CN111683930B - 新型异噁唑化合物或其盐 - Google Patents
新型异噁唑化合物或其盐 Download PDFInfo
- Publication number
- CN111683930B CN111683930B CN201880077258.8A CN201880077258A CN111683930B CN 111683930 B CN111683930 B CN 111683930B CN 201880077258 A CN201880077258 A CN 201880077258A CN 111683930 B CN111683930 B CN 111683930B
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- CN
- China
- Prior art keywords
- isoxazole
- methyl
- phenyl
- trifluoroethyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 isoxazole compound Chemical class 0.000 title claims abstract description 339
- 150000003839 salts Chemical class 0.000 title claims abstract description 107
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 53
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 203
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 106
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 56
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 241000244206 Nematoda Species 0.000 claims description 30
- 230000000895 acaricidal effect Effects 0.000 claims description 30
- 241000238876 Acari Species 0.000 claims description 28
- 239000000642 acaricide Substances 0.000 claims description 26
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 17
- VXHIJMMJKGJYSY-UHFFFAOYSA-N 3-(2-fluoro-4-methyl-5-propylsulfinylphenyl)-5-(trifluoromethyl)-1,2-oxazole Chemical compound FC1=C(C=C(C(=C1)C)S(=O)CCC)C1=NOC(=C1)C(F)(F)F VXHIJMMJKGJYSY-UHFFFAOYSA-N 0.000 claims description 14
- 239000005645 nematicide Substances 0.000 claims description 14
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- 235000013601 eggs Nutrition 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
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- 239000002689 soil Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 230000001069 nematicidal effect Effects 0.000 claims description 7
- 230000003151 ovacidal effect Effects 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 231100000194 ovacidal Toxicity 0.000 claims description 5
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
- 230000003129 miticidal effect Effects 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 abstract description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- 125000001544 thienyl group Chemical group 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
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- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
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- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
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- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
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- 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
- 229940035339 tri-chlor Drugs 0.000 description 1
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- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-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
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 239000004061 uncoupling agent Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 150000004669 very long chain fatty acids Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000009029 wenxiao Substances 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010048 yiguan Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- 229950006967 zoxazolamine Drugs 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract
本发明的目的在于提供控制害虫的异噁唑化合物或其盐。本发明提供由式(I)表示的异噁唑化合物或其盐,其中R表示C1‑6烷基或C1‑4卤代烷基;A1及A2相同或不同,各自为卤素或C1‑6烷基;B1表示氢、卤素或C1‑6烷基;B2表示C1‑6烷基、C1‑4卤代烷基或者经取代或未取代的芳基C1‑4卤代烷基;并且,n表示0至2的整数。
Description
技术领域
本发明涉及新型的异噁唑化合物或盐。
背景技术
近年来,一些杀虫剂、杀螨剂或杀线虫剂的使用由于环境污染和残留农药在环境中的逐渐积累而受到限制。
由于长期使用杀螨剂而导致螨虫近年来出现了针对杀螨剂的抗性,因此已难以通过使用已知的杀螨剂来实现控螨。因此,急需开发具有与市售的杀螨剂或杀线虫剂不同的作用的新型杀螨剂或杀线虫剂。
例如,专利文献WO2002/018352及WO97/046530中记载了被苯基取代而得到的异噁唑衍生物。异噁唑衍生物中苯基的3位被限定为烷基磺酰基。这些专利中完全没有公开除草剂以外的用途。
于1986年出版的农业与生物化学(Agricultural and Biological Chemistry)[50(10),2591(1986)]中记载了含有被3-甲硫基取代而得到的异噁唑衍生物的植物生长调节剂,但并未记载该异噁唑衍生物作为害虫控制剂用于农业或园艺的目的。
专利文献JP2008-308448A中公开了由下式(II)表示的化合物:
其中R1表示烷基、链烯基或环烷基;A表示卤素、烷基、链烯基、炔基、环烷基、(羟基亚氨基)甲基、(烷氧基亚氨基)甲基、杂芳基或氰基;X表示卤素;m为0至3的整数;n为0至1的整数;并且Q表示杂芳基或类似的基团。
上述出版物还公开了由下式(III)表示的化合物:
其中Z1和Z2表示氢、卤素、硝基、氰基、经取代或未取代的氨基、经取代或未取代的烷基、经取代或未取代的烷氧基、经取代或未取代的烷基硫基或类似的基团;并且R1、A、X、m和n的定义如上所述。
该出版物还公开了由式(II)和(III)表示的化合物显示杀螨活性和杀线虫活性。
然而,同一出版物的实例中仅示明了由式(II)和(III)表示的化合物以300ppm的高浓度显示出针对二斑叶螨(two-spotted spider mite)和柑橘红蜘蛛(citrus redmite)的杀螨活性,但没有记载针对螨虫卵的效果。
此外,虽然由式(III)表示的化合物之中,n为0的所述由式(III)表示的化合物是特别优选的,但其杀螨活性和杀卵活性是根本不足的。
现有技术文献
专利文献
专利文献1:WO2002/018352
专利文献2:WO97/046530
专利文献3:JP2008-308448A
非专利文献
非专利文献1:农业与生物化学,50(10),2591(1986)
发明内容
用于解决课题的手段
本发明提供不仅针对螨的成虫具有优异效果、而且针对虫卵或卵也具有优异效果的异噁唑化合物或其盐。
本发明也提供即使以低浓度使用时仍然针对螨及/或卵具有优异的控制效果的异噁唑化合物或其盐。
本发明还提供对于已获得对现有杀螨剂的抗性的螨及/或卵具有高控制效果的异噁唑化合物或其盐。
本发明也提供含有上述异噁唑化合物或其盐的杀螨剂、杀卵剂以及杀线虫剂。
具体而言,本申请的发明人经过大量研究,发现由下述通式(I)表示的化合物或其盐在低浓度时显示出优异的杀螨活性。同时,由式(I)表示的化合物也显示出用于农业和园艺用途的、针对害虫、尤其针对以二斑叶螨、柑橘红蜘蛛和神泽氏叶螨(Kanzawa spidermite)为代表的螨的杀卵活性。进而,本申请的发明人发现由式(I)表示的化合物在低浓度时针对例如根结线虫、根腐线虫等线虫具有极其优异的杀线虫活性,从而完成了本发明。
因此,本发明涉及由下式(I)表示的新型异噁唑化合物或其盐。
更具体而言,本发明包括以下实施方式:
项1:
由式(I)表示的异噁唑化合物或其盐,
其中,
R表示C1-6烷基或C1-4卤代烷基;
A1及A2相同或不同,各自为卤素或C1-6烷基;
B1表示氢、卤素或C1-6烷基;
B2表示C1-6烷基、C1-4卤代烷基或者经取代或未取代的芳基C1-4卤代烷基;并且
n表示0至2的整数。
项2:
根据项1的异噁唑化合物或其盐,其中R为正丙基或2,2,2-三氟乙基。
项3:
根据项1或2的异噁唑化合物或其盐,其中A1为氟、氯或甲基。
项4:
根据项1至3中任一项的异噁唑化合物或其盐,其中A2为氟、氯或甲基。
项5:
根据项1至4中任一项的异噁唑化合物或其盐,其中B1为氢或甲基。
项6:
根据项1至5中任一项的异噁唑化合物或其盐,其中B2为二氟甲基、三氟甲基、氯二氟甲基、五氟乙基、七氟丙基或二氟(苯基)甲基。
项7:
根据项1至6中任一项的异噁唑化合物或其盐,其中n为0或1的整数。
项8:
根据项1的异噁唑化合物或其盐,其选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(七氟丙基)异噁唑;
5-(二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
5-(二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟(苯基)甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟(苯基)甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
项9:
根据项1的异噁唑化合物或其盐,其选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(七氟丙基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
项10:
根据项1的异噁唑化合物或其盐,其选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
5-(氯二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
项11:
根据项1的异噁唑化合物或其盐,其选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
项12:
害虫控制剂,其包含根据项1至11中任一项的异噁唑化合物或其盐作为活性成分。
项12-1:
杀螨剂,其包含根据项1至11中任一项的异噁唑化合物或其盐作为活性成分。
项12-2:
杀线虫剂,其包含根据项1至11中任一项的异噁唑化合物或其盐作为活性成分。
项13:
农业用组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项14:
用于控制害虫的组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项15:
杀螨组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项16:
杀卵组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项17:
杀线虫组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项18:
用于控制螨的组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项19:
用于控制虫卵(egg)或卵(ovum)的组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项20:
用于控制线虫的组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项21:
用于控制螨的用途的组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项22:
用于控制虫卵或卵的用途的组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项23:
用于控制线虫的用途的组合物,其包含根据项1至11中任一项的异噁唑化合物或其盐。
项24:
使用根据项1至11中任一项的异噁唑化合物或其盐来控制害虫的方法。
项24-1:
使用根据项1至11中任一项的异噁唑化合物或其盐来控制螨的方法。
项24-2:
使用根据项1至11中任一项的异噁唑化合物或其盐来控制线虫的方法。
项25:
用于控制害虫的方法,其包括将根据项1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤。
项25-1:
用于控制螨的方法,其包括将根据项1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤。
项25-2:
用于控制线虫的方法,其包括将根据项1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤。
项26:
用于控制害虫的方法,其包括将有效量的根据项1至11中任一项的异噁唑化合物或其盐施用至害虫、害虫的栖息处或预期栖息的场所。
项26-1:
用于控制螨的方法,其包括将有效量的根据项1至11中任一项的异噁唑化合物或其盐施用至螨、螨的栖息处或预期栖息的场所。
项26-2:
用于控制线虫的方法,其包括将有效量的根据项1至11中任一项的异噁唑化合物或其盐施用至线虫、线虫的栖息处或预期栖息的场所。
项27:
杀螨的方法,其包括将根据项1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤。
项28:
杀螨的方法,其包括将有效量的根据项1至11中任一项的异噁唑化合物或其盐施用至螨、螨的栖息处或预期栖息的场所。
项29:
杀卵的方法,其包括将根据项1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤。
项30:
杀卵的方法,其包括将有效量的根据项1至11中任一项的异噁唑化合物或其盐施用至卵或预期产卵的场所。
项31:
杀线虫的方法,其包括将根据项1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤。
项32:
杀线虫的方法,其包括将有效量的根据项1至11中任一项的异噁唑化合物或其盐施用至线虫、线虫的栖息处或线虫的预期栖息场所。
项33:
根据项1至11中任一项的异噁唑化合物或其盐的作为杀螨剂的用途。
项34:
异噁唑化合物或其盐的作为杀螨剂的用途,其中,所述异噁唑化合物选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(七氟丙基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
项35:
根据项1至11中任一项的异噁唑化合物或其盐的作为杀卵剂的用途。
项36:
异噁唑化合物或其盐的作为杀卵剂的用途,其中,所述异噁唑化合物选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
5-(氯二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
项37:
根据项1至11中任一项的异噁唑化合物或其盐的作为杀线虫剂的用途。
项38:
异噁唑化合物或其盐的作为杀线虫剂的用途,其中,所述异噁唑化合物选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(全氟乙基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)磺酰基)苯基)-5-(全氟丙基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(全氟丁基)异噁唑;
5-(二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二甲基-5-((2,2,2-三氟乙基)磺酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二氟-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二氯-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
5-(二氟(苯基)甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
5-(二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
需要注意的是,除了明确示出的组合以外,还可将上述特征中的一个或多个以上述特征中一个或多个的组合的形式提供。本领域技术人员可根据需要对下文的详细说明进行阅读和理解以知晓本发明的更多实施方式及优点。
发明的优异效果
根据本发明,能够提供针对害虫具有优异的控制效果的异噁唑化合物或其盐。
特别地,根据本发明,可提供即使在低浓度时也不仅针对螨的成虫具有优异效果、而且针对虫卵具有优异效果的异噁唑化合物或其盐;及含有这些化合物的杀螨剂。
此外,利用本发明,可提供对于已获得对现有杀螨剂的抗性的螨具有高控制效果的异噁唑化合物或其盐、及含有这些化合物的杀螨剂。
除此以外,本发明的异噁唑化合物或其盐对于线虫具有优异的控制效果,可提供含有这些化合物的杀线虫剂。
具体实施方式
以下,参考实例更详细地说明本发明,但本发明的技术范围不限于这些例子。在说明书全文中,除非另有具体说明,则单数表达应理解为包含复数形式的概念。因此,除非另有具体说明,则单数用词(例如,英文中的“一个(a)”、“一种(an)”、“该(the)”等)也应理解为包含复数形式的概念。此外,除非另有具体说明,则本公开文本中使用的术语应理解为基于本领域中常用的含义使用。因此,除非另有定义,则本公开文本中使用的所有专门用语及科学技术用语的含义与本发明所属领域的技术人员通常理解的术语含义相同。在冲突的情况下,以本说明书(包括定义在内)为优先。
异噁唑化合物或其盐
本发明提供由式(I)表示的异噁唑化合物或其盐:
其中R、A1、A2、B1、B2和n的定义如上所述。
以下示出本说明书中使用的各基团的具体例。
本说明书中的术语“未取代的”是指该基团仅由基础基团(base group)构成。此外,除非另有特别说明,则当基团未被记载为“经取代的”而使用基础基团的名称记载时,表示“未取代的”基团。
另一方面,术语“经取代的”是指基础基团的任意的氢原子被与基础基团相同或不同的基团取代。“经取代的”基团可以被一个、两个或更多的取代基取代。两个或更多的取代基可以相同或不同。
“取代基”只要是化学上允许的、且达成本发明的效果即可,没有特别限定。
“取代基”的例子包括:卤素原子,例如氟原子、氯原子、溴原子、碘原子或类似的原子;C1-6烷基,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、正己基或类似的基团;C3-8环烷基,例如环丙基、环丁基、环戊基、环己基、环庚基或类似的基团;C2-6链烯基,例如乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基或类似的基团;C3-8环烯基,例如2-环丙烯基、2-环戊烯基、3-环己烯基、4-环辛烯基或类似的基团;C2-6炔基,例如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-甲基-3-丁炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、2-甲基-3-戊炔基、1-己炔基、1,1-二甲基-2-丁炔基或类似的基团;C1-6烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基或类似的基团;C2-6链烯基氧基,例如乙烯基氧基、烯丙氧基、丙烯氧基、丁烯氧基或类似的基团;C2-6炔基氧基,例如乙炔氧基、炔丙氧基或类似的基团;C6-10芳基,例如苯基、萘基或类似的基团;C6-10芳基氧基,例如苯氧基、1-萘氧基或类似的基团;C7-11芳烷基,例如苄基、苯乙基或类似的基团;C7-11芳烷基氧基,例如苄氧基、苯乙氧基或类似的基团;C1-7酰基,例如甲酰基、乙酰基、丙酰基、苯甲酰基、环己基羰基或类似的基团;C1-7酰基氧基,例如甲酰氧基、乙酰氧基、丙酰氧基、苯甲酰氧基、环己基羰基氧基或类似的基团;C1-6烷氧基羰基,例如甲氧基羰基、乙氧基羰基、正丙氧基羰基、异丙氧基羰基、正丁氧基羰基、叔丁氧基羰基或类似的基团;羧基;羟基;氧代基;C1-6卤代烷基,例如氯甲基、氯乙基、三氟甲基、1,2-二氯正丙基、1-氟正丁基、全氟正戊基或类似的基团;C2-6卤代链烯基,例如2-氯-1-丙烯基、2-氟-1-丁烯基或类似的基团;C2-6卤代炔基,例如4,4-二氯-1-丁炔基、4-氟-1-戊炔基、5-溴-2-戊炔基或类似的基团;C1-6卤代烷氧基,例如2-氯正丙氧基、2,3-二氯丁氧基或类似的基团;C2-6卤代链烯基氧基,例如2-氯丙烯氧基、3-溴丁烯氧基或类似的基团;C6-10卤代芳基,例如4-氯苯基、4-氟苯基、2,4-二氯苯基或类似的基团;C6-10卤代芳基氧基,例如4-氟苯基氧基、4-氯-1-萘氧基或类似的基团;卤代C1-7酰基,例如氯乙酰基、三氟乙酰基、三氯乙酰基、4-氯苯甲酰基或类似的基团;氰基;异氰基;硝基;异氰酸酯基;氰酸酯基;氨基;C1-6烷基氨基,例如甲氨基、二甲基氨基、二乙基氨基或类似的基团;C6-10芳基氨基,例如苯胺基、萘基氨基或类似的基团;C7-11芳烷基氨基,例如苄基氨基、苯乙基氨基或类似的基团;C1-7酰基氨基,例如甲酰基氨基、乙酰基氨基、丙酰基氨基、丁酰基氨基、异丙基羰基氨基、苯甲酰基氨基或类似的基团;C1-6烷氧基羰基氨基,例如甲氧基羰基氨基、乙氧基羰基氨基、正丙氧基羰基氨基、异丙氧基羰基氨基或类似的基团;未取代或经取代的氨基羰基,例如氨基羰基、二甲基氨基羰基、苯基氨基羰基、N-苯基-N-甲基氨基羰基或类似的基团;经亚氨基取代的C1-6烷基,例如亚氨基甲基、(1-亚氨基)乙基、(1-亚氨基)正丙基或类似的基团;经羟基亚氨基取代的C1-6烷基,例如羟基亚氨基甲基、(1-羟基亚氨基)乙基、(1-羟基亚氨基)丙基、甲氧基亚氨基甲基、(1-甲氧基亚氨基)乙基或类似的基团;巯基;异硫氰酸酯基;硫氰酸酯基;C1-6烷基硫基,例如甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基或类似的基团;C2-6链烯基硫基,例如乙烯基硫基、烯丙硫基或类似的基团;C2-6炔基硫基,例如乙炔基硫基、炔丙基硫基或类似的基团;C6-10芳基硫基,例如苯基硫基、萘基硫基或类似的基团;杂环基硫基,例如噻唑基硫基、吡啶基硫基或类似的基团;C7-11芳烷基硫基,例如苄基硫基、苯乙基硫基或类似的基团;(C1-6烷基硫基)羰基,例如(甲硫基)羰基、(乙硫基)羰基、(正丙硫基)羰基、(异丙硫基)羰基,(正丁硫基)羰基、(异丁硫基)羰基、(仲丁硫基)羰基、(叔丁硫基)羰基或类似的基团;C1-6烷基亚硫酰基,例如甲基亚硫酰基、乙基亚硫酰基、叔丁基亚硫酰基或类似的基团;C2-6链烯基亚硫酰基,例如烯丙基亚硫酰基或类似的基团;C2-6炔基亚硫酰基,例如炔丙基亚硫酰基或类似的基团;C6-10芳基亚硫酰基,例如苯基亚硫酰基或类似的基团;杂环基亚硫酰基,例如噻唑基亚硫酰基、吡啶基亚硫酰基或类似的基团;C7-11芳烷基亚硫酰基,例如苄基亚硫酰基、苯乙基亚硫酰基或类似的基团;C1-6烷基磺酰基,例如甲磺酰基、乙磺酰基、叔丁基磺酰基或类似的基团;C2-6链烯基磺酰基,例如烯丙基磺酰基或类似的基团;C2-6炔基磺酰基,例如炔丙基磺酰基或类似的基团;C6-10芳基磺酰基,例如苯基磺酰基或类似的基团;杂环基磺酰基,例如噻唑基磺酰基、吡啶基磺酰基或类似的基团;C7-11芳烷基磺酰基,例如苄基磺酰基、苯乙基磺酰基或类似的基团;五元杂芳基,例如吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、三唑基、噁二唑基、噻二唑基、四唑基或类似的基团;六元杂芳基,例如吡啶基、吡嗪基、嘧啶基、哒嗪基、三嗪基或类似的基团;饱和杂环基,例如吖丙啶基、环氧基、吡咯烷基、四氢呋喃基、哌啶基、哌嗪基、吗啉基或类似的基团;经三个C1-6烷基取代的甲硅烷基,例如三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基或类似的基团;三苯基甲硅烷基或类似的基团;等等。
卤素的例子包括但不特别限定于氟、氯、溴、碘、及类似的物质等。
C1-6烷基的例子包括但不特别限定于C1-6直链或支链的烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、正己基、及类似的基团。
C1-4卤代烷基的例子包括但不特别限定于被1至9个、优选1至5个卤素原子取代的C1-4直链或支链烷基,例如氟甲基、氯甲基、溴甲基、碘甲基、二氟甲基、二氯甲基、三氯甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基,2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基、2,2,3,3-四氟丙基、3,3-二氟丙基、2,3,3-三氟丙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、七氟丙基、4,4-二氟丁基、4,4,4-三氟丁基、3,4,4-三氟丁基、3,3,4,4-四氟丁基、3,3,4,4-五氟丁基、七氟异丁基、九氟丁基及类似的基团。
芳基的例子包括但不特别限定于苯基、1-萘基、2-萘基及类似的基团。
芳基C1-6烷基的例子包括但不特别限定于氟(苯基)甲基、氯(苯基)甲基、二氟(苯基)甲基、二氯(苯基)甲基、1-萘基二氟甲基、2-萘基二氟甲基、1-萘基二氯甲基、2-萘基二氯甲基及类似的基团。
由式(I)表示的化合物的盐只要是农业上可允许的即可,可以是任意种类的盐。盐的例子包括:无机酸盐,例如盐酸盐、硫酸盐、硝酸盐、及类似的物质;有机酸盐,例如乙酸盐、甲磺酸盐、及类似的物质;碱金属盐,例如钠盐、钾盐、及类似的物质;碱土金属盐,例如镁盐、钙盐、及类似的物质;季铵盐,例如二甲基铵、三乙基铵、及类似的物质;等等。
符号n表示0至2的整数。
本发明的化合物(I)之中,优选的化合物是R为C1-6烷基和C1-4卤代烷基的化合物,更优选的化合物(I)是R为正丙基或2,2,2-三氟乙基的化合物。
本发明的化合物(I)之中,优选的化合物是A1为C1-6烷基的化合物,另一优选的化合物是A1为氟、氯或甲基的化合物,更优选的化合物(I)是A1为甲基的化合物。
本发明的化合物(I)之中,优选的化合物是A2为卤素和C1-6烷基的化合物,更优选的化合物(I)是A2为氟、氯或甲基的化合物。
本发明的化合物(I)之中,优选的化合物是B1为氢或甲基的化合物。
本发明的化合物(I)之中,优选的化合物是B2为C1-4卤代烷基或者经取代或未取代的芳基C1-4卤代烷基的化合物,更优选的化合物(I)是B2为二氟甲基、三氟甲基、氯二氟甲基、五氟乙基、七氟丙基或二氟(苯基)甲基的化合物。
本发明的化合物(I)之中,优选的化合物是n为0或1的整数的化合物。
术语“控制”涵盖杀死、消灭、减少和驱除。例如,“控制螨”涵盖杀死螨、消灭螨、减少螨、和驱除螨。这同样适用于“控制剂”。
制备异噁唑化合物或其盐的方法:
可按照以下反应路线1至路线3容易地制备本发明的由式(I)表示的异噁唑化合物,但不限于这些方法。
[反应路线1]
其中R、A1、A2、B1和B2的定义如上所述。
步骤1-1
步骤1-1为下述步骤:准备化合物(IV)和羟胺,在碱及溶剂的存在下来制造化合物(V)。根据取代基B1及/或B2的种类,化合物(V)可以不在该步骤中被分离,并可以进一步发生脱水反应而被转化为由式(Ia)表示的化合物(反应路线1-1):
[反应路线1-1]
其中R、A1、A2、B1和B2的定义如上所述。
上述的反应在合适的溶剂中实施,或者无溶剂地实施。在溶剂中实施上述反应时,溶剂只要对于上述反应为惰性即可,没有限定。这样的溶剂的例子包括:脂肪酸或脂环烃类溶剂,例如正己烷、环己烷、正庚烷及类似的物质;芳烃类溶剂,例如苯、氯苯、甲苯、二甲苯及类似的物质;卤代烃类溶剂,例如二氯甲烷、1,2-二氯乙烷、氯仿、和四氯化碳及类似的物质;醚类溶剂,例如乙醚、四氢呋喃(THF)、1,4-二氧杂环己烷及类似的物质;酯类溶剂,例如乙酸甲酯、乙酸乙酯及类似的物质;乙腈;酰胺类溶剂,例如N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮及类似的物质;和亚砜类溶剂,例如二甲基亚砜、环丁砜及类似的物质;H2O;乙酸,优选甲醇、乙醇和甲苯。可单独使用上述溶剂中的任一者,或根据需要而使用上述中两种以上的组合。
相对于1摩尔化合物(IV)而言,溶剂的用量通常为1.0至20升,优选为1.0至10升。
上述的反应可在无碱条件下或碱的存在下实施。上述之中,优选在碱的存在下实施反应。作为碱,可广泛使用常规已知的碱,碱的例子包括:无机碱,例如碱金属碳酸盐,例如碳酸钠、碳酸钾、碳酸铯、碳酸氢钾、碳酸氢钠及类似的物质;碱金属氢氧化物,例如氢氧化钠、氢氧化钾及类似的物质;碱金属氢化物,例如氢化钠和氢化钾及类似的物质;碱金属醇化物,例如甲醇钠、乙醇钠、叔丁醇钾及类似的物质;有机碱,例如吡啶、三乙胺、二乙胺、二甲胺、甲胺、咪唑、苯并咪唑、二异丙基乙胺、4-二甲基氨基吡啶、哌啶及类似的物质;等等,优选吡啶。使用这些碱中的任何单独一种,或它们中的两种以上的组合。
相对于1摩尔化合物(IV)而言,碱的用量通常为1.0至5.0摩尔,优选为1.0至2.0摩尔。
所使用的羟胺为盐酸羟胺、硫酸羟胺或羟胺水合物,优选盐酸羟胺。
相对于1摩尔化合物(IV)而言,羟胺的用量通常为1.0至5.0摩尔,优选为1.0至2.0摩尔。
反应温度根据起始化合物、反应试剂、溶剂等而变化,但通常为-40℃至反应体系中的回流温度,优选为50至150℃。
反应时间根据化合物、反应试剂、溶剂和反应温度等而变化,但通常为10分钟至48小时,优选为20分钟至24小时,更优选为1至10小时。
该步骤中使用的化合物(IV)可按照已知方法来制造(例如,JP2008-260706A和WO2007/081019中记载的方法)。
步骤1-2
步骤1-2为下述步骤:准备化合物(V)和亚硫酰氯,在碱及溶剂的存在下来制造本发明的由式(I)表示的化合物中n为0的、由式(Ia)表示的化合物(反应路线1-2):
[反应路线1-2]
其中R、A1、A2、B1和B2的定义如上所述。
上述的反应在合适的溶剂中实施,或者无溶剂地实施。在溶剂中实施上述反应时,溶剂只要对于上述反应为惰性即可,没有限定。这样的溶剂的例子包括:脂肪酸或脂环烃类溶剂,例如正己烷、环己烷、正庚烷及类似的物质;芳烃类溶剂,例如苯、氯苯、甲苯、二甲苯及类似的物质;卤代烃类溶剂,例如二氯甲烷、1,2-二氯乙烷、氯仿、和四氯化碳及类似的物质;醚类溶剂,例如乙醚、四氢呋喃(THF)、1,4-二氧杂环己烷及类似的物质;酯类溶剂,例如乙酸甲酯、乙酸乙酯及类似的物质;乙腈;酰胺类溶剂,例如N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮及类似的物质;和亚砜类溶剂,例如二甲基亚砜、环丁砜及类似的物质,优选甲苯。可单独使用上述溶剂中的任一者,或根据需要而使用上述中两种以上的组合。
相对于1摩尔化合物(V)而言,溶剂的用量通常为0.5至20升,优选为0.5至10升。
上述的反应可在无碱条件下或碱的存在下实施。上述之中,优选在碱的存在下实施反应。作为碱,可广泛使用常规已知的碱,碱的例子包括:无机碱,例如碱金属碳酸盐,例如碳酸钠、碳酸钾、碳酸铯、碳酸氢钾、碳酸氢钠及类似的物质;碱金属氢氧化物,例如氢氧化钠、氢氧化钾及类似的物质;碱金属氢化物,例如氢化钠和氢化钾及类似的物质;碱金属醇化物,例如甲醇钠、乙醇钠、叔丁醇钾及类似的物质;有机碱,例如吡啶、三乙胺、二乙胺、二甲胺、甲胺、咪唑、苯并咪唑、二异丙基乙胺、4-二甲基氨基吡啶、哌啶及类似的物质;等等,优选吡啶。使用这些碱中的任何单独一种,或它们中的两种以上的组合。
相对于1摩尔化合物(V)而言,碱的用量通常为1.0至5.0摩尔,优选为1.0至2.0摩尔。
相对于1摩尔化合物(V)而言,亚硫酰氯的用量通常为1.0至6.0摩尔,优选为1.0至3.0摩尔。
反应温度根据起始化合物、反应试剂、溶剂等而变化,但通常为-40℃至反应体系中的回流温度,优选为0至120℃。
反应时间根据化合物、试剂、溶剂和反应温度等而变化,但通常为10分钟至48小时,优选为20分钟至24小时,更优选为1至10小时。
[反应路线2]
其中R、A1、A2、B1和B2的定义如上所述。
L表示甲基或乙基。
G表示离去基团,离去基团的例子包括:卤素,例如氯、溴、和碘;经取代或未取代的C1-6烷基磺酸酯;经取代或未取代的芳基磺酸酯。取代基的例子包括上述的取代基,例如卤素和C1-6烷基。
步骤2-1
步骤2-1为下述步骤:准备化合物VI和化合物(VII)或化合物(VIII),在碱及溶剂的存在下来制造化合物(IX)(反应路线2-1):
[反应路线2-1]
其中R、A1、A2、B1、B2和L的定义如上所述。
上述的反应在合适的溶剂中实施,或者无溶剂地实施。在溶剂中实施上述反应时,溶剂只要对于上述反应为惰性即可,没有限定。这样的溶剂的例子包括:脂肪酸或脂环烃类溶剂,例如正己烷、环己烷、正庚烷及类似的物质;芳烃类溶剂,例如苯、氯苯、甲苯、二甲苯及类似的物质;卤代烃类溶剂,例如二氯甲烷、1,2-二氯乙烷、氯仿、和四氯化碳及类似的物质;醚类溶剂,例如乙醚、四氢呋喃(THF)、1,4-二氧杂环己烷及类似的物质;酯类溶剂,例如乙酸甲酯、乙酸乙酯及类似的物质;乙腈;酰胺类溶剂,例如N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮及类似的物质;和亚砜类溶剂,例如二甲基亚砜、环丁砜及类似的物质,优选四氢呋喃和N,N-二甲基甲酰胺。可单独使用上述溶剂中的任一者,或根据需要而使用上述中两种以上的组合。
相对于1摩尔化合物(VI)而言,溶剂的用量通常为0.5至20升,优选为0.5至10升。
上述的反应可在无碱条件下或碱的存在下实施。上述之中,优选在碱的存在下实施反应。作为碱,可广泛使用常规已知的碱,碱的例子包括:无机碱,例如碱金属碳酸盐,例如碳酸钠、碳酸钾、碳酸铯、碳酸氢钾、碳酸氢钠及类似的物质;碱金属氢氧化物,例如氢氧化钠、氢氧化钾及类似的物质;碱金属氢化物,例如氢化钠和氢化钾及类似的物质;碱金属醇化物,例如甲醇钠、乙醇钠、叔丁醇钾及类似的物质;有机碱,例如吡啶、三乙胺、二乙胺、二甲胺、甲胺、咪唑、苯并咪唑、二异丙基乙胺、4-二甲基氨基吡啶、哌啶及类似的物质;等等,优选吡啶、氢化钠和甲醇钠。使用这些碱中的任何单独一种,或它们中的两种以上的组合。
相对于1摩尔化合物(VI)而言,碱的用量通常为1.0至5.0摩尔,优选为1.0至2.0摩尔。
相对于1摩尔化合物(VI)而言,化合物(VII)或化合物(VIII)的用量通常为1.0至3.0摩尔,优选为1.0至2.0摩尔。
反应温度根据起始化合物、试剂、溶剂等而变化,但通常为-40℃至反应体系中的回流温度,优选为0至120℃。
反应时间根据化合物、试剂、溶剂和反应温度等而变化,但通常为10分钟至48小时,优选为10分钟至48小时,更优选为20分钟至24小时。
步骤2-2
步骤2-2为下述步骤:准备化合物(IX)和羟胺,在碱及溶剂的存在下来制备化合物(X)。根据取代基B1及/或B2的种类,化合物(X)可以不在该步骤中被分离,并可能进一步发生脱水反应而被转化为由式(Ia)表示的化合物(反应路线2-2):
[反应路线2-2]
其中R、A1、A2、B1和B2的定义如上所述。
上述的反应在合适的溶剂中实施,或者无溶剂地实施。在溶剂中实施上述反应时,溶剂只要对于上述反应为惰性即可,没有限定。这样的溶剂的例子包括:脂肪酸或脂环烃类溶剂,例如正己烷、环己烷、正庚烷及类似的物质;芳烃类溶剂,例如苯、氯苯、甲苯、二甲苯及类似的物质;卤代烃类溶剂,例如二氯甲烷、1,2-二氯乙烷、氯仿、和四氯化碳及类似的物质;醚类溶剂,例如乙醚、四氢呋喃(THF)、1,4-二氧杂环己烷及类似的物质;酯类溶剂,例如乙酸甲酯、乙酸乙酯及类似的物质;乙腈;酰胺类溶剂,例如N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮及类似的物质;和亚砜类溶剂,例如二甲基亚砜、环丁砜及类似的物质;H2O;乙酸,优选甲醇、乙醇和甲苯。可单独使用上述溶剂中的任一者,或根据需要而使用上述中两种以上的组合。
相对于1摩尔化合物(IX)而言,溶剂的用量通常为1.0至20升,优选为1.0至10升。
上述的反应可在无碱条件下或碱的存在下实施。上述之中,优选在碱的存在下实施反应。作为碱,可广泛使用常规已知的碱,碱的例子包括:无机碱,例如碱金属碳酸盐,例如碳酸钠、碳酸钾、碳酸铯、碳酸氢钾、碳酸氢钠及类似的物质;碱金属氢氧化物,例如氢氧化钠、氢氧化钾及类似的物质;碱金属氢化物,例如氢化钠和氢化钾及类似的物质;碱金属醇化物,例如甲醇钠、乙醇钠、叔丁醇钾及类似的物质;有机碱,例如吡啶、三乙胺、二乙胺、二甲胺、甲胺、咪唑、苯并咪唑、二异丙基乙胺、4-二甲基氨基吡啶、哌啶及类似的物质;等等,优选吡啶。使用这些碱中的任何单独一种,或它们中的两种以上的组合。
相对于1摩尔化合物(IX)而言,碱的用量通常为1.0至5.0摩尔,优选为1.0至2.0摩尔。
所使用的羟胺为盐酸羟胺、硫酸羟胺或羟胺水合物,优选盐酸羟胺。
相对于1摩尔化合物(IX)而言,羟胺的用量通常为1.0至5.0摩尔,优选为1.0至2.0摩尔。
反应温度根据起始化合物、反应试剂、溶剂等而变化,但通常为-40℃至反应体系中的回流温度,优选为50至150℃。
反应时间根据化合物、反应试剂、溶剂和反应温度等而变化,但通常为10分钟至48小时,优选为20分钟至24小时,更优选为1至10小时。
该步骤中使用的化合物(IX)也可按照已知的方法来制造(例如,J.Org.Chem.,55,1959-1964(1990)中记载的方法)。
步骤2-3
步骤2-3为下述步骤:准备化合物(X)和亚硫酰氯,在碱及溶剂的存在下来制造化合物(XI)(反应路线2-3):
[反应路线2-3]
其中A1、A2、B1和B2的定义如上所述。
上述的反应在合适的溶剂中实施,或者无溶剂地实施。在溶剂中实施上述反应时,溶剂只要对于上述反应为惰性即可,没有限定。这样的溶剂的例子包括:脂肪酸或脂环烃类溶剂,例如正己烷、环己烷、正庚烷及类似的物质;芳烃类溶剂,例如苯、氯苯、甲苯、二甲苯及类似的物质;卤代烃类溶剂,例如二氯甲烷、1,2-二氯乙烷、氯仿、和四氯化碳及类似的物质;醚类溶剂,例如乙醚、四氢呋喃(THF)、1,4-二氧杂环己烷及类似的物质;酯类溶剂,例如乙酸甲酯、乙酸乙酯及类似的物质;乙腈;酰胺类溶剂,例如N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮及类似的物质;和亚砜类溶剂,例如二甲基亚砜、环丁砜及类似的物质,优选甲苯。可单独使用上述溶剂中的任一者,或根据需要而使用上述中两种以上的组合。
相对于1摩尔化合物(X)而言,溶剂的用量通常为0.5至20升,优选0.5至10升。
上述的反应可在无碱条件下或碱的存在下实施。上述之中,优选在碱的存在下实施反应。作为碱,可广泛使用常规已知的碱,碱的例子包括:无机碱,例如碱金属碳酸盐,例如碳酸钠、碳酸钾、碳酸铯、碳酸氢钾、碳酸氢钠及类似的物质;碱金属氢氧化物,例如氢氧化钠、氢氧化钾及类似的物质;碱金属氢化物,例如氢化钠和氢化钾及类似的物质;碱金属醇化物,例如甲醇钠、乙醇钠、叔丁醇钾及类似的物质;有机碱,例如吡啶、三乙胺、二乙胺、二甲胺、甲胺、咪唑、苯并咪唑、二异丙基乙胺、4-二甲基氨基吡啶、哌啶及类似的物质;等等,优选吡啶。使用这些碱中的任何单独一种,或它们中的两种以上的组合。
相对于1摩尔化合物(X)而言,碱的用量通常为1.0至5.0摩尔,优选为1.0至2.0摩尔。
相对于1摩尔化合物(X)而言,亚硫酰氯的用量通常为1.0至6.0摩尔,优选为1.0至3.0摩尔。
反应温度根据起始化合物、试剂、溶剂等而变化,但通常为-40℃至反应体系中的回流温度,优选为0至120℃。
反应时间根据化合物、试剂、溶剂和反应温度等而变化,但通常为10分钟至48小时,优选为20分钟至24小时,更优选为1至10小时。
步骤2-4
步骤2-4为下述步骤:准备化合物(XI)和氯磺酸,在无溶剂条件下或在溶剂的存在下来制造化合物(XII)。也可通过在化合物(XI)的磺化后进行氯磺酰化来制造(反应路线2-4):
[反应路线2-4]
其中A1、A2、B1和B2的定义如上所述。
用于氯磺酰化的试剂没有特别限定,包括例如氯磺酸等。使用氯磺酸时,该步骤可经一步而实施。对于氯磺酰化而言,可使用包括磺化和之后的氯化的两步法。化合物(XII)可如下制造:使异噁唑化合物(XI)与磺化试剂反应来制造经HOSO2取代的化合物(XI),然后使该含有HOSO2-的化合物(XI)与氯化剂反应。
用于硫酸化的试剂没有特别限定,可举出例如氯磺酸和硫酸。用于氯化的氯化剂的例子包括但不特别限定于氯、POCl3、SOCl2、SO2Cl2、和草酰氯。
使用氯磺酸时,在反应中使用的化合物(XI)与氯磺酸之间的比率没有特别限定,可以从广泛的范围中适当选择。相对于1摩尔化合物(XI)而言,氯磺酸的用量通常为1.0至50摩尔,优选为2.0至20摩尔。
使用磺化试剂和氯化剂时,在化合物(XI)与磺化试剂的反应中,所使用的磺化试剂与氯化剂之间的比率没有特别限定,可以从广泛的范围中适当选择。相对于1摩尔化合物(XI)而言,磺化试剂的用量通常为1.0至50摩尔,优选为1.0至20摩尔。在反应中使用的化合物(XI)与氯化剂的比率没有特别限定,可以从广泛的范围中适当选择。相对于1摩尔化合物(XI)而言,氯化剂的用量通常为1.0至50摩尔,优选为1.0至20摩尔。
上述的反应在合适的溶剂中实施,或者无溶剂地实施。在溶剂中实施上述反应时,溶剂只要对于上述反应为惰性即可,没有限定。这样的溶剂的例子包括:卤代烃类溶剂,例如二氯甲烷、1,2-二氯乙烷、氯仿、和四氯化碳、及类似的物质,优选氯仿。
相对于1摩尔化合物(XI)而言,溶剂的用量通常为1.0至20升,优选为1.0至10升。
反应温度根据起始化合物、试剂、溶剂等而变化,但通常为-40℃至反应体系中的回流温度,优选为0至80℃。
反应时间根据化合物、试剂、溶剂和反应温度等而变化,但通常为10分钟至48小时,优选为5分钟至24小时。
步骤2-5
步骤2-5为下述步骤:准备还原剂和化合物(XII),在溶剂的存在下或无溶剂的条件下来制造化合物(XIII)(反应路线2-5):
[反应路线2-5]
其中A1、A2、B1和B2的定义如上所述。
在反应中使用的化合物(XII)与还原剂之间的比率没有特别限定,可以从广泛的范围中适当选择。
作为还原剂,可广泛使用任何常规已知的还原剂,还原剂的例子包括:磷化合物,例如三苯基膦及类似的物质;含有金属和酸的还原剂,例如锌和酸、锡(II)和酸、铁和酸;和特定的还原剂,例如还原剂红磷、碘、二氯二甲基硅烷-锌-二甲基乙酰胺、氢化铝锂、及类似的物质。酸的例子包括:有机酸,例如乙酸及类似的物质;和无机酸,例如盐酸、硫酸及类似的物质。
在反应中使用的化合物(XII)与还原剂之间的比率没有特别限定,可以从广泛的范围中适当选择。
相对于1摩尔化合物(XII)而言,锌和酸的用量通常为1.0至50.0摩尔,优选为1.0至20.0摩尔。
上述的反应在合适的溶剂中实施。溶剂只要对于该反应为惰性即可,没有限定。这样的溶剂的例子包括:H2O;羧酸类溶剂,例如乙酸、丙酸及类似的物质;醇类溶剂,例如甲醇、乙醇、正丙醇、异丙醇及类似的物质。可单独使用上述溶剂中的任一者,或根据需要而使用它们中的两种以上的组合,优选H2O及醇,更优选H2O和异丙醇。
相对于1摩尔化合物(XII)而言,溶剂的用量通常为1.0至20升,优选为1.0至10升。
反应温度根据起始化合物、反应试剂、溶剂等而变化,但通常为-40℃至反应体系中的回流温度,优选为0至150℃。
反应时间根据化合物、试剂、溶剂和反应温度等而变化,但通常为10分钟至48小时,优选为5分钟至24小时。
步骤2-6
步骤2-6为下述步骤:准备化合物(XIII)和烷化剂(alkyl agent)(XIV),在碱及溶剂的存在下来制造本发明的由式(I)表示的化合物中n为0的、由式(Ia)表示的化合物(反应路线2-6):
[反应路线2-6]
其中R、A1、A2、B1、B2和G的定义如上所述。
在反应中使用的硫醇化合物(XIII)与烷化剂(XIV)之间的比率没有特别限定,可以从广泛的范围中适当选择。相对于1摩尔化合物(XIII)而言,烷化剂(XIV)的用量通常为1.0至5.0摩尔,优选为1.0至2.0摩尔。
上述的反应可在无碱条件下或碱的存在下实施。上述之中,优选在碱的存在下实施反应。作为碱,可广泛使用常规已知的碱,碱的例子包括:无机碱,例如碱金属碳酸盐,例如碳酸钠、碳酸钾、碳酸铯、碳酸氢钾、碳酸氢钠及类似的物质;碱金属氢氧化物,例如氢氧化钠、氢氧化钾及类似的物质;碱金属氢化物,例如氢化钠和氢化钾及类似的物质;碱金属醇化物,例如甲醇钠、乙醇钠、叔丁醇钾及类似的物质;有机碱,例如吡啶、三乙胺、二乙胺、二甲胺、甲胺、咪唑、苯并咪唑、二异丙基乙胺、4-二甲基氨基吡啶、哌啶及类似的物质;等等,优选碱金属碳酸盐及碱金属氢化物,更优选碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠和氢化钠。使用这些碱中的任何单独一种,或它们中的两种以上的组合。
相对于1摩尔化合物(XIII)而言,碱的用量通常为1.0至5.0摩尔,优选为1.0至3.0摩尔。
上述的反应可通过进一步添加自由基引发剂来实施。自由基引发剂的例子包括但不特别限定于亚硫酸、亚硫酸盐、Rongalite(化合物名称,甲醛次硫酸氢钠)、亚硫酸加合物等。可将碱与自由基引发剂组合使用。
使用自由基引发剂时,作为其添加量,相对于1摩尔化合物(XIII)而言,自由基引发剂的用量通常为0.1至10.0摩尔,优选为0.1至5.0摩尔。
上述的反应在合适的溶剂中实施。溶剂的例子包括:脂肪酸或脂环烃类溶剂,例如正己烷、环己烷、正庚烷及类似的物质;芳烃类溶剂,例如苯、氯苯、甲苯、二甲苯及类似的物质;卤代烃类溶剂,例如二氯甲烷、1,2-二氯乙烷、氯仿、四氯化碳及类似的物质;醚类溶剂,例如乙醚、THF、1,4-二氧杂环己烷及类似的物质;酯类溶剂,例如乙酸甲酯、乙酸乙酯及类似的物质;乙腈;酰胺类溶剂,例如DMF、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮及类似的物质;亚砜类溶剂,例如二甲基亚砜、环丁砜及类似的物质;极性溶剂,例如醇类溶剂,例如甲醇、乙醇、异丙醇及类似的物质;水;等等。可单独使用上述溶剂中的任一者,或根据需要而使用上述中两种以上的组合。
相对于1摩尔化合物(XIII)而言,溶剂的用量通常为1.0至20升,优选为1.0至10升。
反应温度根据起始化合物、试剂、溶剂等而变化,但通常为-40℃至反应体系中的回流温度,优选为0至100℃。
反应时间根据化合物、试剂、溶剂和反应温度等而变化,但通常为5分钟至48小时,优选为10分钟至24小时。
通过步骤2-6中所示的方法得到的由式(Ia)表示的化合物被从反应混合物中容易地分离,并且可通过使用例如过滤、溶剂萃取、蒸馏、重结晶、柱色谱等典型的分离手段和纯化手段来进行纯化。反应结束后,由式(Ia)表示的化合物可在不从反应体系分离的情况下供于下一反应。
[反应路线3]
步骤3
步骤3为下述步骤:准备由式(Ia)表示的化合物和氧化剂,在溶剂的存在下制备本发明的由式(I)表示的化合物中n为1和2的、由式(Ib)表示的化合物(反应路线3):
[反应路线3]
其中n’表示1至2的整数;R、A1、A2、B1和B2的定义如上所述。
上述的反应在合适的溶剂中实施,或者无溶剂地实施。在溶剂中实施上述反应时,溶剂只要对于上述反应为惰性即可,没有限定。这样的溶剂的例子包括:脂肪酸或脂环烃类溶剂,例如正己烷、环己烷、正庚烷及类似的物质;芳烃类溶剂,例如苯、氯苯、甲苯、二甲苯及类似的物质;卤代烃类溶剂,例如二氯甲烷、1,2-二氯乙烷、氯仿、和四氯化碳及类似的物质;醚类溶剂,例如乙醚、四氢呋喃(THF)、1,4-二氧杂环己烷及类似的物质;酯类溶剂,例如乙酸甲酯、乙酸乙酯及类似的物质;乙腈;酰胺类溶剂,例如N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮及类似的物质;和酮类溶剂,例如丙酮、甲基乙基酮、环己酮及类似的物质;和亚砜类溶剂,例如二甲基亚砜、环丁砜及类似的物质;H2O;乙酸,优选二氯甲烷、氯仿、甲醇、乙醇和甲苯。可单独使用上述溶剂中的任一者,或根据需要而使用上述中两种以上的组合。
相对于1摩尔由式(Ia)表示的化合物而言,溶剂的用量通常为0.5至20升,优选为0.5至10升。
上述的反应可在氧化剂的存在下实施。作为氧化剂,只要氧化剂能将硫化物氧化为亚砜即可,可以使用任何已知的氧化剂,氧化剂的例子包括下述物质的组合:过酸,例如过甲酸、过乙酸、过三氟乙酸、过苯甲酸、间氯过苯甲酸(mCPBA)、邻羰基过苯甲酸及类似的物质;烷基氢过氧化物,例如过氧化氢、叔丁基过氧化氢、异丙苯过氧化氢及类似的物质;和四烷氧化钛,例如四异丙醇钛及类似的物质;重铬酸盐,例如重铬酸盐、重铬酸钠、重铬酸钾及类似的物质;和高锰酸类,例如高锰酸、高锰酸钠、高锰酸钾及类似的物质;等等,优选间氯过苯甲酸(mCPBA)和过氧化氢。使用这些氧化剂中的任何单独一种,或它们中的两种以上的组合。
相对于1摩尔由式(Ia)表示的化合物而言,碱的用量通常为1.0至10.0摩尔,优选为1.0至5.0摩尔。
上述的反应还可通过添加催化剂而实施。
反应温度根据起始化合物、试剂、溶剂等而变化,但通常为-20℃至反应体系中的回流温度,优选为-10至60℃。
反应时间根据化合物、试剂、溶剂和反应温度等而变化,但通常为10分钟至48小时,优选为20分钟至24小时。
通过步骤3中所示的方法得到的由式(Ib)表示的化合物被从待纯化的反应混合物中容易地分离,所述纯化使用例如过滤、溶剂萃取、蒸馏、重结晶、柱色谱等典型的分离手段和纯化手段来进行。
反应路线1至反应路线3中所示的反应完成后得到的各种由式(I)表示的化合物可以被从反应混合物中容易地分离,并通过例如过滤、溶剂萃取、蒸馏、重结晶、柱色谱等已知的分离技术和纯化技术进行纯化。
本发明涉及的螨控制剂和线虫控制剂可以根据需要而含有农用化学制剂中通常使用的添加剂成分(载体)。
添加剂成分可以是载体(例如,固体载体或液体载体)、表面活性剂、粘结剂或增粘剂、增稠剂、着色剂、铺展剂、粘着剂、抗冻剂、凝固抑制剂、崩解剂、分解抑制剂等。根据需要,可使用其他添加剂成分例如防腐剂、蔬菜屑片等。这些添加剂成分可使用一种,或使用两种以上的组合。
对上述添加剂成分进行说明。
固体载体可以是:例如,矿物载体,例如叶蜡石粘土、高岭土、硅石粘土、滑石、硅藻土、沸石、膨润土、酸性粘土、活性粘土、凹凸棒粘土(Attapulgus clay)、蛭石、珍珠岩、浮石、白炭(例如,合成硅酸或合成硅酸盐)、二氧化钛及类似的物质;蔬菜载体,例如木粉、玉米秆、核桃壳、果核、稻壳、锯末、麦麸、豆粉、粉状纤维素、淀粉、糊精、糖精及类似的物质;无机盐载体,例如碳酸钙、硫酸铵、硫酸钠、氯化钾及类似的物质;和聚合物载体,例如聚乙烯、聚丙烯、聚氯乙烯、聚乙酸乙烯酯、乙烯-乙酸乙烯酯共聚物、脲醛树脂及类似的物质。
液体载体可以是:例如,一元醇,例如甲醇、乙醇、丙醇、异丙醇、丁醇、环己醇及类似的物质;多元醇,例如乙二醇、二乙二醇、丙二醇、己二醇、聚乙二醇、聚丙二醇、甘油及类似的物质;多元醇衍生物,例如丙烯型二元醇醚及类似的物质;酮,例如丙酮、甲基乙基酮、甲基异丁基酮、二异丁基酮、环己酮、异佛尔酮及类似的物质;醚,例如乙醚、1,4-二氧杂环己烷、溶纤剂、二丙醚、四氢呋喃及类似的物质;脂肪族烃,例如正构烷烃、环烷烃、异构烷烃、煤油、矿物油及类似的物质;芳香烃,例如甲苯、C9-10烷基苯、二甲苯、溶剂石脑油(solvent naphtha)、烷基萘、高沸点芳香烃及类似的物质;卤代烃,例如1,2-二氯乙烷、氯仿、四氯化碳及类似的物质;酯,例如乙酸乙酯、邻苯二甲酸二异丙酯、邻苯二甲酸二丁酯、邻苯二甲酸二辛酯、己二酸二甲酯及类似的物质;内酯,例如γ-丁内酯及类似的物质;酰胺,例如二甲基甲酰胺、二乙基甲酰胺、二甲基乙酰胺、N-烷基吡咯烷酮及类似的物质;腈,例如乙腈及类似的物质;硫化合物,例如二甲基亚砜及类似的物质;蔬菜油,例如豆油、菜籽油、棉籽油、椰子油、蓖麻油及类似的物质;和水。
对于表面活性剂,没有特别限定。但表面活性剂优选在水中凝胶化或溶胀。表面活性剂可以是:例如,非离子型表面活性剂,例如山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇酐脂肪酸酯、蔗糖脂肪酸酯、聚氧乙烯脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脂肪酸二酯、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯二烷基苯基醚、聚氧乙烯烷基苯基醚-甲醛缩合物、聚氧乙烯聚氧丙烯嵌段聚合物、烷基聚氧乙烯聚丙烯嵌段聚合醚(alkylpolyoxyethylene polypropylene block polymer ether)、聚氧乙烯烷基胺、聚氧乙烯脂肪酰胺、聚氧乙烯脂肪酸二苯基醚、聚亚烷基苄基苯基醚、聚氧化烯苯乙烯基苯基醚、乙炔二醇、聚氧化烯加成乙炔二醇、聚氧乙烯醚型有机硅、酯型有机硅、含氟表面活性剂、聚氧乙烯蓖麻油、聚氧乙烯氢化蓖麻油及类似的物质;阴离子表面活性剂,例如烷基硫酸盐、聚氧乙烯烷基醚硫酸盐、聚氧乙烯烷基苯基醚硫酸盐、聚氧乙烯苯乙烯基苯基醚硫酸盐、烷基苯磺酸盐、木质素磺酸盐、烷基磺基琥珀酸盐、萘磺酸盐、烷基萘磺酸盐、萘磺酸-甲醛缩合物盐、烷基萘磺酸-甲醛缩合物盐、脂肪酸盐、聚羧酸盐、N-甲基脂肪酸肌氨酸盐(N-methyl-fatty acid sarcosinate)、树脂酸盐、聚氧乙烯烷基醚磷酸盐、聚氧乙烯烷基苯基醚磷酸盐及类似的物质;阳离子表面活性剂,包括:烷基胺盐,例如月桂胺盐酸盐、硬脂胺盐酸盐、油胺盐酸盐、硬脂胺乙酸盐、硬脂基氨基丙基胺乙酸盐、烷基三甲基氯化铵、烷基二甲基苄基氯化铵及类似的物质;两性表面活性剂,例如甜菜碱型(例如,二烷基二氨基乙基甜菜碱或烷基二甲基苄基甜菜碱)、氨基酸型(例如,二烷基氨基甘氨酸或烷基二甲基苄基甘氨酸)及类似的物质。
粘结剂和增粘剂可以是:例如,羧甲基纤维素或其盐、糊精、水溶性淀粉、黄原胶、瓜尔胶、蔗糖、聚乙烯吡咯烷酮、阿拉伯树胶、聚乙烯醇、聚乙酸乙烯酯、聚丙烯酸钠、平均分子量为6,000至20,000的聚乙二醇、平均分子量为100,000至5,000,000的聚氧化乙烯、和天然的磷脂(例如,脑磷脂酸或卵磷脂)
增稠剂可以是:例如,水溶性聚合物,例如黄原胶、瓜尔胶、羧甲基纤维素、聚乙烯吡咯烷酮、羧基乙烯基聚合物、丙烯酸聚合物、淀粉衍生物、多糖及类似的物质;和无机细粉,例如高纯度膨润土、白炭及类似的物质。
着色剂可以是:例如,无机颜料,例如氧化铁、氧化钛、普鲁士蓝及类似的物质;和有机染料,如茜素染料、偶氮染料、金属酞菁染料及类似的物质。
铺展剂可以是:例如,有机硅类表面活性剂、纤维素粉、糊精、加工淀粉、聚氨基甲酸螯合物、交联聚乙烯吡咯烷酮、马来酸和苯乙烯、甲基丙烯酸共聚物、多元醇聚合物与二羧酸酐形成的半酯、聚苯乙烯磺酸的水溶性盐。
粘着剂可以是:例如,表面活性剂(例如,二烷基磺基琥珀酸钠、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚或聚氧乙烯脂肪酸酯)、石蜡、萜烯、聚酰胺树脂、聚丙烯酸盐、聚氧乙烯、蜡、聚乙烯烷基醚、烷基酚-甲醛缩合物、合成树脂乳液。
抗冻剂可以是例如多元醇(例如,乙二醇、二乙二醇、丙二醇或甘油)。
凝固抑制剂可以是例如多糖(例如,淀粉、海藻酸、甘露糖或半乳糖)、聚乙烯吡咯烷酮、白炭、酯胶和石油树脂。
崩解剂可以是例如三聚磷酸钠、六偏磷酸钠、硬脂酸金属盐、纤维素粉、糊精、甲基丙烯酸酯共聚物、聚乙烯吡咯烷酮、聚氨基甲酸螯合物、磺化苯乙烯-异丁烯-马来酸酐共聚物、和淀粉聚丙烯腈接枝共聚物。
分解抑制剂可以是:例如,干燥剂,例如沸石、生石灰、氧化镁及类似的物质;抗氧化剂,例如酚类、胺类、硫类、磷酸类及类似的物质;紫外线吸收剂,例如水杨酸类、二苯甲酮类及类似的物质。
本发明涉及的害虫控制剂含有上述的添加剂成分时,它们的基于重量的含量选自下述范围:载体(例如,固体载体或液体载体)的情况下,通常为5至95%,优选为20至90%;表面活性剂的情况下,通常为0.1至30%,优选为0.5至10%;其他添加剂的情况下,通常为0.1至30%,优选为0.5至10%。
本发明涉及的害虫控制剂用于选自粉尘剂、粉尘-颗粒混合物、颗粒剂、可湿性粉剂、水溶性浓缩物、水分散性颗粒剂、片剂、大粒剂、可乳化浓缩物、油剂、溶液、可流动浓缩物、乳剂、微乳剂、悬乳剂、超低容量制剂、微胶囊、发烟剂、气雾剂、诱饵剂、糊剂等中的任何制剂中。
在制剂的实际使用中,可使用制剂自身或在使用稀释剂(例如,水)以规定浓度稀释后使用。可通过下述通常使用的方法来施用含有本发明涉及的化合物的制剂或其稀释产物:例如,分散(例如,喷洒、喷雾、雾化、粉末分散、颗粒分散、水面上分散或箱内(inbox)分散)、土中施用(例如,混合或浸润)、表面施用(例如,涂布、粉末敷涂或覆盖)、浸泡、毒饵、烟熏及类似的方法。也可以将上述的活性成分与牲畜饲料混合,以避免害虫、尤其是牲畜排泄物中的害虫的侵扰和生长。
可以适当选择本发明涉及的害虫控制剂中的活性成分的比例(重量%)以满足需求。活性成分可以在例如以下范围中适当选择。
粉尘剂、粉尘-颗粒混合物等中:
0.01至20%,优选0.05至10%;
颗粒剂等中:
0.1至30%,优选0.5至20%;
可湿性粉剂、水分散性颗粒剂等中:
1至70%,优选5至50%;
水溶性浓缩物、溶液等中:
1-95%,优选10至80%;
可乳化浓缩物等中:
5至90%,优选10至80%;
油剂等中:
1至50%,优选5至30%;
可流动浓缩物等中:
5至60%,优选10至50%;
乳剂、微乳剂、悬乳剂等中:
5至70%,优选10至60%;
片剂、诱饵、糊剂等中:
1至80%,优选5至50%;
发烟剂等中:
0.1至50%,优选为1至30%;
气雾剂等中:
0.05至20%,优选0.1至10%。
制剂在以合适的浓度稀释后进行喷雾,或直接施用。
将本发明涉及的害虫控制剂在用稀释剂稀释后使用时,活性成分的浓度通常为0.1至5,000ppm。使用制剂自身时,每单位面积的施用量以活性成分化合物计为0.1至5,000g/公顷;但施用量不限于此。
另外,本发明涉及的害虫控制剂在仅将本发明涉及的化合物用作活性成分时是充分有效的。但是,本发明涉及的害虫控制剂可以根据需要而与肥料和农用化学品(例如杀虫剂、杀螨剂、杀线虫剂、增效剂、杀真菌剂、抗病毒剂、引诱剂、除草剂、植物生长调节剂等)混合或组合使用。在这种情况下,显示出更高的效果。
以下为可以混合或组合使用的已知的杀虫剂、杀螨剂、杀线虫剂和增效剂化合物的例子。
1. 乙酰胆碱酯酶抑制剂
(1A)氨基甲酸酯类:棉铃威(alanycarb)、涕灭威(aldicarb)、涕灭砜威(aldoxycarb)、恶虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、西维因(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、杀虫丹(ethiofencarb)、仲丁威(fenobucarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭虫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、XMC(蚜灭多,vamidothion)、灭杀威(xylylcarb);
(1B)有机磷酸酯类:高灭磷(acephate)、甲基吡噁磷(azamethiphos)、益棉磷(azinphosethyl)、保棉磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifosmethyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、除线特(diamidafos)、二嗪农(diazinon)、敌敌畏(dichlorvos)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、蔬果磷(dioxabenzofos)、乙拌磷(disulfoton)、DSP(O,O-二乙基O-(4-二甲基氨基磺酰基苯基)硫代磷酸酯,O,O-diethyl O-(4-dimethylsulfamoylphenyl)phosphorothioate))、EPN(O-乙基O-4-硝基苯基苯基硫代磷酸酯,O-ethyl O-4-nitrophenylphenylphosphonothioate)、乙硫磷(ethion)、灭线磷(ethoprophos)、乙嘧硫磷(etrimfos)、氨磺磷(famphur)、克线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、地虫硫膦(fonofos)、噻唑磷(fosthiazate)、丁硫环磷(fosthietan)、庚烯磷(heptenophos)、衣胺磷(isamidofos)、氯唑磷(isazophos)、甲基异柳磷(isofenphos-methyl)、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯(isopropyl O-(methoxyaminothio-phosphoryl)salicylate)、异噁唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、砜吸磷(oxydemeton-methyl)、异亚砜磷(oxydeprofos)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫膦(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、甲基嘧啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、丙虫磷(propaphos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、虫线磷(thionazin)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭多(vamidothion)、除线磷(dichlofenthion)、新烟磷(imicyafos)、水胺硫磷(isocarbophos)、倍硫磷亚砜(mesulfenfos)、吡氟硫磷(flupyrazofos)。
2. GABA门控氯离子通道拮抗剂
(2A)环戊二烯有机氯类:氯丹(chlordane)、硫丹(endosulfan)、γ-BHC(六氯化苯);
(2B)苯基吡唑类:乙酰虫腈(acetoprole)、乙虫清(ethiprole)、氟虫清(fipronil)、匹弗普罗(pyrafluprole)、吡啶醇(pyriprole)、RZI-02-003(编号)。
3. 钠通道调节剂
(3A)拟除虫菊酯类/拟除虫菊素:氟丙菊酯(acrinathrin)、烯丙菊酯(allethrin,包括右旋-顺式-反式体和右旋反式体)、联苯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物烯丙菊酯S-环戊烯基异构体(bioallethrin S-cyclopentenyl)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin,包括β-氟氯氰菊酯)、三氟氯氰菊酯(cyhalothrin,包括γ-三氟氯氰菊酯和λ-三氟氯氰菊酯)、氯氰菊酯(cypermethrin,包括α-氯氰菊酯、β-氯氰菊酯、θ-氯氰菊酯、和ζ-氯氰菊酯)、苯醚氰菊酯(cyphenothrin,包括(IR)反式异构体)、溴氰菊酯(deltamethrin)、烯炔菊酯(empenthrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、苄螨醚(halfenprox)、咪炔菊酯(imiprothrin)、甲氧苄氟菊酯(metofluthrin)、苄氯菊酯(permethrin)、苯氧司林(phenothrin,包括(IR)反式异构体)、炔丙菊酯(prallethrin)、丙氟菊酯(profluthrin)、除虫菊酯(pyrethrine)、苄呋菊脂(resmethrin)、RU15525(编号)、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、四甲司林(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、ZX18901(编号)、氟胺氰菊酯(fluvalinate,包括τ-氟胺氰菊酯)、四氟醚菊酯(tetramethylfluthrin)、氯氟醚菊酯(meperfluthrin);
(3B)DDT/甲氧氯:DDT(1,1,1-三氯-2,2-双(4-氯苯基)乙烷),甲氧氯
3. 烟碱型乙酰胆碱受体激动剂/拮抗剂
(4A)新烟碱类:啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam);
(4B)烟碱类:硫酸烟碱(nicotine-sulfate)
4. 烟碱型乙酰胆碱受体别构激活剂
斯皮诺素类:多虫菌素(spinetoram)、多杀霉素(spinosad)
5. 氯离子通道激活剂
阿维菌素类(avermectins)、杀螨菌素类(milbemycins):阿巴美丁(abamectin)、甲胺基阿维菌素苯甲酸盐(emamectin benzoate)、雷皮菌素(lepimectin)、密灭汀(milbemectin)、伊维菌素(ivermectin)、抗螨素复合体(polynactins)
6. 拟保幼激素
苯虫醚(diofenolan)、氢化保幼素(hydroprene)、丙诺保幼素(kinoprene)、甲醚菊酯(methothrin)、苯氧威(fenoxycarb)、吡丙醚(pyriproxyfen)
7. 各种非专一性(多位点)抑制剂
1,3-二氯丙烯、DCIP(双(2-氯-1-甲基乙基)醚)、二溴化乙烯、溴甲烷、三氯硝基甲烷、磺酰氟
8. 拒食素
吡蚜酮(pymetrozine)、氟啶虫酰胺(flonicamid)、吡氟喹虫唑(pyrifluquinazon)
9. 螨生长抑制剂
四螨嗪(clofentezine)、氟螨嗪(diflovidazin)、噻螨酮(hexythiazox)、乙螨唑(etoxazole)
10. 昆虫中肠膜微生物干扰剂
BT(球形芽孢杆菌,Bacillus sphaericus)剂:球形芽孢杆菌(Bacillussphaericus)、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis subsp.aizawai)、苏云金牙孢杆菌以色列亚种(Bacillus thuringiensis subsp.israelensis)、苏云金芽孢杆菌塔克亚种(Bacillus thuringiensis subsp.kurstaki)、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subsp.tenebrionis)、Bt作物蛋白(CrylAb、Cry1Ac、CrylFa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb、Cry34/35Ab1)、日本金龟子芽孢杆菌(Bacilluspopilliae)、枯草芽孢杆菌(Bacillus subtillis);
11. 线粒体ATP合酶抑制剂
杀螨隆(diafenthiuron);有机锡杀螨剂(organotin miticides);三唑锡(azocyclotin)、三环锡(cyhexatin)、苯丁锡(fenbutatin oxide);炔螨特(propargite)、三氯杀螨砜(tetradifon);
12. 氧化磷酸化解耦联剂(通过干扰质子梯度)
虫螨腈(chlorfenapyr)、DNOC(6-甲基-2,4-二硝基苯酚);
13. 烟碱型乙酰胆碱受体通道阻遏剂
沙蚕毒素类似物:杀虫磺(bensultap)、杀螟丹(cartap)、杀虫环(thiocyclam)、杀虫单(thiosultap);
14. O型几丁质生物合成抑制剂
苯甲酰脲类:双三氟虫脲(bistrifluron)、定虫隆(chlorfluazoron)、除虫脲(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、虱螨脲(lufenuron)、氟酰脲(novaluron)、多氟脲(noviflumuron)、氟苯脲(teflubenzuron)、杀铃脲(triflumuron)、啶蜱脲(fluazuron)
15. 1型几丁质生物合成抑制剂
噻嗪酮(buprofezin)
16. 双翅目蜕皮干扰剂
环丙氨嗪(cyromazine)
17. 蜕皮激素受体激动剂(促进蜕皮)
双酰肼类杀虫药剂:环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)、虫酰肼(tebufenozide)
18. 章鱼胺受体激动剂
双甲脒(amitraz)
19. 线粒体复合物III电子传递抑制剂
伏蚁腙(hydramethylnon)、灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)、腈吡螨酯(cyenopyrafen)
20. 线粒体复合物II电子传递抑制剂
丁氟螨酯(cyflumetofen)、腈吡螨酯(cyenopyrafen)、NNI-0711(编号)
21. 线粒体复合物I电子传递抑制剂(METI)
METI杀螨剂和杀虫剂:喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、哒螨灵(pyridaben)、嘧螨醚(pyrimidifen)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)
其他:鱼藤酮(rotenone)
22. 钠通道阻遏剂
茚虫威(indoxacarb)、氰氟虫腙(metaflumizon)
23. 脂合成抑制剂
季酮酸衍生物:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat)
24. 线粒体复合物IV电子传递抑制剂
磷化铝、磷化氢(phosphine)、磷化锌、氰化钙
25. 神经抑制剂(作用方式未知)
联苯肼酯(bifenazate)
26. 乌头酸酶抑制剂
氟乙酸钠
27. 增效剂
胡椒基丁醚(piperonyl butoxide)、DEF(三硫代亚磷酸S,S,S-三丁酯)
28. 雷诺丁受体调节剂
氯虫苯甲酰胺(chlorantraniliprole)、氟虫酰胺(flubendiamide)、氰虫酰胺(cyantraniliprole)
29. 作用方式未知的化合物
印楝素(azadirachtin)、酰胺弗门特(amidoflumet)、benclothiaz、杀螨特(benzoximate)、溴螨酯(bromopropylate)、灭螨猛(chinomethionat)、CL900167(编号)、冰晶石(cryolite)、三氯杀螨醇(dicofol)、环虫腈(dicyclanil)、除螨灵(dienochlor)、敌螨通(dinobuton)、六苯丁锡氧(fenbutatin oxide)、苯硫威(fenothiocarb)、氟烯线砜(fluensulfone)、嘧虫胺(flufenerim)、磺菌胺(flsulfamide)、水黄皮素(karanjin)、威百亩(metham)、美赐平(methoprene)、甲氧虫酰肼(methoxyfenozide)、异硫氰酸甲酯(methylisothiocyanate)、三氟甲吡醚(pyridalyl)、吡氟喹虫唑(pyrifluquinazon)、磺苯醚隆钠(sulcofuron-sodium)、氟虫胺(sulfluramid)、氟啶虫胺腈(sulfoxaflor)、氟吡呋喃酮(flupyradifurone)、氟奎因(flometoquin)、IKI-3106(编号)
30. 昆虫病原真菌、线虫致病微生物
球孢白僵菌(Beauveria bassiana)、卵孢白僵菌(Beauveria tenella)、蜡蚧轮枝菌(Verticillium lecanii)、细脚拟青霉(Pacilimyces tenuipes)、玫烟色拟青霉(Paecilomyces fumosoroceus)、布氏白僵菌(Beauveria brongniartii)、瘤捕单顶孢菌(Monacrosporium phymatophagum)、穿刺芽孢杆菌(Pasteuriapenetrans)
32. 性外激素
(Z)-11-十六碳烯醛、(Z)-11-十六碳烯乙酸酯、斜纹夜蛾性诱剂A(litlure-A)、斜纹夜蛾性诱剂B(litlure-B)、Z-13-二十碳烯-10-酮、(Z,E)-9,12-十四碳二烯乙酸酯、(Z)-9-十四碳烯-1-醇、(Z)-11-十四碳烯乙酸酯、(Z)-9,12-十四碳二烯乙酸酯、(Z,E)-9,11-十四碳二烯乙酸酯
接下来,以下为可以混合或组合使用的已知的杀真菌剂或疾病损害控制剂化合物的例子。
1. 核酸生物合成抑制剂
酰基丙氨酸类:苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、呋霜灵(furalaxyl)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M);
噁唑烷酮类:噁霜灵(oxadixyl);
丁内酯类:clozylacon、甲呋酰胺(ofurace);
羟基-(2-氨基)嘧啶类:乙嘧酚磺酸酯(bupirimate)、甲菌定(dimethirimol)、乙菌定(ethirimol);
异噁唑类:噁霉灵(hymexazol);
异噻唑啉酮类:辛噻酮(octhilinone);
羧酸类:噁喹酸
2. 有丝分裂抑制剂和细胞分化抑制剂
苯并咪唑类:苯菌灵(benomyl)、棉萎灵(carbendazim)、呋喃基苯并咪唑(fuberidazole)、噻苯咪唑(thiabendazole);
托布津类:托布津(thiophanate)、甲基托布津(thiophanate-methyl);
N-苯基氨基甲酸酯类:乙霉威(diethofencarb);
甲苯甲酰胺类:苯酰菌胺(zoxamide);
苯基脲类:戊菌隆(pencycuron);
吡啶基甲基苯甲酰胺类:氟吡菌胺(fluopicolide)
3. 呼吸抑制剂
嘧啶胺类:氟嘧菌胺(diflumetorim);
羧酰胺类:麦锈灵(benodanil)、福多宁(flutolanil)、灭锈胺(mepronil)、氟吡菌酰胺(fluopyram)、呋菌胺(fenfuram)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、噻呋酰胺(thifluzamide)、联苯吡菌胺(bixafen)、呋吡菌胺(furametpyr)、吡唑萘菌胺(isopyrazam)、氟唑菌苯胺(penflufen)、吡噻菌胺(penthiopyrad)、氟唑环菌胺(sedaxane)、啶酰菌胺(boscalid)、氟唑菌酰胺(fluxapyroxad)、异丙噻菌胺(isofetamid)、苯并烯氟菌唑(benzovindiflupyr);
甲氧基丙烯酸酯类:嘧菌酯(azoxystrobin)、烯肟菌酯(enestroburin)、啶氧菌酯(picoxystrobin)、唑菌酯(pyraoxystrobin)、丁香菌酯(coumoxystrobin)、烯肟菌酯(enoxastrobin)、氟菌螨酯(flufenoxystrobin);
甲氧基氨基甲酸酯类:吡唑醚菌酯(pyraclostrobin)、唑胺菌酯(pyrametostrobin)、氯啶菌酯(triclopyricarb);
氧基亚氨基乙酸酯类:醚菌酯(kresoxim-methyl)、肟菌酯(trifloxystrobin);
氧基亚氨基乙酰胺类:醚菌胺(dimoxystrobin)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin)、烯肟菌胺(fenaminstrobin);
噁唑烷二酮类:噁唑菌酮(famoxadone);
二氢二噁嗪类:氟嘧菌酯(fluoxastrobin);
咪唑啉酮类:咪唑菌酮(fenamidone);
氨基甲酸苄酯类:吡本卡布(pyribencarb);
氰基咪唑类:氰霜唑(cyazofamid);
氨磺酰基-三唑类:安美速(amisulbrom);
巴豆酸二硝基苯酯类:乐杀螨(binapacryl)、甲基敌螨普(methyldinocap)、敌螨普(dinocap);
2,6-二硝基苯胺类:氟啶胺(fluazinam);
嘧啶酮腙类:嘧菌腙(ferimzone);
三苯基锡:TPTA、TPTC、TPTH;
噻吩羧酰胺类:硅噻菌胺(silthiofam)
三唑并嘧啶胺类:唑嘧菌胺(ametoctradin)
4. 氨基酸和蛋白合成抑制剂
苯胺基嘧啶类:嘧菌环胺(cyprodinil)、嘧菌胺(mepanipyrim)、嘧霉胺(pyrimethanil);
烯醇吡喃糖醛酸:灭瘟素(blasticidin-S)、灭粉霉素(mildiomycin);
己吡喃糖基抗生素:春日霉素(kasugamycin);
吡喃葡糖基抗生素:链霉素;
四环素抗生素:土霉素
5. 信号转导抑制剂
喹啉:喹氧灵(quinoxyfen);
喹唑啉类:丙氧喹啉(proquinazid);
苯基吡咯类:拌种咯(fenpiclonil)、咯菌腈(fludioxonil);
二羧酰亚胺类:乙菌利(chlozolinate)、异菌脲(iprodione)、腐霉利(procymidone)、乙烯菌核利(vinclozolin)
6. 脂质合成抑制剂和膜完整性抑制剂
硫代磷酸酯类:敌瘟磷(edifenphos)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos);
二硫戊环类:稻瘟灵(isoprothiolane);
芳香烃类:联苯、地茂散(chloroneb)、氯硝胺(dicloran)、五氯硝基苯、四氯硝基苯、甲基立枯磷(tolclofos-methyl);
1,2,4-噻二唑类:氯唑灵(etridiazole);
氨基甲酸酯类:碘代丙炔基丁基甲胺酸酯(iodocarb)、霜霉威盐酸盐(propamocarb-hydrochloride)、胺丙威(prothiocarb);
肉桂酰胺类:烯酰吗啉(dimethomorph)、氟吗啉(flumorph);
缬氨酰胺氨基甲酸酯类:苯噻菌胺异丙酯(benthiavalicarb-isopropyl)、异丙菌胺(iprovalicarb)、缬菌胺(valifenalate);
扁桃酰胺类:双炔酰菌胺(mandipropamid);
枯草芽孢杆菌及其产生的杀真菌脂肽:枯草芽孢杆菌(菌株:QST 713)
7. 膜中甾醇生物合成抑制剂
哌嗪类:嗪胺灵(triforine);
吡啶类:碇斑肟(pyrifenox);
嘧啶类:氯苯嘧啶醇(fenarimol)、噻菌醇(nuarimol);
咪唑类:抑霉唑(imazalil)、噁咪唑延胡索酸盐(oxpoconazole-fumarate)、稻瘟酯(pefurazoate)、咪鲜胺(prochloraz)、氟菌唑(triflumizole);
三唑类:氧环唑(azaconazole)、联苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、苯醚甲环唑(difenoconazole)、烯唑醇(diniconazole)、烯唑醇M(diniconazole-M)、氟环唑(epoxiconazole)、乙环唑(etaconazole)、腈苯唑(fenbuconazole)、氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、亚胺唑(imibenconazole)、种菌唑(ipconazole)、叶菌唑(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、三唑醇(triadimenol)、灭菌唑(triticonazole)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、喹唑(quinconazole);
吗啉类:艾敌吗啉(aldimorph)、十二环吗啉(dodemorph)、丁苯吗啉(fenpropimorph)、十三吗啉(tridemorph);
哌啶类:苯锈啶(fenpropidin)、粉病灵(piperalin);
螺环缩酮胺类:螺环菌胺(spiroxamine);
羟基酰替苯胺类:环酰菌胺(fenhexamid);
硫代氨基甲酸酯类:稗草畏(pyributicarb);
烯丙基胺类:萘替芬(naftifine)、特比萘芬(terbinafine)
8. 葡聚糖合成抑制剂
吡喃葡糖基类抗生素:有效霉素(validamycin);
肽基吡啶核苷酸化合物:多抗霉素(polyoxin)
9. 黑色素合成抑制剂
异苯并呋喃酮类:苯酞;
吡咯并喹啉类:咯喹酮(pyroquilon);
三唑并苯并噻唑类:三环唑(tricyclazole);
羧酰胺类:环丙酰菌胺(carpropamid)、双氯氰菌胺(diclocymet);
丙酰胺类:氰菌胺(fenoxanil)
10. 宿主植物防御诱导剂
苯并噻二唑类:阿拉酸式苯-S-甲基(acibenzolar-S-methyl);
苯并异噻唑类:烯丙异噻唑(probenazole);
噻二唑羧酰胺类:噻酰菌胺(tiadinil)、异噻菌胺(isotianil)
天然产物:海带多糖(laminarin)
11. 作用方式未知的化合物
铜化合物:氢氧化铜、二辛酸铜、氧氯化铜、硫酸铜、氧化亚铜、喹啉铜、波尔多液、壬基酚磺酸铜(copper nonyl phenol sulphonate);
硫化合物:硫磺;
二硫代氨基甲酸盐/酯类:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram)、丙森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram)、硫杂灵(cufraneb);
邻苯二甲酰亚胺类:克菌丹(captan)、灭菌丹(folpet)、避蚊胺(captafol);
氯腈类:百菌清(chlorothalonil);
磺酰胺类:抑菌灵(dichlofluanid)、对甲抑菌灵(tolyfluanid);
胍类:双胍盐、双胍辛烷基苯磺酸盐(iminoctadine-albesilate)、双胍辛胺三乙酸盐、多果定(dodine);
其他化合物:敌菌灵(anilazine)、二噻农(dithianon)、霜脲氰(cymoxanil)、乙膦(铝、钙、钠)、亚磷酸和亚磷酸盐、叶枯酞(tecloftalam)、咪唑嗪(triazoxide)、磺菌胺(flusulfamide)、哒菌清(diclomezine)、磺菌威(methasulfocarb)、噻唑菌胺(ethaboxam)、环氟菌胺(cyflufenamid)、苯菌酮(metrafenone)、碳酸氢钾、碳酸氢钠、BAF-045(编号)、(5,7-二甲氧基-2-(2,4,6-三氯苯基)-[1,2,4]三唑并[1,5-a]嘧啶)、BAG-010(编号)、苯噻硫氰(benthiazole)、布罗波尔(bronopol)、香芹酮(carvone)、灭螨猛(chinomethionat)、棉隆(dazomet)、DBEDC、咪菌威(debacarb)、双氯酚(dichlorophen)、野燕枯甲基硫酸盐(difenzoquat-methyl sulfate)、二甲基二硫醚(dimethyl disulfide)、二苯胺(diphenylamine)、乙氧基喹啉(ethoxyquin)、氟联苯菌(flumetover)、唑呋草(fluoroimide)、氟噻菌灵(flutianil)、呋喃甲酸(furancarboxylic acid)、威百亩(metam)、代森钠(nabam)、纳他霉素(natamycin)、氯草定(nitrapyrin)、间硝酞异丙酯(nitrothal-isopropyl)、邻苯基苯酚、曙嗪唑(oxazinylazole)、硫酸羟喹啉(oxyquinoline sulfate)、叶枯净(phenazine oxide)、聚氨基甲酸酯、甲氧苯唳菌(pyriofenone)、胺苯吡菌酮(fenpyrazamine)、银、氯啶菌酯(pyrisoxazole)、异丁乙氧喹啉(tebufloquin)、甲磺菌胺(tolnifanide)、水杨菌胺(trichlamide)、矿物油、有机油、托普洛卡(tolprocarb)、奥赛普林(oxathiapiprolin)
以下示出可以混合或组合使用的已知的除草化合物和植物生长调节剂的例子。
A1. 乙酰辅酶A羧化酶(ACCase)抑制剂
(A1-1)芳氧基苯氧基丙酸酯类:炔草酯(clodinafop-propargyl)、氰氟草酯(cyhalofop-butyl)、禾草灵(diclofop-methyl)、高禾草灵(diclofop-P-methyl)、精噁唑禾草灵(fenoxaprop-P-ethyl)、吡氟禾草灵(fluazifop-butyl)、精吡氟禾草灵(fluazifop-P-butyl)、盖草能(haloxyfop)、氯氟乙禾灵(haloxyfop-etotyl)、高效盖草能(haloxyfop-P)、噁唑酰草胺(metamifop)、喔草酯(propaquizafop)、喹禾灵(quizalofop-ethyl)、精喹禾灵(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、噻唑禾草灵(fenthiaprop-ethyl);
(A1-2)环己二酮类:禾草灭(alloxydim)、丁苯草酮(butroxydim)、烯草酮(clethodim)、噻草酮(cycloxydim)、环苯草酮(profoxydim)、烯禾啶(sethoxydim)、吡喃草酮(tepraloxydim)、三甲苯草酮(tralkoxydim);
(A1-3)苯基吡唑啉类:氯氨吡啶酸(aminopyralid)、草吡唑(pinoxaden);
B. 乙酰乳酸合酶(ALS)抑制剂
(B-1)咪唑啉酮类:咪草酸甲酯(imazamethabenz-methyl)、咪草啶酸(imazamox)、甲咪唑烟酸(包括与胺形成的盐等)、灭草烟(imazapyr)(包括与异丙基胺形成的盐等)、灭草喹(imazaquin)、咪草烟(imazethapyr);
(B-2)嘧啶氧苯甲酸酯:双草醚(bispyribac-sodium)、嘧啶肟草醚(pyribenzoxim)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac-methyl)、嘧草硫醚(pyrithiobac-sodium)、吡丙醚(pyrimisulfan)、氟酮磺草胺(triafamone);
(B-3)磺酰基氨基羰基三唑啉酮类:氟唑磺隆(flucarbazone-sodium)、噻烯卡巴腙(thiencarbazone)(包括钠盐、甲酯等)、丙苯磺隆(propoxycarbazone-sodium)、丙苯磺隆钠盐(procarbazone-sodium)、iofensulfuron-sodium;
(B-4)磺酰脲类:酰嘧磺隆(amidosulfuron)、四唑嘧磺隆(azimsulfuron)、苄嘧磺隆(bensulfuron-methyl)、氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、醚磺隆(cinosulfuron)、环丙嘧磺隆(cyclosulfamuron)、胺苯磺隆(ethametsulfuron-methyl)、乙氧嘧磺隆(ethoxysulfuron)、啶嘧磺隆(flazasulfuron)、甲基酰嘧磺隆钠盐(flupyrsulfuron-methyl-sodium)、甲酰胺磺隆(foramsulfuron)、氯吡嘧磺隆(halosulfuron-methyl)、唑吡嘧磺隆(imazosulfuron)、甲基碘磺隆钠盐(iodosulfulon-methyl-sodium)、甲基二磺隆(mesosulfuron-methyl)、甲基噻吩磺隆(thifensulfuron-methyl)、醚苯磺隆(triasulfuron)、甲基苯磺隆(tribenuron-methyl)、三氟啶磺隆钠(trifloxysulfuron-sodium)、氟胺磺隆(triflusulfuron-methyl)、三氟甲磺隆(tritosulfuron)、嘧苯胺磺隆(orthosulfamuron)、propgirisulfuron、嗪吡嘧磺隆(metazosulfuron)、氟吡磺隆(flucetosulfuron);
(B-5)三唑并嘧啶类:氯酯磺草胺(cloransulam-methyl)、双氯磺草胺(diclosulam)、双氟磺草胺(florasulam)、唑嘧磺草胺(flumetsulam)、磺草唑胺(metosulam)、五氟磺草胺(penoxsulam)、甲氧磺草胺(pyroxsulam);
C1. 光系统II中光合作用的抑制剂(1)
(C1-1)苯基氨基甲酸酯类:甜菜安(desmedipham)、苯敌草(phenmedipham);
(C1-2)哒嗪酮类:氯草敏(chloridazon)、溴莠敏(brompyrazon);
(C1-3)三嗪类:莠灭净(ametryn)、阿特拉津(atrazine)、氰草津(cyanazine)、敌草净(desmetryne)、异戊乙净(dimethametryn)、克菊特(eglinazine-ethyl)、扑灭通(prometon)、扑草净(prometryn)、扑灭津(propazine)、西玛津(simazine)、西草净(simetryn)、甲氧去草净(terbumeton)、特丁津(terbuthylazine)、特丁净(terbutryn)、草达津(trietazine);
(C1-4)三嗪酮类:苯嗪草酮(metamitron)、嗪草酮(metribuzin);
(C1-5)三唑啉酮类:氨唑草酮(amicarbazone);
(C1-6)尿嘧啶类:除草定(bromacil)、环草定(lenacil)、特草定(terbacil);
C2. 光系统II中光合作用的抑制剂(2)
(C2-1)酰胺类:蔬草灭(pentanochlor)、敌稗(propanil);
(C2-2)脲类:氯溴隆(chlorbromuron)、氯麦隆(chlorotoluron)、枯草隆(chloroxuron)、噁唑隆(dimefuron)、敌草隆(diuron)、磺噻隆(ethidimuron)、非草隆(fenuron)、伏草隆(fluometuron)、异丙隆(isoproturon)、异噁隆(isouron)、利谷隆(linuron)、甲基苯噻隆(methabenzthiazuron)、秀谷隆(metobromuron)、甲氧隆(metoxuron)、绿谷隆(monolinuron)、草不隆(neburon)、环草隆(siduron)、丁噻隆(tebuthiuron)、吡喃隆(metobenzuron);
C3. 光系统II中光合作用的抑制剂(3)
(C3-1)苯并噻二嗪酮(Benzothiadiazone)类:灭草松(bentazone);
(C3-2)腈类:杀草全(bromofenoxim)、溴苯腈(bromoxynil)(包括丁酸酯、辛酸酯、庚酸酯等)、碘苯腈(ioxynil);
(C3-3)苯基哒嗪类:达草醇(pyridafol)、哒草特(pyridate);
D.光系统I电子受体
(D-1)联吡啶鎓盐类:敌草快(diquat)、百草枯二氯化物(paraquat dichloride);
E.原卟啉原氧化酶(PPO)抑制剂
(E-1)二苯醚类:氟锁草醚钠(acifluorfen-sodium)、甲羧除草醚(bifenox)、甲氧除草醚(chlomethoxyfen)、氯氟草醚乙酯(ethoxyfen-ethyl)、乙羧氟草醚(fluoroglycofen-ethyl)、氟磺胺草醚(fomesafen)、乳氟禾草灵(lactofen)、氧氟吩(oxyfluorfen);
(E-2)N-苯基邻苯二甲酰亚胺类:吲哚酮草酯(cinidon-ethyl)、氟烯草酸(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、氯酰亚胺(chlorphthalim);
(E-3)噁二唑类:丙炔噁草酮(oxadiargyl)、噁草灵(oxadiazon);
(E-4)噁唑烷二酮类:环戊噁草酮(pentoxazone);
(E-5)苯基吡唑类:异丙吡草酯(fluazolate)、吡草醚(pyraflufen-ethyl);
(E-6)嘧啶二酮类:双苯嘧草酮(benzfendizone)、氟丙嘧草酯(butafenacil)、苯嘧磺草胺(saflufenacil)、tiafenacil;
(E-7)噻二唑类:哒草氟(fluthiacet-methyl)、噻二唑草胺(thidiazimin);
(E-8)三唑啉酮类:唑啶草酮(azafenidin)、唑草酯(carfentrazone-ethyl)、甲磺草胺(sulfentrazone)、bencarbazone;
(E-9)其他化合物:氟哒嗪草酯(flufenpyr-ethyl)、氟唑草胺(profluazol)、双唑草腈(pyraclonil)、SYP-298(编号)、SYP-300(编号);
F1. 八氢番茄红素脱氢酶步骤(PDS)中类胡萝卜素生物合成的抑制剂
(F1-1)哒嗪酮类:达草灭(norflurazon);
(F1-2)嘧啶羧酰胺类:氟酰草胺(diflufenican)、氟吡酰草胺(picolinafen);
(F1-3)其他化合物:氟丁酰草胺(beflubutamid)、氟啶酮(fluridone)、氟咯草酮(flurochloridone)、呋草酮(flurtamone);
F2. 4-羟苯基丙酮酸双加氧酶(HPPD)抑制剂
(F2-1)Callistemone类:甲基磺草酮(mesotrione);
(F2-2)异噁唑类:磺酰草吡唑(pyrasulfotole)、异噁唑草酮(isoxaflutole)、异氯草酮(isoxachlortole);
(F2-3)吡唑类:吡草酮(benzofenap)、吡唑特(pyrazolate)、苄草唑(pyrazoxyfen)、苯唑草酮(topramezone);
(F2-4)三酮类:磺草酮(sulcotrione)、呋喃磺草酮(tefuryltrione)、环磺酮(tembotrione)、磺酰草吡唑(pyrasulfotole)、苯唑草酮(topramezone)、氟吡草酮(bicyclopyrone);
F3. 类胡萝卜素生物合成抑制剂(未知的靶位点)
(F3-1)二苯醚类:苯草醚(aclonifen);
(F3-2)异噁唑烷酮类:广灭灵(clomazone);
(F3-3)三唑类:杀草强(amitrole);
G.EPSP合酶抑制剂(芳香族氨基酸生物合成抑制剂)
(G-1)甘氨酸类:草甘膦(包括钠盐、胺盐、丙胺盐、异丙胺盐、二甲胺盐、三甲基硫盐等);
H.谷氨酰胺合成酶抑制剂
(H-1)次膦酸类:双丙氨酰膦(bilanafos)、草铵膦(glufosinate)(包括胺盐、钠盐等);
I.二氢叶酸(DHP)合成酶抑制剂
(I-1)氨基甲酸酯类:黄草灵(asulam);
K1.微管装配抑制剂
(K1-1)苯胺类:炔苯酰草胺(propyzamide)、牧草胺(tebutam);
(K1-2)苯甲酸类:敌草索(chlorthal-dimethyl);
(K1-3)二硝基苯胺类:乙丁氟灵(benfluralin)、仲丁灵(butralin)、敌乐胺(dinitramine)、乙丁烯氟灵(ethalfluralin)、氟消草(fluchloralin)、黄草消(oryzalin)、二甲戊灵(pendimethalin)、氨基丙氟灵(prodiamine)、氟乐灵(trifluralin);
(K1-4)氨基磷酸酯类:甲基胺草磷(amiprophos-methyl)、抑草磷(butamifos);
(K1-5)吡啶类:氟硫草定(dithiopyr)、噻唑烟酸(thiazopyr);
K2.有丝分裂/微管组装抑制剂
(K2-1)氨基甲酸酯类:卡草胺(carbetamide)、氯苯胺灵(chlorpropham)、苯胺灵(propham)、灭草灵(swep)、隆草特(karbutilate);
K3.超长链脂肪酸(VLCFAs)抑制剂(细胞分裂抑制剂)
(K3-1)乙酰胺类:草乃敌(diphenamid)、敌草胺(napropamide)、萘丙胺(naproanilide);
(K3-2)氯乙酰胺类:乙草胺(acetochlor)、草不绿(alachlor)、丁草胺(butachlor)、丁烯草胺(butenachlor)、乙酰甲草胺(diethatyl-ethyl)、二甲草胺(dimethachlor)、噻吩草胺(dimethenamid)、高效噻吩草胺(dimethenamid-P)、吡唑草胺(metazachlor)、异丙甲草胺(metolachlor)、烯草胺(pethoxamid)、丙草胺(pretilachlor)、扑草胺(propachlor)、异丙草胺(propisochlor)、精异丙甲草胺(S-metolachlor)、噻吩草胺(thenylchlor);
(K3-3)氧乙酰胺类:氟噻草胺(flufenacet)、苯噻草胺(mefenacet);
(K3-4)四唑啉酮类:四唑酰草胺(fentrazamide);
(K3-5)其他化合物:莎稗磷(anilofos)、溴丁酰草胺(bromobutide)、唑草胺(cafenstrole)、茚草酮(indanofan)、哌草磷(piperophos)、苯磺噁唑草(fenoxasulfone)、砜吡草唑(pyroxasulfone)、三唑酰草胺(ipfencarbazone);
L.纤维素合成抑制剂
(L-1)苯甲酰胺类:异噁酰草胺(isoxaben);
(L-2)腈类:敌草腈(dichlobenil)、草克乐(chlorthiamid);
(L-3)三唑并甲酰胺类:氟胺草唑(flupoxam);
M.解偶联剂(膜破坏剂)
(M-1)二硝基酚类:特乐酚(dinoterb)、DNOC(包括胺盐、钠盐等);
N.脂质生合成抑制剂(不包括乙酰辅酶A羧化酶(ACCase)抑制剂)
(N-1)苯并呋喃类:呋草黄(benfuresate)、乙氧呋草黄(ethofumesate);
(N-2)卤代羧酸类:茅草枯(dalapon)、四氟丙酸(flupropanate)、TCA(三氯乙酸)(包括钠盐、钙盐、氨盐等);
(N-3)二硫代磷酸酯类:地散磷(bensulide);
(N-4)硫代氨基甲酸酯类:苏达灭(butylate)、草灭特(cycloate)、哌草丹(dimepiperate)、EPTC、戊草丹(esprocarb)、禾草敌(molinate)、坪草丹(orbencarb)、克草猛(pebulate)、苄草丹(prosulfocarb)、禾草丹(thiobencarb)、仲草丹(tiocarbazil)、野麦畏(triallate)、灭草猛(vernolate);
O.合成生长素
(O-1)苯甲酸类:草灭平(chloramben)、2,3,6-TBA(2,3,6-三氯苯甲酸)、麦草畏(dicamba)(包括胺盐、二乙胺盐、异丙胺盐、二甘醇胺盐、钠盐、锂盐等);
(O-2)苯氧羧酸类:2,4,5-T、2,4-D(包括胺盐、二乙胺盐、三乙醇胺盐、异丙胺盐、钠盐、锂盐等)、2,4-DB(4-(2,4-二氯苯氧基)丁酸)、氯甲酰草胺(clomeprop)、滴丙酸(dichlorprop)、精滴丙酸(dichlorprop-P)、MCPA((4-氯-2-甲基苯氧基)乙酸)、酚硫杀(MCPA-thioethyl)、MCPB(4-(4-氯-2-甲基苯氧基)丁酸)(包括钠盐、乙酯等)、2-甲-4-氯丙酸(mecoprop)(包括钠盐、钾盐、异丙胺盐、三乙醇胺盐、二甲胺盐等)、高2-甲-4-氯丙酸(mecoprop-P);
(O-3)吡啶羧酸类:二氯吡啶酸(clopyralid)、氟草烟(fluroxypyr)、毒莠定(picloram)、定草酯(triclopyr)、绿草定酯(triclopyr-butotyl)、氟氯吡啶酯(halauxifen-methyl);
(O-4)喹啉羧酸类:二氯喹啉酸(quinclorac)、喹草酸(quinmerac);
(O-5)其他化合物:草除灵(benazolin);
P.生长素转运抑制剂
(P-1)邻氨甲酰苯甲酸盐(Phthalamate)类:抑草生(naptalam)(包括与钠形成的盐等);
(P-2)缩氨基脲类:二氟吡隆(diflufenzopyr);
Z.作用方式未知的化合物
强氟燕灵(flamprop-M)(包括甲酯、乙酯和异丙酯)、麦草氟(flamprop)(包括甲酯、乙酯和异丙酯)、甲基氯芴素(chlorflurenol-methyl)、环庚草醚(cinmethylin)、可灭隆(cumyluron)、杀草隆(daimuron)、甲基杀草隆(methyldymuron)、野燕枯(difenzoquat)、乙氧苯草胺(etobenzanid)、调节膦(fosamine)、稗草畏(pyributicarb)、噁嗪草酮(oxaziclomefone)、丙烯醛、AE-F-150954(编号)、环丙嘧啶酸(aminocyclopyrachlor)、氰胺、heptamaloxyloglucan、茚嗪氟草胺(indaziflam)、三嗪氟草胺(triaziflam)、灭藻醌(quinoclamine)、内氧草索钠盐(endothal-disodium)、棉胺宁(phenisopham)、SL-573(编号)(1-环丙基甲基-6-甲氧基-4-苯基-2(1H)-喹唑啉酮)、cyclopyrimonate;植物生长调节剂:1-甲基环丙烯、1-萘乙酰胺、2,6-二异丙基萘、4-CPA((4-氯苯氧基)乙酸)、苄基氨基嘌呤、嘧啶醇、艾维激素(aviglycine)、香芹酮、矮壮素、调果酸(cloprop)、座果酸(cloxyfonac)、座果酸钾、环丙酸酰胺、细胞分裂素、丁酰肼、敌草克(dikegulac)、噻节因(dimethipin)、乙烯磷(ethephon)、吲熟酯(ethychlozate)、氟节胺(flumetralin)、抑草丁(flurenol)、调嘧醇(flurprimidol)、氯吡脲(forchlorfenuron)、赤霉酸、抗倒胺(inabenfide)、吲哚乙酸、吲哚丁酸、马来酰肼、氟磺酰草胺(mefluidide)、缩节胺(mepiquat chloride)、正癸醇、多效唑(paclobutrazol)、调环酸钙(prohexadione-calcium)、茉莉酮(prohydrojasmon)、杀雄啉(sintofen)、噻苯隆(thidiazuron)、三十烷醇、抗倒酯(trinexapac-ethyl)、烯效唑(uniconazole)、单克素(uniconazole-P)、4-氧代-4-(2-苯基乙基)氨基丁酸(化学名称,CAS登录号:1083-55-2)。
接下来,以下为可以混合或组合使用的已知的安全剂的例子。
解草嗪(benoxacor)、解草噁唑(furilazole)、烯丙酰草胺(dichlormid)、dicyclonone、DKA-24(N1,N2-二烯丙基-N2-二氯乙酰基甘氨酰胺)、AD-67(4-二氯乙酰基-1-氧杂-4-氮杂螺环[4.5]癸烷)、PPG-1292(2,2-二氯-N-(1,3-二氧杂环己烷-2-基甲基)-N-(2-丙烯基)乙酰胺)、R-29148(3-二氯乙酰基-2,2,5-三甲基-1,3-噁唑烷)、解毒喹(cloquintcet-methyl)、1,8-萘二甲酸酐、吡咯二酸二乙酯(mefenpyrdiethyl)、吡唑解草酸(mefenpyr)、吡唑解草乙酯(mefenpyr-ethyl)、解草唑(fenchlorazole O ethyl)、解草啶(fenclorim)、MG-191(2-二氯甲基-2-甲基-1,3-二氧杂环己烷)、解草胺腈(cyometrinil)、解草胺(flurazole)、氟草肟(fluxofenim)、双苯噁唑酸(isoxadifen)、双苯噁唑酸乙酯(isoxadifen-ethyl)、2-甲-4-氯丙酸(mecoprop)、MCPA、杀草隆(daimuron)、2,4-D((2,4-二氯苯氧基)乙酸)、MON 4660(编号)(4-(二氯乙酰基)-1-氧杂-4-氮杂螺环[4.5]癸烷)、解草腈(oxabetrinil)、环丙磺酰胺(cyprosulfamide)、低级烷基取代的苯甲酸、TI-35(编号)和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺(化学名称,CAS登录号:129531-12-0)。
如上述构成的本发明的害虫控制剂针对直翅目、缨翅目、半翅目、鞘翅目、双翅目、鳞翅目、膜翅目、弹尾目、缨尾目、蜚蠊目、等翅目、啮虫目、食毛目、虱目的害虫、植食性螨类、植物寄生性线虫、植物寄生性软体害虫、其他作物害虫、公害害虫、卫生害虫、寄生虫等显示优异的控制效果。以下生物物种为这些害虫的示例。
直翅目害虫可以是例如:
螽蜇科:黑胫钩额草螽等;
蟋蟀科:黄脸油葫芦等;
蛩蠊科:东方蝼蛄;
蝗科:小稻蝗(Oxya hyla intricate)、飞蝗、草地血黑蝗(Melanoplussanguinipes)等;
锥头蝗科:长额负蝗;
丛蟋科:Euscrytus japonicus;
蚤蝗科:日本蚤蝗(Xya japonicus)等。
缨翅目害虫可以是例如:
蓟马科:花蓟马、西花蓟马、茶黄蓟马、棕榈蓟马、葱蓟马等;
管蓟马科:柿管蓟马(Ponticulothrips diospyrosi)、稻管蓟马等。
半翅目害虫可以是例如:
蝉科:姬草蝉等;
尖胸沫蝉科:白带尖胸沫蝉等;
角蝉科:褐角蝉等;
叶蝉科:葡萄叶蝉(Arboridia apicalis)、茶小绿叶蝉、黑尾叶蝉(Nephotettixcincticeps)、电光叶蝉(Recilia dorsalis)等;
麦腊蝉科:端斑五脊菱蜡蝉(Pentastiridius apicalis)等;
飞虱科:灰飞虱、褐飞虱、白背飞虱等;
缟飞虱科:缟飞虱(Nisia nervosa)等;
袖蜡蝉科:Kamendaka saccharivora等;
小头飞虱科(Cixidia okunii):Achilus flammeus等;
广翅蜡蝉科:Orosanga japonicus等;
蛾蜡蝉科:蛾蜡蝉(Mimophantia maritima)等;
木虱科:梨木虱(Cacopsylla pyrisuga)等;
丽木虱科:芒果丽木虱(Calophya mangiferae)等;
根瘤蚜科:葡萄根瘤蚜(Daktulosphaira vitifoliae)等;
球蚜科:落叶松球蚜、铁杉球蚜等;
蚜科:豌豆蚜、棉蚜、绣线菊蚜、萝卜蚜、桃蚜、麦二叉蚜、禾谷缢管蚜等;
粉虱科:茶树黑刺粉虱、烟粉虱、银叶粉虱、温室粉虱等;
绵蚧科:草履蚧、柑橘吹棉蚧等;
粉蚧科:菠萝粉蚧(Dysmicoccus brevipes)、柑桔粉蚧(Planococcus citri)、康氏粉蚧等;
蜡蚧科:角蜡蚧(Ceroplastes ceriferus)等;
仁蚧科:甘蔗仁蚧(Aclerda takahasii)等;
盾蚧科:红圆蚧(Aonidella aurantii)、梨圆蚧、矢尖蚧(Unaspis yanonensis)等;
盲蝽科:豆荚草盲蝽(Lygus hesperus)、赤须盲蝽(Trigonotyluscaelestialium)等;
网蝽科:杜鹃网蝽、梨花网蝽等;
椿科:北二星蝽、稻褐蝽、稻绿蝽、小珀蝽等;
龟蝽科:筛豆龟蝽等;
长蝽科:甘蔗异背长蝽等;
束长蝽科:日本束长蝽(Malcus japonicus)等;
红蝽科:离斑棉红蝽等;
蛛缘蝽科:大稻缘蝽(Leptocorisa acuta)、中华稻缘蝽等;
缘蝽科:纹须同缘蝽(Anacanthocoris striicornis)等;
姬缘蝽科:黄伊缘蝽(Rhopalus maculatus)等;
臭虫科:温带臭虫等。
鞘翅目害虫可以是例如:
金龟科:铜色丽金龟(Anomara cuprea)、姬金龟(Anomara rufocuprea)、日本弧丽金龟、犀角金龟(Oryctes rhinoceros)等;
叩甲科:Agriotes ogurae、Melanotus okinawensis、Melanotos fortnumifortnumi等;
皮蠹科:小圆皮蠹(Anthrenus verbasci)等;
长蠹总科:二突异翅长蠹(Heterobostrychus hamatipennis)等;
窃蠹科:药材甲等;
蛛甲科:棕蛛甲(Pitinus clavipes)等;
谷盗科:大谷盗(Tenebroides manritanicus)等;
郭公虫科:赤足郭公虫;
露尾甲科:酱曲露尾甲等;
锯谷盗科:米扁虫(Ahasverus advena)等;
扁谷盗科:锈赤扁谷盗等;
瓢虫科:墨西哥豆瓢虫、茄二十八星瓢虫等;
拟步甲科:黄粉甲虫(Tenebriomolitor)、赤拟谷盗等;
芫菁科:豆芫菁等;
天牛科:光肩星天牛(Anoplophora glabripennis)、、葡萄虎天牛(Xylotrechuspyrrhoderus)、松墨天牛(Monochamus alternatus)等;
豆象科:绿豆象(Callosobruchus chinensis)等;
叶甲科:马铃薯甲虫、玉米根叶甲、小猿叶甲、黄曲条菜跳甲等;
三锥象甲科:甘薯小象甲(Cylas formicarius)等;
象甲科:苜蓿叶象甲(Hypera postica)、蔬菜叶象甲(Listroderescostirostris)、西印度甘薯象甲(Euscepes postfasciatus)等;
粗吻象鼻虫科(Erirhinidae):稻象(Echinocnemus bipunctatus)、稻水象甲(Lissorhoptrus oryzophilus)等;
椰象鼻虫科(Dryophthoridae):玉米象(Sitophilus zeamais)、草皮步行象鼻虫(sphenophrusvenatus)等;
小蠹科(Scolytidae):松纵坑切梢小蠹(Tomicus piniperda)等;
长小蠹科:台日截尾长小蠹(Crossotarsus niponicus)等;
粉蠹科:褐粉蠹(Lyctus brunneus)等。
双翅目害虫可以是例如:
大蚊科:Tipila aino等;
毛蚊科:黑色小毛蚊等;
蕈蚋科:Exechia shiitakevora等;
黑翅蕈蚋科:马铃薯蕈蚊(Pnyxia scabiei)等;
瘿蚊科:大豆荚瘿蚊、黑森瘿蚊(Mayetiola destructor)等;
蚊科:埃及伊蚊、淡色库蚊(Culex pipiens pallens)等;
蚋科:牛蚋(Simulim takahasii)等;
摇蚊科:稻摇蚊等;
虻科:密斑虻(Chrysops suavis)、三角虻(Tabanus trigonus)等;
食蚜蝇科:洋葱平颜食蚜蝇(Eumerus strigatus)等;
实蝇科:桔小实蝇、日本樱桃实蝇(Euphranta japonia)、地中海实蝇等;
潜蝇科:三叶斑潜蝇、豌豆彩潜蝇等;
秆蝇科(Chloropidae):黑腹麦秆蝇(Meromyza nigriventris)等;
果蝇科:铃木氏果蝇(Drosophila suzukii)、黑腹果蝇(Drosophilamelanogaster)等;
水蝇科:水稻潜叶蝇等;
虱蝇科:马虱蝇(Hippobosca equina)等;
粪蝇科:笹川粪蝇等;
花蝇科:葱蝇、灰地种蝇等;
厕蝇科:夏厕蝇等;
蝇科:家蝇、厩螫蝇等;
麻蝇科:棕尾别麻蝇(Sarcophaga peregrina)等;
胃蝇科:肠胃蝇等;
皮蝇科:纹皮蝇等;
狂蝇科:羊狂蝇等。
鳞翅目害虫可以是例如:
蝙蝠蛾科:淡缘蝠蛾等;
日蛾科:葡萄日蛾(Antispila ampelopsia)等;
木蠢蛾科:六星黑点豹蠹蛾(Zeuzera leuconotum)等;
卷蛾科:乱纹苹果卷叶蛾(Archips fuscocupreanus)、棉褐带卷蛾(Adoxophyesorana fasciata)、梨小食心虫(Grapholita molesta)、茶长卷蛾(Homona magnanima)、大豆食心虫、苹果蠹蛾等;
纹蛾科:女贞细卷蛾(Eupoecilia ambiguella)等;
蓑蛾科:黑艳避债蛾(Bambalina sp.)、茶避债蛾(Eumeta minuscula)等;
谷蛾科:谷蛾(Nemapogon granella)、衣蛾(Tinea translucens)等;
棱巢蛾科:梨角折蛾(Bucculatrix pyrivorella)等;
潜蛾科:桃潜叶蛾等;
细蛾科:茶细蛾、金纹小潜细蛾(Phyllonorycter ringoniella)等;
叶潜蛾科:柑桔潜叶蛾(Phyllocnistis citrella)等;
粗顶蛾科:葱菜蛾(Acrolepiopsis sapporensis)等;
巢蛾科:小菜蛾(Plutella xylostella)、苹果巢蛾(Yponomeuta orientalis)等;
银蛾科(Argyresthidae):苹果银蛾(Argyresthia conjugella)等;
透翅蛾科(Sesidae):葡萄透翅蛾(Nokona regalis)等;
麦蛾科:马铃薯块茎蛾(Phthorimaea operculella)、麦蛾、棉红铃虫等;
蛀果蛾科:桃蛀果蛾(Carposina sasakii)等;
斑蛾科:梨星毛虫等;
刺蛾科:黄刺蛾(Monema flavescens)等;
草螟科:稻巢螟(Ancylolomia japonica)、二化螟、稻纵卷叶螟(Cnaphalocrosismedinalis)、亚洲玉米螟(Ostrinia furnacalis)、欧洲玉米螟(Ostrinia nubilalis)等;
螟蛾科:干果斑螟(Cadra cautella)、大蜡螟(Galleria mellonella)等;
羽蛾科:葡萄羽蛾(Nippoptilia vitis)等;
凤蝶科:柑橘凤蝶等;
粉蝶科:菜粉蝶等;
弄蝶科:直纹稻弄蝶(Parnara guttata guttata)等;
尺蛾科:大造桥虫(Ascotis selenaria)等;
枯叶蛾科:赤松毛虫、黄褐天幕毛虫(Malacosomaneustrium testaceum)等;
天蛾科:甘薯天蛾(Agrius convolvuli)等;
毒蛾科:茶毛虫(Arna pseudoconspersa)、舞毒蛾(Lymantria dispar)等;
灯蛾科:美国白蛾(Hyphantria cunea)等;
夜蛾科:小地老虎(Agrotis ipsilon)、豆银纹夜蛾(Autographa nigrisigna)、棉铃虫、玉米夜蛾(Helicoverpa zea)、烟芽夜蛾、甜菜夜蛾、斜纹夜蛾等。
膜翅目害虫可以是例如:
三节叶蜂科:玫瑰黄腹三节叶蜂(Arge pagana)等;
叶蜂科:栗叶峰、黄翅菜叶蜂(Athalia rosae ruficornis)等;
瘿蜂科:板栗瘿蜂(Dryocosmus kuriphilus)等;
胡蜂科:黄色雀蜂(Vespa simillima xanthoptera)等;
蚁科:红火蚁等;
切叶蜂科:蔷薇切叶蜂(Megachile nipponica)等。
弹尾目害虫可以是例如:
圆跳虫科:黄星圆跳虫(Bourletiella hortensis)等。
缨尾目害虫可以是例如:
衣鱼科:蠹鱼、毛衣鱼等。
蜚蠊目害虫可以是例如:
蜚蠊科:美洲大蠊;
姬蜚蠊科:德国小蠊等。
等翅目害虫可以是例如:
木白蚁科:小楹白蚁(Incisitermes minor)等;
鼻白蚁科:台湾乳白蚁等;
白蚁科:黑翅土白蚁等。
啮虫目害虫可以是例如:
窃啮科(Trogiidae):尘虱等;
虱啮科:Liposcelis corrodens等。
食毛目害虫可以是例如:
短角鸟虱科:翼虱(Lipeurus caponis)等;
啮毛虱科:牛毛虱(Damalinia bovis)等。
虱目害虫可以是例如:
血虱科:猪血虱(Haematopinus suis)等;
虱科(Pediculine):人虱(Pediculus humanus)等;
颚虱科:棘颚虱(Linognathus setosus)等;
阴虱科:阴虱(Phthrius pubis)等。
植食性螨可以是例如:
真足螨科:麦圆叶爪螨(Penthaleus major)等;
跗线螨科:樱草狭跗线螨(Phytonemus pallidus)、茶黄螨等;
蒲螨科:Siteroptes sp.等;
细须螨科:葡萄短须螨(Brevipalpus lewisi)等;
杜克螨科(Tuckerellidae):孔雀杜克螨(Tuckerella pavoniformis)等;
叶螨科:北始叶螨(Eotetranychus boreus)、柑桔全爪螨(Panonychus citri)、苹果全爪螨(Panonychus ulmi)、二斑叶螨、神泽氏叶螨(Tetranychus kanzawai)等;
纳瘿螨科:松三毛瘿螨(Trisetacus pini)等;
瘿螨科:桔刺皮节蜱(Aculops pelekassi)、梨上瘿螨(Epitrimerus pyri)、柑桔锈螨(Phyllocoptruta oleivola)等;
羽爪瘿螨科:Diptacus crenatae等;
粉螨科:椭圆食粉螨、腐食酪螨、罗宾根螨(Rhizoglyphus robini)等。
植物寄生性线虫可以是例如:
长针科:标准剑线虫(Xiphinema index)等;
毛刺科:微小拟毛刺线虫(Paratrichodorus minor)等;
小杆科:Rhabditella sp.等;
垫刃科(Tylenchidae):Aglenchus sp.等;
锥垫刃科(Tylodoridae):Cephalenchus sp.等;
粒科:草莓芽线虫、马铃薯茎线虫(Ditylenchus destructor)等;
纽带科:肾形线虫(Rotylenchulus reniformis)、双宫螺旋线虫等;
针线虫科:弯曲针线虫等;
根结线虫科:根结线虫(Meloidogyne incognita)、北方根结线虫(Meloidogynehapla)等;
异皮科:马铃薯金线虫(Globodera rostochiensis)、大豆胞囊线虫(Heteroderaglycines)等;
端垫刃科(Telotylenchidae):马齿苋矮化线虫(Tylenchorhynchus claytoni)等;
裸毛科(Psilenchidae):Psilenchus sp.等;
环科:Criconemoides sp.等;
半穿刺科:柑桔根线虫(Tylenchulus semipenetrans)等;
球线虫科(Spaeronematidae):山茶球线虫(Sphaeronema camelliae)等;
短体科:Sphaeronema camelliae、柑桔穿孔线虫(Radopholus citrophilus)、香蕉穿孔线虫(Radopholus similis)、异常珍珠线虫、穿刺短体线虫、咖啡短体线虫(Pratylenchus coffeae)等;
小齿线虫科(Iotonchiidae):伞菌褶瘤线虫(Iotonchium ungulatum)等;
真滑刃科(Aphelenchidae):燕麦真滑刃线虫等;
滑刃科(Aphelenchoididae):叶芽线虫、草莓滑刃线虫等;
寄生滑刃科:松材线虫等。
植物寄生性软体害虫可以是例如:
球螺科(Pilidae):福寿螺(Pomacea canaliculata)等;
皱足蛞蝓科:宽足蛞蝓(Leavicaulis alte)等;
玛瑙螺科:非洲大蜗牛等;
嗜粘液蛞蝓科:双线嗜粘液蛞蝓等;
琥珀螺科:Succinea lauta等;
圆盘蜗牛科(Didcidae):浅圆盘螺等;
琥珀蜗牛科:虾夷琥珀贝(Zonitoides yessoensis)等;
蛞蝓科:黄蛞蝓、野蛞蝓(Deroceras reticulatum)等;
鳖甲蜗牛科:Parakaliella harimensis等;
巴蜗牛科(Bradybaenidae):琉球球蜗牛(Acusta despecta sieboldiana)、同型巴蜗牛(Bradybaena similaris)等。
例如有害动物、造成不适的动物、卫生害虫、牲畜害虫、寄生虫等其他害虫可以是:例如,
蜱螨亚纲巨刺螨科:林禽刺螨(Ornithonyssus sylvialum)等;
瓦螨科:雅氏瓦螨(Varroa jacobsoni)等;
皮刺螨科:鸡皮刺螨等;
巨刺螨科:林禽刺螨(Ornithonyssus sylvialum)等;
硬蜱科:微小牛蜱(Boophilus microplus)、血红扇头蜱、长角血蜱等;
疥螨科:疥螨等;
等足目卷壳虫科:普通卷甲虫(Armadillidium vulgare)等;
十足目螯虾科:克氏原螯虾等;
鼠妇科:普通卷甲虫(Armadillidium vulgare)等;
唇足纲害虫:蚰蜓目蚰蜒科(Scutigeromorpha Sutigeridae)、花蚰蜓(Thereuonema tuberculata)、蜈蚣目越南巨人蜈蚣(Scolopendromorpha Scolopendrasubpinipes)等。
倍足纲害虫:带马陆目奇马陆科的温室马陆(Polydesmida ParadoxosomatidaeOxidus gracillis)等。
蜘蛛目红背蜘蛛(Araneae Latrodectus hasseltii):Theridiiadae hasseltii等;
管巢蛛科:日本红螯蛛(Chiracanthium japonicum)等;
蝎目:土耳其黑肥尾蝎(Androctonus crassicauda)等;
寄生圆虫:人蛔虫、管状属线虫(Syphacia sp.)、班氏吴策线虫(Wucherebiabancrofti)等;
寄生扁虫:肝蛭(Distomum sp.)、卫氏并殖吸虫(Paragonimus westermanii)、横川后殖吸虫、日本血吸虫、链状带绦虫、牛带绦虫(Taeniarhynchus saginatus)、棘球绦虫(Echinococcus sp.)、阔节裂头绦虫等。
本发明涉及的害虫控制剂也针对已对现有害虫控制剂具有抗性的上述害虫等显示控制效果。此外,本发明涉及的控制剂可以施用于因基因改造或农业配种等而已对昆虫、疾病、除草剂等具有抗性的植物。
接下来,以实例的形式对本发明涉及的化合物的制造方法、制剂化方法及施用进行详细说明。但是,本发明并非仅限于这些例子。
对用于制造本发明涉及的化合物的中间体的制造方法也进行了说明。
实施例
参考以下的制备例、制剂例和试验例对本发明进行更详细的说明。但是,本发明不限于这些实施例。此外,可以在不脱离本发明范围的范围内进行变更。
制备例1
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑(化合物1)的制备
(1)4,4,4-三氟-1-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-1,3-丁二酮
在将温度维持为0至10℃的情况下,向1-(5-(2,2,2-三氟乙基硫基)-2-氟-4-甲基苯基)乙酮(10.0g,37.0mmol)的THF(100mL)溶液中分三次加入NaH(矿物油中为60%,2.20g,55.0mmol)。于该温度搅拌20分钟后,缓缓加入三氟乙酸乙酯(7.88g,55.0mmol),将反应混合物于室温搅拌1小时。然后将反应混合物投入冰水中,使用2M HCl溶液酸化,然后使用乙酸乙酯(3x 100mL)萃取。然后将合并的有机层用蒸馏水(2x 100mL)洗涤,用硫酸钠干燥,并在减压下浓缩,由此得到粗产物(14.0g)。如此得到的粗产物不经任何纯化而继续使用。
1H NMR(CDCl3):8.13(d,J=6.8Hz,1H),7.09(d,J=12.4Hz,1H),6.68(m,1H),3.39(q,J=9.6Hz,2H),2.54(s,3H).
(2)3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)-4,5-二氢异噁唑-5-醇
于10℃向4,4,4-三氟-1-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-1,3-丁二酮(1.0g,2.70mmol)的乙醇(25mL)溶液中加入盐酸羟胺(0.29g,4.10mmol),然后将混合物于80℃搅拌3小时。蒸馏乙醇后,利用乙酸乙酯(3x 10mL)萃取残余物。将合并的有机层用盐水洗涤,用硫酸钠干燥,过滤并在减压下浓缩,由此得到粗产物。然后通过柱色谱(乙酸乙酯∶正己烷=1∶2)纯化残余物,成功得到3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)-4,5-二氢异噁唑-5-醇(0.45g,收率为43.2%)。
1H NMR(CDCl3):8.05(d,J=7.2Hz,1H),7.05(d,J=11.6Hz,1H),3.75-3.80(m,1H),3.55-3.63(m,1H),3.38(q,J=9.6Hz,2H),2.51(s,3H).
(3)3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑(化合物1)
于室温向3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)-4,5-二氢异噁唑-5-醇(6.50g,17.0mmol)的甲苯(80mL)溶液中加入亚硫酰氯(3.07g,26.0mmol)和吡啶(5.36g,68.0mmol)。然后将混合物于100℃加热1小时。冷却至室温后,使用二氯甲烷(3x 100mL)萃取反应混合物。然后将合并的有机层用盐水洗涤,用硫酸钠干燥,过滤并在减压下浓缩。然后通过柱色谱(乙酸乙酯∶正己烷=1∶4)纯化残余物,成功得到3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑(6.10g,收率为98.5%)。
1H NMR(CDCl3):8.18(d,J=7.2Hz,1H),7.11-7.14(m,2H),3.40(q,J=9.6Hz,2H),2.54(s,3H).
制备例2
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-4-甲基-5-(三氟甲基)异噁唑(化合物37)的制备
(1)2-氟-N-甲氧基-N,4-二甲基苯甲酰胺
于0℃向2-氟-4-甲基苯甲酸(20.0g,130mmol)的二氯甲烷(200mL)溶液中加入N,O-二甲基羟胺(18.9g,190mmol)、N-(3-二甲基氨基丙基)-N-乙基碳二亚胺盐酸盐(37.3g,190mmol)、1-羟基苯并三唑水合物(26.3g,190mmol)和二异丙基乙胺(72mL,390mmol)。然后将反应混合物于室温搅拌1小时。然后,将反应混合物投入冰水中,使用乙酸乙酯(3x100mL)萃取。然后将合并的有机层用蒸馏水(2x 100mL)洗涤,用硫酸钠干燥,并在减压下浓缩,由此得到粗产物(22.0g,86%)。如此得到的粗产物不经任何纯化而继续使用。
1H NMR(CDCl3):7.32(t,J=7.6Hz,1H),6.99(d,J=7.6Hz,1H),6.91(d,J=10.8Hz,1H),3.57(s,3H),3.33(s,3H),2.37(s,3H).
(2)1-(2-氟-4-甲基苯基)-1-丙酮
于0℃向2-氟-N-甲氧基-N,4-二甲基苯甲酰胺(8.0g,40.0mmol)的无水THF(150ml)溶液中滴入乙基溴化镁(80mL,80.0mmol,THF中的1M溶液)。然后将反应混合物于室温搅拌3小时。然后,将反应混合物投入冰水中,使用乙酸乙酯(3x 100mL)萃取。然后将合并的有机层用蒸馏水(2x 100mL)洗涤,用硫酸钠干燥,并在减压下浓缩,由此得到粗产物(3.20g,48%)。如此得到的粗产物不经任何纯化而继续使用。
1H NMR(CDCl3):7.78(t,J=8.0Hz,1H),7.02(d,J=8.0Hz,1H),6.93(d,J=12Hz,1H),2.94-2.99(m,2H),1.19(t,J=7.2Hz,3H).
(3)4,4,4-三氟-1-(2-氟-4-甲基苯基)-2-甲基-1,3-丁二酮
于-20℃向1-(2-氟-4-甲基苯基)-1-丙酮(5.0g,30.0mmol)的无水THF(60mL)溶液中滴入双(三氟甲基甲硅烷基)酰胺锂(7.5g,45.0mmol)。于该温度搅拌30分钟后,于-20℃缓缓加入三氟乙酸乙酯(6.41g,45.0mmol)。将反应混合物于室温搅拌6小时。然后将反应混合物投入冰水中,使用2M HCl溶液酸化,使用乙酸乙酯(3x 80ml)萃取。然后将合并的有机层用蒸馏水(2x 50mL)洗涤,用硫酸钠干燥,并在减压下浓缩,由此得到粗产物(7.2g)。如此得到的粗产物不经任何纯化而继续使用(377(M+H),通过LC-MS得到的纯度为46%)。
(4)3-(2-氟-4-甲基苯基)-4-甲基-5-(三氟甲基)-4,5-二氢异噁唑-5-醇
于室温向4,4,4-三氟-1-(2-氟-4-甲基苯基)-2-甲基-1,3-丁二酮(7.2g,27.0mmol)的乙醇(50mL)溶液中加入盐酸羟胺(3.81g,54.0mmol),然后使混合物于80℃回流3小时。蒸馏乙醇后,使用乙酸乙酯(3x 100mL)萃取残余物。将合并的有机层用盐水洗涤,用硫酸钠干燥,过滤并在减压下浓缩,由此得到粗产物。然后将残余物通过色谱法(乙酸乙酯∶正己烷=1∶1)纯化,成功得到3-(2-氟-4-甲基苯基)-4-甲基-5-(三氟甲基)-4,5-二氢异噁唑-5-醇(3.0g,收率为39%)。
1H NMR(CDCl3):7.55(t,J=8.0Hz,1H),7.30(d,J=8.0Hz,1H),6.98(d,J=12.4Hz,1H),3.98-4.07(m,1H),3.32(bs,1H),2.40(s,3H),1.26(d,J=7.6Hz,3H).
(5)3-(2-氟-4-甲基苯基)-4-甲基-5-(三氟甲基)异噁唑
于0℃向N2下的3-(2-氟-4-甲基苯基)-4-甲基-5-(三氟甲基)-4,5-二氢异噁唑-5-醇(3.0g,10.8mmol)的甲苯(20mL)溶液中加入亚硫酰氯(2.03g,16.2mmol)和吡啶(6.61g,54.0mmol)。然后将混合物于100℃加热1小时。冷却至室温后,使用二氯甲烷(3x80mL)萃取反应混合物。然后将合并的有机层用盐水洗涤,用硫酸钠干燥,过滤并在减压下浓缩。然后将残余物通过色谱法(乙酸乙酯∶正己烷=1∶4)纯化,成功得到3-(2-氟-4-甲基苯基)-4-甲基-5-(三氟甲基)异噁唑(2.0g,收率为71%)。
1H NMR(CDCl3):7.39(t,J=7.6Hz,1H),7.09(d,J=7.6Hz,1H),7.04(d,J=10.8Hz,1H),2.43(s,3H),2.13(t,J=2.0Hz,3H).
(6)4-氟-2-甲基-5-(4-甲基-5-(三氟甲基)异噁唑-3-基)苯磺酰氯
在将反应混合物的温度维持为低于30℃的情况下,向3-(2-氟-4-甲基苯基)-4-甲基-5-(三氟甲基)异噁唑(2.0g,7.71mmol)中缓缓加入氯磺酸(4.49g,38.6mmol)。然后,将得到的混合物加热至70℃并保持4小时。冷却至室温后,将反应混合物小心地投入冰中,滤取沉淀,用蒸馏水充分洗涤,干燥,由此得到0.80g的粗产物。如此得到的粗产物不经任何纯化而继续使用。
1H NMR(CDCl3):8.30(d,J=6.8Hz,1H),7.32(d,J=10Hz,1H),2.88(s,3H),2.16(t,J=2.0Hz,3H).
(7)4-氟-2-甲基-5-(4-甲基-5-(三氟甲基)异噁唑-3-基)苯硫醇
在N2下于0℃向4-氟-2-甲基-5-(4-甲基-5-(三氟甲基)异噁唑-3-基)苯磺酰氯(0.80g,2.23mmol)的经搅拌的甲苯(20mL)溶液中加入三苯基膦(2.34g,8.90mmol)。然后,将反应混合物于100℃加热1小时。反应完成后,将反应混合物冷却至室温,然后加入1NNaOH溶液(20ml)。层分离后,将水层用乙酸乙酯(3x 50mL)洗涤。然后将水层用6N HCl溶液(30mL)酸化。通过过滤收集得到的沉淀,用蒸馏水(3x 50mL)洗涤,在真空中干燥,成功得到作为白色固体的标题产物(0.16g,收率为22%)。如此得到的粗产物不经任何纯化而继续使用。
1H NMR(CDCl3):7.44(d,J=6.8Hz,1H),7.07(d,J=10.4Hz,1H),3.49(s,1H),2.41(s,3H),2.13(t,J=2.0Hz,3H).
(8)3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-4-甲基-5-(三氟甲基)异噁唑(化合物37)
将4-氟-2-甲基-5-(4-甲基-5-(三氟甲基)异噁唑-3-基)苯硫醇(0.140g,0.48mmol)的二甲基甲酰胺(4mL)溶液冷却至0℃。然后,向其中依次加入碳酸钾(0.10g,0.72mmol)和三氟碘乙烷(0.201g,0.96mmol),然后将得到的混合物于室温搅拌6小时。然后,将反应混合物投入蒸馏水中,使用二氯甲烷(3x 25mL)萃取。将合并的有机层用蒸馏水洗涤,用硫酸钠干燥,过滤并在减压下浓缩,由此得到粗产物。然后通过柱色谱(乙酸乙酯∶正己烷=1∶5)纯化残余物,成功得到3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-4-甲基-5-(三氟甲基)异噁唑(0.082g,收率为45.7%)。
1H NMR(CDCl3):7.67(d,J=7.2Hz,1H),7.14(d,J=10.4Hz,1H),3.37(q,J=9.2Hz,2H),2.56(s,3H),2.13(t,J=2.0Hz,3H).
制备例3
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑(化合物2)的制备
于-5至0℃向3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑(6.10g,17.0mmol)的二氯甲烷(70mL)溶液中加入m-CPBA(纯度为70%,4.19g,17.0mmol)。将反应混合物于-5至10℃搅拌30分钟,然后使用饱和NaHCO3溶液(70mL)淬灭。进行层分离,使用二氯甲烷(3x 75mL)萃取水性级分。将合并的有机层用饱和NaHCO3溶液(2x 50mL)洗涤,用硫酸钠干燥,在减压下除去溶剂。然后通过柱色谱(乙酸乙酯∶正己烷=1∶1)纯化残余物,成功得到作为白色固体的3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑(6.0g,收率为94.3%)。
1H NMR(CDCl3):8.61(d,J=7.2Hz,1H),7.15-7.19(m,2H),3.43-3.55(m,2H),2.84(s,3H).
制备例4
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)磺酰基)苯基)-5-(三氟甲基)异噁唑(化合物3)的制备
于-5至0℃向3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑(0.100g,0.28mmol)的二氯甲烷(5mL)溶液中加入m-CPBA(纯度为70%,0.208g,0.84mmol)。将反应混合物于室温搅拌24小时,然后用饱和NaHCO3溶液(10mL)淬灭。进行层分离,使用二氯甲烷(3x 25mL)萃取水性级分。将合并的有机层用饱和NaHCO3溶液(2x20mL)洗涤,用硫酸钠干燥,在减压下除去溶剂。然后通过柱色谱(二氯甲烷∶正己烷=1∶1)纯化残余物,成功得到作为白色固体的3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)磺酰基)苯基)-5-(三氟甲基)异噁唑(0.053g,收率为49%)。
1H NMR(CDCl3):8.73(d,J=7.2Hz,1H),7.26-7.28(m,1H),7.16(d,J=2.8Hz,1H),3.97(q,J=8.8Hz,2H),2.78(s,3H).
制备例5
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑(化合物22)的制备
(1)4-氯-2-甲基-5-(5-(三氟甲基)异噁唑-3-基)苯磺酰氯
在将反应混合物的温度维持为低于30℃的情况下,向3-(2-氯-4-甲基苯基)-5-(三氟甲基)异噁唑(5.0g,19.1mmol)中缓缓加入氯磺酸(11.1g,95.5mmol)。然后,将得到的混合物加热至80℃并保持18小时。冷却至室温后,将反应混合物小心地投入冰中,滤取沉淀,用蒸馏水充分洗涤,干燥,由此得到6.1g的粗产物。如此得到的粗产物不经任何纯化而继续使用。
1H NMR(CDCl3):8.48(s,1H),7.63(s,1H),7.21(s,1H),2.84(s,3H).
(2)4-氯-2-甲基-5-(5-(三氟甲基)异噁唑-3-基)苯硫醇
于室温向4-氯-2-甲基-5-(5-(三氟甲基)异噁唑-3-基)苯磺酰氯(6.1g,16.9mmol)与冰乙酸(60mL)的混合物中分批地加入锌粉(5.5g,84.5mmol)。然后,使得到的混合物回流4小时。冷却至室温后,将反应混合物用蒸馏水和乙酸乙酯稀释,通过硅藻土床进行过滤。将有机层用蒸馏水充分洗涤,用硫酸钠干燥,过滤并在减压下浓缩,由此得到作为淡黄色固体的3.89g的粗产物。如此得到的粗产物不经任何纯化而继续使用。
1H NMR(CDCl3):7.69(s,1H),7.32(s,1H),7.19(s,1H),3.43(s,1H),2.37(s,3H).
(3)3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑(化合物22)
将4-氯-2-甲基-5-(5-(三氟甲基)异噁唑-3-基)苯硫醇(3.89g,13.2mmol)的二甲基甲酰胺(20mL)溶液冷却至0℃。然后,向冷却后的溶液中依次加入碳酸钾(2.7g,19.8mmol)和三氟碘乙烷(5.3g,19.8mmol),然后将得到的混合物于室温搅拌6小时。然后,将反应混合物投入蒸馏水中,使用二氯甲烷(3x 25mL)萃取。将合并的有机层用蒸馏水洗涤,用硫酸钠干燥,过滤并在减压下浓缩,由此得到粗产物。然后通过柱色谱(乙酸乙酯∶正己烷=1∶5)纯化残余物,成功得到3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑(3.90g,收率为78.8%)。
1H NMR(CDCl3):7.87(s,1H),7.40(s,1H),7.12(s,1H),3.44(q,J=9.6Hz,2H),2.50(s,3H).
制备例6
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑(化合物23)的制备
于-5至0℃向3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑(0.300g,0.798mmol)的二氯甲烷(25mL)溶液中加入m-CPBA(纯度为65%,0.212g,0.798mmol)。将反应混合物于-5至10℃搅拌30分钟,然后使用饱和NaHCO3溶液(70mL)淬灭。进行层分离,使用二氯甲烷(3x 25mL)萃取水性级分。将合并的有机层用饱和NaHCO3溶液(2x 50mL)洗涤,用硫酸钠干燥,在减压下除去溶剂。然后通过柱色谱(乙酸乙酯:正己烷=1∶1)纯化残余物,成功得到作为白色固体的3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑(0.280g,收率为90.0%)。
1H NMR(CDCl3):8.34(s,1H),7.47(s,1H),7.10(s,1H),3.40-3.52(m,2H),2.46(s,3H).
以下表1中列举了本发明的代表性化合物,但本发明不限于这些化合物。
表1中所示的除了制备例1至6中得到的化合物以外的化合物是通过与制备例1至6相似的方法或说明书中记载的方法制造的。
表1中的缩写如下所示。
F:氟,Cl:氯,Me:甲基,CF3:三氟甲基,CF2CF3:五氟乙基,CF2CF2CF3:七氟丙基,CF2CF2CF2CF3:九氟丁基,CHF2:二氟甲基,CF2Cl:氯二氟甲基,Ph:苯基,CF2Ph:二氟(苯基)甲基。
表1:
表2:属于本发明的式(I)的合成化合物的详细情况及1H NMR:
制剂例1:乳剂
将10份本发明的各化合物溶解于45份150和35份N-甲基吡咯烷酮中。向其中加入10份乳化剂(商品名:/>3005X,Toho Chemical Industry Co.,Ltd.制)。通过搅拌将混合物混合,制成10%乳剂。
制剂例2:可湿性粉剂
将20份本发明的各化合物加入至2份十二烷基硫酸钠、4份木质素磺酸钠、20份合成水合二氧化硅的细粉、和54份粘土的混合物中。使用果汁搅拌机,通过搅拌将混合物混合,制成20%可湿性粉剂。
制剂例3:颗粒剂
向5份本发明的各化合物中加入2份十二烷基苯磺酸钠、10份膨润土、和83份粘土,通过搅拌将各混合物充分混合。向其中加入适量的水。进一步搅拌得到的混合物,使用造粒机制成颗粒。将颗粒剂在空气中干燥,制成5%颗粒剂。
制剂例4:粉尘剂
将1份本发明的各化合物溶解于适量的丙酮中。向其中加入5份合成水合二氧化硅的细粉、0.3份酸性磷酸异丙酯(PAP)、和93.7份粘土。使用果汁搅拌机,通过搅拌将混合物混合,通过蒸发除去丙酮,制成1%粉尘剂。
制剂例5:可流动制剂
将20份本发明的各化合物与含有3份聚氧乙烯三苯乙烯基苯基醚磷酸酯三乙醇胺和0.2份426R的20份水混合。将混合物供于使用DYNO-Mill的湿法粉碎,与含有8份丙二醇和0.32份黄原胶的60份水混合,制成20%水中混悬剂。
以下,给出试验例来证明本发明的化合物可用作杀螨剂和杀线虫剂的活性成分。
化合物A是JP2008-308448A的说明书中言及的代表性化合物。该化合物A与[I-Ib]No.2-1的化合物一致。
试验例1(针对二斑叶螨的杀螨试验)
将一片无纺布(4.5x 5.5cm)通过在塑料杯盖上形成的切口悬挂于塑料杯内。将水倒入杯中后,用杯盖将杯子盖住。然后将一片芸豆叶(约3.5x 4.5cm)置于充分浸泡的无纺布上。将附有二斑叶螨(约30只供试螨)的另一片芸豆叶置于第一片叶片上方,将无纺布和叶片置于温度为25±2℃、湿度为40%的恒温箱中过夜。翌日早晨,在螨群已移至下方叶片时除去上方的叶片。
向本发明的化合物的甲醇溶液中加入Sorpol 355(Tobo Kagaku Co.,Ltd.制)的水溶液(100ppm),由此制备含有本发明的化合物(100ppm和5ppm)的杀螨制剂。
将这些杀螨制剂喷洒至叶片上,将叶片在空气中干燥后,置于恒温箱(25±2℃,湿度为50%)中。在2天后计算二斑叶螨的死亡率。该试验的结果示于表3:
表3
在5ppm时显示100%死亡率的化合物(来自表3)如下:
化合物编号:2、8、19、23、35、38、43、44、55和56。
试验例2(针对二斑叶螨的杀卵试验)
将一片无纺布(4.5x 5.5cm)通过在塑料杯盖上形成的切口悬挂于塑料杯内。将水倒入杯中后,用杯盖将杯子盖住。然后将一片芸豆叶(约3.5x 4.5cm)置于充分浸泡的无纺布上。将20只二斑叶螨的雌性成虫置于叶片上方,将无纺布和叶片置于温度为25±2℃、湿度为40%、16小时光照、8小时黑暗的恒温箱中。
翌日,再次调整雌性成虫的数量使其为20只,然后将2mL以与试验例1相同的方式制备的含有本发明的化合物(10ppm)的杀螨制剂喷洒至叶片上,将叶片在空气中干燥后,置于恒温箱(25±2℃,湿度为50%)中。在喷洒杀螨制剂后第6天计算二斑叶螨的杀卵率。
该试验的结果示于表4:
表4
在10ppm时显示100%死亡率的化合物(来自表4)如下:
化合物编号:2、17、19、23、35、38、43、44、55和56。
在表3中于5ppm时显示100%死亡率、且在表4中于10ppm时显示100%死亡率的化合物(来自表3和表4)如下:
化合物编号:2、19、23、35、38、43、44、55和56。
试验例3(针对二斑叶螨的杀螨试验(内吸活性))
针对芸豆罐(直径为6.5cm,高度为6.5cm),于播种8天后,以10mg a.i./罐用10mL试验化合物溶液浸湿罐。施用后,将植物置于温度为25±2℃的温室中。5天后,将来自经处理的罐的一片芸豆叶(约3.5x 4.5cm)置于充分浸泡的无纺布上。将二斑叶螨(约30只供试螨)置于叶片上,将杯置于温度为25±2℃的恒温箱中。在2天后计算二斑叶螨成虫的死亡率。显示50%以上的死亡率的化合物如下:
化合物编号:2、16、17、23、35、43、44和49。
试验例4(针对根结线虫的杀线虫试验)
向装有2/3瓶海砂(8g)的广口玻璃小瓶中加入1mL所期望浓度(40ppm)的试验化合物和1mL线虫悬浮液(500只线虫/mL)。拉伸封口膜密封瓶口,在中央穿孔。将2-3周龄的番茄植株于茎部切下,插入试验小瓶中。将小瓶保存于温度为25±2℃的恒温箱中。在2周后,将植株小心地从小瓶中取出,评价根结瘤。评价基于0-4分的评分(0分为无侵染,4分为100%侵染)进行。根据表5所示的指数来判断根结的损害程度:
表5
根结指数 | 根结形成程度 |
4 | 观察到无数的结,且根的生长受到抑制 |
3 | 在整条根上观察到许多结 |
2 | 观察到结 |
1 | 观察到明显的结 |
0 | 未观察到结 |
显示1以下的根结瘤指数的化合物如下:
化合物编号:2、5、9、10、13、14、17、19、20、23、25、27、29、31、35、38、40、43、44、46、49、50、55和56。
(注意事项)
如上所述,通过本发明的优选实施例来对本发明进行了说明。然而,应当理解的是,本发明的范围应仅以权利要求书为基准。可以理解的是,本文中引用的专利、专利申请和文献以参考方式并入本申请,如同其内容被具体描述在本文中。本申请基于2017年11月30日向印度专利局(印度知识产权局)提交的印度专利申请号201711042933主张优先权,其全部内容以参考方式并入本文。
产业上的可利用性
本发明的异噁唑化合物针对广范围的害虫、例如螨和植物寄生性线虫显示优异的控制效果,可用作农业和园艺用途的杀螨剂或杀线虫剂。
Claims (33)
2.根据权利要求1的异噁唑化合物或其盐,其中R为正丙基或2,2,2-三氟乙基。
3.根据权利要求1或2的异噁唑化合物或其盐,其中A1为氟、氯或甲基。
4.根据权利要求1或2的异噁唑化合物或其盐,其中A2为氟、氯或甲基。
5.根据权利要求1或2的异噁唑化合物或其盐,其中B1为氢或甲基。
6.根据权利要求1或2的异噁唑化合物或其盐,其中B2为二氟甲基、三氟甲基、氯二氟甲基、五氟乙基、七氟丙基或苯基二氟甲基。
7.根据权利要求1或2的异噁唑化合物或其盐,其中n为0或1的整数。
8.根据权利要求1的异噁唑化合物或其盐,其选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(七氟丙基)异噁唑;
5-(二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
5-(二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟(苯基)甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟(苯基)甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
9.根据权利要求1的异噁唑化合物或其盐,其选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(七氟丙基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
10.根据权利要求1的异噁唑化合物或其盐,其选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
5-(氯二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
11.根据权利要求1的异噁唑化合物或其盐,其选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
12.害虫控制剂,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐作为活性成分。
13.农业用组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐。
14.用于控制害虫的组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐。
15.杀螨组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐。
16.杀卵组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐,其中,所述异噁唑化合物不是5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑。
17.杀线虫组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐。
18.用于控制螨的组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐。
19.用于控制虫卵或卵的组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐,其中,所述异噁唑化合物不是5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑。
20.用于控制线虫的组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐。
21.用于控制螨的用途的组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐。
22.用于控制虫卵或卵的用途的组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐,其中,所述异噁唑化合物不是5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑。
23.用于控制线虫的用途的组合物,其包含根据权利要求1至11中任一项的异噁唑化合物或其盐。
24.用于控制害虫的方法,其包括将根据权利要求1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤。
25.杀螨的方法,其包括将根据权利要求1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤。
26.杀卵的方法,其包括将根据权利要求1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤,其中,所述异噁唑化合物不是5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑。
27.杀线虫的方法,其包括将根据权利要求1至11中任一项的异噁唑化合物或其盐施用至植物或植物周边、或者种植植物的土壤。
28.根据权利要求1至11中任一项的异噁唑化合物或其盐的作为杀螨剂的用途。
29.异噁唑化合物或其盐的作为杀螨剂的用途,其中,所述异噁唑化合物选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(七氟丙基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
30.根据权利要求1至11中任一项的异噁唑化合物或其盐的作为杀卵剂的用途,其中,所述异噁唑化合物不是5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑。
31.异噁唑化合物或其盐的作为杀卵剂的用途,其中,所述异噁唑化合物选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
5-(氯二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
32.根据权利要求1至11中任一项的异噁唑化合物或其盐的作为杀线虫剂的用途。
33.异噁唑化合物或其盐的作为杀线虫剂的用途,其中,所述异噁唑化合物选自由下述组成的组:
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(全氟乙基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)磺酰基)苯基)-5-(全氟丙基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(全氟丁基)异噁唑;
5-(二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(二氟(苯基)甲基)-3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二甲基-5-((2,2,2-三氟乙基)磺酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二氟-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2,4-二氯-5-((2,2,2-三氟乙基)硫基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-(丙基亚硫酰基)苯基)-5-(三氟甲基)异噁唑;
3-(2-氟-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-4-甲基-5-(三氟甲基)异噁唑;
5-(二氟(苯基)甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(氯二氟甲基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(氯二氟甲基)异噁唑;
5-(二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)硫基)苯基)异噁唑;
5-(氯二氟甲基)-3-(2,4-二甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)异噁唑;
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)-5-(二氟甲基)异噁唑;和
3-(2-氯-4-甲基-5-((2,2,2-三氟乙基)亚硫酰基)苯基)-5-(二氟甲基)异噁唑。
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AR113861A1 (es) | 2020-06-17 |
KR102639171B1 (ko) | 2024-02-22 |
JP2021504394A (ja) | 2021-02-15 |
JP7202024B2 (ja) | 2023-01-11 |
MA50937A (fr) | 2020-10-07 |
HUE059992T2 (hu) | 2023-01-28 |
US20200288717A1 (en) | 2020-09-17 |
KR20200093574A (ko) | 2020-08-05 |
BR112020010706A2 (pt) | 2021-09-28 |
CN111683930A (zh) | 2020-09-18 |
ES2920057T3 (es) | 2022-08-01 |
TW201925181A (zh) | 2019-07-01 |
EP3717461B1 (en) | 2022-06-15 |
TWI795477B (zh) | 2023-03-11 |
AU2018374625A1 (en) | 2020-06-04 |
CA3082870A1 (en) | 2019-06-06 |
PL3717461T3 (pl) | 2022-10-10 |
WO2019106584A1 (en) | 2019-06-06 |
AU2018374625B2 (en) | 2023-06-29 |
EP3717461A1 (en) | 2020-10-07 |
US11116218B2 (en) | 2021-09-14 |
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