TW201843138A - 三取代矽基甲基苯氧基喹啉及類似物 - Google Patents
三取代矽基甲基苯氧基喹啉及類似物 Download PDFInfo
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- TW201843138A TW201843138A TW107114969A TW107114969A TW201843138A TW 201843138 A TW201843138 A TW 201843138A TW 107114969 A TW107114969 A TW 107114969A TW 107114969 A TW107114969 A TW 107114969A TW 201843138 A TW201843138 A TW 201843138A
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- Prior art keywords
- alkyl
- group
- halogen atoms
- formula
- aryl
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- 150000001875 compounds Chemical class 0.000 claims abstract description 226
- 238000000034 method Methods 0.000 claims abstract description 140
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- 125000000217 alkyl group Chemical group 0.000 claims description 307
- -1 hydroxyimino Chemical group 0.000 claims description 171
- 125000005843 halogen group Chemical group 0.000 claims description 147
- 125000000623 heterocyclic group Chemical group 0.000 claims description 79
- 125000003118 aryl group Chemical group 0.000 claims description 60
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- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 41
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 33
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
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- 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
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- KNDVJPKNBVIKML-UHFFFAOYSA-N tetraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(CN2N=C(N=N2)C(F)(F)F)=NN1C1=NC=CC=C1Cl KNDVJPKNBVIKML-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
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- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
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- 229950007146 tigolaner Drugs 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
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- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
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- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
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- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 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
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-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
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
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- ROVMHMGRSYLCTP-UHFFFAOYSA-N trimethyl-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]silane Chemical compound CC1(C)OB(C[Si](C)(C)C)OC1(C)C ROVMHMGRSYLCTP-UHFFFAOYSA-N 0.000 description 1
- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-O tritert-butylphosphanium Chemical compound CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-O 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
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000001113 umbilicus Anatomy 0.000 description 1
- 239000004061 uncoupling agent Substances 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.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 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 244000000006 viral plant pathogen Species 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- JRPGMCRJPQJYPE-UHFFFAOYSA-N zinc;carbanide Chemical compound [CH3-].[CH3-].[Zn+2] JRPGMCRJPQJYPE-UHFFFAOYSA-N 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Abstract
本發明係關於殺真菌活性化合物,更具體言之,係關於三取代矽基甲基苯氧基喹啉及其類似物、用於其製備之製程及中間體以及其作為殺真菌活性化合物、尤其呈殺真菌劑組合物形式的用途。本發明亦係關於用於使用此等化合物或包含其之組合物控制植物之植物病原性真菌的方法。
Description
本發明係關於殺真菌活性化合物,更具體言之,係關於三取代矽基甲基苯氧基喹啉及其類似物、用於其製備之製程及中間體以及其作為殺真菌活性化合物、尤其呈殺真菌劑組合物形式的用途。本發明亦係關於用於使用此等化合物或包含其之組合物控制植物之植物病原性真菌的方法。
已知一些芳氧基喹啉展現殺真菌活性。
在日本專利申請案JP-2014/124411及國際專利申請案WO 2013/002205中,某些苯氧基喹啉一般涵蓋於許多下式化合物之廣泛揭示內容中:其中D及E表示5員至7員環;X表示O、NH或N-C1
-C8
烷基;B (或Y)表示C或N;且R表示各種基團中之:視情況經取代之烷氧基、視情況經二取代之胺基、視情況經取代之且視情況經氧化之烷基硫基或硝基。然而,JP-2014/124411及WO2013/002205既不揭示亦不表明提供其中R表示三取代矽基甲基的化合物。
在日本專利申請案JP-2014/166991中,某些苯氧基喹啉一般涵蓋於許多下式化合物之廣泛揭示內容中:其中A表示5員至7員環;D表示5員至7員烴類或雜環類環;X表示O、S、未經取代或經取代之碳或氮原子;Z及B獨立地表示C或N;且R表示基團CR1
R2
R3
、C=O-R3
、CR3
=CRa
Rb
、CR3
=NRc
、C6
-C10
芳基、炔基或CN。
在國際專利申請案WO 2011/081174中,某些苯氧基喹啉一般涵蓋於許多下式化合物之廣泛揭示內容中:其中D及E表示5員至7員環;X表示O、NH或N-C1
-C8
烷基;B (或Y)表示C或N;且R表示各種基團中之:視情況經取代之烷氧基、視情況經二取代之胺基、視情況經取代之且視情況經氧化之烷基硫基或硝基。然而,JP-2014/124411及WO2013/002205既不揭示亦不表明提供其中R表示三取代矽基甲基的化合物。
在國際專利申請案WO 2012/161071中,某些苯氧基喹啉一般涵蓋於許多下式化合物之廣泛揭示內容中:其中D表示5員至7員環;A1
、A2
、A3
及A4
獨立地表示C或N,條件為An
中之至少一者為N;且R表示視情況經取代之烷基或氰基。然而,WO 2012/161071既不揭示亦不表明提供其中R表示三取代矽基甲基的化合物。
然而,由於例如在活性範圍、毒性、選擇率、施加量、殘餘物之形成及有利製造方面,對殺真菌劑活性化合物之生態及經濟需求不斷增加,且由於問題亦可與抗性相關,持續需要開發在至少一些領域中比已知化合物及組合物具有優勢的新穎殺真菌化合物及組合物。
因此,本發明提供如本文下文所描述之三取代矽基甲基苯氧基喹啉及其類似物,其可用作殺真菌劑。
活性成分
本發明提供式(I)化合物:(I) 其中 · Z係選自由以下組成之群:氫原子、鹵素原子、C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、包含至多9個可相同或不同之鹵素原子的C2
-C8
鹵代烯基、C2
-C8
炔基、包含至多9個可相同或不同之鹵素原子的C2
-C8
鹵代炔基、C3
-C7
環烷基、C4
-C7
環烯基、羥基、C1
-C8
烷氧基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷氧基、芳基、雜環基、甲醯基、C1
-C8
烷基羰基、(羥亞胺基)C1
-C8
烷基、(C1
-C8
烷氧基亞胺基)C1
-C8
烷基、羧基、C1
-C8
烷氧基羰基、胺甲醯基、C1
-C8
烷基胺甲醯基、二-C1
-C8
烷基胺甲醯基、胺基、C1
-C8
烷胺基、二-C1
-C8
烷胺基、硫基、C1
-C8
烷基硫基、C1
-C8
烷基亞磺醯基、C1
-C8
烷基磺醯基、C1
-C6
三烷基矽基、氰基及硝基, 其中該C1
-C8
烷基、C2
-C8
烯基、C2
-C8
炔基及C1
-C8
烷氧基可經一或多個Za
取代基取代,且其中該C3
-C7
環烷基、C4
-C7
環烯基、芳基及雜環基可經一或多個Zb
取代基取代; · n表示0、1、2、3或4; · L表示O、S、SO、SO2
、CR4
R5
或NR6
,其中 o R4
及R5
係獨立地選自由以下組成之群:氫原子、鹵素原子、羥基、C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C1
-C8
烷氧基及包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷氧基,或其可與其所連接之碳原子一起形成羰基; o R6
係選自由以下組成之群:氫原子、C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、包含至多9個可相同或不同之鹵素原子的C2
-C8
鹵代烯基、C3
-C8
炔基、包含至多9個可相同或不同之鹵素原子的C3
-C8
鹵代炔基、C3
-C7
環烷基、包含至多9個可相同或不同之鹵素原子的C3
-C7
鹵代環烷基、C3
-C7
環烷基-C1
-C8
烷基、甲醯基、C1
-C8
烷基羰基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基羰基、C1
-C8
烷氧基羰基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷氧基羰基、C1
-C8
烷基磺醯基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基磺醯基、芳基-C1
-C8
烷基及苯磺醯基,其中該C1
-C8
烷基、C2
-C8
烯基、C3
-C8
炔基可經一或多個R6a
取代基取代,且其中該C3
-C7
環烷基、C3
-C7
環烷基-C1
-C8
烷基、芳基-C1
-C8
烷基及苯磺醯基可經一或多個R6b
取代基取代; · X係獨立地選自由以下組成之群:鹵素原子、C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、包含至多9個可相同或不同之鹵素原子的C2
-C8
鹵代烯基、C2
-C8
炔基、包含至多9個可相同或不同之鹵素原子的C2
-C8
鹵代炔基、C3
-C7
環烷基、C4
-C7
環烯基、羥基、C1
-C8
烷氧基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷氧基、C1
-C6
三烷基矽基、C1
-C6
三烷基矽基甲基、氰基及硝基, 其中該C1
-C8
烷基、C2
-C8
烯基、C2
-C8
炔基及C1
-C8
烷氧基可經一或多個Xa
取代基取代,且該C3
-C7
環烷基及C4
-C7
環烯基可經一或多個Xb
取代基取代; · W為CY1
或N,其中: - Y1係選自由以下組成之群:氫原子、鹵素原子、C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、包含至多9個可相同或不同之鹵素原子的C2
-C8
鹵代烯基、C2
-C8
炔基、包含至多9個可相同或不同之鹵素原子的C2
-C8
鹵代炔基、C3
-C7
環烷基、C4
-C7
環烯基、羥基、C1
-C8
烷氧基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷氧基、芳基、雜環基、甲醯基、C1
-C8
烷基羰基、(羥亞胺基)C1
-C8
烷基、(C1
-C8
烷氧基亞胺基)C1
-C8
烷基、羧基、C1
-C8
烷氧基羰基、胺甲醯基、C1
-C8
烷基胺甲醯基、二-C1
-C8
烷基胺甲醯基、胺基、C1
-C8
烷胺基、二-C1
-C8
烷胺基、硫基、C1
-C8
烷基硫基、C1
-C8
烷基亞磺醯基、C1
-C8
烷基磺醯基、C1
-C6
三烷基矽基、氰基及硝基, 其中該C1
-C8
烷基、C2
-C8
烯基、C2
-C8
炔基及C1
-C8
烷氧基可經一或多個Y1a
取代基取代,且其中該C3
-C7
環烷基、C4
-C7
環烯基、芳基及雜環基可經一或多個Y1b
取代基取代; · Y2
、Y3
、Y4
及Y5
係獨立地選自由以下組成之群:氫原子、鹵素原子、C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、包含至多9個可相同或不同之鹵素原子的C2
-C8
鹵代烯基、C2
-C8
炔基、包含至多9個可相同或不同之鹵素原子的C2
-C8
鹵代炔基、C3
-C7
環烷基、C4
-C7
環烯基、羥基、C1
-C8
烷氧基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷氧基、芳基、雜環基、甲醯基、C1
-C8
烷基羰基、(羥亞胺基)C1
-C8
烷基、(C1
-C8
烷氧基亞胺基)C1
-C8
烷基、羧基、C1
-C8
烷氧基羰基、胺甲醯基、C1
-C8
烷基胺甲醯基、二-C1
-C8
烷基胺甲醯基、胺基、C1
-C8
烷胺基、二-C1
-C8
烷胺基、硫基、C1
-C8
烷基硫基、C1
-C8
烷基亞磺醯基、C1
-C8
烷基磺醯基、C1
-C6
三烷基矽基、氰基及硝基, 其中該C1
-C8
烷基、C2
-C8
烯基、C2
-C8
炔基及C1
-C8
烷氧基可分別地經一或多個Y2a
、Y3a
、Y4a
或Y5a
取代基取代,且其中該C3
-C7
環烷基、C4
-C7
環烯基、芳基及雜環基可分別地經一或多個Y2b
、Y3b
、Y4b
或Y5b
取代基取代; · R1
係選自由以下組成之群:C1
-C8
烷基、C2
-C8
烯基、C2
-C8
炔基、C3
-C7
環烷基、C4
-C7
環烯基、芳基及雜環基, 其中該C1
-C8
烷基、C2
-C8
烯基及C2
-C8
炔基可經一或多個R1a
取代基取代,且其中該C3
-C7
環烷基、C4
-C7
環烯基、芳基及雜環基可經一或多個R1b
取代基取代; · R2
係選自由以下組成之群:羥基、C1
-C8
烷氧基、C1
-C8
烷基、C2
-C8
烯基、C2
-C8
炔基、C3
-C7
環烷基、C4
-C7
環烯基、芳基及雜環基, 其中該C1
-C8
烷氧基、C1
-C8
烷基、C2
-C8
烯基及C2
-C8
炔基可經一或多個R2a
取代基取代,且其中該C3
-C7
環烷基、C4
-C7
環烯基、芳基及雜環基可經一或多個R2b
取代基取代; · 當R1
及R2
表示C1
-C8
烷基或C2
-C8
烯基時,其可與其所連接之矽原子一起形成C3
-C8
矽雜環烷基環或C4
-C8
矽雜環烯基環,其中該C3
-C8
矽雜環烷基環或C4
-C8
矽雜環烯基環可經一或多個R1b
取代; · R3
係選自由以下組成之群:氫原子、鹵素原子、C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、C2
-C8
炔基、C3
-C7
環烷基、C4
-C7
環烯基、羥基、C1
-C8
烷氧基、芳基、芳基-C1
-C8
烷基、雜環基、雜環基-C1
-C8
烷基、羥基-C1
-C8
烷基、C1
-C8
烷氧基-C1
-C8
烷基、C1
-C8
烷基羰氧基-C1
-C8
烷基、芳氧基-C1
-C8
烷基、雜環基氧基-C1
-C8
烷基、胺基-C1
-C8
烷基、C1
-C8
烷胺基-C1
-C8
烷基、二-C1
-C8
烷胺基-C1
-C8
烷基、芳胺基-C1
-C8
烷基、二-芳胺基-C1
-C8
烷基、雜環胺基-C1
-C8
烷基、C1
-C8
烷基羰基胺基-C1
-C8
烷基、C1
-C8
烷氧基羰基胺基-C1
-C8
烷基、C1
-C8
烷基硫基-C1
-C8
烷基、C1
-C8
烷基亞磺醯基-C1
-C8
烷基、C1
-C8
烷基磺醯基-C1
-C8
烷基及氰基-C1
-C8
烷基, 其中該C1
-C8
烷基、C2
-C8
烯基及C2
-C8
炔基可經一或多個R3a
取代基取代,且其中該C3
-C7
環烷基、C4
-C7
環烯基、芳基、芳基-C1
-C8
烷基、雜環基、雜環基-C1
-C8
烷基、芳氧基-C1
-C8
烷基及雜環基氧基-C1
-C8
烷基可經一或多個R3b
取代基取代; · R3
及X在該X鄰近CH2
-SiR1
R2
R3
時可與其分別連接之矽原子及碳原子一起形成5員、6員或7員部分飽和雜環,其中該5員、6員或7員部分飽和雜環可經一或多個R3b
取代基取代; · 當R2
表示C1
-C8
烷氧基且R3
表示C1
-C8
烷氧基或C1
-C8
烷基時,其可與其所連接之矽原子一起形成5員、6員或7員雜環,其中該5員、6員或7員雜環可經一或多個R2b
取代基取代; · Za
、R1a
、R2a
、R3a
、R6a
、Xa
、Y1a
、Y2a
、Y3a
、Y4a
及Y5a
係獨立地選自由以下組成之群:硝基、羥基、氰基、羧基、胺基、硫基、五氟-λ6
-硫基、甲醯基、胺甲醯基、胺基甲酸根、C3
-C7
環烷基、具有1至5個鹵素原子之C3
-C8
鹵代環烷基、C1
-C8
烷胺基、二-C1
-C8
烷胺基、C1
-C8
烷氧基、具有1至5個鹵素原子之C1
-C8
鹵代烷氧基、C1
-C8
烷基硫基、具有1至5個鹵素原子之C1
-C8
鹵代烷基硫基、C1
-C8
烷基羰基、具有1至5個鹵素原子之C1
-C8
鹵代烷基羰基、C1
-C8
烷基胺甲醯基、二-C1
-C8
烷基胺甲醯基、C1
-C8
烷氧基羰基、具有1至5個鹵素原子之C1
-C8
鹵代烷氧基羰基、C1
-C8
烷基羰氧基、具有1至5個鹵素原子之C1
-C8
鹵代烷基羰氧基、C1
-C8
烷基羰基胺基、具有1至5個鹵素原子之C1
-C8
鹵代烷基羰基胺基、C1
-C8
烷基亞磺醯基、具有1至5個鹵素原子之C1
-C8
鹵代烷基亞磺醯基、C1
-C8
烷基磺醯基及具有1至5個鹵素原子之C1
-C8
鹵代烷基磺醯基; · Zb
、R1b
、R2b
、R3b
、R6b
、Xb
、Y1b
、Y2b
、Y3b
、Y4b
及Y5b
係獨立地選自由以下組成之群:鹵素原子、硝基、羥基、氰基、羧基、胺基、硫基、五氟-λ6
-硫基、甲醯基、胺甲醯基、胺基甲酸根、C1
-C8
烷基、C3
-C7
環烷基、具有1至5個鹵素原子之C1
-C8
鹵代烷基、具有1至5個鹵素原子之C3
-C8
鹵代環烷基、C2
-C8
烯基、C2
-C8
炔基、C1
-C8
烷胺基、二-C1
-C8
烷胺基、C1
-C8
烷氧基、具有1至5個鹵素原子之C1
-C8
鹵代烷氧基、C1
-C8
烷基硫基、具有1至5個鹵素原子之C1
-C8
鹵代烷基硫基、C1
-C8
烷基羰基、具有1至5個鹵素原子之C1
-C8
鹵代烷基羰基、C1
-C8
烷基胺甲醯基、二-C1
-C8
烷基胺甲醯基、C1
-C8
烷氧基羰基、具有1至5個鹵素原子之C1
-C8
鹵代烷氧基羰基、C1
-C8
烷基羰氧基、具有1至5個鹵素原子之C1
-C8
鹵代烷基羰氧基、C1
-C8
烷基羰基胺基、具有1至5個鹵素原子之C1
-C8
鹵代烷基羰基胺基、C1
-C8
烷基硫基、具有1至5個鹵素原子之C1
-C8
鹵代烷基硫基、C1
-C8
烷基亞磺醯基、具有1至5個鹵素原子之C1
-C8
鹵代烷基亞磺醯基、C1
-C8
烷基磺醯基及具有1至5個鹵素原子之C1
-C8
鹵代烷基磺醯基; 以及其鹽、N-氧化物、金屬錯合物、類金屬錯合物及光學活性異構體或幾何異構體。
如本文所用,表述「一或多個取代基」係指基於可用鍵結位點之數目,在一個至可能之最多個取代基的範圍內之多個取代基,其限制條件為滿足穩定性及化學可行性之條件。
如本文所用,鹵素意謂氟、氯、溴或碘;甲醯基意謂-CH(=O);羧基意謂-C(=O)OH;羰基意謂-C(=O)-;胺甲醯基意謂-C(=O)NH2
;N-羥基胺甲醯基意謂-C(=O)NHOH;三氟甲磺醯基意謂-SO2
-CF3
;SO表示亞碸基團;SO2
表示碸基團;雜原子意謂硫、氮或氧;亞甲基意謂雙自由基-CH2
-;芳基通常意謂苯基或萘基;除非以不同方式提供,雜環基意謂5員至7員環,較佳地5員至6員環,其可為部分飽和或不飽和的,包含獨立地選自由N、O、S組成之清單的1至4個雜原子。如本文所用,術語「雜環基」涵蓋雜芳基。
如本文所用,表述「5員至7員環」中之術語「員」指定構成環之骨架原子之數目。
如本文所用,含有此等術語之烷基、烯基及炔基以及部分可為直鏈或分支鏈的。
當胺基或任何其他含胺基基團之胺基部分經兩個可相同或不同之取代基取代時,該等兩個取代基與其所連接之氮原子一起可形成雜環基,較佳地5員至7員雜環基,其可經取代或可包括其他雜原子,例如N-嗎啉基或哌啶基。
視化合物中之不對稱中心數而定,本發明化合物中之任一者可以一或多種光學或對掌性異構體形式存在。因此,本發明同樣係關於其所有光學異構體及外消旋或非外消旋混合物(術語「非外消旋」表示不同比例之對映異構體之混合物)且係關於呈各種比例之所有可能立體異構體的混合物。非對映異構體及/或光學異構體可根據一般熟習此項技術者本身已知之方法來分離。
視化合物中之雙鍵數而定,本發明化合物中之任一者亦可以一或多種幾何異構體形式存在。因此,本發明同樣係關於所有幾何異構體且係關於呈各種比例之所有可能的混合物。幾何異構體可根據一般熟習此項技術者本身已知之通用方法來分離。
視鏈或環之取代基之相對位置(同側/反側或順式/反式)而定,本發明化合物中之任一者亦可以一或多種幾何異構體形式存在。因此,本發明同樣係關於所有同側/反側(或順式/反式)異構體及呈各種比例之所有可能同側/反側(或順式/反式)混合物。同側/反側(或順式/反式)異構體可根據一般熟習此項技術者本身已知之通用方法來分離。
當本發明化合物可以互變異構形式存在時,即使當不明確地提及此時,本發明亦涵蓋此類化合物之任何互變異構形式。
式(I)化合物在本文中稱為「活性成分」。
在上式(I)中,Z係較佳地選自由以下組成之群:氫原子、鹵素原子、羥基、C1
-C6
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷基、C1
-C6
烷氧基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷氧基及氰基;更佳地,Z為氫原子或C1
-C6
烷基;甚至更佳地,Z為氫原子或甲基。
在上式(I)中,n較佳地為0或1。
在上式(I)中,L較佳地為O、N或CH2
,更佳地為O。
在上式(I)中,較佳地,X獨立地為鹵素原子、C1
-C6
烷基或C1
-C6
三烷基矽基甲基,更佳地X獨立地為氯原子、氟原子或甲基。
在上式(I)中,較佳地,Y1
、Y2
、Y3
、Y4
或Y5
獨立地選自由以下組成之群:氫原子、鹵素原子、C1
-C6
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷基、C1
-C6
烷氧基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷氧基及氰基;更佳地,Y1
、Y2
、Y3
、Y4
或Y5
係獨立地選自由以下組成之群:氫原子、鹵素原子、C1
-C6
烷基及包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷基;甚至更佳地,Y1
、Y2
、Y3
、Y4
或Y5
獨立地為鹵素原子、氟原子、氯原子、甲基或三氟甲基。
在上式(I)中,R1
較佳地為C1
-C6
烷基,更佳地為甲基。
在上式(I)中,R2
較佳地為C1
-C6
烷基,更佳地為甲基。
在上式(I)中,R3
係較佳地選自由以下組成之群:羥基、C1
-C6
烷基、C2
-C6
烯基、C1
-C6
烷氧基、可經取代之芳基(例如,苯基及C1
-C6
烷氧基-苯基)、芳基-C1
-C6
烷基、雜環基及雜環基-C1
-C6
烷基;更佳地,R3
係選自由以下組成之群:羥基、C1
-C6
烷基、C2
-C6
烯基、C1
-C6
烷氧基、芳基、芳基-C1
-C6
烷基及雜環基;甚至更佳地,R3
為羥基、甲基、乙烯基、異丙氧基、苯基、噻吩基或苯甲基。
在一些實施例中,根據本發明之化合物為式(I)化合物,其中: ● W為CY1
,其中Y1
如上文所揭示;較佳地,Y1
係選自由以下組成之群:氫原子、鹵素原子、C1
-C6
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷基、C1
-C6
烷氧基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷氧基及氰基;更佳地,Y1
係選自由以下組成之群:氫原子、鹵素原子、C1
-C6
烷基及包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷基;甚至更佳地,Y1
為氫原子、氟原子、氯原子、甲基或三氟甲基; ● Y2
、Y3
、Y4
或Y5
如上文所揭示;較佳地,Y2
、Y3
、Y4
或Y5
係獨立地選自由以下組成之群:氫原子、鹵素原子、C1
-C6
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷基、C1
-C6
烷氧基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷氧基及氰基;更佳地,Y2
、Y3
、Y4
或Y5
係獨立地選自由以下組成之群:氫原子、鹵素原子、C1
-C6
烷基及包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷基;甚至更佳地,Y2
、Y3
、Y4
或Y5
獨立地為氫原子、氟原子、氯原子、甲基或三氟甲基。 ● L如上文所揭示;較佳地,L為O、NH或CH2
; ● X如上文所揭示;較佳地,X獨立地為鹵素原子、C1
-C6
烷基或C1
-C6
三烷基矽基甲基;更佳地,X獨立地為氯原子、氟原子或甲基; ● n如上文所揭示;較佳地,n為0或1; ● R1
、R2
及R3
如本文所揭示;較佳地,R1
為C1
-C6
烷基,更佳地為甲基;較佳地,R2
為C1
-C6
烷基,更佳地為甲基;較佳地,R3
係選自由以下組成之群:羥基、C1
-C6
烷基、C2
-C6
烯基、C1
-C6
烷氧基、可經取代之芳基、芳基-C1
-C6
烷基、雜環基及雜環基-C1
-C6
烷基;更佳地地,R3
係選自由以下組成之群:羥基、C1
-C6
烷基、C2
-C6
烯基、C1
-C6
烷氧基、芳基、芳基-C1
-C6
烷基及雜環基;甚至更佳地,R3
為羥基、甲基、乙烯基、異丙氧基、苯基、噻吩基或苯甲基。
在一些其他實施例中,根據本發明之化合物為式(I)化合物,其中: ● W為N; ● Y2
、Y3
、Y4
或Y5
如上文所揭示;較佳地,Y2
、Y3
、Y4
或Y5
係獨立地選自由以下組成之群:氫原子、鹵素原子、C1
-C6
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷基、C1
-C6
烷氧基、包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷氧基及氰基;更佳地,Y2
、Y3
、Y4
或Y5
係獨立地選自由以下組成之群:氫原子、鹵素原子、C1
-C6
烷基及包含至多9個可相同或不同之鹵素原子的C1
-C6
鹵代烷基;甚至更佳地,Y2
、Y3
、Y4
或Y5
獨立地為氫原子、氟原子、氯原子、甲基或三氟甲基。 ● L如上文所揭示;較佳地,L為O、NH或CH2
; ● X如上文所揭示;較佳地,X獨立地為鹵素原子、C1
-C6
烷基或C1
-C6
三烷基矽基甲基;更佳地,X獨立地為氯原子、氟原子或甲基; ● n如上文所揭示;較佳地,n為0或1; ● R1
、R2
及R3
如本文所揭示;較佳地,R1
為C1
-C6
烷基,更佳地為甲基;較佳地,R2
為C1
-C6
烷基,更佳地為甲基;較佳地,R3
係選自由以下組成之群:羥基、C1
-C6
烷基、C2
-C6
烯基、C1
-C6
烷氧基、可經取代之芳基、芳基-C1
-C6
烷基、雜環基及雜環基-C1
-C6
烷基;更佳地地,R3
係選自由以下組成之群:羥基、C1
-C6
烷基、C2
-C6
烯基、C1
-C6
烷氧基、芳基、芳基-C1
-C6
烷基及雜環基;甚至更佳地,R3
為羥基、甲基、乙烯基、異丙氧基、苯基、噻吩基或苯甲基。
關於根據本發明之化合物之取代基之上文所提及偏好可以各種方式組合。因此,較佳特徵之此等組合提供根據本發明之化合物的子類。根據本發明之較佳化合物之該等子類之實例為: - L之較佳特徵與R1
、R2
、R3
、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z之一或多個較佳特徵; - R1
之較佳特徵與L、R2
、R3
、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z之一或多個較佳特徵; - R2
之較佳特徵與L、R1
、R3
、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z之一或多個較佳特徵; - R3
之較佳特徵與L、R1
、R2
、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z之一或多個較佳特徵; - n之較佳特徵與L、R1
、R2
、R3
、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z之一或多個較佳特徵; - X之較佳特徵與L、R1
、R2
、R3
、n、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z之一或多個較佳特徵; - Y1
之較佳特徵與L、R1
、R2
、R3
、n、X、Y2
、Y3
、Y4
、Y5
、W及Z之一或多個較佳特徵; - Y2
之較佳特徵與L、R1
、R2
、R3
、n、X、Y1
、Y3
、Y4
、Y5
、W及Z之一或多個較佳特徵; - Y3
之較佳特徵與L、R1
、R2
、R3
、n、X、Y1
、Y2
、Y4
、Y5
、W及Z之一或多個較佳特徵; - Y4
之較佳特徵與L、R1
、R2
、R3
、n、X、Y1
、Y2
、Y3
、Y5
、W及Z之一或多個較佳特徵; - Y5
之較佳特徵與L、R1
、R2
、R3
、n、X、Y1
、Y2
、Y3
、Y4
、W及Z之一或多個較佳特徵; - W之較佳特徵與L、R1
、R2
、R3
、n、X、Y1
、Y2
、Y3
、Y4
、Y5
及Z之一或多個較佳特徵; - Z之較佳特徵與L、R1
、R2
、R3
、n、p、X以及Y1
、Y2
、Y3
、Y4
、Y5
及W之一或多個較佳特徵;
在根據本發明之化合物之取代基之較佳特徵的此等組合中,該等較佳特徵亦可選自L、R1
、R2
、R3
、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z中之每一者的更佳特徵以便形成根據本發明之化合物的最佳子類。
用於製備活性成分之製程
本發明亦係關於用於製備式(I)化合物之製程。
如本文所定義之式(I)化合物可藉由製程P1來製備,該製程P1包含以下步驟:使式(II)之鹵代甲基芳基或其鹽中之一者:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義,且U1
表示氯原子、溴原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基,與式(IIIa)之二矽基衍生物反應:其中R1
、R2
及R3
如本文所定義。
製程P1可在諸如鈀之過渡金屬催化劑存在下進行,且適當時在膦配位體或N-雜環碳烯配位體存在下進行,適當時在鹼存在下進行,且適當時在溶劑存在下根據已知製程(Organic Letters (2003),5
, 3483, Organic Letters (2007),9
, 3785及其中所引用之參考文獻)進行。
式(II)之衍生物(其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義且U1
表示氯原子或溴原子)可根據已知製程藉由式(IV)之甲苯衍生物或其鹽中之一者的基團鹵化來製備:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義。
式(IV)之衍生物(其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義)可根據製程P4製備。
式(II)之衍生物(其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義且U1
表示氯原子、溴原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基)可根據已知製程藉由式(V)之羥甲基衍生物或其鹽中之一者的鹵化或磺化來製備:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義。
式(IIIa)之二矽基衍生物為已知的或可藉由已知製程來製備。
其中R3
表示羥基的式(I)化合物可由其中R3
表示C1
-C6
烷氧基的式(I)化合物(其本身藉由製程P1製備)根據已知製程(Organic Letters (2003),5
, 3483)藉由酸性水解來製備。
其中R3
表示氟原子的式(I)化合物可藉由已知製程(Synlett (2012),23
, 1064及其中所引用之參考文獻)由其中R3
表示C1
-C6
烷氧基的式(I)化合物(其本身由製程P1製備)來製備,或可藉由已知製程(EP1908472)由R3
表示羥基的式(I)化合物來製備。
製程P1可在諸如金屬鹽或錯合物之催化劑存在下進行。出於此目的,適合之金屬衍生物為過渡金屬催化劑,諸如鈀。出於此目的,適合之金屬鹽或錯合物為例如:氯化鈀、乙酸鈀、肆(三苯基膦)鈀(0)、雙(二苯亞甲基丙酮)鈀(0)、參(二苯亞甲基丙酮)二鈀(0)、雙(三苯基膦)二氯化鈀(II)、[1,1'-雙(二苯膦基)二茂鐵]二氯化鈀(II)、雙(苯烯丙基)二氯化二鈀(II)、雙(烯丙基)-二氯化二鈀(II)或[1,1'-雙(二-第三丁基膦基)二茂鐵]二氯化鈀(II)。
亦可藉由單獨添加至鈀鹽與配位體或鹽之反應來在反應混合物中產生鈀錯合物,諸如三乙基膦、三-第三丁基膦、三第三丁基鏻四氟硼酸鹽、三環己基膦、2-(二環己基膦)聯苯、2-(二-第三丁基膦)聯苯、2-(二環己基膦)-2'-(N,N-二甲胺基)二苯基、2-(第三丁基膦)-2'-(N,N-二甲胺基)聯苯、2-二-第三丁基膦-2',4',6'-三異丙基聯苯2-二環己基膦基-2',4',6'-三異丙基聯苯、2-二環己基膦基-2,6'-二甲氧基聯苯、2-二環己基膦基-2',6'-二異丙氧基聯苯、三苯基膦、參-(鄰甲苯基)膦、3-(二苯膦基)苯磺酸鈉、參-2-(甲氧基-苯基)膦、2,2'-雙(二苯膦基)-1,1'-聯萘、1,4-雙(二苯膦基)丁烷、1,2-雙(二苯膦基)乙烷、1,4-雙(二環己基膦)丁烷、1,2-雙(二環己基膦)-乙烷、2-(二環己基膦)-2'-(N,N-二甲胺基)-聯苯、1,1'-雙(二苯膦基)-二茂鐵、(R)-(-)-1-[(S)-2-二苯基-膦基)二茂鐵基]乙基二環己基膦、參-(2,4-第三丁基-苯基)亞磷酸鹽、二(1-金剛烷基)-2-嗎啉基苯基膦或1,3-雙(2,4,6-三甲基苯基)咪唑鎓氯化物。
亦宜選擇來自商業目錄之適當催化劑及/或配位體,諸如Strem Chemicals之「Metal Catalysts for Organic Synthesis」或Strem Chemicals之「Phosphorous Ligands and Compounds」。
用於進行製程P1之適合之鹼可為此類反應習用之無機鹼及有機鹼。較佳使用:鹼土金屬或鹼金屬氫氧化物,諸如氫氧化鈉、氫氧化鈣、氫氧化鉀或其他氫氧化銨衍生物;鹼土金屬、鹼金屬或氟化銨,諸如氟化鉀、氟化銫或氟化四丁銨;鹼土金屬或鹼金屬碳酸鹽,諸如碳酸鈉、碳酸鉀、碳酸氫鉀、碳酸氫鈉或碳酸銫;鹼金屬或鹼土金屬乙酸鹽,諸如乙酸鈉、乙酸鋰、乙酸鉀或乙酸鈣;鹼金屬或鹼土金屬磷酸鹽,諸如鹼性磷酸三鉀;鹼金屬醇化物,諸如第三丁醇鉀或第三丁醇鈉;三級胺,諸如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二環己基甲胺、N,N-二異丙基乙胺、N-甲基哌啶、N,N-二甲胺基吡啶、二氮雜二環辛烷(DABCO)、二氮雜二環壬烯(DBN)或二氮雜雙環十一烯(DBU);以及芳族鹼,諸如吡啶、甲基吡啶、二甲基吡啶或三甲基吡啶。
用於進行製程P1之適合之溶劑可為習用惰性有機溶劑。較佳使用:視情況選用之鹵化、脂族、脂環或芳族烴,諸如石油醚、戊烷、己烷、庚烷、環己烷、甲基環己烷、苯、甲苯、二甲苯或十氫萘;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,諸如乙醚、二異丙基醚、甲基第三丁基醚、甲基第三戊基醚、二噁烷、四氫呋喃、2-甲基四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,諸如乙腈、丙腈、正丁腈或異丁腈或苯甲腈;醯胺,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基甲醯苯胺、N-甲基吡咯啶酮或六甲基磷醯三胺;脲,諸如1,3-二甲基-3,4,5,6-四氫-2(1H)-嘧啶酮;酯,諸如乙酸甲酯或乙酸乙酯;亞碸,諸如二甲亞碸;或碸,諸如環丁碸;及其混合物。
亦可能宜用諸如水或醇之共溶劑進行製程P1,該醇諸如甲醇、乙醇、丙醇、異丙醇或第三丁醇。
製程P1可在諸如氬氣或氮氣氛圍之惰性氛圍中進行。當進行製程P1時,每莫耳式(II)化合物可採用1莫耳或過量之式(IIIa)化合物及1至5莫耳鹼及0.01至20莫耳%之鈀錯合物。亦有可能以其他比率使用反應組分。藉由已知方法進行處理。
如本文所定義之式(I)化合物可藉由製程P2來製備,該製程P2包含以下步驟:使式(VI)化合物或其鹽中之一者:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義,且U2
表示氯原子、溴原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基,與式(IIIb)之硼衍生物反應:其中W3
表示硼衍生物,諸如,硼酸、硼酸酯或三氟硼酸鉀衍生物; R1
及R2
獨立地表示C1
-C8
烷基、C2
-C8
烯基、C3
-C7
環烷基、芳基或雜環基;以及 R3
表示氫原子或C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、C2
-C8
炔基、C3
-C7
環烷基、C4
-C7
環烯基、芳基、芳基-C1
-C8
烷基、C1
-C8
烷氧基、雜環基、雜環基-C1
-C8
烷基、羥基-C1
-C8
烷基、C1
-C8
烷氧基-C1
-C8
烷基、C1
-C8
烷基羰氧基-C1
-C8
烷基、芳氧基-C1
-C8
烷基、雜環基氧基-C1
-C8
烷基、胺基-C1
-C8
烷基、C1
-C8
烷胺基-C1
-C8
烷基、二-C1
-C8
烷胺基-C1
-C8
烷基、芳胺基-C1
-C8
烷基、二-芳胺基-C1
-C8
烷基、雜環胺基-C1
-C8
烷基、C1
-C8
烷基羰基胺基-C1
-C8
烷基、C1
-C8
烷氧基羰基胺基-C1
-C8
烷基、C1
-C8
烷基硫基-C1
-C8
烷基、C1
-C8
烷基亞磺醯基-C1
-C8
烷基、C1
-C8
烷基磺醯基-C1
-C8
烷基或氰基-C1
-C8
烷基。
應理解,該R1
、R2
及R3
中之任一者可如關於式(I)化合物之R1
、R2
及R3
所揭示而經取代。
式(VI)之衍生物(其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義且U2
表示氯原子、溴原子或碘原子)可根據已知製程(Patai's Chemistry of Functional Groups - Amino, Nitroso, Nitro and Related Groups - 1996)藉由重氮化式(VII)之苯胺或其鹽中之一者來製備:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義。
式(VII)之苯胺可根據已知製程(Patai's Chemistry of Functional Groups - Amino, Nitroso, Nitro and Related Groups - 1996)藉由還原硝基來製備。
式(IIIb)之硼衍生物為已知的,或可由已知製程來製備。
製程P2可在諸如鈀之過渡金屬催化劑存在下且適當時在膦配位體或N-雜環碳烯配位體存在下,且適當時在鹼存在下且適當時在溶劑存在下進行。出於此目的,適合的鈀鹽或錯合物可如關於製程P1所揭示。
用於進行製程P2之適合的鹼可如關於製程P1所揭示。
用於進行製程P2之適合的溶劑可如關於製程P1所揭示。
亦可能宜用諸如水或醇之共溶劑進行根據本發明之製程P2,該醇諸如甲醇、乙醇、丙醇、異丙醇或第三丁醇。
製程P2可在惰性氛圍中進行。當進行製程P2時,每莫耳式(VI)化合物可採用1莫耳或過量之式(IIIb)化合物及1至5莫耳鹼以及0.01至20莫耳%之過渡金屬錯合物。亦有可能以其他比率使用反應組分。藉由已知方法進行處理。
如本文所定義之式(I)化合物可藉由製程P3來製備,該製程P3包含以下步驟:使式(VI)化合物或其鹽中之一者:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義,且U2
表示氯原子、溴原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基,與式(IIIc)之衍生物反應:其中M1
表示鹼金屬,諸如可藉由1至2個配位體錯合之鋰;或過渡金屬,諸如可藉由1至2個配位體錯合之鹵代鎂或可藉由1至2個配位體錯合之鹵代鋅; R1
及R2
獨立地表示C1
-C8
烷基、C2
-C8
烯基、C3
-C7
環烷基、芳基或雜環基;以及 R3
表示氫原子或C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、C2
-C8
炔基、C3
-C7
環烷基、C4
-C7
環烯基、芳基、芳基-C1
-C8
烷基、C1
-C8
烷氧基、雜環基、雜環基-C1
-C8
烷基、羥基-C1
-C8
烷基、C1
-C8
烷氧基-C1
-C8
烷基、C1
-C8
烷基羰氧基-C1
-C8
烷基、芳氧基-C1
-C8
烷基、雜環基氧基-C1
-C8
烷基、胺基-C1
-C8
烷基、C1
-C8
烷胺基-C1
-C8
烷基、二-C1
-C8
烷胺基-C1
-C8
烷基、芳胺基-C1
-C8
烷基、二-芳胺基-C1
-C8
烷基、雜環胺基-C1
-C8
烷基、C1
-C8
烷基羰基胺基-C1
-C8
烷基、C1
-C8
烷氧基羰基胺基-C1
-C8
烷基、C1
-C8
烷基硫基-C1
-C8
烷基、C1
-C8
烷基亞磺醯基-C1
-C8
烷基、C1
-C8
烷基磺醯基-C1
-C8
烷基或氰基-C1
-C8
烷基。
應理解,該R1
、R2
及R3
中之任一者可如關於式(I)化合物之R1
、R2
及R3
所揭示而經取代。
式(IIIc)化合物可商購或可根據已知製程自對應鹵化衍生物藉由與鎂金屬、鋅金屬或鋰金屬較佳地在無水條件下反應來獲得;或藉由鹵素/金屬交換使用烷基鋰試劑或格林納試劑或由烷基鋰試劑或格林納試劑製備之所製造錯合物較佳地在無水條件下來獲得;或藉由金屬/金屬交換使用氯化鋅或格林納試劑較佳地在無水條件下獲得。
製程P3可在諸如鈀之過渡金屬催化劑存在下且適當時在膦配位體或N-雜環碳烯配位體存在下,且適當時在鹼存在下且適當時在溶劑存在下進行。出於此目的,適合的鈀鹽或錯合物可如關於製程P3所揭示。
用於進行製程P3之適合的鹼可如關於製程P1所揭示。
用於進行製程P3之適合的溶劑可如關於製程P1所揭示。
製程P3可在惰性氛圍中進行。當進行製程P3時,每莫耳式(VI)化合物可採用1莫耳或過量之式(IIIc)化合物及1至5莫耳鹼以及0.01至20莫耳%之過渡金屬錯合物。亦有可能以其他比率使用反應組分。藉由已知方法進行處理。
式I化合物可藉由製程P4製備,該製程P4包含如以下反應流程所示使式(VIII)化合物或其鹽中之一者與式(IX)化合物反應的步驟:製程P4 其中L表示O、S或NR6
; U3
表示氯原子、溴原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基; R1
及R2
獨立地表示C1
-C8
烷基、C2
-C8
烯基、C3
-C7
環烷基、芳基或雜環基;以及 R3
表示氫原子或C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、C2
-C8
炔基、C3
-C7
環烷基、C4
-C7
環烯基、芳基、芳基-C1
-C8
烷基、雜環基、雜環基-C1
-C8
烷基、羥基-C1
-C8
烷基、C1
-C8
烷氧基-C1
-C8
烷基、C1
-C8
烷基羰氧基-C1
-C8
烷基、芳氧基-C1
-C8
烷基、雜環基氧基-C1
-C8
烷基、胺基-C1
-C8
烷基、C1
-C8
烷胺基-C1
-C8
烷基、二-C1
-C8
烷胺基-C1
-C8
烷基、芳胺基-C1
-C8
烷基、二-芳胺基-C1
-C8
烷基、雜環胺基-C1
-C8
烷基、C1
-C8
烷基羰基胺基-C1
-C8
烷基、C1
-C8
烷氧基羰基胺基-C1
-C8
烷基、C1
-C8
烷基硫基-C1
-C8
烷基、C1
-C8
烷基亞磺醯基-C1
-C8
烷基、C1
-C8
烷基磺醯基-C1
-C8
烷基或氰基-C1
-C8
烷基; 以及n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義。
應理解,該R1
、R2
及R3
中之任一者可如關於式(I)化合物之R1
、R2
及R3
所揭示而經取代。
式(IX)化合物為可商購的,或可藉由熟知製程製備。
製程P4可在諸如鈀之過渡金屬催化劑存在下且適當時在膦配位體或N-雜環碳烯配位體存在下進行;或在諸如銅之過渡金屬催化劑存在下且適當時在配位體存在下進行;且適當時在鹼存在下且適當時在溶劑存在下根據已知製程(Organic Letters (2012),14
, 170;Organic Letters (2002), 4, 1623及其中所引用之參考文獻)進行。
適合的基於鈀之催化劑可如關於製程P1所揭示。
出於此目的,適合的銅鹽或錯合物及其水合物為:例如銅金屬、碘化亞銅(I)、氯化亞銅(I)、溴化亞銅(I)、氯化銅(II)、溴化銅(II)、氧化銅(II)、氧化亞銅(I)、乙酸銅(II)、乙酸亞銅(I)、噻吩-2-甲酸亞銅(I)、氰化亞銅(I)、硫酸銅(II)、雙(2,2,6,6-四甲基-3,5-庚二酮酸)銅、三氟甲烷磺酸銅(II)、六氟磷酸肆(乙腈)亞銅(I)、四氟硼酸肆(乙腈)亞銅(I)。
亦可藉由單獨添加至銅鹽與配位體或鹽之反應來在反應混合物中產生銅錯合物,諸如乙二胺、N,N-二甲基伸乙基二胺、N,N'-二甲基伸乙基二胺、外消旋-反-1,2-二胺基環己烷、外消旋-反-N,N'-二甲基環己烷-1,2-二胺、1,1'-聯萘-2,2'-二胺、N,N,N',N'-四甲基乙二胺、脯胺酸、N,N-二甲基甘胺酸、喹啉-8-醇、吡啶、2-胺基吡啶、4-(二甲胺基)吡啶、2,2'-二吡啶基、2,6-二(2-吡啶基)吡啶、2-吡啶甲酸、2-(二甲胺基甲基)-3-羥基吡啶、1,10-啡啉、3,4,7,8-四甲基-1,10-啡啉、2,9-二甲基-1,10-啡啉、4,7-二甲氧基-1,10-啡啉、N,N'-雙[(E)-吡啶-2-基亞甲基]環己烷-1,2-二胺、N-[(E)-苯基亞甲基]、N-[(E)-苯基亞甲基]-環己胺、1,1,1-參(羥基甲基)乙烷、乙二醇、2,2,6,6-四甲基庚烷-3,5-二酮、2-(2,2-二甲基丙醯基)環己酮、乙醯基丙酮、二苯甲基甲烷、2-(2-甲基丙醯基)環己酮、聯苯-2-基(二-第三丁基)膦、伸乙基雙-(二苯基膦)、N,N-二乙基水楊醯胺、2-羥基苯甲醛肟、側氧基[(2,4,6-三甲基苯基)胺基]乙酸或1H-吡咯-2-甲酸。
亦宜從商業目錄(諸如Strem Chemicals之「Metal Catalysts for Organic Synthesis」)或綜述(Chemical Society Reviews (2014),43
, 3525; Coordination Chemistry Reviews (2004),248
, 2337及其中之參考文獻)選擇適當的催化劑及/或配位體。
用於進行製程P4之適合的鹼可如關於製程P1所揭示。
用於進行製程P4之適合的溶劑可如關於製程P1所揭示。
製程P4可在惰性氛圍中進行。當進行方法P4時,每莫耳式(VIII)化合物可採用1莫耳或過量之式(IX)化合物及1至5莫耳鹼以及0.01至20莫耳%之過渡金屬錯合物。亦有可能以其他比率使用反應組分。藉由已知方法進行處理。
式(I)化合物可藉由製程P5來製備,該製程P5包含如以下反應流程所示使式(X)化合物或其鹽中之一者與式(XI)化合物反應的步驟:製程P5 其中L表示CR4
R5
; R4
及R5
獨立地表示氫原子或C1
-C8
烷基; U4
表示溴原子、氯原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基; W1
表示硼衍生物,諸如,硼酸、硼酸酯或三氟硼酸鉀衍生物; R1
及R2
獨立地表示C1
-C8
烷基、C2
-C8
烯基、C3
-C7
環烷基、芳基或雜環基; R3
表示氫原子、C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、C2
-C8
炔基、C3
-C7
環烷基、C4
-C7
環烯基、芳基、芳基-C1
-C8
烷基、C1
-C8
烷氧基、雜環基、雜環基-C1
-C8
烷基、羥基-C1
-C8
烷基、C1
-C8
烷氧基-C1
-C8
烷基、C1
-C8
烷基羰氧基-C1
-C8
烷基、芳氧基-C1
-C8
烷基、雜環基氧基-C1
-C8
烷基、胺基-C1
-C8
烷基、C1
-C8
烷胺基-C1
-C8
烷基、二-C1
-C8
烷胺基-C1
-C8
烷基、芳胺基-C1
-C8
烷基、二-芳胺基-C1
-C8
烷基、雜環胺基-C1
-C8
烷基、C1
-C8
烷基羰基胺基-C1
-C8
烷基、C1
-C8
烷氧基羰基胺基-C1
-C8
烷基、C1
-C8
烷基硫基-C1
-C8
烷基、C1
-C8
烷基亞磺醯基-C1
-C8
烷基、C1
-C8
烷基磺醯基-C1
-C8
烷基或氰基-C1
-C8
烷基;以及 n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義。
應理解,該R1
、R2
及R3
中之任一者可如關於式(I)化合物之R1
、R2
及R3
所揭示而經取代。
式(XI)化合物可藉由已知製程(Journal of the American Chemical Society (1957),79
, 6540; Journal of Organic Chemistry (2000), (65), 4913; Tetrahedron Letters (2002),43
, 8569)製備。
製程P5可在諸如鈀之過渡金屬催化劑存在下且適當時在膦配位體或N-雜環碳烯配位體存在下,且適當時在鹼存在下且適當時在溶劑存在下進行。出於此目的,適合的鈀鹽或錯合物可如關於製程P1所揭示。
用於進行製程P5之適合的鹼可如關於製程P1所揭示。
用於進行製程P5之適合的溶劑可如關於製程P1所揭示。
亦可能宜用諸如水或醇之共溶劑進行根據本發明之製程P5,該醇諸如甲醇、乙醇、丙醇、異丙醇或第三丁醇。
製程P5可在惰性氛圍中進行。當進行方法P5時,每莫耳式(X)化合物可採用1莫耳或過量之式(XI)化合物及1至5莫耳鹼以及0.01至20莫耳%之過渡金屬錯合物。亦有可能以其他比率使用反應組分。藉由已知方法進行處理。
式(I)化合物可藉由製程P6製備,該製程P6包含如以下反應流程所示使式(VIII)化合物或其鹽中之一者與式(XII)化合物反應的步驟:製程P6 其中L表示CR4
R5
; R4
及R5
獨立地表示氫原子、C1
-C8
烷氧基或C1
-C8
烷基; U3
表示溴原子、氯原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基; W2
表示硼衍生物,諸如,硼酸、硼酸酯或三氟硼酸鉀衍生物; R1
及R2
獨立地表示C1
-C8
烷基、C2
-C8
烯基、C3
-C7
環烷基、芳基或雜環基; R3
表示氫原子或C1
-C8
烷基、包含至多9個可相同或不同之鹵素原子的C1
-C8
鹵代烷基、C2
-C8
烯基、C2
-C8
炔基、C3
-C7
環烷基、C4
-C7
環烯基、芳基、芳基-C1
-C8
烷基、C1
-C8
烷氧基、雜環基、雜環基-C1
-C8
烷基、羥基-C1
-C8
烷基、C1
-C8
烷氧基-C1
-C8
烷基、C1
-C8
烷基羰氧基-C1
-C8
烷基、芳氧基-C1
-C8
烷基、雜環基氧基-C1
-C8
烷基、胺基-C1
-C8
烷基、C1
-C8
烷胺基-C1
-C8
烷基、二-C1
-C8
烷胺基-C1
-C8
烷基、芳胺基-C1
-C8
烷基、二-芳胺基-C1
-C8
烷基、雜環胺基-C1
-C8
烷基、C1
-C8
烷基羰基胺基-C1
-C8
烷基、C1
-C8
烷氧基羰基胺基-C1
-C8
烷基、C1
-C8
烷基硫基-C1
-C8
烷基、C1
-C8
烷基亞磺醯基-C1
-C8
烷基、C1
-C8
烷基磺醯基-C1
-C8
烷基或氰基-C1
-C8
烷基;以及 n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義。
應理解,該R1
、R2
及R3
中之任一者可如關於式(I)化合物之R1
、R2
及R3
所揭示而經取代。
式(XII)化合物可由式(XI)化合物藉由已知製程(Tetrahedron Letters (2003),44
, 233及Chemistry Letters (2002), 780)來製備。
製程P6可在諸如鈀之過渡金屬催化劑存在下且適當時在膦配位體或N-雜環碳烯配位體存在下,且適當時在鹼存在下且適當時在溶劑存在下進行。出於此目的,適合的鈀鹽或錯合物可如關於製程P1所揭示。
用於進行製程P6之適合的鹼可如關於製程P1所揭示。
用於進行製程P6之適合的溶劑可如關於製程P1所揭示。
亦可能宜用諸如水或醇之共溶劑進行根據本發明之製程P6,該醇諸如甲醇、乙醇、丙醇、異丙醇或第三丁醇。
製程P6可在惰性氛圍中進行。當進行方法P6時,每莫耳式(VIII)化合物可採用1莫耳或過量之式(XII)化合物及1至5莫耳鹼以及0.01至20莫耳%之過渡金屬錯合物。亦有可能以其他比率使用反應組分。藉由已知方法進行處理。
製程P1、P2、P3、P4、P5及P6通常在大氣壓下進行。亦有可能在加壓或減壓下操作。
當進行製程P1、P2、P3、P4、P5及P6時,可在相對廣範圍內改變反應溫度。一般而言,此等製程係在-78℃至200℃、較佳為-78℃至150℃之溫度下進行。控制該等製程之溫度的方式為使用微波技術。
一般而言,反應混合物係在減壓下濃縮。剩餘之殘餘物可藉由諸如層析或結晶之已知方法自可仍然存在之任何雜質中釋放。
藉由習用方法進行處理。一般而言,用水處理反應混合物,且分離出有機相且在乾燥後於減壓下濃縮。適當時,剩餘殘餘物可藉由諸如層析、結晶或蒸餾之習用方法自仍可存在之任何雜質釋放。
式(I)化合物可根據上文所描述之製備之通用製程來製備。然而應理解,基於其常識及可用之公開案,習此相關技藝之人士將能夠根據所需合成的每一化合物之特殊性來調整該等方法。
用於製備活性成分之中間體
本發明亦係關於用於製備式(I)化合物的中間體。
因此,本發明係關於式(IIa)化合物以及其可接受之鹽:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義,且U1a
表示氯原子、溴原子或碘原子。
在化學資料庫及/或供應商資料庫中提及下式(IIa)之化合物,但無使得此等化合物能夠製備及分離之任何參考文獻或資訊: - 3-[2-氯-6-(氯甲基)苯氧基]喹啉[2115263-99-3], - 3-[2-(溴甲基)苯氧基]喹啉[1984429-33-5], - 3-[2-(溴甲基)-4-甲基苯氧基]喹啉[1965664-20-3], - 3-[2-(氯甲基)-4-甲基苯氧基]喹啉[1965657-18-4], - 3-[5-氯-2-(氯甲基)苯氧基]喹啉[1965173-09-4], - 3-[2-(溴甲基)-6-氟苯氧基]喹啉[1962784-34-4], - 3-[2-(溴甲基)-4-氟苯氧基]喹啉[1962432-94-5], - 3-[2-(氯甲基)-6-氟苯氧基]喹啉[1944013-78-8], - 3-[2-(溴甲基)-3-氟苯氧基]喹啉[1937855-08-7], - 3-[2-(溴甲基)-6-氯苯氧基]喹啉[1937132-69-8], - 3-[4-溴-2-(氯甲基)苯氧基]喹啉[1937073-70-5], - 3-[2-(氯甲基)-3-氟苯氧基]喹啉[1929477-21-3], - 3-[4-氯-2-(氯甲基)苯氧基]喹啉[1929007-47-5], - 3-[2-(溴甲基)-4-氯苯氧基]喹啉[1928589-74-5], - 3-[2-(氯甲基)苯氧基]喹啉[1927507-10-5], - 3-[5-溴-2-(溴甲基)苯氧基]喹啉[1927507-06-9], - 3-[2-(溴甲基)-3-氯苯氧基]喹啉[1927140-37-1], - 3-[2-(氯甲基)-4-氟苯氧基]喹啉[1927074-67-6], - 3-[5-溴-2-(氯甲基)苯氧基]喹啉[1926940-89-7], - 3-[3-氯-2-(氯甲基)苯氧基]喹啉[1926940-83-1], - 3-[4-溴-2-(溴甲基)苯氧基]喹啉[1925651-81-5],及 - 3-[2-(溴甲基)-5-氯苯氧基]喹啉[1925623-80-8]。 根據本發明之較佳式(IIa)化合物為: - 3-[3-氯-2-(氯甲基)苯氧基]喹啉, - 3-[2-(氯甲基)-3-氟苯氧基]喹啉,及 - 3-[2-(溴甲基)苯氧基]-8-氟喹啉。
本發明亦係關於式(V)化合物以及其可接受之鹽:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義, 其限制條件為該式(V)化合物不表示: - {2-溴-6-[(8-氟喹啉-3-基)氧基]苯基}甲醇[1314009-28-3],及 - {2-氯-6-[(8-氟喹啉-3-基)氧基]苯基}甲醇[1314009-25-0]。
在化學資料庫及/或供應商資料庫中提及下式(V)之化合物,但無使得此等化合物能夠製備及分離之任何參考文獻或資訊: - {2-[(3-胺基喹喏啉-2-基)氧基]苯基}甲醇[1975425-47-8], - [5-甲基-2-(喹啉-3-基氧基)苯基]甲醇[1965687-80-2], - [2-氯-6-(喹啉-3-基氧基)苯基]甲醇[1965406-17-0], - [5-氯-2-(喹啉-3-基氧基)苯基]甲醇[1965406-09-0], - [2-氟-6-(喹啉-3-基氧基)苯基]甲醇[1963098-24-9], - [5-溴-2-(喹啉-3-基氧基)苯基]甲醇[1962859-44-4], - {2-[(3-甲基喹喏啉-2-基)氧基]苯基}甲醇[1958608-15-5], - [2-(喹喏啉-2-基氧基)苯基]甲醇[1940088-23-2], - [3-氯-2-(喹啉-3-基氧基)苯基]甲醇[1936861-82-3], - [3-氟-2-(喹啉-3-基氧基)苯基]甲醇[1929748-13-9], - [4-氯-2-(喹啉-3-基氧基)苯基]甲醇[1928858-16-5], - [5-氟-2-(喹啉-3-基氧基)苯基]甲醇[1927140-33-7], - [2-(喹啉-3-基氧基)苯基]甲醇[1927074-65-4],及 - [4-溴-2-(喹啉-3-基氧基)苯基]甲醇 [1926940-80-8]。
根據本發明之較佳式(V)化合物為: - {2-[(8-氟喹啉-3-基)氧基]苯基}甲醇, - [2-氟-6-(喹啉-3-基氧基)苯基]甲醇,及 - [2-氯-6-(喹啉-3-基氧基)苯基]甲醇。
組合物及調配物
本發明進一步係關於一種組合物,詳言之用於控制非所需微生物之組合物。可將組合物施加至微生物及/或其生境中。
該組合物通常包含一或多種式(I)化合物及至少一種農業上適合之助劑,例如載劑及/或界面活性劑。
載劑為固體或液體、天然或合成的、有機或無機物質,其一般為惰性的。該載劑一般改良化合物至例如植物、植物部分或種子之施加。適合之固體載劑
之實例包括(但不限於):銨鹽;天然石粉,諸如高嶺土、黏土、滑石、白堊、石英、綠坡縷石、蒙脫石或矽藻土;及合成石粉,諸如經細微粉碎二氧化矽、氧化鋁及矽酸鹽。通常適用於製備顆粒之固體載劑之實例包括(但不限於):碾碎且分級之天然岩石,諸如方解石、大理石、浮石、海泡石及白雲石;合成的無機及有機粉末顆粒;及有機材料(諸如紙張、鋸屑、椰子殼、玉米穗軸及菸草梗)之顆粒。適合液體載劑
之實例包括(但不限於)水、有機溶劑及其組合。適合之溶劑
之實例包括例如來自以下各類之極性及非極性有機化學液體:芳族及非芳族烴(諸如環己烷、石蠟、烷基苯、二甲苯、甲苯烷基萘、氯化芳族物或氯化脂族烴,諸如氯苯、氯乙烯或二氯甲烷);醇及多元醇(其亦可視情況經取代、醚化及/或酯化,諸如丁醇或二醇);酮(諸如丙酮、甲基乙基酮、甲基異丁基酮或環己酮);酯(包括脂肪及油);以及(聚)醚、未經取代及經取代之胺、醯胺(諸如二甲基甲醯胺)、內醯胺(諸如N-烷基咯啶酮)及內酯、碸及亞碸(諸如二甲亞碸)。載劑亦可為液化氣態填充劑(亦即在標準溫度下及在標準壓力下為氣態的液體),例如,氣溶膠推進劑,諸如,鹵代烴、丁烷、丙烷、氮氣及二氧化碳。載劑之量的範圍以組合物之重量計通常為1至99.99%、較佳地5至99.9%、更佳地10至99.5 %及最佳地20至99%。
界面活性劑可為離子(陽離子或陰離子)或非離子界面活性劑,諸如離子或非離性乳化劑、泡沫形成劑、分散劑、濕潤劑及其任何混合物。適合之界面活性劑之實例包括(但不限於):聚丙烯酸之鹽、木質磺酸之鹽、酚磺酸或萘磺酸之鹽、乙烯及/或環氧丙烷與脂肪醇、脂肪酸或脂肪胺之聚縮合物(聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如烷芳基聚二醇醚)、經取代酚(較佳為烷基酚或芳基酚)、磺化丁二酸酯之鹽、牛磺酸衍生物(較佳為牛磺酸烷酯)、聚乙氧基化醇或酚之磷酸酯、多元醇之脂肪酯及含有硫酸酯、磺酸酯及磷酸酯之化合物之衍生物(例如烷基磺酸酯、硫酸烷酯、芳基磺酸酯)、蛋白質水解產物、木質亞硫酸鹽廢液及甲基纖維素。界面活性劑通常在式(I)化合物及/或載劑不溶於水且用水進行施加時使用。於是,界面活性劑之量通常在組合物之5至40 wt%範圍內。
適合之助劑之其他實例包括:拒水劑;乾燥劑;黏合劑(黏著劑、增黏劑、固定劑,諸如羧甲基纖維素;呈粉末、顆粒或膠乳形式之天然及合成聚合物,諸如阿拉伯膠、聚乙烯醇及聚乙酸乙烯酯;諸如腦磷脂及卵磷脂之天然磷脂及合成磷脂;聚乙烯吡咯啶酮;及泰勒士(tylose));增稠劑;穩定劑(例如,低溫穩定劑、防腐劑、抗氧化劑、光穩定劑或改良化學及/或物理穩定性之其他試劑);染料或顏料(諸如無機顏料,例如氧化鐵、氧化鈦及普魯士藍;有機染料,例如茜素、偶氮及金屬酞菁染料);消泡劑(例如,聚矽氧消泡劑及硬脂酸鎂);防腐劑(例如,二氯酚及苯甲醇半縮甲醛);輔助增稠劑(纖維素衍生物、丙烯酸衍生物、三仙膠、經改質黏土及細微粉碎二氧化矽);黏著劑;赤黴素及處理助劑;礦物及植物油;香料;蠟;營養素(包括微量營養素,諸如鐵、錳、硼、銅、鈷、鉬及鋅之鹽);保護性膠體;搖溶性物質;滲透劑;螯合劑及錯合物形成劑。
助劑之選擇與本發明化合物之預期應用模式及/或其物理特性有關。另外,助劑可經選擇以向組合物或自其製備之使用形式賦予特定特性(工業、物理及/或生物特性)。助劑之選擇可允許針對特定需求定製組合物。
組合物可呈任何習用形式,諸如溶液(例如水溶液)、乳液、可濕潤粉末、水基及油基懸浮液、粉末、粉塵、糊狀物、可溶性粉末、可溶性顆粒、用於散佈之顆粒、懸浮乳劑濃縮物、浸漬有一或多種式(I)化合物之天然或合成產物、肥料以及聚合物質之微膠囊。式(I)化合物可以懸浮、乳化或溶解形式存在。
可將組合物作為備用調配物提供至終端使用者,亦即組合物可藉由適合裝置(諸如噴灑或撒粉裝置)直接施加至植物或種子。或者,組合物可以濃縮物形式提供至終端使用者,該濃縮物在使用之前必須經稀釋,較佳地用水稀釋。
組合物可以習知方式製備,例如藉由使式(I)化合物與諸如本文上文所揭示之一或多種適合助劑混合來製備。
組合物一般含有0.01至99 wt%、0.05至98 wt%、較佳地0.1至95 wt%、更佳地0.5至90 wt%、最佳地1至80 wt%之式(I)化合物。組合物可能包含兩種或多於兩種式(I)化合物。在此情況下,概述之範圍係指式(I)化合物之總量。
混合物 / 組合
式(I)化合物及包含其之組合物可與如殺真菌劑、殺細菌劑、殺蟎劑、殺線蟲劑、殺昆蟲劑、除草劑、肥料、生長調節劑、安全劑或訊息化合物之其他活性成分混合。此可使活性範圍變寬或防止出現耐藥性。已知殺真菌劑、殺昆蟲劑、殺蟎劑、殺線蟲劑及殺細菌劑之實例揭示於Pesticide Manual,第17版中。
可與式(I)化合物混合之尤佳殺真菌劑之實例為:
1) 麥角固醇生物合成之抑制劑,例如(1.001)環克座(cyproconazole)、(1.002)待克利(difenoconazole)、(1.003)依普座(epoxiconazole)、(1.004)環醯菌胺(fenhexamid)、(1.005)苯鏽啶(fenpropidin)、(1.006)芬普福(fenpropimorph)、(1.007)胺苯吡菌酮(fenpyrazamine)、(1.008)氟喹唑(fluquinconazole)、(1.009)護汰芬(flutriafol)、(1.010)依滅列(imazalil)、(1.011)依滅列硫酸鹽(imazalil sulfate)、(1.012)種菌唑(ipconazole)、(1.013)滅特座(metconazole)、(1.014)邁克尼(myclobutanil)、(1.015)巴克素(paclobutrazol)、(1.016)撲克拉(prochloraz)、(1.017)普克利(propiconazole)、(1.018)丙硫菌唑(prothioconazole)、(1.019)啶菌噁唑(Pyrisoxazole)、(1.020)螺環菌胺(spiroxamine)、(1.021)得克利(tebuconazole)、(1.022)四克利(tetraconazole)、(1.023)三泰隆(triadimenol)、(1.024)三得芬(tridemorph)、(1.025)滅菌唑(triticonazole)、(1.026) (1R,2S,5S)-5-(4-氯苯甲基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)環戊醇、(1.027) (1S,2R,5R)-5-(4-氯苯甲基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)環戊醇、(1.028) (2R)-2-(1-氯環丙基)-4-[(1R)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.029) (2R)-2-(1-氯環丙基)-4-[(1S)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.030) (2R)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.031) (2S)-2-(1-氯環丙基)-4-[(1R)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.032) (2S)-2-(1-氯環丙基)-4-[(1S)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.033) (2S)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.034) (R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(1.035) (S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(1.036) [3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(1.037) 1-({(2R,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧環戊-2-基}甲基)-1H-1,2,4-三唑、(1.038) 1-({(2S,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧環戊-2-基}甲基)-1H-1,2,4-三唑、(1.039) 1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.040) 1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸鹽、(1.041) 1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸鹽、(1.042) 2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.043) 2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.044) 2-[(2R,4S,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.045) 2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.046) 2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.047) 2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.048) 2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.049) 2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.050) 2-[1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.051) 2-[2-氯-4-(2,4-二氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.052) 2-[2-氯-4-(4-氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.053) 2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.054) 2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)戊-2-醇、(1.055)甲分三康唑(Mefentrifluconazole)、(1.056) 2-{[3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.057) 2-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.058) 2-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.059) 5-(4-氯苯甲基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)環戊醇、(1.060) 5-(烯丙基硫基)-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.061) 5-(烯丙基硫基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.062)5-(烯丙基硫基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.063) N'-(2,5-二甲基-4-{[3-(1,1,2,2-四氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.064) N'-(2,5-二甲基-4-{[3-(2,2,2-三氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.065) N'-(2,5-二甲基-4-{[3-(2,2,3,3-四氟丙氧基)苯基]硫基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.066) N'-(2,5-二甲基-4-{[3-(五氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.067) N'-(2,5-二甲基-4-{3-[(1,1,2,2-四氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.068) N'-(2,5-二甲基-4-{3-[(2,2,2-三氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.069) N'-(2,5-二甲基-4-{3-[(2,2,3,3-四氟丙基)硫基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.070) N'-(2,5-二甲基-4-{3-[(五氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.071) N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.072) N'-(4-{[3-(二氟甲氧基)苯基]硫基}-2,5-二甲基苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.073) N'-(4-{3-[(二氟甲基)硫基]苯氧基}-2,5-二甲基苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.074) N'-[5-溴-6-(2,3-二氫-1H-茚-2-基氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基亞胺基甲醯胺、(1.075) N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基亞胺基甲醯胺、(1.076) N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.077) N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.078) N'-{5-溴-6-[(順-4-異丙基環己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.079) N'-{5-溴-6-[(反-4-異丙基環己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.080) N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.081)伊分三康唑(Ipfentrifluconazole)。 2)錯合物I或II處之呼吸鏈之抑制劑,例如(2.001)苯丙烯氟菌唑(benzovindiflupyr)、(2.002)必殺吩(bixafen)、(2.003)白可列(boscalid)、(2.004)萎鏽靈(carboxin)、(2.005)氟吡菌醯胺(fluopyram)、(2.006)福多寧(flutolanil)、(2.007)氟唑菌醯胺(fluxapyroxad)、(2.008)福拉比(furametpyr)、(2.009)艾索非他米(Isofetamid)、(2.010)吡唑萘菌胺(isopyrazam)(抗差向異構對映異構體1R,4S,9S)、(2.011)吡唑萘菌胺(抗差向異構對映異構體1S,4R,9R)、(2.012)吡唑萘菌胺(抗差向異構外消旋體1RS,4SR,9SR)、(2.013)吡唑萘菌胺(同側差向異構外消旋體1RS,4SR,9RS及抗差向異構外消旋體1RS,4SR,9SR之混合物)、(2.014)吡唑萘菌胺(同側差向異構對映異構體1R,4S,9R)、(2.015)吡唑萘菌胺(同側差向異構對映異構體1S,4R,9S)、(2.016)吡唑萘菌胺(同側差向異構外消旋體1RS,4SR,9RS)、(2.017)噴福芬(penflufen)、(2.018)吡噻菌胺(penthiopyrad)、(2.019)吡二氟甲多芬(pydiflumetofen)、(2.020)吡瑞氟密得(Pyraziflumid)、(2.021) 氟唑環菌胺(sedaxane)、(2.022) 1,3-二甲基-N-(1,1,3-三甲基-2,3-二氫-1H-茚-4-基)-1H-吡唑-4-甲醯胺、(2.023) 1,3-二甲基-N-[(3R)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-甲醯胺、(2.024) 1,3-二甲基-N-[(3S)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-甲醯胺、(2.025) 1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)聯苯-2-基]-1H-吡唑-4-甲醯胺、(2.026) 2-氟-6-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氫-1H-茚-4-基)苯甲醯胺、(2.027) 3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氫-1H-茚-4-基)-1H-吡唑-4-甲醯胺、(2.028) 3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-甲醯胺、(2.029) 3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-甲醯胺、(2.030)氟因菌唑(Fluindapyr)、(2.031) 3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲醯胺、(2.032) 3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲醯胺、(2.033) 5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.034) N-(2-環戊基-5-氟苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.035) N-(2-第三丁基-5-甲基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.036) N-(2-第三丁基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.037) N-(5-氯-2-乙基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.038) 甲醯胺基嘧磺隆(isoflucypram)、(2.039) N-[(1R,4S)-9-(二氯亞甲基)-1,2,3,4-四氫-1,4-甲橋萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.040) N-[(1S,4R)-9-(二氯亞甲基)-1,2,3,4-四氫-1,4-甲橋萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.041) N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.042) N-[2-氯-6-(三氟甲基)苯甲基]-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.043) N-[3-氯-2-氟-6-(三氟甲基)苯甲基]-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.044) N-[5-氯-2-(三氟甲基)苯甲基]-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.045) N-環丙基-3-(二氟甲基)-5-氟-1-甲基-N-[5-甲基-2-(三氟甲基)苯甲基]-1H-吡唑-4-甲醯胺、(2.046) N-環丙基-3-(二氟甲基)-5-氟-N-(2-氟-6-異丙基苯甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.047) N-環丙基-3-(二氟甲基)-5-氟-N-(2-異丙基-5-甲基苯甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.048) N-環丙基-3-(二氟甲基)-5-氟-N-(2-異丙基苯甲基)-1-甲基-1H-吡唑-4-硫代碳醯胺、(2.049) N-環丙基-3-(二氟甲基)-5-氟-N-(2-異丙基苯甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.050) N-環丙基-3-(二氟甲基)-5-氟-N-(5-氟-2-異丙基苯甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.051) N-環丙基-3-(二氟甲基)-N-(2-乙基-4,5-二甲苯甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.052) N-環丙基-3-(二氟甲基)-N-(2-乙基-5-氟苯甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.053) N-環丙基-3-(二氟甲基)-N-(2-乙基-5-甲基苯甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.054) N-環丙基-N-(2-環丙基-5-氟苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.055) N-環丙基-N-(2-環丙基-5-甲基苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.056) N-環丙基-N-(2-環丙基苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.057)吡丙菌醯胺(pyrapropoyne)。 3)錯合物III之呼吸鏈之抑制劑,例如:(3.001)辛唑嘧菌胺(ametoctradin)、(3.002)吲唑磺菌胺(amisulbrom)、(3.003)亞托敏(azoxystrobin)、(3.004)甲香菌酯(coumethoxystrobin)、(3.005)丁香菌酯(coumoxystrobin)、(3.006)賽座滅(cyazofamid)、(3.007)醚菌胺(dimoxystrobin)、(3.008)亞烷基嘧菌酯(enoxastrobin)、(3.009)凡殺同(famoxadone)、(3.010)咪唑菌酮(fenamidone)、(3.011)氟菌蟎酯(flufenoxystrobin)、(3.012)氟嘧菌酯(fluoxastrobin)、(3.013)克收欣(kresoxim-methyl)、(3.014)苯氧菌胺(metominostrobin)、(3.015)肟醚菌胺(orysastrobin)、(3.016)啶氧菌酯(picoxystrobin)、(3.017)百克敏(pyraclostrobin)、(3.018)唑胺菌酯(pyrametostrobin)、(3.019)唑菌酯(pyraoxystrobin)、(3.020)三氟敏(trifloxystrobin)、(3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)亞乙基]胺基}氧基)甲基]苯基}-2-(甲氧亞胺基)-N-甲基乙醯胺、(3.022) (2E,3Z)-5-{[1-(4-氯苯基)-1H-吡唑-3-基]氧基}-2-(甲氧亞胺基)-N,3-二甲基戊-3-烯醯胺、(3.023) (2R)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙醯胺、(3.024) (2S)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙醯胺、(3.025) (3S,6S,7R,8R)-2-甲基丙酸8-苯甲基-3-[({3-[(異丁醯氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)胺基]-6-甲基-4,9-二側氧基-1,5-二氧雜環壬-7-基酯、(3.026) 杏仁菌酯(mandestrobin)、(3.027) N-(3-乙基-3,5,5-三甲基環己基)-3-甲醯胺基-2-羥苯甲醯胺、(3.028) (2E,3Z)-5-{[1-(4-氯-2-氟苯基)-1H-吡唑-3-基]氧基}-2-(甲氧亞胺基)-N,3-二甲基戊-3-烯醯胺、(3.029) {5-[3-(2,4-二甲基苯基)-1H-吡唑-1-基]-2-甲基苯甲基}胺基甲酸甲酯、(3.030)甲基四菌唑(metyltetraprole)、(3.031)吡啶醯菌胺(florylpicoxamid)。 4)有絲分裂及細胞分裂之抑制劑,例如:(4.001)貝芬替(carbendazim)、(4.002)乙黴威(diethofencarb)、(4.003)噻唑菌胺(ethaboxam)、(4.004)氟吡菌胺(fluopicolide)、(4.005)賓克隆(pencycuron)、(4.006)腐絕(thiabendazole)、(4.007)甲基多保淨(thiophanate-methyl)、(4.008)座賽胺(zoxamide)、(4.009) 3-氯-4-(2,6-二氟苯基)-6-甲基-5-苯基噠嗪、(4.010) 3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基噠嗪、(4.011) 3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)噠嗪、(4.012) 4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.013) 4-(2-溴-4-氟苯基)-N-(2-溴-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.014) 4-(2-溴-4-氟苯基)-N-(2-溴苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.015) 4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.016) 4-(2-溴-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.017) 4-(2-溴-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.018) 4-(2-氯-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.019) 4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.020) 4-(2-氯-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.021) 4-(2-氯-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.022) 4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基噠嗪、(4.023) N-(2-溴-6-氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.024) N-(2-溴苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.025) N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。 5)能夠具有多位點作用之化合物,例如:(5.001)波多混合物、(5.002)四氯丹(captafol)、(5.003)卡丹(captan)、(5.004)四氯異苯腈、(5.005)氫氧化銅、(5.006)環烷酸銅、(5.007)氧化銅、(5.008)鹼性氯氧化銅、(5.009)硫酸銅(2+)、(5.010)腈硫醌、(5.011)多寧(dodine)、(5.012)福爾培(folpet)、(5.013)鋅錳乃浦(mancozeb)、(5.014)錳乃浦(maneb)、(5.015)免得爛(metiram)、(5.016)免得爛鋅(metiram zinc)、(5.017)咢辛-銅(oxine-copper)、(5.018)甲基鋅乃浦(propineb)、(5.019)硫及包括鈣多硫化物之硫製劑、(5.020)得恩地(thiram)、(5.021)鋅乃浦(zineb)、(5.022)益穗(ziram)、(5.023) 6-乙基-5,7-二側氧基-6,7-二氫-5H-吡咯并[3',4':5,6][1,4]二噻并[2,3-c][1,2]噻唑-3-甲腈。 6)能夠誘導宿主防護之化合物,例如:(6.001)甲噻活素、(6.002)異噻菌胺(isotianil)、(6.003)撲殺熱(probenazole)、(6.004)汰敵寧(tiadinil)。 7)胺基酸及/或蛋白質生物合成之抑制劑,例如:(7.001)嘧菌環胺、(7.002)春日黴素、(7.003)水合春日黴素鹽酸鹽、(7.004)土黴素、(7.005)嘧黴胺、(7.006) 3-(5-氟-3,3,4,4-四甲基-3,4-二氫異喹啉-1-基)喹啉。 8)ATP產生之抑制劑,例如(8.001)矽噻菌胺。 9)細胞壁合成之抑制劑,例如:(9.001)苯噻菌胺(benthiavalicarb)、(9.002)達滅芬(dimethomorph)、(9.003)氟嗎啉(flumorph)、(9.004)纈黴威(iprovalicarb)、(9.005)雙炔醯菌胺(mandipropamid)、(9.006)丁吡嗎啉(pyrimorph)、(9.007)威利芬那雷特(valifenalate)、(9.008) (2E)-3-(4-第三丁基苯基)-3-(2-氯吡啶-4-基)-1-(嗎啉-4-基)丙-2-烯-1-酮、(9.009) (2Z)-3-(4-第三丁基苯基)-3-(2-氯吡啶-4-基)-1-(嗎啉-4-基)丙-2-烯-1-酮。 10)脂質及膜合成之抑制劑,例如:(10.001)霜黴威(propamocarb)、(10.002)霜黴威鹽酸鹽、(10.003)脫克松(tolclofos-methyl)。 11)黑色素生物合成之抑制劑,例如:(11.001)三賽唑(tricyclazole)、(11.002) {3-甲基-1-[(4-甲基苯甲醯基)胺基]丁-2-基}胺基甲酸2,2,2-三氟乙酯。 12)核酸合成之抑制劑,例如:(12.001)本達樂(benalaxyl)、(12.002)本達樂-M (精苯霜靈(kiralaxyl))、(12.003)滅達樂(metalaxyl)、(12.004)滅達樂-M (右滅達樂(mefenoxam))。 13)信號轉導之抑制劑,例如:(13.001)護汰寧(fludioxonil)、(13.002)依普同(iprodione)、(13.003)撲滅寧(procymidone)、(13.004)丙氧喹啉(proquinazid)、(13.005)快諾芬(quinoxyfen)、(13.006)免克寧(vinclozolin)。 14)能夠充當解偶聯劑之化合物,例如:(14.001)扶吉胺(fluazinam)、(14.002)敵蟎普(meptyldinocap)。 15)其他化合物,例如:(15.001)脫落酸、(15.002)苯噻硫氰、(15.003)吡托沙嗪(bethoxazin)、(15.004)卡巴西黴素、(15.005)香芹酮、(15.006)蟎離丹(chinomethionat)、(15.007)硫雜靈(cufraneb)、(15.008)環氟菌胺、(15.009)克絕(cymoxanil)、(15.010)環丙磺醯胺、(15.011)氟替尼(flutianil)、(15.012)三乙膦酸鋁、(15.013)三乙膦酸鈣、(15.014)三乙膦酸鈉、(15.015)異硫氰酸甲酯、(15.016)滅芬農(metrafenone)、(15.017)米多黴素(mildiomycin)、(15.018)納他黴素(natamycin)、(15.019)二甲基二硫代胺基甲酸鎳、(15.020)酞菌酯、(15.021)奧斯莫卡(oxamocarb)、(15.022)奧賽普林(oxathiapiprolin)、(15.023)奧克斯芬塞林(oxyfenthiin)、(15.024)五氯苯酚及鹽、(15.025)亞磷酸及其鹽、(15.026)霜黴威三乙膦酸鹽、(15.027)甲氧苯唳菌(氯芬酮)、(15.028)特普弗洛奎(tebufloquin)、(15.029)克枯爛(tecloftalam)、(15.030)甲磺菌胺(tolnifanide)、(15.031) 1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氫-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、(15.032) 1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氫-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、(15.033) 2-(6-苯甲基吡啶-2-基)喹唑啉、(15.034)二吡蚜酮(dipymetitrone)、(15.035) 2-[3,5-雙(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-(丙-2-炔-1-基氧基)苯基]-4,5-二氫-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.036) 2-[3,5-雙(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氯-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氫-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.037) 2-[3,5-雙(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氟-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氫-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.038) 2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2-基]喹唑啉、(15.039)甲烷磺酸2-{(5R)-3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-噁唑-5-基}-3-氯苯基酯、(15.040)甲烷磺酸2-{(5S)-3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-噁唑-5-基}-3-氯苯基酯、(15.041)依普氟芬喹(Ipflufenoquin)、(15.042) 2-{2-氟-6-[(8-氟-2-甲基喹啉-3-基)氧基]苯基}丙-2-醇、(15.043)甲烷磺酸2-{3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-噁唑-5-基}-3-氯苯基酯、(15.044)甲烷磺酸2-{3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-噁唑-5-基}苯基酯、(15.045) 2-苯基苯酚及鹽、(15.046) 3-(4,4,5-三氟-3,3-二甲基-3,4-二氫異喹啉-1-基)喹啉、(15.047)喹富滅靈(quinofumelin)、(15.048) 4-胺基-5-氟嘧啶-2-醇(互變異構形式:4-胺基-5-氟嘧啶-2(1H)-酮)、(15.049) 4-側氧基-4-[(2-苯乙基)胺基]丁酸、(15.050) 5-胺基-1,3,4-噻二唑-2-硫醇、(15.051) 5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩-2-苯磺醯肼、(15.052) 5-氟-2-[(4-氟苯甲基)氧基]嘧啶-4-胺、(15.053) 5-氟-2-[(4-甲基苯甲基)氧基]嘧啶-4-胺、(15.054) 9-氟-2,2-二甲基-5-(喹啉-3-基)-2,3-二氫-1,4-苯并噁氮呯、(15.055){6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亞甲基]胺基}氧基)甲基]吡啶-2-基}胺基甲酸丁-3-炔-1-基酯、(15.056) (2Z)-3-胺基-2-氰基-3-苯基丙烯酸乙酯、(15.057)吩嗪-1-甲酸、(15.058) 3,4,5-三羥基苯甲酸丙酯、(15.059)喹啉-8-醇、(15.060)喹啉-8-醇硫酸酯(2:1)、(15.061) {6-[({[(1-甲基-1H-四唑-5-基)(苯基)亞甲基]胺基}氧基)甲基]吡啶-2-基}胺基甲酸第三丁酯、(15.062) 5-氟-4-亞胺基-3-甲基-1-[(4-甲基苯基)磺醯基]-3,4-二氫嘧啶-2(1H)-酮、(15.063)胺基吡芬(aminopyrifen)。
如本文上文所描述之類別(1)至(15)之所有提出的混合搭配物可以游離化合物形式及/或(若其官能基使得此可能)其農業上可接受之鹽形式存在。
式(I)化合物及包含其之組合物亦可與一或多種生物控制劑組合。
可與式(I)化合物及包含其之組合物組合的生物控制劑之實例為:
(A)選自由以下組成之群的抗細菌劑: (A1)細菌,諸如(A1.1)枯草桿菌,詳言之菌株QST713/AQ713 (可以SERENADE OPTI或SERENADE ASO之形式自美國Bayer CropScience LP獲得,具有NRRL寄存編號B21661且描述於美國專利第6,060,051號中);(A1.2)解澱粉芽孢桿菌,詳言之菌株D747 (可以Double Nickel™之形式自美國Certis獲得,具有寄存編號FERM BP-8234且揭示於美國專利第7,094,592號中);(A1.3)短小芽孢桿菌,詳言之菌株BU F-33 (具有NRRL寄存編號50185);(A1.4)枯草桿菌變種解澱粉芽孢桿菌菌株FZB24 (可以Taegro®形式自美國Novozymes獲得);(A1.5)類芽孢桿菌屬菌株,其具有寄存編號NRRL B-50972或寄存編號NRRL B-67129且描述於國際專利公開案第WO 2016/154297號中;以及 (A2)真菌,諸如(A2.1)出芽短梗黴菌,詳言之菌株DSM14940之芽生孢子;(A2.2)菌株DSM 14941之出芽短梗黴菌芽生孢子;(A2.3)出芽短梗黴菌,詳言之菌株DSM14940及DSM14941之芽生孢子的混合物; (B)選自由以下組成之群的殺真菌劑: (B1)細菌,例如(B1.1)枯草桿菌,詳言之菌株QST713/AQ713 (可以SERENADE OPTI或SERENADE ASO之形式自美國Bayer CropScience LP獲得,其具有NRRL寄存編號B21661且描述於美國專利第6,060,051號中);(B1.2)短小芽孢桿菌,詳言之菌株QST2808 (可以SONATA®形式自美國Bayer CropScience LP獲得,其具有寄存編號NRRL B-30087且描述於美國專利第6,245,551號中);(B1.3)短小芽孢桿菌,詳言之菌株GB34 (可以Yield Shield®之形式自德國Bayer AG獲得);(B1.4)短小芽孢桿菌,詳言之菌株BU F-33 (具有NRRL寄存編號50185);(B1.5)解澱粉芽孢桿菌,詳言之菌株D747 (可以Double Nickel™之形式自美國Certis獲得,其具有寄存編號FERM BP-8234且揭示於美國專利第7,094,592號中);(B1.6)枯草桿菌Y1336 (可以BIOBAC®
WP形式自臺灣Bion-Tech獲得,其在臺灣以註冊號4764、5454、5096及5277註冊為生物殺真菌劑);(B1.7)解澱粉芽孢桿菌菌株MBI 600 (可以SUBTILEX形式自BASF SE獲得);(B1.8)枯草桿菌菌株GB03 (可以Kodiak®形式自德國Bayer AG獲得);(B1.9)枯草桿菌變種解澱粉芽孢桿菌菌株FZB24 (可自Novozymes Biologicals Inc., Salem, Virginia或Syngenta Crop Protection, LLC, Greensboro, North Carolina以殺真菌劑TAEGRO®
或TAEGRO®
ECO (EPA註冊號70127-5)形式獲得);(B1.10)蕈狀桿菌分離株J (可以BmJ TGAI或WG自美國Certis獲得);(B1.11)地衣芽孢桿菌,詳言之菌株SB3086 (可以EcoGuard TM生物殺真菌劑及Green Releaf自Novozymes獲得);(B1.12)類芽孢桿菌屬菌株,其具有寄存編號NRRL B-50972或寄存編號NRRL B-67129且描述於國際專利公開案第WO 2016/154297號中。
在一些實施例中,生物控制劑為產生豐原素(fengycin)或大側柏素(plipastatin)類化合物、伊枯草菌素(iturin)類化合物及/或表面活性素類化合物的枯草桿菌或解澱粉芽孢桿菌菌株。對於先前技術,參見以下評論文章:Ongena, M.等人, 「Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol,」 Trends in Microbiology,第16卷,第3期,2008年3月,第115-125頁。能夠產生脂肽之芽孢桿菌菌株包括枯草桿菌QST713 (可以SERENADE OPTI或SERENADE ASO形式自美國Bayer CropScience LP獲得,其具有NRRL寄存編號B21661且描述於美國專利第6,060,051號中);解澱粉芽孢桿菌菌株D747 (可以Double Nickel™形式自美國Certis獲得,其具有寄存編號FERM BP-8234且揭示於美國專利第7,094,592號中);枯草桿菌MBI600 (可以SUBTILEX®
形式自Becker Underwood獲得,US EPA登記號71840-8);枯草桿菌Y1336 (可以BIOBAC®
WP形式自臺灣Bion-Tech獲得,其在臺灣以註冊號4764、5454、5096及5277註冊為生物殺真菌劑);解澱粉芽孢桿菌,詳言之菌株FZB42 (可以RHIZOVITAL®
形式自德國ABiTEP獲得);以及枯草桿菌變種解澱粉芽孢桿菌FZB24 (可自Novozymes Biologicals Inc., Salem, Virginia或Syngenta Crop Protection, LLC, Greensboro, North Carolina以殺真菌劑TAEGRO®
或TAEGRO®
ECO (EPA註冊號70127-5)形式獲得);以及 (B2)真菌,例如:(B2.1)盾殼黴(Coniothyrium minitans
),詳言之菌株CON/M/91-8 (寄存編號DSM-9660;例如來自Bayer之Contans®
);(B2.2)核果梅奇酵母(Metschnikowia fructicola
),詳言之菌株NRRL Y-30752 (例如,Shemer®);(B2.3) 赫色小球殼孢菌(Microsphaeropsis ochracea
) (例如,來自Prophyta之Microx®);(B2.5)木黴菌屬,包括深綠木黴菌,菌株SC1,其描述於國際申請案第PCT/IT2008/000196號中;(B2.6)里法伊哈氏木黴菌(Trichoderma harzianum rifai
)菌株KRL-AG2 (亦稱為菌株T-22/ATCC 208479,例如來自美國BioWorks之PLANTSHIELD T-22G、Rootshield®及TurfShield);(B2.14)粉紅膠黴菌(Gliocladium roseum
)菌株321U,其來自W.F. Stoneman Company LLC;(B2.35)黃色籃狀菌(Talaromyces flavus
)菌株V117b;(B2.36)棘孢木黴(Trichoderma asperellum
)菌株ICC 012,來自Isagro;(B2.37)棘孢木黴菌株SKT-1 (例如,來自Kumiai Chemical Industry之ECO-HOPE®);(B2.38)深綠木黴菌菌株CNCM I-1237 (例如,來自法國Agrauxine之Esquive®WP);(B2.39)深綠木黴菌菌株第V08/002387號;(B2.40)深綠木黴菌菌株NMI編號V08/002388;(B2.41)深綠木黴菌菌株NMI編號V08/002389;(B2.42)深綠木黴菌菌株NMI編號V08/002390;(B2.43)深綠木黴菌菌株LC52 (例如,Agrimm Technologies Limited之Tenet);(B2.44)深綠木黴菌菌株ATCC 20476 (IMI 206040);(B2.45)深綠木黴菌菌株T11 (IMI352941/CECT20498);(B2.46)鉤狀木黴菌(Trichoderma harmatum
);(B2.47)哈氏木黴菌;(B2.48)里法伊哈氏木黴菌T39
(例如,來自美國Makhteshim之Trichodex®);(B2.49) 哈氏木黴菌,詳言之,菌株KD (例如,來自Biological Control Products之Trichoplus,SA (由Becker Underwood獲得));(B2.50)哈氏木黴菌菌株ITEM 908 (例如,來自Koppert之Trianum-P);(B2.51)哈氏木黴菌菌株TH35 (例如,Mycontrol之Root-Pro);(B2.52)青綠木黴菌(Trichoderma virens
)(亦稱為青綠黏帚黴(Gliocladium virens
)),詳言之菌株GL-21 (例如,美國Certis之SoilGard 12G);(B2.53)綠色木黴菌(Trichoderma viride
)菌株TV1 (例如,Koppert之Trianum-P);(B2.54)白粉寄生孢(Ampelomyces quisqualis
),詳言之菌株AQ 10 (例如,意大利IntrachemBio之AQ 10®);(B2.56)出芽短梗黴菌(Aureobasidium pullulans
),詳言之菌株DSM14940之芽生孢子;(B2.57)出芽短梗黴菌,詳言之菌株DSM 14941之芽生孢子;(B2.58)出芽短梗黴菌,詳言之菌株DSM14940及DSM 14941之芽生孢子的混合物(例如,瑞士bio-ferm之Botector®);(B2.64)芽枝狀枝孢菌(Cladosporium cladosporioides
)菌株H39 (Stichting Dienst Landbouwkundig Onderzoek);(B2.69)鏈抱黏帚菌(Gliocladium catenulatum) (同義詞:鏈狀粉紅黏帚黴(Clonostachys rosea f . catenulate
))菌株J1446 (例如,AgBio Inc之Prestop®
以及例如Kemira Agro Oy之Primastop®);(B2.70)菌株KV01之臘蚧輪刺孢菌(Lecanicillium lecanii
) (以前被稱為臘蚧輪枝菌)分生孢子(例如,Koppert/Arysta之Vertalec®);(B2.71)蠕形青黴(Penicillium vermiculatum
);(B2.72)異常畢赤酵母(Pichia anomala
)菌株WRL-076 (NRRL Y-30842);(B2.75)深綠木黴菌菌株SKT-1 (FERM P-16510);(B2.76)深綠木黴菌菌株SKT-2 (FERM P-16511);(B2.77)深綠木黴菌菌株SKT-3 (FERM P-17021);(B2.78)蓋姆斯木黴菌(Trichoderma gamsii
)(先前之綠色木黴)菌株ICC080 (IMI CC 392151 CABI,例如AGROBIOSOL DE MEXICO, S.A. DE C.V.之BioDerma);(B2.79)哈氏木黴菌菌株DB 103 (例如,Dagutat Biolab之T-Gro 7456);(B2.80)多孔木黴菌(Trichoderma polysporum
)菌株IMI 206039 (例如,瑞典BINAB Bio-Innovation AB之Binab TF WP);(B2.81)基座狀木黴菌(Trichoderma stromaticum
)(例如,巴西Ceplac之Tricovab);(B2.83)奧德曼細基格孢(Ulocladium oudemansii
),詳言之菌株HRU3 (例如,Botry-Zen Ltd, NZ之Botry-Zen®);(B2.84)黃萎輪枝孢(Verticillium albo - atrum
)(以前之大麗輪枝菌)菌株WCS850 (CBS 276.92;例如Tree Care Innovations之Dutch Trig);(B2.86)垣輪枝孢菌(Verticillium chlamydosporium
);(B2.87)棘孢木黴菌株ICC 012及蓋姆斯木黴菌菌株ICC 080之混合物(來自美國Bayer CropScience LP之被稱為例如BIO-TAMTM
的產品)。
可與式(I)化合物及包含其之組合物組合的生物控制劑之其他實例為: 選自由以下組成之群的細菌:蠟樣芽胞桿菌(Bacillus cereus
),詳言之蠟狀芽孢桿菌(B . cereus
)菌株CNCM I-1562及強固芽胞桿菌(Bacillus firmus
)菌株I-1582 (寄存編號CNCM I-1582);枯草桿菌菌株OST 30002 (寄存編號NRRL B-50421);蘇力菌(Bacillus thuringiensis
),詳言之蘇雲金芽孢桿菌以色列亞種(B . thuringiensis
subspeciesisraelensis
)(血清型H-14),菌株AM65-52 (寄存編號ATCC 1276),蘇雲金芽孢桿菌亞莎華亞種(B . thuringiensis subsp . aizawai
),詳言之菌株ABTS-1857 (SD-1372),蘇雲金芽孢桿菌庫斯塔克亞種(B . thuringiensis subsp . kurstaki
)菌株HD-1,蘇雲金芽孢桿菌擬步行甲亞種(B . thuringiensis subsp . tenebrionis
)菌株NB 176 (SD-5428);穿刺巴斯德芽菌(Pasteuria penetrans
),巴斯德氏菌屬(腎狀線蟲)-PR3 (寄存編號ATCC SD-5834);細黃鏈黴菌(Streptomyces microflavus
)菌株AQ6121 (=QRD 31.013,NRRL B-50550);及鮮黃鏈黴菌菌株AQ 6047 (寄存編號NRRL 30232); 選自由以下組成之群的真菌及酵母:白殭菌(Beauveria bassiana
),詳言之菌株ATCC 74040;輪枝菌屬(Lecanicillium spp
.),詳言之菌株HRO LEC 12;黑殭菌(Metarhizium anisopliae
),詳言之菌株F52 (DSM3884或ATCC 90448);玫煙色擬青黴(Paecilomyces fumosoroseus ;
現為Isaria fumosorosea
),詳言之菌株IFPC 200613或菌株Apopka 97 (寄存編號ATCC 20874);及淡紫擬青黴(Paecilomyces lilacinus
),詳言之淡紫擬青黴菌株251 (AGAL 89/030550); 選自由以下組成之群的病毒:茶姬捲葉蛾(Adoxophyes orana
)(夏季水果捲葉蛾)顆粒體病毒(granulosis virus;GV);蘋果蠹蛾(Cydia pomonella
)(蘋果捲葉蛾)顆粒體病毒(GV);番茄夜蛾(Helicoverpa armigera
)(棉鈴蟲)核多角體病毒(NPV);甜菜菜蛾(Spodoptera exigua
)(甜菜夜蛾) mNPV;草地黏蟲(Spodoptera frugiperda
)(秋夜蛾) mNPV;及灰翅夜蛾(Spodoptera littoralis
)(非洲棉葉蟲) NPV。 可以『接種劑』形式添加至植物或植物部分或植物器官且由於其特定特性而有助於植物生長及植物健康的細菌及真菌。實例為:農桿菌屬(Agrobacterium spp .
)、莖瘤固氮根瘤菌(Azorhizobium caulinodans
)、固氮螺旋菌屬(Azospirillum spp .
)、固氮菌屬(Azotobacter spp
.)、慢生根瘤菌屬(Bradyrhizobium spp
.)、伯克霍爾德菌屬(Burkholderia spp
.)(詳言之洋蔥伯克霍爾德氏菌(以前被稱為洋蔥假單胞菌))、巨孢囊黴屬(Gigaspora spp
.)或單孢球囊黴(Gigaspora monosporum
)、叢枝菌根菌屬(Glomus spp
.)、蠟蘑菌屬(Laccaria spp
.)、布氏乳桿菌(Lactobacillus buchneri
)、類球囊黴屬(Paraglomus spp .
)、彩色豆馬勃(Pisolithus tinctorus
)、假單胞菌屬(Pseudomonas spp .
)、根瘤菌屬(Rhizobium spp
.)(詳言之三葉草根瘤菌)、麥蕈屬(Rhizopogon spp .
)、硬皮馬勃屬(Scleroderma spp .
)、兔蕈屬(Suillus spp
.)及鏈黴菌屬(Streptomyces spp .
)。 可用作生物控制劑的包括蛋白質及次級代謝物的植物萃取物及由微生物形成的產物,諸如蒜(Allium sativum
)、中亞苦蒿(Artemisia absinthium
)、印楝素(azadirachtin)、Biokeeper WP、黑決明(Cassia nigricans
)、苦皮藤(Celastrus angulatus
)、藜屬土荊芥(Chenopodium anthelminticum
)、甲殼素、Armour-Zen、歐洲鱗毛蕨(Dryopteris filix - mas
)、問荊(Equisetum arvense
)、Fortune Aza、薄荷油(Fungastop)、Heads Up (藜麥皂素萃取物)、除蟲菊/
除蟲菊精、蘇林南苦木(Quassia amara
)、櫟屬(Quercus
)、皂皮樹屬(Quillaja
)、Regalia、「Requiem™殺昆蟲劑」、魚藤酮、魚尼丁/理阿諾鹼、聚合草(Symphytum officinale
)、菊蒿(Tanacetum vulgare
)、瑞香草酚、Triact 70、TriCon、旱金蓮(Tropaeulum majus
)、異株蕁麻(Urtica dioica
)、藜蘆鹼(Veratrin)、槲寄生(Viscum album
)、十字花科萃取物,詳言之油菜粉或芥末粉。
分別可與式(I)化合物及包含其之組合物混合的殺昆蟲劑、殺蟎劑及殺線蟲劑之實例為: (1)乙醯膽鹼酯酶(AChE)抑制劑,諸如胺基甲酸酯類,例如棉靈威(alanycarb)、得滅克(aldicarb)、惡蟲威(bendiocarb)、免扶克(benfuracarb)、丁酮威(butocarboxim)、丁酮碸威(butoxycarboxim)、加保利(carbaryl)、加保扶(carbofuran)、丁基加保扶(carbosulfan)、殺蟲丹(ethiofencarb)、仲丁威(fenobucarb)、複滅蟎(formetanate)、呋線威(furathiocarb)、葉蟬散(isoprocarb)、滅賜克(methiocarb)、納乃得(methomyl)、速滅威(metolcarb)、歐殺滅(oxamyl)、比加普(pirimicarb)、安丹(propoxur)、硫敵克(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混滅威(trimethacarb)、XMC及滅殺威(xylylcarb);或有機磷酸酯,例如歐殺松(acephate)、亞滅松(azamethiphos)、乙基穀速松(azinphos-ethyl)、甲基穀速松(azinphos-methyl)、硫線磷(cadusafos)、氯氧磷(chlorethoxyfos)、克芬松(chlorfenvinphos)、氯甲磷(chlormephos)、甲基陶斯松(chlorpyrifos-methyl)、蠅毒磷(coumaphos)、殺螟腈(cyanophos)、甲基硫代內吸磷(demeton-S-methyl)、大利松(diazinon)、二氯松(dichlorvos)/DDVP、雙特松(dicrotophos)、大滅松(dimethoate)、甲基毒蟲畏(dimethylvinphos)、二硫松(disulfoton)、EPN、愛殺松(ethion)、普伏松(ethoprophos)、伐滅磷(famphur)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、芬殺松(fenthion)、噻唑磷(fosthiazate)、庚烯磷(heptenophos)、新菸磷(imicyafos)、異柳磷(isofenphos)、O-(甲氧基胺基硫基-磷醯基)水楊酸異丙酯、加福松(isoxathion)、馬拉硫磷(malathion)、滅蚜磷(mecarbam)、達馬松(methamidophos)、滅大松(methidathion)、美文松(mevinphos)、亞素靈(monocrotophos)、二溴磷(naled)、氧樂果(omethoate)、甲基滅多松(oxydemeton-methyl)、甲基巴拉松(parathion-methyl)、賽達松(phenthoate)、福瑞松(phorate)、裕必松(phosalone)、益滅松(phosmet)、福賜米松(phosphamidon)、巴賽松(phoxim)、甲基亞特松(pirimiphos-methyl)、布飛松(profenofos)、巴胺磷(propetamphos)、普硫松(prothiofos)、吡唑硫磷(pyraclofos)、噠嗪硫磷(pyridaphenthion)、喹惡磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、雙硫磷(temephos)、託福松(terbufos)、樂本松(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三落松(triazophos)、三氯松(triclorfon)及蚜滅多(vamidothion)。 (2) GABA閘控氯離子通道阻斷劑,諸如環戊二烯-有機氯類,例如氯丹(chlordane)及安殺番(endosulfan)或苯基吡唑(非潑羅(fiproles)),例如乙蟲清(ethiprole)及費普尼(fipronil)。 (3)鈉通道調節劑,諸如擬除蟲菊酯類,例如阿納寧(acrinathrin)、丙烯除蟲菊酯(allethrin)、d-順式反式丙烯菊酯、d-反式丙烯菊酯、畢芬寧(bifenthrin)、生物丙烯菊酯、S-環戊烯基生物丙烯菊酯異構體、苄呋菊脂(bioresmethrin)、乙氰菊脂(cycloprothrin)、賽扶寧(cyfluthrin)、β-賽扶寧、賽洛寧(cyhalothrin)、λ-賽洛寧、γ-賽洛寧、賽滅寧(cypermethrin)、α-賽滅寧、β-賽滅寧、θ-賽滅寧、ξ-賽滅寧、賽酚寧[(1R)-反式異構體]、第滅寧(deltamethrin)、烯炔菊酯[(EZ)-(1R)-異構體]、益化利(esfenvalerate)、依芬寧(etofenprox)、芬普寧(fenpropathrin)、芬化利(fenvalerate)、護賽寧(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-福化利(tau-fluvalinate)、苄蟎醚(halfenprox)、依普寧(imiprothrin)、噻嗯菊酯(kadethrin)、甲氧苄氟菊酯(momfluorothrin)、百滅寧(permethrin)、苯醚菊酯[(1R)-反式異構體]、普亞列寧(prallethrin)、除蟲菊精(除蟲菊)、苄呋菊脂(resmethrin)、矽護芬(silafluofen)、七氟菊酯(tefluthrin)、治滅寧(tetramethrin)、治滅寧[(1R)-異構體]、泰滅寧(tralomethrin)及拜富寧(transfluthrin)或DDT或甲氧滴滴涕(methoxychlor)。 (4)菸鹼乙醯膽鹼受體(nAChR)競爭性調節劑,諸如新菸鹼類似物類,例如啶蟲脒(acetamiprid)、可尼丁(clothianidin)、呋蟲胺(dinotefuran)、吡蟲啉(imidacloprid)、烯啶蟲胺(nitenpyram)、噻蟲啉(thiacloprid)及噻蟲嗪(thiamethoxam)或菸鹼或氟啶蟲胺腈(sulfoxaflor)或氟吡呋喃酮(flupyradifurone)。 (5)菸鹼乙醯膽鹼受體(nAChR)異位調節劑,諸如賜諾殺類(spinosyn),例如斯平托蘭(spinetoram)及賜諾殺(spinosad)。 (6)麩胺酸閘控氯離子通道(GluCl)異位調節劑,諸如阿維菌素類(avermectin)/米爾倍黴素類(milbemycin),例如阿巴汀(abamectin)、因滅汀苯甲酸酯(emamectin benzoate)、林皮沒丁(lepimectin)及密滅汀(milbemectin)。 (7)青少年激素模擬物,諸如青少年激素類似物,例如烯蟲乙酯(hydroprene)、烯蟲炔酯(kinoprene)及美賜平(methoprene)或芬諾克(fenoxycarb)或百利普芬(pyriproxyfen)。 (8)各種非特異性(多位點)抑制劑,諸如烷基鹵化物,例如溴化甲烷及其他烷基鹵化物;或氯化苦或磺醯氟或硼砂或牙垢催吐劑或異氰酸甲酯產生劑,例如必速滅(diazomet)及威百畝(metam)。 (9)弦音器官(Chordotonal Organ)之調節劑,諸如派滅淨(pymetrozine)或氟啶蟲醯胺(flonicamid)。 (10)蟎生長抑制劑,諸如克芬蟎(clofentezine)、合賽多(hexythiazox)及氟蟎嗪(diflovidazin)或依殺蟎(etoxazole)。 (11)昆蟲腸膜之微生物瓦解劑,諸如蘇力菌以色列亞種、枯草芽孢桿菌、蘇力菌亞莎華亞種、蘇力菌庫斯塔克亞種、蘇力菌擬步行甲亞種亞種及B.t.植物蛋白:Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/35Ab1。 (12)粒線體ATP合成酶之抑制劑,諸如ATP瓦解劑,諸如汰芬諾克(diafenthiuron)或有機錫化合物,例如三唑錫(azocyclotin)、錫蟎丹(cyhexatin)及芬布錫(fenbutatin oxide)或毆蟎多(propargite)或四氯殺蟎碸(tetradifon)。 (13)經由破壞質子梯度氧化磷酸化之去偶合劑,諸如克凡派(chlorfenapyr)、DNOC及氟蟲胺(sulfluramid)。 (14)菸鹼乙醯膽鹼受體通道阻斷劑,諸如殺蟲磺(bensultap)、培丹鹽酸鹽(cartap hydrochloride)、硫賜安(thiocylam)及殺蟲雙鈉(thiosultap-sodium)。 (15)甲殼素生物合成之抑制劑,0型,諸如雙三氟蟲脲(bistrifluron)、克福隆(chlorfluazuron)、二福隆(diflubenzuron)、氟環脲(flucycloxuron)、氟芬隆(flufenoxuron)、六伏隆(hexaflumuron)、祿芬隆(lufenuron)、諾伐隆(novaluron)、多氟脲(noviflumuron)、得福隆(teflubenzuron)及三福隆(triflumuron)。 (16)甲殼素生物合成之抑制劑,1型,例如布芬淨(buprofezin)。 (17)脫皮干擾劑(特定言之用於雙翅目,亦即雙翅目昆蟲),諸如賽滅淨(cyromazine)。 (18)蛻皮激素受體促效劑,諸如環蟲醯肼(chromafenozide)、合芬隆(halofenozide)、滅芬諾(methoxyfenozide)及得芬諾(tebufenozide)。 (19)章魚胺受體促效劑,諸如三亞蟎(amitraz)。 (20)粒線體複合物III電子傳輸抑制劑,諸如伏蟻腙(hydramethylnone)或亞醌蟎(acequinocyl)或嘧蟎酯(fluacrypyrim)。 (21)粒線體複合物I電子傳輸抑制劑,諸如來自METI殺蟎劑之群,例如芬殺蟎(fenazaquin)、芬普蟎(fenpyroximate)、嘧蟎醚(pyrimidifen)、比達本(pyridaben)、得芬瑞(tebufenpyrad)及脫芬瑞(tolfenpyrad)或魚藤酮(rotenone)(魚藤(Derris))。 (22)電壓依賴性鈉通道阻斷劑,諸如因得克(indoxacarb)或氰氟蟲胺(metaflumizone)。 (23)乙醯CoA羧化酶之抑制劑,諸如特窗酸(tetronic acid)及特特拉姆酸(tetramic acid)衍生物,例如賜派芬(spirodiclofen)、螺甲蟎酯(spiromesifen)及螺蟲乙酯(spirotetramat)。 (24)粒線體錯合物IV電子傳輸抑制劑,諸如膦,例如磷化鋁、磷化鈣、膦及磷化鋅;或氰化物,例如氰化鈣、氰化鉀及氰化鈉。 (25)粒線體複合物II電子傳輸抑制劑,諸如β-開托利(beta-ketonitrile)衍生物,例如腈吡蟎酯(cyenopyrafen)及丁氟蟎酯(cyflumetofen),及甲苯胺類,諸如吡氟蟎酯(pyflubumide)。 (28)理阿諾鹼受體調節劑,諸如二醯胺類,例如氯蟲苯甲醯胺(chlorantraniliprole)、氰強尼普羅(cyantraniliprole)及氟蟲雙醯胺(flubendiamide), (29)其他活性化合物,諸如雙丙環蟲酯(Afidopyropen)、阿福拉納(Afoxolaner)、印楝素(Azadirachtin)、苯氯噻(Benclothiaz)、苯蟎特(Benzoximate)、畢芬載(Bifenazate)、溴蟲氟苯雙醯胺(Broflanilide)、溴蟎酯(Bromopropylate)、蟎離丹(Chinomethionat)、右旋反式氯丙炔菊酯(Chloroprallethrin)、冰晶石(Cryolite)、右旋反式氯丙炔菊酯(Cyclaniliprole)、環氧蟲啶(Cycloxaprid)、氯氟氰蟲醯胺(Cyhalodiamide)、二氯加士(Dicloromezotiaz)、開樂散(Dicofol)、ε-甲氧苄氟菊酯(epsilon-Metofluthrin)、ε-單氟菊酯(ε-Momfluthrin)、孚蟎喹(Flometoquin)、三氟咪啶醯胺(Fluazaindolizine)、氟噻蟲碸(Fluensulfone)、氟芬內林(Flufenerim)、氟菌蟎酯(Flufenoxystrobin)、丁蟲腈(Flufiprole)、福薩豐(Fluhexafon)、氟吡菌醯胺(Fluopyram)、弗拉拉納(Fluralaner)、氣釀醯胺(Fluxametamide)、呋喃蟲醯肼(Fufenozide)、戊吡蟲胍(Guadipyr)、右旋七氟甲醚菊酯(Heptafluthrin)、氯噻啉(Imidaclothiz)、依普同(Iprodione)、κ-畢芬寧(kappa-Bifenthrin)、κ-七氟菊酯(kappa-Tefluthrin)、洛替拉納(Lotilaner)、氯氟醚菊酯(Meperfluthrin)、哌蟲啶(Paichongding)、啶蟲丙醚(Pyridalyl)、哌氟喹腙(Pyrifluquinazon)、嘧蟎胺(Pyriminostrobin)、螺蝴雙醋(Spirobudiclofen)、四氟醚菊酯(Tetramethylfluthrin)、氟氰蟲醯胺(Tetraniliprole)、四氯蟲醯胺(Tetrachlorantraniliprole)、泰格藍喏(Tigolaner)、硫噁唑芬(Tioxazafen)、硫氟肟醚(Thiofluoximate)、三氟苯嘧啶(Triflumezopyrim)及碘甲烷(iodomethane);其他基於強固芽胞桿菌(Bacillus firmus)之製劑(I-1582, BioNeem, Votivo),以及以下化合物:1-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯基}-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(自WO2006/043635已知)(CAS 885026-50-6)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚-3,4'-哌啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(自WO2003/106457已知)(CAS 637360-23-7)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]哌啶-4-基}-4-(三氟甲基)苯基]異菸鹼醯胺(自WO2006/003494已知)(CAS 872999-66-1)、3-(4-氯-2,6-二甲基苯基)-4-羥基-8-甲氧基-1,8-二氮螺[4.5]癸-3-烯-2-酮(自WO 2010052161已知)(CAS 1225292-17-0)、碳酸3-(4-氯-2,6-二甲基苯基)-8-甲氧基-2-側氧基-1,8-二氮螺[4.5]癸-3-烯-4-基乙酯(自EP2647626已知)(CAS 1440516-42-6)、4-(丁-2-炔-1-基氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(自WO2004/099160已知)(CAS 792914-58-0)、PF1364 (自JP2010/018586已知)(CAS 1204776-60-2)、N-[(2E)-1-[(6-氯吡啶-3-基)甲基]吡啶-2(1H
)-亞基]-2,2,2-三氟乙醯胺(自WO2012/029672已知)(CAS 1363400-41-2)、(3E
)-3-[1-[(6-氯-3-吡啶基)甲基]-2-伸吡啶基]-1,1,1-三氟-丙-2-酮(自WO2013/144213已知)(CAS 1461743-15-6)、N
-[3-(苯甲基胺甲醯基)-4-氯苯基]-1-甲基-3-(五氟乙基)-4-(三氟甲基)-1H
-吡唑-5-甲醯胺(自WO2010/051926已知)(CAS 1226889-14-0)、5-溴-4-氯-N
-[4-氯-2-甲基-6-(甲基胺甲醯基)苯基]-2-(3-氯-2-吡啶基)吡唑-3-甲醯胺(自CN103232431已知)(CAS 1449220-44-3)、4-[5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異噁唑基]-2-甲基-N
-(順-1-氧離子基-3-硫雜環丁烷基)-苯甲醯胺、4-[5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異噁唑基]-2-甲基-N
-(反式-1-氧離子基-3-硫雜環丁烷基)-苯甲醯胺及4-[(5S
)-5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異噁唑基]-2-甲基-N
-(順-1-氧離子基-3-硫雜環丁烷基)苯甲醯胺(自WO 2013/050317 A1已知)(CAS 1332628-83-7)、N -
[3-氯-1-(3-吡啶基)-1H
-吡唑-4-基]-N
-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]-丙醯胺、(+)-N
-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N
-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]-丙醯胺及(-)-N -
[3-氯-1-(3-吡啶基)-1H
-吡唑-4-基]-N
-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]-丙醯胺(自WO 2013/162715 A2、WO 2013/162716 A2、US 2014/0213448 A1已知)(CAS 1477923-37-7)、5-[[(2E
)-3-氯-2-丙烯-1-基]胺基]-1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(三氟甲基)亞磺醯基]-1H-吡唑-3-甲腈(自CN 101337937 A已知)(CAS 1105672-77-2)、3-溴-N
-[4-氯-2-甲基-6-[(甲胺基)硫酮基甲基]苯基]-1-(3-氯-2-吡啶基)-1H
-吡唑-5-甲醯胺(硫代苯甲酸胺,自CN 103109816 A已知)(CAS 1232543-85-9);N -
[4-氯-2-[[(1,1-二甲基乙基)胺基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-3-(氟甲氧基)-1H
-吡唑-5-甲醯胺(自WO 2012/034403 A1已知)(CAS 1268277-22-0)、N -
[2-(5-胺基-1,3,4-噻二唑-2-基)-4-氯-6-甲基苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺(自WO 2011/085575 A1已知)(CAS 1233882-22-8)、4-[3-[2,6-二氯-4-[(3,3-二氯-2-丙烯-1-基)氧基]苯氧基]丙氧基]-2-甲氧基-6-(三氟甲基)-嘧啶(自CN 101337940 A已知)(CAS 1108184-52-6);(2E
)-及2(Z
)-2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亞乙基]-N
-[4-(二氟甲氧基)苯基]-肼甲醯胺(自CN 101715774 A已知)(CAS 1232543-85-9);3-(2,2-二氯乙烯基)-2,2-二甲基-4-(1H
-苯并咪唑-2-基)苯基-環丙烷甲酸酯(自CN 103524422 A已知)(CAS 1542271-46-4);(4aS
)-7-氯-2,5-二氫-2-[[(甲氧基羰基)[4-[(三氟甲基)硫代]苯基]胺基]羰基]-茚并[1,2-e][1,3,4]氧二氮雜環己烯-4a(3H
)-甲酸甲酯(自CN 102391261 A已知)(CAS 1370358-69-2);6-去氧-3-O -
乙基-2,4-二-O
-甲基-1-[N -
[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1H
-1,2,4-三唑-3-基]苯基]胺基甲酸酯]-α-L-吡喃甘露糖(自US 2014/0275503 A1已知)(CAS 1181213-14-8);8-(2-環丙基甲氧基-4-三氟甲基-苯氧基)-3-(6-三氟甲基-噠嗪-3-基)-3-氮雜-雙環[3.2.1]辛烷(CAS 1253850-56-4)、(8-抗)-8-(2-環丙基甲氧基-4-三氟甲基-苯氧基)-3-(6-三氟甲基-噠嗪-3-基)-3-氮雜-雙環[3.2.1]辛烷(CAS 933798-27-7)、(8-同側)-8-(2-環丙基甲氧基-4-三氟甲基-苯氧基)-3-(6-三氟甲基-噠嗪-3-基)-3-氮雜-雙環[3.2.1]辛烷(自WO 2007040280 A1、WO 2007040282 A1已知)(CAS 934001-66-8)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)硫代]-丙醯胺(自WO 2015/058021 A1、WO 2015/058028 A1已知)(CAS 1477919-27-9)及N-[4-(胺基硫酮基甲基)-2-甲基-6-[(甲胺基)羰基]苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺(自CN 103265527 A已知)(CAS 1452877-50-7)、5-(1,3-二噁烷-2-基)-4-[[4-(三氟甲基)苯基]甲氧基]-嘧啶(自WO 2013/115391 A1已知)(CAS 1449021-97-9)、3-(4-氯-2,6-二甲基苯基)-4-羥基-8-甲氧基-1-甲基-1,8-二氮螺[4.5]癸-3-烯-2-酮(自WO 2010/066780 A1、WO 2011/151146 A1已知)(CAS 1229023-34-0)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-1,8-二氮螺[4.5]癸烷-2,4-二酮(自WO 2014/187846 A1已知)(CAS 1638765-58-8)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-2-側氧基-1,8-二氮螺[4.5]癸-3-烯-4-基-碳酸乙酯(自WO 2010/066780 A1、WO 2011151146 A1已知)(CAS 1229023-00-0)、N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-吡啶基亞基]-2,2,2-三氟-乙醯胺(自DE 3639877 A1、WO 2012029672 A1已知)(CAS 1363400-41-2)、[N(E
)]-N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-吡啶基亞基]-2,2,2-三氟-乙醯胺(自WO2016005276 A1已知)(CAS 1689566-03-7)、[N(Z
)]-N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-吡啶基亞基]-2,2,2-三氟-乙醯胺(CAS 1702305-40-5)、3-內-3-[2-丙氧基-4-(三氟甲基)苯氧基]-9-[[5-(三氟甲基)-2-吡啶基]氧基]-9-氮雜雙環[3.3.1]壬烷(自WO 2011/105506 A1、WO 2016/133011 A1已知)(CAS 1332838-17-1)。
可與式(I)化合物及包含其之組合物混合的安全劑之實例為:例如解草酮(benoxacor)、(庚基)解毒喹(cloquintocet)、解草胺腈(cyometrinil)、環丙磺醯胺、二氯丙烯胺、(乙基)解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、呋喃解草唑(furilazole)、雙苯噁唑酸(isoxadifen(-ethyl))、吡唑解草酯(mefenpyr(-diethyl))、萘二甲酸酐、解草腈(oxabetrinil)、2-甲氧基-N-({4-[(甲基胺甲醯基)胺基]苯基}磺醯基)苯甲醯胺(CAS 129531-12-0)、4-(二氯乙醯基)-1-氧雜-4-氮雜螺[4.5]癸烷(CAS 71526-07-3)、2,2,5-三甲基-3-(二氯乙醯基)-1,3-噁唑啶(CAS 52836-31-4)。
可與式(I)化合物及包含其之組合物混合的除草劑之實例為: 乙草胺(Acetochlor)、三氟羧草醚(acifluorfen)、鈉三氟羧草醚(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、草毒死(allidochlor)、禾草滅(alloxydim)、鈉禾草滅(alloxydim-sodium)、莠滅淨(ametryn)、胺唑草酮(amicarbazone)、先甲草胺(amidochlor)、醯嘧磺隆(amidosulfuron)、4-胺基-3-氯-6-(4-氯-2-氟-3-甲基苯基)-5-氟吡啶-2-甲酸、環丙嘧啶酸(aminocyclopyrachlor)、環丙嘧啶酸鉀(aminocyclopyrachlor-potassium)、環丙嘧啶酸甲酯(aminocyclopyrachlor-methyl)、氯胺吡啶酸(aminopyralid)、殺草強(amitrole)、胺磺酸銨(ammoniumsulfamate)、莎稗磷(anilofos)、黃草靈(asulam)、莠去津(atrazine)、草芬定(azafenidin)、四唑嘧磺隆(azimsulfuron)、氟丁醯草胺(beflubutamid)、草除靈(benazolin)、草除靈乙酯(benazolin-ethyl)、氟草胺(benfluralin)、呋草磺(benfuresate)、苄嘧磺隆(bensulfuron)、苄嘧磺隆甲酯(bensulfuron-methyl)、地散磷(bensulide)、滅草松(bentazone)、苯并雙環酮(benzobicyclon)、吡草酮(benzofenap)、雙環比隆(bicyclopyron)、必芬諾(bifenox)畢拉草(bilanafos)、鈉畢拉草(bilanafos-sodium)、雙草醚(bispyribac)、雙草醚鈉(bispyribac-sodium)、除草定(bromacil)、溴丁醯草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、丁酸溴苯腈(bromoxynil-butyrate)、溴苯腈鉀、庚酸溴苯腈及辛酸溴苯腈、比芬農(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、比達寧(butralin)、丁苯草酮(butroxydim)、丁草敵(butylate)、唑草胺(cafenstrole)、長殺草(carbetamide)、克繁草(carfentrazone)、乙基克繁草(carfentrazone-ethyl)、克爛本(chloramben)、氯溴隆(chlorbromuron)、伐草克(chlorfenac)、伐草克鈉、燕麥酯(chlorfenprop)、氯甲丹(chlorflurenol)、甲基氯甲丹、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、乙基氯嘧磺隆、氯鄰苯二甲醯亞胺(chlorophthalim)、綠麥隆(chlorotoluron)、敵草索(chlorthal-dimethyl)、氯磺隆(chlorsulfuron)、吲哚酮草酯(cinidon)、吲哚酮草酯(cinidon-ethyl)、環庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、氯醯草膦(clacyfos)、克草同(clethodim)、炔草酸(clodinafop)、炔草酸(clodinafop-propargyl)、可滅蹤(clomazone)、稗草胺(clomeprop)、畢克草(clopyralid)、氯酯磺草胺(cloransulam)、甲基氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氰胺、氰草津(cyanazine)、環草敵(cycloate)、環密草敵(cyclopyrimorate)、環磺隆(cyclosulfamuron)、環殺草(cycloxydim)、氰氟草酯(cyhalofop)、氰氟草丁酯(cyhalofop-butyl)、環草津(cyprazine)、2,4-D,2,4-D-丁氧基乙酯(2,4-D,2,4-D-butotyl)、2,4-D,2,4-D-丁基、2,4-D,2,4-D-二甲基銨、2,4-D,2,4-D-二乙醇胺、2,4-D,2,4-D-乙基、2,4-D,2,4-D-2-乙基己基、2,4-D,2,4-D-異丁基、2,4-D,2,4-D-異辛基、2,4-D,2,4-D-異丙基銨、2,4-D,2,4-D-鉀、2,4-D,2,4-D-三異丙醇銨及2,4-D,2,4-D-三乙醇胺、2,4-DB,2,4-DB-丁基、2,4-DB,2,4-DB-二甲基銨、2,4-DB,2,4-DB-異辛基、2,4-DB,2,4-DB-鉀及2,4-DB,2,4-DB-鈉、殺草隆(daimuron/dymron)、茅草枯(dalapon)、邁隆(dazomet)、正癸醇、甜菜安(desmedipham)、DTP (detosyl-pyrazolate)、麥草畏(dicamba)、敵草腈(dichlobenil)、2-(2,4-二氯苯甲基)-4,4-二甲基-1,2-噁唑啶-3-酮、2-(2,5-二氯苯甲基)-4,4-二甲基-1,2-噁唑啶-3-酮、滴丙酸(dichlorprop)、滴丙酸-P、禾草靈(diclofop)、甲基禾草靈、禾草靈-P-甲酯(diclofop-P-methyl)、雙氯磺草胺(diclosulam)、苯敵快(difenzoquat)、吡氟草胺(diflufenican)、二氟吡隆(diflufenzopyr)、二氟吡隆鈉、噁唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、異戊乙淨(dimethametryn)、二甲噻草胺(dimethenamid)、二甲噻草胺-P、二甲磺隆(dimetrasulfuron)、敵樂胺(dinitramine)、特樂酚(dinoterb)、草乃敵(diphenamid)、敵草快(diquat)、敵草快二溴化物、氟硫草定(dithiopyr)、達有龍(diuron)、DNOC、草多索(endothal)、EPTC、戊草丹(esprocarb)、乙丁烯氟靈(ethalfluralin)、胺苯磺隆(ethametsulfuron)、甲基胺苯磺隆、乙嗪草酮(ethiozin)、乙呋草黃(ethofumesate)、氯氟草醚(ethoxyfen)、乙基氯氟草醚、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-9600、F-5231 (亦即N-{2-氯-4-氟-5-[4-(3-氟丙基)-5-側氧基-4,5-二氫-1H-四唑-1-基]苯基}乙烷磺醯胺)、F-7967 (亦即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮)、精噁唑禾草靈(fenoxaprop)、精噁唑禾草靈-P、乙基精噁唑禾草靈、精噁唑禾草靈-P-乙酯、異噁苯碸(fenoxasulfone)、喹喏啉草酮(fenquinotrione)、四唑醯草胺(fentrazamide)、麥草氟(flamprop)、麥草氟異丙酯、麥草氟甲酯、嘧啶磺隆(flazasulfuron)、雙氟磺草胺(florasulam)、吡氟禾草靈(fluazifop)、吡氟禾草靈-P、吡氟禾草靈丁酯、吡氟禾草靈-P-丁酯、氟酮磺隆(flucarbazone)、氟酮磺隆鈉、氟吡磺隆(flucetosulfuron)、氟消草(fluchloralin)、氟噻草胺(flufenacet)、氟噠嗪草酯(flufenpyr)、氟噠嗪草乙酯、唑嘧磺草胺(flumetsulam)、氟胺草酯(flumiclorac)、氟胺草戊酯、丙炔氟草胺(flumioxazin)、伏草隆(fluometuron)、抑草丁(flurenol)、抑草丁丁酯、抑草丁二甲基銨及抑草丁甲酯、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚乙酯、四氟丙酸、氟啶嘧磺隆(flupyrsulfuron)、氟啶嘧磺隆甲基鈉、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟草定(fluroxypyr)、氟草菸1-甲基庚基酯(fluroxypyr-meptyl)、呋草酮(flurtamone)、氟噻草酯(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、氟磺胺草醚鈉、甲醯嘧磺隆(foramsulfuron)、殺木膦(fosamine)、草銨膦(glufosinate)、草銨膦銨、草銨膦-P-鈉、草銨膦-P-銨、草銨膦-P-鈉、嘉磷塞(glyphosate)、嘉磷塞銨、嘉磷塞異丙銨、嘉磷塞二銨、嘉磷塞二甲基銨、嘉磷塞鉀、嘉磷塞鈉及嘉磷塞三甲基硫、H-9201 (亦即O-(2,4-二甲基-6-硝苯)O-乙基異丙基硫代磷醯胺)、氟氯吡啶酯(halauxifen)、氟氯吡啶甲酯、氟硝磺醯胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆甲酯、精吡氟氯禾靈(haloxyfop)、精吡氟氯禾靈-P、精吡氟氯禾靈乙氧基乙酯、精吡氟氯禾靈-P-乙氧基乙酯、精吡氟氯禾靈甲酯、精吡氟氯禾靈-P-甲酯、六嗪同(hexazinone)、HW-02 (亦即1-(二甲氧基磷醯基)乙基-(2,4-二氯苯氧基)乙酸酯)、咪草酸(imazamethabenz)、咪草酸甲酯、甲氧咪草菸(imazamox)、甲氧咪草菸銨、甲咪唑菸酸(imazapic)、甲咪唑菸酸銨鹽、滅草菸、滅草菸異丙基銨鹽、滅草喹(imazaquin)、滅草喹銨鹽、咪草菸(imazethapyr)、咪草菸亞胺鎓(imazethapyr-immonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、茚嗪氟草胺(indaziflam)、碘甲磺隆(iodosulfuron)、碘甲磺隆甲基鈉、碘苯腈(ioxynil)、碘苯腈辛酸酯、碘苯腈鉀及碘苯腈鈉、艾分卡巴腙(ipfencarbazone)、異丙隆(isoproturon)、異惡隆(isouron)、異噁草胺(isoxaben)、異噁唑草酮(isoxaflutole)、卡草靈(karbutilate)、KUH-043 (亦即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺醯基)-5,5-二甲基-4,5-二氫-1,2-噁唑)、克螺多克(ketospiradox)、乳氟禾草靈(lactofen)、環草定(lenacil)、利穀隆(linuron)、MCPA、MCPA丁氧基乙酯、MCPA二甲基胺、MCPA-2-乙基己酯、MCPA異丙基胺、MCPA鉀及MCPA鈉、MCPB、MCPB甲酯、MCPB乙酯及MCPB鈉、2-甲-4-氯丙酸、2-甲-4-氯丙酸鈉及2-甲-4-氯丙酸丁氧基乙酯、2-甲-4-氯丙酸-P、2-甲-4-氯丙酸-P-丁氧基乙酯、2-甲-4-氯丙酸-二甲基銨、2-甲-4-氯丙酸-2-乙基己酯及2-甲-4-氯丙酸鉀、苯噻醯草胺(mefenacet)、氟磺醯草胺(mefluidide)、甲基二磺隆(mesosulfuron)、甲基二磺隆甲酯、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百畝、噁唑醯草胺(metamifop)、苯嗪草酮(metamitron)、吡草胺(metazachlor)、雙醚氯吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、甲硫喃磺隆(methiopyrsulfuron)、甲硫草除靈(methiozolin)、硫氰酸甲酯、溴穀隆(metobromuron)、異丙甲草胺(metolachlor)、高效異丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、賽克津(metribuzin)、甲磺隆(metsulfuron)、甲磺隆甲酯、稻得壯(molinat)、綠穀隆(monolinuron)、單嘧磺隆(monosulfuron)、單嘧磺隆酯、MT-5950 (亦即N-(3-氯-4-異丙基苯基)-2-甲基戊醯胺)、NGGC-011、敵草胺(napropamide)、NC-310 (亦即[5-(苯甲氧基)-1-甲基-1H-吡唑-4-基](2,4-二氯苯基)甲酮)、草不隆(neburon)、菸嘧磺隆(nicosulfuron)、壬酸(天竺葵酸)、達草滅(norflurazon)、油酸(脂肪酸)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺樂靈(oryzalin)、丙炔噁草酮(oxadiargyl)、噁草酮(oxadiazon)、環氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefon)、乙氧氟草醚(oxyfluorfen)、巴拉割(paraquat)、巴拉割二氯化物、克草猛(pebulate)、二甲戊樂靈(pendimethalin)、平速爛(penoxsulam)、五氯酚、環戊噁草酮(pentoxazone)、烯草胺(pethoxamid)、石油、甜菜寧(phenmedipham)、胺氯吡啶酸(picloram)、氟吡草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、氟嘧磺隆甲酯、氨基丙氟靈(prodiamine)、環苯草酮(profoxydim)、撲滅通(prometon)、撲草淨(prometryn)、撲草胺(propachlor)、敵稗(propanil)、喔草酯(propaquizafop)、撲滅津(propazine)、苯胺靈(propham)、異丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆鈉、丙嘧磺隆(propyrisulfuron)、戊炔草胺(propyzamide)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、雙唑草腈(pyraclonil)、吡草醚(pyraflufen)、吡草醚乙酯、磺醯草吡唑(pyrasulfotole)、吡唑特(pyrazolynate/pyrazolate)、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆乙酯、苄草唑(pyrazoxyfen)、酯草醚(pyribambenz)、異丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、吡啶達醇(pyridafol)、噠草特(pyridate)、環酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧草醚甲酯(pyriminobac-methyl)、嘧啶硫蕃(pyrimisulfan)、嘧硫草醚(pyrithiobac)、嘧硫草醚鈉(pyrithiobac-sodium)、嘧氧碸(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、莫克草(quinoclamine)、快伏草(quizalofop)、快伏草乙酯(quizalofop-ethyl)、快伏草-P (quizalofop-P)、快伏草-P-乙酯(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、碸嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、西殺草(sethoxydim)、環草隆(siduron)、西瑪津(simazine)、西草淨(simetryn)、SL-261、磺草酮(sulcotrion)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆甲酯(sulfometuron-methyl)、磺醯磺隆(sulfosulfuron)、SYN-523、SYP-249(亦即5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸1-乙氧基-3-甲基-1-側氧基丁-3-烯-2-基酯)、SYP-300 (亦即1-[7-氟-3-側氧基-4-(丙-2-炔-1-基)-3,4-二氫-2H-1,4-苯并噁嗪-6-基]-3-丙基-2-硫酮基咪唑啶-4,5-二酮、2,3,6-TBA、TCA (三氯乙酸)、TCA鈉、得匍隆(tebuthiuron)、特呋喃隆(tefuryltrione)、環磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草靈(terbucarb)、甲氧去草淨(terbumeton)、特丁津(terbuthylazin)、去草淨(terbutryn)、甲氧噻草(thenylchlor)、胺噻草定(thiazopyr)、噻酮磺隆(thiencarbazone)、噻酮磺隆甲酯(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆甲酯(thifensulfuron-methyl)、禾草丹(thiobencarb)、氟丙嘧草酯(tiafenacil)、禾草敵(tolpyralate)、苯吡唑草酮(topramezone)、肟草酮(tralkoxydim)、氟酮磺草胺(triafamone)、野麥畏(triallate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、苯磺隆甲酯(tribenuron-methyl)、綠草定(triclopyr)、草達津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆鈉(trifloxysulfuron-sodium)、三氟草嗪(trifludimoxazin)、氟樂靈(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆甲酯(triflusulfuron-methyl)、三氟甲磺隆(tritosulfuron)、硫酸脲、滅草猛(vernolate)、XDE-848、ZJ-0862 (亦即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苯甲基}苯胺)及以下化合物:
植物生長調節劑之實例為: 酸化苯并噻二唑、酸化苯并噻二唑-S-甲酯、5-胺基乙醯丙酸、嘧啶醇、6-苯甲基胺基嘌呤、芸苔素內酯(Brassinolid)、兒茶素(catechine)、氯化克美素(chlormequat chloride)、坐果安(cloprop)、環丙酸醯胺(cyclanilide)、3-(環丙-1-烯基)丙酸、丁醯肼(daminozide)、邁隆(dazomet)、正癸醇、敵草克(dikegulac)、敵草克鈉(dikegulac-sodium)、草多索(endothal)、草多索二鉀(endothal-dipotassium)、草多索二鈉及草多索單(N,N-二甲基烷基銨)、益收生長素(ethephon)、氟節胺(flumetralin)、抑草丁(flurenol)、抑草丁丁酯(flurenol-butyl)、調嘧醇(flurprimidol)、氯吡脲(forchlorfenuron)、赤黴酸、依納素(inabenfide)、吲哚-3-乙酸(IAA)、4-吲哚-3-基丁酸、稻瘟靈(isoprothiolane)、撲殺熱、茉莉酸、順丁烯二醯肼、縮節胺(mepiquat chloride)、1-甲基環丙稀、茉莉酸甲酯、2-(1-萘基)乙醯胺、1-萘基乙酸、2-萘氧基乙酸、硝基酚鹽混合物、巴克素(paclobutrazol)、N-(2-苯乙基)-β-丙胺酸、N-苯基鄰胺甲醯苯甲酸、調環酸(prohexadione)、調環酸鈣(prohexadione-calcium)、茉莉酮(prohydrojasmone)、水楊酸、獨腳金內酯(strigolactone)、四氯硝基苯(tecnazene)、噻苯隆(thidiazuron)、三十烷醇(triacontanol)、抗倒酯(trinexapac)、抗倒乙酯(trinexapac-ethyl)、斯脫得(tsitodef)、烯效唑(uniconazole)、烯效唑-P (uniconazole-P)。
方法及用途
式(I)化合物及包含其之組合物具有強殺微生物活性及/或植物防禦調節潛力。其可用於控制非所需微生物,諸如非所需真菌及細菌。如本文下文中更詳細地描述,其可尤其適用於作物保護(其控制引起植物病害之微生物)或尤其適用於保護材料(例如,工業材料、木材、儲存貨物)。更具體言之,式(I)化合物或包含其之組合物可用以保護種子、發芽植物、所冒出苗木、植物、植物部分、果實、收穫物及/或植物生長之土壤免受非所需微生物傷害。
如本文中所用,控制(control/controlling)涵蓋非所需微生物之保護性、治癒性及根除性處理。非所需微生物可為病原性細菌、病原性病毒、病原性卵菌或病原性真菌,更具體言之可為植物病原性細菌、植物病原性病毒、植物病原性卵菌或植物病原性真菌。如本文下文中所詳細描述,此等植物病原性微生物為廣泛範圍之植物病害之致病原因。
更特定言之,式(I)化合物及包含其之組合物可用作殺真菌劑。出於本說明書之目的,術語「殺真菌劑」係指可用於作物保護以供控制非所需真菌(諸如根腫菌、壺菌、接合菌、子囊菌、擔子菌及半知菌)及/或控制卵菌的化合物或組合物。
式(I)化合物及包含其之組合物亦可用作抗細菌劑。詳言之,其可適用於作物保護,例如用於控制非所需細菌,諸如假單胞菌科、根瘤菌科、黃單胞菌科、腸內菌科、棒狀桿菌科及鏈絲菌科。
式(I)化合物及包含其之組合物亦可用作作物保護中的抗病毒劑。舉例而言,式(I)化合物及包含其之組合物可對植物病毒引起之病害有效,該等植物病毒諸如菸草嵌紋病毒(TMV)、菸草脆裂病毒(tobacco rattle virus)、菸草矮化病毒(TStuV)、菸草捲葉病毒(VLCV)、菸草脈葉藍嵌紋病毒(TVBMV)、菸草壞死性矮縮病毒(TNDV)、菸草條紋病毒(TSV)、馬鈴薯病毒X (PVX)、馬鈴薯病毒Y、馬鈴薯病毒S、馬鈴薯病毒M及馬鈴薯病毒A、馬鈴薯奧古巴嵌紋病毒(potato acuba mosaic virus;PAMV)、馬鈴薯帚頂病毒(PMTV)、馬鈴薯卷葉病毒(PLRV)、苜蓿花葉病毒(AMV)、胡瓜嵌紋病毒(CMV)、胡瓜綠色斑駁花葉病毒(CGMMV)、胡瓜黃化病毒(CuYV)、西瓜嵌紋病毒(WMV)、番茄斑萎病毒(TSWV)、番茄輪點病毒(TomRSV)、甘蔗嵌紋病毒(SCMV)、水稻矮縮病毒、水稻條斑病毒、水稻黑條矮縮病毒、草莓斑紋病毒(SMoV)、草莓鑲脈病毒(SVBV)、草莓輕度黃邊病毒(SMYEV)、草莓連葉病毒(SCrV)、蠶豆萎凋病毒(BBWV)及甜瓜壞死性斑點病毒(MNSV)。
本發明亦係關於一種用於控制非所需微生物之方法,非所需微生物詳言之為非所需植物病原性微生物,諸如非所需真菌、卵菌及細菌,該方法包含向該等微生物及/或其生境(向植物、植物部分、種子、果實或向植物生長之土壤)施加一或多種式(I)化合物或包含其之組合物的步驟。
通常,當式(I)化合物及包含其之組合物用於治癒性或保護性方法以控制植物病原性真菌及/或植物病原性卵菌時,將其有效量及植物可相容量施加至植物、植物部分、果實、種子或施加至植物生長的土壤或基質。可用於培育植物的適合基質包括:無機類基質,諸如礦棉,詳言之岩棉、珍珠岩、砂或礫石;有機基質,諸如泥炭、松樹皮或鋸屑;及石油類基質,諸如聚合泡沫或塑膠珠粒。有效量及植物可相容量意謂足以控制或毀壞耕地上存在或易在耕地上出現的真菌,且不會引起該等作物之任何顯著的植物毒性症狀。視待控制之真菌、作物類型、作物生長階段、氣候條件以及各別式(I)化合物及包含其之組合物而定,此類量可在廣泛圍內變化。此量可藉由熟習此項技術者能力範圍內之系統田間試驗來測定。
植物及植物部分
可將式(I)化合物及包含其之組合物施加至任何植物或植物部分。
植物意謂所有植物及植物群體,諸如所需及非所需野生植物或作物植物(包括天然存在之作物植物)。作物植物可為藉由習知育種及最佳化方法或藉由生物技術及基因工程方法或此等方法之組合可獲得的植物,包括經基因修飾之植物(GMO或轉殖基因植物)及可受及不受植物育種者權利保護達植物栽培品種。
經基因修飾之植物(GMO或轉殖基因植物)為異源基因已穩定整合於基因組中之植物。表述「異源基因」基本上意謂在植物外部且在引入核、葉綠體或粒線體基因組中時提供或組裝的基因。此基因藉由表現相關蛋白質或多肽或藉由下調或抑制植物中存在之其他基因(使用例如反義技術、共抑制技術、RNA干擾-RNAi技術或微RNA-miRNA技術)賦予轉形植物新的或改良的農藝特性或其他特性。位於基因組中之異源基因亦稱為轉殖基因。由在植物基因組中之特定位置定義之轉殖基因稱為轉形或轉殖基因事件。
應將植物栽培品種理解為意謂具有新特性(「性狀」)且已藉由習知育種、藉由突變誘發或藉由重組DNA技術獲得的植物。其可為栽培品種、變種、生物型或基因型。
應將植物部分理解為意謂地上及地下之植物的所有部分及器官,諸如幼芽、葉片、針葉、莖梗(stalk)、莖(stem)、花朵、子實體、果實、種子、根部、塊莖及根莖。植物部分亦包括收穫的物質及無性與有性繁殖物質,例如插條、塊莖、根莖、幼枝及種子。
可根據本發明之方法處理之植物包括以下:棉、亞麻、葡萄藤、果實、蔬菜,諸如薔薇科(Rosaceae sp .
) (例如梨果,諸如蘋果及梨,以及核果,諸如杏、櫻桃、杏仁及桃,及軟果實,諸如草莓)、茶藨子科(Ribesioidae sp .
)、胡桃科(Juglandaceae sp .
)、樺科(Betulaceae sp .
)、漆樹科(Anacardiaceae sp .
)、山毛櫸科(Fagaceae sp .
)、桑科(Moraceae sp .
)、木樨科(Oleaceae sp .
)、獼猴桃科(Actinidaceae sp .
)、樟科(Lauraceae sp .
)、芭蕉科(Musaceae sp .
) (例如香蕉樹及種植園)、茜草科(Rubiaceae sp .
) (例如咖啡豆)、茶科(Theaceae sp .
)、梧桐科(Sterculiceae sp .
)、芸香科(Rutaceae sp .
) (例如檸檬、橙及葡萄柚);茄科(Solanaceae sp .
) (例如蕃茄)、百合科(Liliaceae sp .
)、菊科(Asteraceae sp .
) (例如萵苣)、傘形科(Umbelliferae sp .
)、十字花科(Cruciferae sp .
)、藜科(Chenopodiaceae sp .
)、葫蘆科(Cucurbitaceae sp .
) (例如胡瓜)、蔥科(Alliaceae sp .
) (例如韭菜、洋蔥)、蝶形花科(Papilionaceae sp .
) (例如豆類);主要作物植物,諸如禾本科(Gramineae sp .
) (例如玉米、草皮、穀物,諸如小麥、粗麥、水稻、大麥、燕麥、栗及黑小麥)、菊科(Asteraceae sp .
) (例如向日葵)、十字花科(Brassicaceae sp .
) (例如白甘藍菜、紅甘藍菜、椰菜、花椰菜、球芽甘藍、白菜、球莖甘藍、小蘿蔔及油菜、芥末、辣根及水芹)、豆科(Fabacae sp .
) (例如豆類、花生)、蝶形花科(Papilionaceae sp .
) (例如大豆)、茄科(Solanaceae sp .
) (例如馬鈴薯)、藜科(Chenopodiaceae sp .
) (例如糖用甜菜、飼料甜菜、紅頭菜、甜菜);適用的植物及用於園林及森林區域之觀賞植物;及經基因修飾的各種各樣的此等植物中之各者。
可藉由上文所揭示之方法處理之植物及植物栽培品種包括抗一或多種生物性逆境的植物及植物栽培品種,亦即,該等植物展示對動物及微生物害蟲之更佳防禦,諸如抵抗線蟲、昆蟲、蟎、植物病原性真菌、細菌、病毒及/或類病毒。
可藉由上文所揭示之方法處理之植物及植物栽培品種包括抗一或多種非生物性逆境的彼等植物。非生物性逆境條件可包括例如乾旱、低溫暴露、熱暴露、滲透壓力、洪水、增加之土壤鹽度、增加之礦物質暴露、臭氧暴露、高光暴露、氮養分之有限可用性、磷養分之有限可用性、避蔭。
可藉由上文所揭示之方法處理之植物及植物栽培品種包括表徵為產量特徵增強之彼等植物。該等植物之產量增加可為例如改良植物生理學、生長及發育(諸如水利用效率、水保持效率、改良氮使用、增強碳同化、改良光合成、增加發芽效率及加快成熟)之結果。產量可另外受改良之植物株型影響(在逆境及非逆境條件下),該改良之植物株型包括(但不限於)早期開花、對雜交種子生產之開花控制、幼苗活力、植物大小、節間數目及距離、根生長、種子大小、果實大小、豆莢大小、豆莢或穗數目、每個豆莢或穗之種子數目、種子質量、增強之種子填充、降低之種子散佈度、降低之豆莢開裂性及抗倒伏性。其他產量性狀包括種子組成,諸如,例如棉或澱粉之碳水化合物含量及組成、蛋白質含量、油含量及組成、營養值、抗營養化合物之還原、經改良可加工性及更佳儲存穩定性。
可藉由上文所揭示之方法處理之植物及植物栽培品種包括為雜交植物之植物及植物栽培品種,該等雜交植物已表現大體上引起較高產量、活力、健康及抗生物及非生物逆境之雜種優勢或雜交活力的特徵。
可藉由上文所揭示之方法處理之植物及植物栽培品種(藉由諸如基因工程之植物生物技術方法獲得)包括為除草劑耐受性植物之植物及植物栽培品種,亦即對一或多種給定除草劑耐受的植物。此類植物可藉由遺傳轉形或藉由選擇含有賦予此類除草劑耐受性之突變之植物獲得。
可藉由上文所揭示之方法處理之植物及植物栽培品種(藉由諸如基因工程之植物生物技術方法獲得)包括為昆蟲抗性轉殖基因植物之植物及植物栽培品種,亦即對某些靶標昆蟲之攻擊具有抗性的植物。此類植物可藉由遺傳轉形或藉由選擇含有賦予此類昆蟲抗性之突變之植物來獲得。
可藉由上文所揭示之方法處理之植物及植物栽培品種(藉由諸如基因工程之植物生物技術方法獲得)包括為病害抗性轉殖基因植物之植物及植物栽培品種,亦即對某些靶標昆蟲之攻擊具有抗性的植物。此類植物可藉由遺傳轉形或藉由選擇含有賦予此類昆蟲抗性之突變之植物來獲得。
可藉由上文所揭示之方法處理之植物及植物栽培品種(藉由諸如基因工程之植物生物技術獲得)包括對非生物逆境耐受之植物及植物栽培品種。此類植物可藉由遺傳轉形或藉由選擇含有賦予此類逆境耐受性之突變之植物獲得。
可藉由上文所揭示之方法處理之植物及植物栽培品種(藉由諸如基因工程之植物生物技術方法獲得)包括展示更改所收穫產物之數量、品質及/或儲存穩定性及/或更改所收穫產物之特定成分之特性的植物及植物栽培品種。
可藉由上文所揭示之方法處理之植物及植物栽培品種(藉由諸如基因工程之植物生物技術方法獲得)包括具有經更改纖維特徵之植物及植物栽培品種(諸如,棉植物)。此類植物可藉由遺傳轉形或藉由選擇含有賦予此類經更改纖維特徵之突變之植物獲得。
可藉由上文所揭示之方法處理之植物及植物栽培品種(藉由諸如基因工程之植物生物技術方法獲得)包括具有經更改油概況特徵之植物及植物栽培品種,諸如油菜或相關蕓薹屬植物。此類植物可藉由遺傳轉形或藉由選擇含有賦予此類經更改油概況特徵之突變之植物獲得。
可藉由上文所揭示之方法處理之植物及植物栽培品種(藉由諸如基因工程之植物生物技術方法獲得)包括具有經更改落粒性特徵之植物及植物栽培品種,諸如油菜或相關蕓薹屬植物。此類植物可藉由遺傳轉形或藉由選擇含有賦予此類經更改落粒性特徵之突變之植物來獲得,且包括具有延遲或降低落粒性之植物,諸如油菜植物。
可藉由上文所揭示之方法處理之植物及植物栽培品種(藉由諸如基因工程之植物生物技術方法獲得)包括具有經更改轉譯後蛋白修飾模式之植物及植物栽培品種,諸如菸草植物。
病原體
可根據本發明治療之真菌性病害之病原體的非限制性實例包括: 由白粉病病原體引起之病害,該等白粉病病原體例如:白粉病菌屬(Blumeria
species),例如禾本科布氏白粉菌(Blumeria graminis
);叉絲單囊殼屬(Podosphaera
species),例如白叉絲單囊殼(Podosphaera leucotricha
);單絲殼屬(Sphaerotheca
species),例如單絲殼白粉菌(Sphaerotheca fuliginea
);鉤絲殼屬(Uncinula
species),例如葡萄白粉病菌(Uncinula necator
); 由銹病病原體引起之病害,該等銹病病原體例如:膠鏽菌屬(Gymnosporangium
species),例如褐色膠鏽菌(Gymnosporangium sabinae
);駝孢鏽菌屬(Hemileia
species),例如咖啡駝孢鏽菌(Hemileia
vastatrix);層鏽菌屬(Phakopsora
species),例如大豆鏽菌(Phakopsora pachyrhizi
)或層鏽層假尾孢菌(Phakopsora meibomiae
);柄鏽菌屬(Puccinia
species),例如麥類葉銹病菌(Puccinia recondita
)、禾柄鏽菌奧德條形柄鏽菌(Puccinia graminis oder Puccinia striiformis);單孢鏽菌屬(Uromyces
species),例如菜豆銹病菌(Uromyces appendiculatus
); 由來自卵菌之群的病原體引起之病害,該等病原體例如:白銹病屬(Albugo
species),例如白鏽菌(Albugo candida
);萵苣露菌病菌屬(Bremia
species),例如萵苣露菌病(Bremia lactucae
);霜黴菌屬(Peronospora
species),例如豌豆霜黴菌(Peronospora pisi
)或芸苔根腫菌(P . brassicae
);疫黴菌屬(Phytophthora
species),例如致病疫黴(Phytophthora infestans
);單軸黴屬(Plasmopara
species),例如葡萄生單軸黴(Plasmopara viticola
);假霜黴屬(Pseudoperonospora
species),例如葎草假霜黴(Pseudoperonospora humuli
)或古巴假霜黴菌(Pseudoperonospora cubensis
);腐黴菌屬(Pythium
species),例如終極腐黴菌(Pythium ultimum
); 由例如以下引起之葉斑病及葉萎病:鏈隔孢菌屬(Alternaria
species),例如立枯鏈隔孢菌(Alternaria solani
);尾孢菌屬(Cercospora
species),例如甜菜尾孢菌(Cercospora beticola
);黑星病菌屬(Cladiosporium
species),例如黃瓜黑星病菌(Cladiosporium cucumerinum
);旋孢腔菌屬(Cochliobolus
species),例如禾旋孢腔菌(Cochliobolus sativus) (分生孢子形式:內臍蠕孢屬(Drechslera
),同義詞:長蠕孢(Helminthosporium
))或宮部旋孢腔菌(Cochliobolus miyabeanus
);刺盤孢屬(Colletotrichum
species),例如菜豆炭疽病菌(Colletotrichum lindemuthanium
);棒孢黴屬(Corynespora
species),例如多主棒孢黴(Corynespora cassiicola
);孔雀斑菌屬(Cycloconium
species),例如油橄欖孔雀斑菌(Cycloconium oleaginum
);黑點病菌屬(Diaporthe species),例如柑橘黑點病菌(Diaporthe citri
);痂囊腔菌屬(Elsinoe
species),例如柑桔痂囊腔菌(Elsinoe fawcettii
);炭疽病菌屬(Gloeosporium
species),例如桃炭疽病菌(Gloeosporium
laeticolor);小叢殼屬(Glomerella
species),例如圍小叢殼菌(Glomerella cingulata
);球座菌屬(Guignardia
species),例如葡萄球座菌(Guignardia bidwelli
);小球腔菌屬(Leptosphaeria
species),例如十字花科小球腔菌(Leptosphaeria maculans
);稻瘟菌屬(Magnaporthe
species),例如稻瘟菌(Magnaporthe grisea
);微結節菌屬(Microdochium
species),例如雪黴枯葉病菌(Microdochium nivale
);球腔菌屬(Mycosphaerella
species),例如禾生球腔菌(Mycosphaerella graminicola
)、落花生球腔菌(Mycosphaerella arachidicola
)或斐濟球腔菌(Mycosphaerella fijiensis
);暗球腔菌屬(Phaeosphaeria
species),例如小麥葉枯病菌(Phaeosphaeria nodorum
);核腔菌屬(Pyrenophora
species),例如大麥網斑病菌(Pyrenophora teres
)或偃麥草核腔菌(Pyrenophora tritici repentis
);柱隔孢屬(Ramularia
species),例如柱隔孢(Ramularia collo-cygni)或白斑柱隔孢;雲紋病菌屬(Rhynchosporium
species),例如大麥雲紋病菌(Rhynchosporium secalis
);殼針孢屬(Septoria
species),例如芹菜小殼針孢(Septoria apii
)或番茄殼針孢(Septoria lycopersici
);殼多孢屬(Stagonospora
species),例如穎枯殼針孢(Stagonospora nodorum
);核瑚菌屬(Typhula
species),例如肉孢核瑚菌(Typhula incarnata
);黑星菌屬(Venturia
species),例如蘋果黑星病菌(Venturia inaequalis
); 由例如以下引起之根部及莖稈病害:伏革菌屬(Corticium
species),例如禾穀鐮孢伏革菌(Corticium graminearum
);鐮菌屬(Fusarium
species),例如尖孢鐮刀菌(Fusarium oxysporum
);頂囊殼屬(Gaeumannomyces
species),例如禾草頂囊殼菌(Gaeumannomyces graminis
);根腫菌屬(Plasmodiophora
species),例如甘藍根腫菌(Plasmodiophora brassicae
);絲核菌屬(Rhizoctonia
species),例如立枯絲核菌(Rhizoctonia solani
);帚枝黴屬(Sarocladium
species),例如稻葉鞘腐敗病菌(Sarocladium oryzae
);小核菌屬(Sclerotium
species),例如稻小核菌(Sclerotium oryzae
);塔普斯菌屬(Tapesia
species),例如塔普斯梭狀芽胞桿菌(Tapesia acuformis
);根串珠黴屬(Thielaviopsis
species),例如菫菜根腐病菌(Thielaviopsis basicola
); 由例如以下引起之穗及圓錐花序病害(包括玉米穗軸):鏈隔孢菌屬(Alternaria
species),例如鏈隔孢菌屬(Alternaria spp .
);麴菌屬(Aspergillus
species),例如黃麴菌(Aspergillus flavus
);分枝孢子菌屬(Cladosporium
species),例如芽枝狀枝孢黴(Cladosporium cladosporioides
);麥角菌屬(Claviceps
species),例如紫黑麥角菌(Claviceps purpurea
);鐮菌屬(Fusarium
species),例如黃色鐮孢菌(Fusarium culmorum
);赤黴菌屬(Gibberella
species),例如玉米赤黴(Gibberella zeae
);小畫線殼屬(Monographella
species),例如雪黴小畫線殼(Monographella nivalis
);殼多孢菌屬(Stagnospora
species),例如穎枯殼針孢(Stagonospora nodorum
); 由黑穗病真菌引起之病害,該等黑穗病真菌例如:蜀黍小黑穗病菌屬(Sphacelotheca
species),例如高粱絲黑粉菌(Sphacelotheca reiliana
);腥黑粉菌屬(Tilletia
species),例如小麥矮腥黑粉菌(Tilletia caries
或Tilletia
controversa);條黑粉菌屬(Urocystis
species),例如隱條黑粉菌(Urocystis occulta
);黑粉菌屬(Ustilago
species),例如麥散黑粉菌(Ustilago nuda
); 由例如以下引起之果腐病:黃麴菌;葡萄孢屬(Botrytis
species),例如灰葡萄孢菌(Botrytis cinerea
);鏈核盤菌屬(Monilinia
species),例如拉克撒鏈核盤菌(Monilinia laxa
);青黴菌屬(Penicillium
species),例如擴展青黴(Penicillium expansum
)或產紫青黴(Penicillium purpurogenum
);根黴菌屬(Rhizopus
species),例如匍枝根黴(Rhizopus stolonifer
);核盤菌屬(Sclerotinia
species),例如向日葵核盤菌(Sclerotinia sclerotiorum
);輪枝孢屬(Verticilium
species),例如黃萎輪枝黴(Verticilium alboatrum
); 種子及土壤媒介腐病及萎病以及由例如以下引起之苗木病害:鏈隔孢菌屬,例如甘藍鏈隔孢菌(Alternaria brassicicola
);絲囊黴屬(Aphanomyces
species),例如兵豆絲囊黴(Aphanomyces euteiches
);殼二孢屬(Ascochyta
species),例如晶狀殼二孢(Ascochyta lentis
);麴菌屬,例如黃麴菌;分枝孢子菌屬,例如多主枝孢黴(Cladosporium herbarum
);旋孢腔菌屬,例如禾旋孢腔菌(分生孢子形式:內臍蠕孢屬,同義詞:長蠕孢);刺盤孢屬,例如仙人掌炭疽刺盤孢菌(Colletotrichum coccodes
);鐮菌屬,例如黃色鐮孢菌;赤黴菌屬,例如玉米赤黴;殼球孢屬(Macrophomina
species),例如萊豆殼球孢(Macrophomina phaseolina
);微結節菌屬,例如雪黴枯葉病菌;小畫線殼屬,例如雪黴小畫線殼;青黴菌屬,例如擴展青黴;莖點黴屬(Phoma
species),例如黑脛莖點黴(Phoma lingam
);擬莖點黴屬(Phomopsis
species),例如大豆擬莖點黴;疫黴菌屬(Phytophthora
species),例如惡疫黴(Phytophthora cactorum
);核腔菌屬,例如大麥核腔菌;梨孢屬(Pyricularia
species),例如稻梨孢(Pyricularia oryzae
);腐黴菌屬,例如終極腐黴菌;絲核菌屬,例如立枯絲核菌;根黴菌屬,例如酒麴菌;小核菌屬,例如白絹病小核菌(Sclerotium rolfsii
);殼針孢屬,例如穎枯殼針孢;核瑚菌屬,例如內孢核瑚菌;輪枝菌屬,例如大麗花輪枝孢; 由例如以下引起之癌症、蟲癭及叢枝病:叢赤殼屬(Nectria
species),例如,仁果幹癌叢赤殼(Nectria galligena
); 由例如以下引起之萎病:輪枝菌屬,例如長孢輪枝菌(Verticillium longisporum
);鐮菌屬,例如尖孢鐮刀菌; 由例如以下引起之葉片、花及果實之畸形:外擔菌屬(Exobasidium
species),例如,壞損外擔菌(Exobasidium vexans
);外囊菌屬(Taphrina
species),例如,畸形外囊菌(Taphrina deformans
); 由例如以下引起之木本植物之退行性病害:埃斯卡屬(Esca
species),例如,根黴格孢菌(Phaeomoniella
chlamydospora)、褐枝頂孢黴(Phaeoacremonium
aleophilum)或地中海嗜藍孢孔菌(Fomitiporia
mediterranea);靈芝屬(Ganoderma
species),例如,島靈芝(Ganoderma boninense
); 由以下引起之植物塊莖之病害:絲核菌屬(Rhizoctonia
species),例如,立枯絲核菌(Rhizoctonia solani
);長蠕孢屬,例如,立枯長蠕孢菌; 由細菌性病原體引起之病害,該等細菌性病原體例如黃單孢菌屬(Xanthomonas
species),例如野油菜黃單胞菌(Xanthomonas campestris pv . oryzae
);假單胞菌屬,例如甜瓜細菌性葉斑病菌(Pseudomonas syringae pv . lachrymans
);歐文菌屬(Erwinia
species),例如解澱粉歐文菌(Erwinia amylovora
);黃龍病菌屬(Liberibacter
species),例如柑橘黃龍病(Liberibacter asiaticus
);變形菌屬(Xyella
species),例如葉緣焦枯病菌(Xylella fastidiosa
);羅爾斯頓菌屬(Ralstonia
species),例如茄科羅爾斯頓菌(Ralstonia solanacearum
);基氏菌屬(Dickeya
species),例如立枯基氏菌(Dickeya solani
);棍狀桿菌屬,例如密執安棍狀桿菌(Clavibacter michiganensis
);鏈黴菌屬,例如疥鏈黴菌(Streptomyces scabies
)。 大豆病害: 由例如以下引起的葉片、莖、豆莢及種子之真菌性病害:鏈隔孢菌屬葉斑病(細極鏈隔孢菌;Alternaria spec . atrans tenuissima
),炭疽病(赤葉枯刺盤孢菌變種;Colletotrichum gloeosporoides dematium var . truncatum
),褐斑病(大豆褐紋殼針孢;Septoria glycines
),尾孢菌葉斑病及枯萎病(菊池尾孢菌;Cercospora kikuchii
),笄黴屬葉枯病(漏斗笄黴菌;Choanephora infundibulifera trispora
(同義)),dactuliophora
葉斑病(Dactuliophora
甘胺酸),霜黴病(東北霜黴;Peronospora manshurica
),內臍蠕孢枯萎病(格利思尼內臍蠕孢;Drechslera glycini
),辣椒葉斑病(大豆灰斑病菌),小光腔菌葉斑病(三葉草小光腔菌;Leptosphaerulina trifolii
),葉點黴葉斑病(大豆生葉點黴;Phyllosticta sojaecola
),豆莢及莖稈枯萎病(大豆擬莖點黴),白粉病(白粉病菌;Microsphaera diffusa
),鬚殼孢葉斑病(鬚殼孢甘胺酸),絲核菌氣根、葉及網脈枯萎病(立枯絲核菌;Rhizoctonia solani
),銹病(大豆鏽菌(Phakopsora pachyrhizi
)、層鏽層假尾孢菌(Phakopsora meibomiae
)),瘡斑病(痂圓孢菌甘胺酸),匍柄黴葉枯病(匍柄黴;Stemphylium botryosum
),猝死症(棒形鐮刀菌;Fusarium virguliforme
),靶斑病(多主棒孢黴;Corynespora cassiicola
)。 由例如以下引起之根及莖基部真菌性病害:黑根腐病(野百合尾孢菌;Calonectria crotalariae
),炭腐病(菜豆立枯病菌;Macrophomina phaseolina
),鐮菌枯萎病或萎蔫病、根腐病以及豆莢及根頸腐病(尖孢鐮刀菌、直喙鐮孢、半裸鐮孢、木賊鐮孢),細圓盤黴根腐病(褐紅壞死病病菌;Mycoleptodiscus terrestris
),赤殼菌(侵菅新赤殼菌;Neocosmospora vasinfecta
),豆莢及莖稈枯萎病(大豆黑點病菌;Diaporthe phaseolorum
),莖潰瘍(大豆黑點病菌變種;Diaporthe phaseolorum var . caulivora
),疫黴菌腐病(大雄疫黴菌;Phytophthora megasperma
),褐莖腐病(大豆莖褐腐病菌;Phialophora gregata
),腐黴菌腐病(瓜果腐黴、畸雌腐黴、德巴利腐黴、群結腐黴、終極腐黴),絲核菌根腐病、莖腐病及猝倒病(立枯絲核菌),核盤菌莖腐病(向日葵核盤菌),核盤菌白絹病(白絹病核盤菌;Sclerotinia rolfsii
),根串珠黴根腐病(菫菜根腐病菌)。
黴菌毒素
另外,式(I)化合物或包含其之組合物可降低所收穫物質及自其製備之食品與飼料中之徵菌毒素含量。黴菌毒素尤其但非排他地包括以下:脫氧雪腐鐮刀菌烯醇(deoxynivalenol) (DON)、雪腐鐮刀菌醇(nivalenol)、15-Ac-DON、3-Ac-DON、T2-毒素及HT2-毒素、伏馬菌素(fumonisins)、玉米赤黴烯酮(zearalenon)、串珠鐮刀菌素(moniliformin)、鐮刀菌素(fusarin)、蛇形菌素(diaceotoxyscirpenol) (DAS)、白僵菌素(beauvericin)、恩鐮孢菌素(enniatin)、福撒羅多育麴菌素(fusaroproliferin)、福撒羅菌素(fusarenol)、赭麴菌素(ochratoxins)、散毒素(patulin)、麥角生物鹼(ergot alkaloid)及黃麴黴毒素(aflatoxins),其可例如藉由以下真菌產生:鐮刀菌屬(Fusarium spec .
),諸如銳頂鐮刀菌(F . acuminatum
)、亞洲鐮刀菌(F . asiaticum
)、燕麥鐮刀菌(F . avenaceum
)、克地鐮刀菌(F . crookwellense
)、黃色鐮刀菌(F . culmorum
)、禾穀鐮刀菌(F . graminearum
) (玉米赤黴菌(Gibberella zeae
))、木賊鐮刀菌(F . equiseti
)、水稻鐮刀菌(F . fujikoroi
)、香蕉鐮刀菌(F . musarum
)、尖鐮孢菌(F . oxysporum
)、串珠鐮刀菌(F . proliferatum
)、梨孢鐮刀菌(F . poae
)、小麥莖基腐病菌假禾穀鐮刀菌(F . pseudograminearum
)、接骨木鐮刀菌(F . sambucinum
)、蕉草鐮刀菌(F . scirpi
)、半裸鐮刀菌(F . semitectum
)、立枯鐮刀菌(F . solani
)、擬枝孢鐮刀菌(F . sporotrichoides
)、穀物鐮刀菌(F . langsethiae
)、膠孢鐮刀菌(F . subglutinans
)、三線鐮刀菌(F . tricinctum
)、輪枝樣鐮刀菌(F . verticillioides
)等,以及藉由以下產生:麴菌屬(Aspergillus spec .
),諸如黃麴菌(A . flavus
)、寄生麴菌(A . parasiticus
)、稻米麴菌(A . nomius
)、赭麴菌(A . ochraceus
)、棒麴菌(A . clavatus
)、土麴菌(A . terreus
)、雜色麴菌(A . versicolor
),青黴菌屬(Penicillium spec .
),諸如疣孢青黴菌(P . verrucosum
)、鮮綠青黴菌(P . viridicatum
)、桔青黴(P . citrinum
)、擴展青黴(P . expansum
)、棒狀青黴(P . claviforme
)、洛克福耳青黴菌(P . roqueforti
),麥角菌屬(Claviceps spec .
),諸如菊麥角菌(C . purpurea
)、紡綞形麥角菌(C . fusiformis
)、雀稗麥角菌(C . paspali
)、非洲麥角菌(C . africana
),葡萄穗黴菌屬(Stachybotrys spec .
)及其他。
物質保護
式(I)化合物及包含其之組合物亦可用於保護物質,尤其用於保護抗植物病原性真菌之攻擊及破壞的工業物質。
另外,式(I)化合物及包含其之組合物可單獨或與其他活性成分組合用作防污組合物。
本上下文中的工業物質應理解為意謂已經製備以用於工業中的無生命物質。舉例而言,欲保護以免受微生物改變或破壞之工業物質可為黏著劑、膠、紙張、壁紙及紙板/卡紙板、紡織物、地毯、皮革、原木、纖維及紙巾、塗料及塑膠製品、冷卻潤滑劑以及可受微生物影響或破環之其他物質。亦可在欲保護之物質的範疇內提及可被微生物之增殖減弱的生產設備及建築物之部分(例如水冷卻電路、冷卻及加熱系統以及通風及空調單元)。本發明範疇內之工業物質較佳地包括黏著劑、膠料、紙張及卡片、皮革、原木、塗料、冷卻潤滑劑及熱傳遞流體,更佳地原木。
式(I)化合物及包含其之組合物可防止有害影響,諸如腐壞、腐爛、變色、脫色或黴形成。
就原木處理而言,式(I)化合物及包含其之組合物亦可用以抵抗易在木材上或內部生長之真菌性病害。
木材意謂所有類型之原木種類,及欲用於建築之此原木之所有加工類型,例如實木、高密度木板、層壓板及合板。另外,式(I)化合物及包含其之組合物可用以保護與鹽水或微鹹水接觸之物件(尤其為船殼、螢幕、網、建築物、繫泊船及信號系統)免於積垢。
式(I)化合物及包含其之組合物亦可用於保護儲存貨物。應將儲存貨物理解為意謂蔬菜或動物來源之天然物質或其經處理產品,其具有天然來源且需要長期保護。蔬菜來源之儲存貨物(例如植物或植物部分,諸如莖、葉片、塊莖、種子、果實、穀粒)可在剛收穫後或在藉由(預)乾燥、濕潤、粉碎、研磨、擠壓或焙烤之處理後受到保護。儲存貨物亦包括木材,其未經處理(諸如建築木材、電線桿及障壁)或呈成品形式(諸如傢俱)。動物來源之儲存貨物為例如獸皮、皮革、皮草及毛髮。式(I)化合物及包含其之組合物可防止有害影響,諸如腐壞、腐爛、變色、脫色或黴形成。
能夠降解或改變工業物質之微生物包括(例如)細菌、真菌、酵母、藻類及黏液生物體。式(I)化合物及包含其之組合物較佳地抵抗真菌,尤其黴菌、使原木變色及毀壞原木之真菌(子囊菌、擔子菌、半知菌及接合菌),以及抵抗黏液生物體及藻類。實例包括以下屬之微生物:鏈隔孢菌屬(Alternaria
),諸如互生鏈隔孢菌(Alternaria tenuis
);麴菌屬(Aspergillus
),諸如黑麴菌(Aspergillus niger
);毛殼菌屬(Chaetomium
),諸如球毛殼菌(Chaetomium globosum
);粉孢革菌屬(Coniophora
),諸如單純粉孢革菌(Coniophora puetana
);香菇屬(Lentinus
),諸如虎皮香菇(Lentinus tigrinus
);青黴菌屬(Penicillium
),諸如藍色青黴菌(Penicillium glaucum
);多孔菌屬(Polyporus
),諸如變色多孔菌(Polyporus versicolor
);短梗黴屬(Aureobasidium
),諸如出芽短梗黴菌(Aureobasidium pullulans
);核莖點黴屬(Sclerophoma
),諸如綠頂核莖點黴(Sclerophoma pityophila
);木黴菌屬(Trichoderma
),諸如綠色木黴菌(Trichoderma viride
);長喙殼菌屬(Ophiostoma spp .
);長喙殼屬(Ceratocystis spp .
);腐殖菌屬(Humicola spp .
);彼得殼屬(Petriella spp .
);毛束黴屬(Trichurus spp .
);革蓋菌屬(Coriolus spp .
);黏褶菌屬(Gloeophyllum spp .
);側耳屬(Pleurotus spp .
);臥孔菌屬(Poria spp .
);乾朽菌屬(Serpula spp .
)及乾酪菌屬(Tyromyces spp .
);枝孢菌屬(Cladosporium spp .
);擬青黴菌屬(Paecilomyces spp .
);白黴菌屬(Mucor spp .
);埃希氏桿菌屬(Escherichia
),諸如大腸桿菌(Escherichia coli
);假單胞菌屬(Pseudomonas
),諸如綠膿桿菌(Pseudomonas aeruginosa
);葡萄球菌屬(Staphylococcus
),諸如金黃色葡萄球菌(Staphylococcus aureus
);念珠菌屬(Candida spp .
)及酵母屬(Saccharomyces spp .
),諸如釀酒酵母(Saccharomyces cerevisae
)。
種子處理
式(I)化合物及包含其之組合物亦可用以保護種子免受非所需微生物影響,諸如植物病原性微生物,例如植物病原性真菌或植物病原性卵菌。如本文所用,術語種子
包括休眠種子、經滲調(primed)種子、預發芽種子及具有冒出之根及葉片之種子。
因此,本發明亦係關於一種用於保護種子免受非所需微生物影響之方法,其包含用式(I)化合物及包含其之組合物處理種子的步驟。
用式(I)化合物或包含其之組合物處理種子,不僅保護種子免受植物病原性微生物影響,且亦保護萌發種子、所冒出幼苗及自經處理種子冒出後之植物。因此,本發明亦係關於一種用於保護種子、萌發種子及所冒出幼苗之方法。
種子處理可在播種之前、播種時或播種不久後進行。
當在播種前進行種子處理(例如,所謂的種子上施加)時,可如下進行種子處理:可將種子置放於具有所需量之式(I)化合物或包含其之組合物之攪拌機中,攪拌種子及式(I)化合物或包含其之組合物直至實現種子上之均勻分佈為止。適當時,可隨後乾燥種子。
本發明亦係關於塗佈有式(I)化合物或包含其之組合物的種子。
較佳地,種子在處理過程中不出現損害之足夠穩定之狀態下進行處理。一般而言,種子可在收穫與播種後不久之間之任何時間進行處理。習用使用已自植物分離且自穗軸、殼、梗、外殼、絨毛或果實之果肉釋放的種子。舉例而言,有可能使用已收穫、清潔及經乾燥至水分含量降至小於15重量%的種子。或者,亦有可能使用在乾燥之後例如已用水處理且隨後再次乾燥的種子、或剛好滲調後之種子、或儲存於滲調條件下之種子或預發芽種子、或在育苗盤、膠帶或紙張上播種之種子。
施加至種子之式(I)化合物或包含其之組合物之量通常為使得種子出芽不減弱或所得植物不受損害之量。此必須特別地確定,以防式(I)化合物在某些施加量下將呈現植物毒性效果。當判定待施加至種子的式(I)化合物之量以便以最少量所採用之化合物達成最佳種子及萌發植物保護時,轉殖基因植物之固有表現型亦應納入考慮。
式(I)化合物可原樣直接施加至種子,亦即無需使用任何其他組分且無需稀釋。包含一或多種式(I)化合物之組合物亦可施加至種子。
式(I)化合物及包含其之組合物適合於保護任何植物品種之種子。較佳種子為穀類(諸如,小麥、大麥、粗麥、栗、黑小麥及燕麥)、油菜、玉米、棉、大豆、水稻、馬鈴薯、向日葵、菜豆、咖啡、豆類、甜菜(例如,糖用甜菜及飼料甜菜)、花生、蔬菜(諸如,番茄、胡瓜、洋蔥及萵苣)、草坪及觀賞植物。更佳的為小麥、大豆、油菜、玉米及水稻之種子。
式(I)化合物及包含其之組合物可用於處理轉殖基因種子,尤其能夠表現針對害蟲、除草損害或非生物性逆境起作用之多肽或蛋白質的植物之種子,由此增加保護作用。能夠表現針對害蟲、除草損害或非生物性逆境起作用之多肽或蛋白質的植物之種子可含有至少一種允許表現該多肽或蛋白質之異源基因。轉殖基因種子中的此等異源基因可來源於例如以下屬之微生物:芽孢桿菌屬(Bacillus)、根瘤菌屬(Rhizobium)、假單胞菌屬(Pseudomonas)、沙雷菌屬(Serratia)、木黴菌屬(Trichoderma)、棍狀桿菌屬(Clavibacter)、叢枝菌根菌屬(Glomus)或膠黴屬(Gliocladium)。此等異源基因較佳地來源於芽孢桿菌屬,在此情況下基因產物有效抵抗歐洲玉米螟及/或西方玉米根蟲。尤佳地,異源基因來源於蘇力菌。
施加
式(I)化合物可原樣或例如以以下形式施加:備用溶液、乳液、水基或油基懸浮液、粉末、可濕潤粉末、糊、可溶粉末、粉塵、可溶顆粒、用於散佈之顆粒、懸浮乳劑濃縮物、浸漬有式(I)化合物之天然產物、浸漬有式(I)化合物之合成物質、肥料或聚合物質中之微膠囊劑。
以習用方式、例如藉由澆水、噴灑、霧化、散佈、撒粉、發泡、塗抹及類似者實現施加。亦可藉由超低量方法經由滴灌系統或浸液施加來部署式(I)化合物,以沿溝施加或將其噴射至田埂或土埂中。另外可藉助於傷口密封、塗層或其他傷口敷裹來施加式(I)化合物。
施加至植物、植物部分、果實、種子或土壤之式(I)化合物的有效及植物相容量將視各種因素而定,該等因素諸如所用化合物/組合物、處理之對象(植物、植物部分、果實、種子或土壤)、處理類型(撒粉、噴灑、拌種)、處理之用途(治癒性及保護性)、微生物類型、微生物之發展階段、微生物之敏感性、作物生長階段及環境條件。
當式(I)化合物用作殺真菌劑時,施加量可在相對廣範圍內改變,該範圍視施加種類而定。對於處理植物部分(諸如葉片),施加量的範圍可為0.1至10 000 g/ha,較佳地10至1000 g/ha,更佳地50至300 g/ha (在藉由澆水或滴注施加之情況下,甚至可降低施加量,尤其在使用諸如石棉或珍珠岩之惰性基質時)。對於處理種子,施加量的範圍可為0.1至200公克/100公斤種子,較佳地1至150公克/100公斤種子,更佳地2.5至25公克/100公斤種子,甚至更佳地2.5至12.5公克/100公斤種子。對於處理土壤,施加量的範圍可為0.1至10 000 g/ha,較佳地1至5000 g/ha。
此等施加量僅為實例且並不意欲限制本發明之範疇。
可根據以下實例來進一步理解本發明教示的態樣,該等實例不應理解為以任何方式限制本發明教示的範疇。
實例
表1以非限制性方式說明根據本發明之式(I)化合物之實例:
在下文表1中提及之式(I)化合物根據詳述於下文中關於特定實例及本文中所揭示之製程之一般描述的程序來製備。
在表1中,除非另外說明,否則M+H (ApcI+)意謂如在經由正型大氣壓化學電離之質譜分析中所觀測到之分子離子峰加1 a.m.u. (原子質量單位)。
在表1中,logP值係根據EEC Directive 79/831 Annex V.A8藉由HPLC (高效液相層析)在逆相管柱(C 18)上使用以下所述方法測定: 溫度:40℃;移動相:0.1%甲酸水溶液及乙腈水溶液;線性梯度:10%乙腈至95%乙腈; 使用具有已知logP值(在兩個連續烷酮之間使用線性內插法藉由滯留時間測定logP值)之未分支烷-2-酮(包含3至16個碳原子)進行校準。使用200 nm至400 nm之UV光譜及層析信號之峰值測定λ最大值。
在表1中,(X)n
殘基對苯環之連接點係基於苯環之上文編號。表 1 :
注意:Me:甲基;iPr:異丙基
表2以非限制性方式來說明根據本發明之式(IIa)化合物以及其可接受之鹽之實例:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義,且U1a
表示氯原子、溴原子或碘原子。
在表2中,M+H (ApcI+)及logP如表1所定義。
在表2中,(X)n
殘基對苯環之連接點係基於苯環之上文編號。表 2 :
表3以非限制性方式來說明根據本發明之式(V)化合物以及其可接受之鹽之實例:其中L、n、X、Y1
、Y2
、Y3
、Y4
、Y5
、W及Z如本文所定義。
在表3中,M+H (ApcI+)及logP如表1所定義。
在表3中,(X)n
殘基對苯環之連接點係基於苯環之上文編號。表 3 :
表4提供表1中所選編號之化合物的NMR資料(1
H)。
所選實例之1
H-NMR資料以1
H-NMR峰清單之形式陳述。對於每一信號峰值,λ值以ppm表示且信號強度在括號中表示。
在所印刷之NMR頻譜實例中,尖銳信號之強度與信號高度(cm)相關且展示信號強度之實際關係。自寬信號可展示信號之若干峰值或中間值及其相較於頻譜中之最密集信號之相對強度。
1
H-NMR峰清單類似於經典1
H-NMR印刷圖且因此通常含有經典NMR說明中所列之所有峰。另外,其可如經典1
H-NMR印刷圖一樣展示溶劑信號、目標化合物之立體異構體(其亦為本發明之目的)及/或雜質之峰。為在溶劑及/或水之δ範圍(delta-range)中展示化合物信號,溶劑之一般峰(例如d6
-DMSO中之DMSO峰)及水之峰展示於吾人之1
H-NMR峰清單中且通常平均具有較高強度。
目標化合物之立體異構體之峰及/或雜質之峰通常平均具有比目標化合物(例如具有大於90%之純度)之峰低的強度。此類立體異構體及/或雜質對於特定製備製程可為典型的。因此其峰可經由「副產物指紋」幫助辨認吾人之製備製程之再現。
用已知方法(MestreC、ACD模擬,以及用憑經驗評估之期望值)計算目標化合物之峰的專家可視情況使用另外的強度過濾器按需要分離目標化合物之峰。此分離將類似於經典1
H-NMR說明處之相關峰挑選。
具有峰清單之NMR資料描述之其他細節可見於研究公開資料庫第564025號之公開案「Citation of NMR Peaklist Data within Patent Applications」中。表 4
:NMR峰清單
製備實例 製備實例 1 :
2-甲基-3-{2-[(三甲基矽基)甲基]苯氧基}喹啉(化合物I.05)之製備 在氬氣下於乾燥RadleysTM
小瓶中,在80℃下加熱150 mg (0.47 mmol) 3-(2-溴苯氧基)-2-甲基喹啉及153 mg (0.71 mmol)三甲基[(4,4,5,5-四甲基-1,3,2-二氧雜硼戊環-2-基)-甲基]矽烷於3 mL四氫呋喃與溶解於0.5 mL水中之36 mg (0.048 mmol) 1,1'-雙(二苯基-膦基)二茂鐵鈀(II)氯化物及466 mg (1.43 mmol)碳酸銫中的混合物60小時。經冷卻反應混合物經矽藻土餅過濾。將矽藻土餅用四氫呋喃洗滌,且將有機相在真空下濃縮,得到249 mg殘餘物。藉由矽膠管柱層析(梯度正庚烷/乙酸乙酯)純化此殘餘物以產生33 mg (20%) 2-甲基-3-{2-[(三甲基矽基)甲基]苯氧基}喹啉。LogP = 5.05。質量(M+H) = 322。
製備實例 2 :
3-(2-{[二甲基(2-噻吩基)矽基]甲基}苯氧基)-8-氟喹啉(化合物I.46)之製備步驟 1 :
3-[2-(溴甲基)苯氧基]-8-氟喹啉之製備 向841 mg (3.32 mmol) 8-氟-3-(2-甲基苯氧基)喹啉於40 mL四氯化碳中之溶液中添加484 mg (1.66 mmol) 1,3-二溴-5,5-二甲基內醯脲及57 mg (0.166 mmol)過氧化二苯甲醯。將反應混合物在用螢光燈[G23燈泡-11 W-900流明]照射時加熱回流8小時。將經冷卻之混合物倒入硫代硫酸鈉水溶液且用二氯甲烷萃取。有機相經硫酸鎂乾燥且在真空下濃縮,得到1.26 g油狀橙色殘餘物。藉由矽膠管柱層析(正庚烷/乙酸乙酯 97/3)純化此殘餘物以產生694 mg (62%)被約10%之3-[2-(二溴甲基)苯氧基]-8-氟喹啉污染的3-[2-(溴甲基)苯氧基]-8-氟喹啉。LogP = 3.65。質量(M+H) = 332。
步驟 2 :
3-(2-{[二甲基(2-噻吩基)矽基]甲基}苯氧基)-8-氟喹啉之製備 在氬氣下於乾燥RadleysTM
小瓶中,在70℃下加熱100 mg (0.30 mmol) 3-[2-(溴甲基)苯氧基]-8-氟喹啉、174 mg (0.60 mmol) 1,1,2,2-四甲基-1,2-二(2-噻吩基)二矽烷、1.8 mg (0.006 mmol)聯苯-2-基(二-第三丁基)膦[Johnphos]、2.6 mg (0.015 mmol)二氯化鈀(II)及0.15 mL (0.90 mmol) N,N-二異丙基乙胺於5 mL乾燥N-甲基吡咯啶酮中之混合物3小時。將經冷卻反應混合物用LiCl飽和水溶液稀釋,且用乙酸乙酯萃取。有機萃取物經硫酸鎂乾燥。將有機相在真空下濃縮以產生326 mg呈黑色油狀物之殘餘物。藉由製備型HPLC (梯度乙腈/水+0.1% HCO2
H)純化產生43 mg (36%) 3-{[2-{[二甲基(2-噻吩基)矽基]甲基}苯氧基)-8-氟喹啉。LogP = 5.60。質量(M+H) = 394。
製備實例 3 :
[2-氯-6-(喹啉-3-基氧基)苯甲基] (二甲基)矽烷醇(化合物I.25)之製備 在氬氣下於乾燥RadleysTM
小瓶中,在80℃下加熱128 mg (0.42 mmol)3-[(3-氯-2-(氯甲基)苯氧基]喹啉、179 mg (0.84 mmol) 1,2-二乙氧基-1,1,2,2-四甲基二甲矽烷、13 mg (0.042 mmol)聯苯-2-基(二-第三丁基)膦、3.7 mg (0.021 mmol)二氯化鈀(II)及0.21 mL (1.26 mmol) N,N-二異丙基乙胺於5 mL乾燥N-甲基吡咯啶酮中之混合物8小時。將經冷卻反應混合物用LiCl飽和水溶液稀釋,且用乙酸乙酯萃取。有機萃取物經硫酸鎂乾燥。將有機相在真空下濃縮以產生330 mg橙棕色殘餘物。藉由製備型HPLC (梯度乙腈/水+0.1% HCO2
H)純化產生75 mg (49%) [2-氯-6-(喹啉-3-基氧基)苯甲基](二甲基)矽烷醇。LogP = 3.48。質量(M+H) = 344。
製備實例 4 :
8-氟-2-甲基-3-{2-[(三甲基矽基)甲基]苯氧基}喹啉(化合物I.17)之製備 在-78℃下向0.6 mL (0.72 mmol)之1.2 M三甲基矽烷基甲基氯化鎂於四氫呋喃中的溶液添加0.9 mL (0.63 mmol)之0.7 M氯化鋅於四氫呋喃中的溶液。在-78℃下攪拌溶液1小時。另外添加100 mg (0.3 mmol) 3-(2-溴苯氧基)-8-氟-2-甲基-喹啉、13.7 mg (0.015 mmol)參(二苯亞甲基丙酮)二鈀及8.7 mg (0.03 mmol)三第三丁基膦四氟硼酸鹽,且使混合物緩慢地返回室溫,隨後在100℃加熱1小時。經冷卻之反應混合物經矽藻土餅過濾且在真空下濃縮。將殘餘物用水稀釋、用乙酸乙酯萃取且經硫酸鎂乾燥。將有機相在真空下濃縮以產生150 mg褐色油狀物。藉由矽膠管柱層析(梯度正庚烷/乙酸乙酯 90/10)純化此殘餘物以產生80 mg (78%) 8-氟-2-甲基-3-{2-[(三甲基矽基)-甲基]苯氧基}喹啉。LogP = 5.85。質量(M+H) = 340。
生物資料 實例 A : 對稻梨孢 ( Pyricularia oryzae ) 之活體外細胞測試
溶劑: 二甲亞碸 培養基: 14.6 g無水D-葡萄糖(VWR), 7.1 g真菌蛋白腖(Oxoid), 1.4 g顆粒狀酵母提取物(Merck),QSP 1公升 接種物: 孢子懸浮液
將所測試化合物溶解於二甲亞碸及用於製備所需濃度範圍之溶液。用於檢定之二甲亞碸之最終濃度為≤1%。
製備稻梨孢之孢子懸浮液且稀釋至所需孢子密度。
評估化合物抑制液體培養基檢定中孢子出芽及菌絲體生長的能力。以所需濃度將化合物添加至具有孢子之培養基。在培養5天之後,藉由菌絲體生長之光譜量測來測定化合物之真菌毒性。藉由比較含有殺真菌劑之孔中之吸光度值與無殺真菌劑之對照孔中之吸光度來測定真菌生長之抑制。
在此測試中,根據本發明之以下化合物在20 ppm活性成分之濃度下展示70%與79%之間的功效:I.43、I.51、I.55、I.58、I.61、I.63、I.64
在此測試中,根據本發明之以下化合物在20 ppm活性成分之濃度下展示80%與89%之間的功效:I.08、I.15、I.26、I.33、I.35、I.38、I.45、I.48、I.60、I.65
在此測試中,根據本發明之以下化合物在20 ppm活性成分之濃度下展示90%與100%之間的功效:I.01、I.02、I.03、I.04、I.05、I.06、I.07、I.09、I.10、I.11、I.12、I.13、I.14、I.16、I.18、I.19、I.20、I.23、I.28、I.29、I.30、I.31、I.32、I.34、I.37、I.39、I.40、I.42、I.44、I.46、I.50、I.52、I.54、I.59
實例 B : 對豆刺盤孢菌 ( Colletotrichum lindemuthianum ) 之活體外細胞測試
溶劑: 二甲亞碸 培養基: 14.6 g無水D-葡萄糖(VWR), 7.1 g真菌蛋白腖(Oxoid), 1.4 g顆粒狀酵母提取物(Merck),QSP 1公升 接種物: 孢子懸浮液
將所測試化合物溶解於二甲亞碸及用於製備所需濃度範圍之溶液。用於檢定之二甲亞碸之最終濃度為≤1%。
製備豆刺盤孢菌之孢子懸浮液且稀釋至所需孢子密度。
評估化合物抑制液體培養基檢定中孢子出芽及菌絲體生長的能力。以所需濃度將化合物添加至具有孢子之培養基。在培養5天之後,藉由菌絲體生長之光譜量測來測定化合物之真菌毒性。藉由比較含有殺真菌劑之孔中之吸光度值與無殺真菌劑之對照孔中之吸光度來測定真菌生長之抑制。
在此測試中,根據本發明之以下化合物在20 ppm活性成分之濃度下展示70%與79%之間的功效:I.35、I.39、I.43、I.54、I.62
在此測試中,根據本發明之以下化合物在20 ppm活性成分之濃度下展示80%與89%之間的功效:I.08、I.12、I.16、I.24、I.26、I.29、I.37、I.41、I.45、I.48、I.57、I.65
在此測試中,根據本發明之以下化合物在20 ppm活性成分之濃度下展示90%與100%之間的功效:I.01、I.02、I.03、I.04、I.05、I.06、I.07、I.09、I.10、I.11、I.13、I.14、I.15、I.18、I.19、I.20、I.22、I.23、I.25、I.27、I.30、I.32、I.33、I.34、I.40、I.44、I.46、I.47、I.56、I.59、I.60、I.61、I.63、I.64
實例 C : 對 灰葡萄孢菌 ( Botrytis cinerea )( 灰黴 ) 之活體內預防性測試
溶劑: 5% 以二甲亞碸之體積計 10% 以丙酮之體積計 乳化劑: 每毫克活性成份1 µL Tween® 80
使活性成分在二甲亞碸/丙酮/Tween® 80之混合物中可溶且均質化,且隨後在水中將其稀釋至所需濃度。
藉由噴灑如上文所描述製備之活性成分處理小黃瓜之幼株。僅用丙酮/二甲亞碸/Tween® 80之水溶液處理對照植株。
在24小時之後,植株因用灰葡萄孢菌孢子之水性懸浮液噴灑葉片而受到污染。經污染之小黃瓜植株在17℃下且在90%之相對濕度下培育4至5天。
在接種後4至5天對測試進行評估。0%意謂對應於對照植株之功效的功效,而100%之功效意謂未觀測到病害。
在此測試中,根據本發明之以下化合物在500 ppm活性成份之濃度下展示70%與79%之間的功效:I.01、I.40
在此測試中,更具本發明之以下化合物在500 ppm活性成份之濃度下展示80%與89%之間的功效:I.32、I.63
在此測試中,根據本發明之以下化合物在500 ppm活性成份之濃度下展示90%與100%之間的功效:I.02、I.05、I.07、I.10、I.11、I.12、I.13、I.14、I.17、I.18、I.20、I.22、I.24、I.25、I.26、I.27、I.31、I.33、I.34、I.44、I.46、I.47、I.56、I.60、I.61
實例 D : 對豆刺盤孢菌 (Colletotrichum lindemuthianum
)( 豆類之葉斑病 ) 之活體內預防性測試
溶劑: 5% 以二甲亞碸之體積計 10% 以丙酮之體積計 乳化劑: 每毫克活性成份1 µL Tween® 80
使活性成分在二甲亞碸/丙酮/Tween® 80之混合物中可溶且均質化,且隨後在水中將其稀釋至所需濃度。
藉由噴灑如上文所描述製備之活性成分處理豆類之幼株。僅用丙酮/二甲亞碸/Tween® 80之水溶液處理對照植株。
在24小時之後,植株因用豆刺盤孢菌孢子之水性懸浮液噴灑葉片而受到污染。使經污染之豆類植株在20℃下且在100%相對濕度下培育24小時,且隨後在20℃下且在90%相對濕度下培育6天。
在接種後7天對測試進行評估。0%意謂對應於對照植株之功效的功效,而100%之功效意謂未觀測到病害。
在此測試中,根據本發明之以下化合物在500 ppm活性成份之濃度下展示70%與79%之間的功效:I.32、I.33、I.56、I.64
在此測試中,根據本發明之以下化合物在500 ppm活性成份之濃度下展示80%與89%之間的功效:I.11、I.22、I.31、I.38、I.40
在此測試中,根據本發明之以下化合物在500 ppm活性成份之濃度下展示90%與100%之間的功效:I.05、I.06、I.10、I.13、I.14、I.17、I.19、I.20、I.25、I.27、I.44、I.46、I.47、I.51、I.61;
實例 E :對 蘋果黑星病菌 (Venturia inaequalis
)( 蘋果 ) 之活體內預防性測試
溶劑: 24.5重量份之丙酮 24.5重量份之二甲基乙醯胺 乳化劑: 1重量份之烷芳基聚乙二醇醚
為產生適合的活性成分製劑,將1重量份之活性成分與所述量之溶劑及乳化劑混合,且將濃縮物用水稀釋至所需濃度。
為測試預防性活性,以所述施加量用活性化合物製劑噴灑幼株。在噴塗已乾燥之後,對植株接種引起蘋果瘡痂病(蘋果黑星病菌)之病原之水性分生孢子懸浮液,且隨後在約20℃及100%之相對大氣濕度下的培育箱中保持1天。
接著將植株置放於在約21℃及約90%之相對大氣濕度下的溫室中。
在接種後10天對測試進行評估。0%意謂對應於未處理對照物之功效的功效,而100%之功效意謂未觀測到病害。
在此測試中,根據本發明之以下化合物在250 ppm活性成分之濃度下展示90%與100%之間的功效:I.31
實例 F : 對大麥網斑病 ( Pyrenophora teres ) ( 大麥 ) 之活體內預防性測試
溶劑: 49重量份之N,N-二甲基乙醯胺 乳化劑: 1重量份之烷芳基聚乙二醇醚
為產生適合的活性成分製劑,將1重量份之活性成分與所述量之溶劑及乳化劑混合,且將濃縮物用水稀釋至所需濃度。
為測試預防性活性,以所述施加量用活性化合物製劑噴灑幼株。在噴塗已乾燥之後,對該等植株噴灑大麥網斑病菌之孢子懸浮液。使植株在約20℃及約100%之相對大氣濕度的培育箱中保持48小時。
將植株置放置在約20℃之溫度及約80%之相對大氣濕度下的溫室中。
在接種後8天對測試進行評估。0%意謂對應於未處理對照物之功效的功效,而100%之功效意謂未觀測到病害。
在此測試中,根據本發明之以下化合物在500 ppm活性成份之濃度下展示70%與79%之間的功效:I.13、I.18
Claims (15)
- 一種式(I)化合物:其中 Z係選自由以下組成之群:氫原子、鹵素原子、C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、包含至多9個可相同或不同之鹵素原子的C2 -C8 鹵代烯基、C2 -C8 炔基、包含至多9個可相同或不同之鹵素原子的C2 -C8 鹵代炔基、C3 -C7 環烷基、C4 -C7 環烯基、羥基、C1 -C8 烷氧基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷氧基、芳基、雜環基、甲醯基、C1 -C8 烷基羰基、(羥亞胺基)C1 -C8 烷基、(C1 -C8 烷氧基亞胺基)C1 -C8 烷基、羧基、C1 -C8 烷氧基羰基、胺甲醯基、C1 -C8 烷基胺甲醯基、二-C1 -C8 烷基胺甲醯基、胺基、C1 -C8 烷胺基、二-C1 -C8 烷胺基、硫基、C1 -C8 烷基硫基、C1 -C8 烷基亞磺醯基、C1 -C8 烷基磺醯基、C1 -C6 三烷基矽基、氰基及硝基, 其中該C1 -C8 烷基、C2 -C8 烯基、C2 -C8 炔基及C1 -C8 烷氧基可經一或多個Za 取代基取代,且其中該C3 -C7 環烷基、C4 -C7 環烯基、芳基及雜環基可經一或多個Zb 取代基取代; n表示0、1、2、3或4; L表示O、S、SO、SO2 、CR4 R5 或NR6 ,其中 R4 及R5 係獨立地選自由以下組成之群:氫原子、鹵素原子、羥基、C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C1 -C8 烷氧基及包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷氧基,或其可與其所連接之碳原子一起形成羰基; R6 係選自由以下組成之群:氫原子、C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、包含至多9個可相同或不同之鹵素原子的C2 -C8 鹵代烯基、C3 -C8 炔基、包含至多9個可相同或不同之鹵素原子的C3 -C8 鹵代炔基、C3 -C7 環烷基、包含至多9個可相同或不同之鹵素原子的C3 -C7 鹵代環烷基、C3 -C7 環烷基-C1 -C8 烷基、甲醯基、C1 -C8 烷基羰基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基羰基、C1 -C8 烷氧基羰基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷氧基羰基、C1 -C8 烷基磺醯基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基磺醯基、芳基-C1 -C8 烷基及苯磺醯基,其中該C1 -C8 烷基、C2 -C8 烯基、C3 -C8 炔基可經一或多個R6a 取代基取代,且其中該C3 -C7 環烷基、C3 -C7 環烷基-C1 -C8 烷基、芳基-C1 -C8 烷基及苯磺醯基可經一或多個R6b 取代基取代; X係獨立地選自由以下組成之群:鹵素原子、C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、包含至多9個可相同或不同之鹵素原子的C2 -C8 鹵代烯基、C2 -C8 炔基、包含至多9個可相同或不同之鹵素原子的C2 -C8 鹵代炔基、C3 -C7 環烷基、C4 -C7 環烯基、羥基、C1 -C8 烷氧基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷氧基、C1 -C6 三烷基矽基、C1 -C6 三烷基矽基甲基、氰基及硝基, 其中該C1 -C8 烷基、C2 -C8 烯基、C2 -C8 炔基及C1 -C8 烷氧基可經一或多個Xa 取代基取代,且該C3 -C7 環烷基及C4 -C7 環烯基可經一或多個Xb 取代基取代; W為CY1 或N,其中: Y1係選自由以下組成之群:氫原子、鹵素原子、C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、包含至多9個可相同或不同之鹵素原子的C2 -C8 鹵代烯基、C2 -C8 炔基、包含至多9個可相同或不同之鹵素原子的C2 -C8 鹵代炔基、C3 -C7 環烷基、C4 -C7 環烯基、羥基、C1 -C8 烷氧基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷氧基、芳基、雜環基、甲醯基、C1 -C8 烷基羰基、(羥亞胺基)C1 -C8 烷基、(C1 -C8 烷氧基亞胺基)C1 -C8 烷基、羧基、C1 -C8 烷氧基羰基、胺甲醯基、C1 -C8 烷基胺甲醯基、二-C1 -C8 烷基胺甲醯基、胺基、C1 -C8 烷胺基、二-C1 -C8 烷胺基、硫基、C1 -C8 烷基硫基、C1 -C8 烷基亞磺醯基、C1 -C8 烷基磺醯基、C1 -C6 三烷基矽基、氰基及硝基, 其中該C1 -C8 烷基、C2 -C8 烯基、C2 -C8 炔基及C1 -C8 烷氧基可經一或多個Y1a 取代基取代,且其中該C3 -C7 環烷基、C4 -C7 環烯基、芳基及雜環基可經一或多個Y1b 取代基取代; Y2 、Y3 、Y4 及Y5 係獨立地選自由以下組成之群:氫原子、鹵素原子、C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、包含至多9個可相同或不同之鹵素原子的C2 -C8 鹵代烯基、C2 -C8 炔基、包含至多9個可相同或不同之鹵素原子的C2 -C8 鹵代炔基、C3 -C7 環烷基、C4 -C7 環烯基、羥基、C1 -C8 烷氧基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷氧基、芳基、雜環基、甲醯基、C1 -C8 烷基羰基、(羥亞胺基)C1 -C8 烷基、(C1 -C8 烷氧基亞胺基)C1 -C8 烷基、羧基、C1 -C8 烷氧基羰基、胺甲醯基、C1 -C8 烷基胺甲醯基、二-C1 -C8 烷基胺甲醯基、胺基、C1 -C8 烷胺基、二-C1 -C8 烷胺基、硫基、C1 -C8 烷基硫基、C1 -C8 烷基亞磺醯基、C1 -C8 烷基磺醯基、C1 -C6 三烷基矽基、氰基及硝基, 其中該C1 -C8 烷基、C2 -C8 烯基、C2 -C8 炔基及C1 -C8 烷氧基可分別地經一或多個Y2a 、Y3a 、Y4a 或Y5a 取代基取代,且其中該C3 -C7 環烷基、C4 -C7 環烯基、芳基及雜環基可分別地經一或多個Y2b 、Y3b 、Y4b 或Y5b 取代基取代; R1 係選自由以下組成之群:C1 -C8 烷基、C2 -C8 烯基、C2 -C8 炔基、C3 -C7 環烷基、C4 -C7 環烯基、芳基及雜環基, 其中該C1 -C8 烷基、C2 -C8 烯基及C2 -C8 炔基可經一或多個R1a 取代基取代,且其中該C3 -C7 環烷基、C4 -C7 環烯基、芳基及雜環基可經一或多個R1b 取代基取代; R2 係選自由以下組成之群:羥基、C1 -C8 烷氧基、C1 -C8 烷基、C2 -C8 烯基、C2 -C8 炔基、C3 -C7 環烷基、C4 -C7 環烯基、芳基及雜環基, 其中該C1 -C8 烷氧基、C1 -C8 烷基、C2 -C8 烯基及C2 -C8 炔基可經一或多個R2a 取代基取代,且其中該C3 -C7 環烷基、C4 -C7 環烯基、芳基及雜環基可經一或多個R2b 取代基取代; 當R1 及R2 表示C1 -C8 烷基或C2 -C8 烯基時,其可與其所連接之矽原子一起形成C3 -C8 矽雜環烷基環或C4 -C8 矽雜環烯基環, 其中該C3 -C8 矽雜環烷基環或C4 -C8 矽雜環烯基環可經一或多個R1b 取代; R3 係選自由以下組成之群:氫原子、鹵素原子、C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、C2 -C8 炔基、C3 -C7 環烷基、C4 -C7 環烯基、羥基、C1 -C8 烷氧基、芳基、芳基-C1 -C8 烷基、雜環基、雜環基-C1 -C8 烷基、羥基-C1 -C8 烷基、C1 -C8 烷氧基-C1 -C8 烷基、C1 -C8 烷基羰氧基-C1 -C8 烷基、芳氧基-C1 -C8 烷基、雜環基氧基-C1 -C8 烷基、胺基-C1 -C8 烷基、C1 -C8 烷胺基-C1 -C8 烷基、二-C1 -C8 烷胺基-C1 -C8 烷基、芳胺基-C1 -C8 烷基、二-芳胺基-C1 -C8 烷基、雜環胺基-C1 -C8 烷基、C1 -C8 烷基羰基胺基-C1 -C8 烷基、C1 -C8 烷氧基羰基胺基-C1 -C8 烷基、C1 -C8 烷基硫基-C1 -C8 烷基、C1 -C8 烷基亞磺醯基-C1 -C8 烷基、C1 -C8 烷基磺醯基-C1 -C8 烷基及氰基-C1 -C8 烷基, 其中該C1 -C8 烷基、C2 -C8 烯基及C2 -C8 炔基可經一或多個R3a 取代基取代,且其中該C3 -C7 環烷基、C4 -C7 環烯基、芳基、芳基-C1 -C8 烷基、雜環基、雜環基-C1 -C8 烷基、芳氧基-C1 -C8 烷基及雜環基氧基-C1 -C8 烷基可經一或多個R3b 取代基取代; R3 及X在該X鄰近CH2 -SiR1 R2 R3 時可與其分別連接之矽原子及碳原子一起形成5員、6員或7員部分飽和雜環,其中該5員、6員或7員部分飽和雜環可經一或多個R3b 取代基取代; 當R2 表示C1 -C8 烷氧基且R3 表示C1 -C8 烷氧基或C1 -C8 烷基時,其可與其所連接之矽原子一起形成5員、6員或7員雜環,其中該5員、6員或7員雜環可經一或多個R2b 取代基取代; Za 、R1a 、R2a 、R3a 、R6a 、Xa 、Y1a 、Y2a 、Y3a 、Y4a 及Y5a 係獨立地選自由以下組成之群:硝基、羥基、氰基、羧基、胺基、硫基、五氟-λ6 -硫基、甲醯基、胺甲醯基、胺基甲酸根、C3 -C7 環烷基、具有1至5個鹵素原子之C3 -C8 鹵代環烷基、C1 -C8 烷胺基、二-C1 -C8 烷胺基、C1 -C8 烷氧基、具有1至5個鹵素原子之C1 -C8 鹵代烷氧基、C1 -C8 烷基硫基、具有1至5個鹵素原子之C1 -C8 鹵代烷基硫基、C1 -C8 烷基羰基、具有1至5個鹵素原子之C1 -C8 鹵代烷基羰基、C1 -C8 烷基胺甲醯基、二-C1 -C8 烷基胺甲醯基、C1 -C8 烷氧基羰基、具有1至5個鹵素原子之C1 -C8 鹵代烷氧基羰基、C1 -C8 烷基羰氧基、具有1至5個鹵素原子之C1 -C8 鹵代烷基羰氧基、C1 -C8 烷基羰基胺基、具有1至5個鹵素原子之C1 -C8 鹵代烷基羰基胺基、C1 -C8 烷基亞磺醯基、具有1至5個鹵素原子之C1 -C8 鹵代烷基亞磺醯基、C1 -C8 烷基磺醯基及具有1至5個鹵素原子之C1 -C8 鹵代烷基磺醯基; Zb 、R1b 、R2b 、R3b 、R6b 、Xb 、Y1b 、Y2b 、Y3b 、Y4b 及Y5b 係獨立地選自由以下組成之群:鹵素原子、硝基、羥基、氰基、羧基、胺基、硫基、五氟-λ6 -硫基、甲醯基、胺甲醯基、胺基甲酸根、C1 -C8 烷基、C3 -C7 環烷基、具有1至5個鹵素原子之C1 -C8 鹵代烷基、具有1至5個鹵素原子之C3 -C8 鹵代環烷基、C2 -C8 烯基、C2 -C8 炔基、C1 -C8 烷胺基、二-C1 -C8 烷胺基、C1 -C8 烷氧基、具有1至5個鹵素原子之C1 -C8 鹵代烷氧基、C1 -C8 烷基硫基、具有1至5個鹵素原子之C1 -C8 鹵代烷基硫基、C1 -C8 烷基羰基、具有1至5個鹵素原子之C1 -C8 鹵代烷基羰基、C1 -C8 烷基胺甲醯基、二-C1 -C8 烷基胺甲醯基、C1 -C8 烷氧基羰基、具有1至5個鹵素原子之C1 -C8 鹵代烷氧基羰基、C1 -C8 烷基羰氧基、具有1至5個鹵素原子之C1 -C8 鹵代烷基羰氧基、C1 -C8 烷基羰基胺基、具有1至5個鹵素原子之C1 -C8 鹵代烷基羰基胺基、C1 -C8 烷基硫基、具有1至5個鹵素原子之C1 -C8 鹵代烷基硫基、C1 -C8 烷基亞磺醯基、具有1至5個鹵素原子之C1 -C8 鹵代烷基亞磺醯基、C1 -C8 烷基磺醯基及具有1至5個鹵素原子之C1 -C8 鹵代烷基磺醯基; 以及其鹽、N-氧化物、金屬錯合物、類金屬錯合物及光學活性異構體或幾何異構體。
- 如請求項1之式(I)化合物,其中Z係選自由以下組成之群:氫原子、鹵素原子、羥基、C1 -C6 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C6 鹵代烷基、C1 -C6 烷氧基、包含至多9個可相同或不同之鹵素原子的C1 -C6 鹵代烷氧基及氰基。
- 如請求項1或2之式(I)化合物,其中L為O、N或CH2 。
- 如前述請求項中任一項之式(I)化合物,其中X獨立地為鹵素原子、C1 -C6 烷基或C1 -C6 三烷基矽基甲基。
- 如前述請求項中任一項之式(I)化合物,其中Y1 、Y2 、Y3 、Y4 或Y5 係獨立地選自由以下組成之群:氫原子、鹵素原子、C1 -C6 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C6 鹵代烷基、C1 -C6 烷氧基、包含至多9個可相同或不同之鹵素原子的C1 -C6 鹵代烷氧基及氰基。
- 如前述請求項中任一項之式(I)化合物,其中R1 及/或R2 為C1 -C6 烷基。
- 如前述請求項中任一項之式(I)化合物,其中R3 係選自由以下組成之群:羥基、C1 -C6 烷基、C2 -C6 烯基、C1 -C6 烷氧基、可經一或多個R3b 取代之芳基、芳基-C1 -C6 烷基、雜環基及雜環基-C1 -C6 烷基。
- 如前述請求項中任一項之式(I)化合物,其中W為CY1 ,其中Y1 如請求項1或5中所敍述。
- 如請求項1至7中任一項之式(I)化合物,其中W為N。
- 一種組合物,其包含一或多種如請求項1至9中任一項之式(I)化合物及至少一種農業上適合之助劑。
- 一種用於控制非所需植物病原性微生物的方法,其包含向該等微生物及/或其生境施加一或多種如請求項1至9中任一項之式(I)化合物或如請求項10之組合物的步驟。
- 一種用於製備如請求項1至9中任一項之式(I)化合物的製程,其包含以下步驟:使式(II)之鹵代甲基芳基或其鹽中之一者:其中L、n、X、Y1 、Y2 、Y3 、Y4 、Y5 、W及Z如請求項1中所敍述,且U1 表示氯原子、溴原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基, 與式(IIIa)之二矽基衍生物反應:其中R1 、R2 及R3 如請求項1中所敍述。
- 一種用於製備如請求項1至9中任一項之式(I)化合物的製程,其包含以下步驟: (a)使式(VI)化合物或其鹽中之一者:其中L、n、X、Y1 、Y2 、Y3 、Y4 、Y5 、W及Z如請求項1中所敍述,且U2 表示氯原子、溴原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基, 與式(IIIb)之硼衍生物反應:其中W3 表示硼衍生物, R1 及R2 獨立地表示C1 -C8 烷基、C2 -C8 烯基、C3 -C7 環烷基、芳基或雜環基;以及 R3 表示氫原子或C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、C2 -C8 炔基、C3 -C7 環烷基、C4 -C7 環烯基、芳基、芳基-C1 -C8 烷基、C1 -C8 烷氧基、雜環基、雜環基-C1 -C8 烷基、羥基-C1 -C8 烷基、C1 -C8 烷氧基-C1 -C8 烷基、C1 -C8 烷基羰氧基-C1 -C8 烷基、芳氧基-C1 -C8 烷基、雜環基氧基-C1 -C8 烷基、胺基-C1 -C8 烷基、C1 -C8 烷胺基-C1 -C8 烷基、二-C1 -C8 烷胺基-C1 -C8 烷基、芳胺基-C1 -C8 烷基、二-芳胺基-C1 -C8 烷基、雜環胺基-C1 -C8 烷基、C1 -C8 烷基羰基胺基-C1 -C8 烷基、C1 -C8 烷氧基羰基胺基-C1 -C8 烷基、C1 -C8 烷基硫基-C1 -C8 烷基、C1 -C8 烷基亞磺醯基-C1 -C8 烷基、C1 -C8 烷基磺醯基-C1 -C8 烷基或氰基-C1 -C8 烷基;或 (b)使式(VI)化合物或其鹽中之一者:其中L、n、X、Y1 、Y2 、Y3 、Y4 、Y5 、W及Z如請求項1中所敍述,且U2 表示氯原子、溴原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基, 與式(IIIc)之衍生物反應:其中M1 表示鹼金屬或過渡金屬, R1 及R2 獨立地表示C1 -C8 烷基、C2 -C8 烯基、C3 -C7 環烷基、芳基或雜環基;以及 R3 表示氫原子或C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、C2 -C8 炔基、C3 -C7 環烷基、C4 -C7 環烯基、芳基、芳基-C1 -C8 烷基、C1 -C8 烷氧基、雜環基、雜環基-C1 -C8 烷基、羥基-C1 -C8 烷基、C1 -C8 烷氧基-C1 -C8 烷基、C1 -C8 烷基羰氧基-C1 -C8 烷基、芳氧基-C1 -C8 烷基、雜環基氧基-C1 -C8 烷基、胺基-C1 -C8 烷基、C1 -C8 烷胺基-C1 -C8 烷基、二-C1 -C8 烷胺基-C1 -C8 烷基、芳胺基-C1 -C8 烷基、二-芳胺基-C1 -C8 烷基、雜環胺基-C1 -C8 烷基、C1 -C8 烷基羰基胺基-C1 -C8 烷基、C1 -C8 烷氧基羰基胺基-C1 -C8 烷基、C1 -C8 烷基硫基-C1 -C8 烷基、C1 -C8 烷基亞磺醯基-C1 -C8 烷基、C1 -C8 烷基磺醯基-C1 -C8 烷基或氰基-C1 -C8 烷基;或 (c)使式(VIII)化合物或其鹽中之一者與式(IX)化合物反應:其中L表示O、S或NR6 , R1 及R2 獨立地表示C1 -C8 烷基、C2 -C8 烯基、C3 -C7 環烷基、芳基或雜環基, R3 表示氫原子或C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、C2 -C8 炔基、C3 -C7 環烷基、C4 -C7 環烯基、芳基、芳基-C1 -C8 烷基、雜環基、雜環基-C1 -C8 烷基、羥基-C1 -C8 烷基、C1 -C8 烷氧基-C1 -C8 烷基、C1 -C8 烷基羰氧基-C1 -C8 烷基、芳氧基-C1 -C8 烷基、雜環基氧基-C1 -C8 烷基、胺基-C1 -C8 烷基、C1 -C8 烷胺基-C1 -C8 烷基、二-C1 -C8 烷胺基-C1 -C8 烷基、芳胺基-C1 -C8 烷基、二-芳胺基-C1 -C8 烷基、雜環胺基-C1 -C8 烷基、C1 -C8 烷基羰基胺基-C1 -C8 烷基、C1 -C8 烷氧基羰基胺基-C1 -C8 烷基、C1 -C8 烷基硫基-C1 -C8 烷基、C1 -C8 烷基亞磺醯基-C1 -C8 烷基、C1 -C8 烷基磺醯基-C1 -C8 烷基或氰基-C1 -C8 烷基,及 U3 表示氯原子、溴原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基;或 (d)使式(VIII)化合物或其鹽中之一者與式(IX)化合物反應其中L表示O、S或NR6 , R1 及R2 獨立地表示C1 -C8 烷基、C2 -C8 烯基、C3 -C7 環烷基、芳基或雜環基;以及 R3 表示氫原子或C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、C2 -C8 炔基、C3 -C7 環烷基、C4 -C7 環烯基、芳基、芳基-C1 -C8 烷基、C1 -C8 烷氧基、雜環基、雜環基-C1 -C8 烷基、羥基-C1 -C8 烷基、C1 -C8 烷氧基-C1 -C8 烷基、C1 -C8 烷基羰氧基-C1 -C8 烷基、芳氧基-C1 -C8 烷基、雜環基氧基-C1 -C8 烷基、胺基-C1 -C8 烷基、C1 -C8 烷胺基-C1 -C8 烷基、二-C1 -C8 烷胺基-C1 -C8 烷基、芳胺基-C1 -C8 烷基、二-芳胺基-C1 -C8 烷基、雜環胺基-C1 -C8 烷基、C1 -C8 烷基羰基胺基-C1 -C8 烷基、C1 -C8 烷氧基羰基胺基-C1 -C8 烷基、C1 -C8 烷基硫基-C1 -C8 烷基、C1 -C8 烷基亞磺醯基-C1 -C8 烷基、C1 -C8 烷基磺醯基-C1 -C8 烷基或氰基-C1 -C8 烷基;或 (e)使式(X)化合物或其鹽中之一者與式(XI)化合物反應:其中L表示CR4 R5 , R4 及R5 獨立地表示氫原子或C1 -C8 烷基, U4 表示溴原子、氯原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基; W1 表示硼衍生物, R1 及R2 獨立地表示C1 -C8 烷基、C2 -C8 烯基、C3 -C7 環烷基、芳基或雜環基;以及 R3 表示氫原子、C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、C2 -C8 炔基、C3 -C7 環烷基、C4 -C7 環烯基、芳基、芳基-C1 -C8 烷基、C1 -C8 烷氧基、雜環基、雜環基-C1 -C8 烷基、羥基-C1 -C8 烷基、C1 -C8 烷氧基-C1 -C8 烷基、C1 -C8 烷基羰氧基-C1 -C8 烷基、芳氧基-C1 -C8 烷基、雜環基氧基-C1 -C8 烷基、胺基-C1 -C8 烷基、C1 -C8 烷胺基-C1 -C8 烷基、二-C1 -C8 烷胺基-C1 -C8 烷基、芳胺基-C1 -C8 烷基、二-芳胺基-C1 -C8 烷基、雜環胺基-C1 -C8 烷基、C1 -C8 烷基羰基胺基-C1 -C8 烷基、C1 -C8 烷氧基羰基胺基-C1 -C8 烷基、C1 -C8 烷基硫基-C1 -C8 烷基、C1 -C8 烷基亞磺醯基-C1 -C8 烷基、C1 -C8 烷基磺醯基-C1 -C8 烷基或氰基-C1 -C8 烷基;或 (f)使式(VIII)化合物或其鹽中之一者與式(XII)化合物反應:其中L表示CR4 R5 , R1 及R2 獨立地表示C1 -C8 烷基、C2 -C8 烯基、C3 -C7 環烷基、芳基或雜環基, R3 表示氫原子或C1 -C8 烷基、包含至多9個可相同或不同之鹵素原子的C1 -C8 鹵代烷基、C2 -C8 烯基、C2 -C8 炔基、C3 -C7 環烷基、C4 -C7 環烯基、芳基、芳基-C1 -C8 烷基、C1 -C8 烷氧基、雜環基、雜環基-C1 -C8 烷基、羥基-C1 -C8 烷基、C1 -C8 烷氧基-C1 -C8 烷基、C1 -C8 烷基羰氧基-C1 -C8 烷基、芳氧基-C1 -C8 烷基、雜環基氧基-C1 -C8 烷基、胺基-C1 -C8 烷基、C1 -C8 烷胺基-C1 -C8 烷基、二-C1 -C8 烷胺基-C1 -C8 烷基、芳胺基-C1 -C8 烷基、二-芳胺基-C1 -C8 烷基、雜環胺基-C1 -C8 烷基、C1 -C8 烷基羰基胺基-C1 -C8 烷基、C1 -C8 烷氧基羰基胺基-C1 -C8 烷基、C1 -C8 烷基硫基-C1 -C8 烷基、C1 -C8 烷基亞磺醯基-C1 -C8 烷基、C1 -C8 烷基磺醯基-C1 -C8 烷基或氰基-C1 -C8 烷基, R4 及R5 獨立地表示氫原子、C1 -C8 烷氧基或C1 -C8 烷基, U3 表示溴原子、氯原子、碘原子、甲磺醯基、甲苯磺醯基或三氟甲磺醯基;以及 W2 表示硼衍生物。
- 一種式(IIa)化合物以及其可接受之鹽:其中L、n、X、Y1 、Y2 、Y3 、Y4 、Y5 、W及Z如請求項1中所敍述,且U1a 表示氯原子、溴原子或碘原子。
- 一種式(V)化合物以及其可接受之鹽:其中L、n、X、Y1 、Y2 、Y3 、Y4 、Y5 、W及Z如請求項1中所敍述, 其限制條件為該式(V)化合物不表示: {2-溴-6-[(8-氟喹啉-3-基)氧基]苯基}甲醇[1314009-28-3],及 {2-氯-6-[(8-氟喹啉-3-基)氧基]苯基}甲醇[1314009-25-0]。
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KR20160072155A (ko) | 2013-10-17 | 2016-06-22 | 다우 아그로사이언시즈 엘엘씨 | 살충성 화합물의 제조 방법 |
EP3057430A4 (en) | 2013-10-17 | 2017-09-13 | Dow AgroSciences LLC | Processes for the preparation of pesticidal compounds |
TW201613866A (en) | 2014-07-07 | 2016-04-16 | Bayer Cropscience Ag | Process for preparing fluorinated iminopyridine compounds |
JP6398125B2 (ja) | 2015-02-17 | 2018-10-03 | 日本曹達株式会社 | 農薬組成物 |
CN114292799A (zh) | 2015-03-26 | 2022-04-08 | 拜耳作物科学有限合伙公司 | 新型类芽孢杆菌属菌株、抗真菌化合物以及它们的使用方法 |
AR106515A1 (es) * | 2015-10-29 | 2018-01-24 | Bayer Cropscience Ag | Sililfenoxiheterociclos trisustituidos y análogos |
WO2017178408A1 (en) * | 2016-04-15 | 2017-10-19 | Syngenta Participations Ag | Microbiocidal silicon containing aryl derivatives |
-
2018
- 2018-05-02 US US16/610,038 patent/US20200275656A1/en not_active Abandoned
- 2018-05-02 CN CN201880029313.6A patent/CN110582484A/zh active Pending
- 2018-05-02 JP JP2019559843A patent/JP2020519575A/ja active Pending
- 2018-05-02 EP EP18722951.3A patent/EP3619197A1/en not_active Withdrawn
- 2018-05-02 BR BR112019023030-0A patent/BR112019023030A2/pt not_active Application Discontinuation
- 2018-05-02 WO PCT/EP2018/061206 patent/WO2018202712A1/en unknown
- 2018-05-03 AR ARP180101169A patent/AR111676A1/es unknown
- 2018-05-03 TW TW107114969A patent/TW201843138A/zh unknown
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JP2020519575A (ja) | 2020-07-02 |
AR111676A1 (es) | 2019-08-07 |
US20200275656A1 (en) | 2020-09-03 |
WO2018202712A1 (en) | 2018-11-08 |
CN110582484A (zh) | 2019-12-17 |
EP3619197A1 (en) | 2020-03-11 |
BR112019023030A2 (pt) | 2020-06-02 |
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