CN1171775A - 氟代丁烯基酯 - Google Patents
氟代丁烯基酯 Download PDFInfo
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- CN1171775A CN1171775A CN95197158A CN95197158A CN1171775A CN 1171775 A CN1171775 A CN 1171775A CN 95197158 A CN95197158 A CN 95197158A CN 95197158 A CN95197158 A CN 95197158A CN 1171775 A CN1171775 A CN 1171775A
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- compound
- general formula
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- alkyl
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- 150000002148 esters Chemical class 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 49
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 144
- -1 carbalkoxy Chemical group 0.000 claims description 59
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 22
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- 125000003545 alkoxy group Chemical group 0.000 claims description 21
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
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- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
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- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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- C07C271/14—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
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- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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- C07C271/66—Y being a hetero atom
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- C07C311/52—Y being a hetero atom
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
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Abstract
本发明涉及通式(Ⅰ)的氟代丁烯酯,其中R1为氢或卤素和R2为右面的一个基,其中V,Y,Z,R3和R5的含义同说明书,涉及制备它们的方法和中间体,涉及它们用于控制动物害虫。
Description
本发明涉及新的氟代丁烯基酯,涉及它们的制备方法,涉及使用它们控制虫害,尤其是控制农业、林业在产品和物材存贮保护中及卫生界碰到的昆虫、蜘蛛类及线虫。
已知一些氟代丁烯化合物具有杀线虫活性(见于WO88/00183)。不过这些化合物活性强度和杀菌谱不总是完全满意,尤其是低比例使用和低浓度使用时不能令人满意。
本发明提供了通式(I)的新化合物。(I)其中R1为氢或卤素和R2为(a)或(b)之一的基(a)或
(b)其中Y为氧或硫,Z为氧、硫或NR4,R3为氢,随意取代的烷基,烯基,环烷基,芳基,芳烷基,烷氧羰基,芳氧羰基,芳磺酰基或杂芳基,R4为氢或随意取代的烷基,烷硫基,烯基,环烷基,芳基,芳烷基或杂芳基,R3和R4一块与它们相连的氮原子形成随意取代的环,该环随意含氧、硫或氮环(该氮随意被烷基,芳基或芳烷基取代),或R2为(c)基,(c)
其中
V为氧或NR6和
R5和R6各自独立为氢,具有1至12个碳原子的脂肪基,芳基或杂环基,它们至少被1个取代基取代,这些取代基选自烷基,氰基,三甲基硅基,羟基,烷氧基,卤素,硝基,氨基,烷氨基,二烷基氨基,SH,烷硫基,苯基,或被羧酸基,磺酸基,磷酸基,亚磷酸基,酯基,硫酯基或提到的酸的酰胺基取代,该酰胺基随意地烷基单取代或双取代,或
R5和R6一块与它们相连的氮原子形成氨基酸或形成再随意外加上一个氧,硫或氮的杂环,它们至少随意被烷基,氰基,三甲基硅基,羟基,烷氧基,卤素,硝基,氨基,烷氨基,二烷基氨基,SH,烷硫基,苯基或羧酸基,磺酸基,磷酸基或亚磷酸基,或被提到的羧酸的酯基,硫酯基或酰胺基取代,该酰胺基随意被烷基单取代或双取代,或
R5在R6为氢的情况下为OR7,COR7,NR7R8,SO2R9,或P(=O)R10R11中的一个基,其中
R7和R8各自独立为氢,烷基或芳基,
R9为氢,烷基,卤代烷基或芳基,
R10和R11各自独立为氢,烷基,芳基,烷氧基,芳氧基,烷硫基,
芳硫基,氨基,烷氨基,二烷基氨基或芳氨基,
本发明还提供了通式(I)的化合物的盐。
通式(I)的化合物可以以几何异构体和/或光学异构体或以不同组成的异构体的混合物存在。本发明即涉及纯异构体也涉及异构体的混合物。
具有羧基或羟基的通式(I)的化合物能够与不同的阳离子结合成盐,例如与碱金属或碱土金属离子,例如与钠离子,钾离子,钙离子,镁离子或季铵离子,例如异丙基铵离子或吡啶离子成盐。
其中R1,R3,R5,V,Y,Z的含义同上,
其中
其中Y,Z,和R3的含义同上,反应时有稀释剂和随意的碱存在,或β)通式(IV)的异(硫代)氰酸酯反应,
YCN-R3 (IV)
其中R1和Y的含义同上,与通式(VI)的化合物反应,
H-Z-R3 (VI)
其中Z和R3的含义同上,反应时有稀释剂和随意的碱存在,或D)通式(VII)的化合物(VII)
其中R1和Y的含义同上,与通式(VIII)的化合物反应,
H-S-R3 (VIII)
其中R3的含义同上,反应时有稀释剂和随意的碱存在,
通式(Ic)的化合物可由已知化合物(其中有些化合物可作为商品买到)制备,或从按已知方法容易制备的化合物制备(参见制备实施例),
最后发现通式(I)的新化合物具有强生物活性,特别是适于控制动物虫害,尤其是控制在农业、林业,产品和物材保护中及卫生界碰到的昆虫、蜘蛛类及线虫。
通式(I)提供了本发明的化合物的一般定义,
现在解释上下文中提到的通式中列出的优选的取代基或取代基范围。
R1优选为氢,氟或氯
其中Y为氧或硫
Z为氧,硫或NR4
R3为氢,或C1-C10烷基,该烷基随意被卤素,氰基,羧基,苯基,氨基(该氨基随意被C2-C7亚烷基(C2-C7 alkanediyl)取代或被相同的或不同的C1-C8烷基单取代或双取代),C1-C8烷氧基,C1-C8烷硫基或氨羰基(该氨羰基随意被C2-C7-亚烷基(C2-C7-alkanediyl)取代,被相同或不同的C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C3-C8环烷基,C3-C8卤代环烷基,C1-C4烷基-C3-C8环烷基,或被苯基或苄基取代,苯基和苄基均可随意地被卤素,氰基,硝基,C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C1-C8卤代烷氧基,C1-C8烷硫基或C1-C8卤代烷硫基取代),或为随意被卤素取代的C3-C8烯基,或为随意被卤素或C1-C6烷基取代的C3-C8环烷基,或为苯基,苄基,苯氧羰基或苯基砜基,它们各自均为随意被卤素,氰基,硝基,C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C1-C8卤代烷氧基,C1-C8烷硫基,C1-C8卤代烷硫基,C1-C8烷氧羰基或SCN取代,或为卤素或C1-C6烷基随意取代的含1至3个氮原子的5元或6元杂环,或为卤素或C1-C6烷氧基随意取代的C1-C8烷氧羰基。R4优选为氢,或随意被卤素,氰基,氨基(该氨基随意被C2-C7亚烷基(C2-C7-alkanediyl)取代或随意被相同或不同的C1-C8烷基单取代或双取代),C1-C8烷氧基,C1-C8烷硫基或氨羰基(该氨羰基随意被C2-C7-亚烷基(C2-C7-alkanediyl)取代或被相同或不同的C1-C8烷基,C1-C8卤代烷基,C3-C8环烷基,C3-C8卤代环烷基,C1-C4烷基-C3-C8环烷基单取代或双取代,或被苯基或苄基取代,它们各自随意被卤素,氰基,硝基,C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C1-C8卤代烷氧基,C1-C8烷硫基,或C1-C8卤代烷硫基取代),或为卤素随意取代的C1-C6烷硫基,或为卤素随意取代的C3-C8烯基,或为卤素或C1-C6烷基随意取代的环烷基,或为苯基或苄基,它们各自随意被卤素,氰基,硝基,C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C1-C8卤代烷氧基,C1-C8烷硫基,C1-C8卤代烷硫基,C1-C8烷氧羰基或SCN取代,或为卤素或C1-C6烷基随意取代的含1至3个氮原子的随意取代的5元或6元杂环,或R3和R4一块与它们相连的氮原子形成4至8元环,形成随意被C1-C8烷基取代的随意含氧、硫或氮(该氮随意被C1-C8烷基,苯基或苄基取代)的环。R1尤其优选为氟。R2尤其优选为下式的基其中Y为氧或硫,Z为氧,硫或NR4,R3为氢,或随意被氟,氯,氰基,羧基,苯基,氨基(该氨基随意被C2-C6亚烷基(C2-C6-alkanediyl)取代或被相同或不同的C1-C6烷基单取代或双取代),C1-C6烷氧基,C1-C6烷硫基或氨羰基(该氨羰基随意被C2-C6亚烷基(C2-C6-alkanediyl)取代或被相同或不同的C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C3-C7环烷基,C3-C7卤代环烷基,C1-C3-烷基-C3-C7环烷基单取代或双取代,或被苯基或苄基取代,它们各自随意被卤素,氰基,硝基,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷硫基或C1-C6卤代烷硫基)取代的C1-C6烷基,或为随意被氟,氯或C1-C4烷基取代的C4-C8环烷基,或为苯基,苄基,苯氧羰基或苯砜基,它们各自随意被氟,氯,氰基,硝基,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷硫基,C1-C6卤代烷硫基,C1-C6烷氧羰基或SCN取代,或为氟,氯或C1-C4烷氧基随意取代的C1-C6烷氧羰基。R4尤其优选为氢,或为C1-C6烷基,氟或氯随意取代的C1-C4烷硫基,或C4-C8环烷基,或R3和R4一块与它们相连接的氮原子形成4至8元环,形成随意被C1-C6烷基取代的随意含氧,硫或氮(该氮随意被C1-C6烷基,苯基或苄基取代)的环。R1非常特别优选为氟。R2非常特别优选为下式的基其中Y为氧,Z为氧,硫或NR4,R3为氢,或随意被氟,氯,氰基,羧基,苯基,氨基(该氨基随意被C2-C6亚烷基(C2-C6-alkanediyl)取代或被相同或不同的C1-C6烷基单取代或双取代),C1-C6烷氧基,C1-C6烷硫基或氨羰基(该氨羰基随意被C2-C6亚烷基(C2-C6-alkanediyl)取代或被相同或不同的C1-C4烷基,C1-C4烷氧基单取代或双取代,或被苯基或苄基取代,它们各自随意被卤素,氰基,硝基,C1-C6烷基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C1-C6烷硫基或C1-C6卤代烷硫基)取代的C1-C6烷基,或为C1-C4烷基随意取代的C4-C8环烷基,或为苯基,苄基,苯氧羰基或苯砜基,它们各自随意被氟,氯,氰基,硝基,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,C1-C4卤代烷硫基或C1-C4烷氧羰基取代,或为氟,氯,或C1-C4烷氧基随意取代的C1-C4烷氧羰基。R4非常特别优选为氢,或为C1-C4烷基,为氟或氯随意取代的C1-C3烷硫基,或C4-C6环烷基,或R3和R4一起与它们相连的氮原子形成4至8元环,或形成C1-C4烷基取代的随意含氧,硫或氮(该氮随意被C1-C4烷基或苄基随意取代)的环。
上述的基团或描述的一般的或优选的定义用于终产物和对应地用于原料和中间体。这些基团的定义能按需相互结合,也就是说可能在各自优选的范围之间结合。
按照本发明,优选给予含上述作为优选的含义的组合的通式(Ia)和(Ib)的化合物。
按照本发明,特别的优选给予含上述作为特别优选的组合的通式(Ia)和(Ib)的化合物。
按照本发明,非常特别的优选给予含上述作为非常特别优选的组合的通式(Ia)和(Ib)的化合物。
进一步优选的化合物组是通式(Ic)的化合物,特别是其中Z为氧和R5为脂肪基优选为低级烷基特别是乙基的化合物。
在上下文给定的基的定义中,烃基,例如烷基或烯基-以及与杂原子相连的,例如烷氧基或烷硫基-在各种情况下尽可能为直链或支链。
与基团R5,R6,R7,R8,R9,R10和R11的定义中使用的术语理解如下:
术语“卤素”意指氟、氯、溴、碘。
术语“烷基”为直链或支链C1-C7烷基。
术语“低级烷基”为直链或支链C1-C4烷基。
术语“脂肪基”为饱和或不饱和的,含1至10个碳原子(或如所说)的直链或支链烷基,或含2至10个碳原子(或如所说)的直链或支链烯基。
术语“烷氧基”为经由氧原子连接的低级烷基。
术语“烷硫基”为经由硫原子连接的低级烷基。
术语“烷氧羰基”为羧基的低级羧酸的烷基酯。
术语“羧酸基,磺酸基,磷酸基或亚磷酸基或提到的酸的酯,硫酯或酰胺”意指其中至少一个碳原子已被羧基取代的脂肪基,或其中至少一个氢原子已被磺酸基,亚磷酸基或磷酸基和提到的酸的低级烷基酯、低级烷基硫酯或酰胺(该酰胺随意被1个或2个低级烷基取代)取代的脂肪基。
术语“氨基酸”意指NR5R6随意被天然或非天然氨基酸的氨基取代。
术语“芳香基”或“芳基”意指随意象上面所述的取代的苯基。
术语“杂环基”指环中至少含1个非碳元素的任何环。杂原子可以是氧,氮,硫或其它元素。杂环的例子有噻二唑,吡啶,噻唑,异噻唑,噁唑,咪唑,吡唑,***,苯并噻唑,含硫杂环,吗啉,哌啶,哌嗪,或吡咯烷,它们至少被一个取代基取代,这些取代基来自氰基,三甲基硅基,羟基,烷氧基,卤素,硝基,氨基,SH,烷硫基,羧基,烷氧羰基,苯基,羧酸基,磺酸基,磷酸基,亚磷酸基,或这些酸的酯,硫代酯或酰胺。
按照本发明的方法Aβ)制备通式(I)的化合物时,如果用例如3,4,4-三氟-丁-3-烯醇和异氰酸苯酯作原料,那么可以用下面的反应路线来描述反应:
按照本发明的方法C)制备通式(I)的化合物时,如果用例如氯甲酸-(3,4,4-三氟-丁-3-烯)-酯和环己胺为原料,那么可以用下面的反应路线来描述反应:
所有上面描述的制备通式(I)的化合物的方法Aα,Aβ,B,C和D的特征在于其中反应在稀释剂的存在下进行。
这些方法中的适宜稀释剂均为常规溶剂。
特别适合的稀释剂为随意卤代的脂肪烃或芳香烃,醚或腈,例如环己烷,甲苯,氯苯,氯仿,二氯甲烷,二氯乙烷,二氧六环,四氢呋喃,***或乙腈。
所有上面描述的制备通式(I)的化合物的方法Aα,B,C和D的特征在于其中反应随意地在碱存在下进行。
方法Aα,B,C和D中适宜的碱均为常规质子受体,特别适宜的碱为碱金属氢氧化物,或碱土金属氢氧化物,碱金属碳酸盐,或碱土金属碳酸盐,或碱金属碳酸氢盐,或碱土金属碳酸氢盐,或含氮碱。例子包括氢氧化钠,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,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)和二氮杂双环十一烯(DBU)。
上面描述的制备通式(I)的化合物的方法Aβ的特征在于其中反应随意地在催化剂的存在下进行。
适宜的催化剂为例如二氮杂双环辛烷(DABCO),三乙胺或吡啶或有机锡化物,例如二月桂酸二丁基锡。
上面描述的方法Aα,Aβ,B,C和D中的反应温度在各种情况下可以在相对宽的范围变化。在方法Aα,B,C和D中,反应一般在-10℃和150℃之间进行。优选在0℃和90℃之间进行。在方法Aβ中,反应一般在0℃和120℃之间进行,优选在20℃和100℃之间进行。
在方法Aα中通式(II)和(III)以及方法B中通式(IIa)和(III)的原料比为1∶1至2∶1。
在方法Aβ中通式(II)和(IV)的原料比例一般在2∶1和l∶2之间;优选为等量使用。
在方法C中的通式(V)和(VI)的原料以及方法D中的通式(VII)和通式(VIII)的原料比例一般分别在1∶1和10∶1之间。
上面描述的方法Aα,Aβ,B,C和D一般在大气压下实施。上面描述的方法Aα,Aβ,B,C和D后处理时,将反应混合物例如用水稀释,用有机溶剂萃取,然后浓缩有机相。
在方法Aα和Aβ中使用的通式(II)的原料为已知的,并可以按已知方法制备(参见例如WO 92/15555)。
在方法Aα和B中也使用的通式(III)或(IIIa)的原料为已知的和/或可以按已知方法制备。通式(III)或(IIIa)的化合物例如可以通过醇,硫醇或通式(VI)的胺按已知方法与光气或硫代光气反应制得(参见例如Houben-Weyl,Methoden der Organischem Chemie,BandE4,S.407 ff.,Georg Thieme Verlag Stuttgart,NeW York,1983)。
在方法Aβ中用作原料的通式(IV)的异硫代氰酸酯是有机化学中用于合成的已知化合物。
在方法C中使用的通式(V)的原料虽然是新化合物,但可以通过已知方法制备。例如通式(II)的化合物按常规方法(见上面)与光气或硫代光气反应可以制得通式(V)的化合物。
在方法C中也使用的通式(VI)的原料一般是有机化学中用于合成的已知化合物。
在方法D中使用的通式(VII)的原料虽然是新化合物,但可以按已知方法制备。例如通式(IIa)的化合物按本质上已知的方法(见上面)与光气或硫代光气反应可以制得通式(VII)的化合物。
在方法D中也使用的通式(VIII)的原料一般是有机化学中用于合成的已知化合物。
这类活性化合物适合于控制有害动物,尤其是控制在农业,林业,在产品和物材保藏中及卫生界碰到的昆虫,蜘蛛类及线虫。它们无论是对正常敏感的害虫还是对抗药的害虫,以及对所述害虫的发育全过程或发育的某些阶段都有拮抗活性。上面提到的害虫包括:
来自等足目,例如Oniscus asellus,Armadillidium vulgare以及Porcellio Scaber。
来自等足目的,例如Blaniulus guttulatus。
来自唇足亚纲的,例如Carpophagus的地蜈蚣属和蚰蜓科的种。
来自综合亚纲的,例如immaculata的蚰蜒科。
来自总尾目的,例如衣鱼。
来自弹尾目的,例如有刺的棘跳。
来自直翅目的,例如东方蠊,美国蜚蠊,马德拉蜚蠊,德国蠊,家蟋,蝼蛄种,非洲飞蝗,异黑蝗和沙漠蝗。
来自革翅目的,例如欧洲球螋。
来自等翅目的,例如散白蚁种。
来自虱目的,例如体虱,血虱种和毛虱种。
来自食毛目的,例如嚼虱种和畜虱种。
来自缨翅目的,例如温室条篱蓟马和烟蓟马。
来自半翅目的,例如扁盲蝽种,棉红蝽intermedius,方背皮蝽,温带臭虫,长红猎蝽和维猎蝽种。
来自半翅目的,例如甘蓝粉虱,木薯粉虱,温室粉虱,棉蚜,甘蓝蚜,茶藨隐瘤蚜、豆卫矛蚜,苹果蚜,苹果棉蚜,梅大尾蚜,葡萄根瘤蚜,瘿绵蚜种,麦长管蚜,瘤蚜种,忽布疣蚜,禾谷缢管蚜,小叶蝉种,具二叶的钝鼻殃叶蝉,黑尾叶蝉,水木坚蚧,乌盔蚧,灰飞虱,褐飞虱,红肾圆盾蚧,常春藤圆盾蚧,粉蚧种,和木虱种。
来自鳞翅目的,例如红铃麦蛾,松尺蠖,Cheimatobia brumata,苹细蛾,苹果巢蛾,菜蛾,黄褐天幕毛虫,黄毒蛾,毒蛾种,棉潜蛾,桔潜蛾,地老虎种,切根虫种,夜蛾种,埃及金钢钻,实夜蛾种,甜菜夜蛾,甘蓝夜蛾,松夜蛾,litura夜蛾,灰翅夜蛾种,粉纹夜蛾,苹果小卷蛾,菜粉蝶种,禾草螟种,玉米螟,地中海粉斑螟,Galleriamellonella,幕谷蛾,袋谷蛾,褐织蛾,亚麻黄卷蛾,reticulana卷蛾,枞色卷蛾,Clysia ambiguella,茶长卷蛾和栎绿卷蛾。
来自鞘翅目的,例如家具窃蠹,谷蠹,具被的锥胸豆象属,菜豆象,北美家天牛,杨树萤叶甲,马铃薯叶甲,辣根猿叶甲,叶甲种,油菜金头跳甲,墨西哥大豆瓢虫,甜菜隐食甲种,锯谷盗,花象种,谷象种,黑葡萄耳象,香蕉根颈象,白菜粉龟象,紫苜蓿叶象,皮蠹种,斑皮蠹种,圆皮蠹种,粉蠹种,aeneus露尾甲,蛛甲种,黄蛛甲,裸蛛甲,谷盗种,黄粉虫,叩头虫种,西方五月鳃角金龟,欧洲鳃角金龟和和褐新西兰肋翅鳃角金龟。
来自膜翅目的,例如锯角叶蜂种,叶蜂种,蚁种,法老蚁和胡蜂种。
来自双翅目的,例如伊蚊种,桉蚊种,库蚊种,黑尾果蝇,家蝇种,厕蝇种,红头蝇种,绿蝇种,金蝇种,疽蝇种,胃蝇种,Hyppobosca种,厩螫蝇种,狂蝇种,皮蝇种,虻种,Tannia种,黑毛蚊,瑞曲麦杆蝇,晚麦草种蝇,甜菜泉蝇,地中海蜡实蝇,橄榄大实蝇和欧洲大蚊。
来自蚤目的,例如印鼠客蚤,角叶蚤种。
来自蛛形纲的,例如Scorpio maurus和Latrodectus mactans。
来自蜱螨目的,例如粗脚粉螨,锐缘螨种,钝缘蜱种,鸡皮刺螨,茶藨瘿螨,桔芸锈螨,牛蜱种,扇头蜱种,花蜱种,璃眼蜱种,硬蜱种,痒螨种,瘁螨种,Sarcoptes种,跗线螨种,苜蓿苔螨,金爪螨种和叶螨种。
The phytoparasitic nematodes包括Pratylenchus种,Radopholussimilis,Ditylenchus dipsaci,Tylenchulus semipenetrans,狭体叩头虫种,Globodera种,Meloidogyne种,Aphelenchoides种,Longidorus种,Xiphinema种和Trichodorus种。
本发明的通式(I)的化合物特别显示了优秀的杀昆虫和杀线虫活性。用于杀叶生和土壤生昆虫时,它们显示强活性,例如显示强的杀芥子杵lavae(Phaedon cochleariae)和菱信背蛾(Plutella maculipcunis)的蠋。当用于杀线虫时,它们具有例如强的杀Meloidogyne incognita活性。
本发明的化合物不仅有预防作用,还可用于叶***和根***抗虫害。
本发明的通式(I)的活性化合物进一步地还具有杀真菌作用,例如有杀大米中Pyricularia oryzea的作用。
这类活性化合物可以转变为常用剂型,例如转变为溶液剂,乳化剂,可湿粉剂,悬浮剂,粉剂,粉尘剂,糊剂,可溶性粉剂,颗粒剂,悬浮剂-乳化剂浓缩物,用活性化合物浸渍的天然物和合成物,以及用高聚物制作的极细胶囊。
这些剂型按已知方法生产,例如通过活性化合物与扩展剂混合,即与液体溶剂和/或固体载体混合,随意地使用表面活性剂,即使用乳化剂和/或分散剂和/或泡沫形成剂。
使用水作为扩展剂时,亦可使用有机溶剂作为助溶剂。作为液体溶剂,适宜的主要有:芳烃,例如二甲苯、甲苯或烷基萘,氯代芳香烃和氯代脂肪烃,例如氯苯、氯乙烯、二氯甲烷、脂肪烃,例如环己烷或链烷烃,例如石油醚馏分,矿物油和植物油,醇类,例如丁醇或甘油,以及它们的醚或酯,酮类,例如丙酮,甲基乙基酮,甲基异丁基酮或环己酮,强极性溶剂,例如二甲基甲酰胺和二甲基亚砜以及水。适宜的固体载体有:例如铵盐和研磨的天然物料,例如高岭土,粘土,滑石,白垩,石英,活性白土,蒙脱土或硅藻土,以及研磨的合成物料,例如高分散的硅胶,氧化铝和硅酸盐,适宜作颗粒剂的固体载体有:例如粉碎的和分级的天然岩石,例如方解石,大理石,浮石,海泡石和白云石,以及无机和有机粉的合成颗粒,以及有机物料的颗粒,例如锯末,可可壳,玉米碎块和烟草杆;适宜的乳化剂和/或泡沫形成剂有:例如非离子型和阴离子型乳化剂,例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,烷基磺酸酯,烷基硫酸酯,芳基磺酸酯以及蛋清水解产物;合适的分散剂有:例如木素亚硫酸盐废液以及甲基纤维素。
粘合剂,例如羧甲基纤维素和粉状、颗粒状或胶乳状的天然的及合成的高聚物,例如***胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,例如脑磷脂和卵磷脂,以及合成的磷脂,可以用于配方。进一步的辅加剂为矿物油和植物油。
亦可使用着色剂,例如无机颜料,例如氧化铁,二氧化钛,和普鲁氏兰,以及有机染料,例如茜素染料,叠氮染料和金属酞菁染料和微量营养物质,例如铁、锰、硼、铜、钴,钼和锌等金属的盐。
配方一般包(创按重量计)0.1%至95%的活性化合物,优选含0.5%至90%的活性化合物。
新的活性化合物能以它的商品配方以及使用的形态存在,可以按这些配方制备,作为与其它活性化合物的混合物,例如与杀昆虫剂,引诱剂、消毒剂、抗菌剂、杀螨剂、杀线虫剂、杀真菌剂,生产调节物质或除草剂的混合物。杀昆虫剂包括,例如磷酸酯,氨基甲酸酯,羧酸酯,氯代烃,苯尿,以及特别是通过微生物产生的化合物质。
特别有利的成分的例子如下:杀真菌剂:
2-氨基丁烷;2-苯氨基-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-羧酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)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-羟基喹啉硫酸酯;(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧]苯基}-3-甲氧基丙烯酸酯;(E)-甲氧基亚氨基[α-(邻-甲苯氧)-O-甲苯基]乙酸甲酯;2-苯基苯酚(OPP),aldimorph,ampropylfos,敌菌灵,氮康唑,benalaxyl,麦锈灵,benomyl,乐杀螨,联苯,bitertanol,灭瘟素,bromuconazole,bupirimate,buthiobate,石硫合剂,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌清,chlozolinate,硫杂灵,cymoxanil,cyproconazole,cyprofuram,双氯酚,diclobutrazol,diclofluanid,diclomezine,氯硝胺,diethofencarb,difenoconazole,甲菌定,dimethomorph,diniconazole,敌螨普,二苯胺,dipyrithione,ditalimfos,二噻农,多果定,敌菌酮,克瘟散,epoxyconazole,乙菌啶,etridiazolè,fenarimol,fenbuconazole,fenfuram,fenitropan,fenpiclonil,fenpropidin,fenpropimorph,fentinacetate,fentinhydroxide,ferbam,ferimzone,fluazinam,fludioxonil,fluoromide,fluquinconazole,flusilazole,flusulphamide,flutolanil,flutriafol,灭菌丹,fosetyl-铝,fthalide,麦穗宁,furalaxyl,furmecyclox,双胍盐,六氯苯,hexaconazole,hymexazol,imazalil,imibenconazole,iminoctadine,iprobenfos(IBP),iprodione,富士一号,春雷毒素,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉-铜,和Bordeaux混合物。mancopper,代森锰锌,代森锰,mepanipyrim,mepronil,metalaxyl,metconazole,methasulphocarb,methfuroxam,代森联,metsulphovax,myclobutanil,福镁镍,nitrothal-isopropyl,muarimol,ofurace,axadixyl,oxamocarb,氧化萎锈灵,pefurazoate,penconazole,pencycuron,phosdiphen,四氯苯酞,多马霉素,粉病灵,福代锌,多氧霉素,噻菌灵,prochloraz,procymidone,propamocarb,propiconazole,甲基代森锌,定菌灵,pyrifenox,pyrimethanil,pyroguilon,五氯硝基苯(PCNB),硫和硫制剂,tebuconazole,tecloftalam,tecnazene,tetraconazole,涕必灵,thicyofen,甲基托布津,福美双,tolclophosmethyl,对甲抑菌灵,triadimefon,triadimenol,triazoxide,trichlamide,tricyclazole,克啉菌,triflumizole,嗪氨灵,triticonazole,有效霉素A,vinclozolin,代森锌,福美锌,杀细菌剂:溴硝灭二醇,双氯酚,nitrapyrin,福美镍,春雷霉素,octhilinone,呋喃羧酸,土霉素,噻菌灵,链霉素,tecloftalam,硫酸铜和其它铜制剂。杀昆虫剂/杀螨剂/杀线虫剂:abamectin,AC 303630,高灭磷,acrinathrin,alanycarb,涕灭威,alphamethrin,amitraz,avermectin,AZ 60541,azadirachtin,谷硫磷A,谷硫磷M,azocyclotin,苏芸金杆菌,噁虫威,benfuracarb,bensultap,beta-cyfluthrin,bifenthrin,丁苯成,brofenprox,溴硫磷A,bufencarb,buprofezin,butocarboxim,butylpyridaben,cadusafos,西维因,虫螨威,三硫磷,carbosulphan,巴丹,CGA l57419,CGA 184699,chloethocarb,chlorethoxyfos,毒虫畏,chlorfluazuron,氯甲磷,毒死蜱,chlorpyrifos M,顺-灭虫菊,clocythrin,clofentezine,杀螟腈,cycloprothrin,cyfluthrin,cyhalothrin,cyhexatin,cypermethrin,cyromazine,deltamethrin,一○五九M,一○五九S,甲基一○五九,diafenthiuron,二嗪农,除线磷,敌敌畏,dicliphos,百治磷,乙硫磷,diflubenzuron,乐果,dimethylvinphos,敌杀磷,乙拌磷,克瘟散,emamectin,esfenvalerate,ethiofencarb,乙硫磷,ethofenprox,ethoprophos,etrimphos,fenamiphos,fenazaquin,fenbutatinaxide,杀螟松,fenobucarb,fenothiocarb,fenoxycarb,fenpropathrin,fenpyrad,fenpyroximate,倍硫磷,fenvalerate,fipronil,fluazinam,flucycloxuron,flucythrinate,flufenoxuron,flufenprox,fluvalinate,地虫磷,安果,fosthiazate,fubfenprox,furathiocarb,六六六,heptenophos,hexaflumuron,hexythiazox,imidacloprid,iprobenfos,isazophos,isofenphos,isoprocarb,异噁唑磷,ivermectin,lambda-cyhalothrin,lufenuron,马拉松,灭蚜磷,速灭磷,mesulphenfos,蜗牛敌,methacrifos,甲胺磷,杀扑磷,灭虫威,灭多虫,metolcarb,milbemectin,久效磷,moxidectin,二溴磷,NC l84,NI 25,nitenpyram,氧化乐果,oxamyl,砜吸磷M,oxydeprofos,一六○五A,一六○五M,permethrin,稻丰散,三九一一,伏杀磷,亚胺硫磷,磷胺,腈肟磷,抗蚜威,虫螨磷M,虫螨磷A,profenofos,猛杀威,丙虫磷,残杀威,prothiofos,发果,pymetrozin,pyrachlofos,pyridaphenthion,pyresmethrin,除虫菊,pyridaben,pyrimidifen,pyriproxyfen,喹噁磷,RH 5992,杀抗松,sebufos,silafluofen,sulphotep,sulprofos,tebufenozid,tebufenpyrad,tebupirimifos,teflubenzuron,tefluthrin,temephos,叔丁威,terbufos,杀虫畏,thiafenox,thiodicarb,thiofanox,thiomethon,硫磷嗪,thuringiensin,tralomethrin,triarathen,***啉,triazuron,敌百虫,triflumuron,trimethacarb,蚜灭多,二甲威,xylylcarb,YI 5301/5302,zetamethrin,
亦可以与别的已知活性化合物掺合,例如与除草剂或肥料和促生长化合物掺合。
本发明的活性化合物可以进一步地以它们的商品配方和以从这些配方制备的使用形存在,作为与协同剂的混合物。协同剂是增加活性化合物作用的化合物,协同剂本身设有必要是有活性的。
从商品配方制备的使用形态的活性化合物的量可以在大的限度内变化。使用形态的活性化合物的浓度可以是从活性化合物的重量的0.0000001至95%,优选的为0.0001至1%(按重量计)。
化合物按适合于使用形态的常规方式使用。
当用于杀卫生界害虫和储存的产品的害虫时,活性化合物在木材,粘土上有优秀的残留作用,对用石灰处理的底物上的碱具有良好的稳定性。
本发明的活性化合物不仅具有杀灭植物,卫生和保藏的产品中的害虫的作用,还可以在兽医中杀灭动物寄生虫(外寄生物),例如硬蜱,软蜱,痂螨,沙螨,蝇(叮和吸),寄生蝇幼虫,虱、发虱、鸟虱和蚤。这些寄生虫包括:
来自Anoplurida目的,例如血虱种,毛虱虫种,虱种,phtirus种,管虱种;
来自食毛目的和粗颈豆象亚科和Ischnocerina目的,例如毛羽虱种,禽虱种,巨羽虱种,牛羽虱种,Werneckiella种,Lepikentron种,畜虱种,嚼虱种,猫羽虱种;
来自双翅目的和直裂部亚目的和直裂部的,例如伊蚊种,按蚊种,库蚊种,蚋种,真蚋种,白蛉种,Lutzomyia种,蚊总科,斑虻种,hybomitra种,黄虻种,虻属,麻虻属,philipomyia种,蜂虱蝇属,家蝇属,齿股蝇属,厩螯蝇属,东方角蝇种,Morellia属,厕蝇属,舌蝇属,丽蝇属,绿蝇属,金蝇属,黑须污蝇,麻蝇属,狂蝇属,皮蝇属,胃蝇属,虱蝇属,羊虱蝇属和蜱蝇属。
来自蚤目的,例如,蚤种,栉首蚤属,客蚤属,角叶蚤属。
来自半翅目的,例如,臭虫属,锥猎蝽属,红猎蝽属和Panstrongylus种。
来自蜚蠊目的,例如东方蠊,美洲大蠊,德国蠊,棕带蠊。
来自粉螨科(Acarida)亚族和Meta目和Mesostigmata目的,例如锐缘蜱属,钝缘蜱属,Otabius种,硬蜱属,花蜱属,牛蜱属,草蜱属,血蜱属,璃眼蜱属,扇头蜱属,皮刺螨属,Raillietia种,Pneumonyssus种,Sternostoma种和蜂螨属。
来自Actinedida(Prostigmata)目和Acaridida(Astigmata)目的,例如,蜂盾螨属,Cheyletiella种,Ornithocheyletia种,Myobia种,Psorergates种,蠕形螨属,恙螨属,黑斯象属,粉螨属,腐食螨属,Caloglyphus种,Hypodectes种,Pterolichus种,瘁螨属,痒螨属,耳疥螨属,疥螨属,耳螨属,脚螨属,Cytodites种和鸡雏螨属。
例如与微小牛蜱和铜绿蝇相比,它们显示优秀的活性。
本发明的通式(I)的活性化合物也适用于控制危害农业家畜的节肢动物,例如控制危害牛、羊、山羊、马、猪、猴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,例如狗、猫、笼鸟,缸养鱼以及所谓的实验动物,例如仓鼠,荷兰猪,大鼠和小鼠的节肢动物。通过控制这些节肢动物,目的在于降低家畜的死亡率以及减小工作量(在肉类、牛奶、毛皮、皮革、蛋、蜜等等中的工作量),以便有可能使用本发明的活性化合物更经济,更简单地饲养动物。
在兽医领域里,本发明的活性化合物以已知的方式内服给药,例如以片剂、胶囊、饮料、药水、颗粒剂、膏剂、丸剂、食饲剂、栓剂等内服,通过非肠道给药,例如注射(肌肉注射,皮下注射,静脉注射,腹膜内注射等等),植入给药,鼻腔给药,经皮给药,例如以浸渍剂或溶液剂,喷雾剂,注入剂和点入剂,洗剂,粉尘剂给药,以及借助于含活性化合物的成形物,例如借助含活性化合物的颈圈,耳套,尾记,翼带,笼头,标记器件等给药。
当给牲畜,家畜,家养动物等给药时,通式(I)的活性化合物能以含1至80%量的活性化合物的配方(例如粉,乳化液,流动性物料)给药,或直接使用,或按100至10000的因子稀释,或以化学浴的形式使用。
本发明的通式(I)的化合物进一步发现具有强的杀灭可毁坏农作物的昆虫的作用。
下面的昆虫可以作为例子及优选的例子提到,但没有任何限制的意味。甲虫类,例如:北美家大牛,Pilosis缘象,家具窃蠹,极死窃蠹,梳角细脉窃蠹,Dendrobium pertinex,松窃蠹,Priobium carpini,褐粉蠹,africanus粉蠹,南方粉蠹,烁粉蠹,柔毛粉蠹,Trogoxylon aequale,鳞毛粉蠹,材小蠹种,黑材小蠹种,咖啡黑长蠹,槲长蠹,Heterobostrychusbrunneus,长蠹种,竹长蠹。革翅目,例如:大树蜂,枞大树蜂,taignus枞大树蜂,augur枞大树蜂。白蚁科目,例如木白蚁,flavicollis,麻头堆砂白蚁,异白蚁,欧美散白蚁,Reticulitermessantonensis,Reticulitermes lucifugus,达尔文澳白蚁,nevadensis白蚁,家白蚁。Bristlefails,例如衣鱼。
在本文中工业品应理解为非生活物料,例如优选为合成物料,胶水,浆糊,纸以及纸板,皮,木头,木材产品以及涂料。
特别优选防止昆虫侵害的物料为木头和木材产品。
可以用本发明的组合物或含这类组合物的混合物保护的木头和木材产品应理解为,例如建筑木材,木梁,铁路枕木,桥梁部件,栈桥,木轮,轴,制模板,容器,电杆,木防护套,木窗和木门,胶合板,粒子板,细木工人的工具,或用于建造房屋或细木的非常普通的木材产品。
活性化合物可以以浓缩物的形式或以常用配方,例如粉末剂,颗粒剂,溶液剂,悬浮剂,乳化剂,或膏剂使用。
提到的配方可按文献的已知方法制备,例如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,水驱斥剂,如果适宜的话与干燥剂和紫外线稳定剂,如果适宜的话与着色剂如颜料以及其它辅料混合。
用于保护木料和木材的杀昆虫的组合物或浓缩液包含本发明的活性化合物,按重量计,浓度为0.0001至95%,特别为0.001至60%。
组合物或浓缩液的用量取决于介质上的昆虫的种类和发生虫害的情形。使用的最优比例可根据被测系列的每种情形确定。不过,一般地说,以被保护的物料的按重量计算使用0.0001至20%的活性化合物已足够,优选为0.001至10%。
使用的溶剂和/或稀释剂为有机溶剂或溶剂的混合物和/或油状或油状的有机溶剂或低挥发性溶剂的混合物和/或极性有机溶剂或溶剂混合物和/或水,适宜的乳化剂和/或保湿剂。
优选使用的有机溶剂为蒸发数高于35,闪点高于30℃,优选高于45℃的油状或油性溶剂。使用的这类油状和油性溶剂为挥发度低,不溶于水的矿物油或它们的芳香性馏分,或含矿物油的溶剂混合物,优选为石油溶剂,石油产品和/或烷基苯。
有利于使用的化合物为沸程为170至200℃的矿物油,沸程为170至220℃的石油溶剂,沸程为250至350℃的锭子油,沸程为160至280℃的石油产品或芳香化合物,精萜等等。
在优选的实施方案中使用沸程为180至210℃的液态脂肪烃,或沸程为180至220℃的芳香烃和脂肪烃的高沸点混合物和/或锭子油和/或一氯萘,优选的为α一氯萘。
蒸发数高于35,闪点高于30℃,优选为高于45℃的低挥发度的有机油状或油性溶剂可以部分被高或中挥发度的有机化学溶剂取代,条件是得到的溶剂混合物的蒸发数也高于35,闪点高于30℃,优选高于45℃,而且杀昆虫/杀真菌混合物或溶于该溶剂混合物,或可乳化于该溶剂混合物。
在优选的实施方案中,有机化学溶剂或溶剂混合物,或脂肪极性有机化学溶剂或溶剂混合物的部分被取代。优选使用的化合物为含羟基和/或酯和/或醚基的脂肪有机化学溶剂,例如乙二醇醚,酯等等。
本发明范围内使用的有机化学粘合剂为合成树脂和/或文献中已知的并能用水稀释和/或在使用的有机化学溶剂中可溶或可分散或可乳化的粘合干燥油,尤其是由以下树脂组成的或包含以下树脂的粘合剂:丙烯酸酯树脂,乙烯基树脂,例如聚乙酸乙烯酯,聚酯树脂,聚缩合树脂或聚加成树脂,聚氨酯树脂,醇酸树脂或改性的醇酸树脂,酚醛树脂,烃树脂,例如茚/香豆酮树脂,有机硅树脂,干性植物和/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化液,分散液或溶剂的形式使用。高达10%重量的沥青或沥青样物质亦可用作粘合剂。此外,也可以使用着色剂,颜料,水驱斥剂,气味掩盖物质和抑制剂或文献已知的抗腐蚀剂等等。
按照本发明,组合物或浓缩液优选包含至少一种作为有机化学粘合剂的醇酸树脂或改性的醇酸树脂和/或干性植物油。按照本发明优选使用的醇酸树脂的油含量按重量计超过45%,优选为50%至68%。
上面提到的所有或有些粘合剂能够被固定剂(混合物)或增塑剂(混合物)取代。这些附加剂的目的在于防止活性化合物挥发和结晶或沉淀。它们优选取代0.01至30%粘合剂(使用的粘合剂定义为100%)。
增塑剂来自邻苯二甲酸酯类化合物,例如来自邻苯二甲酸二丁酯,邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯,来自磷酸酯,例如磷酸三丁酯,来自己二酸酯,例如己二酸二-(2-乙基己基)酯,来自硬脂酸酯,例如硬脂酸丁酯或硬脂酸戊酯,来自油酸酯,例如油酸丁酯,来自甘油醚,或相对高分子量的乙二醇醚,甘油酯和对甲苯磺酸酯。
固定剂的化学基础是聚乙烯基烷基醚,例如聚乙烯基甲基醚,或酮类,例如二苯甲酮,或1,2-亚乙基二苯甲酮。
特别适合的溶剂或稀释剂还是水,合适的话,为水与一种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。
通过大规模的工业浸渍操作,例如真空操作,双真空操作或加压操作可使木材达到特别有效的保护。
合适的话,立即可用的组合物可以包含别的杀昆虫剂,合适的话,可以再含一种或多种杀真菌剂。
可以掺和的适宜的外加组分优选为在WO 94/29268中提到的杀昆虫剂和杀真菌剂。那个文件中提到的化合物明确地用为参考掺入本申请。
非常特别优选的可掺和的组分为杀昆虫剂,例如毒死蜱、腈肟磷、Silafluofin,alphamethrin,cyfluthrin,cypermethrin,deltamethrin,permethrin,imidacloprid,NI-25,flufenoxuron,hexaflumuron,和triflumuron,和杀真菌剂,例如epoxyconazole,hexaconazole,azaconazole,propiconazole,tebuconazole,cyproconazole,metconazole,imazalil,抑菌灵,对甲抑菌灵,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。
从下面的实施例可以看出本发明的活性化合物的制备和应用。
制备实施例
实施例I-1
CF2=CF-CH2-CH2-O-CO-OC2H5 (I-1)
在冰冷却下往6.3g(50mmol)3,4,4-三氟丁-3-烯醇与50ml二氯甲烷的溶液中先滴加5.4g(50mmol)氯甲酸乙酯,再滴加5.4g(53mmol)三乙胺。使溶液升温至20℃,并继续搅拌过夜。用水稀释后产品用二氯乙烷萃取,萃取液减压浓缩。残留物在30mmHg柱压力下蒸馏,在80℃蒸出(3,4,4-三氟丁-3-烯基)碳酸乙酯。
产量2.9g(理论量的30%)。
实施例I-2(I-2)
将3.5g(22.5mmol)异氰酸-2,6-二氟苯酯加到2.8g(20mmol)3,4,4-三氟丁-3-烯醇与20mi二氯甲烷的溶液中。于40℃搅拌过夜后,溶液用水洗,分出有机相,用无水硫酸镁干燥。减压除去溶剂。残留物用环己烷研磨。
产量5.4g(理论量的96%)。
m.p.56-60℃。实施例I-3(I-3)
在10℃和搅拌下往5.0g(32mmol)N,N-六亚甲基羟基乙酰胺和3.1g(30mmol)三乙胺与50ml二氯甲烷的溶液中滴加5.65g(30mmol)氯甲酸3,4,4-三氟丁-3-烯酯。溶液搅拌过夜,用二氯甲烷稀释,用水洗。分出有机相,减压浓缩,油状残留物用硅胶色谱纯化,用氯仿/乙酸乙酯(4∶1)洗脱。得到4.2g(理论量的45.6%)期待的碳酸酯,为油状物,logp=2.47。
验测定。
室温下往10.1g(0.1mol)三乙胺,6.0g(0.048mol)盐酸甘氨酸甲酯与50ml四氢呋喃(THF)的溶液中滴加3ml(0.05mmol)CS2。室温搅拌大约25分钟后,缓慢加9.45g(0.05mol)4-溴-1,1,2-三氟丁-1-烯,并在室温下继续搅拌过夜。减压蒸去溶剂,残留物溶入***。溶液用水洗4次,无水硫酸镁干燥,减压蒸去***。残留物用色谱纯化(硅胶,HPLC,用14%乙酸乙酯/己烷洗脱)。得7.8g粗产品,其中4.3g放在冰箱中直至结晶。减压下快速过滤和干燥,得到2.5g上面描述的化合物,为无色固体,mp:37-39℃。元素分析:元素 计算值 实测值C 35.16 35.26H 3.69 3.70N 5.13 5.10S 23.46 23.40实施例I-39
冰冷下往5g(0.03mol)原黄酸钾与35ml二甲基甲酰胺(DMF)的溶液中加6.24g(0.033mol)4-溴-1,1.2-三氟丁-1-烯,室温下继续搅拌过夜。混合物倾到300ml水中并用***萃取。***层用水洗4次,无水硫酸镁干燥,减压浓缩。得到5.52g上面描述的化合物,为清亮的黄色液体。元素分析:元素 计算值 实测值C 36.51 36.63H 3.94 3.97S 27.85 27.74
按照实施例I-38的方法,用等当量的盐酸甘氨酸叔丁酯代替甘氨酸甲酯。
得到的粗产品后处理之后用20%乙酸乙酯/己烷重结晶2次。得到2.35g上面描述的化合物,为无色固体,mp.70-72℃。元素分析:元素 计算值 实测值C 41.89 42.04H 5.11 5.05N 4.44 4.43S 20.33 20.27实施例I-41步骤A
41.43g(0.3mol)亚磷酸二乙酯,9g(0.3mol)多聚甲醛和3.04g(0.03mol)三乙胺于60至70℃加热。发生放热反应,温度升至120至125℃,溶液变清亮。该溶液于120℃搅拌10分钟,冷却,加一些二氯甲烷,溶液减压浓缩。残留物减压干燥。得到49.6g。分子式为HO-CH2-P(=O)(OC2H5)2的化合物为澄清液体。步骤B
在冰冷却下,往10g(0.059mol)步骤A中得到的化合物与20ml CS2的溶液中缓慢加入3.89g(0.059mol)85%KOH。溶液于室温搅拌2小时,加150ml***,再继续搅拌2小时。滤去沉淀,用***洗,减压干燥。得到13.69g分子式为的化合物,为黄色固体。步骤C
室温下,往4g(0.022ml)4-溴-1,1,2-三氟丁-1-烯与30mlDMF的溶液中一点一点加5g(0.0177mol)步骤B中得到的化合物。反应混合物室温搅拌过夜,倾到300ml水中并用***萃取。***层用水洗4次,无水硫酸镁干燥,浓缩。得到4.76g上面描述的终产物,为清亮的黄色液体。元素分析:元素 计算值 实测值C 34.09 34.18H 4.58 4.58S 18.20 18.14实施例I-42
冰冷却下,将10.3ml(0.078mol)溴代三乙基硅烷与10ml乙腈的溶液滴加到2.3g(0.0065mol)实施例I-41的化合物与15ml乙腈的溶液中。溶液于室温搅拌过夜,减压蒸去溶剂。残留物与过量的甲醇室温搅拌4小时。然后减压蒸去甲醇,产品减压干燥。得到1.96g上面描述的化合物,为无色固体,mp:73-75℃。元素分析:元素 计算值 实测值C 24.33 24.38H 2.72 2.70S 21.65 21.75
使用实施例I-38的方法,用等当量盐酸N-甲基甘氨酸叔丁酯代替盐酸甘氨酸甲酯,制得该化合物。为无色固体,mp:35-37℃。元素分析:元素 计算值 实测值C 43.76 43.83H 5.51 5.52N 4.25 4.23S 19.47 19.40
实施例I-46
按照实施例I-38的方法,从对应的前体开始制得实施例I-44,I-45和I-46的化合物。原料的制备
冰冷却和搅拌下,往30g(0.24mol)3,4,4-三氟丁-3-烯醇中通28g(0.28mol)光气,混合物然后于20℃再搅拌5小时。用氮气鼓泡除去过量的光气后,油状的残留物蒸馏。得到沸点为72-74℃/100mm的无色氯化物21.2g(理论量的46.8%)。
应用实施例
实施例A关键性的浓度试验试验方法:Meloidogyne incognita溶剂:4份重量的丙酮乳化剂:1份重量的烷基芳基聚乙二醇醚
为生产活性化合物的适宜的制品,1份重量的活性化合物与所述量的溶剂混合,加入所述量的乳化剂,浓缩物用水稀释到所需浓度。
活性化合物的制品与被待测线虫严重污染的土壤紧密混合。制品中的活性化合物的浓度无实际重要性,仅仅每单位体积的化合物的量,以ppm(=mg/l)给出,是决定因素。处理过的土壤转移到锅里并播种莴苣,温室保持25℃。
三周后检查莴苣根部寄生的线虫(根瘤),活性化合物的有效程度以百分数表示。若完全防止寄生,那么有效程度为100%,若寄生的水平与未用药用治疗但土壤污染程度相等的对照的植物一样,那么有效程度为0%。该试验中,例如制备实施例I-4和I-5的化合物在20ppm的例证活性化合物浓度下显示的有效程度为100%。
实施例B
幼虫试验溶剂:7份重量二甲基甲酰胺乳化剂:1份重量烷基芳基聚乙二醇醚
为生产适宜的活性化合物的制品,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,浓缩物用水稀释到所需浓度。
菜叶(Brassica oleracea)用注入法注入所需浓度的活性化合物的制品,并用芥甲壳虫幼虫(phaedon幼虫)寄生,菜叶仍保持潮湿。
在专门的时间周期之后,测定破坏的百分数。100%指所有的芥甲壳虫幼虫都被杀死;0%指所有的芥甲壳虫幼虫毫无伤害。在该试验中,7天后例如制备实施例I-6的化合物作为例证性的活性化合物在0.1%浓度下对幼虫产生100%破坏作用。
实施例Cplutella试验溶剂:7份重量二甲基甲酰胺乳化剂:1份重量烷基芳基聚乙二醇醚
为生产适宜的活性化合物的制品,1份重量的活性化合物与所述量的溶剂及所述量的乳化剂混合,浓缩物用水稀释到所需浓度。
菜叶(Brassica oleracea)用注入法注入所需浓度的活性化合物的制品,当叶子仍然潮湿时寄生上绫纹背蛾的蠋(plutella maculipcnnis)。
特定的时间周期后,测定蠋毁坏的百分数。所有的蠋都被杀死定为100%;没有一个蠋被杀死定为0%。
在该试验中,7天以后,例如制备实施例I-2,I-4,I-5,I-6和I-8作为例证性活性化合物,浓度为0.1%时对蠋的杀死率达100%。实施例DSpodoptera试验溶剂:7份重量二甲基甲酰胺乳化剂:1份重量烷基芳基聚乙二醇醚
为生产适宜的活性化合物的制品,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,浓缩物用水稀释到所需的浓度。
菜叶(Brassica oleracea)用注入法注入所需浓度的活性化合物的制品,菜叶仍然潮湿时用owlet蛾(Spodoptera frugiperda)的蠋寄生。
在特定的时间周期之后,测定蠋毁坏的百分数。所有的蠋都被杀死定为100%;没有一个蠋被杀死定为0%。
在该试验中,7天以后,例如制备实施例I-5和I-7的化合物作为例证性活性化合物,浓度为0.1%时对蠋的杀死率达100%。
实施例ENephotettix试验溶剂:7份重量二甲基甲酰胺乳化剂:1份重量烷基芳基聚乙二醇醚
为生产适宜的活性化合物的制品,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,浓缩物用水稀释到所需浓度。
水稻秧(Oryzae sative)用注入法注入所需浓度的活性化合物制品,当秧苗仍然潮湿时用绿水稻叶跳虫(Nophotettix)的幼虫(incticeps)寄生。
期望的时间周期后,测定杀死幼虫的百分数。所有的叶跳虫的幼虫都被杀死定为100%,没有一只幼虫被杀死定为0%。
在该实验中,6天后,例如制备实施例I-2,I-4,I-5,I-6,I-7和I-8的化合物作为例证性活性化合物,浓度为0.1%时,对跳虫幼虫的杀死率达100%。
实施例F
用boophilus microplus耐药/SP-耐药的Parkhurst株作试验。试验动物:已经吸血的成年雌蜱溶剂:35份重量的乙二醇单甲醚乳化剂:35份重量的壬烷基酚聚乙二醇醚
为生产适宜的配方,3份重量的活性化合物与上面指出的7份重量的溶剂-乳化剂混合物混合,浓缩物用水稀释到所需浓度。
10个成年Boophilus microplus res.在被测的活性化合物中浸渍1分钟。转移到塑料杯中并在控制的环境室中保存后,测得蝉毁坏的程度。
100%定为所有的蜱都被杀死;0%定为没有一个蜱被杀死。在该试验中,例如制备实施例I-5,I-6和I-7的化合物作为例证性活性化合物,浓度为1000ppm时,对蜱的杀死率达100%。
实施例G
用绿头苍蝇幼虫试验/发育-抑制作用试验动物:lucilia cuprina幼虫溶剂:25份重量乙二醇单甲醚乳化剂:35份重量壬烷基苯酚聚乙二醇醚
为生产适宜的配方,3份重量的活性化合物与上面指出的7份重量的溶剂-乳化剂混合,用水将得到的浓乳化液稀释至所需浓度。
往装有大约1cm3马肉和0.5ml待测的活性化合物制品的试管中引入大约20只幼虫。24小时和48小时后,测定活性化合物制品的活性。将试管转移到用沙铺底的杯中。再过2天后,除去试管,将蛹计数。
用未治疗的对照发育时间的1.5倍之后孵出的苍蝇数判定活性化合物制品的活性。无蝇孵出定为100%;所有的苍蝇都正常孵出定为0%。
在该试验中,例如制备实施例I-1,I-4和I-8的化合物作为例证性活性化合物,浓度为1000ppm时,毁蛹率达100%。
实施例H杀线虫试验(土豆和大豆)
本试验按美国专利5,389,680进行。该说明书明确编入本申请。
在该实验中(方法2),制备实施例I-39的化合物在每锅1mg浓度时显示的活性为91至100%,在每锅0.2mg浓度时显示的活性为75至90%,在每锅0.04mg浓度时显示的活性不足50%。
Claims (11)
1.通式(I)的化合物(I)其中R1为氢或卤素和R2为基团(a)或(b)(a)或(b)其中Y为氧或硫,Z为氧、硫或NR4,R3为氢或随意取代的烷基,烯基,环烷基,芳基,芳烷基,烷氧羰基,芳氧羰基,芳磺酰基或杂芳基,和R4为氢或分别随意取代的芳基,烷硫基,烯基,环烷基,芳基,芳烷基,杂芳基,或R3和R4与它们相连的氮原子一块形成随意取代的随意含氧、硫或氮(该氮随意被烷基,芳基或芳烷基取代)的环,或为基团(C)(c)其中V为氧或NR6和R5和R6各自独立为氢,1至12个碳原子的脂肪基,芳香基或杂环基,它们的每个都随意被至少一个取代基取代,取代基来自烷基,氰基,三甲基硅基,羟基,烷氧基,卤素,硝基,氨基,烷氨基,二烷基氨基,SH,烷硫基,苯基,或被羧酸基,磺酸基,磷酸基或亚磷酸基或这些酸的酯,硫酯或酰胺取代,该酰胺随意被烷基单取代或双取代,或R5和R6与它们相连的氮原子一块形成一氨基酸或随意另外含氧,硫或氮的杂环基,它们每个都随意被烷基,氰基,三甲基硅基,羟基,烷氧基,卤素,硝基,氨基,烷氨基,二烷基氨基,SH,烷硫基,苯基或羧酸基,磺酸基,磷酸基或亚磷酸基或这些酸的酯,硫酯或酰胺基单取代,该酰胺基随意被烷基单取代或双取代,或R5为OR7,COR7,NR7R8,SO2R9或P(=O)R10R11之一的基,在各种情况下R6为氢,R7和R8各自独立为氢,烷基或芳基,R9为氢,烷基,卤代烷基或芳基,和R10和R11各自独立为氢,烷基,芳基,烷氧基,芳氧基,烷硫基,芳硫基,氨基,烷氨基,二烷基氨基或芳氨基,以及它们的盐。
5.制备权利要求2的通式(Ia)或(Ib)化合物的方法,其特征在于A)通式(II)的氟丁烯醇(II)其中R1的含义同权利要求1与以下化合物反应α)与通式(III)的化合物在稀释剂和随意在碱存在下反应(III)其中Y,Z和R3的含义同权利要求1,或β)与通式(IV)的异(硫)氰酸酯在稀释剂和随意在催化剂的存在下反应,
YCN-R3 (IV)或B)通式(IIa)的氟丁烯硫醇(IIa)其中R1的含义同上与通式(IIIa)的化合物在稀释剂或随意在碱的存在下反应,(IIIa)其中Y和R3的含义同上,或C)通式(V)的化合物(V)其中R1和Y的含义同上与通式(VI)的化合物在稀释剂或随意在碱的存在下反应,
H-S-R3 (VIII)其中R3的含义同上。
8.杀虫剂,其特征在于它们包含至少一种权利要求1的通式(I)的化合物。
9.使用权利要求1的通式(I)的化合物控制动物害虫。
10.控制动物害虫的方法,其特征在于根据权利要求1的通式(I)的化合物使其作用于害虫上和/或它们的栖息地上。
11.制备控制动物害虫的组合物的方法,其特征在于根据权利要求1的通式(I)的化合物与扩展剂和/或表面活性剂混合。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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US08/003,987 | 1993-01-15 | ||
DEP4439335.0 | 1994-11-04 | ||
DE4439335A DE4439335A1 (de) | 1994-11-04 | 1994-11-04 | Kohlensäure- und Carbamidsäurefluorbutenylester |
US398795P | 1995-10-06 | 1995-10-06 |
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CN1171775A true CN1171775A (zh) | 1998-01-28 |
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CN95197158A Pending CN1171775A (zh) | 1994-11-04 | 1995-11-02 | 氟代丁烯基酯 |
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EP (1) | EP0789683A1 (zh) |
JP (1) | JPH10508592A (zh) |
CN (1) | CN1171775A (zh) |
AU (1) | AU3927195A (zh) |
BR (1) | BR9509592A (zh) |
CA (1) | CA2204241A1 (zh) |
DE (1) | DE4439335A1 (zh) |
FI (1) | FI971863A0 (zh) |
HU (1) | HUT77297A (zh) |
NO (1) | NO971767L (zh) |
WO (1) | WO1996014289A1 (zh) |
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US5866711A (en) * | 1996-09-13 | 1999-02-02 | E. I. Du Pont De Nemours And Company | Fluorocyanate and fluorocarbamate monomers and polymers thereof |
JPWO2004108662A1 (ja) * | 2003-05-15 | 2006-07-20 | クミアイ化学工業株式会社 | フェニルスルホニルカーバメイト誘導体及び農園芸用植物病害防除剤 |
CN116583541A (zh) * | 2021-09-24 | 2023-08-11 | 宁德时代新能源科技股份有限公司 | 粘结剂化合物、导电粘结剂及包含其的二次电池 |
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US3689662A (en) * | 1970-12-10 | 1972-09-05 | Wayne C Jaeschke | Nematocidel use of 3,4,4-trifluoro-3-butenylthio methylidene compounds |
US4748186A (en) * | 1986-06-30 | 1988-05-31 | Fmc Corporation | S-trifluorobutenyl derivatives and pesticidal uses thereof |
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1994
- 1994-11-04 DE DE4439335A patent/DE4439335A1/de not_active Withdrawn
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1995
- 1995-11-02 CN CN95197158A patent/CN1171775A/zh active Pending
- 1995-11-02 EP EP95937045A patent/EP0789683A1/de not_active Withdrawn
- 1995-11-02 WO PCT/EP1995/004298 patent/WO1996014289A1/de not_active Application Discontinuation
- 1995-11-02 JP JP8515039A patent/JPH10508592A/ja active Pending
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- 1995-11-02 AU AU39271/95A patent/AU3927195A/en not_active Abandoned
- 1995-11-02 CA CA002204241A patent/CA2204241A1/en not_active Abandoned
- 1995-11-02 HU HU9702041A patent/HUT77297A/hu unknown
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WO1996014289A1 (de) | 1996-05-17 |
HUT77297A (hu) | 1998-03-30 |
MX9703193A (es) | 1997-11-29 |
JPH10508592A (ja) | 1998-08-25 |
AU3927195A (en) | 1996-05-31 |
DE4439335A1 (de) | 1996-05-09 |
NO971767D0 (no) | 1997-04-17 |
NO971767L (no) | 1997-04-17 |
EP0789683A1 (de) | 1997-08-20 |
FI971863A (fi) | 1997-04-30 |
BR9509592A (pt) | 1997-09-30 |
CA2204241A1 (en) | 1996-05-17 |
FI971863A0 (fi) | 1997-04-30 |
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