CN1042630C - 取代的氮杂环烷烃及其制备方法、用途和含其的杀害虫组合物 - Google Patents
取代的氮杂环烷烃及其制备方法、用途和含其的杀害虫组合物 Download PDFInfo
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- CN1042630C CN1042630C CN93119682A CN93119682A CN1042630C CN 1042630 C CN1042630 C CN 1042630C CN 93119682 A CN93119682 A CN 93119682A CN 93119682 A CN93119682 A CN 93119682A CN 1042630 C CN1042630 C CN 1042630C
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- alkyl
- ethyl
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- 150000001335 aliphatic alkanes Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 85
- 238000002360 preparation method Methods 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims description 125
- -1 6-chloro-pyridin-3-yl Chemical group 0.000 claims description 92
- 239000002585 base Substances 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 241000238631 Hexapoda Species 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 5
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- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
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- 229910052801 chlorine Inorganic materials 0.000 description 38
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 35
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- 238000012360 testing method Methods 0.000 description 19
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- 230000008859 change Effects 0.000 description 7
- 125000001188 haloalkyl group Chemical group 0.000 description 7
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 7
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- 125000002877 alkyl aryl group Chemical group 0.000 description 6
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- 150000003254 radicals Chemical class 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
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- 239000000975 dye Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
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- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
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- 239000002689 soil Substances 0.000 description 5
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- 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 4
- 241001465754 Metazoa Species 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
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- 229940117389 dichlorobenzene Drugs 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
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- 150000008282 halocarbons Chemical class 0.000 description 1
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- 125000005842 heteroatom Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
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- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 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 1
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- 150000007517 lewis acids Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
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- 235000019508 mustard seed Nutrition 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229940102127 rubidium chloride Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
本发明涉及通式(Ⅰ)的取代氮杂环烷烃,它们的制备方法以及它们作为杀害虫剂的应用。其中R1、R2、R3、R4、Y和Z的定义同说明书所述。
Description
本发明涉及新的取代的氮杂(环)烷烃,它们的制备方法,以及它们作为杀虫剂,特别是作为杀昆虫剂的应用。
业已知道,某些杂环化合物具有杀昆虫的性质(参见EP-A192060)。
R1代表五元或六元杂环基,该环含有1、2、3或4个氮原子和/或1或2个氧原子或硫原子作为杂原子环的成员-杂原子的数目是1、2、3或4-且该环可被以下基团任意取代:卤素、氰基、硝基、烷基、卤代烷基、链烯基、卤代链烯基、链炔基、烷氧基、卤代烷氧基、链烯基氧基、卤代链烯基氧基、链炔基氧基、烷基硫基、卤代烷基硫基、链烯基硫基、卤代链烯基硫基、链炔基硫基、烷基亚磺酰基、卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基、氨基、烷基氨基、二烷基氨基、芳基、芳基硫基、芳基氨基、芳烷基、甲酰氨基、烷基羰基氨基、甲酰基、氨基甲酰基、烷基羰基和/或烷氧基羰基。
R2代表羟基烷基、多羟基烷基、烷氧基烷基或多烷氧基烷基,
R3代表氢、烷基、羟基烷基、二羟基烷基、烷氧基烷基或二烷氧基烷基,
R2和R3一起代表羟基烷二基、二羟基烷二基、烷氧基烷二基、二烷氧基烷二基、氧代烷二基或二氧代烷二基,
R4代表氢、烷基(该烷基可被卤素、氰基、烷氧基、烷基硫基、二烷基氨基、三烷基甲硅烷基、烷氧基羰基、羧基、氨基甲酰基、烷基氨基羰基或二烷基氨基羰基,或被基团R1任意取代,其中R1的定义同上所述)、链烯基(可被卤素任意取代)、链炔基、苄基(可被卤素、氰基、硝基、烷基、卤代烷基、烷氧基或烷氧羰基任意取代)、甲酰基、烷基羰基(可被卤素、氰基、苯基、苯氧基或烷氧基任意取代)、环烷基羰基(可被卤素和/或烷基任意取代)、链烯基羰基(可被卤素任意取代)、苯基羰基或萘基羰基(它们可被卤素、烷基、卤代烷基、氰基、硝基、烷氧基和/或烷氧基羰基任意取代)、烷氧基羰基、苄氧基羰基、苯氧基羰基、烷硫羰基、苄硫羰基、苯硫羰基、烷基氨基羰基、二烷基氨基羰基、苯基氨基羰基(可被卤素、氰基、硝基、烷基、卤代烷基、烷氧基、卤代烷氧基、烷基硫基、卤代烷基硫基或烷氧羰基任意取代)、苯甲酰氨基羰基(可被卤素、烷基或卤代烷基任意取代)、苯磺酰基氨基羰基(可被卤素、烷基、卤代烷基、烷氧基、卤代烷氧基或烷氧基羰基任意取代)、烷基硫基(可被卤素任意取代)、苯基硫基(可被卤素、硝基或烷基任意取代)、烷基亚磺酰基、烷基磺酰基(可被卤素任意取代)、苯基亚磺酰基(可被卤素、硝基或烷基任意取代)、苯基磺酰基或萘基磺酰基(它们可被卤素、氰基、硝基、烷基、卤代烷基、烷氧基、卤代烷氧基和/或烷氧基羰基任意取代)、二烷基(硫代)磷酰基、烷基-烷氧基-(硫代)磷酰基或二烷氧基(硫代)磷酰基,
Y代表氮或CH基,并且
Z代表氰基或硝基。
用下列方法,可得到通式(Ⅰ)的新的取代氮杂(环)烷烃,即如果:
(a)任选地在酸接受体的存在下,任选地在催化剂的存在下或任选地在稀释剂的存在下,将通式(Ⅱ)的氮杂烷烃与通式(Ⅲa)的卤代化合物和/或通式(Ⅲb)的卤代化合物进行反应,其中R1、Y和Z的定义同上所述,
X-R2 (Ⅲa)
X-R3 (Ⅲb)其中,R2和R3的定义同上所述,以及
X代表卤素,
或者
(b)任选地在有反应助剂时并任选在稀释剂的存在下将通式(Ⅰ)的化合物(其中R2或R3代表二烷氧基烷基并且R1、R4、Y和Z的定义同上所述)加热,
或者
(c)任选地在有反应助剂时并任选地在稀释剂的存在下,将通式(Ⅰ)的化合物(其中R2和R3一起代表氧代烷二基并且R1、R4、Y和Z的定义同上所述)与氢化剂进行反应,
或者
(d)将通式(Ⅰ)的化合物(其中R2和R3一起代表烷氧基烷二基或二烷氧基烷二基并且R1、R4、Y和Z的定义同上所述)与卤化氢和/或碱金属卤化物在稀释剂的存在下反应,
或者
(e)任选地在酸结合剂的存在下并且任选地在稀释剂的存在下,将通式(Ⅰ)的化合物(其中R2和R3一起代表羟基烷二基或二羟基烷二基并且R1、R4、Y和Z的定义同上所述)与通式(Ⅳ)的烷基化试剂进行反应,
X1-R (Ⅳ)其中,
R代表烷基以及
X1代表卤素或基团-O-SO2-O-R(其中R的定义同上所述),
或者
(f)任选地在酸接受体的存在下并任选地在稀释剂的存在下,将通式(Ⅰ)的化合物(其中R4代表氢并且R1、R2、R3、Y和Z的定义同上所述)与通式(Ⅴ)的卤素化合物进行反应,
X-R4 (Ⅴ)其中,
X代表卤素并且
R4的定义同上所述,但不包括氢。
通式(Ⅰ)的新的取代氮杂(环)烷烃的显著特征在于它们作为杀昆虫剂的高活性。
本发明优先涉及式(Ⅰ)化合物,其中:
R1代表选自由以下基团组成的系列的五元至六元的杂环基:呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-或1,2,4-三唑基、噁唑基、异噁唑基、1,2,4-或1,3,4-噁二唑基、噻唑基、异噻唑基、1,2,3-或1,2,4-或1,2,5-或1,3,4-噻二唑基、吡啶基、哒嗪基、嘧啶基和吡嗪基,这些杂环基可被下列基团任意取代:氟、氯、溴、碘、氰基、硝基、C1-C4-烷基(可被氟和/或氯任意取代)、C2-C4-链烯基(可被氟和/或氯任意取代)、C2-C4-链炔基、C1-C4-烷氧基(可被氟和/或氯任意取代)、C3-C4-链烯基氧基(可被氟和/或氯任意取代)、C3-C4-链炔基氧基、C3-C4-烷基硫基(可被氟和/或氯任意取代)、C3-C4-链烯基硫基(可被氟和/或氯任意取代)、C3-C4-链炔基硫基、C1-C4-烷基亚磺酰基(可被氟和/或氯任意取代)、C1-C4-烷基磺酰基(可被氟和/或氯任意取代)、氨基、C1-C4-烷基基、二-(C1-C4-烷基)氨基、苯基、苯氧基、苯基硫基、苯基氨基、苄基、甲酰基氨基、C1-C4-烷基-羰基氨基、甲酰基、氨基甲酰基、C1-C4-烷基羰基和/或C1-C4-烷氧基-羰基,
R2代表C1-C6-羟基烷基、二羟基-C1-C6-烷基、C1-C4-烷氧基-C1-C4-烷基或二-(C1-C4-烷氧基)-C1-C4-烷基,
R3代表氢、C1-C6-烷基、C1-C6-羟基烷基、二羟基-C1-C6-烷基、C1-C4-烷氧基-C1-C4-烷基或二-(C1-C4-烷氧基)-C1-C4-烷基,或
R2和R3一起代表羟基-C2-C4-烷二基、二羟基-C2-C4-烷二基、C1-C4-烷氧基-C2-C4-烷二基、二-(C1-C4-烷氧基)-C2-C4-烷二基、氧代-C2-C4-烷二基或二氧代-C2-C4-烷二基,
R4代表氢、C1-C4烷基(可被以下基团任意取代:氟、氯、氰基、C1-C4-烷氧基、C1-C4-烷基硫基、二-(C1-C4-烷基)-氨基、三甲基甲硅烷基、C1-C4-烷氧基-羰基、羧基、氨基甲酰基、C1-C4-烷基-氨基羰基、二-(C1-C3-烷基)-氨基羰基,或被上述对R1的优选定义的杂环基(包括可能的取代基)任意取代)。C2-C4-链烯基(可被氟或氯任意取代)、C2-C4-链炔基、苄基(可被氟、氯、氰基、硝基、C1-C2-烷基、三氟甲基、C1-C2-烷氧基或C1-C2烷氧基羰基任意取代)、甲酰基、C1-C20-烷基-羰基(可被氟、氯、溴、苯基、苯氧基或C1-C4-烷氧基任意取代)、C3-C6-环烷基羰基(可被氟、氯和/或C1-C4-烷基任意取代)、C2-C20-链烯基-羰基(可被氟和/或氯任意取代)、苯基羰基或萘基羰基(它们可被氟、氯、溴、C1-C4-烷基、三氟甲基、氰基、硝基、C1-C4-烷氧基和/或C1-C4-烷氧基-羰基任意取代)、C1-C20-烷氧基-羰基、苄氧基羰基、苯氧基羰基、C1-C4-烷硫羰基、苄硫-羰基、苯硫-羰基、C1-C6-烷基氨基-羰基、二-(C1-C4-烷基)-氨基-羰基、苯基氨基-羰基(可被以下基团任意取代:氟、氯、溴、氰基、硝基、C1-C4-烷基、三氟甲基、C1-C4-烷氧基、C1-C2-氟烷氧基、C1-C2-氯氟烷氧基、C1-C4-烷基硫基、C1-C2氟烷基硫基、C1-C2-氯氟烷基硫基或C1-C4-烷氧基羰基)、苯甲酰基氨基-羰基(可被氟、氯、溴、甲基或三氟甲基任意取代)、苯基磺酰基氨基-羰基(可被氟、氯、溴、甲基、三氟甲基、C1-C4-烷氧基、C1-C2-氟烷氧基、C1-C2-氯氟烷氧基或C1-C4-烷氧基羰基任意取代)、C1-C4-烷基硫基(可被氟和/或氯任意取代)、苯基硫基(可被氟、氯、溴、硝基或甲基任意取代)、C1-C4-烷基亚磺酰基、C1-C4烷基磺酰基(可被氟和/或氯任意取代)、苯基亚磺酰基(可被氟、氯、溴、硝基或甲基任意取代)、苯基磺酰基或萘基磺酰基(它们可被以下基团任意取代:氟、氯、溴、氰基、硝基、甲基、三氟甲基、C1-C4-烷氧基、C1-C2-氟烷氧基、C1-C2-氯氟烷氧基和/或C1-C4-烷氧基羰基)、二甲基(硫代)磷酰基、C1-C4-烷基-C1-C4-烷氧基-(硫代)磷酰基或二(C1-C4-烷氧基)-(硫代)磷酰基,
Y代表氮或基团CH,并且
Z代表氰基或硝基。
本发明特别涉及式(Ⅰ)化合物,其中:
R1代表选自由下列基团组成的五元至六元杂环基:吡唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,5-噻二唑基、吡啶基、吡嗪基和嘧啶基,这些杂环基可被下列基团任意取代:氟、氯、溴、氰基、硝基、C1-C2-烷基(可被氟和/或氯任意取代)、C1-C2-烷氧基(可被氟和/或氯任意取代)、C1-C2-烷基硫基(可被氟和/或氯任意取代)或C1-C2-烷基磺酰基(可被氟和/或氯任意取代),
R2代表C1-C4-羟基烷基、二羟基-C1-C4-烷基、C1-C3-烷氧基-C1-C3-烷基或二-(C1-C3-烷氧基)-C1-C3-烷基,
R3代表氢、C1-C4-烷基、C1-C4-羟基烷基、二羟基-C1-C4-烷基、C1-C3-烷氧基-C1-C3烷基或二-(C1-C3-烷氧基)-C1-C3-烷基,或
R2和R3一起代表羟基-C2-C3-烷二基、二羟基-C2-C3-烷二基、C1-C3-烷氧基-C2-C3-烷二基、二-(C1-C3-烷氧基)-C2-C3-烷二基、氧代-C2-C3-烷二基或二氧代-C2-C3-烷二基,
R4代表氢、甲基、乙基、烯丙基、炔丙基、甲酰基、C1-C8-烷基羰基(可被氟和/或氯任意取代)、C1-C8-烷氧基-羰基、苄基氧基羰基、苯氧基羰基、苄基(可被氟或氯任意取代)或二-(C1-C2-烷氧基)-(硫代)磷酰基,
Y代表氮或基团CH,并且
Z代表氰基或硝基。
特别优选的式(Ⅰ)化合物是,其中:
R1代表6-氯-3-吡啶基(6-氯-吡啶-3-基)或代表-2-氯-5-噻唑基(2-氯-噻唑-5-基),
R2代表羟基甲基、羟基乙基、羟基丙基、二羟基乙基、二羟基丙基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、二甲氧基乙基或二乙氧基乙基,
R3代表氢、甲基、乙基、羟基甲基、羟基乙基、羟基丙基、二羟基乙基、二羟基丙基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、二甲氧基乙基或二乙氧基乙基,
R2和R3一起代表氧代乙烷-1,2-二基、二氧代乙烷-1,2-二基、羟基乙烷-1,2-二基、二羟基乙烷-1,2-二基、甲氧基乙烷-1,2-二基、乙氧基乙烷-1,2-二基、二甲氧基乙烷-1,2-二基或二乙氧基乙烷-1,2-二基,
R4代表氢或甲基,
Y代表氮或基团CH,并且
Z代表氰基或硝基。
在根据本发明的通式(Ⅰ)化合物的定义中的如上所述的烃基,例如烷基,包括与杂原子结合,如在烷氧基中那样,应尽可能在每种情形中是直链或支链的。
通常,卤素代表氟、氯、溴或碘,优选氟、氯或溴,特别优选氟或氯。
上面列举的一般基团的定义或说明,或那些列于优选范围内的定义或说明,以相应的方式不仅对式(Ⅰ)的终产物有效,也对具有式(Ⅰ)的起始化合物和中间体有效。
基团的定义可按要求组合在一起,因而也在各自优选的范围内。
如果,例如,将1-(2-氯-噻唑-5-基-甲基)-2-硝基亚甲基-5-氧代-咪唑烷和硼氢化钠用作起始化合物,则根据本发明的方法(C)的反应过程可用以下反应式表示:
如果,例如,将1-(6-氯-吡啶-3-基-甲基)-2-氰基亚甲基-4-甲氧基-咪唑啉和溴化氢用作起始化合物,则根据本发明的方法(d)的反应过程可用以下反应式表示:
为制备式(Ⅰ)化合物,在根据本发明的方法(a)中可用作起始化合物的氮杂烷烃一般可用式(Ⅱ)定义。
在式(Ⅱ)中,R1、Y和Z优选或特别优选地具有上面已经说明的含义,那些含义与根据本发明的式(Ⅰ)化合物的描述有关,对R1、Y和Z的定义是其中优选或特别优选的。
式(Ⅱ)起始化合物是已知的和/或可由本身已知的方法制备
(参见:EP-A 302389,EP-A 306696,EP-A 364844,
EP-A 375907,EP-A 376297,EP-A 381130,EP-A 418199,
EP-A 425978,EP-A 428941,EP-A 452782)。
根据本发明的方法(a)另外用作起始化合物来制备式(Ⅰ)化合物的卤化物一般由式(Ⅲa)和式(Ⅲb)定义。
在式(Ⅲa)和式(Ⅲb)中,R2和R3优选或特别优选地具有上面已经说明的含义,那些含义与根据本发明的式(Ⅰ)化合物的描述有关,对R2和R3的定义是其中优选或特别优选的;X在每种情形中优选代表氯或溴。
对于有机合成,式(Ⅲa)和(Ⅲb)起始化合物是已知化合物。
一般用于此类反应的所有酸结合剂均可在根据本发明的方法(a)中用作酸接受体。优选使用的是那些碱金属或碱土金属氢化物,例如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属氢氧化物,例如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属碳酸盐和碳酸氢盐,例如钠和钾的碳酸盐或碳酸氢盐,以及碳酸钙,碱金属乙酸盐,例如乙酸钠和乙酸钾,碱金属醇化物,例如钠和钾的甲醇盐、乙醇盐、丙醇盐、异丙醇盐、丁醇盐、异丁醇盐和叔丁醇盐,另外还有碱性氮化合物,例如三甲胺、三乙胺、三丙胺、三丁基胺、二异丁基胺、二环己基胺、乙基二异丙基胺、乙基二环己基胺、乙基二异丙基胺、乙基二环己基胺、N,N-二甲基苄基胺、N,N-二甲基-苯胺、吡啶、2-甲基-吡啶、3-甲基-吡啶、4-甲基-吡啶、2,4-二甲基-吡啶、2,6-二甲基-吡啶、2-乙基-吡啶、4-乙基-吡啶和5-乙基-2-甲基-吡啶、1,5-二氮杂双环-[4,3,0]-壬-5-烯(DBN)、1,8-二氮杂双环[5,4,0]-十一-7-烯(DBU)和1,4-二氮杂双环-[2,2,2]-辛烷(DABCO)。
根据本发明的方法(a)任选地在催化剂的存在下进行。在此合适的催化剂特别有,碱金属盐例如氯化钾、氯化铷和氯化铯。
为制备式(Ⅰ)的新型化合物根据本发明的方法(a)优选地使用稀释剂来进行。在此,实际上所有惰性有机溶剂都是合适的稀释剂。这些优选包括脂肪族和芳香族、并且可任意卤代的烃,例如戊烷、己烷、庚烷、环己烷、石油醚、汽油、石油英、苯、甲苯、二甲苯、二氯甲烷、氯代乙烯、氯仿、四氯化碳、氯苯和邻-二氯苯;醚类,例如二乙基醚和二丁基醚、乙二醇二甲基醚和二乙二醇二甲基醚、四氢呋喃和二噁烷;酮类,例如丙酮、甲基乙基酮、甲基异丙基酮、和甲基异丁基酮;酯类,例如乙酸甲酯和乙酸乙酯;腈类,例如乙腈和丙腈;酰胺类,例如二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮,以及二甲亚砜、四氢噻吩砜和六甲基磷三酰胺。
在根据本发明的方法(a)中,反应温度可在相当宽的范围内变化。一般来说,可用0℃和200℃之间的温度,优选20℃到150℃之间的温度。
根据本发明的方法(a)通常在大气压下进行。但是,也可能在升高或降低的压力下进行。
为进行根据本发明的方法(a),在每种情形中所要求的起始化合物通常使用近似相等的摩尔量。但是,在每种情形中所用的两种组份,将其中之一以较大的过量使用也是可能的。反应通常在合适的稀释剂中、在酸接受体的存在下以及任选地在催化剂的存在下进行,并且将反应混合物在每种情形中所要求的温度下搅拌几个小时。在根据本发明的方法(a)中,每种情形均可按照常规的方法进行后处理(参见制备实施例)。
在根据本发明的方法(b)中用作起始化合物的化合物通常用式(Ⅰ)定义,条件是R2或R3代表二烷氧基烷基。此时,基团R1、R2、R3、R4、Y和Z优选或特别优选具有上面已经说明的含义,那些含义在对根据本发明的式(Ⅰ)化合物的描述的范围内,是其中优选或特别优选的。
根据本发明,上面所描述的用于方法(b)的式(Ⅰ)起始化合物是新的化合物;它们可用根据本发明的方法(a)来制备。
根据本发明的方法(b)任选地是在有反应助剂的存在下进行。此处合适的反应助剂具体有路易斯酸,例如三氟化硼或三氯化铝,也可为无机酸,例如盐酸、硫酸、甲磺酸、苯磺酸和对-甲苯磺酸。
根据本发明的方法(b)优选的是在使用稀释剂的情况下进行。在此处,那些在根据本发明的方法(a)的描述中已被提到的稀释剂是合适的。另外,水,以及醇类,例如甲醇、乙醇、正-或异-丙醇和正-或异-或仲-或叔-丁醇,也可在方法(b)中有利地用作稀释剂。
在根据本发明的方法(b)中,反应温度可在相当宽的范围内变化。一般来说,可用的温度在20℃到150℃之间,优选使用40℃到100℃之间的温度。
根据本发明的方法(b)通常在大气压下进行。但是,将其在升高或降低的压力下进行也是可能的。
为进行根据本发明的方法(b),通常在室温下将反应组分混合,然后在所要求的温度下搅拌直至反应结束。后处理工作可按常规方法进行(参见制备实施例)。
在根据本发明方法(c)中用作起始化合物的化合物通常由式(Ⅰ)定义,条件是R2和R3一起代表氧代烷二基。此时,基团R1、R2、R3、R4、Y和Z优选或特别优选具有上面已经说明的含义,那些含义在对根据本发明的式(Ⅰ)化合物的描述的范围内,是其中优选或特别优选的。
根据本发明,上面描述的用于方法(c)的式(Ⅰ)起始化合物是新的化合物;它们可按根据本发明的方法(a)来制备。
根据本发明的方法(c)可用氢化剂实现。此处合适的试剂特别有,金属氢化复合物,例如硼氢化锂(LiBH4)、氢化锂铝(LiAlH4)和硼氢化钠(NaBH4),它们适合于将羰基化合物氢化成羟基化合物。
方法(c)任选地在有反应助剂的存在下进行。此处合适的反应助剂最好是酸,例如盐酸、硫酸或乙酸。
实现方法(c)最好使用稀释剂。此处,那些在根据本发明的方法(a)的描述中已经提到的稀释剂是非常合适的。另外,水、醇类,例如甲醇、乙醇、正-或异-丙醇,另外还有羧酸,例如乙酸和丙酸,也可有利地用作在方法(c)中的稀释剂。
在根据本发明的方法(c)中,反应温度可在相当宽的范围内变化。一般来说,可用-20℃到+50℃之间的温度,优选使用0℃到+30℃之间的温度。
根据本发明的方法(c)通常在大气压下进行。但是在升高或降低的压力下进行也是可能的。
为进行根据本发明的方法(c),在每种情形中所要求的起始化合物通常使用近似相等的摩尔量。但是也可能将每种情形中所用的两个组份中的一个以较大过量地使用。反应通常在合适的稀释剂中、在有反应助剂的存在下进行,并且将反应混合物在每种情形中所要求的温度下搅拌。在根据本发明的方法(c)中的后处理工作在每种情形中均按常规方法实现(参见制备实施例)。
在根据本发明的方法(d)中用作起始化合物的化合物通常由式(Ⅰ)定义,条件是R2和R3一起代表烷氧基烷二基或二烷氧基烷二基。此时,基团R1、R2、R3、R4、Y和Z优选地或特别优选地具有上面已经说明的含义,那些含义在根据本发明的式(Ⅰ)化合物的描述的范围内,是其中优选或特别优选的。
根据本发明,上面描述的用于方法(d)的式(Ⅰ)起始化合物是新的化合物;它们可通过根据本发明的方法(a)或(b)来制备。
根据本发明的方法(d)是在卤化氢和/或碱金属卤化物的存在下进行。优选地使用氯化氢或溴化氢,和/或相应的钠或钾的卤化物,即钠或钾的氯化物或溴化物。
优选地使用稀释剂来进行方法(d)。除水以外,此处优先适用的还有那些在根据本发明的方法(a)的描述中已经被提到的稀释剂。
在根据本发明的方法(d)中,反应温度可在相当宽的范围内变化。一般来说,所用的温度在0℃到100℃之间,优选地使用20℃到80℃之间的温度。
根据本发明的方法(d)通常在大气压下进行。但是在升高或降低的压力下进行也是可能的。
为进行根据本发明的方法(d),每种情形中所要求的起始化合物通常使用近似相等的摩尔量。但是在每种情形中所用的两个组份中的一个以较大的过量使用也是可能的。反应通常在合适的稀释剂中进行,并且将反应混合物在每种情形中所必需的温度下搅拌几小时。在根据本发明的方法(d)中,每种情形均按常规方法进行后处理(参见制备实施例)。
在根据本发明的方法(e)中用作起始化合物的化合物通常由式(Ⅰ)定义,条件是R2和R3一起代表羟基烷二基或二羟基烷二基。此时,基团R1、R2、R3、R4、Y和Z优选地具有上面已经说明的含义,在根据本发明的式(Ⅰ)化合物的描述的范围内,是其中优选或特别优选的。
根据本发明,上面所描述的用于方法(e)的式(Ⅰ)起始化合物是新的化合物。它们可通过根据本发明的方法(c)或(d)来制备。
为制备式(Ⅰ)化合物,在根据本发明的方法(e)中另外用作起始化合物的烷基化试剂通常由式(Ⅳ)定义。
在式(Ⅳ)中,
R优选地代表C1-C4-烷基,最好是甲基或乙基,并且
X优选地代表氯、溴或碘,或基团-O-SO2-OR,其中R的定义同上。
对于有机合成,式(Ⅳ)起始化合物是已知的化合物。
根据本发明的方法(e)优选地在有酸接受体的存在下进行。此处优选适用的是那些上面在根据本发明的方法(a)的描述中已被提到的酸结合剂。
根据本发明的方法(e)最好使用稀释剂进行。此处优先适用的是上面在根据本发明的方法(a)的描述中已被提到的那些稀释剂。
在根据本发明的方法(e)中,反应温度可在相当宽的范围内变化。通常使用0℃到150℃之间的温度,优选使用20℃到100℃之间的温度。
根据本发明的方法(e)通常在大气压下进行。但在升高或降低的压力下进行也是可能的。
为进行根据本发明的方法(e),每种情形中所要求的起始化合物通常使用近似相等的摩尔量。但是,将在每种情形中所用的两个组份中的一个以较大的过量使用也是可能的。反应通常在适合的稀释剂中、在有酸接受体的存在下进行,并且将反应混合物在每种情形中必需的温度下搅拌几个小时。在根据本发明的方法(e)中,每种情形均按常规方法进行后处理(参见制备实施例)。
在根据本发明的方法(f)中用作起始化合物的化合物通常由式(Ⅰ)定义,条件是R4代表氢。此处,基团R1、R2、R3、Y和Z优选地或特别优选地具有上面已经说明的含义,在根据本发明的式(Ⅰ)化合物的描述的范围内,是其中优选或特别优选的。
根据本发明,上面所描述的用于方法(f)的式(Ⅰ)起始化合物是新的化合物;它们可通过根据本发明的方法(a)~(d)制备。
为制备式(Ⅰ)化合物,在根据本发明的方法(f)中另外用作起始化合物的卤素化合物通常由式(Ⅴ)定义。
在式(Ⅴ)中,R4优选地或特别优选地具有上面已经说明的含义,这些含义与根据本发明的式(Ⅰ)化合物的描述有关,R4是其中优选或特别优选的。
X优选代表氟、氯、溴或碘,最好代表氯或溴。
对于有机合成,式(Ⅴ)起始化合物是已知的化合物。
根据本发明的方法(f)反应优选地是在有酸接受体存在的条件下进行。此处,优先适用的是上面在根据本发明的方法(a)的描述中已被提到的那些酸结合剂。
根据本发明的方法(f)最好使用稀释剂进行。此处,优先适用的是上面在根据本发明的方法(a)的描述中已被提到的那些稀释剂。
在根据本发明的方法(f)中,反应温度可在相当宽的范围内变化。通常使用0℃到150℃之间的温度,优选使用20℃到100℃之间的温度。
根据本发明的方法(f)通常在大气压下进行。但在升高或降低的压力下进行也是可能的。
为进行根据本发明的方法(f),在每种情形中所要求的起始化合物通常用近似相等的摩尔量。但是,将每种情形中所用的两个组份中的一个以较大的过量使用也是可能的。反应通常在合适的稀释剂中,在酸接受体的存在下进行,并且将反应混合物在每种情形中所要求的温度下搅拌几个小时。在根据本发明的方法(f)中,每种情形均按常规方法进行后处理。
只要是植物对它有很好的耐受性并且它对温血动物有较小的毒性,该活性化合物就适用于控制有害动物,特别是昆虫、蛛形纲动物和线虫,这些害虫可见于农业、林业、贮存的产品和原材料的保护以及卫生领域中。这些化合物对有正常敏感性和对药物有耐受性的害虫种系以及对害虫的所有或各个发展阶段都是有活性的。上面提到的害虫包括:
等足目,例如,潮虫、平甲和鼠妇。
倍足亚纲,例如,具斑马陆。
唇足纲,例如,食果地蜈蚣和蚰蜒属。
综合纲,例如,庭院么蚰。
缨尾目,例如,西洋衣鱼。
弹尾目,例如,具刺跳虫。直翅目,例如,东方蜚蠊、美洲蟒蠊、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,犀白蚁属。
虱目,例如,葡萄根瘤蚜、瘿绵蚜属、体虱、血虱属和长颚虱属。
食毛目,例如,嚼虱属和畜虱属。
缨翅目,例如,温室条篱蓟马和烟蓟马。
异翅亚目,例如,扁盾蝽属、红蝽属、方背皮蝽、温带臭虫、长红猎蝽和锥猎蝽属。
半翅目,例如,甘蓝粉虱、木薯粉虱、温室粉虱、棉蚜、甘蓝蚜、茶藨隐瘤蚜、Doralis fabae、Doralis pomi、苹果绵蚜、梅大尾蚜、麦长管蚜、瘤蚜属、忽布疣蚜、禾谷缢管蚜、小绿叶蝉属、双叶叶蝉、黑尾叶蝉、水木坚蚧、乌盔蚧、灰飞虱、褐飞虱、红肾园盾蚧、常春藤园盾蚧、粉蚧属、木虱属。
鳞翅目,例如,红铃麦蛾、松尺蠖、冬尺蠖蛾、苹细蛾、苹果巢蛾、菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜蛾、桔潜蛾、地老虎属、切根虫属、夜蛾属、埃及金刚钻、实夜蛾属、莎草夜蛾、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、灰翅夜蛾属、粉纹夜蛾、苹果小卷蛾、菜粉蝶属、禾草螟属、玉米螟、地中海粉斑螟、大蜡螟、幕谷蛾、袋谷蛾、褐织蛾、亚麻黄卷蛾、具网卷叶蛾、枞色卷蛾、葡萄果蠹蛾、茶长卷蛾和栎绿卷蛾。
鞘翅目,例如,家具窃蠹、谷蠹、Bruchidius obtectus、大豆象、北美家天牛、杨树萤叶甲、马铃薯叶甲、辣根猿叶甲、条叶甲属、油菜金头跳甲、墨西哥豆飘虫、隐食甲属、锯谷盗、花象属、谷象属、黑葡萄耳象、香蕉根颈象、白菜籽龟象、紫苜蓿叶象、皮蠹属(Dermestesspp.)、皮蠹属(Trogoderma spp.)、园皮蠹属、毛皮蠹属、粉蠹属、油菜花露尾甲、蛛甲属、黄蛛属、裸蛛甲、拟谷盗属、黄粉虫、叩甲属、宽胸叩头虫属、西方五月鳃角金龟、马铃著鳃角金龟以及褐新西兰肋翅鳃角金龟。
膜翅目,例如,锯角叶蜂属、叶蜂属、蚁属、法老蚁和胡蜂属。
双翅目,例如,伊蚊属、按蚊属、库蚁属、黑尾果蝇、家蝇属、厕蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、厩螫蝇属、狂蝇属、皮蝇属、虻属、螗蜩属、花圆毛纹、瑞典麦杆蝇、草种蝇属、甜菜泉蝇、地中海实蝇、橄榄大实蝇和欧洲大蚊。
蚤目,例如,印度客蚤和叶蚤属。
蛛形纲,例如,Scorpio maurus和黑寡妇球腹蛛。
蜱螨目,例如,粗脚粉螨、锐缘蜱属、钝缘蜱属、鸡皮利螨、茶藨瘿螨、桔芸锈螨、牛蜱属、扇头蜱属、花蜱属、璃眼蜱属、硬蜱属、痒螨属(Psoroptes spp.)、痒蜱属(Chorioptes spp.)、疥螨属、跗线螨属、苜蓿苔螨、全爪螨属和叶螨属。
植物寄生虫线虫包括草地垫刃线虫属、内侵线虫属、双垫刃属、柑桔垫刃线虫、异皮线虫属、根结线虫属、滑刃线虫属、Longidorusspp.,剑线虫属和Trichodorus spp.。
根据本发明的式(Ⅰ)活性化合物的显著特征在于其非常好的杀昆虫活性。它们作为叶子杀昆虫剂和作为地面杀昆虫剂均展现出很强的作用,例如可用它们抗甲虫幼虫(如辣根猿叶甲)、抗水稻叶跳虫(如黑尾叶蝉)和抗叶子蚜早(如桃蚜和豆卫矛蚜)。
根据本发明的式(Ⅰ)活性化合物也适用于杀灭节肢动物,这些节肢动物寄生于农业产出的家畜例如,牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅和蜜蜂,其它宠物,例如狗、猫、笼养鸟和缸养鱼,还有所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。通过杀灭这些节肢动物,牲畜的死亡例数以及生产率(对于肉、奶、羊毛、皮革、蛋、蜂蜜等)的降低应该减少,这样,通过应用根据本发明的活性化合物,使更经济更简单的畜牧业成为可能。
在兽医方面,根据本发明的活性化合物是以已知的方式应用:例如可通过以下形式内用:片剂、胶囊剂、饮剂、兽用顿服药、颗粒剂、膏剂、丸剂、搀在饲料中喂予的方法以及栓剂,通过非胃肠道施用,例如,通过注射(肌肉内)、经鼻给药,以以下形式经皮肤施用;浸泡或洗浴、喷洒、倾倒以及定点涂擦、洗涤和搽粉,也可用含有活性化合物的某种形状的物品帮助施用,例如颈圈、耳戳、尾签、肢带、笼头、标记装置等。
依据它们具体的物理的和/或化学的性质,活性化合物可被转变成常规使用的制剂,例如溶液剂、乳剂、悬浮液剂、粉剂、泡剂、膏剂、颗粒剂、气雾剂、混有活性化合物的天然与合成的材料、在聚合物质中和在包衣组分中用于种子的非常精细的胶囊剂,另外还有用燃烧装置使用的制剂,例如熏筒、熏罐、熏卷等,以及超低容量(ULV)冷雾和暖雾制剂。
这些制剂用已知的方式生产,例如通过将活性化合物与以下增量剂混合:即液体溶剂、在压力下的液化气,和/或固体载体,任选地与以下表面活性剂混合使用:即乳化剂和/或分散剂,和/或发泡剂。在以水用作增量剂时,例如,有机溶剂也可用作辅助溶剂。合适的液体溶剂主要有:芳香族化合物,例如二甲苯、甲苯或烷基萘,氯化的芳香烃或氯化脂肪烃,例如氯苯、氯乙烯或二氯甲烷,脂肪烃,例如环己烷或链烷烃,如矿物油馏份,醇类,例如丁醇或乙二醇以及它们的醚和酯,酮类,例如丙酮、甲基乙基酮、甲基异丁基酮或环己酮,强极性溶剂,例如二甲基甲酰胺和二甲亚砜,以及水;被液化的气体增量剂或载体是指在环境温度和大气压下是气态的液体,例如气雾推进剂,如卤化烃以及丁烷、丙烷、氮气和二氧化碳;合适的固体载体有:例如碾碎的天然矿物,如高岭土、粘土、滑石、白垩、石英、活性白土、蒙脱土、或硅藻土,以及碾碎的合成矿物,例如高分散性二氧化硅、氧化铝和硅酸盐;用于颗粒剂的合适的固体载体有:例如压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,以及无机和有机粉的合成颗粒,还有有机材料如椰子壳、玉米芯和烟草杆的颗粒;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,如烷基芳基聚乙二醇醚、烷基磺酸酯、硫酸烷基酯、芳基磺酸酯以及白蛋白水解产物;合适的分散剂有:例如木素亚硫酸盐废液和甲基纤维素。
在制剂中可使用的粘附剂有,例如,羧甲基纤维素和以粉末、颗粒或乳胶形式的天然与合成的聚合物,如阿拉伯胶、聚乙烯醇和聚乙烯乙酸酯,还有天然磷脂,如脑磷脂和卵磷脂以及合成的磷脂。其它的添加剂可以是矿物和植物油。
也可使用色素,例如无机颜料,如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,以及痕量营养素如铁、镁、硼、铜、钴、钼和锌的盐。
制剂中通常含有0.1~95%(以重量计)的活性化合物,最好在0.5~90%之间。
根据本发明的活性化合物可以存在于它们的市售制剂中,也可存在于由这些制剂制得的使用形式中,作为与以下其它活性化合物形成的混合物:例如杀昆虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节物质或除草剂。杀昆虫剂包括例如,磷酸酯、氨基甲酸酯、羧酸酯、氯代烃、苯脲、特别是由微生物产生的物质。
根据本发明的活性化合物可以存在于它们的市售制剂中,也可存在于由这些制剂制得的使用形式中,作为与增效剂形成的混合物。增效剂是增加活性化合物的作用的化合物,对于加入的增效剂本身并不要求它必须具有活性。
由市售制剂制得的使用形式的活性化合物含量可在宽的范围内变化。使用形式的活性化合物的浓度可以是0.0000001~95%(以重量计)的活性化合物,优选0.0001~1%(以重量计)。
具体应用是以适合于使用形式的常规方式实现的。
当用于抗卫生学虫害和贮存产品的虫害时,活性化合物的特征在于在木头和粘土上有极好的残留作用以及对用石灰处理的物质上的碱有很好的稳定性。
制备实施例:
实施例1
(方法(a))
将1.15g(5.0mmol)的1-(6-氯-吡啶-3-基-甲基)-2-硝基胍、0.76g(5.5mmol)的碳酸钾、0.09g(0.5mmol)的氯化铯、0.92ml(5.5mmol)的溴乙醛二乙缩醛和5ml二甲基甲酰胺的混合物加热到125℃,同时搅拌,并在此温度下搅拌2小时。在加入另外的0.76g(5.5mmol)的碳酸钾和另外的0.92ml(5.5mmol)的溴乙醛二乙缩醛后,将混合物在125℃再搅拌2小时。
冷却到室温之后,再将混合物用冰水稀释到约四倍体积,并用二氯甲烷萃取。将有机相用硫酸钠干燥,然后过滤。浓缩滤液,其残渣用冰冷的环己烷浸渍。将在此过程中仍不溶的糖浆状粗品用柱层析(硅胶;二氯甲烷/乙酸乙酯1∶1)纯化。
这样得到了0.16g(理论值的9%)的1-(6-氯-吡啶-3-基-甲基)-1-(2,2-二乙氧基乙基)-2-硝基胍,为非晶形第二级份。
1H-NMR(CDCl3,δ):-CH(OC2H5)2 4.59ppm(三重峰)
<方法(b)>
将1.45g(4.2mmol)的1-(6-氯-吡啶-3-基-甲基)-1-(2,2-二乙氧基-乙基)-2-硝基-胍和44ml乙醇的混合物加热到78℃,在另外加入0.725ml(7.25mmol)的浓盐酸后,将混合物在此温度下搅拌15分钟。
冷却到室温后,将混合物用乙酸乙酯稀释到约3倍体积,然后用碳酸氢钾水溶液中和。分出有机相,用硫酸钠干燥然后过滤。浓缩滤液,残渣再用柱层析(硅胶;二氯甲烷/甲醇15∶1)纯化。得到1.2g(理论值的95%)1-(6-氯-吡啶-3-基-甲基)-2-硝基亚氨基-4-乙氧基-咪唑烷,为非晶形的第二级份。
1H-NMR(DMSO3,δ):4-CH 5.90ppm
5-CH2 3.70ppm(多重峰)实施例3
将4.2g(15.5mmol)的1-(6-氯-吡啶-3-基-甲基)-2-硝基亚氨基-5-氧代-咪唑烷溶解在495ml的四氢呋喃中,然后向该溶液加入25.2ml(25.2mmol的HCl)1N盐酸。
将混合物冷却到15℃,在此温度下向混合物中滴加42ml 4%浓度的硼氢化钠水溶液。再搅拌30分钟后,将溶液倾出与不溶性固体分离并浓缩。然后加入200ml饱和的氯化钠水溶液,再将该混合物用乙酸乙酯萃取3次,每次200ml。
将合并的有机相用硫酸钠干燥,然后过滤。浓缩滤液,残渣用200ml的乙酸乙酯/乙腈(10∶1)的溶液浸渍,并通过抽滤分离仍不溶的产物。
第一个产品级份:0.6g的棕黄色晶体。将滤液在硅胶柱上分离。
第二个产品级份:2.8g的无色晶体;
熔点:192℃
总产率:3.4g(理论值的80%)的1-(6-氯-吡啶-3-基-甲基)-2-硝基亚氨基-5-羟基-咪唑烷。
实施例4
将0.36g(1.2mmol)的1-(6-氯-吡啶-3-基-甲基)-2-硝基亚氨基-4-乙氧基-咪唑烷、36ml四氢呋喃、36ml饱和的氯化钠水溶液和2.4ml 1N盐酸的混合物在45℃下搅拌105分钟。
冷却到室温后,用碳酸氢钾溶液将两相反应混合物调到pH8,然后用乙酸乙酯萃取3次。将合并的萃取液用硫酸钠干燥,并且过滤。浓缩滤液,残渣用乙醚浸渍,得到的晶状产物通过抽滤分离。
得到0.143g(理论值的44%)的1-(6-氯-吡啶-3-基-甲基)-2-硝基亚氨基-4-羟基-咪唑烷,熔点为170℃。
<方法(e)>
将1.1g(4.0mmol)的1-(6-氯-吡啶-3-基-甲基)-2-硝基亚氨基-5-羟基-咪唑烷溶于10ml的二甲基甲酰胺中,然后在搅拌的情况下向该溶液分批加入0.24g(8.0mmol)的氢化钠。将此混合物在15℃下搅拌30分钟。然后在+5℃下向其中滴加0.5ml(8.0mmol)碘甲烷,再将反应混合物在20℃下搅拌2小时。然后将混合物用水稀释到约3倍体积,再用乙酸乙酯萃取3次。用硫酸钠干燥合并的萃取液并过滤。浓缩滤液,再将残渣用柱层析(硅胶/乙酸乙酯)分离。
得到0.80g(理论值的67%)的1-(6-氯-吡啶-3-基-甲基)-2-硝基亚氨基-3-甲基-5-甲氧基-咪唑烷,为非晶形的第三级分。
1H-NMR(CDCl3,)OCH3 3.26ppm(单峰)
NCH3 3.01ppm(单峰)
应用实施例
实施例A
猿叶甲属幼虫试验
溶剂:7份(以重量计)二甲基甲酰胺
乳化剂:1份(以重量计)烷基芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(以重量计)活性化合物与所述量的溶剂和所述量的乳化剂混合,并将该浓溶液用水稀释到所要求的浓度。
通过将卷心菜叶(花椰)(Brassica oleracea)浸在具有所要求的浓度的活性化合物制剂中对其进行处理,然后在叶子仍然湿润时,使其感染上芥子甲虫幼虫(辣根猿叶甲)。
经过所要求的时间后,测定用%表示的杀灭情况。100%指的是所有甲虫幼虫均被杀死;0%是指没有甲虫幼虫被杀死。
在该试验中,例如,根据制备实施例(1)、(3)、(5)和(6)所得到的化合物,在活性化合物的浓度为0.1%时,在7天后,显示出对试验动物的100%杀灭率。
实施例B
叶蝉试验
溶剂:7份(以重量计)二甲基甲酰胺
乳化剂:1份(以重量计)烷基芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(以重量计)活性化合物与所述量的溶剂和所述量的乳化剂混合,再将该浓溶液用水稀释到所要求的浓度。
通过将水稻秧苗(Oryza sativa)浸在具有所要求浓度的活性化合物的制剂中对其进行处理,在秧苗仍然湿润时,使其感染上绿稻叶跳虫(黑尾叶蝉)的幼虫。
经过所要求的时间以后,测定以%表示的杀灭情况。100%是指所有叶子跳虫均被杀死;0%是指没有杀死任何叶子跳虫。
在该试验中,例如,按照制备实施例(1)、(3)、(5)和(8)获得的化合物,在活性化合物的浓度为0.1%时,在6天之后,显示出对试验动物100%的杀灭率。
实施例C
瘤蚜属试验
溶剂:7份(以重量计)二甲基甲酰胺
乳化剂:1份(以重量计)烷基芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(以重量计)活性化合物与所述量的溶剂和所述量的乳化剂混合,再将该浓溶液用水稀释到所要求的浓度。
通过将严重感染了绿桃蚜虫(桃蚜)的卷心菜叶(花椰)浸在具有所要求浓度的活性化合物制剂中,对其进行处理。
经过所要求的时间之后,测定以%表示的杀灭率。100%是指所有的试验昆虫均被杀死;0%是指未杀死任何蚜虫。
在该试验中,例如,按照制备实施例(1)和(5)获得的化合物,在活性化合物的浓度为0.1%时,在6天以后,显示出对试验动物100%的杀灭率。
实施例D
蚜属试验(内吸收作用)
溶剂:7份(以重量计)二甲基甲酰胺
乳化剂:1份(以重量计)烷基芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(以重量计)活性化合物与所述量的溶剂和所述量的乳化剂混合,并将该浓溶液用水稀释到所要求的浓度。
将已经严重感染上黑大豆蚜虫(豆卫矛蚜)的大豆植株(蚕豆)逐棵用20ml具有所要求的浓度的活性化合物制剂进行浇灌,方法是使活性化合物制剂渗入土壤中而不润湿秧苗。通过根将活性化合物吸收然后到达秧苗。
经过所要求的时间之后,测定以%表示的杀灭率。100%是指所有试验昆虫均被杀死;0%是指未杀死任何试验昆虫。
在该试验中,例如,按照制备实施例(3)和(5)获得的化合物,在活性化合物的浓度为0.1%时,在4天之后,显示出对试验动物的100%的杀灭率。
实施例E
临界浓度试验/根的内吸收作用
试验昆虫:桃蚜
溶剂:4份(以重量计)丙酮
乳化剂:1份(以重量计)烷基芳基聚乙二醇醚
为制得合适的活性化合物制剂,将1份(以重量计)活性化合物与所述量的溶剂混合,加入所述量的乳化剂,再将该浓溶液用水稀释到所要求的浓度。
将活性化合物制剂与土壤很好地混合。活性化合物在制剂中的浓度实际上并不重要,只有每单位体积的土壤中的活性化合物的量(以重量计)(以ppm(=mg/L)给出)才是决定性的。将处理过的土转移到盆中并种上卷心菜(花椰)。活性化合物可通过这种方法由植物的根从土壤中吸收并运输到叶子。
为了说明根内吸收作用,7天后将叶子感染上上述的试验昆虫。再过2天后,通过计算或估量死的昆虫数进行评估。从死亡数率推断对活性化合物的根的内吸收作用。如果所有试验动物均被杀死则为100%,如果仍然存活的试验昆虫与未经处理的对照实例中数目一样多则为0%。
在该试验中,例如,按照制备实施例(1)和(3)获得的化合物,在活性化合物的浓度为20ppm时,显示出对试验动物100%的杀灭率。
实施例F
绿头蝇幼虫试验
试验动物:铜绿蝇(lucilia cuprina)幼虫
乳化剂:35份(以重量计)乙二醇单甲基醚
35份(以重量计)壬基酚聚乙二醇醚
为制得合适的活性化合物制剂,将3份(以重量计)活性化合物与7份(以重量计)上述混合物混合,由此获得的浓乳液再用水稀释到每种情形中所要求的浓度。
将约20只铜绿蝇幼虫放在盛有约1cm3的马肉和0.5ml活性化合物的试管中。24小时后,测定活性化合物制剂的效果。100%是指所有绿头蝇幼虫均被杀死;0%是指未杀死任何绿头蝇幼虫。
在该试验中,例如,按照制备实施例(1)、(2)、(4)、(5)和(8)所得的化合物显示出很好的效果。
Claims (5)
其中
R1代表6-氯-吡啶-3-基或2-氯-噻唑-5-基;
R2代表羟基甲基、羟基乙基、羟基丙基、二羟基乙基、二羟基丙基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、二甲氧基乙基或二乙氧基乙基;
R3代表氢、甲基、乙基、羟基甲基、羟基乙基、羟基丙基、二羟基乙基、二羟基丙基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、二甲氧基乙基或二乙氧基乙基;或者
R2和R3一起代表氧代乙烷-1,2-二基、二氧代乙烷-1,2-二基、羟基乙烷-1,2-二基、二羟基乙烷-1,2-二基、甲氧基乙烷-1,2-二基、乙氧基乙烷-1,2-二基、二甲氧基乙烷-1,2-二基或二乙烷氧基乙烷-1,2-二基;
R4代表氢或甲基;
Y代表氮或基团CH;并且
Z代表氰基或硝基。
2、通式(Ⅰ)的取代的氮杂环烷烃的制备方法:其中R1、R2、R3、R4、Y和Z的定义同权利要求1中定义;
该方法的特征在于:
(a)任选地在酸接受体的存在下,任选地在催化剂的存在下或任选地在稀释剂的存在下,将通式(Ⅱ)的氮杂烷烃与通式(Ⅲa)的卤代化合物和/或通式(Ⅲb)的卤代化合物进行反应,其中R1、Y和Z的定义同上所述,
X-R2(Ⅲa)
X-R3(Ⅲb)其中,R2、R3的定义同上所述,以及X代表卤素;或者
(b)任选地在反应助剂存在下并且任选在稀释剂的存在下加热通式(Ⅰ)的化合物,其中R2或R3代表二烷氧基烷基并且R1、R4、Y和Z的定义同上所述;或者
(c)任选地在反应助剂存在下并且任选在稀释剂的存在下,将通式(Ⅰ)的化合物,其中R2或R3代表二烷氧基烷基并且R1、R4、Y和Z的定义同上所述,与氢化剂进行反应;或者
(d)将通式(Ⅰ)的化合物,其中R2或R3一起代表二烷氧基烷二基或二烷氧基烷二基并且R1、R4、Y和Z的定义同上所述,与卤化氢和/或碱金属卤化物在稀释剂的存在下反应;或者
(e)任选地在酸结合剂的存在下并且任选地在稀释剂的存在下,将通式(Ⅰ)的化合物,其中R2或R3一起代表羟基烷或二羟基烷二基并且R1、R4、Y和Z的定义同上所述,与通式(Ⅳ)的烷基化试剂进行反应,
X1-R (Ⅳ)
其中
R代表烷基以及
X1代表卤素或基团-O-SO2-OR,其中R的定义同上所述;或者
(f)任选地在酸接受体的存在下并且任选地在稀释剂的存在下,将通式(Ⅰ)的化合物,其中R4代表氢并且R1、R2、R3、Y和Z的定义同上所述,与通式(Ⅴ)的卤素化合物进行反应,
X-R4(Ⅴ)
其中
X代表卤素并且
R4的定义同上所述,但不包括氢。
3、一种杀害虫组合物,其特征在于至少含有一种权利要求1的式(Ⅰ)的取代氮杂环烷烃化合物。
4、权利要求1的式(Ⅰ)的取代氮杂环烷烃化合物在杀灭害虫中的用途。
5.一种杀灭害虫的方法,其特征在于让权利要求1的式(Ⅰ)的取代氮杂环烷烃化合物作用于害虫和/或其栖息地。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DEP4236204.0 | 1992-10-27 | ||
DE4236204A DE4236204A1 (de) | 1992-10-27 | 1992-10-27 | Substituierte Aza(cyclo)alkane |
Publications (2)
Publication Number | Publication Date |
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CN1090844A CN1090844A (zh) | 1994-08-17 |
CN1042630C true CN1042630C (zh) | 1999-03-24 |
Family
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Application Number | Title | Priority Date | Filing Date |
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CN93119682A Expired - Fee Related CN1042630C (zh) | 1992-10-27 | 1993-10-27 | 取代的氮杂环烷烃及其制备方法、用途和含其的杀害虫组合物 |
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Country | Link |
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US (2) | US5461069A (zh) |
EP (1) | EP0595125B1 (zh) |
JP (1) | JP3419049B2 (zh) |
KR (1) | KR100290318B1 (zh) |
CN (1) | CN1042630C (zh) |
DE (2) | DE4236204A1 (zh) |
ES (1) | ES2086849T3 (zh) |
IL (1) | IL107380A (zh) |
TW (1) | TW244351B (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2610988B2 (ja) | 1989-03-09 | 1997-05-14 | 日本バイエルアグロケム 株式会社 | 新規ヘテロ環式化合物及び殺虫剤 |
US6232309B1 (en) | 1989-03-09 | 2001-05-15 | Nihon Bayer Agrochem K.K. | Insecticidal heterocyclic compounds |
US5434181A (en) * | 1993-10-26 | 1995-07-18 | Mitsui Toatsu Chemicals, Inc. | Furanyl insecticide |
JP2001515888A (ja) * | 1997-09-08 | 2001-09-25 | ノバルティス アクチエンゲゼルシャフト | 農薬としてのヘテロ環式化合物 |
CN102919259A (zh) * | 2012-10-11 | 2013-02-13 | 成都科利隆生化有限公司 | 双胍三辛烷基苯磺酸盐和氟啶胺的农药组合物 |
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EP0192060A1 (de) * | 1985-02-04 | 1986-08-27 | Nihon Bayer Agrochem K.K. | Heterocyclische Verbindungen |
EP0386565A1 (en) * | 1989-03-09 | 1990-09-12 | Nihon Bayer Agrochem K.K. | Heterocyclic compounds |
EP0425978A2 (en) * | 1989-10-24 | 1991-05-08 | Agro-Kanesho Co., Ltd. | Nitroguanidine compounds and insecticides |
EP0455000A1 (en) * | 1990-04-03 | 1991-11-06 | MITSUI TOATSU CHEMICALS, Inc. | Dialkoxymethylimidazolidine derivatives, preparation thereof, insecticides containing same as an effective ingredient and intermediates therefor |
EP0483052A1 (de) * | 1990-09-18 | 1992-04-29 | Ciba-Geigy Ag | Picolinoxide |
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JPH0717621B2 (ja) * | 1986-03-07 | 1995-03-01 | 日本バイエルアグロケム株式会社 | 新規ヘテロ環式化合物 |
DE3726265A1 (de) * | 1987-08-07 | 1989-02-16 | Wolff Walsrode Ag | Verpackungen aus gereckten siegelbaren mehrschichtfolien mit verbesserter transparenz |
IL93159A (en) * | 1989-01-31 | 1996-11-14 | Takeda Chemical Industries Ltd | Process for the production of 1,1,1-trihalogen-2-nitroethanes |
HU214992B (hu) * | 1989-10-06 | 1998-12-28 | Nippon Soda Co. Ltd. | Eljárás aminszármazékok előállítására és ilyen vegyületeket tartalmazó inszekticid készítmények |
IL99161A (en) * | 1990-08-17 | 1996-11-14 | Takeda Chemical Industries Ltd | History of guanidine A process for their preparation and preparations from pesticides that contain them |
EP0547557B1 (en) * | 1991-12-16 | 1994-07-27 | MITSUI TOATSU CHEMICALS, Inc. | N-vinylimidazolidine derivatives, preparation thereof, insecticides containing same as an effective ingredient and intermediates thereof |
-
1992
- 1992-10-27 DE DE4236204A patent/DE4236204A1/de not_active Withdrawn
-
1993
- 1993-09-27 TW TW082107932A patent/TW244351B/zh active
- 1993-10-14 DE DE59302595T patent/DE59302595D1/de not_active Expired - Fee Related
- 1993-10-14 ES ES93116618T patent/ES2086849T3/es not_active Expired - Lifetime
- 1993-10-14 EP EP93116618A patent/EP0595125B1/de not_active Expired - Lifetime
- 1993-10-20 US US08/139,350 patent/US5461069A/en not_active Expired - Lifetime
- 1993-10-22 KR KR1019930022077A patent/KR100290318B1/ko not_active IP Right Cessation
- 1993-10-25 IL IL107380A patent/IL107380A/xx not_active IP Right Cessation
- 1993-10-26 JP JP29000893A patent/JP3419049B2/ja not_active Expired - Fee Related
- 1993-10-27 CN CN93119682A patent/CN1042630C/zh not_active Expired - Fee Related
-
1995
- 1995-05-18 US US08/443,528 patent/US5565459A/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0192060A1 (de) * | 1985-02-04 | 1986-08-27 | Nihon Bayer Agrochem K.K. | Heterocyclische Verbindungen |
EP0386565A1 (en) * | 1989-03-09 | 1990-09-12 | Nihon Bayer Agrochem K.K. | Heterocyclic compounds |
EP0425978A2 (en) * | 1989-10-24 | 1991-05-08 | Agro-Kanesho Co., Ltd. | Nitroguanidine compounds and insecticides |
EP0455000A1 (en) * | 1990-04-03 | 1991-11-06 | MITSUI TOATSU CHEMICALS, Inc. | Dialkoxymethylimidazolidine derivatives, preparation thereof, insecticides containing same as an effective ingredient and intermediates therefor |
EP0483052A1 (de) * | 1990-09-18 | 1992-04-29 | Ciba-Geigy Ag | Picolinoxide |
Also Published As
Publication number | Publication date |
---|---|
DE59302595D1 (de) | 1996-06-20 |
EP0595125A1 (de) | 1994-05-04 |
US5461069A (en) | 1995-10-24 |
IL107380A (en) | 1997-09-30 |
KR100290318B1 (ko) | 2001-09-17 |
JP3419049B2 (ja) | 2003-06-23 |
IL107380A0 (en) | 1994-01-25 |
EP0595125B1 (de) | 1996-05-15 |
KR940009173A (ko) | 1994-05-20 |
ES2086849T3 (es) | 1996-07-01 |
US5565459A (en) | 1996-10-15 |
CN1090844A (zh) | 1994-08-17 |
TW244351B (zh) | 1995-04-01 |
JPH06220018A (ja) | 1994-08-09 |
DE4236204A1 (de) | 1994-04-28 |
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