CN1071322C - 5,6-二氢-1,3-噁嗪类化合物的制备方法 - Google Patents
5,6-二氢-1,3-噁嗪类化合物的制备方法 Download PDFInfo
- Publication number
- CN1071322C CN1071322C CN96195705A CN96195705A CN1071322C CN 1071322 C CN1071322 C CN 1071322C CN 96195705 A CN96195705 A CN 96195705A CN 96195705 A CN96195705 A CN 96195705A CN 1071322 C CN1071322 C CN 1071322C
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- Prior art keywords
- alkyl
- replaces
- randomly
- phenyl
- substituting group
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 24
- LUSYNJGQFRRKIA-UHFFFAOYSA-N 5,6-dihydro-2h-1,3-oxazine Chemical class C1CC=NCO1 LUSYNJGQFRRKIA-UHFFFAOYSA-N 0.000 title abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 62
- -1 phenylalkenyl Chemical group 0.000 claims abstract description 55
- 238000002360 preparation method Methods 0.000 claims abstract description 35
- 150000001408 amides Chemical class 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 15
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007789 gas Substances 0.000 claims abstract description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 7
- 239000005977 Ethylene Substances 0.000 claims abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 4
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 4
- 238000010572 single replacement reaction Methods 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- DWDAZFJBSZTCCM-UHFFFAOYSA-N [O]C1CCCCC1 Chemical compound [O]C1CCCCC1 DWDAZFJBSZTCCM-UHFFFAOYSA-N 0.000 claims description 2
- VBXAEFHLULAXHG-UHFFFAOYSA-N nitrosomethylbenzene Chemical compound O=NCC1=CC=CC=C1 VBXAEFHLULAXHG-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 9
- 230000002508 compound effect Effects 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract description 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 91
- 229910052731 fluorine Inorganic materials 0.000 description 69
- 239000011737 fluorine Substances 0.000 description 69
- 229910052801 chlorine Inorganic materials 0.000 description 67
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 66
- 125000001309 chloro group Chemical group Cl* 0.000 description 55
- 125000001153 fluoro group Chemical group F* 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 20
- 229910052794 bromium Inorganic materials 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 5
- 150000003851 azoles Chemical class 0.000 description 5
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- 244000025254 Cannabis sativa Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UFTHEDBYLPFRDP-UHFFFAOYSA-N 5,6-dihydro-2h-oxazine Chemical class C1CC=CNO1 UFTHEDBYLPFRDP-UHFFFAOYSA-N 0.000 description 3
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
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- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-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
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- 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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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
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Abstract
本发明提供了制备式(Ⅰ)5,6-二氢-1,3-嗪化合物(其中一些为已知化合物)的新方法:
其中:
A代表取代苯基,或代表在所有情况下任选取代的萘基、吡啶基、噻吩基或吡唑基,和
B代表氢,烷基,烷氧基烷基,烷硫基烷基,卤代烷基,链烯基,任选取代的环烷基,或在所有情况下任选取代的苯基、苯基烷基、苯氧基烷基、苯硫基烷基、吡啶基或2-或3-吡咯基,
该方法包括在氯化氢气体和催化剂存在下,将式(Ⅱ)酰胺衍生物:
与乙烯反应。新的5,6-二氢-1,3-嗪化合物可用于杀灭动物害虫。
Description
本发明涉及制备5,6-二氢-1,3-噁嗪类化合物的新方法(其中所述化合物部分为新的),涉及新的5,6-二氢-1,3-噁嗪类化合物,并涉及用于其制备的新中间体以及它们用于杀灭动物害虫的应用。
而且,还已知,5,6-二氢-1,3-噁嗪类化合物可以根据下列反应式按下所述制备:首先使式(A)氨基醇与式(C)酰氯反应,其后用脱水剂环化所得的式(D)酰氨基醇:(参见EP-A 0 635 500和WO-A 94/14783)。
此外,还已知5,6-二氢-1,3-噁嗪类化合物可以根据下列反应式按下所述制备:在铑配合物存在下,如果合适的话在加有二膦情况下,使式(E)氨基醇与式(F)的腈类化合物反应:(参见JP-A 06 298 746)。
然而,用这些已知合成方法得到的产物收率并不能令人满意,特别是当采用全合成方法,即包括作为起始物质的式(A)和(E)氨基醇的制备时更是如此:因为经过众多反应步骤和采用昂贵的前体和还原剂,氨基醇仅能以不能令人满意的收率得到,同时由于大量还原剂和溶剂的使用,和某些步骤必须在惰性气体保护下进行,还存在一些另外技术问题。
现已发现,式(Ⅰ)5,6-二氢-1,3-噁嗪类化合物可按下面所述制备:其中:A代表取代的苯基,或代表在每种情况下任选取代的萘基、吡啶基、噻吩基或吡唑基,和B代表氢,烷基,烷氧基烷基,烷硫基烷基,卤代烷基,链烯基,任选取代的环烷基,或在每种情况下任选取代的苯基、苯基烷基、苯基链烯基、苯氧基烷基、苯硫基烷基、吡啶基或2-或3-吡咯基,在氯化氢气体和催化剂存在下,如果合适的话在稀释剂存在下,将下式(Ⅱ)酰胺衍生物与乙烯反应:
其中:
A和B的定义同上,和
R1和R2相同或不同,并各自代表烷基,或者与它们所键连的N原子一起代表任选取代的杂环。
虽然由于乙烯的低反应性,一般不能显著地发生所期望的反应,但令人惊奇的是,本发明方法能够以良好的收率和极高的纯度得到式(Ⅰ)5,6-二氢-1,3-噁嗪类化合物。
因此,本发明的反应具有容易进行的优点,同时具有改进的收率,特别是当目的在于全合成方法,即考虑前体的制备时更是如此(参见制备实施例)。
式(Ⅰ)提供了本发明所制备的化合物的一般定义。在上下文中的所述通式内提到的优选的取代基或基团范围在下文中予以说明。A优选代表苯基,它被选自卤素,C1-C6烷基,C1-C6烷氧基,C1-C6烷硫基,C1-C6卤代烷基,C1-C6卤代烷氧基,C1-C6卤代烷硫基,硝基,氰基或苯基的相同或不同取代基单取代至五取代,其中的苯基取代基本身则又任选地被选自卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷硫基和C1-C6卤代烷硫基的相同或不同取代基单取代至五取代,
或代表萘基,它任选地被选自卤素,C1-C6烷基,C1-C6烷氧基和C1-C6卤代烷氧基的相同或不同取代基单取代至三取代,
或代表吡啶基,它任选地被选自卤素,C1-C6烷基,C1-C6烷氧基,C1-C6卤代烷基,C1-C6卤代烷氧基和氰基的相同或不同取代基单取代至三取代,
或代表噻吩基,它任选地被选自卤素和C1-C6烷基的相同或不同取代基单取代至三取代,
或代表吡唑基,它任选地被选自卤素和C1-C3烷基的相同不同取代基单取代至三取代。B优选代表氢,C1-C6烷基,C1-C6烷氧基-C1-C6烷基,C1-C6烷硫基-C1-C6烷基,C1-C6卤代烷基和C2-C6链烯基,
或代表C3-C7环烷基,它任选地被选自卤素,C1-C6烷基,C1-C6烷氧基,C1-C6卤代烷基和C1-C6卤代烷氧基的相同或不同取代基单取代至五取代,
或代表吡啶基,它任选地被选自卤素,C1-C6烷基,C1-C6烷氧基,C1-C6卤代烷基,C1-C6卤代烷氧基和氰基的相同或不同取代基单取代至三取代,
或代表α-吡咯基或β-吡咯基,它们各自任选地被选自卤素和C1-C4烷基的相同或不同取代基单取代或二取代,
或代表被羟基,CHO,氰基,羧基,多-C1-C8烷氧基-C1-C8烷基或C1-C8烷氧基羰基取代的苯基,
或代表苯基,苄基,苯乙-1-基,苯乙-2-基,苯氧基甲基,苯硫基甲基,苯硫基乙-1-基,苯氧基乙-1-基,苯氧基乙-2-基或苯乙烯基,它们各自任选地被相同或不同的取代基在苯环上单取代至五取代,在每种情况下的适宜取代基为:
卤素,
C1-C18烷基,
C1-C8烷氧基-C1-C8烷基,
C1-C8卤代烷氧基,
C1-C4卤代烷基,
C1-C18烷氧基,它任选地被另外1至3个氧原子间断,
C1-C18烷硫基,
C1-C8卤代烷硫基,
苯基-二-(C1-C8)烷基甲硅烷基,
三-(C1-C8)烷基甲硅烷基,
3,4-二氟亚甲二氧基(3,4-difluoromethylenedioxo),
3,4-四氟-1,2-亚乙二氧基(3,4-tetrafluoroethylenedioxo),
稠合苯并基团,
稠合C3-C4亚烷基,
任选地被卤素,C1-C4烷基或C3-C6环烷基取代的苄基亚氨基氧基甲基,
环己基或环己基氧基,它们各自任选地被C1-C6烷基,C1-C6烷氧基,环己基或苯基取代,
吡啶氧基,它任选地被选自卤素,C1-C4烷基和C1-C4卤代烷基的相同或不同取代基单取代或二取代,
苯基,苯基-C1-C6烷基,苯氧基,苯硫基,苯基-C1-C6烷氧基或苄硫基,它们各自任选地被选自卤素,C1-C12烷基,C1-C4卤代烷基,C1-C12烷氧基,C1-C6卤代烷氧基,C1-C6烷氧基-C1-C6烷基,C1-C6烷氧基-乙烯氧基,C1-C6烷硫基和C1-C6卤代烷硫基的相同或不同取代基单取代至五取代。A特别优选代表苯基,它被选自氟,氯,溴,C1-C3烷基,C1-C3烷氧基,C1-C3烷硫基,被选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,被选自氟和氯的相同或不同取代基单取代至五取代的C1-C4烷氧基,SCF3,SCHF2,硝基,氰基,或苯基的相同或不同取代基单取代至五取代,其中的苯基取代基本身则又任选地被选自氟,氯,溴,C1-C4烷基,C1-C4烷氧基,C1-C4烷硫基,被选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,被选自氟和氯的相同或不同取代基单取代至五取代的C1-C4烷氧基,SCF3或SCHCF2的相同或不同取代基单取代至五取代,
或代表萘基,它任选地被选自氟,氯,C1-C6烷基,C1-C6烷氧基和被选自氟和氯的相同或不同取代基单取代至三取代的C1-C6烷氧基的相同或不同取代基单取代至三取代,
或代表吡啶基,它任选地被选自氟,氯,C1-C3烷基,C1-C3烷氧基,CF3,OCF3和氰基的相同或不同取代基单取代或二取代,
或代表噻吩基,它任选地被选自氯,溴,甲基和乙基的相同或不同取代基单取代或二取代,
或代表吡唑基,它任选地被选自氟,氯,溴和C1-C3烷基的相同或不同取代基单取代至三取代,B特别优选代表氢,C1-4烷基,C1-4烷氧基-C1-4烷基,C1-4烷硫基-C1-4烷基,C1-4卤代烷基或C2-C6链烯基,
或代表环丙基,环戊基或环己基,它们各自任选地被选自氟,氯,溴,C1-C3烷基,C1-C3烷氧基,CF3和OCF3的相同或不同取代基单取代至三取代,
或代表吡啶基,它任选地被选自氟,氯,C1-C3烷基,C1-C3烷氧基,CF3,OCF3和氰基的相同或不同取代基单取代或二取代,
或代表α-吡咯基或β-吡咯基,它们各自任选地被选自氟,氯和C1-C3烷基的相同或不同取代基单取代或二取代,
或代表苯基,它被CHO,氰基,羟基,羧基,多-C1-C8烷氧基-C1-C6烷基或C1-C8烷氧基羰基取代,
或代表苯基,苄基,苯乙-1-基,苯乙-2-基,苯氧基甲基,苯硫基甲基,苯硫基乙-1-基,苯氧基乙-1-基,苯氧基乙-2-基或苯乙烯基,它们各自任选地被相同或不同的取代基在苯环上单取代至四取代,在每种情况下的适宜取代基为:
氟,氯,溴,
C1-C18烷基,
C1-C6烷氧基-C1-C8烷基,
被选自氟和氯的相同或不同取代基单取代至六取代的C1-C8烷氧基,
被选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,
C1-C18烷氧基或-(OC2H4)1-3-O-C1-C6烷基,
C1-C15烷硫基,
被选自氟和氯的相同或不同取代基单取代至六取代的C1-C8烷硫基,
三-(C1-C6)烷基甲硅烷基,
苯基-二-(C1-C6)-烷基甲硅烷基,
3,4-二氟亚甲二氧基,
3,4-四氟-1,2-亚乙二氧基,
稠合苯并基团,
稠合C4亚烷基,
环己基或环己氧基,它们各自任选地被C1-C4烷基,C1-C4烷氧基,环己基或苯基取代,
吡啶氧基,它任选地被选自氟,氯和CF3的相同或不同取代基单取代或二取代,
苯基,苯基-C1-C6烷基,苯氧基,苯硫基,苯基-C1-C6烷氧基或苄硫基,它们各自任选地被选自氟,氯,溴,C1-C12烷基,由选自氟和氯的相同或不同取代基单取代至六取代的C1-C4烷基,C1-C12烷氧基,由选自氟和氯的相同或不同取代基单取代至六取代的C1-C4烷氧基,或C1-C4烷氧基-C1-C4烷基,C1-C4烷氧基乙烯氧基,C1-C4烷硫基或由选自氟和氯的相同或不同取代基单取代至六取代的C1-C4烷硫基的相同或不同取代基单取代至四取代。A更特别优选代表苯基,它被选自氟,氯,溴,C1-C3烷基,C1-C3烷氧基,C1-C3烷硫基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C4烷氧基,SCF3,SCHF2,硝基,氰基,或苯基的相同或不同取代基单取代至三取代,其中所述的苯基取代基本身又任选地被选自氟,氯,溴,C1-C3烷基,C1-C3烷氧基,C1-C3烷硫基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C4烷氧基,SCF3或SCHF2的相同或不同取代基单取代至四取代。B更特别优选氢,C1-C4烷基,C1-C2烷氧基-C1-C4烷基,C1-C2烷硫基-C1-C4烷基,C1-C2卤代烷基或C2-C4链烯基,
或代表环丙基,环戊基或环己基,它们各自任选地被选自氟,氯,CH3,C2H5,OCH3,CF3或OCF3的相同或不同取代基单取代至三取代,
或代表吡啶基,它任选地被选自氟,氯,CH3,C2H5,OCH3,CF3,OCF3和氰基的相同或不同取代基单取代或二取代,
或代表α-吡咯基或β-吡咯基,它们各自任选地被选自氟,氯,CH3和C2H5的相同或不同取代基单取代或二取代,
或代表被CHO,羟基,氰基,羧基,二-C1-C6烷氧基-C1-C4烷基或C1-C6烷氧基羰基取代的苯基,
或代表苯基,苄基,苯乙-1-基,苯乙-2-基,苯氧基甲基,苯硫基甲基,苯硫基乙-1-基,苯氧基乙-1-基,苯氧基乙-2-基或苯乙烯基,它们各自任选地被相同或不同的取代基在苯环上单取代至三取代,其中每种情况下的适宜取代基为:
氟,氯,溴,
C1-C18烷基,
C1-C6烷氧基-C1-C8烷基,
由选自氟和氯的相同或不同取代基单取代至六取代的C1-C8烷氧基,
由选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,
C1-C18烷氧基或-(OC2H4)1-3-O-C1-C6-烷基,
C1-C15烷硫基,
由选自氟和氯的相同或不同取代基单取代至六取代的C1-C8烷硫基,
三-(C1-C6)烷基甲硅烷基,
苯基-二-(C1-C6)烷基甲硅烷基,
3,4-二氟亚甲二氧基,
3,4-四氟-1,2-亚乙基二氧基,
稠合苯并基团,
稠合C4-亚烷基,
环己基或环己氧基,它们各自任选地被C1-C4烷基,C1-C4烷氧基,环己基或苯基取代,
吡啶氧基,它任选地被选自氟,氯和CF3的相同或不同取代基单取代或二取代,
苯基,苯基-C1-C6烷基,苯氧基,苯硫基,苯基-C1-C6烷氧基或苄硫基,它们各自任选地被选自下述相同或不同的取代基单取代至四取代:氟,氯,溴,C1-C12烷基,由氟或氯单取代至六取代的C1-C4烷基,或C1-C12烷氧基,由选自氟和氯的相同或不同取代基单取代至六取代的C1-C4烷氧基,或C1-C4烷氧基-C1-C4烷基,C1-C4烷氧基-乙烯氧基,C1-C4烷硫基或由选自氟和氯的相同或不同取代基单取代至六取代的C1-C4烷硫基。
本发明可制备的优选化合物为式(Ⅰa)化合物:其中:A具有上述一般的,优选的,特别优选的以及更特别优选的含义,和B1代表被相同或不同取代基单取代至五取代的苯基,适宜的取代基为上述B中所述的有关苯基的优选的,特别优选的和更优选的那些取代基。
本发明可制备的特别优选的一组化合物为式(Ⅰ)化合物:其中:A代表被选自氟和氯的相同或不同取代基单取代或二取代的苯基,以及B代表被选自氟,氯,溴,C1-C8烷基,C1-C8烷氧基,C1-C4卤代烷基,C1-C4卤代烷氧基,C1-C8烷硫基和C3-C6环烷基的相同或不同取代基单取代至三取代的苯基,或
代表被苯基,苯基-C1-C3烷基,苯氧基或苄氧基单取代的苯基,其中的取代基本身各自可任选地被选自氟,氯,溴,C1-C6烷基,C1-C6烷氧基,C1-C4卤代烷基和C1-C4卤代烷氧基的相同或不同取代基在苯基部分上单取代或二取代,
或代表吡啶基或2-或3-吡咯基,它们各自任选地被选自氟,氯,甲基,乙基和三氟甲基的相同或不同取代基单取代或二取代,或
代表被CHO,羟基,氰基,羧基,二-C1-C6烷氧基-C1-C4烷基或C1-C6烷氧基羰基取代的苯基。
例如,如果在HCl气体和作为催化剂的四氯化钛存在下,使用N-[吗啉-4-基-(4-叔丁基苯基)-甲基1-2,6-二氟苯甲酰胺和乙烯作为起始物质,则本发明方法的反应过程可用下述反应式表示:式(Ⅱ)提供了在本发明方法中用作起始物质的酰胺衍生物的一般定义。在式(Ⅱ)中,A和B优选或特别优选具有上述本发明可制备的式(Ⅰ)化合物的描述中关于A和B的优选的,特别优选的或更特别优选的定义中早已指出的那些含义。
R1和R2相同或不同,并优选代表C1-C4烷基,特别是甲基,乙基或正-或异-丙基,或者与它们所键连的N原子一起代表5-或6-元杂环,它任选地被相同或不同取代基单取代至五取代,优选单取代或二取代,并且任选含有一个或两个另外的杂原子,优选一个另外的杂原子,如O,S,或NR,可提及的取代基特别是C1-C4烷基和C1-C4烷氧基,并且R代表烷基,优选C1-C4烷基,或任选取代的芳基,特别是被相同或不同的取代基任选地单取代或二取代的苯基,可提及的优选的取代基包括:卤素,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4烷硫基和C1-C4卤代烷硫基。
其中B代表氢的某些式(Ⅱ)酰胺衍生物是已知化合物(例如,参见Liebigs Annalen 343,207(1905)和Bull.Soc.Chim.France 1979,Ⅱ,409-414)。
例如,式(Ha)酰胺衍生物可按下所述制备:如果合适的话在稀释剂存在下,将式(Ⅲ)酰胺:
A-CO-NH2 (Ⅲ)其中:A的定义同上,与式(Ⅳ)醛:
B2-CHO (Ⅳ)其中:B2的定义同上,和式(Ⅴ)胺反应:其中:R1和R2的定义同上。
作为制备式(Ⅱ)酰胺衍生物的起始物质所需的式(Ⅱ)酰胺,式(Ⅳ)醛和式(Ⅴ)仲胺通常是已知的,或可用一般公知的方式制备。
用于实施式(Ⅱ)酰胺衍生物制备方法的合适稀释剂包括此类反应常规使用的所有惰性有机溶剂。优选使用下述溶剂:醇,如甲醇或乙醇;酯,如乙酸甲酯或乙酸乙酯;醚,如乙醚,甲基叔丁基醚,乙二醇二甲醚,四氢呋喃或二噁烷,此外还有腈类,如乙腈;以及任选的卤代脂族,脂环族或芳族烃,如二氯甲烷,氯仿,四氯化碳,己烷,环己烷,苯,甲苯,二甲苯或氯苯;还包括亚砜,如二甲亚砜。
当实施式(Ⅱ)酰胺衍生物的制备方法时,反应温度可在较宽范围内变化,一般地,方法是在0至120℃,优选10-100℃的温度下进行。
当实施式(Ⅱ)酰胺衍生物的制备方法时,一般每摩尔式(Ⅲ)酰胺使用1.0至1.5摩尔,优选1.0至1.2摩尔式(Ⅳ)醛和1.0至2.0摩尔,优选1.0至1.2摩尔式(Ⅴ)仲胺。
利用常规方法进行反应并后处理和分离反应产物。
如果合适的话,式(Ⅱ)酰胺衍生物也可以按本发明方法直接,即无需分离,与乙烯反应,得到最终式(Ⅰ)产物(同样参见制备实施例)。
当用于杀灭动物害虫时,新的式(Ⅱa)酰胺衍生物也显示出良好的生物作用。
本发明制备式(Ⅰ)化合物的方法是在氯化氢气体和催化剂存在下进行。合适的催化剂为路易斯酸,优选过渡金属卤化物,特别是四氯化钛,四氯化锡和二氯化锌。
本发明方法优选在稀释剂存在下进行。
合适的稀释剂为常规有机溶剂,例如,任选的卤代脂族,脂环族或芳族烃。这些包括,例如,氯苯,二氯苯,石油醚,己烷,环己烷,二氯甲烷,氯仿和四氯化碳。
当实施本发明方法时,反应温度可在较宽范围内变化,一般地,本方法是在-120至+120℃,优选10-100℃的温度下进行。
在此温度下,本方法优选在密封容器(高压釜)中,于反应混合物所产生的内部压力下进行。然而,也可以通过在大气压力下,将乙烯通过反应混合物来进行,其中未消耗的乙烯可任选地再循环使用。
另外的可能性是在低温(大约-110℃)下在乙烯中进行缩合并在此温度下进行反应。
为实施本发明方法,相对于每摩尔式(Ⅱ)酰胺衍生物,一般使用1至5摩尔,优选1至3摩尔乙烯和在每种情况下使用1至5摩尔,优选1至4摩尔氯化氢气体和催化剂。
后处理按常规方式进行,优选在0至10℃温度下(冷却)将反应混合物调节成碱性并用一般的常规方式分离最终产物。
按本发明方法制备的式(Ⅰ)5,6一二氢-1,3-噁嗪化合物大部分是已知的(参见例如EP-A-0635 500和WO-A 94/14783),它们可用于杀灭有害动物。
新的式(Ⅰb)化合物同样构成了本发明的主题:其中:A的定义同上,和D代表在每种情况下任选取代的2-或3-吡咯基,或被CHO,氰基,羧基,多烷氧基烷基或烷氧基羰基取代的苯基。
依据取代基的性质,式(Ⅰb)化合物也可以以几何和/或旋光异构体或各种组合异构体的混合物形式存在。本发明还涉及纯净异构体和异构体混合物。
而且,还发现式(Ⅰb)化合物可用下述的本发明方法制备。
最后,还发现新的式(Ⅰb)化合物非常适于杀灭动物害虫,特别是节肢动物和线虫。
令人惊奇的是,本发明的式(Ⅰb)化合物显示出远高于结构最相近化合物防治动物害虫的活性。
式(Ⅰb)提供了本发明化合物的一般定义。
在上下文中的所述通式内提到的优选的取代基或基团范围在下文中予以说明。A优选代表苯基,它被选自卤素,C1-C6烷基,C1-C6烷氧基,C1-C6烷硫基,C1-C6卤代烷基,C1-C6代烷氧基,C1-C6卤代烷硫基,硝基,氰基和苯基的相同或不同取代基单取代至五取代,其中的取代基苯基本身则任选地被选自卤素,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷硫基和C1-C6卤代烷硫基的相同或不同取代基单取代至五取代,
或代表任选地被相同或不同取代基单取代至三取代的萘基,可提及的取代基包括卤素,C1-C6烷基,C1-C6烷氧基和C1-C6卤代烷氧基,
或代表任选地被相同或不同取代基单取代至三取代的吡啶基,可提及的取代基包括卤素,C1-C6烷基,C1-C6烷氧基,C1-C6卤代烷基,C1-C6卤代烷氧基和氰基,
或代表任选地被相同或不同取代基单取代至三取代的噻吩基,可提及的取代基包括卤素和C1-C6烷基,
或代表任选地被相同不同取代基单取代至三取代的吡唑基,可提及的取代基包括卤素和C1-C3烷基。D优选代表2-吡咯基或3-吡咯基,它们各自任选地被选自卤素和C1-C4烷基的相同或不同取代基单取代或二取代,
或代表被CHO,氰基,羧基,多-C1-C8烷氧基-C1-C8烷基或C1-C8烷氧基羰基取代的苯基。A特别优选代表苯基,它被选自氟,氯,溴,C1-C3烷基,C1-C3烷氧基,C1-C3烷硫基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C4烷氧基,SCF3,SCHF2,硝基,氰基,和苯基的相同或不同取代基单取代至五取代,其中的取代基苯基本身则又任选地被选自氟,氯,溴,C1-C4烷基,C1-C4烷氧基,C1-C4烷硫基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C4烷氧基,SCF3和SCHF2的相同或不同取代基单取代至五取代,
或代表任选地被相同或不同取代基单取代至三取代的萘基,可提及的取代基包括氟,氯,C1-C6烷基,C1-C6烷氧基和被选自氟和氯的相向或不同取代基单取代至三取代的C1-C6烷氧基,
或代表任选地被相同或不同取代基单取代或二取代的吡啶基,可提及的取代基包括氟,氯,C1-C3烷基,C1-C3烷氧基,CF3,OCF3和氰基,
或代表任选地被相同或不同取代基单取代或二取代的噻吩基,可提及的取代基包括氯,溴,甲基或乙基,
或代表任选地被相同不同取代基单取代至三取代的吡唑基,可提及的取代基包括氟,氯,溴和C1-C3烷基。D特别优选代表2-吡咯基或3-吡咯基,它们各自任选地被选自氟,氯和C1-C3烷基的相同或不同取代基单取代或二取代的,
或代表被CHO,氰基,羧基,多-C1-C8-烷氧基-C1-C6-烷基或C1-C8烷氧基羰基取代的苯基。A特别优选代表苯基,它被选自氟,氯,溴,C1-C3烷基,C1-C3烷氧基,C1-C3烷硫基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,由选自氟和氯的相同或不同取代基单取代至三取代的C1-C4烷氧基,SCF3,SCHF2,硝基,氰基,和苯基的相同或不同取代基单取代至三取代,其中的取代基苯基本身则又任选地被选自氟,氯,溴,C1-C3烷基,C1-C3烷氧基,C1-C3烷硫基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C2烷基,由选自氟和氯的相同或不同取代基单取代至五取代的C1-C4烷氧基,SCF3和SCHF2的相同或不同取代基单取代至五取代,D更特别优选代表2-吡咯基或3-吡咯基,它们各自任选地被选自氟,氯,CH3和C2H5的相同或不同取代基单取代或二取代的,或代表被CHO,氰基,羧基,多-C1-C6-烷氧基-C1-C4-烷基或C1-C6烷氧基羰基取代的苯基。A特别优选地代表被选自氟和氯的相同或不同取代基单取代或二取代的苯基。D特别优选地代表任选地被选自氟,氯,甲基和乙基的相同或不同取代基单取代或二取代的2-或3-吡咯基,或代表被CHO,氰基,羧基,二-C1-C6-烷氧基-C1-C4-烷基或C1-C6烷氧基羰基取代的苯基。
活性化合物适于杀灭在农业、森林、贮存产品和材料的保护以及卫生区中遇到的有害动物,优选节肢动物和线虫。它们对正常敏感和抗性的种属以及对所有或某些生长阶段都具有活性。上述有害动物包括:
等足目,例如,潮虫,草莓卷蛾和带鼠妇。
倍足纲目,例如,具斑马陆。
唇足亚纲目,例如,食果地蜈蚣和蚰蜒。
综合纲目,例如,庭院幺蚰。
缨尾目,例如,西洋衣鱼。
弹尾目,例如,具刺跳虫。
直翅目,例如,东方非蠊,美洲大蠊,马得拉蜚蠊,德国小蠊,家蟋蟀,蝼蛄属,热带飞蝗,长额负蝗和沙漠蝗。
革翅目,例如,欧洲球螋。
等翅目,例如,白蚁属。
虱目,例如,忽布瘤额蚜,瘿绵蚜属,体虱,血虱属和长颚虱属。
食毛目,例如,羽虱属和啮虱属。
缨翅目,例如,温室条蓟马和棉蓟马。
异翅亚目,例如,蝽属,棉红蝽,甜菜拟网蝽,臭虫,长红蜡蝽和猎蝽属。
同翅目,例如,甘蓝粉虱,棉粉虱,温室白粉虱,棉蚜,甘蓝蚜,茶鹿隐瘤额蚜,甜菜蚜,苹果蚜,苹果棉蚜,桃大尾蚜,麦长管蚜,瘤额蚜属,忽布瘤额蚜,粟缢管蚜,微叶蝉属,纹叶蝉,黑尾叶蝉,李蜡蚧,揽珠蜡蚧,稻灰飞虱,稻褐飞虱,红圆蚧,夹竹桃园蚧,粉蚧属和木虱属。
鳞翅目,例如,红铃虫,松尺蠖,冬天蛾,苹果细蛾,樱桃巢蛾,小菜蛾,天幕毛虫,黄毒蛾,毒蛾属,棉潜叶蛾,桔叶潜蛾,地老虎属,切根虫属,夜蛾属(Feltia spp.),埃及金刚钻,棉铃虫属,甜菜夜蛾,甘蓝夜蛾,小眼夜蛾,斜纹夜蛾,粘虫属,粉纹夜蛾,苹果蠹蛾,粉蝶属,螟属,玉米螟,地中海粉螟,大蜡螟,袋衣蛾,网衣蛾,褐织夜蛾,亚麻黄卷蛾,烟卷蛾,云杉卷叶蛾,葡萄果蠹蛾,茶长卷蛾和栎绿卷叶蛾。
鞘翅目,例如,家具窃蠹,谷蠹,大豆象,家天牛,赤杨紫跳甲,马铃薯甲虫,辣根猿叶甲,叶甲属,油菜兰跳甲,墨西哥豆瓢虫,隐食甲属,锯谷盗,象甲属,米象属,葡萄黑象甲,香蕉蛙基象甲,甘蓝荚象甲,苜蓿叶象甲,皮蠹属,斑皮蠹属,圆皮蠹属,黑皮蠹属,粉蠹属,油菜花露尾甲,蛛甲属,金黄蛛甲,麦蛛甲,拟谷盗属,黄粉甲,叩甲属,金针虫属,金龟,六月金龟和新西兰肋翅鳃角金龟。
膜翅目,例如,松叶蜂属,叶蜂属,蚁属,厨蚁和胡蜂属。
双翅目,例如,伊蚊属,按蚁属,库蚁属,黄猩猩果蝇,家蝇属,厩蝇属,红头丽蝇,绿蝇属,果蝇属,疽蝇属,胃蝇属,虱蝇属,螯蝇属,鼻蝇属,皮蝇属,虻属,螗蜩,花园毛蚊,瑞典麦杆蝇,麦花蝇属,甜菜潜叶蝇,地中海实蝇,油橄榄实蝇和欧洲大蚊。
蚤目,例如,东方鼠蚤和角叶蚤属。
蛛形纲目,例如,蝎(Scorpio maurus)和黑寡妇。
蜱螨目,例如,粗脚粉螨,锐缘蜱属,鸡皮刺螨,Eriophyes ribis,柑桔锈螨,牛蜱属,扇头蜱属,花蜱属,璃眼蜱属,硬蜱属,瘙螨属,痒螨属,疥螨属,跗线螨属,苜蓿台螨,全爪螨属和红叶螨属。
本发明化合物表现出较强的杀虫和杀螨活性。
本发明的化合物特别成功地用于杀灭对植物有害的昆虫,如辣根猿叶虫的幼虫或稻黑尾叶蝉的幼虫或小菜蛾的蜀。
活性化合物可转化成常规助剂,如溶液,乳剂,可湿性粉剂,悬浮液,粉剂,撒粉剂(dusting agent),糊剂,可溶性粉剂,粒剂,悬浮乳液浓缩物,浸渍有活性化合物的天然和合成物料,聚合物基料的微小胶囊。
这些制剂可用已知方法制备,例如,通过将活性化合物与增量剂混合制备,所述增量剂为液体溶剂和/或固体填料,并且其中任选地使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
在使用水作为增量剂的情况下,还可使用有机溶剂作为助溶剂。合适的液体溶剂主要有:芳烃,如二甲苯,甲苯或烷基萘,氯代芳烃和氯代脂肪烃,如氯苯,氯乙烯或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏分,矿物油和植物油,醇类,如丁醇或乙二醇以及它们的醚和酯,酮类,如丙酮,甲乙酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲亚砜,以及水。
合适的固体填料包括:
例如,铵盐和粉状天然矿物质,如高岭土,粘土,滑石,白垩,石英,活性白土,硅镁土或硅藻土,以及粉状合成物质,如细碎二氧化硅,氧化铝和硅酸盐;颗粒剂的合适固体填料有:例如粉碎并分级的天然岩石,如方解石,大理石,浮石,海泡石和白云石,以及无机和有机金属的合成粒剂,以及有机物料的颗粒如锯屑,椰子壳,玉米芯和烟草杆;合适的乳化剂和/或发泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白质水解产物;合适的分散剂有:例如木质素亚硫酸盐废液和甲基纤维素。
制剂中还可使用粘合剂如羧甲基纤维素和粉状,粒状或胶乳形式的天然和合成聚合物,如阿拉伯胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,以及合成磷脂。其它添加剂可以为矿物油和植物油。
可以使用着色剂如无机颜料,例如氧化铁,二氧化钛和普鲁士蓝,以及有机染料,如茜素染料,偶氮染料和金属酞菁染料,以及痕量营养物如铁、锰、硼、铜、钴、钼和锌的盐。
制剂一般包括0.1-95%重量活性化合物,优选0.5-90%。
本发明的活性化合物可以其市售的制剂和由这些制剂制备的作为与其它活性化合物混合的混合物形式存在。所述其它活性化合物为杀虫剂,引诱剂,灭菌剂,杀菌剂,杀螨剂,杀线虫剂,杀真菌剂,生长调节剂或除草剂。例如,杀虫剂包括磷酸酯类,氨基甲酸酯类,羧酸酯类,氯代烃类,苯脲类,微生物产生的物质等。
混合物中的特别有利的组分的实例如下:杀真菌剂:2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基嘧啶;2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧基苯基)乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)嘧啶-4-基氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP),aldimorph,氨丙磷酸,敌菌灵,戊环唑,苯霜灵,麦锈灵,苯菌灵,乐杀螨,联苯,双苯三唑醇,灭瘟素-S,糖菌唑,磺嘧菌灵,粉病定,多硫化钙,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌清,乙菌利,硫杂灵,霜脲氰,环唑醇,酯菌胺,双氯酚,苄氯三唑醇,抑菌灵,哒菌清,氯硝胺,乙霉威,噁醚唑,甲菌定,烯酰吗啉,烯唑醇,敌螨普,二苯基胺,吡菌硫,灭菌磷,二噻农,多果定,敌菌酮,克瘟散,epoxyconazole,乙菌定,氯唑灵,异嘧菌醇,fenbuconazole,呋菌胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,薯瘟锡,毒菌锡,福美铁,嘧菌腙,氟啶胺,fludioxonil,氟菌安,fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋氨丙灵,拌种胺,双胍盐,六氯苯,己唑醇,土菌消,烯菌灵,酰胺唑,双胍辛醋酸盐,异稻瘟净(IBP),异丙定,富士一号,春雷霉素,铜制剂如氢氧化铜,萘甲酸铜,氯氧化铜,硫酸铜,氧化铜,喔星铜和碱式硫酸铜混合物,锰铜混剂,代森锰锌,代森锰,嘧菌胺,灭锈胺,氨丙灵,羟菌唑,磺菌威,甲呋菌胺,代森联,噻菌胺,腈菌唑,二甲基二硫基氨基甲酸镍,间硝酞异丙酯,氟苯嘧啶醇,甲呋酰胺,噁霜灵,oxamocarb,氧化萎锈灵,稻瘟酯,戊菌唑,戊菌隆,稻病磷,四氯苯酞,多马霉素,粉病灵,福代锌,多氧霉素,噻菌灵,丙氯灵,杀菌利,百维灵,丙环唑,甲基代森锌,定菌磷,啶斑肟,pyrimethanil,咯喹酮。五氯硝基苯(PCNB),硫黄粉和硫制剂,戊唑醇,叶枯酞,四氯硝基苯,氟醚唑,涕必灵,噻菌腈,甲基托布津,福美双,甲基立枯磷,对甲抑菌灵,唑菌酮,唑菌醇,唑菌嗪,杨菌胺,三环唑,克啉菌,氟菌唑,嗪氨灵,triticonazole,有效霉素A,烯菌酮,代森锌,福美锌杀细菌剂:溴硝丙二醇,双氯酚,氯定,二甲基二硫基氨基甲酸镍,春雷霉素,异噻菌酮,呋喃羧酸,土霉素,噻菌灵,链霉素,叶枯酞,硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:齐墩螨素,AC303630,高灭磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰,虫螨脒,齐墩螨素,AZ 6054l,azadirachtin,谷硫磷A,谷硫磷M,唑环锡,苏云金杆菌,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,联苯菊酯,BPMC,brofenprox,溴硫磷A,合杀威,噻嗪酮,丁叉威,butylpyridaben,硫线磷,丙烯腈,虫螨威,三硫磷,丁硫克百威,巴丹,CGA157419,CGA184699,chloethocarb,chlorethoxyfos,毒虫畏,定虫隆,氯甲磷,毒死蜱,毒死蜱M,顺-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,溴氰菊酯,一0五九M,一0五九S,甲基一0五九,杀螨隆,二嗪农,除线磷,敌敌畏,dicliphos,百治磷,乙硫磷,氟脲杀,乐果,甲基毒虫畏,敌杀磷,乙拌磷,克瘟散,emamectin,高氰戊菊酯,苯虫威,乙硫磷,醚菊酯,唑啶草,氧嘧啶磷,克线磷,分扑萄酯,杀螨锡,杀螟松,fenobucarb,苯硫威,双氧威,甲氰菊酯,fenpyrad,唑螨酯,倍硫磷,杀灭菊酯,fironil,fluazinam,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫磷,安果,噻唑硫磷,fubfenprox,呋线威。HCH,庚虫磷,氟铃脲,噻螨酮,咪蚜胺,iprobenfos,异唑磷,丙胺磷,异丙威,异噁唑磷,ivermectin,氯氟氰菊酯,lufenuron,马拉松,灭蚜磷,速灭磷,mesulfenphos,蜗牛敌,methacrifos,甲胺磷,杀扑磷,灭虫威,灭多虫,metolcarb,milbemectin,久放磷,moxidectin,二溴磷,NC184,NI25,nitenpyram,氧化乐果,甲氨叉威,亚砜吸磷,异砜磷,一六0五A,一六0五M,氯菊酯,稻丰散,三九一一,伏杀磷,亚胺硫磷,磷胺,腈肟磷,抗蚜威,虫螨磷M,虫螨磷A,溴丙磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,打杀磷,反灭虫菊,除虫菊,哒螨酮,pyrimidifen,蚊蝇醚,喹噁磷,RH5992杀抗松,sebufos,silafluofen,硫特普,乙丙硫磷,tebufenozid,tebufenpyrad,tebupirimiphos,伏虫隆,七氟菊酯,双硫磷,叔丁威,特丁磷,杀虫畏,thiafenox,硫双灭多威,特氨叉威,甲基乙拌磷,硫磷嗪,thuringiensin,四溴菊酯,苯赛螨,三唑磷,triazuron,敌百虫,杀虫隆,trimethacarb,蚜灭多,XMC,xylylcarb,YI5301/5302,zetamethrin。除草剂:
例如,酰替苯胺类,如吡氟草胺和敌稗;芳基羧酸如二氯吡啶甲酸,麦草畏和毒莠定;芳氧基链烷羧酸如2,4-滴,2,4-滴丁酸,2,4-滴丙酸,氟草烟,2甲4氯,MCPP和绿草定;芳氧基-苯氧基-链烷羧酸酯,如氯甲草,噁唑禾草灵,吡氟禾草灵,吡氟氯禾灵和喹禾灵;azinones如杀草敏和达草灭;氨基甲酸酯类如氯苯胺灵,异苯敌草,苯敌草和苯胺灵;氯乙酰苯胺如草不绿,刈草胺,去草胺,吡草胺,丙草安,丙草胺和毒草胺;二硝基苯胺类,如黄草消,胺硝草和氟乐灵,二苯醚如三氟锁草醚,甲羧除草醚,乙羧氟草醚,氟黄胺草醚,halosafen,乳氟禾草和氟硝草醚;脲类如绿麦隆,敌草隆,伏草隆,异丙隆,利谷隆和噻唑隆;羟基胺类如枯杀达,烯草酮,噻草酮,稀禾定和肟草酮;咪唑啉酮类如咪草烟,咪草酯,灭草烟和灭草喹;腈如溴苯腈,敌草腈和碘苯腈;氧乙酰胺类如苯噻草胺,磺酰脲类如amidosulfuron,苄嘧黄隆,氯嘧黄隆,绿黄隆,醚黄隆,甲黄隆,烟嘧黄隆,氟嘧黄隆,噻黄隆,醚苯黄隆和苯黄隆;硫代氨基甲酸酯类,例如苏达灭,草灭特,燕麦敌,EPTC,禾草畏,草达灭,苄草丹,杀草丹和野麦畏;三嗪类,如阿特拉津,草津津,西玛津,西草津,去草津和特丁津;三嗪酮类,如六嗪同,苯嗪草和赛克津;其它除草剂如氨基三唑,呋草黄,噻草平,环庚草醚,异噁草酮,二氯吡啶酸,苯敌快,氟硫草定,灭草呋喃,氟咯草酮,草铵膦,草甘膦,isoxaben,达草止,二氯喹啉酸,喹草酸草甘膦盐和灭草环。
此外,本发明的活性化合物可以其市售制剂和由这些制剂制备的作为与增效剂混合的混合物形式存在。增效剂为能增加活性化合物活性的化合物,但所加入的增效剂本身不一定具有活性。
由其市售制剂制备的使用形式中的活性化合物的含量可在较宽范围内变化。使用形式中的活性化合物的浓度为0.0000001-95wt%活性化合物,优选0.0001-1wt%。
化合物可以适合于使用形式的常规方式使用。
当用于防治卫生害虫和贮藏产品的害虫时,活性化合物表现出对木头和粘土具有优越的残留作用,以及对石灰基质的碱性具有良好的稳定性。
室温下,在高压釜中,用干燥氯化氢气体饱和3g(7.7mmol)N-[吗啉-4-基-(4-叔丁基苯基)-甲基]-2,6-二氟苯甲酰胺的20ml无水二氯甲烷溶液和25ml(25mmol)氯化钛溶液(1M二氯甲烷溶液)。随后在大约0℃下,通入乙烯大约20至30分钟,其后将混合物在70℃和大约14巴内部压力下搅拌24小时,接着将反应混合物与大约100ml冰水一起搅拌,并在0℃下用氢氧化钠溶液调节成碱性,用二氯甲烷重复提取。合并的有机相用硫酸镁干燥并浓缩。油状残留物用色谱法提纯。
得到0.83g(理论值的32.5%)4-(4-叔丁基苯基)-2-(2,6-二氟苯基)-5,6-二氢-4H-1,3-噁嗪。
50℃下,将3.5g(20mmol)2-氯-6-氟苯甲酰胺与3.4g(21mmol)4-叔丁基苯甲醛和2.1g(24mmol)吗啉在40ml二氯甲烷中一同搅拌18小时。
冷却后,反应混合物用45ml氯化钛(Ⅳ)(1M二氯甲烷溶液)处理,并在高压釜中于室温下用干燥氯化氢气体饱和。随后在大约0℃下通入乙烯大约20至30分钟,其后在70℃和大约14巴内部压力下搅拌混合物24小时。接着将反应混合物与大约150ml冰水一起搅拌,并在0℃下用氢氧化钠溶液调节成碱性,用二氯甲烷重复提取。合并的有机相用硫酸镁干燥并浓缩。油状残留物用色谱法提纯。
得到1.38g(理论值的30%)4-(4-叔丁基苯基)-2-(2-氯-6-氟苯基)-5,6-二氢-4H-1,3-噁嗪,logP等于4.71。
按照实施例1和2的方法并类似一般的方法说明,可得到下列通式(Ⅰ)的化合物:表1(表1续)(表1续)表2
(表2续)(表2续)
(表2续)(表2续)表3
(表3续)(表3续)(表3续)(表3续)(表3续)(表3续)(表3续)
(表3续)(表3续)(表3续)(表3续)(表3续)(表3续)(表3续)(表3续)(表3续)(表3续)(表3续)(表3续) (表3续)
(表3续)实施例555下表中使用了下列缩写词:Me=甲基Et=乙基Pr=丙基Bu=丁基Pen=戊基Ph=苯基表4 式(Ⅱa)起始物质的制备实施例(Ⅱa-1)
实施例 | Ym | Xn |
343536373839404142434445464748495051525354 | 2,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2,6-F2 | 4-ClH4-OCH34-O-CH-(CH3)24-O-C8H17(n)2-Cl3-Cl2,6-Cl22,4-Cl22,4,5-Cl3H4-Cl4-OCH34-O-CH-(CH3)24-O-C8H17(n)2-Cl3-Cl2,6-Cl22,4-Cl22,4,5-Cl34-F |
实施例 | Ym | Xn |
84858687888990919293949596979899100101102103104105106107108109110111112113 | 2,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F22,6-F2 | 2,5-Cl22,6-F22-F,4-Cl2-Cl,4-Br2-Br,4-F2-Br,6-F2-Br,4-Cl2-Cl,3-F2-Cl,3-Br2-Cl,3-CH32-Cl,4-OEt2-Cl,4-CH32-Cl,3-OPh2-Cl,3-t-butyl2-F,3-Cl2-Br,3-Cl3-Br,4-Cl2-Cl,4-CF32-Cl,4-t-butyl2-Cl,4-OCH2CF32-Br,4-OEt2-F,4-t-butyl2,4-(CH3)22,3-(CH3)23-Br,4-OEt2-OEt,4-Cl2-OEt,4-t-butyl2-OEt,5-Cl2-OEt,5-Br2-OCH2-C2H5,5-Br |
实施例 | Ra | Rb | (Rc)q |
150151152153154155156157158159160161162163164165166167168169170 | HHFClClHFClFClHFClFClFFFFFCl | FClFFClClFFFFClFFFFFFFFFF | HHHHH2-F2-F2-F3-F3-F4-F4-F4-F2-F,4-F2-F,4-F2-F,4-Cl2-F,4-(CH2)4CH32-F,4-(CH2)5CH32-F,4-(CH2)6CH32-F,4-(CH2)7CH32-F,4-(CH2)7CH3 |
实施例 | Ra | Rb | (Rc)q |
302303304305306307308309310311312313314315316317318319320321322323324325 | FFFHFHClClFFFFFFFFFClFFFFClF | FFFClFFFClFFFFFFFFFFFFFFFF | 3-CH2CH(CH3)24-CH2CH(CH3)24-CH(CH3)CH2CH23-C(CH3)33-C(CH3)34-C(CH3)34-C(CH3)34-C(CH3)33-(CH2)4CH34-(CH2)4CH33-(CH2)2CH(CH3)24-(CH2)2CH(CH3)23-C(CH3)2CH2CH34-C(CH3)2CH2CH33-CH2C(CH3)34-CH2C(CH3)33-(CH2)5CH33-(CH2)5CH34-(CH2)5CH33-(CH2)3CH(CH3)24-(CH2)3CH(CH3)23-(CH2)6CH33-(CH2)6CH34-(CH2)6CH3 |
实施例 | Ra | Rb | (Rc)q |
526527528539530531532533534535536537538539540541542543544 | ClClFFFClClFFFFFClFFFClFF | ClFFFFFFFFFFFFFFFFFF | 3-Cl,4-OCH2CH3,5-Cl2-OCH2CF3,4-Cl,5-Cl2-OCH2CH3,4-Cl,5-Br2-OCH2CH2CH3,4-Cl,5-Br2-OCH2CH2CH3,4-Cl,5-CH2CH32-OCH2CH2CH3,4-Cl,5-CH2CH33-CH2CH3,4-Cl,5-CH2CH32-OCH3,4-CH3,5-Cl2-OCH2CH3,3-CH3,5-Cl2-CH3,4-CH3,5-CH33-CH3,4-OCH(CH3)2,5-CH33-CH3,4-O(CH2)2CH(CH3)2,5-CH33-CH3,4-O(CH2)2CH(CH3)2,5-CH32-OCH3,3-C(CH3)3,5-CH32-CH3,3-CH3,4-CH3,5-CH32-OCH3,3-CH(CH3)2,5-CH2CH33-C(CH3)3,4-OCH3,5-C(CH3)32-F,4-(CH2)6CH3,6-F2-Cl,3-F,5-F |
将13.6g(84mmol)4-叔丁基苯甲醛和8.5g(97.7mmol)吗啉加到12.8g(81.5mmol)2,6-二氟苯甲酰胺的100ml无水甲醇溶液中,在大约40-50℃下搅拌反应混合物24小时。其后与大约100ml冰水一同搅拌,抽滤出沉淀,水洗并干燥。
将3.5g(20mmol)2-氯-6-氟苯甲酰胺与3.4g(21mmol)4-叔丁基苯甲醛和2.1g(24.1mmol)吗啉在30ml甲醇中于50℃下一起搅拌18小时。冷却后,将反应混合物与100ml冰水一同搅拌,抽滤出所形成的沉淀,水洗并干燥。
得到6.3g(理论值的77.4%)N-[吗啉-4-基-(4-叔丁基苯基)-甲基]-2-氯-6-氟-苯甲酰胺,熔点180-181℃。
按照实施例(Ⅱa-1)和(Ⅱa-2)的方法并类似一般的制备说明,制得下列式(Ⅱa)起始物质。表A 表A(续)表A(续)用途实施例实施例菜蛾试验溶剂: 7份重量的二甲基甲酰胺乳化剂: 1份重量的烷芳基聚乙二醇醚
为制备活性化合物的合适制剂,将1份重量的活性化合物与所述量的溶剂和所述量的乳化剂混合,并用水稀释浓缩物至所需浓度。
通过将甘蓝叶(Brassica oleracea)浸入到所希望浓度的活性化合物的制剂中进行处理,并用小菜蛾(Plutella maculipennis)的蜀感染,同时叶子仍然保持湿润。
在指定的时间后,测定杀灭程度(%)。100%表示所有的蜀都被杀死;0%表示没有一个蜀被杀死。
在此试验中,7天后,实施例Ⅱa-5的化合物在示范性的0.1%的活性化合物浓度下能引起100%杀灭。
Claims (6)
其中:
A代表苯基,它被选自卤素、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6卤代烷硫基、硝基、氰基或苯基的相同或不同取代基单取代至五取代,其中的苯基取代基本身则又任选地被选自卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基和C1-C6卤代烷硫基的相同或不同取代基单取代至五取代,或
代表萘基,它任选地被选自卤素、C1-C6烷基、C1-C6烷氧基和C1-C6卤代烷氧基的相同或不同取代基单取代至三取代,或
代表吡啶基,它任选地被选自卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基和氰基的相同或不同取代基单取代至三取代,或
代表噻吩基,它任选地被选自卤素和C1-C6烷基的相同或不同取代基单取代至三取代,或
代表吡唑基,它任选地被选自卤素和C1-C3烷基的相同不同取代基单取代至三取代;和B代表氢、C1-C6烷基、C1-C6烷氧基-C1-C6烷基、C1-C6烷硫基-C1-C6烷基、C1-C6卤代烷基和C2-C6链烯基,或
代表C3-C7环烷基,它任选地被选自卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基和C1-C6卤代烷氧基的相同或不同取代基单取代至五取代,或
代表吡啶基,它任选地被选自卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基和氰基的相同或不同取代基单取代至三取代,或
代表α-吡咯基或β-吡咯基,它们各自任选地被选自卤素和C1-C4烷基的相同或不同取代基单取代或二取代,或
代表被羟基、CHO、氰基、羧基、多-C1-C8烷氧基-C1-C8烷基或C1-C8烷氧基羰基取代的苯基,或
代表苯基、苄基、苯乙-1-基、苯乙-2-基、苯氧基甲基、苯硫基甲基、苯硫基乙-1-基、苯氧基乙-1-基、苯氧基乙-2-基或苯乙烯基,它们各自任选地被相同或不同的取代基在苯环上单取代至五取代,在每种情况下的适宜取代基为:
卤素、
C1-C18烷基、
C1-C8烷氧基-C1-C8烷基、
C1-C8卤代烷氧基、
C1-C4卤代烷基、
C1-C18烷氧基,它任选地被另外1至3个氧原子间断、
C1-C18烷硫基、
C1-C8卤代烷硫基、
三-(C1-C8)烷基甲硅烷基、
苯基-二-(C1-C8)烷基甲硅烷基、
3、4-二氟亚甲二氧基、
3、4-四氟亚乙二氧基、
稠合苯并基团、
稠合C3-C4亚烷基,
任选地被卤素、C1-C4烷基或C3-C6环烷基取代的苄基亚氨基氧基甲基,
环己基或环己基氧基,它们各自任选地被C1-C6烷基、C1-C6烷氧基、环己基或苯基取代,
吡啶氧基,它任选地被选自卤素、C1-C4烷基和C1-C4卤代烷基的相同或不同取代基单取代或二取代、
苯基、苯基-C1-C6烷基、苯氧基、苯硫基、苯基-C1-C6烷氧基或苄硫基,它们各自任选地被选自卤素、C1-C12烷基、C1-C4卤代烷基、C1-C12烷氧基、C1-C6卤代烷氧基、C1-C6烷氧基-C1-C6烷基、C1-C6烷氧基-乙烯氧基、C1-C6烷硫基和C1-C6卤代烷硫基的相同或不同取代基单取代至五取代,其特征是:在氯化氢气体和催化剂存在下,如果合适的话在稀释剂存在下,使式(Ⅱ)酰胺衍生物与乙烯反应,
其中:
A和B的定义同上,和
R1和R2相同或不同,代表C1-C4烷基,或者与它们所键连的N原子一起代表5-或6-元杂环,所述杂环任选地被相同或不同取代基单取代至五取代,并且任选含有一个或两个另外的杂原子,取代基是C1-C4烷基和C1-C4烷氧基。
3.杀虫剂组合物,其特征是它们包括至少一种权利要求2的式(Ⅰb)化合物。
4.权利要求2的式(Ⅰb)化合物在杀灭害虫方面的应用。
5.杀灭害虫的方法,其特征是使权利要求2的式(Ⅰb)化合物作用于害虫和/或它们的环境。
6.权利要求2的式(Ⅰb)化合物在制备杀虫剂组合物方面的应用。
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DE19518681A DE19518681A1 (de) | 1995-05-22 | 1995-05-22 | Verfahren zur Herstellung von 5,6-Dihydro-1,3-oxazinen |
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WO2012177896A1 (en) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
PE20140868A1 (es) | 2011-06-24 | 2014-07-18 | Amgen Inc | Antagonistas trpm8 y su uso en tratamientos |
US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
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EP0394850A1 (de) * | 1989-04-28 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 5,6-Dihydro-4H-1,3-oxazinen |
WO1993022296A1 (de) * | 1992-05-04 | 1993-11-11 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von substituierten oxazolinen und/oder oxazinen |
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DE1545671A1 (de) * | 1965-05-05 | 1969-08-07 | Huels Chemische Werke Ag | Verfahren zur Herstellung von 4H-5,6-Dihydro-1,3-oxazinen |
DE1670475A1 (de) * | 1967-09-29 | 1971-01-28 | Huels Chemische Werke Ag | Verfahren zur Herstellung von in 4-Stellung substituierten 4H-5,6-Dihydro-1,3-oxazinen |
DE2049160C3 (de) * | 1970-10-07 | 1980-01-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 4,4-Dimethyl-5,6-dihydro-13-oxazinen |
EP0675115A1 (en) * | 1992-12-25 | 1995-10-04 | Nippon Soda Co., Ltd. | Heterocyclic derivative and pest control agent |
US5538967A (en) * | 1995-01-18 | 1996-07-23 | E. I. Du Pont De Nemours And Company | Arthropodicidal oxazines and thiazines |
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EP0394850A1 (de) * | 1989-04-28 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 5,6-Dihydro-4H-1,3-oxazinen |
WO1993022296A1 (de) * | 1992-05-04 | 1993-11-11 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von substituierten oxazolinen und/oder oxazinen |
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