CN106661021A - 具有含硫取代基的杀有害生物活性杂环衍生物 - Google Patents
具有含硫取代基的杀有害生物活性杂环衍生物 Download PDFInfo
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- CN106661021A CN106661021A CN201580036892.3A CN201580036892A CN106661021A CN 106661021 A CN106661021 A CN 106661021A CN 201580036892 A CN201580036892 A CN 201580036892A CN 106661021 A CN106661021 A CN 106661021A
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- YGBMMMOLNODPBP-GWGZPXPZSA-N s-ethyl (2e,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienethioate Chemical compound CCSC(=O)\C=C(/C)\C=C\CC(C)CCCC(C)(C)OC YGBMMMOLNODPBP-GWGZPXPZSA-N 0.000 description 1
- LSMIOFMZNVEEBR-ICLSSMQGSA-N scilliroside Chemical compound C=1([C@@H]2[C@@]3(C)CC[C@H]4[C@@]([C@]3(CC2)O)(O)C[C@H](C2=C[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC[C@@]24C)OC(=O)C)C=CC(=O)OC=1 LSMIOFMZNVEEBR-ICLSSMQGSA-N 0.000 description 1
- 239000002795 scorpion venom Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
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- SDLBJIZEEMKQKY-UHFFFAOYSA-M silver chlorate Chemical compound [Ag+].[O-]Cl(=O)=O SDLBJIZEEMKQKY-UHFFFAOYSA-M 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229940125794 sodium channel blocker Drugs 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 239000011655 sodium selenate Substances 0.000 description 1
- 235000018716 sodium selenate Nutrition 0.000 description 1
- 229960001881 sodium selenate Drugs 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 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
- ZEVCJZRMCOYJSP-UHFFFAOYSA-N sodium;2-(dithiocarboxyamino)ethylcarbamodithioic acid Chemical compound [Na+].SC(=S)NCCNC(S)=S ZEVCJZRMCOYJSP-UHFFFAOYSA-N 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
- WQQPDTLGLVLNOH-UHFFFAOYSA-M sodium;4-hydroxy-4-oxo-3-sulfobutanoate Chemical class [Na+].OC(=O)CC(C([O-])=O)S(O)(=O)=O WQQPDTLGLVLNOH-UHFFFAOYSA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
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- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- 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
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
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- 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
- 229940063650 terramycin Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- BPJYAXCTOHRFDQ-UHFFFAOYSA-L tetracopper;2,4,6-trioxido-1,3,5,2,4,6-trioxatriarsinane;diacetate Chemical compound [Cu+2].[Cu+2].[Cu+2].[Cu+2].CC([O-])=O.CC([O-])=O.[O-][As]1O[As]([O-])O[As]([O-])O1.[O-][As]1O[As]([O-])O[As]([O-])O1 BPJYAXCTOHRFDQ-UHFFFAOYSA-L 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- YTQVHRVITVLIRD-UHFFFAOYSA-L thallium sulfate Chemical compound [Tl+].[Tl+].[O-]S([O-])(=O)=O YTQVHRVITVLIRD-UHFFFAOYSA-L 0.000 description 1
- 229940119523 thallium sulfate Drugs 0.000 description 1
- 229910000374 thallium(I) sulfate Inorganic materials 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
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- UZKQTCBAMSWPJD-UQCOIBPSSA-N trans-Zeatin Natural products OCC(/C)=C\CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-UQCOIBPSSA-N 0.000 description 1
- UZKQTCBAMSWPJD-FARCUNLSSA-N trans-zeatin Chemical compound OCC(/C)=C/CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-FARCUNLSSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 235000011351 tree mallow Nutrition 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
- 229950001353 tretamine Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- NRHFWOJROOQKBK-UHFFFAOYSA-N triphenyltin;hydrate Chemical compound O.C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 NRHFWOJROOQKBK-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- 241001515965 unidentified phage Species 0.000 description 1
- SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 description 1
- 229950006929 uredepa Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000017468 valeriana Nutrition 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- FVECELJHCSPHKY-JLSHOZRYSA-N veratridine Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 FVECELJHCSPHKY-JLSHOZRYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- 239000002578 wasp venom Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229940023877 zeatin Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- A01N55/08—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catching Or Destruction (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
具有化学式(I)的化合物,
Description
本发明涉及含硫取代基的杀有害生物活性(尤其是杀虫活性的)杂环衍生物,涉及用于制备那些化合物的中间体,涉及包含那些化合物的组合物,并且涉及它们用于控制动物有害生物(包括节肢动物并且尤其是昆虫或蜱螨目的代表)的用途。
具有杀有害生物作用的杂环化合物是已知的并描述于例如WO 2012/086848和WO2013/018928中。
现在已经发现具有含硫的苯基和吡啶基取代基的杀有害生物活性杂环6/5-二环衍生物。
本发明因此涉及具有化学式I的化合物,
其中
A表示CH或N;
每个R彼此独立地是C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基硫烷基、C1-C4卤代烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4卤代烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷氧基羰基、C1-C6烷基氨基、C2-C8二烷基氨基、卤素、氰基、氰基C1-C4烷基、三(C1-C4烷基)甲硅烷基、C1-C4烷氧基C1-C4烷氧基、C1-C4烷基硫烷基C1-C4烷氧基或硝基;
或每个R彼此独立地是苯基、嘧啶基、噻唑基、吡啶基、咪唑基、吡唑基、噁唑基或噁二唑基;其中所述苯基、嘧啶基、噻唑基、吡啶基、咪唑基、吡唑基、噁唑基或噁二唑基本身可以是被独立地选自下组的取代基单取代至多取代的,该组由以下各项组成:卤素、C1-C6烷基和氰基;
n是0、1、2、3、4或5;
X是S、SO或SO2;
R1是C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基、被选自下组的取代基单-、二-或三取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;或R1是被选自下组的取代基单取代或多取代的C3-C6环烷基-C1-C4烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;
或R1是C2-C6烯基、C2-C6卤代烯基或C2-C6炔基;
R2是卤素、C1-C4卤代烷基或被一个或两个选自下组的取代基取代的C1-C4卤代烷基,该组由以下各项组成:羟基、甲氧基和氰基;
或R2是C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、O(C1-C4卤代烷基)或-C(O)C1-C4卤代烷基;
或R2是C3-C6环烷基,其可以是被选自下组的取代基单取代或多取代的,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且
X1是O、S或NR3,其中R3是氢、C1-C4烷基、C2-C6烯基、C2-C6炔基、C1-C4烷氧基-C1-C4烷基或C3-C6环烷基;
以及那些化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。
具有至少一个碱性中心的具有化学式I的化合物可以与以下酸形成例如酸加成盐,这些酸为:例如强无机酸(例如矿物酸,例如高氯酸、硫酸、硝酸、亚硝酸、磷酸或氢卤酸),强有机羧酸(例如未经取代的或像被卤素取代的C1-C4烷羧酸,例如乙酸(像饱和或不饱和的二羧酸),例如草酸、丙二酸、琥珀酸、马来酸、富马酸或邻苯二甲酸(像羟基羧酸),例如抗坏血酸、乳酸、苹果酸、酒石酸或柠檬酸,或像苯甲酸),或有机磺酸(例如未经取代的或像被卤素取代的C1-C4烷-或芳基磺酸,例如甲烷-或对甲苯磺酸)。具有至少一个酸性基团的具有化学式I的化合物可以例如,与碱形成盐(例如矿物盐(像碱金属或碱土金属盐,例如钠盐、钾盐或镁盐)),与氨或有机胺(像吗啉、哌啶、吡咯烷、单-、二-或三-低级-烷基胺(例如乙基-、二乙基-、三乙基-或二甲基丙胺),或单-、二-或三羟基-低级-烷基胺(例如单-、二-或三乙醇胺))形成盐。
在取代基定义中出现的烷基可以是直链的或支链的,并且是例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、己基、壬基、癸基以及它们的支链异构体。烷基硫烷基、烷基亚磺酰基、烷基磺酰基、烷氧基、烯基和炔基基团衍生自所提及的烷基基团。烯基和炔基基团可以是单或多不饱和的。
卤素一般是氟、氯、溴或碘。相应地,这也适用于与其他含义结合的卤素,例如卤代烷基或卤代苯基。
卤代烷基基团优选地具有从1至6个碳原子的链长。卤代烷基是例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基以及2,2,2-三氯乙基。
烷氧基是例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基并且还是同分异构的戊氧基以及己氧基基团。
烷氧基烷基基团优选地具有1至6个碳原子的链长。
烷氧基烷基是,例如甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、正丙氧基甲基、正丙氧基乙基、异丙氧基甲基或异丙氧基乙基。
烷氧基羰基是,例如甲氧基羰基(其为C1烷氧基羰基)、乙氧基羰基、丙氧基羰基、异丙氧基羰基、正丁氧基羰基、叔丁氧基羰基、正戊氧基羰基或己氧基羰基。
这些环烷基基团优选地具有从3至6个环碳原子,例如环丙基、环丁基、环戊基和环己基。
在本发明的上下文中,取代基定义中的“单到多取代的”典型地是指,取决于取代基的化学结构,单取代的到七次取代的,优选是单取代的到五次取代的,更优选是单、二或三取代的。
根据本发明的具有化学式I的化合物还包括在盐形成期间可以形成的水合物。
在本发明的一个实施例中,具有化学式I的化合物是优选的,其中每个R彼此独立地是C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基硫烷基、C1-C4卤代烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4卤代烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷氧基羰基、C1-C6烷基氨基、C2-C8二烷基氨基、卤素、氰基或硝基;
R1是C1-C4烷基,C1-C4卤代烷基,C3-C6环烷基,C3-C6环烷基-C1-C4烷基,被卤素单-、二-或三取代的C3-C6环烷基;或R1是C2-C6烯基、C2-C6卤代烯基或C2-C6炔基;
R2是卤素、C1-C4卤代烷基或被一个或两个羟基取代的C1-C4卤代烷基;或R2是C1-C4卤代烷基硫烷基、C1-C4卤代烷基磺酰基或O(C1-C4卤代烷基)。
具有化学式I的化合物的优选的组由具有化学式I-1的化合物表示
其中R、R2和n是如以上在化学式I下所定义的;
Xa1是S、SO或SO2;
Ra1是甲基、乙基、正丙基、异丙基或环丙基甲基;以及这些化合物的农业上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。在具有化学式I-1的化合物的这个优选的组中,n是1,R是卤素、C1-C4卤代烷基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基硫烷基、C1-C4烷基磺酰基、氰基、氰基C1-C4烷基、三(C1-C4烷基)甲硅烷基、C1-C4烷基硫烷基C1-C4烷氧基、吡唑基、或噁二唑基(优选是卤素、氰基或C1-C4卤代烷基),R2优选地是C1-C4卤代烷基,Xa1优选地是SO2并且Ra1优选地是乙基。
具有化学式I的化合物的另外的优选的组由具有化学式I-2的化合物表示
其中R、R2和n是如以上在化学式I下所定义的;并且其中Xa2是S、SO或SO2;Ra2是甲基、乙基、正丙基、异丙基或环丙基甲基;以及这些化合物的农业上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。在具有化学式I-2的化合物的这个另外的优选的组中,n是1,R是卤素或C1-C4卤代烷基,R2优选地是C1-C4卤代烷基,Xa1优选地是SO2并且Ra1优选地是乙基。
在以上优选的组的化学式中的自由基代表甲基。
尤其优选的具有化学式I的化合物由具有化学式Ia的化合物表示
其中
X2是SO2;
X3是N-C1-C4烷基;
R4是C1-C4烷基;
R5是卤素、C1-C4卤代烷基、氰基或C1-C4烷氧基;
C1-C4烷基、C1-C4卤代烷氧基、C1-C4烷基硫烷基、C1-C4烷基磺酰基、氰基、氰基C1-C4烷基、三(C1-C4烷基)甲硅烷基、C1-C4烷基硫烷基C1-C4烷氧基、吡唑基、或噁二唑基;具体地R5是卤素、C1-C4卤代烷基、氰基或C1-C4烷氧基;
n是1、2或3;并且
R6是C1-C4卤代烷基。
另一个尤其优选的具有化学式I的化合物由具有化学式Ib的化合物表示
其中
A是N或CH;
X2是S或SO2;
X3是N-C1-C4烷基;
R7是C1-C4烷基;
R8是卤素、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷基、C1-C4卤代烷氧基、C1-C4烷基硫烷基、C1-C4烷基磺酰基、氰基、氰基C1-C4烷基、三(C1-C4烷基)甲硅烷基、C1-C4烷基硫烷基C1-C4烷氧基、吡唑基、或噁二唑基;具体地R8是卤素、氰基、C1-C4卤代烷基或C1-C4烷氧基;
n是0、1、2或3;优选是1、2或3;并且
R9是C1-C4卤代烷基。
根据本发明的用于制备具有化学式I的化合物的方法通过本领域普通技术人员已知的方法来进行。更具体地,可以通过将具有化学式II的化合物与具有化学式III的化合物进行反应制备具有化学式I的化合物(如描述在方案1中),其中Xb1可以是卤素(优先地是氯、溴、或碘)或磺酸酯(例如像三氟甲磺酸酯),并且Yb1可以是硼衍生的官能团(如例如B(OH)2或B(ORb1)2,其中Rb1可以是C1-C4烷基基团或这两个基团ORb1可以与硼原子一起形成一个五元环(如例如频哪醇硼酸酯))。在化学式II和III中,A、X1、R1、R2、R、X和n是如在化学式I中所描述的。该反应可以通过基于钯的催化剂(例如四(三苯基膦)钯)、在碱(如碳酸钠)的存在下、在溶剂或溶剂混合物(像例如1,2-二甲氧基乙烷和水的混合物)中、优选地在惰性气氛下进行催化。该反应温度可以优先地在从室温至反应混合物的沸点的范围內。
在以下方案中,取代基Rn具有与上文描述的化学式I中的取代基(R)n相同的含义。
方案1:
也可以通过将具有化学式IV的化合物与具有化学式V的化合物进行反应制备具有化学式I的化合物(如描述在方案2中),其中Xb2可以是卤素(优先地氯、溴、或碘)或磺酸酯(像例如三氟甲磺酸酯),并且Yb2可以是硼衍生的官能团(如例如B(OH)2或B(ORb2)2,其中Rb2可以是C1-C4烷基基团或这两个基团ORb2可以与硼原子一起形成一个五元环(如例如频哪醇硼酸酯))。在化学式IV和V中,A、X1、R1、R2、R、X和n是如在化学式I中所描述的。该反应可以通过基于钯的催化剂(例如四(三苯基膦)钯)、在碱(如碳酸钠)的存在下、在溶剂或溶剂混合物(像例如1,2-二甲氧基乙烷和水的混合物)中、优选地在惰性气氛下进行催化。该反应温度可以优选地在从环境温度至反应混合物的沸点的范围内。
方案2
具有化学式IV的化合物
(其中
R1、R2、X、X1和A是如以上在化学式I下所定义的,并且Yb2是-B(OH)2、-B(ORb2)2(其中Rb2是C1-C4烷基或(4,4,5,5-四甲基-1,3,2-二噁环戊硼烷基团)))是新颖的,被特别地研发用于制备根据本发明的具有化学式I的化合物,并因此代表了本发明的另外的目的。
可以通过具有化学式I-a2的化合物(其中A、R、R1、R2、X1和n具有在化学式I中所定义的值,并且X是-SO-)的氧化反应来制备具有化学式I-a3的化合物(其中A、R、R1、R2、X1和n具有在化学式I中所定义的值,并且X是-SO2-)。该反应可以用试剂(像例如过酸(如过氧乙酸或间氯过氧化苯甲酸、或氢过氧化物(如例如过氧化氢或叔丁基氢过氧化物)、或无机氧化剂(如单过氧焦硫酸盐或高锰酸钾))进行。在上文描述的类似的条件下,以相似的方式,可以通过具有化学式I-a1的化合物(其中A、R、R1、R2、X1和n具有在化学式I中所定义的值,并且X是-S-)的氧化反应来制备具有化学式I-a2的化合物(其中A、R、R1、R2、X1和n具有在化学式I中所定义的值,并且X是-SO-)。这些反应可以在与这些条件相容的各种有机或水性溶剂中,以从低于0℃高至溶剂体系的沸点的温度进行。将具有化学式1-a1的化合物转化为具有化学式1-a2和1-a3的化合物在方案3中描述。
方案3
也可以通过将具有化学式VI的化合物与具有化学式VII的化合物进行反应来制备具有化学式I-a1的化合物(方案4),其中A、R、R1、R2、X1和n具有在化学式I中所定义的值,并且X是硫并且M是金属或非金属阳离子。在方案4中,假定阳离子M是单价的,但也可以考虑与多于一个S-R1基团相关联的多价阳离子。优选的阳离子是例如锂、钠、钾或铯。为了这个转化起作用,Xb3是离去基团像例如氟、氯、溴或碘,或芳基-或烷基磺酸酯,但也可以考虑许多其他离去基团。该反应可以在溶剂(优选是非质子溶剂)中,在低于0℃的温度或高至反应混合物的沸点的温度下进行。
方案4
可以通过将具有化学式VIII的化合物与具有化学式IX的化合物(其中Xb4可以是卤素(优先地氯、溴或碘)或磺酸酯(像例如三氟甲磺酸酯),最优选是溴或碘,并且Yb4可以是硼衍生的官能团(如例如B(OH)2或B(ORb4)2,其中Rb4可以是C1-C4烷基基团或这两个基团ORb4可以与硼原子一起形成一个五元环(如例如频哪醇硼酸酯))进行反应来制备具有化学式VI的化合物(其中Xb3是离去基团像例如氟、氯、溴或碘,或芳基-或烷基磺酸盐(如三氟甲磺酸酯),或任何其他相似的离去基团)(方案5)。在化学式VI、VIII和IX中,A、X1、R2、R、和n是如在化学式I中所描述的。该反应可以通过基于钯的催化剂(例如四(三苯基膦)钯)、在碱(如碳酸钠)的存在下、在溶剂或溶剂混合物(像例如1,2-二甲氧基乙烷和水的混合物)中、优选地在惰性气氛下进行催化。该反应温度可以优先地在从室温至反应混合物的沸点的范围内。
方案5
在方案6中描述的可替代地方法中,也可以通过将具有化学式X的化合物(其中Xb3是离去基团像例如氟、氯、溴或碘,或芳基-或烷基磺酸酯(例如三氟甲磺酸酯),或任何其他相似的离去基团)与具有化学式XI的化合物(其中Xb5可以是卤素(优先是氯、溴或碘)或磺酸酯(像例如三氟甲磺酸酯),最优选是溴或碘,并且Yb5可以是硼衍生的官能团(如例如B(OH)2或B(ORb5)2,其中Rb5可以是C1-C4烷基基团或这两个基团ORb5以与硼原子一起形成一个五元环(如例如频哪醇硼酸酯))进行反应来制备具有化学式VI的化合物。在化学式VI、X和XI中,A、X1、R2、R、和n是如在化学式I中所描述的。该反应可以通过基于钯的催化剂(例如四(三苯基膦)钯)、在碱(如碳酸钠)的存在下、在溶剂或溶剂混合物(像例如1,2-二甲氧基乙烷和水的混合物)中、优选地在惰性气氛下进行催化。该反应温度可以优先地在从室温至反应混合物的沸点的范围内。
方案6
也可以通过将具有化学式XIII的化合物与具有化学式XIV的化合物在各种正式脱水条件下进行反应来制备具有化学式I的化合物(方案7),其中A、R、R1、R2、X、X1和n具有在化学式I中所描述的值。这些方法是本领域普通技术人员已知的或例如描述在WO 2009/131237、WO 2011/043404、WO 2011/040629、WO 2010/125985、WO 2012/086848、WO 2013/018928、WO 2013/191113、WO 2013/180193和WO 2013/180194中。这些方式是众所周知的并且已经在例如WO 2011/040629或WO 2009/131237(X1是氧)、WO 2011/088990或无机化学学报(Inorg.Chimica Acta),358(9),2701-2710;2005(X1是硫)以及美国化学会志(J.Am.Chem.Soc.),132(5),1545-1557,2010或WO 2008/128968(X1是NR3)中描述。
方案7
描述具有化学式XIII的化合物和具有化学式XIV的化合物之间向具有化学式I的化合物的反应的方法在方案8中进行了更详细的概述:
方案8
通过本领域普通技术人员已知的和描述于例如四面体(Tetrahedron),61(46),10827-10852,2005中的方法,将具有化学式XIV的化合物(其中A、R、R1、X和n是如先前描述的)激活为具有化学式XIV-a的化合物(方案8)。例如其中X0是氯的化合物是通过在催化量的DMF的存在下,在惰性溶剂(例如二氯甲烷或THF)中,在20℃至100℃之间的温度(优选25℃)下用例如草酰氯或亚硫酰氯进行处理形成的。在溶剂(例如四氢呋喃)中,任选地在碱(例如三乙胺或吡啶)的存在下用具有化学式XIII的化合物(其中R2和X1是如在化学式I中所定义的)处理XIV-a产生具有化学式XV的化合物。可替代地,可以通过在惰性溶剂(例如吡啶或四氢呋喃(THF))中,任选地在碱(例如三乙胺)的存在下,在50℃-180℃之间的温度下,用二环己基碳二亚胺(DCC)或1-乙基-3-(3-二甲基氨基丙基)碳二亚胺(EDC)处理具有化学式XIV的化合物,以给出被激活的种类XIV-a(其中X0分别是X01和X02)来制备具有化学式I的化合物。然后,这样获得的具有化学式XV的化合物可通过在酸催化剂(例如甲磺酸、或对甲苯磺酸)的存在下,在惰性溶剂(例如N-甲基吡咯烷酮或二甲苯)中,在25℃-180℃之间(优选130℃-170℃)的温度下,进行脱水(例如通过加热该化合物,任选地在微波中照射)被转化为具有化学式I的化合物。先前已经在WO 2010/125985中描述了这类方法。可替代地,在惰性溶剂(例如THF)中,在25℃-50℃之间的温度下,可使用三苯基膦、二异丙基偶氮二羧酸盐将具有化学式XV的化合物转化为具有化学式I的化合物(其中X1是O)。先前已经针对这类转化描述了这类光延反应(Mitsunobu)条件(参见WO 2009/131237)。
以类似的方式(方案9),可以通过用活性剂(像例如草酰氯或亚硫酰氯)或碳二亚胺试剂与具有化学式XVI的化合物(其中A、R和n具有对于化学式I所定义的值)进行反应以产生被激活的种类XVI-a,随后通过与具有化学式XIII的化合物(其中R2和X1是如在化学式I中所描述的)进行反应来制备具有化学式VI的化合物(其中Xb3是离去基团像例如氟、氯、溴或碘,或芳基-或烷基磺酸酯(例如三氟甲磺酸酯),或任何其他相似的离去基团)。该具有化学式XVII的中间体化合物可以是分离的,但优先地以与上文描述的用于将化合物XV转化为具有化学式I的化合物的相似的方式转化为具有化学式VI的化合物。
方案9
以与上文描述的相似的方式,可以通过将具有化学式XVIII的化合物,分别是具有化学式XVIII的化合物的活化形式XVIII-a(其中A是碳或氮,并且Xb3是离去基团像例如氟、氯、溴或碘,或芳基-或烷基磺酸盐(例如三氟甲磺酸酯)并且Xb4可以是卤素(优先是氯、溴或碘)或磺酸盐(像例如三氟甲磺酸酯),最优选是溴或碘)与具有化学式XIII的化合物(其中X1和R2是如在化学式I中所定义的)进行反应来制备具有化学式VIII的化合物(如描述在方案10中)。该具有化学式XIX的中间体化合物可以是分离的,但优先地以与上文描述的相似的方式(将化合物XV转化为具有化学式I的化合物)转化为具有化学式VIII的化合物。
方案10
以与上文描述的相似的方式,可以通过将具有化学式XX的化合物,分别是具有化学式XX的化合物的活化形式XX-a(其中A是碳或氮,并且其中R1和X是如先前所定义的,并且其中Xb4可以是卤素(优先是氯、溴或碘)或磺酸盐(像例如三氟甲磺酸酯),最优选是溴或碘)与具有化学式XIII的化合物(其中X1和R2是如在化学式I中所定义的)进行反应来制备具有化学式II的化合物(如描述在方案10a中)。该具有化学式XXI的中间体化合物可以是分离的,但优先地以与上文描述的相似的方式(将化合物XV转化为具有化学式I的化合物)转化为具有化学式II的化合物。
方案10a
可以通过将具有化学式VIII的化合物(其中A、R2和X1是如在化学式I中所定义的,并且其中Xb3是离去基团像例如氟、氯、溴或碘,或芳基-或烷基磺酸酯(例如三氟甲磺酸酯),优先是氟或氯,并且其中Xb4是卤素(优先是氯、溴或碘)或磺酸酯(像例如三氟甲磺酸酯),最优选是溴或碘)与具有化学式VII的化合物(其中R1是如在化学式I中所定义的,并且M金属或非金属阳离子)进行反应来制备具有化学式II-a1的化合物(其中X是硫)(方案11)。在方案11中,假定阳离子M是单价的,但也可以考虑与多于一个S-R1基团相关联的多价阳离子。优选的阳离子是例如锂、钠、钾或铯。该反应可以在溶剂(优选是极性非质子溶剂)中,在低于0℃的温度或高至反应混合物的沸点的温度下进行。
方案11
可以通过将具有化学式II-a2的化合物(其中A、R1、R2和X1具有如在化学式I中所定义的值,并且X是-SO-,并且其中Xb4是卤素(优先是氯、溴或碘)或磺酸盐(像例如三氟甲磺酸酯))的氧化反应来制备具有化学式II-a3的化合物(其中A、R1、R2和X1具有如在化学式I中所定义的值,并且X是-SO2-,并且其中Xb4是卤素(优先是氯、溴或碘)或磺酸盐(例如三氟甲磺酸酯)(方案12)。该反应可以用试剂(像例如过酸(如过氧乙酸或间氯过氧化苯甲酸、或氢过氧化物(例如过氧化氢或叔丁基氢过氧化物)、或无机氧化剂(如单过氧焦硫酸盐或高锰酸钾),优选是间氯过氧化苯甲酸)进行反应。以相似的方式,可以通过将具有化学式II-a1的化合物(其中A、R1、R2和X1具有如在化学式I中所定义的值,并且X是-S-,并且其中Xb4是卤素(优先是氯、溴或碘)或磺酸盐(像例如三氟甲磺酸酯))的氧化反应来制备具有化学式II-a2的化合物(其中A、R1、R2和X1具有如在化学式I中所定义的值,并且X是-SO-,并且其中Xb4是卤素(优先是氯、溴或碘)或磺酸盐(像例如三氟甲磺酸酯)。这些反应可以在与这些条件相容的各种有机或水性溶剂中,以从低于0℃高至溶剂体系的沸点的温度进行。
方案12
许多具有化学式V和XI的化合物(其中R和n具有如在化学式I中所定义的值,并且其中Xb2和Xb5是如上文所定义的)是可商购的或可以通过类似于在文献中描述的程序被本领域的技术人员获得的。
大量的具有化学式III的化合物是可商购的或可以由本领域普通技术人员制备。本领域普通技术人员熟知的许多化学转化可以被用于从多种多样和容易获得的起始材料开始(例如仅引用少量),在具有化学式III-a的芳香化合物(其中Zb1是氢)与强碱(如丁基锂或二异丙基氨基锂或(i-PrMgCl,LiCl))氢提取(步骤A),随后将具有化学式III-b的金属化中间体(其中Zb2是金属(例如如Li+或MgCl+)与例如硼酸三烷基酯反应(步骤B)来获得化学式III的硼酸衍生物(方案13)。另一个获得具有化学式III-b的有机金属中间体的方法是从具有化学式III-a的化合物(其中Zb1是氯、溴或碘)与有机金属种类(像丁基锂或有机金属化合物)经金属-卤素交换,或直接用金属(像镁)金属化(步骤C)。
经双频哪醇二硼烷在具有化学式III-a的化合物(其中Zb1是氯、溴、碘或三氟甲磺酸酯)上的钯催化反应引入频哪醇硼酸盐官能团基团是另一个常用的策略(方案13,步骤D)。在方案13中的具有化学式III-a、III-b和III的化合物中,R和n具有如在化学式I中所定义的值。本领域技术人员将能够选择适当的制备方法以根据R和n的值从化学式III-a获得具有化学式III的化合物。
方案13
在方案13中描述的相同制备方法可以应用于具有化学式IX的中间体的合成。
具有化学式IV的化合物(其中A、X、X1、R1和R2是如在化学式I中所描述的)可以从具有化学式II的化合物(其中A、X、X1、R1和R2是如在化学式I中所描述的)制备(方案14)。实际上,具有化学式II的化合物(其中Xb1是氯、溴或碘)可以经金属-卤素交换,用有机金属种类(像例如丁基锂或有机镁化合物)处理以产生具有化学式II-a的中间化合物(其中Zb3是如在方案中所定义的)该反应优先地在无水非质子溶剂(例如THF),在低温度下(在-120℃和0℃之间)(优选地-110℃和-60℃在之间)进行。通过与硼酸酯化合物B(ORb2)3(其中Rb2是C1-C4烷基基团)反应,将具有化学式II-a的中间有机金属化合物优选地直接转化为具有化学式IV的化合物。取决于硼酸酯的性质、反应处理条件和处理条件,可以形成硼酸IV(其中Yb2是-B(OH)2)或二烷基硼酸酯IV(其中Yb2是-B(ORb2)2)。
经与双频哪醇乙硼烷B2Pin2的钯催化反应在具有化学式II(其中A、X、X1、R1和R2是如在化学式I中所定义的,并且其中Xb1是氯、溴、碘或三氟甲磺酸酯)化合物上引入频哪醇硼酸酯官能团是另一种常见的策略。产生环硼酸酯IV(其中Yb2是)的该反应可以在非质子溶剂中,在碱的存在下(优选是弱碱,例如乙酸钾KOAc)进行。[1,1′-双(二苯基膦基)二茂铁]二氯钯(II),也称为二氯化钯dppf或Pd(dppf)Cl2是用于这类反应的常见催化剂。该反应的温度优选地在0℃和反应混合物的沸点之间。
方案14
这些反应物可以在碱的存在下发生反应。适合的碱的实例是碱金属或碱土金属氢氧化物、碱金属或碱土金属氢化物、碱金属或碱土金属酰胺、碱金属或碱土金属醇盐、碱金属或碱土金属乙酸盐、碱金属或碱土金属碳酸盐、碱金属或碱土金属二烷基酰胺或碱金属或碱土金属烷基甲硅烷基酰胺、烷基胺、亚烷基二胺、游离的或N-烷基化的饱和或不饱和的环烷基胺、碱性杂环、氢氧化铵以及碳环胺。可以提及的实例是氢氧化钠、氢化钠、氨基钠、甲醇钠、乙酸钠、碳酸钠、叔丁醇钾、氢氧化钾、碳酸钾、氢化钾、二异丙氨基锂、双(三甲基硅烷基)酰胺钾、氢化钙、三乙胺、二异丙基乙胺、三亚乙基二胺、环己胺、N-环己基-N,N-二甲胺、N,N-二乙苯胺、吡啶、4-(N,N-二甲氨基)吡啶、奎宁环、N-甲基吗啉、苄基三甲基铵氢氧化物以及1,8-二氮杂二环[5.4.0]十一-7-烯(DBU)。
具有化学式XX的化合物可以通过与文献中描述的那些类似的方法制备(方案15)。例如,在本领域技术人员已知的条件下,可以通过具有化学式XXII的化合物(其中RLG是C1-C4烷基)的皂化反应来制备具有化学式XX的化合物(其中X是S,R1是乙基,A是N并且Xb4是溴)。
方案15
在上文描述的条件下,可以通过用试剂M-S-R1(其中R1是如在化学式I中所定义的并且M是金属或非金属阳离子)处理具有化学式XXIII的化合物(其中RLG是C1-C4烷基)来制备具有化学式XXII的化合物(其中RLG是C1-C4烷基)。涉及例如甲硫醇钠或乙硫醇钠作为试剂M-S-R1的这类方法是众所周知的,并且先前已在例如WO 2014/152738中进行了描述。
可以通过具有化学式XXIV的化合物(其中RLG是C1-C4烷基,并且其中Xb3是离去基团像例如氟、氯、溴或碘,或芳基-或烷基磺酸酯(例如三氟甲磺酸酯),或任何其他相似的离去基团,并且其中A、R和n是如在化学式I中所定义的)与具有化学式VII的化合物(其中R1是如在化学式I中所定义的,X是硫并且M是金属或非金属阳离子)进行反应来制备具有化学式XIV的化合物(其中X是硫,并且其中A、R1、R和n是如在化学式I中所定义的)(方案16)。在方案16中,假定阳离子M是单价的,但也可以考虑与多于一个S-R1基团相关联的多价阳离子。优选的阳离子是例如锂、钠、钾或铯。该反应可以在溶剂(优选是非质子溶剂,例如N,N-二甲基甲酰胺)中,在低于0℃的温度或高至反应混合物的沸点的温度下进行。
方案16
在本领域技术人员已知的条件下,在具有化学式XXIV的化合物与如上文描述的具有化学式VII的化合物之间的反应之后可以进行皂化反应步骤以将-COORLG基团(其中RLG是C1-C4烷基)转化为-COOH官能团。方便地,皂化可以伴随取代步骤,从而允许具有化学式XIV的化合物的直接分离。
可以通过具有化学式XXV的化合物(其中RLG是C1-C4烷基,并且其中Xb3是离去基团像例如氟、氯、溴或碘,或芳基-或烷基磺酸酯(例如三氟甲磺酸酯),或任何其他相似的离去基团,并且其中A是如在化学式I中所定义的,并且其中Xb4是卤素(优先是氯、溴或碘)或磺酸酯(像例如三氟甲磺酸酯),最优选是溴或碘)与具有化学式IX的化合物(其中R和n是如在化学式I中所定义的,并且其中Yb4可以是硼衍生的官能团(例如B(OH)2或B(ORb4)2,其中Rb4可以是C1-C4烷基基团或这两个基团ORb4可以与硼原子一起形成一个五元环(如例如频哪醇硼酸酯))进行反应来制备具有化学式XXIV的化合物(其中RLG是C1-C4烷基,并且其中Xb3是离去基团像例如氟、氯、溴或碘,或芳基-或烷基磺酸酯(例如三氟甲磺酸酯),或任何其他相似的离去基团,并且其中A、R和n是如在化学式I中所定义的)(方案17)。该反应可以通过基于钯的催化剂(例如四(三苯基膦)钯)、在碱(如碳酸钠)的存在下、在溶剂或溶剂混合物(像例如1,2-二甲氧基乙烷和水的混合物)中、优选地在惰性气氛下进行催化。该反应温度可以优先地在从室温至反应混合物的沸点的范围内。这些是已知的,并且已经先前描述在例如WO2003/027061中。
方案17
在本领域技术人员已知的条件下,可以从具有化学式XVIII的化合物通过酯化反应的方式(涉及具有化学式RLGOH的醇(其中RLG是C1-C4烷基))来制备具有化学式XXV的化合物和具有化学式XXIII的化合物(其中RLG是C1-C4烷基)。
这些试剂能按照原样彼此进行反应,即:不用添加溶剂或稀释剂。然而,在大多数情况下,加入一种惰性溶剂或稀释剂或这些的混合物是有利的。如果该反应在碱的存在下进行,那么这些过量使用的碱(如三乙胺、吡啶、N-甲基吗啉或N,N-二乙苯胺)还可以充当溶剂或稀释剂。
该反应有利地是在从约-80℃到约+140℃,优选从约-30℃到约+100℃,在许多情况下在介于环境温度与约+80℃之间的温度下进行。
一种具有化学式I的化合物能以一种本身已知的方法转化为另一种具有化学式I的化合物,这是通过以常规方式将该起始的具有化学式I的化合物的一个或多个取代基用根据本发明的另一个或其他的一个或多个取代基的替代来实现的。
取决于所选的适合各自情况的反应条件以及起始材料,有可能例如,在一个反应步骤中仅将一个取代基用根据本发明的另一个取代基替代,或者在同一个反应步骤中可以将多个取代基用多个根据本发明的其他取代基来替代-。
具有化学式I的这些化合物的盐能以本身已知的方式进行制备。因此,例如,具有化学式I的化合物的酸加成盐是通过用一种适合的酸或一种合适的离子交换试剂进行处理来获得的,并且与碱的盐是通过用一种适合的碱或用一种合适的离子交换试剂进行处理来获得的。
具有化学式I的化合物的盐能以常规方式转化为游离的化合物I、酸加成盐(例如通过用一种合适的碱性化合物或用一种合适的离子交换试剂进行处理)以及碱盐(例如通过用一种合适的酸或用一种合适的离子交换试剂进行处理)。
具有化学式I的化合物的盐能以一种本身已知的方式转化为具有化学式I的化合物的其他盐、酸加成盐,例如转变成为其他酸加成盐,例如通过在一种合适的溶剂中用一种酸的合适的金属盐(比如一种钠、钡或银盐,例如用乙酸银)来处理一种无机酸的盐(比如盐酸盐),在该溶剂中,所形成的一种无机盐(例如氯化银)是不溶的并且因此从该反应混合物中沉淀出。
取决于程序或反应条件,具有成盐特性的这些具有化学式I的化合物能以游离形式或盐的形式获得。
具有化学式I的化合物和适当时其互变异构体(在每种情况下呈游离形式或呈盐形式)能够以可能的异构体之一的形式或以这些异构体的混合物的形式,例如以纯异构体(例如对映体和/或非对映异构体)形式或以异构体混合物(例如对映异构体混合物,例如外消旋体;非对映异构体混合物或外消旋体混合物)形式存在,取决于分子中存在的不对称碳原子的数目、绝对和相对构型和/或取决于分子中存在的非芳香族双键的构型;本发明涉及纯异构体以及可能的所有异构体混合物,并且在上下文的每种情况下,甚至在没有具体提及立体化学细节的每种情况下,都应该从这层意义上来理解。
处于游离形式或盐形式的具有化学式I的化合物的非对映异构体混合物或外消旋体的混合物(它们的获得可以取决于已选定的起始材料和程序)能够在这些组分的物理化学差异的基础上,例如通过分步结晶、蒸馏和/或层析法用一种已知的方法分离成纯的非对映异构体或外消旋体。
能够以类似方式获得的对映异构体混合物(例如外消旋体)可以通过已知方法拆分成光学对映体,例如通过从光学活性溶剂再结晶;通过在手性吸附剂上的层析法,例如在乙酰纤维素上的高效液相层析法(HPLC);借助于合适的微生物,通过用特异性固定酶裂解;通过形成包括化合物,例如使用手性冠醚,其中仅一个对映异构体被络合;或通过转化成非对映异构盐,例如通过使碱性最终产物外消旋体与光学活性酸(例如羧酸,例如樟脑、酒石酸或苹果酸或磺酸,例如樟脑磺酸)反应,并且分离能够以此方式获得的非对映异构体混合物,例如基于其不同溶解度通过分步结晶,从而给出非对映异构体,从这些非对映异构体可以通过合适的试剂(例如碱性试剂)的作用使所希望的对映异构体变成游离。
纯的非对映异构体或对映异构体能根据本发明来获得,不仅是通过分离合适的异构体混合物,还可以是通过普遍已知的非对映立体选择性或对映选择性合成的方法,例如通过根据本发明利用一种合适的立体化学的起始材料进行该方法。
可以通过将具有化学式I的化合物与一种适合的氧化剂(例如H2O2/尿素加合物)在酸酐(例如,三氟乙酸酐)存在下进行反应制备N-氧化物。此类氧化反应从文献,例如从药物化学杂志(J.Med.Chem.)32(12),2561-73,1989或WO 00/15615中已知。
如果这些单独的组分具有不同的生物活性,有利的是在每种情况下分离或合成该生物学上更有效的异构体,例如对映异构体或非对映异构体,或者异构体混合物,例如对映异构体混合物或非对映异构体混合物。
这些具有化学式I的化合物以及适当时其互变异构体(在每种情况下处于游离形式或盐形式)如果适当的话还能以水合物的形式获得和/或包括其他的溶剂,例如可以用于以固体形式存在的化合物的结晶的那些。
根据以下表1到6的这些化合物可以根据上述的这些方法来制备。随后的这些实例旨在说明本发明并且展示优选的具有化学式I的化合物。
表X:该表披露了具有化学式I-1a的39个取代基定义X.001至X.039:
其中Ra1、R2、G1、G2、G3、G4和G5是如以下定义的:
表X:
以及表X的化合物的N-氧化物。
表1:该表披露了具有化学式I-1a的39个化合物1.001至1.039,其中Xa1是S,并且Ra1、R2、G1、G2、G3、G4和G5是如表X中所定义的。例如,化合物No.1.010具有以下结构:
表2:该表披露了具有化学式I-1a的39个化合物2.001至2.039,其中Xa1是SO,并且Ra1、R2、G1、G2、G3、G4和G5是如表X中所定义的。
表3:该表披露了具有化学式I-1a的39个化合物3.001至3.039,其中Xa1是SO2,并且Ra1、R2、G1、G2、G3、G4和G5是如表X中所定义的。
表Y:该表披露了具有化学式I-2a的39个取代基定义Y.001至Y.039:
其中Ra2、R2、G1、G2、G3、G4和G5是如以下定义的:
表Y:
以及表Y的化合物的N-氧化物。
表4:该表披露了具有化学式I-2a的39个化合物4.001至4.039,其中Xa2是S,并且Ra2、R2、G1、G2、G3、G4和G5是如表Y中所定义的。
表5:该表披露了具有化学式I-2a的39个化合物5.001至5.039,其中Xa2是SO,并且Ra2、R2、G1、G2、G3、G4和G5是如表Y中所定义的。
表6:该表披露了具有化学式I-2a的39个化合物6.001至6.039,其中Xa2是SO2,并且Ra2、R2、G1、G2、G3、G4和G5是如表Y中所定义的。
根据本发明的具有化学式I的化合物在有害生物控制领域中是有预防和/或治疗价值的活性成分,即使是在低的施用量下,它们具有非常有利的杀生物谱并且是温血物种、鱼以及植物良好耐受的。根据本发明的这些活性成分作用于正常敏感的以及还有抗药的动物有害生物(如昆虫或蜱螨目的代表)的所有的或个别的发育阶段。根据本发明的活性成分的杀昆虫或杀螨活性可以本身直接显示,亦即或者立即或者仅在过去一些时间之后(例如在蜕皮期间)发生破坏有害生物;或间接显示,例如降低产卵和/或孵化率。
上述动物有害生物的实例是:
来自蜱螨目,例如,
下毛瘿螨属(Acalitus spp.)、针刺瘿螨属(Aculus spp)、窄瘿螨属(Acaricalusspp.)、瘤瘿螨属(Aceria spp.)、粗脚粉螨(Acarus siro)、钝眼蜱属(Amblyomma spp.)、锐缘蜱属(Argas spp.)、牛蜱属(Boophilus spp.)、短须螨属(Brevipalpus spp.)、苔螨属(Bryobia spp)、上三节瘿螨属(Calipitrimerus spp.)、皮螨属(Chorioptes spp.)、鸡皮刺螨(Derma-nyssus gallinae)、表皮螨属(Dermatophagoides spp)、始叶螨属(Eotetranychus spp)、瘿螨属(Eriophyes spp.)、半跗线螨属(Hemitarsonemus spp)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、小爪螨属(Olygonychus spp)、钝缘蜱属(Ornithodoros spp.)、侧多食跗线螨(Polyphagotarsone latus)、全爪螨属(Panonychusspp.)、桔芸锈螨(Phyllocoptruta oleivora)、植食螨(Phytonemus spp.)、跗线螨属(Polyphagotarsonemus spp)、痒螨属(Psoroptes spp.)、扇头蜱属(Rhipicephalusspp.)、根嗜螨属(Rhizoglyphus spp.)、疥螨属(Sarcoptes spp.)、狭跗线螨属(Steneotarsonemus spp)、跗线属(Tarsonemus spp.)以及叶螨属(Tetranychus spp.);
来自虱目,例如,
血虱属、长颚虱属、人虱属、天疱疮属以及木虱属;
来自鞘翅目,例如,
缺隆叩甲属、欧洲鳃角金龟(Amphimallon majale)、东方异丽金龟、花象属、蜉金龟属、玉米拟花萤(Astylus atromaculatus)、Ataenius属、甜菜隐食甲(Atomarialinearis)、甜菜胫跳甲、萤叶甲属(Cerotoma spp)、单叶叩甲属、根颈象属、绿金龟、象虫属、圆头犀金龟属、圆头犀金龟属、根萤叶甲属、阿根廷兜虫(Diloboderus abderus)、食植瓢虫属、Eremnus属、黑异爪蔗金龟、咖啡果小蠹、Lagria vilosa、马铃薯甲虫、稻水象属、Liogenys属、Maecolaspis属、栗色绒金龟、Megascelis属、Melighetes aeneus、金龟属、Myochrous armatus、锯谷盗属、耳喙象属(Otiorhynchus spp.)、鳃角金龟属、斑象属、丽金龟属、油菜跳甲属、Rhyssomatus aubtilis、劫根蠹属、金龟子科、米象属、麦蛾属、伪切根虫属、Sphenophorus属、大豆茎象、拟步行虫属、拟谷盗属以及斑皮蠹属;
来自双翅目,例如,
伊蚊属、疟蚊属、高梁芒蝇、橄榄果实蝇(Bactrocea oleae)、花园毛蚊、迟眼蕈蚊属(Bradysia spp.)、红头丽蝇、小条实蝇属、金蝇属、库蚊属、黄蝇属、寡鬃实蝇属、地种蝇属、黑腹果蝇、厕蝇属、胃蝇属、Geomyza tripunctata、舌蝇属、皮蝇属、虱蝇属、斑潜蝇属Liriomyza、绿蝇属、潜蝇属、家蝇属、狂蝇属、瘿蚊属、瑞典麦秆蝇、藜泉蝇、草种蝇属、绕实蝇属、Rivelia quadrifasciata、Scatella属、蕈蚊属、刺蝇属、虻属、绦虫属及大蚊属;
来自半翅目,例如,
瘤缘蝽(Acanthocoris scabrator)、绿蝽属、苜蓿盲蝽、Amblypelta nitida、海虾盾缘蝽(Bathycoelia thalassina)、土长蝽属、臭虫属、Clavigralla tomentosicollis、盲蝽属(Creontiades spp.)、可可瘤盲蝽、Dichelops furcatus、棉红蝽属、Edessa属、美洲蝽属(Euchistus spp.)、六斑菜蝽(Eurydema pulchrum)、扁盾蝽属、茶翅蝽、具凹巨股长蝽(Horcias nobilellus)、稻缘蝽属、草盲蝽属、热带硕蚧属、卷心菜斑色蝽(Murgantiahistrionic)、Neomegalotomus属、烟盲蝽(Nesidiocoris tenuis)、绿蝽属、拟长蝽(Nysiussimulans)、Oebalus insularis、皮蝽属、壁蝽属、红猎蝽属、可可盲蝽象、Scaptocoriscastanea、黑蝽属(Scotinophara spp.)、Thyanta属、锥鼻虫属、木薯网蝽(Vatigailludens);
无网长管蚜属、Adalges spp、Agalliana ensigera、塔尔吉奥尼木虱(Agonoscenatargionii)、粉虱属(Aleurodicus spp.)、刺粉虱属(Aleurocanthus spp)、甘蔗穴粉虱、软毛粉虱(Aleurothrixus floccosus)、甘蓝粉虱(Aleyrodes brassicae)、棉叶蝉(Amarascabiguttula)、檬果长突叶蝉(Amritodus atkinson)、肾圆盾蚧属、蚜科、蚜属、蚧属(Aspidiotus spp.)、茄沟无网蚜、马铃薯木虱(Bactericera cockerelli)、小粉虱属、短尾蚜属(Brachycaudus spp)、甘蓝蚜、喀木虱属、双尾蚜(Cavariella aegopodii Scop.)、蜡蚧属、褐圆蚧、网籽草叶圆蚧、大叶蝉属(Cicadella spp)、大白叶蝉(Cofana spectra)、隐瘤蚜属、叶蝉属(Cicadulina spp)、褐软蚧、玉米黄翅叶蝉、裸粉虱属、柑橘木虱、麦双尾蚜、西圆尾蚜属、小绿叶蝉属、苹果绵蚜、葡萄斑叶蝉属、蜡蛤属、赤桉木虱(Glycaspisbrimblecombei)、菜缢管蚜、大尾蚜属(Hyalopterus spp)、超瘤蚜种、檬果绿叶蝉(Idioscopus clypealis)、非洲叶蝉(Jacobiasca lybica)、灰飞虱属、球坚蚧、蛎盾蚧属、萝卜蚜(Lopaphis erysimi)、Lyogenys maidis、长管蚜属、沫蝉属(Mahanarva spp)、蛾蜡蝉科(Metcalfa pruinosa)、麦无网蚜、Myndus crudus、瘤蚜属、台湾韭蚜、黑尾叶蝉属、褐飞虱属(Nilaparvata spp.)、梨大绿蚜、狗牙根草芥壳虫(Odonaspis ruthae)、寄生甘蔗绵蚜、杨梅缘粉虱、考氏木虱、片盾蚧属、瘿绵蚜属、玉米蜡蝉、扁角飞虱属、忽布疣蚜、根瘤蚜属、动性球菌属、白盾蚧属、粉蚧属、棉盲蝽(Pseudatomoscelis seriatus)、木虱属、棉蚧(Pulvinaria aethiopica)、笠圆盾蚧属、Quesada gigas、电光叶蝉(Recilia dorsalis)、缢管蚜属、黑盔蚧属、带叶蝉属、二叉蚜属、麦蚜属(Sitobion spp.)、白背飞虱、三角苜蓿跳虫(Spissistilus festinus)、条斑飞虱(Tarophagus Proserpina)、声蚜属、粉虱属、Tridiscus sporoboli、葵粉蚧属(Trionymus spp.)、非洲木虱、桔矢尖蚧、火焰斑叶蝉(Zygina flammigera)、Zyginidia scutellaris;
来自膜翅目,例如,
顶切叶蚁属、三节叶蜂属(Arge spp.)、布切叶白蚁属、茎叶蜂属、松叶蜂属、锯角叶蜂科、松叶蜂(Gilpinia polytoma)、梨实蜂属、毛蚁属、小黄家蚁、新松叶蜂属、农蚁属、Slenopsis invicta、水蚁属以及胡蜂属;
来自等翅目,例如,
家白蚁属、白蚁(Corniternes cumulans)、楹白蚁属、大白蚁属、澳白蚁属、小白蚁属、散白蚁属、热带火蚁
来自鳞翅目,例如,
长翅卷蛾属、褐带卷蛾属、透翅蛾属、地夜蛾属、棉叶虫、Amylois属、黎豆夜蛾、黄卷蛾属、银蛾属(Argyresthia spp.)、带卷蛾属、丫纹夜蛾属、棉潜蛾、玉米楷夜蛾、粉斑螟蛾、桃蛀果蛾、禾草螟属、卷叶蛾属、越蔓桔草螟(Chrysoteuchia topiaria)、葡萄果蠹蛾、卷叶螟属、云卷蛾属、纹卷蛾属、鞘蛾属、磷翅目粉蝶、Cosmophila flava、草螟属、大菜螟、苹果异形小卷蛾、黄杨木蛾、小卷蛾属、黄杨绢野螟、杆草螟属、苏丹棉铃虫、金刚钻属、非洲茎螟、粉螟属、叶小卷蛾属(Epinotia spp)、细斑灯蛾、Etiella zinckinella、花小卷蛾属、环针单纹蛾、黄毒蛾属、切根虫属、Feltia jaculiferia、Grapholita属、绿青虫蛾、实夜蛾属、菜螟、切叶野螟属(Herpetogramma spp)、美国白蛾、番茄蠹蛾、Lasmopalpuslignosellus、旋纹潜叶蛾、潜叶细蛾属、葡萄花翅小卷蛾、Loxostege bifidalis、毒蛾属、潜蛾属、幕枯叶蛾属、甘蓝夜蛾、烟草天蛾、Mythimna属、夜蛾属、秋尺蛾属、Orniodesindica、欧洲玉米螟、超小卷蛾属、褐卷蛾属、小眼夜蛾、蛀茎夜蛾、Pectinophoragossypiela、咖啡潜叶蛾、一星黏虫、马铃薯麦蛾、菜粉蝶、粉蝶属、小菜蛾、芽蛾属、尺叶蛾属、薄荷灰夜蛾、西方豆地香(Richia albicosta)、白禾螟属(Scirpophaga spp.)、蛀茎夜蛾属、长须卷蛾属、灰翅夜蛾属、棉大卷叶螟、兴透翅蛾属、异舟蛾属、卷叶蛾属、粉纹夜蛾、番茄斑潜蝇、以及巢蛾属;
来自食毛目,例如,
畜虱属和啮毛虱属;
来自直翅目,例如,
蠊属、小蠊属、蝼蛄属、马德拉蜚蠊、飞蝗属、北痣蟋蟀(Neocurtillahexadactyla)、大蠊属、痣蟋蟀属(Scapteriscus spp)、以及沙漠蝗属;
来自啮虫目,例如,
虱啮属(Liposcelis spp);
来自蚤目,例如,
角叶蚤属、栉头蚤属和印鼠客蚤;
来自缨翅目,例如,
Calliothrips phaseoli、花蓟马属、阳蓟马属、褐带蓟马属、单亲蓟马属(Parthenothrips spp.)、橙花苷硬蓟马(Scirtothrips aurantii)、豆蓟马(Sericothripsvariabilis)、带蓟马属、蓟马属;
来自缨尾目,例如,衣鱼(Lepisma saccharina)。
根据本发明的这些活性成分可以用于控制,即限制或毁灭,出现在特别是在植物上,尤其是在农业、园艺和森林中的有用植物和观赏植物上,或在这样的植物的器官如果实、花、叶、秆、根茎或根上的上述类型的有害生物,并且在某些情况下,甚至在较晚的时间点形成的植物器官上仍然针对这些有害生物的保护。
合适的目标作物特别是谷物,如小麦、大麦、黑麦、燕麦、稻、玉米或高粱;甜菜,如糖或饲料甜菜;果实,例如仁果,核果或无核水果,如苹果、梨、李子、桃、扁桃、樱桃或浆果,例如草莓、树莓或黑莓;豆科农作物,如豆类、滨豆、豌豆或大豆;油料作物,如油菜、芥菜、婴栗、橄榄、葵花、椰子、蓖麻、可可或落花生;瓜类作物,如南瓜、黄瓜或甜瓜;纤维植物,如棉花、亚麻、大麻或黄麻;柑橘属果实,如桔、柠檬、葡萄柚或橘;蔬菜,如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯或甜椒;樟科植物,如鳄梨、樟属或樟脑;并且还有烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、葡萄藤、啤酒花、车前草科、橡胶植物和观赏植物。
例如,本发明可以用于任何以下观赏植物物种:藿香蓟属(Ageratum spp.)、心叶假面花属(Alonsoa spp.)、银莲花属、南非葵属坎普森斯(Anisodontea capsenisis)、春黄菊属、金鱼草、紫菀属、秋海棠属(例如,丽格海棠(B.elatior)、四季海棠(B.semperflorens)、土柏瑞海棠(B.tubéreux))、叶子花属、屈曲叶短毛菌属、芸苔属(观赏)、蒲包花属(Calceolaria spp.)、甜辣椒、长春花属、美人蕉属、矢车菊属、菊属、瓜叶菊属(瓜叶菊海事(C.maritime))、金鸡菊属、红景天、火红萼距花、大丽花属、翠雀属(Delphinium spp.)、荷包牡丹(Dicentra spectabilis)、Dorotheantus spp.、洋桔梗、连翘属、倒挂金钟属、天竺葵鼠曲草、非洲菊属、千日红、天芥菜属、向日葵属、木槿属、霍滕西亚属(Hortensia spp.)、绣球花属、嫣红蔓(Hypoestes phyllostachya)、凤仙属(非洲凤仙花)、爱瑞丝(Iresines spp)、高凉菜属(Kalanchoe spp.)、马缨丹(Lantana camara)、三月花葵(Lavatera trimestris)、狮耳花、百合属、番杏科肉质植物属(Mesembryanthemumspp.)、猴面花属、美国薄荷属、龙面花属、万寿菊属、石竹属(康乃馨)、美人蕉属、加州酢浆草属(Oxalis spp.)、雏菊属(Bellis spp.)、天竺葵属(Pelargonium spp.)(盾叶天竺葵(P.peltatum)、天竺葵(P.Zonale))、堇菜属(Viola spp.)(三色堇)、矮牵牛属(Petuniaspp.)、草夹竹桃属(Phlox spp.)、香茶菜属(Plecthranthus spp.)、一品红(Poinsettiaspp.)、爬山属虎(北美爬山虎(P.quinquefolia)、地锦(P.tricuspidata))、报春属(Primula spp.)、毛茛属(Ranunculus spp.)、杜鹃属(Rhododendron spp.)、蔷薇属(玫瑰)、金光菊属、紫罗兰属、鼠尾草属、紫扇花(Scaevola aemola)、蛾蝶花(Schizanthuswisetonensis)、景天属、茄属、素菲妮属(Surfinia spp.)、万寿菊属(Tagetes spp.)、尼口缇娜属(Nicotinia spp.)、马鞭草属、菰属(Zinnia spp.)以及其他花坛植物。
例如,本发明可以用于任何以下蔬菜物种:葱属(大蒜、洋葱、火葱(A.oschaninii)、韭葱、冬葱、大葱)、雪维菜、芹菜属(Apium graveolus)、天门冬属、甜菜、芸苔属(Brassica spp.)(甘蓝、大白菜、芜青)、甜辣椒(Capsicum annuum)、鹰嘴豆、苣荬菜、毛菊苣(Cichorum spp.)(菊苣、苦苣)、西瓜、黄瓜属(黄瓜、西瓜(C.Melo))、南瓜属(西葫芦、笋瓜)、菜蓟属(菜蓟、刺苞菜蓟)、胡萝卜、茴香、金丝桃属、莴苣属、番茄属(番茄、樱桃番茄)、薄荷属、罗勒属(Ocimum basilicum)、香芹(Petroselinum crispum)、菜豆属(菜豆、多花菜豆)、豌豆、萝卜(Raphanus sativus)、食用大黄、迷迭香属、鼠尾草属(Salvia spp.)、鸦葱(Scorzonera hispanica)、茄子(Solanum melongena)、石竹目、新缬草属属(Valerianella spp.)(野苣、棉毛岩(V.eriocarpa))和蚕豆。
优选的观赏物种包括非洲紫罗兰、秋海棠、大丽花、非洲菊、八仙花、马鞭草、蔷薇、金盏花、一品红、紫菀、矢车菊、金鸡菊类、翠雀属、美国薄荷属、草夹竹桃、黄雏菊、景天、矮牵牛花、堇菜属、凤仙花、天竺葵、菊花、毛茛属植物、倒挂金钟、鼠尾草、霍滕西亚、迷迭香、鼠尾草、圣约翰草(St.Johnswort)、薄荷、甜椒、番茄和黄瓜。
根据本发明的这些活性成分尤其适合于控制棉花、蔬菜、玉米、水稻以及大豆作物上的扁豆蚜、黄瓜条叶甲、烟芽夜蛾、桃蚜、小菜蛾以及海灰翅夜蛾。根据本发明的这些活性成分另外尤其适合于控制甘蓝夜蛾(优选地在蔬菜上)、苹果蠹蛾(优选地在苹果上)、小绿叶蝉(优选地在蔬菜、葡萄园里)、马铃薯叶甲(优选地在马铃薯上)以及二化螟(优选地在水稻上)。
在另一个方面,本发明还可涉及控制由植物寄生的线虫(内寄生的-、半内寄生的-以及外寄生的线虫)对植物或其部分引起损害的一种方法,尤其是以下植物寄生的线虫,如根结线虫(root knot nematodes)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)、花生根结线虫(Meloidogyne arenaria)以及其他根结线虫属种类(Meloidogyne species);孢囊形成线虫(cyst-forming nematodes)、马铃薯金线虫(Globodera rostochiensis)以及其他球孢囊线虫属种类(Globodera species);禾谷孢囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、红三叶异皮线虫(Heterodera trifolii)、以及其他异皮线虫属种类(Heterodera species);种瘿线虫(Seed gall nematodes)、粒线虫属种类(Anguina species);茎及叶面线虫(Stem andfoliar nematodes)、滑刃线虫属种类(Aphelenchoides species);刺毛线虫(Stingnematodes)、长尾刺线虫(Belonolaimus longicaudatus)以及其他刺线虫属种类;松树线虫(Pine nematodes)、松材线虫(Bursaphelenchus xylophilus)以及其他伞滑刃属种类(Bursaphelenchus species);环形线虫(Ring nematodes)、环线虫属种类(Criconemaspecies)、小环线虫属种类(Criconemella species)、轮线虫属种类(Criconemoidesspecies)、中环线虫属种类(Mesocriconema species);茎及鳞球茎线虫(Stem and bulbnematodes)、腐烂茎线虫(Ditylenchus destructor)、鳞球茎茎线虫(Ditylenchusdipsaci)以及其他茎线虫属种类(Ditylenchus species);锥线虫(Awl nematodes)、锥线虫属种类(Dolichodorus species);螺旋线虫(Spiral nematodes)、多头螺旋线虫(Heliocotylenchus multicinctus)以及其他螺旋线虫属种类(Helicotylenchusspecies);鞘及鞘形线虫(Sheath and sheathoid nematodes)、鞘线虫属种类(Hemicycliophora species)以及半轮线虫属种类(Hemicriconemoides species);潜根线虫属种类(Hirshmanniella species);支线虫(Lance nematodes)、冠线虫属种类(Hoploaimus species);假根结线虫(false rootknot nematodes)、珍珠线虫属种类(Nacobbus species);针状线虫(Needle nematodes)、横带长针线虫(Longidoruselongatus)以及其他长针线虫属种类(Longidorus species);大头针线虫(Pinnematodes)、短体线虫属种类(Pratylenchus species);腐线虫(Lesion nematodes)、花斑短体线虫(Pratylenchus neglectus)、穿刺短体线虫(Pratylenchus penetrans)、弯曲短体线虫(Pratylenchus curvitatus)、古氏短体线虫(Pratylenchus goodeyi)以及其他短体线虫属种类(Pratylenchus species);柑桔穿孔线虫(Burrowing nematodes)、香蕉穿孔线虫(Radopholus similis)以及其他内侵线虫属种类(Radopholus species);肾形线虫(Reniform nematodes)、罗柏氏盘旋线虫(Rotylenchus robustus)、肾形盘旋线虫(Rotylenchus reniformis)以及其他盘旋线虫属种类(Rotylenchus species);盾线虫属种类(Scutellonema species);短粗根线虫(Stubby root nematodes)、原始毛刺线虫(Trichodorus primitivus)以及其他毛刺线虫属种类(Trichodorus species)、拟毛刺线虫属种类(Paratrichodorus species);矮化线虫(Stunt nematodes)、马齿苋矮化线虫(Tylenchorhynchus claytoni)、顺逆矮化线虫(Tylenchorhynchus dubius)以及其他矮化线虫属种类(Tylenchorhynchus species);柑桔线虫(Citrus nematodes)、穿刺线虫属种类(Tylenchulus species);短剑线虫(Dagger nematodes)、剑线虫属种类(Xiphinemaspecies);以及其他植物寄生的线虫种类,如亚粒线虫属(Subanguina spp.)、Hypsoperine属、大刺环线虫属(Macroposthonia spp.)、Melinius属、刻点胞囊属(Punctodera spp.)、以及五沟线虫属(Quinisulcius spp.)。
本发明的这些化合物还具有针对软体动物的活性。这些软体动物的实例包括,例如苹果螺科;阿勇蛞蝓属(Arion)(灰黑阿勇蛞蝓(A.ater)、环斑阿勇蛞蝓(A.circumscriptus)、庭院阿勇蛞蝓(A.hortensis)、红棕阿勇蛞蝓(A.rufus));巴蜗牛科(灌木巴蜗牛(Bradybaena fruticum));蜗牛属(庭院蜗牛(C.hortensis),森林蜗牛(C.nemoralis));ochlodina;灰蛞蝓属(Deroceras)(野灰蛞蝓(D.agrestis)、D.empiricorum、田灰蛞蝓(D.laeve)、庭园灰蛞蝓(D.reticulatum));圆盘螺属(Discus)(D.rotundatus);Euomphalia;土蜗属(Galba)(截形土蜗(G.trunculata));小蜗牛属(Helicelia)(伊塔拉小蜗牛(H.itala)、布维小蜗牛(H.obvia));大蜗牛科Helicigonaarbustorum);Helicodiscus;大蜗牛属(Helix)(开放大蜗牛(H.aperta));蛞蝓属(Limax)(灰黑蛞蝓(L.cinereoniger)、黄蛞蝓(L.flavus),边缘蛞蝓(L.marginatus),大蛞蝓(L.maximus),柔蛞蝓(L.tenellus));椎实螺属(Lymnaea);Milax(M.gagates、M.marginatus、M.sowerbyi);钻螺属(Opeas);瓶螺属(Pomacea)(P.canaticulata);瓦娄蜗牛属(Vallonia)和Zanitoides。
术语“作物”应理解为还包括通过使用重组DNA技术进行了转化而能够合成一种或多种选择性作用毒素的作物植物,这些毒素例如已知,例如来自产毒素的细菌,尤其是芽孢杆菌属的那些。
可通过所述转基因植物表达的毒素包括,例如杀昆虫蛋白质,例如杀昆虫蛋白质,例如来自于枯草芽孢杆菌或日本甲虫芽孢杆菌的杀昆虫蛋白质;或来自于苏云金芽孢杆菌的杀昆虫蛋白质,例如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质,例如光杆状茵属或致病杆菌属,例如发光光杆状茵、嗜线虫致病杆菌;由动物产生的毒素,例如蝎毒素、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,例如链霉菌毒素;植物凝集素,例如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类;蛋白酶抑制剂,例如胰蛋白酶抑制剂、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),例如蓖麻蛋白、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,例如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,例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、几丁酶和葡聚糖酶。
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区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。在经修饰毒素的情况下,天然产生的毒素的一个或多个氨基酸被置换。在这种氨基酸置换中,优选将非天然存在的蛋白酶识别序列插入毒素中,例如在Cry3A055的情况下,一种组织蛋白酶-G-识别序列被插入Cry3A毒素(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的普通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-0 367 474、EP-A-0 401 979以及WO 90/13651中已知。
包含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)和蛾(鳞翅目)中发现。
包含一种或多种编码杀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,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del’Hobit)27,F-31 790圣苏维尔(St.Sauveur),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盐的耐受性。
2.Bt176玉米,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del’Hobit)27,F-31 790圣苏维尔(St.Sauveur),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玉米还转基因地表达PAT酶以达到对除草剂草丁膦铵盐的耐受性。
3.MIR604玉米,来自先正达种子公司,霍比特路27,F-31 790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。此类转基因玉米植物的制备描述于WO 03/018810中。
4.MON 863玉米,来自孟山都欧洲公司(Monsanto Europe S.A.)270-272特弗伦大道(Avenue de Tervuren),B-1150布鲁塞尔(Brussels),比利时,登记号C/DE/02/9。MON863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司,270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/ES/96/02。
6.1507玉米,来自先锋海外公司(Pioneer Overseas Corporation),特德斯科大道(Avenue Tedesco),7B-1160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盐的耐受性。
7.NK603×MON 810玉米,来自孟山都公司(Monsanto Europe S.A.),270-272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NK 603和MON 810杂交,由常规育种的杂交玉米品种构成。NK603×MON 810玉米转基因表达由土壤杆菌属菌株CP4获得的CP4EPSPS蛋白质,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。
抗昆虫的植物的转基因作物还描述于BATS(生物安全与可持续发展中心(ZentrumBiosicherheit und Nachhaltigkeit),BATS中心(Zentrum BATS),克拉斯崔舍(Clarastrasse)13,巴塞尔(Basel)4058,瑞士)报告2003(http://bats.ch)中。
术语“作物”应当被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具有选择性作用的抗病原物质的作物,这些抗病原物质例如所谓的“病程相关蛋白”(PRP,参见例如EP-A-0 392 225)。此类抗病原物质以及能够合成此类抗病原物质的转基因植物的实例例如从EP-A-0 392225、WO 95/33818和EP-A-0 353 191是已知的。生产此类转基因植物的方法对于本领域的技术人员通常是已知的并且描述于例如以上提及的公开物中。
作物也可以经修饰以增加对真菌(例如镰刀霉、炭疽病或疫霉菌)、细菌(例如假单胞菌)或病毒(例如马铃薯卷叶病毒、番茄斑萎病毒、黄瓜花叶病毒)病原体的抗性。
作物还包括那些具有对线虫(如大豆异皮线虫)的增加的抗性的作物。
具有对非生物性胁迫的耐受力的作物包括那些例如通过NF-YB或本领域中已知的其他蛋白质的表达具有对干旱、高盐、高温、寒冷、霜或光辐射的增加的耐受力的作物。
可以通过这样的转基因植物表达的抗病原物质包括,例如离子通道阻断剂,如钠和钙通道的阻断剂,例如病毒的KP1,KP4或KP6毒素;芪合酶、联苄合酶;几丁质酶;葡聚糖酶;所谓的“病程相关蛋白”(PRP,参见例如EP-A-0 392 225);通过微生物产生的抗病原物质,例如植物病原防御中涉及的肽抗生素类或杂环抗生素类(参见例如WO 95/33818)或蛋白质或多肽因子(所谓的“植物病害抗性基因”,如WO 03/000906所述)。
根据本发明的组合物的其他使用领域是保护所储存的货物和储藏室并且保护原材料,例如木材、纺织品、地板或建筑物,以及在卫生部门中,尤其是保护人类、家畜以及多产的牲畜免遭所提及类型的有害生物。
本发明还提供了一种用于控制有害生物(如蚊科和其他的疾病媒介物;同样参见http://www.who.int/malaria/vector_control/irs/en/)的方法。在一个实施例中,用于控制有害生物的方法包括通过涂刷、轧制、喷雾、涂布或浸渍,向该目标有害生物、它们的场所或表面或基质施用本发明的组合物。通过举例,通过本发明的方法预期了一种表面(如,墙、天花板或地板表面)的IRS(室内滞留喷雾)施用。在另一个实施例中,考虑到了将此类组合物施用于一种基底,如无纺或织物材料,该材料处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中使用)。
在一个实施例中,用于控制此类有害生物的方法包括向该目标有害生物、它们的场所或表面或基质施用一种杀有害生物有效量的本发明的组合物,以便于在该表面或基质上提供有效的滞留的杀有害生物活性。此类施用可以通过涂刷、轧制、喷雾、涂布或浸渍本发明的杀有害生物组合物来进行。通过举例,本发明的方法预期了一种表面(如,墙、天花板或地板表面)的IRS施用,以便于在该表面上提供有效的滞留的杀有害生物活性。在另一个实施例中,预期了施用此类组合物以用于在一种基底上的有害生物的滞留的控制,该基底是例如处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中使用)的织物材料。
有待处理的基底(包括无纺物、织物或网织品)可以由天然纤维,如,棉花、拉菲亚树叶纤维、黄麻、亚麻、剑麻、粗麻布或羊毛,或合成纤维,如聚酰胺、聚酯、聚丙烯、聚丙烯腈等等制成。聚酯是特别适合的。纺织品处理的方法是已知的,例如WO 2008/151984、WO2003/034823、US 5631072、WO 2005/64072、WO 2006/128870、EP 1724392、WO 2005113886或WO 2007/090739。
根据本发明的这些组合物的用途的其他范围是针对所有观赏树木连同所有种类的果树和坚果树的树木注射/树干处理领域。
在树木注射/树干处理领域中,根据本发明的这些化合物特别适合于对抗来自上述的鳞翅目和来自鞘翅目的钻木昆虫,尤其是对抗下表A和B中列出的钻木虫:
表A.具有经济重要性的外来钻木虫的实例。
表B.具有经济重要性的本地钻木虫的实例。
本发明也可以用于控制任何可以存在于草坪草中的昆虫有害生物,包括例如甲虫、毛虫、火蚁、地面珍珠(ground pearls)、千足虫、潮虫、螨虫、蝼蛄、介壳虫、粉蚧蜱、沫蝉、南方麦小蝽以及蛴螬。本发明可以用于控制处于其生命周期的多种阶段的昆虫有害生物,包括卵、幼虫、若虫和成虫。
具体而言,本发明可用于控制用草坪草的根部喂养的昆虫有害生物,该昆虫有害生物包括蛴螬(如圆头犀金龟属(Cyclocephala spp.)(例如标记的金龟子,C.lurida)、Rhizotrogus spp.(例如欧洲金龟子,欧洲切根鳃金龟(R.majalis))、黄栌属(Cotinusspp.)(例如绿六月甲虫(Green June beetle),C.nitida)、弧丽金龟属(Popillia spp.)(例如日本甲虫,龟纹瓢虫(P.japonica))、鳃角金龟属(Phyllophaga spp.)(例如五月/六月甲虫)、Ataenius属(例如草坪草黑金龟(Black turfgrass ataenius),A.spretulus)、绒毛金龟属(Maladera spp.)(例如亚洲花园甲虫(Asiatic garden beetle),M.castanea)以及Tomarus属),地面珍珠(硕蚧属(Margarodes spp.)),蝼蛄(褐黄色的、南方的、以及短翅的;痣蟋蟀属(Scapteriscus spp.),非洲蝼蛄(Gryllotalpa africana))以及大蚊幼虫(leatherjackets)(欧洲大蚊(European crane fly),大蚊属(Tipula spp.))。
本发明还可以用于控制茅草住宅的草坪草的昆虫有害生物,该昆虫有害生物包括粘虫(如秋夜蛾(fall armyworm)草地贪夜蛾(Spodoptera frugiperda),和常见夜蛾一星黏虫(Pseudaletia unipuncta))、切根虫,象鼻虫(尖隐喙象属(Sphenophorus spp.),如S.venatus verstitus和牧草长喙象(S.parvulus))以及草地螟(如草螟属(Crambus spp.)和热带草地螟,Herpetogramma phaeopteralis)。
本发明还可以用于控制在地上生长的并用草坪草叶子喂养的草坪草中的昆虫有害生物,该昆虫有害生物包括麦小蝽(如南方麦小蝽,南方杆长蝽(Blissus insularis))、狗牙根螨(Bermudagrass mite)(Eriophyes cynodoniensis)、盖氏虎尾草粉蚧(草竹粉蚧(Antonina graminis))、两线沫蝉(Propsapia bicincta)、叶蝉、切根虫(夜蛾科)、以及麦二叉蚜。
本发明还可以用于控制草坪草中的其他有害生物,如在草坪中创建蚁巢的外引红火蚁(红火蚁(Solenopsis invicta))。
在卫生领域中,根据本发明的这些组合物是有效地对抗外寄生虫如硬蜱、软蜱、疥螨、秋螨、蝇(叮咬和舔舐)、寄生性蝇幼虫,虱、发虱、鸟虱和蚤。
此类寄生虫的实例是:
虱目:血虱属、长腭虱属、人虱属以及阴虱属、管虱属。
食毛目:毛羽虱属、短角鸟虱属、鸭虱属、牛羽虱属、Werneckiella属、Lepikentron属、畜虱属、啮毛虱属以及猫羽虱属。
双翅目及长角亚目和短角亚目,例如伊蚊属、按蚊属、库蚊属、蚋属、真蚋属、白蛉属、罗蛉属、库蠓属、斑虻属、驼背虻属、黄虻属、虻属、麻虻属、Philipomyia spp.、蜂虱蝇属、家蝇属、齿股蝇属、螫蝇属、黑角蝇属、莫蝇属、厕蝇属、舌蝇属、丽蝇属、绿蝇属、金蝇属、污蝇属、麻蝇属、狂蝇属、皮蝇属、胃蝇属、虱蝇属、羊虱蝇属和蜱蝇属。
蚤目,例如蚤属、栉头蚤属、客蚤属、角叶蚤属。
异翅目,例如臭虫属、锥蝽属、红猎蝽属、锥蝽属。
蜚蠊目,例如东方蜚蠊、美洲大蠊、德国小蠊以及夏柏拉蟑螂属。
蜱螨亚纲(螨科)和后气门目和中气门目,例如锐缘蜱属、钝缘蜱属、耳蜱属、硬蜱属、钝眼蜱属、牛蜱属、革蜱属、血蜱属、璃眼蜱属、扇头蜱属、皮刺螨属、刺利螨属、肺刺螨属、胸刺螨属和瓦螨属。
轴螨目(前气门亚目)和粉螨目(无气门亚目),例如蜂盾螨属、姬螯属、禽螯螨属、肉螨属、疮螨属、蠕形螨属、恙螨属、牦螨属、粉螨属、食酪螨属、嗜木螨属、颈下螨属、翅螨属、痒螨属、皮螨属、耳疥螨属、疥螨属、耳螨属、鸟疥螨属、胞螨属以及鸡雏螨属。
根据本发明的这些组合物还适用于保护材料如木材、纺织品、塑料、粘合剂、胶、漆料、纸张和卡片、皮革、地板和建筑等免受昆虫侵染。
根据本发明的组合物可以用于例如抵抗以下有害生物:甲虫,例如北美家天牛、长毛天牛、家具窃蠹、红毛窃蠹、梳角细脉窃蠹、石斛、松芽枝窃蠹、松产品窃蠹、褐粉蠹、非洲粉蠹、南方粉蠹、栎粉蠹、柔毛粉蠹、胸粉蠹、鳞毛粉蠹、材小蠹属、条木小蠹属、咖啡黑长蠹、树长蠹、棕异翅长蠹、双棘长蠹属与竹长蠹;以及膜翅类昆虫,例如蓝黑树蜂、云杉大树蜂、泰加大树蜂与大树蜂;以及白蚁,例如欧洲木白蚁、麻头堆砂白蚁、印巴结构木异白蚁、黄胸散白蚁、桑特散白蚁、散白蚁、达尔文澳白蚁、内华达古白蚁与家白蚁;以及蛀虫,例如衣鱼。
根据本发明的化合物可以按未经修饰的形式用作杀有害生物剂,但它们大体上以多种方式使用配制辅助剂(如载体、溶剂以及表面活性物质)被配制成组合物。这些配制品可以处于不同的实体形式,例如,处于以下形式:撒粉剂、凝胶、可湿性粉剂、水可分散性颗粒剂、水可分散性片剂、泡腾压缩片剂、可乳化的浓缩物、微可乳化浓缩物、水包油乳剂、可流动油、水性分散体、油性分散体、悬乳剂、胶囊悬浮液、可乳化的颗粒剂、可溶性液体、水可溶性浓缩物(以水或水混溶性有机溶剂作为载体)、浸渍的聚合物膜或处于已知的其他形式,例如从关于杀有害生物剂的FAO和WHO标准的发展和使用的手册(Manual onDevelopment and Use of FAO and WHO Specifications for Pesticides),联合国,二次修订,第5版,(2010)中已知的。此类配制品可以直接使用或者可以使用前稀释再使用。可以利用例如水、液体肥料、微量营养素、生物有机体、油或溶剂来稀释。
可以通过例如将活性成分与配制辅助剂混合来制备这些配制品以便获得处于精细分散固体、颗粒、溶液、分散体或乳液形式的组合物。这些活性成分还可以与其他辅助剂(例如精细分散固体、矿物油、植物或动物的油、改性的植物或动物的油、有机溶剂、水、表面活性物质或它们的组合)来一起配制。
这些活性成分还可以被包含于非常精细的微胶囊中。微胶囊在多孔载体中包含活性成分。这使活性成分能以受控的量值(例如,缓慢释放)释放到环境中。微胶囊通常具有从0.1至500微米的直径。它们含有的活性成分的量按重量计是胶囊重量的约从25%至95%。这些活性成分可以处于整体性的固体的形式、处于固体或液体分散体中的精细颗粒的形式或处于合适溶液的形式。包囊的膜可以包括例如天然的或合成的橡胶,纤维素、苯乙烯/丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯或化学改性的聚合物以及淀粉黄原酸盐、或本领域的普通技术人员已知的其他聚合物。可替代地,可以形成非常精细的微胶囊,其中活性成分在基础物质的固体基质中是以精细分散颗粒的形式被包含的,但这些微胶囊本身未经包裹。
适合于制备根据本发明的这些组合物的配制辅助剂本身是已知的。作为液体载体可以使用:水、甲苯、二甲苯、石油醚、植物油、丙酮、甲基乙基酮、环己酮、酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、碳酸丁烯酯、氯苯、环己烷、环己醇、乙酸烷基酯的乙酸、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对-二乙基苯、二甘醇、松脂酸二乙二醇酯、二甘醇乙醚、二甘醇乙基醚、二甘醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲基醚、双丙甘醇二苯甲酸酯、二丙二醇、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乳酸乙酯、乙二醇、乙二醇丁基醚、乙二醇甲基醚、γ-丁内酯、丙三醇、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸异戊基酯、乙酸异冰片基酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异亚丙基丙酮、甲氧基丙醇、甲基异戊基酮、甲基异丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、间二甲苯、正己烷、正辛胺、十八烷酸、辛胺乙酸酯、油酸、油烯基胺、邻二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸亚丙酯、丙二醇、丙二醇甲基醚、对-二甲苯、甲苯、磷酸三乙酯、三乙二醇、二甲苯磺酸、石蜡、矿物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇甲基醚、二乙二醇甲基醚、甲醇、乙醇、异丙醇以及更高分子量的醇,例如戊醇、四氢呋喃醇、己醇、辛醇、乙二醇、丙二醇、甘油、N-甲基-2-吡咯烷酮等。
适合的固体载体是,例如滑石、二氧化钛、叶蜡石粘土、硅石、凹凸棒石粘土、硅藻土、石灰石、碳酸钙、膨润土、钙蒙脱土、棉籽壳、小麦粉、大豆粉、浮石、木粉、胡桃壳粉、木素和类似的物质。
许多表面活性物质可以有利地用在固体和液体配制品两者中,尤其是在使用前可被载体稀释的那些配制品中。表面活性物质可以是阴离子的、阳离子的、非离子的或聚合的并且它们可以用作乳化剂、湿润剂或悬浮剂或用于其他目的。典型的表面活性物质包括例如烷基硫酸酯的盐,诸如十二烷基硫酸二乙醇铵;烷基芳基磺酸酯的盐,诸如十二烷基苯磺酸钙;烷基酚/氧化烯加成产物。诸如乙氧基化壬基苯酚;醇/氧化烯加成产物,诸如乙氧基化十三烷醇;皂,诸如硬脂酸钠;烷基萘磺酸酯的盐,诸如二丁基萘磺酸钠;磺基丁二酸盐的二烷基酯,诸如二(2-乙基己基)磺基丁二酸钠;山梨糖醇酯,诸如山梨糖醇油酸酯;季铵,诸如氯化十二烷基三甲基铵,脂肪酸的聚乙二醇酯,诸如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及磷酸单-和二-烷酯的盐;以及还有描述在例如“麦卡琴清洁剂和乳化剂年鉴(McCutcheon’s Detergents and Emulsifiers Annual)”,MC出版公司(MCPublishing Corp.),新泽西州里奇伍德(Ridgewood,New Jersey),1981中的其他物质。
可以用于杀有害生物配制品的其他辅助剂包括结晶作用抑制剂、粘度改性剂、悬浮剂、染料、抗氧化剂、发泡剂、光吸收剂、混合助剂、消泡剂、络合剂、中和或pH改变的物质与缓冲液、腐蚀抑制剂、香料、湿润剂、吸收增强剂、微量营养素、增塑剂、助流剂、润滑剂、分散剂、增稠剂、防冻剂、杀微生物剂、以及液体与固体化肥。
根据本发明的这些组合物可以包括一种添加剂,该添加剂包括植物或动物来源的油、矿物油、此类油的烷基酯或此类油与油衍生物的混合物。在根据本发明的组合物中的油添加剂的量总体上是该待施用的混合物的0.01%到10%。例如,可以在该喷雾混合物已经制备以后将该油添加剂以所希望的浓度加入喷雾罐中。优选的油添加剂包括矿物油或植物来源的油,例如菜籽油、橄榄油或葵花籽油;乳化的植物油;植物来源的油的烷基酯,例如甲基衍生物;或动物来源的油,诸如鱼油或牛脂。优选的油添加剂包括C8-C22脂肪酸的烷基酯,尤其是C12-C18脂肪酸的甲基衍生物,例如月桂酸、棕榈酸以及油酸(分别为月桂酸甲酯、棕榈酸甲酯和油酸甲酯)的甲基酯。许多油衍生物获知于除草剂辅助剂纲要(Compendium ofHerbicide Adjuvants),第10版,南伊利诺伊大学,2010。
这些本发明组合物总体上包括按重量计从0.1%至99%,尤其是按重量计从0.1%至95%的本发明的化合物以及按重量计从1%至99.9%的配制辅助剂,该配制辅助剂优选地包括按重量计从0至25%的表面活性物质。而商用产品可以优选地被配制为浓缩物,最终使用者将通常使用稀释配制品。
施用率在宽范围之内变化并且取决于土壤的性质、施用方法、作物植物、有待控制的有害生物、主要气候条件、以及受施用方法支配的其他因素、施用时间以及目标作物。一般来讲,可以将化合物以从1l/ha至2000l/ha,尤其是从10l/ha到1000l/ha的比率施用。
优选的配制品可以具有以下成分(重量%):
可乳化的浓缩物:
活性成分:1%至95%,优选地60%至90%
表面活性剂:1%至30%,优选地5%至20%
液体载体:1%至80%,优选地1%至35%
尘剂:
活性成分:0.1%至10%,优选0.1%至5%
固体载体:99.9%至90%,优选99.9%至99%
悬浮液浓缩物:
活性成分:5%至75%,优选10%至50%
水:94%至24%,优选88%至30%
表面活性剂:1%至40%,优选地2%至30%
可湿性粉剂:
活性成分:0.5%至90%,优选地1%至80%
表面活性剂:0.5%至20%,优选地1%至15%
固体载体:5%至95%,优选15%至90%
颗粒剂:
活性成分:0.1%至30%,优选0.1%至15%
固体载体:99.5%至70%,优选97%至85%
以下实例进一步展示了(但不限制)本发明。
可湿性粉剂 | a) | b) | c) |
活性成分 | 25% | 50% | 75% |
木质素磺酸钠 | 5% | 5% | - |
十二烷基硫酸钠 | 3% | - | 5% |
二异丁基萘磺酸钠 | - | 6% | 10% |
苯酚聚乙二醇醚(7-8mol的氧化乙烯环氧乙烷) | - | 2% | - |
高度分散的硅酸 | 5% | 10% | 10% |
高岭土 | 62% | 27% | - |
将该组合与这些辅助剂充分混合并且将混合物在一个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粉末。
将该组合与这些佐剂充分混合并且将混合物在一个适当的研磨机中充分研磨,从而获得了可以直接用于种子处理的粉末。
可乳化性浓缩物 | |
活性成分 | 10% |
辛基苯酚聚乙二醇醚(4-5mol的环氧乙烷) | 3% |
十二烷基苯磺酸钙 | 3% |
蓖麻油聚乙二醇醚(35mol的环氧乙烷) | 4% |
环己酮 | 30% |
二甲苯混合物 | 50% |
在植物保护中可以使用的具有任何所要求的稀释的乳液可以通过用水稀释从这种浓缩物中获得。
尘剂 | a) | b) | c) |
活性成分 | 5% | 6% | 4% |
滑石 | 95% | - | - |
高岭土 | - | 94% | - |
矿物填充剂 | - | - | 96% |
通过将该组合与载体进行混合并且将该混合物在一个适当的研磨机中研磨获得立即可用的尘剂。此类粉剂还可以用于种子的干法敷料。
挤出机颗粒 | |
活性成分 | 15% |
木质素磺酸钠 | 2% |
羧甲基纤维素 | 1% |
高岭土 | 82% |
将该组合与这些辅助剂混合并且研磨,并且将该混合物用水湿润。将混合物挤出并且然后在空气流中干燥。
包衣的颗粒 | |
活性成分 | 8% |
聚乙二醇(mol.wt.200) | 3% |
高岭土 | 89% |
将这种精细研磨的组合在一个混合器中均匀地施用到用聚乙二醇湿润的高岭土中。以此方式获得无尘的包衣的颗粒。
悬浮浓缩剂
将这种精细研磨的组合与这些佐剂紧密地混合,从而给出了一种悬浮液浓缩物,可以使用水稀释从该浓缩物获得任何所希望的悬浮液。使用此类稀释体,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、倾倒或浸渍进行保护。
种子处理用的可流动性浓缩剂
活性成分 | 40% |
丙二醇 | 5% |
共聚物丁醇PO/EO | 2% |
三苯乙烯酚,具有10-20摩尔EO | 2% |
1,2-苯并异噻唑啉-3-酮(处于在水中20%的溶液形式) | 0.5% |
单偶氮-颜料钙盐 | 5% |
硅油(处于在水中75%的乳液的形式) | 0.2% |
水 | 45.3% |
将这种精细研磨的组合与这些佐剂紧密地混合,从而给出了一种悬浮液浓缩物,可以使用水稀释从该浓缩物获得任何所希望的悬浮液。使用此类稀释体,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、倾倒或浸渍进行保护。
缓释的胶囊悬浮剂
将28份的组合与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。将获得的胶囊悬浮剂通过添加0.25份的一种增稠剂以及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。该介质胶囊的直径是8微米-15微米。将产生的配制品施用到种子上作为适合于用于此目的的一种装置中的水性悬浮液。
配制品类型包括乳液浓缩剂(EC)、悬浮浓缩剂(SC)、悬乳剂(SE)、胶囊悬浮剂(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)、可溶性浓缩剂(SL)、超低容量悬浮剂(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩剂(DC)、可湿性粉剂(WP)、可溶性粒剂(SG)或与农业上可接受的佐剂类组合的任何技术上可行的配制品形式。
制备实例:
“Mp”是指以℃计的熔点。自由基表示甲基基团。1H NMR测量值在Brucker 400MHz分光计上记录,化学位移相对于TMS标准品以ppm给出。光谱在如指定的氘代溶剂中测量。用以下LCMS方法中的任一种来表征这些化合物:对于每种化合物获得的特征LCMS值是保留时间(“Rt”以分钟为单位记录)和测量的分子离子(M+H)+或(M-H)-。
LCMS方法:
方法1:
质谱图记录在来自沃特斯公司(Waters)的质谱仪(ZQ单四极杆质谱仪)上,其装备有一种电喷射源(极性:正离子或负离子,毛细管电压:3.00kV,锥孔范围:30-60V,提取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr,质量范围:100至900Da)和一种来自沃特斯公司的Acquity UPLC:二元泵,加热柱室以及二极管阵列检测器。溶剂脱气装置,二元泵,加热柱室以及二极管阵列检测器。柱:沃特斯UPLC HSS T3,1.8μm,30X 2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH:梯度:梯度:0min 0%B,100%A;1.2-1.5min 100%B;流量(ml/min)0.85。
方法2:
来自沃特斯公司的ACQUITY SQD质谱仪(单四极杆质谱仪)上记录光谱,电离方法:电喷射,极性:正离子,毛细管(kV)3.00,锥孔(V)20.00,提取器(V)3.00,源温度(℃)150,去溶剂化温度(℃)400,锥孔气体流量(L/Hr)60,去溶剂化气体流量(L/Hr)700,质量范围:100Da至800Da,DAD波长范围(nm):210至400。方法:使用以下HPLC梯度条件的沃特斯ACQUITY UPLC(溶剂A:水/甲醇9:1,0.1%甲酸,以及溶剂B:乙腈、0.1%甲酸)
柱类型:沃特斯(Waters)ACQUITY UPLC HSS T3;柱长:30mm;柱内径:2.1mm;颗粒尺寸:1.8微米;温度:60℃。
方法3:
光谱记录在来自沃特斯公司的质谱仪(SQD或ZQ单四极杆质谱仪)上,其装备有一种电喷射源(极性:正离子或负离子,毛细管电压:3.00kV,锥孔范围:30-60V,提取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr,质量范围:100至900Da)和一种来自沃特斯公司的Acquity UPLC:二元泵,加热柱室以及二极管阵列检测器。溶剂脱气装置,二元泵,加热柱室以及二极管阵列检测器。柱:沃特斯UPLC HSS T3,1.8μm,30X 2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:0min 0%B,100%A;2.7-3.0min100%B;流量(ml/min)0.85
实例P1:2-[5-(4-氯代苯基)-3-乙基磺酰基-2-吡啶基]-3-甲基-6-(三氟甲基)咪 唑并[4,5-c]吡啶(化合物P1)的制备:
步骤A-1:N-[4-氨基-6-(三氟甲基)-3-吡啶基]氨基甲酸叔丁酯的制备
向6-(三氟甲基)吡啶-3,4-二胺(3.140g,17.73mmol)(可商购的)在四氢呋喃(50ml)中的溶液中添加叔丁氧基羰基叔丁基甲酸酯(4.643g,1.2当量)。将反应混合物在50℃下搅拌20小时,在这段时间之后,添加更多的叔丁氧基羰基叔丁基甲酸酯(1.1g,0.3当量)。在搅拌20小时以上后,将反应混合物在减压下蒸发以留下吸收在二氯甲烷中的固体残余物,冷却至0℃并且将所得悬浮液过滤。该结晶的残余物是N-[4-氨基-6-(三氟甲基)-3-吡啶基]氨基甲酸叔丁酯。LCMS(方法1):278(M+H)+;保留时间:0.79min。
1H NMR(400MHz,CD3CN)δppm:8.28(s,1H);7.09(s,1H);6.94(br.s,1H);5.24(br.s,2H);1.50(s,9H)。
步骤A-2:N-[4-氨基-6-(三氟甲基)-3-吡啶基]-N-甲基-氨基甲酸叔丁酯的制备
在20℃-25℃下,将N-[4-氨基-6-(三氟甲基)-3-吡啶基]氨基甲酸叔丁酯(合成在上文中描述)(3.920g,14.14mmol)在N,N-二甲基甲酰胺(20ml)中的溶液经20分钟添加至氢化钠(0.648g,1.05当量)在N,N-二甲基甲酰胺(30ml)中的搅拌悬浮液中。在气体停止释放15分钟之后,添加碘甲烷(2.21g,1.1当量)。将温度上升至30℃并且在这个水平维持30分钟。然后将反应混合物小心地倾倒进水中(200ml)并且将产物用乙酸乙酯萃取两次。将有机相用盐水洗涤,经硫酸钠进行干燥并在减压下蒸发。将获得的浅棕色固体通过硅胶柱层析,用乙酸乙酯和庚烷的混合物洗脱进行纯化。在从乙酸乙酯-庚烷中再结晶之后,分离出呈无色晶体状的N-[4-氨基-6-(三氟甲基)-3-吡啶基]-N-甲基-氨基甲酸叔丁酯。LCMS(方法1):292(M+H)+;保留时间:0.85min。1H NMR(400MHz,CDCl3)δppm:8.21(s,1H);7.00(s,1H);5.58(br.s,2H);3.18(s,3H);1.43(s,9H)。
步骤A-3:N3-甲基-6-(三氟甲基)吡啶-3,4-二胺的制备
将N-[4-氨基-6-(三氟甲基)-3-吡啶基]-N-甲基-氨基甲酸叔丁酯(3.530g,12.12mmol)(制备在上文中描述)在1,4-二噁烷(50ml)中的溶液用2N水性HCl溶液(18.18ml,3当量)处理并且将所得混合物加热。在约70℃气体释放开始,直到反应混合物已煮沸20分钟。然后在减压下除去大部分二噁烷,并且在冷却至20℃后用碳酸氢钠(3.1g,36.9mmol)处理残余溶液。形成粘稠的浆液,将其用乙酸乙酯萃取。将有机相用盐水洗涤,经硫酸钠进行干燥并在减压下浓缩。获得呈无色晶体状的标题化合物。LCMS(方法1):192(M+H)+;保留时间:0.25min。1H NMR(400MHz,CDCl3)δppm:7.90(s,1H);6.93(s,1H);4.09(br s,2H);3.40(br s,1H);2.95(s,3H)。
步骤B-1:5-溴-3-乙基硫烷基-吡啶-2-甲酸甲酯的制备
向在0℃下搅拌的5-溴-3-氯-吡啶-2-甲酸甲酯(0.100g,0.399mmol)(可商购的)在四氢呋喃中的溶液中添加乙基硫烷基钠(0.034g,1当量)。在该温度下1小时之后,去除冰浴并且继续搅拌20小时。然后将该反应混合物倾倒入水(15ml)中并且用乙酸乙酯萃取两次。将有机相经硫酸钠干燥,并且将溶剂去除。将该残余物经受硅胶快速层析并且将选择的级分蒸发以产生呈无色固体的5-溴-3-乙基硫烷基-吡啶-2-甲酸甲酯。LCMS(方法1):276,278(M+H)+;保留时间:0.92min。1H NMR(400MHz,CDCl3)δppm:8.46(s,1H);7.79(s,1H);4.00(s,3H);2.94(q,J=7.4Hz,2H);1.42(t,J=7.4Hz,3H)。
步骤B-2:5-溴-3-乙基硫烷基-吡啶-2-羧酸的制备
将5-溴-3-乙基硫烷基-吡啶-2-甲酸甲酯(3.900g,14.12mmol)(制备在上文中描述)在甲醇(75ml)和(20ml)的混合物中的溶液在20℃下搅拌,用2N水性氢氧化钠溶液(7.04ml,1.05当量)处理。将该混合物搅拌两小时,然后在减压下排除大多数醇。然后将反应混合物用2N水性HCl溶液处理并且将所得沉淀物过滤出,用水洗涤并且在真空下干燥。获得呈无色固体的标题化合物。LCMS(方法1):260,262(M-H)-;保留时间:0.77min。1H NMR(400MHz,d6-DMSO)δppm:13.4(br s,1H);8.50(s,1H);8.07(s,1H);3.04(q,J=7.53Hz,2H);1.27(t,J=7.53Hz,3H)。
步骤C-1:2-(5-溴-3-乙基硫烷基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶的制备
向5-溴-3-乙基硫烷基-吡啶-2-羧酸(2.800g,10.68mmol)在二氯甲烷(10ml)中的悬浮液中添加一滴N,N-二甲基酰胺,随后添加草酰氯(2.034g,1.400ml,1.5当量)。在气体释放结束后,反应混合物是浅红色溶液。将后者在减压下、在60℃的浴温度下蒸发。残余物形成5-溴-3-乙基硫烷基-吡啶-2-碳酰氯的深红色晶体。
向N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(2.042g,10.68mmol)在四氢呋喃(30ml)中的澄清溶液中添加溶解在四氢呋喃(20ml)中的5-溴-3-乙基硫烷基-吡啶-2-碳酰氯(在上文中描述)溶液。将所得的混合物加热至回流温度。形成大的白色沉淀物。在冷却至20℃之后,该反应混合物过滤并且将滤液在减压下蒸发。将残余物和滤饼合并并且溶解在水中。将溶液通过添加饱和水性碳酸氢钠的溶液中和并且将产物用乙酸乙酯萃取两次。然后有机溶液经硫酸钠干燥并在减压下蒸发以产生呈深棕色胶状的该粗制产物。将该胶吸收进间二甲苯(10ml)中,添加对甲苯磺酸(一水合物)(2.032g,1当量)并且将混合物加热至高达150℃持续8小时。然后将该反应混合物倾倒入水(300ml)中并且用乙酸乙酯萃取两次。在减压下蒸发溶剂之后,将该粗制深棕色产物通过硅胶柱层析,用在庚烷中的乙酸乙酯洗脱进行纯化。将所选级分蒸发以产生呈无色固体的标题化合物。LCMS(方法1):417,419(M+H)+;保留时间:1.04min。1H NMR(400MHz,CDCl3)δppm:8.96(s,1H);8.56(s,1H);8.20(s,1H);7.88(s,1H);4.07(s,3H);2.98(q,J=7.44Hz,2H);1.38(t,J=7.44Hz,3H)。
步骤C-2:2-(5-溴-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶的制备
将2-(5-溴-3-乙基硫烷基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(2.000g,4.79mmol)在二氯甲烷(50ml)中的溶液在冰浴中搅拌并且分部分地添加间氯过氧苯甲酸(2.54g,70%纯度,2.5当量),以这种方法使得反应混合物的温度保持低于10℃。然后去除冰浴,并且在20℃下将混合物搅拌另外的4小时。在该反应完成后,将该混合物与饱和水性碳酸氢钠溶液搅拌。将各相分离并且将该水相用二氯甲烷萃取。将有机层合,经硫酸钠干燥并蒸发。将该残余物经受硅胶柱层析,用在庚烷中的乙酸乙酯洗脱。将选择的级分蒸发并且将残余物用庚烷磨碎以产生呈无色固体的标题化合物。LCMS(方法1):449,451(M+H)+;保留时间:0.95min。1H NMR(400MHz,CDCl3)δppm:9.06(s,1H);9.00(s,1H);8.68(s,1H);8.11(s,1H);3.90(s,3H);3.82(q,2H);1.38(t,3H)。
步骤C-3:2-[5-(4-氯代苯基)-3-乙基磺酰基-2-吡啶基]-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(化合物P1)的制备
在20℃下,将在碳酸钠(0.153ml,2.5当量)和1,2-二甲氧基乙烷(4ml)的2M水溶液中的2-(5-溴-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(0.055g,0.122mmol)、(4-氯代苯基)硼酸(0.023g,1.2当量)的混合物在试管中搅拌,同时将缓慢的氩气流鼓泡通过其持续5分钟。然后添加四三苯基膦钯(0.007g,0.05当量)并且将所得浅棕色混合物在氩气氛下在100℃热油浴中搅拌。随后通过LCMS分析反应混合物的等分试样来跟踪反应的进展。当起始原料耗尽时,将反应混合物用水(10ml)稀释,并且用乙酸乙酯萃取两次。将合并的有机相相继地用水和盐水洗涤,然后经硫酸钠干燥并在减压下浓缩。将棕色油状的残余物通过硅胶快速层析,用庚烷-乙酸乙酯混合物洗脱进行纯化。将选择的级分蒸发以产生呈无色固体的标题化合物。LCMS(方法1):481,483(M+H)+;保留时间:1.09min。1H NMR(400MHz,CDCl3)δppm:9.18(s,1H);9.00(s,1H);8.67(s,1H);8.12(s,1H);7.68(d,2H);7.57(d,2H);3.94(s,3H);3.83(q,2H);1.40(t,3H)。
实例P2:2-[5-(4-氯代苯基)-3-乙基硫烷基-2-吡啶基]-3-甲基-6-(三氟甲基)咪 唑并[4,5-c]吡啶(化合物P15)的制备:
向5-(4-氯-苯基)-3-乙基硫烷基-吡啶-2-羧酸(150mg,0.511mmol)在二氯甲烷(3ml)中的溶液中添加一滴N,N-二甲基酰胺,随后添加草酰氯(0.086ml,1.021mmol,2当量)。在气体释放结束后,反应混合物是浅红色溶液。将后者在减压下、在60℃的浴温度下蒸发以得到红色晶体状的5-(4-氯代苯基)-3-乙基硫烷基-吡啶-2-碳酰氯。
向上述5-(4-氯代苯基)-3-乙基硫烷基-吡啶-2-碳酰氯在二氯甲烷(1ml)和间二甲苯(3ml)中的溶液中添加N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(102.5mg,0.536mmol)。将所得混合物加热至100℃,从而蒸馏出二氯甲烷,并在100℃下继续搅拌30分钟。然后添加对甲苯磺酸(一水合物)(92.3mg,0.536mmol)并且将混合物进一步加热至150℃持续20小时。在冷却至室温之后,将混合物用乙酸乙酯稀释并且将溶液用水洗涤两次。将有机相用盐水洗涤,经硫酸钠进行干燥并在减压下浓缩。将残余物通过硅胶快速层析,用庚烷-乙酸乙酯混合物洗脱进行纯化。将选择的级分蒸发以产生呈固体的标题化合物。LCMS(方法1):449,451(M+H)+;保留时间:1.15min。1H NMR(400MHz,CDCl3)δppm:8.96(s,1H);8.70(s,1H);8.20(s,1H);7.89(s,1H);7.59(d,J=8.44Hz,2H);7.52(d,J=8.44Hz,2H);4.10(s,3H);3.03(q,J=7.44Hz,2H);1.38(t,J=7.44Hz,3H)。
实例P3:2-[5-(4-氯-2-甲基-苯基)-3-乙基磺酰基-2-吡啶基]-3-甲基-6-(三氟 甲基)咪唑并[4,5-c]吡啶(化合物P14)的制备:
将2-[3-乙基磺酰基-5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)-2-吡啶基]-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(下文化合物I1)(50mg,0.101mmol)和1-溴-4-氯-2-甲基-苯(31mg,0.151mmol)在由2M水性碳酸钠(0.2ml)和1,2-二甲氧基乙烷(2ml)组成的溶液中的混合物用氩气冲洗5分钟。然后添加四三苯基膦钯(5.8mg,0.005mmol)并且将所得混合物在氩气氛下在90℃热油浴中搅拌20小时。LCMS分析显示完全的转化并且对于2-[5-(4-氯-2-甲基-苯基)-3-乙基磺酰基-2-吡啶基]-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(化合物P14)的测量数据如下,LCMS(方法1):495/497(M+H)+;保留时间:1.12min。粗混合物的另一个确定的组分是经质子脱硼基化产物2-(3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶,LCMS(方法1):371(M+H)+;保留时间:0.81min。
表P1:具有化学式(I)的化合物的实例
实例I1:中间体2-[3-乙基磺酰基-5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2- 基)-2-吡啶基]-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(化合物I1)的制备:
2-(5-溴-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(制备在上文中描述)(0.050g,0.111mmol)、乙酸钾(0.027g,2.5当量)和4,4,5,5-四甲基-2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)-1,3,2-二氧硼戊环(0.042g,1.5当量)的混合物在1,2-二甲氧基乙烷(3ml)中轻柔地用氩气冲洗,然后添加1,1’-双(二苯基膦基)-二茂铁)二氯钯-二氯甲烷(1:1)复合物(0.005g,0.05当量),并且将浅黄色混合物在惰性气氛下搅拌同时加热至90℃。当起始溴化物耗尽时,将深色反应混合物用水(20ml)稀释,并且用乙酸乙酯萃取两次。将这些合并的有机相经硫酸钠干燥,并且在减压下浓缩。将深棕色胶吸收在二乙醚中并且通过硅藻土垫过滤。将滤液用水(5ml)和1N水性氢氧化钠(0.2ml)的混合物萃取,并且然后将水相用1N-水性盐酸(0.3ml)处理。将沉淀的固体用二乙醚萃取两次。将有机相用盐水洗涤,用硫酸钠干燥并在减压下蒸发以产生呈无色固体的标题化合物。LCMS(方法1):413(M-H)-;827(2M-H)-;415(M+H)+用于相应的硼酸;保留时间:0.77min(在这种情况下,M对应于相应的硼酸而不是频哪醇酯,但NMR显示频哪醇部分)。1H NMR(400MHz,CDCl3)δppm:9.28(s,1H);8.99(s,1H);8.87(s,1H);8.11(s,1H);3.88(s,3H);3.76(q,J=7.4Hz,2H);1.41(s,12H);1.38(t,J=7.4Hz,3H)。
实例I2:5-(4-氯代苯基)-3-乙基硫烷基-吡啶-2-羧酸(化合物I2)的制备:
步骤1:5-溴-3-氯-吡啶-2-甲酸甲酯的制备
向5-溴-3-氯-吡啶-2-羧酸(60g,183.2mmol)在二氯甲烷(700ml)中的轻微浑浊的溶液中逐滴添加N,N-二甲基甲酰胺(1ml)和草酰氯(24.9ml,286.9mmol)。将该浑浊溶液在环境温度下搅拌3小时。将所得黄色溶液冷却至10℃并且向混合物中逐滴添加甲醇(30.8ml,761.3mmol),将温度维持在15℃和20℃之间。将该溶液在环境温度下搅拌过夜。在用水性饱和碳酸氢钠溶液中和后,将有机层用盐水洗涤,经硫酸钠干燥,过滤并蒸发以给出呈黄色固体的5-溴-3-氯-吡啶-2-甲酸甲酯(55g),将其未经进一步纯化而使用。LCMS(方法3):250/252/254(M+1)+,保留时间1.12min。
步骤2:3-氯-5-(4-氯代苯基)吡啶-2-甲酸甲酯的制备
将5-溴-3-氯-吡啶-2-甲酸甲酯(17.33g,69.2mmol)、4-氯代苯基-硼酸(11.36g,72.7mmol)、碳酸钠(14.7g,138.4mmol)在1,2-二-甲氧基乙烷(500ml)和水(50ml)的混合物的溶液用氩气冲洗。添加四(三苯基膦)钯(4.0g,3.5mmol)并且将混合物在90℃下搅拌7小时。添加更多的催化剂(0.5g,0.4mmol)并且将混合物在90℃下搅拌另外的2小时。在冷却之后,将该反应混合物用水和乙酸乙酯进行稀释。将水相分离并且用乙酸乙酯萃取两次。将合并的有机相经硫酸镁干燥并且在真空下浓缩。将残余物经受快速色谱法以给出3-氯-5-(4-氯代苯基)吡啶-2-甲酸甲酯(10.5g)。LCMS(方法3):282/284(M+1)+,保留时间1.63min。
步骤3:5-(4-氯代苯基)-3-乙基硫烷基-吡啶-2-羧酸(化合物I2)的制备
向3-氯-5-(4-氯代苯基)吡啶-2-甲酸甲酯(2.0g,7.1mmol)在15ml N,N-二甲基酰胺中的溶液中添加乙硫醇钠(3.3g,35mmol)。将温度上升至40℃并且将反应混合物在室温下搅拌1小时。将溶液用叔丁基甲基醚稀释并且用冰水萃取。将水相分离并且用乙酸中和并且用叔丁基甲基醚和乙酸乙酯萃取。将合并的有机层经硫酸镁干燥并且在真空中蒸发以给出5-(4-氯-苯基)-3-乙基硫烷基-吡啶-2-羧酸(2.0g),其不经进一步纯化而使用。LCMS(方法3):294/296(M+1)+,保留时间1.42min。
表I1:具有化学式(IV)和(XIV)的中间化合物的实例
通过添加其他有杀昆虫、杀螨和/或杀真菌活性的成分,根据本发明的这些组合物的活性可以显著地加宽,并且适合于当时的环境。具有化学式I的化合物与其他具有杀昆虫、杀螨和/或杀真菌活性的成分的混合物还可以具有进一步地、意料之外的优点,这些优点还可以在更宽的含义上描述为协同活性。例如,植物对其更好的耐受性、降低的植物毒性,昆虫可以在它们的不同发育阶段得到控制或者在它们的生产期间(例如,在研磨或者混合过程中,在它们的储藏或它们的使用过程中)更好的行为。
在这里,合适的活性成分的添加物是例如下面类别的活性成分的代表物:有机磷化合物、硝基苯酚衍生物、硫脲、保幼激素、甲脒、二苯甲酮衍-生物、脲类、吡咯衍生物、氨基甲酸酯、拟除虫菊酯、氯化烃、酰基脲、吡啶基亚甲基氨基衍生物、大环内酯类、新烟碱以及苏云金芽孢杆菌制剂。
以下具有化学式I的化合物与活性成分的混合物是优选的(缩写“TX”意为“选自下组的一种化合物,该组由描述于本发明的表1至6中的化合物组成”):
一种佐剂,该佐剂选自由以下物质组成的组:石油(替代名称)(628)+TX,
一种杀螨剂,该杀螨剂选自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/化学文摘名称)(1059)+TX、2-氟-N-甲基-N-1-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、α-氯氰菊酯(202)+TX、赛硫磷(870)+TX、磺胺螨酯[CCN]+TX、逐磷酰胺(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、AZ60541(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、奔菌灵(62)+TX、苯噁磷(别名)[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(别名)+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(别名)+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、瓜叶菊素(696)+TX、四螨嗪(158)+TX、氯氰碘柳胺(别名)[CCN]+TX、蝇毒磷(174)+TX、巴豆酰甲苯胺(别名)[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、高效氯氟氰菊酯(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-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、内吸磷-S-甲基磺隆(demeton-S-methylsulphon)(1039)+TX、丁醚脲(226)+TX、氯亚胺硫磷(1042)+TX、二嗪农(227)+TX、抑菌灵(230)+TX、敌敌畏(236)+TX、二克磷(dicliphos)(别名)+TX、三氯杀螨醇(242)+TX、百治磷(243)+TX、除螨灵(1071)+TX、甲氟磷(1081)+TX、乐果(262)+TX、二活菌素(别名)(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、邻敌螨消(1090)+TX、硝戊酯(1092)+TX、硝辛酯杀螨剂(1097)+TX、硝丁酯(1098)+TX、敌杀磷(1102)+TX、二苯砜(IUPAC名称)(1103)+TX、双硫仑(别名)[CCN]+TX、乙拌磷(278)+TX、DNOC(282)+TX、多芬纳普(dofenapyn)(1113)+TX、多拉菌素(别名)CCN]+TX、硫丹(294)+TX、因毒磷(1121)+TX、EPN(297)+TX、乙酰氨基阿维菌素(别名)[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(别名)+TX、唑螨酯(345)+TX、芬螨酯(1157)+TX、芬催凡尼尔(fentrifanil)(1161)+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、嘧螨酯(360)+TX、氟佐隆(1166)+TX、氟螨噻(1167)+TX、氟螨脲(366)+TX、氟氰戊菊酯(367)+TX、联氟螨(1169)+TX、氟虫脲(370)+TX、氟氯苯菊酯(372)+TX、氟杀螨(1174)+TX、氟胺氰菊酯(1184)+TX、FMC1137(研究代码)(1185)+TX、伐虫脒(405)+TX、伐虫脒盐酸盐(405)+TX、安果(1192)+TX、胺甲威(1193)+TX、γ-六氯环己烷(430)+TX、果绿定(1205)+TX、苄螨醚(424)+TX、庚烯磷(432)+TX、十六环丙烷(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(别名)(473)+TX、异丙基O-(甲氧基氨基硫代磷酰基)水杨酸酯(IUPAC名称)(473)+TX、伊维菌素(别名)[CCN]+TX、茉酮菊素I(696)+TX、茉酮菊素II(696)+TX、碘硫磷(1248)+TX、林丹(430)+TX、虱螨脲(490)+TX、马拉硫磷(492)+TX、丙螨氰(1254)+TX、灭蚜磷(502)+TX、二噻磷(1261)+TX、二甲噻蒽(别名)[CCN]+TX、虫螨畏(1266)+TX、甲胺磷(527)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、灭多威(531)+TX、溴甲烷(537)+TX、速灭威(550)+TX、速灭磷(556)+TX、自克威(1290)+TX、米尔(557)+TX、米尔贝肟(别名)[CCN]+TX、丙胺氟(1293)+TX、久效磷(561)+TX、茂果(1300)+TX、莫西菌素(别名)[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、尼可霉素(别名)[CCN]+TX、戊氰威(1313)+TX、戊氰威1:1氯化锌复合物(1313)+TX、NNI-0101(化合物代码)+TX、NNI-0250(化合物代码)+TX、氧化乐果(594)+TX、杀线威(602)+TX、异亚砜磷(1324)+TX、砜拌磷(1325)+TX、pp’-DDT(219)+TX、对硫磷(615)+TX、氯菊酯(626)+TX、石油(别名)(628)+TX、芬硫磷(1330)+TX、稻丰散(631)+TX、甲拌磷(636)+TX、伏杀硫磷(637)+TX、硫环磷(1338)+TX、亚胺硫磷(638)+TX、磷胺(639)+TX、辛硫磷(642)+TX、甲基嘧啶磷(652)+TX、氯化松节油(传统名)(1347)+TX、浏阳霉纛(别名)(653)+TX、丙氯诺(1350)+TX、丙溴磷(662)+TX、蜱虱威(1354)+TX、克螨特(671)+TX、强敌(673)+TX、残杀威(678)+TX、乙噻唑磷(1360)+TX、发果(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、喹硫磷(711)+TX、喹硫磷(1381)+TX、R-1492(研究代码)(1382)+TX、RA-17(研究代码)(1383)+TX、鱼藤酮(722)+TX、八甲磷(1389)+TX、硫线磷(别名)+TX、司拉克丁(别名)[CCN]+TX、SI-0009(化合物代码)+TX、苏硫磷(1402)+TX、螺螨酯(738)+TX、甲螨酯(739)+TX、SSI-121(研究代码)(1404)+TX、舒非仑(别名)[CCN]+TX、氟虫胺(750)+TX、治螟磷(753)+TX、硫(754)+TX、SZI-121(研究代码)(757)+TX、氟胺氰菊酯(398)+TX、吡螨胺(763)+TX、TEPP(1417)+TX、叔丁威(别名)+TX、杀虫威(777)+TX、三氯杀螨砜(786)+TX、杀螨素(别名)(653)+TX、杀螨硫醚(1425)+TX、thiafenox(别名)+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(别名)[CCN]+TX、威菌磷(1441)+TX、苯螨噻(1443)+TX、三唑磷(820)+TX、唑蚜威(triazuron)(别名)+TX、敌百虫(824)+TX、氯苯乙丙磷(1455)+TX、三活菌素(别名)(653)+TX、蚜灭磷(847)+TX、氟吡唑虫[CCN]以及YI-5302(复合代码)+TX,
一种杀藻剂,该杀藻剂选自由以下物质组成的组: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物质组成的组:阿巴美丁(1)+TX、克芦磷酯(1011)+TX、多拉克汀(别名)[CCN]+TX、依马克丁(291)+TX、依马克丁苯甲酸酯(291)+TX、依立诺克丁(别名)[CCN]+TX、伊维菌素(别名)[CCN]+TX、米尔倍霉素(别名)[CCN]+TX、莫昔克丁(别名)[CCN]+TX、哌嗪[CCN]+TX、塞拉菌素(selamectin)(别名)[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物质组成的组: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物质组成的组: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(别名)[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扣硫柳汞(别名)[CCN]+TX,
一种生物试剂,该生物试剂选自由以下物质构成的组:棉褐带卷蛾颗粒体病毒(Adoxophyes orana GV)(别名)(12)+TX、放射形土壤杆菌(别名)(13)+TX、捕食螨(Amblyseius spp.)(别名)(19)+TX、芹菜夜蛾核多角体病毒(Anagrapha falcifera NPV)(别名)(28)+TX、Anagrus atomus(别名)(29)+TX、蚜虫寄生蜂(Aphelinus abdominalis)(别名)(33)+TX、棉蚜寄生蜂(Aphidius colemani)(别名)(34)+TX、食蚜瘿蚊(Autographacalifornica NPV)(别名)(35)+TX、苜蓿银纹夜蛾核多角体病毒(Bacillus firmus)(别名)(38)+TX、坚强芽孢杆菌(Bacillus firmus)(别名)(48)+TX、球形芽孢杆菌(Bacillussphaericus Neide)(学名)(49)+TX、苏云金芽孢杆菌(Bacillus thuringiensisBerliner)(学名)(51)+TX、苏云金芽孢杆菌.I(Bacillus thuringiensis subsp.aizawai)(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensissubsp.israelensis)(学名)(51)+TX、苏云金芽孢杆菌日本亚种(Bacillus thuringiensissubsp.japonensis)(学名)(51)+TX、苏云金芽孢杆菌k.(Bacillus thuringiensissubsp.kurstaki)(学名)(51)+TX、苏云金芽孢杆菌t.(Bacillus thuringiensissubsp.tenebrionis)(学名)(51)+TX、球孢白僵茵(Beauveria bassiana)(别名)(53)+TX,布氏白僵茵(Beauveria brongniartii)(别名)(54)+TX、草蜻蛉(Chrysoperla carnea)(别名)(151)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(别名)(178)+TX、苹果蠹蛾颗粒体病毒(Cydia pomonella GV)(别名)(191)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)(别名)(212)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)(别名)(254)+TX、丽蚜小蜂(Encarsia formosa)(学名)(293)+TX、桨角蚜小蜂(Eretmocerus eremicus)(别名)(300)+TX、玉米穗夜蛾核多角体病毒(Helicoverpa zea NPV)(别名)(431)+TX、嗜茵异小杆线虫(Heterorhabditis bacteriophora)和H.megidis(别名)(433)+TX、会聚长足瓢虫(Hippodamia convergens)(别名)(442)+TX、橘粉介壳虫寄生蜂(Leptomastixdactylopii)(别名)(488)+TX、盲蝽(Macrolophus caliginosus)(别名)(491)+TX,甘蓝夜蛾核多角体病毒(Mamestra brassicae NPV)(别名)(494)+TX、Metaphycus helvolus(别名)(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(别名)(575)+TX、小花蝽(别名)(596)+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)(别名)(613)+TX、智利捕植螨(Phytoseiulus persimilis)(别名)(644)+TX、甜菜夜蛾(Spodoptera exigua multicapsid)多核衣壳核多角体病毒(学名)(741)+TX、毛蚊线虫(Steinernema bibionis)(别名)(742)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(别名)(742)+TX、夜蛾斯氏线虫(别名)(742)+TX、Steinernema glaseri(别名)(742)+TX、Steinernema riobrave(另名)(742)+TX、Steinernema riobravis(别名)(742)+TX、Steinernema scapterisci(别名)(742)+TX、斯氏线虫属(Steinernema spp.)(别名)(742)+TX、赤眼蜂属(别名)(826)+TX、西方盲走螨(Typhlodromus occidentalis)(别名)(844)和蜡蚧轮枝茵(Verticillium lecanii)(别名)(848)+TX,
一种土壤消毒剂,该土壤消毒剂选自由以下物质组成的组: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物质组成的组:唑磷嗪(apholate)[CCN]+TX、双(氮丙啶)甲氨基膦硫化物(bisazir)(别名)[CCN]+TX、白消安(别名)[CCN]+TX、除虫脲(250)+TX、迪麦替夫(dimatif)(别名)[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)(别名)[CCN]+TX、涕巴(tepa)[CCN]+TX、硫代六甲磷(thiohempa)(别名)[CCN]+TX、硫涕巴(别名)[CCN]+TX、曲他胺(别名)[CCN]和尿烷亚胺(别名)[CCN]+TX,
一种昆虫信息素,该昆虫信息素选自由以下物质组成的组:(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)(替代名称)[CCN]+TX、西部松小蠹集合信息素(brevicomin)(替代名称)[CCN]+TX、十二碳二烯醇(codlelure)(替代名称)[CCN]+TX、十二碳二烯醇(codlemone)(替代名称)(167)+TX、诱蝇酮(cuelure)(替代名称)(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、多米尼加(dominicalure)(替代名称)[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚(替代名称)[CCN]+TX、南部松小蠹集合信息素(frontalin)(替代名称)[CCN]+TX、诱虫十六酯(gossyplure)(替代名称)(420)+TX、诱杀烯混剂(grandlure)(421)+TX、诱杀烯混剂I(替代名称)(421)+TX、诱杀烯混剂II(替代名称)(421)+TX、诱杀烯混剂III(替代名称)(421)+TX、诱杀烯混剂IV(替代名称)(421)+TX、醋酸十六烯酯(hexalure)[CCN]+TX、齿小蠹二烯醇(ipsdienol)(替代名称)[CCN]+TX、小蠢烯醇(ipsenol)(替代名称)[CCN]+TX、金龟子性诱剂(japonilure)(替代名称)(481)+TX、里尼汀(lineatin)(替代名称)[CCN]+TX、利特乐(litlure)(替代名称)[CCN]+TX、粉纹夜蛾性诱剂(looplure)(替代名称)[CCN]+TX、诱杀酯(medlure)[CCN]+TX、蒙托么克酸(megatomoicacid)(替代名称)[CCN]+TX、诱虫醚(methyl eugenol)(替代名称)(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)(替代名称)[CCN]+TX、oryctalure(替代名称)(317)+TX、非乐康(ostramone)(替代名称)[CCN]+TX、诱虫环(siglure)[CCN]+TX、索地丁(sordidin)(替代名称)(736)+TX、食菌甲诱醇(sulcatol)(替代名称)[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(替代名称)(839)+TX、特诱酮B1(替代名称)(839)+TX、特诱酮B2(替代名称)(839)+TX、特诱酮C(替代名称)(839)和创科尔(trunc-call)(替代名称)[CCN]+TX,
一种昆虫驱避剂,该昆虫驱避剂选自以下物质组成的组: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,
一种杀虫剂,该杀虫剂选自由以下物质组成的组: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-isovalerylindan-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、家蝇磷杀虫剂(别名)[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(别名)[CCN]+TX、除害威(866)+TX、α-氯氰菊酯(202)+TX、α-蜕皮激素(别名)[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(别名)(52)+TX、六氟硅酸钡(别名)[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(别名)(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(别名)+TX、溴苯烯磷(914)+TX、溴烯杀(918)+TX、溴-DDT(别名)[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(别名)+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(别名)(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(别名)+TX、顺式苄呋菊酯(80)+TX、三氟氯氰菊酯(别名)+TX、地虫威(999)+TX、氯氰碘柳胺(别名)[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(别名)[CCN]+TX、巴毒磷(1010)+TX、育畜磷(1011)+TX、冰晶石(别名)(177)+TX、CS708(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(别名)[CCN]+TX、d-柠檬烯(别名)[CCN]+TX、d-胺菊酯(别名)(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(别名)+TX、敌来死(别名)[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(别名)[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(别名)[CCN]+TX、DSP(1115)+TX、脱皮甾酮(别名)[CCN]+TX、EI 1642(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(别名)[CCN]+TX、高氰戊菊酯(302)+TX、依他伏杀(别名)[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(别名)(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(别名)+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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72129(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(别名)(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(别名)+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(别名)+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(别名)[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(别名)+TX、三氯磷酸酯(824)+TX、异皮蝇磷-3(别名)[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(别名)(725)+TX、藜芦碱(别名)(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(别名)+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、四氟唑菊酯(triflumezopyrim)(在WO 2012/092115所公开的)+TX、ε-甲氧苄氟菊酯[240494-71-7]+TX、ε-氟氯氰菊酯(epsilon-momfluorothrin)[1065124-65-3]+TX、氟唑哚唑(fluazaindolizine)[1254304-22-7]+TX、氯碱丙炔菊酯(chloroprallethrin)[399572-87-3]+TX、氟醚酰胺(fluxametamide)[928783-29-3]和(WO 2007/026965)+TX、氯氟氰虫酰胺(cyhalodiamide)[1262605-53-7]+TX、噻唑芬(tioxazafen)[330459-31-9]+TX、布洛尼安(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,
一种杀软体动物剂,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物质组成的组: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(替代名称)(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、AZ60541(化合物代码)+TX、benclothiaz[CCN]+TX、苯茵灵(62)+TX、丁基哒螨酮(butylpyridaben)(替代名称)+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)(替代名称)(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)(替代名称)+TX、乐果(262)+TX、依马克丁(替代名称)[CCN]+TX、苯甲酸依马克丁(291)+TX、依立诺克丁(291)+TX、(替代名称)[CCN]+TX、灭线磷(312)+TX、二溴乙烷(316)+TX、苯线磷(fenamiphos)(326)+TX、吡螨胺(替代名称)+TX、丰索磷(fenpyrad)(1158)+TX、噻唑磷(fosthiazate)(408)+TX、丁硫环磷(fosthietan)(1196)+TX、糠醛(替代名称)[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)(替代名称)[CCN]+TX、糠氨基嘌呤(mecarphon)(替代名称)(210)+TX、甲基灭蚜磷(mecarphon)(1258)+TX、威百亩(519)+TX、威百亩钾盐(替代名称)(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)(替代名称)[CCN]+TX、莫昔克丁(剔名)[CCN]+TX、疣孢漆斑茵(Myrothecium verrucaria)组分(替代名称)(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)(替代名称)+TX、塞拉菌素(selamectin)(替代名称)[CCN]+TX、多杀菌素(737)+TX、叔丁威(terbam)(替代名称)+TX、特丁磷(terbufos)(773)+TX、四氯噻吩(IUPAC/化学文摘名)(1422)+TX、thiaf enox(替代名称)+TX、虫线磷(thionazin)(1434)+TX、三唑磷(triazophos)(820)+TX、triazuron(替代名称)+TX、二甲苯酚[CCN]+TX、YI-5302(化合物代码)和玉米素(替代名称)(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物质组成的组: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物质组成的组: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(别名)(720)+TX,
一种杀鼠剂,该杀鼠剂选自由以下物质组成的组: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(替代名称)(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物质组成的组: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(替代名称)(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物质组成的组: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物质组成的组:衣马宁(imanin)(替代名称)[CCN]和利巴韦林(替代名称)[CCN]+TX,
一种创伤保护剂,该创伤保护剂选自由以下物质组成的组:氧化汞(512)+TX、辛噻酮(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、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、烯肟菌酯{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(bordeaux)混合物[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、SYP-LI90(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、春雷霉素(kasugamycin)[6980-18-3]+TX、磺菌威(methasulfocarb)[66952-49-6]+TX、苯菌酮[220899-03-6]+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-羧酸(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-羧酸(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,并且
微生物包括:鲁氏不动杆菌+TX、支顶孢属奥特那(Acremonium alternatum)+TX+TX、顶头孢霉(Acremonium cephalosporium)+TX、支顶孢属迪斯破瑞(Acremoniumdiospyri)+TX、小支顶孢属(Acremonium obclavatum)+TX、粒体病毒(Adoxophyes oranagranulovirus)(AdoxGV)+Tx、放射形土壤杆菌菌株K84(Galltrol-)+TX、互隔交链孢菌(Alternaria alternate)+TX、链格孢属桂皮+TX、链格孢属德斯垂(Alternariadestruens)+TX、白粉寄生孢+TX、黄曲霉AF36+TX、黄曲霉NRRL 21882+TX、曲霉属+TX、出芽短梗霉菌+TX、固氮螺菌属+TX、(+TX,TAZO)+TX、固氮菌+Tx、固氮菌克如可(Azotobacter chroocuccum)+TX、固氮菌赛斯特(Azotobacter cysts)(Bionatural Blooming)+TX、解淀粉芽孢杆菌+TX、蜡样芽胞杆菌+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、环状芽胞杆菌+TX、坚强芽孢杆菌(+TX、BioNem-+TX,)+TX、坚强芽孢杆菌菌株I-1582+TX、浸麻芽孢杆菌+TX、芽孢杆菌盐细菌(Bacillus marismortui)+Tx、巨大芽胞杆菌+TX、分支芽孢杆菌菌株AQ726+TX、芽孢杆菌乳头状突起(乳白色孢子粉)+TX、矮小芽孢杆菌属+TX、矮小芽孢杆菌菌株GB34+Tx、矮小芽孢杆菌菌株AQ717+TX、矮小芽孢杆菌菌株QST 2808(+TX,Ballad)+TX、芽孢杆菌斯巴瑞克(Bacillus spahericus)+TX、芽孢杆菌属+TX、芽孢杆菌属菌株AQ175+TX、芽孢杆菌属菌株AQ177+TX、芽孢杆菌属菌株AQ178+TX、微小芽孢杆菌菌株QST 713(+TX、+TX、)+TX、微小芽孢杆菌菌株QST 714+TX、微小芽孢杆菌菌株AQ153+TX、微小芽孢杆菌菌株AQ743+TX、微小芽孢杆菌菌株QST3002+TX、微小芽孢杆菌菌株QST3004+Tx、微小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aizawai GC 91+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis israelensis)(+TX、+TX、)+TX、苏云金芽孢杆菌克瑞斯达克(Bacillus thuringiensis kurstaki)(+TX、+TX、+TX、+TX、Scutella+TX、Turilav+TX、+TX、Dipel+TX、+TX、)+TX、苏云金芽孢杆菌克瑞斯达克BMP 123+TX、苏云金芽孢杆菌克瑞斯达克HD-1(Bioprotec-CAF/)+TX、苏云金芽孢杆菌菌株BD#32+TX、苏云金芽孢杆菌菌株AQ52+TX、苏云金芽孢杆菌变种aizawai(+TX、)+TX、细菌属(+TX、+TX、)+TX、番茄溃疡(bacteriophage of Clavipacter michiganensis)+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+TX、葡萄孢属cineria+TX、慢生型大豆根瘤菌+TX、短短芽孢杆菌+TX、苏云金芽孢杆菌tenebrionis+TX、比特布斯特(BtBooster)+TX、洋葱伯克霍尔德菌(Burkholderia cepacia)(+TX、+TX、Blue)+TX、唐菖蒲伯克霍尔德菌(Burkholderia gladii)+TX、唐菖蒲伯克霍尔德菌(Burkholderia gladioli)+TX、伯克霍德菌属(Burkholderia spp.)+TX、加拿大蓟真菌(Canadian thistle fungus)(CBHCanadian)+TX、乳酪假丝酵母(Candida butyri)+TX、无名假丝酵母(Candida famata)+TX、念珠菌属果实(Candida fructus)+TX、光滑念珠菌(Candidaglabrata)+TX、吉利蒙念珠菌(Candida guilliermondii)+TX、口津假丝酵母(Candidamelibiosica)+TX、假丝酵母菌株O+TX、近平滑假丝酵母(Candida parapsilosis)+TX、菌膜假丝酵母(Candida pelliculosa)+TX、铁红假丝酵母(Candida pulcherrima)+TX、假丝酵母瑞扣非(Candida reukaufii)+TX、假丝酵母(Candida saitoana)(Bio-+TX、)+TX、清酒假丝酵母(Candida sake)+TX、假丝酵母属(Candida spp.)+TX、假丝酵母泰尼斯(Candida tenius)+TX、肠杆菌属(Cedecea dravisae)+TX、产黄纤维单胞菌(Cellulomonas flavigena)+TX、螺卷毛壳(Chaetomium cochliodes)(Nova-)+TX、球毛壳菌(Chaetomium globosum)(Nova-)+TX、色素细菌菌株(Chromobacteriumsubtsugae strain)PRAA4-1T+TX、芽枝状枝孢(Cladosporiumcladosporioides)+TX、枝孢属孢菌(Cladosporium oxysporum)+TX、分子孢子菌(Cladosporium chlorocephalum)+TX、分子孢子菌属(Cladosporium spp.)+TX、极细枝孢霉(Cladosporium tenuissimum)+TX、粉红粘帚霉(Clonostachys rosea)+TX、炭疽菌(Colletotrichum acutatum)+TX、盾壳霉(Coniothyrium minitans)(Cotans)+TX、盾壳霉属(Coniothyrium spp.)+TX、浅白隐球酵母(Cryptococcus albidus)+TX、土生隐球菌(Cryptococcus humicola)+TX、隐球菌(Cryptococcusinfirmo-miniatus)+TX、罗伦隐球酵母(Cryptococcus laurentii)+TX、隐球菌颗粒体病毒(Cryptophlebia leucotreta granulovirus)+TX、贪铜菌肯佩斯(Cupriavidus campinensis)+TX、蛾颗粒体病毒(Cydia pomonella granulovirus)(CYD-)+TX、蛾颗粒体病毒(Cydia pomonella granulovirus)(+TX、Madex+TX、Madex Max/)+TX、帚梗柱孢属利维(Cylindrobasidium laeve)+TX、帚梗柱孢属(Cylindrocladium)+TX、汉逊德巴利酵母(Debaryomyceshansenii)+TX、内脐蠕孢属哈瓦尼恩斯(Drechslera hawaiinensis)+TX、阴沟肠杆菌(Enterobacter cloacae)+TX、肠杆菌科(Enterobacteriaceae)+TX、恩么费维勒塔(Entomophtora virulenta)+TX、黑附球菌(Epicoccum nigrum)+TX、黑附球菌(Epicoccum purpurascens)+TX、黑附球菌属(Epicoccum spp.)+TX、花状双皮菌(Filobasidium floriforme)+TX、镰孢菌(Fusarium acuminatum)+TX、厚垣镰孢霉(Fusarium chlamydosporum)+TX、尖孢镰刀菌(Fusarium oxysporum)(/Biofox )+TX、层生镰刀菌(Fusarium proliferatum)+TX、镰刀菌属(Fusarium spp.)+TX、白地霉(Galactomyces geotrichum)+TX、链孢粘帚霉(Gliocladium catenulatum)(+TX、)+TX、红粘帚霉(Gliocladium roseum)+TX、粉红粘帚霉属(Gliocladium spp.)+TX、绿色粘帚霉(Gliocladium virens)+TX、颗粒体病毒(Granulovirus)+TX、盐芽孢杆菌(Halobacillushalophilus)+TX、岸喜盐芽孢杆菌(Halobacillus litoralis)+TX、特氏盐芽孢杆菌(Halobacillus trueperi)+TX、盐单胞菌属(Halomonas spp.)+TX、盐单胞菌亚玻璃粘菌(Halomonas subglaciescola)+TX、盐弧菌属变型(Halovibrio variabilis)+TX、葡萄汁有孢汉逊酵母(Hanseniaspora uvarum)+TX、棉铃虫核型多角体病毒(Helicoverpa armigeranucleopolyhedrovirus)+TX、玉蜀黍属核多角体病病毒(Helicoverpa zeanuclear polyhedrosis virus)+TX、异黄酮-芒柄花黄素(Isoflavone-formononetin)+TX、柠檬克勒克酵母(Kloeckera apiculata)+TX、克勒克酵母(Kloeckera spp.)+TX、大链壶菌(Lagenidium giganteum)+TX、长胞梭菌(Lecanicillium longisporum)+TX、霜霉菌(Lecanicillium muscarium)+TX、毒蛾属核多角体病毒(Lymantria Dispar nucleopolyhedrosis virus)+TX、嗜盐海球菌(Marinococcus halophilus)+TX、格式梅拉菌(Meirageulakonigii)+TX、绿僵菌(Metarhizium anisopliae)+TX、绿僵菌(Metarhizium anisopliae)(Destruxin)+Tx、梅奇酵母属(Metschnikowiafruticola)+TX、美极梅奇酵母(Metschnikowia pulcherrima)+TX、微座孢属(Microdochium dimerum)+TX、小单孢菌属(Micromonospora coerulea)+TX、微球藻(Microsphaeropsis ochracea)+TX、白色麻扣倒(Muscodor albus)620+TX、麻扣倒菌株(Muscodor roseus strain)A3-5+TX、菌根属(Mycorrhizaespp.)(+TX、Root)+TX、菌根有孔疣苔属菌株(Myrotheciumverrucaria strain)AARC-0255+TX、BROS+TX、蛇口壳属菌株(Ophiostoma piliferum strain)D97+TX、粉质拟青霉(Paecilomycesfarinosus)+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)9PFR-+TX、)+TX、拟青霉属(Paecilomyces linacinus)(Biostat )+TX、拟青霉属菌株(Paecilomyces lilacinus strain)251(MeloCon)+TX、多粘类芽孢杆菌(Paenibacillus polymyxa)+TX、成团泛菌(Pantoea agglomerans)(BlightBan C9-)+TX、泛菌属(Pantoea spp.)+TX、巴斯德氏芽菌属(Pasteuria spp.)+TX、巴斯德氏菌(Pasteuria nishizawae)+TX、黄灰青霉(Penicillium aurantiogriseum)+TX、青霉菌比莱(Penicillium billai)(+TX、)+TX、短密青霉(Penicilliumbrevicompactum)+TX、常现青霉(Penicillium frequentans)+TX、灰黄青霉(Penicilliumgriseofulvum)+TX、产紫青霉菌(Penicillium purpurogenum)+TX、青霉菌属(Penicilliumspp.)+TX、纯绿色肯霉(Penicillium viridicatum)+TX、禾谷镰刀菌(Phlebiopsisgigantean)+TX、解磷细菌(phosphate solubilizing bacteria)+TX、隐地疫霉(Phytophthora cryptogea)+TX、疫霉菌(Phytophthorapalmivora)+TX、异常毕赤酵母(Pichia anomala)+TX、毕赤酵母属(Pichiaguilermondii)+TX、毕赤酵母(Pichia membranaefaciens)+TX、指甲毕赤酵母(Pichiaonychis)+TX、毕赤酵母属叶柄(Pichia stipites)+TX、绿脓杆菌(Pseudomonasaeruginosa)+TX、假单胞菌(Pseudomonas aureofasciens)(Spot-Less)+TX、洋葱假单胞菌(Pseudomonas cepacia)+TX、绿针假单胞菌(Pseudomonaschlororaphis)+TX、假单胞菌起皱(Pseudomonas corrugate)+TX、荧光假单胞菌菌株(Pseudomonas fluorescens strain)A506(BlightBan)+TX、恶臭假单胞菌(Pseudomonas putida)+TX、假单胞菌(Pseudomonas reactans)+TX、假单胞菌属(Pseudomonas spp.)+TX、丁香假单胞菌(Pseudomonas syringae)(Bio-)+TX、绿黄假单胞菌(Pseudomonas viridiflava)+TX、荧光假单胞菌(Pseudomons fluorescens)+TX、荧光假单胞菌菌株(Pseudozyma flocculosa strain)PF-A22 UL(Sporodex)+TX、纵沟柄锈菌(Puccinia canaliculata)+TX、柄锈菌(Pucciniathlaspeos)(Wood)+TX、腐霉属普柔刊卓(Pythium paroecandrum)+TX、寡雄腐霉(Pythium oligandrum)(+TX、)+TX、腐霉属普瑞佩鲁(Pythiumperiplocum)+Tx、水生拉恩菌(Rhanella aquatilis)+TX、拉恩氏菌属(Rhanella spp.)+TX、根瘤菌(Rhizobia)(+TX、)+TX、丝核菌(Rhizoctonia)+TX、红球菌属菌株(Rhodococcus globerulus strain)AQ719+TX、红冬孢酵母属(Rhodosporidiumdiobovatum)+TX、圆红冬孢酵母菌(Rhodosporidium toruloides)+TX、红酵母属(Rhodotorula spp.)+TX、黏红酵母(Rhodotorula glutinis)+TX、禾本红酵母(Rhodotorula graminis)+TX、粘膜红酵母(Rhodotorula mucilagnosa)+TX、深红酵母(Rhodotorula rubra)+TX、酿酒酵母(Saccharomyces cerevisiae)+TX、玫瑰红球菌(Salinococcus roseus)+TX、小核盘菌(Sclerotinia minor)+TX、小核盘菌(Sclerotiniaminor)+TX、柱顶孢霉属(Scytalidium spp.)+TX、镰孢菌(Scytalidiumuredinicola)+TX、多角体病毒(Spodoptera exigua nuclear polyhedrosis virus)(Spod-+TX、)+TX、灵杆菌(Serratia marcescens)+TX、普城沙雷菌(Serratiaplymuthica)+TX、沙雷氏菌属(Serratia spp.)+TX、粪生粪壳菌(Sordaria fimicola)+TX、多角体病毒(Spodoptera littoralis nucleopolyhedrovirus)+TX、红掷孢酵母(Sporobolomyces roseus)+TX、嗜麦芽寡养单胞菌(Stenotrophomonas maltophilia)+TX、不吸水链霉菌(Streptomyces ahygroscopicus)+TX、链霉菌(Streptomycesalbaduncus)+TX、链霉菌脱落(Streptomyces exfoliates)+TX、鲜黄链霉菌(Streptomycesgalbus)+TX、灰平链霉菌(Streptomyces griseoplanus)+TX、灰绿链霉菌(Streptomycesgriseoviridis)+TX、利迪链霉菌(Streptomyces lydicus)+TX、利迪链霉菌(Streptomyces lydicus)WYEC-108+Tx、紫色链霉菌(Streptomyces violaceus)+TX、小立毛藓(Tilletiopsis minor)+Tx、铁艾酵母属(Tilletiopsis spp.)+TX、棘孢木霉(Trichoderma asperellum)(T34)+Tx、木霉菌株(Trichoderma gamsii)+TX、深绿木霉(Trichoderma atroviride)+TX、钩状木霉(Trichoderma hamatum)TH 382+TX、哈茨木霉(Trichodermaharzianum rifai)+TX、哈茨木霉(Trichoderma harzianum)T-22(Trianum-+TX、PlantShield+TX、+TX、Trianum-)+TX、哈茨木霉(Trichoderma harzianum)T-39+TX、木霉属伊哈特(Trichodermainhamatum)+TX、康氏木霉(Trichoderma koningii)+TX、木霉属(Trichoderma spp.)LC 52+TX、木素木霉(Trichoderma lignorum)+TX、长柄木霉(Trichodermalongibrachiatum)+TX、多孢子菌(Trichoderma polysporum)(Binab)+TX、紫杉木霉(Trichoderma taxi)+TX、绿木霉(Trichoderma virens)+TX、绿木霉(Trichodermavirens)(绿粘帚霉(formerly Gliocladium virens)GL-21)+TX、绿色木霉(Trichoderma viride)+TX、木霉应变(Trichoderma viride strain)ICC 080+TX、茁芽丝孢酵母(Trichosporon pullulans)+TX、毛孢子菌属(Trichosporon spp.)+TX、粉红聚端孢属(Trichothecium spp.)+TX、粉红单端胞霉(Trichothecium roseum)+TX、小菜蛾菌株(Typhula phacorrhiza strain)94670+TX、小菜蛾菌株(Typhula phacorrhiza strain)94671+TX、黑细极格孢(Ulocladium atrum)+TX、奥德曼细基格孢(Ulocladium oudemansii)(Botry-)+TX、玉蜀黍黑粉菌(Ustilagomaydis)+TX、各种各样的细菌并且补充微量营养物(Natural)+Tx、各种各样的真菌(Millennium)+TX、轮枝菌(Verticillium chlamydosporium)+TX、蜡蚧轮枝菌(Verticillium lecanii)(+TX、)+TX、Vip3Aa20+TX、维管状杆菌(Virgibaclillus marismortui)+TX、野油菜黄单胞菌梨孢镰刀菌(Xanthomonascampestris 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、Molt-+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 C-)+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)(Isomate-)+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、Check-+TX、紫杉醇;以及
微生物包括:蚜小蜂属(Aphelinus abdominalis)+Tx、蚜茧蜂(Aphidius ervi)(Aphelinus-)+TX、抑虱跳小蜂属泼哌亚(Acerophagus papaya)+TX、二星瓢虫(Adalia bipunctata)(Adalia-)+TX、二星瓢虫(Adalia bipunctata)+TX、二星瓢虫(Adalia bipunctata)+TX、橘蜡蚧(Ageniaspiscitricola)+Tx、阿根多胚跳小蜂属(Ageniaspis fuscicollis)+TX、钝绥螨(Amblyseiusandersoni)(+TX、Andersoni-)+TX、钝绥螨属(Amblyseiuscalifornicus)(+TX,)+TX、胡瓜钝绥螨(Amblyseius cucumeris)(+TX、Bugline)+TX、伪钝绥螨(Amblyseius fallacis)+TX、钝绥螨属斯维克(Amblyseius swirskii)(Bugline+TX、Swirskii-)+TX、奥氏钝绥螨(Amblyseius womersleyi)+TX、刺虱黑蜂(Amitushesperidum)+TX、缨翅缨小蜂属奥特姆(Anagrus atomus)+TX、棕腹非洲树蛙(Anagyrusfusciventris)+TX、缨翅缨小蜂属卡玛丽(Anagyrus kamali)+TX、缨翅缨小蜂属咾克(Anagyrus loecki)+TX、缨翅缨小蜂属破度道斯(Anagyrus pseudococci)+TX、扁角跳小蜂属本菲斯(Anicetus benefices)+TX、金小蜂(Anisopteromalus calandrae)+TX、林地花蝽(Anthocoris nemoralis)(Anthocoris-)+TX、蚜小蜂属(Aphelinusabdominalis)(+TX、)+TX、蚜小蜂属安斯克(Aphelinus asychis)+TX、科列马阿布拉小蜂(Aphidius colemani)+TX、棉长管蚜蚜茧蜂(Aphidiuservi)+TX、烟蚜茧蜂(Aphidius gifuensis)+TX、桃赤蚜蚜茧蜂(Aphidiusmatricariae)(Aphipar-)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)+TX、黄蚜小蜂(Aphytislingnanensis)+TX、印巴黄金蚜小蜂(Aphytis melinus)+TX、蜚卵啮小蜂(Aprostocetushagenowii)+TX、马桑菌株(Atheta coriaria)+TX、熊蜂属(Bombus spp.)+TX、欧洲熊蜂(Bombus terrestris)(Natupol)+TX、欧洲熊蜂(Bombusterrestris)(+TX,)+TX、头肿腿蜂属斯黛瑞斯(Cephalonomiastephanoderis)+TX、黑缘红(Chilocorus nigritus)+TX、普通草蛉(Chrysoperla carnea)+TX、普通草蛉(Chrysoperla carnea)+TX、通草蛉属鸢尾草(Chrysoperla rufilabris)+TX、瑟姬小蜂属英格努乌斯(Cirrospilus ingenuus)+TX、瑟姬小蜂属寄生蜂(Cirrospilus quadristriatus)+TX、瑟姬小蜂属菲利斯到(Citrostichusphyllocnistoides)+TX、冈崎釉小蜂(Closterocerus chamaeleon)+TX、釉小蜂属(Closterocerus spp.)+TX、克虱跳小蜂属破米特(Coccidoxenoides perminutus)+TX、食蚧蚜小蜂属扣破瑞(Coccophagus cowperi)+TX、食蚧蚜小蜂属力克吶(Coccophagus lycimnia)+TX、螟黄足盘绒茧蜂(Cotesia flavipes)+TX、菜蛾绒茧蜂(Cotesia plutellae)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(+TX、)+TX、日本方头甲(Cybocephalus nipponicus)+TX、反颚茧蜂(Dacnusasibirica)+Tx、反颚茧蜂(Dacnusa sibirica)+TX、潜蝇姬小蜂(Diglyphusisaea)+TX、小黑瓢虫(Delphastus catalinae)+Tx、小黑盗(Delphastus pusillus)+TX、长尾潜蝇茧蜂(Diachasmimorpha krausii)+TX、长尾潜蝇茧蜂(Diachasmimorpha longicaudata)+TX、长凹姬蜂属株库达(Diaparsis jucunda)+TX、长尾潜蝇茧蜂属阿里嘎瑞恩斯(Diaphorencyrtus aligarhensis)+TX、潜蝇姬小蜂(Diglyphus isaea)+TX、潜蝇姬小蜂(Diglyphus isaea)(+TX,)+TX、反颚茧蜂(Dacnusa sibirica)(+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(Encarsiaformosa)(Encarsia+TX、+TX、En-)+TX、浆角蚜小蜂(Eretmoceruseremicus)+TX、蚜小蜂属股德鲁普(Encarsia guadeloupae)+TX、海地恩蚜小蜂(Encarsia haitiensis)+TX、细扁食蚜蝇(Episyrphus balteatus)+TX、蚜小蜂属思博尼(Eretmoceris siphonini)+TX、浆角蚜小蜂加利福尼科斯(Eretmoceruscalifornicus)+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(Eretmocerushayati)+Tx、蒙氏桨角蚜小蜂(Eretmocerus mundus)(+TX、Eretline)+TX、桨角斯本尼(Eretmocerus siphonini)+TX、光缘瓢虫属(Exochomus quadripustulatus)+TX、Feltiella acarisuga+TX、Feltiella acarisuga+TX、阿里山潜蝇茧蜂(Fopius arisanus)+TX、桔小实蝇(Fopius ceratitivorus)+TX、芒柄花黄素(Formononetin)(Wirless)+TX、细腰凶蓟马(Franklinothrips vespiformis)+TX、静走螨属(Galendromus occidentalis)+TX、棱角肿腿蜂属(Goniozuslegneri)+TX、麦蛾茧蜂(Habrobracon hebetor)+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(Heterorhabditis bacteriophora)(NemaShield+TX、+TX、Terranem-+TX、+TX、+TX、B-+TX、NemAttack+TX、)+TX、大异小杆线虫(Heterorhabditis megidis)(Nemasys+TX、BioNem+TX、Exhibitline+TX、Larvanem-)+TX、斑长足瓢虫(Hippodamia convergens)+TX、尖狭下盾螨(Hypoaspis aculeifer)(Aculeifer-+TX、Entomite-)+TX、兵下盾螨(Hypoaspis miles)(Hypoline+TX、Entomite-)+Tx、黑色枝跗瘿蜂(Lbalialeucospoides)+TX、负泥虫姬蜂副楼科斯(Lecanoideus floccissimus)+TX、负泥虫姬蜂恩版的目(Lemophagus errabundus)+TX、负泥虫姬蜂安瑞斯(Leptomastidea abnormis)+TX、丽扑跳小蜂属(Leptomastix dactylopii)+TX、丽扑跳小蜂属(Leptomastixepona)+TX、Lindorus lophanthae+TX、Lipolexis oregmae+Tx、叉叶绿蝇(ucilia caesar)+TX、柄瘤蚜茧蜂属(Lysiphlebus testaceipes)+TX、乌苏里蝮(Macrolophuscaliginosus)(Mirical-+TX、Macroline+TX、)+TX、Mesoseiuluslongipes+TX、阔柄跳小蜂属福禄勿(Metaphycus flavus)+TX、阔柄跳小蜂属隆斯贝瑞(Metaphycus lounsburyi)+TX、角纹脉褐蛉(Micromus angulatus)+TX、花翅跳小蜂属(Microterys flavus)+TX、窃蝇金小蜂属和蛹小蜂属+TX、新螯蜂属(Neodryinus typhlocybae)+TX、加州新小绥螨(Neoseiulus californicus)+TX、胡瓜钝绥螨(Neoseiulus cucumeris)+TX、加州钝绥螨(Neoseiulus fallacis)+TX、Nesideocoris tenuis(+TX、)+TX、古铜黑蝇(Ophyraaenescens)+TX、食螨小花蝽(Orius insidiosus)(Thripor-+TX、Oriline)+TX、小花蝽属(Orius laevigatus)(Thripor-+TX、Oriline)+TX、小花蝽属蛛丝鲁斯(Orius majusculus)(Oriline)+Tx、小黑花椿象(Orius strigicollis)(Thripor-)+TX、Pauesia juniperorum+TX、瓢虫柄腹姬小蜂(Pediobius foveolatus)+TX、蜚蠊(Phasmarhabditis hermaphrodita)+TX、Phymastichus coffea+TX、小植绥螨属(Phytoseiulus macropilus)+TX、智利小植绥螨(Phytoseiulus persimilis)(+TX、Phytoline )+TX、捕食性椿象(Podisus maculiventris)+TX、寄生蝇(Pseudacteon curvatus)+TX、寄生性蚤蝇(Pseudacteon obtusus)+TX、寄生蚤蝇(Pseudacteon tricuspis)+TX、玉棒跳小蜂属(Pseudaphycus maculipennis)+TX、短背茧蜂属梅西卡纳(Pseudleptomastix mexicana)+TX、短背茧蜂属菲利斯(Psyllaephaguspilosus)+Tx、短背茧蜂属(Psyttalia concolor)(康普里)+TX、刺桐属(Quadrastichusspp.)+TX、根瘤菌楼酚斯(Rhyzobius lophanthae)+TX、澳洲瓢虫(Rodolia cardinalis)+TX、瘤胃杀头(Rumina decollate)+TX、长柄杜英(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(Steinernema feltiae)(+TX、Nemasys+TX、BioNem+TX、Steinernema-+TX、+TX、+TX、Exhibitline+TX、Scia-+TX、)+TX、斯氏线虫克瑞斯(Steinernemakraussei)(Nemasys+TX、BioNem+TX、Exhibitline)+TX、斯氏线虫肉布瑞(Steinernema riobrave)(+TX、)+TX、斯氏线虫斯盖普特斯(Steinernema scapterisci)(Nematac)+TX、斯氏线虫属(Steinernema spp.)+TX、斯氏线虫(Steinernematid spp.)(Guardian)+TX、深点食螨瓢虫(Stethoruspunctillum)+TX、亮腹釉小蜂(Tamarixia radiate)+TX、啮小蜂属(Tetrastichus setifer)+TX、Thripobius semiluteus+TX、长尾小蜂属(Torymussinensis)+TX、甘蓝夜蛾赤眼蜂(Trichogramma brassicae)(Tricholine)+TX、甘蓝夜蛾赤眼蜂(Trichogramma brassicae)(Tricho-)+TX、广赤眼蜂(Trichogrammaevanescens)+TX、微小赤眼蜂(Trichogramma minutum)+TX、玉米螟赤眼蜂(Trichogrammaostriniae)+TX、亦眼蜂普兰恩瑞(Trichogramma platneri)+TX、短管赤眼蜂(Trichogramma pretiosum)+TX、螟黑点瘤姬蜂(Xanthopimpla stemmator)、以及
其他生物制剂包括:脱落酸+TX、+TX、紫癜(Chontrol)+TX、盘长孢状刺盘孢(Colletotrichum gloeosporioides)+TX、辛酸铜盐(CopperOctanoate)+TX、δ陷阱(Delta traps)(Trapline)+TX、解淀粉欧文氏菌(Erwinia amylovora)(Harpin)(+TX、Ni-HIBIT Gold)+TX、磷酸铁+TX、漏斗诱捕器(Funnel traps)(Trapline)+TX、+TX、Grower's+TX、单环芸苔甾内酯(Homo-brassonolide)+TX、磷酸铁(Lilly Miller WorryFree Ferramol Slug&Snail)+TX、MCP冰雹诱捕器(MCP hail trap)(Trapline)+TX、简爪茧蜂属超子(Microctonus hyperodae)+TX、根腐病(Mycoleptodiscusterrestris)(Des-)+TX、+TX、+TX、+TX、信息素罗网(Pheromone trap)(Thripline)+TX、碳酸氢钾(+TX、脂肪酸的钾盐+TX、硅酸钾溶液(Sil-)+TX、碘化钾+potassiumthiocyanate+TX、SuffOil-+Tx、蜘蛛毒+TX、蝗虫微孢子虫(Nosema locustae)(Semaspore Organic Grasshopper)+TX、粘着诱捕器(Sticky traps)(Trapline+TX、Rebell)+TX和诱捕器(Traps)(Takitrapline y+)+TX。
在活性成分之后的括号中的参考例如[3878-19-1]是指化学文摘的登记号。以上描述的混合配对物是已知的。当活性成分包括在“杀有害生物剂手册(The PesticideManual)”[杀有害生物剂手册-全球概览(The Pesticide Manual-A World Compendium);第13版;编著:C.D.S.汤姆林(TomLin);英国农作物保护委员会(The Pesticide Manual-AWorld Compendium;Thirteenth Edition;Editor:C.D.S.TomLin;The British CropProtection Council)]中时,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)之下描述。当以上对具体的化合物加入“[CCN]”时,所讨论的化合物包括在“农药通用名纲要(Compendium of PesticideCommon Names)”中,该纲要在互联网上可得:[A.Wood(伍德);农药通用名纲要,版权1995-2004];例如化合物“乙酰虫腈”在互联网址http://www.alanwood.net/pesticides/acetoprole.html下进行了描述。
上述的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。如果名称不是“通用名”,那么对于特定化合物在圆括号内给出了作为代替而使用的该名称的性质;在这种情况下,使用IUPAC名称、IUPAC/化学文摘名称、“化学名称”、“传统名称”、“化合物名称”、或“研究代码”,或者如果既没有使用这些名称之一,也没有使用“通用名”,那么使用的是“别名”。“CAS登记号”意指化学文摘登记号。
选自表1至6的具有化学式I的化合物与上述活性成分的活性成分混合物包括选自表1至6的化合物和上述活性成分,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。
以上描述的混合物可以被用于控制有害生物的方法中,该方法包括将一种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,除了一种通过手术或疗法用于处理人或动物体的方法以及对于人或动物体实施的诊断方法。
包含选自表1至6的具有化学式I的化合物以及一种或多种如以上描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到表6的这些具有化学式I的化合物和如上所述活性成分的顺序对于实施本发明并不是至关重要的。
根据本发明的这些组合物还可以包含其他固体或液体助剂,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一种本身已知的方式,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;和在至少一种助剂存在下,例如通过透彻混合活性成分与一种或一些助剂和/或与一种或一些助剂一起研磨活性成分来制备。用于制备这些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。
组合物的施用方法、也就是说控制以上提及的类型的有害生物的方法,例如喷洒、雾化、喷粉、涂刷、敷料、散射或浇注,选择这些方式以适合当时环境的既定目标;并且这些组合物用于控制以上提及的类型的有害生物的用途是本发明的其他主题。典型的浓度比是在0.1与1000ppm之间,优选地在0.1与500ppm之间的活性成分。每公项的施用量总体上是每公项1到2000g活性成分,尤其是10到1000g/ha,优选地10到600g/ha。
在作物保护领域中,优选的施用方法是施用至这些植物的叶(叶施药),可能的是选择施用的频率和比率以符合所提及的有害生物的侵染风险。可替代地,该活性成分可以通过根系统(内吸作用)到达植物,这是通过用一种液体组合物将这些植物的所在地浸透或者通过将固体形式的活性成分引入植物的所在地(例如引入土壤,例如以颗粒(土施)的形式)来实现的。在水稻作物的情况下,这样的颗粒剂可以被计量加入淹水的稻田中。
本发明的这些化合物及其组合物还适合于植物繁殖材料的保护(例如种子,像果实、块茎或籽粒,或者苗圃植物)对抗上述类型的有害生物。可以用该化合物在种植前对该繁殖材料进行处理,例如可以在播种前对种子进行处理。可替代地,该化合物可以施用至种子籽粒(包衣),这是通过将籽粒浸渍入液体组合物中或通过施涂一种固体组合物层实现的。当该繁殖材料被种植在施用处时,还可能例如在条播期间将这些组合物施入种子犁沟。这些用于植物繁殖材料的处理方法和因此处理的植物繁殖材料是本发明另外的主题。典型的处理比率将取决于有待控制的植物以及有害生物/真菌,通常在每100kg种子1克至200克之间,优选在每100kg种子5克至150克之间,例如在每100kg种子10克至100克之间。
术语种子包括所有种类的种子以及植物繁殖体,包括但并不限于真正的种子、种子块、吸盘、谷粒、鳞球茎、果实、块茎、谷物、根茎、插条、切割枝条以及类似物并且在一个优选的实施例中是指真正的种子。
本发明还包括用具有化学式I的化合物包衣或处理的种子或含有具有化学式I的化合物的种子。尽管成分的更多或更少的部分可以渗透到该种子材料中,这取决于施用的方法,术语“包衣或处理和/或含有”通常表示在施用的时候,在大多数情况下,该活性成分在该种子的表面。当所述种子产物(再)种植时,它可以吸收该活性成分。在一个实施例中,本发明使得一种其上粘附有具有化学式(I)的化合物的植物繁殖材料可得。此外,由此可得一种包括用具有化学式(I)的化合物处理过的植物繁殖材料的组合物。
种子处理包括本领域中已知的所有适合的种子处理技术,例如拌种、种子包衣、种子撒粉、浸种以及种子造粒。可以通过任何已知的方法实现具有化学式I的化合物的种子处理施用,例如,在这些种子播种之前或播种/种植过程中喷雾或通过撒粉。
生物实施例:
实例B1:对抗海灰翅夜蛾(埃及棉叶虫)的活性
(杀幼虫剂,饲喂/残留接触活性,预防的)
将棉叶圆片放在24孔微量滴定板中的琼脂上并用测试溶液喷洒。在干燥之后,将叶圆片用5只L1期幼虫进行侵染。在经过处理之后(DAT)3天,针对死亡率、驱虫效果、摄食行为和生长调节对样品进行检查。
在本次测试中,在400ppm的浓度下,化合物P1、P2、P14、P3、P4、P5、P6、P7、P8、P9、P11、P12、P13、P15、P27、P22、P21、P20、P23、P25、P35、P34、P32、P30、P36和P37显示出超过80%的活性。
实例B2:对抗小菜蛾(Plutella xylostella)(小菜蛾(Diamond back moth))的活
性:
(杀幼虫剂,饲喂/残留接触活性,预防的)
将具有人工饲料的24孔微量滴定平盘(MTP)通过移液管用测试溶液进行处理。在干燥之后,用L2期幼虫对MTP上的实验对象进行侵染(10-15/孔)。在5天的孵育期之后,针对幼虫死亡率、拒食情况和生长调节对样品进行检查。
在本次测试中,在400ppm的浓度下,化合物P1、P2、P14、P3、P5、P6、P7、P8、P9、P10、P11、P12、P13、P15、P27、P22、P21、P20、P38、P23、P28、P26、P25、P35、P34、P32、P31、P36和P37显示出超过80%的活性。
实例B3:对抗黄瓜条叶甲(玉米根虫)的活性
(在玉米苗上的L2幼虫,喂养/接触,预防性)
将放在24孔微量滴定板中的琼脂层上的玉米芽通过喷洒用测试溶液进行处理。在干燥之后,用L2期幼虫对MTP上的实验对象进行侵染(6-10/孔)。在5天的孵育期之后,针对幼虫死亡率和生长调节对样品进行检查。
在本次测试中,在400ppm的浓度下,化合物P1、P2、P14、P3、P4、P5、P6、P7、P8、P9、P10、P11、P12、P13、P15、P33、P27、P22、P21、P38、P23、P28、P26、P25、P35、P34、P32、P36和P37显示出超过80%的活性。
实例B4:对抗西花蓟马(西方花蓟马)的活性:
(混合种群,摄食/接触,预防的)
将向日葵叶圆片放在24孔微量滴定板中的琼脂上并用测试溶液喷雾。在干燥之后,将叶圆片用混合年龄的花蓟马种群侵染。在7DAT的孵育期之后,针对死亡率和特殊效应(例如植物毒性)对样品进行检查。
在本次测试中,在400ppm的浓度下,化合物P1、P7、P13、P15、P22、P29和P36显示出超过80%的活性。
实例B5:对抗烟粉虱(棉粉虱)的活性
(杀成虫剂接触活性,预防性的),成虫
将棉叶圆片放在24孔微量滴定板中的琼脂上并用测试溶液喷洒。在干燥之后,将叶圆片用成年粉虱进行侵染。在7DAT的孵育期之后,针对死亡率和特殊效应(例如植物毒性)对样品进行检查。
在本次测试中,在400ppm的浓度下,化合物P1、P2、P3、P5、P7、P8、P13、P27、P22、P20、P25、P34和P36显示出超过80%的活性。
实例B6:对抗埃及伊蚊(黄热病蚊子)的活性:
在乙醇中,以200ppm的施用率,将试验溶液施加到12孔组织培养皿。一旦沉积物干燥,将五天、两天至五天大的成年雌性埃及伊蚊添加到每个孔中,并且在棉塞中保持10%的蔗糖溶液。引入后一小时,进行击倒评估,并且在引入后24小时和48小时,评估死亡率。
以下化合物在48h后对埃及伊蚊给出至少80%的控制:P1、P2、P7、P13、P22和P27。
实例B7:对抗海灰翅夜蛾(埃及棉叶虫)的活性
(系统活性)
将测试化合物用移液管施用到24孔平板中并且与琼脂进行混合。将莴苣种子放在琼脂上并且用另一块也包含琼脂的平板封闭该多孔板。7天之后,根已经将该化合物吸收并且莴苣已经生长进入盖平板。现在将这些莴苣叶切到盖平板中。将夜蛾属卵吸移穿过一块潮湿凝胶印记纸上的塑料模板及其所封闭的平板。感染之后5天,针对死亡率、驱虫效果、摄食行为以及生长调节检查样品。
在本次测试中,在12.5ppm的浓度下,化合物P1、P2、P3、P5、P6、P7、P13、P27、P22、P21、P23、P25、P35和P36显示出至少80%的活性。
实例B8:对抗桃蚜(青桃蚜)的活性
(饲喂/残留接触活性,预防的),混合种群
将向日葵叶圆片放在一个24孔微量滴定板中的琼脂上并用测试溶液喷洒。在干燥之后,将这些叶圆片用混合年龄的蚜虫群体侵染。在6DAT的孵育期之后,针对死亡率和特殊效应(例如植物毒性)对样品进行检查。
在本次测试中,在400ppm的浓度下,化合物P1、P2、P14、P3、P5、P6、P7、P8、P9、P11、P12、P13、P21、P20、P23、P28、P25、P34、P32、P31、P29、P36和P37显示出超过80%的活性。
实例B9:对抗桃蚜(青桃蚜)的活性
(系统/饲喂活性,治疗的),混合种群
将受到混合年龄的蚜虫群体侵染的豌豆幼苗的根部直接放在测试溶液中。在引入之后6天,针对死亡率和对植物的特殊效应对样品进行检查。
在本次测试中,在24ppm的浓度下,化合物P8、P34和P32显示出至少80%的活性。
实例B10:对抗大豆褐椿(Euschistus heros)(新热带褐臭蝽)的活性
将24孔微量滴定板中的琼脂上的大豆叶用从10'000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。干燥之后,将叶用N-2期若虫进行侵染。侵染5天之后,针对死亡率对这些样品进行评估。
在本次测试中,在400ppm的浓度下,化合物P1、P2、P14、P3、P5、P6、P7、P11、P12、P13、P15、P33、P27、P22、P21、P23、P25、P35、P34、P32、P36和P37显示出超过80%的活性。
实例B11:对抗烟蓟马(葱蓟马)的活性
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并且用从10'000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将这些叶圆片用一个混合年龄的蓟马种群侵染。侵染6天之后,针对死亡率对这些样品进行评估。
以下化合物在400ppm施用率下得到至少80%的死亡率:
P7、P13和P36
实例B12:对抗二点叶螨(二斑叶螨)的活性
将24孔微量滴定板中的琼脂上的豆叶圆片用从10'000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将这些叶圆片用一个混合年龄的螨种群侵染。侵染8天之后,针对混合种群(流动平台)的死亡率对这些样品进行评估。
以下化合物在400ppm施用率下得到至少80%的死亡率:P4和P36。
Claims (12)
1.一种具有化学式I的化合物,
其中
A表示CH或N;
每个R彼此独立地是C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基硫烷基、C1-C4卤代烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4卤代烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷氧基羰基、C1-C6烷基氨基、C2-C8二烷基氨基、卤素、氰基、氰基C1-C4烷基、三(C1-C4烷基)甲硅烷基、C1-C4烷氧基C1-C4烷氧基、C1-C4烷基硫烷基C1-C4烷氧基或硝基;
或每个R彼此独立地是苯基、嘧啶基、噻唑基、吡啶基、咪唑基、吡唑基、噁唑基或噁二唑基;其中所述苯基、嘧啶基、噻唑基、吡啶基、咪唑基、吡唑基、噁唑基或噁二唑基本身可以是被独立地选自下组的取代基单取代至多取代的,该组由以下各项组成:卤素、C1-C6烷基和氰基;
n是0、1、2、3、4或5;
X是S、SO或SO2;
R1是C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基、被选自下组的取代基单取代、二取代或三取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;或R1是被选自下组的取代基单取代或多取代的C3-C6环烷基-C1-C4烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;
或R1是C2-C6烯基、C2-C6卤代烯基或C2-C6炔基;
R2是卤素、C1-C4卤代烷基或被一个或两个选自下组的取代基取代的C1-C4卤代烷基,该组由以下各项组成:羟基、甲氧基和氰基;
或R2是C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、O(C1-C4卤代烷基)或-C(O)C1-C4卤代烷基;
或R2是C3-C6环烷基,其可以是被选自下组的取代基单取代或多取代的,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且
X1是O、S或NR3,其中R3是氢、C1-C4烷基、C2-C6烯基、C2-C6炔基、C1-C4烷氧基-C1-C4烷基或C3-C6环烷基;
以及那些化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。
2.根据权利要求1所述的具有化学式I的化合物,由以下具有化学式I-1的化合物表示
其中
R、R2和n是如在权利要求1中的化学式I下所定义的;
Xa1是S、SO或SO2;并且
Ra1是甲基、乙基、正丙基、异丙基或环丙基甲基。
3.根据权利要求2所述的具有化学式I-1的化合物,其中
n是1并且R是卤素、氰基或C1-C4卤代烷基。
4.根据权利要求1所述的具有化学式I的化合物,由以下具有化学式I-2的化合物表示
其中
R、R2和n是如在权利要求1中的化学式I下所定义的;
Xa2是S、SO或SO2;并且
Ra2是甲基、乙基、正丙基、异丙基或环丙基甲基。
5.根据权利要求4所述的具有化学式I-2的化合物,其中
n是1并且R是卤素、氰基或C1-C4卤代烷基。
6.根据权利要求1所述的具有化学式I的化合物,由具有化学式Ia的化合物表示
其中
X2是SO2;
X3是N-C1-C4烷基;
R4是C1-C4烷基;
R5是卤素、C1-C4卤代烷基、氰基或C1-C4烷氧基;
n是1、2或3;并且
R6是C1-C4卤代烷基。
7.根据权利要求1所述的具有化学式I的化合物,由具有化学式Ib的化合物表示
其中
A是N或CH;
X2是S或SO2;
X3是N-C1-C4烷基;
R7是C1-C4烷基;
R8是卤素、氰基、C1-C4卤代烷基或C1-C4烷氧基;
n是0、1、2或3;并且
R9是C1-C4卤代烷基。
8.一种具有化学式IV的化合物
其中
R1、R2、X、X1和A是如在权利要求1中的化学式I下所定义的,并且Yb2是-B(OH)2、-B(ORb2)2,其中Rb2是C1-C4烷基或4,4,5,5-四甲基-1,3,2-二噁环戊硼烷-2-基。
9.一种杀有害生物组合物,其包含至少一种根据权利要求1所述的具有化学式I的化合物或适当时其互变异构体作为活性成分以及至少一种助剂,所述化合物在所有情况下为游离形式或农用化学上可用的盐形式。
10.一种用于控制有害生物的方法,该方法包括将根据权利要求9所述的组合物施用于这些有害生物或其环境中,除了一种通过手术或疗法用于处理人或动物体的方法以及对于人或动物体实施的诊断方法。
11.一种用于保护植物繁殖材料免受有害生物攻击的方法,该方法包括用根据权利要求9所述的组合物处理该繁殖材料或该繁殖材料所种植的场所。
12.根据权利要求11中所述的方法处理的植物繁殖材料。
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CN103261170A (zh) * | 2010-12-24 | 2013-08-21 | 住友化学株式会社 | 稠杂环化合物及其用于害虫防治的用途 |
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CN114746403A (zh) * | 2019-11-27 | 2022-07-12 | 先正达农作物保护股份公司 | 用于制备5-氯-吡啶-2-甲酸以及具有3-含硫取代基的甲酸酯的方法 |
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CA2954238A1 (en) | 2016-01-14 |
KR20170029554A (ko) | 2017-03-15 |
WO2016005263A1 (en) | 2016-01-14 |
US10051864B2 (en) | 2018-08-21 |
BR112017000269B1 (pt) | 2020-06-02 |
US20170156329A1 (en) | 2017-06-08 |
EP3166941B1 (en) | 2018-01-10 |
RU2017103953A (ru) | 2018-08-08 |
US9775353B2 (en) | 2017-10-03 |
CN106661021B (zh) | 2019-06-14 |
MX2017000305A (es) | 2017-04-27 |
JP2017523167A (ja) | 2017-08-17 |
ES2663523T3 (es) | 2018-04-13 |
US20170354151A1 (en) | 2017-12-14 |
JP6663907B2 (ja) | 2020-03-13 |
EP3166941A1 (en) | 2017-05-17 |
BR112017000269A2 (pt) | 2018-06-05 |
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