CN1225632A - 取代的n-(5-异噻唑基)-硫代酰胺 - Google Patents
取代的n-(5-异噻唑基)-硫代酰胺 Download PDFInfo
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- CN1225632A CN1225632A CN 97196503 CN97196503A CN1225632A CN 1225632 A CN1225632 A CN 1225632A CN 97196503 CN97196503 CN 97196503 CN 97196503 A CN97196503 A CN 97196503A CN 1225632 A CN1225632 A CN 1225632A
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- alkyl
- fluorine
- different
- halogen atom
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- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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Abstract
本发明涉及新的式(Ⅰ)的N-(5-异噻唑基)-硫代酰胺、其制备方法及其用于防治动物害虫的应用。式(Ⅰ)中R1、R2、R3、R4和Y各如说明书中所定义。
Description
本发明涉及新的取代的N-(5-异噻唑基)-硫代酰胺、其制备方法及其用于防治动物害虫的应用。
业已知道,某些N-(5-异噻唑基)-酰胺具有杀虫性能(参见,例如,WO-95/31448和DE-A-19542372)。
然而,这些化合物的效力和活性谱,特别是在低施用量和浓度下,并非完全令人满意。
因此,本发明提供新的式(Ⅰ)的取代的N-(5-异噻唑基)-硫代酰胺其中R1代表烷基、卤代烷基、烷氧基烷基、烷硫基烷基、烷氧基、烷硫基或任选取代的环烷基,R2代表氢、卤素、氰基、硝基、氰硫基、烷氧基羰基、链烯氧基羰基、烷硫基、卤代烷硫基、烷基亚磺酰基、卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基或硫代氨基甲酰基,R3代表氢、烷基、卤代烷基、烷氧基烷基、烷基羰基、烷基磺酰基,代表芳基羰基、芳基磺酰基或芳基烷基,它们各任选被取代,或代表任选取代的环烷基,R4代表任选取代的芳基、任选取代的环烷基或任选取代的环烯基,和Y代表任选取代的亚烷基、亚烯基或亚烷氧基。
再者,业已发现,如下获得式(Ⅰ)化合物A)式(Ⅱ)化合物其中R1、R2和R3各如上所定义a)与式(Ⅲ)化合物反应,
R4-Y-CS-G (Ⅲ)
其中
R4和Y各如上所定义,和
G代表离去基团,例如,卤素(特别是氯)、咪唑基、苯并咪唑基、1,2,4-***基、吡唑基或苯并***基,
或b)与式(Ⅳ)的二硫代酯反应
Alk-S-CS-Y-R4 (Ⅳ)
其中
R4和Y各如上所定义,和
Alk代表烷基(例如,甲基或乙基)或CH2COOM,其中
M代表碱金属(例如,钠或钾),
其中
R1、R2、R3、R4和Y各如上所定义,
与硫化剂反应,如果适宜在稀释剂存在下进行反应。
最后,业已发现,新的式(Ⅰ)化合物具有突出的生物性能,且非常适合于防治动物害虫,特别是在农业、森林、贮存商品和材料的保护以及在卫生方面上出现的昆虫、蜱螨和线虫。
出人意外的是,本发明的取代的N-(5-异噻唑基)-硫代酰胺对动物害虫的活性比相似结构的已知化合物好得多。
式(Ⅰ)提供本发明化合物的一般定义。
列于上下文中提供的化学式中的优选取代基或基团的范围在下文中进行说明。R1优选代表C1-C4-烷基、具有1至5个相同或不同卤原子如氟、氯和溴原子的C1-C4-卤代烷基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷硫基-C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基,或代表任选由选自C1-C4-烷基和卤素的相同或不同取代基单至三取代的C3-C6-环烷基。R2优选代表氢、卤素、氰基、硝基、氰硫基、C1-C4-烷氧基羰基、C2-C4-链烯氧基-羰基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷硫基、C1-C4-烷基亚磺酰基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基亚磺酰基、C1-C4-烷基磺酰基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基磺酰基,或代表硫代氨基甲酰基。R3优选代表氢、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷基-羰基、C1-C4-烷基磺酰基,代表苯基羰基、苯基磺酰基或苄基,它们各任选在苯环上由相同或不同的取代基单至三取代,可能的取代基在每一种情况下为卤素、硝基、氰基、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C2-卤代烷基、C1-C4-烷氧基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C2-卤代烷氧基或具有1至5个相同或不同卤原子如氟和氯原子的C1-C2-卤代烷硫基,或代表任选由选自C1-C4-烷基和卤素的相同或不同取代基单至三取代的C3-C6-环烷基。R4优选代表苯基,它任选由相同或不同的取代基单至三取代,可能的取代基为卤素、硝基、氰基、C1-C12-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C12-卤代烷基、C1-C12-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C12-卤代烷氧基、C1-C12-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C12-卤代烷硫基、C2-C12-链烯基、具有1至5个相同或不同卤原子如氟和氯原子的C2-C12-卤代链烯基、任选由选自C1-C4-烷基和卤素的相同或不同取代基单至三取代的C3-C8-环烷基,以及苯基、苯氧基、苯硫基、苄基或苄氧基,它们各任选特别是在苯基部分由选自下列的相同或不同取代基单至三取代:卤素、硝基、氰基、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷硫基、C1-C4-烷硫基-C1-C4-烷基、C1-C4-烷基磺酰基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基磺酰基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、硫代氨基甲酰基、C1-C4-烷氧基亚氨基-C1-C4-烷基和任选被C1-C4-烷基取代的噁二唑基,或代表C3-C8-环烷基或C5-C8-环烯基,它们各任选由相同或不同的取代基单至三取代,可能的取代基为:C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基、C3-C8-环烷基,以及苯基,该苯基任选由选自下列的相同或不同取代基单至三取代:卤素、氰基、硝基、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基和具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基。Y优选代表C1-C6-亚烷基、C1-C6-羟基亚烷基、C1-C4-烷氧基-C1-C6-亚烷基、C1-C4-烷基羰氧基-C1-C6-亚烷基、氰基-C1-C6-亚烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代亚烷基;C1-C4-亚烷氧基、C2-C4-亚链烯基或C3-C6-环烷基-C1-C4-亚烷基,它们任选由选自氟、氯和甲基的相同或不同取代基单至三取代。R1特别优选代表甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基;CH2F、CHF2、CF3、CH2Cl、CH2Br、CRClCH3;甲氧基、乙氧基、甲氧基甲基、乙氧基甲基;甲硫基甲基或环丙基。R2特别优选代表氢、氯、溴、氰基、硝基、氰硫基;甲氧基羰基、乙氧基羰基、异丙氧基羰基、正丙氧基羰基;烯丙氧基羰基;SCF3、SCCl2F、SOCF3、SOCCl2F、SO2CF3、SO2CCl2F、SCHF2、SOCHF2、SO2CHF2或CSNH2。R3特别优选代表氢、甲基、乙基、正或异丙基;甲氧基甲基、乙氧基甲基、正丙氧基甲基、正丁氧基甲基;甲基羰基、甲基磺酰基;苯基羰基或苄基,此二基团均任选由选自氟、氯、甲基和三氟甲基的相同或不同的取代基单或二取代;或环丙基。R4特别优选代表苯基,它任选由相同或不同的取代基单至三取代,可能的取代基为卤素、硝基、氰基、C1-C12-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C12-卤代烷基、C1-C4-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷硫基、C2-C4-链烯基、具有1至5个相同或不同卤原子如氟和氯原子的C2-C4-卤代链烯基,和苯氧基、苯硫基或苄氧基,后三个各任选由选自下列的相同或不同的取代基单至三取代:卤素、硝基、氰基、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷硫基、C1-C4-烷硫基-C1-C4-烷基、C1-C4-烷基磺酰基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基磺酰基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、硫代氨基甲酰基、C1-C4-烷氧基亚氨基-C1-C2-烷基和任选被C1-C2-烷基取代的1,2,4-噁二唑-3-基。Y特别优选代表下列基团之一:-CH2-,-CH(CH3)-,-CH(C2H5)-,-CH(n-C3H7)-,-CH(i-C3H7)-,-CH2CH2-,-CH(OH)-,-CH(OCH3)-,-CH(O-CO-CH3)-,-CH(CN)-,-CHF-,-CHCl-,,CH=CH-或-CH2O-,
其中在每一种情况下,基团左侧连接到硫羰基上。R1非常特别优选代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基;CH2F、CHF2、CF3、CH2Cl、CH2Br、甲氧基或乙氧基。R2非常特别优选代表氢、氯、溴、氰基、硝基、氰硫基、甲氧基羰基或乙氧基羰基。R3非常特别优选代表氢、甲基、乙基、甲氧基甲基、乙氧基甲基、甲基羰基、苯基羰基或甲基磺酰基。R4非常特别优选代表苯基,它任选由相同或不同的取代基单至三取代,可能的取代基为氟、氯、溴、硝基、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基;甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基;甲硫基、CF3、OCF3、OCHF2、SCF3、SCCl2F、CH2Br、CH2Cl,以及苯氧基,该苯氧基任选由选自下列的相同或不同的取代基单至三取代:氟、氯、溴、硝基、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基、甲硫基、甲硫基甲基、CF3、OCF3、OCHF2、SCF3、SCCl2F、CH2Br、CH2Cl、乙酰基、乙基羰基、甲氧基羰基、甲基磺酰基、三氟甲基磺酰基、硫代氨基甲酰基、甲氧基亚氨基甲基、1-(甲氧基亚氨基)乙基、1-(乙氧基亚氨基)乙基、1,2,4-噁二唑-3-基或5-甲基-1,2,4-噁二唑-3-基。Y非常特别优选代表-CH2-或-CH(CH3)-。
优选的本发明化合物是式(ⅠA)或(ⅠB)的物质:其中R1、R2和R3具有上面提到的一般、优选、特别优选和非常特别优选的含义,和X1、X2、X3、X4和X5代表上文在R4中对苯基和/或苯氧基提到的一般、优选、特别优选和非常特别优选的取代基,和X1、X2、X3和X4在每一情况下还可以代表氢。
另一组优选的化合物是这样的式(ⅠA)或(ⅠB),其中苯氧基是在NR3-CS-CH2-或NR3-CS-CH(CH3)-基的对位,且这些化合物中,特别优选的是其中取代基X1、X2、X3和X4代表氢的化合物。
上面提到的一般或优选的基团定义和说明适合于终产物,并且同样适合于起始原料和中间体。这些基团定义可以按需要相互组合,即,也可以是各自优选的范围间的组合。
本发明优选的是那些存在上文给出的优选含义之组合的式(Ⅰ)化合物。
本发明特别优选的是那些存在上文给出的特别优选含义之组合的式(Ⅰ)化合物。
本发明非常特别优选的是那些存在上文给出的非常特别优选含义之组合的式(Ⅰ)化合物。
在上下文给出的基团的定义中,烃基如烷基或链烯基——包括与杂原子组合时如烷氧基或烷硫基——各可以是直链或其可能的支链。
除了制备实施例外,可以具体提到下列式(ⅠC)化合物:
表A
R1 | R2 | R3 | Y | X |
C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5 | ClClClClClClClClClClClClClCl | HHHHHHHHHHHHHH | CH2CH2CH2CH2CH2CH2CH2CH2CH2CHCH3CHCH3CHCH3CHCH3CHCH3 | 4-NO24-Cl4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CO2CH34-CN4-NO24-Cl4-OCF34-CF3 |
R1 | R2 | R3 | Y | X |
C2H5C2H5C2H5C2H 5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5 | ClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHCH3CH3CH3CH3COCH3HHHHHHHHHHHHHHCH3CH3 | CHCH3CHCH3CHCH3CHCH3CHCH3CH2CH2CHCHCH2OCH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CHCH3CH2CH2CHCHCH2OCH2CH2 | 4-SCF34-SCH34-SO2CH34-SO2CF34-CO2CH34-CN4-CN4-CN4-CN4-NO24-OCF34-Cl4-CN4-CN4-NO24-Cl4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CO2CH34-CN4-CN4-CN4-CN4-CN4-NO2 |
R1 | R2 | R3 | Y | X |
C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrBrNO2NO2NO2NO2NO2NO2NO2NO2NO2CO2EtCO2EtCO2EtCO2EtClCO2EtCO2EtCO2EtCO2EtCO2EtCO2EtCO2EtCO2EtCO2EtCO2MeCO2MeCO2Me | CH3CH3COCH3HHHHHHHHHHHHHHHHHHHHHHHHHH | CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CHCHCH2OCH2CH2CH2 | 4-OCF34-Cl4-CN4-CN4-NO24-Cl4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CN4-NO24-Cl4-OCF34-CN4-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CO2CH34-CN4-CN4-CN4-CN4-NO24-Cl |
R1 | R2 | R3 | Y | X |
CH3CH3C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5CH3CH3CH3 | CO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCNCNCNCNCNCNCNCNCNCNCSNH2CSNH2CSNH2CSNH2CSNH2CSNH2CSNH2CSNH2CSNH2SCNSCNSCN | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CHCHCH2OCH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2 | 4-OCF34-CF34-CN4-NO24-Cl4-OCF34-CF34-NO24-Cl4-CF34-SCF34-SO2CH34-SO2CF34-CO2CH34-CN4-CN4-CN4-CN4-NO24-Cl4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CN4-NO24-Cl |
R1 | R2 | R3 | Y | X |
CH3CH3CH3CH3CH3CH3OC2H5OC2H5OC2H5OC2H5 | SCNSCNSCNSCNSCNSCNCO2EtCO2EtCO2EtCO2Et | HHHHHHHHHH | CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2 | 4-OCF34-CF34-SCF34-SCH34-SO2CH34-SO2CF34-CN4-NO24-Cl4-OCF3 |
根据方法(B),使用例如N-(4-氯-3-乙基-5-噻唑基)-4-(4-氰基苯氧基)-苯基乙酰胺作为起始原料和Lawesson试剂(2,4-双-(4-甲氧基苯基)-1,3-二硫杂-2,4-二磷杂烷-2,4-二硫化物作为硫化剂,本发明方法之途径可以由下列反应方案来表示:
进行本发明方法(Aa)和(Ab)时需作为起始原料的大多数的式(Ⅱ)的N-(5-异噻唑基)酰胺是已知的(参见,本文开头所引述的专利申请),或它们可以用其中描述的方法制备。
在本发明方法(Aa)中另需用作起始原料的式(Ⅲ)化合物是通常已知的有机化学的化合物。式(Ⅲ)中,G优选代表咪唑基(参见,例如,《李必希化学记事》[Liebigs Ann.Chem.]739,201(1970))。
式(Ⅳ)提供进行本发明方法(Ab)时另需作为起始原料的二硫代酯的一般定义。在此式(Ⅳ)中,Alk优选代表甲基或CH2COONa。
式(Ⅳ)的二硫代酯是已知的(参见,例如,《四面体》[Tetrahedron]2663(1984),《化学研究杂志》[J.Chem.Research](M)2701(1988),《化学工业》[Chem.Ind.](伦敦)803,1974;《俄罗斯化学通讯》[Russ.Chem.Rev.]45,1035(1976)和/或它们可以用已知的相似方法制备。
进行本发明方法(B)时需要的式(Ⅴ)化合物是由本文开头所引述的专利申请中已知的,或它们可以用描述于其中的方法制备。
进行本发明方法(B)时优选的硫化剂是五硫化二磷或Lawesson试剂[2,4-双-(4-甲氧基苯基)-1,3-二硫杂-2,4-二磷杂烷-2,4-二硫化物](参见,《四面体》[Tetrahedron]第41卷,第22期,5061页等(1985))。
描述于上文的制备式(Ⅰ)化合物的方法(Aa)是在稀释剂存在下进行的。适合的稀释剂是所有的常规溶剂。
优选的是使用任选卤代的脂族或芳族烃,醚类或腈类,如环己烷、甲苯、氯苯、氯仿、二氯甲烷、二氯乙烷、二噁烷、四氢呋喃、***或乙腈。
描述于上文的制备式(Ⅰ)化合物的方法(Aa)是在碱存在下进行的(参见,例如,《化学公报》[Chem.Ber.]98,829(1965);《李必希化学记事》[Liebigs Ann.Chem.]739,201(1970)和636(1973))。
适合用于方法(Aa)的碱是所有的常规质子受体。优选的是使用碱金属或碱土金属氢氧化物、碱金属或碱土金属碳酸盐或碳酸氢盐或含氮碱。实例包括氢氧化钠、氢氧化钙、碳酸钾、碳酸氢钠、三乙胺、二苄胺、二异丙胺、吡啶、喹啉、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)和二氮杂二环十一碳烯(DBU)。
在所述的方法(Aa)中,反应温度可以在相对宽的范围内变化。通常,反应是在-40℃至+200℃,优选在0℃至100℃间的温度下进行。
当进行描述于上文的制备式(Ⅰ)化合物的方法(Aa)时,每摩尔的式(Ⅱ)5-氨基异噻唑通常采用1至2摩尔,优选1至1.5摩尔的式(Ⅲ)化合物。
在一些情况下,在此有利地是采用式(Ⅱ)的5-氨基异噻唑的氢卤酸盐形式,例如,特别是,盐酸盐。
终产物的后处理和分离是用通常已知的方式进行的。
适合于进行本发明方法(Ab)的稀释剂是所有的常规溶剂。优选的是使用任选卤代的脂族或芳族烃,如二氯甲烷、二氯乙烷、环己烷、甲苯或氯苯。
然而,此方法也可以在无溶剂未稀释下进行。
进行本发明方法(Ab)时,反应温度可以在相对宽的范围内变化。通常,此方法在0℃至150℃,优选在20℃至120℃间的温度下进行。
当进行本发明方法(Ab)时,每摩尔的式(Ⅲ)吡啶胺通常采用1至3摩尔,优选1至1.5摩尔的式(Ⅳ)的二硫代酯。后处理是用常规方法进行的。
进行本发明方法(B)的优选稀释剂是烃类,如甲苯、二甲苯、四氢化萘、己烷或环己烷。
进行本发明方法(B)时,反应温度可以在相对宽的范围内变化。通常,此方法是在0℃至200℃,优选在20℃至150℃间的温度下进行。
当进行本发明方法(A)时,每摩尔的式(Ⅱ)化合物通常采用1至3摩尔,优选1至2摩尔的硫化剂。后处理是用常规方法进行的。
式(Ⅰ)化合物也可以如下获得:
Hal’-Mg-Y-R4 (Ⅶ)其中Hal’代表卤素(特别是氯或溴),和Y和R4各如上所定义,反应用常规的方法进行(在此方面,参见JACS4849(1955))。式(Ⅰa)的N-(5-异噻唑基)-硫代酰胺其中
E-CO-CH2-R4 (Ⅷ)其中E代表氢或甲基,和R4如上所定义,(在此方面,参见,例如Pet.Chem.USSR(Engl.Transl.)345(1993))。
如果适宜,本发明的式(Ⅰ)的取代的N-(5-异噻唑基)-硫代酰胺可以用已知的方式转化成其相应的N-氧化物或其盐衍生物;它们也构成本申请的主题。
本发明活性化合物具有良好的植物耐受性,并且对温血动物毒性低,适合防治动物害虫,特别是出现在农业、森林、贮藏产品和材料保护以及卫生方面上的昆虫、蜱螨和线虫。它们可以优选用作植物保护剂。它们对正常的敏感和抗性种类和对所有或某些生长发育阶段有活性。上述害虫包括:
等足目,例如,潮虫(Oniscus asellus)、平甲虫(Armadillidiumvulgare)和斑鼠妇(Porcellio scaber)。
倍足目,例如,具斑马陆(Blaniulus guttulatus)。
唇足目,例如,食果地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigera spec)。
综合目,例如,庭院幺蚰(Scutigerella immaculata)。
缨尾目,例如,西洋衣鱼(Lepisma saccharina)。
弹尾目,例如,具棘跳虫(Onychiurus armatus)。
直翅目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattella germanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locusta migratoriamigratorioids)、殊种蚱蜢(Melanoplus differentiaiis)和沙漠蝗(Schistocerca gregaria)。
革翅目,例如,欧洲球螋(Forficula auricularia)。
等翅目,例如,犀白蚁属(Reticulitermes spp.)。
虱目,例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)和颚虱属(Linognathus spp.)。
食毛目,例如,啮毛虱属(Trichodectes spp.)和畜属虱(Damalinea spp.)。
缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thrips tabaci)。
半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercusintermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimexlectularius)、长红猎蝽(Rhodnius prolixus)和锥蝽属(Triatomaspp.)。
同翅目,例如,甘蓝粉虱(Aleurodes brassicae)、甘薯粉虱(Bemisia tabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevicoryne brassicae)、茶隐瘤蚜(Cryptomyzus ribis)、甜菜蚜(Aphis fabae)、苹果蚜(Aphispomi)、苹果绵蚜(Eriosoma lanigerum)、桃大尾蚜(Hyalopterusarundinis)、美核桃根瘤蚜(Phylloxera vaststrix)、瘿绵蚜属(Pemphigus spp.)、麦长管蚜(Macrosiphum avenae)、瘤额蚜属(Myzus spp.)、忽布疣蚜(Phorodon humili)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoasca spp.)、钝鼻叶蝉(Euscelis bilobatus)、黑尾叶蝉(Nephotettix cincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetia oleae)、灰稻虱(Laodelphax striatellus)、稻褐飞虱(Nilaparvata lugens)、红肾园盾蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotushederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupalus piniarius)、冬尺蛾(Cheimatobia brumata)、苹细蛾(Lithocolletis blancardella)、苹果巢蛾(Hyponomeutapadella)、小菜蛾(Plutella maculipennis)、天幕毛虫(Malacosomaneustris)、黄毒蛾(Euproctis chrysorrhoea)、毒蛾属(Lymantriaspp.)、棉潜蛾(Bucculatrix thurberiella)、桔潜叶蛾(Phyllocnistis citrella)、地老虎属(Agrotis spp.)、切根虫属(Euxoa spp.)、夜蛾属(Feltia spp.)、棉斑实蛾(Eariasinsulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾(Spodopteraexigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolisflammea)、斜纹夜蛾(Prodenia litura)、灰翅夜蛾属(Spodopteraspp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsapomonella)、粉蝶属(Pieris spp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestia kuehniella)、大蜡螟(Galleria mellonella)、幕衣蛾(Tineola bisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophilapseudospretella)、亚麻黄卷蛾(Cacoecia podana)、织网衣蛾(Capuareticulana)、云松卷蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homona magnanima)和栎绿卷蛾(Tortrix viridana)。
鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizoperthadominica)、Bruchidius obtectus、大豆象(Acanthoscelidesobtectus)、家天牛(Hylotrupes bajulus)、赤杨紫跳甲(Agelasrticaalni)、马铃薯甲虫(Leptinotarsa decemlineata)、辣根猿叶甲(Phaedon cochleariae)、条叶甲属(Diabrotica spp.)、油菜蓝跳甲(Psylliodes chrysocephala)、墨西哥豆甲(Epilachnavarivestis)、隐翅甲属(Atomaria spp.)、锯谷盗(Oryzaephilussurinamensis)、花象甲属(Anthonomus spp.)、米象属(Sitophilusspp.)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、香蕉根象甲(Cosmopolites sordidus)、甘蓝荚象甲(Ceuthorrhynchusassimilis)、苜蓿叶象虫(Hypera postica)、皮蠹属(Dermestesspp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptushololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Triboliumspp.)、黄粉虫(Tenebrio molitor)、叩头虫属(Agriotes spp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolonthamelolontha)、马铃薯鳃角金龟(Amphimallon sostitialis)和褐新西兰肋翅鳃角金龟(Costelytra zealandica)。
膜翅目,例如,锯角叶蜂属(Diprion spp.)、叶蜂属(Hoplocampaspp.)、田蚁属(Lasius spp.)、小家蚁(Monomorium pharaonis)和胡蜂(Vespa spp.)。
双翅目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophila melanogaster)、蝇属(Musca spp.)、厕蝇属(Fannia spp.)、红头丽蝇(Calliphoraerythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyiaspp.)、疽蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hyppobosca spp.)、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、虻属(Tabanus spp.)、螗蜩属(Tannia spp.)、花园毛蚊(Bibio hortulanus)、瑞典麦杆蝇(Oscinella frit)、草种蝇属(Phorbia spp.)、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitis capitata)、油榄实蝇(Dacus oleae)和沼泽大蚊(Tipula paludosa)。
蚤目,例如,印鼠客蚤(Xenopsylla cheopis)和毛列蚤属(Ceratophyllus spp.)。
蛛形目,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectusmactans)。
蜱螨目,例如,粗脚粉螨(Acarus siro)、隐喙蜱属(Argasspp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssusgallinae)、茶瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptrutaoleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalusspp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptesspp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)和叶螨属(Tetranychus spp.)。
植物寄生线虫包括例如垫刃线虫(Pratylenchus spp.)、毕肖穿孔线虫(Radopholus similis)、起绒草茎线虫(Ditylenchus dipsaci)、半穿刺线虫(Tylenchulus semipenetrana)、异皮线虫(Heteroderaspp.)、囊线虫(Globodera spp.)、根结线虫(Meloidogyne spp.)、滑刃线虫(Aphelechoides spp.)、长针线虫(Longidorus spp.)、剑线虫(Xiphinema spp.)和髦根线虫(Trichodorus spp.)。
本发明式(Ⅰ)化合物的特别突出之处在于其高的杀虫和杀螨活性。
它们可以采用来特别成功地防治植食性昆虫,如防治辣根猿叶甲幼虫(Phaedon cochlaeriae)、小菜蛾(Plutella maculipennis)毛虫、黑尾叶蝉(Nephotettix cinctriceps)和草地贪夜蛾(Spodopterafrugiperda)幼虫,或防治植食性螨,如防治温室的二点叶螨(Tetranychus urticae)。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、可溶性粉剂、颗粒剂、悬浮乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微细胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与扩充剂(即液体和/或与固体载体)混合,任选地与表面活性剂(即乳化剂和/或分散剂和/或起泡剂)混合。
在用水作扩充剂的情况下,也可以用有机溶剂作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯、甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份、矿物和植物油,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水。
适合的固体载体是:
例如铵盐和磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的固体载体适合的有:例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如***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,和合成磷脂。其它可能的添加剂是矿物油和植物油。
也可能使用着色剂,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,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
本发明活性化合物可以其商业上可得的制剂和由这些制剂制备的使用形式存在,所述的制剂为与例如如下的其它活性化合物的混合物:杀虫剂、引诱剂、不育剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂。杀虫剂包括例如磷酸酯类、氨基甲酸酯类、羧酸酯类、氯代烃类、苯基脲类、由微生物生产的物质,及其它。
特别有利的混合配对物是例如下列:
杀真菌剂:
2-氨基丁烷、2-苯胺基-4-甲基-6-环丙基-嘧啶;2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苯甲基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基-苯氧基)嘧啶-4-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP)、aldimorph、氨丙磷酸、敌菌灵、戊环唑、苯霜灵、碘萎灵、苯菌灵、乐杀螨、联苯、双苯***醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氰、环唑醇、酯菌胺、防霉酚、苄氯***醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克菌散、环氧唑(epoxyconazole)、乙嘧啶、氯唑灵、双氯苯嘧啶、苯氰唑、呋菌胺、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、fludioxonil、氟氯菌核利、fluquinconazole、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、四氯苯酞、麦穗宁、呋霜灵、拌种胺、双胍辛、六氯苯、己唑醇、甲羟异噁唑、抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净、异菌脲、稻瘟灵、春日霉素、铜制剂(如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物)、双代混剂、代森锰锌、代森锰、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、担菌胺、代森联、噻菌胺、腈菌唑、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、噁酰胺、oxamocarb、氧化萎锈灵、稻瘟酯、戊菌唑、戊菌隆、稻病磷、稻瘟酞、匹马菌素、哌啶宁、多氧霉素、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、***酮、***醇、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、稻纹散、乙烯菌核利、代森锌、福美锌。
杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、AC303630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、阿维菌素(avermectin)、AZ60541、苦楝素、乙基谷硫磷、谷硫磷、***锡、苏芸金杆菌、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、CGA157419、CGA184699、除线威、氯氧磷、毒虫畏、定虫隆、氯甲硫磷、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷Ⅱ、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二噁硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、氟虫腈、氟啶胺、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、吡虫啉、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC184、定虫咪、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊酯、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH5992、水杨硫磷、硫线磷、氟硅菊酯、治螟磷、甲丙硫磷、虫酰肼、吡螨胺(tebufenpyrad)、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、***磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、YI5301/5302、zetamethrin。
也可能是与其它已知活性化合物如除草剂或与肥料和生长调节剂的混合物。
此外,本发明活性化合物可以以其商业上可得的制剂和以由这些制剂制备的使用形式存在。这些制剂可以是与增效剂的混合物。增效剂是可以增加活性化合物活性,而所添加的增效剂本身无需有活性的化合物。
由商业上可得的制剂制备的使用形式中的活性化合物的含量可以在相当宽的范围内变化。使用形式的活性化合物浓度可以是按重量计0.0000001至95%的活性化合物,优选在按重量计0.0001至1%间。
化合物以适合于使用形式的常规方式采用的。
当防治卫生和贮藏产品方面的害虫时,活性化合物对木材和陶土具有优异的残留作用和对石灰处理过的底物上的碱具有良好的稳定性。
本发明活性化合物不仅对植物、卫生和贮藏产品害虫有活性,而且在兽医方面,对动物寄生虫(体外寄生虫)如硬蜱、软蜱、兽疥螨、恙螨、(叮咬和吸吮)蝇、寄生蝇幼虫、虱、毛虱、羽虱和蚤有活性。这些寄生虫包括:
虱目,例如,血虱属(Haematopinus spp.)、颚虱属(Linognathusspp.)、虱属(Pediculus spp.)、阴虱属(Phthirus spp.)和盲虱属(Solenoptes spp.)。
食毛目及amblycerina和细角亚目(Ischnocerina),例如,毛鸟虱属(Trimenopon spp.)、短角鸟虱属(Menopon spp.)、豆虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiellaspp.、Lepikentron spp.、畜虱属(Damalinea spp.)、啮毛虱属(Trichodectes spp.)和猫虱属(Felicola spp.)。
双翅目及长角亚目和短角亚目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simuliumspp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、卢蚊属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotusspp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、Braula spp.、蝇属(Musca spp.)、齿股蝇(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、血蝇属(Haematobiaspp.)、Morellia spp.、厕蝇属(Fannia spp.)、舌蝇属(Glossinaspp.)、丽蝇属(Calliphora spp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、肉蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hippobosca spp.)、蜱蝇属(lipoptena spp.)和羊虱蝇属(Melophagus spp.)。
蚤目,例如,蚤属(Pulex spp.)、栉头蚤属(Ctenocephalidesspp.)、鼠客蚤属(Xenopsylla spp.)和毛列蚤属(Ceratophyllusspp.)。
半翅目,例如,臭虫属(Cimex spp.)、锥蝽属(Triatoma spp.)、红腹猎蝽属(Rhodnius spp.)和全圆蝽属(Panstrongylus spp.)。
蜚蠊目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国小蠊(Blattela germanica)和棕带蠊属(Suppella spp.)。
螨亚纲及后气亚目(Metastigmata)和中气亚目(mesostigmata),例如,隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodorus spp.)、残喙蜱属(Otabius spp.)、硬蜱属(Ixodes spp.)、花蜱属(Amblyommaspp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemaphysalis spp.)、眼玻蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)、刺皮螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸口螨属(Sternostoma spp.)和瓦螨属(Varroa spp.)。
Actinedida(前气孔亚目)和粉螨目(无气孔亚目),例如,蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形属(Demodex spp.)、恙螨属(Trombiculaspp.)、牦螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophaus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、瘙螨属(Psoroptesspp.)、痒螨属(Chorioptes spp.)、耳癞螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、痂螨属(Notoedres spp.)、疙螨属(Knemidocoptes spp.)、胞螨属(Cytodites spp.)和皮膜螨属(Laminosioptes spp.)。
本发明式(Ⅰ)活性化合物也适合防治侵害如下动物的节肢动物:农业生产性牲畜例如牛、绵羊、山羊、马、猪、猴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,如狗、猫、笼养鸟、水箱中的鱼,和所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。防治这些节肢动物时,旨在降低死亡和生产性(肉、奶、毛、皮、蛋、蜜等等)损耗。这样,采用本发明活性化合物使更经济有效的畜牧业成为可能。
本发明活性化合物可以使用在兽医方面,使用是以已知的方式,通过内部施用,例如以片剂、胶囊、饮用水、兽用顿服剂、颗粒剂、膏剂、大丸剂、食入法、栓剂的方式,通过非经肠道施药,例如注射(肌内、皮下、静脉内、腹腔内等)、植入,经鼻施用,经皮施用,例如通过沐浴或浸蘸、喷雾、浇泼、点涂、洗刷、喷粉的方式,以及借助含有活性化合物的成形物件,如颈环、耳标、尾牌、腿箍、笼头、标记设备等。
当用于畜禽、家养动物等时,式(Ⅰ)的活性化合物可以以制剂的形式(例如粉剂、乳剂、可流动粉剂)的使用,所述的制剂中含有按重量计1至80%的活性化合物,该制剂可以直接施用或稀释100至10000倍后施用,或者它们可以以化学浴的形式使用。
而且现已发现,本发明式(Ⅰ)化合物对破坏工业材料的昆虫具有强的杀虫作用。
可以列举且是优选的昆虫是下列,但不限于这些昆虫:
甲虫如
家天牛(Hylotrupes bajulus)、Chlorophorus pilosis、具斑窃蠹(Anobium punctatum)、Xestobium rufovillosum、Ptilinuspecticornis、Dendrobium pertinex、Ernobium mollis、Priobiumcarpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(L.africanus)、平颈粉蠹(L.planicollis)、桴粉蠹(L.linesris)、L.pubescens、Trogoxylon aequale、鳞毛粉蠹(Minthes rugicollis)、小蠹(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apatemonachus)、槲长蠹(Bostyrchus capucins)、Heterobostrychusbrunneus、Sinoxylon spec.、竹长蠹(Dinoderus minutus)。
革翅目,如
小钢青树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、U.gigas taignus、U.augur。
白蚁,如
木白蚁(Kalotermes flavicollis)、隐白蚁(Cryptotermesbrevis)、灰点异白蚁(Heterotermes indicola)、黄胸散白蚁(Reticulitermes flavipes)、R.santonecsis、R.lucifugus、澳洲白蚁(Mastotermes darwiniensis)、Zootermopsisnevadensis、家白蚁(Coptotermes formosanus)。
衣鱼
如西洋衣鱼(Lepisma saccharina)。
在本文中,工业材料应理解为无生命的材料如优选的是聚合材料、胶水、粘性材料、纸和板、皮革、木材和衍生的木制品、和漆。
木材和木制品是非常特别优选的受保护而使之不被昆虫侵害的材料。
可以用本发明的药剂或含有之的组合物保护的木材和衍生的木制品应理解为有下列含义,例如,建筑木料、木梁、铁道枕木、桥梁组件、突堤、木车、盒、箱、容器、电线杆、木质矿道顶木、木制的门窗、胶合板、碎料板、木工的制品、或通常用在建筑或细木工中的木制品。
本发明活性化合物可以以其原样、以其浓缩物或通常的常规制剂使用。所述的常规制剂是例如可湿性粉剂、颗粒剂、溶液、悬浮剂、乳剂或膏剂。
上述制剂可以以本身已知的方式制备,例如通过将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂、如果需要脱水剂和UV稳定剂和如果需要着色剂和染料和其它加工辅助剂混合。
用于保护木材和木制品的杀虫组合物或浓缩物包含浓度为按重量计0.0001至95%,特别是按重量计0.001至60%的活性化合物。
采用的组合物或浓缩物的量取决于昆虫的种类和发生情况,以及介质。所用最佳量可以在每种情况下由一系列试验来确定。然而,一般而言,以所要保护的材料为基准,采用按重量计0.0001至20%,优选按重量计0.001至10%的活性化合物已足矣。
所用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油性或油样有机化学溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水,且如果适宜乳化剂和/或润湿剂。
优选采用的有机化学溶剂是油性或油样溶剂,所述的溶剂具有大于35的挥发度和高于30℃的闪点,优选高于45℃。用作这种油性或油样溶剂的物质是低挥发性的,且不溶于水,这类物质适合的有矿物油或其芳族馏份且含有矿物油的溶剂混合物,优选是石油溶剂、石油和/或烷基苯。
可以有利地使用的物质是沸程为170到220℃的矿物油、沸程为170到220℃的石油溶剂、沸程为250到350℃的碇子油、沸程为160到280℃的石油或松节油精。
在优选的实施方案中,所用的物质是沸程为180至210℃的液体脂族烃或沸程为180至220℃的芳族或脂族烃的高沸点混合物和/或碇子油和/或单氯萘,优选α-单氯萘。
挥发度高于35且闪点高于30℃,优选高于45℃的低挥发性有机油性或油样溶剂,可以部分地由高或中挥发性的有机化学溶剂置换,其前提条件是,溶剂混合物也具有高于35的挥发度且闪点高于30℃,优选高于45℃,且杀虫剂/杀真菌剂混合物在此溶剂混合物中是可溶的或可乳化的。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物或脂族极性有机化学溶剂或溶剂混合物被置换。优选采用的物质是含有羟基和/或酯和/或醚基团的脂族有机化学溶剂,如例如乙二醇醚、酯类等。
在本发明范围内使用的有机化学粘合剂是本身已知的粘合干性油和/或合成树脂,它们可以用水稀释和/或在所采用的有机化学溶剂中是可溶的、可分散的或可乳化的,特别是那些由如下组成,或包含如下成分的粘合剂:丙烯酸树酯、乙烯树脂,例如聚乙酸乙烯酯、聚酯树酯、缩聚或加聚树脂、聚氨酯树脂、醇酸树脂或改性的醇酸树脂、苯酚树脂、烃类树脂如茚-香豆酮树脂、硅氧烷树脂、干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘合剂。
用作粘合剂的合成树脂可以以乳液、分散液或溶液的形式使用。沥青或沥青状物质也可以用作粘合剂的物质,其量至多为按重量计10%。此外,可以采用特别是颜料、防水剂、抑臭剂和抑制剂或抗腐蚀剂等。
根据本发明,组合物或浓缩物优选含有至少一种醇酸树脂或改性醇酸树脂和/或干性植物油作为有机化学粘合剂。根据本发明所优选采用的物质是油含量超过按重量计45%,优选50至68%的醇酸树脂。
所有的或部分上述粘合剂可以由固定剂(混合物)或增塑剂(混合物)置换。这些添加剂是旨在防止活性化合物挥发和结晶或沉淀。它们优选置换0.01至30%的粘合剂(以所用的粘合剂的100%为基准)。
增塑剂来自属于下列化学分类的物质:邻苯二甲酸酯类,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯,磷酸酯类,如磷酸三丁酯,己二酸酯类,如二(2-乙基己基)己二酸酯,硬脂酸酯,如硬脂酸丁酯或硬脂酸戊酯,油酸酯类,如油酸丁酯,甘油醚类或高分子量乙二醇醚类、甘油酯类和对甲苯磺酸酯类。
固定剂化学上基于聚乙烯基烷基醚类如聚乙烯基甲基醚,或酮类如二苯甲酮或亚乙基二苯甲酮。
特别适合的溶剂或稀释剂也可以是水,如果适宜是水与一或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
特别有效的木材保护通过工业规模的浸渍工艺,例如真空、双真空或压力工艺的方式获得。
如果适宜,直接可用的组合物可以包含一种或多种其它杀虫剂和(如果适宜)也可以有一或多种杀真菌剂。
可能混合于其中的另外的合适组分优选是WO94/29268中提到的杀虫剂和杀真菌剂。在上述文献中提到的化合物明确地说是本发明申请的一部分。
可以非常特别优选地混合于其中的组分是杀虫剂如毒死蜱、辛硫磷、硅氟菊酯、氟氯氰菊酯、甲体氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫灵、啶虫脒、氟虫脲、氟铃脲和杀虫隆,以及杀真菌剂如环氧唑(epoxyconazole)、己唑醇、戊环醇、丙环唑、戊唑醇、环唑醇、metconazole、抑霉唑、苯氟磺胺、甲苯氟磺胺、3-碘代-2-丙炔基丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明活性化合物的制备和应用可以用下列实施例说明。
制备实施例
(方法B)
将0.50g(1.25mol)N-(3-乙基-4-氯-异噻唑基)-4-(4-氰基苯氧基)-苯基-乙酰胺和0.97g(3.26mmol)的Lawesson试剂在20ml甲苯中加热回流7小时,并将混合物浓缩,将粗产物通过硅胶柱色谱(流动相:二氯甲烷)纯化。
由此给出0.16g(理论值的31%)N-(3-乙基-4-氯-异噻唑基)-4-(4-氰基苯氧基)-苯基硫代乙酰胺。
熔点177-178℃。
应用实施例
实施例A
辣根猿叶甲幼虫(Phaedon larvae)试验
溶剂: 7份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将l份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍湿润时,放入辣根猿叶甲(Phaedoncochleariae)幼虫。
经过一定的时间后,确定杀死%。100%是指所有的幼虫均被杀死;0%是指没有幼虫被杀死。
在此试验中,例如,在活性化合物浓度为0.1%的条件下,7天后,制备实施例化合物1杀死100%的幼虫。
Claims (10)
2.根据权利要求1的式(Ⅰ)化合物,其中R1代表C1-C4-烷基、具有1至5个相同或不同卤原子如氟、氯和溴原子的C1-C4-卤代烷基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷硫基-C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基,或代表任选由选自C1-C4-烷基和卤素的相同或不同取代基单至三取代的C3-C6-环烷基,R2代表氢、卤素、氰基、硝基、氰硫基、C1-C4-烷氧基羰基、C2-C4-链烯氧基-羰基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷硫基、C1-C4-烷基亚磺酰基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基亚磺酰基、C1-C4-烷基磺酰基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基磺酰基,或代表硫代氨基甲酰基,R3代表氢、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷基-羰基、C1-C4-烷基磺酰基,代表苯基羰基、苯基磺酰基或苄基,它们各任选在苯环上由相同或不同的取代基单至三取代,可能的取代基在每一种情况下为卤素、硝基、氰基、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C2-卤代烷基、C1-C4-烷氧基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C2-卤代烷氧基或具有1至5个相同或不同卤原子如氟和氯原子的C1-C2-卤代烷硫基,或代表任选由选自C1-C4-烷基和卤素的相同或不同取代基单至三取代的C3-C6-环烷基,R4代表苯基,它任选由相同或不同的取代基单至三取代,可能的取代基为卤素、硝基、氰基、C1-C12-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C12-卤代烷基、C1-C12-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C12-卤代烷氧基、C1-C12-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C12-卤代烷硫基、C2-C12-链烯基、具有1至5个相同或不同卤原子如氟和氯原子的C2-C12-卤代链烯基、任选由选自C1-C4-烷基和卤素的相同或不同取代基单至三取代的C3-C8-环烷基,以及苯基、苯氧基、苯硫基、苄基或苄氧基,它们各任选由选自下列的相同或不同取代基单至三取代:卤素、硝基、氰基、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷硫基、C1-C4-烷硫基-C1-C4-烷基、C1-C4-烷基磺酰基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基磺酰基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、硫代氨基甲酰基、C1-C4-烷氧基亚氨基-C1-C4-烷基和任选被C1-C4-烷基取代的噁二唑基,或代表C3-C8-环烷基或C5-C8-环烯基,它们各任选由相同或不同的取代基单至三取代,可能的取代基为:C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基、C3-C8-环烷基,以及苯基,该苯基任选由选自下列的相同或不同取代基单至三取代:卤素、氰基、硝基、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基和具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基,和Y代表C1-C6-亚烷基、C1-C6-羟基亚烷基、C1-C4-烷氧基-C1-C6-亚烷基、C1-C4-烷基羰氧基-C1-C6-亚烷基、氰基-C1-C6-亚烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代亚烷基;C1-C4-亚烷氧基、C2-C4-亚链烯基或C3-C6-环烷基-C1-C4-亚烷基,它们任选由选自氟、氯和甲基的相同或不同取代基单至三取代。
3.根据权利要求1的式(Ⅰ)化合物,其中R1代表甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基;CH2F、CHF2、CF3、CH2Cl、CH2Br、CHClCH3;甲氧基、乙氧基、甲氧基甲基、乙氧基甲基;甲硫基甲基或环丙基,R2代表氢、氯、溴、氰基、硝基、氰硫基;甲氧基羰基、乙氧基羰基、异丙氧基羰基、正丙氧基羰基;烯丙氧基羰基;SCF3、SCCl2F、SOCF3、SOCCl2F、SO2CF3、SO2CCl2F、SCHF2、SOCHF2、SO2CHF2或CSNH2,R3代表氢、甲基、乙基、正或异丙基;甲氧基甲基、乙氧基甲基、正丙氧基甲基、正丁氧基甲基;甲基羰基、甲基磺酰基;苯基羰基或苄基,此二基团均任选由选自氟、氯、甲基和三氟甲基的相同或不同的取代基单或二取代;或环丙基,R4代表苯基,它任选由相同或不同的取代基单至三取代,可能的取代基为卤素、硝基、氰基、C1-C12-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C12-卤代烷基、C1-C4-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷硫基、C2-C4-链烯基、具有1至5个相同或不同卤原子如氟和氯原子的C2-C4-卤代链烯基,和苯氧基、苯硫基或苄氧基,它们各任选由选自下列的相同或不同的取代基单至三取代:卤素、硝基、氰基、C1-C4-烷基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷氧基、C1-C4-烷硫基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷硫基、C1-C4-烷硫基-C1-C4-烷基、C1-C4-烷基磺酰基、具有1至5个相同或不同卤原子如氟和氯原子的C1-C4-卤代烷基磺酰基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、硫代氨基甲酰基、C1-C4-烷氧基亚氨基-C1-C2-烷基和任选被C1-C2-烷基取代的1,2,4-噁二唑-3-基,和Y代表下列基团之一:-CH2-,-CH(CH3)-,-CH(C2H5)-,-CH(n-C3H7)-,-CH(i-C3H7)-,-CH2CH2-,-CH(OH)-,-CH(OCH3)-,-CH(O-CO-CH3)-,-CH(CN)-,-CHF-,-CHCl-,
,-CH=CH-或-CH2O-,其中在每一种情况下,基团左侧连接到硫羰基上。
4.根据权利要求1的式(Ⅰ)化合物,其中R1代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基;CH2F、CHF2、CF3、CH2Cl、CH2Br、甲氧基或乙氧基,R2代表氢、氯、溴、氰基、硝基、氰硫基、甲氧基羰基或乙氧基羰基,R3代表氢、甲基、乙基、甲氧基甲基、乙氧基甲基、甲基羰基、苯基羰基或甲基磺酰基,R4代表苯基,它任选由相同或不同的取代基单至三取代,可能的取代基为氟、氯、溴、硝基、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基;甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基;甲硫基、CF3、OCF3、OCHF2、SCF3、SCCl2F、CH2Br、CH2Cl,以及苯氧基,该苯氧基任选由选自下列的相同或不同的取代基单至三取代:氟、氯、溴、硝基、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基、甲硫基、甲硫基甲基、CF3、OCF3、OCHF2、SCF3、SCCl2F、CH2Br、CH2Cl、乙酰基、乙基羰基、甲氧基羰基、甲基磺酰基、三氟甲基磺酰基、硫代氨基甲酰基、甲氧基亚氨基甲基、1-(甲氧基亚氨基)乙基、1-(乙氧基亚氨基)乙基、1,2,4-噁二唑-3-基或5-甲基-1,2,4-噁二唑-3-基,Y代表-CH2-或-CH(CH3)-。
6.农药,其特征在于,它们含有至少一种权利要求1中的式(Ⅰ)化合物。
7.权利要求1的式(Ⅰ)化合物防治有害生物的应用。
8.防治有害生物的方法,其特征在于,使式(Ⅰ)化合物作用于有害生物和/或其栖生地。
9.制备农药的方法,其特征在于,将式(Ⅰ)化合物与扩充剂和/或表面活性剂混合。
10.权利要求1的式(Ⅰ)化合物制备农药的应用。
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PE20010830A1 (es) * | 2000-01-28 | 2001-09-06 | Syngenta Ltd | Derivados de azol insecticidas o fungicidas y composiciones que los comprenden |
WO2005040162A1 (en) * | 2003-10-27 | 2005-05-06 | Basf Aktiengesellschaft | 5-(2-arylacetamido)isothiazole compounds i |
KR100859891B1 (ko) | 2004-08-26 | 2008-09-23 | 화이자 인코포레이티드 | 단백질 키나제 억제제로서 거울상이성질체적으로 순수한아미노헤테로아릴 화합물 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1595992A1 (de) * | 1966-04-06 | 1970-02-12 | Merck Ag E | Neue 3-Chlor-4-cyan-isothiazole und diese enthaltende insektizide Mittel |
DE1954179A1 (de) * | 1969-10-28 | 1971-05-06 | Merck Anlagen Gmbh | Acylaminoisothiazolsalze |
CA2189573A1 (en) * | 1994-05-17 | 1995-11-23 | Ronald E. Hackler | N-(5-isothiazolyl)amide pesticides |
JPH08245561A (ja) * | 1995-03-09 | 1996-09-24 | Takeda Chem Ind Ltd | 殺有害生物活性チオアミド誘導体、イソチアゾール誘導体、それらの用途 |
DE19542372A1 (de) * | 1995-11-14 | 1997-05-15 | Bayer Ag | Acylierte 5-Aminoisothiazole |
-
1996
- 1996-07-16 DE DE1996128569 patent/DE19628569A1/de not_active Withdrawn
-
1997
- 1997-07-03 JP JP10505570A patent/JP2000515135A/ja active Pending
- 1997-07-03 CN CN 97196503 patent/CN1225632A/zh active Pending
- 1997-07-03 WO PCT/EP1997/003523 patent/WO1998002424A1/de not_active Application Discontinuation
- 1997-07-03 AU AU35410/97A patent/AU3541097A/en not_active Abandoned
- 1997-07-03 EP EP97931766A patent/EP0912532A1/de not_active Withdrawn
- 1997-07-03 BR BR9710322A patent/BR9710322A/pt unknown
Also Published As
Publication number | Publication date |
---|---|
BR9710322A (pt) | 1999-08-17 |
EP0912532A1 (de) | 1999-05-06 |
DE19628569A1 (de) | 1998-01-22 |
WO1998002424A1 (de) | 1998-01-22 |
AU3541097A (en) | 1998-02-09 |
JP2000515135A (ja) | 2000-11-14 |
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