CN1494549A - 具有杀虫特性的4"-位取代的阿凡曼菌素 - Google Patents
具有杀虫特性的4"-位取代的阿凡曼菌素 Download PDFInfo
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- CN1494549A CN1494549A CNA028057694A CN02805769A CN1494549A CN 1494549 A CN1494549 A CN 1494549A CN A028057694 A CNA028057694 A CN A028057694A CN 02805769 A CN02805769 A CN 02805769A CN 1494549 A CN1494549 A CN 1494549A
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- Prior art keywords
- alkyl
- formula
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- halogenated
- alkoxy
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- 239000005660 Abamectin Substances 0.000 title description 90
- 230000000361 pesticidal effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- -1 n-octyl Chemical group 0.000 claims abstract description 89
- 239000000203 mixture Substances 0.000 claims abstract description 71
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 27
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 241000238631 Hexapoda Species 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 241000607479 Yersinia pestis Species 0.000 claims description 15
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 10
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 6
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 6
- 230000001850 reproductive effect Effects 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 3
- SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical compound [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 239000003905 agrochemical Substances 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 239000002904 solvent Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 239000002585 base Substances 0.000 description 35
- 239000012074 organic phase Substances 0.000 description 32
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 23
- 239000012071 phase Substances 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- 230000000694 effects Effects 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- 238000010898 silica gel chromatography Methods 0.000 description 15
- 238000010025 steaming Methods 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- 239000011737 fluorine Substances 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- 230000000996 additive effect Effects 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000012752 auxiliary agent Substances 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
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- 150000002170 ethers Chemical class 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- 241000244206 Nematoda Species 0.000 description 6
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- 239000003999 initiator Substances 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
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- 125000000335 thiazolyl group Chemical group 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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- 238000010189 synthetic method Methods 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
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- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 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
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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
- 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 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
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N47/14—Di-thio analogues thereof
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- A—HUMAN NECESSITIES
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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- A—HUMAN NECESSITIES
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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Abstract
本发明涉及式(I)所示化合物,式中R1为C1-C12烷基,C3-C8环烷基或C2-C12链烯基;R2为H,未取代或一至五取代的C1-C12烷基或未取代或一至五取代的C1-C12链烯基;R3为C2-C12烷基,一至五取代的C1-C12烷基,未取代或一至五取代的C1-C6烷氧基-C1-C6烷基,未取代或一至五取代的C3-C12环烷基,C2-C12链烯基,C2-C12炔基;或R2和R3共同为亚烷基桥或亚烯基桥;上述定义的限制条件是,如果R2为H,R3为2-羟乙基,异丙基,正辛基或苄基则R1不是仲丁基或异丙基,或者,在适当的情况下为其E/Z异构体,E/Z异构体混合物和/或互变异构体;本发明还涉及上述化合物及其互变异构体的制备和使用方法,其活性化合物选自这些化合物和它们的互变异构体的农药以及这些化合物和组合物的制备方法及其应用。
Description
本发明涉及(1)下式所示化合物
式中
R1为C1-C12烷基,C3-C8环烷基或C2-C12链烯基;
R2为H,未取代或一至五取代的C1-C12烷基或未取代或一至五取代的C2-C12链烯基;
R3为C2-C12烷基,一至五取代的C1-C12烷基,未取代或一至五取代的C3-C12环烷基,未取代或一至五取代的C1-C6烷氧基-C1-C6烷基,未取代或一至五取代的C2-C12链烯基,未取代或一至五取代的C2-C12炔基;或
R2和R3共同为三至七员的亚烷基桥或四至七员的亚烯基桥,其中CH2基团可被O,S或NR4取代;
上述提到的烷基,烷氧烷基,链烯基,炔基,亚烷基,亚烯基和环烷基的取代基选自OH,卤素,卤素-C1-C2烷基,CN,SCN,NO2,C2-C6炔基,未取代或被一至三个甲基取代的C3-C8环烷基,降冰片烯基,未取代或被一至三个甲基取代的C3-C8环烯基;C3-C8卤代环烷基,C1-C12烷氧基,C3-C8环烷氧基,C1-C12烷硫基,C3-C8环烷硫基,C1-C12卤代烷硫基,C1-C12烷基亚磺酰基,C3-C8环烷基亚磺酰基,C1-C12卤代烷基亚磺酰基,C3-C8卤代烷基亚磺酰基,C1-C12烷基磺酰基,C3-C8环烷基磺酰基,C1-C12卤代烷基磺酰基,C3-C8卤代环烷基磺酰基,C2-C8链烯基,C2-C8炔基,-N(R8)2,此处两个R8分别是-C(=O)R5,-O-C(=O)R6,-NHC(=O)R5,-S-C(=S)R6,-P(=O)(OC1-C6烷基)2,-S(=O)2R9,-NH-S(=O)2R9,-OC(=O)-C1-C6烷基-S(=O)2R9;
芳基,苄基,杂环基,芳氧基,苄氧基,杂环氧基,芳硫基,苄硫基,杂环硫基,以及根据环上取代的可能性,这些芳基,杂环基,芳氧基,苄氧基,杂环氧基,芳硫基,苄硫基或杂环硫基可以被一至五取代的,取代基选自OH,卤素,CN,NO2,C1-C12烷基,C3-C8环烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C12烷硫基,C1-C12卤代烷硫基,C1-C6烷氧基-C1-C6烷基,二甲氨基-C1-C6烷氧基,C2-C8链烯基,C2-C8炔基,苯氧基,苯基-C1-C6烷基,亚甲基二氧基,-C(=O)R5,-O-C(=O)R6,-NH-C(=O)R6,-N(R8)2,式中两个R8可以各不相同;C1-C6烷基亚磺酰基,C3-C8环烷基亚磺酰基,C1-C6卤代烷基亚磺酰基,C3-C8卤代环烷基亚磺酰基,C1-C6烷基磺酰基,C3-C8环烷基磺酰基,C1-C6卤代烷基磺酰基和C3-C8卤代环烷基磺酰基;
R4为H,C1-C8烷基,羟基-C1-C8烷基,C3-C8环烷基,C2-C8链烯基,C2-C8炔基,苯基,苄基,-C(=O)R5,或-CH2-C(=O)-R5;
R5为H,OH,SH,-N(R8)2,式中两个R8可以不相同;C1-C24烷基,C2-C12链烯基,C1-C8羟基烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C6烷氧基-C1-C6烷基,C1-C6烷氧基-C1-C6烷氧基,C1-C6烷氧基-C1-C6烷氧基-C1-C6烷基,C1-C12烷硫基,C2-C8链烯基氧基,C2-C8炔基氧基,NH-C1-C6烷基-C(=O)R7,-N(C1-C6烷基)-C1-C6烷基-C(=O)-R7,-O-C1-C2烷基-C(=O)R7,-C1-C6烷基-S(=O)2R9,芳基,苄基,杂环基,芳氧基,苄基氧基,杂环氧基;或者为环上未取代或分别被卤素,硝基,C1-C6烷基,C1-C6烷氧基,C1-C6卤代烷基或C1-C6卤代烷氧基一至三取代的芳基,苄基,杂环基,芳氧基,苄氧基或杂环氧基;
R6为H,C1-C24烷基,C1-C12卤代烷基,C1-C12羟基烷基,C2-C8链烯基,C2-C8炔基,C1-C6烷氧基-C1-C6烷基,(NR8)2,式中两个R8可以互不相同;-C1-C6烷基-C(=O)R8,-C1-C6烷基-S(=O)2R9,芳基,苄基,杂环基;或者根据环上取代的可能性,被OH,卤素,CN,NO2,C1-C12烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C12烷硫基和,C1-C12卤代烷硫基一至三取代的芳基,苄基或杂环基;
R7为H,OH,由OH,或-S(=O)2-C1-C6烷基选择性取代的C1-C-24烷基,C1-C12链烯基,C1-C12炔基,C1-C12烷氧基,C1-C6烷氧基-C1-C6烷基,C1-C6烷氧基-C1-C6烷氧基,C2-C8链烯基氧基,芳基,芳氧基,苄氧基,杂环基,杂环氧基或-N(R8)2,式中两个R8可以互不相同;
R8为H,由一至五个选自卤素,C1-C6烷氧基,羟基和氰基选择性取代的C1-C6烷基,C1-C8环烷基,芳基,苄基,杂芳基;或根据环上取代的可能性由选自OH,卤素,CN,NO2,C1-C12烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C12烷硫基和C1-C12卤代烷硫基一至三取代的芳基,苄基或杂芳基;
R9为H,由一至五个选自卤素,C1-C6烷氧基,羟基和氰基选择性取代的C1-C6烷基;芳基,苄基,杂芳基;或根据环上取代的可能性由选自OH,卤素,CN,NO2,C1-C12烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C12烷硫基和C1-C12卤代烷硫基一至三取代的芳基,苄基或杂芳基;
上述定义的限制条件是如果R2为H和R3为2-羟基乙基,异丙基,正辛基或苄基则R1不是仲丁基或异丙基;
或者如果适当的话,式(I)也表示为E/Z异构体,E/Z异构体混合物和/或互变异构体;
本发明还涉及上述化合物,它们的异构体和互变异构体的制备过程,以及上述化合物,它们的异构体和互变异构体的应用;选自这些化合物和它们的互变异构体作为活性化合物的农药;以及应用这些组合物防治害虫的方法。
文献提议某些大环内酯化合物用于防治害虫。然而,这些已知化合物的生物特性并不是完全令人满意的,因此,仍然需要提供具有杀虫特性,特别是用于防治害虫和蜱螨目的代表虫种的其它化合物本发明提供的式(I)所示的化合物达到了这一目的。
本发明要求保护的化合物是阿凡曼菌素的衍生物,对于那些技术熟练的人来说阿凡曼菌素是已知的。它们是一组结构相近具有农药活性的化合物,通过一株除虫链霉菌(Streptomyces avermitilis)发酵而获得。阿凡曼菌素的衍生物也可由方便的化学合成获得。
由除虫链霉菌(Streptomyces avermitilis)获得的阿凡曼菌素称为Ala,Alb,A2a,A2b,Bla,Blb,B2a,B2b,称作“A”和“B”的化合物在5一位上分别连有一个甲氧基和OH基,“a”系列和“b”系列化合物在25-位的取代基R1分别是仲丁基和异丙基。在化合物中的名称中数字1意指22和23位上的原子是由双键连接起来的;数字2意指它们是由单键连接起来的,且23-位碳原子上带有一个OH基。在本发明的叙述中,上述命名法表示,在本发明的非天然存在的阿凡曼菌素衍生物中,其的特定结构类型相应于天然存在的阿凡曼菌素。本发明要求保护的是B1系列化合物的衍生物,特别是阿凡曼菌素Bla和阿凡曼菌素Blb的衍生物的混合物。
式(I)所示的一些化合物能产生互变异构体,因而在本发明的叙述中,如果适当的话,式(I)所示化合物也应理解为包括了相应的互变异构体,即使在各种例子中未特别提到也应如此理解。
除非另外定义,本发明上下文中采用的一般术语的含义如下:
除非另外定义,在每种情况下含碳基团和含碳化合物都含有1至6个碳原子,优选1至4个碳原子,特别优选1或2个碳原子。
卤素,自身作为一个基团以及作为其它基团和化合物如卤代烷基,卤代烷氧基和卤代烷硫基的结构元素,是指氟,氯,溴或碘,优选氟,氯或溴,特别优选氟或氯。
烷基,自身作为一个基团以及作为其它基团和化合物如卤代烷基,烷氧基和烷硫基的结构元素,是指直链的甲基,乙基,丙基,丁基,式基,己基,庚基或辛基,或者指支链的烷基如异丙基,异丁基,仲丁基,叔丁基,异戊基,新戊基或异己基。在各种情况下考虑的都是基团或所叙及的化合物所含的碳原子数。
环烷基,自身作为一个基团以及作为其它基团和化合物如卤代环烷基,环烷基氧基,环烷基硫基,是指环丙基,环丁基,环戊基,环己基,环庚基或环辛基,在各种情况下考虑的都是基团或所叙及的化合物所含的碳原子数。
链烯基,自身作为一个基团以及作为其它基团和化合物的结构元素,是指直链基团如乙烯基,烯丙基,2-丁烯基,3-戊烯基,1-己烯基,1-庚烯基,1,3-己二烯基,1,3-辛二烯基,或者是指支链基团,如异丙烯基,异丁烯基,异戊二烯基,叔戊烯基,异己烯基,异庚烯基,或异辛烯基。在各种情况下考虑的都是基团所具有的碳原子数以及共轭或孤立的双键,优选具有3至12个碳的链烯基,更优选3至6个碳特别是3或4个碳的链烯基。
炔基,自身作为一个基团以及作为其它基团和化合物的结构元素,是指直链基团如乙炔基,丙炔基,2-丁炔基,3-戊炔基,1-己炔基,1-庚炔基,3-己烯-1-炔基,或1.5-庚二烯-3-炔基,或者指支链基团如3-甲基丁-1-炔基,4-乙基戊炔-1-基,4-甲基己-2-炔基,或2-甲基庚炔-3-基,在各种情况下考虑的都是基团或涉及的化合物的碳原子数和共轭或孤立的双键。优选具有3至12个碳的炔基,更优选3至6个碳特别是3或4个碳的炔基。
亚烷基和亚烯基是指直链的或支链的桥联部分,特别是指-CH2CH2CH2-,-CH2CH2CH2CH2-,-CH2CH2CH2CH2CH2-,-CH2(CH3)CH2CH2-,-CH2C(CH3)2CH2-,-CH2CH=CHCH2-,或-CH2CH=CHCH2CH2-。
卤素取代的含碳基团如卤素取代的烷基,链烯基,炔基,环烷基,烷氧基或烷硫基,可以是部分卤代的或全卤代的,其中多卤代时,卤素取代基可以相同也可以不同。卤代烷基自身作为一个取代基以及作为其它基团和化合物如卤代烷氧基或卤代烷硫基的结构元素的例子是被氟,氯和/或溴一至三取代的甲基,如CHF2或CF3;被氟,氯和/或溴一至五取代的乙基,如CH2CF3,CF2CF3,CF2CCl3,CF2CHCl2,CF2CHF2,CF2CFCl2,CF2CHBr2,CF2CHClF1,CF2CHBrF,或CClFCHClF;被氟,氯和/或溴一至七取代的丙基或异丙基,如
CH2CHBrCH2Br,CF2CHFCF3,CH2CF2CF3,或CH(CF3)2;被氟,氯和/或溴一至九取代的丁基或其异构体之一,为CF(CF3)CHFCF3或CH2(CF2)2CF3;被氟,氯和/或溴一至十一取代的戊基或其异构体之一,如CF(CF3)(CHF2)CF3或CH2(CF2)3CF3;以及被氟,氯和/或溴一至十三取代的己基或其异构体之一,如
(CH2)4CHBCH2Br,CF2(CHF)4CF3,CH2(CF2)4CF3或
C(CF3)2(CHF)2CF3。
芳基特指苯基,萘基,蒽基,菲基,苝基或芴基,优选苯基。
杂环基应理解为三至七员单环,可以是饱和的或不饱和的,并且含有1至3个杂原子,选自由N,O和S组成的基团;或者是8至14个原子组成的双环体系,它们可以是饱和的或不饱和的,可以在一个环上或在两个环上分别含有N,O和S中的一或两个杂原子。
优选的杂环基有,经一个碳原子而相连接的哌啶基,哌嗪基,氧杂环丙烷基,吗啉基,硫杂吗啉基,吡啶基,N-氧化吡啶基,嘧啶基,吡嗪基,均-三嗪基,1,2,4一三嗪基,噻吩基,噻吩基,呋喃基,二氢呋喃基,四氢呋喃基,吡喃基,四氢吡喃基,吡咯基,吡咯啉基,吡咯烷基,吡唑基,咪唑基,咪唑啉基,噻唑基,异噻唑基,三唑基,恶唑基,噻二唑基,噻唑啉基,噻唑烷基,恶二唑基,苯二甲酰亚氨基,苯并噻吩基,喹啉基,喹喔啉基,苯并呋喃基,苯并味唑基,苯并吡咯基,苯并噻唑基,二氢吲哚基,异二氢吲哚基,苯并吡喃酮基,吲唑基,硫杂萘基,苯并呋喃基,喋啶基或嘌呤基,以及噻吩基,苯并呋喃基,苯并噻唑基,四氢吡喃基或吲哚基;特别优选吡啶基和噻唑基。这里涉及的杂环基优选没有取代的,或者-取决于在环系上取代的可能性-可以由1至3个取代基取代,这些取代基包括卤素,=O,-OH,=S,SH,硝基,C1-C6烷基,C1-C6羟基烷基,C1-C6烷氧基,C1-C6卤代烷基,C1-C6卤代烷氧基,苯基,苄基,-C(=O)-R6和-CH2-C(=O)-R6。
在本发明叙述的内容中,优选的是:
(2)式(I)中R1为异丙基或仲丁基的(1)的化合物,优选异丙基和仲丁基呈现为混合物的那些化合物;
(3)式(I)中(2)的化合物,式中R2为H;
(4)式(I)中(2)的化合物,式中R2为C1-C8烷基,特别优选甲基;
(5)式(I)中(2)的化合物,式中R2为乙基;
(6)式(I)中(2)的化合物,式中R2为正丙基;
(7)式(I)中(1)到(6)的化合物,式中R3未被取代,或被取代,优选未被取代的C2-C5烷基;
(8)式(I)中(1)到(7)的化合物,式中R3为乙基;
(9)式(I)中(1)到(7)的化合物,式中R3为正丙基;
(10)式(I)中(2)到(7)的化合物,式中R3为异丙基;
(11)式(I)中(1)到(7)的化合物,式中R3为正丁基,仲丁基,异丁基或叔丁基;
(12)式(I)中(1)到(6)的化合物,式中R3未被取代,或被取代,优选未取代的C6-C12烷基;
(13)式(I)中(1)或(2)的化合物,式中R2和R3共同为-CH2CH2CH2-或-CH2CH2CH2CH2-;
(14)式(I)中(1)或(2)的化合物,式中R2和R3共同为-CH2CH2-O-CH2CH2-或-CH2CH2-N(CH3)-CH2CH2-;
(15)式(I)中(1)到(6)的化合物,式中R3为取代的C1-C4烷基而取代基选自OH,卤素,C3-C8环烷基,C3-C8未取代的或被一至三个甲基取代的环烯基,C1-C12烷氧基,C2-C8炔基,-C(=O)R5,-NHC(=O)R6,-P(=O)(OC1-C6烷基)2;苯基,萘基,蒽基,菲基,芴基,苝基或根据环上取代的可能性,未取代或一至五取代的杂环基;
特别优选R3的取代基选自下述基团的那些化合物:卤素,C3-C8环烷基,C2-C8炔基,-C(=O)R5,-NHC(=O)R6,-P(=O)(OC1-C6烷基)2;根据环上取代的可能性,未取代或一至三取代的苯基,萘基,蒽基,吡啶基,噻唑基,咪唑基,呋喃基,喹啉基,吡唑基;
(16)式(I)中(1)到(6)的化合物,式中R3为苯环上携有一至三个取代基的苄基,取代基选自OH,卤素,CN,NO2,
C1-C2烷基,二甲氨基-C1-C4烷氧基,C3-C6环烷基,C1-C2卤代烷基,C1-C2烷氧基,C1-C2卤代烷氧基,苯氧基,苯基-C1-C6烷基,苯基-C1-C4链烯基,未取代或氯取代,甲氧基取代或三氯甲基取代的苄氧基,亚甲基二氧基,-C(=O)R5,-O-C(=O)R6和
NHC(=O)R6;
R5为H,OH,NH2,NH(C1-C2)烷基,N(C1-C2烷基)2,-O-C1-C2烷基-C(=O)-R7,-NHC1-C2烷基-C(=O)-R7,C1-C6烷基,C1-C2烷氧基,C1-C2烷氧基-C1-C2烷氧基,C2-C4链烯基氧基,C2-C4炔基氧基,苯基,苯氧基,苄氧基,NH-苯基,NH-C1-C6烷基-C(=O)-R7;或者是被卤素,硝基,甲氧基,三氟甲基或三氟甲氧基取代的苯基,苯氧基,苄氧基,NH-苯基;
R6为H,C1-C3烷基,苯基或苄基,以及
R7为H,OH,NH2,NH(C1-C12烷基),N(C1-C12烷基)2,C1-C12烷基,C1-C12烷氧基,C1-C6烷氧基-C1-C6烷氧基,C2-C8链烯基氧基,苯基,苯氧基,苄氧基或NH-苯基;
(17)式(I)所示(1)到(6)的化合物,式中R3为
C1-C4烷基-C(=O)R5,特别是-CH2-C(=O)R5;以及
R5为H,OH,NH2,NH(C1-C2烷基),N(C1-C2烷基)2,C1-C4烷基,C1-C12烷氧基,C2-C4链烯基氧基,苯基,苯氧基,苄氧基,NH-苯基,NH-C1-C2烷基-C(=O)-O-C1-C2烷基-苯基,-P(=O)(OC1-C6烷基);或者是被氯,氟,甲氧基,三氟甲基或三氟甲氧基取代的苯基,苯氧基,苄氧基或NH-苯基;
特别是R5为C1-C12烷氧基的那些化合物;
(18)式(I)所示(1)到(6)的化合物,式中R3为
C2-C6烷基-NHC(=O)R6以及R6为H,C1-C4烷基,C2-C4链烯基,C2-C4炔基,苯基或苄基;
(19)式(I)所示(1)到(6)的化合物,式中R3为-CH2-杂环基;
优选的杂环基有吡啶基,呋喃基,四氢呋喃基,吡喃基,四氢吡喃基,吡唑基,咪唑基,噻唑基,苯并噻吩基,喹啉基,喹喔啉基,苯并呋喃基,苯并咪唑基,苯并吡咯基,苯并噻唑基,吲哚基,苯并吡喃酮基或吲唑基,上术取代基可以是未取代的或分别被卤素,三氟甲基,三氟甲氧基或硝基一或二取代;特别优选未取代的或被卤素,三氟甲基,三氟甲氧基或硝基分别一至二取代的吡啶基,呋喃基,吡唑基,咪唑基,噻唑基,苯并咪唑基,苯并吡咯基,苯并噻唑基或吲哚基;尤其是优选未取代或被卤素,三氟甲基,三氟甲氧基或硝基一至二取代的吡唑基或噻唑基,更优选被氯一取代的基团;
(20)式(I)所示(1)到(6)的化合物,式中R3为C2-C10链烯基,优选未取代或被C2-C4炔基,-C(=O)-C1-C4烷氧基,-C(=O)-C1-C4烷基-苯甲酰基,苯基或卤素一或二取代,特别是一取代的C2-C4链烯基;更优选R3为-CH2-CH=CH2的那些化合物;
(21)式(I)所示(1)到(6)的化合物,式中R3为支链未取代的C4-C10烷基;
(22)式(I)所示(1)到(6)的化合物,式中R3为支链取代的C3-C10烷基;
(23)式(I)所示(1)到(6)的化合物,式中R3为未取代的苄基;
(24)式(I)所示(1)到(6)的化合物,式中R3为-CH2CH2CN,-CH2CH2-CO-C1-C4烷基,-CH2CH2CO-苯基或-CH2CH2-CO-C1-C4烷氧基,优选-CH2CH2CN或-CH2CH2-CO-C1-C4烷氧基,特别优选CH2CH2-CN;
(25)式(I)所示(1)到(6)的化合物,式中R3为
-CH2CH2CH2-O-CO-C1-C4烷基,-CH2CH2CH2-O-CO-芳基,CH2CH2CH2-CO-C1-C4烷氧基,-CH2CH2-CO取代的C1-C4烷基,-CH2CH2-CO-取代的芳基,-CH2CH2-CO-取代的烷氧基;优选
-CH2CH2CH2-O-CO-烷基或CH2CH2CH2-O-CO-芳基,特别优选-CH2CH2CH2-O-CO-C1-C4烷基或-CH2CH2CH2-O-CO-苯基,最优选-CH2CH2CH2-O-CO-甲基;
(26)式(I)所示(1)到(6)的化合物,式中R3为-NHC(=O)R5所取代,优选R3为-(CH2)3-NHC(=O)R5;
(27)式(I)所示(1)到(6)的化合物,式中R3为
-S-C(=S)R6所取代,优选R3为-(CH2)3-S-C(=S)R6;
(28)式(I)所示(1)到(6)的化合物,式中R3为
-NH-S(=O)2R9所取代,优选R3为-(CH2)3-NH-S(=O)2R9;
(29)式(I)所示(1)到(6)的化合物,式中R3为
-OC(=O)-C1-C6烷基-S(=O)2R9所取代,优选R3为
-(CH2)3-OC(=O)-C1-C6烷基-S(=O)2R9;
(30)式(I)所示(1)到(6)的化合物,式中R3为一取代的C1-C6烷氧基-C1-C6烷基;
(31)本发明给出了优选的式(I)所示化合物,列于表中,如果适宜的话还包括它们的E/Z异构体和E/Z异构体的混合物;特别优选下述化合物
4″-脱氧-4″-表-N-乙氨基阿凡曼菌素B1;
4″-脱氧-4″-表-N-正丙基阿凡曼菌素B1;
4″-脱氧-4″-表-(N-乙基-N-甲基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(N-甲基-N-正丙基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(N-异丙基-N-甲基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(N-甲基-N-丙烯基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(N-甲基-N-乙氧碳基甲基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(N-甲基-N-苄基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(N-甲基-N-二氟甲基苯基甲基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(N-甲基-N-2.5-二氯苯基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(N-甲基-N-2.5-二氟苯基甲基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(N-甲基-N-2,3,4-三氟苯基甲基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-(1-吡咯啉基)阿凡曼菌素B1;
4″-脱氧-4″-表-(1-氮杂环丁基)阿凡曼菌素B1;
4″-脱氧-4″-表-[N-(2-羟基-2-甲基丙基)-N-甲基氨基]阿凡曼菌素B1;
4″-脱氧-4″-表-[N-(3-乙酰氧基丙基)-N-甲基氨基]阿凡曼菌素B1;
4″-脱氧-4″-表-N-(2-氰基乙基氨基)阿凡曼菌素B1;
4″-脱氧-4″-表-N-[(6-氯-3-吡啶基甲基)氨基]阿凡曼菌素B1;以及
4″-脱氧-4″-表-(N-甲基-N-[3-{2-氧代-2-苯基乙氧羰基}烯丙基]氨基)阿凡曼菌素B1;
本发明还提供了制备式(I)所示化合物的方法,而且,如果适当的话还包括了互变异构体的制备方法,具体如下
(A)为制备式(I)所示的化合物,该化合物的R1与式(I)中(1)的定义相同,R2为H而R3为R31-CH-R32,式中R32为C1-C6烷基,苯基,杂环基或取代的C1-C6烷基,苯基或杂环基而R32为H或未取代的C1-C5烷基,于是
式(I)所示的一个能由已知方法制备的已知化合物,其R1与式(I)中(1)的定义相同而R2和R3为H,该化合物在一种还原剂的存在下与化合物R31-C(=O)R32反应,式中R31和R32与前述定义相同;或
(B)为制备式(1a)所示的化合物,其中R1和R2与式(I)的(1)中的含义相同且R3与式(I)的(1)中的定义相同,H除外,使能由本身已知的方法制备的其中R1和R2与式(I)所示的定义相同且R3为H的式(1a)所示的化合物与式R3-Hal所示的化合物反应,其中R3与式(I)的(1)中的定义相同且Hal为卤素,特别是溴或碘;或
(C)为制备式(I)所示的化合物,其中R1和R2与前述式(I)的(1)中的含义相同,R3为羟基取代的-CH2-C1-C11烷基,
使式(I)所示的化合物,其中R1和R2与式(I)的(1)中的含义相同,R3为-C(=O)-R5取代的C1-C11烷基以及R5为OH或烷氧基,与一种还原剂及应;或
(D)为制备式(I)所示的化合物,其中R1和R2与前述式(I)的(1)中的含义相同,R3为COOH-取代的C1-C12烷基,
使式(I)所示的化合物,其中R1和R2与前述式(I)的(1)中的含义相同,R3为-C(=O)-R5-取代的C1-C12烷基且R5为C1-C6烷氧基或苄氧基,与一种碱或一种还原剂反应;或
(E)为制备式(I)所示的化合物,其中R1和R3与前述式(I)含(1)中的含义相同且R2为甲基,
使式(I)所示的化合物,其中R1和R3与前述式(I)的(1)中的含义相同且R2为H,与甲基-Hal反应,其中Hal是卤素,特别是溴或碘;或与甲醛在一种还原剂的存在下反应;或
(F)为制备式(I)所示的化合物,式中R1和R2与前述式(I)的(1)中的含义相同而R3为-C(=O)N(R10)2-取代的C1-C12烷基并且式中两个R10分别是H或未取代的或取代的C1-C12烷基,
使式(I)所示的化合物,式中R1和R2与前述式(I)的(1)中的含义相同,R3为-C(=O)R5-取代的C1-C12烷基而R5为OH,与式NH(R10)2所示的化合物在脱水剂的存在下反应,R10为H或未取代的或取代的C1-C12烷基;或
(G)为制备式(I)所示的化合物,式中R1和R2与前述式(I)的(1)中的定义相同而R3为羟基代的C4-C12烷基,
使式(I)所示的化合物,式中R1和R2与前述式(I)的(1)中的含义相同,R3为-C(=O)-R5-取代的C1-C5烷基以及R5为C1-C12烷氧基,与两摩尔的C1-C3烷基镁卤化物或C1-C3烷基锂试剂反应;或
(H)为制备式(I)所示的化合物,式中R1与前述式(I)的(1)中的定义相同而R2和R3同为三至七员的亚烷基桥或四至七员的亚烯基桥,其中一个CH2基团可被O,S或NR4所替代,而R4与前述式(I)的(1)中的含义相同,
使式(I)所示的化合物,式中R1与式(I)的(1)中的定义相同而R2和R3为H,与式卤素-(C3-C7亚烷基)-卤素或卤素-(C4-C7亚烯基)-卤素所示的化合物反应,卤素优选溴或碘,且式中一个CH2基团可被O,S或NR4替代,而R4与前述式(I)的(1)中的含义相同:或
(I)为制备式(I)所示的化合物,式中R1与式(I)的(1)中的含义相同而R2和R3相同,其含义与式(I)中(1)的含义相同,
使式(I)所示的化合物,其中R1与式(I)的(1)中的含义相同而R2和R3均为H,与两摩尔的式R3-卤素所示的化合物反应,R3与式(I)的含义相同,而卤素优选溴或碘;或
(J)为制备式(I)所示的化合物,式中R2和R3相同,为未取代或一至五取代的-CH2-C1-C11烷基,未取代的或一至五取代的-CH2-C1-C11链烯基或未取代或一至五取代的-CH2-C1-C11炔基,
使式(I)所示的化合物,式中R1与式(I)中(1)的含义相同而R2和R3均为H,在一种还原剂的存在下与两摩尔的式R31-CHO所示的化合物反应,其中R31为未取代或一至五取代的C1-C11烷基,未取代或一至五取代的C1-C11链烯基或未取代或一至五取代的C1-C11炔基。
上述与式(I)所示化合物的互变异构体有关的解释同样适用于上下文中就它们的互变异构体而言提到的起始物。
文中描述的反应以已知的方式进行,例如无溶剂条件下或通常在适当的溶剂,稀释剂或混合溶剂的存在下进行,如果需要反应可以在冷却下,室温或加热条件下进行,例如反应温度范围大致从-80℃到反应介质的沸腾温度,优选大约从0℃到+150℃,而且如果需要,反应还可在一个封闭的容器中,压力下,惰性气氛中和/或无水条件下进行。特别有利的反应条件可在实施例中找到。
反应时间是不严格的,优选从0.1小时到大约24小时,特别优选从大约0.5小时到大约10小时;
产物的分离用常规方法,例如可用过滤,结晶,蒸馏或层析,或者这些方法适当的结合。
文中涉及的用于制备式(I)所示化合物以及它们的已知的互变异构体的起如物可以由已知的方法制备,如下述例子的说明。
方法(A)
溶剂和稀释剂的例子包括:芳香族、脂肪族和脂环族碳氢化合物以及卤代烃,如苯,甲苯,二甲苯,1,3,5一三甲苯,四氢化萘,氯苯,二氯苯,溴苯,石油醚,己烷,氯代己烷,二氯甲烷,三氯甲烷,四氯甲烷,二氯乙烷,三氯乙烯或四氯乙稀;醚类,如二乙醚,二丙醚,二异丙醚,二丁醚,叔丁基甲基醚,乙二醇单甲醚,乙二醇单乙醚,乙二醇二甲醚,二甲氧基二乙醚,四氢呋喃或二氧六环;醇类,如甲醇,乙醇,丙醇,异丙醇,丁醇,乙二醇或丙三醇;羧酸类,如乙酸或甲酸;酰胺类,如N,N一二甲基甲酰胺,N,N一二乙基甲酰胺,N,N一二甲基乙酰胺,N-甲基吡咯烷酮或六甲基磷酰胺;腈类,如乙腈或丙腈;以及亚砜类,如二甲亚砜,以及水;或者上述溶剂的混合物;
优选醚类,醇类,水和羧酸类,特别优选四氢呋喃,乙酸或水。
有利于反应进行的温度范围为大约室温到所用溶剂的沸点,优选10到30℃。
在优选的方法A的实施例中反应在室温四氢呋喃中乙酸存在下进行,特别优选的条件在实施例P1.1中叙及到。
方法(B)
溶剂和稀释剂的例子包括:芳香族,脂肪族和脂环族碳氢化合物和卤代烃以及醚,如方法(A)所列;酮类,如丙酮,甲基乙基酮或甲基异丁基硐;醇类,如甲醇,乙醇,丙醇,异丙醇,丁醇,乙二醇或丙三醇;羧酸酯类,如乙酸甲脂,或苯甲酸酯类;酰胺类,如方法(A)所列;腈类,为乙腈或丙腈;以及亚砜类,如二甲亚砜;以及水;或者上述溶剂的混合物;
优选水,有机酸酯,卤代烃和芳香烃;特别优选水与有机溶剂形成的两相混合物。
有利于反应进行的温度范围大约从室温到所用溶剂的沸点温度,优选室温到90℃,特别优选室温到60℃,以及碱的存在有利于反应的进行,优选无机碱,如氢氧化钠,氢氧化钾,碳酸钠或碳酸氢钠。
特别优选的反应条件作为例子在实施例P1.2,P1.3,P2.1和P2.7中已被叙及。
方法(C)
溶剂和烯释剂的例子包括:方法(A)所列芳香族,脂肪族和脂环族碳氢化合物以及卤代烃和醚类,酰胺类和腈类;以及亚砜类,如二甲亚砜;或上述溶剂的混合;优选醚类和烃类。
有利于反应进行的温度范围为0℃到所使用溶剂的沸点,优选
0℃到室温。反应的最佳优选条件,作为例子在实施例P2.2中已涉及
方法(D)
适当的溶剂包括方法(A)提到的那些种类;此外还包括酮类,如丙酮,甲基乙基酮和甲基异丁基酮;以及羧酸,如乙酸或甲酸;羧酸酯,如乙酸甲酯,乙酸乙酯,或苯甲酸酯,
有利于反应进行的温度范围为大约从室温到所采用溶剂的沸点,以及反应在无机碱存在下进行,为氢氧化锂,氢氧化钠,氢氧化钾,碳酸钠或碳酸氢钠。
对于本方法最为优选的条件已在实施例P2.6中叙及。
也有可能选择一种反应类型作为上述方法的替代,在该类反应中采用一种还原剂,特别是选用分子氢作还原剂,更为优选四氢呋喃和水的混合物作为溶剂,在重金属催化剂,特别是在Pd催化剂存在下的反应。
对于本方法最佳优选条件作为例子在实施例P2.5中叙及。
方法(E)
适当的溶剂包括类型(B)提到的那些类型,优选有机酸酯,卤代烃和芳香烃,特别优选水和酯形成的两相混合物。
有利反应进行的条件是,温度以0℃到使用溶剂的沸点,优选室温到60℃,以及在碱的存在下进行,优选无机碱,氢氧化钠,氢氧化钾,碳酸钠或碳酸氢钠。
对于本方法特别优选的条件作为例子在实施例P2.3中已叙及。
在一个替代的具体实施例中,适当的溶剂包括了上述提到的溶剂,忧选醚,醇,水和羧酸与氢化物,如硼氢化钠,优选NaCNBH3的结合。
对于本方法特别优选的条件作为例子在实施例P2.4中已叙及。
方法(F)
溶剂和稀释剂的例子包括:芳香族,脂肪族和脂环族碳氢化合物以及卤代烃,方法(A)所列的醚类,酰胺类和腈类;酮类,如丙酮,甲基乙基酮或甲基异丁基酮,羧酸酯类,如乙酸甲酯,乙酸乙酯或苯甲酸酯;亚砜类,如二甲亚砜;或上述溶剂的混合物;
最佳优选的溶剂为有机酸酯类,如乙酸乙酯。
使用的脱水剂是通常的多肽偶联剂,优选碳二亚胺和羟基苯并三唑。
有利于反应进行的条件是温度范围为0℃到所用溶剂的沸点,优选室温。
反应最佳优选条件,作为例子在实施例P2.8中已叙及。
方法(G)
溶剂和稀释剂的例子包括:优选方法(A)所列的芳香族,脂肪族和脂环族碳氢化合物和醚类;以及亚砜类,如二甲亚砜,或上述溶剂的混合物,醚类,优选四氢呋喃。
有利于反应进行的温度范围为0℃到所用溶剂的沸点,优选0℃到室温。
反应的最佳优选条件,作为例子在实施例P2.10中已叙及。
方法(H)
适宜的溶剂包括类型(B)提到的那些种类,优选水,有机酸酯,卤代烃和芳香烃,特别优选上述有机溶剂和水的两相混合物。
有利于反应进行的条件为,温度范围从0℃到所用溶剂的沸点,优选90℃到所用溶剂的沸点,以及有碱的存在,优选无机碱,如氢氧化钠,氢氧化钾,碳酸钠或碳酸氢钠。
反应的最佳优选条件,作为例子在实施例P3.2中叙及。
方法(I)
适宜的溶剂包括类型(B)提到的那些种类,优选水,有机酸酯,卤代烃和芳香烃,特别优选水与上述有机溶剂的两相混合物。
有利反应进行的条件包括:温度范围从0℃到所用溶剂的沸点,优选90℃到沸点,以及有碱的存在,优选无机碱,如氢氧化钠,氢氧化钾,碳酸钠或碳酸氢钠。
反应的最佳优选条件,作为例子,在实施例P3.1中已叙及。
方法(J)
适宜的溶剂包括类型(B)提到的那些种类,优选水,有机酸酯和醇,特别优选水和醚的两相混合物。
有利反应进行的温度范围从0℃到所用溶剂的沸点,优选室温。
反应的最佳优选条件,作为例子在实施例P3.3中已叙及。
式(I)所示化合物可以是可能的异构体之一或混合物的形式,可以是纯异构体的形式或异构体混合物的形式,例如外消旋混合物的形式;如果在各种例子中未提及立体化学的细节,按照上下文的内容,可解释为本发明既涉及了纯的异构体,也涉及了外消施混合物。
消旋体能够由已知的方法解析为光活性对映体,这些方法包括:在光活性溶剂中重结晶,在手性吸附剂上层析,例如在乙酰纤维素上进行高压液相层析,借助适当的微生物的帮助,用特异性固定化酶进行拆分,经过包合物的形成,例如手性冠醚只与一种异构体产生复合物。
除相应异构体混合物的分离外,本发明也可以由通常已知的对映选择性合成方法获得纯的光学异构体,例如采用有相应适当立体化学的起始物按本发明方法进行的合成。
在单一组份有不同的生物活性时,在各种情况下无论是分离还是合成都是有利于生物活性更好的异构体。
式(I)所示化合物也可以它们的水合物的形式和/或包合其它溶剂的形式而获得,例如可以包合用于固体形式化合物结晶的溶剂。
本发明叙及了所有过程的实施例,根据这些实施例一个可以作为起始物或过程任何阶段的中间体的化合物可以用作起始物,根据这些实施例一些或全部步骤都可以进行或者以衍生物的形式或其消旋体或对映体形式应用的起始物均可在反应条件下形成。
在本发明的那些方法中,优选采用那些在形成式(I)所示化合物时最佳优选得到的起始物和中间体。
本发明特别涉及到在实施例P1.1到P4.3所描述的制备过程。
在害虫防治领域本发明所叙及的式(I)所示的化合物显示有价值的预防和治疗活性的活性成份,具有非常有利的杀虫谱和很宽的活性谱,甚至在很低的浓度下也是如此,而温血动物,鱼和植物对其却有很好的耐药性。令人惊奇的是它们同样适用于防治植物害虫和人类的体内外寄生虫以及牲畜,家养动物和宠物的体内外寄生虫。它们对正常敏感动物害虫的各个发育阶段有效,而且对具有抗性的动物害虫如昆虫和蜱螨,线虫,条虫和金龟等的代表性害虫也是有效的。同时还能保护有益生物。本发明叙及的活性成分的杀虫杀螨活性可以直接显示出来,也就是说,害虫的死亡率可以立即发生或者在一定时间之后发生例如脱皮,或者可以间接地显示其杀虫杀螨活性,例如在减少产卵和/或孵化率方面活性良好,相当于至少百分之50到60的死亡率。
所说的动物害虫包括,例如欧洲专利申请EP-A-736252,第5页第55行至第6页第55行提到的那些害虫。因而这些害虫也包括在本发明之中。
使用本发明的化合物来防治线虫也是可能的,这些害虫包括,例如
根疣线虫禽,胞囊线虫属和茎叶线虫属;特别是异皮线虫,如Heterodera schachtii,Heferodora avenae和Heterodera trifvlii;Globoderaspp,如Globodera rostochiensis;根瘤线虫,如Meloidogyneincognifa和Meloidogyne javawica;Radopholus spp,如Radopholus simiis;Pratylenchus,如Pratylenchus neglecfelns和Pratylenchus Penefrans;Tylenchulus,如Tylenchulus semipenetrans;Longidorus,Trichodorus,Xiphinema,Ditylenchus,Apheenchoides和Anguina;insbesondere Meloidogyne,如Meloidogyne incognita,以及Heferodera,如Heferodera glycines。
本发明的一个特别重要方面是在植物保护中用于防治寄生的取食害虫。
本发明的化合物用于防治,也就是说用于抑制或消灭前面提到的存在于植物上的各种类型的害虫,特别是存在于农业,园艺和森林中的有用植物和观赏植物上的害虫,或存在于这些植物的某些部位,如果实,花,叶,茎,炔茎或根上的害虫,而且在某些情况下生长后期的这些植物部位仍能被保护不被这些害虫侵害。
目标作物重点包括:谷类作物,如小麦,大麦,黑麦,燕麦,水稻,玉米和高梁;甜菜类,如甜菜和饲料甜菜;水果类,包括梨果类,核果类和无核水果类,如苹果,梨,李子,桃,杏,樱桃和浆果类,如草莓,木莓和黑莓;豆科类植物,如蚕豆,扁豆,豌豆和大豆;油料作物,如油菜,芥菜,罂栗,橄榄,向日葵,椰子,蓖麻,可可和落花生;葫芦科植物,如葫芦,黄瓜和瓜类;纤维植物,如棉花,亚麻,大麻和黄麻,柑桔类植物,如桔子,柠檬,柚子和中国柑桔;蔬菜,如菠菜,莴苣,芦笋,白菜,胡萝卜,洋葱,西红柿,土豆和辣椒;月桂科植物,如鳄梨,肉桂和樟脑;以及烟草,坚果,咖啡,茄子,糖甘蔗,茶,胡椒,葡萄,蛇麻草,香蕉,天然橡胶和观赏植物等。
本发明叙及的化合物在其它方面的应用还包括用于保护储藏物品,储藏室和各种原材料,也用于卫生方面,特别是用于防治家养动物,牲畜的上述各类害虫,特别是用于保护家养动物,如猫,狗免于跳蚤,扁虱和线虫的攻击。
于是本发明还叙及农药组合物,如乳油,浓悬浮剂,可直接喷雾或可稀释的溶液,可展性糊剂,稀乳液,可湿性粉剂,可溶性粉剂,可分散粉剂,粉剂,粒剂,高聚物微囊剂,它们至少含有本发明叙及的化合物,配方的选择与预期的目标和一般环境一致。
在上述组合物中使用的活性组份是纯的固体,如以一定大小颗粒使用,或者同时至少有一种常规加工技术采用的助剂,如添加剂,即溶剂,固体载体,或表面活性剂。在保护人类,家养动物,牲畜和宠物领域,不言而喻的是仅能使用生理上可容许的添加剂。
作为加工助剂,被采用的例如固体载体,溶剂,稳定剂,“缓释”助剂,着色彩和选择性表面活性物质(表面活性剂)。适宜的载体和助剂包括所有常规使用的物质。本发明叙及的组合物中,作为助剂,如溶剂,固体载体,表面活性化合物,非离子表面活性剂,阴离子表面活性剂,阳离子表面活性剂以及其它助剂都在考虑的范围内,例如在专利EP-A736252第7页第51行到第8页第39行所叙述的那些助剂。
用于农作物保护和人类,家养动物和牲畜防治的组合物通常含有0.1-99%,优选0.1-95%的活性组份和1-99.9%,优选5-99.9%的至少一种固体的或液体的助剂,上述组合物通常还包括0-25%,优选0.1-20%的表面活性剂(%=重量百分数)。然而商业产品将优先被加工成浓剂,而终端使用者通常应用活性成份显著降低的稀释制剂。
本发明叙及的化合物和由它们构成的组合物对动物害虫的作用可以通过加入其它杀虫剂,杀螨剂或杀线虫剂显著地扩大并适应给定的环境。适当的添加剂包括,例如下列各类活性成份的代表:有机磷化合物,硝基酚及其衍生物,甲脒类,脲类,氨基甲酸酯类,拟除虫菊酯类,氯代烃及其芽孢杆菌属苏云金杆菌制剂。
特别适合的例子包括:甲基吡恶磷,毒虫畏,乙嘧盼磺酸酯,氯氰菊酯,高顺氯氰菊酯,灭蝇胺,杀螨隆,二嗪磷,敌敌畏,百治磷,dicyclanil,双氧威,fluazuron,呋线威,氯唑磷,碘硫磷,烯虫炔酯,lufenuron,虫螨畏,杀扑磷,久效磷,磷胺,丙溴磷,diofenolan,由芽孢杆菌属苏云金杆菌菌株GC91或NCTC11821获得的物质,pymetrozine,溴螨酯,烯虫酯,乙拌磷,喹硫磷,氟胺氰菊酯,杀虫环,二甲硫吸磷,涕灭威,保棉磷,丙硫克百威,氟氯菊酯,噻嗪酮,克百威,dibutylaminothio,杀螟丹,定虫隆,毒死蜱,氟氯氰菊酯,顺式氯氰菊酯,zeta-氯氰菊酯,溴氰菊酯,除虫脲,硫丹,乙硫苯威,杀螟硫磷,喹螨醚,仲丁威,氰戊菊酯,安果,灭棱威,庚烯磷,吡虫啉,叶蝉散,甲胺磷,灭多威,速灭磷,对硫磷,甲基对硫磷,优杀硫磷,抗蚜威,残杀威,伏虫隆,特丁磷,唑蚜威,阿凡曼菌素,tebufenozide,氟虫氰,氟氯氰菊酯,硅醚菊酯,唑螨酯,哒螨酮,primicarb,蚊蝇醚,嘧虫醚,nematorin,吡虫稀,啶虫脒,从植物中获得的一种杀虫活性提取物,一种含杀虫活性线虫的制剂,一种含有杀虫活性真菌的制剂,一种含有杀虫活性细菌的制剂,AC303630,乙酰甲胺磷,氟酯菊酯,棉铃威,双虫脒,AZ60541,azinphos A,azinphos M,三唑锡,恶虫威,杀虫磺,brofenprox,bromophos A(bromophos-溴硫磷),合杀威,丁酮威,butylpyridaben,硫线磷,甲萘威,三硫磷,chloethocarb,chloethoxyfos,氯甲硫磷,cis-res-methrin,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,三环锡,demeton M(demefon-内吸磷),demetors,demeton-s-methyl,酚线磷,dicliphos,乙硫磷,乐果,甲基毒虫畏,敌恶磷,克瘟散,埃马菌素,高氰戊菊酯,醚菊酯,灭线磷,乙嘧硫磷,虫胺磷,苯丁锡,苯硫威,甲氰菊酯,fenpyrad,倍硫磷,氟啶胺,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,地虫硫磷,噻唑磷,fubfenprox,林丹,氟铃脲,噻嗪酮,IKI220,异稻瘟净,异丙胺磷,恶唑磷,依维菌素,氟氯氰菊酯,马拉硫磷,灭蚜蜱,mesulfenphos,蜗牛散,速灭威,milbemectin,moxidectin,二溴磷,NC184,氧乐果,杀线威,oxydemethon M,异砜磷,氯氧酯,稻丰散,甲拌磷,亚胺硫磷,辛硫磷,pirimiphos-M(pirimiphos-mefhyl甲基嘧啶磷),pirimiphos-A,猛杀威,丙虫磷,丙硫磷,发果,pyrachlophos,pyrada-phenthion,pyresmethrin,除虫菊酯,RH5992,果蔬磷,sebufos,治螟磷,甲丙硫磷,吡螨胺,tebupirimphos,七氟菊酯,双硫磷,特灭威,杀虫畏,thiacloprid,thiamethoxam,thiafenox,硫双威,久效威,虫线磷,苏云金杆菌,四溴菊酯,苯赛螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,蚜灭多,灭杀威,YI5301/5302,zetnmethrin,DPX-MP062,RH-2485,D2341或XMC(甲基氨基甲酸二甲苯酯)。
特别优选的农作物保护产品具有下列组成(%=重量百分数):
乳油:
活性成分: 1-90%,优选5-20%
表面活性剂: 1-30%,优选10-20%
溶剂: 5-98%,优选70-85%
粉剂:
活性成分: 0.1-10%,优选0.1-1%
固体载体: 99.9-90%,优选99.9-99%
浓悬浮剂:
活性成分: 5-75%,优选10-50%
水: 94-24%,优选88-30%
表面活性剂: 1-40%,优选2-30%
可湿性粉剂:
活性成分: 0.5-90%,优选1-80%
表面活性剂: 0.5-20%,优选1-15%
固体载体: 5-99%,优选15-98%
粒剂:
活性成分: 0.5-30%,优选3-15%
固体载体: 99.5-70%,优选97-85%
本发明叙及的组合物也可以含有其它固体或液体,如稳定剂,如植物油或环氧化植物油(如环氧化椰子油,油菜子油或大豆油),消泡剂,如硅油,防腐剂,粘度调节剂,粘合剂和/或增粘剂及其肥料或其它能够产生特殊效果的活性成分。如杀螨剂,抗菌剂,杀菌剂,杀线虫剂,软体动物杀灭剂或选择性除草剂。
本发明叙及的农作物保护产品由已知的方式制备,倒如,在没有助剂的情况下研磨,筛分和/或挤压固体活性成分或活性成分的混合物成为一定大小的颗粒,以及在至少一种添加剂存在的情况下混合或研磨活性成分或活性成分与助剂的混合物。本发明还叙及了制备化合物的方法以及应用式(I)所示化合物制备这些化合物。
本发明也叙及了这些作物保护产品的使用方法,即防治害虫的方法,如喷雾,雾化,喷粉,涂抹,包衣,撒布或浇泼,选用的方法与预定的目标,通常环境以及防治害虫的种类相一致,活性成分的典型浓度为0.1-1000ppm,优选0.1-500ppm,每公顷通常使用1-2000克活性成分,优选10-1000克/公顷,最佳优选20-600克/公顷。
应用于作物保护领域的优选方法是施用于植物的叶面(叶面施用),施用的次数和比率取决于目标害虫的危害程度。然而当用液体制剂侵润植物所在地或当活性成分以固体的形式,如以粒剂的形式混合入植物所在地(土壤施用)时,活性成分也能够通过根部进入植物体(内吸作用),在水稻作物的情况下,可以施用计算量的这些粒剂到淹没的水稻田。
本发明的作物保护产品也适于保护植物繁殖材料,如种子,果实,块茎或谷粒,或植物的插条不受动物害虫的危害。在种植前,繁殖材料可用组合物处理:如种子在播种前可以包衣。本发明的活性物质也可用于谷粒(涂抹),其方法或者是种子在液体制剂中浸泡或者是用固体制剂涂抹。在种植繁殖材料时组合物也可用于种植地点,如施用于播种期间的种子垄沟。本发明也叙及到处理植物繁殖材料的方法和处理的植物繁殖材料。
制备实施例:
实施例P1.1:4″-脱氧-4″-表-(N-3-氟代苯基甲氨基)阿凡曼菌素B1
1.0克4″-脱氧-4″-表-氨基阿凡曼菌素B1溶解在12亳升四氢呋喃中,加入1.8亳升乙酸,0.2毫升水和0.18毫升3-氟苯甲醛,然后加入90毫升氰硼氢化钠。混合物在室温下搅拌12小时。用乙酸乙酯和饱和氯化钠溶液提取;有机相用硫酸钠干燥,蒸除溶剂。残余物用硅胶柱层析纯化(己烷/乙酸乙酯),得4″-脱氧-4″-表-(N-3-氟代苯基甲氨基)阿凡曼菌素B1。
实施例P1.2:4″-脱氧-4″-表-N-乙基氨基阿凡曼菌素B1
4.0克4″-脱氧-4″-表-氨基阿凡曼菌素B1溶解在24毫升乙酸乙酯中,加入7.4毫升碘乙烷和24毫升碳酸氢钠(1N水溶液)。混合物在室温下猛烈搅拌14小时,分离水相和有机相;有机相用硫酸钠干燥然后蒸除溶剂。残余物在硅胶柱上层析纯化(己烷/乙酸乙酯),得到4″-脱氧-4″-表-N-乙氨基阿凡曼菌素B1。
实施例P1.3:4″-脱氧-4″-表-N-(异丙氧羰基甲基)氨基阿凡曼菌素
B1
300毫克4″-脱氧-4″-表-氨基阿凡曼菌素B1溶解在3毫升乙酸乙酯中。加入620毫升溴乙酸异丙酯和3毫升碳酸氢钠(1N水溶液)。混合物在室温下猛烈搅拌18小时。分离水相和有机相,有机相用硫酸钠干燥然后蒸除溶剂。残余物用硅胶柱层析纯化(己烷/乙酸乙酯),得4″-脱氧-4″-表-N-(异丙氧羰基甲基)氨基阿凡曼菌素B1。
实施例P2.1:4″-脱氧-4″-表-(N-甲基-N-1-丙烯-3-基氨基)阿凡曼菌
素B1
600毫升4″-脱氧-4″-表-甲氨基阿凡曼菌素B1溶解在6毫升乙酸乙酯中,加入0.56毫升烯丙基溴和6毫升碳酸氢钠(1N水溶液)。混合物在60℃下猛烈搅拌18小时,然后冷却。分离水相和有机相,有机相用硫酸钠干燥,然后蒸除溶剂,残余物用硅胶柱层析纯化(己烷/乙酸乙酯),得4″-脱氧-4″-表-(N-甲基-N-1-丙烯-3-基氨基)阿凡曼菌素B1。
实施例P2.2:4″-脱氧-4″-表-(N-2-羟乙基-N-甲氨基)阿凡曼菌素
B1
第一步:4.55克4″-脱氧-4″-表-甲氨基阿凡曼菌素B1溶解在45毫升乙酸乙酯中。加入8.6克溴代乙酸乙酯和45毫升碳酸氢钠(1N水溶液)。混合物在60℃下猛烈搅拌18小时,冷却。分离水相和有机相,有机相用硫酸钠干燥,蒸除溶剂。残余物用硅胶柱层析纯化(己烷/乙酸乙酯),得4″-脱氧-4″-表-(N-甲基-N-乙氧羰基甲基氨基)阿凡曼菌素B1。
第二步:300毫克4″-脱氧-4″-表-(N-甲基-N-乙氧羰基甲氨基)阿凡曼菌素B1溶解在6毫升甲苯中。室温搅拌下加入1.3毫升二异丁基氢化铝(1,2摩尔的甲苯溶液)。15分钟后用乙酸乙酯和饱和氨化铵溶液提取。分离水相和有机相;有机相用硫酸钠干燥,蒸除溶剂。残余物用硅胶柱层析纯化,得4″-脱氧-4″-表-(N-2-羟乙基-N-甲氨基)阿凡曼菌素B1。
实施例P2.3:4″-脱氧-4″-表-(N-异丙基-N-甲氨基)阿凡曼菌素B1
2.0克4″-脱氧-4″-表-异丙氨基阿凡曼菌素B1溶解在20毫升乙酸乙酯中。加入4毫升碘甲烷和20毫升碳酸氢钠(1N水溶液),该混合物在60℃下猛烈搅拌14小时,然后冷却。分离水相和有机相;有机相用硫酸钠干燥,蒸除溶剂。残余物用硅胶柱层析纯化(乙酸乙酯),得4″-脱氧-4″-表-(N-异丙基-N-甲氨基)阿凡曼菌素B1。
实施例P2.4:4″-脱氧-4″-表-(N-异丙基-N-甲氨基)阿凡曼菌素B1
9.14克4″-脱氧-4″-表-异丙氨基阿凡曼菌素B1溶解在100毫升甲醇中。加入15毫升新戊酸和25毫升甲醛溶液(37%水溶液)。然后再加入0.7克氰硼氢化钠。混合物在室温下搅拌1小时,然后真空蒸除甲醇,残余物用乙酸乙酯和饱和碳酸氢钠提取。分离水相和有机相。有机相用硫取钠干燥,然后蒸除溶剂。残余物用硅胶柱层析纯化(乙酸乙酯/甲醇),得4″-脱氧-4″-表-(N-异丙基-N-甲基氨基)阿凡曼菌素B1。
实施例P2.5:4″-脱氧-4″-表-(N-羧甲基-N-甲氨基)阿凡曼菌素B1
第一步:10克4″-脱氧-4″-表-甲氧基阿凡曼菌素B1溶液在100毫升磅放氢钠(1N水溶液)。混合物在60℃下猛烈搅拌5天,然后冷却。分离水相和有机相,有机相用硫酸钠干燥,蒸除溶剂。残余物用硅胶柱层析纯化(已烷/乙酸乙酯),得4″-脱氧-4″-表-(N-苄氧羰基甲基-N-甲氨基)阿凡曼菌素B1。
第二步:7.8克4″-脱氧-4″-表-(N-苄氧碳基甲基-N-甲氨基)阿凡曼菌素B1溶解在100毫升四氢呋喃中。加入780毫克钯(碳上5%),然后在室温通常压力下氢化。1小时后氢的吸取停止。混合物通过硅藻土过滤,蒸除溶剂得4″-脱氧-4″-表-(N-羧甲基-N-甲氨基)阿凡曼菌素B1。
实施例P2.6:4″-脱氧-4″-表-(N-羧甲基-N-甲氨基)阿凡曼菌素B1
第一步:15克4″-脱氧-4″-表-甲氨基阿凡曼菌素B1溶于120毫升碳酸氢钠(1N水溶液)。混合物在60℃下猛烈搅拌5天,然后冷却。分离水相和有机相,有机相用硫酸钠干燥,蒸除溶剂。残余物用硅胶柱层析纯化(己烷/乙酸乙酯),得4″-脱氧-4″-表-(N-甲氧羰基甲基氨基-N-甲基)阿凡曼菌素B1。
第二步:10克4″-脱氧-4″-表-(N-甲氧羰基甲基氨基-N-甲基)阿凡曼菌素B1溶于90毫升四氢呋喃中。加入10毫升水和440毫克氢氧化锂一水合物,然后在室温下搅拌14小时。用水和二乙醚提取,分去水相后冷冻干燥。残余物用乙酸乙酯和柠檬酸(10%水溶液)提取,有机相用硫酸钠干燥后蒸除溶剂,得4″-脱氧-4″-表-(N-羧甲基-N-甲氨基)阿凡曼菌素B1。
实施例P2.7:4″-脱氧-4″-表-(N-乙基-N-甲氨基)阿凡曼菌素B1
8.0克4″-脱氧-4″-表-N-甲氨基阿凡曼菌素B1溶解在50毫升乙酸乙酯中。加入15毫升碘乙烷和50毫升碳酸氢钠(1N水溶液)。混合物在60℃下猛烈搅拌2天。分离水相和有机相,有机相用硫酸钠干燥后蒸除溶剂。残余物用硅胶柱层析纯化(乙酸乙酯/甲醇),得4″-脱氧-4″-表-(N-乙基-N-甲氨基)阿凡曼菌素B1。
实施例P2.8:4″-脱氧-4″-表-{N-[(1-苄氧羰基乙基氨基甲酰基)甲
基]-N-甲氨基}阿凡曼菌素B1
500毫克4″-脱氧-4″-表-(N-羧甲基-N-甲氨基)阿凡曼菌素B1溶解在5毫升乙酸乙酯中,然后加入170毫克L-丙氨酸苄酯,72毫克1-羟基-7-氮杂苯并三唑和110毫克N,N一二环己基碳二亚胺。室温下搅拌7天。混合物用乙酸乙酯和碳酸氢钠(1N水溶液)提取,有机相用硫酸钠干燥,然后蒸除溶剂。残余物用硅胶柱层析纯化,得4″-脱氧-4″-表-{N-[(1-苄氧碳基乙基氨基甲酰基)甲基]-N-甲氨基}阿凡曼菌素B1。
实施例P2.9:4″-脱氧-4″-表-{N-[(1-苄氧碳基乙基氨基甲酰基)甲
基]-N-甲氨基}阿凡曼菌素B1
160毫克4″-脱氧-4″-表-{N-[(1-苄氧羰基乙基氨基甲酰基)甲基]-N-甲氨基}阿凡曼菌素B1溶解在10毫升四氢呋喃中,加入50毫克钯(碳上5%),然后在室温和通常压力下氢化。3小时后吸氢停止。混合物通过硅藻土过滤,蒸除溶剂得4″-脱氧-4″-表-{N-[(1-羧乙基氨基甲酰基)甲基]-N-甲氨基}阿凡曼菌素B1。
实施例P2.10:4″-脱氧-4″-表-[N-(2-羟基-2-甲基丙基)-N-甲氨基]
阿凡曼菌素B1
300毫升4″-脱氧-4″-表-(N-甲基-N-乙氧羰基甲基氨基)阿凡曼菌素B1(来自实施例P2.2第一步)溶解在6毫升四氢呋喃中,室温搅拌下加入0.64毫升甲基溴化镁(3摩尔/升乙醚溶液)。1小时后用乙酸乙酯和饱和氯化铵溶液提取。分离水相和有机相,有机相用硫酸钠干燥,然后蒸除溶剂。残余物用硅胶柱层析纯化(乙酸乙酯/甲醇),得4″-脱氧-4″-表-[N-(2-羟基-2-甲基丙基)-N-甲氨基]阿凡曼菌素B1.
实施例P3.1:4″-脱氧-4″-表-[N,N-双(1-苯基-1-丙烯-3-基)氨基]
阿凡曼菌素B1
3.48克4″-脱氧-4″-表-氨基阿凡曼菌素B1溶解在40毫升乙酸乙酯中。加入4.62克3-溴-1-苯基-1-丙烯和40毫升碳酸氢钠(1N水溶液)。混合物在60℃下猛烈搅拌3天,然后冷却。分离水相和有机相;有机相用硫酸钠干燥,然后蒸除溶剂。残余物用硅胶柱层析纯化(己烷/乙酸乙酯),得4″-脱氧-4″-表-[N,N-双(1-苯基-1-丙烯-3-基)氨基]阿凡曼菌素B1
实施例P3.2:4″-脱氧-4″-表-(氮杂环丁-1-基)阿凡曼菌素B1
300毫克4″-脱氧-4″-表-氨基阿凡曼菌素B1溶解在1毫升甲苯中。加入0.106毫升1,3一二溴丙烷和1毫升碳酸氢钠(1N水溶液)。混合物在90℃下猛烈搅拌24小时,然后冷却。分离水相和有机相;有机相用硫酸钠干燥,蒸除溶剂。残余物用硅胶柱层析纯化(乙酸乙酯/甲醇),得4″-脱氧-4″-表-(氮杂环丁-1-基)阿凡曼菌素B1。
实施例P3.3:4″-脱氧-4″-表-[N,N-双(3,3一二甲基丁基)氨基] 阿凡曼菌素B1。
0.87克4″-脱氧-4″-表-氨基阿凡曼菌素B1溶解在10毫升四氢呋喃中。加入1毫升新戊酸,0.1毫升水和0.60克3,3一二甲基丁醛,然后再加入0.38克氰硼氢化钠。混合物在室温下搅拌14小时。用乙酸乙酯和碳酸氢钠(1N水溶液)提取;有机相用硫酸钠干燥,然后蒸除溶剂。残余物用硅胶柱层析纯化(己烷/乙酸乙酯),得4″-脱氧-4″-表-[N,N-双(3,3一二甲基丁基)氨基]阿凡曼菌素B1。
实施例P4.1:4″-脱氧-4″-表-[N-(3-乙酰氧基丙基)-N-甲氨基]阿凡 曼菌素B1。
100毫克4″-脱氧-4″-表-[N-(3-碘代丙基)-N-甲氨基]阿凡曼菌素B1和100毫克乙酸钠溶解在2毫升N,N一二甲基甲酰胺中。将混合物加热到60℃,然后在此温度下搅拌90分钟。将混合物冷却到室温后用乙醚提取。分出有机相并用碳酸氢钠(1N水溶液)洗涤,硫酸钠干燥。蒸除溶剂后残余物以己烷/乙酸乙酯为洗脱液硅胶上纯化,得4″-脱氧-4″-表-[N-(3-乙酰氧基丙基)-N-甲氨基]阿凡曼菌素B1。
实施例P4.2:4″-脱氧-4″-表-[N-(3-碘代丙基)-N-甲氨基]阿凡曼菌
素B1。
3克4″-脱氧-4″-表-N-甲氨基阿凡曼菌素BI和9毫升1,3一二碘丙烷溶液在9毫升乙酸乙酯中。加入18毫升碳酸氢钠溶液(1N水溶液),然后混合物在60℃下搅拌3天。将混合物冷却到室温,分出有机相并用硫酸钠干燥。蒸除溶剂后残余物以己烷/乙酸乙酯为洗脱剂在硅胶柱上纯化,得4″-脱氧-4″-表-[N-(3-碘代丙基)-N-甲氨基]阿凡曼菌素B1。
实施例P4.3:4″-脱氧-4″-表-N-(2-氰基乙基氨基)阿凡曼菌素B1
872毫克4″-脱氧-4″-表-N-氨基阿凡曼菌素B1溶解在5毫升甲醇中。加入212毫克丙烯腈后混合物在室温下搅拌3天。蒸除溶剂后残余物以己烷/乙酸乙酯为洗脱液在硅胶上纯化,得4″-脱氧-4″-表-N-(2-氰基乙基胺基)阿凡曼菌素B1。
由于在大多数情况下所涉及的化合物都是以阿凡曼菌素衍生物B1a和Blb的混合物出现,通过常规的物理常数如熔点或折光指数来进行表征没有意义。因此,化合物用保留时间来表征,保当时间由HPLC(高效液相色谱)来测定。此外,术语Bla代表主要成分,其中R1为仲丁基,通常含量大于80%,B1b表示次要成分,其中R1为异丙基。分别给出Bla和Blb衍生物保留时间的化合物是非对映异构体,它们可以由色谱法分离。如果仅仅在Bla或Blb栏内给出一个保留时间,则化合物为纯的Bla或Blb组份。它们可以在操作中获得。Bla或Blb组份的正确结构由质谱法指定。HPLC分析采用了下述方法:
HPLC梯度条件
溶剂A: | 0.01%三氟乙酸水溶液 | ||
溶剂B: | 0.01%三氟乙酸乙腈溶液 | ||
时间[分] | A[%] | B[%] | 流速[微升/分] |
00.110151717.122 | 80505008080 | 2550951001002020 | 500500500500500500500 |
柱类型柱长柱内径温度 | YMC-Pack ODS-AQ125mm2mm40℃ |
化合物层析用YMC-Pack ODS-AQ柱系德国465.4 Schermbeck,Ahe Raesfelderstrasse 6,YMC制造。
表1:式(1)所示化合物,式中R1为仲丁基(Bla)或异丙基(Blb),R2为H:
表2:式(1)所示化合物,式中R1为仲丁基(Bla)或异丙基(Blb),R2为甲基:
No. | R3 | 保留时间(分) | |
B1a | B1b | ||
2.292.302.312.322.332.342.352.362.372.382.392.402.412.422.432.442.452.462.472.482.492.502.512.522.532.542.552.562.572.582.592.602.612.622.632.64 | (4-叔丁基苯基)甲基(4-氟苯基)甲基(4-溴苯基)甲基2-溴烯丙基-CH2-C(=O)-O-i-丙基-CH2-C(=O)-O-CH2-CH2-O-CH3(2,3,4-三氟苯基)甲基(2,4,5-三氟苯基)甲基(2,3,6-三氟苯基)甲基(3,5-二溴苯基)甲基(3-氟-6-溴苯基)甲基(2,3-二氯苯基)甲基(2,6-二氯苯基)甲基(2,5-二氯苯基)甲基(3,4-二氯苯基)甲基(2-氟-3-氯苯基)甲基(2-氯-4-氟苯基)甲基(2,5-二氟苯基)甲基(2,6-二氟苯基)甲基(2,3-二氟苯基)甲基((3,5-二氟苯基)甲基(3-溴苯基)甲基(2-氯苯基)甲基(2-氟苯基)甲基(3-氟苯基)甲基(4-碘苯基)甲基(2-碘苯基)甲基(4-硝基苯基)甲基(3-硝基苯基)甲基(2-氯-5-[三氟甲基]苯基)甲基(3-氟-5-[三氟甲基]苯基)甲基(3,5-二氯苯基)甲基(2-三氟甲基苯基)甲基(3-三氟甲氧基苯基)甲基(4-氰基苯基)甲基(2-氰基苯基)甲基 | 8.326.887.50 | 7.946.497.07 |
表3:式(1)所示化合物,式中R1为仲丁基(Bla)或异丙基(Blb):
用于农作物保护的剂型实施例(%=重量百分数)
实施例F1:乳油 a) b) c)
活性化合物 25% 40% 50%
十二烷基苯磺酸钙 5% 8% 6%
蓖麻油聚乙二醇醚(36摩尔EO) 5% - -
三丁基酚聚乙二醇醚(30摩尔EO) - 12% 4%
环己酮 - 15% 20%
二甲苯混合物 - 65% 25%20%
仔细研磨的活性化合物与添加剂混合后得到乳油,该乳油用水稀释可得所需浓度的乳液。
实施例F2:溶液 a) b) c) d)
活性化合物 80% 10% 5% 95%
乙=醇单甲醚 - 20% - -
聚乙二醇(MW400) - - 70% -
N-甲基吡咯烷-2-酮 20% - - -
环氧化椰子油 - - - 1%
石油醚(沸程:160~190°) - - 94% -
仔细研磨的活性化合物和添加剂混合后得溶液,该溶液适于以微滴的形式使用。
实施例F3:粒剂 a) b) c) d)
活性化合物 5% 10% 8% 21%
高岭土 94% - 79% 54%
细分硅酸 1% - 13% 7%
美国活性白土 - 90% - 18%
将活性化合物溶于二氯甲烷,喷雾在载体上,减压下蒸去溶剂。
实施例F4:可湿性粉剂 a) b) c)
活性化合物 25% 50% 75%
本素磺酸钠 5% 5% -
二异丁基秦磺酸钠 3% - 5%
辛基酚聚乙二醇醚(7-8摩尔EO) - 6% 10%
细分硅酸 5% 10% 10%
高岭土 62% 27% -
活性化合物和添加剂混合后在适当的磨上碾磨。所得可湿性粉剂用水稀释后可得所需浓度的悬浮液。
实施例F5:乳油
活性化合物 10%
辛基酚聚乙二醇醚 3%
十二烷基苯磺酸钙 3%
蓖麻油聚乙二醇醚(36摩尔EO) 4%
环己酮 30%
二甲苯混合物 50%
将仔细研磨的活性化合物与添加剂混合后得到乳油,该乳油用水稀释可得所需浓度的乳液。
实施例F6:挤压粒剂
活性化合物 10%
本素磺酸钠 2%
羧甲基纤维素 1%
高岭土 87%
活性化合物与添加剂混合后研磨,用水润湿,挤压成粒,并在空气流下干燥。
实施例F7:涂抹粒剂
活性化合物 3%
聚乙二醇(MW200) 3%
高岭土 94%
将高岭土用聚乙二醇润湿,在一个混合器中将仔细研磨的活性化合物均匀地涂在上述高岭土上,得到无粉尘的涂抹粒剂。
实施例F8:浓悬浮剂
活性化合物 40%
乙二醇 10%
壬基酚聚乙二醇醚(15摩尔EO) 6%
木素磺酸钠 10%
羧甲基纤维素 1%
甲醛水溶液(37%) 0.2%
硅油水乳液(75%) 0.8%
水 32%
将仔细研磨的活性化合物与添加剂混合得浓悬浮剂,该浓悬浮剂用水稀释可得所需浓度的悬浮剂。
生物学实施例:
实施例B1:对海灰翅夜蛾的活性
大豆幼苗用含12.5ppm活性化合物的水乳液喷雾,待喷雾层干后,移植上10个一龄海灰翅夜蛾幼虫,放入塑料容器中。三天后通过比较处理和未处理的幼虫死亡数和饲料损失量来确定虫口减少的百分数和饲料损失的百分数。
在此试验中,表列化合物显示出良好的活性,特别是化合物
1.001,1.002,1.003,1.004,1.005,1.006,1.007,1.008,1.009,1.010,1.011,
1.012,1.013,1.014,1.015,1.016,1.017,1.018,1.019,1.020,1.021,1.022,1.023,1.024,
1.025,1.026,1.027,1.028,1.029,1.030,1.031,1.032,1.033,1.034,1.035,1.036,1.037,
1.038,1.039,1.040,1.041,1.042,1.043,1.044,1.045 1.046,1.047,1.048,1.050,1.051,
1.052,1.053,1.054,1.055,1.056,1.057,1.058,1.059,1.060,1.061,1.062,1.063,1.064,
1.131,1.132,1.133,1.134,1.135,1.136,1.137,1.138,1.138,1.139,1.140,1.141,1.142,
1.143,1.144,1.145,1.146,1.147,1.148,1.149,1.150,1.151,1.152,1.153,1.154,1.155,
1.156,1.157,1.158,2.001,2.002,2.003,2.004,2.005,2.006,2.007,2.008,2.009,2.010,
2.011,2.012,2.013,2.014,2.015,2.016,2.017,2.018,2.019,2.020,2.021,2.022,2.023,
2.024,2.025,2.026,2.027,2.028,2.029,2.030,2.031,2.032,2.033,2.034,2.035,2.036,
2.037,2.038,2.039,2.040,2.041,2.042,2.043,2.044,2.045,2.046,2.047,2.048,2.049,
2.050,2.051,2.052,2.053,2.054,2.055,2.056,2.057,2.058,2.059,2.060,2.061,2.062,
2.063,2.064,2.065,2.066,2.067,2.068,2.069,2.070,2.071,2.072,2.073,2.074,2.075,
2.076,2.077,2.078,2.079,2.080,2.081,3.001,3.002,3.003,3.004,3.005,3.006,3.007,
3.008,3.009,3.010,3.011和3.012
引起的虫口减少率大于80%。
实施例B2:对海灰翅夜蛾的内吸活性
将玉米苗放入受试溶液中,六天后,切下叶片,放置在皮氏培养皿的润湿滤纸上,移植12-15个L1龄的海灰翅夜蛾幼虫。4天后,通过比较处理和未处理植株上幼虫死亡数来确定虫口减少的百分数(活性百分数)。
在此试验中,表列化合物显示出良好的活性。特别是化合物
1.001,1.002,1.003,1.004,1.005,1.006,1.007,1.008,1.009,1.010,1.012,
1.013,1.014,1.015,1.016,1.017,1.018,1.019,1.020,1.021,1.022,1.023,1.024,1.025,
1.026,1.027,1.028,1.029,1.030,1.031,1.032,1.033,1.034,1.035,1.036,1.037,1.038,
1.039,1.040,1.041,1.042,1.043,1.044,1.045 1.046,1.047,1.048,1.049,1.050,1.051,
1.052,1.053,1.054,1.055,1.056,1.057,1.058,1.059,1.060,1.061,1.062,1.064,1.065,
1.066,1.067,1.068,1.069,1.070,1.071,1.072,1.073,1.074,1.075,1.076,1.077,1.078,
1.079,1.080,1.081,1.082,1.083,1.084,1.085,1.086,1.087,1.088,1.089,1.090,1.091,
1.092,1.093,1.094,1.095,1.096,1.097,1.098,1.099,1.100,1.101,1.102,1.103,1.104,
1.105,1.106,1.107,1.108,1.109,1.110,1.111,1.112,1.113,1.114,1.115,1.116,1.117,
1.118,1.119,1.120,1.121,1.122,1.123,1.124,1.125,1.126,1.127,1.128,1.129,1.130,
1.065,1.066,1.067,1.068,1.069,1.070,1.071,1.072,1.073,1.074,1.075,1.076,1.077,
1.078,1.079,1.080,1.081,1.082,1.083,1.084,1.085,1.066,1.087,1.088,1.089,1.090,
1.091,1.092,1.093,1.094,1.095,1.096,1.097,1.098,1.099,1.100,1.101,1.102,1.103,
1.104,1.106,1.107,1.109,1.110,1.111,1.112,1.113,1.114,1.115,1.116,1.117,1.118,
1.119,1.120,1.121,1.122,1.123,1.124,1.125,1.126,1.127,1.128,1.129,1.130,1.131,
1.132,1.133,1.134,1.135,1.136,1.137,1.138,1.138,1.139,1.140,1.141,1.142,1.143,
1.144,1.145,1.146,1.147,1.148,1.149,1.150,1.151,1.152,1.153,1.154,1.155,1.156,
1.157,1.158,2.001,2.002,2.003,2.004,2.005,2.006,2.007,2.008,2.009,2.010,2.011,
2.012,2.013,2.014,2.015,2.016,2.017,2.018,2.019,2.020,2.021,2.022,2.023,2.023.
2.024,2.025,2.026,2.027,2.028,2.029,2.030,2.031,2.032,2.033,2.034,2.035,2.036,
2.037,2.038,2.039,2.040,2.041,2.042,2.043,2.044,2.045,2.046,2.047,2.048,2.049,
2.050,2.051,2.052,2.053,2.054,2.055,2.056,2.057,2.058,2.059,2.060,2.061,2.062,
2.063,2.064,2.065,2.066,2.067,2.068,2.069,2.070,2.071,2.072,2.073,2.074,2.075,
2.076,2.077,2.078,2.079,2.080,2.081,3.001,3.002,3.003,3.004,3.005,3.006,3.007,
3.008,3.009,3.010,3.011和3.012
引起的虫口减少率大于80%。
实施例B3:对烟草夜蛾的活性
在皮氏培养皿中放入一层合成饲料,其上放入滤纸,在滤纸上引入30~35粒出生0~24小时的烟芽夜蛾卵。然后用吸液管将0.8毫升受试溶液加在滤纸上。6天后进行评价。通过比较滤纸上处理与未处理死亡卵和幼虫数来确定虫口死亡百分数(活性百分数)。
在此试验中,表列化合物显示了良好的活性。特别是化合物
1.001,1.002,1.003,1.004,1.005,1.006,1.007,1.008,1.009,1.010,1.011,
1.012,1.013,1.014,1.015,1.016,1.017,1.018,1.019,1.020,1.021,1.022,1.023,1.024,
1.025,1.026,1.027,1.028,1.029,1.030,1.031,1.032,1.033,1.034,1.035,1.036,1.037,
1.038,1.039,1.040,1.041,1.042,1.043,1.044,1.045,1.046,1.047,1.048,1.052,1.053,
1.054,1.055,1.056,1.057,1.069,1.070,1.071,1.072,1.073,1.074,1.075,1.076,1.078,
1.079,1.080,1.081,1.082,1.083,1.084,1.085,1.086,1.087,1.088,1.089,1.090,1.091,
1.092,1.093,1.094,1.095,1.096,1.097,1.098,1.099,1.100,1.101,1.102,1.103,1.104,
1.107,1.109,1.110,1.111,1.112,1.113,1.114,1.115,1.116,1.117,1.118,1.119,1.120,
1.121,1.122,1.123,1.124,1.125,1.126,1.127,1.128,1.129,1.130,1.131,1.132,1.133,
1.134,1.135,1.136,1.137,1.138,1.138,1.139,1.140,1.141,1.142,1.143,1.144,1.145,
1.147,1.148,1.149,1.150,1.151,1.152,1.153,1.154,1.155,1.156,1.157,1.158,2.001,
2.002,2.003,2.005,2.006,2.007,2.008,2.009,2.010,2.011,2.012,2.013,2.014,2.015,
2.016,2.017,2.018,2.019,2.020,2.021,2.026,2.027,2.028,2.029,2.030,2.031,2.032,
2.033,2.034,2.035,2.036,2.037,2.038,2.039,2.040,2.042,2.043,2.044,2.045,2.046,
2.047,2.048,2.049,2.050,2.051,2.052,2.053,2.054,2.055,2.056,2.057,2.058,2.059,
2.062,2.063,2.064,2.066,2.067,2.068,2.069,2.070,2.071,2.073,2.074,2.075,2.076,
2.077,2.078,2.079,2.080,2.081,3.001,3.002,3.003,3.004,3.005,3.006,3.007,3.008,
3.009和3.010
引起的虫口减少率大于80%。
实施例B4:对小菜蛾幼虫的活性
白菜幼苗用活性化合物含量为12.5ppm的乳液喷雾。待喷雾层干燥后,在幼苗上移植10只小菜蛾幼虫,然后放入塑料容器中。3天后评价。通过比较处理和未处理幼虫死亡数和饲料损失数来确定虫口减少百分数和饲料损失百分数(活性百分数)。
在此试验中,表列化合物对小菜蛾显示出良好的活性,特别是化合物
1.001,1.002,1.003,1.004,1.005,1.006,1.007,1.008,1.009,1.010,1.011,1.012,1.013,1.014,1.015,1.016,1.017,1.018,1.019,1.020,1.021,1.022,1.023,1.024,1.025,1.026,1.027,1.028,1.029,1.030,1.031,1.032,1.033,1.034,1.035,1.037,1.038,1.039,1.040,1.041,1.042,1.043,1.046,1.050,1.051,1.052,1.053,1.054,1.055,1.056,1.057,1.058,1.060,1.061,1.070,1.075,1.082,1.083,1.084,1.085,1.086,1.087,1.088,1.089,1.090,1.091,1.092,1.093,1.094,1.095,1.096,1.097,1.098,1.099,1.100,1.101,1.102,1.104,1.113,1.114,1.115,1.116,1.117,1.118,1.119,1.120,1.121,1.122,1.123,1.125,1.126,1.127,1.128,1.129,1.130,1.131,1.132,1.133,1.134,1.135,1.138,1.140,1.141,1.142,1.143,1.144,1.145,1.147,1.149,1.151,1.152,1.153,1.154,1.155,1.156,1.157,1.158,2.001,2.002,2.003,2.005,2.006,2.007,2.008,2.009,2.010,2.011,2.012,2.013,2.014,2.015,2.017,2.018,2.019,2.020,2.021,2.022,2.026,2.027,2.028,2.029,2.030,2.031,2.032,2.033,2.034,2.035,2.042,2.046,2.057,2.068,2.070,2.073,2.077,2.078,3.001,3.002,3.003,3.004,3.005,3.006,3.007,3.008和3.009
引起的虫口减少率大于80%。
实施例B5:对西花蓟马的活性
在盛有琼脂的皮氏培养皿内放入豆类植物叶片,然后在喷雾室内用受试溶液喷雾,在叶片上移植混合种群的西花蓟马。10天后评价。通过比较处理和未处理虫口来确定减少百分率(活性百分数)。
特别是,化合物
1.027,1.037,1.038,1.039,1.040,1.050,1.061,1.065,
1.068,1.082,2.005,2.006,2.007,2.008,2.009,2.010,2.011,2.012,2.013,2.014,2.015,
2.016,2.017,2.018,2.020,2.021,2.026,2.027,2.028,2.029,2.030,2.032,2.033,2.034,
2.036,2.038,2.040,2.042,2.046,2.047,2.049,2.050,2.051,2.055,2.057,2.062,2.070,
2.071,2.072,3.003,3.006和3.012
引起的害虫虫口减少率大于80%。
实施例B6:对带斑黄瓜叶甲的活性
用活性化合物含量为12.5ppm的水乳液喷雾玉米幼苗,喷雾层干后,移植10只二龄带斑黄瓜叶甲于其上,放入塑料容器。6天后,通过比较处理和未处理死亡的幼虫来确定虫口的减少率(活性百分数)。
在此试验中,表列化合物显示了良好的活性,特别是化合物
1.002,1.003,1.004,1.005,1.006,1.007,1.008,1.009,1.010,1.011,1.012,
1.013,1.014,1.015,1.016,1.017,1.018,1.019,1.020,1.021,1.022,1.023,1.024,1.025,
1.027,1.028,1.029,1.030,1.031,1.032,1.033,1.034,1.035,1.037,1.038,1.039,1.040,
1.041,1.042,1.043,1.045,1.046,1.047,1.048,1.052,1.053,1.054,1.055,1.056,1.057,
1.058,1.059,1.063,1.064,1.065,1.066,1.067,1.068,1.069,1.070,1.071,1.072,1.074,
1.075,1.076,1.077,1.078,1.079,1.080,1.081,1.082,1.083,1.084,1.085,1.086,1.087,
1.088,1.090,1.091,1.092,1.093,1.094,1.095,1.096,1.097,1.098,1.099,1.100,1.101,
1.102,1.104,1.105,1.107,1.108,1.109,1.111,1.113,1.114,1.115,1.116,1.117,1.118,
1.119,1.120,1.121,1.122,1.123,1.125,1.126,1.127,1.128,1.129,1.130,1.131,1.132,
1.133,1.134,1.135,1.136,1.137,1.138,1.139,1.140,1.141,1.142,1.143,1.144,1.145,
1.147,1.148,1.149,1.150,1.151,1.152,1.153,1.154,1.155,1.156,1.157,1.158,2.001,
2.002,2.003,2.004,2.005,2.006,2.007,2.008,2.009,2.010,2.011,2.012,2.013,2.014,
2.015,2.016,2.017,2.018,2.019,2.020,2.021,2.022,2.025,2.026,2.027,2.028,2.030,
2.031,2.032,2.033,2.034,2.046,2.050,2.051,2.052,2.056,2.073,2.074,2.076,2.077,
3.001,3.002,3.004,3.005,3.006,3.007,3.008和3.009
引起的虫口减少率大于80%。
实施例7:对棉叶螨的活性
向豆类幼苗上移植混合种群的棉叶螨,1天后用活性化合物含量为12.5ppm的水乳液喷雾,并在25℃下保温6天,然后评价。通过比较处理和未处理植株上的卵和幼虫的死亡数来确定虫口的减少率(活性百分数)。
在此试验中,表列化合物显示出良好的活性。特别是化合物
1.001,1.002,1.003,1.004,1.005,1.006,1.007,1.008,1.009,1.010,1.011,1.012,1.013,1.014,1.015,1.016,1.017,1.018,1.019,1.020,1.021,1.022,1.023,1.024,1.025,1.026,1.027,1.028,1.029,1.030,1.031,1.032,1.033,1.034,1.035,1.036,1.037,1.038,1.039,1.040,1.041,1.042,1.043,1.044,1.045 1.046,1.047,1.048,1.049,1.050,1.051,1.052,1.053,1.054,1.055,1.056,1.057,1.058,1.059,1.060,1.061,1.062,1.063,1.064,1.065,1.066,1.067,1.068,1.069,1.070,1.071,1.072,1.073,1.074,1.075,1.076,1.077,1.078,1.079,1.080,1.081,1.082,1.083,1.084,1.085,1.086,1.087,1.088,1.089,1.090,1.091,1.092,1.093,1.094,1.095,1.096,1.097,1.098,1.099,1.100,1.101,1.102,1.103,1.104,1.105,1.106,1.107,1.108,1.109,1.110,1.111,1.112,1.113,1.114,1.115,1.116,1.117,1.118,1.119,1.120,1.121,1.122,1.123,1.124,1.126,1.127,1.128,1.129,1.130,1.131,1.132,1.133,1.134,1.135,1.136,1.137,1.138,1.139,1.140,1.141,1.142,1.143,1.144,1.145,1.146,1.147,1.148,1.149,1.150,1.151,1.152,1.153,1.154,1.155,1.156,1.157,1.158,2.001,2.002,2.003,2.004,2.005,2.006,2.007,2.008,2.009,2.010,2.011,2.012,2.013,2.014,2.015,2.016,2.017,2.018,2.019,2.020,2.021,2.022,2.023,2.024,2.025,2.026,2.027,2.028,2.029,2.030,2.031,2.032,2.033,2.034,2.035,2.036,2.037,2.038,2.039,2.040,2.041,2.042,2.043,2.044,2.045,2.046,2.047,2.048,2.049,2.051,2.052,2.053,2.054,2.055,2.056,2.057,2.058,2.059,2.060,2.061,2.062,2.063,2.064,2.065,2.066,2.067,2.068,2.069,2.070,2.071,2.072,2.073,2.074,2.075,2.076,2.077,2.078,2.079,2.081,3.001,3.002,3.003,3.004,3.005,3.006,3.007,3.008,3.009,3.010,3.011和3.012
引起的虫口减少率大于80%。
Claims (8)
1.式(I)所示化合物
式中
R1为C1-C12烷基,C3-C8环烷基或C2-C12链烯基;
R2为H,未取代或一至五取代的C1-C12烷基或未取代或一至五取代的C2-C12链烯基;
R3为C2-C12烷基,一至五取代的C1-C12烷基,未取代或一至五取代的C3-C12环烷基,未取代或一至五取代的C1-C6烷氧基-C1-C6烷基,未取代或一至五取代的C2-C12链烯基,未取代或一至五取代的C2-C12炔基;或
R2和R3共同为三至七员的亚烷基桥或四至七员的亚烯基桥,其中CH2基团可被O,S或NR4取代;
上述提到的烷基,烷氧烷基,链烯基,炔基,亚烷基,亚烯基和环烷基的取代基选自OH,卤素,卤素-C1-C2烷基,CN,SCN,NO2,C2-C6炔基,未取代或被一至三个甲基取代的C3-C8环烷基,降冰片烯基,未取代或被一至三个甲基取代的C3-C8环烯基;C3-C8卤代环烷基,C1-C12烷氧基,C3-C8环烷氧基,C1-C12烷硫基,C3-C8环烷硫基,C1-C12卤代烷硫基,C1-C12烷基亚磺酰基,C3-C8环烷基亚磺酰基,C1-C12卤代烷基亚磺酰基,C3-C8卤代烷基亚磺酰基,C1-C12烷基磺酰基,C3-C8环烷基磺酰基,C1-C12卤代烷基磺酰基,C3-C8卤代环烷基磺酰基,C2-C8链烯基,C2-C8炔基,-N(R8)2,此处两个R8分别是-C(=O)R5,-O-C(=O)R6,-NHC(=O)R5,-S-C(=S)R6,-P(=O)(OC1-C6烷基)2,-S(=O)2R9,-NH-S(=O)2R9,-OC(=O)-C1-C6烷基-S(=O)2R9;
芳基,苄基,杂环基,芳氧基,苄氧基,杂环氧基,芳硫基,苄硫基,杂环硫基,以及根据环上取代的可能性,这些芳基,杂环基,芳氧基,苄氧基,杂环氧基,芳硫基,苄硫基或杂环硫基可以被一至五取代的,取代基选自OH,卤素,CN,NO2,C1-C12烷基,C3-C8环烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C12烷硫基,C1-C12卤代烷硫基,C1-C6烷氧基-C1-C6烷基,二甲氨基-C1-C6烷氧基,C2-C8链烯基,C2-C8炔基,苯氧基,苯基-C1-C6烷基,亚甲基二氧基,-C(=O)R5,-O-C(=O)R6,-NH-C(=O)R6,-N(R8)2,式中两个R8可以各不相同;C1-C6烷基亚磺酰基,C3-C8环烷基亚磺酰基,C1-C6卤代烷基亚磺酰基,C3-C8卤代环烷基亚磺酰基,C1-C6烷基磺酰基,C3-C8环烷基磺酰基,C1-C6卤代烷基磺酰基和C3-C8卤代环烷基磺酰基;
R4为O,C1-C8烷基,羟基-C1-C8烷基,C3-C8环烷基,C2-C8链烯基,C2-C8炔基,苯基,苄基,-C(=O)R5,或-CH2-C(=O)-R5;
R5为H,OH,SH,-N(R8)2,式中两个R8可以不相同;C1-C24烷基,C2-C12链烯基,C1-C8羟基烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C6烷氧基-C1-C6烷基,C1-C6烷氧基-C1-C6烷氧基,C1-C6烷氧基-C1-C6烷氧基-C1-C6烷基,C1-C12烷硫基,C2-C8链烯基氧基,C2-C8炔基氧基,NH-C1-C6烷基-C(=O)R7,-N(C1-C6烷基)-C1-C6烷基-C(=O)-R7,-O-C1-C2烷基-C(=O)R7,-C1-C6烷基-S(=O)2R9,芳基,苄基,杂环基,芳氧基,苄基氧基,杂环氧基;或者为环上未取代或分别被卤素,硝基,C1-C6烷基,C1-C6烷氧基,C1-C6卤代烷基或C1-C6卤代烷氧基一至三取代的芳基,苄基,杂环基,芳氧基,苄氧基或杂环氧基;
R6为H,C1-C24烷基,C1-C12卤代烷基,C1-C12羟基烷基,C2-C8链烯基,C2-C8炔基,C1-C6烷氧基-C1-C6烷基,(NR8)2,式中两个R8可以互不相同;-C1-C6烷基-C(=O)R8,-C1-C6烷基-S(=O)2R9,芳基,苄基,杂环基;或者根据环上取代的可能性,被OH,卤素,CN,NO2,C1-C12烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C12烷硫基和,C1-C12卤代烷硫基一至三取代的芳基,苄基或杂环基;
R7为H,OH,由OH,或-S(=O)2-C1-C6烷基选择性取代的C1-C-24烷基,C1-C12链烯基,C1-C12炔基,C1-C12烷氧基,C1-C6烷氧基-C1-C6烷基,C1-C6烷氧基-C1-C6烷氧基,C2-C8链烯基氧基,芳基,芳氧基,苄氧基,杂环基,杂环氧基或-N(R8)2,式中两个R8可以互不相同;
R8为H,由一至五个选自卤素,C1-C6烷氧基,羟基和氰基选择性取代的C1-C6烷基,C1-C8环烷基,芳基,苄基,杂芳基;或根据环上取代的可能性由选自OH,卤素,CN,NO2,C1-C12烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C12烷硫基和C1-C12卤代烷硫基一至三取代的芳基,苄基或杂芳基;
R9为H,由一至五个选自卤素,C1-C6烷氧基,羟基和氰基选择性取代的C1-C6烷基;芳基,苄基,杂芳基;或根据环上取代的可能性由选自OH,卤素,CN,NO2,C1-C12烷基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C1-C12烷硫基和C1-C12卤代烷硫基一至三取代的芳基,苄基或杂芳基;
上述定义的限制条件是如果R2为H和R3为2-羟基乙基,异丙基,正辛基或苄基则R1不是仲丁基或异丙基;
或者,如果合适的话,式(I)所示化合物的E/Z异构体,E/Z异构体混合物和/或互变异构体。
2.含有至少一种如权利要求1中所述的式(I)所示化合物作为活性化合物和至少一种辅剂的农药。
3.一种防治害虫的方法,其中将如权利要求2中所述的组合物施用于害虫或害虫栖息地。
4.制备如权利要求2所述的组合物的方法,该组合物含有至少一种辅剂,其中活性化合物与辅剂密切混合和/或一起研磨。
5.如权利要求1中所述的式(I)所示化合物用于制备如权利要求2所述的组合物的用途。
6.权利要求2所述的组合物用于防治害虫的用途。
7.根据权利要求3所述的保护植物繁殖材料的方法,其中繁殖材料或繁殖材料种植的地点受到处理。
8.按照权利要求7叙及的方法处理的植物繁殖材料。
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CN103396465B (zh) * | 2013-07-19 | 2016-01-20 | 中国农业科学院植物保护研究所 | 一种阿维菌素烟碱二效价化合物及其制备和应用 |
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JP2004523562A (ja) | 2004-08-05 |
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RU2003127403A (ru) | 2005-03-27 |
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RU2334755C2 (ru) | 2008-09-27 |
MA26089A1 (fr) | 2004-04-01 |
CZ20032289A3 (cs) | 2003-11-12 |
WO2002068441A2 (en) | 2002-09-06 |
HUP0303265A2 (hu) | 2004-01-28 |
KR100872733B1 (ko) | 2008-12-08 |
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CA2435494A1 (en) | 2002-09-06 |
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BRPI0207652B1 (pt) | 2018-10-30 |
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AR032856A1 (es) | 2003-11-26 |
CA2435494C (en) | 2011-04-19 |
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