物质调配组合物视需要分别包含惯用的粘合剂、湿润剂、分散剂、乳化剂、渗透剂、溶剂、填料或载体。
在使用时,将以商购通常形式提供的浓缩液视需要以惯用的方式稀释,例如,用水稀释可湿性的粉剂、可乳化的浓缩液、分散液及也有时稀释微粒剂。粉剂形式的制品和粒化的制品以及可喷洒的溶液在使用前通常不再用其它惰性物质稀释。
必要的施用量以外在的条件如温度、湿度以及其他条件而变化。其可以在较宽的限制范围内变动,例如,介于0.0005和10.0千克/公顷之间或更多的活性物质,优选则介于0.001和5千克/公顷之间。
根据本发明的活性物质可以以其商购的常规调配组合物形式提供以及以这些调配组合物与其它活性物质(如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂)的混合物所制备的使用形式提供。
用于控制有害虫类的制剂包括例如磷酸酯、氨基甲酸酯、羧酸酯、甲脒、锡化合物及通过微生物体产生的物质。
在混合物中优选的组份是:
1.来自磷化合物组
乙酰甲胺磷、甲基吡噁磷、益棉磷、保棉磷、溴硫磷、乙基溴硫磷、硫线磷(F-67825)、氯乙氧磷(Chlorethoxyphos)、毒虫畏、氯甲硫磷、毒死蜱、甲基毒死蜱、内吸磷、甲基内吸磷、砜吸磷、氯亚胺硫磷、二嗪磷、敌敌畏、百治磷、乐果、乙拌磷、苯硫磷、乙硫磷、灭线磷、乙嘧硫磷、伐灭磷、虫胺磷、杀螟硫磷、线虫磷、倍硫磷、地虫硫磷、安果、噻唑磷(ASC-66824)、庚烯磷、氯唑磷、异拌磷、噁唑磷、马拉硫磷、虫螨畏、甲胺磷、杀扑磷、蔬果磷、速灭磷、久效磷、二溴磷、氧乐果、亚砜吸磷、对硫磷、甲基对硫磷、稻丰散、甲拌磷、伏杀硫磷、硫环磷、磷虫威(BAS-301)、亚胺硫磷、磷胺、辛硫磷、嘧啶磷、乙基嘧啶磷、甲基嘧啶磷、丙溴磷、丙虫磷、胺丙畏、丙硫磷、吡唑硫磷、吡达潘噻恩(Pyridapenthion)、喹硫磷、甲丙硫磷、双硫磷、特丁磷、丁基嘧啶磷、杀虫畏、二甲硫吸磷、三唑磷、敌百虫、蚜灭多;
2.来自氨基甲酸酯组
棉铃威(OK-135)、涕灭威、仲丁威(BPMC)、甲萘威、克百威、丁硫克百威(Carbosulfan)、除线威(Cloethocarb)、丙硫克百威、乙硫苯威(Ethiofencarb)、呋线威(Furathiocarb)、HCN-801、叶蝉散、灭多威、邻-枯烯基丁酰基(甲基)氨基甲酸甲酯(5-methyl-m-cumenylbutyryl(methyl)carbamate)、杀线威、抗蚜威、残杀威、硫双威、久效威(thiofanox)、1-甲硫基(亚乙基氨基)-N-甲基-N-(吗啉硫代)氨基甲酸酯(UC 51717)、三阿萨密特(Triazamate);
3.来自羧酸酯组
氟酯菊酯、烯丙菊酯、甲体氯氰菊酯、(E)-(1R)-顺式-2,2-二甲基-3-(2-氧硫烷-3-亚基甲基)环丙烷羧酸5-苄基-3-呋喃甲酯(5-Benzyl-3-furylmethyl-(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate)、氟氯氰菊酯、乙体氯氰菊酯、生物烯丙菊酯、生物烯丙菊酯((S)-环戊基异构体)、生物苄呋菊酯、氟氯菊酯、(1RS)-反式-3-(4-叔丁苯基)-2,2-二甲基环丙烷羧酸(RS)-1-氰基-1-(6-苯氧基-2-吡啶基)甲酯(NCI 85193)、乙氰菊酯(Cycloprothrin)、氰氟菊酯(Cyfluthrin)、格林奈(Cyhalothrin)、氟氰戊菊酯(Cythithrin)、氯氰菊酯、苯醚氰菊酯、溴氰菊酯、烯炔菊酯(Empenthrin)、高氰戊菊酯(Esfenvalerate)、五氟苯菊酯(Fenfluthrin)、甲氰菊酯、氰戊菊酯、溴氟菊酯(flubrocythrinate)、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯(D异构体)、依密丙菊酯、(Imiprothrin)(S-41311)、氯氟氰菊酯、氯菊酯、苯氧菊酯((R)异构体)、炔酮菊酯(prallethrin)、除虫菊酯(天然产物)、苄呋菊酯、七氟菊酯、胺菊酯、θ-氯氰菊酯(TD-2344)、四溴菊酯,反氟菊酯(Transfluthrin)、ξ-氯氰菊酯(F-56701);
4.来自脒组
双虫脒、杀虫脒;
5.来自锡化合物组
三环锡、苯丁锡;
6.其它
齐墩螨素、ABG-9008、灭螨醌、艾扎丁、啶虫咪、安纳葛瑞发番西秦瑞(Anagrapha falcitera)、AKD-1022、AKD-3059、AKD-3088、AL-9811、环虫酰肼(ANS-118)、苏云金杆菌、白僵菌属巴其安纳(Beauveriabassiana)、杀虫磺、联苯肼酯(D-2341)、乐杀螨、BJL-932、溴螨酯、BAJ-2740(spirodiclofen)、BTG-504、BTG-505、噻嗪酮、毒杀芬、杀螟丹、氯杀螨(Chlorbenzilate)、溴虫腈(Chlorfenapyr)、定虫隆、2-(4-氯苯基)-4,5-二苯基噻吩(苯塞螨UBI-T 930)、氯芬泰辛(Chlorfentezine)、chloproxyfen、clothianidine、环虫酰肼(Chromafenozide)(ANS-118)、A-184699、(2-萘甲基)环丙烷羧酸酯(Ro12-0470)、灭蝇胺、CM-OO2X、DBI-3204、噻虫嗪(Diacloden,Thiamethoxam)、戴尔芬脲(Diafenthiuron)、N-(3,5-二氯基-4-(1,1,2,3,3,3-六氟基-1-丙氧基)苯基)氨基甲酰基)-2-氯基苯并羰亚胺酸乙酯、滴滴涕、三氯杀螨醇、除虫脲、N-(2,3-二氢-3-甲基-1,3-噻唑-2-亚基)-2,4-二甲苯胺、消螨通、二硝酯、苯虫醚、DPX-062、埃玛菌素-苯甲酸酯(MK-244)、硫丹、艾噻普耳(Ethiprole,Sulfethiprole)、醚菊酯(Ethofenprox)、乙螨唑(YI-5301)、喹螨醚、双氧威、氟虫腈、啶蜱脲(Fluzauron)、氯螨嗪(Flumite)(氟芬辛(Flufenzine),SZI-121)、2-氟基-5-(4-(4-乙氧苯基)-4-甲基-1-戊基)二苯醚(MTI 800)、颗粒层增殖及核型多角体病病毒(Granulose-undKernpolyederviren)、唑螨酯、芬索卡(Fenthiocarb)、Fluacrypyrim、氟螨嗪、氟螨噻、氟螨脲、氟虫脲(Flufenoxuron)、三氟醚菊酯(ICI-A5683)、Fluproxyfen、FMC-F6028、林丹、氯虫酰肼(Halofenozide)(RH-0345)、溴氟醚菊酯(Halofenprox)(MTI-732)、氟铃脲(DE-473)、噻螨酮、HOI-9004、伏蚁腙(AC 217300)、虱螨脲(Lurfenuron)、吡虫啉、茚虫威(Indoxacarb)(DPX-MP062)、凯密特(Kanemite)(AKD-2023)、M-020、呋虫胺、伊维素菌(Ivermectin)、M-020、IKA-2000、IKI-220、MKI-245、甲氧虫酰肼(Methoxyfenozide)(Intrepid,RH-2485)、弥拜菌素、NC-196、Neemgard、烯啶虫胺(Nitenpyram)(TI-304)、2-硝甲基-4,5-二氢-6H-噻嗪(DS 52618)、2-硝甲基-3,4-二氢噻唑(SD 35651)、2-硝基亚甲基-1,2-噻嗪-3-基氨基甲酸醛(噻虫醛(WL 108477))、NC-196、NNI-0001、Nidintefuran、蚊蝇醚(S-71639)、pirydaryl、protrifenbute、蚊蝇醚、NC-196、NC-1111、NNI-9768、氟酰脲(Novaluron)(MCW-275)、OK-9701、吲哚酯、OK-9602、克螨特、吡蚜酮、哒螨酮、嘧螨醚(SU-8801)、氯虫酰肼、甲氧虫酰肼、RYI-210、S-1283、S-1833、SB7242、弥拜菌素、氟硅菊酯(Silafluofen)、希拉达丁(Silomadine)(CG-177)、多杀菌素(Spinosad)、嘧螨醚、虫酰肼、吡螨胺(Tebufenpyrad)(MK-239)、伏虫隆、三氯杀螨砜、杀螨硫醚、噻虫啉(Thiacloprid)、杀虫环(Thiocyclam)、Thiamethoxam、TI-435、唑虫酰胺(Tolfenpyrad)(OMI-88)、三阿萨密特(Triazamate)(RH-7988)、杀虫隆、增效炔醚(Verbutin)、维泰利克(Vertalec)(Mykotal)、乙螨唑和Yi-6101。
上述用于组合物的成分为已知的活性物质,其中大部分在Ch.RWorthing,S.B.Walker,The Pesticide Manual,第12版,British CropProtection Council Farnham,2000中有描述。
作为文献已知的杀真菌剂类,其可以依照本发明的方式与式(I)的化合物组合的,例如是以下的产品:
Aldimorph、Andoprim、敌菌灵、氧唑菌、BAS 450F、苯霜灵、麦锈灵、苯菌灵、乐杀螨、双苯三唑醇、糠菌唑、粉病定、敌菌丹、克菌丹、多菌灵、萎锈灵、氟噁菌、酯菌胺、抑菌灵、哒菌清、苄氯三唑、乙霉威、噁醚唑(CGA 169374)、Difluconazole、甲菌定、烯酰吗啉、烯唑醇、敌螨普、二噻农、吗菌灵、多果定、克瘟散、乙菌定、氯唑灵(Etridiazot)、异嘧菌醇、呋菌胺、拌种咯、苯锈啶、丁苯吗啉、薯瘟锡、毒菌锡、嘧菌腙(TF164)、氟啶胺、Fluobenzimine、喹唑菌酮、Fluorimide、氟硅唑、氟酰胺、粉唑醇、灭菌丹、藻菌磷、麦穗宁、磺菌胺(MT-F 651)、呋氨丙灵、呋菌唑、拌种胺、双胍盐、己唑醇、腈嘧菌酯、烯菌灵、酰胺唑、异稻瘟净、异丙定、富士一号、环戊唑醇、铜化合物如(铜氧化氯、8-羟基喹啉-铜、铜氧化物C)、代森锰锌、代森锰、嘧菌胺(KIF 3535)、环戊唑菌、丙氧灭绣胺、甲霜灵、磺菌威、甲呋菌胺、溴氟唑菌、腈菌唑、代森钠、Nitrothalidopropyl、氟苯嘧啶醇、甲呋菌胺、噁霜灵、氧化萎锈灵、戊菌唑、戊菌隆、辛唑酮、噻菌灵、甲基代森锌、丙氯灵、杀菌利、百维灵、丙环唑、胺丙威、比锈灵、定菌磷、啶斑肟、咯喹酮、吡咪唑菌、腈苯唑、硫磺粉、戊唑醇、TF167、涕必灵、噻菌腈、Thiofanatemethyl、福美双、甲基立枯磷、对甲抑菌灵、三唑酮、唑菌醇、三环唑、克啉菌、氟菌唑、嗪氨灵、有效霉素、Vinchiozolin、氟苄酰胺、代森锌、十二烷基磺酸钠、十二烷基硫酸钠、C13/C15-醇醚磺酸钠、鲸蜡硬脂磷酸酯钠、二辛基磺基丁二酸钠、异丙基萘磺酸钠、亚甲基联萘磺酸钠、十六烷基三甲基铵氯化物、长链的伯(仲或叔)铵盐、烷基亚丙基铵盐、溴化十二烷基嘧啶鎓盐、羟乙基化的季化的脂肪铵盐、氯化烷基二甲基苄基铵盐和1-羟乙基-2-烷基咪唑啉。
以商购调配组合物已配备的剂型的活性物质含量可以为0.00000001至95重量%,优选介于0.00001和1重量%之间。
以适合于剂型的惯用方式应用。
因此本发明还提供式(I)化合物或其盐在控制有害昆虫,蜱螨类和/或线虫类上的用途。
本发明还提供控制有害昆虫、蜘蛛类和/或线虫类的方法,其包含将有效量的式(I)化合物或其盐施用于所述害虫或希望产生效用的区域。
根据本发明的活性物质也适用于控制在人类和兽医学医药领域以及动物饲养领域中的内寄生虫和外寄生虫。根据本发明的活性物质的应用在此以已知的方式以例如片剂、胶囊、口服液、粒剂形式的口服应用,以例如浸没(浸蘸)、喷溅(喷洒)、浇洒(倾泻和点滴(pour-on andspot-on))和敷粉形式的表皮应用以及例如注射形式的胃肠外应用。
因此,本发明也提供式(I)化合物或其盐在制备用于人类和/或动物的药品(优选为兽医用药)中的用途,尤其是在控制内-和/或外寄生虫上的用途。
因此,根据本发明的式(I)化合物特别优选用于冶疗温血动物,尤其是用于家畜饲养中,(例如牛、绵羊、猪及家禽类如鸡、鹅等)。在本发明优选的具体实施方案中,将化合物视需要以适合的调配组合物并视需要与饮用水或食料一起经口服给动物用药。因为对于粪便排泄物是较有效的,使得昆虫在动物粪便中的发育和容易受到抑制。各种适宜的剂量和调配组合物是特别取决于家畜的种类和发育阶段及病害风险,并通过依据惯用方法是容易测定及确定的。例如,所述化合物可以用0.01至1mg/kg体重的剂量应用于牛。
除了其对害虫的致命效果外,式(I)化合物也具有显著的驱虫效果。
在本发明中,驱虫剂意指对其它生命有机体,尤其是有害的害虫及讨厌的害虫,具有防范或驱除效果的物质或物质混合物。此概念也包含抗食用效果(Antifeeding-Effekt),即干扰或防止食物摄取,抑制排卵或对族群的发展具有影响。
因此,本发明也提供式(I)化合物或其盐在取得上述效果(尤其是在生物实例中所指明的害虫的情况中)上的用途。
本发明也提供用来防范或驱除有害生物体的方法,其中是将一或多种式(I)化合物或其盐施用于欲防范或驱除的有害生物体的区域。
施用于植物是意指植物的处理或也包括种子的处理。
至于对族群的影响方面,也可在族群的发展期间先后观察到药效,其效果是可以叠加的。在此种情况中,个别效果本身可能仅具有明显低于100%的效果,但最终全部效果仍可达100%。
此外,式(I)化合物或其盐的特征在于,在欲充分取得上述效果的情况下,在比通常直接抗虫较早的时间点施用此组合物。其效果通常可持续长时间,如此可取得超过二个月的作用期。
这些效果可在昆虫、蜘蛛类及其它上述害虫中观察到。
除了上述的施用方法外,根据本发明的式(I)化合物表现有突出的系统效果。因此,若该活性物质以液体或固体形式直接施用于植物附近(例如施用于土壤的粒剂,在流动的稻田施用)时,也可通过植物的部分,包括地下和地上的部分(例如根、茎、叶),将活性物质带给植物。
此外,根据本发明的活性物质以特殊的形式可用于处理植物的和生殖性的增殖物,例如谷类、蔬菜类、棉花、稻米、甜菜和其它作物和装饰植物的种子和其它作物和装饰植物,还有植物性增殖的作物和装饰植物的球茎、插条和块茎。所述处理可以在此于播种前或栽种前进行(例如借助种子涂覆的特殊技术、以液体或固体形式或如种子盒治疗法拌种)或通过特殊技术(例如沟犁)在播种或栽种期间或之后进行。所使用的活性物质量可根据施用情形在相当大的范围内变化。一般而言,施用量介于1克和10公斤活性物质/公顷土壤表面之间。
式(I)化合物也可用于控制已知作物或尚在开发中的经遗传工程改变的植物。转基因植物通常显示特别有利的性质,例如针对某些杀虫剂的抗性,尤其是针对某些除草剂的抗性,针对植物疾病或引起植物疾病的病原体(例如某些昆虫类或微生物如真菌、细菌或病毒)的抗性。其它的特殊性质涉及收成产物的数量、质量、贮存性、组分和特殊内容物。所以,转基因植物具有经提高的淀粉含量或经调整的淀粉品质或所收成的产物的脂肪酸组分不同于已知的。
优选应用于经济上重要的有用植物和装饰植物的转基因作物,例如谷类如小麦、大麦、黑麦、燕麦、粟、稻、木薯和玉米,或作物如甜菜、棉花、大豆、油菜、马铃薯、蕃茄、豌豆及其它蔬菜类。
当用于基因转殖作物,尤其是那些对昆虫具有抗性的基因转殖作物上时,除了那些在其它作物中可观察到的对抗有害生物体的效果外,还常观察到施用于所述基因转殖作物中的特殊效果,例如经过变更或特殊扩展的可控制的害虫谱或者是改变的可用于施用的施用量。
因此,本发明还提供式(I)化合物在控制基因转殖作物中的有害生物体方面的用途。
根据本发明的化合物的用途除了直接施用于害虫外,还包括任何其它将式(I)化合物作用于害虫的施用法,此类间接施用为,例如在应用中,如在土壤中、植物上或害虫体内分解成式(I)化合物或降解成式(I)化合物的化合物。
所提及的德国专利申请案10148290.6(本专利申请主张其优先权)及其包含的摘要的内容并为本说明书的组成部分。
下面实施例是用来说明本发明而非限制本发明。
A.化学实例
实施例A
4-三氟甲基烟酸-(四氢吡喃-4-基酰胺)
在0℃下,将于少许二氯甲烷中的0.63克(3.0毫摩尔)4-三氟烟酰氯滴加入0.30克(3.0毫摩尔)4-氨基四氢吡喃(借助四氢吡喃-4-酮的还原性胺化制备;NH3/H2/Ni,100巴,50℃)和0.35克(3.5毫摩尔)三乙胺于25毫升二氯甲烷中的溶液中。将混合物在室温下再搅拌2小时,然后,加入饱和的氯化钠溶液,分离物质相。将用水相二次与二氯甲烷充分搅拌。将合并的有机相干燥并浓缩。获得0.46克(67.8%理论值)无色固体产物,其熔点为149-150℃。
实例B
4-三氟甲基烟酸-(四氢噻喃-4-基酰胺)
类似于实例A,在三乙胺的存在下,将等摩尔量的4-氨基-四氢噻喃(由四氢噻喃-4-酮经相对应的肟,并随后在四氢呋喃中进行铅氢化锂(Lithiumalanat)的还原而制得)与4-三氟甲基-碱酰氯进行反应。在进行硅胶(醋酸乙酯)色谱法后获得酰胺,其为熔点为161-163℃的无色固体,(产率51.3%理论值)。
实例C
4-三氟甲基烟酸-(四氢噻喃-4-基酰胺)-S-氧化物
在0℃下,将于25毫升二氯甲烷中的1.23克(5毫摩尔)70%的3-氯过苯甲酸滴加入1.45克(5毫摩尔)4-三氟甲基烟酸-(四氢噻喃-4-基酰胺)(实例B)于50毫升二氯甲烷中的溶液中。将混合物在室温下搅拌6小时,与碳酸钠溶液充分搅拌,并将有机相干燥。浓缩后产生无色油,与醋酸乙酯磨擦后结晶。经真空吸滤后获得1.0克产物(65.3%理论值),其熔点为243-244℃。
实例D
4-三氟甲基烟酸-(四氢噻喃-4-基酰胺)-S,S-二氧化物
在0℃下,将于50毫升二氯甲烷中的2.46克(10毫摩尔)70%强度3-氯过苯甲酸滴加入1.45克(5毫摩尔)4-三氟甲基烟酸-(四氢噻喃-4-基酰胺)(实例B)于50毫升二氯甲烷中的溶液中。将混合物在室温下搅拌6小时,与碳酸钠溶液充分搅拌,并将有机相干燥。浓缩后产生无色油,与醋酸乙酯磨擦后结晶。经真空吸滤后获得1.3克产物(80.7%理论值),其熔点为248℃(分解)。
实例E
4-三氟甲基烟酸-(2,2-二甲基-1,3-二噁-环己基酰胺)
在0.50克对-甲苯磺酸水合物(p-Toluolsulfonsaeurehydrat)的存在下,将于50毫升甲苯中的2.64克(10毫摩尔)N-(4-三氟甲基烟酰基)丝氨醇和4.20克(40毫摩尔)丙酮二甲基乙缩醛在80℃下搅拌12小时,并将形成的甲醇以蒸馏移除。冷却后,用稀释的氢氧化钠溶液和水充分搅拌,并将有机相干燥及浓缩。获得1.5克无色固体产物(49.3%理论值),其熔点为155-156℃。
起始物质N-(4-三氟甲基烟酰基)丝氨醇的制备方法
将在100毫升干四氢呋喃中的3.9克(20毫摩尔)4-三氟甲基于烟酸和3.2克(20毫摩尔)羰基二咪唑在40-50℃下搅拌6小时。冷却后,加入1.8克(20毫摩尔)丝氨醇,并在50-60℃下继续搅拌4小时。在抽除溶剂后所得的粗产物在硅胶上进行色谱法纯化。获得2.9克产物(55.3%理论值),其熔点为155-156℃。
下列表中所列的化合物可以类似方法制备。
表1
表2
B.调配组合物实例
a)将10重量份的活性物质与作为惰性物质的90重量份的滑石粉混合,并在锤磨机中粉碎,以制备喷粉剂。
b)将25重量份的活性物质、作为惰性物的65重量份的含高邻土的石英、作为湿润剂及分散剂的10重量份的木素磺酸钾及1重量份的油酰甲基牛磺酸钠混合,并在针状盘式磨机中研磨,以制备可轻易分散在水中的可湿润的分散剂。
c)将40重量份的活性物质与7重量份的磺化琥珀酸半酯、2重量份的木素磺酸钠盐及51重量份的水混合,并在球磨机中研磨成小于5微米的粒度,以制备可轻易分散在水中的分散式浓缩液。
d)由15重量份的活性物质、作为溶剂的75重量份的环己烷及作为乳化剂的10重量份乙氧化的壬基酚(10EO)制备可乳化的浓缩液。
e)由2至15重量份的活性物质及惰性颗粒截体物质(如硅镁土、浮石颗粒和/或石英砂)制备粒剂。适当地使用具有30%固体份额的实施例b)的可湿性粉剂的悬浮液,并将其喷在硅镁土颗粒的表面上,干燥并直接混合。可湿性粉剂的重量份额约占5%而惰性载体物质约占制备的粒剂的95%。
C.生物实施例
在下列实施例1至3中,若浓度为500ppm(根据活性物质的含量)或更少的化合物对有害生物体产生50%或更高的效果,则此化合物便被认为具有活性。
实施例1
将具有胚根的发芽的蚕豆籽(Vicia faba)移至其内装填了自来水的棕色玻璃瓶内,随即殖入约100只黑豆蚜虫(甜菜蚜)。然后,将植物和蚜虫浸入待检测的配制好的化合物水溶液中5秒。将水滴干后,将植物和蚜虫置于空调柜中(光照16小时/天,25℃,40-60%相对大气湿度)。贮存3和6天后,确定化合物对蚜虫所造成的死亡率。结果发现下列实例的化合物有活性:3,8,9,11,17,18,19,21,22(顺式),22(反式),24,30(顺式),30(反式),31(顺式),124,134,135,161,163,164,166,203,216,219,353和356。
实施例2
将具有胚根的发芽的蚕豆籽(Vicia faba)移至其内装填了自来水的棕色玻璃瓶内,然后,将4毫升待检测的配制好的化合物水溶液中移入棕色玻璃瓶内。将约100只黑豆蚜虫(甜菜蚜)大量殖入蚕豆。然后,将植物和蚜虫置于空调柜中(光照16小时/天,25℃,40-60%相对大气湿度)。贮存3和6天后,以蚜虫的死亡率确定化合物的根系效果。结果发现下列实例的化合物有活性:3,8,9,10,11,12,17,18,19,21,22(顺式),22(反式),24,30(顺式),30(反式),31(顺式),35,124,128,134,135,161,162,163,164,165,166,203,216,219,237,250,353和356。
实施例3
在各具有两片发育良好的叶子的菜豆植物上喷洒待检测的配制好的化合物水溶液至滴湿。晾干后,将分别为一株处理过的菜豆、一株未处理过的菜豆和一株以白蝇(温室粉虱)重度感染过的菜豆置于一处。将植物置于25℃及60%相对湿度的洗衣房内。48小时后,测定在处理过和未处理过的植物上的虫卵数。通过相对比较在未处理过的菜豆上的虫卵数(分别相当于100%)和处理过的菜豆上的虫卵数确定驱虫作用的程度。结果发现下列实例的化合物有活性:19。
实施例4
在各具有三片发育良好的叶子的黄豆株上喷洒待检测的配制好的化合物水溶液至滴湿。晾干后,将分别为一株处理过的植物及一株未处理过的植物,与一株以一群蓟马种的苜蓿蓟马侵染过的植物置于一处。将植物保持在空调柜中(23℃,50-60%相对湿度)。处理14天后,确定处理过和未处理过的植物上的叶子损伤情形。通过相对比较在未处理过的植物上的叶子损伤情形(分别相当于100%)和处理过的植物上的叶子损伤情形确定驱虫作用的程度。在此驱虫测试中,结果发现下列实例的化合物有活性:19。
Claims (20)
1.一种式(I)的酰胺及其盐类,
其中符号及标示的定义如下:
X 为CH或N;
Y 为O或S;
n 为0或1;
R1 为(C1-C4)-卤烷基;
R2,R3 彼此独立地为氢、(C1-C4)-烷基、(C1-C4)-卤烷基或卤素;
R4 为氢、(C1-C10)-烷基、(C3-C10)-环烷基、(C3-C10)-链烯基或(C3-C10)-炔基,其中所述烷基、环烷基、链烯基或炔基基团可以至多三个氢原子被卤素原子所取代,若被氟原子取代,则可被至多最大数目的氟原子取代;
R5 为含有至少一个氧、硫、氮和/或硅环原子的脂族杂环,其为未经取代或被一至六个单价基团所取代,且可为螺环、稠合环或双环系统的一部分。
2.如权利要求1的式(I)所示的酰胺及其盐类,其中R5为含有一个氧环原子、一个硫环原子、一个氮环原子、一个硅环原子、二个氧环原子或二个硫环原子的四至八员的脂族杂环,其中该硫环原子以-S(O)p-的形式存在,且p为0、1、2。
3.如权利要求1或2的式(I)所示的酰胺及其盐类,其中R5是式(II)的杂脂基,
其中A和/或B为含有至少一个氧、硫、氮或硅环原子的单元,且该环可另外含有一或二个羰基,此一或二个羰基可与该杂单元一起形成内酯、内酰胺或酰亚胺单元;且其中,若A为氧且B为氮,则这些单元可直接相邻,而在A和B为杂原子单元的所有其它情况中,这些单元必须以至少一个饱和的碳单元分开;
m 为0或1至6;
R6 根据m,而为相同或相异,且分别为未经取代或被一或多个相同或不同的基团所取代的(C1-C10)-烷基、(C2-C10)-链烯基、(C2-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基或(C8-C10)-环炔基,或为基团R7,其中
R7 为卤素、氰基、硝基、羟基、硫基、氨基、(C1-C10)-烷酰基、(C3-C10)-烯酰基、(C3-C10)-炔酰基、(C3-C10)-环烷酰基、(C1-C10)-烷氧基、(C3-C10)-烯氧基、(C3-C10)-炔氧基、(C3-C10)-环烷氧基、(C4-C10)-环烯氧基、(C3-C8)-环烷基-(C1-C4)-烷氧基、(C4-C8)-环烯基-(C1-C4)-烷氧基、(C3-C8)-环烷基-(C3-C4)-烯氧基、(C4-C8)-环烯基-(C3-C4)-烯氧基、(C1-C4)-烷基-(C3-C8)-环烷氧基、(C2-C4)-链烯基-(C3-C8)-环烷氧基、(C2-C4)-炔基-(C3-C8)-环烷氧基、(C1-C4)-烷基-(C4-C8)-环烯氧基、(C2-C4)-链烯基-(C4-C8)-环烯氧基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、(C1-C4)-烷氧基-(C3-C4)-烯氧基、氨基甲酰基、(C1-C8)-一或-二烷基氨基甲酰基、(C3-C8)-一或-二环烷基氨基甲酰基、(C1-C8)-烷氧羰基、(C3-C8)-环烷氧羰基、(C1-C8)-烷酰氧基、(C3-C8)-环烷酰氧基、(C1-C8)-烷酰氨基、(C3-C8)-烯酰氨基、(C3-C8)-环烷酰氨基、(C3-C8)-环烷基-(C1-C4)-烷酰氨基、上述最后四种基团的N-(C1-C4)-烷氨基类似物、(C1-C10)-烷硫基、(C3-C10)-烯硫基、(C3-C10)-炔硫基、(C3-C8)-环烷硫基、(C4-C8)-环烯硫基、(C3-C8)-环烷基-(C1-C4)-烷硫基、(C4-C8)-环烯基-(C1-C4)-烷硫基、(C3-C8)-环烷基-(C3-C4)-烯硫基、(C4-C8)-环烯基-(C3-C4)-烯硫基、(C1-C4)-烷基-(C3-C8)-环烷硫基、(C2-C4)-链烯基-(C3-C8)-环烷硫基、(C2-C4)-炔基-(C3-C8)-环烷硫基、(C1-C8)-烷基-(C4-C8)-环烯硫基、(C2-C6)-链烯基-(C4-C8)-环烯硫基、(C1-C10)-烷基亚硫酰基、(C3-C4)-烯基亚硫酰基、(C3-C4)-炔基亚硫酰基、(C3-C10)-环烷基亚硫酰基、(C4-C10)-环烯基亚硫酰基、(C3-C8)-环烷基-(C1-C4)-烷基亚硫酰基、(C4-C8)-环烯基-(C1-C4)-烷基亚硫酰基、(C3-C8)-环烷基-(C3-C4)-烯基亚硫酰基、(C4-C8)-环烯基-(C3-C4)-烯基亚硫酰基、(C1-C4)-烷基-(C3-C8)-环烷基亚硫酰基、(C2-C4)-链烯基-(C3-C8)-环烷基亚硫酰基、(C2-C4)-炔基-(C3-C8)-环烷基亚硫酰基、(C1-C4)-烷基-(C4-C8)-环烯基亚硫酰基、(C2-C3)-链烯基-(C4-C8)-环烯基亚硫酰基、(C1-C10)-烷基磺酰基、(C3-C10)-烯基磺酰基、(C3-C10)-炔基磺酰基、(C3-C10)-环烷基磺酰基、(C4-C10)-环烯基磺酰基、(C3-C8)-环烷基-(C1-C4)-烷基磺酰基、(C4-C8)-环烯基-(C1-C4)-烷基磺酰基、(C3-C8)-环烷基-(C3-C4)-烯基磺酰基、(C4-C8)-环烯基-(C3-C4)-烯基磺酰基、(C1-C4)-烷基-(C3-C8)-环烷基磺酰基、(C2-C4)-链烯基-(C3-C8)-环烷基亚硫酰基、(C3-C6)-炔基-(C3-C8)-环烷基磺酰基、(C1-C4)-烷基-(C4-C8)-环烯基磺酰基、(C3-C4)-链烯基-(C4-C8)-环烯基磺酰基、(C1-C10)-烷氨基、(C3-C10)-烯氨基、(C3-C10)-炔氨基、(C3-C8)-环烷氨基、(C4-C8)-环烯氨基、(C3-C8)-环烷基-(C1-C4)-烷氨基、(C4-C8)-环烯基-(C1-C4)-烷氨基、(C3-C8)-环烷基-(C3-C4)-烯氨基、(C4-C8)-环烯基-(C3-C4)-烯氨基、(C1-C4)-烷基-(C3-C8)-环烷氨基、(C2-C4)-链烯基-(C3-C8)-环烷氨基、(C2-C4)-炔基-(C3-C8)-环烷氨基、(C1-C4)-烷基-(C4-C8)-环烯氨基、(C2-C4)-链烯基-(C4-C8)-环烯氨基、前述最后十四种基团的N-(C1-C4)-烷氨基类似物、(C1-C10)-三烷基甲硅烷基、芳基、芳酰基、杂环羰基、芳氧基、芳硫基、芳氨基、N-(C1-C4)-烷基-芳氨基、前述最后二种基团的N-(C1-C4)-烷氨基类似物、芳基-(C1-C4)-烷氧基、芳基-(C3-C4)-烯氧基、芳基-(C1-C4)-烷硫基、芳基-(C3-C4)-烯硫基、芳基-(C1-C4)-烷氨基、芳基-(C3-C4)-烯氨基、上述最后一种基团的N-(C1-C4)-烷氨基类似物、芳基-(C1-C8)-二烷基甲硅烷基、二芳基-(C1-C8)-烷基甲硅烷基、三芳基甲硅烷基、杂环基、杂环氧基、杂环硫基或杂环氨基,其中所述的芳基或杂环基的环形部分为未经取代或被一或多个选自下列组的基团所取代:卤素、氰基、硝基、氨基、羟基、硫基、(C1-C4)-烷基、(C1-C4)-卤烷基、(C3-C8)-环烷基、(C1-C4)-烷氧基、(C1-C4)-卤烷氧基、(C1-C4)-烷硫基、(C1-C4)-卤烷硫基、(C1-C4)-烷氨基、(C1-C4)-二烷氨基、三甲基甲硅烷基和(C1-C4)-烷酰基;
其中,任选地连接在相同碳原子上的二个烷基R6可与此碳原子一同形成螺环系统,或者
任选地连接在不同碳原子上的二个烷基R6可与式(II)的脂族杂环一同形成稠合或双环系统,或再者,式(II)的杂脂环系统与另一芳基或杂芳基系统一起形成稠合环系统;
且,如果R6为(C1-C10)-烷基、(C2-C10)-链烯基、(C2-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基或(C8-C10)-环炔基,则所述残基为未经取代或经R11基团单-或多取代的,
R11具有上述R7的定义;且其中,在所有属于R6、R7和R11的所述基团中,与碳原子连接的氢未经取代或被至多三个卤素原子所取代,若被氟原子取代,则可被至多最大数目的氟原子取代。
4.如权利要求3的式(I)所示的酰胺及其盐类,其中A和/或B是至少含有一个-O-、-S(O)0,1,2-、-NR8-或-SiR9R10-环原子的单元,其中
R8 为氢、(C1-C10)-烷基、(C3-C10)-链烯基、(C3-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基、芳基、杂环基、(C1-C10)-烷酰基、(C3-C10)-烯酰基、(C3-C10)-炔酰基、(C4-C8)-环烷酰基、芳酰基、杂环羰基、氨基甲酰基、(C1-C6)-一或-二烷基氨基甲酰基、(C3-C10)-一或-二环烷基氨基甲酰基、(C1-C10)-烷氧羰基、(C3-C10)-环烷氧羰基、(C1-C10)-烷基磺酰基、(C3-C10)-烯基磺酰基、(C3-C6)-炔基磺酰基、(C3-C10)-环烷基磺酰基、(C4-C10)-环烯基磺酰基、(C3-C10)-环烷基-(C1-C10)-烷基磺酰基、(C4-C8)-环烯基-(C1-C4)-烷基磺酰基、(C3-C8)-环烷基-(C3-C4)-烯基磺酰基、(C4-C8)-环烯基-(C3-C4)-烯基磺酰基、(C1-C4)-烷基-(C3-C8)-环烷基磺酰基、(C2-C4)-链烯基-(C3-C8)-环烷基磺酰基、(C2-C4)-炔基-(C3-C8)-环烷基磺酰基、(C1-C4)-烷基-(C4-C8)-环烯基磺酰基、(C2-C4)-链烯基-(C4-C8)-环烯基磺酰基、羟基、(C1-C10)-烷氧基、(C3-C10)-烯氧基、(C3-C10)-炔氧基、(C3-C10)-环烷氧基、(C4-C10)-环烯氧基、(C3-C8)-环烷基-(C1-C4)-烷氧基、(C4-C8)-环烯基-(C1-C4)-烷氧基、(C3-C8)-环烷基-(C3-C4)-烯氧基、(C4-C8)-环烯基-(C3-C4)-烯氧基、(C1-C4)-烷基-(C3-C8)-环烷氧基、(C2-C4)-链烯基-(C3-C8)-环烷氧基、(C2-C4)-炔基-(C3-C8)-环烷氧基、(C1-C4)-烷基-(C4-C8)-环烯氧基、(C2-C4)-链烯基-(C4-C8)-环烯氧基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、(C1-C4)-烷氧基-(C3-C4)-烯氧基、芳氧基、芳基-(C1-C10)-烷氧基、芳基-(C3-C10)-烯氧基或芳基-(C3-C10)-炔氧基,且上述为R8的基团是未经取代的基团或可被一或多个选自下列组的基团所取代:氰基、硝基、氨基、羟基、硫基、(C1-C4)-烷基、(C3-C10)-环烷基、(C1-C4)-烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷氨基和(C1-C4)-烷酰基;R9和R10为(C1-C10)-烷基、(C2-C10)-链烯基、(C2-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基、(C8-C10)-环炔基、芳基、芳基-(C1-C4)-烷基或杂环基,且其中,所有属于R8、R9、R10的所述基团中,与碳原子连接的氢未经取代或被一至三个卤素原子所取代,若被氟原子取代,则可被至多最大数目的氟原子取代。
5.如权利要求3的式(I)所示的酰胺及其盐类,其中R5是式(II)的五至七员的脂族杂环,其环中具有一或二个杂原子单元A和/或B和另外一个羰基,此羰基可与该杂单元一起形成内酯或内酰胺单元。
6.如权利要求3的式(I)所示的酰胺及其盐类,其中R6是(C1-C10)-烷基、(C2-C10)-链烯基、(C2-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基或(C8-C10)-环炔基,且所述基团为未经取代或可被R11所单-或多取代,其中R11具有上述权利要求3中所给出的意义。
7.如权利要求3的式(I)所示的酰胺及其盐类,其中芳基、芳酰基、杂环羰基、芳氧基、芳硫基、芳氨基、N-(C1-C4)-烷基-芳氨基、前述最后二种基团的N-(C1-C4)-烷氨基类似物、芳基-(C1-C4)-烷氧基、芳基-(C3-C4)-烯氧基、芳基-(C1-C4)-烷硫基、芳基-(C3-C4)-烯硫基、芳基-(C1-C4)-烷氨基、芳基-(C3-C4)-烯氨基、上述最后基团的N-(C1-C4)-烷氨基类似物、芳基-(C1-C8)-二烷基甲硅烷基、二芳基-(C1-C8)-烷基甲硅烷基、三芳基甲硅烷基、杂环基、杂环氧基、杂环硫基和杂环氨基,其中上述的芳基或杂环基的环形部分为未经取代或被一或多个选自下列组的基团所取代:卤素、氰基、硝基、氨基、羟基、硫基、(C1-C4)-烷基、(C1-C4)-卤烷基、(C3-C8)-环烷基、(C1-C4)-烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷氨基或(C1-C4)-烷酰基。
8.如权利要求1-7中一或多项的式(I)所示的酰胺及其盐类,其中X为-CH-,Y为-O-且n为0。
9.如权利要求1-8中一或多项的式(I)所示的酰胺及其盐类,其中R1为被F和/或Cl所单取代或多取代的(C1-C4)-烷基。
10.如权利要求9的式(I)所示的酰胺及其盐类,其中R1是CF3、CHF2或CF2Cl。
11.一种用于制备如权利要求1-10中一或多项的式(I)所示的酰胺及其盐类的方法,其中权利要求1,包含式(III)的羧酸,
其中X,R1,R2、R3、和n具有如权利要求1中所定义的意义,以其活性衍生物形式,在一种碱的存在下,与式(IV)的化合物反应,其中R4和R5具有如权利要求1中所定义的意义
HNR4R5 (IV)
12.一种具有杀昆虫、杀螨、杀蜱、杀线虫、杀软体动物和/或杀真菌作用的组合物,其特征在于,包含至少一种如权利要求1-10的一或多项的式(I)化合物及其盐类。
13.如权利要求12的组合物,其在于混合物中具有载体和/或表面活性剂。
14.如权利要求1-10的一或多项的式(I)化合物及其盐类的用途,其用于控制有害生物体。
15.如权利要求14的用途,用于控制在转基因作物中的有害生物体。
16.如权利要求1-10的一或多项的式(I)化合物及其盐类的用途,用于防范或驱除害虫。
17.如权利要求1-10的一或多项的式(I)化合物及其盐类的用途,用于制备人用和/或动物用的药剂。
18.如权利要求1-10的一或多项的式(I)化合物及其盐类的用途,用于制备控制内和外寄生虫的药剂。
19.一种用于控制有害昆虫、蜘蛛和/或线虫的方法,其中将有效量的如权利要求1-10的一或多项的式(I)化合物及其盐类施用在这些害虫上或希望产生效用的区域。
20.一种用于防范或驱除有害生物体的方法,其中将如权利要求1-10的一或多项的式(I)化合物及其盐类施用至欲防范或驱除有害生物体的区域。
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EP3375778A1 (en) * | 2017-03-14 | 2018-09-19 | Artax Biopharma Inc. | Aryl-piperidine derivatives |
EP3617196B1 (en) | 2017-04-27 | 2023-06-07 | Ishihara Sangyo Kaisha, Ltd. | N-(4-pyridyl) nicotinamide compound or salt thereof |
US10526278B2 (en) | 2017-10-19 | 2020-01-07 | Wisconsin Alumni Research Foundation | Inhibitors of quorum sensing receptor LasR |
WO2019154665A1 (en) * | 2018-02-07 | 2019-08-15 | Basf Se | New pyridine carboxamides |
BR112021008995A2 (pt) * | 2018-12-26 | 2021-08-10 | Raqualia Pharma Inc. | derivados heterocíclicos como bloqueadores de nav1.7 e nav1.8 |
CN115215848B (zh) * | 2021-04-20 | 2024-04-19 | 中国药科大学 | 蛋白激酶抑制剂及其衍生物、制备方法、药物组合物和应用 |
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JP2994182B2 (ja) * | 1992-07-23 | 1999-12-27 | 石原産業株式会社 | アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤 |
FR2725719B1 (fr) * | 1994-10-14 | 1996-12-06 | Jouveinal Inst Rech | Diazepino-indoles inhibiteurs de phosphodiesterases iv |
TW366261B (en) * | 1996-04-02 | 1999-08-11 | Nihon Nohyaku Co Ltd | Pyridine-2,3-dicarboxylic acid diamide derivatives and herbicides comprising said derivatives as active ingredient |
JPH10195072A (ja) * | 1997-01-17 | 1998-07-28 | Sumitomo Chem Co Ltd | ピリジン−3−カルボキサミド化合物またはその塩およびその用途 |
AR023071A1 (es) * | 1998-12-23 | 2002-09-04 | Syngenta Participations Ag | Compuestos de piridincetona, compuestos intermediarios, composicion herbicida e inhibidora del crecimiento de plantas, metodo para controlar la vegetacion indeseada, metodo para inhibir el crecimiento de las plantas, y uso de la composicion para controlar el crecimiento indeseado de plantas. |
HUP0300406A3 (en) * | 2000-03-22 | 2003-10-28 | Bayer Cropscience Gmbh | Heterocyclic acylsulfimides, a method for their production, compositions containing them and their use as pesticides |
DE10014006A1 (de) * | 2000-03-22 | 2001-09-27 | Aventis Cropscience Gmbh | Heterocyclische Acylsulfimine, Verfahren zu ihrer Herstellung , sie enthalten Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
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2001
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2002
- 2002-09-14 DE DE50210172T patent/DE50210172D1/de not_active Expired - Lifetime
- 2002-09-14 ES ES02777107T patent/ES2287321T3/es not_active Expired - Lifetime
- 2002-09-14 EP EP02777107A patent/EP1434485B1/de not_active Expired - Lifetime
- 2002-09-14 BR BR0213594-9A patent/BR0213594A/pt not_active IP Right Cessation
- 2002-09-14 KR KR1020047004542A patent/KR100918790B1/ko not_active IP Right Cessation
- 2002-09-14 JP JP2003531812A patent/JP4366518B2/ja not_active Expired - Fee Related
- 2002-09-14 WO PCT/EP2002/010330 patent/WO2003028459A1/de active IP Right Grant
- 2002-09-14 CN CNB028188977A patent/CN100408574C/zh not_active Expired - Fee Related
- 2002-09-14 AP APAP/P/2004/003023A patent/AP2004003023A0/en unknown
- 2002-09-14 DK DK02777107T patent/DK1434485T3/da active
- 2002-09-14 HU HU0401684A patent/HUP0401684A3/hu unknown
- 2002-09-14 AT AT02777107T patent/ATE362313T1/de active
- 2002-09-14 MX MXPA04002886A patent/MXPA04002886A/es active IP Right Grant
- 2002-09-14 PT PT02777107T patent/PT1434485E/pt unknown
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- 2002-09-26 AR ARP020103636A patent/AR036682A1/es not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
---|---|
CO5570635A2 (es) | 2005-10-31 |
US7332509B2 (en) | 2008-02-19 |
ES2287321T3 (es) | 2007-12-16 |
MXPA04002886A (es) | 2004-07-15 |
ATE362313T1 (de) | 2007-06-15 |
CN100408574C (zh) | 2008-08-06 |
PT1434485E (pt) | 2007-08-23 |
BR0213594A (pt) | 2004-08-31 |
JP2005504105A (ja) | 2005-02-10 |
AR036682A1 (es) | 2004-09-29 |
WO2003028459A8 (de) | 2004-04-29 |
AP2004003023A0 (en) | 2004-06-30 |
US20040006047A1 (en) | 2004-01-08 |
KR20040039439A (ko) | 2004-05-10 |
ZA200401524B (en) | 2005-07-27 |
KR100918790B1 (ko) | 2009-09-25 |
DK1434485T3 (da) | 2007-09-24 |
EP1434485B1 (de) | 2007-05-16 |
JP4366518B2 (ja) | 2009-11-18 |
DE50210172D1 (de) | 2007-06-28 |
CY1107713T1 (el) | 2013-04-18 |
DE10148290A1 (de) | 2003-04-17 |
HUP0401684A2 (hu) | 2004-12-28 |
EP1434485A1 (de) | 2004-07-07 |
HUP0401684A3 (en) | 2005-06-28 |
WO2003028459A1 (de) | 2003-04-10 |
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