CN1311780A - 取代的3-硫代氨基甲酰基吡唑类化合物 - Google Patents
取代的3-硫代氨基甲酰基吡唑类化合物 Download PDFInfo
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- CN1311780A CN1311780A CN99809285A CN99809285A CN1311780A CN 1311780 A CN1311780 A CN 1311780A CN 99809285 A CN99809285 A CN 99809285A CN 99809285 A CN99809285 A CN 99809285A CN 1311780 A CN1311780 A CN 1311780A
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- HQGBNXIKIHVWIR-UHFFFAOYSA-N 1h-pyrazole-5-carbothioamide Chemical class NC(=S)C=1C=CNN=1 HQGBNXIKIHVWIR-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 34
- -1 haloalkylthioalkyl Chemical group 0.000 claims description 139
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 117
- 125000001424 substituent group Chemical group 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 150000002367 halogens Chemical class 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 239000000460 chlorine Substances 0.000 claims description 36
- 229910052801 chlorine Inorganic materials 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 239000011737 fluorine Substances 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
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- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
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- 241001465754 Metazoa Species 0.000 claims description 14
- 239000005864 Sulphur Substances 0.000 claims description 14
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
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- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 5
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
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- 229910021419 crystalline silicon Inorganic materials 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 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 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
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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
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及通式(Ⅰ)的新的取代的3-硫代氨基甲酰基吡唑类化合物,其中m,n,R1,R2,R3和Ar具有说明书中给出的定义。本发明还涉及它们的制备方法和它们作为杀虫剂的用途。
Description
本发明涉及新的取代的3-硫代氨基甲酰基吡唑类化合物、它们的多种制备方法和它们作为杀虫剂的用途。
已知各种各样的取代的氨基吡唑对于抗害虫是高度有效的(参见例如WO97/22593,WO97/44340,EP295117,EP807668,EP738713,EP352944,EP201852,EP418016,EP659745,US5688966,US5631381,US5629335)。但是,特别是在某些害虫和/或低施用浓度情况下,先前技术的化合物的药效和/或持久性不完全在所有应用领域都令人满意。
因此,本发明提供通式(Ⅰ)的新的取代的3-硫代氨基甲酰基吡唑类化合物其中R1代表H2N-CS-,m代表0或1的数,n代表0,1或2的数,R2代表烷基,链烯基,炔烃基,氰基烷基,氰硫基烷基,硝基烷基,烷硫基烷基,烷基亚磺酰基烷基,烷基磺酰基烷基,卤代烷硫基烷基,卤代烷基亚磺酰基烷基,卤代烷基磺酰基烷基,链烯基硫基烷基,链烯基亚磺酰基烷基,链烯基磺酰基烷基,炔烃基硫基烷基,炔烃基亚磺酰基烷基,炔烃基磺酰基烷基,烷氧羰基烷基,卤代烷氧羰基烷基,烷氧羰基,链烯基氧基羰基,卤代烷氧羰基,烷基羰基,烷氧基烷基,卤代烷氧基烷基,烷氧基烷硫基烷基,烷氧基烷基亚磺酰基烷基,烷氧基烷基磺酰基烷基,卤代烷氧基烷硫基烷基,卤代烷氧基烷基亚磺酰基烷基,卤代烷氧基烷基磺酰基烷基,烷基氨基烷基,二烷基氨基烷基,三烷基甲硅烷基烷基;各自任选被取代的环烷基,环烯基或环烷基烷基;还代表芳基,杂芳基,芳基烷基,杂芳基烷基,芳基氧基烷基,芳基硫基烷基,芳基亚磺酰基烷基,芳基磺酰基烷基,芳基烷基氧基烷基,芳基烷基硫基烷基,芳基烷基亚磺酰基烷基或芳基烷基磺酰基烷基,这些基团各自任选在芳基部分或杂芳基部分被取代,R2在m=0情况下还代表氰硫基,卤素,硝基,氰基,羟基,卤代烷基,卤代链烯基,氯磺酰基,烷氧基,卤代烷氧基,链烯基氧基,卤代链烯基氧基,烷基羰基氧基,甲酰基,三烷基甲硅烷基乙炔基,任选被取代的芳基氧基或代表下面的基团之一:-NHR4,-NR4R5,-NHNH2,-CONH2,-CSNH2,-CONR4R5,-SO2NR4R5,-CR6=NOR7,-CH(OH)R8或-CH(CN)OR9,其中R4和R5各自独立地代表氢,氰基,烷基或者各自任选被取代的芳基或芳烷基,R6代表氢或烷基,R7代表氢,烷基或任选被取代的芳烷基,R8代表烷基或卤代烷基和R9代表烷基,R3代表氢,氨基,卤素或代表下面的基团之一:-NH-CO-R10,-NHR11,-OR12,-SR12或-NR13-CX-C(R14,R15,R16)其中R10代表烷基,卤代烷基,烷氧基烷基或者各自任选被取代的苯基,苯氧基或吡啶基,R11代表烷基,链烯基,炔烃基,甲酰基,烷基羰基,卤代烷基羰基或烷氧羰基,R12代表烷基,链烯基,炔烃基,任选被取代的芳烷基,二烷基氨基烷基或代表基团-P(=Y)(OR17)(SR18),其中R17和R18各自独立地代表烷基和Y代表氧或硫,R13代表氢,烷基,烷氧基烷基,炔丙基,烯丙基,烷氧羰基,烷基羰基,任选被取代的苄基或基团-CO-C(R14,R15,R16),R14代表氢,烷基,卤代烷基,卤素或任选被取代的苯基和R15代表氢,烷基,卤代烷基,卤素,卤代烷氧基烷基,烷硫基烷基,烷基亚磺酰基烷基,烷基磺酰基烷基,烷氧基(烷氧基)r烷基,其中r=0-4,羟基,烷氧羰基烷基或烷氧基,或R14和R15与它们连接的碳原子一起代表任选地具有至多2个杂原子的3-至7-元环系和R16代表羟基,烷氧基,卤代烷氧基,烷氧基(烷氧基)p,其中p=1-4,或卤代烷氧基(烷氧基)q,其中q=1-4,和X代表氧或硫,和Ar代表各自任选被取代的苯基或吡啶基。
此外,发现进行下面的反应时得到式(Ⅰ)的新的取代的3-硫代氨基甲酰基吡唑类化合物:a)如果适当在反应助剂存在下和如果适当在稀释剂存在下,使式(Ⅱ)的3-氰基吡唑衍生物与硫化氢反应其中Ar,R2,R3,m和n如上定义,或者b)如果适当在稀释剂存在下和如果适当在反应助剂存在下,使式(Ⅲ)的3-硫代氨基甲酰基吡唑衍生物与式(Ⅳ)的烃硫基(sulphenyl)卤反应其中Ar如上定义和R3-1代表下面的基团之一:-NHR11,-OR12或-NR13-CX-C(R14,R15,R16),其中R10至R16和X如上定义,
Hal-S-R2 (Ⅳ)其中R2如上定义和Hal代表卤素,特别是氯或溴,或者c)如果适当在稀释剂存在下和如果适当在催化剂存在下,用氧化剂氧化根据方法(a)或(b)获得的式(Ⅰa)的3-硫代氨基甲酰基吡唑衍生物其中Ar,R2和R3如上定义。
最后发现,新的式(Ⅰ)的3-硫代氨基甲酰基吡唑衍生物具有卓越的生物性能并且特别适合用于防治动物害虫,特别是农业,林业和储藏品保护以及材料保护和卫生领域遇到的昆虫,蛛形纲和线虫。
式(Ⅰ)提供了根据本发明的化合物的一般定义。
下面详细说明上文和下文提到的结构式中的基团的优选取代基或范围。R2优选代表(C1-C6)-烷基,(C2-C6)-链烯基,(C2-C6)-炔烃基,氰基-(C1-C4)-烷基,氰硫基-(C1-C4)-烷基,硝基-(C1-C4)-烷基,(C1-C6)-烷硫基-(C1-C4)-烷基,(C1-C6)-烷基亚磺酰基-(C1-C4)-烷基,(C1-C6)-烷基磺酰基-(C1-C4)-烷基,具有1-6个卤原子的(C1-C4)-卤代烷硫基-(C1-C4)-烷基,具有1-6个卤原子的(C1-C4)-卤代烷基亚磺酰基-(C1-C4)-烷基,具有1-6个卤原子的(C1-C4)-卤代烷基磺酰基-(C1-C4)-烷基,(C2-C6)-链烯基硫基-(C1-C4)-烷基,(C2-C6)-链烯基亚磺酰基-(C1-C4)-烷基,(C2-C6)-链烯基磺酰基-(C1-C4)-烷基,(C2-C6)-炔烃基硫基-(C1-C4)-烷基,(C2-C6)-炔烃基亚磺酰基-(C1-C4)-烷基,(C2-C6)-炔烃基磺酰基-(C1-C4)-烷基,(C1-C4)-烷氧羰基-(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷氧羰基-(C1-C4)-烷基,(C1-C6)-烷氧-羰基,(C1-C6)-烷基羰基,(C1-C6)-烷氧基-(C1-C4)-烷基,具有1-6个卤原子的(C1-C6)-卤代烷氧基-(C1-C4)-烷基,(C1-C4)-烷氧基-(C1-C4)-烷硫基-(C1-C4)-烷基,(C1-C4)-烷氧基-(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基,烷氧基-(C1-C4)-烷基磺酰基-(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷氧基-(C1-C4)-烷硫基-(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷氧基-(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷氧基-(C1-C4)-烷基磺酰基-(C1-C4)-烷基,(C1-C4)-烷基氨基-(C1-C4)-烷基,二-(C1-C4)-烷基氨基-(C1-C4)-烷基,三-(C1-C4)-烷基甲硅烷基-(C1-C4)-烷基;或者代表各自任选被相同或不同的取代基一-至五-取代的(C3-C6)-环烷基,(C5-C6)-环烯基或(C3-C6)-环烷基-(C1-C2)-烷基,其中可能的取代基是:(C1-C4)-烷基,(C1-C4)-烷氧基,卤素,具有1-5个卤原子的(C1-C4)-卤代烷基和具有1-5个卤原子的(C1-C4)-卤代烷氧基;或者代表苯基,苯基-(C1-C2)-烷基,苯氧基-(C1-C2)-烷基,苯硫基-(C1-C2)-烷基,苯基亚磺酰基-(C1-C2)-烷基,苯基磺酰基-(C1-C2)-烷基,苯基-(C1-C2)-烷氧基-(C1-C2)-烷基,苯基-(C1-C2)-烷硫基-(C1-C2)-烷基,苯基-(C1-C2)-烷基亚磺酰基-(C1-C2)-烷基,苯基-(C1-C2)-烷基磺酰基-(C1-C2)-烷基,吡啶基或吡啶基-(C1-C2)-烷基,这些基团各自任选被相同或不同的取代基一-至三-取代,其中可能的苯基或吡啶基取代基是:卤素,(C1-C6)-烷基,(C2-C6)-链烯基,(C1-C6)-烷氧基,(C2-C6)-链烯基氧基,(C1-C4)-烷硫基,(C1-C4)-烷基亚磺酰基,(C1-C4)-烷基磺酰基;各自具有1-5个卤原子的(C1-C6)-卤代烷基,(C2-C4)-卤代链烯基,(C1-C4)-卤代烷氧基,(C1-C4)-卤代烷硫基,(C1-C4)-卤代烷基亚磺酰基和(C1-C4)-卤代烷基磺酰基;氰基,硝基,羟基,肼基,(C1-C6)-二烷基肼基,氨基,(C1-C6)-烷基氨基,二-(C1-C6)-烷基氨基,(C1-C6)-烷基亚氨基,(C1-C4)-烷基羰基,(C1-C4)-烷基羰基氧基;各自任选被一至三个相同或不同的选自卤素,(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷基,(C1-C4)-烷氧基和各自具有1-5个卤原子的(C1-C4)-卤代烷氧基和(C1-C4)-卤代烷硫基的取代基取代的苯基或苯氧基,SF5或者基团
其中R’和R”各自独立地代表氢或(C1-C6)-烷基和Z代表-CO或-SO2,R2在m=O情况下还优选代表氰硫基,氯,溴,碘,硝基,氰基,羟基,氯磺酰基,(C1-C4)-烷氧基,(C2-C4)-链烯基氧基;各自具有1-5个卤原子的(C1-C4)-卤代烷基,(C2-C4)-卤代链烯基,(C1-C4)-卤代烷氧基和(C2-C4)-卤代链烯基氧基;(C1-C4)-烷基羰基氧基,甲酰基,三-(C1-C4)-烷基甲硅烷基乙炔基;或者代表任选被相同或不同的取代基一-至五-取代的苯氧基,其中可能的取代基是上文对于R2已经提到的苯基取代基,以及优选代表下面的基团之一:-NHR4,-NR4R5,-NHNH2,-CONH2,-CSNH2,-CONR4R5,-SO2NR4R5,-CR6=NOR7,-CH(OH)R8或-CH(CN)OR9,其中R4和R5各自独立地优选代表氢,氰基,(C1-C4)-烷基或者代表各自任选被相同或不同的取代基一-至五-取代的苯基或苄基,其中可能的取代基是上文对于R2已经提到的苯基取代基,R6优选代表氢或(C1-C4)-烷基,R7优选代表氢,(C1-C4)-烷基或任选被相同或不同的取代基一-至五-取代的苄基,其中可能的取代基是上文对于R2已经提到的苯基取代基,R8优选代表(C1-C4)-烷基或具有1-5个卤原子的(C1-C4)-卤代烷基,R9优选代表(C1-C4)-烷基,R3优选代表氢,氨基,氯,溴,碘或代表下面的基团之一:-NH-CO-R10,-NHR11,-OR12,-SR12或-NR13-CX-C(R14,R15,R16)其中R10优选代表(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷基,(C1-C4)-烷氧基-(C1-C4)-烷基或者代表各自任选被相同或不同的取代基一-至五-取代的苯基,苯氧基或吡啶基,其中可能的取代基是上文对于R2已经提到的苯基取代基,R11优选代表(C1-C4)-烷基,(C2-C4)-链烯基,(C2-C4)-炔烃基,甲酰基,(C1-C4)-烷基羰基,具有1-5个卤原子的(C1-C4)-卤代烷基羰基或(C1-C4)-烷氧羰基,R12优选代表(C1-C4)-烷基,(C2-C4)-链烯基,(C2-C4)-炔烃基,二-(C1-C4)-烷基氨基-(C1-C4)-烷基;任选被相同或不同的取代基一-至五-取代的苯基-(C1-C2)-烷基,其中可能的取代基是上文对于R2已经提到的苯基取代基,或代表基团-P(=Y)(OR17)(SR18),其中R17和R18各自独立地优选代表(C1-C4)-烷基和Y代表氧或硫,R13优选代表氢,(C1-C4)-烷基,(C1-C4)-烷氧基-(C1-C4)-烷基,炔丙基,烯丙基,(C1-C4)-烷氧羰基,(C1-C4)-烷基羰基,代表任选被相同或不同的取代基一-至五-取代的苄基,其中可能的取代基是上文对于R2已经提到的苯基取代基,或代表基团-CO-C(R14,R15,R16),R14优选代表氢,(C1-C4)-烷基,卤素,具有1-5个卤原子的(C1-C4)-卤代烷基,或代表任选被相同或不同的取代基一-至五-取代的苯基,其中可能的取代基是上文对于R2已经提到的苯基取代基,R15优选代表氢,(C1-C4)-烷基,卤素,各自具有1-5个卤原子的(C1-C4)-卤代烷基和(C1-C4)-卤代烷氧基-(C1-C4)-烷基,(C1-C4)-烷硫基-(C1-C4)-烷基,(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基,(C1-C4)-烷基磺酰基-(C1-C4)-烷基,(C1-C4)-烷氧基-[(C1-C4)-烷氧基]r-(C1-C4)-烷基,其中r=0-2,羟基,(C1-C4)-烷氧羰基-(C1-C4)-烷基和(C1-C4)-烷氧基,或R14和R15与它们连接的碳原子一起优选代表任选地具有至多2个相同或不同的例如O,S或N原子的杂原子的5-至6或7-元环系,R16优选代表羟基,(C1-C4)-烷氧基,具有1-5个卤原子的(C1-C4)-卤代烷氧基或(C1-C4)-烷氧基-[(C1-C4)-烷氧基]q,其中q=1或2,X优选代表氧或硫,和Ar优选代表苯基或吡啶基,其各自任选被相同或不同的取代基一-至三-取代,其中可能的取代基各自是上文对于R2已经提到的苯基取代基。R2特别优选代表(C1-C4)-烷基,(C2-C4)-链烯基,(C2-C4)-炔烃基,氰基-(C1-C2)-烷基,氰硫基-(C1-C2)-烷基,硝基-(C1-C2)-烷基,(C1-C4)-烷硫基-(C1-C2)-烷基,(C1-C4)-烷基亚磺酰基-(C1-C2)-烷基,(C1-C4)-烷基磺酰基-(C1-C2)-烷基,具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷硫基-(C1-C2)-烷基,各具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基亚磺酰基-(C1-C2)-烷基和(C1-C2)-卤代烷基磺酰基-(C1-C2)-烷基,(C2-C4)-链烯基硫基-(C1-C2)-烷基,(C2-C4)-炔烃基硫基-(C1-C2)-烷基,(C1-C2)-烷氧羰基-(C1-C2)-烷基,具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷氧羰基-(C1-C2)-烷基,(C1-C4)-烷氧羰基,(C1-C4)-烷基羰基,(C1-C4)-烷氧基-(C1-C2)-烷基,(C1-C2)-烷氧基-(C1-C2)-烷硫基-(C1-C2)-烷基,具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷氧基-(C1-C2)-烷硫基-(C1-C2)-烷基,(C1-C2)-烷基氨基-(C1-C2)-烷基,二-(C1-C2)-烷基氨基-(C1-C2)-烷基;代表环丙基,环戊基和环己基,这些基团各自任选被相同或不同的取代基一-至三取代,其中可能的取代基是:甲基,乙基,甲氧基,乙氧基,氟,氯,溴,三氟甲基和三氟甲氧基;和代表苯基,苄基,苯氧基甲基,苯氧基乙基,苯硫基甲基,苯硫基乙基,苄基氧基甲基,苄基硫基甲基,吡啶基或吡啶基甲基,这些基团各自任选被相同或不同的取代基一-至三-取代,其中可能的苯基或吡啶基取代基是:氟,氯,溴,(C1-C4)-烷基,烯丙基,(C1-C4)-烷氧基,烯丙基氧基,(C1-C2)-烷硫基,各自具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基或(C1-C2)-卤代烷氧基或(C1-C2)-卤代烷硫基;氰基,硝基,羟基,肼基,二甲基肼基,氨基,甲基氨基,二甲基氨基,亚氨基甲基,(C1-C2)-烷基羰基,(C1-C2)-烷基羰基氧基;各自任选被相同或不同的选自氟,氯,溴,甲基,乙基,甲氧基,三氟甲基,三氟甲氧基和三氟甲硫基的取代基一-至二-取代的苯基或苯氧基;SF5或者基团其中R’和R”各自独立地代表氢或(C1-C4)-烷基和Z代表-CO或-SO2,R2在m=0情况下还特别优选代表SCN,氯,碘,硝基,氰基,羟基,氯磺酰基,(C1-C2)-烷氧基,烯丙基氧基;各自具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基或(C1-C2)-卤代烷氧基;(C1-C2)-烷基羰基氧基,甲酰基,-C≡C-Si(CH3)3;代表任选被相同或不同的取代基一-至二-取代的苯氧基,其中可能的取代基是上文对于R2已经提到的取代基;还代表-CONH2,-CSNH2,-CON(CH3)2,-CON(C2H5)2,-CH=NOCH3,-CH=NOC2H5,-CH(CH3)=NOCH3和-CH(OH)CF3,R3特别优选代表氢,氨基,氯,(C1-C4)-烷基氨基,还代表基团-NH-CO-R10,其中R10特别优选代表(C1-C4)-烷基,具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基,还代表各自任选被相同或不同的取代基一-至二-取代的苯基和苯氧基,其中可能的取代基是上文对于R2已经提到的苯基取代基,Ar特别优选代表苯基或吡啶基,它们各自任选被相同或不同的选自下面的取代基一-至三-取代:氟,氯,溴,各自具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基和(C1-C2)-卤代烷氧基和(C1-C2)-卤代烷硫基和(C1-C2)-卤代烷基亚磺酰基和(C1-C2)-卤代烷基磺酰基,(C1-C2)-烷基,(C1-C2)-烷氧基,肼基,二甲基肼基,氨基,甲基氨基,二甲基氨基,氰基,SF5或者基团其中R’和R”各自独立地代表氢或(C1-C4)-烷基和Z代表CO或SO2。R2非常特别优选代表CH3,C2H5,-CH2-CH=CH2,-C≡CH,-CH2-C≡CH,-CH2-CN,-CH2-SCN,-CH2-NO2,-CH2-S-CH3,-CH2-S-C2H5,-CH2CH2-S-CH3,-CH2CH2-S-C2H5,-CH2-SO-C2H5,-CH2-SO2-C2H5,-CH2-S-CF3,CH2-SO-CF3,CH2-SO2-CF3,-CH2-S-CH2-CH=CH2,-CH2-S-CH2-C≡CH,-CH2-CO-OCH3,-CH2-CO-OC2H5,-(CH2)2-CO-OCH3,-(CH2)2-CO-OC2H5,-CH2-CO-OCF3,-CO-OCH3,-CO-OC2H5,-CO-CH3,-CO-C2H5,-CH2-OCH3,-CH2-OC2H5,-CH2-S-CH2CH2-O-C2H5,-CH2-S-CH2CH2-O-CH2CF3,-CH2-NHC2H5,-CH2CH2-N(CH3)2,-CH2CH2-N(C2H5)2,环丙基,和代表苄基,苄基氧基甲基,苄基硫基甲基,苯氧基甲基,苯氧基乙基,苯硫基甲基或苯硫基乙基,这些基团各自任选被相同或不同的的取代基一-至三取代,其中可能的苯基取代基各自是:氟,氯,三氟甲基,三氟甲氧基,三氟甲硫基,甲氧基,肼基,二甲基肼基,氨基,甲基氨基,二甲基氨基,氰基,甲硫基,-CONH2,-CSNH2,苯基,氯苯基,氟苯基,二氯苯基,苯氧基,氯代苯氧基,氟代苯氧基和二氯苯氧基,R2在m=0的情况下另外非常特别优选代表SCN,氯,碘,硝基,氰基,-OCH3,-CF3,-OCF3,-O-COCH3,-CSNH2,-CON(CH3)2,-CH=NOCH3和-CH(OH)CF3,R3非常特别优选代表氢,氨基,氯,-NHCH3,-NHC2H5,-NH-CO-CF3,
和
Ar非常特别优选代表苯基或2-吡啶基,它们各自任选被相同或不同的选自下列的取代基二-或三取代:F,Cl,Br,CF3,OCF3,SCF3,SOCF3,SO2CF3,OCH2CF3,CH3或SF5。
上述的或优选的基团定义或说明适用于终产物和相应的起始物和中间体。这些基团定义可以根据需要相互组合,即包括各优选范围之间的组合。
根据本发明优选给出式(Ⅰ)的化合物,其包含上述优选(优选的)定义的组合。
根据本发明特别优选给出式(Ⅰ)的化合物,其包含上述特别优选定义的组合。
根据本发明非常特别优选给出式(Ⅰ)的化合物,其包含上述非常特别优选定义的组合。
在上文和下文的基团定义中,烃基,例如烷基或链烯基-也包括与杂原子结合的情况,例如在烷氧基或烷硫基中-只要有可能,各自是直链或支链的。
表1-14列出了新的取代的3-硫代氨基甲酰基吡唑的实例:表1表1的化合物相当于其中的通式(ⅠB),使用下面的取代基的组合: 表2表2包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表3表3包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表4表4包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表5表5包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表6表6包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表7表7包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表8表8包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表9表9包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表10表10包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表11表11包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表12表12包括其中的通式(ⅠB)的化合物,表1中列出的取代基的组合适用于R2,n和R3。表13表13的化合物相当于其中的通式(ⅠB),使用下面的取代基的组合:表14表14的化合物相当于其中的通式(ⅠC),使用下面的取代基的组合:
使用,例如,1-(2,6-二氯-4-三氟甲基苯基)-3-硫代氨基甲酰基-5-乙基氨基-吡唑和乙硫基氯为起始物,则根据本发明的方法(b)的反应过程可以用下面的反应式表示:
用作进行根据本发明的方法(a)的起始物的式(Ⅱ)的3-氰基吡唑衍生物是已知的(参见,例如,EPO295117,GB2308365,WO98/04530和WO97/07102)和/或可以类似于已知方法制备。
用作进行根据本发明的方法(b)的起始物的式(Ⅲ)的3-硫代氨基甲酰基吡唑衍生物是新的,并且其中一些构成本申请人早期申请的一部分主题(参见1 996年4月12日的德国专利申请19650197)。
式(Ⅴ)的3-氰基吡唑是已知的(参见EP659745)和/或它们可以通过一般常规方法获得。
还用作根据本发明方法(b)的起始物的式(Ⅳ)的烃硫基卤一般是已知的有机化学的化合物,和/或可以通过已知的方法制备。
用作根据本发明方法(c)的起始物的式(Ⅰa)的3-硫代氨基甲酰基吡唑衍生物是根据本发明的化合物。
优选使用稀释剂进行根据本发明的方法(a)。合适的稀释剂实际上是所有惰性有机溶剂。这些优选包括脂肪族和芳香族的,任选被卤化的烃,例如戊烷,己烷,庚烷,环己烷,石油醚,挥发油,石油英,苯,甲苯,二甲苯,二氯甲烷,二氯乙烯,氯仿,四氯甲烷,氯苯和邻-二氯苯;醚类,例如乙醚和丁醚,乙二醇二甲基醚和二甘醇二甲基醚,四氢呋喃和二噁烷;酮类,例如丙酮,甲基乙基酮,甲基异丙基酮或甲基异丁基酮;酯类,例如乙酸甲酯或乙酸乙酯;腈类,例如乙腈或丙腈;酰胺类,例如二甲基甲酰胺,二甲基乙酰胺和N-甲基吡咯烷酮,还有二甲亚砜;环丁砜或六甲基磷酸三酰胺。
适合用作根据本发明的方法(a)的反应助剂是这类反应常规使用的所有的碱。优选使用碱性氮化合物,例如三甲基胺,三乙基胺,三丙基胺,三丁基胺,二异丁基胺,二环己基胺,乙基二异丙基胺,乙基二环己基胺,N,N-二甲基苄基胺,N,N-二甲基苯胺,吡啶,2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、2-乙基-、4-乙基-和5-乙基-2-甲基-吡啶,1,5-二氮杂双环[4,3,0]-壬-5-烯(DBN),1,8-二氮杂双环[5,4,0]-十一-7-烯(DBU)和1,4-二氮杂双环-[2,2,2]-辛烷(DABCO),也可以使用过量的反应助剂作为稀释剂。
在根据本发明方法(a)中,反应温度可以在一个相当大的范围内变化。一般情况下,该方法在0℃和100℃之间的温度下进行,优选在10℃和80℃之间的温度下进行。
一般情况下,根据本发明的方法(a)在大气压下进行。但是也可以在加压或减压下操作。
在进行本发明方法(a)时,一般过量使用硫化氢。反应一般在合适的稀释剂中在碱性氮化合物存在下进行。通过常规方法进行后处理(参见制备实施例)。
用于进行根据本发明的方法(b)的合适的稀释剂是惰性有机溶剂。这些特别包括脂肪族,脂环族或芳香族的,任选被卤化的烃,例如汽油,苯,甲苯,二甲苯,氯苯,石油醚,己烷,环己烷,二氯甲烷,氯仿,四氯化碳;醚类,例如乙醚,二噁烷,四氢呋喃或乙二醇二甲基醚和二甘醇二甲基醚或二乙基醚;酮类,例如丙酮或丁酮;腈类,例如乙腈或丙腈;酰胺类,例如二甲基甲酰胺,二甲基乙酰胺,N-甲基甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酸三酰胺;酯类,例如乙酸乙酯,亚砜,例如二甲基亚砜,或者酸,例如乙酸。
如果适当,根据本发明的方法(b)可以在反应助剂存在下进行。合适的反应助剂是所有常规的无机或有机碱。这些包括例如,碱金属氢氧化物,例如氢氧化钠和氢氧化钾,碱土金属碳酸盐或碳酸氢盐,例如碳酸钠,碳酸钾或碳酸氢钠,还有叔胺,例如三乙胺,N,N-二甲基苯胺,吡啶,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)。
在进行根据本发明方法(b)时,反应温度可以在一个相当大的范围内变化。一般情况下,该方法在-20℃和+120℃之间的温度下进行,优选在0℃和+50℃之间的温度下进行。
在进行本发明方法(b)时,对于每摩尔的式(Ⅲ)的4-取代的1-芳基吡唑一般使用1.0-2.5摩尔,优选1.0-1.5摩尔的式(Ⅳ)的烃硫基卤和如果适当,1.0-2.5摩尔,优选1.0-1.5摩尔的反应助剂。一般通过常规方法进行反应和后处理以及反应产物的分离。
用于进行根据本发明方法(c)的合适的氧化剂是常规用于硫氧化作用的所有氧化剂。特别合适的是过氧化氢,有机过酸,例如过乙酸,间-氯过苯甲酸,和对硝基过苯甲酸或大气氧。
用于进行根据本发明方法(c)的合适的稀释剂同样是惰性有机溶剂。优选使用烃,例如汽油,苯,甲苯,己烷或石油醚;氯代烃,例如二氯甲烷,1,2-二氯乙烷,氯仿,四氯化碳或氯苯;醚类,例如乙醚,二噁烷或四氢呋喃;羧酸,例如乙酸或丙酸,或者偶极非质子惰性溶剂,例如乙腈,丙酮,乙酸乙酯或二甲基甲酰胺。
如果适当,根据本发明方法(c)可以在酸结合剂存在下进行。合适的酸结合剂是常规使用的所有有机和无机酸结合剂。优选使用碱金属或碱土金属的氢氧化物,乙酸盐或碳酸盐,例如氢氧化钙,氢氧化钠,乙酸钠或碳酸钠。
如果适当,根据本发明方法(c)可以在合适的催化剂存在下进行。合适的催化剂是常规用于这样的硫氧化作用的所有金属盐催化剂。可以提到的例子是钼酸铵和钨酸钠。
在进行根据本发明方法(c)时,反应温度可以在一个相当大的范围内变化。一般情况下,该方法在-20℃和+70℃之间的温度下进行,优选在0℃和+50℃之间的温度下进行。
在进行本发明方法(c)时,如果硫的氧化作用在亚砜阶段终止时,对于每摩尔的式(Ⅰa)的化合物一般使用0.8-1.2摩尔,优选等当量的氧化剂。对于氧化为砜,则对于每摩尔的式(Ⅰa)的化合物一般使用1.8-3.0摩尔,优选2倍摩尔量的氧化剂。通过常规方法进行反应和后处理以及终产物的分离。
任选地,在稀释剂例如特别是醇(优选乙醇)/水混合物存在下,在-80℃和50℃之间的温度下,优选-50℃和室温之间的温度下,优选以等摩尔量使用式(Ⅵ)的卤化物,如果适当也可以稍微过量,使式(Ⅰb)的3-硫代氨基甲酰基-4-氰硫基-吡唑以一般常规方式与式(Ⅵ)的卤化物反应,也可以获得根据本发明的式(Ⅰa)的取代的3-硫代氨基甲酰基吡唑其中Ar和R3如上定义,
Hal-R2 (Ⅵ)其中Hal和R2如上定义。
这些活性化合物适于防治动物害虫,特别是农业、林业、储藏品保护和材料保护以及卫生领域所遇到昆虫、蛛形纲和线虫。它们具有好的植物耐受性并且对温血动物毒性低。它们可以优选用作植物保护剂。它们对正常敏感性和抗性种类都有活性,并且在害虫发育的所有阶段或部分阶段有效。上述害虫包括:等足目(Isopoda),例如Oniscus aselluse,鼠妇(Armadillidiumvulgare)和Porcellio scaber。多足纲目(Diplopoda),例如Blaniulus gutttulatus。唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.)。综合纲目(Symphyla),例如Scutigerella immaculata。缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina)。弹尾目(Collembola),例如Onychiurus armatus。直翅目(Orthoptera),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),灶马(Acheta domesticus),蝼蛄属(Gryllotalpa spp.),热带飞蝗(Locusta migratoriamigratorioides),长额负蝗(Melanoplus differentialis)和Schistocerca gregaria。革翅目(Dermaptera),例如欧洲球螋(Forficula auricularia)。等翅目(Isoptera),例如白蚁属(Reticulitermes spp.)。虱目(Anoplura),例如头虱(Pediculus humanus corporis),盲虱属(Haematopinus spp.)和长额虱(Linognathus spp.)。食毛目(Mallophaga),例如羽虱属(Trichodectes spp.)和Damalinea spp.。缨翅目(Thysanoptera),例如温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thrips tabaci)。异翅亚目(Heteroptera),例如褐盾蝽属(Eurygasterspp.),Dysdercus intermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimex lectularius),Rhodnius prolixus和吸血猎蝽属(Triatoma spp.)。同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisiatabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphisgossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphis fabae),Aphis pomi,苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterusarundinis),Phylloxera vastatrix,Pemphigus spp.,Macrosiphumavenae,瘤额蚜(Myzus spp.),忽布瘤额蚜(Phorodon humuli),粟缢管蚜(Rhopasiphum padi),叶蝉属(Empoasca spp.),Euscelisbilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecanium corni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphax striatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiella aurantii),Aspidiotus hederae,粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。鳞翅目(Lepidoptera),例如,红铃虫(Pectinophora gossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletis blancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutella maculipennis),天幕毛虫(Malacosomaneustria),Euproctis chrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrix thurberiella),Phyllocnisticitrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Feltia spp.),埃及金刚钻(Earias insulana),夜蛾属(Heliothisspp.),甜菜夜蛾(Spodoptera exigua),甘蓝夜蛾(Mamestrabrassicae),Panolis flammea,斜纹夜蛾(Spodoptera litura),夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsa pomonella),粉蝶属(Pieris spp.),螟(Chilospp.),Pyrausta nubilalis,Ephestia kuehniella,大黄螟(Galleria mellonella),袋衣蛾(Tineola bisselliella),网衣蛾(Tinea pellionella),褐织叶蛾(Hofmannophilapseudospretella),Cacoecia podana,Capua reticulana,云杉卷叶蛾(Choristoneura fumiferana),葡萄果蠹蛾(Clysiaambiguella),茶黄卷叶蛾(Homona magnanima)和栎绿卷叶蛾(Tortrix viridana)。鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,Bruchidius obtectus,大豆象(Acanthoscelides obtectus),家天牛(Hylotrupes bajulus),Agelastica alni,甲铃薯甲虫(Leptinotarsa decemlineata),Phaedon cochleariae,叶甲属(Diabrotica spp.),油菜兰跳甲(Psylliodes chrysocephala),墨西哥豆瓢虫(Epilachnavarivestis),Atomaria spp.,锯胸谷盗(Oryzaephilussurinamens),象甲属(Anthonomus spp.),米象属(Sitophilusspp.),Otiorrhynchus sulcatus,香蕉蛛基象甲(Cosmopolitessordidus),Ceuthorrhynchus assimilis,苜宿叶象甲(Hyperapostica),皮蠹属(Dermestes spp.),皮蠹属(Trogoderma spp.),皮蠹属(Anthrenus spp.),黑皮蠹(Attagenus spp.),粉蠹(Lyctusspp.),Meligethes aeneus,蛛甲属(Ptinus spp.),金黄蛛甲(Niptus hdoleucus),麦蛛甲(Gibbium psylliodes),拟谷稻属(Tribolium spp.),黄粉甲(Tenebrio molitor),扣甲属(Agriotesspp.),金针虫属(Conoderus spp.),Melolontha meiolontha,六月金龟子(Amphimallon solstitialis)和Costelytra zealandica。膜翅属(Hymenoptera),例如锯角叶蜂属(Diprion spp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomoriumpharaonis),和胡蜂(Vespa spp.)。双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anophelesspp.),库蚊(Culex spp.),黄猩猩果蝇(Drosophila melanogaster),家蝇(Musca spp.),厩蝇(Fannia spp.),红头丽蝇(Calliphoraerythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyia spp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,螫蝇属(Stomoxys spp.),鼻蝇属(Oestrus spp.),皮蝇属(Hydodermaspp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinella frit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyia hyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacus oleae)和欧洲大蚊(Tipula paludosa)。蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis),和角叶蚤属(Ceratophyllus spp.)。蛛形纲(Arachnida),例如Sciopio maurus,黑寡妇球腹蛛(Latrodectus mactans)。蜱螨目(Acarina),例如,粗脚粉螨(Acarus siro),隐喙蚍(Argasspp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssusgallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilus spp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyomma spp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptesspp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.),和红叶螨属(Tetranychus spp.)。
寄生植物线虫包括短体线虫属(Pratylenchus spp.),相似穿孔线虫(Radopholus similis),起绒草茎线虫(Dityl enchus dipsaci),半穿刺线虫(Tylenchulus semipenetrans),异皮线虫属(Heteroderaspp.),异皮线虫(Globodera spp.),根结线虫属(Meloidogyne spp.),滑刃线虫属(Aphelenchoides spp.),长针线虫属(Longodorus spp.),剑线虫属(Xiphinema spp.)和毛刺线虫属(Trichodorus spp.)。
本发明式(Ⅰ)的化合物特别具有高的杀昆虫活性。其可以特别成功地用来防治植物病原体害虫,例如抗草地粘虫(Spodopterafrugiperda)毛虫和桃蚜(Myzus persicae)。
活性化合物可以配制成常规制剂,例如溶液、乳液、可湿性粉末、悬浮剂、粉剂、粉尘剂、糊剂、可溶性粉末、颗粒剂、混悬乳油、浸有活性化合物的天然的和合成的材料,和包裹在聚合物中的细微胶囊。
这些型剂用已知的方式生产,例如,通过将活性化合物与扩充剂即液体溶剂和/或固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
如果使用的扩充剂是水,则也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳香族化合物和氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂肪烃类,如环己烷或石蜡,例如矿物油馏份,矿物油和植物油,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,如二甲基甲酰胺和二甲亚砜,以及水。
作为固体载体合适的有:
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;用于颗粒剂的适合的固体载体有:例如压碎和破碎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:例如锯木屑、椰壳、玉米穗轴和烟茎;合适的乳化剂和/或起泡剂有: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,芳基磺酸盐以及蛋白水解产物;合适的分散剂有: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,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可以使用染料,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。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
本发明活性化合物可以以其商售制剂以及由这些制剂制备的使用形式,作为与其它活性化合物的混合物存在,所述其它活性化合物是例如杀昆虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂,生长调节剂或除草剂。杀昆虫剂特别包括例如磷酸酯,氨基甲酸酯,羧酸酯,氯代烃,苯基脲和通过微生物制备的物质等等。
混合物中共成分的例子是下面的化合物:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoprim,敌菌灵,戊环唑,嘧菌酯,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacril-isobutyl,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌,多菌灵,萎锈灵,carvon,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,嘧菌环胺,酯菌胺,
咪菌威,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨噁唑酮,
克瘟散,氟环唑,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,腈苯唑,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,氟喹唑,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,炔呋菊酯,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine,iminoctadinealbesilate,iminoctadine triacetate),iodocarb,种菌唑,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,叶菌唑,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫代氨基甲酸镍,酞菌酯,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,嘧霉胺,咯喹酮,氯吡呋醚,
quinconazole,五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,调环烯,氟嘧唑,噻菌灵,噻菌腈,噻呋酰胺,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,灭菌唑,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
腈菌胺,代森锌,福美锌,还有
Dagger G,
OK-8705,
OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-a-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-a-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基}-氨基甲酸异丙酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮-0-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘代甲基)-磺酰基]-4-甲基-苯,
1-[[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2’,6’-二溴-2-甲基-4'-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-N-碳酰苯胺,
2,6-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
2,6-二氯-5-(甲硫基)-4-嘧啶基-硫代氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘代-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-a-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴代甲基)戊烷二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异氰硫基甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈,
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲烷胺,
8-羟基喹啉硫酸盐,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)-氧基]-2,5-噻吩二羧酸酯,
顺-1-(4-氯代苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉]盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
碳酸氢钾,
甲烷四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯代乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯代乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯代-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲烷亚氨酰胺,
N-甲酰基-N-羟基-DL-丙氨酸钠盐,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯,
O-甲基S-苯基-苯基丙基硫代氨基磷酸酯,
S-甲基1,2,3-苯并噻二唑-7-硫代甲酸酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃-3’-酮,
杀细菌剂:
bromopol,双氯酚,氯甲基吡啶,二甲基二硫代氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/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,双虫脒,avermectin,AZ60541,azadirachtin,azinphos-A,保棉磷,三唑锡,
苏云金杆菌,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,CGA157419,CGA184699,chloethocarb,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,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯-β,氯氟氰菊酯,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,酚线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,甲基毒虫畏,敌噁磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,氯氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,氟虫腈,吡氟禾草灵,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,
HCH,庚烯磷,氟铃脲,噻螨酮,
吡虫啉,异稻瘟净,氯唑磷,异丙胺磷,叶蝉散,噁唑磷,ivermectin,
氯氟氰菊酯,虱螨脲,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,moxidectin,
二溴磷,NC184,NI25,烯啶虫胺,
氧乐果,杀线威,亚砜吸磷,异砜磷,
对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,甲基嘧啶磷,嘧啶磷-A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,吡蚜酮,吡唑硫磷,pyradaphenthion,pyresmethrin,除虫菊酯,哒螨酮,嘧螨醚,蚊蝇醚,
喹硫磷,
RH5992,
蔬果磷,sebufos,氟硅菊酯,治螟硫磷,甲丙硫磷,
虫酰肼,吡螨胺,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效磷,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,
芽灭多,XMC,灭杀威,YI5301/5302,zetamethrin。
也可能是与其它已知的活性化合物例如除草剂或与化肥和生长调节剂的混合物。
当作为杀虫剂时,根据本发明的活性化合物还可以以其商售制剂和以由这些制剂制备的使用形式作为与增效剂的混合物存在。增效剂是提高活性化合物作用而其自身不必要有活性的化合物。
由商售制剂制备的使用形式的活性化合物含量可以在宽范围内变化。使用形式的活性化合物的浓度可以是0.0000001-95%重量活性化合物,优选0.0001-1%重量。
以适于这些使用形式的常规方式应用这些化合物。
当用来杀卫生领域害虫和储存产品害虫时,这些活性化合物特征在于对木材和粘土有极好的有后效的作用,以及对用石灰处理过的物质上的碱有好的稳定性。
本发明活性化合物不仅对杀植物,卫生领域和储存产品害虫有活性,而且还用于兽药领域,杀动物寄生虫(外寄生虫),例如硬蜱,软蜱,马痒螨,恙螨,蝇(叮和吮),寄生蝇幼虫,虱,头虱,皮革虱和蚤。这样的寄生虫包括:
虱目(Anolpurida),例如,血虱属(Haematopinus spp.),长颚虱(Linognathus spp.),虱属(Pediculus spp.),阴虱属(Phtirusspp.),和管虱属(Solenopotes spp.)。
食毛目咬虱(Mallophagida)和Amblycerina及Ischnocerina亚目,例如毛羽虱属(Trimenopon spp.),Menopon spp.,巨羽虱属(Trinoton spp.),牛羽虱属(Bovicola spp.),Werneckiella spp.,Lepikentron spp.,Damalina spp.,Trichodectes spp.,Felcolaspp.。
双翅目(Diptera)和长角亚目(Nematocerina)和Brachycerina亚目,例如伊蚊(Aedes spp.),斑按蚊属(Anopheles spp.),库蚊(Culex spp.),蚋属(Simulium spp.),全毛真蚋(Eusimulium spp.),白蛉(Phlebotomus spp.),罗蛉属(Lutzomyia spp.),库蠓(Culicoides spp.),斑虻(Chrysops spp.),瘤虻(Hybomitra spp),Atylotus spp.,虻属(Tabanus spp.),麻虻属(Haematopotaspp.),Philipomyia spp.,Braul a spp.,Musca spp.,齿股蝇属(Hydrotuea spp.),螫蝇(Stomoxys spp.),Haematobia spp.,Morellia spp.,厕蝇(Fannia spp.),Glossina spp.,Calliphoraspp.,Lucilia spp.,Chrysomyia spp.,Wohlfahrtia spp.,别麻蝇(Sarcophaga spp.),Oestrus spp.,皮蝇(Hypoderma spp.),Gasterophilus spp.,虱蝇(Hippobosca spp.),Lipoptena spp.和Melophagus spp.。蚤目(Siphonapterida),例如,蚤属(Pulex spp.),Ctenocephalides spp.,鼠蚤(Xenopsylla spp.),和角叶蚤(Ceratophyllus spp.)。
异翅亚目(Heteropterida),例如,臭虫属(Cimex spp.),吸血猎蝽属(Triatoma spp.),Rhodnius spp.,和全圆蝽属(Panstrongylusspp.)。
非蠊目(Blattarida),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),德国小蠊(Blattela germanica)和非蠊属(Supella spp.)。
螨亚类(Acarida)和后胸气门目(Metastigmata)和中胸气门目(Mesostigmata),例如,隐喙蜱属(Argas spp.),喙蜱属(Ornithodorus spp.),耳残喙蜱(Otabius spp.),硬蜱(Ixodesspp.),花蜱属(Amblyomma spp.),牛蜱属(Boophilus spp.),矩头蜱(Dermacentor spp.),Haemophysalis spp.,璃眼蜱(Hyalommaspp.),头蜱属(Rhipicephalus spp.),鸡皮刺螨(Dermanyssusspp.),瑞立绦虫(Raillietia spp.),Pneumonyssus spp.,Sternostoma spp.,和Varroa spp.。
Actinedida(恙螨亚目,Prostigmata)和Acaridida(Astigmata),例如Acarapis spp.,姬螯螨属(Cheyletiella spp.),Ornithocheyletia spp.,Myobia spp.,疥螨(Psorergates spp.),蠕形螨(Demodex spp.),恙螨(Trombicula spp.),Listrophorusspp.,粗脚粉螨(Acarus spp.),酪螨(Tyrophagus spp.),嗜木螨(Caloglyphus spp.),Hypodectes spp.,翼衣螨属(Pterolichusspp.),恙螨(Psoroptes spp.),恙螨(Chorioptes spp.),Otodectes spp.,疥螨(Sarcoptes spp.),Notoedres spp.,足螨(Knemidocoptes spp.,),Cytodites spp.,和Laminosioptesspp.。
例如它们表现出抗蝇(舍蝇,Musca domestca)的好的活性,抗铜绿蝇(Lucilla cuprina)蝇幼虫的发育抑制活性和抗猫蚤(Ctenocephalides felis)和抗蜱(微小牛蜱,Boophilus microplus)的好的活性,也以抑制产卵的形式。
本发明式(Ⅰ)的活性化合物也适于防治侵染农业生产家畜的节肢动物门,所述家畜是例如牛,绵羊,山羊,马,猪,驴,骆驼,水牛,兔子,鸡,火鸡,鸭,鹅和蜜蜂,其它宠物,例如狗,猫,笼养的鸟和鱼缸养殖鱼,和称之为实验室动物的动物,例如仓鼠,豚鼠,大鼠和小鼠。通过防治这些节肢动物门,可以避免家畜死亡并且避免产品量的减少(产品例如肉,奶,毛,皮革,蛋,蜂蜜等),因此通过使用本发明活性化合物可以实现更经济更简单的动物饲养。
在兽药领域,本发明活性化合物以已知方式通过肠给药,例如以片剂,胶囊,饮剂,顿服药,颗粒剂,糊剂,巨丸剂,送食法和栓剂的形式;通过肠胃外给药,例如通过注射(肌内,皮下,静脉内,腹膜内等),埋入,通过鼻给药,通过以例如浸渍或浸浴,喷洒,倒施和点施,洗用和撒粉的形式皮肤使用,也可以借助于含有活性化合物的用模子做的物品,例如颈圈,耳饰,尾饰,腿带,笼头,标记物等而使用。
当对牲畜,家禽,宠物等使用时,本发明式(Ⅰ)活性化合物可以作为以1-80%重量比的量含有活性化合物的制剂(例如粉末剂,乳剂,可流动性组合物)而被使用,直接使用或者稀释100-10000倍后使用,或者可以以化学浴形式使用。
另外,还发现本发明式(Ⅰ)的化合物还具有杀破坏工业材料的昆虫的强的杀昆虫作用。
作为优选例子可以提到下面的昆虫,但是不受此限制:
甲虫,例如
家天牛(Hylotrupes bajulus),Chlorophorus pilosis,家具窃蠹(Anobium punctatum),Xestobium rufovillosum,Ptilinuspecticornis,Dendrobium pertinex,Ernobius mollis,Priobiumcarpini,欧洲竹粉蠹(Lyctus brunneus),Lyctus africanus,平颈粉蠹(Lyctus planicollis),Lyctus linearis,Lyctuspubescens,Trogoxylon aequale,Minthes rugicollis,小蠹虫种(Xyleborus spec.),Tryptodendron spec.,Apate monachus,Bostrychus capucins,Heterobostrychus branneus,Simoxylonspec.,和竹长蠹(Dinoderus minutus)。
膜翅目(Hymenopterans),例如
钢青小树蜂(Sirex juvencus),枞大树蜂(Urocerus gigas),Urocerus gigas taignus和Urocerus augur。
白蚁,例如
Kalotermes flavicollis,Cryptotermesbrevis,Heterotermes indicola,Reticulitermes flavipes,Reticulitermes santonensis,Reticulitermes lucifugus,澳洲白蚁(Mastotermes darwiniensis),Zootermopsis nevadensis和台湾家白蚁(Coptotermes formosanus)。
Bristle-tail,例如西洋衣鱼(Lepisma saccharina)。
本发明中所涉及的工业材料理解为非生命材料,例如,优选塑料,粘合剂,胶料,纸和纸板,皮革,木材和木材加工产品以及涂料。
要非常特别优选保护使不受昆虫侵染的材料是木材和木材加工产品。
可以用本发明试剂或含有这样一种试剂的混合物保护的木材和木材加工产品理解为是,例如建筑木材加工品,木梁,铁轨枕木,建桥木料,码头,木制运载工具,箱子,制模板,容器,电线杆,木桶,木窗,木门,胶合板,颗粒板,接合物,或者在房屋建筑或细木工行业很普通使用的木产品。
活性化合物可以以本身使用,以乳油形式或者一般的常规制剂使用,例如粉末剂,颗粒剂,溶液,混悬剂,乳剂或糊剂。
提到的制剂可以以本身已知的方法制备,例如通过混合活性化合物和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,如果合适,干燥剂和UV稳定剂和,如果合适,着色剂和颜料和还有其它加工助剂。
用于保护木料和木制品的杀昆虫组合物或浓缩物含有0.0001-95%重量比浓度的本发明活性化合物,特别是0.001-60%重量比。
使用的组合物或浓缩物的量取决于害虫的物种和发生,并取决于基质。施用的最佳比例每种情况下可以通过试验系列来确定。但是,一般情况下,使用以要保护的材料为基础的0.0001-20%重量,优选0.001-10%重量的活性化合物足够了。
使用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或油或象油一样的低挥发性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/或水和,如果合适,乳化剂和/或湿润剂。
优选使用的有机化学溶剂是具有大于35的挥发数和高于30℃,优选高于45℃的闪点的油或象油一样的溶剂。作为具有低挥发性并且在水中不溶解的这类油和象油一样的溶剂而使用的物质是合适的矿物油或其芳香烃级分,或者含有矿物油的溶剂混合物,优选石油溶剂,石油和/或烷基苯。
有利地使用沸点范围是170-220℃的矿物油,沸点范围是170-220℃的石油溶剂,沸点范围是250-350℃的锭子油,沸点范围是160-280℃的石油和芳香烃,松节油精油等。
在优选的实施方案中,使用沸点范围是180-210℃的液体脂肪烃或者沸点范围是180-220℃的芳香烃和脂肪烃的高沸点混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
具有大于35的挥发数和高于30℃,优选高于45℃闪点的低挥发性有机油或象油一样的溶剂可以部分替换成高挥发性或中等挥发性的有机化学溶剂,前提是该溶剂混合物也具有大于35的挥发数和高于30℃,优选高于45℃的闪点,并且杀昆虫剂/杀真菌剂混合物在该溶剂混合物中是可溶解的或可乳化的。
根据优选的实施方案,部分有机化学溶剂或溶剂混合物替换成脂肪族极性有机化学溶剂或溶剂混合物。优选使用具有羟基和/或酯基和/或醚基的脂肪族有机化学溶剂,例如乙二醇醚,酯等。
本发明中使用的有机化学粘合剂是本身已知的合成树脂和/或粘合干燥油,它们是水可稀释的和/或在使用的有机化学溶剂中是可溶解的或可分散的或可乳化的,特别是粘合剂由下面的物质组成或者含有下面的物质:丙烯酸树脂,乙烯树脂,例如聚乙酸乙烯酯,聚酯树脂,缩聚物或加聚物树脂,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,例如茚/苯并呋喃树脂,有机硅树脂,干燥植物油和/或干燥油和/或以天然和/或合成树脂为基础的物理干燥粘合剂。
作为粘合剂使用的合成树脂可以以乳液,分散液或溶液的形式使用。最多10%重量的沥青或沥青状物质也可以作为粘合剂使用。另外,可以使用本身已知的着色剂,颜料,防水剂,气味掩蔽物质和抑制剂或防腐蚀剂等。
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的醇酸树脂,和/或一种干燥植物油作为有机化学粘合剂。根据本发明,优选使用油含量大于45%重量,优选50-68%重量的醇酸树脂。
上面提到的粘合剂的所有或部分粘合剂可以替换成固定剂(混合物)或增塑剂(混合物)。这些添加剂是为了防止活性化合物的挥发以及结晶或沉淀。优选替换0.01-30%的粘合剂(以使用的100%粘合剂为基础)。
增塑剂来自邻苯二甲酸酯类,例如邻苯二甲酸二丁酯,邻苯二甲酸二辛酯或邻苯二甲酸苄酯丁酯,磷酸酯类,例如磷酸三丁酯,己二酸酯类,例如己二酸二-(2-乙基己基)酯,硬脂酸酯类,例如硬脂酸丁酯或硬脂酸戊酯,油酸酯类,例如油酸丁酯,甘油醚或较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,例如二苯酮或二苯乙酮(ethylenebenzophenone)。
可能的溶剂或稀释剂特别是水,如果合适,作为与一种或几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作用是通过大量的工业化浸渍方法实现的,例如真空,双倍真空或加压方法。
如果合适,即用型组合物可以另外含有其它的杀虫剂和,如果合适,另外一种或几种杀真菌剂。
可能的另外的混合组分优选是W094/29268中提到的杀虫剂和杀真菌剂。该文献中提到的化合物明确地引入本申请作为参考。
可以提到的非常特别优选的混合组分是杀虫剂,例如毒死稗,辛硫磷,氟硅菊酯,甲体氯氰菊酯,氟氯氰菊酯,氯氰菊酯,溴氰菊酯,氯菊酯,吡虫啉,NI-25,氟虫脲,氟铃脲和杀虫隆,和杀真菌剂,例如氟环唑(epoxyconazole),己唑醇,戊环唑,环丙唑,戊唑醇,环唑醇,叶菌唑,抑霉唑,苯氟磺胺,甲苯氟磺胺,氨基甲酸3-碘代-2-丙炔基丁酯,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从下面的实施例说明。制备实施例
将0.8g(2.1mmol)的5-氨基-3-氰基-4-乙硫基-1-(2,6-二氯-4-三氟甲基-苯基)-吡唑(参见EP295117)溶解于30ml无水吡啶和2ml三乙胺中。室温下,缓慢通入硫化氢,温度升至28℃。60分钟后,反应完全。浓缩反应混合物,并且通过硅胶色谱纯化粗产物(环己烷/乙酸乙酯:2/1)。
得到0.4g(理论量的46%)5-氨基-4-乙硫基-1-(2,6-二氯-4-三氟甲基-苯基)-3-硫代氨基甲酰基-吡唑,熔点101℃。
类似于实施例1和/或根据对制备的一般性说明获得下面表A中列出的式(Ⅰ)的化合物:表A
[1H-NMR:于DMSO中,使用TMS为内标,δ单位ppm]应用实施例实施例A瘤额蚜(Myzus)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
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和乳化剂混合,用水将浓缩物稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理被桃蚜(Myzus persicae)严重侵染的甘蓝叶(Brassica oleracea)。
一定时间后,测定杀死百分率。100%表示所有的蚜虫都已经被杀死;0%表示没有杀死一只蚜虫。
在该项试验中,以0.1%例示的活性化合物浓度,各自6天后,例如制备实施例1的化合物表现出90%的杀死率,制备实施例2和8的化合物表现出100%的杀死率。
实施例B草地粘虫(Spodoptera frugiperda)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
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和乳化剂混合,用水将浓缩物稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),然后在叶子还湿润的时候使草地粘虫(Spodoptera frugiperda)毛虫群居其上。
一定时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
在该项试验中,以0.1%例示的活性化合物浓度,7天后,例如制备实施例2的化合物表现出85%的杀死率。
实施例C用蝇(舍蝇,Musca domestca)试验试验动物:舍蝇成虫,Reichswald品种(OP,SP,氨基甲酸酯抗性)溶剂:二甲亚砜
将20mg的活性化合物溶解于1ml二甲亚砜中,通过用蒸馏水稀释制备稀浓度。
用移液管将2ml该活性化合物制剂移至相应尺寸的玻璃皿上的滤纸圆片(直径9.5cm)上。滤纸圆片干燥后,将25只试验动物转移到玻璃皿中后覆盖。
1,3,5,24和48小时后,测定该活性化合物制剂的活性。100%表示所有的蝇都已经被杀死;0%表示没有杀死一只蝇。
在该项试验中,以100ppm例示的活性化合物浓度,例如制备实施例2的化合物表现出100%的活性。
实施例D蝇幼虫试验/发育抑制活性试验动物: 铜绿蝇(Lucilia cuprina)幼虫溶剂: 二甲亚砜
将20mg的活性化合物溶解于1ml二甲亚砜中,通过用蒸馏水稀释制备稀浓度。
向盛有大约1cm3马肉和0.5ml活性化合物制剂的试管中加入大约20只铜绿蝇幼虫。24和48小时后,测定活性化合物的活性。将试管转移放置在底部覆盖沙子的杯中。又过了2天后,取出试管并且计数蛹数。
通过未处理对照物发育时间的1.5倍时间后孵化的蝇的数目评价活性化合物制剂的活性。100%表示没有孵化出蝇;0%表示所有的蝇正常孵化。
在该试验中,以100ppm例示的活性化合物浓度,例如制备实施例1和2的化合物表现出100%的活性。
实施例E微小牛蜱(Boophilus microplus)抗性试验/SP-抗性Parkhurst品种试验动物:自身吸食充足的雌性成虫溶剂: 二甲亚砜
将20mg的活性化合物溶解于1ml二甲亚砜中,通过用蒸馏水稀释制备稀浓度。
10只微小牛蜱抗性成虫在要试验的活性化合物的制剂中浸入1分钟,将动物转移到塑料杯中并且放置于气候化室内,然后测定杀死率。
100%表示所有的蜱都已经被杀死;0%表示没有杀死一只蜱。
在该项试验中,以100ppm例示的活性化合物浓度,例如制备实施例1的化合物表现出100%的活性。
实施例F微小牛蜱(Boophilus microplus)抗性试验/SP-抗性Parkhurst品种试验动物:自身吸食充足的雌性成虫溶剂: 二甲亚砜
将20mg的活性化合物溶解于1ml二甲亚砜中,通过用蒸馏水稀释制备稀浓度。
该项试验重复5次。将1μl溶液注入腹部,将动物转移到玻璃皿中并且放置于气候化室内,7天后,对于卵的状况的抑制进行活性对照。100%的活性表示没有一只蜱产卵。
在该项试验中,以20μg/动物例示的活性化合物浓度,例如制备实施例1和2的化合物表现出100%的活性。
实施例G用猫蚤试验/口服给药试验动物:猫蚤(Ctenocephalides felis)成虫溶剂:二甲亚砜(DMSO)
为了制备合适的制剂,用20mg活性化合物和1ml的DMSO制备合适的活性化合物溶液。向3ml柠檬酸化牛血中加入15μl该制剂。
将10只禁食的成虫蚤(Ctenocephalides felis,“Georgi”品种)置于顶部和底部用纱布密封的室(直径3.2cm)中。将底部用parafilm密封的金属圆筒置于该室之上。圆筒中盛有3ml血/活性化合物制剂,蚤可以通过parafilm膜摄食。血液温热至37℃,而蚤室温度调节到25℃。对照物与相同体积的DMSO混合不加入化合物。该项试验重复三次。
28小时后,测定死亡百分率%(=死亡的蚤)。
在该项试验中,以100ppm例示的活性化合物浓度,例如制备实施例2的化合物表现出100%的活性。
实施例H猿叶甲(Phaedon)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
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和乳化剂混合,用含有乳化剂的水将浓缩物稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并且在叶子还湿润的时候用辣根猿叶甲(Phaedon cochleariae)幼虫侵染。
一定时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
在该项试验中,以0.1%例示的活性化合物浓度,7天后,例如制备实施例1-9的化合物表现出100%的杀死率。
Claims (8)
1.通式(Ⅰ)的取代的3-硫代氨基甲酰基吡唑类化合物其中R1代表H2N-CS-,m代表0或1的数,n代表0,1或2的数,R2代表烷基,链烯基,炔烃基,氰基烷基,氰硫基烷基,硝基烷基,烷硫基烷基,烷基亚磺酰基烷基,烷基磺酰基烷基,卤代烷硫基烷基,卤代烷基亚磺酰基烷基,卤代烷基磺酰基烷基,链烯基硫基烷基,链烯基亚磺酰基烷基,链烯基磺酰基烷基,炔烃基硫基烷基,炔烃基亚磺酰基烷基,炔烃基磺酰基烷基,烷氧羰基烷基,卤代烷氧羰基烷基,烷氧羰基,链烯基氧基羰基,卤代烷氧羰基,烷基羰基,烷氧基烷基,卤代烷氧基烷基,烷氧基烷硫基烷基,烷氧基烷基亚磺酰基烷基,烷氧基烷基磺酰基烷基,卤代烷氧基烷硫基烷基,卤代烷氧基烷基亚磺酰基烷基,卤代烷氧基烷基磺酰基烷基,烷基氨基烷基,二烷基氨基烷基,三烷基甲硅烷基烷基;各自任选被取代的环烷基,环烯基或环烷基烷基;还代表芳基,杂芳基,芳基烷基,杂芳基烷基,芳基氧基烷基,芳基硫基烷基,芳基亚磺酰基烷基,芳基磺酰基烷基,芳基烷基氧基烷基,芳基烷基硫基烷基,芳基烷基亚磺酰基烷基或芳基烷基磺酰基烷基,这些基团各自任选在芳基部分或杂芳基部分被取代,R2在m=0情况下还代表氰硫基,卤素,硝基,氰基,羟基,卤代烷基,卤代链烯基,氯磺酰基,烷氧基,卤代烷氧基,链烯基氧基,卤代链烯基氧基,烷基羰基氧基,甲酰基,三烷基甲硅烷基乙炔基,任选被取代的芳基氧基或代表下面的基团之一:
-NHR4,-NR4R5,-NHNH2,-CONH2,-CSNH2,-CONR4R5,-SO2NR4R5,-CR6=NOR7,-CH(OH)R8或-CH(CN)OR9,其中R4和R5各自独立地代表氢,氰基,烷基或者各自任选被取代的芳基或芳烷基,R6代表氢或烷基,R7代表氢,烷基或任选被取代的芳烷基,R8代表烷基或卤代烷基和R9代表烷基,R3代表氢,氨基,卤素或代表下面的基团之一:-NH-CO-R10,-NHR11,-OR12,-SR12或-NR13-CX-C(R14,R15,R16)其中R10代表烷基,卤代烷基,烷氧基烷基或者各自任选被取代的苯基,苯氧基或吡啶基,R11代表烷基,链烯基,炔烃基,甲酰基,烷基羰基,卤代烷基羰基或烷氧羰基,R12代表烷基,链烯基,炔烃基,任选被取代的芳烷基,二烷基氨基烷基或代表基团-P(=Y)(OR17)(SR18),其中R17和R18各自独立地代表烷基和Y代表氧或硫,R13代表氢,烷基,烷氧基烷基,炔丙基,烯丙基,烷氧羰基,烷基羰基,任选被取代的苄基或基团-CO-C(R14,R15,R16),R14代表氢,烷基,卤代烷基,卤素或任选被取代的苯基和R15代表氢,烷基,卤代烷基,卤素,卤代烷氧基烷基,烷硫基烷基,烷基亚磺酰基烷基,烷基磺酰基烷基,烷氧基(烷氧基)r烷基,其中r=0-4,羟基,烷氧羰基烷基或烷氧基,或R14和R16与它们连接的碳原子一起代表任选地具有至多2个杂原子的3-至7-元环系和R16代表羟基,烷氧基,卤代烷氧基,烷氧基(烷氧基)p,其中p=1-4,或卤代烷氧基(烷氧基)q,其中q=1-4,和X代表氧或硫,和Ar代表各自任选被取代的苯基或吡啶基。
2.根据权利要求1的取代的3-硫代氨基甲酰基吡唑类化合物,其特征在于R1代表H2N-CS-,m代表0或1的数,n代表0,1或2的数,R2代表(C1-C6)-烷基,(C2-C6)-链烯基,(C2-C6)-炔烃基,氰基-(C1-C4)-烷基,氰硫基-(C1-C4)-烷基,硝基-(C1-C4)-烷基,(C1-C6)-烷硫基-(C1-C4)-烷基,(C1-C6)-烷基亚磺酰基-(C1-C4)-烷基,(C1-C6)-烷基磺酰基-(C1-C4)-烷基,具有1-6个卤原子的(C1-C4)-卤代烷硫基-(C1-C4)-烷基,具有1-6个卤原子的(C1-C4)-卤代烷基亚磺酰基-(C1-C4)-烷基,具有1-6个卤原子的(C1-C4)-卤代烷基磺酰基-(C1-C4)-烷基,(C2-C6)-链烯基硫基-(C1-C4)-烷基,(C2-C6)-链烯基亚磺酰基-(C1-C4)-烷基,(C2-C6)-链烯基磺酰基-(C1-C4)-烷基,(C2-C6)-炔烃基硫基-(C1-C4)-烷基,(C2-C6)-炔烃基亚磺酰基-(C1-C4)-烷基,(C2-C6)-炔烃基磺酰基-(C1-C4)-烷基,(C1-C4)-烷氧羰基-(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷氧羰基-(C1-C4)-烷基,(C1-C6)-烷氧-羰基,(C1-C6)-烷基羰基,(C1-C6)-烷氧基-(C1-C4)-烷基,具有1-6个卤原子的(C1-C6)-卤代烷氧基-(C1-C4)-烷基,(C1-C4)-烷氧基-(C1-C4)-烷硫基-(C1-C4)-烷基,(C1-C4)-烷氧基-(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基,烷氧基-(C1-C4)-烷基磺酰基-(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷氧基-(C1-C4)-烷硫基-(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷氧基-(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷氧基-(C1-C4)-烷基磺酰基-(C1-C4)-烷基,(C1-C4)-烷基氨基-(C1-C4)-烷基,二-(C1-C4)-烷基氨基-(C1-C4)-烷基,三-(C1-C4)-烷基甲硅烷基-(C1-C4)-烷基;或者代表各自任选被相同或不同的取代基一-至五-取代的(C3-C6)-环烷基,(C5-C6)-环烯基或(C3-C6)-环烷基-(C1-C2)-烷基,其中可能的取代基是:(C1-C4)-烷基,(C1-C4)-烷氧基,卤素,具有1-5个卤原子的(C1-C4)-卤代烷基和具有1-5个卤原子的(C1-C4)-卤代烷氧基;或者代表苯基,苯基-(C1-C2)-烷基,苯氧基-(C1-C2)-烷基,苯硫基-(C1-C2)-烷基,苯基亚磺酰基-(C1-C2)-烷基,苯基磺酰基-(C1-C2)-烷基,苯基-(C1-C2)-烷氧基-(C1-C2)-烷基,苯基-(C1-C2)-烷硫基-(C1-C2)-烷基,苯基-(C1-C2)-烷基亚磺酰基-(C1-C2)-烷基,苯基-(C1-C2)-烷基磺酰基-(C1-C2)-烷基,吡啶基或吡啶基-(C1-C2)-烷基,这些基团各自任选被相同或不同的取代基一-至三-取代,其中可能的苯基或吡啶基取代基是:卤素,(C1-C6)-烷基,(C2-C6)-链烯基,(C1-C6)-烷氧基,(C2-C6)-链烯基氧基,(C1-C4)-烷硫基,(C1-C4)-烷基亚磺酰基,(C1-C4)-烷基磺酰基;各自具有1-5个卤原子的(C1-C6)-卤代烷基,(C2-C4)-卤代链烯基,(C1-C4)-卤代烷氧基,(C1-C4)-卤代烷硫基,(C1-C4)-卤代烷基亚磺酰基和(C1-C4)-卤代烷基磺酰基;氰基,硝基,羟基,肼基,(C1-C6)-二烷基肼基,氨基,(C1-C6)-烷基氨基,二-(C1-C6)-烷基氨基,(C1-C6)-烷基亚氨基,(C1-C4)-烷基羰基,(C1-C4)-烷基羰基氧基;各自任选被相同或不同的选自卤素,(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷基,(C1-C4)-烷氧基和各自具有1-5个卤原子的(C1-C4)-卤代烷氧基和(C1-C4)-卤代烷硫基的取代基一至三取代取代的苯基或苯氧基,SF5或者基团
其中R’和R”各自独立地代表氢或(C1-C6)-烷基和Z代表-CO或-SO2,R2在m=0情况下还代表氰硫基,氯,溴,碘,硝基,氰基,羟基,氯磺酰基,(C1-C4)-烷氧基,(C2-C4)-链烯基氧基;各自具有1-5个卤原子的(C1-C4)-卤代烷基,(C2-C4)-卤代链烯基,(C1-C4)-卤代烷氧基和(C2-C4)-卤代链烯基氧基;(C1-C4)-烷基羰基氧基,甲酰基,三-(C1-C4)-烷基甲硅烷基乙炔基或者代表任选被相同或不同的取代基一-至五-取代的苯氧基,其中可能的取代基是上文对于R2已经提到的苯基取代基,或代表下面的基团之一:-NHR4,-NR4R5,-NHNH2,-CONH2,-CSNH2,-CONR4R5,-SO2NE4R5,-CR6=NOR7,-CH(OH)R8或-CH(CN)OR9,其中R4和R5各自独立地代表氢,氰基,(C1-C4)-烷基或者代表各自任选被相同或不同的取代基一-至五-取代的苯基或苄基,其中可能的取代基是上文对于R2已经提到的苯基取代基,R6代表氢或(C1-C4)-烷基,R7代表氢,(C1-C4)-烷基或任选被相同或不同的取代基一-至五-取代的苄基,其中可能的取代基是上文对于R2已经提到的苯基取代基,R8代表(C1-C4)-烷基或具有1-5个卤原子的(C1-C4)-卤代烷基,R9代表(C1-C4)-烷基,R3代表氢,氨基,氯,溴,碘或代表下面的基团之一:-NH-CO-R10,-NHR11,-OR12,-SR12或-NR13-CX-C(R14,R15,R16)其中R10代表(C1-C4)-烷基,具有1-5个卤原子的(C1-C4)-卤代烷基,(C1-C4)-烷氧基-(C1-C4)-烷基或者代表各自任选被相同或不同的取代基一-至五-取代的苯基,苯氧基或吡啶基,其中可能的取代基是上文对于R2已经提到的苯基取代基,R11代表(C1-C4)-烷基,(C2-C4)-链烯基,(C2-C4)-炔烃基,甲酰基,(C1-C4)-烷基羰基,具有1-5个卤原子的(C1-C4)-卤代烷基羰基或(C1-C4)-烷氧羰基,R12代表(C1-C4)-烷基,(C2-C4)-链烯基,(C2-C4)-炔烃基,二-(C1-C4)-烷基氨基-(C1-C4)-烷基;任选被相同或不同的取代基一-至五-取代的苯基-(C1-C2)-烷基,其中可能的取代基是上文对于R2已经提到的苯基取代基,或代表基团-P(=Y)(OR17)(SR18),其中R17和R18各自独立地代表(C1-C4)-烷基和Y代表氧或硫,R18代表氢,(C1-C4)-烷基,(C1-C4)-烷氧基-(C1-C4)-烷基,炔丙基,烯丙基,(C1-C4)-烷氧羰基,(C1-C4)-烷基羰基;或者代表苄基,其任选被相同或不同的取代基一-至五-取代,其中可能的取代基是上文对于R2已经提到的苯基取代基,或代表基团-CO-C(R14,R15,R16),R14代表氢,(C1-C4)-烷基,卤素,具有1-5个卤原子的(C1-C4)-卤代烷基,或代表任选被相同或不同的取代基一-至五-取代的苯基,其中可能的取代基是上文对于R2已经提到的苯基取代基,R15代表氢,(C1-C4)-烷基,卤素,各自具有1-5个卤原子的(C1-C4)-卤代烷基和(C1-C4)-卤代烷氧基-(C1-C4)-烷基,(C1-C4)-烷硫基-(C1-C4)-烷基,(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基,(C1-C4)-烷基磺酰基-(C1-C4)-烷基,(C1-C4)-烷氧基-[(C1-C4)-烷氧基]r-(C1-C4)-烷基,其中r=0-2,羟基,(C1-C4)-烷氧羰基-(C1-C4)-烷基和(C1-C4)-烷氧基,或R14和R15与它们连接的碳原子一起代表任选地具有至多2个相同或不同的如O,S或N原子的杂原子的5-至6或7-元环系,R16代表羟基,(C1-C4)-烷氧基,具有1-5个卤原子的(C1-C4)-卤代烷氧基或(C1-C4)-烷氧基-[(C1-C4)-烷氧基]q,其中q=1或2,X代表氧或硫,和Ar代表苯基或吡啶基,其各自任选被相同或不同的取代基一-至三-取代,其中可能的取代基各自是上文对于R2已经提到的苯基取代基。
3.根据权利要求1的取代的3-硫代氨基甲酰基吡唑类化合物,其特征在于R1代表H2N-CS-,m代表0或1的数,n代表0,1或2的数,R2代表(C1-C4)-烷基,(C2-C4)-链烯基,(C2-C4)-炔烃基,氰基-(C1-C2)-烷基,氰硫基-(C1-C2)-烷基,硝基-(C1-C2)-烷基,(C1-C4)-烷硫基-(C1-C2)-烷基,(C1-C4)-烷基亚磺酰基-(C1-C2)-烷基,(C1-C4)-烷基磺酰基-(C1-C2)-烷基,具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷硫基-(C1-C2)-烷基,各具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基亚磺酰基-(C1-C2)-烷基和(C1-C2)-卤代烷基磺酰基-(C1-C2)-烷基,(C2-C4)-链烯基硫基-(C1-C2)-烷基,(C2-C4)-炔烃基硫基-(C1-C2)-烷基,(C1-C2)-烷氧羰基-(C1-C2)-烷基,具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷氧羰基-(C1-C2)-烷基,(C1-C4)-烷氧羰基,(C1-C4)-烷基羰基,(C1-C4)-烷氧基-(C1-C2)-烷基,(C1-C2)-烷氧基-(C1-C2)-烷硫基-(C1-C2)-烷基,具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷氧基-(C1-C2)-烷硫基-(C1-C2)-烷基,(C1-C2)-烷基氨基-(C1-C2)-烷基,二-(C1-C2)-烷基氨基-(C1-C2)-烷基;或者代表环丙基,环戊基和环己基,这些基团各自任选被相同或不同的取代基一-至三取代,其中可能的取代基是:甲基,乙基,甲氧基,乙氧基,氟,氯,溴,三氟甲基和三氟甲氧基;或者代表苯基,苄基,苯氧基甲基,苯氧基乙基,苯硫基甲基,苯硫基乙基,苄基氧基甲基,苄基硫基甲基,吡啶基或吡啶基甲基,这些基团各自任选被相同或不同的取代基一-至三-取代,其中可能的苯基或吡啶基取代基是:氟,氯,溴,(C1-C4)-烷基,烯丙基,(C1-C4)-烷氧基,烯丙基氧基,(C1-C2)-烷硫基,各自具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基或(C1-C2)-卤代烷氧基或(C1-C2)-卤代烷硫基;氰基,硝基,羟基,肼基,二甲基肼基,氨基,甲基氨基,二甲基氨基,亚氨基甲基,(C1-C2)-烷基羰基,(C1-C2)-烷基羰基氧基;各自任选被相同或不同的选自氟,氯,溴,甲基,乙基,甲氧基,三氟甲基,三氟甲氧基和三氟甲硫基的取代基一-至二-取代的苯基或苯氧基;SF5或者基团其中R’和R”各自独立地代表氢或(C1-C4)-烷基和Z代表-CO或-SO2,R2在m=0情况下还代表SCN,氯,碘,硝基,氰基,羟基,氯磺酰基,(C1-C2)-烷氧基,烯丙基氧基;各自具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基或(C1-C2)-卤代烷氧基;(C1-C2)-烷基羰基氧基,甲酰基,-C≡C-Si(CH3)3;或者代表任选被相同或不同的取代基一-至二-取代的苯氧基,其中可能的取代基是上文对于R2已经提到的取代基;或者代表-CONH2,-CSNH2,-CON(CH3)2,-CON(C2H5)2,-CH=NOCH3,-CH=NOC2H5,-CH(CH3)=NOCH3和-CH(OH)CF3,R3代表氢,氨基,氯,(C1-C4)-烷基氨基,还代表基团-NH-CO-R10,其中R10代表(C1-C4)-烷基,具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基,还代表各自任选被相同或不同的取代基一-至二-取代的苯基和苯氧基,其中可能的取代基是上文对于R2已经提到的苯基取代基,Ar代表苯基或吡啶基,它们各自任选被相同或不同的选自下面的取代基一-至三-取代:氟,氯,溴;各自具有1-5个相同或不同的选自氟,氯和溴的卤原子的(C1-C2)-卤代烷基和(C1-C2)-卤代烷氧基和(C1-C2)-卤代烷硫基和(C1-C2)-卤代烷基亚磺酰基和(C1-C2)-卤代烷基磺酰基;(C1-C2)-烷基,(C1-C2)-烷氧基,肼基,二甲基肼基,氨基,甲基氨基,二甲基氨基,氰基,SF5或者基团其中R’和R”各自独立地代表氢或(C1-C4)-烷基和Z代表CO或SO2。
4.根据权利要求1的取代的3-硫代氨基甲酰基吡唑类化合物,特征在于R1代表H2N-CS-,m代表0或1的数,n代表0,1或2的数,R2代表CH3,C2H5,-CH2-CH=CH2,-C≡CH,-CH2-C≡CH,-CH2-CN,-CH2-SCN,-CH2-NO2,-CH2-S-CH3,-CH2-S-C2H5,-CH2CH2-S-CH3,-CH2CH2-S-C2H5,-CH2-SO-C2H5,-CH2-SO2-C2H5,-CH2-S-CF3,CH2-SO-CF3,CH2-SO2-CF3,-CH2-S-CH2-CH=CH2,-CH2-S-CH2-C≡CH,-CH2-CO-OCH3,-CH2-CO-OC2H5,-(CH2)2-CO-OCH3,-(CH2)2-CO-OC2H5,-CH2-CO-OCF3,-CO-OCH3,-CO-OC2H5,-CO-CH3,-CO-C2H5,-CH2-OCH3,-CH2-OC2H5,-CH2-S-CH2CH2-O-C2H5,-CH2-S-CH2CH2-O-CH2CF3,-CH2-NHC2H5,-CH2CH2-N(CH3)2,-CH2CH2-N(C2H5)2,环丙基;或者代表苄基,苄基氧基甲基,苄基硫基甲基,苯氧基甲基,苯氧基乙基,苯硫基甲基或苯硫基乙基,这些基团各自任选被相同或不同的的取代基一-至三取代,其中可能的苯基取代基各自是:氟,氯,三氟甲基,三氟甲氧基,三氟甲硫基,甲氧基,肼基,二甲基肼基,氨基,甲基氨基,二甲基氨基,氰基,甲硫基,-CONH2,-CSNH2,苯基,氯苯基,氟苯基,二氯苯基,苯氧基,氯代苯氧基,氟代苯氧基和二氯苯氧基,R2在m=0的情况下代表SCN,氯,碘,硝基,-OCH3,-CF3,-OCF3,-O-COCH3,
-CSNH2,-CON(CH3)2,-CH=NOCH3和-CH(OH)CF3,R3代表氢,氨基,氯,-NHCH3,-NHC2H5,-NH-CO-CF3,
和
Ar代表苯基或2-吡啶基,它们各自任选被相同或不同的选自F,Cl,Br,CF3,OCF3,SCF3,SOCF3,SO2CF3,OCH2CF3,CH3和SF5的取代基二-或三取代。
5.制备权利要求1-4任-项的取代的3-硫代氨基甲酰基吡唑类化合物的方法,特征在于a)如果适当在反应助剂存在下和如果适当在稀释剂存在下,使式(Ⅱ)的3-氰基吡唑衍生物与硫化氢反应其中Ar,R2,R3,m和n如权利要求1-4任一项中所定义,或者b)如果适当在稀释剂存在下和如果适当在反应助剂存在下,使式(Ⅲ)的3-硫代氨基甲酰基吡唑衍生物与式(Ⅳ)的烃硫基卤反应其中Ar如权利要求1-4任一项中所定义和R3-1代表下面的基团之一:-NHR11,-OR12或-NR13-CX-C(R14,R15,R16),其中R10至R16和X如权利要求1-4任一项中所定义,
7.权利要求1-4任一项的至少一种3-硫代氨基甲酰基吡唑类化合物防治动物害虫的用途。
8.杀虫剂组合物,特征在于含有至少一种权利要求1-4任一项的3-硫代氨基甲酰基吡唑类化合物和常规扩充剂。
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DE19824487.8 | 1998-06-02 | ||
DE19824487A DE19824487A1 (de) | 1998-06-02 | 1998-06-02 | Substituierte 3-Thiocarbamoylpyrazole |
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EP (1) | EP1084111A1 (zh) |
JP (1) | JP2002517382A (zh) |
KR (1) | KR20010043814A (zh) |
CN (1) | CN1311780A (zh) |
AU (1) | AU750089B2 (zh) |
BR (1) | BR9910896A (zh) |
CA (1) | CA2333715A1 (zh) |
DE (1) | DE19824487A1 (zh) |
HK (1) | HK1039937A1 (zh) |
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US20050234119A1 (en) * | 2004-04-16 | 2005-10-20 | Soll Mark D | Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals |
ES2444016T3 (es) | 2004-11-11 | 2014-02-21 | Merial Limited | Derivados de vinilaminopirazol como pesticidas |
DE102006061538A1 (de) | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Kombinationsprodukt zur Bekämpfung von Parasiten an Tieren |
DE102006061537A1 (de) | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Mittel zur Bekämpfung von Parasiten an Tieren |
WO2013000572A1 (de) | 2011-06-30 | 2013-01-03 | 2LUTION GmbH | Mittel zur bekämpfung von parasiten an tieren |
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TWI579274B (zh) | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備1-芳基-5-烷基吡唑化合物的改良方法 |
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DE3602728A1 (de) | 1985-05-17 | 1986-11-20 | Bayer Ag, 51373 Leverkusen | Schaedlingsbekaempfungsmittel auf basis von pyrazolderivaten |
US5547974A (en) | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
US5232940A (en) | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
GB8920521D0 (en) | 1989-09-11 | 1989-10-25 | May & Baker Ltd | New compositions of matter |
GB9120641D0 (en) * | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
DE4343832A1 (de) | 1993-12-22 | 1995-06-29 | Bayer Ag | Substituierte 1-Arylpyrazole |
US5629335A (en) * | 1995-04-07 | 1997-05-13 | Rhone-Poulenc Inc. | Pesticidal 1-arylpyrazole-3-carboximidothioic acid esters |
ATE189676T1 (de) | 1995-04-21 | 2000-02-15 | Rhone Poulenc Agrochimie | Herstellungsverfahren für 1- (chloroaryl)heterozyklische pestizide |
DK143796A (da) | 1995-12-20 | 1997-06-21 | Rhone Poulenc Agrochimie | Nye pesticider |
US5753030A (en) | 1996-05-13 | 1998-05-19 | Bayer Corporation | Crystal growth modifiers for perylene pigments |
US6037312A (en) | 1996-05-23 | 2000-03-14 | Idemitsu Kosan Co., Ltd. | Isoxazole derivatives |
US5688966A (en) | 1996-07-26 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Compounds and method for synthesizing sulfoindocyanine dyes |
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EP1084111A1 (de) | 2001-03-21 |
WO1999062886A1 (de) | 1999-12-09 |
CA2333715A1 (en) | 1999-12-09 |
DE19824487A1 (de) | 1999-12-09 |
JP2002517382A (ja) | 2002-06-18 |
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