CN108349915A - 杀微生物的苯胺衍生物 - Google Patents
杀微生物的苯胺衍生物 Download PDFInfo
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- CN108349915A CN108349915A CN201680064433.0A CN201680064433A CN108349915A CN 108349915 A CN108349915 A CN 108349915A CN 201680064433 A CN201680064433 A CN 201680064433A CN 108349915 A CN108349915 A CN 108349915A
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- radical
- alkyl
- optionally substituted
- alkoxy
- aryl
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- 229960000996 pyrantel pamoate Drugs 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- MRUMAIRJPMUAPZ-UHFFFAOYSA-N quinolin-8-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CN=C2C(O)=CC=CC2=C1 MRUMAIRJPMUAPZ-UHFFFAOYSA-N 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
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- 239000003001 serine protease inhibitor Substances 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
- 229920002545 silicone oil Polymers 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
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- LOGJGKGBKZOEKZ-UHFFFAOYSA-N sordidin Natural products O1C2(C)CC(C)C1(CC)OC(C)C2 LOGJGKGBKZOEKZ-UHFFFAOYSA-N 0.000 description 1
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- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
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- 108010076424 stilbene synthase Proteins 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 229960002135 sulfadimidine Drugs 0.000 description 1
- ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 235000013616 tea Nutrition 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
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YJINQJFQLQIYHX-UHFFFAOYSA-N tetradec-11-enyl acetate Chemical compound CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 150000005326 tetrahydropyrimidines Chemical class 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-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
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-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
- IGOWHGRNPLFNDJ-UHFFFAOYSA-N tricos-9t-ene Natural products CCCCCCCCCCCCCC=CCCCCCCCC IGOWHGRNPLFNDJ-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- XBRCDWHXULVEFB-UHFFFAOYSA-N triphenyltin(1+) Chemical compound C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 XBRCDWHXULVEFB-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 206010061393 typhus Diseases 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 239000004560 ultra-low volume (ULV) liquid Substances 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002578 wasp venom Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
具有式(I)的化合物
Description
本发明涉及杀微生物的苯胺衍生物,例如作为活性成分,该苯胺衍生物具有杀微生物活性、特别是杀真菌活性。本发明还涉及这些苯胺衍生物的制备,涉及包含这些苯胺衍生物中的至少一种的农用化学组合物,并且涉及这些苯胺衍生物或其组合物在农业或园艺中用于控制或防止植物、收获的粮食作物、种子或非生命材料被致植物病的微生物,优选是真菌侵染的用途。
WO 01/14339和WO 01/05769披露了杀真菌活性的杂环芳香族酰胺化合物。
根据本发明,提供了具有式(I)的化合物:
其中,
R1是C1-C6烷氧基或C1-C6酰氨基,其中C1-C6烷氧基和C1-C6酰氨基任选地被R9表示的1至3个基团取代;并且
R2是羟基、C1-C6酰氧基、C1-C6烷氧基C1-C6烷氧基或C1-C6酰氧基C1-C6烷氧基,其中C1-C6酰氧基、C1-C6烷氧基C1-C6烷氧基和C1-C6酰氧基C1-C6烷氧基任选地被R9表示的1至3个基团取代;或者
R1和R2连同它们所附接的碳原子一起形成1,3-噁唑环;
R3是氢、C1-C6烷基、C1-C6烷氧基或C3-C6环烷基;
R4、R5、R6和R7独立地是氢、卤素、C1-C6烷基或C1-C6烷氧基,其中C1-C6烷基和C1-C6烷氧基任选地被R9表示的1至3个基团取代;
R8是C3-C9环烷基,其任选地被R10表示的1至5个基团取代,其中R10独立地选自羟基、卤素、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基,其中C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基任选地被R9表示的1至3个基团取代;或者
R8是C3-C9环烷基,其任选地被R10表示的1或2个基团取代,其中R10独立地选自C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基、杂芳基C1-C6烷基、=O、=C(R11)2、=NOR11或=N-N(R11)2,其中C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基或杂芳基C1-C6烷基任选地被R9表示的1至3个基团取代;或者
R8是C3-C9环烷基,其任选地被R10表示的1个基团取代,其中R10是螺环的3至10元饱和的或部分不饱和的碳环系统或杂环系统,该系统含有1至3个杂原子,所述杂原子选自氧、氮和硫,并且任选地被卤素、C1-C4烷基或=O表示的1至5个基团取代;
R9独立地选自卤素、氰基、C1-C4烷基和C1-C4烷氧基,其中C1-C4烷基和C1-C4烷氧基任选地被卤素表示的1至5个基团取代;
R11是氢、C1-C6烷基、C2-C6烯基、C2-C6炔基或芳基,其中C1-C6烷基、C2-C6烯基、C2-C6炔基和芳基任选地被R9表示的1至3个基团取代;并且
X是CH或N;
或其盐或N-氧化物;
其条件是具有式(I)的化合物不是3-羟基-4-甲氧基-N-[4-(3,3,5,5-四甲基环己氧基)苯基]吡啶-2-甲酰胺。
出人意料地,为实际目的,已经发现了具有式(I)的新颖化合物有着非常有利水平的生物活性,用来保护植物免受真菌引起的疾病的侵害。
根据本发明的第二方面,提供了如下农用化学组合物,其含有杀真菌有效量的根据本发明所述的具有式(I)的化合物。
根据本发明的第三方面,提供了用于控制或预防有用植物被致植物病微生物侵染的方法,其中将杀真菌有效量的具有式(I)的化合物,或包含这种化合物作为活性成分的组合物施用至这些植物、其部分或其场所。
根据本发明的第四方面,提供了具有式(I)的化合物作为杀真菌剂的用途。根据本发明的这个特定方面,所述用途可以排除通过手术或疗法来治疗人体或动物体的方法。
当取代基被表示为“被任选地取代”时,这是指它们可以带有或可以不带有一个或多个相同的或不同的取代基,例如一个、两个或三个R9取代基。例如,被1、2或3个卤素取代的C1-C6烷基可以包括但不限于-CH2Cl、-CHCl2、-CCl3、-CH2F、-CHF2、-CF3、-CH2CF3或-CF2CH3基团。作为另一个实例,被1、2或3个卤素取代的C1-C6烷氧基可以包括但不限于CH2ClO-、CHCl2O-、CCl3O-、CH2FO-、CHF2O-、CF3O-、CF3CH2O-或CH3CF2O-基团。
如本文中所使用的,术语“羟基(hydroxyl)”或“羟基(hydroxy)”代表-OH基团。
如本文中所使用的,术语“氰基”是指-CN基团。
如本文中所使用的,术语“卤素”是指氟、氯、溴或碘。
如本文中所使用的,术语“C1-C6烷基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,该烃链基团不含不饱和现象,具有从一至六个碳原子,并且其通过单键附接至该分子的剩余部分。术语“C1-C4烷基”应被相应地解释。C1-C6烷基的实例包括但不限于甲基、乙基、正丙基、正丁基、正戊基、正己基及其异构体,例如异丙基、异丁基、仲丁基、叔丁基或异戊基。“C1-C6亚烷基”基团是指C1-C6烷基的相应定义,不同之处在于该基团是通过两个单键附接至该分子的剩余部分。C1-C6亚烷基的实例包括但不限于-CH2-、-CH2CH2-和-(CH2)3-。
如本文中所使用的,术语“C2-C6烯基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,该烃链基团含有至少一个可以是(E)-或(Z)-构型的双键,具有从二至六个碳原子,其通过单键附接至该分子的剩余部分。术语“C2-C4烯基”和“C2-C3烯基”应相应地解释。C2-C6烯基的实例包括但不限于乙烯基(ethenyl)(乙烯基(vinyl))、丙-1-烯基、丙-2-烯基(烯丙基)和丁-1-烯基。
如本文所使用的,术语“C2-C6炔基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,该烃链基团包含至少一个三键,具有从二至六个碳原子,并且其通过单键附接至该分子的剩余部分。术语“C2-C4炔基”和“C2-C3炔基”应相应地解释。C2-C6炔基的实例包括但不限于乙炔基、丙-1-炔基、丁-1-炔基。
如本文所使用的,术语“C1-C6烷氧基”是指具有式-ORa的基团,其中Ra是如上通常定义的C1-C6烷基基团。术语“C1-C4烷氧基”应被相应地解释。C1-C6烷氧基的实例包括但不限于甲氧基、乙氧基、1-甲基乙氧基(异丙氧基)、丙氧基、丁氧基、1-甲基丙氧基和2-甲基丙氧基。
如本文所使用的,术语“C3-C9环烷基”是指属于单或双环饱和环系统并含有3至9个碳原子的基团,其可以包括亚烷基桥联的环系统。C3-C6环烷基和C3-C5环烷基应相应地解释。C3-C9环烷基的实例包括但不限于:环丙基、1-甲基环丙基、2-甲基环丙基、环丁基、环戊基和环己基、环庚基、环辛基或降冰片基。
如本文所使用的,术语“杂环状基”或“杂环基”是指稳定的5或6元非芳香族单环,其包含1、2或3个杂原子,或9或10元双环,其包含1、2、3、4或5个杂原子(包括1、2或3个杂原子),其中杂原子独立地选自氮、氧和硫。所述杂环基基团可以经碳原子或杂原子键结至分子的剩余部分。杂环基的实例包括但不限于吖丙啶基、氮杂环丁烷基、氧杂环丁烷基、硫杂环丁烷基、四氢呋喃基、吡咯烷基、吡唑烷基、咪唑烷基、哌啶基、哌嗪基、吗啉基、二氧戊环基、二硫杂环戊烷基和噻唑烷基。
如在本文所使用的,术语“芳基”是指仅由碳原子和氢原子组成的芳香族环系统,该芳香族环系统可以是单环的-、二环的-或三环的。这样的环系统的实例包括苯基、萘基、蒽基、茚基或菲基。
如本文所使用的,术语“芳基C1-C6烷基”是指通过如上所定义的C1-C6烷基基团附接至该分子的其余部分的芳基环。芳基C1-C6烷基的实例包括但不限于苄基或2-苯基乙基。
如本文使用的,术语“杂芳基”是指包含1、2、3或4个单独地选自氮、氧和硫的杂原子的5元或6元芳族单环基团。杂芳基的实例包括但不限于呋喃基、吡咯基、噻吩基、吡唑基、咪唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、三唑基、四唑基、吡嗪基、哒嗪基、嘧啶基或吡啶基。
如本文所使用的,术语“杂芳基C1-C6烷基”是指通过如上所定义的C1-C6烷基基团附接至该分子的其余部分的杂芳基环。
如本文所使用的,术语“芳基氧基”是指具有式-ORa的基团,其中Ra是如上通常定义的芳基基团。芳氧基包括但不限于苯氧基。
如本文所使用的,术语“杂芳基氧基”是指具有式-ORa的基团,其中Ra是如上通常定义的杂芳基基团。
如本文所使用的,术语“C2-C6酰基”是指基团RaC(=O)-,其中Ra是如上通常定义的C1-C5烷基基团或芳基基团。酰基基团包括但不限于乙酰基、丙酰基和苯甲酰基。
如本文所使用的,术语“C1-C6酰基氧基”是指具有式-ORb的基团,其中Rb是如上通常定义的甲酰基或C2-C6酰基基团。C1-C6酰基氧基基团包括但不限于乙酰氧基。
如本文所使用的,术语“C1-C6酰氨基”是指具有式-NHRc的基团,其中Rc是如上通常定义的甲酰基或C2-C6酰基基团。
如本文所使用的,术语“C1-C6烷氧基-C1-C6烷氧基”是指基团-ORa-ORb,其中Ra是如上通常定义的C1-C6亚烷基基团并且Rb是如上通常定义的C1-C6烷基基团。
如本文所使用的,术语“C1-C6酰氧基-C1-C6烷氧基”是指基团-ORa-OC(=O)-Rb,其中如上通常定义的,Ra是C1-C6亚烷基基团并且Rb是C1-C6烷基基团。
如本文所使用的,术语C1-C6烷基硫基是指-SRa基团,其中Ra是如上通常所定义的C1-C6烷基基团。
如本文所使用的,术语“噁唑”是指1,3-噁唑。
如本文所使用的,术语C1-C6烷基磺酰基是指-S(O)2Ra基团,其中Ra是如上通常所定义的C1-C6烷基基团。
如本文所使用的,术语C1-C6烷基羰基氧基是指-OC(=O)Ra基团,其中Ra是如上通常所定义的C1-C6烷基基团。
如本文所使用的,=O表示氧代基团,例如在羰基(-C(=O)-)基团中所见。
如本文所使用的,关于R8被R10任选取代的术语“螺环的”是指取代导致螺环部分(由2或3个环组成)的形成并且被R10促成螺环部分的环成员(即,3至10元、3至6元等)的数目包括了与R8共有的螺环碳被计数。
一种或多种可能不对称的碳原子出现在具有式(I)的化合物中,表明这些化合物能以光学异构体形式出现,即对映体或非对映体的形式。作为围绕单键的受限旋转的结果,还可能存在阻转异构体。式(I)旨在包括所有那些可能的异构体形式及其混合物。本发明包括具有式(I)的化合物的所有那些可能的异构体形式及其混合物。同样地,式(I)旨在包括所有可能的互变异构体。本发明包括针对具有式(I)的化合物的所有可能的互变异构形式。
在每种情况下,根据本发明所述的具有式(I)的这些化合物是自由形式、氧化形式(如N-氧化物)或盐形式(如农艺学上可用的盐形式)。
N-氧化物是叔胺的氧化形式或含氮杂芳香族化合物的氧化形式。例如,A.Albini和S.Pietra于1991年在博卡拉顿(Boca Raton)CRC出版社出版的名为“Heterocyclic N-oxides[杂环N-氧化物]”一书中描述了它们。
关于具有式(I)的化合物,以下清单提供了取代基R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11以及X的定义,包括优选的定义。对于这些取代基中的任何一个,以下给出的任何定义都可以结合以下或在本文件中的其他地方给出的任何其他取代基的任何定义。
R1是C1-C6烷氧基或C1-C6酰氨基,其中C1-C6烷氧基和C1-C6酰氨基任选地被R9表示的1至3个基团取代;优选地,R1是C1-C6烷氧基,更优选地是C1-C4烷氧基,甚至更优选地是甲氧基、乙氧基或异丙氧基,并且最优选地是甲氧基。
R2是羟基、C1-C6酰氧基、C1-C6烷氧基C1-C6烷氧基或C1-C6酰氧基C1-C6烷氧基,其中C1-C6酰氧基、C1-C6烷氧基C1-C6烷氧基和C1-C6酰氧基C1-C6烷氧基任选地被R9表示的1至3个基团取代。优选地,R2是羟基、C1-C4酰氧基或C1-C4酰氧基C1-C4烷氧基,并且更优选地是羟基、乙酰氧基或异丁酰基氧基甲氧基。
在本发明的一些实施例中,R1是C1-C4烷氧基并且R2是羟基。
在本发明的其他实施例中,R1和R2连同它们所附接的碳原子一起形成噁唑环。
R3是氢、C1-C6烷基、C1-C6烷氧基或C3-C6环烷基。优选地,R3是氢、甲基或甲氧基,并且更优选地是氢。
R4、R5、R6和R7独立地是氢、卤素、C1-C6烷基或C1-C6烷氧基,其中C1-C6烷基和C1-C6烷氧基任选地被R9表示的1至3个基团取代。优选地,R4、R5、R6和R7独立地是氢或卤素;或者R4是卤素(例如,氟或氯)并且R5、R6和R7是氢。
在本发明的一些实施例中,R4是卤素、C1-C6烷基或C1-C6烷氧基,其中C1-C6烷基和C1-C6烷氧基任选地被R9表示的1至3个基团取代。优选地,R4是氢、氟或氯,并且R5、R6和R7是氢。
R8是C3-C9环烷基,其任选地被R10表示的1至5个基团取代,其中R10独立地选自羟基、卤素、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基,其中C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基任选地被R9表示的1至3个基团取代;或是C3-C9环烷基,其任选地被R10表示的1至2个基团取代,其中R10独立地选自C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基、杂芳基C1-C6烷基、=O、=C(R11)2、=NOR11或=N-N(R11)2,其中C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基或杂芳基C1-C6烷基任选地被R9表示的1至3个基团取代;或是C3-C9环烷基,其任选地被R10表示一个基团取代,其中R10是螺环的3至10元饱和的或部分不饱和的碳环系统或杂环系统,该系统含有1至3个杂原子,所述杂原子选自氧、氮和硫,任选地被卤素、C1-C4烷基或=O表示的1至5个基团取代。
在本发明的某些实施例中,R8是C3-C9环烷基,其任选地被R10表示的1个基团取代,其中R10是螺环的3至6元饱和的或部分不饱和的碳环系统或杂环系统,该系统含有1至3个杂原子,所述杂原子选自氧、氮和硫,任选地被卤素、C1-C4烷基或=O表示的1至5个基团取代。
可替代地,R8是C3-C6环烷基,其任选地被R10表示的1个基团取代,其中R10是螺环的3至6元(或3至5元)饱和的或部分不饱和的碳环系统或杂环系统,该系统含有1或2个杂原子,所述杂原子选自氧、氮和硫,任选地被卤素、C1-C4烷基或=O表示的1至3个基团取代。
优选地,R8是C3-C9环烷基,其任选地被R10表示的1至3个基团取代,其中R10独立地选自羟基、卤素、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基;或是C3-C9环烷基,其任选地被R10表示的1至2个基团取代,其中R10独立地选自C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基、杂芳基C1-C6烷基、=O、=C(R11)2、=NOR11或=N-N(R11)2,其中C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基或杂芳基C1-C6烷基任选地被R9表示的1至3个基团取代;或是C3-C9环烷基,其任选地被R10表示的1个基团取代,其中R10是螺环的3至10元(或3至6元)饱和的或部分不饱和的碳环系统或杂环系统,该系统含有1或2个杂原子,所述杂原子选自氧、氮和硫,任选地被卤素、C1-C4烷基或=O表示的1至3个基团取代。
更优选地,R8是C7-C9环烷基,其任选地被R10表示的1至5个基团取代,其中R10独立地选自羟基、卤素、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基,其中C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基任选地被R9表示的1至3个基团取代;或是C3-C9环烷基,其任选地被R10表示的1至2个基团取代,其中R10独立地选自C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基、杂芳基C1-C6烷基、=O、=C(R11)2、=NOR11或=N-N(R11)2,其中C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基或杂芳基C1-C6烷基任选地被R9表示的1至3个基团取代;或是C3-C9环烷基,其任选地被R10表示的1个基团取代,其中R10是螺环的3至10元(或3至6元)饱和的或部分不饱和的碳环系统或杂环系统,该系统含有1或2个杂原子,所述杂原子选自氧、氮和硫,任选地被卤素、C1-C4烷基或=O表示的1至3个基团取代。
甚至更优选地,R8是C5-C8环烷基,其任选地被R10表示的1或2个基团取代,其中R10独立地选自羟基、C1-C6烷基、C1-C6烷基羰氧基、C3-C6环烷基、芳基、=C(R11)2、=NOR11;或者R8是C5-C8环烷基,其任选地被R10表示的1个基团取代,R10是螺环的1,3-二氧戊环-2-基,其中C1-C6烷基、C3-C6环烷基、芳基、=C(R11)2和=NOR11任选地被R9表示的1至3个基团取代,或者螺环的1,3-二氧戊环-2-基任选地被卤素、C1-C4烷基或=O表示的1至3个基团取代;并且R11独立地选自氢、C1-C6烷基、C2-C6烯基、C2-C6炔基和芳基。
仍然更优选地,R8是C5-C8环烷基,其任选地被R10表示的1或2个基团取代,其中R10独立地选自羟基、C1-C4烷基、C1-C6烷基羰氧基、C6环烷基、苯基、=C(R11)2或=NOR11,并且R11独立地选自氢、C1-C4烷基、C2-C4烯基、C2-C4炔基和苯基。
在本发明的一些实施例中,在具有式(I)的化合物中,当R8是环己基时,只有一个碳环原子(位置2-至6-)可以被R9表示的两个基团(其是甲基)取代。在本发明的其他实施例中,在具有式(I)的化合物中,当R8是被R9表示的四个基团(其是甲基)取代的环己基并且其中R9由两个二甲基部分组成时,环己基的2-或4-位置中的至少一个是二甲基取代的。
在本发明的另一个实施例中,在具有式(I)的化合物中,当R8是被R9表示的四个基团(其是甲基)取代的环己基并且其中两个环己基环碳位置各自被两个甲基基团取代时,R3、R4、R5、R6和R7中的至少一个不是氢。
R9独立地选自卤素、氰基、C1-C4烷基和C1-C4烷氧基,其中C1-C4烷基和C1-C4烷氧基任选地被卤素表示的1至5个基团取代。优选地,R9是氯、氟、氰基、甲基、甲氧基或乙氧基。优选地,每个取代的R1、R2、R4、R5、R6、R7或R10基团具有一个或多个R9取代基,并且更优选地具有一个R9取代基。
R10独立地选自羟基、卤素、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C3-C6环烷基、C2-C6烯基、C2-C6炔基、C1-C6烷基羰氧基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基、杂芳基C1-C6烷基、=O、=C(R11)2、=NOR11或=N-N(R11)2,其中C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基和杂芳基C1-C6烷基任选地被R9表示的1至3个基团取代。优选地,R10是C1-C6烷基、C3-C6环烷基、芳基、=C(R11)2、=NOR11或螺环的1,3-二氧戊环-2-基,其任选地被R9表示的1至3个基团取代,或其中螺环的1,3-二氧戊环-2-基任选地被卤素、C1-C4烷基或=O表示的1至3个基团取代,其中R11独立地选自氢、C1-C6烷基、C2-C6烯基、C2-C6炔基和芳基。更优选地,R10是C1-C4烷基、C6环烷基、苯基、=C(R11)2或=NOR11,其中R11独立地选自氢、C1-C4烷基、C2-C4烯基、C2-C4炔基和苯基。
在本发明的一些实施例中,R10是螺环的3至10元饱和的或部分不饱和的碳环系统或杂环系统,该系统含有1至3个杂原子,所述杂原子选自氧、氮和硫,任选地被卤素、C1-C4烷基或=O取代。
R11是氢、C1-C6烷基、C2-C6烯基、C2-C6炔基或芳基,其中C1-C6烷基、C2-C6烯基、C2-C6炔基和芳基任选地被R9表示的1至3个基团取代。优选地,R11是氢、C1-C6烷基或芳基。甚至更优选地,R11是氢或C1-C6烷基。
X是CH或N。优选地,X是N。
根据本发明,R1、R2、R4、R5、R6、R7、R10和R11可以任选地被1、2或3个R9取代基取代。R8可以任选地被1、2、3、4或5个R10取代基取代,特别是被1或2个R10取代基取代。
根据本发明,具有式(I)的化合物可以是如下,其中:
优选地,R1是C1-C6烷氧基,其任选地被R9表示的1至3个基团取代;
R2是羟基、C1-C6酰氧基或C1-C6酰氧基C1-C6烷氧基,其中C1-C6酰氧基和C1-C6酰氧基C1-C6烷氧基任选地被R9表示的1至3个基团取代;或者
R1和R2连同它们所附接的碳原子一起形成1,3-噁唑环;
R3是氢、甲基或甲氧基;
R4、R5、R6和R7独立地是氢或卤素;
R8是C5-C8环烷基,其任选地被R10表示的1至2个基团取代;
R9独立地选自羟基、氯、氟、甲基、甲氧基或乙氧基;
R10独立地选自C1-C6烷基、C1-C6烷氧基、C3-C6环烷基、芳基、芳氧基、芳基C1-C6烷基、=C(R11)2、=NOR11和=O;
R11独立地选自氢、C1-C6烷基、C2-C6烯基、C2-C6炔基和芳基;并且
X是CH或N。
更优选地,R1是C1-C4烷氧基;
R2是羟基、C1-C4酰氧基或C1-C4酰氧基C1-C4烷氧基;
R3是氢、甲基或甲氧基;
R4是氢或卤素;
R5、R6和R7独立地是氢或卤素;
R8是C5-C8环烷基,其任选地被R10表示的1或2个基团取代;
R10独立地选自C1-C4烷基、C3-C6环烷基、芳基、=C(R11)2和=NOR11;
R11独立地选自氢、C1-C6烷基、C2-C6烯基、C2-C6炔基和芳基;并且
X是N。
甚至更优选地,R1是甲氧基;
R2是羟基或C1-C4酰氧基C1-C4烷氧基;
R3是氢;
R4是氢或氟;
R5、R6和R7是氢;
R8是环己基、环庚基或环辛基,其任选地被R10表示的1或2个基团取代;
R10是C1-C4烷基或芳基;并且
X是N。
优选地,根据式(I)所述的化合物选自:
N-[4-(环戊氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环戊氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环己氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环己氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(4,4-二甲基环己氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(4,4-二甲基环己氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[2-氟-4-(3,3,5,5-四甲基环己氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环庚氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环庚氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环辛氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环辛氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺。
本发明还涉及具有式I-1的化合物:
其中R3、R4、R5、R6、R7和R8具有针对式I所述的定义。R3、R4、R5、R6、R7和R8的优选的定义是如针对式(I)所定义的。
本发明还涉及具有式I-2的化合物:
其中R3、R4、R5、R6、R7和R8具有如针对式I所述的定义。R3、R4、R5、R6、R7和R8的优选的定义是如针对式(I)所定义的。
本发明还涉及具有式I-3的化合物:
其中R3、R4、R5、R6、R7和R8具有如针对式(I)所述的定义。R3、R4、R5、R6、R7和R8的优选的定义是如针对式(I)所定义的。
本发明还涉及具有式I-4的化合物:
其中R3、R4、R5、R6、R7和R8具有如针对式(I)所述的定义。R3、R4、R5、R6、R7和R8的优选的定义是如针对式(I)所定义的。
本发明还涉及具有式I-5的化合物:
其中R3、R4、R5、R6、R7和R8具有如针对式(I)所述的定义。R3、R4、R5、R6、R7和R8的优选的定义是如针对式(I)所定义的。
本发明还涉及具有式I-6的化合物:
其中R1、R2、R4、R5、R6、R7、R8和X具有如针对式(I)所述的定义。R1、R2、R4、R5、R6、R7、R8和X的优选的定义是如针对式(I)所定义的。
本发明还涉及具有式I-7的化合物:
其中R1、R2、R3、R8和X具有如针对式(I)所述的定义。R1、R2、R3、R8和X的优选的定义是如针对式(I)所定义的。
本发明另外的优选实施例是实施例E-I.a至E-I.t,这些实施例被定义为由选自如下所述的式(I.a)至(I.t)组成的组的一个式所表示的具有式(I)的化合物,其中在式(I.a)至(I.t)中,取代基R3、R4、R5、R6、R7和R8的含义具有上述优选含义或相应表1中给出的含义1至300之一。
例如,实施例E-I.a由具有式(I.a)的化合物表示
并且取代基R3、R4、R5、R6、R7和R8具有如上所定义的含义或表1中给出的含义1至300之一。
实施例E-I.b至E-I.t相应地被定义,并且取代基R3、R4、R5、R6、R7和R8具有如上所定义的含义或相应表1中给出的含义1至300之一。
本发明所述的化合物可以如在以下方案中所示来制备,其中(除非另外说明)每一变量的定义是如以上针对具有式(I)的化合物所定义的。
根据本发明具有式(I-A)的化合物(其中R1、R2、R4、R5、R6、R7、R8和X是如针对式(I)所定义的)可以通过使具有式(II)的化合物(其中R1、R2和X是如针对式(I)所定义的并且R12是羟基、卤素或C1-C6烷氧基)与具有式(III)的化合物(其中R4、R5、R6、R7和R8是如针对式(I)所定义的)以及与碱或肽偶联剂转化来获得。这在下面的方案1中示出。
方案1
具有式(III)的化合物(其中R4、R5、R6、R7和R8是如针对式(I)定义的)可以通过将具有式(IV)的化合物(其中R4、R5、R6、R7和R8是如针对式(I)定义的)在还原条件下,例如催化加氢或与铁粉和盐酸转化来获得。这在下面的方案2中示出。
方案2
具有式(IV)的化合物(其中R4、R5、R6、R7和R8是如针对式(I)定义的)可以通过将具有式(V)的化合物(其中R4、R5、R6和R7是如针对式(I)定义的)与具有式(VI)的化合物(其中R8是如针对式(I)定义的并且R13是羟基、卤素(优选地是氯或溴)或磺酸盐(优选地是甲磺酸盐))与碱或在三信反应(Mitsunobu reaction)的条件下转化来获得。这在下面的方案3中示出。
方案3
可替代地,具有式(IV)的化合物(其中R4、R5、R6、R7和R8是如针对式(I)定义的)可以通过将具有式(VII)的化合物(其中R4、R5、R6和R7是如针对式(I)定义的)与具有式(VIII)的化合物(其中R8是如针对式(I)定义的)以及与碱转化来获得。这在下面的方案4中示出。
方案4
可替代地,具有式(I-A)的化合物(其中R1、R2、R4、R5、R6、R7、R8和X是如针对式(I)所定义的)可以通过将具有式(IX)的化合物(其中R1、R2、R4、R5、R6、R7和X是如针对式(I)定义的)与具有式(VI)的化合物(其中R8是如针对式(I)定义的并且R13是羟基、卤素(优选地是氯或溴)或磺酸盐(优选地是甲磺酸盐))与碱或在三信反应(Mitsunobu reaction)的条件下转化来获得。这在下面的方案5中示出。
方案5
具有式(IX)的化合物(其中R1、R2、R4、R5、R6、R7和X是如针对式(I)定义的)可以通过将具有式(II)的化合物(其中R1、R2和X是如针对式(I)定义的并且R12是羟基、卤素或C1-C6烷氧基)与具有式(X)的化合物(其中R4、R5、R6和R7是如针对式(I)定义的)以及与碱或肽偶联剂转化来获得。这在下面的方案6中示出。
方案6
可替代地,具有式(I-A)的化合物(其中R1、R2、R4、R5、R6、R7、R8和X是如针对式(I)定义的)可以通过将具有式(XI)的化合物(其中R1、R2、R4、R5、R6、R7和X是如针对式(I)定义的)与具有式(VIII)的化合物(其中R8是如针对式(I)定义的)以及与碱转化来获得。这在下面的方案7中示出。
方案7
具有式(XI)的化合物(其中R1、R2、R4、R5、R6、R7和X是如针对式(I)定义的)可以通过将具有式(II)的化合物(其中R1、R2和X是如针对式(I)定义的并且R12是羟基、卤素或C1-C6烷氧基)与具有式(XII)的化合物(其中R4、R5、R6和R7是如针对式(I)定义的)与碱或肽偶联剂转化来获得。这在下面的方案8中示出。
方案8
具有式(X)的化合物(其中R4、R5、R6和R7是如针对式(I)定义的)可以通过将具有式(V)的化合物(其中R4、R5、R6和R7是如针对式(I)定义的)在还原条件下,例如催化加氢或与铁粉和盐酸转化来获得。这在下面的方案9中示出。
方案9
具有式(XII)的化合物(其中R4、R5、R6和R7是如针对式(I)定义的)可以通过将具有式(VII)的化合物(其中R4、R5、R6和R7是如针对式(I)定义的)在还原条件下,例如催化加氢或与铁粉和盐酸转化来获得。这在下面的方案10中示出。
方案10
令人惊讶的是,为了实际的用途,已经发现了具有式(I)的新颖的化合物有着非常有利水平的生物活性,可用来保护植物免受真菌引起的疾病的侵害。
可以在农业部门和相关领域中使用具有式(I)的化合物,用作例如用于控制植物有害生物的活性成分,或者在非生命材料上使用用于控制腐败微生物或对人潜在有害的有机体。该新颖化合物的特色是使用比率低但活性高,植物耐受良好以及不危害环境。它们有非常有用的治疗的、预防的和系统性的特质并且可以用于保护无数栽培植株。具有式(I)的化合物可以用于抑制或破坏在多种不同的有用植物作物的植物或植物部分(果实、花、叶子、茎、块茎、根)上出现的有害生物,同时还保护了例如稍后生长的那些植物部分免于致植物病的微生物的侵害。
本发明还涉及通过处理植物或植物繁殖材料和/或收获的粮食作物(其中将有效量的具有式(I)的化合物施用于植物、其部分或其场所)来控制或预防植物或植物繁殖材料和/或易受微生物攻击的收获的食物作物免受侵害的方法。
还能使用具有式(I)的化合物作为杀真菌剂。如本文中使用的,术语“杀真菌剂”意指控制、修饰或防止真菌生长的化合物。术语“杀真菌有效量”意指能够对真菌生长产生影响的这样一种化合物或此类化合物的组合的量。控制或修饰的影响包括所有从自然发育的偏离,例如杀死、阻滞等,并且预防包括在植物内或上面预防真菌感染的屏障或其他防御构造。
也可以将具有式(I)的化合物作为处理植物繁殖材料(如种子,例如果实、块茎、或谷物)、或植物插条(如大米)的拌种剂,用于保护对抗真菌感染或土壤里的致植物病的真菌。可以在种植之前将繁殖材料用包括具有式(I)的化合物的组合物处理,例如可以在播种之前敷裹种子。
还可以通过在液体配制品中浸渍种子或通过用一种固体配制品包衣它们,从而将根据本发明的活性成分施用至谷物(包衣)。还可以在种植该繁殖材料时,将该组合物施用至种植位点,例如在播种期间施用至种子的犁沟。本发明还涉及处理植物繁殖材料的这样的方法,并且涉及如此处理的植物繁殖材料。
此外,根据本发明所述的这些化合物可以用于控制相关领域的真菌,这些领域是例如在工业材料(包括木材以及与木材有关的工业产品)的保护中、在食品存储中、在卫生管理中。
此外,本发明还可以用于保护非生命材料(例如木料、墙板和涂料)免受真菌攻击。
具有式(I)的化合物,例如针对疾病的真菌和真菌载体以及致植物病的细菌和病毒可能是有效的。这些疾病的真菌和真菌载体以及致植物病的细菌和病毒是例如:
伞枝梨头霉、链格孢属、丝囊霉属、壳二孢属、曲霉属(包括黄曲霉、烟曲霉、构巢曲霉、黑曲霉、土曲霉)、短梗霉属(包括出芽短梗霉(A.pullulans))、皮炎芽生菌、小麦白粉病菌、莴苣盘梗霉(Bremia lactucae)、葡萄座腔菌属(包括葡萄溃疡病菌(B.dothidea)、树花地衣葡萄座腔菌(B.obtusa))、葡萄孢属(包括灰葡萄孢(B.cinerea))、念珠菌属(包括白色念珠菌、光滑球念珠菌(C.glabrata)、克鲁斯念珠菌(C.krusei)、萄牙念珠菌(C.lusitaniae)、近平滑念珠菌(C.parapsilosis)、热带念珠菌(C.tropicalis))、Cephaloascus fragrans、长喙壳属、尾孢属(包括褐斑病菌(C.arachidicola))、晚斑病菌(Cercosporidium personatum)、枝孢霉属、麦角菌、粗球孢子菌、旋孢腔菌属、炭疽菌属(包括香蕉炭疽病菌(C.musae))、新型隐球菌、间座壳属(Diaporthe spp)、亚隔孢壳属、内脐蠕孢属、痂囊腔菌属、表皮癣菌属、梨火疫病菌、白粉菌属(包括菊科白粉菌(E.cichoracearum))、葡萄顶枯病菌(Eutypa lata)、镰刀菌属(包括大刀镰刀菌、禾谷镰刀菌、F.镰刀菌、串珠镰刀菌、胶孢镰刀菌、茄病镰刀菌、尖孢镰刀菌、层出镰刀菌)、小麦全蚀病菌(Gaeumannomyces graminis)、藤仓赤霉菌(Gibberella fujikuroi)、煤烟病菌(Gloeodes pomigena)、香蕉炭疽盘长孢菌(Gloeosporium mmusarum)、苹果炭疽病菌(Glomerella cingulate)、葡萄球座菌(Guignardia bidwellii)、植物受桧胶锈菌(Gymnosporangium juniperi-virginianae)、长蠕孢属、驼孢锈菌属、组织胞浆菌属(包括荚膜组织胞浆菌(H.capsulatum))、红线病菌、Leptographium lindbergi、辣椒白粉病菌(Leveillula taurica)、松针散盘壳(Lophodermium seditiosum)、雪霉叶枯菌(Microdochium nivale)、小孢子菌属、链核盘菌属、毛霉属、球腔菌属(包括禾生球腔菌、苹果黑点病菌(M.Pomi))、树梢枯病菌、云杉病菌、副球孢子菌属、青霉属(包括指状青霉、意大利青霉)、霉样真霉属、指霜霉属(包括玉蜀黍指霜霉、菲律宾霜指霉和高粱指霜霉)、霜霉属、颖枯壳针孢、豆薯层锈菌、桑黄火木针层孔菌(Phellinu igniarus)、瓶霉蚁属、茎点霉属、葡萄生拟茎点菌(Phomopsis viticola)、疫霉菌属(包括致病疫霉菌)、单轴霉属(包括霍尔斯单轴霉菌、葡萄霜霉病菌(P.viticola))、格孢腔菌属、叉丝单囊壳属(包括白叉丝单囊壳(P.leucotricha))、禾谷多粘菌(Polymyxa graminis)、甜菜多粘菌(Polymyxabetae)、小麦基腐病菌(Pseudocercosporella herpotrichoides)、假单胞菌属、假霜霉属(包括黄瓜霜霉病菌、葎草假霜霉)、Pseudopeziza tracheiphila、霜霉属属(包括大麦柄锈菌(P.hordei)、小麦叶锈病菌(P.recondita)、条形柄锈菌(P.Striiformis)、小麦褐锈菌(P.triticina))、埋核盘菌属、核腔菌属、梨孢属(包括稻瘟病菌(P.oryzae))、腐霉属(包括终极腐霉菌)、柱隔孢属、丝核菌属、微小根毛霉(Rhizomucor pusillus)、少根根霉、喙孢属、丝孢菌属(包括尖端赛多孢子菌和多育赛多孢子菌)、煤点病(Schizothyrium pomi)、核盘菌属、小核菌属、壳针孢属(包括颖枯壳针孢(S.nodorum)、小麦壳针孢(S.tritici))、草莓白粉病菌(Sphaerotheca macularis)、棕丝单囊壳(Sphaerotheca fusca)(黄瓜白粉病菌(Sphaerotheca fuliginea))、孢子丝菌属(Sporothorix)、颖枯壳多孢(Stagonosporanodorum)、匍柄霉属(Stemphylium)、毛韧革菌(Stereum hirsutum)、水稻枯纹病菌(Thanatephorus cucumeris)、根串珠霉(Thielaviopsis basicola)、腥黑粉菌属、木霉属(包括哈茨木霉)、拟康氏木霉、绿色木霉)、毛癣菌属、核瑚菌属、葡萄钩丝壳、条黑粉菌属(Urocystis)、黑粉菌属(Ustilago)、黑星菌属(包括苹果黑星菌(V.inaequalis))、轮枝孢属、以及黄单胞菌属。
在本发明的范围内,有待保护的目标作物和/或有用植物典型地包括多年生和一年生作物,如浆果植物,例如黑莓、蓝莓、蔓越莓、树莓以及草莓;谷类,例如大麦、玉米(maize,corn)、小米、燕麦、水稻、黑麦、高粱、黑小麦以及小麦;纤维植物,例如棉花、亚麻、大麻、黄麻以及剑麻;大田作物,例如糖甜菜和饲料甜菜、咖啡豆、啤酒花、芥菜、油菜(卡诺拉)、罂粟、甘蔗、向日葵、茶以及烟草;果树,例如苹果、杏、鳄梨、香蕉、樱桃、柑橘、油桃、桃、梨以及李子;草,例如百慕大草、蓝草、本特草、蜈蚣草、牛毛草、黑麦草、圣奥古斯丁草以及结缕草;药草,如罗勒、琉璃苣、细香葱、胡荽、薰衣草、独活草、薄荷、牛至、荷兰芹、迷迭香、鼠尾草以及百里香;豆类,例如菜豆、小扁豆、豌豆以及大豆;坚果,例如杏仁、腰果、落花生、榛子、花生、山核桃、开心果以及核桃;棕榈植物,例如油棕榈;观赏植物,例如花卉、灌木和树;其他树木,例如可可、椰子、橄榄以及橡胶;蔬菜,例如芦笋、茄子、西兰花、卷心菜、胡萝卜、黄瓜、大蒜、莴苣、西葫芦、甜瓜、秋葵、洋葱、胡椒、马铃薯、南瓜、大黄、菠菜以及番茄;以及葡萄藤,例如葡萄。
术语“有用植物”应当理解为包括由于常规育种方法或基因工程致使其对于除草剂(像溴草腈)或除草剂类(例如像HPPD抑制剂、ALS抑制剂,例如氟嘧磺隆、氟丙磺隆和三氟啶磺隆、EPSPS(5-烯醇-丙酮-莽草酸-3-磷酸-合成酶)抑制剂、GS(谷氨酰胺合成酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)耐受的有用植物。已经通过常规育种方法(诱变)变得对咪唑啉酮例如甲氧咪草烟具有耐受力的作物的一个实例是夏季油菜(卡诺拉(Canola))。已经通过基因工程方法致使对除草剂或除草剂类耐受的作物的实例包括草甘膦和草丁膦抗性玉米品种,它们在Herculex和商标名下是可商购的。
术语“有用植物”应当理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的有用的植物,这些毒素如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
这样的植物的实例是:(玉米品种,表达CryIA(b)毒素);YieldGard(玉米品种,表达CryIIIB(b1)毒素);YieldGard(玉米品种,表达CryIA(b)和CryIIIB(b1)毒素);(玉米品种,表达Cry9(c)毒素);Herculex(玉米品种,表达CryIF(a2)毒素以及实现对除草剂草丁膦铵的耐受性的酶膦丝菌素N-乙酰转移酶(PAT));NuCOTN(棉花品种,表达CryIA(c)毒素);Bollgard(棉花品种,表达CryIA(c)毒素);Bollgard(棉花品种,表达CryIA(c)和CryIIA(b)毒素);(棉花品种,表达VIP毒素);(马铃薯品种,表达CryIIIA毒素);GT Advantage(GA21耐草甘膦性状),CB Advantage(Bt11玉米螟(CB)性状),Rw(玉米根虫性状)以及
术语“作物”应当理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的作物植物,所述毒素是如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
可以通过这样的转基因植物表达的毒素包括例如来自蜡样芽孢杆菌或日本甲虫芽孢杆菌的杀昆虫蛋白;或来自苏云金芽孢杆菌的杀昆虫蛋白,如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或线虫寄生性细菌的杀昆虫蛋白,例如光杆状茵属或致病杆菌属,如发光光杆状茵、嗜线虫致病杆菌;由动物产生的毒素,如蝎毒素、蜘蛛毒素、黄蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,如链霉菌毒素;植物凝集素,如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类;蛋白酶抑制剂,如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯贮存蛋白(patatin)、半胱氨酸蛋白酶抑制剂、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕皮类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕皮激素抑制剂、HMG-COA-还原酶;离子通道阻断剂,如钠通道或钙通道阻断剂;保幼激素酯酶、利尿激素受体、茋合酶、联苄合酶、几丁酶以及葡聚糖酶。
在本发明背景下,δ-内毒素例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A应理解为显然还包括混合型毒素、截短的毒素和经修饰的毒素。混合型毒素是通过那些蛋白的不同结构域的新组合重组产生的(参见例如,WO 02/15701)。截短的毒素(例如截短的Cry1Ab)是已知的。在经修饰的毒素的情况下,天然存在的毒素的一个或多个氨基酸被置换。在这样的氨基酸置换中,优选地将非天然存在的蛋白酶识别序列插入毒素中,例如像在Cry3A055的情况下,组织蛋白酶-G-识别序列被插入Cry3A毒素中(参见WO 03/018810)。
这样的毒素或能够合成这样的毒素的转基因植物的实例披露于例如EP-A-0 374753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878以及WO 03/052073中。
用于制备这样的转基因植物的方法对于本领域技术人员是已知的并且描述在例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367474、EP-A-0 401 979以及WO 90/13651中已知。
包括在转基因植物中的毒素使得植物对有害昆虫有耐受性。这些昆虫可以存在于任何昆虫分类群,但尤其是通常在甲虫(鞘翅目)、双翅昆虫(双翅目)以及蝴蝶(鳞翅目)中发现。
包含一种或多种编码杀昆虫剂抗性并且表达一种或多种毒素的基因的转基因植物是已知的并且其中一些是可商购的。这样的植物的实例是:(玉米品种,表达Cry1Ab毒素);YieldGard(玉米品种,表达Cry3Bb1毒素);YieldGard(玉米品种,表达Cry1Ab以及Cry3Bb1毒素);(玉米品种,表达Cry9C毒素);Herculex(玉米品种,表达Cry1Fa2毒素以及实现对除草剂草丁膦铵的耐受性的酶膦丝菌素N-乙酰转移酶(PAT));NuCOTN(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac和Cry2Ab毒素);(棉花品种,表达Vip3A和Cry1Ab毒素);(马铃薯品种,表达Cry3A毒素); GT Advantage(GA21耐草甘膦性状),CB Advantage(Bt11玉米螟(CB)性状)以及
这样的转基因作物的其他实例是:
1.Bt11玉米,来自Syngenta Seeds SAS[先正达种子公司],Chemin de l'Hobit[霍比特路]27,F-31 790St.Sauveur,France[圣苏维尔,法国],登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达截短的Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt11玉米还转基因地表达PAT酶以达到对除草剂草丁膦铵的耐受性。
2.Bt176玉米,来自Syngenta Seeds SAS[先正达种子公司],Chemin de l'Hobit[霍比特路]27,F-31 790St.Sauveur,France[圣苏维尔,法国],登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt176玉米还转基因表达PAT酶以实现对除草剂草丁膦铵盐的耐受性。
3.MIR604玉米,来自Syngenta Seeds SAS[先正达种子公司],Chemin de l'Hobit[霍比特路]27,F-31 790St.Sauveur,France[圣苏维尔,法国],登记号C/FR/96/05/10。通过转基因表达经修饰的Cry3A毒素使之具有昆虫抗性的玉米。此毒素是通过插入组织蛋白酶-G-蛋白酶识别序列而经修饰的Cry3A055。这样的转基因玉米植物的制备描述于WO 03/018810中。
4.MON 863玉米,来自Monsanto Europe S.A.[孟山都欧洲公司],270-272Avenuede Tervuren[特弗伦大道],B-1150Brussels,Belgium[布鲁塞尔,比利时],登记号C/DE/02/9。MON 863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自Monsanto Europe S.A.[孟山都欧洲公司],270-272Avenuede Tervuren[特弗伦大道],B-1150Brussels,Belgium[布鲁塞尔,比利时],登记号C/ES/96/02。
6. 1507玉米,来自Pioneer Overseas Corporation[先锋海外公司],AvenueTedesco[特德斯科大道],7B-1160Brussels,Belgium[布鲁塞尔,比利时],登记号C/NL/00/10。遗传改性的玉米,表达蛋白质Cry1F以获得对某些鳞翅目昆虫的抗性,并且表达PAT蛋白质以获得对除草剂草丁膦铵的耐受性。
7.NK603×MON 810玉米,来自Monsanto Europe S.A.[孟山都欧洲公司],270-272Avenue de Tervuren,B-1150Brussels,Belgium[特弗伦大道,B-1150布鲁塞尔,比利时],登记号C/GB/02/M3/03。通过将遗传修饰的品种NK603和MON 810杂交,由常规育种的杂交玉米品种构成。NK603×MON810玉米转基因地表达由土壤杆菌属菌株CP4获得的蛋白质CP4EPSPS,使之耐除草剂(含有草甘膦),以及由苏云金芽孢杆菌库尔斯塔克亚种获得的Cry1Ab毒素,使之耐某些鳞翅目昆虫,包括欧洲玉米螟。
如本文使用的术语“场所”意指植物在其中或其上生长的地方,或栽培植物的种子被播种的地方,或种子将要被置于土壤中的地方。它包括土壤、种子以及幼苗,连同建立的植被。
术语“植物”是指植物的所有有形部分,包括种子、幼苗、幼树、根、块茎、茎、秆、叶和果实。
术语“植物繁殖材料”应当理解为表示植物的生殖部分,如种子,所述部分可以用于所述植物的繁殖,以及营养性材料,如插条或块茎(例如马铃薯)。可以提及,例如种子(在严格意义上)、根、果实、块茎、球茎、根茎以及植物的部分。还可以提及在发芽后或破土后将被移植的发芽植物和幼小植物。这些幼小植物可以通过浸渍进行完全或部分处理而在移植之前进行保护。优选地,“植物繁殖材料”应当理解为表示种子。
在此提及的使用其俗名的杀有害生物剂是已知的,例如,从“The PesticideManual[杀有害生物剂手册]”,第15版,英国作物保护委员会(British Crop ProtectionCouncil)2009。
具有式(I)的化合物能以未修饰的形式使用,或者优选地,与配制品领域中常规使用的佐剂一起使用。为此目的,它们可以按已知方式便利地配制为可乳化浓缩物、可包衣的糊剂、直接可喷雾的或可稀释的溶液或悬浮液、稀释乳液、可湿性粉剂、可溶性粉剂、尘剂、颗粒以及还有封装物,例如在聚合物的物质中。对于这些组合物的类型,根据预期的目的以及盛行环境来选择施用方法,例如喷洒、雾化、撒粉、播散、包衣或倾倒。这些组合物还可以含有另外的佐剂,例如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂,以及肥料、微量营养素供体或其他用于获得特殊效果的配制品。
适当的载体以及佐剂,例如对于农业用途,可以是固体或液体的并且是在配制品技术中有用的物质,例如天然或再生的矿物物质,溶剂、分散体、湿润剂、增粘剂、增稠剂、粘合剂或肥料类。例如这样的载体在WO97/33890中有描述。
具有式(I)的化合物通常以组合物的形式使用并且可同时地或与另外的化合物顺序地施用于作物区域或待处理的作物。例如,这些另外的化合物可以是影响植物生长的肥料或微量营养素供体或其他制剂。它们还可以是选择性除草剂或非选择性除草剂,连同杀昆虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或几种这些制剂的混合物,如果希望的话与配制品领域中通常使用的另外的载体、表面活性剂或促进施用的佐剂一起。
具有式(I)的这些化合物可以按控制或保护抵抗致植物病微生物的(杀真菌的)组合物的形式使用,这些组合物包括至少一种具有式(I)的化合物或至少一种优选的如上所定义的个别化合物作为活性成分(处于游离形式或以农业上可用的盐形式),并且包括至少一种上述佐剂。
本发明提供了如下组合物,优选杀真菌组合物,其包括至少一种具有式(I)的化合物、农业上可接受的载体以及可任选地佐剂。农业上可接受的载体是例如适合农业用途的载体。这些农业载体在本领域是熟知的。优选地,除了包括具有式(I)的化合物,所述组合物可以包括至少一种或多种杀有害生物活性化合物,例如另外的杀真菌活性成分。
具有式(I)的化合物可以是组合物的唯一活性成分,或者适当时它可以与一种或多种另外的活性成分(例如杀有害生物剂、杀真菌剂、增效剂、除草剂或植物生长调节剂)混合。在一些情况下,另外的活性成分会导致出人意料的协同活性。
适合的另外的活性成分的实例包括以下项:无环氨基酸(acycloamino acid)杀真菌剂、脂肪族氮杀真菌剂、酰胺杀真菌剂、苯胺杀真菌剂、抗生素杀真菌剂、芳香族杀真菌剂、含砷杀真菌剂、芳基苯基酮杀真菌剂、苯甲酰胺杀真菌剂、苯甲酰苯胺杀真菌剂、苯并咪唑杀真菌剂、苯并噻唑杀真菌剂、植物杀真菌剂、桥联联苯基杀真菌剂、氨基甲酸酯杀真菌剂、苯氨甲酸酯杀真菌剂、康唑杀真菌剂、铜杀真菌剂、二甲酰亚胺杀真菌剂、二硝基苯酚杀真菌剂、二硫代氨基甲酸酯杀真菌剂、二硫戊环杀真菌剂、糠酰胺杀真菌剂、糠苯胺杀真菌剂、酰肼真菌剂、咪唑杀真菌剂、汞杀真菌剂、吗啉杀真菌剂、有机磷杀真菌剂、有机锡杀真菌剂、氧硫杂环己二烯(oxathiin)杀真菌剂、噁唑杀真菌剂、苯硫酰胺杀真菌剂、多硫化物杀真菌剂、吡唑杀菌剂、吡啶杀真菌剂、嘧啶杀真菌剂、吡咯杀真菌剂、季铵杀真菌剂、喹啉杀真菌剂、醌杀真菌剂、喹喔啉杀真菌剂、嗜球果伞素杀真菌剂、磺酰苯胺(sulfonanilide)杀真菌剂、噻二唑杀真菌剂、噻唑杀真菌剂、噻唑烷杀真菌剂、硫代氨基甲酸酯杀真菌剂、噻吩杀真菌剂、三嗪杀真菌剂、三唑杀真菌剂、三唑并嘧啶杀真菌剂、尿素杀真菌剂、缬氨酰胺(valinamide)杀真菌剂以及锌杀真菌剂。
适合的另外的活性成分的实例也包括以下:3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(9-二氯亚甲基-1,2,3,4-四氢-1,4-甲撑-萘-5-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸甲氧基-[1-甲基-2-(2,4,6-三氯苯基)-乙基]-酰胺、1-甲基-3-二氟甲基-1H-吡唑-4-甲酸(2-二氯亚甲基-3-乙基-1-甲基-茚满-4-基)-酰胺(1072957-71-1)、1-甲基-3-二氟甲基-1H-吡唑-4-甲酸(4’-甲基磺酰基-联苯基-2-基)-酰胺、1-甲基-3-二氟甲基-4H-吡唑-4-甲酸[2-(2,4-二氯-苯基)-2-甲氧基-1-甲基-乙基]-酰胺、(5-氯-2,4-二甲基-吡啶-3-基)-(2,3,4-三甲氧基-6-甲基-苯基)-甲酮、(5-溴-4-氯-2-甲氧基-吡啶-3-基)-(2,3,4-三甲氧基-6-甲基-苯基)-甲酮、2-{2-[(E)-3-(2,6-二氯-苯基)-1-甲基-丙-2-烯-(E)-亚基氨基氧基甲基]-苯基}-2-[(Z)-甲氧基亚氨基]-N-甲基-乙酰胺、3-[5-(4-氯-苯基)-2,3-二甲基-异噁唑烷-3-基]-吡啶、(E)-N-甲基-2-[2-(2,5-二甲基苯氧基甲基)苯基]-2-甲氧基-亚氨基乙酰胺、4-溴-2-氰基-N,N-二甲基-6-三氟甲基苯并咪唑-1-磺胺、a-[N-(3-氯-2,6-二甲苯基)-2-甲氧基乙酰胺基]-y-丁内酯、4-氯-2-氰基-N,-二甲基-5-对甲苯基咪唑-1-磺胺、N-烯丙基-4,5,-二甲基-2-三甲基甲硅烷基噻吩-3-甲酰胺、N-(l-氰基-1,2-二甲基丙基)-2-(2,4-二氯苯氧基)丙酰胺、N-(2-甲氧基-5-吡啶基)-环丙烷甲酰胺、(.+-.)-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-2-醇、2’,6’-二溴-2-甲基-4-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲酰苯胺、1-咪唑基-1-(4’-氯苯氧基)-3,3-二甲基丁-2-酮、甲基(E)-2-[2-[6-(2-氰基苯氧基)嘧啶-4-基氧基]苯基]3-甲氧基丙烯酸脂、甲基(E)-2-[2-[6-(2-硫基胺基苯氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[6-(2-氟苯氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[6-(2,6-二氟苯氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[3-(嘧啶-2-基氧基)苯氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[3-(5-甲基嘧啶-2-基氧基)-苯氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[3-(苯基-磺酰基氧基)苯氧基]苯基-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[3-(4-硝基苯氧基)苯氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-苯氧基苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-(3,5-二甲基-苯甲酰基)吡咯-1-基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-(3-甲氧基苯氧基)苯基]-3-甲氧基丙烯酸脂、甲基(E)-2[2-(2-苯基乙烯-1-基)-苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-(3,5-二氯苯氧基)吡啶-3-基]-3-甲氧基丙烯酸脂、甲基(E)-2-(2-(3-(1,1,2,2-四氟乙氧基)苯氧基)苯基)-3-甲氧基丙烯酸脂、甲基(E)-2-(2-[3-(α-羟基苄基)苯氧基]苯基)-3-甲氧基丙烯酸脂、甲基(E)-2-(2-(4-苯氧基吡啶-2-基氧基)苯基)-3-甲氧基丙烯酸脂、甲基(E)-2-[2-(3-正丙基氧基-苯氧基)苯基]3-甲氧基丙烯酸脂、甲基(E)-2-[2-(3-异丙基氧基苯氧基)苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[3-(2-氟苯氧基)苯氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-(3-乙氧基苯氧基)苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-(4-叔丁基-吡啶-2-基氧基)苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[3-(3-氰基苯氧基)苯氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[(3-甲基-吡啶-2-基氧基甲基)苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[6-(2-甲基-苯氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-(5-溴-吡啶-2-基氧基甲基)苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-(3-(3-碘吡啶-2-基氧基)苯氧基)苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-[2-[6-(2-氯吡啶-3-基氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸脂、甲基(E),(E)-2-[2-(5,6-二甲基吡嗪-2-基甲基肟基甲基)苯基]-3-甲氧基丙烯酸脂、甲基(E)-2-{2-[6-(6-甲基吡啶-2-基氧基)嘧啶-4-基氧基]苯基}-3-甲氧基-丙烯酸脂、甲基(E),(E)-2-{2-(3-甲氧基苯基)甲基肟基甲基]-苯基}-3-甲氧基丙烯酸脂、甲基(E)-2-{2-(6-(2-叠氮基苯氧基)-嘧啶-4-基氧基]苯基}-3-甲氧基丙烯酸脂、甲基(E),(E)-2-{2-[6-苯基嘧啶-4-基)-甲基肟基甲基]苯基}-3-甲氧基丙烯酸脂、甲基(E),(E)-2-{2-[(4-氯苯基)-甲基肟基甲基]-苯基}-3-甲氧基丙烯酸脂、甲基(E)-2-{2-[6-(2-正丙基苯氧基)-1,3,5-三嗪-4-基氧基]苯基}-3-甲氧基丙烯酸脂、甲基(E),(E)-2-{2-[(3-硝基苯基)甲基肟基甲基]苯基}-3-甲氧基丙烯酸脂、3-氯-7-(2-氮杂-2,7,7-三甲基-辛-3-烯-5-碱)、2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺、3-碘-2-丙炔醇、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、2,3,3-三碘烯丙醇、3-溴-2,3-二碘-2-丙烯醇、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-丙炔基环己基-氨基甲酸酯、3-碘-2-丙炔基苯基氨基甲酸酯;苯酚衍生物,如三溴苯酚、四氯酚、3-甲基-4-氯酚、3,5-二甲基-4-氯酚、苯氧乙醇、二氯酚、邻苯基苯酚、间苯基苯酚、对苯基苯酚、2-苄基-4-氯酚、5-羟基-2(5H)-呋喃酮;4,5-二氯二噻唑啉酮、4,5-苯并二噻唑啉酮、4,5-三亚甲基二噻唑啉酮、4,5-二氯-(3H)-1,2-二硫基-3-酮、3,5-二甲基-四氢-1,3,5-噻二嗪-2-硫酮、N-(2-对氯苯甲酰乙基)-氯化六甲撑四胺、活化酯、八九十混酸(acypetacs)、棉铃威、阿苯达唑、杀螟丹(aldimorph)、蒜素、烯丙醇、辛唑嘧菌胺、吲唑磺菌胺、阿姆巴(amobam)、氨丙膦酸(ampropylfos)、敌菌灵、福美砷(asomate)、金色制霉素(aureofungin)、阿扎康唑、阿扎芬定(azafendin)、氧化福美双杀菌剂(azithiram)、嘧菌酯、钡多硫化物、苯霜灵、苯霜灵-M、麦锈灵(benodanil)、苯菌灵、敌菌腙、丙唑草隆(bentaluron)、苯噻菌胺、苯噻硫氰、氯化苄烷铵、节烯酸(benzamacril)、苯杂吗(benzamorf)、苯甲羟肟酸、苯并烯氟菌唑(benzovindiflupyr)、黄连素、百杀辛(bethoxazin)、双苯三唑醇(biloxazol)、乐杀螨、联苯基、联苯三唑醇、硫双二氯酚、联苯吡菌胺(bixafen)、杀稻瘟菌素-S、啶酰菌胺、溴菌腈、糠菌唑、乙嘧酚磺酸酯、丁硫啶、丁胺多硫化钙、敌菌丹、克菌丹、吗菌威、多菌灵、多菌灵盐酸盐、萎锈灵、加普胺、香芹酮、CGA41396、CGA41397、灭螨猛、壳聚糖、灭痕唑(chlobenthiazone)、双胺灵、氯醌、氯芬唑、地茂散、氯化苦、百菌清、克氯得(chlorozolinate)、乙菌利、氯咪巴唑、克霉唑、克拉康(clozylacon)、含铜的化合物如乙酸铜、碳酸铜、氢氧化铜、环烷酸铜、油酸铜、氯氧化铜、氧基喹啉铜、硅酸铜、硫酸铜、树脂酸铜、铬酸铜锌和波尔多混合物、甲酚、硫杂灵、福美铜氯(cuprobam)、亚铜的氧化物、氰霜唑、环菌胺(cyclafuramid)、放线菌酮、环氟菌胺、霜脲氰、氰菌灵(cypendazole)、环唑醇、嘧菌环胺、棉隆、咪菌威、癸磷锡、脱氢乙酸、二-2-吡啶基二硫化物1,1'-二氧化物、苯氟磺胺、抑菌灵(dichlofluanid)、哒菌清、二氯萘醌、氯硝胺、双氯酚、菌核利、苄氯三唑醇、双氯氰菌胺、乙霉威、苯醚甲环唑、野燕枯、二氟林、O,O-二异-丙基-S-苄基硫代磷酸盐、地美福唑(dimefluazole)、菌核净、地美康唑(dimetconazole)、烯酰吗啉、二甲嘧酚、烯唑醇、烯唑醇-M、敌螨通、敌螨普、邻敌螨消、硝戊酯(dinopenton)、硝辛酯(dinosulfon)、硝丁酯(dinoterbon)、二苯胺、双吡硫翁、戒酒硫、灭菌磷(ditalimfos)、二噻农、二硫基醚、十二烷基二甲基氯化铵、十二环吗啉、多地辛、多果定、十二烷基胍醋酸盐、敌菌酮、敌瘟磷、烯肟菌酯、氟环唑、乙环唑、代森硫(etem)、噻唑菌胺、乙嘧酚、乙氧喹、乙蒜素(ethilicin)、乙基(Z)-N-苄基-N([甲基(甲基-硫代亚乙基氨基-氧基羰基)氨基]硫基)-β-氨基丙酸乙酯、土菌灵、恶唑菌酮、咪唑菌酮、地克松、咪菌腈、氯苯嘧啶醇、腈苯唑、甲呋酰胺、环酰菌胺、种衣酯、氰菌胺、拌种咯、苯锈啶、丁苯吗啉、胺苯吡菌酮、三苯锡醋酸盐、三苯基氢氧化锡、福美铁、嘧菌腙、氟啶胺、咯菌腈、氟美托、氟吗啉、氟吡菌胺(flupicolide)、氟吡菌酰胺、唑呋草、三氟苯唑(fluotrimazole)、氟嘧菌酯、氟喹唑、氟硅唑、磺菌胺、氟酰胺(flutanil)、氟酰胺、粉唑醇、氟唑菌酰胺、灭菌丹、甲醛、三乙膦酸、麦穗宁、呋霜灵、福拉比、二甲呋酰胺、呋菌唑、糠醛、茂谷乐、呋菌隆、果绿定、灰黄霉素、双胍辛胺、丙烯酸喹啉酯(halacrinate)、六氯苯、六氯丁二烯、六氯酚、己唑醇、环己硫磷(hexylthiofos)、汞加芬(hydrargaphen)、羟基异噁唑、恶霉灵、抑霉唑、抑霉唑硫酸盐、亚胺唑、双胍辛胺、双胍辛胺三乙酸酯、枯瘟净(inezin)、碘代丙炔基丁基甲胺酸酯(iodocarb)、种菌唑、ipfentrifluconazole、异稻瘟净、异菌脲、丙森锌、异丙基丁基氨基甲酸酯、稻瘟灵、吡唑萘菌胺、异噻菌胺、氯苯咪菌酮(isovaledione)、浸种磷(izopamfos)、春雷霉素、醚菌酯-甲基、LY186054、LY211795、LY248908、代森锰锌、双炔酰菌胺、代森锰、邻酰胺、咪卡病西(mecarbinzid)、精甲霜灵、氯氟醚菌唑、嘧菌胺、灭锈胺、氯化汞、氯化亚汞、消螨多(meptyldinocap)、甲霜灵、精甲霜灵-M、威百亩、肼叉噁唑酮(metazoxolon)、叶菌唑、磺菌威、呋菌胺、甲基溴、甲基碘、异硫氰酸甲酯、代森联、代森联-锌、苯氧菌胺、苯菌酮、噻菌胺、代森环(milneb)、吗啉胍(moroxydine)、腈菌唑、甲菌利(myclozolin)、代森钠(nabam)、那他霉素、田安、福美镍、硝基苯乙烯、酞菌酯、氟苯嘧啶醇、异噻菌酮、呋酰胺、有机汞化合物类、肟醚菌胺、蛇床子素(osthol)、噁霜灵、环氧嘧磺隆、氟噻唑吡乙酮(oxathiapiprolin)、奥辛-铜(oxine-copper)、噁喹酸、欧伯克唑(oxpoconazole)、氧化萎锈灵、苯吡醇(parinol)、稻瘟酯、戊菌唑、戊菌隆、戊苯吡菌胺、五氯酚、吡噻菌胺、氰烯菌酯、叶枯净、氯瘟磷(phosdiphen)、疫霉灵-Al、磷酸类、苯酞、啶氧菌酯、粉病灵、多氨基甲酸酯、多氧菌素D、多氧瑞莫(polyoxrim)、代森联(polyram)、烯丙苯噻唑、咪鲜胺、腐霉利、普罗帕脒(propamidine)、霜霉威、丙环唑、丙森锌、丙酸、丙氧喹啉、硫菌威(prothiocarb)、丙硫菌唑、氟唑菌酰羟胺(pydiflumetofen)、比锈灵、唑菌胺酯、唑胺菌酯(pyrametrostrobin)、唑菌酯、定菌磷、吡菌苯威、啶菌腈(pyridinitril)、啶斑肟、嘧霉胺、吡奥芬酮(pyriofenone)、咯喹酮、吡氯灵(pyroxychlor)、氯吡呋醚、吡咯尼林、季铵化合物、羟基喹啉基乙酮(quinacetol)、醌菌腙(quinazamid)、唑喹菌酮(quinconazole)、灭螨猛、喹氧灵、五氯硝基苯、吡咪唑(rabenzazole)、蛔蒿素(santonin)、环苯吡菌胺(sedaxane)、硅噻菌胺、硅氟唑、西克唑(sipconazole)、五氯酚钠、螺环菌胺、链霉素、硫、戊苯砜(sultropen)、戊唑醇、异丁乙氧喹啉(tebfloquin)、叶枯酞、四氯硝基苯、福代硫、氟醚唑、噻苯达唑、噻二氟(thiadifluor)、噻菌腈(thicyofen)、噻氟菌胺、2-(硫氰基甲硫基)苯并噻唑、硫菌灵-甲基、克杀螨(thioquinox)、塞仑、噻酰菌胺、亚胺唑(timibenconazole)、硫氰苯甲酰胺(tioxymid)、立枯磷-甲基、对甲抑菌灵、三唑酮、三唑醇、威菌磷(triamiphos)、嘧菌醇(triarimol)、丁三唑、咪唑嗪、三环唑、十三吗啉、肟菌酯、啶虫咪(triflumazole)、嗪氨灵、氟菌唑、灭菌唑、烯效唑、福美甲胂(urbacide)、井岗霉素、霜霉灭(valifenalate)、威百、乙烯菌核利、氰菌胺(zarilamid)、代森锌、福美锌、苯酰菌胺。
本发明的化合物也可以与驱蠕虫药剂组合使用。这样的驱蠕虫药剂包括选自大环内酯类化合物的化合物,如伊维菌素、阿维菌素、阿巴美丁、依马克丁、依立诺克丁、多拉克汀、司拉克丁、莫昔克丁、奈马克丁以及米尔倍霉素衍生物,如在EP-357460、EP-444964以及EP-594291中所述。另外的驱蠕虫药剂包括半合成及生物合成阿维菌素/米尔倍霉素衍生物,如在US-5015630、WO-9415944以及WO-9522552中所述的那些。另外的驱蠕虫药剂包括苯并咪唑类,如阿苯达唑、坎苯达唑、芬苯达唑、氟苯达唑、甲苯达唑、奥芬达唑、奥苯达唑、帕苯达唑、以及所述类别的其他成员。另外的驱蠕虫药剂包括咪唑并噻唑类以及四氢嘧啶类,如四咪唑、左旋咪唑、双羟萘酸噻嘧啶、奥克太尔或莫仑太尔。另外的驱蠕虫药剂包括杀吸虫剂(如三氯苯达唑和氯舒隆)以及杀绦虫剂(如吡喹酮和依西太尔)。
本发明的化合物可以与对郝青酰胺(paraherquamide)/马可氟汀(marcfortine)类驱蠕虫药剂的衍生物及类似物以及抗寄生虫噁唑啉(如在US-5478855、US-4639771和DE-19520936中所披露的)组合使用。
本发明的化合物可以与如WO-9615121中所述的一般种类二氧吗啉抗寄生虫剂的衍生物及类似物以及还与驱蠕虫活性的环状缩酚肽(例如WO-9611945、WO-9319053、WO-9325543、EP-626375、EP-382173、WO-9419334、EP-382173、以及EP-503538中所述的那些)组合使用。
本发明的化合物可以与其他杀体外寄生虫药组合使用;例如氟虫腈;拟除虫菊酯;有机磷酸酯;昆虫生长调节剂(例如虱螨脲);蜕皮激素促效剂(例如虫酰肼及其类似物);新烟碱(例如吡虫啉及其类似物)。
本发明的化合物可与萜烯生物碱组合使用,例如在WO 95/19363或WO04/72086中描述的那些,特别是其中公开的化合物。
可以与本发明的化合物组合使用的此类生物活性化合物的其他实例包括(但不局限于)以下:
有机磷酸酯:乙酰甲胺磷、甲基吡噁磷、乙基谷硫磷、甲基谷硫磷、溴硫磷、乙基溴硫磷、硫线磷、四氯乙磷(chlorethoxyphos)、毒死蜱、氯芬磷、氯甲磷、内吸磷、内吸磷-S-甲基、内吸磷-S-甲基砜、氯亚胺硫磷、二嗪磷、敌敌畏、百治磷、乐果、乙拌磷、乙硫磷、灭线磷、氧嘧啶磷、伐灭磷、苯线磷、杀螟硫磷、丰索磷、倍硫磷、吡氟硫磷、地虫磷、安果、噻唑磷、庚烯磷、氯唑磷、异丙磷、异噁唑磷、马拉硫磷、虫螨畏、甲胺磷、杀扑磷、甲基对硫磷、速灭磷、久效磷、二溴磷、氧乐果、甲基氧代内吸磷、对氧磷、对硫磷、甲基对硫磷、稻丰散、伏杀硫磷、硫环磷、磷克、亚胺硫磷、磷胺、甲拌磷、肟硫磷、虫螨磷、虫螨磷-甲基、丙溴磷、丙虫磷、普乙塔磷斯(proetamphos)、丙硫磷、吡唑硫磷、哒嗪硫磷、喹硫磷、硫灭克磷、替美磷、特丁磷、丁基嘧啶磷、司替罗磷、西美东(thimeton)、三唑磷、敌百虫、灭蚜硫磷。
氨基甲酸酯:棉铃威、涕灭威、2-仲丁苯基甲基氨基甲酸酯、丙硫克百威、甲萘威、克百威、丁硫克百威、地虫威、乙硫苯威、苯氧威、芬硫克、呋线威、HCN-801、异丙威、茚虫威、灭虫威、灭多虫、5-甲基-间-异丙苯基丁炔基(甲基)氨基甲酸酯、杀线威、抗蚜威、残杀威、硫双威、久效威、唑蚜威、UC-51717。
拟除虫菊酯:氟丙菊酯、烯丙菊酯、α-氯氰菊酯(alphametrin)、5-苄基-3-呋喃基甲基(E)-(1R)-顺式-2,2-二甲基-3-(2-氧硫杂环戊-3-亚基甲基)环丙烷羧酸酯、联苯菊酯、β-氟氯氰菊酯、氟氯氰菊酯、α-氯氰菊酯(α-cypermethrin)、β-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、联苯菊酯、NCI-85193、乙氰菊酯、氯氟氰菊酯、cythithrin、苯醚氰菊酯、溴氰菊酯、炔戊菊酯、高氰戊菊酯、醚菊酯、五氟苯菊酯、甲氰菊酯、氰戊菊酯、氟氰菊酯、氟氯苯菊酯、氟胺氰菊酯(D异构体)、炔咪菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、氯菊酯、苯醚菊酯、炔丙菊酯、除虫菊酯(天然产物)、苄呋菊酯、胺菊酯、四氟苯菊酯、θ-氯氰菊酯、氟硅菊酯、t-氟胺氰菊酯、七氟菊酯、四溴菊酯、ζ-氯氰菊酯。
节肢动物生长调节剂:a)甲壳质合成抑制剂:苯甲酰脲:定虫隆、除虫脲、氟佐隆、氟螨脲、氟虫脲、氟铃脲、虱螨脲、双苯氟脲、伏虫脲、杀虫脲、噻嗪酮、苯虫醚、噻螨酮、乙螨唑、四螨嗪(clofentazin);b)蜕皮激素拮抗剂:氯虫酰肼、甲氧虫酰肼、虫酰肼;c)保幼激素类似物:吡丙醚、烯虫酯(包括S-烯虫酯)、苯氧威;d)脂质生物合成抑制剂:螺螨酯。
其他抗寄生虫药:灭螨醌、双甲脒、AKD-1022、ANS-118、印楝素、苏云金芽孢杆菌、杀虫磺、联苯肼酯、乐杀螨、溴螨酯、BTG-504、BTG-505、毒杀芬、杀螟丹、敌螨酯、杀虫脒、溴虫腈、环虫酰肼、噻虫胺、赛灭净、噻虫嗪(diacloden)、杀螨隆、DBI-3204、二活菌素、二羟基甲基二羟基吡咯烷、敌螨通、敌螨普、硫丹、乙虫腈、醚菊酯、喹螨醚、氟螨嗪(flumite)、MTI-800、唑螨酯、嘧螨酯、氟螨噻、溴氟菊酯、氟螨嗪、三氟醚、苄螨醚(fluproxyfen)、苄螨醚(halofenprox)、氟蚁腙、IKI-220、水硅钠石、NC-196、印度薄荷草(neem guard)、尼敌诺特呋喃(nidinorterfuran)、烯啶虫胺、SD-35651、WL-108477、啶虫丙醚、克螨特、普罗芬布特(protrifenbute)、吡蚜酮、哒螨酮、嘧螨醚、NC-1111、R-195、RH-0345、RH-2485、RYI-210、S-1283、S-1833、SI-8601、氟硅菊酯、硅罗玛汀(silomadine)、多杀菌素、吡螨胺、三氯杀螨砜、四抗菌素、噻虫啉、杀虫环、噻虫嗪、唑虫酰胺、唑蚜威、三乙多杀菌素、三活菌素、增效炔醚、波塔雷克(vertalec)、YI-5301。
生物剂:苏云金芽孢杆菌亚莎华亚种(Bacillus thuringiensis ssp aizawai)、苏云金芽孢杆菌库斯塔克亚种(kurstaki)、苏云金芽孢杆菌δ内毒素、杆状病毒、昆虫病原细菌、病毒以及真菌。
杀细菌剂:金霉素、土霉素、链霉素。
其他生物剂:恩氟沙星、非班太尔、喷沙西林、美洛昔康、头孢氨苄、卡那霉素、匹莫苯、克仑特罗、奥美拉唑、硫姆林、贝那普利、皮瑞普(pyriprole)、头孢喹肟、氟苯尼考、布舍瑞林、头孢维星、托拉菌素、头孢噻呋、卡洛芬、美氟腙、吡喹酮、三氯苯达唑。
具有式(I)的化合物与活性成分的以下混合物是优选的。缩写“TX”意指选自在表1或表2(如下)中描述的化合物1.a.1-1.a.300至1.t.1-1.t.300的组(实施例E-I.a至E-I.t)的一种化合物。
一种佐剂,该佐剂选自由以下组成的物质组:石油(628)+TX,
一种杀螨剂,该杀螨剂由以下物质组成的组:1,1-二(4-氯苯基)-2-乙氧基乙醇(IUPAC名称)(910)+TX、2,4-二氯苯基苯磺酸酯(IUPAC/化学文摘名)(1059)+TX、2-氟-N-甲基-N-I-萘乙酰胺(IUPAC名称)(1295)+TX、4-氯苯基苯基砜(IUPAC名称)(981)+TX、阿维菌素(1)+TX、灭螨醌(3)+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、a-氯氰菊酯(202)+TX、赛硫磷(870)+TX、磺胺螨酯[CCN]+TX、果满磷(872)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、杀螨特(881)+TX、三氧化二砷(882)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、益棉磷(44)+TX、保棉磷(45)+TX、偶氮苯(IUPAC名称)(888)+TX、三唑锡(46)+TX、偶氮磷(889)+TX、苯菌灵(62)+TX、benoxafos[CCN]+TX、苯螨特(71)+TX、苯甲酸苄酯(IUPAC名称)[CCN]+TX、联苯肼酯(74)+TX、氟氯菊酯(76)+TX、乐杀螨(907)+TX、溴灭菊酯+TX、溴烯杀(918)+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX、溴螨酯(94)+TX、噻嗪酮(99)+TX、丁酮威(103)+TX、丁酮砜威(104)+TX、丁基哒螨灵+TX、石硫合剂(IUPAC名称)(111)+TX、毒杀芬(941)+TX、氯灭杀威(943)+TX、甲萘威(115)+TX、克百威(118)+TX、三硫磷(947)+TX、CGA 50’439(研究代码)(125)+TX、灭螨猛(126)+TX、杀螨醚(959)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、溴虫腈(130)+TX、杀螨醇(968)+TX、杀螨酯(970)+TX、敌螨特(971)+TX、毒虫畏(131)+TX、乙酯杀螨醇(975)+TX、伊托明(977)+TX、灭虫脲(978)+TX、丙酯杀螨醇(983)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(994)+TX、瓜菊酯I(696)+TX、瓜菊酯II(696)+TX、瓜菊酯(696)+TX、四螨嗪(158)+TX、氯氰碘柳胺[CCN]+TX、蝇毒磷(174)+TX、巴豆酰甲苯胺[CCN]+TX、巴毒磷(1010)+TX、硫杂灵(1013)+TX、果虫磷(1020)+TX、丁氟螨酯(CAS登记号:400882-07-7)+TX、氯氟氰菊酯(196)+TX、三环锡(199)+TX、氯氰菊酯(201)+TX、DCPM(1032)+TX、DDT(219)+TX、田乐磷(1037)+TX、田乐磷-0(1037)+TX、田乐磷-S(1037)+TX、内吸磷(1038)+TX、甲基内吸磷(224)+TX、内吸磷-0(1038)+TX、甲基内吸磷-0(224)+TX、内吸磷-S(1038)+TX、甲基内吸磷-S(224)+TX、砜吸磷-S(1039)+TX、丁醚脲(226)+TX、氯亚胺硫磷(IO42)+TX、二療磷(227)+TX、苯氟磺胺(230)+TX、敌敌畏(236)+TX、dicliphos+TX、三氯杀螨醇(242)+TX、百治磷(243)+TX、遍地克(1071)+TX、甲氟磷(1081)+TX、乐果(262)+TX、二甲杀螨霉素(653)+TX、消螨酚(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、消螨通(269)+TX、敌螨普(270)+TX、敌螨普-4[CCN]+TX、敌螨普-6[CCN]+TX、二硝酯(1090)+TX、硝戊酯(1092)+TX、硝辛酯(1097)+TX、硝丁酯(1098)+TX、敌噁磷(1102)+TX、二苯砜(IUPAC名称)(1103)+TX、双疏醒[CCN]+TX、乙拌磷(278)+TX、DNOC(282)+TX、苯氧炔螨(1113)+TX、多拉菌素[CCN]+TX、硫丹(294)+TX、因毒磷(1121)+TX、EPN(297)+TX,依普菌素[CCN]+TX、乙硫磷(309)+TX、益硫磷(1134)+TX、乙螨唑(320)+TX、乙嘧硫磷(1142)+TX、抗螨唑(1147)+TX、喹螨醚(328)+TX、苯丁锡(330)+TX、苯硫威(337)+TX、甲氰菊酯(342)+TX、吡螨胺+TX、唑螨酯(345)+TX、芬螨酯(1157)+TX、氟硝二苯胺(1161)+TX、氰戊菊酯(349)+TX、氟虫猜(354)+TX、嘧螨酯(360)+TX、啶蜱脲(1166)+TX、氟螨噻(1167)+TX、氟环脲(366)+TX、氟氰戊菊酯(367)+TX、联氟螨(1169)+TX、氟芬隆(370)+TX、氟氯苯菊酯(372)+TX、氟杀螨(1174)+TX、氟胺氰菊酯(1184)+TX、FMC 1137(研发代码)(1185)+TX、杀螨脒(405)+TX、盐酸杀螨脒(405)+TX、安果(1192)+TX、胺甲威(1193)+TX、γ-HCH(430)+TX、果绿定(1205)+TX、苄螨醚(424)+TX、庚烯磷(432)+TX、十六烷基环丙烷羧酸酯(IUPAC/化学文摘名称)(1216)+TX、噻螨酮(441)+TX、碘甲烷(IUPAC名称)(542)+TX、水胺硫磷(473)+TX、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯(IUPAC名称)(473)+TX、伊佛霉素[CCN]+TX、茉莉菊酯I(696)+TX、茉莉菊酯II(696)+TX、碘硫磷(1248)+TX、灵丹(430)+TX、氯芬奴隆(490)+TX、马拉硫磷(492)+TX、丙螨氰(1254)+TX、灭蚜磷(502)+TX、地安磷(1261)+TX、甲硫芬[CCN]+TX、虫螨畏(1266)+TX、甲胺磷(527)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、灭多虫(531)+TX、甲基溴(537)+TX、速灭威(550)+TX、速灭磷(556)+TX、兹克威(1290)+TX、密灭汀(557)+TX、米尔贝肟[CCN]+TX、丙胺氟(1293)+TX、久效磷(561)+TX、茂果(1300)+TX、莫昔克丁[CCN]+TX、二溴磷(567)+TX、NC-184(化合物代码)+TX、NC-512(化合物代码)+TX、氟蚁灵(1309)+TX、华光霉素[CCN]+TX、戊氰威(1313)+TX、戊氰威1:1氯化锌络合物(1313)+TX、NNI-0101(化合物代码)+TX、NNI-0250(化合物代码)+TX、氧乐果(594)+TX、草氨酰(602)+TX、异亚砜磷(1324)+TX、砜拌磷(1325)+TX、pp'-DDT(219)+TX、对硫磷(615)+TX、苄氯菊酯(626)+TX、石油(628)+TX、芬硫磷(1330)+TX、稻丰散(631)+TX、甲拌磷(636)+TX、伏杀磷(637)+TX、硫环磷(1338)+TX、亚胺硫磷(638)+TX、磷胺(639)+TX、辛硫磷(642)+TX、嘧啶磷-甲基(652)+TX、聚氯萜烯(传统名称)(1347)+TX、浏阳霉素(别名)(653)+TX、丙氯醇(1350)+TX、丙溴磷(662)+TX、蜱虱威(1354)+TX、克螨特(671)+TX、巴胺磷(673)+TX、残杀威(678)+TX、乙噻唑磷(1360)+TX、发硫磷(1362)+TX、除虫菊酯I(696)+TX、除虫菊酯(II)(696)+TX、除虫菊酯(696)+TX、哒螨灵(699)+TX、哒嗪硫磷(701)+TX、嘧螨醚(706)+TX、嘧硫磷(1370)+TX、喹恶磷(711)+TX、喹硫磷(1381)+TX、R-1492(研发代码)(1382)+TX、RA-17(研发代码)(1383)+TX、鱼藤酮(722)+TX、八甲磷(1389)+TX、克线丹+TX、司拉克丁[CCN]+TX、SI-0009(化合物代码)+TX、苏硫磷(1402)+TX、螺螨酯(738)+TX、螺甲螨酯(739)+TX、SSI-121(研发代码)(1404)+TX、舒非仑[CCN]+TX、氟虫胺(750)+TX、治螟磷(753)+TX、硫磺(754)+TX、SZI-121(研发代码)(757)+TX、氟胺氰菊酯(tau-fluvalinate)(398)+TX、吡螨胺(763)+TX、TEPP(1417)+TX、叔丁威+TX、杀虫畏(777)+TX、四氯杀螨砜(786)+TX、杀螨素(653)+TX、杀螨好(1425)+TX、噻芬诺+TX、抗虫威(1431)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、克杀螨(1436)+TX、苏云金素[CCN]+TX、威菌磷(1441)+TX、苯螨噻(1443)+TX、三唑磷(820)+TX、唑蚜威+TX、三氯磷酸酯(824)+TX、三氯丙氧磷(1455)+TX、三活菌素(653)+TX、蚜灭多(847)+TX、氟吡唑虫[CCN]和YI-5302(化合物代码)+TX,
一种杀藻剂,该杀藻剂选自由以下组成的物质组:3-苯并[b]噻吩-2-基-5,6-二氢-1,4,2-噁噻嗪-4-氧化物[CCN]+TX、二辛酸铜(IUPAC名称)(170)+TX、硫酸铜(172)+TX、cybutryne[CCN]+TX、二氢萘醌(dichlone)(1052)+TX、双氯酚(232)+TX、茵多酸(295)+TX、三苯锡(fentin)(347)+TX、熟石灰[CCN]+TX、代森钠(nabam)(566)+TX、灭藻醌(quinoclamine)(714)+TX、醌萍胺(quinonamid)(1379)+TX、西玛津(730)+TX、三苯锡乙酸盐(IUPAC名称)(347)和氢氧化三苯锡(IUPAC名称)(347)+TX,
一种驱蠕虫剂,该驱蠕虫剂选自由以下组成的物质组:阿巴美丁(1)+TX、克芦磷酯(1011)+TX、多拉克汀[CCN]+TX、依马克丁(291)+TX、依马克丁苯甲酸酯(291)+TX、依立诺克丁[CCN]+TX、伊维菌素[CCN]+TX、米尔倍霉素[CCN]+TX、莫昔克丁[CCN]+TX、哌嗪[CCN]+TX、塞拉菌素(selamectin)[CCN]+TX、多杀菌素(737)和硫菌灵(thiophanate)(1435)+TX,
一种杀鸟剂,该杀鸟剂选自由以下组成的物质组:氯醛糖(127)+TX、异狄氏剂(1122)+TX、倍硫磷(346)+TX、吡啶-4-胺(IUPAC名称)(23)和士的宁(745)+TX,
一种杀细菌剂,该杀细菌剂选自由以下组成的物质组:1-羟基-1H-吡啶-2-硫酮(IUPAC名称)(1222)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、8-羟基喹啉硫酸盐(446)+TX、溴硝醇(97)+TX、二辛酸铜(IUPAC名称)(170)+TX、氢氧化铜(IUPAC名称)(169)+TX、甲酚[CCN]+TX、双氯酚(232)+TX、双吡硫翁(1105)+TX、多地辛(1112)+TX、敌磺钠(fenaminosulf)(1144)+TX、甲醛(404)+TX、汞加芬[CCN]+TX、春雷霉素(483)+TX、春雷霉素盐酸盐水合物(483)+TX、二(二甲基二硫代氨基甲酸盐)镍(IUPAC名称)(1308)+TX、三氯甲基吡啶(nitrapyrin)(580)+TX、辛噻酮(octhilinone)(590)+TX、奥索利酸(606)+TX、土霉素(611)+TX、羟基喹啉硫酸钾(446)+TX、烯丙苯噻唑(probenazole)(658)+TX、链霉素(744)+TX、链霉素倍半硫酸盐(744)+TX、叶枯酞(766)+TX、和硫柳汞[CCN]+TX,
一种生物试剂,该生物试剂选自由以下组成的物质组:棉褐带卷蛾颗粒体病毒(Adoxophyes orana GV)(12)+TX、放射形土壤杆菌(13)+TX、钝绥螨属(Amblyseius spp.)(19)+TX、芹菜夜蛾核多角体病毒(Anagrapha falcifera NPV)(28)+TX、Anagrus atomus(29)+TX、短距蚜小蜂(Aphelinus abdominalis)(33)+TX、棉蚜寄生蜂(Aphidiuscolemani)(34)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)(35)+TX、苜蓿银纹夜蛾核多角体病毒(Autographa californica NPV)(38)+TX、坚硬芽孢杆菌(Bacillus firmus)(48)+TX、球形芽孢杆菌(Bacillus sphaericus Neide)(学名)(49)+TX、苏云金芽孢杆菌(Bacillusthuringiensis Berliner)(学名)(51)+TX、苏云金芽孢杆菌鲇泽亚种(Bacillusthuringiensis subsp.aizawai)(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subsp.israelensis)(学名)(51)+TX、苏云金芽孢杆菌日本亚种(Bacillusthuringiensis subsp.japonensis)(学名)(51)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subsp.kurstaki)(学名)(51)+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subsp.tenebrionis)(学名)(51)+TX、球孢白僵茵(Beauveria bassiana)(53)+TX、布氏白僵茵(Beauveria brongniartii)(54)+TX、草蜻蛉(Chrysoperla carnea)(151)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(178)+TX、苹果蠹蛾颗粒体病毒(Cydia pomonella GV)(191)+TX、西伯利亚离颚茧蜂(Dacnusasibirica)(212)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)(254)+TX、丽蚜小蜂(Encarsiaformosa)(学名)(293)+TX、桨角蚜小蜂(Eretmocerus eremicus)(300)+TX、玉米穗夜蛾核多角体病毒(Helicoverpa zea NPV)(431)+TX、嗜茵异小杆线虫(Heterorhabditisbacteriophora)和H.megidis(433)+TX、会聚长足瓢虫(Hippodamia convergens)(442)+TX、橘粉介壳虫寄生蜂(Leptomastix dactylopii)(488)+TX、盲蝽(Macrolophuscaliginosus)(491)+TX、甘蓝夜蛾核多角体病毒(Mamestra brassicae NPV)(494)+TX、Metaphycus helvolus(522)+TX、黄绿绿僵茵(Metarhizium anisopliae var.acridum)(学名)(523)+TX、金龟子绿僵菌小孢变种(Metarhizium anisopliae var.anisopliae)(学名)(523)+TX、松黄叶蜂(Neodiprion sertifer)核多角体病毒和红头松树叶蜂(N.lecontei)核多角体病毒(575)+TX、小花蝽属(596)+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)(613)+TX、智利捕植螨(Phytoseiulus persimilis)(644)+TX、甜菜夜蛾(Spodopteraexigua multicapsid)多核衣壳核多角体病毒(学名)(741)+TX、毛蚊线虫(Steinernemabibionis)(742)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(742)+TX、夜蛾斯氏线虫(742)+TX、Steinernema glaseri(742)+TX、Steinernema riobrave(742)+TX、Steinernema riobravis(742)+TX、蝼蛄斯氏线虫(742)+TX、斯氏线虫属(Steinernemaspp.)(742)+TX、赤眼蜂属(826)+TX、西方盲走螨(Typhlodromus occidentalis)(844)和蜡蚧轮枝茵(Verticillium lecanii)(848)+TX,
一种土壤消毒剂,该土壤消毒剂选自由以下组成的物质组:碘甲烷(IUPAC名称)(542)和甲基溴(537)+TX,
一种化学不育剂,该化学不育剂选自由以下组成的物质组:唑磷嗪(apholate)[CCN]+TX、双(氮丙啶)甲氨基膦硫化物(bisazir)[CCN]+TX、白消安[CCN]+TX、除虫脲(250)+TX、迪麦替夫(dimatif)[CCN]+TX、六甲蜜胺(hemel)[CCN]+TX、六甲磷(hempa)[CCN]+TX、甲基涕巴(metepa)[CCN]+TX、甲硫涕巴(methiotepa)[CCN]+TX、不育特(methyl apholate)[CCN]+TX、不孕啶(morzid)[CCN]+TX、氟幼脲(penfluron)[CCN]+TX、涕巴(tepa)[CCN]+TX、硫代六甲磷(thiohempa)[CCN]+TX、硫涕巴[CCN]+TX、曲他胺[CCN]和尿烷亚胺[CCN]+TX,
一种昆虫信息素,该昆虫信息素选自由以下组成的物质组:(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇(IUPAC名称)(222)+TX、(E)-十三碳-4-烯-1-基乙酸酯(IUPAC名称)(829)+TX、(E)-6-甲基庚-2-烯-4-醇(IUPAC名称)(541)+TX、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯(IUPAC名称)(779)+TX、(Z)-十二碳-7-烯-1-基乙酸酯(IUPAC名称)(285)+TX、(Z)-十六碳-11-烯醛(IUPAC名称)(436)+TX、(Z)-十六碳-11-烯-1-基乙酸酯(IUPAC名称)(437)+TX、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯(IUPAC名称)(438)+TX、(Z)-二十-13-烯-10-酮(IUPAC名称)(448)+TX、(Z)-十四碳-7-烯-1-醛(IUPAC名称)(782)+TX、(Z)-十四碳-9-烯-1-醇(IUPAC名称)(783)+TX、(Z)-十四碳-9-烯-1-基乙酸酯(IUPAC名称)(784)+TX、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯(IUPAC名称)(283)+TX、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯(IUPAC名称)(780)+TX、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯(IUPAC名称)(781)+TX、14-甲基十八-1-烯(IUPAC名称)(545)+TX、4-甲基壬醛-5-醇与4-甲基壬醛-5-酮(IUPAC名称)(544)+TX、α-多纹素(multistriatin)[CCN]+TX、西部松小蠹集合信息素(brevicomin)[CCN]+TX、十二碳二烯醇(codlelure)[CCN]+TX、十二碳二烯醇(codlemone)(167)+TX、诱蝇酮(cuelure)(179)+TX、环氧十九烷(disparlure)(277)+TX、十二碳-8-烯-1基乙酸酯(IUPAC名称)(286)+TX、十二碳-9-烯-1-基乙酸酯(IUPAC名称)(287)+TX、十二碳-8+TX、10-二烯-1-基乙酸酯(IUPAC名称)(284)+TX、dominicalure[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚[CCN]+TX、南部松小蠹集合信息素(frontalin)[CCN]+TX、诱虫十六酯(gossyplure)(420)+TX、诱杀烯混剂(grandlure)(421)+TX、诱杀烯混剂I(421)+TX、诱杀烯混剂II(421)+TX、诱杀烯混剂III(421)+TX、诱杀烯混剂IV(421)+TX、醋酸十六烯酯(hexalure)[CCN]+TX、齿小蠹二烯醇(ipsdienol)[CCN]+TX、小蠢烯醇(ipsenol)[CCN]+TX、金龟子性诱剂(japonilure)(481)+TX、lineatin[CCN]+TX、litlure[CCN]+TX、粉纹夜蛾性诱剂(looplure)[CCN]+TX、诱杀酯(medlure)[CCN]+TX、megatomoic acid[CCN]+TX、诱虫醚(methyl eugenol)(540)+TX、诱虫烯(muscalure)(563)+TX、十八-2,13-二烯-1-基乙酸酯(IUPAC名称)(588)+TX、十八-3,13-二烯-1-基乙酸酯(IUPAC名称)(589)+TX、贺康彼(orfralure)[CCN]+TX、oryctalure(317)+TX、非乐康(ostramone)[CCN]+TX、诱虫环(siglure)[CCN]+TX、sordidin(736)+TX、食菌甲诱醇(sulcatol)[CCN]+TX、十四-11-烯-1-基乙酸酯(IUPAC名称)(785)+TX、特诱酮(839)+TX、特诱酮A(839)+TX、特诱酮B1(839)+TX、特诱酮B2(839)+TX、特诱酮C(839)和trunc-call[CCN]+TX,
一种昆虫驱避剂,该昆虫驱避剂选自由以下组成的物质组:2-(辛基硫代)乙醇(IUPAC名称)(591)+TX、避蚊酮(butopyronoxyl)(933)+TX、丁氧基(聚丙二醇)(936)+TX、己二酸二丁酯(IUPAC名称)(1046)+TX、邻苯二甲酸二丁酯(1047)+TX、丁二酸二丁酯(IUPAC名称)(1048)+TX、避蚊胺[CCN]+TX、避蚊胺[CCN]+TX、驱蚊酯(dimethyl carbate)[CCN]+TX、乙基己二醇(1137)+TX、己脲[CCN]+TX、甲喹丁(methoquin-butyl)(1276)+TX、甲基新癸酰胺[CCN]+TX、氨羰基甲酸酯(oxamate)[CCN]和羟哌酯[CCN]+TX,
一种杀昆虫剂,该杀昆虫剂选自由以下组成的物质组:1-二氯-1-硝基乙烷(IUPAC/化学文摘名称)(1058)+TX、1,1-二氯-2,2-双(4-乙基苯基)乙烷(IUPAC名称)(1056)+TX、1,2-二氯丙烷(IUPAC/化学文摘名称)(1062)+TX、具有1,3-二氯丙烯的1,2-二氯丙烷(IUPAC名称)(1063)+TX、1-溴-2-氯乙烷(IUPAC/化学文摘名称)(916)+TX、2,2,2-三氯-1-(3,4-二氯苯基)乙酸乙酯(IUPAC名)(1451)+TX、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸酯(IUPAC名)(1066)+TX、2-(1,3-1,3-二硫戊烷-2-基)苯基二甲基氨基甲酸酯(IUPAC/化学文摘名称)(1109)+TX、2-(2-叔氧基乙氧基)乙基硫氰酸酯(IUPAC/化学文摘名称)(935)+TX、2-(4,5-二甲基-1,3-二氧戊环-2-基)苯基甲基氨基甲酸酯(IUPAC/化学文摘名称)(1084)+TX、2-(4-氯-3,5-二甲基苯氧基)乙醇(IUPAC名)(986)+TX、2-氯乙烯基二乙基磷酸酯(IUPAC名)(984)+TX、2-咪唑烷酮(IUPAC名)(1225)+TX、2-异戊酰基茚满-1,3-二酮(IUPAC名)(1246)+TX、2-甲基(丙-2-炔基)氨基苯基甲基氨基甲酸酯(IUPAC名)(1284)+TX、2-硫氰酸醇乙基月桂酸酯(IUPAC名)(1433)+TX、3-溴-1-氯丙-1-烯(IUPAC名)(917)+TX、3-甲基-1-苯基吡唑-5-基二甲基氨基甲酸酯(IUPAC名)(1283)+TX、4-甲基(丙-2-炔基)氨基-3,5-二甲苯基基甲基氨基甲酸酯(IUPAC名)(1285)+TX、5,5-二甲基-3-氧代环己-1-烯基二甲基氨基甲酸酯(IUPAC名)(1085)+TX、阿维菌素(1)+TX、乙酰甲胺磷(2)+TX、啶虫脒(4)+TX、家蝇磷杀昆虫剂[CCN]+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、丙烯腈(IUPAC名)(861)+TX、棉铃威(15)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、艾氏剂(864)+TX、烯丙菊酯(17)+TX、阿洛氨菌素[CCN]+TX、除害威(866)+TX、α-氯氰菊酯(202)+TX、α-蜕皮激素[CCN]+TX、磷化铝(640)+TX、赛果(870)+TX、果满磷(872)+TX、灭害威(873)+TX、胺吸磷杀螨剂(875)+TX、草酸氢胺吸磷(amiton hydrogen oxalate)(875)+TX、双甲脒(24)+TX、新烟碱(877)+TX、乙基杀扑磷(883)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、印楝素(别名)(41)+TX、甲基吡啶磷(42)+TX、乙基谷硫磷(44)+TX、甲基谷硫磷(45)+TX、偶氮磷(889)+TX、苏云金芽孢杆菌δ内毒素(52)+TX、六氟硅酸钡[CCN]+TX、多硫化钡(IUPAC/化学文摘名称)(892)+TX、熏菊酯[CCN]+TX、拜耳22/190(研究代码)(893)+TX、拜耳22408(研究代码)(894)+TX、恶虫威(58)+TX、丙硫克百威(60)+TX、杀虫磺(66)+TX、β-氟氯氰菊酯(194)+TX、β-氯氰菊酯(203)+TX、联苯菊酯(76)+TX、生物丙烯菊酯(78)+TX、生物丙烯菊酯S-环戊烯基异构体(79)+TX、戊环苄呋菊酯[CCN]+TX、生物氯菊酯(908)+TX、苄呋菊脂(80)+TX、双(2-氯乙基)醚(IUPAC名)(909)+TX、双三氟虫脲(83)+TX、硼砂(86)+TX、溴灭菊酯+TX、溴苯烯磷(914)+TX、溴烯杀(918)+TX、溴-DDT[CCN]+TX、溴硫磷(920)+TX、溴硫磷-乙基(921)+TX、合杀威(924)+TX、稻虱净(99)+TX、畜虫威(926)+TX、特嘧硫磷(927)+TX、丁酮威(103)+TX、丁酯磷(932)+TX、丁酮砜威(104)+TX、丁基哒螨灵+TX、硫线磷(109)+TX、砷酸钙[CCN]+TX、氰化钙(444)+TX、多硫化钙(IUPAC名称)(111)+TX、毒杀芬(941)+TX、氯灭杀威(943)+TX、西维因(115)+TX、卡巴呋喃(118)+TX、二硫化碳(IUPAC/化学文摘名称)(945)+TX、四氯化碳(IUPAC名)(946)+TX、三硫磷(947)+TX、丁硫克百威(119)+TX、杀螟丹(123)+TX、盐酸杀螟丹(123)+TX、瑟瓦定(725)+TX、冰片丹(960)+TX、氯丹(128)+TX、十氯酮(963)+TX、杀虫脒(964)+TX、盐酸杀虫脒(964)+TX、氯氧磷(129)+TX、溴虫腈(130)+TX、毒虫畏(131)+TX、氟啶脲(132)+TX、氯甲磷(136)+TX、氯仿[CCN]+TX、氯化苦(141)+TX、氯腈肟磷(989)+TX、氯吡唑磷(990)+TX、毒死蜱(145)+TX、毒死蜱-甲基(146)+TX、虫螨磷(994)+TX、环虫酰肼(150)+TX、瓜菊酯I(696)+TX、瓜菊酯II(696)+TX、瓜菊酯(696)+TX、顺式-苄呋菊脂+TX、顺式苄呋菊酯(80)+TX、三氟氯氰菊酯+TX、地虫威(999)+TX、氯氰碘柳胺[CCN]+TX、噻虫胺(165)+TX、乙酰亚砷酸铜[CCN]+TX、砷酸铜[CCN]+TX、油酸铜[CCN]+TX、蝇毒磷(174)+TX、畜虫磷(1006)+TX、克罗米通[CCN]+TX、巴毒磷(1010)+TX、育畜磷(1011)+TX、冰晶石(177)+TX、CS 708(研究代码)(1012)+TX、苯腈磷(1019)+TX、杀螟腈(184)+TX、果虫磷(1020)+TX、环虫菊酯[CCN]+TX、乙氰菊脂(188)+TX、氟氯氰菊酯(193)+TX、三氟氯氰菊酯(196)+TX、氯氰菊酯(201)+TX、苯氰菊酯(206)+TX、灭蝇胺(209)+TX、畜蜱磷[CCN]+TX、d-柠檬烯[CCN]+TX、d-胺菊酯(788)+TX、DAEP(1031)+TX、棉隆(216)+TX、DDT(219)+TX、一甲呋喃丹(1034)+TX、溴氰菊酯(223)+TX、田乐磷(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(1038)+TX、内吸磷-甲基(224)+TX、内吸磷-O(1038)+TX、内吸磷-O-甲基(224)+TX、内吸磷-S(1038)+TX、内吸磷-S-甲基(224)+TX、横吸怜(demeton-S-methylsulphon)(1039)+TX、丁醚脲(226)+TX、氯亚胺硫磷(1042)+TX、二胺磷(1044)+TX、二嗪农(227)+TX、异氯硫磷(1050)+TX、除线磷(1051)+TX、敌敌畏(236)+TX、二克磷+TX、敌来死[CCN]+TX、百治磷(243)+TX、地昔尼尔(244)+TX、狄氏剂(1070)+TX、5-甲基吡唑-3-基磷酸二乙基酯(IUPAC名)(1076)+TX、除虫脲(250)+TX、双羟丙茶碱[CCN]+TX、四氟甲醚菊酯[CCN]+TX、甲氟磷(1081)+TX、地麦威(1085)+TX、乐果(262)+TX、苄菌酯(1083)+TX、甲基毒虫畏(265)+TX、敌蝇威(1086)+TX、消螨酚(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、丙硝酚(1093)+TX、戊硝酚(1094)+TX、地乐酚(1095)+TX、呋虫胺(271)+TX、苯虫醚(1099)+TX、蔬果磷(1100)+TX、二氧威(1101)+TX、敌杀磷(1102)+TX、乙拌磷(278)+TX、噻喃磷(1108)+TX、DNOC(282)+TX、多拉菌素[CCN]+TX、DSP(1115)+TX、脱皮甾酮[CCN]+TX、EI1642(研究代码)(1118)+TX、甲氨基阿维菌素(291)+TX、甲氨基阿维菌素苯甲酸盐(291)+TX、EMPC(1120)+TX、烯炔菊酯(292)+TX、硫丹(294)+TX、因毒磷(1121)+TX、安特灵(1122)+TX、EPBP(1123)+TX、EPN(297)+TX、保幼醚(1124)+TX、依立诺克丁[CCN]+TX、高氰戊菊酯(302)+TX、依他伏杀[CCN]+TX、杀虫丹(308)+TX、乙硫磷(309)+TX、乙虫清(310)+TX、益果-甲基(1134)+TX、灭线磷(312)+TX、甲酸乙酯(IUPAC名)[CCN]+TX、乙基-DDD(1056)+TX、二溴化乙烯(316)+TX、二氯化乙烯(化学名称)(1136)+TX、环氧乙烷[CCN]+TX、醚菊酯(319)+TX、乙嘧硫磷(1142)+TX、EXD(1143)+TX、氨磺磷(323)+TX、克线磷(326)+TX、抗螨唑(1147)+TX、皮蝇硫磷(1148)+TX、乙苯威(1149)+TX、五氟苯菊酯(1150)+TX、杀螟硫磷(335)+TX、仲丁威(336)+TX、非诺克林(1153)+TX、苯氧威(340)+TX、吡氯氰菊酯(1155)+TX、甲氰菊酯(342)+TX、吡螨胺+TX、丰索磷(1158)+TX、倍硫磷(346)+TX、倍硫磷-乙基[CCN]+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、氟尼胺(358)+TX、氟虫双酰胺(CAS登记号:272451-65-7)+TX、伏康脲(1168)+TX、氟环脲(366)+TX、氟氰戊菊酯(367)+TX、联氟螨(1169)+TX、嘧虫胺[CCN]+TX、氟芬隆(370)+TX、三氟醚(1171)+TX、氟氯苯菊酯(372)+TX、氟胺氰菊酯(1184)+TX、FMC 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15525(研究代码)(723)+TX、RU25475(研究代码)(1386)+TX、鱼尼丁(1387)+TX、利阿诺定(传统名称)(1387)+TX、沙巴藜芦(725)+TX、八甲磷(1389)+TX、克线丹+TX、司拉克丁[CCN]+TX、SI-0009(化合物代码)+TX、SI-0205(化合物代码)+TX、SI-0404(化合物代码)+TX、SI-0405(化合物代码)+TX、氟硅菊酯(728)+TX、SN72129(研究代码)(1397)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟化钠(IUPAC/化学文摘名称)(1399)+TX、六氟硅酸钠(1400)+TX、五氯酚钠(623)+TX、硒酸钠(IUPAC名称)(1401)+TX、硫氰酸钠[CCN]+TX、苏硫磷(1402)+TX、多杀菌素(737)+TX、螺甲螨酯(739)+TX、螺虫乙酯(CCN)+TX、磺苯醚隆(746)+TX、磺苯醚隆-钠(746)+TX、氟虫胺(750)+TX、治螟磷(753)+TX、氟化硫酰基(756)+TX、硫丙磷(1408)+TX、焦油(758)+TX、氟胺氰菊酯(tau-fluvalinate)(398)+TX、噻螨威(1412)+TX、TDE(1414)+TX、虫酰肼(762)+TX、吡螨胺(763)+TX、丁基嘧啶磷(764)+TX、氟苯脲(768)+TX、七氟菊酯(769)+TX、双硫磷(770)+TX、TEPP(1417)+TX、环戊烯丙菊酯(1418)+TX、叔丁威+TX、特丁磷(773)+TX、四氯乙烷[CCN]+TX、杀虫畏(777)+TX、胺菊酯(787)+TX、θ-氯氰菊酯(204)+TX、噻虫啉(791)+TX、噻芬诺+TX、噻虫嗪(792)+TX、苯噻硫磷(1428)+TX、抗虫威(1431)+TX、杀虫环(798)+TX、草酸氢杀虫环(798)+TX、硫敌克(799)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、硫磷嗪(1434)+TX、杀虫双(803)+TX、杀虫双(thiosultap-sodium)(803)+TX、苏云金素[CCN]+TX、唑虫酰胺(809)+TX、四溴菊酯(812)+TX、四氟苯菊酯(813)+TX、反氯菊酯(1440)+TX、威菌磷(1441)+TX、唑蚜威(818)+TX、三唑磷(820)+TX、唑呀威+TX、三氯磷酸酯(824)+TX、异皮蝇磷-3[CCN]+TX、毒壤膦(1452)+TX、三氯丙氧磷(1455)+TX、杀虫隆(835)+TX、混杀威(840)+TX、烯虫硫酯(1459)+TX、蚜灭多(847)+TX、氟吡唑虫[CCN]+TX、藜芦定(725)+TX、藜芦碱(725)+TX、XMC(853)+TX、灭杀威(854)+TX、YI-5302(化合物代码)+TX、C-氯氰菊酯(205)+TX、zetamethrin+TX、磷化辞(640)+TX、zolaprofos(1469)和ZXI 8901(研究代码)(858)+TX、氰虫酰胺[736994-63-19]+TX、氯虫苯甲酰胺[500008-45-7]+TX、腈吡螨酯[560121-52-0]+TX、丁氟螨酯[400882-07-7]+TX、新喹唑啉[337458-27-2]+TX、乙基多杀菌素[187166-40-1+187166-15-0]+TX、螺虫乙酯[203313-25-1]+TX、砜虫啶[946578-00-3]+TX、丁烯氟虫腈[704886-18-0]+TX、氯氟醚菊酯[915288-13-0]+TX、四氟醚菊酯(tetramethylfluthrin)[84937-88-2]+TX、三氟苯嘧啶(在WO2012/092115所公开的)+TX、fluxametamide(WO 2007/026965)+TX、ε-甲氧苄氟菊酯[240494-71-7]+TX、ε-momfluorothrin[1065124-65-3]+TX、fluazaindolizine[1254304-22-7]+TX、氯碱丙炔菊酯(chloroprallethrin)[399572-87-3]+TX、fluxametamide[928783-29-3]+TX、cyhalodiamide[1262605-53-7]+TX、tioxazafen[330459-31-9]+TX、broflanilide[1207727-04-5]+TX、丁烯氟虫腈(flufiprole)[704886-18-0]+TX、环溴虫酰胺(cyclaniliprole)[1031756-98-5]+TX、氟氰虫酰胺(tetraniliprole)[1229654-66-3]+TX、戊吡虫胍(guadipyr)(描述于WO 2010/060231中)+TX、环氧虫啶(cycloxaprid)(描述于WO 2005/077934中)+TX,
杀软体动物剂,该杀软体动物剂选自由以下物质组成的组:二(三丁基锡)氧化物(IUPAC名称)(913)+TX、溴乙酰胺[CCN]+TX、砷酸钙[CCN]+TX、除线威(cloethocarb)(999)+TX、乙酰亚砷酸铜[CCN]+TX、硫酸铜(172)+TX、三苯锡(347)+TX、磷酸铁(IUPAC名称)(352)+TX、四聚乙醛(518)+TX、灭虫威(530)+TX、氯硝柳胺(576)+TX、氯硝柳胺乙醇胺盐(576)+TX、五氯酚(623)+TX、五氯苯氧化钠(623)+TX、噻螨威(tazimcarb)(1412)+TX、硫双威(799)+TX、三丁基氧化锡(913)+TX、杀螺吗啉(trifenmorph)(1454)+TX、混杀威(trimethacarb)(840)+TX、乙酸三苯基锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX、皮瑞普(pyriprole)[394730-71-3]+TX,
一种杀线虫剂,该杀线虫剂选自由以下组成的物质组:AKD-3088(化合物代码)+TX、1,2-二溴-3-氯丙烷(IUPAC/化学文摘名)(1045)+TX、1,2-二氯丙烷(IUPAC/化学文摘名)(1062)+TX、1,2-二氯丙烷与1,3-二氯丙烯(IUPAC名称)(1063)+TX、1,3-二氯丙烯(233)+TX、3,4-二氯四氢噻吩1,1-二氧化物(IUPAC/化学文摘名)(1065)+TX、3-(4-氯苯基)-5-甲基绕丹宁(IUPAC名称)(980)+TX、5-甲基-6-硫代-1,3,5-噻二嗪烷-3-基乙酸(IUPAC名称)(1286)+TX、6-异戊烯基氨基嘌呤(210)+TX、阿巴美丁(1)+TX、乙酰虫腈[CCN]+TX、棉铃威(15)+TX、涕灭威(aldicarb)(16)+TX、涕灭砜威(aldoxycarb)(863)+TX、AZ 60541(化合物代码)+TX、benclothiaz[CCN]+TX、苯茵灵(62)+TX、丁基哒螨酮(butylpyridaben)+TX、硫线磷(cadusafos)(109)+TX、克百威(carbofuran)(118)+TX、二硫化碳(945)+TX、丁硫克百威(119)+TX、氯化苦(141)+TX、毒死蜱(145)+TX、除线威(cloethocarb)(999)+TX、细胞分裂素(cytokinins)(210)+TX、棉隆(216)+TX、DBCP(1045)+TX、DCIP(218)+TX、除线特(diamidafos)(1044)+TX、除线磷(dichlofenthion)(1051)+TX、二克磷(dicliphos)+TX、乐果(262)+TX、依马克丁[CCN]+TX、苯甲酸依马克丁(291)+TX、依立诺克丁(291)+TX、[CCN]+TX、灭线磷(312)+TX、二溴乙烷(316)+TX、苯线磷(fenamiphos)(326)+TX、吡螨胺+TX、丰索磷(fenpyrad)(1158)+TX、噻唑磷(fosthiazate)(408)+TX、丁硫环磷(fosthietan)(1196)+TX、糠醛[CCN]+TX、GY-81(研究代码)(423)+TX、速杀硫磷(heterophos)[CCN]+TX、碘甲烷(IUPAC名称)(542)+TX、isamidofos(1230)+TX、氯唑磷(isazofos)(1231)+TX、激动素(kinetin)[CCN]+TX、糠氨基嘌呤(mecarphon)(210)+TX、甲基灭蚜磷(mecarphon)(1258)+TX、威百亩(519)+TX、威百亩钾盐(519)+TX、威百亩钠盐(519)+TX、甲基溴(537)+TX、异硫氰酸甲酯(543)+TX、杀螨菌素肟(milbemycin oxime)[CCN]+TX、莫昔克丁(剔名)[CCN]+TX、疣孢漆斑茵(Myrothecium verrucaria)组分(565)+TX、NC-184(化合物代码)+TX、杀线威(602)+TX、甲拌磷(636)+TX、磷胺(639)+TX、磷虫威(phosphocarb)[CCN]+TX、硫线磷(sebufos)+TX、塞拉菌素(selamectin)[CCN]+TX、多杀菌素(737)+TX、叔丁威(terbam)+TX、特丁磷(terbufos)(773)+TX、四氯噻吩(IUPAC/化学文摘名)(1422)+TX、thiaf enox+TX、虫线磷(thionazin)(1434)+TX、三唑磷(triazophos)(820)+TX、triazuron+TX、二甲苯酚[CCN]+TX、YI-5302(化合物代码)和玉米素(210)+TX、fluensulfone[318290-98-1]+TX,
一种硝化作用抑制剂,该硝化作用抑制剂选自由以下组成的物质组:乙基黄原酸钾[CCN]以及氯啶(nitrapyrin)(580)+TX,
一种植物激活剂,该植物激活剂选自由以下组成的物质组:噻二唑素(acibenzolar)(6)+TX、噻二唑素-S-甲基(6)+TX、烯丙苯噻唑(probenazole)(658)和大虎杖(Reynoutria sachalinensis)提取物(720)+TX,
一种杀鼠剂,该杀鼠剂选自由以下组成的物质组:2-异戊酰茚满-1,3-二酮(IUPAC名称)(1246)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、α-氯代醇[CCN]+TX、磷化铝(640)+TX、安妥(880)+TX、三氧化二砷(882)+TX、碳酸钡(891)+TX、双鼠脲(912)+TX、溴鼠隆(89)+TX、溴敌隆(91)+TX、溴鼠胺(92)+TX、氰化钙(444)+TX、氮醛糖(127)+TX、氯鼠酮(140)+TX、维生素D3(850)+TX、氯灭鼠灵(1004)+TX、克灭鼠(1005)+TX、杀鼠萘(175)+TX、杀鼠嘧啶(1009)+TX、鼠得克(246)+TX、噻鼠灵(249)+TX、敌鼠钠(273)+TX、维生素D2(301)+TX、氟鼠灵(357)+TX、氟乙酰胺(379)+TX、鼠朴定(1183)+TX、盐酸鼠朴定(1183)+TX、γ-HCH(430)+TX、HCH(430)+TX、氢氰酸(444)+TX、碘甲烷(IUPAC名称)(542)+TX、林旦(430)+TX、磷化镁(IUPAC名称)(640)+TX、甲基溴(537)+TX、鼠特灵(1318)+TX、毒鼠磷(1336)+TX、磷化氢(IUPAC名称)(640)+TX、磷[CCN]+TX、杀鼠酮(1341)+TX、亚砷酸钾[CCN]+TX、灭鼠优(1371)+TX、海葱糖苷(1390)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟乙酸钠(735)+TX、士的宁(745)+TX、硫酸铊[CCN]+TX、杀鼠灵(851)以及磷化锌(640)+TX,
一种增效剂,该增效剂选自由以下组成的物质组:2-(2-丁氧基乙氧基)乙基胡椒基酯(IUPAC名称)(934)+TX、5-(1,3-苯并二氧杂环戊烯-5-基)-3-己基环己-2-烯酮(IUPAC名称)(903)+TX、具有橙花叔醇的法呢醇(324)+TX、MB-599(研究代码)(498)+TX、MGK 264(研究代码)(296)+TX、增效醚(piperonyl butoxide)(649)+TX、增效醛(piprotal)(1343)+TX、增效酯(propyl isomer)(1358)+TX、S421(研究代码)(724)+TX、增效散(sesamex)(1393)+TX、芝麻林素(sesasmolin)(1394)和亚砜(1406)+TX,
一种动物驱避剂,该动物驱避剂选自由以下组成的物质组:蒽醌(32)+TX、氯醛糖(127)+TX、环烷酸铜[CCN]+TX、王铜(171)+TX、二嗪磷(227)+TX、二环戊二烯(化学名称)(1069)+TX、双胍盐(guazatine)(422)+TX、双胍醋酸盐(422)+TX、灭虫威(530)+TX、吡啶-4-胺(IUPAC名称)(23)+TX、塞仑(804)+TX、混杀威(trimethacarb)(840)+TX、环烷酸锌[CCN]和福美锌(856)+TX,
一种杀病毒剂,该杀病毒剂选自由以下组成的物质组:衣马宁[CCN]和利巴韦林[CCN]+TX,
一种创伤保护剂,该创伤保护剂选自由以下组成的物质组:氧化汞(512)+TX、辛噻酮(octhilinone)(590)和甲基硫茵灵(802)+TX,
以及生物活性化合物,这些化合物选自由以下物质组成的组:阿扎康唑[60207-31-0]+TX、苯并烯氟菌唑[1072957-71-1]+TX、联苯三唑醇[70585-36-3]+TX、糠菌唑[116255-48-2]+TX、环唑醇[94361-06-5]+TX、苯醚甲环唑[119446-68-3]+TX、烯唑醇[83657-24-3]+TX、氟环唑[106325-08-0]+TX、腈苯唑[114369-43-6]+TX、氟喹唑[136426-54-5]+TX、氟硅唑[85509-19-9]+TX、粉唑醇[76674-21-0]+TX、己唑醇[79983-71-4]+TX、抑霉唑[35554-44-0]+TX、亚胺唑[86598-92-7]+TX、种菌唑[125225-28-7]+TX、叶菌唑[125116-23-6]+TX、腈菌唑[88671-89-0]+TX、稻瘟酯[101903-30-4]+TX、戊菌唑[66246-88-6]+TX、丙硫菌唑[178928-70-6]+TX、啶斑肟(pyrifenox)[88283-41-4]+TX、丙氯灵[67747-09-5]+TX、丙环唑[60207-90-1]+TX、硅氟唑(simeconazole)[149508-90-7]+TX、戊唑醇[107534-96-3]+TX、氟醚唑[112281-77-3]+TX、三唑酮[43121-43-3]+TX、三唑酮[55219-65-3]+TX、氟菌唑[99387-89-0]+TX、灭菌唑[131983-72-7]+TX、三环苯嘧醇[12771-68-5]+TX、氯苯嘧啶醇[60168-88-9]+TX、氟氯苯嘧啶醇[63284-71-9]+TX、乙嘧酚磺酸酯(bupirimate)[41483-43-6]+TX、甲菌定(dimethirimol)[5221-53-4]+TX、乙菌定(ethirimol)[23947-60-6]+TX、十二环吗啉[1593-77-7]+TX、苯锈啶(fenpropidine)[67306-00-7]+TX、丁苯吗啉[67564-91-4]+TX、螺环菌胺[118134-30-8]+TX、十三吗啉[81412-43-3]+TX、嘧菌环胺[121552-61-2]+TX、嘧菌胺[110235-47-7]+TX、嘧霉胺(pyrimethanil)[53112-28-0]+TX、拌种咯[74738-17-3]+TX、咯菌腈(fludioxonil)[131341-86-1]+TX、苯霜灵(benalaxyl)[71626-11-4]+TX、呋霜灵(furalaxyl)[57646-30-7]+TX、甲霜灵[57837-19-1]+TX、R-甲霜灵[70630-17-0]+TX、呋酰胺[58810-48-3]+TX、恶霜灵(Oxadixyl)[77732-09-3]+TX、苯菌灵[17804-35-2]+TX、多菌灵[10605-21-7]+TX、咪菌威(debacarb)[62732-91-6]+TX、麦穗宁[3878-19-1]+TX、噻苯达唑[148-79-8]+TX、乙菌利(chlozolinate)[84332-86-5]+TX、菌核利(dichlozoline)[24201-58-9]+TX、异菌脲(Iprodione)[36734-19-7]+TX、myclozoline[54864-61-8]+TX、腐霉利(procymidone)[32809-16-8]+TX、乙烯菌核利(vinclozoline)[50471-44-8]+TX、啶酰菌胺(boscalid)[188425-85-6]+TX、萎锈灵[5234-68-4]+TX、甲呋酰苯胺[24691-80-3]+TX、氟酰胺(Flutolanil)[66332-96-5]+TX、灭锈胺[55814-41-0]+TX、氧化萎锈灵[5259-88-1]+TX、吡噻菌胺(penthiopyrad)[183675-82-3]+TX、噻呋菌胺[130000-40-7]+TX、双胍盐[108173-90-6]+TX、多果定(dodine)[2439-10-3][112-65-2](游离键)+TX、双胍辛胺(iminoctadine)[13516-27-3]+TX、嘧菌酯[131860-33-8]+TX、醚菌胺[149961-52-4]+TX、enestroburin{Proc.BCPC,Int.Congr.,Glasgow.2003,1,93}+TX、氟嘧菌酯[361377-29-9]+TX、甲基醚菌酯[143390-89-0]+TX、苯氧菌胺[133408-50-1]+TX、肟菌酯[141517-21-7]+TX、肟醚菌胺[248593-16-0]+TX、啶氧菌酯[117428-22-5]+TX、唑菌胺酯[175013-18-0]+TX、福美铁[14484-64-1]+TX、代森锰锌[8018-01-7]+TX、代森锰[12427-38-2]+TX、代森联[9006-42-2]+TX、甲代森锌(propineb)[12071-83-9]+TX、塞仑[137-26-8]+TX、代森锌[12122-67-7]+TX、福美锌[137-30-4]+TX、敌菌丹(captafol)[2425-06-1]+TX、克菌丹[133-06-2]+TX、苯氟磺胺[1085-98-9]+TX、唑啶草(fluoroimide)[41205-21-4]+TX、灭菌丹[133-07-3]+TX、甲苯氟磺胺[731-27-1]+TX、波尔多混合剂[8011-63-0]+TX、氢氧化铜(copperhydroxid)[20427-59-2]+TX、氯化铜(copperoxychlorid)[1332-40-7]+TX、硫酸铜(coppersulfat)[7758-98-7]+TX、氧化铜(copperoxid)[1317-39-1]+TX、代森锰铜(mancopper)[53988-93-5]+TX、喹啉铜(oxine-copper)[10380-28-6]+TX、敌螨普(dinocap)[131-72-6]+TX、酞菌酯(nitrothal-isopropyl)[10552-74-6]+TX、克瘟散[17109-49-8]+TX、异稻瘟净(iprobenphos)[26087-47-8]+TX、稻瘟灵(isoprothiolane)[50512-35-1]+TX、氯瘟磷(phosdiphen)[36519-00-3]+TX、克菌磷(pyrazophos)[13457-18-6]+TX、甲基托氯磷(tolclofos-methyl)[57018-04-9]+TX、苯并噻二唑(acibenzolar-S-methyl)[135158-54-2]+TX、敌菌灵[101-05-3]+TX、苯噻菌胺[413615-35-7]+TX、灭瘟素(blasticidin)-S[2079-00-7]+TX、灭螨猛(chinomethionat)[2439-01-2]+TX、地茂散(chloroneb)[2675-77-6]+TX、百菌清[1897-45-6]+TX、环氟菌胺[180409-60-3]+TX、霜脲氰[57966-95-7]+TX、二氯萘醌(dichlone)[117-80-6]+TX、双氯氰菌胺(diclocymet)[139920-32-4]+TX、哒菌酮(diclomezine)[62865-36-5]+TX、氯硝胺(dicloran)[99-30-9]+TX、乙霉威(diethofencarb)[87130-20-9]+TX、烯酰吗啉[110488-70-5]+TX、SYPL190(Flumorph)[211867-47-9]+TX、二噻农(dithianon)[3347-22-6]+TX、噻唑菌胺(ethaboxam)[162650-77-3]+TX、土菌灵(etridiazole)[2593-15-9]+TX、恶唑菌酮[131807-57-3]+TX、咪唑菌酮(fenamidone)[161326-34-7]+TX、稻瘟酰胺(Fenoxanil)[115852-48-7]+TX、三苯锡(fentin)[668-34-8]+TX、嘧菌腙(ferimzone)[89269-64-7]+TX、氟啶胺(fluazinam)[79622-59-6]+TX、氟吡菌胺(fluopicolide)[239110-15-7]+TX、磺菌胺(flusulfamide)[106917-52-6]+TX、环酰菌胺[126833-17-8]+TX、福赛得(fosetyl-aluminium)[39148-24-8]+TX、恶霉灵(hymexazol)[10004-44-1]+TX、丙森锌[140923-17-7]+TX、IKF-916(赛座灭(Cyazofamid))[120116-88-3]+TX、春日霉素(kasugamycin)[6980-18-3]+TX、磺菌威(methasulfocarb)[66952-49-6]+TX、苯菌酮[220899-03-6]+Tx、氟噻唑吡乙酮(oxathiapiprolin)[1003318-67-9]+TX、戊菌隆(pencycuron)[66063-05-6]+TX、苯酞[27355-22-2]+TX、多氧霉素(polyoxins)[11113-80-7]+TX、噻菌灵(probenazole)[27605-76-1]+TX、百维威(propamocarb)[25606-41-1]+TX、碘喹唑酮(proquinazid)[189278-12-4]+TX、乐喹酮(pyroquilon)[57369-32-1]+TX、喹氧灵[124495-18-7]+TX、五氯硝苯[82-68-8]+TX、硫[7704-34-9]+TX、噻酰菌胺[223580-51-6]+TX、咪唑嗪(triazoxide)[72459-58-6]+TX、三环唑[41814-78-2]+TX、嗪氨灵[26644-46-2]+TX、有效霉素[37248-47-8]+TX、苯酰菌胺(zoxamide)(RH7281)[156052-68-5]+TX、双炔酰菌胺(mandipropamid)[374726-62-2]+TX、吡蚜酮(isopyrazam)[881685-58-1]+TX、塞德因(sedaxane)[874967-67-6]+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(9-二氯亚甲基-1,2,3,4-四氢-1,4-桥亚甲基-萘-5-基)-酰胺(披露于WO 2007/048556中)+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3’,4’,5’-三氟-联苯基-2-基)-酰胺(披露于WO 2006/087343中)+TX、[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(环丙基羰基)氧基]-1,3,4,4a,5,6,6a,12,12a,12b-十氢-6,12-二羟基-4,6a,12b-三甲基-11-氧代-9-(3-吡啶基)-2H,11H萘并[2,1-b]吡喃并[3,4-e]吡喃-4-基]甲基-环丙甲酸酯[915972-17-7]+TX以及1,3,5-三甲基-N-(2-甲基-1-氧丙基)-N-[3-(2-甲基丙基)-4-[2,2,2-三氟-1-甲氧基-1-(三氟甲基)乙基]苯基]-1H-吡唑-4-甲酰胺[926914-55-8]+TX;lancotrione[1486617-21-3]+TX;氯氟吡啶酯[943832-81-3]+TX;ipfentrifluconazole[1417782-08-1]+TX;氯氟醚菌唑[1417782-03-6]+TX;quinofumelin[861647-84-9]+TX;右旋反式氯丙炔菊酯[399572-87-3]+TX;氯氟氰虫酰胺[1262605-53-7]+TX;三氟咪啶酰胺[1254304-22-7]+TX;fluxametamide[928783-29-3]+TX;ε-甲氧苄氟菊酯[240494-71-7]+TX;ε-momfluorothrin[1065124-65-3]+TX;氟唑菌酰羟胺(pydiflumetofen)[1228284-64-7]+TX;κ-联苯菊酯[439680-76-9]+TX;broflanilide[1207727-04-5]+TX;dicloromezotiaz[1263629-39-5]+TX;dipymetitrone[16114-35-5]+TX;pyraziflumid[942515-63-1]和κ-七氟菊酯[391634-71-2]+TX;以及
微生物剂,包括:鲁氏不动杆菌+TX、交替支顶孢菌(Acremonium alternatum)+TX+TX、头孢支顶孢菌(Acremonium cephalosporium)+TX+TX、柿树支顶孢菌(Acremoniumdiospyri)+Tx、棍棒状支顶孢菌(Acremonium obclavatum)+TX、苹果小卷叶蛾颗粒体病毒(Adoxophyes orana granulovirus)(AdoxGV)+TX、放射形土壤杆菌菌株K84+TX、交链格孢菌+Tx、决明子链格孢菌(Alternaria cassia)+TX、毁坏链格孢菌(Alternaria destruens)+TX、使君子白粉寄生孢(Ampelomycesquisqualis)+TX、黄曲霉AF36+TX、黄曲霉NRRL 21882+Tx、曲霉属物种+TX、出芽短梗霉菌+TX、固氮螺菌属+TX、(+TX、TAZO)+TX、固氮菌属+TX、褐球固氮菌(Azotobacter chroocuccum)+TX、囊肿固氮菌(Azotobacter cysts)(Bionatural Blooming)+TX、解淀粉芽孢杆菌+TX、蜡样芽孢杆菌+TX、角质孢子芽孢杆菌菌株(Bacillus chitinosporus strain)CM-1+TX、角质孢子芽孢杆菌菌株(Bacillus chitinosporus strain AQ746+TX、地衣芽孢杆菌菌株HB-2(BiostartTM )+TX、地衣芽孢杆菌菌株3086(+TX、Green)+TX、环状芽孢杆菌+TX、坚强芽孢杆菌(+TX、+TX、)+TX、坚强芽孢杆菌菌株I-1582+TX、软化芽孢杆菌(Bacillus macerans)+TX、死海芽孢杆菌(Bacillus marismortui)+TX、巨大芽孢杆菌+TX、蕈状芽孢杆菌菌株AQ726+TX、乳头状芽孢杆菌(Bacillus papillae)(Milky Spore)+Tx、短小芽孢杆菌物种+TX、短小芽孢杆菌菌株GB34(Yield)+TX、短小芽孢杆菌菌株AQ717+TX、短小芽孢杆菌菌株QST2808(+TX、Ballad)+TX、球形芽孢杆菌(Bacillus sphaericus)+Tx、芽孢杆菌属物种+Tx、芽孢杆菌属物种菌株AQ175+TX、芽孢杆菌属物种菌株AQ177+TX、芽孢杆菌属物种菌株AQ178+TX、枯草芽孢杆菌菌株QST713(+TX、+TX、)+TX、枯草芽孢杆菌菌株QST 714+TX、枯草芽孢杆菌菌株AQ153+TX、枯草芽孢杆菌属菌株AQ743+TX、枯草芽孢杆菌菌株QST3002+TX、枯草芽孢杆菌菌株QST3004+TX、枯草芽孢杆菌变种解淀粉芽孢杆菌菌株FZB24(+TX、)+TX、苏云金芽孢杆菌Cry 2Ae+TX、苏云金芽孢杆菌Cry1Ab+TX、苏云金芽孢杆菌鲇泽变种(Bacillus thuringiensis aizawai)GC91+TX、苏云金芽孢杆菌以色列亚种(+TX、+TX、)+TX、苏云金芽孢杆菌库斯塔克亚种(+TX、+TX、+TX、+TX、Scutella+TX、Turilav+TX、+TX、Dipel+TX、+TX、)+TX、苏云金芽孢杆菌库斯塔克亚种BMP 123+TX、苏云金芽孢杆菌库斯塔克亚种HD-1+TX、苏云金芽孢杆菌菌株BD#32+TX、苏云金芽孢杆菌菌株AQ52+TX、苏云金芽孢杆菌鲇泽变种(+TX、)+Tx、细菌物种(+TX、+TX、)+TX、Clavipacter michiganensis噬菌体+TX、+TX、球孢白僵菌(+TX、Brocaril)+TX、球孢白僵菌GHA(Mycotrol+TX、Mycotrol+TX、)+TX、布氏白僵菌(+TX、Schweizer+TX、)+Tx、白僵菌属物种+TX、灰葡萄孢菌+TX、慢生型大豆根瘤菌+TX、短短芽孢杆菌+TX、苏云金芽孢杆菌拟布甲亚种(Bacillus thuringiensis tenebrionis)+TX、BtBooster+TX、洋葱伯克霍尔德菌(+TX、+TX、Blue)+TX、Burkholderia gladii+TX、唐菖蒲伯克霍尔德菌+Tx、伯克霍尔德菌属物种+TX、加拿大蓟真菌(Canadian thistlefungus)(CBH Canadian)+TX、乳酪假丝酵母+TX、无名假丝酵母+TX、Candidafructus+TX、光滑假丝酵母+TX、高里假丝酵母+TX、口津假丝酵母+TX、橄榄假丝酵母菌株O+TX、近平滑假丝酵母+TX、菌膜假丝酵母+TX、铁红假丝酵母+TX、瑞氏假丝酵母(Candidareukaufii)+TX、水解假丝酵母(Candida saitoana)(+TX、)+TX、清酒假丝酵母+TX、假丝酵母属物种+TX、Candida tenius+TX、Cedecea dravisae+TX、产黄纤维单胞菌+TX、螺卷毛壳+TX、球毛壳菌+TX、Chromobacteriumsubtsugae菌株PRAA4-1T+TX、枝孢样枝孢霉+TX、孢枝孢菌+TX、Cladosporiumchlorocephalum+TX、分支孢子菌属物种+TX、极细分支孢子菌(Cladosporiumtenuissimum)+TX、粉红粘帚霉+TX、炭疽菌+TX、盾壳霉(Cotans)+TX、盾壳霉属物种+TX、浅白隐球酵母+TX、土生隐球菌+TX、Cryptococcusinfirmo-miniatus+TX、罗伦隐球酵母+TX、Cryptophlebia leucotreta granulovirus+TX、Cupriavidus campinensis+TX、苹果蠹蛾颗粒体病毒+TX、苹果蠹蛾颗粒体病毒(+TX、Madex+TX、Madex Max/)+TX、Cylindrobasidium laeve+TX、枝双孢霉属(Cylindrocladium)+TX、Drechslera hawaiinensis+TX、阴沟肠杆菌+TX、肠杆菌科+TX、毒力虫霉+TX、黑附球菌(Epicoccum nigrum)+TX、黑附球菌(Epicoccum purpurascens)+TX、附球菌属+TX、花状线黑粉菌(Filobasidium floriforme)+TX、锐顶镰孢菌+TX、厚垣镰孢霉+TX、尖镰孢(/Biofox)+TX、层生镰孢+TX、镰孢属+TX、溶磷白地霉(Galactomycesgeotrichum)+TX、链孢粘帚霉(+TX、)+TX、粉红粘帚霉+TX、粘帚霉属+TX、绿色粘帚霉+TX、颗粒体病毒属+TX、嗜盐盐芽孢杆菌(Halobacillus halophilus)+TX、沿岸盐芽孢杆菌(Halobacillus litoralis)+TX、特氏盐芽孢杆菌(Halobacillus trueperi)+TX、盐单胞菌属+TX、冰下盐单胞菌(Halomonas subglaciescola)+TX、盐弧菌变型(Halovibrio variabilis)+TX、葡萄汁有孢汉逊酵母+TX、棉铃虫核型多角体病毒+TX、玉米穗虫核型多角体病毒+TX、异黄酮-芒柄花黄素+TX、柠檬克勒克酵母+TX、克勒克酵母属+TX、大链壶菌(Lagenidium giganteum)+TX、长孢蜡蚧菌(Lecanicilliumlongisporum)+TX、蜡蚧轮枝菌(Lecanicillium muscarium)+TX、舞毒蛾核多角体病毒+TX、嗜盐海球菌+TX、格氏梅拉菌(Meirageulakonigii)+TX、绿僵菌+TX、绿僵菌(Destruxin)+TX、Metschnikowiafruticola+TX、美极梅奇酵母(Metschnikowia pulcherrima)+TX、Microdochium dimerum+TX、蓝色小单孢菌(Micromonospora coerulea)+TX、Microsphaeropsis ochracea+TX、Muscodor albus 620+TX、Muscodorroseus菌株A3-5+TX、菌根属(Mycorrhizae spp.)(+TX、Root)+TX、疣孢漆斑菌菌株AARC-0255+TX、BROS+TX、Ophiostoma piliferum菌株D97+TX、粉质拟青霉(Paecilomyces farinosus)+TX、玫烟色拟青霉(+TX、)+TX、淡紫拟青霉(Paecilomyces linacinus)(Biostat)+TX、淡紫拟青霉菌株251(MeloCon)+TX、多粘类芽孢杆菌+TX、成团泛菌(BlightBan)+TX、泛菌属+TX、巴斯德氏芽菌属+TX、Pasteuria nishizawae+TX、黄灰青霉+TX、Penicillium billai(+TX、)+TX、短密青霉+TX、常现青霉+TX、灰黄青霉+TX、产紫青霉+TX、青霉菌属+TX、纯绿色肯霉+TX、大伏革菌(Phlebiopsisgigantean)+TX、解磷细菌+TX、隐地疫霉+TX、棕榈疫霉+TX、异常毕赤酵母+TX、Pichia guilermondii+TX、膜醭毕赤氏酵母+TX、指甲毕赤酵母+TX、树干毕赤酵母+TX、铜绿假单胞菌+TX、致金色假单胞菌(Pseudomonasaureofasciens)(Spot-Less)+TX、洋葱假单胞菌+TX、绿针假单胞菌+TX、皱褶假单胞菌(Pseudomonas corrugate)+TX、荧光假单胞菌菌株A506(BlightBan)+TX、恶臭假单胞菌+TX、Pseudomonas reactans+TX、假单胞菌属+TX、丁香假单胞菌+TX、绿黄假单胞菌+TX、荧光假单胞菌+TX、Pseudozyma flocculosa菌株PF-A22UL(Sporodex)+TX、纵沟柄锈菌(Pucciniacanaliculata)+TX、Puccinia thlaspeos(Wood)+TX、侧雄腐霉菌(Pythiumparoecandrum)+TX、寡雄腐霉(+TX、)+TX、缠器腐霉+TX、水生拉恩菌(Rhanella aquatilis)+TX、拉恩菌属+TX、根瘤菌(+TX、)+TX、丝核菌属+TX、球状红球菌菌株AQ719+TX、双倒卵形红冬孢酵母菌(Rhodosporidiumdiobovatum)+TX、圆红冬孢酵母菌+TX、红酵母属+TX、粘红酵母+TX、禾本红酵母+TX、胶红酵母(Rhodotorula mucilagnosa)+TX、深红酵母+TX、酿酒酵母+TX、玫瑰色盐水球菌(Salinococcus roseus)+TX、小核盘菌+TX、小核盘菌+TX、柱顶孢霉属+TX、Scytalidium uredinicola+TX、甜菜夜蛾核型多角体病毒(+TX、)+TX、粘质沙雷氏菌+TX、普城沙雷菌+TX、沙雷氏菌属+TX、粪生粪壳菌+TX、海灰翅夜蛾核型多角体病毒+TX、红掷孢酵母+TX、嗜麦芽寡养单胞菌+TX、不吸水链霉菌+TX、白丘链霉菌(Streptomyces albaduncus)+TX、脱叶链霉菌+TX、鲜黄链霉菌+TX、灰平链霉菌+TX、灰绿链霉菌+TX、利迪链霉菌+TX、利迪链霉菌WYEC-108+TX、紫色链霉菌+TX、小铁艾酵母(Tilletiopsis minor)+TX、铁艾酵母属+TX、棘孢木霉(T34)+TX、盖姆斯木霉(Trichoderma gamsii)+TX、深绿木霉+TX、钩状木霉TH 382+TX、里法哈茨木霉(Trichoderma harzianumrifai)+TX、哈茨木霉T-22(+TX、PlantShield+TX、+TX、)+TX、哈茨木霉T-39+TX、非钩木霉(Trichoderma inhamatum)+TX、康宁木霉+TX、木霉属LC 52+TX、木素木霉+TX、长柄木霉+TX、多孢木霉(Trichoderma polysporum)(Binab)+TX、紫杉木霉+TX、绿色木霉+TX、绿色木霉(原来称为绿色粘帚霉GL-21)+TX、绿色木霉+TX、绿色木霉菌株ICC 080+TX、茁芽丝孢酵母+TX、毛孢子菌属+TX、单端孢属+TX、粉红单端孢+TX、Typhula phacorrhiza菌株94670+TX、Typhula phacorrhiza菌株94671+TX、黑细基格孢+TX、奥德曼细基格孢(Ulocladium oudemansii)+TX、玉蜀黍黑粉菌+TX、各种细菌和补充营养素(Natural)+TX、各种真菌(Millennium)+TX、厚垣轮枝孢菌+TX、蜡蚧轮枝菌(+TX、)+TX、Vip3Aa20+TX、Virgibaclillus marismortui+TX、野油菜黄单胞菌(Xanthomonas campestris pv.Poae)+TX、伯氏致病杆菌(Xenorhabdus bovienii)+TX、嗜线虫致病杆菌(Xenorhabdus nematophilus);以及
植物提取物,包括:松油+TX、印楝素(Plasma Neem+TX、+TX、+TX、+TX、植物IGR(+TX、)+TX、菜籽油(Lilly Miller)+TX、土荆芥附近荆芥(Chenopodium ambrosioidesnear ambrosioides)+TX、菊花浓汁(Chrysanthemum extract)+TX、提取印楝油(extract of neem oil)+TX、唇形科的精油+TX、丁香迷迭香薄荷的提取物和百里香精油(Garden insect)+TX、甜菜碱+TX、大蒜+TX、柠檬草精油+TX、印度楝树精油+TX、猫薄荷(薄荷精油)+TX、荆芥卡塔琳娜州(Nepeta catarina)+TX、尼古丁+TX、牛至精油+TX、胡麻科精油+TX、除虫菊+TX、皂皮树+TX、大虎杖(Reynoutriasachalinensis)(+TX、)+TX、鱼藤酮(Eco)+TX、芸香料植物提取物+TX、豆油(Ortho)+TX、茶树精油(Timorex)+TX、百里香精油+TX、MMF+TX、+TX、迷迭香芝麻薄荷百里香和肉桂提取物的混合物(EF)+TX、丁香迷迭香和薄荷提取物的混合物(EF)+TX、丁香薄荷大蒜油和薄菏的混合物(Soil)+TX、高岭土+TX、储存葡萄糖的褐藻以及
信息素,包括:黑头火虫信息素(3M Sprayable Blackheaded Fireworm)+TX、鳕鱼蛾信息素(Codling Moth Pheromone)(派拉蒙分配器(Paramountdispenser)-(CM)/Isomate)+TX、葡萄莓果蛾信息素(Grape Berry MothPheromone)(3M MEC-GBM Sprayable)+TX、稻纵卷叶螟性信息素(Leafrollerpheromone)(3M MEC-LR Sprayable)+TX、家蝇信息素(Muscamone)(Snip7Fly+TX、Starbar Premium Fly)+TX、东方水果蛾信息素(Oriental Fruit MothPheromone)(3M oriental fruit moth sprayable)+TX、桃树钻信息素(Peachtree Borer Pheromone)+TX、番茄蛾类信息素(Tomato PinwormPheromone)(3M Sprayable)+TX、衣透斯特粉末(Entostat powder)(从棕榈树提取)(Exosex)+TX、(E+TX、Z+TX、Z)-3+TX、8+TX、11醋酸十四酯+TX、(Z+TX,Z+TX,E)-7+TX、11+TX、13-十六碳三烯醛+TX、(E+TX,Z)-7+TX、9-十二碳二烯-1-基乙酸酯+TX、2-甲基-1-丁醇+TX、乙酸钙+TX、+TX、+TX、+TX、紫杉醇;以及
宏生物剂,包括:短距蚜小蜂(Aphelinus abdominalis)+TX、阿尔蚜茧蜂(Aphidius ervi)+TX、Acerophagus papaya+TX、二星瓢虫(Adaliabipunctata)+TX、二星瓢虫+TX、二星瓢虫(Adaliabipunctata)+TX、串茧跳小蜂(Ageniaspis citricola)+TX、巢蛾多胚跳小蜂(Ageniaspisfuscicollis)+TX、安氏钝绥螨(Amblyseius andersoni)(+TX、Andersoni-)+TX、加州钝绥螨(Amblyseius californicus)(+TX、)+TX、胡瓜钝绥螨(Amblyseius cucumeris)(+TX、Bugline)+TX、伪钝绥螨(Amblyseius fallacis)+TX、斯氏钝绥螨(Amblyseius swirskii)(Bugline+TX、)+TX、奥氏钝绥螨(Amblyseius womersleyi)+TX、粉虱细蜂(Amitus hesperidum)+TX、原缨翅缨小蜂(Anagrus atomus)+TX、暗腹长索跳小蜂(Anagyrus fusciventris)+TX、卡玛长索跳小蜂(Anagyrus kamali)+TX、Anagyrus loecki+TX、粉蚧长索跳小蜂(Anagyrus pseudococci)+TX、红蜡蚧扁角跳小蜂(Anicetus benefices)+TX、金小蜂(Anisopteromalus calandrae)+TX、林地花蝽(Anthocoris nemoralis)+TX、短距蚜小蜂(Aphelinusabdominalis)(+TX、)+TX、短翅蚜小蜂(Aphelinus asychis)+TX、科列马阿布拉小蜂(Aphidius colemani)+TX、阿尔蚜茧蜂(Aphidius ervi)+TX、烟蚜茧蜂(Aphidius gifuensis)+TX、桃赤蚜蚜茧蜂(Aphidiusmatricariae)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)+TX、食蚜瘿蚊+TX、岭南蚜小蜂(Aphytis lingnanensis)+TX、印巴黄金蚜小蜂(Aphytis melinus)+TX、蠊卵长尾啮小蜂(Aprostocetus hagenowii)+TX、隐翅虫(Atheta coriaria)+TX、熊蜂属(Bombus spp.)+TX、欧洲熊蜂(Bombusterrestris)(Natupol)+TX、欧洲熊蜂(+TX、)+TX、Cephalonomia stephanoderis+TX、黑背红瓢虫(Chilocorus nigritus)+TX、普通草蛉(Chrysoperla carnea)+TX、普通草蛉(Chrysoperla carnea)+TX、红通草蛉(Chrysoperla rufilabris)+TX、Cirrospilus ingenuus+TX、Cirrospilus quadristriatus+TX、白星橘啮小蜂(Citrostichus phyllocnistoides)+TX、Closterocerus chamaeleon+TX、Closterocerus属+TX、Coccidoxenoides perminutus+TX、Coccophagus cowperi+TX、赖食蚧蚜小蜂(Coccophagus lycimnia)+TX、螟黄足盘绒茧蜂(Cotesia flavipes)+TX、菜蛾盘绒茧蜂(Cotesia plutellae)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(+TX、)+TX、日本方头甲(Cybocephalus nipponicus)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)+TX、豌豆潜蝇姬小蜂(Diglyphus isaea)+TX、小黑瓢虫(Delphastus catalinae)+TX、Delphastuspusillus+TX、Diachasmimorpha krausii+TX、长尾潜蝇茧蜂(Diachasmimorphalongicaudata)+TX、Diaparsis jucunda+TX、阿里食虱跳小蜂(Diaphorencyrtusaligarhensis)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)(+TX、)+TX、西伯利亚离颚茧蜂(Dacnusasibirica)(+TX、)+TX、歧脉跳小蜂属(Diversinervus spp.)+TX、盾蚧长缨蚜小蜂(Encarsia citrina)+TX、丽蚜小蜂(Encarsia formosa)(Encarsia+TX、+TX、)+TX、浆角蚜小蜂(Eretmocerus eremicus)+TX、哥德恩蚜小蜂(Encarsia guadeloupae)+TX、海地恩蚜小蜂(Encarsia haitiensis)+TX、细扁食蚜蝇(Episyrphus balteatus)+TX、Eretmoceris siphonini+TX、浆角蚜小蜂(Eretmocerus californicus)+TX、浆角蚜小蜂(Eretmocerus eremicus)(+TX、Eretline)+TX、浆角蚜小蜂(Eretmocerus eremicus)+TX、海氏桨角蚜小蜂(Eretmocerus hayati)+TX、蒙氏桨角蚜小蜂(Eretmocerus mundus)(+TX、Eretline)+TX、Eretmocerus siphonini+TX、四斑光缘瓢虫(Exochomusquadripustulatus)+TX、食螨瘿蚊(Feltiella acarisuga)+TX、食螨瘿蚊(Feltiella acarisuga)+TX、阿里山潜蝇茧蜂(Fopius arisanus)+TX、Fopiusceratitivorus+TX、芒柄花黄素(Formononetin)(Wirless)+TX、细腰凶蓟马(Franklinothrips vespiformis)+TX、西方静走螨(Galendromusoccidentalis)+TX、莱氏棱角肿腿蜂(Goniozus legneri)+TX、麦蛾柔茧蜂(Habrobraconhebetor)+TX、异色瓢虫(Harmonia axyridis)+TX、异小杆线虫属(Heterorhabditis spp.)(Lawn)+TX、嗜菌异小杆线虫(Heterorhabditisbacteriophora)(NemaShield+TX、+TX、+TX、+TX、+TX、+TX、+TX、)+TX、大异小杆线虫(Heterorhabditis megidis)(Nemasys+TX、BioNem+TX、Exhibitline+TX、)+TX、集栖瓢虫(Hippodamia convergens)+TX、尖狭下盾螨(Hypoaspis aculeifer)(+TX、)+TX、兵下盾螨(Hypoaspis miles)(Hypoline+TX、)+TX、黑色枝跗瘿蜂(Lbalialeucospoides)+TX、Lecanoideus floccissimus+TX、Lemophagus errabundus+TX、三色丽突跳小蜂(Leptomastidea abnormis)+TX、Leptomastix dactylopii+TX、长角跳小蜂(Leptomastix epona)+TX、Lindorus lophanthae+TX、Lipolexis oregmae+TX、叉叶绿蝇(Lucilia caesar)+TX、茶足柄瘤蚜茧蜂(Lysiphlebus testaceipes)+TX、暗黑长脊盲蝽(Macrolophus caliginosus)(+TX、Macroline+TX、)+TX、Mesoseiulus longipes+TX、黄色阔柄跳小蜂(Metaphycus flavus)+TX、Metaphycus lounsburyi+TX、角纹脉褐蛉(Micromus angulatus)+TX、黄色花翅跳小蜂(Microterys flavus)+TX、Muscidifurax raptorellus和Spalangiacameroni+TX、Neodryinus typhlocybae+TX、加州新小绥螨(Neoseiuluscalifornicus)+TX、瓜钝绥螨(Neoseiulus cucumeris)+TX、虚伪新小绥螨(Neoseiulus fallacis)+TX、Nesideocoris tenuis(+TX、)+TX、古铜黑蝇(Ophyra aenescens)+TX、狡小花蝽(Orius insidiosus)(+TX、Oriline)+TX、无毛小花蝽(Orius laevigatus)(+TX、Oriline)+TX、大型小花蝽(Orius majusculus)(Oriline)+TX、小黑花椿象(Orius strigicollis) +TX、Pauesia juniperorum+TX、酸酱瓢虫腹柄姬小蜂(Pediobiusfoveolatus)+TX、Phasmarhabditis hermaphrodita+TX、Phymastichuscoffea+TX、Phytoseiulus macropilus+TX、智利小植绥螨(Phytoseiulus persimilis)(+TX、Phytoline)+TX、斑腹刺益蝽(Podisus maculiventris)+TX、Pseudacteon curvatus+TX、Pseudacteon obtusus+TX、Pseudacteon tricuspis+TX、Pseudaphycus maculipennis+TX、Pseudleptomastix mexicana+TX、具毛嗜木虱跳小蜂(Psyllaephagus pilosus)+TX、同色短背茧蜂(Psyttalia concolor)(complex)+TX、胯姬小蜂属(Quadrastichus spp.)+TX、Rhyzobius lophanthae+TX、澳洲瓢虫(Rodoliacardinalis)+TX、Rumina decollate+TX、Semielacher petiolatus+TX、麦长管蚜(Sitobion avenae)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(Nematac+TX、+TX、BioNem+TX、+TX、+TX、)+TX、夜蛾斯氏线虫(+TX、Nemasys+TX、BioNem+TX、+TX、+TX、+TX、Exhibitline+TX、+TX、)+TX、锯蜂线虫(Steinernema kraussei)(Nemasys+TX、BioNem+TX、 )+TX、里奥布拉夫线虫(Steinernema riobrave)(+TX、)+TX、蝼蛄斯氏线虫(Steinernema scapterisci)(Nematac)+TX、斯氏线虫属(Steinernema spp.)+TX、Steinernematid属(Guardian)+TX、深点食螨瓢虫(Stethorus punctillum)+TX、亮腹釉小蜂(Tamarixiaradiate)+TX、Tetrastichus setifer+TX、Thripobius semiluteus+TX、中华长尾小蜂(Torymus sinensis)+TX、甘蓝夜蛾赤眼蜂(Trichogramma brassicae)(Tricholine)+TX、甘蓝夜蛾赤眼蜂(Trichogramma brassicae)+TX、广赤眼蜂(Trichogramma evanescens)+TX、微小赤眼蜂(Trichogramma minutum)+TX、玉米螟赤眼蜂(Trichogramma ostriniae)+TX、宽脉赤眼蜂(Trichogramma platneri)+TX、短管赤眼蜂(Trichogramma pretiosum)+TX、螟黑点瘤姬蜂(Xanthopimpla stemmator);以及
其他生物剂,包括:脱落酸+TX、+TX、银叶菌(Chondrostereumpurpureum)(Chontrol)+TX、盘长孢状刺盘孢+TX、辛酸铜盐+TX、δ陷阱(Delta trap)(Trapline)+TX、解淀粉欧文氏菌(+TX、Ni-HIBIT Gold)+TX、磷酸高铁+TX、漏斗陷阱(Trapline)+TX、+TX、Grower's+TX、高油菜素内酯+TX、磷酸铁(Lilly Miller Worry FreeFerramol Slug&Snail)+TX、MCP冰雹陷阱(Trapline)+TX、Microctonushyperodae+TX、Mycoleptodiscus terrestris+TX、+TX、+TX、+TX、信息素陷阱(Thripline)+TX、碳酸氢钾+TX、脂肪酸的钾盐+TX、硅酸钾溶液 +TX、碘化钾+硫氰酸钾+TX、+TX、蜘蛛毒+TX、蝗虫微孢子虫(Semaspore OrganicGrasshopper)+TX、粘着陷阱(Trapline+TX、Rebell)+TX以及陷阱(Takitrapline y+)+TX。
在活性成分之后的括号中的参考例如[3878-19-1]是指化学文摘登记号。以上描述的混合配对物是已知的。当活性成分包括在以下文献中时:"The Pesticide Manual"[The Pesticide Manual-A World Compendium;Thirteenth Edition;Editor:C.D.S.TomLin;The British Crop Protection Council][“杀有害生物剂手册”[杀有害生物剂手册-一本世界手册;第十三版;编者:C.D.S.TomLin;英国农作物保护委员会]],它们在上文对于特定化合物在圆括号内给定的条目编号之下描述于该手册中;例如,化合物“阿巴美丁”在条目编号(1)之下进行了描述。其中“[CCN]”是对于上文的特定化合物来加上的,所述的化合物包括在“Compendium of Pesticide Common Names[农药通用名概要]”中,它们可以在国际互联网[A.Wood;Compendium of Pesticide Common Names,1995-2004]中查到;例如,化合物“乙酰虫腈”描述于国际互联网地址http://www.alanwood.net/pesticides/acetoprole.html。
上述活性成分中大部分在上文是通过所谓的“通用名”、相关的“ISO通用名”或在个别情况下使用的另一个“通用名”来提及。若其名称不是“通用名”,则所使用的名称种类以特定化合物的圆括号中所给出的名称来代替;在该情形下,使用IUPAC名称、IUPAC/化学文摘名、“化学名称”、“传统名称”、“化合物名”或“研究代码”,或若既不使用上述名称也不使用“通用名”,则使用别名。“CAS登记号”意指化学文摘登记号。
选自表1或表2(如下)所述的化合物1.a.1-1.a.300至1.t.1-1.t.300的具有式(I)的化合物与上述活性成分的活性成分混合物优选地是处于从100:1至1:6000的混合比率,尤其是从50:1至1:50,更尤其是处于从20:1至1:20的比率,甚至更尤其从10:1至1:10,非常尤其是从5:1和1:5,尤其优选的是从2:1至1:2的比率给出的,并且从4:1至2:1的比率同样是优选的,特别是处于1:1,或5:1,或5:2,或5:3,或5:4,或4:1,或4:2,或4:3,或3:1,或3:2,或2:1,或1:5,或2:5,或3:5,或4:5,或1:4,或2:4,或3:4,或1:3,或2:3,或1:2,或1:600,或1:300,或1:150,或1:35,或2:35,或4:35,或1:75,或2:75,或4:75,或1:6000,或1:3000,或1:1500,或1:350,或2:350,或4:350,或1:750,或2:750,或4:750的比率。那些混合比率是按重量计的。
如上描述的混合物可以被用于控制有害生物的方法中,该方法包括将含如上描述的混合物的组合物施用于有害生物或其环境中,通过手术或疗法用于处理人或动物体的方法以及在人或动物体上实施的诊断方法除外。
包含选自表1或表2(如下)所述的化合物1.a.1-1.a.300至1.t.1-1.t.300中的一个的具有式(I)的化合物以及一种或多种如上所述的活性成分的混合物可以例如以一种单一的“掺水即用”的形式施用,以组合的喷洒混合物(该混合物由这些单一活性成分的单独配制品构成)(例如一种“桶混制剂”)施用,并且当以一种顺序的方式(即,一个在另一个适度短的时期之后,例如几小时或几天)施用时组合使用这些单独活性成分来施用。施用选自表1或表2(如下)所述的化合物1.a.1-1.a.300至1.t.1-1.t.300的具有式(I)的化合物和如上所述的一种或多种活性成分的顺序对于实施本发明并不是至关重要的。
根据本发明的组合物还可以包含其他固体或液体助剂,诸如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅酮油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂的存在下,例如通过紧密混合活性成分与一种或多种助剂和/或将活性成分与一种或多种助剂一起研磨来制备。用于制备组合物的这些方法和用于制备这些组合物的化合物(I)的用途也是本发明的主题。
本发明的另一方面涉及具有式(I)的化合物的、或优选的如以上定义的单独的化合物的、包括至少一种具有式(I)的化合物或至少一种优选的如以上定义的单独的化合物的组合物的、或包括至少一种具有式(I)的化合物或至少一种优选的如以上定义的单独的化合物的如以上定义与其他杀真菌剂或杀昆虫剂混合的杀真菌或杀昆虫混合物的用途,用于控制或防止植物(例如有用植物(例如作物))、它们的繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料免于被昆虫或致植物病微生物(优选是真菌有机体)侵染。
本发明的另一方面涉及控制或防止植物(例如有用植物(例如作物))、它们的繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料免于被昆虫或致植物病的或腐败微生物或对人潜在有害的有机体(尤其是真菌有机体)侵染的方法,该方法包括将具有式(I)的化合物或优选的如以上定义的单独的化合物作为活性成分施用至这些植物、植物的各部分或至其底部、它们的繁殖材料、或非生命材料的任何部分。
控制或防止是指将被昆虫或致植物病的或腐败微生物或对人潜在有害的有机体(尤其是真菌有机体)的侵染减少至这样一个被证明改进的水平。
控制或防止作物被致植物病微生物(尤其是真菌)或昆虫侵染的优选的方法是叶面施用,该方法包括施用具有式(I)的化合物、或含有至少一种所述化合物的农用化学组合物。施用频率和施用比率将取决于受相应的病原体或昆虫侵染的风险。然而,具有式(I)的化合物还可以通过用一种液体配制品浸泡该植物的底部或者通过将处于固体形式的化合物例如以颗粒的形式(土壤施用)施用到土壤而经由土壤通过根(内吸作用)渗透该植物。在水稻作物中,可以将此种颗粒施用到灌水的稻田中。具有式(I)的化合物还可以通过用一种杀真菌剂的液体配制品浸渍种子或块茎、或用一种固体配制品对其进行涂覆而施用到种子(涂层)上。
一种配制品,例如一种包含具有式(I)的化合物、以及(如果希望的话)一种固体或液体佐剂或用于封装具有式(I)的化合物的单体的组合物,可以按已知方式,典型地通过将该化合物与增充剂(例如溶剂、固体载体以及,任选地表面活性化合物(表面活性剂))进行密切地混合和/或研磨来进行制备。
有利的施用比率通常是从5g至2kg的活性成分(a.i.)/公顷(ha),优选地从10g至1kg a.i./ha,最优选地从20g至600g a.i./ha。当作为种子浸泡试剂使用时,适宜的剂量是从10mg至1g活性物质/kg种子。
当本发明所述的组合用于处理种子时,比率为0.001g至50g具有式(I)的化合物/kg种子、优选从0.01g至10g/kg种子,这一般是足够的。
本发明的组合物能以任何常规形式使用,例如,以双包装、干种子处理用的粉剂(DS)、种子处理用的乳液(ES)、种子处理用的可流动性浓缩物(FS)、种子处理用的溶液(LS)、种子处理用的水分散性粉剂(WS)、种子处理用的胶囊悬浮液(CF)、种子处理用的凝胶(GF)、乳液浓缩物(EC)、悬浮浓缩物(SC)、悬浮乳液(SE)、胶囊悬浮液(CS)、水分散性粒剂(WG)、可乳化性粒剂(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、分散性油悬剂(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩物(SL)、超低容量悬浮液(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩物(DC)、可湿性粉剂(WP)或与农业上可接受的佐剂组合的任何技术上可行的配制品的形式。
能以常规方式生产这样的组合物,例如通过混合活性成分与适当的配制惰性剂(稀释剂、溶剂、填充剂及任选地其他配制成分,例如表面活性剂、杀生物剂、防冻剂、黏着剂、增稠剂及提供辅佐效果的化合物)。还可以使用意欲长期持续药效的常规缓释配制品。特别地,有待以喷雾形式(如水分散性浓缩物(例如EC、SC、DC、OD、SE、EW、EO等)、可湿性粉剂及颗粒)施用的配制品可以含有表面活性剂(如湿润剂和分散剂)及提供辅佐效果的其他化合物,例如甲醛与萘磺酸盐、烷基芳基磺酸盐、木质素磺酸盐、脂肪烷基硫酸盐及乙氧基化烷基酚和乙氧基化脂肪醇的缩合产物。
使用本发明的组合及稀释剂,以适合的拌种配制品形式,例如具有对种子的良好粘着性的水性悬浮液或干粉剂形式,用自身已知的方式将拌种配制品施用至种子。在本领域这样的拌种配制品是已知的。这样的拌种配制品可以包含封胶形式的单一活性成分或活性成分的组合,例如为缓释胶囊或微胶囊。
通常,配制品包括按重量计从0.01%至90%的活性成分,从0至20%的农业上可接受的表面活性剂及10%至99.99%的固体或液体配制惰性剂和一种或多种辅助剂,该活性剂是由至少具有式(I)的化合物与组分(B)和(C)一起,以及任选地其他活性剂(特别是杀微生物剂或防腐剂或类似物)组成的。按重量计,组合物的浓缩形式通常包含在约2%与80%之间,优选在约5%与70%之间的活性剂。按重量计,配制品的施用形式可以例如包含从0.01%至20%,优选从0.01%至5%的活性剂。而商用的产品将优选地被配制为浓缩物,该最终使用者将通常使用稀释的配制品。
接下来的实例用来阐明本发明。本发明的化合物与已知的化合物的区别可以在于在低施用率下更大的疗效,这可以由本领域的普通技术人员使用在实例中概述的实验程序,使用更低的施用率(如果必要的话)例如,50ppm、12.5ppm、6ppm、3ppm、1.5ppm、0.8ppm、0.2ppm来证实。
具有式(I)的化合物可以具有任何数量的益处,尤其包括针对保护植物对抗由真菌引起的疾病的有利水平的生物活性或对于用作农用化学品活性成分的优越特性(例如,更高的生物活性、有利的活性谱、增加的安全性(包括改善的作物耐受性)、改进的物理-化学特性、或增加的生物可降解性)。
实例
实例1:本实例说明N-[4-(环己氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺(化合物I.b.66)的制备。
a)3-羟基-4-甲氧基-吡啶-2-甲酸甲酯的制备
将浓硫酸(1.4ml,27mmol)逐滴添加至在375ml甲醇中的3-羟基-4-甲氧基-吡啶-2-甲酸(15g,89mmol)的悬浮液中。将反应混合物加热回流16小时(h),然后再添加1.4ml的浓硫酸。将反应混合物再加热24h后,再添加1.4ml的浓硫酸。将反应混合物再加热24h后,将混合物冷却至室温。在减压下除去溶剂并将残余物吸收在水中。通过添加碳酸氢钠使该水相达到pH8,并且然后用乙酸乙酯萃取。将有机层用盐水洗涤,经硫酸钠进行干燥并在减压下蒸发。将剩余物在70ml的己烷中搅拌30分钟(min),过滤并干燥,以给予3-羟基-4-甲氧基-吡啶-2-甲酸甲酯。M.p.157℃-158℃。1H-NMR(400MHz,CDCl3):δ=3.99(s,3H),4.09(s,3H),6.97(d,1H),8.20(d,1H),10.88(bs,1H)。
b)4-甲氧基-3-[(4-甲氧基苯基)甲氧基]吡啶-2-甲酸甲酯的制备
在室温下,将氰化钠(1.8g,47mmol)分批添加至在100ml的N,N-二甲基甲酰胺中的3-羟基-4-甲氧基-吡啶-2-甲酸甲酯(7.1g,39mmol)溶液中。将反应混合物在该温度下搅拌1h,并且然后添加4-甲氧基苄基氯(7.6g,47mmol)。将反应混合物加热至40℃持续16h,然后冷却至室温,倾倒入水中并且用乙酸乙酯萃取。将有机层用盐水洗涤,经硫酸钠进行干燥并在减压下蒸发。将剩余物通过硅胶色谱法,使用乙酸乙酯和庚烷作为洗脱液纯化,以给予4-甲氧基-3-[(4-甲氧基苯基)甲氧基]吡啶-2-甲酸甲酯。1H-NMR(400MHz,CDCl3):δ=3.82(s,3H),3.93(s,3H),3.96(s,3H),5.05(s,2H),6.89(d,2H),6.97(d,1H),7.41(d,2H),8.32(d,1H)。
c)N-[4-(环己氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺(化合物I.b.66)的制备
将三甲基铝(在庚烷中的0.7ml的2M溶液,1.5mmol)缓慢地添加至在10ml的甲苯中的4-甲氧基-3-[(4-甲氧基苯基)甲氧基]吡啶-2-甲酸甲酯(0.3g,1.0mmol)和4-(环己氧基)苯胺(0.2g,1.1mmol)溶液中。将反应混合物在室温下搅拌16h,然后通过添加20ml的2N盐酸酸化并再搅拌30min。通过添加饱和碳酸氢钠水溶液中和后,添加乙酸乙酯并将混合物通过硅藻土过滤。将滤液的各相分离,并且用乙酸乙酯萃取水相。将合并的有机层用盐水洗涤,经硫酸钠进行干燥并在减压下蒸发。将剩余物通过硅胶色谱法,使用乙酸乙酯和庚烷作为洗脱液纯化,以给予N-[4-(环己氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺(化合物I.b.66)。1H-NMR(400MHz,CDCl3):δ=1.32-1.40(m,2H),1.48-1.59(m,4H),1.77-1.84(m,2H),1.96-2.02(m,2H),3.97(s,3H),4.22(q,1H),6.89-6.97(m,3H),7.58(d,2H),8.01(d,1H),9.82(s,1H),12.30(s,1H)。
实例2:本实例说明N-[4-(4,4-二甲基环己氧基)-2-氟-苯基]-1,3-苯并恶唑-7-甲酰胺(化合物I.r.133)的制备。
a)4-(4,4-二甲基环己氧基)-2-氟-1-硝基-苯的制备
将偶氮二甲酸二异丙酯(1.3g,6.1mmol)逐滴添加至在20ml的四氢呋喃中的三苯基膦(1.6g,6.1mmol)、3-氟-4-硝基苯酚(1.0g,6.1mmol)和4.4-二甲基环己醇(0.65g,5.1mmol)的溶液中。将反应混合物在室温下搅拌16h,然后用乙酸乙酯和水稀释。分离各相,将有机层用水洗涤,经硫酸镁进行干燥并在减压下蒸发。将剩余物通过硅胶色谱法,使用乙酸乙酯和庚烷作为洗脱液纯化,以给予4-(4,4-二甲基环己氧基)-2-氟-1-硝基-苯。1H-NMR(400MHz,CDCl3):δ=0.98(s,3H),0.99(s,3H),1.25-1.31(m,2H),1.50-1.56(m,2H),1.69-1.77(m,2H),1.86-1.92(m,2H),4.32(q,1H),6.68-6.75(m,2H),8.07(t,1H)。
b)4-(4,4-二甲基环己氧基)-2-氟-苯胺的制备
将4-(4,4-二甲基环己氧基)-2-氟-1-硝基-苯(0.8g,3.0mmol)溶解在15ml的乙醇中并且在室温下,在氢气和催化剂量的10%钯碳的存在下,搅拌2h。随后将反应混合物通过硅藻土过滤并用乙酸乙酯冲洗。在减压下除去溶剂,以给予4-(4,4-二甲基环己氧基)-2-氟-苯胺。1H-NMR(400MHz,CDCl3):δ=0.94(s,3H),0.98(s,3H),1.20-1.29(m,2H),1.43-1.68(m,4H),1.78-1.89(m,2H),3.43(bs,2H),4.04(q,1H),6.55(dd,1H),6.61-6.71(m,2H)。
c)N-[4-(4,4-二甲基环己氧基)-2-氟-苯基]-1,3-苯并恶唑-7-甲酰胺(化合物I.r.133)的制备
将三乙胺(0.45g,4.5mmol)和1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓-3-氧化六氟磷酸盐(0.51g,1.35mmol)连续地添加至在11ml的乙腈中的1,3-苯并恶唑-7-甲酸(0.15g,0.9mmol)的溶液中。将混合物在室温下搅拌15min并且然后添加4-(4,4-二甲基环己氧基)-2-氟-苯胺(0.21g,0.9mmol)。将反应混合物在室温下搅拌16h并且然后用氯仿稀释。将Isolute添加至混合物中,然后将全部挥发物在减压下除去,将剩余粉末置于色谱柱的顶部上并且通过硅胶色谱法,使用乙酸乙酯和庚烷作为洗脱液纯化,以给予N-[4-(4,4-二甲基环己氧基)-2-氟-苯基]-1,3-苯并恶唑-7-甲酰胺(化合物I.r.133)。1H-NMR(400MHz,CDCl3):δ=0.99(s,3H),1.01(s,3H),1.27-1.35(m,2H),1.52-1.60(m,2H),1.68-1.79(m,2H),1.87-1.96(m,2H),4.25(q,1H),6.79(d,2H),7.59(t,1H),8.04(d,1H),8.28-8.33(m,2H),8.39(t,1H),8.99(bs,1H)。
下表1展示了根据本发明所述的具有式(I)的单独的化合物的实例。
表1:根据本发明所述的具有式(I)的单独的化合物(1.a.1-1.a.300至1.t.1-
1.t.300)。
其中有:
a)具有式(I.a)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
b)具有式(I.b)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的,其条件是具有式1.I.b的化合物不是3-羟基-4-甲氧基-N-[4-(3,3,5,5-四甲基环己氧基)苯基]吡啶-2-甲酰胺。
c)具有式(I.c)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
d)具有式(I.d)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
e)具有式(I.e)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
f)具有式(I.f)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
g)具有式(I.g)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
h)具有式(I.h)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
i)具有式(I.i)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
j)具有式(I.j)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
k)具有式(I.k)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
m)具有式(I.m)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
n)具有式(I.n)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
o)具有式(I.o)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
p)具有式(I.p)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
q)具有式(I.q)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
r)具有式(I.r)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
s)具有式(I.s)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
t)具有式(I.t)的300种化合物:
其中R3、R4、R5、R6、R7和R8是如在表1中所定义的。
贯穿本说明书,以摄氏度(℃)给出温度并且“m.p.”是指熔点。LC/MS是指液相色谱质谱,并且该装置的说明和方法是:(来自沃特斯公司(Waters)的ACQUITY UPLC,Phenomenex Gemini C18,3μm颗粒尺寸,110m,30x 3mm柱,1.7mL/min,60℃,H2O+0.05%HCOOH(95%)/CH3CN/MeOH 4:1+0.04%HCOOH(5%)-2min-CH3CN/MeOH 4:1+0.04%HCOOH(5%)-0.8min,来自沃特斯公司(Waters)的ACQUITY SQD质谱仪,电离方法:电喷射(ESI),极性:正离子,毛细管电压(kV)3.00,锥孔电压(V)20.00,提取器(V)3.00,源温度(℃)150,去溶剂化温度(℃)400,锥孔反吹气流(L/Hr)60,去溶剂化气流(L/Hr)700))。
表2:表1中选定化合物的熔点和LC/MS数据。
配制品实例
将所述活性成分与所述佐剂充分混合并且将混合物在适当的研磨机中充分研磨,从而获得了可以用水稀释而给出所希望的浓度的悬浮液的可湿性粉剂。
将该活性成分与这些佐剂充分混合并且将混合物在适当的研磨机中充分研磨,从而提供可以直接用于种子处理的粉末。
可乳化浓缩剂
在植物保护中可以使用的具有任何所要求的稀释度的乳液可以通过用水稀释从这种浓缩剂获得。
通过将活性成分与载体混合并且将所述混合物在适合的研磨机中研磨而获得即用型尘剂。此类粉剂还可以用于种子的干拌种。
挤出机颗粒剂
将活性成分与所述佐剂混合并且研磨,并且将混合物用水润湿。将混合物挤出并且然后在空气流中干燥。
涂覆的颗粒剂
活性成分[具有式(I)的化合物] 8%
聚乙二醇(mol.wt.200) 3%
高岭土 89%
将该精细研磨的活性成分在一个混合器中均匀地施用到用聚乙二醇湿润的高岭土上。以此方式获得无尘的包衣的颗粒剂。
悬浮液浓缩剂
将精细地研磨的活性成分与佐剂紧密地混合,得到悬浮液浓缩物,从所述悬浮液浓缩物可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、浇注或浸渍进行保护。
种子处理用的可流动性浓缩物
将精细地研磨的活性成分与佐剂紧密地混合,得到悬浮液浓缩物,从所述悬浮液浓缩物可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、浇注或浸渍进行保护。
缓释的胶囊悬浮剂
将28份的具有式(I)的化合物的组合与2份的芳香族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-聚苯基异氰酸酯-混合物(8:1)进行混合。将该混合物在1.2份的聚乙烯醇、0.05份的消泡剂以及51.6份的水的混合物中进行乳化直至达到所希望的颗粒尺寸。向这个乳液中添加在5.3份的水中的2.8份的1,6-二氨基己烷混合物。将该混合物搅拌直至聚合反应完成。
将获得的胶囊悬浮液通过添加0.25份的增稠剂以及3份的分散剂进行稳定。该胶囊悬浮剂配制品包括28%的活性成分。所述介质胶囊的直径是8微米-15微米。
将所得配制品作为适用于此目的装置中的水性悬浮液施用到种子上。
生物学实例
茄链格孢菌/番茄/叶圆片(早枯病)
将番茄叶圆片栽培品种贝蒂(cv.Baby)置于多孔板(24孔格式)的琼脂上,并且用DMSO和Tween20配制的测试化合物进行喷雾并在水中稀释。在施用后2天,用真菌的孢子悬浮液接种这些叶圆片。在气候箱中,在12/12h(照明/黑暗)的光方案下,在23℃/21℃(白天/夜晚)和80%相对湿度(rh)下孵育接种的叶圆片,并且在未处理的对照叶圆片中出现适当水平的疾病损害时(施用后5-7天),作为与未处理的相比时的疾病控制百分比来评估化合物的活性。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.66、I.b.133、1.b.168和I.c.273在200ppm下给出至少80%的疾病控制。
小麦白粉病菌(Blumeria graminis f.sp.tritici)(Erysiphe graminis
f.sp.Tritici)/小麦/叶圆片预防法(小麦上的白粉病)
将小麦叶碎片栽培品种坎斯勒(cv.Kanzler)置于多孔板(24孔格式)的琼脂上,并且用DMSO和Tween20配制的测试化合物进行喷雾,并在水中稀释。在施用后1天,通过在这些测试板之上摇动白粉病感染的植物来接种叶圆片。在气候箱中,在24h黑暗、随后是12h照明/12h黑暗的光方案下,在20℃和60%rh下孵育接种的叶圆片,并且在未处理的对照叶段上出现适当水平的疾病损害时(施用后6-8天),作为与未处理的相比时的疾病控制百分比来评估化合物的活性。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.133、I.b.268、I.c.273和I.b.298在200ppm下给出至少80%的疾病控制。
灰葡萄孢菌(Botryotinia fuckelian,Botrytis cinerea)/液体培养(灰霉病)
将来自冷冻储存的真菌分生孢子直接混入营养肉汤(沃格尔(Vogels)肉汤)中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃进行孵育并且施用之后3-4天通过光度法测定对生长的抑制。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.31、I.b.66、I.b.133、I.b.178、I.b.193、I.b.231、I.b.256、I.b.268、I.b.271、I.b.273、I.b.123、I.c.148、I.b.166、I.b.168、I.b.183、I.b.203、I.b.283、I.b.293和I.b.298在200ppm下给出至少80%的疾病控制。
黄色镰刀菌/液体培养(赤霉病)
将来自低温储存的真菌分生孢子直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃进行孵育并且施用之后3-4天通过光度法测定对生长的抑制。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物1.b.193和I.c.273在200ppm下给出至少80%的疾病控制。
小麦全蚀病菌(Gaeumannomyces graminis)/液体培养(谷类全蚀病)
将来自低温储存的菌丝体片段直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃进行孵育并且施用之后4-5天通过光度法测定对生长的抑制。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.31、I.b.66、I.b.128、I.b.133、I.b.178、I.b.188、I.b.193、I.b.211、I.b.231、I.b.236、I.b.241、I.b.246、I.b.251、I.b.256、I.b.268、I.b.271、I.b.273、I.b.33、I.b.68、I.b.73、I.b.123、I.c.148、I.b.151、I.b.166、I.b.168、I.b.183、I.b.201、I.b.203、I.b.283、I.b.288、I.b.293、I.b.298和I.c.298在200ppm下给出至少80%的疾病控制。
瓜小丛壳菌(Glomerellalagenarium)(瓜类炭疽菌(Colletotrichum
lagenarium))/液体培养(炭疽病)
将来自低温储存的真菌分生孢子直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃孵育并且在施用后3至4天通过光度法测量对生长的抑制。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.31、I.b.66、I.b.128、I.b.133、I.b.178、I.b.193、I.b.231、I.b.241、I.b.246、I.b.251、I.b.256、I.b.268、I.b.271和I.b.273、I.b.68、I.b.123、I.c.148、I.b.151、I.b.166、I.b.168、I.b.183、I.b.203、I.b.283、I.b.288、I.b.293和I.c.298在200ppm下给出至少80%的疾病控制。
稻瘟病菌(Magnaporthe grisea)(稻瘟病(Pyricularia oryzae))/稻/叶圆片预
防(稻瘟病(Rice Blast))
将稻叶段栽培品种宝利拉(cv.Ballila)置于多孔板(24孔格式)的琼脂上,并且用DMSO和Tween20配制的测试化合物进行喷雾,并在水中稀释。在施用后2天之后,用真菌的孢子悬浮液接种这些叶片段。在气候箱中,在24h黑暗、随后是12h光照/12h黑暗的光方案下,在22℃和80%rh下孵育这些接种的叶段,并且在未处理的对照叶圆片中出现适当水平的疾病损害时(施用后5至7天),作为与未处理的相比时的疾病控制百分比来评估化合物的活性。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.268、I.b.273、I.b.168和I.b.298在200ppm下给出至少80%的疾病控制。
雪腐明梭孢(Monographella nivalis)(雪霉叶枯菌(Microdochium nivale))/液
体培养(谷类根腐病)
将来自低温储存的真菌分生孢子直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃进行孵育并且施用之后4-5天通过光度法测定对生长的抑制。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.31、I.b.66、I.b.128、I.b.133、I.b.178、I.b.188、I.b.193、I.b.231、I.b.236、I.b.241、I.b.246、I.b.251、I.b.256、I.b.268、I.b.271、I.b.273、I.b.68、I.b.73、I.b.78、I.b.123、I.c.148、I.b.151、I.b.166、I.b.168、I.b.183、I.b.201、I.b.203、I.b.283、I.b.288、I.b.293、I.b.298和I.c.298在200ppm下给出至少80%的疾病控制。
落花生球腔菌(Mycosphaerella arachidis)(落花生尾孢菌(Cercospora
arachidicola))/液体培养(早期叶斑病)
将来自低温储存的真菌分生孢子直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃孵育并且施用后4-5天通过光度法测定对生长的抑制。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.31、I.b.66、I.b.128、I.b.133、I.b.178、I.b.193、I.b.231、I.b.251、I.b.256、I.b.268、I.b.271、I.b.273、I.b.123、I.c.148、I.b.151、I.b.166、I.b.168、I.b.183、I.b.201、I.b.203、I.b.283、I.b.293、I.b.298和I.c.298在200ppm下给出至少80%的疾病控制。
禾生球腔菌(Mycosphaerella graminicola)(小麦壳针孢(Septoria tritici))/
液体培养(叶枯病(Septoria blotch))
将来自低温储存的真菌分生孢子直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃孵育并且施用后4至5天通过光度法测定对生长的抑制。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.31、I.b.66、I.b.128、I.b.133、I.b.178、I.b.188、I.b.193、I.b.231、I.b.236、I.b.246、I.b.251、I.b.256、I.b.268、I.b.271、I.b.273、I.b.33、I.b.68、I.b.78、I.b.123、I.c.148、I.b.151、I.b.166、I.b.168、I.b.183、I.b.201、I.b.203、I.b.283、I.b.288、I.b.293、I.b.298和I.c.298在200ppm下给出至少80%的疾病控制。
圆核腔菌(Pyrenophora teres)/大麦/叶圆片预防性(网斑病)
将大麦叶段栽培品种哈索(cv.Hasso)置于多孔板(24孔格式)的琼脂上,并且用DMSO和Tween20配制的测试化合物进行喷雾,并在水中稀释。在施用后2天之后,用真菌的孢子悬浮液接种这些叶片段。在气候箱中,在12h照明/12h黑暗的光方案下,在20℃和65%rh下培养这些接种的叶段,并且在未处理的对照叶圆片中出现适当水平的疾病损害时(施用后5至7天),作为与未处理的相比时的疾病控制百分比来评估化合物的活性。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.133、I.b.268、I.b.273、I.b.168、I.c.273和I.c.298在200ppm下给出至少80%的疾病控制。
水稻纹枯病菌(立枯丝核菌)/液体培养(根腐病,猝倒病):
将新培养的液体培养真菌的菌丝体片段直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将试验化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌材料的营养肉汤。将这些测试板在24℃孵育并且施用后3至4天通过光度法测定对生长的抑制。
在这一测试中,当在相同条件下与示出广泛的疾病发展的未处理的对照叶圆片相比时,在配制品中化合物I.b.128、I.b.193和I.b.168在200ppm下给出至少80%的疾病控制。
Claims (15)
1.一种具有式(I)的化合物:
其中,
R1是C1-C6烷氧基或C1-C6酰氨基,其中C1-C6烷氧基和C1-C6酰氨基任选地被R9表示的1至3个基团取代;并且
R2是羟基、C1-C6酰氧基、C1-C6烷氧基C1-C6烷氧基或C1-C6酰氧基C1-C6烷氧基,其中C1-C6酰氧基、C1-C6烷氧基C1-C6烷氧基和C1-C6酰氧基C1-C6烷氧基任选地被R9表示的1至3个基团取代;或者
R1和R2连同它们所附接的碳原子一起形成1,3-噁唑环;
R3是氢、C1-C6烷基、C1-C6烷氧基或C3-C6环烷基;
R4、R5、R6和R7独立地是氢、卤素、C1-C6烷基或C1-C6烷氧基,其中C1-C6烷基和C1-C6烷氧基任选地被R9表示的1至3个基团取代;
R8是C3-C9环烷基,其任选地被R10表示的1至5个基团取代,其中R10独立地选自羟基、卤素、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基,其中C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基任选地被R9表示的1至3个基团取代;或者
R8是C3-C9环烷基,其任选地被R10表示的1或2个基团取代,其中R10独立地选自C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基、杂芳基C1-C6烷基、=O、=C(R11)2、=NOR11或=N-N(R11)2,其中C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基或杂芳基C1-C6烷基任选地被R9表示的1至3个基团取代;或者
R8是C3-C9环烷基,其任选地被R10表示的1个基团取代,其中R10是螺环的3至10元饱和的或部分不饱和的碳环系统或杂环系统,该系统含有1至3个杂原子,所述杂原子选自氧、氮和硫,并且任选地被卤素、C1-C4烷基或=O表示的1至5个基团取代;
R9独立地选自卤素、氰基、C1-C4烷基和C1-C4烷氧基,其中C1-C4烷基和C1-C4烷氧基任选地被卤素表示的1至5个基团取代;
R11是氢、C1-C6烷基、C2-C6烯基、C2-C6炔基或芳基,其中C1-C6烷基、C2-C6烯基、C2-C6炔基和芳基任选地被R9表示的1至3个基团取代;并且
X是CH或N;
或其盐或N-氧化物;
其条件是具有式(I)的化合物不是3-羟基-4-甲氧基-N-[4-(3,3,5,5-四甲基环己氧基)苯基]吡啶-2-甲酰胺。
2.根据权利要求1所述的化合物,其中R1是C1-C4烷氧基并且R2是羟基。
3.根据权利要求1或权利要求2所述的化合物,其中R3是氢。
4.根据权利要求1至3中任一项所述的化合物,其中R4选自卤素、C1-C6烷基或C1-C6烷氧基,其中C1-C6烷基和C1-C6烷氧基任选地被R9表示的1至3个基团取代。
5.根据权利要求1至3中任一项所述的化合物,其中R4是氢、氟、氯并且R5、R6和R7是氢。
6.根据权利要求1至5中任一项所述的化合物,其中R8是C3-C9环烷基,其任选地被R10表示的1至3个基团取代,其中R10独立地选自羟基、卤素、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基;或者
R8是C3-C9环烷基,其任选地被R10表示的1或2个基团取代,其中R10独立地选自C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基、杂芳基C1-C6烷基、=O、=C(R11)2、=NOR11或=N-N(R11)2,其中C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基或杂芳基C1-C6烷基任选地被R9表示的1至3个基团取代;或者
R8是C3-C9环烷基,其任选地被R10表示的1个基团取代,其中R10是螺环的3至10元饱和或部分不饱和的碳环系统或杂环系统,该系统含有1或2个杂原子,所述杂原子选自氧、氮和硫,并且任选地被卤素、C1-C4烷基或=O表示的1至3个基团取代。
7.根据权利要求1至5中任一项所述的化合物,其中,R8是C7-C9环烷基,其任选地被R10表示的1至5个基团取代,其中R10独立地选自羟基、卤素、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基,其中C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、C2-C6烯基、C2-C6炔基或C1-C6烷基羰氧基任选地被R9表示的1至3个基团取代;或者
R8是C3-C9环烷基,其任选地被R10表示的1或2个基团取代,其中R10独立地选自C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基、杂芳基C1-C6烷基、=O、=C(R11)2、=NOR11或=N-N(R11)2,其中C3-C6环烷基、芳基、杂芳基、芳氧基、杂芳氧基、芳基C1-C6烷基或杂芳基C1-C6烷基任选地被R9表示的1至3个基团取代;或者
R8是C3-C9环烷基,其任选地被R10表示的1个基团取代,其中R10是螺环的3至10元饱和或部分不饱和的碳环系统或杂环系统,该系统含有1或2个杂原子,所述杂原子选自氧、氮和硫,并且任选地被卤素、C1-C4烷基或=O表示的1至3个基团取代。
8.根据权利要求1至6中任一项所述的化合物,其中R8是C5-C8环烷基,其任选地被R10表示的1或2个基团取代,其中R10独立地选自羟基、C1-C6烷基、C1-C6烷基羰氧基、C3-C6环烷基、芳基、=C(R11)2、=NOR11或螺环的1,3-二氧戊环-2-基,其中C1-C6烷基、C3-C6环烷基、芳基、=C(R11)2和=NOR11任选地被R9表示的1至3个基团取代,或其中螺环的1,3-二氧戊环-2-基任选地被卤素、C1-C4烷基或=O表示的1至3个基团取代;并且
R11独立地选自氢、C1-C6烷基、C2-C6烯基、C2-C6炔基和芳基。
9.根据权利要求8所述的化合物,其中R8是C5-C8环烷基,其任选地被R10表示的1或2个基团取代,其中R10独立地选自羟基、C1-C4烷基、C1-C6烷基羰氧基、C6环烷基、苯基、=C(R11)2或=NOR11,并且R11独立地选自氢、C1-C4烷基、C2-C4烯基、C2-C4炔基和苯基。
10.根据权利要求1至9中任一项所述的化合物,其中X是N。
11.根据权利要求1所述的化合物,其选自以下中的任一项:
N-[4-(环戊氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环戊氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环己氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环己氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(4,4-二甲基环己氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(4,4-二甲基环己氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[2-氟-4-(3,3,5,5-四甲基环己氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环庚氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环庚氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;
N-[4-(环辛氧基)苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺;或者
N-[4-(环辛氧基)-2-氟-苯基]-3-羟基-4-甲氧基-吡啶-2-甲酰胺。
12.一种农用化学组合物,包含杀真菌有效量的根据权利要求1至11中任一项所述的具有式(I)的化合物。
13.根据权利要求12所述的组合物,进一步包含至少一种另外的活性成分和/或农用化学上可接受的稀释剂或载体。
14.一种控制或预防有用植物被植物病原性微生物侵染的方法,其中将杀真菌有效量的根据权利要求1至11中任一项所述的具有式(I)的化合物或包含这种化合物作为活性成分的组合物施用至所述植物、其部分或其场所。
15.根据权利要求1至11中任一项所述的化合物或根据权利要求12或权利要求13所述的组合物作为杀真菌剂的用途。
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- 2016-11-03 BR BR112018008947A patent/BR112018008947A8/pt not_active Application Discontinuation
- 2016-11-03 CN CN201680064433.0A patent/CN108349915A/zh active Pending
- 2016-11-03 JP JP2018541544A patent/JP2018538362A/ja active Pending
- 2016-11-03 EP EP16794251.5A patent/EP3371153A1/en not_active Withdrawn
- 2016-11-03 US US15/773,467 patent/US10357035B2/en not_active Expired - Fee Related
- 2016-11-03 WO PCT/EP2016/076579 patent/WO2017076982A1/en active Application Filing
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Also Published As
Publication number | Publication date |
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WO2017076982A1 (en) | 2017-05-11 |
US20180317482A1 (en) | 2018-11-08 |
BR112018008947A2 (pt) | 2018-10-30 |
JP2018538362A (ja) | 2018-12-27 |
BR112018008947A8 (pt) | 2019-02-26 |
US10357035B2 (en) | 2019-07-23 |
EP3371153A1 (en) | 2018-09-12 |
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