CN103003268A - 作为杀微生物剂的异噁唑、异噻唑、呋喃以及噻吩化合物 - Google Patents
作为杀微生物剂的异噁唑、异噻唑、呋喃以及噻吩化合物 Download PDFInfo
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- CN103003268A CN103003268A CN2011800352768A CN201180035276A CN103003268A CN 103003268 A CN103003268 A CN 103003268A CN 2011800352768 A CN2011800352768 A CN 2011800352768A CN 201180035276 A CN201180035276 A CN 201180035276A CN 103003268 A CN103003268 A CN 103003268A
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- unsubstituted
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- phenyl
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title description 25
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 title description 2
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- 229910052731 fluorine Inorganic materials 0.000 claims description 26
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
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- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims description 3
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- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- JJSYXNQGLHBRRK-SFEDZAPPSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-SFEDZAPPSA-N 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
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- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
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- CTPKSRZFJSJGML-UHFFFAOYSA-N sulfiram Chemical compound CCN(CC)C(=S)SC(=S)N(CC)CC CTPKSRZFJSJGML-UHFFFAOYSA-N 0.000 description 1
- 229950008316 sulfiram Drugs 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229940063650 terramycin Drugs 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 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
- 239000004753 textile Substances 0.000 description 1
- BXBMHLIYMZRCNK-UHFFFAOYSA-H thallium(3+);trisulfate Chemical compound [Tl+3].[Tl+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BXBMHLIYMZRCNK-UHFFFAOYSA-H 0.000 description 1
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 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
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
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- 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
- 230000000699 topical effect Effects 0.000 description 1
- 231100000033 toxigenic Toxicity 0.000 description 1
- 230000001551 toxigenic effect Effects 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 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
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
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- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- DFQMKYUSAALDDY-MQEBUAKTSA-N trinactin Chemical compound C[C@@H]([C@@H]1CC[C@@H](O1)C[C@H](OC(=O)[C@H](C)[C@H]1CC[C@H](O1)C[C@H](CC)OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@@H](CC)OC(=O)[C@@H]1C)CC)C(=O)O[C@@H](C)C[C@@H]2CC[C@H]1O2 DFQMKYUSAALDDY-MQEBUAKTSA-N 0.000 description 1
- DFQMKYUSAALDDY-UHFFFAOYSA-N trinactin Natural products CC1C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(C)CC2CCC1O2 DFQMKYUSAALDDY-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
- 241000701366 unidentified nuclear polyhedrosis viruses 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
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 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
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 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
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及一种具有化学式I的化合物:
Description
本发明涉及新颖的包含叔醇(或其醚)部分的化合物,尤其是包含呋喃-3-基-甲醇部分的化合物、包含异噁唑-4-基-甲醇部分的化合物、包含异噻唑-4-基-甲醇部分的化合物和/或包含噻吩-3-基-甲醇部分的化合物;它们在用于控制和/或防止在植物中的微生物侵染(特别是真菌侵染)的组合物以及方法中的用途;并且涉及用于制备这些化合物的方法。
对于植物而言,严重的微生物侵染,特别是真菌侵染(系统或局部)的发病率继续增加。
杀真菌剂是天然或合成来源的化合物,它们起到的作用是保护植物免于真菌引起的损害。目前的农业方法很大程度上依赖于使用杀真菌剂。实际上,一些作物不使用杀真菌剂时不能有效地生长。使用杀真菌剂允许栽培者增加作物的产量并且因此增加该作物的价值。已经发展了许多杀真菌的试剂。然而,真菌侵染的治疗仍然是一个主要问题。此外,杀真菌剂耐受性已经变成了一个严重的问题,使得这些试剂对于一些农业用途是无效的。这样,对于发展新的杀真菌化合物存在一种需要。
本发明因此涉及具有化学式(I)的化合物
其中
X是S或O;
Y是C-H或N;
R1是未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2- 8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;或一个取代的5至10-元芳香族杂环;
R2是H;卤素,未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C7-15芳烷基;取代的C7- 15芳烷基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;未取代的C6-10芳硫基-C1-8烷基;取代的C6-10芳硫基-C1-8烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;一个取代的5至10-元芳香族杂环;未取代的C1-8烷基甲硅烷基;或取代的C1-8烷基甲硅烷基;
R3是未取代的C6-10芳基;取代的C6-10芳基;未取代的C1-8烷基;取代的C1-8烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C7-15芳基链烯基;取代的C7-15芳基链烯基;未取代的C7-15芳基炔基;取代的C7-15芳基炔基
R4是H;未取代的C1-C8烷基;取代的C1-C8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;
R5是一个未取代的5至10元芳香族杂环;或一个取代的5至10元芳香族杂环;
除非另外指明,这些取代基R1、R2、R3、R4以及R5是未取代的或取代的,优选这些取代基是未取代的或经以下给出的取代基取代的。
在具有化学式(I)的化合物中的烷基、链烯基以及烷氧基是直链的或者支链的。卤素优选地表示F、Cl、Br、I,并且更优选的卤素表示F或者Cl。
在具有化学式(I)的化合物中的取代的烷基、取代的链烯基、取代的炔基、取代的烷氧基、取代的芳基和/或芳香族杂环基的优选的取代基选自下列取代基:F,Cl,Br,I,-OH,-CN,硝基,-C1-4烷氧基,-C1-4烷硫基,C1-4烷基,C2-4链烯基,C2-4链烯基,C2-4炔基,-C(O)H,-C(O)(C1-4烷基),-C(O)(C1-4烷氧基),-C(O)NH2,-C(O)NH(C1-4烷基),-C(O)N(C1-4烷基)(C1-4烷基),-OC(O)NH(C1-4烷基),-OC(O)N(C1-4烷基)(C1-4烷基),-NHC(O)(C1-4烷基),-NHC(O)(C1-4烷氧基),-N(C1-4烷基)C(O)(C1-4烷基),-N(C1-4烷基)C(O)(C1-4烷氧基),-OC(O)(C1-4烷基),-OC(O)(C1-4烷氧基),-Si(C1-4烷基)3,-Si(C1-4烷氧基)3,C6-10芳基,C6-10芳氧基,C6-10芳硫基,C6-10杂芳基,-(C1-8-全卤烷基),芳基C2-6炔基,-C2-6链烯基,杂芳基C2-6炔基,-C2-6链烯基,C3-8环烷基;-NR8R9,其中,R8与R9独立地是H、-C1-4烷基-C2-4链烯基、-C2-4炔基或者是与在中间的氮结合以形成一个五-或六-元的环,该环可以包括一个或两个或三个的杂原子(除在中间的氮原子外,一个或两个N、O、或S原子),在这种情况下,该杂环是未取代的或者该杂环是由一个或者两个C1-4烷基、-C2-4链烯基取代的或者是取代的-C2-4链烯基、-C2-4炔基或者是取代的-C2-4炔基、-C(O)H、-C(O)(C1-4烷基)、-C(O)(C1-4烷氧基)、-C(O)NH2、-C(O)NH(C1-4烷基)、-C(O)N(C1-4烷基)(C1-4烷基)、-OC(O)NH(C1-4烷基)、-OC(O)N(C1-4烷基)(C1-4烷基)、-NHC(O)(C1-4烷基)、-NHC(O)(C1-4烷氧基)、-N(C1-4烷基)C(O)(C1-4烷基)、-N(C1-4烷基)C(O)(C1-4烷氧基)、-OC(O)(C1-4烷基)、-OC(O)(C1-4烷氧基)、-Si(C1-4烷基)3、-Si(C1-4烷氧基)3、C6-10芳基、C6-10芳氧基、C6-10芳硫基、C6-10杂芳基、-(C1-8-全卤烷基)、芳基C1-4炔基、-C1-6炔基,其中,所有的烷基、链烯基、炔基、烷氧基、芳基、芳氧基、芳硫基或者杂芳基是取代的或者未取代的,优选地,这些取代的基团的取代基仅带有一个另外的取代基,更优选地,这些取代的基团的取代基是不被进一步取代的。
取代的烷基、链烯基、炔基以及烷氧基的更优选的取代基选自下列取代基:-OH、CN、F、Cl、C1-4烷氧基、-C1-4烷硫基、C1-4烷基、C2-4链烯基、C2-4链烯基、C2-4炔基、C6-10芳基、-C1-4烷氨基,更优选-OH、CN、F、Cl、C1-4烷氧基、C1-4烷氨基、-苯基、经Cl或F、-CF3取代的-苯基。这些烷基是支链的或者直链的。最优选的烷基是甲基、乙基、丙基、异丙基、正丁基、叔丁基(1,1-二甲基乙基)、仲-丁基(1-甲基丙基)、异丁基(2-甲基丙基)、戊基、异戊基(iso-pentyl)(3-甲基丁基、异戊基(isoamyl))、1-甲基戊基、1-乙基戊基、己基、庚基、或者辛基。优选的链烯基是乙烯基、丙烯基(1-丙烯基、2-丙烯基)、丁烯基(1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丙烯-1-基、2-甲基丙烯-2-基)、戊烯基(戊-1-烯基、戊-2-烯基、戊-3-烯基、2-甲基丁-1-烯基、3-甲基丁-1-烯基、2-甲基丁-2-烯基、3-甲基丁-2-烯基、2-甲基丁-3-烯基、3-甲基丁-3-烯基、1,2-二甲基丙-2-烯基、1,1-二甲基丙-2-烯基)。优选的炔基是乙炔基、丙炔基(丙-1-炔基或者丙-2-炔基(炔丙基))、丁基(丁-1-炔基、丁-2-炔基、丁-3-炔基)、戊炔基(戊-1-炔基、戊-2-炔基、戊-3-炔基、戊-4-基、3-甲基丁-1-炔基、2-甲基丁-3-炔基、1-甲基丁-3-炔基)。最优选的烷基以及最优选的烷氧基是甲基、乙基、丙基、叔丁基、甲氧基以及乙氧基。甲基、乙基以及甲氧基是非常特别优选的。
优选地,在化学式(I)的化合物中的烷基和/或在化学式(I)的化合物中的烷氧基具有最多两个另外的取代基,更优选地,在化学式(I)的化合物中的烷基和/或在化学式(I)的化合物中的烷氧基带有不多于一个另外的取代基,最优选地,在化学式(I)的化合物中的烷基和/或在化学式(I)的化合物中的烷氧基不被进一步取代。
卤烷基(单独的或者作为一个更大的基团如卤代烷氧基的一部分)是被一个或多个相同或不同的卤素原子取代的烷基,并且是例如三氟甲基、氯二氟甲基、2,2,2-三氟-乙基或2,2-二氟-乙基。
卤链烯基基团各自是被一个或多个相同或不同的卤素原子取代的链烯基基团,并且是例如2,2-二氟乙烯基-乙烯基或1,2-二氯-2-氟-乙烯基。
卤炔基基团各自是被一个或多个相同或不同的卤素原子取代的炔基基团,并且是例如1-氯-丙-2-炔基。
在具有化学式(I)的化合物中的取代的芳基的优选的取代基是选自下列取代基F、Cl、CF3、CN、-OH、硝基、-C1-4烷基、-C1-4烷氧基、-C(O)(C1-4烷氧基)、-C(O)H、-C(O)(C1-4烷基),其中烷基是取代的或者未取代的。在本说明书的上下文中术语“芳基”指一个可以是单环、双环或三环的环系统。此类环的例子包括苯基或萘基、蒽基或菲基。这些芳基基团优选是苯基。
在具有化学式(I)的化合物中的取代的芳基的更优选的取代基是选自下列取代基F、Cl、-C1-4烷基、C1-4烷氧基、-CN、-C(O)(C1-4烷氧基)、-C(O)(C1-4烷基)并且优选地F、Cl是在具有化学式(I)的化合物中的取代的芳基的甚至更优选的取代基。
在具有化学式(I)的化合物中的取代的杂芳基基团(芳香族杂环)的优选的取代基是选自下列取代基F、Cl、CF3、CN、-OH、硝基、-C1-4烷基、-C1-4烷氧基、-C(O)(C1-4烷氧基)、-C(O)H、-C(O)(C1-4烷基),其中烷基是取代的或者未取代的。术语“杂芳基”指芳环系统,该芳环系统包括至少一个杂原子并且由一个单环或两个或更多个稠和的环组成。优选地,单环包含多至三个杂原子并且双环系统包含多至四个杂原子,这些杂原子优选地是选自氮、氧和硫。(5-6元)单环基团的例子包括吡啶基、哒嗪基、嘧啶基、吡嗪基、吡咯基、吡唑基、咪唑基、三唑基、四唑基、呋喃基、苯硫基、噁唑基、异噁唑基、噁二唑基、噻唑基、异噻唑基以及噻二唑基。双环基团的例子包括喹啉基、异喹啉基、噌啉基、喹喔啉基、苯并咪唑基、苯并苯硫基、以及苯并噻二唑基。单环杂芳基优选的,优选包括1至3个选自O、N或S的杂原子的单环,例如吡啶基、哒嗪基、嘧啶基、吡嗪基、吡唑基、呋喃基、苯硫基、噁唑基、异噁唑基、噻唑基,优选吡啶基、吡唑基、呋喃基、苯硫基、噻唑基、吡啶基;并且甚至更优选嘧啶基、吡啶基、喹啉基以及异喹啉基,然而最优选嘧啶基、吡啶基。
这些杂芳基基团优选5至6元芳香族杂环,更优选6元芳香族杂环。
在具有化学式(I)的化合物中的取代的杂芳基基团(芳香族杂环)的更优选的取代基是选自下列取代基F、Cl、-C1-4烷基、C1-4烷氧基、-CN、-C(O)(C1-4烷氧基)、-C(O)(C1-4烷基)并且优选地F、Cl是在具有化学式(I)的化合物中的取代的杂芳基的甚至更优选的取代基。这些杂芳基基团更优选6元芳香族杂环。最优选这些杂芳基基团是未取代的;特别是未取代的吡啶基或嘧啶基,优选未取代的3-吡啶基或5-嘧啶基。
X、Y、R1、R2、R3、R4、和/或R5的优选的值是如以下提出的(以任何组合)。
优选地R1是未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;或一个取代的5至10-元芳香族杂环;
更优选地R1是未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;一个未取代的5至10元芳香族杂环;一个取代的5至10元芳香族杂环;
甚至更优选的R1是未取代的C6-10芳基;取代的C6-10芳基;并且最优选的R1是未取代的苯基;经Cl、F取代的苯基;
优选地R2是H;卤素,未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;未取代的C6-10芳硫基-C1-8烷基;取代的C6-10芳硫基-C1-8烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;一个取代的5至10-元芳香族杂环;未取代的C1-8烷基甲硅烷基;或取代的C1-8烷基甲硅烷基;
更优选地R2是未取代的C1-8烷基;取代的C1-8烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;一个未取代的5至10元芳香族杂环;一个取代的5至10元芳香族杂环;
甚至更优选的R2是未取代的环己基;未取代的苯基;经Cl、F取代的苯基;
最优选的R2是未取代的苯基;经Cl、F取代的苯基;
优选地R3是未取代的C1-8烷基;取代的C1-8烷基;
更优选地R3是未取代的C1-8烷基;取代的C1-8烷基;
甚至更优选的R3是甲基;乙基;
最优选的R3是甲基;乙基;
优选地R4是H;未取代的C1-C8烷基;取代的C1-C8烷基;未取代的C2- 8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;
更优选地R4是H;未取代的C1-C6烷基;取代的C1-C6烷基;
甚至更优选的R4是H;未取代的C1-C4烷基;取代的C1-C4烷基;
最优选的R4是H;甲基;乙基;
优选地R5是一个未取代的5至6元芳香族杂环;或一个取代的5至6元芳香族杂环;
更优选地R5是一个含有一个或两个氮原子的未取代的6元芳香族杂环;或一个含有一个或两个氮原子的取代的6元芳香族杂环;
甚至更优选的R5是一个未取代的吡啶基或嘧啶基;或一个取代的吡啶基或嘧啶基;优选一种未取代的吡啶基或嘧啶基
最优选的R5是未取代的吡啶基或嘧啶基,优选一种未取代的3-吡啶基或5-嘧啶基
在一个另外的实施方案中,R5优选是一个未取代的5至10元芳香族杂环;或一个取代的5至10元芳香族杂环;优选地R5优选是一个未取代的6至10元芳香族杂环;或一个取代的6至10元芳香族杂环;并且甚至更优选的R5是嘧啶基、吡啶基、喹啉基以及异喹啉基。
在一个另外的优选实施方案中,R5是未取代的吡啶基、优选未取代的3-吡啶基。
在一个另外的优选实施方案中,R5是未取代的嘧啶基、优选未取代的5-嘧啶基。
优选地本发明因此涉及具有化学式(I)的化合物
其中
X是S或O;
Y是C-H或N;
R1是未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2- 8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;或一个取代的5至10-元芳香族杂环;
R2是H;卤素,未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C7-15芳烷基;取代的C7- 15芳烷基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;未取代的C6-10芳硫基-C1-8烷基;取代的C6-10芳硫基-C1-8烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;一个取代的5至10-元芳香族杂环;未取代的C1-8烷基甲硅烷基;或取代的C1-8烷基甲硅烷基;
R3是未取代的C6-10芳基;取代的C6-10芳基;未取代的C1-8烷基;取代的C1-8烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C7-15芳基链烯基;取代的C7-15芳基链烯基;未取代的C7-15芳基炔基;取代的C7-15芳基炔基
R4是H;未取代的C1-C8烷基;取代的C1-C8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;
R5是一个未取代的6至10元芳香族杂环;或一个取代的5至10元芳香族杂环;
优选的具有化学式(I)的化合物是以下那些,其中
X是S或O;
Y是C-H或N;
R1是未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2- 8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;或一个取代的5至10-元芳香族杂环;
R2是H;卤素,未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C7-15芳烷基;取代的C7- 15芳烷基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;未取代的C6-10芳硫基-C1-8烷基;取代的C6-10芳硫基-C1-8烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;一个取代的5至10-元芳香族杂环;未取代的C1-8烷基甲硅烷基;或取代的C1-8烷基甲硅烷基;
R3是未取代的C1-8烷基;取代的C1-8烷基;
R4是H;未取代的C1-C8烷基;取代的C1-C8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;
R5是一个未取代的6元芳香族杂环;或一个取代的6元芳香族杂环;
更优选的具有化学式(I)的化合物是以下那些,其中
X是S或O;
Y是C-H或N;
R1是未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;一个未取代的5至10元芳香族杂环;一个取代的5至10元芳香族杂环;
R2是未取代的C1-8烷基;取代的C1-8烷基;未取代的C3-8环烷基;取代的C3- 8环烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;一个未取代的5至10元芳香族杂环;一个取代的5至10元芳香族杂环;
R3是未取代的C1-8烷基;取代的C1-8烷基;
R4是H;未取代的C1-C6烷基;取代的C1-C6烷基;
R5是一个未取代的含有一个或两个氮原子的6元芳香族杂环;或一个取代的含有一个或两个氮原子的6元芳香族杂环;
甚至更优选的具有化学式(I)的化合物是以下那些,其中
X是S或O;
Y是C-H或N;
R1是未取代的C6-10芳基;取代的C6-10芳基;
R2是未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C6-10芳基;取代的C6-10芳基;
R3是甲基;乙基;
R4是H;未取代的C1-C4烷基;取代的C1-C4烷基;
R5是一种未取代的吡啶基或嘧啶基;或一种取代的吡啶基或嘧啶基;优选一种未取代的吡啶基或嘧啶基
最优选的具有化学式(I)的化合物是以下那些,其中
X是S或O;
Y是C-H或N;
R1是未取代的苯基;经Cl、F取代的苯基;
R2是未取代的环己基;未取代的苯基;经Cl、F取代的苯基;
R3是甲基;乙基;
R4是H;甲基;乙基;
R5是未取代的吡啶基或嘧啶基,优选一种未取代的3-吡啶基或5-嘧啶基
在本发明的另外一方面中,本发明的优选的化合物(I)具有化学式(Ia)
并且取代基R1、R2、R3、R4以及R5的含义是如以上对于化学式(I)所给出的。
在本发明的另外一方面中,本发明的优选的化合物(I)具有化学式(Ib)
并且取代基R1、R2、R3、R4以及R5的含义是如以上对于化学式(I)所给出的。
在本发明的另外一方面中,本发明的优选的化合物(I)具有化学式(Ic)
并且取代基R1、R2、R3、R4以及R5的含义是如以上对于化学式(I)所给出的。
在本发明的另外一方面中,本发明的优选的化合物(I)具有化学式(Id)
并且取代基R1、R2、R3、R4以及R5的含义是如以上对于化学式(I)所给出的。
具有化学式(I)的化合物能以不同的几何或光学异构形式或以不同的互变异构的形式存在。可以存在一个或多个手性中心,在这种情况下,具有化学式I的化合物可以作为纯的对映异构体、对映异构体的混合物、纯的非对映异构体或非对映异构体的混合物存在。在该分子中可以存在双键,例如C=C或C=N键,在这种情况下,具有化学式I的化合物可以作为单一的异构体或异构体的混合物存在。可以存在多个互变异构化的中心。本发明涵盖了所有的此类异构体以及互变异构体以及它们的处于所有比例的混合物,连同同位素形式,例如氘化的化合物。由于围绕一个单键的旋转受限,还可能存在旋转对映异构现象。
具有化学式I的化合物可以如在以下方案中所示的进行制备。
可以通过在一种烷基化剂(例如甲基碘)的存在下在碱性条件下对具有化学式(I)的化合物(其中R4是氢)进行处理来制备具有化学式(I)的化合物(其中R4是C1-C6烷基或C1-C6-烷氧基烷基)。合适的碱包括氢化钠或碳酸钾,并且该反应优选是在一种合适的溶剂(例如四氢呋喃)中、在20°C与100°C之间的温度进行。醇的烷化是已知的并且已经如描述于J.March,《高级有机化学》(Advanced Organic Chemistry),第三版,约翰威立出版社(John Wiley and Sons)中。
具有化学式(I)的化合物还可以通过在碱性条件下用化学式(B)的化合物处理化学式(A)的化合物来进行制备。合适的碱包括二异丙基酰氨基锂、丁基锂、六甲基二硅基氨化钠(sodium hexamethyldisilazide),并且该反应优选是在一种合适的溶剂(比如四氢呋喃)中、在-80°C与30°C之间的温度进行。例如,得到具有化学式(I)的化合物的类似方法描述于Alberola,A.等人,《杂环化学期刊》(J.Het.Chem.)1995,32(2),537-41中。
具有化学式(A)的化合物是已知的,或者可以通过已知的方法从已知的化合物来进行制备。
具有化学式(B)的化合物是已知的,或者可以通过已知的方法从已知的化合物来进行制备。
能够以一种相似的方式,在促进卤素-金属交换的条件下,通过用具有化学式(B)的化合物处理具有化学式(C)的化合物(其中Hal是卤素)(优选溴化物或碘化物)来制备具有化学式(I)的化合物。合适的试剂包括丁基锂、叔丁基锂、异丙基溴化镁,并且该反应优选是在一种合适的溶剂(比如四氢呋喃)中、在-80°C与30°C之间的温度进行。例如,得到具有化学式(I)的化合物的类似方法描述于Antequera,T.等人,《杂环》(Heterocycles)1986,24(11),3203-11;Polo,C.等人,《化学纪事,C系列:有机化学和生物化学》(Anales de Quimica,SerieC:Quimica Organica y Bioquimica)1988,84(3),329-32;Polo,C.等人,《杂环》(Heterocycles)1991,32(9),1757-64;Imanishi,Y.等人,WO2005037271;Alberola,A.等人,《合成通讯》(Syn.Comm.)1987,17(10),1207-15中。
在一种合适的溶剂(例如乙腈或乙酸)中、在0°C与150°C之间的温度下,可以通过用一种卤化剂(例如N-溴代琥珀酰亚胺)处理具有化学式(A)的化合物来制备具有化学式(C)的化合物。例如,类似的方法描述于Day,R.A.等人,《合成》(Synthesis)2003,10,1586-1590中。
可替代地,可任选地在催化剂(镧系,优选三氯化铈或镧系三氯化物)的存在下、在一种合适的溶剂(例如四氢呋喃)中、在-80°C与30°C之间的温度下,可以通过将亲核体加成到具有化学式(D)的化合物中来制备具有化学式(I)的化合物。类似的方法例如参见Sauers,R.R.等人,《有机化学期刊》(J.Org.Chem.)1990,55(13),4011-19;Albertola,A.等人,《化学学会期刊》(J.Chem.Soc.,Perkin Trans.)11988,(4),767-70;Nagamine,M.等人,EP253370;Alberola,A.《杂环化学期刊》(J.Het.Chem.)1988,25(1),235-40。
可以通过在碱性条件下用具有化学式(F)的化合物处理具有化学式(A)的化合物来制备具有化学式(D)的化合物。合适的碱包括二异丙基酰氨基锂、丁基锂、六甲基二硅基氨化钠,并且该反应优选是在一种合适的溶剂(比如四氢呋喃)中、在-80°C与30°C之间的温度进行。例如,得到具有化学式(D)的化合物的类似方法描述于Alberola,A.等人,《合成通讯》(Syn.Comm.)1987,17(10),1207-15;Buettelmann,B.WO2009000662中。
具有化学式(D)的化合物是已知的,或者可以通过已知的方法从已知的化合物来进行制备。例如参见Hu,D.-J.等人,《分子》(Molecules)2009,14(3),1288-1303;Diaz-Valenzuela,M.等人,《欧洲化学期刊》(Chemistry AEuropean Journal)2009,15(5),1227-1232;Grecian,S.和Fokin,V.V.《应用化学国际版》(Angew.Chem.Int.Ed.)2008,47(43),8285-8287;Lee,S.-F.等人,WO2007075487;Lee,S.-F.等人,WO2006031631。
另外,可任选地在催化剂(例如氯(III)化铝)的存在下、可任选地在一种合适的溶剂(例如氯苯)中、在20°C与160°C之间的温度下,可以通过将具有化学式(G)的腈硫化物加成到具有化学式(H)的化合物上来制备具有化学式(D)的化合物(其中Y是N并且X是S)。
具有化学式(G)的化合物是已知的,或者可以通过已知的方法从已知的化合物来进行制备。
具有化学式(H)的化合物是已知的,或者可以通过已知的方法从已知的化合物来进行制备。
在一个另外的途径中,可以通过在碱性条件下通过使具有化学式(J)的化合物和具有化学式(K)的化合物发生缩合作用来制备具有化学式(I)(其中Y是N并且X是O)的化合物。或者在有机碱(例如三乙基胺或二异丙基乙胺)的存在下,在一种惰性溶剂(例如1,2-二氯乙烷)中,可任选地在催化剂(例如[Cp*RuCl(cod)])的存在下,在20°C与100°C之间的温度下。或者在有机碱(例如碳酸氢钠)的存在下,在质子溶剂(例如异丙醇)中,在20°C与100°C之间的温度下。例如,类似的方法描述于Grecian,S.和Fokin,V.V.《应用化学国际版》(Angew.Chem.Int.Ed.)2008,47,8285-87以及Liu,Kou-Chang等人,《有机化学期刊》(J.Org.Chem.)1980,45(19),3916-18中。
具有化学式(J)的化合物是已知的,或者可以通过已知的方法从已知的化合物来进行制备。
具有化学式(K)的化合物是已知的,或者可以通过已知的方法从已知的化合物来进行制备。
在一个另外的途径中,可任选地在催化剂(例如氯(III)化铝)的存在下、可任选地在一种合适的溶剂(例如氯苯)中、在20°C与160°C之间的温度下,可以通过使具有化学式(J)的化合物与具有化学式(G)的腈硫化物发生缩合作用来制备具有化学式(I)(其中Y是N并且X是S)的化合物。
给出具有化学式(I)的化合物的反应有利地在疏质子的惰性的有机溶剂中进行。此类溶剂是烃,例如苯,甲苯,二甲苯或环己烷,氯化烃,例如二氯甲烷、三氯甲烷、四氯甲烷或氯苯,醚类,例如二乙基醚、乙二醇二甲基醚、二乙二醇二甲基醚、四氢呋喃或二噁烷,腈类,例如乙腈或丙腈,酰胺类,例如N,N-二甲基甲酰胺、二乙基甲酰胺或N-甲基吡咯烷酮。反应温度有利地在-20°C与+120°C之间。总体上,这些反应是轻微放热的并且通常它们可以在环境温度下进行。为了缩短反应时间,或者还有启动该反应,该混合物可以短时间加热到该反应混合物的沸点。反应时间还可以通过加入几滴碱作为反应催化剂而缩短。适当的碱具体是叔胺类,例如三甲胺、三乙胺、奎宁环、1,4-二氮杂二环[2.2.2]辛烷、1,5-二氮杂二环[4.3.0]壬-5-烯或1.5-二氮杂二环[5.4.0]十一-7-烯。然而,作为碱还可以使用无机碱,例如氢化物,例如氢化钠或氢化钙、氢氧化物,例如氢氧化钠或氢氧化钾,碳酸盐,例如碳酸钠和碳酸钾,或碳酸氢盐,例如碳酸氢钾和碳酸氢钠。这些碱可以像这样使用或者还可以与催化量的相转移催化剂(例如冠醚,特别是18-冠-6)或一种四烷基铵盐一起使用。
式(I)的化合物以及适当时其互变异构体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结晶的那些。
现在已经发现了根据本发明的式(I)的化合物具有(用于实用的目的),一个非常有利的针对由致植物病的微生物(例如,真菌、细菌或病毒)引起的疾病来保护有用植物的活性谱。
本发明因此还涉及一种用于控制或防止有用的植物受到致植物病的微生物侵染的方法,其中将具有化学式(I)的化合物施用到植物、其部分或其场所上。根据本发明的具有化学式(I)的化合物的显著区别在于在低比率施用下优异的活性、良好的植物耐受性并且是环境安全的。它们具有非常有用的治疗、防止和系统特性,并且用于保护多种有用植物。具有化学式(I)的化合物可以被用于抑制或破坏在多种不同的有用植物作物的植物或植物部分(水果、花、叶子、茎、块茎、根)上发生的疾病,同时还保护了稍后生长的那些植物部分例如免于致植物病的微生物。
还有可能使用具有化学式(I)的化合物作为用于治疗植物繁殖材料,特别是种子(水果、块茎、谷粒)以及植物插条(例如稻米)的种子杀菌剂,用于保护对抗真菌侵染连同对抗在土壤中存在的致植物病的真菌。
此外,根据本发明的式(I)的化合物可以用于控制相关领域的真菌,例如在工业材料(包括木材以及与木材有关的工业产品)的保护中,在食品保存中或在卫生管理中。
具有化学式(I)的化合物是例如有效地针对以下类别的致植物病的真菌:半知菌(例如葡萄孢属、梨孢属、长蠕孢属、镰孢霉属、壳针孢属(Septoria)、尾孢属和链格孢霉属)和担子菌(例如丝核菌属、驼孢锈菌属(Hemileia)、柄锈菌属)。此外,它们还对子囊菌纲(例如黑星菌属和白粉菌属、叉丝单囊壳属(Podosphaera)、念珠菌属、钩丝壳属)和卵菌纲(例如疫霉属、腐霉属、单轴霉属)有效。此外,新颖的式(I)的化合物针对以下项是有效的:致植物病的细菌和病毒(例如,针对黄单胞菌属、假单胞菌属、梨火疫病菌连同针对烟草花叶病毒)。式(I)的化合物还是例如针对亚洲大豆锈菌病(大豆锈菌病)是有效的。
在本发明的范围内,有待保护的有用植物典型地包括以下植物物种:谷物(小麦、大麦、黑麦、燕麦、稻、玉米、高粱以及相关物种);甜菜(糖萝卜以及饲用甜菜);梨果、核果以及无核水果(苹果、梨、李子、桃、扁桃、樱桃、草莓、覆盆子和黑莓);豆科植物(豆、滨豆、豌豆、大豆);油科作物(油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻油植物、可可豆、落花生);黄瓜类植物(南瓜、黄瓜、甜瓜);纤维植物(棉花、亚麻、大麻、黄麻纤维);柑橘属水果(桔子、柠檬、葡萄柚、橘子);蔬菜(菠菜、莴苣、天门冬属、甘蓝、胡萝卜、葱头、番茄、马铃薯、红椒);樟科类(鳄梨、樟(cinnamomum)、樟脑)或植物,例如烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、藤本植物、蛇麻、橡胶以及天然橡胶植物,连同观赏植物。
术语“有用植物”应当理解为还包括由于常规育种方法或遗传工程方法而赋予了对多种除草剂(像溴草腈)或多种类别的除草剂(例如像HPPD抑制剂、ALS抑制剂,如氟嘧磺隆、氟丙磺隆和三氟啶磺隆、EPSPS(5-烯醇-丙酮-莽草酸-3-磷酸-合酶(5-enol-pyrovyl-shikimate-3-phosphate-synthase))抑制剂、GS(谷氨酰胺合成酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)的耐受性的有用植物。一个通过常规育种方法(诱变)被赋予对咪唑啉酮类(例如甲氧咪草烟)的耐受性的作物实例是夏季油菜(卡诺拉(Canola))。通过遗传工程方法而被赋予了对多种除草剂或多种除草剂类别的耐受性的作物的实例包括草甘膦和草丁膦抗性玉米品种,它在 和商标名下是可商购的。
术语“有用植物”应理解为还包括已通过使用重组DNA技术转化使其能合成一种或多种选择性作用毒素的作物,所述毒素如已知来自于产生毒素的细菌,尤其是芽抱杆菌属的那些细菌。
这样的植物的实例是:(玉米品种,表达一种CryIA(b)毒素);YieldGard(玉米品种,表达一种CryIIIB(b1)毒素);YieldGard(玉米品种,表达一种CryIA(b)以及一种CryIIIB(b1)毒素);(玉米品种,表达一种Cry9(c)毒素);(玉米品种,表达一种CryIF(a2)毒素以及实现对除草剂草丁膦铵的耐药性的酶草丁膦N-乙酰转移酶(PAT));(棉花品种,表达一种CryIA(c)毒素);(棉花品种,表达一种CryIA(c)毒素);(棉花品种,表达一种CryIA(c)以及一种CryIIA(b)毒素);(棉花品种,表达一种VIP毒素);(马铃薯品种,表达一种CryIIIA毒素);GT Advantage(GA21耐草甘膦性状),CB Advantage(Bt11玉米螟(CB)性状)、RW(玉米根虫性状)以及
术语“有用植物”应理解为还包括已通过使用重组DNA技术转化使其能合成具有选择性作用的抗病原物质的有用的作物,例如像,所谓的“发病机理有关蛋白”(PRP,参见例如EP-A-0392225)。这些抗病原菌物质和能够合成这些抗病原菌物质的转基因植物的实例是已知的,例如EP-A-0392225、WO95/33818和EP-A-0353191。生产这些转基因植物的方法对于本领域的技术人员是普遍公知的并且描述在例如上述公开物中。
如在此使用,术语有用植物的“场所”旨在包含有用植物生长的地方、有用植物的植物繁殖材料播种的地方或有用植物的繁殖材料将放入的土壤中。这样的场所的一个实例是作物植物在其上生长的田地。
术语“植物繁殖材料”应被理解为是指植物的生殖的部分,例如种子、这些部分可以被用于后者的繁殖,以及植物性材料,例如插条或块茎(例如马铃薯)。可以提及,例如种子(在严格意义上)、根、果实、块茎、球茎、根茎以及植物的部分。还可以提及在发芽后或在从土壤中萌发后移植的发芽的植物以及幼小的植物。这些幼小的植物可以在通过浸渍完全或部分处理的移植之前进行保护。优选地,“植物繁殖材料”应理解为是指种子。
具有化学式(I)的化合物能以未改性的形式使用,或者优选地与配方领域中常规使用的载体以及辅助剂一起使用。
因此本发明还涉及针对致植物病微生物进行控制和保护的组合物,这些组合物包括具有化学式(I)的一种化合物以及一种惰性载体,并且涉及控制或防止有用植物被致植物病微生物侵染的方法,其中将一种包括作为活性成分的具有化学式(I)的化合物以及惰性载体的组合物施用至这些植物、其部分或其场所。
对此,用已知方式将具有化学式(I)的化合物和惰性载体方便地配制为乳油、可涂覆的膏、直接可喷洒的或可稀释的溶液、稀释乳液、可湿性粉、可溶性粉剂、粉尘、颗粒,以及还有封装物(例如在聚合物物质中)。对于这种类型的组合物,应用的方法,例如喷雾、雾化、撒粉、散射、涂覆或倾倒,可以根据所打算的目的以及占主导的环境进行选择。这些组合物还可以含有其他辅助剂,例如稳定剂、消泡剂、黏度调节剂、粘合剂、或增粘剂连同肥料、微量营养素供体或用于获得特殊效果的其他配制品。
适合的载体和辅助剂(助剂)可以是固体或液体,并且是在配制品技术中有用的物质,例如天然或再生的矿物质、溶剂、分散剂、湿润剂、增粘剂、增稠剂、粘合剂或肥料。例如在WO97/33890中说明了这样的载体。
具有化学式(I)的化合物或包含具有化学式(I)化合物作为活性成分以及一种惰性载体的组合物可以施用到待处理的植物场所或植物上(与其他化合物同时地或顺序地)。这些其他化合物可以是例如肥料或微量营养素供体或影响植物生长的其他制剂。它们还可以是选择性的除草剂,连同杀昆虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或几种这些制剂的混合物,如果希望的话与配方领域所使用的常规的载体、表面活性剂或促进施用的辅助剂一起。
一种优选的用于施用一种具有化学式(I)的化合物或包含具有化学式(I)的化合物作为活性成分以及一种惰性载体的组合物的方法是叶上施用。施用频率和施用比率取决于受相应的病原体侵染的风险。然而,具有化学式(I)的化合物还可以通过用一种液体配方浸泡该植物的场所或者通过将处于固体形式的化合物施用到土壤上,例如以颗粒的形式(土壤施用)而通过根经由土壤(内吸作用)渗透该植物。在水稻作物中,可以将此种颗粒施用到水浸没的稻田中。具有化学式(I)的化合物还可以通过用一种杀真菌剂的液体配制品浸渍种子或块茎、或用一种固体配制品对其进行涂覆而施用到种子(包衣)上。
以一种已知方式制备一种配制品(即,含具有化学式(I)化合物并且如果希望的话一种固体或液体辅助剂的组合物),典型地通过将该化合物与增充剂,例如溶剂、固体载体以及,可任选地,表面活性化合物(表面活性剂)进行密切地混合和/或研磨。
这些农用化学配制品通常包括按重量计从0.1%至99%,优选地按重量计从0.1%至95%的具有化学式(I)的化合物,按重量计99.9%至1%,优选按重量计99.8%至5%的一种固体或液体辅助剂以及按重量计从0至25%,优选按重量计从0.1%至25%的一种表面活性剂。
尽管优选的是将商用的产品配制为原药(concentrates),最终的使用者通常使用稀释的配制品。
有利的施用比率通常是从5g至2kg的活性成分(a.i.)/公顷(ha),优选地从10g至1kga.i./ha,最优选地从20g至600g a.i./ha。在用作种子浸湿剂时,方便的施用比率是从10mg至1g的活性物质/kg的种子。可以通过试验确定用于所希望的作用的施用比率。它取决于例如作用类型、该有用植物的发育阶段以及施用(地点、时间安排(timing)、施用方法),并且可以由于这些参数在宽泛的限制内变化。
以上说明的具有化学式(I)的化合物或其一种药物盐还可以具有有利的对于处理和/或防止动物中的微生物侵染的活性谱。“动物”可以是任何动物,例如昆虫、哺乳动物、爬行动物、鱼、两栖动物,优选是哺乳动物,最优选是人类。“处理”意思是使用具有微生物侵染的动物来降低或减慢或停止该侵染的增大或扩散,或降低该侵染或治疗该侵染。“防止”意思是使用没有明显的微生物侵染迹象的动物来防止任何将来的侵染,或降低或减慢任何将来的侵染的增大或扩散。
根据本发明,提供了具有化学式(I)的化合物在制造一种用于处理和/或防止动物中的微生物侵染的药物中的用途。还提供了具有化学式(I)的化合物作为一种药用试剂的用途。还提供了具有化学式(I)的化合物作为在动物处理中的一种抗微生物剂的用途。根据本发明,还提供了一种药用组合物,该组合物包括作为活性成分的一种具有化学式(I)的化合物,或其一种药学上可接受的盐,以及一种药学上可接受的稀释剂或载体。该组合物可以被用于处理和/或防止动物中的抗微生物侵染。该药用组合物可以处于一种适于口服给药的形式,例如片剂、锭剂、硬胶囊、水性悬浮液、油状的悬浮液、乳液、可分散的粉、可分散的颗粒、糖浆和酏剂。可替代地,该药用组合物可以处于一种适于局部施用的形式,例如一种喷雾剂、膏状物或洗剂。可替代地,该药用组合物可以处于一种适于肠胃外给药(例如注射)的形式。可替代地,该药用组合物可以是处于吸入形式的,例如一种喷雾剂。
具有化学式(I)的化合物针对多种能够引起动物内的微生物侵染的微生物种类是有效的。此类微生物种类的例子是引起棕色锈(如小麦叶锈病)的那些,造成叶斑的那些,如小麦壳针孢,引起灰霉病的那些,例如葡萄孢菌,引起曲霉菌的那些,例如烟曲霉,黄曲霉(A.flavus),土曲霉A(A.terrus),构巢曲霉A(A.nidulans)和黑曲霉A(A.niger),引起芽生菌病(Blastomycosis)的那些,比如皮炎芽生茵(Blastomyces dermatitidis),引起念珠菌病(Candidiasis)的那些,比如白色念珠菌(Candida albicans),光滑球念珠菌(C.glabrata),热带念珠菌(C.tropicalis),近平滑念珠菌(C.parapsilosis),克鲁斯念珠菌(C.krusei)和萄牙念珠菌(C.lusitaniae);引起球抱子菌病(Coccidioidomycosis)的那些,比如粗球孢子菌(Coccidioidesimmitis)引起隐球菌病(Cryptococcosis)的那些,比如新生隐球菌((Cryptococcus neoformans);引起组织胞浆菌病(Histoplasmosis)的那些,比如荚膜组织抱浆菌(Histoplasma capsulatum)以及引起接合菌病(Zygomycosis)的那些,比如伞枝犁头霉、微小根毛霉(Rhizomucorpusillus)和无根根霉。另外的实例是镰孢霉属,例如尖孢镰刀菌和茄病镰刀菌,以及足放线病菌属,例如尖端赛多孢子菌和多育赛多孢子菌。仍另外的实例是小孢子菌属、发癣菌属、表皮癣菌属、毛霉属、孢子丝菌属、瓶霉菌属、分支孢子菌属、霉样真霉属、副球孢子菌属和组织胞浆菌属。
已经发现了使用另外的、其他的化合物或组合物(例如,另外的、其他有杀生物活性的成分或组合物)与具有化学式(I)的化合物组合出人意料地并且实质性地增强了后者针对真菌的效力,并且反之亦然。此外,本发明的方法针对更宽的此种真菌谱是有效的,这些真菌在单独使用时与这种方法的有效成分斗争。
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是物,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、新烟碱以及苏芸金芽胞杆菌制剂。
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“选自具有化学式(I)的化合物中的一种化合物,或下组的一种化合物,该组由具有描述于本发明的表1至28中的化学式T1.1至T1.28以及T2.1、以及T3.1至T28.217的化合物组成”):
一种助剂,该助剂选自由石油(替代名称(628)+TX)构成的物质,
一种杀螨剂,该杀螨剂选自以下物质组成的组:1,1-二(4-氯苯基)-2-乙氧基乙醇(IUPAC名称)(910)+TX、2,4-二氯苯基苯磺酸酯(IUPAC/化学文摘名)(1059)+TX、2-氟-N-甲基-N-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、氨基硫代盐(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、AVI382(化合物代码)+TX、AZ60541(化合物代码)+TX、益棉磷(44)+TX、保棉磷(azinphos-methyl)(45)+TX、偶氮苯(IUPAC名称)(888)+TX、三唑锡(azacyclotin)(46)+TX、偶氮磷(azothoate)(889)+TX、苯茵灵(62)+TX、苯诺沙磷(benoxafos)(别名)[CCN]+TX、苯螨特(benzoximate)(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(bromocyclene)(918)+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX,溴螨酯(bromopropylate)(94)+TX、噻嗪酮(99)+TX、丁酮威(103)+TX、丁酮砜威(104)+TX、丁酮威(butylpyridaben)(别名)+TX、石硫合剂(calcium polysulfide)(IUPAC名称)(111)+TX、毒杀芬(campheechlor)(941)+TX、氯灭杀威(carbanolate)(943)+TX、甲萘威(115)+TX、克百威(carbofuran)(118)+TX、卡波硫磷(947)+TX、CGA50'439(研究代码)(125)+TX、灭螨猛(chinomethionat)(126)+TX、杀螨醚(chlorbenside)(959)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、溴虫腈(130)+TX、敌螨(968)+TX、杀螨酯(chlorfenson)(970)+TX、敌螨特(chlorfensulphide)(971)+TX、氯芬磷(131)+TX、乙酯杀螨醇(chlorobenzilate)(975)+TX、伊托明(chloromebuform)(977)+TX、灭虫脲(chloromethiuron)(978)+TX、丙酯杀螨醇(chloropropylate)(983)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(chlorthiophos)(994)+TX、瓜菊酯(cinerin)I(696)+TX、瓜菊酯11(696)+TX、瓜叶菊素(cinerins)(696)+TX、四螨嗪(158)+TX、氯氰碘柳胺(别名)[CCN]+TX、库马磷(174)+TX、克罗米通(别名)[CCN]+TX、巴毒磷(crotoxyphos)(1010)+TX、硫杂灵(1013)+TX、果虫磷(cyanthoate)(1020)+TX、丁氟螨酯(CAS登记号:400882-07-7)+TX、三氯氟氰菊酯(196)+TX、三环锡(199)+TX、氯氰菊酯(201)+TX、DCPM(1032)+TX、DDT(219)+TX、田乐磷(demephion)(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(demeton)(1038)+TX、甲基内吸磷(224)+TX、内吸磷-O(1038)+TX、甲基内吸磷-O(224)+TX、内吸磷-S(1038)+TX、甲基内吸磷-S(224)+TX、内吸磷-S-甲基磺隆(demeton-S-methylsulphon)(1039)+TX、杀螨隆(226)+TX、氯亚胺硫磷(dialifos)(1042)+TX、二嗪磷(227)+TX、苯氟磺胺(230)+TX、敌敌畏(236)+TX、甲氟磷(dicliphos)(别名)+TX、开乐散(242)+TX、百治磷(243)+TX、遍地克(1071)+TX、甲氟磷(dimefox)(1081)+TX、乐果(262)+TX、二甲杀螨霉素(dinactin)(别名)(653)+TX、消螨酚(dinex)(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、消螨通(dinobuton)(269)+TX、敌螨普(dinocap)(270)+TX、敌螨普-4[CCN]+TX、敌螨普-6[CCN]+TX、二硝酯(1090)+TX、硝戊酯(dinopenton)(1092)+TX、硝辛酯(dinosulfon)(1097)+TX、硝丁酯(dinoterbon)(1098)+TX、敌恶磷(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、苯氧炔螨(dofenapyn)(1113)+TX、多拉克汀(别名)[CCN]+TX、硫丹(294)+TX、因毒磷(endothion)(1121)+TX、EPN(297)+TX、依立诺克丁(别名)[CCN]+TX、乙硫磷(309)+TX、益硫磷(ethoate-methyl)(1134)+TX、乙螨唑(etoxazole)(320)+TX,乙嘧硫磷(etrimfos)(1142)+TX、抗螨唑(fenazaflor)(1147)+TX、喹螨醚(328)+TX、苯丁锡(fenbutatin oxide)(330)+TX、苯硫威(fenothiocarb)(337)+TX、甲氰菊酯(342)+TX、吡螨胺(fenpyrad)(别名)+TX、唑螨酯(fenpyroximate)(345)+TX、芬螨酯(fenson)(1157)+TX、氟硝二苯胺(fentrifanil)(1161)+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、嘧螨酯(fluacrypyrim)(360)+TX、氟佐隆(1166)+TX、氟螨噻(flubenzimine)(1167)+TX、氟螨脲(366)+TX、氟氰戊菊酯(flucythrinate)(367)+TX、联氟螨(fluenetil)(1169)+TX、氟虫脲(370)+TX、氟氯苯菊酯(flumethrin)(372)+TX、氟杀螨(f1uorbenside)(1174)+TX、氟胺氰菊酯(fluvalinate)(1184)+TX、FMC1137(研究代码)(1185)+TX、抗螨脒(405)+TX、抗螨脒盐酸盐(405)+TX、安硫磷(formothion)(1192)+TX、胺甲威(formparanate)(1193)+TX、銄-HCH(430)+TX、果绿啶(glyodin)(1205)+TX、苄螨醚(halfenprox)(424)+TX、庚烯醚(heptenophos)(432)+TX、十六碳烷基环丙烷羧酸酯(IUPAC/化学文摘名)(1216)+TX、噻螨酮(441)+TX、碘甲烷(IUPAC名称)(542)+TX、水胺硫磷(isocarbophos)(别名)(473)+TX、异丙基0-(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、茉莉菊酯(jasmolin)I(696)+TX、茉莉菊酯II(696)+TX、碘硫磷(jodfenphos)(1248)+TX、林丹(430)+TX、虱螨脲(490)+TX、马拉硫磷(492)+TX、苄丙二腈(malonoben)(1254)+TX、灭蚜磷(mecarbam)(502)+TX、地胺磷(mephosfolan)(1261)+TX、甲硫芬(别名)[CCN]+TX、虫螨畏(methacrifos)(1266)+TX、甲胺磷(527)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、灭多虫(531)+TX、溴甲烷(537)+TX、速灭威(metolcarb)(550)+TX、速灭磷(556)+TX、自克威(mexacarbate)(1290)+TX、米尔螨素(557)+TX、杀螨茵素肟(milbemycin oxime)(别名)[CCN]+TX、丙胺氟磷(mipafox)(1293)+TX、久效磷(561)+TX、茂硫磷(morphothion)(1300)+TX、莫昔克丁(别名)[CCN]+TX、二溴磷(naled)(567)+TX、NC-184(化合物代码)+TX、NC-152(化合物代码)+TX、氟蚊灵(nifluridide)(1309)+TX、尼柯霉素(别名)[CCN]+TX、戊氰威(nitrilacarb)(1313)+TX、戊氰威(nitrilacarb)1:1氯化锌络合物(1313)+TX、NNI-0101(化合物代码)+TX、NNI-0250(化合物代码)+TX、氧乐果(氧乐果)(594)+TX、杀线威(602)+TX、亚异砜磷(oxydeprofos)(1324)+TX、砜拌磷(oxydisulfoton)(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(phosfolan)(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(polychloroterpenes)(传统名称)(1347)+TX,杀螨霉素(polynactins)(别名)(653)+TX、丙氯诺(1350)+TX、丙溴磷(662)+TX、蜱虱威(promacyl)(1354)+TX、克螨特(671)+TX、胺丙畏(propetamphos)(673)+TX、残杀威(678)+TX、乙噻唑磷(prothidathion)(1360)+TX、发硫磷(prothoate)(1362)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊素(pyrethrins)(696)+TX、哒螨灵(699)+TX、哒嗪硫磷(pyridaphenthion)(701)+TX、嘧螨醚(pyrimidifen)(706)+TX、嘧硫磷(1370)+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷(quintiofos)(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(schradan)(1389)+TX、硫线磷(sebufos)(别名)+TX、塞拉菌素(selamectin)(别名)[CCN]+TX、SI-0009(化合物代码)+TX、苏硫磷(sophamide)(1402)+TX、季酮螨酯(738)+TX、螺甲螨酯(739)+TX、SSI-121(研究代码)(1404)+TX、舒非仑(别名)[CCN]+TX、氟虫胺(sulfluramid)(750)+TX、治螟磷(sulfotep)(753)+TX、硫黄(754)+TX、S21-121(研究代码)(757)+TX、氟胺氰菊酯(398)+TX,吡螨胺(763)+TX、TEPP(1417)+TX、叔丁威(terbam)(别名)+TX、司替罗磷(777)+TX、三氯杀螨砜(tetradifon)(786)+TX、杀螨霉素(tetranactin)(别名)(653)+TX、杀螨硫醚(tetrasul)(1425)+TX、久效威(thiafenox)(别名)+TX、抗虫威(thiocarboxime)(1431)+TX、久效威(thiofanox)(800)+TX、甲基乙拌磷(thiometon)(801)+TX、克杀螨(1436)+TX、苏力菌素(thuringiensin)(别名)[CCN]+TX、威茵磷(triamiphos)(1441)+TX、苯噻螨(triarathene)(1443)+TX、三唑磷(820)+TX、唑呀威(triazuron)(别名)+TX、敌百虫(824)+TX、氯苯乙丙磷(trifenofos)(1455)+TX、甲杀螨霉素(trinactin)(别名)(653)+TX、灭蚜硫磷(847)+TX、氟吡唑虫(vaniliprole)[CCN]和YI-5302(化合物代码)+TX,
一种杀藻剂,该杀藻剂选自下组: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,该驱蠕虫剂选自下组:阿维菌素(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,该杀细菌剂由选自下组的物质组成: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,
一种生物剂,该生物剂选自以下物质组成的组:棉褐带卷蛾GV(别名)(12)+TX、放射形土壤杆菌(别名)(13)+TX、钝绥螨属(别名)(19)+TX、芹菜夜蛾NPV(别名)(28)+TX、原缨翅缨小蜂(别名)(29)+TX、苜蓿蚜小蜂(别名)(33)+TX、科曼尼蚜茧蜂(别名)(34)+TX、食蚜瘿蚊(别名)(35)+TX、苜蓿丫纹夜蛾NPV(别名)(38)+TX、坚强芽孢杆菌(别名)(48)+TX、球形芽孢杆菌Neide(学名)(49)+TX、苏云金芽孢杆菌Berliner(学名)(51)+TX、苏云金芽孢杆菌鲇泽亚种(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(学名)(51)+TX、苏云金芽孢杆菌日本亚种(学名)(51)+TX、苏云金芽孢杆菌库斯塔克亚种(学名)(51)+TX、苏云金芽孢杆菌拟步行甲亚种(学名)(51)+TX、球孢白僵菌(别名)(53)+TX、布氏白僵菌(别名)(54)+TX、普通草蛉(别名)(151)+TX、孟氏隐唇瓢虫(别名)(178)+TX、苹果蠹蛾GV(别名)(191)+TX、西伯利亚潜蝇离颚茧蜂(别名)(212)+TX、豌豆潜蝇姬小蜂(别名)(254)+TX、丽蚜小蜂(学名)(293)+TX、浆角蚜小蜂(别名)(300)+TX、美洲棉铃虫NPV(别名)(431)+TX、嗜菌异小杆线虫和异小杆线虫(别名)(433)+TX、锚斑长足瓢(别名)(442)+TX、胭介壳虫跳小蜂(别名)(488)+TX、盲蝽(别名)(491)+TX、甘蓝夜蛾NPV(别名)(494)+TX、Metaphycus helvolus(别名)(522)+TX、金龟子绿僵菌蝗变种(学名)(523)+TX、金龟子绿僵菌anisopliae变种(学名)(523)+TX、欧洲新松叶蜂NPV和红头松树叶蜂NPV(别名)(575)+TX、小花蝽属(别名)(596)+TX、玫烟色拟青霉(别名)(613)+TX、智利捕植螨(别名)(644)+TX、甜菜夜蛾核型多角体病毒(学名)(741)+TX、斯氏线虫(别名)(742)+TX、昆虫病原线虫(别名)(742)+TX、夜蛾斯氏线虫(别名)(742)+TX、格氏线虫(别名)(742)+TX、Steinernemariobrave(别名)(742)+TX、Steinernema riobravis(别名)(742)+TX、蝼蛄斯氏线虫(别名)(742)+TX、斯氏线虫属(别名)(742)+TX、赤眼蜂属(别名)(826)+TX、西方盲走螨(别名)(844)、以及蜡蚧轮枝菌(别名)(848)+TX,
一种土壤消毒剂,该土壤消毒剂选自以下物质构成的组:碘甲烷(IUPAC名祢)(542)和溴甲烷(537)+TX,
一种化学不育剂,该化学不育剂选自以下物质构成的组:唑磷嗪(apholate)[CCN]+TX、bisazir(别名)[CCN]+TX、白消安(别名)[CCN]+TX、除虫脲(250)+TX、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(methylapholate)[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-multistriatin(别名)[CCN]+TX、西部松小蠹集合信息素(brevicomin)(别名)[CCN]+TX、十二碳二烯醇(codlelure)(别名)[CCN]+TX、十二碳二烯醇(codlemone)(别名)(167)+TX、诱蝇酮(cuelure)(别名)(179)+TX、环氧十九烷(disparlure)(277)+TX、十二碳-8-烯-1基乙酸酯(IUPAC名称)(286)+TX、十二碳-9-烯-1-基乙酸酯(IUPAC名称)(287)+TX、十二碳-8+TX、10-二烯-1-基乙酸酯(IUPAC名称)(284)+TX、dominicalure(别名)[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚(别名)[CCN]+TX、南部松小蠹集合信息素(frontalin)(别名)[CCNl+TX、诱虫十六酯(gossyplure)(别名)(420)+TX、诱杀烯混剂(grandlure)(421)+TX、诱杀烯混剂I(别名)(421)+TX、诱杀烯混剂II(别名)(421)+TX、诱杀烯混剂III(别名)(421)+TX、诱杀烯混剂IV(别名)(421)+TX、醋酸十六烯酯(hexalure)[CCN]+TX、ipsdienol(别名)[CCN]+TX、ipsenol(别名)[CCN]+TX、金龟子性诱剂(japonilure)(别名)(481)+TX、lineatin(别名)[CCN]+TX、litlure(别名)[CCN]+TX、looplure(别名)[CCN]+TX、medlure[CCN]+TX、megatomoic acid(别名)[CCN]+TX、诱虫醚(methyl eugenol)(别名)(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)(别名)[CCN]+TX、oryctalure(别名)(317)+TX、非乐康(ostramone)(别名)[CCN]+TX、诱虫环(siglure)[CCN]+TX、sordidin(别名)(736)+TX、sulcatol(别名)[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(别岩)(839)+TX、特诱酮B,(别名)(839)+TX、特诱酮B:(别名)(839)+TX、特诱酮C(别名)(839)和trunc-call(别名)[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(dimethylcarbate)[CCN]+TX、乙基己二醇(1137)+TX、己脲[CCN]+TX、甲喹丁(methoquin-butyl)(1276)+TX、甲基新癸酰胺[CCN]+TX、氨羰基甲酸酯(oxamate)[CCN]和羟哌酯[CCN]+TX,
一种杀昆虫剂,该杀昆虫剂选自以下物质组成的组:1-二氯-1-硝基乙烷(IUPAC/化学文摘名称)(1058)+TX、1,1-二氯-2,2-二(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、带有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、乙酸2,2,2-三氯-1-(3,4-二氯苯基)乙基酯(IUPAC名称)(1451)+TX、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸酯(IUPAC名称)(1066)+TX、二甲基氨基甲酸2-(1,3-二硫杂环戊烷-2-基)苯基酯(IUPAC/化学文摘名称)(1109)+TX、硫氰酸2-(2-丁氧基乙氧基)乙基酯(IUPAC/化学文摘名称)(935)+TX、甲基氨基甲酸2-(4,5-二甲基-1,3-二氧环戊烷-2-基)苯基酯(IUPAC/化学文摘名称)(1084)+TX、2-(4-氯-3,5-二甲苯基氧基)乙醇(IUPAC名称)(986)+TX、2-氯乙烯基二乙基磷酸酯(IUPAC名称)(984)+TX、2-咪唑啉酮(IUPAC名称)(1225)+TX、2-异戊酰基茚满-1,3-二酮(IUPAC名称)(1246)+TX、甲基氨基甲酸2-甲基(丙-2-炔基)氨基苯基酯(IUPAC名称)(1284)+TX、月桂酸2-硫氰基乙基酯(IUPAC名称)(1433)+TX、3-溴-1-氯丙-1-烯(IUPAC名称)(917)+TX、二甲基氨基甲酸3-甲基-1-苯基吡唑-5-基酯(IUPAC名称)(1283)+TX、甲基氨基甲酸4-甲基(丙-2-炔基)氨基-3,5-二甲苯基酯(IUPAC名称)(1285)+TX、二甲基氨基甲酸5,5-二甲基-3-氧代环己-1-烯基酯(IUPAC名称)(1085)+TX、阿维菌素(1)+TX、乙酰甲胺磷(2)+TX、啶虫脒(4)+TX、家蝇磷(别名)[CCN]+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、丙烯腈(IUPAC名称)(861)+TX、棉铃威(15)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、氯甲桥萘(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、赛硫磷(870)+TX、硫代酰胺(872)+TX、灭害威(873)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、新烟碱(877)+TX、乙基杀扑磷(883)+TX、AVI382(化合物代码)+TX、AZ60541(化合物代码)+TX、印楝素(别名)(41)+TX、甲基吡啶磷(42)+TX、谷硫磷-乙基(44)+TX、谷硫磷-甲基(45)+TX、偶氮磷(889)+TX、苏云金芽孢杆菌δ-内毒素类(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、Bayer22/190(研究代码)(893)+TX、Bayer22408(研究代码)(894)+TX、噁虫威(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、生物烯丙菊酯(78)+TX、生物烯丙菊酯S-环戊烯基异构体(别名)(79)+TX、戊环苄呋菊酯(bioethanomethrin)[CCN]+TX、生物氯菊酯(908)+TX、除虫菊酯(80)+TX、二(2-氯乙基)醚(IUPAC名称)(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、溴杀烯(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、噻嗪酮(99)+TX、畜虫威(926)+TX、butathiofos(927)+TX、丁酮威(103)+TX、丁酯膦(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、甲萘威(115)+TX、克百威(118)+TX、二硫化碳(IUPAC/化学文摘名称)(945)+TX、四氯化碳(IUPAC名称)(946)+TX、三硫磷(947)+TX、丁硫克百成(119)+TX、杀螟丹(123)+TX、杀螟丹盐酸盐(123)+TX、西伐丁(别名)(725)+TX、冰片丹(960)+TX、氯丹(128)+TX、开蓬(963)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、氯氧磷(129)+TX、溴虫腈(130)+TX、毒虫畏(131)+TX、定虫隆(132)+TX、氯甲磷(136)+TX、氯仿[CCN]+TX、三氯硝基甲烷(141)+TX、氯辛硫磷(989)+TX、灭虫吡啶(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、灰菊素I(696)+TX、灰菊素II(696)+TX、灰菊素类(696)+TX、顺式苄呋菊酯(cis-resmethrin)(别名)+TX、顺式苄呋菊酯(cismethrin)(80)+TX、功夫菊酯(别名)+TX、除线威(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、克芦磷酯(1011)+TX、冰晶石(别名)(177)+TX、CS708(研究代码)(1012)+TX、苯腈膦(1019)+TX、杀螟睛(184)+TX、果虫磷(1020)+TX、环虫菊酯[CCN]+TX、乙氰菊酯(188)+TX、氟氯氰菊酯(193)+TX、三氯氟氰菊酯(196)+TX、氯氰菊酯(201)+TX、苯氰菊酯(206)+TX、环丙马秦(209)+TX、畜蜱磷(别名)[CCN]+TX、d-柠檬烯(别名)[CCN]+TX、d-四甲菊酯(别名)(788)+TX、DAEP(1031)+TX、棉隆(216)+TX、DDT(219)+TX、decarbofuran(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、内吸磷-S-甲基砜(1039)+TX、丁醚脲(226)+TX、氯亚胺硫磷(1042)+TX、二胺磷(1044)+TX、二嗪磷(227)+TX、异氯磷(1050)+TX、除线磷(1051)+TX、敌敌畏(236)+TX、dicliphos(别名)+TX、dicresyl(别名)[CCN]+TX、百治磷(243)+TX、地昔尼尔(244)+TX、狄氏刑(1070)+TX、二乙基5-甲基吡唑-3-基磷酸酯(IUPAC名称)(1076)+TX、除虫脲(250)+TX、二羟丙茶碱(dilor)(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、苄菊酯(1083)+TX、甲基毒虫畏(265)+TX、敌蝇威(1086)+TX、消螨酚(1089)+TX、消螨酚-diclexine(1089)+TX、丙硝酚(1093)+TX、戊硝酚(1094)+TX、达诺杀(1095)+TX、呋虫胺(271)+TX、苯虫醚(1099)+TX、蔬果磷(1100)+TX、二氧威(1101)+TX、敌恶磷(1102)+TX、乙拌磷(278)+TX、苯噻乙双硫磷(dithicrofos)(1108)+TX、DNOC(282)+TX、多拉克汀(别名)[CCN]+TX、DSP(1115)+TX、蜕皮激素(别名)[CCN]+TX、EI1642(研究代码)(1118)+TX、甲氧基阿维菌素(291)+TX、甲氧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、异狄氏剂(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、牛津郡丙硫磷(etaphos)(别名)[CCN]+TX、乙硫苯威(308)+TX、乙硫磷(309)+TX、乙虫腈(310)+TX、益硫磷-甲基(1134)+TX、灭线磷(312)+TX、甲酸乙酯(IUPAC名称)[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、苯线磷(326)+TX、抗螨唑(1147)+TX、皮蝇磷(1148)+TX、苯硫威(1149)+TX、芬氟司林(1150)+TX、杀螟硫磷(335)+TX、丁苯威(336)+TX、嘧酰虫胺(fenoxacrim)(1153)+TX、苯氧威(340)+TX、吡氯氰菊酯(1155)+TX、甲氰菊酯(342)+TX、吡螨胺(fenpyrad)(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、氟啶虫酰胺(358)+TX、氟虫酰胺(CAS登记号:272451-65-7)+TX、flucofuron(1168)+TX、氟环脲(366)+TX、氟氰戊菊酯(367)+TX、联氟螨(1169)+TX、嘧虫胺[CCN]+TX、氟虫脲(370)+TX、三氟醚菊酯(1171)+TX、氟氯苯菊酯(372)+TX、氟胺氰菊酯(1184)+TX、FMC1137(研究代码)(1185)+TX、地虫磷(1191)+TX、伐虫脒(405)+TX、伐虫脒盐酸盐(405)+TX、安硫磷(1192)+TX、藻螨威(formparanate)(1193)+TX、丁苯硫磷(1194)+TX、福司吡酯(1195)+TX、噻唑酮磷(408)+TX、丁硫环磷(1196)+TX、呋线威(412)+TX、抗虫菊(1200)+TX、γ-氯氟氰菊酯(197)+TX、γ-HCH(430)+TX、双胍盐(422)+TX、双胍醋酸盐(422)+TX、GY-81(研究代码)(423)+TX、苄螨醚(424)+TX、氯虫酰肼(425)+TX、HCH(430)+TX、HEOD(1070)+TX、飞布达(1211)+TX、庚烯磷(432)+TX、速杀硫磷[CCN]+TX、氟铃脲(439)+TX、HHDN(864)+TX、氟蚁腙(443)+TX、氢氰酸(444)+TX、烯虫乙酯(445)+TX、hyquincarb(1223)+TX、吡虫啉(458)+TX、炔咪菊酯(460)+TX、茚虫威(465)+TX、碘甲烷(IUPAC名称)(542)+TX、IPSP(1229)+TX、氯唑磷(1231)+TX、碳氯灵(1232)+TX、水胺硫磷(别名)(473)+TX、异艾氏剂(1235)+TX、异柳磷(1236)+TX、移栽灵(1237)+TX、异丙威(472)+TX、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯(IUPAC名称)(473)+TX、稻瘟灵(474)+TX、异拌磷(1244)+TX、恶唑磷(480)+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、保幼激素I(别名)[CCN]+TX、保幼激素II(别名)[CCN]+TX、保幼激素III(别名)[CCN]+TX、氯戊环(1249)+TX、烯虫炔酯(484)+TX、λ-三氯氟氰菊酯(198)+TX、砷酸铅[CCN]+TX、雷皮菌素(CCN)+TX、对溴磷(1250)+TX、林旦(430)+TX、lirimfos(1251)+TX、虱螨脲(490)+TX、噻唑磷(1253)+TX、间异丙基苯基甲基氨基甲酸酯(IUPAC名称)(1014)+TX、磷化镁(IUPAC名称)(640)+TX、马拉硫磷(492)+TX、特螨腈(1254)+TX、叠氮磷(1255)+TX、灭蚜磷(502)+TX、四甲磷(1258)+TX、灭蚜硫磷(1260)+TX、地安磷(1261)+TX、氯化亚汞(513)+TX、mesulfenfos(1263)+TX、氰氟虫腙(CCN)+TX、威百亩(519)+TX、威百亩钾(别名)(519)+TX、威百亩钠(519)+TX、虫螨畏(1266)+TX、甲胺磷(527)+TX、甲烷磺酰氟(IUPAC/化学文摘名称)(1268)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、杀虫乙烯磷(1273)+TX、灭多威(531)+TX、烯虫酯(532)+TX、甲喹丁(1276)+TX、甲醚菊酯(别名)(533)+TX、甲氧滴滴涕(534)+TX、甲氧苯酰(535)+TX、溴甲烷(537)+TX、异硫氰酸甲酯(543)+TX、甲基氯仿(别名)[CCN]+TX、二氯甲烷[CCN]+TX、甲氧苄氟菊酯[CCN]+TX、速灭威(550)+TX、恶虫酮(1288)+TX、速灭磷(556)+TX、兹克威(1290)+TX、密灭汀(557)+TX、米尔倍霉素(别名)[CCN]+TX、丙胺氟磷(1293)+TX、灭蚁灵(1294)+TX、久效磷(561)+TX、茂硫磷(1300)+TX、莫昔克丁(别名)[CCN]+TX、萘酞磷(别名)[CCN]+TX、二溴磷(567)+TX、萘(IUPAC/化学文摘名称)(1303)+TX、NC-170(研究代码)(1306)+TX、NC-184(化合物代码)+TX、烟碱(578)+TX、硫酸烟碱(578)+TX、氟蚁灵(1309)+TX、烯啶虫胺(579)+TX、硝乙脲噻唑(nithiazine)(1311)+TX、戊氰威(1313)+TX、戊氰威1:1氯化锌络合物(1313)+TX、NNI-0101(化合物代码)+TX、NNI-0250(化合物代码)+TX、降烟碱(传统名称)(1319)+TX、双苯氟脲(585)+TX、多氟脲(586)+TX、O-5-二氯-4-碘苯基O-乙基乙基硫代膦酸酯(IUPAC名称)(1057)+TX、O,O-二乙基O-4-甲基-2-氧代-2H-色烯-7-基硫代膦酸酯(IUPAC名称)(1074)+TX、O,O-二乙基O-6-甲基-2-丙基嘧啶-4-基硫代膦酸酯(IUPAC名称)(1075)+TX、O,O,O',O′-四丙基二硫代焦磷酸酯(IUPAC名称)(1424)+TX、油酸(IUPAC名称)(593)+TX、氧化乐果(594)+TX、杀线威(602)+TX、砜吸磷-甲基(609)+TX、异亚砜磷(1324)+TX、砜拌磷(1325)+TX、pp'-DDT(219)+TX、对-二氯苯[CCN]+TX、对硫磷(615)+TX、对硫磷-甲基(616)+TX、氟幼脲(别名)[CCN]+TX、五氯苯酚(623)+TX、月桂酸五氯苯基酯(IUPAC名称)(623)+TX、氯菊酯(626)+TX、石油油料类(别名)(628)+TX、PH60-38(研究代码)(1328)+TX、芬硫磷(1330)+TX、苯醚菊酯(630)+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、对氯硫磷(1339)+TX、磷胺(639)+TX、磷化氢(IUPAC名称)(640)+TX、辛硫磷(642)+TX、辛硫磷-甲基(1340)+TX、pirimetaphos(1344)+TX、抗蚜威(651)+TX、虫螨磷-乙基(1345)+TX、虫螨磷-甲基(652)+TX、聚氯二环戊二烯异构体类(IUPAC名称)(1346)+TX、聚氯萜类(传统名称)(1347)+TX、亚砷酸钾[CCN]+TX、硫氰酸钾[CCN]+TX、丙炔菊酯(655)+TX、早熟素I(别名)[CCN]+TX、早熟素II(别名)[CCN]+TX、早熟素III(别名)[CCN]+TX、乙酰嘧啶磷(primidophos)(1349)+TX、丙溴磷(662)+TX、丙氟菊酯[CCN]+TX、蜱虱威(1354)+TX、猛杀威(1355)+TX、丙虫磷(1356)+TX、胺丙畏(673)+TX、残杀威(678)+TX、乙噻唑磷(1360)+TX、丙硫磷(686)+TX、发硫磷(1362)+TX、protrifenbute[CCN]+TX、吡蚜酮(688)+TX、吡唑硫磷(689)+TX、吡嗪氟虫腈(pyrafluprole)[CCN]+TX、定菌磷(693)+TX、苄呋菊酯(pyresmethrin)(1367)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊酯类(696)+TX、哒螨灵(699)+TX、啶虫丙醚(700)+TX、哒嗪硫磷(701)+TX、嘧螨醚(706)+TX、嘧硫磷(1370)+TX、吡丙醚(708)+TX、苦木提取物(quassia)(别名)[CCN]+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷-甲基(1376)+TX、畜宁磷(1380)+TX、喹硫磷(quintiofos)(1381)+TX、R-1492(研究代码)(1382)+TX、雷复尼特(别名)[CCN]+TX、苄呋菊酯(719)+TX、鱼藤酮(722)+TX、RU15525(研究代码)(723)+TX、RU25475(研究代码)(1386)+TX、尼亚那(ryania)(别名)(1387)+TX、利阿诺定(传统名称)(1387)+TX、沙巴藜芦(别名)(725)+TX、八甲磷(1389)+TX、硫线磷(别名)+TX、塞拉菌素(别名)[CCN]+TX、SI-0009(化合物代码)+TX、SI-0205(化合物代码)+TX、SI-0404(化合物代码)+TX、SI-0405(化合物代码)+TX、氟硅菊酯(728)+TX、SN72129(研究代码)(1397)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟化钠(IUPAC/化学文摘名称)(1399)+TX、六氟硅酸钠(1400)+TX、五氯酚钠(623)+TX、硒酸钠(IUPAC名称)(1401)+TX、硫氰酸钠[CCN]+TX、苏硫磷(1402)+TX、多杀菌素(737)+TX、螺甲螨酯(739)+TX、螺虫乙酯(CCN)+TX、sulcofuron(746)+TX、sulcofuron-sodium(746)+TX、氟虫胺(750)+TX、治螟磷(753)+TX、磺酰氟(756)+TX、硫丙磷(1408)+TX、焦油类(别名)(758)+TX、τ-氟胺氰菊酯(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、terbam(别名)+TX、特丁硫磷(773)+TX、四氯乙烷[CCN]+TX、杀虫畏(777)+TX、四甲菊酯(787)+TX、θ-氯氰菊酯(204)+TX、噻虫啉(791)+TX、thiafenox(别名)+TX、噻虫嗪(792)+TX、thicrofos(1428)+TX、克虫威(1431)+TX、杀虫环(798)+TX、杀虫环草酸氢盐(798)+TX、硫双威(799)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、虫线磷(1434)+TX、杀虫单(thiosultap)(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、transpermethrin(1440)+TX、威菌磷(1441)+TX、唑蚜威(818)+TX、三唑磷(820)+TX、唑呀威(别名)+TX、敌百虫(824)+TX、trichlormetaphos-3(别名)[CCN]+TX、毒壤膦(1452)+TX、三氯丙氧磷(1455)+TX、杀铃脲(835)+TX、混杀威(840)+TX、烯虫硫酯(1459)+TX、蚜灭磷(847)+TX、vaniliprole[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、zeta-氯氰菊酯(205)+TX、zetamethrin(别名)+TX、磷化锌(640)+TX、丙硫恶唑磷(zolaprofos)(1469)、以及ZXI8901(研究代码)(858)+TX、氰虫酰胺[736994-63-19]+TX、氯虫酰胺[500008-45-7]+TX、唑螨氰(cyenopyrafen)[560121-52-0]+TX、丁氟螨酯[400882-07-7]+TX、氟虫吡喹(pyrifluquinazon)[337458-27-2]+TX、乙基多杀菌素(spinetoram)[187166-40-1+187166-15-0]+TX、螺虫乙酯[203313-25-1]+TX、砜虫啶(sulfoxaflor)[946578-00-3]+TX、丁虫腈(flufiprole)[704886-18-0]+TX、氯氟醚菊酯[915288-13-0]+TX、四氟醚菊酯(tetramethylfluthrin)[84937-88-2]+TX,
一种杀软体动物剂,该杀软体动物剂选自以下物质组成的组: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、醋酸三苯基锡(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(别名)(210)+TX、阿维菌素(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)(别名)+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)(别名)(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)(别名)+TX、乐果(262)+TX、依马克丁(别名)[CCN]+TX、依马克丁苯甲酸酯(291)+TX、依立诺克丁(291)+TX、(别名)[CCN]+TX312)+TX、二溴乙烷(316)+TX、苯线磷(fenamiphos)(326)+TX、吡螨胺(别名)+TX、丰索磷(fenpyrad)(1158)+TX、噻唑磷(fosthiazate)(408)+TX、丁硫环磷(fosthietan)(1196)+TX、糠醛(别名)[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)(别名)[CCN]+TX、糠氨基嘌呤(mecarphon)(别名)(210)+TX、甲基灭蚜磷(mecarphon)(1258)+TX、威百亩(519)+TX、威百亩钾盐(别名)(519)+TX、威百亩钠盐(519)+TX、溴甲烷(537)+TX、异硫氰酸甲酯(543)+TX、杀螨菌素肟(milbemycin oxime)(别名)[CCN]+TX、莫昔克丁(剔名)[CCN]+TX、疣孢漆斑茵(Myrothecium verrucaria)组分(别名)(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)(别名)+TX、塞拉菌素(selamectin)(别名)[CCN]+TX、多杀菌素(737)+TX、叔丁威(terbam)(别名)+TX、特丁磷(terbufos)(773)+TX、四氯噻吩(IUPAC/化学文摘名)(1422)+TX、thiaf enox(别名)+TX、虫线磷(thionazin)(1434)+TX、三唑磷(triazophos)(820)+TX、triazuron(别名)+TX、二甲苯酚[CCN]+TX、YI-5302(化合物代码)和玉米素(别名)(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以下物质构成的组: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,该杀鼠剂选自以下物质组成的组:2-异戊酰基茚满-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-氯醇[CCN]+TX、磷化铝(640)+TX、安妥(880)(antu)+TX、三氧化二砷(882)+TX、碳酸钡(891)+TX、双鼠脲(bisthiosemi)(912)+TX、溴鼠隆(89)+TX、溴敌隆(bromadiolone)(91)+TX、溴鼠胺(92)+TX、氰化钙(444)+TX、氯醛糖(127)+TX、氯鼠酮(chlorophacinone)(140)+TX、维生素d3(别名)(850)+TX、氯灭鼠灵(1004)+TX、克鼠灵(coumafuryl)(1005)+TX、杀鼠醚(coumatetralyl)(175)+TX、鼠立死(1009)+TX、鼠得克(difenacoum)(246)+TX、噻鼠灵(difethialone)(249)+TX、敌鼠(diphacinone)(273)+TX、维生素D2(301)+TX、氟鼠灵(flocoumafen)(357)+TX,氟乙酰胺(fluoroacetamide)(379)+TX、氟鼠啶(flupropadine)(1183)+TX、氟鼠啶盐酸盐(1183)+TX、銄-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、溴甲烷(537)+TX、鼠特灵(norbormide)(1318)+TX、毒鼠灵(phosacetim)(1336)+TX、磷化氢(IUPAC名称)(640)+TX、磷[CCN]+TX、杀鼠酮(pindone)(1341)+TX、亚砷酸钾[CCN]+TX、灭鼠优(pyrinuron)(1371)+TX、海葱素(scilliroside)(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)和磷化锌(640)+TX,
一种增效剂,该增效剂选自以下物质组成的组: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(别名)(324)+TX、MB-599(研究代码)(498)+TX、MGK264(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、sesasmolin(1394)和亚砜(1406)+TX,
一种动物驱避剂,该动物驱避剂选自以下物质组成的组: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,该杀病毒剂选自以下物质组成的组:衣马宁(imanin)(别名)[CCN]和利巴韦林(别名)[CCN]+TX,
一种创伤保护剂,该创伤保护剂选自以下物质组成的组:氧化汞(512)+TX、辛噻酮(octhilinone)(590)和甲基硫茵灵(802)+TX,
以及生物活性的化合物,该化合物选自以下物质组成的组: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(f1usulfamide)[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、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(在WO2007/048556中披露的)+TX、3-二氟甲基-1-甲基-1H-吡唑-4-羧酸[2-(2,4-二氯苯基)-2-甲氧基-1-甲基-乙基]-酰胺(在中WO2008/148570披露的)+TX、1-[4-[4-[(5S)5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基]哌啶-1-基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮+TX、1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基]哌啶-1-基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮[1003318-67-9],两者均在WO2010/123791、WO2008/013925、WO2008/013622和WO2011/051243中第20页披露)+TX、3-二氟甲基-1-甲基-1H-吡唑-4-羧酸(3',4',5'-三氟-二苯-2-基)-酰胺(披露在WO2006/087343中)+TX、以及1-甲基-2-(2,4,5-三氯-噻吩-3-基)-乙基]+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“杀虫剂手册(ThePesticide Manual)”杀虫剂手册-一本世界手册;第13版;编著:C.D.S.TomLin;英国农作物保护委员会(The Pesticide Manual-A WorldCompendium;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“阿维菌素”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“杀虫剂通用名纲要(Compendium of Pesticide Common Names)”中,该纲要在互联网上可得:[A.Wood;杀虫剂通用名纲要,版权1995-2011];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。如果其名称不是“通用名”,则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“开发代号”,或者如果既没有使用这些名称之一,也没有使用“通用名”,则使用的是“替代名称”。“CAS登记号”表示化学文摘登记号。
选自表P的具有化学式I的化合物与上述活性成分的这些活性成分的混合物包括一种选自表P的化合物和一种上述活性成分,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,特别优选地是从2:1至1:2的比率,并且从4:1至2:1的比率同样是优选的,尤其是处于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。那些混合比率被理解为包括,一方面是重量比,并且还有另一方面是摩尔比。
以上描述的混合物可以被用于控制虫害的方法中,该方法包括将一种含如上描述的混合物的组合物施用于害虫或其环境中,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P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P的具有化学式I的化合物和上述活性成分的顺序对于实施本发明并不是至关重要的。
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。
根据本发明的这些组合物以本身己知的方法来制备,在没有助剂的存在下例如通过研磨、筛分和/或压挤固体活性成分以及在至少一种助剂的存在下例如通过将该活性成分与一种或多种佐剂(助剂)一起紧密混合和/或研磨。用于制备这些组合物的这些方法以及用于制备这些组合物的这种化合物I的用途也是本发明的主题。
这些组合物的施用方法,即是控制上述类型的害虫的方法,如喷洒、喷雾,撒粉,刷涂,拌种,撒播或浇灌-它们被选择以适于普遍情况的预期目的-并且这些组合物用于控制上述类型的害虫的用途是本发明的其他主题。典型的浓度比是介于0.1ppm和1000ppm之间,优选介于0.1ppm和500ppm之间的活性成分。每公顷施用量率一般是每公顷1g至2000g的活性成分,特别是10g/ha至1000g/ha,优选10g/ha至600g/ha。
在农作物保护领域中,一种优选的施用方法是施用至这些植物的叶(叶施用),可能的是选择施用的频率和量率以符合所提及的害虫的侵染风险。可替代地,该活性成分可以经根系统(内吸作用)达到植物,这是通过用一种液体组合物将这些植物的所在场所浸透或者通过将固体形式的活性成分引入植物的所在场所(例如引入土壤,例如以颗粒剂(土壤施用)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地加入淹水的稻田中。
根据本发明的这些组合物还适于植物繁殖材料的保护(例如种子,如果实、块茎或籽粒,或者苗圃植物)对抗上述类型的害虫。该繁殖材料可以用上述组合物在种植前进行处理,例如种子可以在播种前进行处理。可替代地,这些组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。
本发明的方法包括向有用的植物、其场所或其繁殖材料上混合地或单独地施用一个协同有效的合计量值的具有化学式(I)化合物以及另一种其他的化合物或组合物(例如,一种另外的其他有杀生物活性的成分或组合物)。
根据本发明的所述组合中的一些具有内吸作用并且可以被用作叶上、土壤和种子处理的杀真菌剂。
使用根据本发明的组合,有可能抑制或破坏致植物病的微生物,这些微生物发生于在多种不同的有用植物的植物或植物部分(水果、花、叶子、茎、块茎、根)上发生的疾病,同时还保护了稍后生长的植物部分免于被致植物病的微生物侵袭。
本发明的组合对于控制在不同的有用的植物或其种子中的真菌是特别有意义的,尤其是大田作物中,例如马铃薯、烟草和甜菜以及小麦、黑麦、大麦、燕麦、稻、玉米、菌苔、棉花、大豆、油菜、豆荚作物、向日葵、咖啡、甘蔗、在园艺和葡萄种植中的果实以及观赏的植物,在蔬菜(例如黄瓜、豆和葫芦)中的真菌。
可以对除包含具有化学式(I)的化合物之外还包含至少一种另外的杀真菌活性化合物的本发明的组合物进行配制,并且可以用与上述单独的具有化学式(I)的杀真菌活性化合物相同的方式施用并使用。
以下非限制性的实例更详细地展示了以上描述的发明而非对其进行限制。
实例1:3-{1-[3-(4-氯-苯基)-5-苯基-异噁唑-4-基]-1-甲氧基-乙基}-吡啶的
合成
步骤1:1-[3-(4-氯-苯基)-5-苯基-异噁唑-4-基]-乙酮的合成
将4-氯-N-羟基亚胺苄基氯化物(4.2g,22mmol;根据以下文件制备:Liu,Kou-Chang等人,《有机化学期刊》(J.Org.Chem.)1980,45(19),3916-18)、4-苯基-3-丁炔-2-酮(2.88g,20mmol,可商购:阿尔德林公司(Aldrich)N°161268)、异丙醇(60ml)以及碳酸氢钠(1.68g,40mmol)装入圆底烧瓶中,并且将该反应混合物在68°C搅拌过夜。将该反应混合物在减压下进行蒸发。将该残余物溶解在乙酸乙酯(100ml)中,用水(2x50ml)洗涤,用盐水(50ml)洗涤,用硫酸镁进行干燥,进行过滤并在减压下进行蒸发以给出6.4g的粗产物。将该粗产物用异丙醚再结晶以给出3.2g的1-[3-(4-氯-苯基)-5-苯基-异噁唑-4-基]-乙酮(产率:54%)。
步骤2:1-[3-(4-氯-苯基)-5-苯基-异噁唑-4-基]-1-吡啶-3-基-乙醇的合成
在惰性气氛下,将溶解在二乙醚(5ml)中的3-溴吡啶(869mg,5.5mmol)冷却至-78°C。随后,在-78°C将正丁基锂(1.6M于己烷中,3.3ml,5.25mmol)逐滴添加至该溶液中,并且在该温度将该反应混合物搅拌30分钟。然后,在-78°C,将溶解在四氢呋喃(10ml)中的1-[3-(4-氯-苯基)-5-苯基-异噁唑-4-基]-乙酮经10分钟的时间逐滴添加至该反应混合物中。移除冷却浴并且允许该反应混合物加温至室温过夜。将该反应用饱和的氯化铵溶液(50ml)进行水解,用乙酸乙酯(2x50ml)进行萃取,将合并的有机相用水(2x25ml)洗涤,用盐水(25ml)洗涤,用硫酸镁进行干燥,进行过滤并在减压下进行蒸发。通过快速色谱法(环己烷/乙酸乙酯:1/1)纯化粗产物以给出1-[3-(4-氯-苯基)-5-苯基-异噁唑-4-基]-1-吡啶-3-基-乙醇。
步骤3:3-{1-[3-(4-氯-苯基)-5-苯基-异噁唑-4-基]-1-甲氧基-乙基}-吡啶的
合成。
在惰性气氛下,在-10°C,将氢化钠(在矿物油中60%的分散度,59mg,1.48mmol)添加至1-[3-(4-氯-苯基)-5-苯基-异噁唑-4-基]-1-吡啶-3-基-乙醇(280mg,0.74mmol)于四氢呋喃(10ml)中的溶液中,并且然后在该温度下添加甲基碘(1g,7.4mmol)。接着在室温将该反应混合物搅拌2小时。将该反应混合物用水进行淬灭,并且用乙酸乙酯(3x25ml)进行萃取。将合并的有机相用水(20ml)、盐水(20ml)进行洗涤,用硫酸镁进行干燥,进行过滤并在减压下进行蒸发。通过快速色谱法纯化粗产物以给出3-{1-[3-(4-氯-苯基)-5-苯基-异噁唑-4-基]-1-甲氧基-乙基}-吡啶。
实例2:1-[3-(4-氯-苯基)-5-苯基-异噻唑-4-基]-1-吡啶-3-基-乙醇的合成
步骤1:5-(4-氯-苯基)-[1,3,4]噁噻唑基-2-酮的合成
在100°C,对在甲苯中的4-氯苯甲酰胺(12g,68.5mmol;可商购,Aldrich C23802)和氯羰基次磺酰氯(10ml,102.8mmol;可商购:Aldrich247138)进行搅拌直到气体释放已经几乎停止。然后通过薄层层析法监测该反应,该薄层层析法显示起始材料的消耗。然后在减压下将该反应混合物进行浓缩,并且将残余物(14.6g)直接用于下一步骤。
步骤2:1-[3-(4-氯-苯基)-5-苯基-异噻唑-4-基]-乙酮的合成
将氯化铝(258mg,1.9mmol)添加至搅拌的5-(4-氯-苯基)-[1,3,4]噻唑基-2-酮(300mg;1.3mmol)和4-苯基-3-丁炔-2-酮(185μL,1.3mmol,可商购:Aldrich 161268)于氯苯中的溶液中。然后将反应混合物在140°C搅拌20分钟。然后该反应混合物在二氯甲烷与饱和的碳酸氢钠水溶液之间进行分配。将有机相分离,并在减压下进行浓缩。将残余物通过快速色谱法纯化以给出225mg的1-[3-(4-氯-苯基)-5-苯基-异噻唑-4-基]-乙酮(产率:55%)。
步骤3:1-[3-(4-氯-苯基)-5-苯基-异噻唑-4-基]-1-吡啶-3-基-乙醇的合成
在惰性气氛下,将溶解在二乙醚(5ml)中的3-溴吡啶(60mg,0.57mmol)冷却至-78°C。随后,在-78°C将正丁基锂(1.6M于己烷中,0.38ml,0.61mmol)逐滴添加至该溶液中,并且在该温度将该反应混合物搅拌30分钟。然后,在-78°C,将溶解在四氢呋喃(5ml)中的1-[3-(4-氯-苯基)-5-苯基-异噻唑-4-基]-乙酮经10分钟的时间逐滴添加至该反应混合物中。移除冷却浴并且允许该反应混合物加温至室温过夜。将该反应用饱和的碳酸氢钠水溶液(30ml)进行水解,用乙酸乙酯(50ml)进行萃取。将有机相用硫酸镁进行干燥,进行过滤并在减压下进行蒸发。通过快速色谱法纯化粗产物以给出1-[3-(4-氯-苯基)-5-苯基-异噻唑-4-基]-1-吡啶-3-基-乙醇。
实例3:1-[3-(4-氯-2-氟-苯基)-5-(2,4-二氟-苯基)-异噁唑-4-基]-1-吡啶-3-基
-乙醇的合成
步骤1:3-(2,4-二氟-苯基)-1-吡啶-3-基-炔丙酮(propynone)的合成
在氮气下并且冷却至-78°C,将正丁基锂(2.0M于环己烷中,50ml,100mmol)逐滴添加至1-乙炔基-2,4-二氟苯(16.6g,120mmol,可商购:Aldrich 556440)于四氢呋喃(200ml)中的溶液中。在该温度,将该反应混合物搅拌30分钟,并且之后逐滴添加稀释于50ml的干四氢呋喃中的N-甲氧基-N-甲基-烟酰胺(16.6g,100mmol,根据以下文献制备:WO2005097760)。在-78°C将该混合物搅拌30分钟并且然后允许加温到室温并且然后搅拌2h。将该反应混合物用饱和的氯化铵溶液(100ml)进行淬灭并且用乙酸乙酯(2x200ml)进行萃取。将合并的有机萃取物用硫酸镁进行干燥,进行过滤并在减压下进行蒸发以给出一种棕色油状物。通过快速色谱法纯化粗产物以给出3-(2,4-二氟-苯基)-1-吡啶-3-基-炔丙酮(7.05g)。
步骤2:[3-(4-氯-2-氟-苯基)-5-(2,4-二氟-苯基)-异噁唑-4-基]-吡啶-3-基-甲
酮的合成
将3-(2,4-二氟-苯基)-1-吡啶-3-基-炔丙酮(20g,82mmol),(22g,106mmol,根据以下文献制备:US2009/143371)以及碳酸氢钠(10.3g,123mmol)一起混合于异丙醇(500ml)中。将该反应混合物在68°C加热过夜。将该反应混合物冷却下来并在减压下进行浓缩。将残余物溶解在EtOAc(200ml)以及盐水(200ml)中。分离有机相并且用乙酸乙酯(2x200mL)萃取水相。将合并的有机层用盐水(2x100ml)洗涤,用硫酸钠进行干燥,进行过滤并且在减压下进行浓缩。在二乙醚中搅拌固体残余物并且进行过滤以给出13g的[3-(4-氯-2-氟-苯基)-5-(2,4-二氟-苯基)-异噁唑-4-基]-吡啶-3-基-甲酮。
步骤3:1-[3-(4-氯-2-氟-苯基)-5-(2,4-二氟-苯基)-异噁唑-4-基]-1-吡啶-3-基
-乙醇的合成
在惰性气氛下,将无水氯化铈(830mg,3.37mmol)添加至[3-(4-氯-2-氟-苯基)-5-(2,4-二氟-苯基)-异噁唑-4-基]-吡啶-3-基-甲酮(1.4g,3.37mmol)于四氢呋喃(20ml)中的溶液中。将该反应混合物冷却至-78°C。在该温度添加甲基锂(1.6M于醚中,8.43ml,13.5mmol),并且将该反应混合物在-78°C搅拌1.5h。将该反应混合物用氯化铵水溶液(25ml)进行水解并且在室温下搅拌几分钟。将该反应混合物用乙酸乙酯(3x40ml)进行萃取。将合并的有机层用盐水(50ml)洗涤,用硫酸镁进行干燥,进行过滤并在减压下进行蒸发。通过快速色谱法纯化残余物以给出1-[3-(4-氯-2-氟-苯基)-5-(2,4-二氟-苯基)-异噁唑-4-基]-1-吡啶-3-基-乙醇。
在表T1、表T2中的另外的化合物通过类似的方法使用适当的起始材料制备。
表T1:
表T2:
以下表3至表28的化合物能以类似的方式获得。
表3涵盖以下类型的217种化合物:
其中R1和R2是如下表3中所描述的并且R4是氢:
| 化合物 | R1 | R2 |
| T3.1 | 4-氯-苯基 | 苯基 |
| T3.2 | 4-氯-苯基 | 4-氯-苯基 |
| T3.3 | 4-氯-苯基 | 3-氯-苯基 |
| T3.4 | 4-氯-苯基 | 2-氯-苯基 |
| T3.5 | 4-氯-苯基 | 2,4-二氯-苯基 |
| T3.6 | 4-氯-苯基 | 2-苯硫基 |
| T3.7 | 4-氯-苯基 | 5-氯-2-苯硫基 |
| T3.8 | 4-氯-苯基 | 5-溴-2-苯硫基 |
| T3.9 | 4-氯-苯基 | 4-氟-苯基 |
| T3.10 | 4-氯-苯基 | 3-氟-苯基 |
| T3.11 | 4-氯-苯基 | 2-氟-苯基 |
| T3.12 | 4-氯-苯基 | 2,4-二氟-苯基 |
| T3.13 | 4-氯-苯基 | 2-氟-4-氯-苯基 |
| T3.14 | 4-氯-苯基 | 2-氯-4-氟-苯基 |
| T3.15 | 4-氯-苯基 | 4-三氟甲基-苯基 |
| T3.16 | 4-氯-苯基 | 3-三氟甲基-苯基 |
| T3.17 | 4-氯-苯基 | 2-三氟甲基-苯基 |
| T3.18 | 4-氯-苯基 | 4-溴-苯基 |
| T3.19 | 4-氯-苯基 | 环己基 |
| T3.20 | 4-氯-苯基 | 环戊基 |
| T3.21 | 4-氯-苯基 | 环丁基 |
| T3.22 | 4-氯-苯基 | 环丙基 |
| T3.23 | 4-氯-苯基 | 叔丁基 |
| T3.24 | 4-氯-苯基 | 仲丁基 |
| T3.25 | 4-氯-苯基 | 异戊基 |
| T3.26 | 4-氯-苯基 | 异丙基 |
| T3.27 | 4-氯-苯基 | Et |
| T3.28 | 4-氯-苯基 | Me |
| T3.29 | 4-氯-苯基 | Cl |
| T3.30 | 4-氯-苯基 | Br |
| T3.31 | 4-氯-苯基 | CF3 |
| T3.32 | 4-氯-2-氟-苯基 | 苯基 |
| T3.33 | 4-氯-2-氟-苯基 | 4-氯-苯基 |
| T3.34 | 4-氯-2-氟-苯基 | 3-氯-苯基 |
| T3.35 | 4-氯-2-氟-苯基 | 2-氯-苯基 |
| T3.36 | 4-氯-2-氟-苯基 | 2,4-二氯-苯基 |
| T3.37 | 4-氯-2-氟-苯基 | 2-苯硫基 |
| T3.38 | 4-氯-2-氟-苯基 | 5-氯-2-苯硫基 |
| T3.39 | 4-氯-2-氟-苯基 | 5-溴-2-苯硫基 |
| T3.40 | 4-氯-2-氟-苯基 | 4-氟-苯基 |
| T3.41 | 4-氯-2-氟-苯基 | 3-氟-苯基 |
| T3.42 | 4-氯-2-氟-苯基 | 2-氟-苯基 |
| T3.43 | 4-氯-2-氟-苯基 | 2,4-二氟-苯基 |
| T3.44 | 4-氯-2-氟-苯基 | 2-氟-4-氯-苯基 |
| T3.45 | 4-氯-2-氟-苯基 | 2-氯-4-氟-苯基 |
| T3.46 | 4-氯-2-氟-苯基 | 4-三氟甲基-苯基 |
| T3.47 | 4-氯-2-氟-苯基 | 3-三氟甲基-苯基 |
| T3.48 | 4-氯-2-氟-苯基 | 2-三氟甲基-苯基 |
| T3.49 | 4-氯-2-氟-苯基 | 4-溴-苯基 |
| T3.50 | 4-氯-2-氟-苯基 | 环己基 |
| T3.51 | 4-氯-2-氟-苯基 | 环戊基 |
| T3.52 | 4-氯-2-氟-苯基 | 环丁基 |
| T3.53 | 4-氯-2-氟-苯基 | 环丙基 |
| T3.54 | 4-氯-2-氟-苯基 | 叔丁基 |
| T3.55 | 4-氯-2-氟-苯基 | 仲丁基 |
| T3.56 | 4-氯-2-氟-苯基 | 异戊基 |
| T3.57 | 4-氯-2-氟-苯基 | 异丙基 |
| T3.58 | 4-氯-2-氟-苯基 | Et |
| T3.59 | 4-氯-2-氟-苯基 | Me |
| T3.60 | 4-氯-2-氟-苯基 | Cl |
| T3.61 | 4-氯-2-氟-苯基 | Br |
| T3.62 | 4-氯-2-氟-苯基 | CF3 |
| T3.63 | 2,4-二氟-苯基 | 苯基 |
| T3.64 | 2,4-二氟-苯基 | 4-氯-苯基 |
| T3.65 | 2,4-二氟-苯基 | 3-氯-苯基 |
| T3.66 | 2,4-二氟-苯基 | 2-氯-苯基 |
| T3.67 | 2,4-二氟-苯基 | 2,4-二氯-苯基 |
| T3.68 | 2,4-二氟-苯基 | 2-苯硫基 |
| T3.69 | 2,4-二氟-苯基 | 5-氯-2-苯硫基 |
| T3.70 | 2,4-二氟-苯基 | 5-溴-2-苯硫基 |
| T3.71 | 2,4-二氟-苯基 | 4-氟-苯基 |
| T3.72 | 2,4-二氟-苯基 | 3-氟-苯基 |
| T3.73 | 2,4-二氟-苯基 | 2-氟-苯基 |
| T3.74 | 2,4-二氟-苯基 | 2,4-二氟-苯基 |
| T3.75 | 2,4-二氟-苯基 | 2-氟-4-氯-苯基 |
| T3.76 | 2,4-二氟-苯基 | 2-氯-4-氟-苯基 |
| T3.77 | 2,4-二氟-苯基 | 4-三氟甲基-苯基 |
| T3.78 | 2,4-二氟-苯基 | 3-三氟甲基-苯基 |
| T3.79 | 2,4-二氟-苯基 | 2-三氟甲基-苯基 |
| T3.80 | 2,4-二氟-苯基 | 4-溴-苯基 |
| T3.81 | 2,4-二氟-苯基 | 环己基 |
| T3.82 | 2,4-二氟-苯基 | 环戊基 |
| T3.83 | 2,4-二氟-苯基 | 环丁基 |
| T3.84 | 2,4-二氟-苯基 | 环丙基 |
| T3.85 | 2,4-二氟-苯基 | 叔丁基 |
| T3.86 | 2,4-二氟-苯基 | 仲丁基 |
| T3.87 | 2,4-二氟-苯基 | 异戊基 |
| T3.88 | 2,4-二氟-苯基 | 异丙基 |
| T3.89 | 2,4-二氟-苯基 | Et |
| T3.90 | 2,4-二氟-苯基 | Me |
| T3.91 | 2,4-二氟-苯基 | Cl |
| T3.92 | 2,4-二氟-苯基 | Br |
| T3.93 | 2,4-二氟-苯基 | CF3 |
| T3.94 | 2,4-二氯-苯基 | 苯基 |
| T3.95 | 2,4-二氯-苯基 | 4-氯-苯基 |
| T3.96 | 2,4-二氯-苯基 | 3-氯-苯基 |
| T3.97 | 2,4-二氯-苯基 | 2-氯-苯基 |
| T3.98 | 2,4-二氯-苯基 | 2,4-二氯-苯基 |
| T3.99 | 2,4-二氯-苯基 | 2-苯硫基 |
| T3.100 | 2,4-二氯-苯基 | 5-氯-2-苯硫基 |
| T3.101 | 2,4-二氯-苯基 | 5-溴-2-苯硫基 |
| T3.102 | 2,4-二氯-苯基 | 4-氟-苯基 |
| T3.103 | 2,4-二氯-苯基 | 3-氟-苯基 |
| T3.104 | 2,4-二氯-苯基 | 2-氟-苯基 |
| T3.105 | 2,4-二氯-苯基 | 2,4-二氟-苯基 |
| T3.106 | 2,4-二氯-苯基 | 2-氟-4-氯-苯基 |
| T3.107 | 2,4-二氯-苯基 | 2-氯-4-氟-苯基 |
| T3.108 | 2,4-二氯-苯基 | 4-三氟甲基-苯基 |
| T3.109 | 2,4-二氯-苯基 | 3-三氟甲基-苯基 |
| T3.110 | 2,4-二氯-苯基 | 2-三氟甲基-苯基 |
| T3.111 | 2,4-二氯-苯基 | 4-溴-苯基 |
| T3.112 | 2,4-二氯-苯基 | 环己基 |
| T3.113 | 2,4-二氯-苯基 | 环戊基 |
| T3.114 | 2,4-二氯-苯基 | 环丁基 |
| T3.115 | 2,4-二氯-苯基 | 环丙基 |
| T3.116 | 2,4-二氯-苯基 | 叔丁基 |
| T3.117 | 2,4-二氯-苯基 | 仲丁基 |
| T3.118 | 2,4-二氯-苯基 | 异戊基 |
| T3.119 | 2,4-二氯-苯基 | 异丙基 |
| T3.120 | 2,4-二氯-苯基 | Et |
| T3.121 | 2,4-二氯-苯基 | Me |
| T3.122 | 2,4-二氯-苯基 | Cl |
| T3.123 | 2,4-二氯-苯基 | Br |
| T3.124 | 2,4-二氯-苯基 | CF3 |
| T3.125 | 2-氟-苯基 | 苯基 |
| T3.126 | 2-氟-苯基 | 4-氯-苯基 |
| T3.127 | 2-氟-苯基 | 3-氯-苯基 |
| T3.128 | 2-氟-苯基 | 2-氯-苯基 |
| T3.129 | 2-氟-苯基 | 2,4-二氯-苯基 |
| T3.130 | 2-氟-苯基 | 2-苯硫基 |
| T3.131 | 2-氟-苯基 | 5-氯-2-苯硫基 |
| T3.132 | 2-氟-苯基 | 5-溴-2-苯硫基 |
| T3.133 | 2-氟-苯基 | 4-氟-苯基 |
| T3.134 | 2-氟-苯基 | 3-氟-苯基 |
| T3.135 | 2-氟-苯基 | 2-氟-苯基 |
| T3.136 | 2-氟-苯基 | 2,4-二氟-苯基 |
| T3.137 | 2-氟-苯基 | 2-氟-4-氯-苯基 |
| T3.138 | 2-氟-苯基 | 2-氯-4-氟-苯基 |
| T3.139 | 2-氟-苯基 | 4-三氟甲基-苯基 |
| T3.140 | 2-氟-苯基 | 3-三氟甲基-苯基 |
| T3.141 | 2-氟-苯基 | 2-三氟甲基-苯基 |
| T3.142 | 2-氟-苯基 | 4-溴-苯基 |
| T3.143 | 2-氟-苯基 | 环己基 |
| T3.144 | 2-氟-苯基 | 环戊基 |
| T3.145 | 2-氟-苯基 | 环丁基 |
| T3.146 | 2-氟-苯基 | 环丙基 |
| T3.147 | 2-氟-苯基 | 叔丁基 |
| T3.148 | 2-氟-苯基 | 仲丁基 |
| T3.149 | 2-氟-苯基 | 异戊基 |
| T3.150 | 2-氟-苯基 | 异丙基 |
| T3.151 | 2-氟-苯基 | Et |
| T3.152 | 2-氟-苯基 | Me |
| T3.153 | 2-氟-苯基 | Cl |
| T3.154 | 2-氟-苯基 | Br |
| T3.155 | 2-氟-苯基 | CF3 |
| T3.156 | 5-氯-2-苯硫基 | 苯基 |
| T3.157 | 5-氯-2-苯硫基 | 4-氯-苯基 |
| T3.158 | 5-氯-2-苯硫基 | 3-氯-苯基 |
| T3.159 | 5-氯-2-苯硫基 | 2-氯-苯基 |
| T3.160 | 5-氯-2-苯硫基 | 2,4-二氯-苯基 |
| T3.161 | 5-氯-2-苯硫基 | 2-苯硫基 |
| T3.162 | 5-氯-2-苯硫基 | 5-氯-2-苯硫基 |
| T3.163 | 5-氯-2-苯硫基 | 5-溴-2-苯硫基 |
| T3.164 | 5-氯-2-苯硫基 | 4-氟-苯基 |
| T3.165 | 5-氯-2-苯硫基 | 3-氟-苯基 |
| T3.166 | 5-氯-2-苯硫基 | 2-氟-苯基 |
| T3.167 | 5-氯-2-苯硫基 | 2,4-二氟-苯基 |
| T3.168 | 5-氯-2-苯硫基 | 2-氟-4-氯-苯基 |
| T3.169 | 5-氯-2-苯硫基 | 2-氯-4-氟-苯基 |
| T3.170 | 5-氯-2-苯硫基 | 4-三氟甲基-苯基 |
| T3.171 | 5-氯-2-苯硫基 | 3-三氟甲基-苯基 |
| T3.172 | 5-氯-2-苯硫基 | 2-三氟甲基-苯基 |
| T3.173 | 5-氯-2-苯硫基 | 4-溴-苯基 |
| T3.174 | 5-氯-2-苯硫基 | 环己基 |
| T3.175 | 5-氯-2-苯硫基 | 环戊基 |
| T3.176 | 5-氯-2-苯硫基 | 环丁基 |
| T3.177 | 5-氯-2-苯硫基 | 环丙基 |
| T3.178 | 5-氯-2-苯硫基 | 叔丁基 |
| T3.179 | 5-氯-2-苯硫基 | 仲丁基 |
| T3.180 | 5-氯-2-苯硫基 | 异戊基 |
| T3.181 | 5-氯-2-苯硫基 | 异丙基 |
| T3.182 | 5-氯-2-苯硫基 | Et |
| T3.183 | 5-氯-2-苯硫基 | Me |
| T3.184 | 5-氯-2-苯硫基 | Cl |
| T3.185 | 5-氯-2-苯硫基 | Br |
| T3.186 | 5-氯-2-苯硫基 | CF3 |
| T3.187 | 环己基 | 苯基 |
| T3.188 | 环己基 | 4-氯-苯基 |
| T3.189 | 环己基 | 3-氯-苯基 |
| T3.190 | 环己基 | 2-氯-苯基 |
| T3.191 | 环己基 | 2,4-二氯-苯基 |
| T3.192 | 环己基 | 2-苯硫基 |
| T3.193 | 环己基 | 5-氯-2-苯硫基 |
| T3.194 | 环己基 | 5-溴-2-苯硫基 |
| T3.195 | 环己基 | 4-氟-苯基 |
| T3.196 | 环己基 | 3-氟-苯基 |
| T3.197 | 环己基 | 2-氟-苯基 |
| T3.198 | 环己基 | 2,4-二氟-苯基 |
| T3.199 | 环己基 | 2-氟-4-氯-苯基 |
| T3.200 | 环己基 | 2-氯-4-氟-苯基 |
| T3.201 | 环己基 | 4-三氟甲基-苯基 |
| T3.202 | 环己基 | 3-三氟甲基-苯基 |
| T3.203 | 环己基 | 2-三氟甲基-苯基 |
| T3.204 | 环己基 | 4-溴-苯基 |
| T3.205 | 环己基 | 环己基 |
| T3.206 | 环己基 | 环戊基 |
| T3.207 | 环己基 | 环丁基 |
| T3.208 | 环己基 | 环丙基 |
| T3.209 | 环己基 | 叔丁基 |
| T3.210 | 环己基 | 仲丁基 |
| T3.211 | 环己基 | 异戊基 |
| T3.212 | 环己基 | 异丙基 |
| T3.213 | 环己基 | Et |
| T3.214 | 环己基 | Me |
| T3.215 | 环己基 | Cl |
| T3.216 | 环己基 | Br |
| T3.217 | 环己基 | CF3 |
表4涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表5涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表6涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表7涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表8涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表9涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表10涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表11涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表12涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表13涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表14涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表15涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是氢。
表16涵盖以下类型的217种化合物:
其中R1和R2是如下表3中所描述的并且R4是甲基:
表17涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表18涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表19涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表20涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表21涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表22涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表23涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表24涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表25涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表26涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表27涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
表28涵盖以下类型的217种化合物:
其中R1和R2是如在表3中所描述的并且R4是甲基。
生物学实例:
这些实例展示了表T1和T2中描述的化合物的杀真菌特性。
方法说明:
葡萄孢菌(Botrytis cinerea)(灰酶菌):将来自冷冻储存的真菌分生孢子直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中以后,添加含有真菌孢子的营养肉汁。将这些测试板在24°C下孵育并且72小时之后通过光度法确定对生长的抑制。
以下化合物在200ppm下给出了对葡萄孢菌至少80%的控制:T1.1、T1.4、T1.5、T1.11、T1.14、T1.15、T1.17、T1.18、T1.19、T1.20、T2.1
小麦壳针孢(叶疱斑症):将来自冷冻储存的真菌分生孢子直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中以后,添加含有真菌孢子的营养肉汁。将这些测试板在24°C下孵育并且72小时之后通过光度法确定对生长的抑制。
以下化合物在200ppm下给出了对小麦壳针孢至少80%的控制:T1.1、T1.2、T1.4、T1.5、T1.11、T1.14、T1.15、T1.17、T1.18、T1.19、T1.20、T2.1
叶锈病菌(Puccinia recondita)(褐锈病(Brown rust)):将小麦叶节置于多孔板(24孔板)的琼脂中并且喷洒试验溶液。干燥之后,将叶片用真菌孢子悬浮液接种。适当的孵育之后,化合物的活性8dpi(孵育之后的天数)被评定为防止性杀真菌活性。
以下化合物在200ppm下给出了对叶锈病菌至少80%的控制:T1.1、T1.5、T1.18、T1.19、T1.20、T2.1。
Claims (9)
1.一种具有化学式(I)的化合物
其中
X是S或O;
Y是C-H或N;
R1是未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2- 8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;或一个取代的5至10-元芳香族杂环;
R2是H;卤素,未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C7-15芳烷基;取代的C7- 15芳烷基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;未取代的C6-10芳硫基-C1-8烷基;取代的C6-10芳硫基-C1-8烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;一个取代的5至10-元芳香族杂环;未取代的C1-8烷基甲硅烷基;或取代的C1-8烷基甲硅烷基;
R3是未取代的C6-10芳基;取代的C6-10芳基;未取代的C1-8烷基;取代的C1-8烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C7-15芳基链烯基;取代的C7-15芳基链烯基;未取代的C7-15芳基炔基;取代的C7-15芳基炔基
R4是H;未取代的C1-C8烷基;取代的C1-C8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;
R5是一个未取代的6至10元芳香族杂环;或一个取代的5至10元芳香族杂环。
2.根据权利要求1所述的化合物,其特征在于
X是S或O;
Y是C-H或N;
R1是未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2- 8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C7-15芳烷基;取代的C7-15芳烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;或一个取代的5至10-元芳香族杂环;
R2是H;卤素,未取代的C1-8烷基;取代的C1-8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;未取代的C1-8烷氧基烷基;取代的C1-8烷氧基烷基;未取代的C1-8卤烷基;取代的C1-8卤烷基;未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C7-15芳烷基;取代的C7- 15芳烷基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;未取代的C6-10芳硫基-C1-8烷基;取代的C6-10芳硫基-C1-8烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳硫基;取代的C6-10芳硫基;一个未取代的5至10-元芳香族杂环;一个取代的5至10-元芳香族杂环;未取代的C1-8烷基甲硅烷基;或取代的C1-8烷基甲硅烷基;
R3是未取代的C1-8烷基;取代的C1-8烷基;
R4是H;未取代的C1-C8烷基;取代的C1-C8烷基;未取代的C2-8链烯基;取代的C2-8链烯基;未取代的C2-8炔基;取代的C2-8炔基;
R5是一个未取代的6元芳香族杂环;或一个取代的5至6元芳香族杂环。
3.根据权利要求2所述的化合物,其特征在于
X是S或O;
Y是C-H或N;
R1是未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基;取代的C6-10芳氧基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;一个未取代的5至10元芳香族杂环;一个取代的5至10元芳香族杂环;
R2是未取代的C1-8烷基;取代的C1-8烷基;未取代的C3-8环烷基;取代的C3- 8环烷基;未取代的C6-10芳基;取代的C6-10芳基;未取代的C6-10芳氧基-C1-8烷基;取代的C6-10芳氧基-C1-8烷基;一个未取代的5至10元芳香族杂环;一个取代的5至10元芳香族杂环;
R3是未取代的C1-8烷基;取代的C1-8烷基;
R4是H;未取代的C1-C6烷基;取代的C1-C6烷基;
R5是一个含有一个或两个氮原子的未取代的6元芳香族杂环;或一个含有一个或两个氮原子的取代的6元芳香族杂环。
4.根据权利要求3所述的化合物,其特征在于
X是S或O;
Y是C-H或N;
R1是未取代的C6-10芳基;取代的C6-10芳基;
R2是未取代的C3-8环烷基;取代的C3-8环烷基;未取代的C6-10芳基;取代的C6-10芳基;
R3是甲基;乙基;
R4是H;未取代的C1-C4烷基;取代的C1-C4烷基;
R5是一种未取代的吡啶基或嘧啶基;或一种取代的吡啶基或嘧啶基;优选一种未取代的吡啶基或嘧啶基。
5.根据权利要求4所述的化合物,其特征在于
X是S或O;
Y是C-H或N;
R1是未取代的苯基;经Cl、F取代的苯基;
R2是未取代的环己基;未取代的苯基;经Cl、F取代的苯基;
R3是甲基;乙基;
R4是H;甲基;乙基;
R5是未取代的吡啶基或嘧啶基,优选一种未取代的3-吡啶基或5-嘧啶基。
6.一种用于防止和/或控制植物和/或植物繁殖材料中的真菌侵染的方法,该方法包括将一种杀真菌有效量的具有化学式(I)的化合物施用到该植物或者植物繁殖材料上或其场所。
7.一种用于控制真菌侵染的组合物,该组合物包括一种具有化学式(I)的化合物以及一种农业上可接受的载体或稀释剂。
8.根据权利要求11所述的组合物,该组合物进一步包括除该具有化学式(I)的化合物之外的至少一种另外的杀真菌活性化合物。
9.根据权利要求8所述的组合物,其中该另外的杀真菌活性化合物是阿拉酸式苯-S-甲基、嘧菌酯、百菌清、环唑醇、嘧菌环胺、苯醚甲环唑、苯锈啶、氟啶胺、咯菌酯、己唑醇、吡蚜酮、双炔酰菌胺、精甲霜灵、戊菌唑、丙环唑、咯喹酮、sedaxane或涕必灵。
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|---|---|---|---|---|
| EP2447261A1 (en) * | 2010-10-29 | 2012-05-02 | Basf Se | Pyrrole, furane and thiophene derivatives and their use as fungicides |
| US8809372B2 (en) | 2011-09-30 | 2014-08-19 | Asana Biosciences, Llc | Pyridine derivatives |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| JP2017078022A (ja) * | 2014-02-28 | 2017-04-27 | クミアイ化学工業株式会社 | イソキサゾール誘導体及びそれを用いた農園芸用植物病害防除剤 |
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| FR1569940A (zh) * | 1967-04-27 | 1969-06-06 | ||
| NO173389C (no) | 1986-07-15 | 1993-12-08 | Nihon Nohyaku Co Ltd | Analogifremgangsm}te og mellomprodukter for fremstilling av tetrapeutisk aktive 1,3,5-tritianderivater |
| CA1340685C (en) | 1988-07-29 | 1999-07-27 | Frederick Meins | Dna sequences encoding polypeptides having beta-1,3-glucanase activity |
| DE69034081T2 (de) | 1989-03-24 | 2004-02-12 | Syngenta Participations Ag | Krankheitsresistente transgene Pflanze |
| US5639949A (en) | 1990-08-20 | 1997-06-17 | Ciba-Geigy Corporation | Genes for the synthesis of antipathogenic substances |
| SE9302332D0 (sv) * | 1993-07-06 | 1993-07-06 | Ab Astra | New compounds |
| EA001148B1 (ru) | 1996-03-11 | 2000-10-30 | Новартис Аг | Производные пиримидин-4-она |
| US5750720A (en) * | 1996-03-28 | 1998-05-12 | Ortho Pharmaceutical Corporation | 4- (thien-3-yl)methyl!-imidazole analgesics |
| WO2005037271A2 (en) | 2003-10-17 | 2005-04-28 | Tanabe Seiyaku Co., Ltd. | Large conductance calcium-activated k channel opener |
| US20050239751A1 (en) | 2004-03-26 | 2005-10-27 | Rigel Pharmaceuticals, Inc. | Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses |
| MX2007002929A (es) | 2004-09-10 | 2007-08-16 | Syngenta Ltd | Isoxazoles sustituidos como funguicidas. |
| DE102005007160A1 (de) | 2005-02-16 | 2006-08-24 | Basf Ag | Pyrazolcarbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| JP2009503099A (ja) * | 2005-08-02 | 2009-01-29 | グラクソ グループ リミテッド | M3ムスカリン性アセチルコリン受容体アンタゴニスト |
| CN102153478B (zh) | 2005-10-25 | 2012-07-11 | 先正达参股股份有限公司 | 用作杀微生物剂的杂环酰胺衍生物 |
| CA2632565A1 (en) | 2005-12-19 | 2007-07-05 | Syngenta Limited | Substituted aromatic heterocyclic compounds as fungicides |
| WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| CL2008001647A1 (es) | 2007-06-08 | 2008-10-10 | Syngenta Participations Ag | Compuestos derivados de feniletil-amida de acido-1h-pirazol-4-carboxilico; compuestos derivados de (feniletil)amina; metodo para controlar o prevenir la infestacion de plantas por parte de microorganismos fitopatogenos; y composicion para el control |
| MX2009014001A (es) | 2007-06-22 | 2010-01-28 | Hoffmann La Roche | Derivados de isoxazol-imidazol. |
| GB0713479D0 (en) * | 2007-07-11 | 2007-08-22 | Syngenta Participations Ag | Substituted aromatic heterocyclic compounds as fungicides |
| ES2531023T3 (es) | 2007-12-04 | 2015-03-09 | Hoffmann La Roche | Derivados de isoxazolo-piridina |
| TWI508962B (zh) | 2009-04-22 | 2015-11-21 | Du Pont | 氮雜環醯胺之固體形態 |
| WO2011051243A1 (en) | 2009-10-29 | 2011-05-05 | Bayer Cropscience Ag | Active compound combinations |
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- 2011-07-19 US US13/810,976 patent/US20130252972A1/en not_active Abandoned
- 2011-07-19 EP EP11733850.9A patent/EP2595985A1/en not_active Withdrawn
- 2011-07-19 BR BR112013001237A patent/BR112013001237A2/pt not_active Application Discontinuation
- 2011-07-19 WO PCT/EP2011/062291 patent/WO2012010567A1/en active Application Filing
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| EP2595985A1 (en) | 2013-05-29 |
| US20130252972A1 (en) | 2013-09-26 |
| BR112013001237A2 (pt) | 2016-05-17 |
| WO2012010567A1 (en) | 2012-01-26 |
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