CN1106146C - 对羟基苯乙酸用于降低杀虫剂的驱避性 - Google Patents
对羟基苯乙酸用于降低杀虫剂的驱避性 Download PDFInfo
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- CN1106146C CN1106146C CN96112296A CN96112296A CN1106146C CN 1106146 C CN1106146 C CN 1106146C CN 96112296 A CN96112296 A CN 96112296A CN 96112296 A CN96112296 A CN 96112296A CN 1106146 C CN1106146 C CN 1106146C
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- alkyl
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- hydroxyphenylaceticacid
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- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 239000002917 insecticide Substances 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 241001674044 Blattodea Species 0.000 claims abstract description 23
- -1 carboxylic acid compound Chemical class 0.000 claims description 56
- 229910019142 PO4 Inorganic materials 0.000 claims description 14
- 239000010452 phosphate Substances 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000005871 repellent Substances 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 230000002940 repellent Effects 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- 230000000361 pesticidal effect Effects 0.000 claims 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 39
- 229910052736 halogen Inorganic materials 0.000 description 22
- 150000002367 halogens Chemical class 0.000 description 22
- 239000002585 base Substances 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 235000021317 phosphate Nutrition 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000002728 pyrethroid Substances 0.000 description 6
- 240000000233 Melia azedarach Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000005667 attractant Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
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- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 235000008429 bread Nutrition 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 230000031902 chemoattractant activity Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002012 dioxanes Chemical class 0.000 description 2
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
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- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/002—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits
- A01N25/006—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits insecticidal
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Food Science & Technology (AREA)
- Toxicology (AREA)
- Insects & Arthropods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及对羟基苯乙酸的新用途,这种新用途是通过本身或与其他化合物的混合来降低杀虫剂在蟑螂防治中的驱避性,本发明还涉及含有这些混合物的防治蟑螂组合物,详细内容见说明书。
Description
本发明涉及对羟基苯乙酸的新用途,这种新用途是通过本身或与其他化合物的混合物来降低杀虫剂,特别是防治蟑螂的杀虫剂的驱避性,以及其中含有对羟基苯乙酸和这种羧酸与其他化合物的混合物的防治蟑螂组合物。
在居室和商业中,蟑螂的侵染是一个相当严重的卫生问题,在许多情况下,对蟑螂的防治是必需的。可是,由于蟑螂的生活类型,对它们的防治非常困难。其中存在的一个特殊的问题是,在实际中许多杀虫剂具有驱避性,这就降低了防治的成功率。
M.K.Rust和D.A.Reierson(Journal of Economic Entomology 70(1)(1977),34-38)描述了应用蟑螂粪便的提取物,以改善毒死蜱、残杀威、二嗪农和氟硅杀的活性,并讨论了降低作为这些杀虫剂的驱避性的这种作用。
A.E.Glaser(International Pest Control 22(1)(1980),7-8 21)描述了对杀螟硫磷出现的同样的现象。
然而,上述方法不适于商业用途,因为通过提取蟑螂的粪便,只有少量的抗驱避物质可提供用作杀虫剂。
根据本发明的抗驱避性对羟基苯乙酸和其与其他化合物的混合物降低了杀虫剂的驱避作用。特别是拟除虫菊酯对蟑螂的驱避作用,并因此增加了昆虫的化学防治组合物的作用。
根据本发明的已知并且稳定的式(I)化合物,以其本身和以与其他化合物的混合物的形式,在昆虫的化学防治组合物中具有很高的活性,且优选用于饵料和喷雾施用。
式(I)化合物可以酸的形式,也可以其盐的形式使用。还可以其游离酸与特定的盐的混合物的形式使用。
可用来制备羟基苯乙酸的特定的盐的碱都是在化学活性化合物中常用的,优选碱金属、碱土金属、铵、烷基铵、二烷基铵、三烷基铵或四烷基铵氢氧化物,更优选为钠、钾、钙或铵氧氧化物,且特别优选为氢氧化钠。
可使用根据本发明的式(I)化合物和/或其与其他化合物的混合物防治蟑螂,即蠊目的昆虫,特别是蠊科的昆虫,优选德国小蠊或大蠊科,优选东方蠊和美洲大蠊,并且也防治其他种的蟑螂,特别优选的是防治德国小蠊。
根据本发明的式(I)化合物和/或其与其他化合物的混合物降低了蟑螂对杀虫剂例如拟除虫菊酯的驱避作用。
上述作用在蟑螂的各种变化的发育期(幼虫,成虫)都存在。在蟑螂防治中,无论使用的防治方法的种类如何,可非常方便地使用对羟基苯乙酸和/或其与其他化合物的混合物。优选地可将其用于化学防治方法中,且如果适合与其他活性剂,如引诱饵料或其他引诱剂、合成或天然存在的杀虫剂等一起使用。
通过简单地思考或简单地研究,可能的是由专家来确定对于特定的使用目的施用的混合物和类型以及较好的施用量。
优选以常规的喷雾方式施用对羟基苯乙酸和/或其与其他化合物的混合物。施用常规制剂时可使用通常使用的施药器械。还可将对羟基苯乙酸和/或其与其他化合物的混合物,如果适合的话,与适合杀虫剂的混合物配制成可被撒布的粉剂或颗粒剂。对羟基苯乙酸和/或其与其他化合物的施用量优选每m20.1至500mg,且更优选每m2 1至200mg(以对羟基苯乙酸为基础)。
当用于含有杀虫剂的饵料中时,将对羟基苯乙酸和/或其与其他化合物的混合物与饵料混合或靠近饵料施用(例如在其顶部)。对羟基苯乙酸和/或其与其他化合物的混合物还可以在相当长的时间内释放的形式(缓释制剂)存在。例如,为此,可将它们结合入聚合物材料、石蜡、蜡等中,或以微胶囊形式存在。可使用的常规设备是捕集器,且通常引诱的饲料的药剂物质是饵料。对羟基苯乙酸和/或其与其他化合物的混合物的优选使用量是每克饵料为0.0001至100mg(更优选0.01至20mg)(以对羟基苯乙酸为基础)。
本发明还涉及防治蟑螂的组合物,其包括如果适合的话,除了常规的载体和助剂和/或其他添加剂(如饵料或引诱剂)外,其中包括对羟基苯乙酸和/或其与其他化合物和混合物和至少一种杀虫活性物质,可以将对羟基苯乙酸和/或其与其他化合物的混合物与其他组分混合或以分离放置的形式存在。
其他化合物意为,特别是有机羧酸,特别优选苯甲酸、苯乙酸、邻氨基苯甲酸、3-(间羟基苯基)丙酸、3-(对羟基苯基)丙酸、2-羟基丙酸、癸酸、棕榈酸、硬脂酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、甲基庚二酸、富马酸或马来酸。
可被使用的杀虫物质是对蟑螂有活性的,且杀虫活性物质和根据本发明的对羟基苯乙酸或混合物之间无有害作用的各种物质。
例如,杀虫活性物质可属于杀虫活性的磷酸酯,氨基甲酸酯,天然存在的除虫菊酯和合戊的拟除虫菊酯,脒基腙,硫酰胺,硝基亚氨基、硝基亚甲基、氰基亚氨基或氰基亚甲基化合物,吡咯烷-2,4-二酮衍生物,吡唑啉衍生物,齐墩螨素(avermectin和ivermecfin)衍生物,即苦楝子素、annonines和/或鱼尼汀。
还可能使用几丁质合成抑制剂(例如triflumeron、duflubenzuron、Lufenuron、氟虫脲等),以及保幼激素和拟态素(例如:蒙五一五、蒙五一二、双氧威、蚊蝇醚等)或“普通药剂”(硼、酵母、烤面包粉等)。
以下可叙述根据本发明特别优选的与对羟基苯乙酸和/或其与其他化合物的混合物配制的杀虫剂:
1)式(II)的甲酰胺酸酯
其中
R1 代表任意取代的碳环基或杂环芳基,或代表任意取代的肟基,下面将详述优选的R1基团,
R2 代表C1-C4烷基,和
R3 代表氢或C1-C4烷基,或代表基团U,其中
U 代表-CO-R4基,其中
R4代表卤素、C1-C4烷基、C1-C4烷氧基,C3-C5链烯氧基,C3-C5链炔氧基、C1-C4烷硫基、C1-C4烷基氨基、二C1-C4烷基氨基或C1-C4烷基羟基氨基,或
代表苯氧基,苯硫基或苯基氨基,它们任意地被卤素、硝基、氰基、三氟甲基、C1-C4烷基、C1-C4烷氧基、C1-C4亚烷二氧基、C1-C4烷硫基或C1-C4烷氧基羰基取代,或
其中
R5代表氢、C1-C4烷基或二C1-C4烷基氨基羰基,和
R6代表C1-C4烷基、C1-C4烷硫基、氰基C1-C4烷硫基或C1-C4烷硫基C1-C4烷基;
或两个R5和R6基团一起代表任意地被氧、硫、SO或SO2间断的C2-C8烷二基,或
其中
U代表基团-Sv(O)w-R7,其中
v代表1或2和
w代表0、1或2、其中在V为2的情况下,w表示0,
R7代表C1-C4烷基、C3-C5链烯基、C3-C5链炔基或C3-C6环烷基,它们可任意地被卤素取代,或代表苯基、苄基或苯乙基、它们可任意地被卤素、氰基、硝基、三氟甲基、三氟甲氧基、三氟甲硫基、 C1-C4烷基或C1-C4烷氧基取代,或代表下式的基团其中
R8代表C1-C4烷基、C3-C5链烯基、C3-C5链炔基、C3-C6环烷基或苄基,和
R9代表C1-C4烷基、C3-C5链烯基、C3-C5链炔基、C3-C6环烷基、苄基、苯乙基、卤代羰基、甲酰基、C1-C4烷基羰基、C1-C4烷氧基羰基、C1-C4烷氧基苯氧基羰基、C3-C5链炔氧基羰基、C3-C5链烯氧基羰基、C1-C4烷硫基羰基、C1-C4烷基氨基羰基、C1-C4烷基羟基氨基羰基、C1-10烷基苯氧基羰基、=C1-C4烷基氨基羰基、苯硫基羰基、苯氧基羰基或2,3-二氢-2,2-二甲基-7-苯并呋喃氧基羰基,或代表苯硫基、苯亚磺酰基、苯磺酰基或苯基,它们可任意地被卤素、氰基、硝基、三氟甲基、C1-C10烷基或C1-C4烷氧基取代,或代表下式基团其中
R10具有上述R5给出的定义,和
R11具有上述R6给出的定义,此外,其中,在基团中,基团R8和R9一起代表具有3至8个碳原子并可任意地被氧或硫原子间断的烃链,且其中R7还可代表基团Sv(O)w-R7被键合的相同的基团。特别优选的活性化合物组分是式II的氨基甲酸酯,其中
R1代表由苯基、萘基、2,3-二氢-7-苯并呋喃基、吡唑基或嘧啶基组成的一组基团,上述基团可任意地被C1-C4烷基、C2-C4链烯基、C1-C4烷氧基、C1-C4烷氧基甲基、C1-C4烷硫基、C1-C4烷硫基甲基、C1-C4烷基氨基、二(C1-C4烷基)氨基、二(C3-C4链烯基)氨基、卤素、二氧戊环基、亚甲二氧基和/或被基团-N=CH-N(CH3)2取代,或其中
R1代表下式的亚烷基氨基
其中
R12和R13具有上述R5和R6分别给出的定义,
R2代表C1-C4烷基,和
R3代表氢或C1-C4烷基(优选氢)。可叙述的式(II)的氨基甲酸酯的实例为下述的N-甲基氨基甲酸酯:2-甲基苯基、2-乙基苯基、2-异丙基苯基、2-仲丁基苯基、2-甲氧基苯基、2-乙氧基苯基、2-异丙氧基苯基、4-甲基苯基、4-乙基苯基、4-正丙基苯基、4-甲氧基苯基、4-乙氧基苯基、4-正丙氧基苯基、3,4,5-三甲基苯基、3,5-二甲基-4-甲硫基苯基、3-甲基-4-二甲基氨基苯基、2-乙硫基甲基苯基、1-萘基、 2,3-二氢-2,2-二甲基-7-苯并呋喃基、2,3-(二甲基亚甲二氧基)苯基、2-(4,5-二甲基-1,3-二氧戊环-1-基)苯基、 1-甲硫基亚乙基氨基、2-甲硫基-2-甲基亚丙基氨基、1-(2-氰基乙硫基)亚乙基氨基和1-亚硫基甲基-2,2-二甲基亚丙基氨基的N-甲基氨基甲酸酯,优选N-甲基氨基甲酸2-异丙氧基苯基酯。2)式(III)的羧酸酯
其中,
R14代表开链烷基或环烷基,其或任意地被下述基团取代:卤素,烷基或环烷基,或任意地被卤素、烷基和/或烷氧基取代的链烯基,或任意地被卤素或任意卤素取代基(其由烷基、烷氧基、亚烷二氧基和/或烷硫基组成)取代的苯基或苯乙烯基,或螺环连接的任意卤素取代的环链烯基(其被任意苯并稠合),且其中
R15代表氢、烷基、卤代烷基、链烯基、链炔基或氰基,和
R16代表任意取代的烷基或芳基或代表杂环基,或与R15和其中被键合的两个基团的碳原子一起形成环戊酮环。
其中
R17代表氢、甲基、氟、氯或溴,和
R18代表甲基、氟、氯、溴、C1-C2氟烷基或C1-C2氯氟烷基,或代表苯基,其任意被卤素和/或任意卤素取代基(其由C1-C4烷基、C1-C4烷氧基、C1-C4烷硫基和/或C1-C2亚烷二氧基组成),或其中R7和R8两个基团代表C2-C5烷二基(亚烷基):
或其中b)R14代表基团
其中
R19代表苯基,其任意被卤素和/或任意取代的卤素基团(其由C1-C4烷基、C1-C4烷氧基、C1-C4烷硫基或C1-C2亚烷二氧基组成)取代,和
R20代表异丙基或环丙基;
或其中c)R14代表甲基或下述基团之一
其中虚线表示可能的双键,和其中
R14代表氢、C1-C4烷基、C1-C4卤代烷基、氰基或乙炔基,和
R16代表由苯基、呋喃基和四氢苯二酰亚氨基组成的基团,其中上述基团可被卤素和/或由C1-C4烷基、C2-C4链烯基、C1-C4烷氧基、C2-C4链烯氧基、C1-C4烷硫基、C1-C2亚烷二氧基、苯氧基和/或苄基组成的一组基团(它们中又可被卤素取代)取代,且其中R6优选代表四氟苯基、3,4-二氯苯基或四氢苯二酰亚氨基,或代表在一个苯环或两个苯环上被卤素(优选氟)取代的苯氧基苯基。天然存在的拟除虫菊酯(如除虫菊)或合成拟除虫菊酯是特别优选的式(III)羧酸酯。
根据本发明特别优选的式(III)羧酸酯的实例可叙述如下:3,4,5,6-四氢苯二酰亚氨基甲基2,2-二甲基-3-(2-甲基丙烯-1-基)环丙烷羧酯、3-苯氧苄基2,2-二甲基-3-(2,2-二氯乙烯基)环丙基羧酸酯、2-氰基-3-苯氧基苄基2,2-二甲基-3-(2,2-二氯乙烯基)环丙烷羧酸酯、α-氰基-4-氟-3-苯氧基苄基2,2-二甲基-3-(2,2-二氯乙烯基)环丙烷羧酸酯、2,3,5,6-四氟苄基2,2-二甲基-3-(2,2-二氯乙烯基)环丙烷羧酸酯、α-氰基-3-苯氧基苄基2,2-二甲基-3-(2,2-二溴乙烯基)环丙烷羧酸酯和α-氰基-3-苯氧基苄基3-甲基-2-(4-氯苯基)丁酸酯。3)式(IV)的磷酸酯或膦酸酯
其中
A是相同或不同的并代表O或S,和
B代表O、S或-NH-,或代表中心P原子和R23之间的直接键,和
R21和R22是相同或不同的并代表任意取代的烷基或芳基,和,
R23代表氢、任意取代的烷基、芳基、杂芳基、芳烷基、链烯基或二恶烷基或肟基,或代表被键合其上的相同的基团。上述特别优选的式(IV)磷酸酯和膦酸酯是下述基团,其中
R21和R22是相同或不同的并代表C1-C4烷基或苯基,
R23代表氢,或代表具有1至4个碳原子的烷基,其任意被卤素、羟基、氰基、任意卤素取代的苯基、氨基甲酰基、烷基磺酰基、烷基亚硫酰基、烷基羰基、烷氧基、烷硫基、烷氧基羰基或在各种情况下具有多达6个碳原子的烷基氨基羰基取代,
R23还代表具有多达4个碳原子的链烯基,其任意被卤素取代的苯基或C1-C4烷氧基羰基取代,或
R23代表以下通式的基团
其中R24和R25具有上述R5和R6给出的定义,或代表氰基或苯基,
R23还代表二恶烷基,其可被键合到R22的相同基团取代,或R23代表键合到其上的相同基团,或R23代表苯基,其任意被甲基、硝基、氰基、卤素和/或甲硫基取代,且其中
R23还特别优选地代表杂芳基,如吡啶基、喹啉基、喹喔啉基、嘧啶基或苯并-1,2,4-三嗪基,它们任意被C1-C4烷氧基、C1-C4烷硫基甲基、C1-C4烷基和/或卤素取代。
下述具体地叙述为:O,O-二甲基、O,O-二乙基-O-(2,2-二氯和2,2-二溴乙烯基)磷酸酯,O,O-二乙基-O-(4-硝基苯基)硫羰磷酸酯,O,O-二甲基-O-(3-甲基-4-甲硫基苯基),硫羰磷酸酯,O,O-二甲基-O-(3-甲基-4-硝基苯基)硫羰磷酸酯,O-乙基-S-正丙基-O-(2,4-二氯苯基)硫羰磷酸酯,O-乙基-S-正丙基-O-(4-甲硫基苯基)硫羰磷酸酯,O,O-二甲基-S-(4-氧代-1,2,3-苯并三嗪-3-基-甲基)硫羰磷酸酯,O-甲基-O-(2-异丙基-6-甲氧基嘧啶-4-基)硫羰甲烷磷酸酯,O,O-二乙基-O-(2-异丙基-6-甲基嘧啶-4-基)硫羰磷酸酯,O,O-二乙基-O-(3-氯-4-甲基-香豆素-7-基)硫羰磷酸酯,O,O-二甲基-2,2,2-三氯-1-羟基乙烷磷酸酯,O,O-二甲基-S-(甲基氨基羰基甲基)硫羰磷酸酯O-甲基-O-(6-甲氧基-2-叔丁基)嘧啶-4-基)硫羰乙烷磷酸酯。4)式(V)的硝基亚甲基、硝基亚氨基、氰基亚氨基或氰基亚甲基衍生物
其中
R30代表C1-C4烷基(优选甲基或乙基),或
R30与R27-起代表任意支链的C2-C5烷二基链(优选-(CH2)2-或-(CH2)3-),和
R31代表氢或C1-C4烷基(优选氢),
R27代表C1-C4烷基(优选甲基或乙基),或与R30一起代表任意支链的C2-C5烷二基链(优选-(CH2)2-或-(CH2)3-)
R28代表NO2或CN,
R29代表任意取代的(优选被卤素和/或C1-C4烷基取代)杂芳基(优选吡啶基)(其中R29特别优选代表2-氯吡啶-5-基)
Q代表=C-或-N-,和
V代表直接键,或代表C1-C3亚烷二基(优选-CH2-)。
以实例的方式将一些特别优选的式(V)化合物具体列示如下:其中R32代表
基在上述通式和基团的定义中,上述基团具有下述一般的和优选的定义:
烷基本身或在烷氧基或烷氧羰基中作为组分的烷基表示具有1至5,优选1至4和特别优选1至3个碳原子的直链或支链烷基,其中可特别叙述的是甲基、乙基、正和异丙基和正、异、仲和叔丁基,且其中甲基和乙基,特别是甲基是被特别选出的。
在任意取代的苯基、苯氧基或苯氧羰基中,苯基环上优选带有1至3个,特别优选1或2个相同或不同的取代基,取代基可以是在活性化合物化学中各种通常的取代基。可叙述的优选取代基为:C1-C4烷基、 C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷基、C1-C4卤代烷氧基、硝基、羟基和卤素(优选氟、氯和、或溴)。
根据它们的特殊的物理和/或化学性质,对羟基苯乙酸和/或其与其他化合物的混合物和/或杀虫物质和对羟基苯乙酸和/或其与其他化合物的混合物与杀虫物质的混合物可被转化成通常的制剂,如溶剂,乳剂,悬浮剂,粉剂,泡沫剂,糊剂,颗粒剂,气雾剂,用活性化合物浸渍的天然和合成材料和在聚合物中的微细胶囊。
这些制剂是以已知方法生产的,例如,通过将活性组分与助剂和/或填充剂,即液体溶剂和/或固体载体混合而生产,制剂中任意地使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。在使用水作用为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适合的液体溶剂主要有:芳香烃,如二甲苯,甲苯或烷基萘,氯代芳烃或氯代脂肪烃,如氯代苯、二氯乙烷或二氯甲烷,脂肪烃,如环已烷或链烷烃,例如矿物油馏份,醇,如丁醇或乙二醇及其醚和酯,酮,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;适合的固体载体有:例如,天然矿物粉末,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱土或硅藻土,和合成矿物粉末,如高分散硅石、氧化铝和硅酸盐;适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石、大理石、浮石、海泡石和白云石,以及无机的合成颗粒和有机粉末,和有机材料的颗粒如锯末、坚果壳、玉米穗茎和烟草茎;适合的乳化剂和/或成泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及白蛋白水解产物;适合的分散剂有:例如木素亚硫酸盐废液和甲基纤维素。
在制剂中可使用粘合剂如羧甲基纤维素和粉末、颗粒或胶乳状合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷酯如脑磷脂和卵磷脂,和合成磷脂。其他粘合剂可以是矿物油和植物油。
可能使用的着色剂如无机颜料,例如氧化铁、氧化钛和普鲁士兰、和有机染料,如茜素染料,偶氮染料金属酞菁染料,和痕量营养素,例如铁、锰、硼、铜、钴、钼和锌盐。
在毒饵制剂中(优选撒布毒饵制剂或固体毒饵制剂),该制剂还可含有引诱蟑螂和/或使它们摄入杀虫病物质的其他添加剂。可使用的引诱剂和饲养物质是在各种制剂中通常使用的,如天然存在或合成产生的物质和/或蟑螂容易摄入的物质,如含有淀粉、蛋白质和/或糖的以谷物或糖为基础的产物。
制剂优选含有0.001至95,特别是0.01至70%重量的对羟基苯乙酸和/或其与其他化合物的混合物。
制剂优选含有(如果适合,除对羟基苯乙酸和/或其与其他化合物的混合物之外)0.1至95,特别是0.5至90%重量的杀虫物质。
防治蟑螂的组合物是以适合的使用形式以常规的方式使用的。
通过下述的实施例来举例说明对羟基苯乙酸和/或基与其他化合物的混合物的生物活性。实施例A 饵料作用的改善
在室(2.25×4.70m)内的2个相对角落的隐藏处,一个角落内放入饮用水另一个角落内放一片面包干。一天后放入20只雄和20只雌蟑螂(德国小蠊),将供摄取的含杀虫剂的饵料罐(杀虫活性化合物:0.5%重量的乙基毒死蜱)放置在距面包干40cm处的墙边。
饵料或是含有对羟基苯乙酸,或是未处理的。
3间室内放入处理的饵料罐,且3间室内放入未处理的饵料罐。
在以后的3天里测定雄性动物和雌性动物的死亡率。
试验结果:
实施例B在实验室试验中喷雾作用的改善
处理类型 | 死亡百分率% | ||
第1天 | 第2天 | 第3天 | |
对照(仅有杀虫剂) | 22 | 42 | 52 |
杀虫剂+10mg对羟基苯乙酸 | 46 | 58 | 63 |
用含有(a)杀虫活性化合物氟氯氰菊酯或(b)氟氯氰菊酯和对羟基苯乙酸的喷雾水溶液向瓷砖喷雾,以使氟氯氰菊酯的施用量为每m2 20mg活性化合物和对羟基苯乙酸的施用量为每m2 1mg。
将上述瓷砖每个都放置在含有水、食物的隐藏处的容器(49×59cm,高度29.5cm)的角落中,并在操作前24小时放入雄和雌德国小蠊(各5个)。每个试验重复5次。
试验结果
实施例C
处理类型 | 死亡百分率% | |
第1天 | 第2天 | |
对照(仅有杀虫剂) | 32 | 44 |
杀虫剂+对羟基苯乙酸 | 68 | 78 |
在实际试验中喷雾作用的改善
在澳大利亚使用含有(a)杀虫活性化合物β-氟氯氰菊酯或(b)β-氟氯氰菊酯和对羟基苯乙酸,使得β-氟氯氰菊酯的施用量为每m26.25mg活性化合物(推荐量的一半),且对羟基苯乙酸的施用量为每m2 1mg。
试验在卫生条件非常差的平面上进行。每个制剂(β-氟氯氰菊酯或β-氟氯氰菊酯和对羟基苯乙酸)处理7至8个组。通过评价处理前和处理后一段时间内的粘合捕集器的捕获量来测定活性。
处理类型 | 7天后降低率% |
对照(仅有杀虫剂) | 37 |
杀虫剂+对羟基苯乙酸 | 65 |
Claims (4)
1.杀虫组合物,其包含:
(A)0.1-95%重量的杀虫剂及
(B)0.001-95%重量的(i)对羟基苯乙酸或其盐或(ii)其与其他羧酸的混合物,其中成分A的驱避作用被成分B降低。
2.根据权利要求1的杀虫组合物,其特征在于,除了任选以盐形式存在的对羟基苯乙酸或其与其他羧酸化合物的混合物外,它们还含有氨基甲酸酯,羧酸酯,磷酸酯、膦酸酯、硝基亚甲基、硝基亚氨基、氰基亚氨基或氰基亚甲基衍生物。
3.制备权利要求1的杀虫组合物的方法,其包含将(i)对羟基苯乙酸或其盐或(ii)其与其它羧酸的混合物与助剂及任选的增量剂混合。
4.权利要求1或2的杀虫组合物用于防治蟑螂的用途。
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DE19528306A DE19528306A1 (de) | 1995-08-02 | 1995-08-02 | Para-Hydroxyphenylessigsäure zur Reduktion der Repellenz von Insektiziden |
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CN111743885B (zh) * | 2020-08-17 | 2022-03-15 | 山东省科学院生物研究所 | 一种对羟基苯乙酸在预防和/或治疗心血管疾病中的应用 |
CN113861154B (zh) * | 2021-10-21 | 2022-09-13 | 华南师范大学 | 一种二氢异香豆素类衍生物及其制备方法与应用 |
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JPS5042053A (zh) * | 1973-08-20 | 1975-04-16 | ||
EP0588203A1 (de) * | 1992-09-18 | 1994-03-23 | Bayer Ag | Schabenbekämpfungsverfahren und Mittel zur Bekämpfung von Schaben |
US5518719A (en) * | 1989-09-08 | 1996-05-21 | Burlington Bio-Medical & Scientific Corp. | Attractants and lures for cockroaches and palmettos |
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JPS5042053A (zh) * | 1973-08-20 | 1975-04-16 | ||
US5518719A (en) * | 1989-09-08 | 1996-05-21 | Burlington Bio-Medical & Scientific Corp. | Attractants and lures for cockroaches and palmettos |
EP0588203A1 (de) * | 1992-09-18 | 1994-03-23 | Bayer Ag | Schabenbekämpfungsverfahren und Mittel zur Bekämpfung von Schaben |
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EP0756821B1 (de) | 2001-03-14 |
NO963218L (no) | 1997-02-03 |
CN1148464A (zh) | 1997-04-30 |
BR9603254A (pt) | 1998-04-28 |
EP0756821A2 (de) | 1997-02-05 |
HUP9602125A2 (en) | 1997-05-28 |
GR3035866T3 (en) | 2001-08-31 |
AU702909B2 (en) | 1999-03-11 |
CA2182349A1 (en) | 1997-02-03 |
TR199600607A2 (tr) | 1997-02-21 |
JPH0940510A (ja) | 1997-02-10 |
ES2155157T3 (es) | 2001-05-01 |
HU9602125D0 (en) | 1996-09-30 |
EP0756821A3 (de) | 1997-11-26 |
JP3963505B2 (ja) | 2007-08-22 |
MX9603133A (es) | 1997-03-29 |
AR003075A1 (es) | 1998-05-27 |
ATE199627T1 (de) | 2001-03-15 |
US5741501A (en) | 1998-04-21 |
SV1996000066A (es) | 1997-02-17 |
DE59606574D1 (de) | 2001-04-19 |
NO963218D0 (no) | 1996-08-01 |
AU6079396A (en) | 1997-02-06 |
BG100761A (en) | 1997-04-30 |
MY112982A (en) | 2001-10-31 |
DE19528306A1 (de) | 1997-02-06 |
PL315467A1 (en) | 1997-02-03 |
KR970009555A (ko) | 1997-03-27 |
PT756821E (pt) | 2001-08-30 |
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