CN1138856A - 取代的噁唑啉 - Google Patents
取代的噁唑啉 Download PDFInfo
- Publication number
- CN1138856A CN1138856A CN95191255A CN95191255A CN1138856A CN 1138856 A CN1138856 A CN 1138856A CN 95191255 A CN95191255 A CN 95191255A CN 95191255 A CN95191255 A CN 95191255A CN 1138856 A CN1138856 A CN 1138856A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- inequality
- substituting group
- group
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002918 oxazolines Chemical class 0.000 title abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 71
- -1 phenylalkenyl Chemical group 0.000 claims abstract description 59
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 41
- 239000000460 chlorine Substances 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 32
- 239000002585 base Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
- 241000607479 Yersinia pestis Species 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 4
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 4
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 4
- XRWNSAQIZMUBNU-UHFFFAOYSA-N 2,3-dichloro-3-fluoroprop-2-enoyl chloride Chemical compound FC(Cl)=C(Cl)C(Cl)=O XRWNSAQIZMUBNU-UHFFFAOYSA-N 0.000 claims description 3
- 150000001414 amino alcohols Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 230000002508 compound effect Effects 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- AHIBWURJLGCHAY-UHFFFAOYSA-N [S].C1=CC=CC=C1 Chemical compound [S].C1=CC=CC=C1 AHIBWURJLGCHAY-UHFFFAOYSA-N 0.000 claims 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000003995 emulsifying agent Substances 0.000 description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241001124076 Aphididae Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000238421 Arthropoda Species 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 241000086608 Empoasca vitis Species 0.000 description 4
- 241000578422 Graphosoma lineatum 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
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 4
- 150000001263 acyl chlorides Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 239000003595 mist Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 241000238876 Acari Species 0.000 description 3
- 235000007516 Chrysanthemum Nutrition 0.000 description 3
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 3
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- JFPCQBWUOJIHLS-UHFFFAOYSA-N 1,1,3,3,3-pentachloro-2-fluoroprop-1-ene Chemical group ClC(Cl)=C(F)C(Cl)(Cl)Cl JFPCQBWUOJIHLS-UHFFFAOYSA-N 0.000 description 2
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- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
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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
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
本发明涉及式(I)的新型的取代噁唑啉,它们的多种制法及它们作为防治害虫剂的应用,
其中
A代表各自任选取代的烷基、烯基、环烷基或环烯基;
B代表各自任选取代的苯基、苯基烷基、苯基烯基、苯氧基烷基或苯硫基烷基;
D代表氢或烷基;
E代表氢或烷基;和
G代表氢或烷基。
Description
本发明涉及新的取代噁唑啉、它们的多种制法及它们在防治动物害虫中的应用。
已知某些噁唑啉衍生物具有杀虫和杀螨特性(参见,EP-A 0 345 775和EP-A 0 432 661)。但这些已知化合物的活性并非在所有应用领域都令人满意,特别是在使用量和浓度低时更是如此。
现已发现式(I)的新型取代的噁唑啉,其中
A代表各自任选取代的烷基、烯基、环烷基或环烯基;
B代表各自任选取代的苯基、苯基烷基、苯基烯基、苯氧基烷基或苯硫基烷
基;
D代表氢或烷基;
E代表氢或烷基;和
G代表氢或烷基。
根据取代基的性质,式(I)化合物也可以几何异构体和/或旋光异构体或不同组成的异构体混合物形式存在。本发明既涉及纯的异构体,也涉及异构体混合物。
B、D、E和G具有上述意义;
A-COOH (III)其中
A、B、D、E和G具有上述意义;或c)必要时在稀释剂存在下,使式(V)的酰胺衍生物与碱反应,其中
A、B、D、E和G具有前述意义,和
X代表离去基团,例如卤素、烷基磺酰氧基或芳基磺酰氧基。
还已发现式(I)的取代的噁唑啉极其适于防治动物害虫。它们对于节肢动物和线虫的活性水平极为出色。
令人吃惊的是,本发明的式(I)的取代的噁唑啉较之结构最接近此新化合物的先有技术化合物表现出好得多的防治动物害虫的活性。
本发明化合物的一般定义由式(I)给出。
A优选代表任选被选自下列基团的相同或不相同取代基取代一次或多次的
C1-C8烷基:卤素、氰基和C1-C4烷氧基,以及苯基、苯氧基、
苄氧基、苯硫基和苄硫基,这些基团中的每一个都任选被选自下列基团的
相同或不相同取代基取代一至三次:卤素、C1-C4烷基、C1-C4
卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫
基和/或C1-C4卤代烷硫基;
代表任选被相同或不相同的卤素取代基取代一或多次的C2-C8烯基;
代表任选被选自下列基团的相同或不相同取代基取代一或多次的C3-
C8环烷基:卤素、C1-C4烷基、C2-C4烯基、C1-C4卤
代烷基或C2-C4卤代烯基:和
代表任选被选自下列基团的相同或不相同取代基取代一或多次的C5-
C7环烯基:卤素、C1-C4烷基和C1-C4卤代烷基。B 优选代表苯基、苄基、苯基乙-1-基、苯基乙-2-基、苯氧基甲基、苯硫基甲基、苯氧基乙-1-基、苯硫基乙-1-基、苯氧基乙-2-基或苯乙烯基,它们各自可任选被相同或不相同取代基取代一至四次,可提及的苯基取代基各自为:卤素,C1-C18烷基,C1-C8烷氧基-C1-C8烷基,C1-C8卤代烷氧基,C1-C4卤代烷基,任选被1-3个其它氧原子间隔的C1-C18烷氧基,C1-C18烷硫基,C1-C8卤代烷硫基,3,4-二氟亚甲二氧基,3,4-四氟亚乙二氧基,任选被C1-C4烷基、C3-C6环烷基和/或卤素取代的苄基亚氨基
氧基甲基,环己基和环己氧基,它们各自任选被C1-C6烷基、C1-C6烷氧基、
环己基或苯基取代,任选被选自下列基团的相同或不相同取代基取代一次或二次的吡啶氧基:
卤素、C1-C4烷基或C1-C4卤代烷基;苯基、苄基、苯氧基、苯硫基、苄氧基和苄硫基,它们各自任选被选自下
列基团的相同或不相同取代基取代一至三次:C1-C12烷基、卤素、
C1-C4卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、
C1-C6烷氧基-C1-C6烷基、C1-C6烷氧基-亚乙氧基、
C1-C6烷硫基和/或C1-C6卤代烷硫基,D 优选代表氢或甲基。E 优选代表氢或甲基。G 优选代表氢或甲基。A 特别优选代表任选被选自下列基团的相同或不相同取代基取代一次或多次的C1-C6烷基:氟、氯、溴、氰基和C1-C2烷氧基,以及苯基、苯氧基、苄氧基、苯硫基和苄硫基,它们各自任选被选自下列基团的相同或不相同取代基取代一或两次:氟、氯、C1-C4烷基、C1-C2卤代烷基、C1-C2烷氧基、C1-C2卤代烷氧基、C1-C2烷硫基和/或C1-C2卤代烷硫基;
代表任选被选自氟、氯和/或溴的相同或不相同取代基取代一或多次的C2-C6烯基;代表任选被选自下列基团的相同或不相同取代基取代一或多次的C3-C8环烷基:氟、氯、C1-C4烷基和C2-C4烯基、以及被氟和/或氯取代的C1-C2烷基或C2-C4烯基;和代表任选被选自下列基团的相同或不相同取代基取代一或多次的C5-C7环烯基:氟、氯和C1-C4烷基以及被氟和/或氯取代的C1-C2烷基。B 特别优选代表苯基、苄基、苯基乙-1-基、苯基乙-2-基、苯氧基甲基、苯硫基甲基、苯氧基乙-1-基、苯氧基乙-2-基、苯硫基乙-1-基或苯乙烯基,它们各自任选被相同或不相同的取代基取代一至四次,可提及的苯基取代基各自为:
F、Cl、Br;
C1-C18烷基;
C1-C6烷氧基-C1-C8烷基;
被选自F和/或Cl的相同或不相同取代基取代一至六次的C1-C8
烷氧基;
被选自F和/或Cl的相同或不相同取代基取代一至五次的C1-C2
烷基;
C1-C18烷氧基和-(OC2H4)1-3-O-C1-C6烷基;
C1-C12烷硫基;
被选自F和/或Cl的相同或不相同取代基取代一至六次的C1-C8
烷硫基;
3,4-二氟亚甲二氧基;
3,4-四氟亚乙二氧基;
下列基团
环己基或环己氧基,它们各自任选被C1-C4烷基、C1-C4烷氧基、
环己基或苯基取代;
吡啶氧基,它任选被选自F、Cl或CF3的相同或不相同取代基取代一次
或两次;苯基、苄基、苯氧基、苯硫基、苄氧基和苄硫基,它们各自任选被选自下
列基团的相同或不相同取代基取代一至三次:C1-C12烷基、F、Cl、
Br、CF3,以及C1-C4烷氧基、被选自F和/或Cl的相同或不相
同取代基取代一至六次的C1-C4烷氧基、C1-C4烷氧基-C1
-C4烷基、C1-C4烷氧基亚乙氧基、C1-C4烷硫基或被选自
F和/或Cl的相同或不相同取代基取代一至六次的C1-C4烷硫基;D 特别优选代表氢或甲基。E 特别优选代表氢或甲基。G 特别优选代表氢或甲基。
本发明的优选化合物还有式(I-1)至(I-10)的一组物质:其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基。其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基。
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基。其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基。其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基。
本发明的更为优选化合物为这样的一组式(I-1)至(I-10)物质,其中A代表任选被相同或不相同取代基取代一至三次的叔丁基,适宜的取代基为上述(A)中所述优选和特别优选的烷基的取代基。
同样,本发明的优选化合物还有这样的一组式(I-1)至(I-10)物质,其中A代表任选被相同或不相同的取代基取代一至五次的环丙基,适宜的取代基为上述(A)中所述优选和特别优选的环烷基的取代基。
另外,本发明的其它优选化合物还有这样的一组式(I-1)至(I-10)物质,其中A代表任选被选自F和/或Cl的相同或不相同的取代基取代一至三次的乙烯基。
其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
D、E和G相同或不相同,并代表氢或甲基,但至少一个取代基代表甲基。其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
D、E和G相同或不相同,并代表氢或甲基,但至少一个取代基代表甲基。其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
D、E和G相同或不相同,并代表氢或甲基,但至少一个取代基代表甲基。
其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
D、E和G相同或不相同,并代表氢或甲基,但至少一个取代基代表甲基。其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
D、E和G相同或不相同,并代表氢或甲基,但至少一个取代基代表甲基。其中
A具有前述一般、优选和特别优选的意义,和
B1代表任选被相同或不相同取代基取代一至四次的苯基,适宜的取代基为
在上述(B)中所述的优选或特别优选的苯基的取代基;和
D、E和G相同或不相同,并代表氢或甲基,但至少一个取代基代表甲基。
本发明更为优选的化合物为这样的式(I-11)至(I-20)物质,其中A代表任选被相同或不相同取代基取代一至三次的叔丁基,适宜的取代基为上述(A)中所述优选和特别优选的烷基的取代基。
同样,本发明的优选化合物还有这样的式(I-11)至(I-20)物质,其中A代表任选被相同或不相同的取代基取代一至五次的环丙基,适宜的取代基为上述(A)中所述优选和特别优选的环烷基的取代基。
另外,本发明的其它优选化合物还有这样的式(I-11)至(I-20)物质,其中A代表任选被选自F和/或Cl的相同或不相同的取代基取代一至三次的乙烯基。
在上述定义本发明化合物过程中提及的烃基,例如烷基,可能时各自为直链或支链,甚至与杂原子结合,如在烷氧基中。
取代基A的实例为下列基团:
-CH2O-,-CH2S-,-CH(CH3)S-,-CH(CH3)O-,-CH2CH2O-R1=按表1,和(R2)m=按表2。
表1
表1(续)
表1(续)
表1(续)
表2
(R2)m | (R2)m |
H | 2-CH3 |
2-Cl | 2-OCH3 |
2-F | 2-OC2H5 |
3-Cl | 3-CH3 |
2,6-Cl2 | 3,5-(CH3)2 |
3,5-Cl2 | 3-OC6H5 |
3,5-F2 | |
2,5-Cl2 | 与R1一起代表 |
3,5-Cl2,2-F | |
2,3-F2 | 3,4-OCF2O-和 |
2,5-F2 | 3,4-OCF2CF2O- |
本发明式(I)化合物各实例为如下:
(续)
(续)
(续)
(续)
式(II)给出了在制备式(I)化合物的本发明方法(a)中用作原料的氨基醇的一般定义。在式(II)中,B、D、E和G优选或具体具有在上述描述式(I)化合物时已提及的B、D、E和G的优选或特别优选的定义。
式(II)的起始化合物是已知的和/或可用已知方法,经还原相应的氨基酸而得(参见Heterocycles 9(1978),1277-1285;J.Org.Chem.43(1978),2539-2541;Liebigs Ann.Chem.1980,122-139;Tetrahedron Lett.26(1985),4971-4974).
式(III)提供了在本发明用于制备式(I)化合物的方法(a)中还需要作为起始物的羧酸的一般定义。在式(III)中,A优选或具体地具有在上述描述式(I)化合物时已提及的A优选或特别优选的意义。
式(III)的起始物为已知的合成有机化学物质,或可用已知方式得到。
本发明的方法(a)和(b)实施时用到脱水剂。有机化学领域中习用的脱水剂都可采用。可优选使用硫酸、多磷酸(PPS)、五氧化二磷(V)、二环己基碳化二亚胺(DCC)、五硫化二磷(V)和三苯膦/三乙胺/四氯化碳体系。
实施本发明方法(a)~(c)的适宜稀释剂为常规的有机溶剂。可优选采用的溶剂为脂族、脂环族或芳香(任选卤代)烃类,例如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿或四氯化碳;醚类,例如二乙基醚、二异丙基醚、二噁烷、四氢呋喃或乙二醇二甲基醚或二乙基醚;酮类,如丙酮、丁酮或甲基异丁基酮;腈类,如乙腈、丙腈或苄腈;酰胺类,如N,N-二甲基甲酰胺和N,N-二甲基乙酰胺,N-甲基-吡咯烷酮或六甲基磷酰胺;酯类,如乙酸甲酯或乙酸乙酯,和亚砜类,如二甲基亚砜,且如果适宜也可有醇类,如甲醇或乙醇。
实施本发明的方法(a)时,反应温度可在相当宽的范围内变化。所述反应一般在0~150℃,优选在10~100℃温度实施。
本发明的方法(a)一般在常压下实施。但也可能在增压或减压-一般为0.1bar~10bar-条件下实施本方法。
在实施本发明的方法(a)时,所需的各种具体起始物一般按大约等摩尔量使用。但也可能使两种具体组分中一种的用量较大过量。反应一般在脱水剂存在下在适宜稀释剂中实施,且反应混合物在所需的具体温度下搅拌数小时。本发明各种方法的后处理均按习用方法进行。
在本发明方法(a)的一个具体实施方案中,也可采用相应的腈类,以代替式(III)的羧酸类,在这种情况下,则优选用催化剂[如氯化锌(II)]代替脱水剂。
式(IV)提供了在本发明制备式(I)化合物的方法(b)中用作起始物的酰氨基-醇类的一般定义。在式(IV)中,A、B、D、E和G优选或具体地具有在上述描述式(I)化合物时已提及的A、B、D、E和G优选或特别优选的意义。
式(IV)的起始物质为已知和/或可通过本身已知的方法制得。
式(IV)的酰氨基-醇类例如可通过下述方式获得:在酸结合剂(例如三乙胺、吡啶、碳酸钾、氢氧化钠或叔丁醇钾)存在下,并在稀释剂(例如甲苯、氯苯、丙酮或乙腈)存在下,在0~100℃温度下,使衍生自式(III)的羧酸的酰氯与式(II)的氨基醇类反应(参照制备实施例)。
衍生自式(III)的羧酸的酰氯为已知的,和/或可用本身已知的方法制得,例如,使式(III)的羧酸与卤化剂,例如亚硫酰氯必要时在稀释剂存在下反应。
一种至令仍不为人知,并也为本发明主题的化合物是式(VI)的α-氟-β,β-二氯烯丙酰氯
Cl2C=CF-COCl (VI)
式(VI)的α-氟-β,β-二氯烯丙酰氯可通过下列方法得到:必要时在催化剂存在下,水解2-氟-1,1,3,3,3-五氯丙烯。适用的催化剂包括路易斯酸、无机酸和它们的酸盐,例如FeCl3、BF3、H2SO4、HCl、KHSO4、NaHSO4等(也可参考实施例)。
根据反应条件(例如酰氯在反应混合物中的停留时间)和所加入的水量,所形成的主要产物α-氟-β,β-二氟烯丙酰氯必要时可部分水解为相应的丙烯酸,后者可然后再转变为酰氯,例如经与亚硫酰氯反应。
在实施本发明方法(b)时,反应温度可以在相当宽的范围内变化。所述反应一般在-20℃~+150℃,优选在0~100℃温度实施。
本发明的方法(b)一般在常压下实施,但也可能在增压或减压下实施-一般在0.1bra至10bar之间。
在实施本发明制备式(I)化合物的方法(b)时,相对于每摩尔式(IV)的酰氨基-醇一般采用1~20摩尔,优选1至5摩尔脱水剂。
在本发明的方法(b)的一个优选实施方案中,将式(IV)的酰氨基-醇首先加入稀释剂中,然后计量加入脱水剂。在所需温度下搅拌反应混合物,直至反应结束,然后以习用方法进行后处理。
式(V)提供了本发明制备式(I)化合物的方法(c)中用作起始物的酰胺衍生物的一般定义。在式(V)中,A、B、D、E和G优选或具体地具有在上述式(I)化合物的说明中已提及的A、B、D、E和G的优选或特别优选的意义;X优选代表氟、氯、溴、碘、C1-C4烷基-磺酰氧基、苯磺酰氧基或甲苯磺酰氧基,特别是氯、溴、甲基磺酰氧基或甲苯磺酰氧基。
式(V)的起始物为已知和/或可用本身已知的方法制得。
式(V)的酰胺衍生物可以下述方式制得:以常规方式,适宜时,在稀释剂和碱存在下,使(IV)的相应酰氨基-醇类与氯化剂[例如亚硫酰氯或五氯化磷(V)]反应,或者适宜时在稀释剂和碱存在下,使(IV)的相应酰氨基-醇类与磺酰化剂[例如甲磺酰氯或p-甲苯磺酰氯]反应。
本发明的方法(c)在碱存在下实施。所有习用的无机碱或有机碱都适用于此。可优选使用的碱为碱金属或碱土金属的氢化物、氢氧化物、氨化物、醇化物、乙酸盐、碳酸盐或碳酸氢盐,例如,氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾或碳酸铵,以及叔胺类,如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
在实施本发明方法(c)时,反应温度可在相当宽的范围内变化。所述反应一般在-20~+150℃,优选在0-100℃温度实施。
本发明的方法(c)一般在常压下实施。但也可能在增压或减压下实施-一般在0.1bar和10bar之间。
在实施本发明制备式(I)化合物的方法(c)时,相对于每摩尔式(V)的酰胺衍生物一般采用1~3摩尔,优选1.0~1.5摩尔的碱。
在本发明方法(c)的一个优选实施方案中,将式(V)的酰胺衍生物和碱在适宜的稀释剂中进行混合;将反应混合物在所需温度下搅拌,直至反应结束,然后以习用方式进行后处理。
活性化合物适用于防治动物害虫,优选节肢动物和线虫,特别是在农业、林业以及储存产品和材料的保护以及卫生部门中出现的昆虫和蜘蛛纲动物。它们对于通常敏感和有抗性的物种及其全部或部分发育阶段均具有活性。上述害虫包括:
等足目,例如潮虫、平甲虫和鼠妇。
倍足目,例如具斑马陆。
唇足目,例如食果地蜈松和蛐蜒属。
扁肩象目,例如庭院么蛐。
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、美洲大蠊、马得拉蜚蠊、德国蠊、家蟋蟀、蝼蛄属,热带飞蝗、殊种蚱蜢和沙漠蝗。
革翅目,例如欧洲球螋。
等翅目,例如犀白蚁属。
虱目,例如葡萄瘤蚜,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,例如温室条蓟马和葱蓟马。
异翅亚目,例如扁盾蝽属,红蝽属,方背皮蝽属,温带臭虫,长红蜡蝽和蜡蝽属。
半翅目,例如甘蓝粉虱,木薯粉虱,温室粉虱,棉蚜,甘蓝蚜,茶蔗隐瘤蚜,Doralis fabae,Doralis Pomi,苹果绵蚜,桃大尾蚜,稠李溢管蚜,微叶蝉属,双叶叶蝉,黑尾时蝉,麦长管蚜,瘤蚜属,忽布庞蚜,李蜡蚧,油榄黑盔蚧,灰飞虱,稻褐飞虱,红圆蚧,夹竹桃圆蚧,粉蚧属和木虱属。
鳞刺目,例如棉红蛉虫,松天蚜,冬天蛾,苹细蛾,苹果巢蛾,小菜蛾,黄褐天幕毛虫,黄毒蛾,毒蛾属,棉潜蛾,桔叶潜蛾,地虎属,刀根虫属,夜蛾属,棉斑实蛾,实夜蛾属,甜菜夜蛾,甘蓝夜蛾,小眼夜蛾,斜纹夜蛾,粘虫属,粉纹夜蛾,苹蠢蛾,粉蝶属,螟属,玉米螟、地中海粉螟,大蜡螟,负袋衣蛾,织网衣蛾,褐织衣蛾,亚麻黄卷蛾,具网卷叶蛾,云松卷蛾,葡萄果蠢蛾,茶长卷蛾和栎绿卷叶蛾。
鞘翅目,例如具斑窃蠢,谷蠢,豆象,大豆象,家天牛,赤杨紫跳甲,马铃薯甲虫,辣根猿叶虫,叶甲属,油菜蓝跳甲,墨西哥豆飘虫,隐金甲属,锯谷盗,花象甲属,谷象属,葡萄黑象甲,香蕉根象甲,甘蓝荚象甲,苜蓿叶象甲,皮蠢属,斑皮蠢属,圆皮蠢属,毛皮蠢属,粉蠢属,油菜花露尾甲,蛛甲属,金黄蛛甲,麦蛛甲,拟谷盗属,大黄粉虫,叩甲属,金针虫属,西方五月鳃角金龟,六月金龟和褐新西兰肋翅鳃角金龟。
膜刺目,例如锯角叶蜂属,叶蜂属,蚁尾属,厕蚁和胡蜂属。
双翅目,如伊蚊属,按蚊属,库蚊属,黄猩猩果蝇,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,厩螯蝇属,狂蝇属,皮蝇属,虻属,螗蜩属,花圆毛蚊,瑞典麦杆蝇,麦花蝇属,菠菜潜叶花蝇,地中海实蝇,油榄实蝇和欧洲大蚊。
蚤目,如印度客蚤和毛列蚤属。
蛛形纲,如蝎和盗蛛。
蜱螨目,如粗脚粉螨,锐缘蜱属,钝缘蜱属,鸡皮刺螨,茶蔗瘿螨,桔芸锈螨,牛蜱属,扁头蜱属,花蜱属,璃眼蜱属,硬蜱属,痒螨属,皮痒螨属,疥螨属,附线螨属,苜蓿苔螨,全爪螨属和叶螨属。
植物寄生性线虫包括草地垫刃线虫属、内侵(穿孔)线虫属的一种(Radopholus similis)、双垫刃线虫属的一种(Ditylenchus dipsaci)、半穿透垫刃线虫(Tylenchulus semipenetrans)、异皮线虫属(Heteroderaspp.)、根结线虫属(Meloidogyne spp.)、滑刃线虫属(Aphelenchoidesspp.)、Longidorus spp.、剑线虫属(Xiphinema spp.)和滑刃线虫属(Trichodorus spp.)。
在使用量适宜时,本发明化合物也表现出杀真菌活性。
活性化合物可调制成常规的制剂,如溶液剂、乳液剂、可湿性粉剂、悬浮液剂、粉末剂、尘剂、糊剂、可溶性粉剂、颗粒剂、悬浮液/乳液浓缩液剂、浸泡了活性化合物的天然和合成材料,用于种子的在高分子物质和包衣组合物中的微胶囊剂,以及与燃烧设备(如熏蒸筒、熏蒸罐、熏蒸盘管等)一起使用的制剂,以及超低容量(ULV)的冷雾(cold mist)和热雾(warm mist)制剂。
这些制剂用已知方法制成,例如可通过下述方法:任选使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂和/或稳定剂)将活性化合物和稀释剂(即液体溶剂和/或固体载体)混合。
如果采用水作稀释剂,则也可用(例如)有机溶剂作助溶剂。适用的液体溶剂主要有:芳族化合物(如二甲苯、甲苯或烷基萘)、氯化芳族化合物或氯代脂族烃类(如氯苯、氯乙烷或二氯甲烷)、脂族烃类(如环己烷或烷属烃,如矿物油馏分、矿物油和植物油)、醇类(如丁醇或乙二醇及它们的醚或酯)、酮类(如丙酮、甲基乙基酮、甲基异丁基酮或环己酮)、强极性溶剂(如二甲基甲酰胺和二甲基亚砜以及水);所谓液化的气体稀释剂或载体指在环境温度和大气压下为气态的液体(如气溶胶抛射剂,例如卤代烃和丁烷、丙烷、氮和二氧化碳);适用的固体载体有:如铵盐和研碎的天然矿物(例如高岭土、粘土、滑石粉、白垩、石英、绿坡缕石、蒙脱土或硅藻土)和研碎的合成矿物(如高分散度硅石、氧化铝和硅酸盐);适用的固体颗粒载体有:如粉碎并分级的天然岩石(例如方解石、大理石、浮石、海泡石和白云石)及合成的无机颗粒和有机粉,和有机材料颗粒(如锯末、椰壳、玉米棒碎块和烟叶杆);适用的乳化剂和/或起泡剂有:如非离子型和阴离子型乳化剂(如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如烷芳基聚乙二醇醚,烷基磺酸盐、烷基硫酸盐、芳基磺酸盐及蛋清水解产物);适用的分散剂有:如亚硫酸纸浆废液和甲基纤维素。
在制剂中可使用粘合剂,例如羧甲基纤维素和粉状、颗粒状或胶乳状天然和合成高聚物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯以及天然磷脂,如脑磷脂和卵磷脂以及合成磷脂。其他添加剂可为矿物油和植物油。
可使用着色剂,如无机颜料(例如氧化铁、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)以及微量的营养素(如铁、锰、硼、铜、钴、钼和锌的盐)。
制剂中一般含有0.1至95%(重量),优选0.5至90%(重量)的活性化合物。
本发明的活性化合物可存在于其市售制剂中和存在于由这些制剂制得的使用形式中,如和其它活性化合物(如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂)的混合物。这些杀虫剂包括,例如磷酸酯、氨基甲酸酯、羧酸酯、氯代烃类、苯脲和微生物等产出的物质。
可列举下列化合物:
acrinathrin、alphamethrin、betacyfluthrin、bifenthrin、brofenprox、Cis-resmethrin、clocythrin、cycloprothrin、cyfluthrin、cyhalothrin、腈二氯苯醚菊脂、deltamethrin、esfenvalerate、etofenprox、分扑菊酯、杀灭菊酯、flucythrinate、fluvalinate lambda-cyhalothrin、二氯苯醚菊脂、pyresmethrin、除虫菊、Silafluofen、tralomethrin、zetamethrin;
alanycarb、苯噁威、benfuracarb、混戊威、丁叉威、西维因、巴丹、乙硫甲威、fenobucarb、fenoxycarb、异丙威、甲硫威、乙肟威、metolcarb、草肟威、灭定威、甲丙威、残杀威、叔丁威、thiodicarb、特氨叉威、trimethacarb、二甲威、xylylcarb:
乙酰甲胺磷、谷硫磷-A、谷硫磷-M、溴硫磷-A、Cadusafos、三硫磷、毒虫畏、氯甲硫磷、毒死蜱、Chlorpyrifos M、杀螟腈、甲基内吸磷、异吸磷-II、异-0五九-II、地亚农、敌敌畏、dicliphos、氯线磷、百治磷、乐果、dimethylvinphos、二噁硫磷、乙拌磷、克瘟散、乙硫磷、乙嘧硫磷、杀螟松、倍硫磷、地虫硫膦、安果、庚虫磷、iprobenfos、异丙三唑硫磷、异噁唑硫磷、马拉硫磷、灭蚜硫磷、mervinphos、mesulfenphos、丁烯硫磷、甲胺磷、三溴磷、氧化乐果、砜吸硫磷、oxydeprofos、对硫磷-A、对硫磷-M、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、肟硫磷、嘧啶硫磷-A、嘧啶硫磷-M、丙虫磷、低毒硫磷、发果、Pyraclophos、打杀磷、喹硫磷、杀虫松、Sebufos、硫特普、乙丙硫磷、杀虫畏、双硫磷、二甲硫吸磷、嗪线磷、敌百虫、三唑硫磷、完灭硫磷;
buprofezin、chlorfluazuron、伏虫脲、flucycloxuron、flufenoxuron、hexaflumuron、pyriproxifen、tebufenozide、teflubenzuron、triflumuron;
imidacloprid、nitenpyram、N-[(6-氯-3-吡啶基)-甲基]-N′-氰基-N-甲基乙酰亚胺-酰胺(NI-25);
abamectin、amitrazin、avermectin、azadirachtin、bensultap、杀虫素、Cyromazine、diafenthiuron、emamectin、ethofenprox、fenpyrad、fipronil、flufenprox、lufenuron、蜗牛敌、milbemectin、Pymetrozine、tebufenpyrad、triazuron;
涕灭威、苯噁威、benfuracarb、呋喃丹、carbosulfan、chlorethoxyfos、cloethocarb、乙拌磷、丙线磷、乙嘧硫磷、克线磷、fipronil、地虫硫膦、fosthiazate、furathiocarb、六六六、异丙三唑硫磷、异丙胺磷、甲硫威、久效磷、Nitenpyram、草肟威、甲拌硫、肟硫磷、低毒硫磷、pyrachlofos、sebufos、silafluofen、tebupirimphos、tefluthrin、特丁磷、thiodicarb、特氨叉威;
唑环锡、butylpyridaben、clofentezine、三环锡、difenthiuron、乙硫磷、emamectin、fenazaquin、螨完锡、fenothiocarb、分扑菊酯、fenpyrad、fenpyroximate、fluazinam、fluazuron、flucycloxuron、flufenoxuron、fluvalihate、fubfenprox、hexythiazox、jvemectin、甲噻硫磷、久效磷、moxidectin、三溴磷、伏杀硫磷、溴丙磷、pyraclofos、pyridaben、pyrimidifen、tebufenpyrad、thuringiensin、triarathene和4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)-1H-吡咯-3-腈(AC 303630);
本发明的活性化合物还可存在于其市售制剂和由这些制制得的使用形式中,如和增效剂的混合物。增效剂为强化活性化合物作用的化合物,而加入的增效剂本身不一定是活性的。
由市售制剂制得的使用形式中的活性化合物的含量可在一个很宽的限度内变化。活性化合物在使用形式中的浓度可为0.0000001%至95%(重量)活性化合物,优选0.0001%至1%(重量)。
本化合物以适用于使用形式的习用方法进行使用。
本发明的活性化合物不仅对植物害虫、卫生领域害虫和储藏产品害虫具有有活性,而且在兽医领域,对防治动物寄生虫(外寄生虫和内寄生虫)也有活性,例如scaly ticks、隐缘蜱科、疥螨科、蜱螨、Trombidae;蝇(叮咬和吸食)、寄生性蝇幼虫、虱目、hair lice、bird lice、蚤目和内寄生蠕虫。例如,它们对蜱(如微小牛蜱)表现出极突出的活性。
本发明的式(I)的活性化合物也适用于防治侵扰农业家畜的节肢动物,农业家畜如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、和蜜蜂,其它家养动物,例如狗、猫、笼养鸟和水族馆的鱼,还有所谓的试验动物,例如田鼠、豚鼠、大鼠和小鼠。通过防治这些节肢动物,旨在减少死亡案例和减产(肉、奶、毛、皮、蛋、蜜等),因此,通过使用本发明的活性化合物,可以使畜牧业更经济、更简单。
在兽医部门中,本发明的活性化合物用已知方式给药,即经肠给药,例如以片剂、胶囊剂、饮剂、灌药剂、颗粒剂、膏剂、大丸剂、饲养过程和栓剂等形式进行;非经肠给药,例如注射法(肌肉注射、皮下注射、静脉注射、腹膜内注射等)、植入法;经鼻给药;经皮给药,例如以浸泡或洗澡、喷雾、泼上或搽上、洗涤和撒粉等形式进行,也可以借助于含有活性化合物的成型制品,例如项圈、耳饰物、尾饰物、肢环(带)、笼头、装饰器具等。
本发明的物质的制备和应用以下述实施例说明。制备实施例
实施例1(方法c)
将1.6ml(0.026mol)45%浓度的氢氧化钠的5ml水溶液滴加到4.3g(0.013mol)于100ml甲醇中回流的N-[2-氯-1-(4-叔丁基苯基)乙基]-2,2-双(氟甲基)-丙酰胺中。反应混合物搅拌回流1小时,然后经蒸馏溶剂而浓缩。残留物用水搅拌,吸滤沉淀,并干燥。
得到3.8g(理论值的99%)2-(1,3-二氟-2-甲基-丙-2-基)-4-(4-叔丁基苯基)-1,3-噁唑基,熔点62-63℃。原料化合物的制备
实施例(IV-1)(步骤1)
将3.3ml(0.024mol)三乙胺加到3.9g(0.02mol)2-氨基-2-(4-叔丁基苯基)-1-乙醇于150ml乙酸乙酯的溶液中,然后在0℃滴加3.7g(0.024mol)2,2-双(氟甲基)丙酰氯。然后令混合物温热至室温,并搅拌过夜。接着吸滤沉淀,用水洗涤滤液数次,分出有机相,用硫酸钠干燥、过滤并浓缩。
将1.05ml(0.0144mol)亚硫酰氯加到在100ml的四氟化碳中的4.5g(0.0144mol)的N-[2-羟基-1-(4-叔丁基苯基)乙基]-2,2-双(氟甲基)丙酰胺(参考步骤1)。反应混合物回流反应1小时。蒸发溶剂后,得到4.3g(理论值的90%)N-[2-氯-1-(4-叔丁基苯基)乙基]-2,2-双(氟甲基)丙酰胺,熔点98℃。实施例2(步骤C)
将2.8ml三乙胺加到于50ml无水四氢呋喃中的3.4g(20mmol)2-(4-甲基苯基)-2-氨基乙醇中,并在0-10℃滴加3.6g(20mmol)3,3-二氯-2-氟烯丙酰氯。在室温下搅拌1小时后,吸滤沉淀,浓缩滤液,残留物用50ml无水甲苯处理,加入4.8g亚硫酰氯,混合物加热回流2小时。真空除去甲苯和过量的亚硫酰氯。残留物再用甲苯处理,分批加入3g(22mmol)叔丁醇钾,混合物在50℃加热,同时用薄层色谱监测。反应混合物用水洗涤,浓缩甲苯相。残留物用硅胶色谱处理,用10∶1正己烷/乙酸乙酯洗脱。
得到2.3g(理论值的41%)2-(2,2-二氯-1-氟乙烯基)-4-(4-甲基苯基)-1,3-噁唑啉。1HNMR(500MHz,CDCl3):2.33(s,3H);4.25(t,1H);7.15(m,4H)。原料化合物的制备
将515g 2-氟-1,1,3,3,3-五氯丙烯和27g三氯化铁(III)作为第一批加料,在110℃经2小时滴加52.6g水。反应混合物在110℃搅拌1小时,并冷却至约70℃,过滤分出固体,并滴加330.2ml亚硫酰氯。回流约2小时后,蒸发除去过量的亚硫酰氯和二氯代氟代烯丙酰氯。
得到233g(理论值的90%)二氯代氟代烯丙酰氯,沸点为134℃。
以相应的方式,并依照制备的一般知识,得到下列式(I)取代的噁唑啉:
续
应用实施例
实施例A棉红螨试验(OP抗性/浸泡处理)
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用含乳化剂的水稀释至所需浓度。
将被各种发育期的棉红螨(Tetranychus urticae)严重侵扰的豆类植物(Phaseolus vulgaris)浸入所需浓度的活性化合物制剂中进行处理。
经过所需时间后,确定百分作用率。100%意味着所有棉红螨都被杀死,0%意味着没有棉红螨被杀死。
在本实验中,例如活性化合物浓度为0.1%的制备实施例8、10的化合物7天后带来至少80%的死亡率。
实施例B草地粘虫试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)浸入所需浓度的活性化合物制剂中进行处理,在叶子仍为湿的状态期间用草地粘虫(Spodoptera frugiperda)毛虫进行侵扰。
经过所需时间后,确定百分死亡率。100%意味着所有毛虫都被杀死,0%意味着没有毛虫被杀死。
在本实验中,例如活性化合物浓度为0.1%的制备实施例1的化合物7天后表现出100%的死亡率。
实施例C菜蛾试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)浸入所需浓度的活性化合物制剂中进行处理,在叶子仍为湿的状态时用菜蛾毛虫(Plutella maculipennis)进行侵扰。
经过所需时间后,确定百分死亡率。100%意味着所有菜蛾毛虫都被杀死,0%意味着没有菜蛾毛虫被杀死。
在本实验中,例如活性化合物浓度为0.1%的制备实施例1和10的化合物7天后表现出100%的死亡率。实施例D黑尾叶蝉试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用水稀释至所需浓度。
把水稻秧苗(Oryzae sativa)浸入所需浓度的活性化合物制剂中进行处理,并在秧苗仍为湿的状态时用黑尾叶蝉幼虫(Nephotettix cincticeps)进行侵扰。
经所需时间后,确定百分死亡率。100%意味着所有黑尾叶蝉被杀死,0%意味着无黑尾叶蝉被杀死。
在本实验中,活性化合物浓度为0.1%的制备实施例8、10和11的化合物7天后表现出至少90%的死亡率。
Claims (10)
2.按权利要求1的式(I)的取代的噁唑啉,其中A 代表任选被选自下列基团的相同或不相同取代基取代一次或多次的C1-
C8烷基:卤素、氰基和C1-C4烷氧基以及各自任选被选自下列基团
的相同或不相同取代基取代一至三次的苯基、苯氧基、苄氧基、苯硫基和
苄硫基:卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧
基、C1-C4卤代烷氧基、C1-C4烷硫基和/或C1-C4卤代烷
硫基;
代表任选被相同或不相同的卤素取代基取代一或多次的C2-C8烯基;
代表任选被选自下列基团的相同或不相同取代基取代一或多次的C3-
C8环烷基:卤素、C1-C4烷基、C2-C4烯基、C1-C4卤
代烷基或C2-C4卤代烯基;和
代表任选被选自下列基团的相同或不相同取代基取代一或多次的C5-
C7环烯基:卤素、C1-C4烷基和C1-C4卤代烷基:和B 代表苯基、苄基、苯基乙-1-基、苯基乙-2-基、苯氧基甲基、苯硫
基甲基、苯氧基乙-1-基、苯硫基乙-1-基、苯氧基乙-2-基或苯
乙烯基,它们各自可任选被相同或不相同取代基取代一至四次,可提
及的苯基取代基各自为:
卤素,
C1-C18烷基,
C1-C8烷氧基-C1-C8烷基,
C1-C8卤代烷氧基,
C1-C4卤代烷基,
任选被1-3个其它氧原子间隔的C1-C18烷氧基,
C1-C18烷硫基,
C1-C8卤代烷硫基,
3,4-二氟亚甲二氧基,
3,4-四氟亚乙二氧基,
任选被C1-C4烷基、C3-C6环烷基和/或卤素取代的苄基亚氨基
氧基甲基,
环己基和环己氧基,它们各自任选被C1-C6烷基、C1-C6烷氧基、
环己基或苯基取代,
任选被选自下列基团的相同或不相同取代基取代一次或二次的吡啶氧基:
卤素、C1-C4烷基或C1-C4卤代烷基;
苯基、苄基、苯氧基、苯硫基、苄氧基和苄硫基,它们各自任选被选自下
列基团的相同或不相同取代基取代一至三次:C1-C12烷基、卤素、
C1-C4卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、
C1-C6烷氧基-C1-C6烷基、C1-C6烷氧基-亚乙氧基、
C1-C6烷硫基和/或C1-C6卤代烷硫基,D代表氢或甲基;E代表氢或甲基;和G代表氢或甲基。
3.按权利要求1的式(I)的取代的噁唑啉,其中A 代表任选被选自下列基团的相同或不相同取代基取代一次或多次的C1-C6烷基:氟、氯、溴、氰基和C1-C2烷氧基,以及各自任选被选自下列基团的相同或不相同取代基取代一或两次的苯基、苯氧基、苄氧基、苯硫基和苄硫基:氟、氯、C1-C4烷基、C1-C2卤代烷基、C1-C2烷氧基、C1-C2卤代烷氧基、C1-C2烷硫基和/或C1-C2卤代烷硫基;代表任选被选自氟、氯和/或溴的相同或不相同取代基取代一或多次的C2-C6烯基;代表任选被选自下列基团的相同或不相同取代基取代一或多次的C3-C8环烷基:氟、氯、C1-C4烷基和C2-C4烯基、以及各自被氟和/或氯取代的C1-C2烷基或C2-C4烯基;和代表任选被选自下列基团的相同或不相同取代基取代一或多次的C5-C7环烯基:氟、氯和C1-C4烷基以及被氟和/或氯取代的C1-C2烷基;和B 代表苯基、苄基、苯基乙-1-基、苯基乙-2-基、苯氧基甲基、苯硫基甲基、苯氧基乙-1-基、苯氧基乙-2-基、苯硫基乙-1-基或苯乙烯基,它们各自任选被相同或不相同的取代基取代一至四次,可提及的苯基取代基各自为:
F、Cl、Br;
C1-C18烷基;
C1-C6烷氧基-C1-C8烷基;
被选自F和/或Cl的相同或不相同取代基取代一至六次的C1-C8
烷氧基;
被选自F和/或Cl的相同或不相同取代基取代一至五次的C1-C2
烷基;
C1-C18烷氧基和-(OC2H4)1-3-O-C1-C6烷基;
C1-C12烷硫基;
被选自F和/或Cl的相同或不相同取代基取代一至六次的C1-C8
环己基或环己氧基,它们各自任选被C1-C4烷基、C1-C4烷氧基、
环己基或苯基取代;
吡啶氧基,它任选被选自F、Cl或CF3的相同或不相同取代基取代一次
或两次:
苯基、苄基、苯氧基、苯硫基、苄氧基和苄硫基,它们各自任选被选自下
列基团的相同或不相同取代基取代一至三次:C1-C12烷基、F、Cl、
Br、CF3,以及C1-C4烷氧基、被选自F和/或Cl的相同或不相
同取代基取代一至六次的C1-C4烷氧基、C1-C4烷氧基-C1
-C4烷基、C1-C4烷氧基亚乙氧基、C1-C4烷硫基或被选自
F和/或Cl的相同或不相同取代基取代一至六次的C1-C4烷硫基;D代表氢或甲基:
E代表氢或甲基;和
G代表氢或甲基。
5.防治害虫的组合物,它含有至少一种权利要求1的式(I)化合物。
6.防治动物害虫的方法,其中使权利要求1的式(I)化合物作用于动物害虫和/或它们的栖息地。
7.权利要求1的式(I)化合物防治动物害虫的用途。
8.制备防治害虫的组合物的方法,其中将权利要求1的式(I)化合物与稀释剂和/或表面活性剂混合。
9.下式的二氯代-氟代烯丙酰氯。
CCl2=CF-COCl.
10.制备权利要求9的二氯代氟代烯丙酰氯的方法,其中必要时在催化剂存在下水解2-氟-1,1,3,3,3-五氯丙烯。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4401099A DE4401099A1 (de) | 1994-01-17 | 1994-01-17 | Substituierte Oxazoline |
DEP4401099.0 | 1994-01-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1138856A true CN1138856A (zh) | 1996-12-25 |
Family
ID=6508027
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN95191255A Pending CN1138856A (zh) | 1994-01-17 | 1995-01-04 | 取代的噁唑啉 |
Country Status (14)
Country | Link |
---|---|
US (1) | US5990140A (zh) |
EP (2) | EP0740660B1 (zh) |
JP (1) | JPH09507493A (zh) |
KR (1) | KR100393732B1 (zh) |
CN (1) | CN1138856A (zh) |
AU (1) | AU698241B2 (zh) |
BR (1) | BR9506516A (zh) |
CZ (1) | CZ210296A3 (zh) |
DE (3) | DE4401099A1 (zh) |
ES (2) | ES2210057T3 (zh) |
HU (1) | HUT76146A (zh) |
PL (1) | PL315520A1 (zh) |
PT (1) | PT1132368E (zh) |
WO (1) | WO1995019349A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19506535A1 (de) * | 1995-02-09 | 1996-08-14 | Bayer Ag | 1,6-Naphthyridoncarbonsäurederivate |
DE19520936A1 (de) * | 1995-06-08 | 1996-12-12 | Bayer Ag | Ektoparasitizide Mittel |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2372409A (en) * | 1943-04-12 | 1945-03-27 | Commercial Solvents Corp | Process for preparing 2-oxazolines |
US2665307A (en) * | 1952-04-02 | 1954-01-05 | Sharples Chemicals Inc | Trichloroacrylyl chloride |
GB1400448A (en) * | 1971-08-25 | 1975-07-16 | Boots Co Ltd | Oxazoline derivatives arylalkanoic acids their preparation and therapeutic compositions containing them |
US3777031A (en) * | 1971-09-09 | 1973-12-04 | Robins Co Inc A H | 2-(p-phenylbenzyl)oxazolines in treating inflammation |
US4045447A (en) * | 1973-06-09 | 1977-08-30 | Bayer Aktiengesellschaft | Process for preparing 2-vinyl oxazolines |
DE2732213A1 (de) * | 1977-07-16 | 1979-01-25 | Bayer Ag | Derivate der cyclopropancarbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als zwischenprodukte zur herstellung von insektiziden |
JPS5718646A (en) * | 1980-07-10 | 1982-01-30 | Nippon Tokushu Noyaku Seizo Kk | Trichloroalkene derivative and agricultural and horticultural fungicide containing said compound as active component |
JPH01228972A (ja) * | 1988-03-10 | 1989-09-12 | Rikagaku Kenkyusho | 2−オキサゾリンの合成法 |
US4977171A (en) * | 1988-06-09 | 1990-12-11 | Yashima Chemical Industrial Co., Ltd. | Oxa- or thia-zoline derivative |
JPH02235872A (ja) * | 1989-03-10 | 1990-09-18 | Nippon Mining Co Ltd | 2―オキサゾリン誘導体及びその製造方法 |
JPH03197469A (ja) * | 1989-05-02 | 1991-08-28 | Nippon Mining Co Ltd | 2―オキサゾリン誘導体の製造方法 |
AU634608B2 (en) * | 1989-12-09 | 1993-02-25 | Kyoyu Agri Co., Ltd. | 2-substituted phenyl-2-oxazoline or thiazoline derivatives, process for producing the same and insectides and acaricides containing the same |
AU658955B2 (en) * | 1992-01-28 | 1995-05-04 | Sumitomo Chemical Company, Limited | An oxazoline derivative, its production and its use |
CZ104797A3 (en) * | 1994-10-06 | 1997-07-16 | Bayer Ag | Substituted biphenyloxazolines, process of their preparation, intermediates for their preparation, preparations in which said substances are comprised and their application |
JPH08258641A (ja) * | 1995-01-26 | 1996-10-08 | Aisan Ind Co Ltd | ナンバープレート用フレーム |
-
1994
- 1994-01-17 DE DE4401099A patent/DE4401099A1/de not_active Withdrawn
-
1995
- 1995-01-04 JP JP7518806A patent/JPH09507493A/ja not_active Ceased
- 1995-01-04 PT PT01109541T patent/PT1132368E/pt unknown
- 1995-01-04 WO PCT/EP1995/000021 patent/WO1995019349A1/de active Application Filing
- 1995-01-04 PL PL95315520A patent/PL315520A1/xx unknown
- 1995-01-04 ES ES01109541T patent/ES2210057T3/es not_active Expired - Lifetime
- 1995-01-04 US US08/669,501 patent/US5990140A/en not_active Expired - Fee Related
- 1995-01-04 EP EP95905118A patent/EP0740660B1/de not_active Expired - Lifetime
- 1995-01-04 EP EP01109541A patent/EP1132368B1/de not_active Expired - Lifetime
- 1995-01-04 CZ CZ962102A patent/CZ210296A3/cs unknown
- 1995-01-04 BR BR9506516A patent/BR9506516A/pt not_active IP Right Cessation
- 1995-01-04 CN CN95191255A patent/CN1138856A/zh active Pending
- 1995-01-04 DE DE59510831T patent/DE59510831D1/de not_active Expired - Fee Related
- 1995-01-04 AU AU13857/95A patent/AU698241B2/en not_active Ceased
- 1995-01-04 KR KR10-2002-7005409A patent/KR100393732B1/ko not_active IP Right Cessation
- 1995-01-04 ES ES95905118T patent/ES2166814T3/es not_active Expired - Lifetime
- 1995-01-04 HU HU9601937A patent/HUT76146A/hu unknown
- 1995-01-04 DE DE59509813T patent/DE59509813D1/de not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
KR100393732B1 (ko) | 2003-08-06 |
HU9601937D0 (en) | 1996-09-30 |
AU1385795A (en) | 1995-08-01 |
EP1132368A2 (de) | 2001-09-12 |
ES2210057T3 (es) | 2004-07-01 |
JPH09507493A (ja) | 1997-07-29 |
US5990140A (en) | 1999-11-23 |
EP0740660A1 (de) | 1996-11-06 |
EP0740660B1 (de) | 2001-11-07 |
ES2166814T3 (es) | 2002-05-01 |
DE59509813D1 (de) | 2001-12-13 |
BR9506516A (pt) | 1997-09-09 |
DE4401099A1 (de) | 1995-07-20 |
PT1132368E (pt) | 2004-04-30 |
WO1995019349A1 (de) | 1995-07-20 |
HUT76146A (en) | 1997-07-28 |
DE59510831D1 (de) | 2003-12-18 |
AU698241B2 (en) | 1998-10-29 |
EP1132368B1 (de) | 2003-11-12 |
PL315520A1 (en) | 1996-11-12 |
EP1132368A3 (de) | 2001-09-19 |
CZ210296A3 (en) | 1996-10-16 |
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