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CN1113875C - 取代的芳族硫代羧酰胺及其作为除草剂的用途 - Google Patents

取代的芳族硫代羧酰胺及其作为除草剂的用途 Download PDF

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Publication number
CN1113875C
CN1113875C CN95193953A CN95193953A CN1113875C CN 1113875 C CN1113875 C CN 1113875C CN 95193953 A CN95193953 A CN 95193953A CN 95193953 A CN95193953 A CN 95193953A CN 1113875 C CN1113875 C CN 1113875C
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methyl
fluorine
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CN95193953A
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CN1155282A (zh
Inventor
K·-H·林克
K·芬代森
R·安德里
M·－W·德韦斯
A·兰达
O·沙尔纳
W·哈斯
H·-J·桑特尔
M·多林格
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Bayer AG
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Bayer AG
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    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
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    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
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Abstract

本发明涉及新的通式(I)所示的取代芳族硫代羧酰胺，及其作为除草剂的用途。式(I)中，R1、R2和R3是氢或各种取代基，Z是可以有取代的单环或双环、饱和或不饱和杂环基、杂环基氨基或杂环基亚氨基。

Description

取代的芳族硫代羧酰胺及其作为除草剂的用途
本发明涉及新的取代的芳族硫代羧酰胺，其制备方法及其作为除草剂的用途。
已经知道某些芳族硫代羧酰胺，例如2，6-二氯苯并硫代酰胺(氯草硫胺)，具有除草性能(参见GB-B 987253)。但是，这种已知化合物的活性，特别是在低施用率和低浓度条件下的活性，在各种应用中并不是完全令人满意的。
现已发明了具有下述通式(I)的新的取代芳族硫代羧酰胺其中：R1代表氢或卤素，R2代表下述基团：
         -A1-A2-A3
其中：
A1代表一个单键，或代表氧、硫、-SO-、-SO2-、-CO-
  或基团-N-A4-，其中A4代表氢、羟基、烷基、链烯基、链
  炔基、烷氧基、芳基、烷基磺酰或芳基磺酰，
A1还代表在所有情况下任选取代的链烷二基、链烯二基、链炔二基、
  环烷二基、环烯二基或芳二基，
A2代表一个单键，或代表氧、硫、-SO-、-SO2-、-CO-
  或基团-N-A4-，其中A4代表氢、羟基、烷基、链烯基、链
  炔基、芳基、烷氧基、烷基磺酰或芳基磺酰，
A2还代表在所有情况下任选取代的链烷二基、链烯二基、链炔二基、
  环烷二基、环烯二基或芳二基，A3代表氢、羟基、氨基、氰基、异氰基、氰硫基、硝基、羧基、氨基甲酰基、硫代氨基甲酰基、磺基、氯磺酰、卤素，或者代表在所有情况下任选取代的烷基、烷氧基、烷硫基、烷基亚磺酰、烷基磺酰、烷氨基、二烷氨基、烷氧羰基、二烷氧基(硫代)磷酰基、链烯基、链烯氧基、链烯氨基、亚烷氨基、链烯氧羰基、链炔基、链炔氧基、链炔氨基、链炔氧羰基、环烷基、环烷氧基、环烷基烷基、环烷基烷氧基、亚环烷基氨基、环烷氧基羰基、环烷基烷氧羰基、芳基、芳氧基、芳烷基、芳烷氧基、芳氧羰基、芳烷氧羰基、杂环基、杂环基烷基、杂环基烷氧基或杂环基烷氧羰基，R3代表氢或卤素、或与R2一起代表链烷二基或链烯二基，该基团可在烃链的始端(或末端)或在烃链中任选含有一个氧原子、硫原子、SO2基团、NH基团、N-烷基、羰基和/或硫代羰基，和Z代表在所有情况下任选取代的单环或双环，饱和或不饱和的杂环基、杂环基氨基或杂环基亚氨基。使下述通式(II)的取代芳族腈：
Figure C9519395300071
其中R1、R2、R3和Z的定义同上；与硫化氢(H2S)或与硫代乙酰胺，任选在反应助剂和任选在稀释剂存在下反应可制得通式(I)的新的取代芳族硫代羧酰胺。
新的通式(I)的取代芳族硫代羧酰胺以其强的和选择性的除草活性而引人注目。
在这些定义中，单独存在或与杂原子相连的，例如在烷氧基、烷硫基或烷氨基中的，饱和或不饱和烃链，例如烷基、链烷二基、链烯基或链炔基，均为直链或支链的。
卤素通常代表氟、氯、溴或碘，优选氟、氯或溴，特别是氟或氯，
本发明优选涉及下述式(I)的化合物，其中R1代表氢、氟、氯或溴，R2代表下述基团
                -A1-A2-A3
其中：
A1代表一个单键，或代表氧、硫、-SO-、-SO2-、-CO-
  或基团-N-A4-，其中A4代表氢、羟基、C1-C4烷基、
  C3-C4链烯基、C3-C4链炔基、C1-C4烷氧基、苯基、
  C1-C4烷基磺酰或苯磺酰，
A1还代表在所有情况下任选被氟或氯取代的C1-C6链烷二基、
  C2-C6链烯二基、C2-C6链炔二基、C3-C6环烷二基、
  C3-C6-环烯二基或亚苯基，
A2代表一个单键，或代表氧、硫、-SO-、-SO2-、-CO-
  或基团-N-A4-，其中A4代表氢、羟基、C1-C4烷基、
  C3-C4链烯基、C3-C4链炔基、C1-C4烷氧基、苯基、
  C1-C4烷基磺酰或苯磺酰，
A2还代表在所有情况下任选被氟或氯取代的C1-C6链烷二基、
  C2-C6链烯二基、C2-C6链炔二基、C3-C6环烷二基、
  C3-C6-环烯二基或亚苯基，
A3代表氢、羟基、氨基、氰基、异氰基、氰硫基、硝基、羧基、氨
  基甲酰基、硫代氨基甲酰基、磺基、氯磺基、卤素，或代表在所
  有情况下任选被卤素-或C1-C4烷氧基取代的烷基、烷氧基、烷
  硫基、烷基亚磺酰基、烷基磺酰基、烷氨基、二烷氨基、烷氧羰
  基或二烷氧基(硫代)磷酰基、这些基团中的每一个基团，在其
  烷基基团中可含有1-6个碳原子，或者代表在所有情况下任选
  卤素取代的链烯基、链烯氧基、链烯氨基、亚烷氨基、链烯氧羰
  基、链炔基、链炔氧基、链炔氨基或链炔氧羰基，这些基团中的
  每一个基团，在其链烯基、亚烷基或链炔基基团中可含有2-6
  个碳原子；或代表在所有情况下任选被卤素、氰基、羧基、C1-
  C4烷基和/或C1-C4烷氧羰基取代的环烷基、环烷氧基、环烷基
  烷基、环烷基烷氧基、亚环烷基氨基、环烷氧羰基或环烷基烷氧
  羰基，其中这些基团中的每一个基团在其环烷基中可含有3-6  个碳原子，在其烷基中任选含有1-4个碳原子；或代表在所有情况下任选被硝基、氰基、羧基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和或C1-C4烷氧羰基取代的苯基、苯氧基、苯基-C1-C4烷基、苯基-C1-C4烷氧基、苯氧羰基或苯基-C1-C4烷氧羰基、(在所有情况下任选全部或部分氢化的)吡咯基、吡唑基、咪唑基、三唑基、呋喃基、噻吩基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、嘧啶基、三嗪基、吡唑基-C1-C4烷基、呋喃基-C1-C4烷基、噻吩基-C1-C4烷基、噁唑基-C1-C4烷基、异噁唑基-C1-C4烷基、噻唑基-C1-C4烷基、吡啶基-C1-C4烷基、嘧啶基-C1-C4烷基、吡唑基甲氧基或呋喃基甲氧基，或代表全氢吡喃基甲氧基或吡啶基甲氧基，R3代表氢、氟、氯或溴，或与R2一起代表链烷二基或链烯二基，其中每个基团最多带有4个碳原子，并可在烃链的始端(或末端)或在烃链中任选地带有一个氧原子、一个硫原子、SO2基团、NH基团、N-C1-C4烷基、羰基和/或硫代羰基；和Z在所有情况下代表单环或双环的，饱和或不饱和的杂环基、杂环基氨基或杂环基亚氨基，其中每个基团在杂环系统中可含有2-6个碳原子和1-4个氮原子，这些基团可任选地含有氧原子或硫原子和/或最多任选含有三个选自-CO-、-CS-、-SO-和/或SO2的基团，并且任选地被选自下述基团的一个或多个基团取代，所述基团包括：硝基、羟基、氨基、氰基、羧基、氨基甲酰基、硫代氨基甲酰基、卤素、C1-C6烷基(该基团可任选地被卤素或C1-C4烷氧基取代)，C2-C6链烯基或C2-C6链炔基(二者均可任选地被卤素取代)，C1-C6烷氧基或C1-C6烷氧羰基(二者均可任选地被卤素或C1-C4烷氧基取代)，C2-C6链烯氧基或C2-C6链炔氧基(二者均可任选地被卤素取代)，C1-C6烷硫基、C2-C6链烯硫基或C2-C6链炔硫基(二者均可任选地被卤素取代)、C1-C6烷氨基或二(C1-C4烷基)氨基、C3-C6环烷基或C3-C6环烷基-C1-C4烷基(二者均可任选地被卤素和/或C1-C4烷基取代)、苯基、苯氧基、苯硫基、
苯基亚磺酰基、苯基磺酰基或苯氨基(在所有情况下均可任选地
被硝基、氰基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-
C4烷氧基、C1-C4卤代烷氧基和/或C1-C4烷氧羰基取代)。
本发明尤其涉及下述式(I)的化合物，其中：R1代表氢、氟或氯，R2代表下述基团
               -A1-A2-A3
其中：
A1代表一个单键，或代表氧、硫、-SO-、-SO2-、-CO-
  或基团-N-A4-，式中A4代表氢、羟基、甲基、乙基、正-
  或异-丙基、甲氧基、乙氧基、正-或异-丙氧基、甲磺酰或乙
  磺酰，
A1还代表亚甲基、乙-1，1-二基、乙-1，2-二基、丙-1，1-二
  基、丙-1，2-二基、丙-1，3-二基、乙烯-1，2-二基、丙烯
  -1，2-二基、丙烯-1，3-二基、乙炔-1，2-二基、丙炔-1，2
  -二基或丙炔-1，3-二基，
A2代表一个单键，或代表氧、硫、-SO-、-SO2-、-CO-
  或基团-N-A4-，式中A4代表氢、羟基、甲基、乙基、正-
  或异-丙基、甲氧基、乙氧基、正-或异-丙氧基、甲磺酰、乙
  磺酰、正-或异-丙磺酰或苯磺酰，
A2还代表亚甲基、乙-1，1-二基、乙-1，2-二基、丙-1，1-二
  基、丙-1，2-二基、丙-1，3-二基、乙烯-1，2-二基、丙烯
  -1，2-二基、丙烯-1，3-二基、乙炔-1，2-二基、丙炔-1，2
  -二基或丙炔-1，3-二基，
A3代表氢、羟基、氨基、氰基、硝基、羧基、氨基甲酰基、磺基、
  氟、氯、溴，或代表在所有情况下任选地被氟、氯、甲氧基或乙
  氧基取代的甲基、乙基、正-或异-丙基、正-、异-、仲-或
  叔丁基、正-、异-、仲-或叔戊基、甲氧基、乙氧基、正-或
  异-丙氧基、正-、异-、仲-或叔丁氧基、正-、异-、仲-
  或叔戊氧基、甲硫基、乙硫基、正-或异-丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰、乙基亚磺酰、正-或异-丙基亚磺酰、甲磺酰、乙磺酰、正-或异-丙磺酰、甲氨基、乙氨基、正-或异-丙氨基、正-、异-、仲-或叔丁氨基、二甲氨基、二乙氨基、甲氧羰基、乙氧羰基、正-或异-丙氧羰基、二甲氧基磷酰、二乙氧基磷酰、二丙氧基磷酰或二异丙氢基磷酰或代表在所有情况下任选被氟或氯取代的丙烯基、丁烯基、丙烯氧基、丁烯氧基、丙烯氨基、丁烯氨基、亚丙氨基、亚丁氨基、丙烯氧基羰基、丁烯氧基羰基、丙炔基、丁炔基、丙炔氧基、丁炔氢基、丙炔氨基、丁炔氨基、丙炔氧基羰基或丁炔氧基羰基，或者代表在所有情况下任选地被氟、氯、氰基、羧基、甲基、乙基、正-或异-丙基、甲氧羰基或乙氧羰基取代的环丙基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙基甲基、环丁基甲基、环戊基甲基、环已基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、亚环戊基氨基、亚环己基氨基、环戊氧基羰基、环己氧基羰基、环戊基甲氧羰基或环己基甲氧羰基，或者代表在所有情况下任选地被硝基、氰基、羧基、氟、氯、溴、甲基、乙基、正-或异-丙基、三氟甲基、甲氧基、乙氧基、正-或异-丙氧基、二氟甲氧基、三氧甲氧基、甲氧羰基和/或乙氧羰基取代的苯基、苯氧基、苄基、苯乙基、苄氧基、苯氧羰基、苄氧羰基，(在所有情况下任选地被完全或部分氢化的)吡咯基、吡唑基、咪唑基、三唑基、呋喃基、噻吩基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、嘧啶基、三嗪基、吡唑甲基、呋喃甲基、噻吩甲基、噁唑甲基、异噁唑甲基、噻唑甲基、吡啶甲基、嘧啶甲基、吡唑甲氧基、呋喃甲氧基或吡啶甲氧基，R3代表氢、氟或氯，或者与R2一起代表在所有情况下含有1-3个碳原子的链烷二基或链烯二基，该基团可在烃链的始端(或末端)或在烃链中任选地含有氧原子、硫原子、NH基团、N-甲基基团、羰基和/或硫代羰基，和Z在所有情况下代表单环或双环饱和或不饱和的杂环基，杂环基氨基，其中在每个杂环体系中带有2-5个碳原子和1～3个氮原
子，该基团还可任选地含有一个氧原子或硫原子和/或任选地含有
最多两个选自-CO-、-CS-、-SO-和/或SO2-的基团，
且该基团可任选地被选自下述基团的一个或多个基团取代，所述
基团包括：硝基、羟基、氨基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、氟、氯、溴；甲基、乙基、正-或异-丙基、正-、
异-、仲-或叔丁基(它们可任选地被氟、氯、甲氧基或乙氧基
取代)；丙烯基、丁烯基、丙炔基或丁炔基(它们在所有情况下
可任选地被氟或氯取代)；甲氧基、乙氧基、正-或异-丙氧基、
正-、异-、仲-或叔丁氧基、甲氧羰基或乙氧羰基(它们在所
有情况下可任选地被氟、氯、甲氧基或乙氧基取代)；丙烯氧基、
丁烯氧基、丙炔氧基或丁炔氧基(它们可任选地被氟或氯取代)；
甲硫基、乙硫基、正-或异-丙硫基、正-、异-、仲-或叔丁
硫基、丙烯硫基、丁烯硫基、丙炔硫基或丁炔硫基(它们在所有
情况下可任选地被氟或氯取代)；甲氨基、乙氨基、正-或异-
丙氨基、正-、异-、仲-或叔丁氨基、二甲氨基或二乙氨基；
环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、
环戊基甲基或环己基甲基(它们在所有情况下可任选地被氟、氯、
甲基、乙基、正-或异-丙基取代)、苯基、苯氧基、苯硫基、
苯基亚磺酰、苯磺酰或苯氨基(它们在所有情况下可任选地被硝
基、氰基、氟、氯、溴、甲基、乙基、正-或异-丙基、三氟甲
基、甲氧基、乙氧基、正-或异一丙氧基、二氟甲氧基、三氟甲
氧基、甲氧羰基或乙氧羰基取代)。
一组特别优选的式(I)化合物是下述式(Ia)、(Ib)和(Ic)的化合物：
Figure C9519395300131
其中：
R1、R2和Z的含义与上述尤为优选方案中定义相同，
R4和R5可以相同或不同，在所有情况下各自独立地代表氢、氟、氯、
甲基或乙基、或在式(Ib)中一起代表氧或硫，和
Q代表氧、硫、N-甲基或N-乙基。
Z在通式(I)和(Ia)、(Ib)和(Ic)中特别代表下述杂环基：
Figure C9519395300132
Figure C9519395300141
其中在各种情况下：
Q1代表选自下述基团的一个基团，这些基团包括：-CO-、-CS-、-CH2-、-CH(OH)-、-CHCl-、-CHBr-、-C(＝CH2)-、-C(＝CHF)-、-C(＝CF2)-、-C(＝CHCl)-、-C(＝CHBr)-、-C(＝CHOCHF2)-、-C(＝CHOCF3)-、-C(＝CHOCH2CF3)-基团，
Q2代表氧、硫或选自下述基团的一个基团，这些基团包括：-CO-、-CS-、-CH2-、-CHF-、-CF2-、-CHCl-、-CHBr-、-CHOCHF2-、-CHOCF3-、-CHOCH2CF3-基团，
R6代表氢、氨基、硝基、氰基、羧基、氨基甲酰基、氟、氯、溴、
  甲基、乙基、正-或异-丙基、环丙基、二氟甲基、三氟甲基、
  一氯二氟甲基、甲氧基、乙氧基、正-或异-丙氧基、二氟甲氧
  基、三氟甲氧基、一氯二氟甲氧基、甲硫基、乙硫基、正-或异
  -丙硫基、二氟甲硫基、三氟甲硫基、一氯二氟甲硫基、甲氨基、
  乙氨基、正-或异-丙氨基、二甲氨基、二乙氨基、甲氧羰基或
  乙氧羰基，和
R7代表氢、羟基、氨基、氰基、甲基、乙基、正-或异-丙基、二
  氟甲基、甲氧基、乙氧基、正-或异-丙氧基，
或者任选地两个相连的基团R6和R6或R7和R7或R6和R7一起代表
在所有情况下可任选地被氟、氯、溴、甲基、乙基、正-或异-丙
基取代的，最多含4个碳原子的链烷二基或链烯二基，该基团可在
烃链的始端(或末端)或烃链中任选地插入氧，硫或选自-SO-、
SO2-、-N(CH3)-或N(C2H5)-的基团。
在上述总的及优选范围内指定列出的基团定义同时适用于式(I)的终产物和制备中所需的各自相应的起始原料和中间体。这些基团的定义可根据需要互相组合，因而它们包括了优选化合物指定范围内的任选所需组合。
本发明式(I)化合物的实例如下所示：第一组
Figure C9519395300161
在该通式中，R1、R2和R3的定义如下所述：合成实例序号      R1       R2                  R31           H         F                     H2           H         Cl                    H3           H         Cl                    Cl4           Cl        F                     H5           F         F                     H6           F         F                     Cl7           F         CH3                  H8           F         C2H5                H9           F         -CH2Cl               H10          F         F                      F11          F         -NHC2H5             H12          F         -CH2CN               H13          F         -N(CH3)SO2C2H5   H14          Cl        -N(CH3)SO2C2H5   H实例号     R1        R2                    R315         Cl         -N(CH3)SO2C2H5    Cl16         F          -NH-COCF3             H17         F          -OH                    H18         Cl         -OH                    H19         F          -CH(CH3)2           H2O         F          -NH-SO2-CH3         H21         F          -SO2-CH3            H22         F          -SO2-O-CH2          H23         F          -SO2-NH-CH3         H24         F          -COOCH3              H25         F          -CO-NH-CH3           H26         Cl         -COOCH3              Cl27         Cl         -COOC2H5            H28         F          -O-C2H5             H29         F          -N(C2H5)SO2C2H5 H3O         F          -N(SO2CH3)2        H31         F          -CO-N(CH3)2         H32         F          -S-CH2-C≡CH         H33         Cl         -S-CH2-C≡CH         F实例号     R1         R2                           R334         F           -S-CH2-C≡CH                 Cl35         F           -O-CH(CH3)-C≡CH             H36         F           -S-CH2-COOCH3               H37         F           -O-CH2CH2-OCH3             H38         F           -O(CH2CH2O)2CH3          H39         F           -O-CH2-CH＝CH2              H4O         F           -O-CH2-C≡CH                 H41         F           -SH                           H42         F           -S-CH3                       H43         F           -S-C2H5                     H44         F           -S-CH(CH3)2                 H45         F           -O-CH2-CF3                  H46         F           -O-CH(CH2F)2                H47         F                    H48         F             H实例号     R1        R2                    R349         F          -NH-SO2C2H5         H50         Cl         -NH-SO2C2H5         H51         F          -NH-SO2C2H5         Cl52         F          -NH-SO2CH(CH3)2     H53         F          -NH-SO2C4H9         H54         F          -N＝CH-OC2H5         H55         F          -N＝C(CH3)OC2H5     H56         F          -N＝C(OCH3)2         H57         F          -N＝CH-N(CH3)2       H58         F          -SCN                    H59         F          -SO2Cl                H60         F          -O-CS-N(CH3)2        H61         F          -S-CO-N(CH3)2        H62         F          -NH-P(O)(CH3)OC2H5  H63         F          -NH-P(O)(OC2H5)2    H64         F          -NH-COC2H5           H65         F          -N(CH3)COCF3         H66         F          -NH-COCH(CH3)2       H67         F          -NH-CO-CO-C(CH3)3    H实例号      R1          R2                     R368          F           -NH-CO-NH2              H69          F           -NH-CO-NHCH3            H70          F           -NH-CO-N(CH3)2         H71          F           -N(COCH3)2             H72          F           -NH-COCH(CH3)Cl         H73          F           -S-CH2-CH＝CH2         H74          Cl          -S-CH2-CH＝CH2         H75          F           -S-CH(CH3)C≡CH         H76          F           -S-CH(CH3)COOC2H5     H77          F           -S(O)-CH3               H78          F               H79          F              H80          F          
Figure C9519395300203
    H实例号      R1         R2                        R381          F        
Figure C9519395300211
              H82          F        
Figure C9519395300212
           H83          F                      H84          F           -O-CH2-CN                  H85          F           -O-SO2CH3                 H86          F           -OCH2-CH(Cl)＝CH2         H87          F           -O-CH2-COOCH3             H88          F           -O-CHF2                    H89          F           -OCOOCH2CH2Cl            -H90          F           -OCH2P(O)(OC2H5)2      H91          Cl          -O-CH(CH3)P(O)(OC2H5)2 H实例号       R1          R2                         R392           F           
Figure C9519395300221
     H93           F                        H94           F            -O-N(C2H5)2               H95           F                        H96           F           
Figure C9519395300224
            H97           F                        Cl98           Cl          
Figure C9519395300226
            H实例号    R1       R2                             R399        F                     F100       F       
Figure C9519395300232
         H101       F       
Figure C9519395300233
          H102       F             H103       F        -NCH(CH3)2SO2C2H5           H104       F        -N(CH3)SO2CH(CH3)2           H105       H        -N(CH3)SO2C2H5               Cl106       Cl       -N(CH3)SO2C4H9               H107       F        -N(CH3)SO2C2H5               H108       F        -N(CH3)SO2CH3                 H109       F        -N(SO2C2H5)2                 H实例号     R1       R2                      R3110        F         -N(SO2CH3)SO2C2H5  H111        F         
Figure C9519395300241
       H112        F         -N(CH3)2               H113        F         -NH2                    H114        Cl        -NH2                    H115        Cl        -O-CH(CH3)2            H116        F         -O-CH(CH3)2            H117        F                         H118        Cl       
Figure C9519395300243
                H119        F         -O-CH2-COOC2H5        H120        F         -S-CH2-COOCH3          H121        F         -S-CH2-COOC2H5        H实例号       R1          R2                               R3122          Cl           -S-CH2-COOC2H5                 H123          F            -CH2-CH(Cl)COOCH3               H124          F            -CH2-CH(Cl)COOC2H5             H125          F            -CH2-CH(Cl)CONHC2H5            H126          Cl           -CH2-CH(Cl)CONHC2H5            H127          Cl          
Figure C9519395300251
  H128          F              H129          F            -COOC3H7-i                      H第二组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第3组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第4组
Figure C9519395300262
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第5组
Figure C9519395300263
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第6组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第7组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第8组
Figure C9519395300273
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第9组
Figure C9519395300281
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第10组
Figure C9519395300282
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第11组
Figure C9519395300283
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第12组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第13组
Figure C9519395300292
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第14组
Figure C9519395300293
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第15组
Figure C9519395300301
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第16组
Figure C9519395300302
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第17组
Figure C9519395300303
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第18组
Figure C9519395300311
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第19组
Figure C9519395300312
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第20组
Figure C9519395300313
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第21组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第22组
Figure C9519395300322
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第23组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第24组
Figure C9519395300331
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第25组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第26组
Figure C9519395300333
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第27组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第28组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第29组
Figure C9519395300343
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第30组
Figure C9519395300351
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第31组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第32组
Figure C9519395300353
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第33组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第34组
Figure C9519395300362
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第35组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第36组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第37组
Figure C9519395300372
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第38组
Figure C9519395300373
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第39组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第40组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第41组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第42组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第43组
Figure C9519395300392
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第44组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第45组
Figure C9519395300401
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第46组
Figure C9519395300402
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第47组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第48组
Figure C9519395300411
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第49组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第50组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第51组
Figure C9519395300421
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第52组
Figure C9519395300422
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第53组
Figure C9519395300423
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第54组
Figure C9519395300431
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第55组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第56组
Figure C9519395300433
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第57组
Figure C9519395300441
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第58组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第59组
Figure C9519395300443
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第60组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第61组
Figure C9519395300452
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第62组
Figure C9519395300453
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第63组
Figure C9519395300461
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第64组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第65组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第66组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第67组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第68组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第69组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第70组
Figure C9519395300482
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第71组
Figure C9519395300483
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第72组
Figure C9519395300491
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第73组
Figure C9519395300492
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第74组
Figure C9519395300493
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第75组
Figure C9519395300501
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第76组
Figure C9519395300502
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第77组
Figure C9519395300503
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第78组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第79组
Figure C9519395300512
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第80组
Figure C9519395300513
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第81组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第82组
Figure C9519395300522
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第83组
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第84组
Figure C9519395300531
在该通式中，R1、R2和R3具有，例如，在上述第一组中的定义。第85组
Figure C9519395300532
在该通式中，R1、R4和R5具有下述定义。实例号    R1         R4          R51         F           CH3         CH32         Cl          CH3         CH33         H           CH3         CH34         F           Cl           CH35         F           Cl           Cl6         F           C2H5      CH3 第86组
在该通式中，R1、R4和R5具有，例如，在上述第85组中的定义。第87组
Figure C9519395300542
在该通式中，R1、R4和R5具有，例如，在上述第85组中的定义。第88组
Figure C9519395300543
在该通式中，R1、R4和R5具有，例如，在上述第85组中的定义。第89组
Figure C9519395300551
在该通式中，R1、R4和R5具有，例如，在上述第85组中的定义。
使用例如2-(2-氟-4-氰基-5-甲氧基苯基)-4-甲基-5-二氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮和硫化氢作为起始物料，本发明方法的反应历程可用下述方程式举例说明：
Figure C9519395300552
在本发明方法中用于制备通式(I)化合物的起始物料的取代芳族腈的总的定义由式(II)给出。在式(II)中，R1、R2、R3和Z优选或特别优选具有已在上文指出的，与式(I)化合物的描述有关的相应优选或特别优选的R1、R2、R3和Z的定义。
式(II)的起始物料是已知的和/或可用已知方法(参见EP-A-370332；DE-A4238125；DE-A4303376；US-P5084084制备实例)制备。
实施本发明方法的适宜溶剂为常用的有机溶剂。具体而言这些溶剂包括：任选卤代的脂肪烃、脂环烃或芳香烃类，例如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿和四氯化碳；醚类，如乙醚、异丙醚、二噁烷、四氢呋喃、乙二醇二甲醚或乙二醇二乙醚；酮类，如丙酮、丁酮或甲基异丁基酮；腈类，如乙腈、丙腈或苄腈；酰胺类，如N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、N-甲基-N-甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酸三酰胺；酯类，如乙酸甲酯或乙酸乙酯；亚砜，如二甲亚砜；氮杂苯类，如吡啶；醇类，如甲醇、乙醇、正-或异-丙醇、乙二醇单甲醚、乙二醇单乙醚、二亚乙基二醇单甲醚、二亚乙基二醇单乙醚，它们与水的混合物或纯水。
本发明方法最好在适宜的反应助剂存在下进行。适宜的反应助剂是所有惯用的无机或有机碱。它们包括：例如，碱土金属或碱金属氢化物、氢氧化钠、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐，例如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵和碱性有机含氮化合物，例如三甲胺、三乙胺、三丁胺、N，N-二甲基苯胺、吡啶、N-甲基哌啶、N，N-二甲氨基吡啶、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)。
当进行本发明方法时，反应温度的变化范围相对较宽。通常反应在0℃～100℃下进行，优选10～80℃。
本发明方法一般在常压下进行，但也可在高压或低压下进行，其范围通常为0.1巴～10巴。
为了实施本发明的方法，式(II)起始物料通常在合适的稀释剂中，于反应助剂存在下导入，并将硫化氢或硫代乙酰胺缓慢计量加入。优选相对大量地过量使用硫化氢或硫代乙酰胺。反应混合物在具体所需温度下搅拌数小时。均依据惯用方法(参见制备例)完成本发明方法。
按照本发明的活性化合物可以用作脱叶剂、干燥剂、阔叶植物毁灭剂，尤其可用作除草剂。所谓杂草，在最广泛的意义上，要理解成生长在不希望其出现的位置上的一切植物。按照本发明的物质是否起到灭生性除草剂或选择性除草剂的作用，基本上取决于用量。
按照本发明的活性化合物的使用可涉及诸如下列植物：
以下各属双子叶杂草：芸苔属、独行菜属、猪殃殃属、繁缕属、母菊属、春黄菊属、牛膝菊属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、番诸属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、蔊菜属、水松叶属、母草属、野芝麻属、婆婆纳属、苘麻属、刺酸模属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、三叶草属、毛莨属和蒲公英属。
以下各属双子叶栽培作物：棉属、大豆属、甜菜属、胡罗卜属、菜豆属、豌豆属、茄属、亚麻属、番薯属、巢菜属、菸草属、番茄属、花生属、芸苔属、莴苣属、黄瓜属和南瓜属。
以下各属单子叶杂草：稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、蟋蟀草属、臂形草属、黑麦草属、雀麦属、燕麦属、莎草属、蜀黍属、冰草属、狗牙根属、雨久花属、飘拂草属、慈姑属、荸荠属、莞草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、翦股颖属、看麦娘属和野豚鼠草属(Apera)。
以下各属单子叶栽培作物：稻属、玉蜀黍属、小麦属、大麦属、燕麦属、黑麦属、蜀黍属、黍属、甘庶属、凤梨属、天门冬属和葱属。
然而，按照本发明的活性化合物的用途绝不仅限于以上各属，而且也以同样的方式扩展到其它植物。
因浓度而异，这类化合物适合于诸如工业场地和铁路线上以及有或无树林的道路和广场上的灭生性除草。同样，这类化合物也可用于多年生栽培植物如森林、装饰性园林、果树园、葡萄园、桔园、坚果园、香蕉园、咖啡园、茶园、橡胶园、油棕园、可可园、软果园和酒花田除草，草坪、草地和牧场除草，以及一年生栽培植物的选择性除草。
本发明通式(I)的化合物尤其适用于采用发芽前和发芽后的方法选择性清除单子叶和双子叶作物中的单子叶和双子叶杂草。
在一定程度上式(I)化合物还具有杀真菌作用，例如可抗稻瘟病(Pyricularia oryzae)。
这些活性化合物可以配成常用制剂，例如溶液、乳液、可湿性粉剂、悬浮液、粉剂、尘剂、膏剂、可溶性粉剂、颗粒剂、悬浮液-乳液浓制剂、浸渍了活性化合物的天然材料和合成材料、及包入聚合物材料中的甚微细胶囊。
这些制剂是用已知方法生产的，例如将活性化合物与增充剂即液体溶剂和/或固体载体混合，任选地使用表面活性剂，即乳化剂和/或分散剂和/或泡沫形成剂。
在使用水作为增充剂的情况下，有机溶剂等也可以用作助溶剂。适用的液体溶剂主要有：芳烃，如二甲苯、甲苯或烷基萘；氯代芳烃和氯代脂族烃，如氯苯、氯乙烯或二氯甲烷；脂族烃，如环己烷或链烷烃，例如石油馏分、矿物油和植物油；醇类如丁醇或二醇；及其醚类和酯类；酮类如丙酮、甲基·乙基酮、甲基·异丁基酮或环己酮；强极性溶剂如二甲基甲酰胺和二甲基亚砜，以及水。
适用的固体载体有：例如铵盐和磨碎的天然无机物，如高岭土、粘土、滑石、白垩、石英、美国活性白土、蒙脱土或硅藻土，及磨碎的合成无机物，如高分散的二氧化硅、氧化铝和硅酸盐；适用于颗粒剂的固体载体有：例如粉碎并分级的天然矿石如方解石、大理石、浮石、海泡石和白云石，以及无机和有机粉末的合成颗粒，和有机材料如锯末、椰子壳、玉米芯和烟草杆的颗粒；适用的乳化剂和/或泡沫形成剂有：例如非离子型和阴离子型乳化剂，如聚氧乙烯脂肪酸酯、聚氧化乙烯脂肪醇醚，例如烷芳基聚二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白质水解产物；适用的分散剂有：例如木质素亚硫酸盐废液和甲基纤维素。
在这些制剂中可以使用粘合剂如羧甲基纤维素及粉末、颗粒或胶乳等形式的天然与合成聚合物，例如阿拉伯树胶、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。进一步可能的添加剂是矿物油和植物油。
也可以使用着色剂，如无机颜料，诸如氧化铁、氧化钛和普鲁士蓝，和有机染料，诸如茜素染料、偶氮染料和金属酞菁染料，及痕量营养物，如铁、锰、硼、铜、钴、钼和锌的盐类。
这些制剂一般含有0.1％-95％(重量)活性化合物，较好是0.5％-90％。
为了控制杂草，按照本发明的活性化合物(原药或其制剂形式)也可与已知的除草剂(成品制剂或可能的罐混物)形成混合物再使用。
用于这类混合物的可能成分是已知的除草剂，例如酰替苯胺类，如吡氟草胺和敌稗；芳基羧酸类，如二氯吡啶甲酸、麦草畏和毒莠定；芳氧基链烷酸类，如2，4-D(2，4-滴)、2，4-DB(2，4-滴丁酸)、2，4-DP(2，4-滴丙酸)、氟氧吡啶(fluroxypyr)、MCPA(2甲4氯)、MCPP(2甲4氯丙酸)和木草畏(triclopyr)、芳氧基-苯氧基链烷酸酯，如禾草灵(diclofop-methyl)、噁唑禾草灵-乙酯(fenoxaprop-ethyl)、禾草枯(fluazifop-butyl)、吡氟氯禾灵-甲酯(haloxyfop-methyl)和2-[4-[(6-氯-2-喹喔啉基)氧]苯氧基]丙酸乙酯(喹禾灵-乙酯quizalofop-ethyl)、连氮酮(azinone)类，例如5-氨基-4-氯-2-苯基哒嗪-3(2H)-酮(Chloridazon)和哒草灭；氨基甲酸酯类，例如氯苯胺灵、异苯敌、苯敌草和苯胺灵、氯乙酰替苯胺类，例如草不绿、灭草胺、去草胺、吡草胺(metazachlor)、甲氧毒草胺(甲代隆)、丙草胺(氯苯胺)和毒草胺；二硝基苯胺类，例如黄草消、芽草平和氟乐灵；二苯醚类，例如三氟羧草醚(氟草灭)、治草醚、氯硝醚(X-52)、草枯醚(氯硝酚钠)、乙羧氟草醚(氟糖酚)(fluoroglycofen)、氟黄胺草醚(虎威)、halosafen、乳氟禾草灵(乳酚)(lactofen)、除草醚和氟草胺；脲类，例如绿麦隆、Cumyluron(JC-940)、敌草隆、沙草隆(草香隆)、伏草隆、异丙隆、利谷隆和噻唑隆；羟胺类，例如枯杀达、烯草酮(乙氧定)(clethodim)、噻草酮(环氧定)(cycloxydim)、烯禾定(禾莠净)和肟草酮(烷氧定)(tralkoxydim)；咪唑啉酮类，例如咪草烟、咪草酯(咪唑甲苯)(imazamethabenz)、灭草烟(咪唑吡啶)(imazapyr)、和咪唑喹啉(imazaquin)；腈类，例如溴苯腈、敌草腈和碘苯腈；氧乙酰胺类，例如苯噻草胺；磺酰脲类，例如AC-014(AC-322140)、(氨基磺隆)(amidosulfuron)、甲基苯磺隆(bensulfuron-methyl)、氯嘧磺隆(酯)(乙基氯默隆)(chlorimuron-ethyl)、绿草隆(阔草脲)、醚磺隆、DPX-47、HOE-404、imazosulfuron、甲基甲磺隆(metsulfuron-methyl)、烟嘧磺隆、氟嘧磺隆、吡嘧磺隆(酯)(pyrazosulfuron-ethyl)、甲基噻磺隆(thifensulfuron-methyl)、醚苯磺隆(triasulfuron)和苯磺隆甲酯(tribenuron-methyl)；硫代氨基甲酸酯类，例如苏达灭、草灭特、燕麦敌、哌草丹、扑草灭、禾草畏、草达灭、卡草丹(扑硫威)(prosulfocarb)、杀草丹和野麦畏；三嗪类，例如阿特拉津、草净津、戊草津、扑草净、西玛津、西草净、去草净和特丁津(terbutylazine)；三嗪酮类，例如敌草灵(hexazinone)、灭它通(metamitron)和赛克津；及其它除草剂，例如氨基三唑、呋草黄、砜草磷、噻草平、吡草酮、溴丁酰草胺、草胺磷、cafenstrole(CH-900)、环庚草醚(辛甲灵)(cinmethylin)、异噁草酮(氯马腙)(clomazone)、稗草胺、氯吡啶(clopyralid)、DEH-112、燕麦清(difenzoquat)、dimethenamid、氟硫草定、草定完、flumetsulam、氟咯草酮(fluorochloridone)、草铵膦、草甘膦、甲基胺草磷、莎稗磷、etobenzanid(HW-52)、异噁苯(isoxaben)、KPP-314、KUH-833、KUH-911、KUH-920、MK-243、萘丙胺、NSK-850、松草噁(噁草灵)、哌草磷、敌稗、吡唑特(pyrazolate)、苄草唑(pyrazoxyfen)、稗草畏(pyributicarb)、草利达(pyridate)、quinchlorac、喹草酸(quinmerac)、sulphosate和2-(3，5-二氯(苯基)-2-(2，2，2-三氯乙基)环氧乙烷(tridiphane)。
与其它已知活性化合物如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养剂及土壤结构改良剂的混合物也可以使用。
这些活性化合物可以原药形式、其制剂形式、或通过进一步稀释而从其制备的使用形式例如可直接使用的溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂加以使用，它们是以浇水、喷雾、雾化或喷洒等习用方式使用的。
按照本发明的活性化合物既可以在植物发芽前也可以植物发芽后施用，它们也可以在播种前混入土壤中。
活性化合物的用量可以在一个很大的范围内变化。这基本上取决于预期效果的性质。一般地说，用量是每公顷土壤表面为10克-10千克活性化合物，较好是50克-5千克/公顷。
以下实例说明本发明活性化合物的制备方法和用途。
制备实例
实施例1
在50℃～60℃，使硫化氢通过5.5g(15mmol)2-(4-氰基-2-氟-5-乙磺酰氨基苯基)-5，6，7，8-四氢-1，2，4-三唑并[4，3-a]吡啶-3(2H)-酮，5ml三乙胺和50ml吡啶的混合物至其饱和点，于60℃将该混合物搅拌30分钟以上。然后将其真空浓缩，残余物与2N盐酸一起搅拌，滤出固体，固体产物用异丙醇重结晶。
得到4.8g(理论值的80％)2-(2-氟-5-乙磺酰氨基-4-硫代氨基甲酰苯基)-5，6，7，8-四氢-1，2，4-三唑并[4，3-a]吡啶-3(2H)-酮，熔点220℃。
实施例2
Figure C9519395300611
将4.04g(0.04mol)三乙胺加至6.3g(0.02mol)的2-(2-氟-4-氰基-5-氨基苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮的100ml丙酮溶液中。让硫化氢于23℃快速通过，内部温度升至33℃。1小时后反应结束。在旋转蒸发器内使溶液浓缩，残余物用异丙醇重结晶。
得到2.9g(理论值的42％)2-(2-氟-4-硫代氨基甲酰-5-氨基苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点161℃。
实施例3
在通入硫化氢的同时，将11g(0.0276mol)2-(2-氟-4-氰基-5-乙磺酰氨基苯基)-4-甲基-5-二氟甲基-2，4-二氢-3H-1，2，4-三唑-3-硫酮于70℃在100ml吡啶中搅拌4.5小时。将该溶液于旋转蒸发器中浓缩，残余物于水中搅拌，该混合物用浓盐酸酸化，滤出沉淀产物，用水洗涤并用异丙醇重结晶。
得到9g(理论值的77％)2-(2-氟-4-硫代氨基甲酰-5-乙磺酰氨基苯基)-4-甲基-5-二氟甲基-2，4-二氢-3H-1，2，4-三唑-3-硫酮，熔点183℃。
用与制备实施例1、2和3相类似方法，依据本发明制备方法的总述，还可以制得如下面表1中所列的式(I)化合物。表I：式(I)化合物的实例：实例号 R1     R2                   R3           Z                  熔点
                                                                   (℃)4      F       F                     H   
Figure C9519395300622
       1105      F       -NH-SO2-C2H5      H           1436      F     
Figure C9519395300624
      H        
Figure C9519395300625
 162实例号 R1     R2                   R3                Z                  熔点
                                                                        (℃)7      F       -NH-SO2-C2H5      H     
Figure C9519395300631
       237三乙铵盐8      F       F                     H     
Figure C9519395300632
           22O9      F       -NH-SO2-C2H5      H                 21810     F       -NH-SO2-C2H5      H    
Figure C9519395300634
              18511     F       F                     H    
Figure C9519395300635
              21812     F       -OC2H5              H    
Figure C9519395300636
             202实例号  R1     R2                    R3           Z                熔点
                                                                   (℃)13      F       -NH-SO2-C2H5       H           21014      F       -NH-SO2-C2H5       H         20315      F       F                     H    
Figure C9519395300643
     18516      F             H          17017      F       -OCH(CH3)2          H    
Figure C9519395300646
       20518      F       OH                    H             250实例号  R1    R2                 R3             Z                  熔点
                                                                   (℃)19      F           H    
Figure C9519395300652
       9820      F     -NH-SO2-C2H5      H            20821      F     -NH-SO2-C2H5      H             5522      F     -NH-SO2-C2H5      H      
Figure C9519395300655
     (非晶形)23      F     -NH-SO2-C2H5      H      
Figure C9519395300656
        18324      F             H      
Figure C9519395300658
     167实例号  R1     R2                       R3          Z                   熔点
                                                                        (℃)25      F       -NH-SO2-CH3            H     
Figure C9519395300661
     13026      F       -NH-SO2-CH3            H     
Figure C9519395300662
      24327      F       F                         H            19928      F       -NH-SO2-C2H5           H     
Figure C9519395300664
       20229      F       -NH-SO2-CH3             H             20030      F       -NH-SO2-CH(CH3)2       H             204实例号  R1       R2                  R3          Z                   熔点
                                                                     (℃)31      F         -NNH-SO2-C2H5     H     
Figure C9519395300671
     19532      F       
Figure C9519395300672
     H     
Figure C9519395300673
     12233      F         -O-CH2-C≡CH         H            19034      F         -NH-SO2-CH3         H     
Figure C9519395300675
       17835      F         -NH-SO2-C3H7       H     
Figure C9519395300676
       20336      F         -NH-SO2-C2H5        H      199实例号  R1       R2                R3           Z                          熔点
                                                      (℃)37      F         -NH-SO2-C2H5    H     
Figure C9519395300681
          15338      F         -NH-SO2-C2H5    H            20639      F         -NH-SO2-C2H5    H                   16740      F         F                    H                  13041      F         -OCH2CF3           H                 17342      F         -OC2H4OCH3        H                 148实例号  R1      R2                R3          Z                   熔点
                                                                  (℃)43      F        -OC2H5           H             15544      F        -OC3H7           H             13045      F        F                    H     
Figure C9519395300693
      13146      F        -OCH(CH3)2        H            20247      F        -OC2H5            H            18548      F        -NH-SO2-C2H5     H     
Figure C9519395300696
     11149      H        -NH-SO2-C2H5     H     
Figure C9519395300697
       118实例号  R1     R2                     R3        Z                  熔点
                                                                   (℃)50      F       -NH-SO2-C3H7-n      H     14351      F       -OC2H4OC2H4OCH3   H  
Figure C9519395300702
   16852      F       -NH-SO2-C3H7-n      H          (非晶形)53      F       -NH-SO2-C3H7-n      H            23254      F       -NH-SO2-C3H7-i      H  
Figure C9519395300705
         22655      F       -NH-SO2-C3H7-i      H            187实例号  R1     R2                      R3           Z                           熔点
                                                                                (℃)56      F       -NH-SO2-C3H7-i        H                     23657      F       -NH-SO2-C3H7-i        H            25258      F       -NH-SO2-C3H7-i        H                       10959      F       -NH-SO2-C3H7-i        H         
Figure C9519395300714
            20760      F       -NH-SO2-C3H7-i        H          
Figure C9519395300715
    21561      F       -N(CH3)-SO2C2H5      H                       102实例号  R1      R2                   R3          Z                熔点
                                                                  (℃)62      F        -NH-SO2-C2H5       H    
Figure C9519395300721
    18563      Cl       -NH-SO2-C2H5       H    
Figure C9519395300722
     12164      F        F                      H    
Figure C9519395300723
      15765      F        -NH-SO2-C2H5       H    
Figure C9519395300724
     19566      F        -OH                     H    
Figure C9519395300725
      193(Z)分解DBU-盐
起始化合物的制备
实施例II-1：
在室温下将5.8g(0.042mol)碳酸钾加至6.3g(0.034mol)4-甲基-3-三氟甲基-1，2，4-三唑啉-5-酮(参见如US 3,780,052)和5.4g(0.034mol)2，4，5-三氟苯基氰(参见EP 191181)的150ml二甲亚砜溶液中，随后将混合物于100℃加热14小时。将冷却的反应混合物置于水中，并将pH值用稀盐酸调节至2，并用二氯甲烷萃取数次来进行处理。合并的有机相用硫酸钠干燥，并在真空中浓缩。残余物用硅胶色谱分离(二氯甲烷洗脱)。
得到熔点为74℃的6.2g(理论值的60％)1-(4-氰基-2，5-二氟苯基)-4-甲基-3-三氟甲基-1，2，4-三唑啉-5-酮。
实施例II-2
于室温下，将0.83g(0.006mol)碳酸钾加至1.52g(0.005mol)1-(4-氰基-2，5-二氟苯基)-4-甲基-3-三氟甲基-1，2，4-三唑啉-5-酮和0.48g(0.05mol)甲磺酰胺的50ml二甲亚砜溶液中，随后将混合物于120℃加热12小时。将冷却后的反应混合物置于水中，用稀盐酸调节至pH2，并用二氯甲烷萃取数次来进行处理。合并的有机相用硫酸钠干燥真空浓缩。残余物用硅胶色谱分离(以二氯甲烷/甲醇＝20∶1洗脱)。
得到熔点为67℃的0.55g(理论值的28％)的1-(4-氰基-2-氟-5-甲磺酰氨基苯基)-4-甲基-3-三氟甲基-1，2，4-三唑啉-5-酮。
实施例II-3
Figure C9519395300741
于0-5℃下，将0.3g(10mmol)氢化钠(80％)加至30ml二甲基甲酰胺和2ml甲苯中的1.8g(10mmol)3-氨基-4，4，4-三氟丁烯酸乙酯起始进料中。将该混合物于0-5℃下搅拌30分钟。混合物冷至-70℃之后，将溶于10ml甲苯中的0.9g(5mmol)4-氰基-2，5-二氟苯基异氰酸酯加入，混合物于-60℃～-70℃搅拌150分钟。移去冷浴后加入2ml乙酸。然后用水将该混合物稀释至约两倍体积，并用乙酸乙酯萃取。浓缩有机相，残余物用异丙基醚重结晶。
得到熔点194℃的1.1g(理论值的69％)1-(4-氰基-2，5-二氟苯基)-3，6-二氢-2，6-二氧代-4-三氟甲基-1-(2H)嘧啶。
实施例II-4
将0.83g(3mmol)1-(4-氰基-2，5-二氟苯基)-3，6-二氢-2，6-二氧代-3，4-二甲基-1(2H)嘧啶，0.32g(3mmol)甲磺酰胺，0.6g碳酸钾和10ml二甲亚砜的混合物于120℃加热10小时。冷却后将混合物倒入冰水中，并用2N盐酸将其酸化。乙酸乙酯萃取，有机相用水洗涤，硫酸钠干燥并过滤。将溶剂从滤液中小心地在水泵真空度下蒸去。
得到0.8g(理论值的76％)的1-(4-氰基-2-氟-5-甲磺酰氨基苯基)-3，6-二氢-2，6-二氧代-3，4-二甲基-1(2H)嘧啶晶体残余物，熔点＞250℃。
用途实施例：
实施例A：
用于幼苗出现在地上以前的实验
溶剂：5重量份丙酮
乳化剂：1重量份烷芳基聚乙二醇醚
将1重量份活性化合物与所述量的溶剂混合，加入所述量的乳化剂，并用水将其稀释至所需浓度，即可制得适用的活性化合物制剂。
将被测植物的种子播种于正常的土壤中，24小时后用活性化合物制剂浇灌。有计划地保持每单位面积的水量恒定。制剂中活性化合物的浓度并不重要，要紧的是每单位面积活性化合物的施用量。三周后，植物的损伤程度以％损伤率形式与末受处理的对照组对比。数值表示：
0％＝无作用(如末处理对照组)
100％＝完全杀死
表A
幼苗长出地面以前的试验/温室活性化合物     施用量     大麦   玉米 苋属   藜属    母菊属    马齿    茄属(合成实例号)   (克/公顷)                                       苋属
(3)          125        0      0    100    100     100     100     100
(5)          125        0      0    100    100     90      90      100
(6)          125        0      30   100    100     95      100     100
(7)          125        30     0    100    100     95      100     95表B幼苗长出地面以前的试验/温室活性化合 施用量  小麦 玉米 苘麻 苋属    藜属   母菊属 马齿 茄属物(合成  (克/公顷)         属                         苋属实例号)19       60      10   0    100  95      100    100    100  10020       60      20   0    100  100     100    100    100  10021       60      0    0    100  100     100    100    100  10022       250     0    20   100  100     100    100    95   10023       60      0    0    95   70      95     100    95   7024       30      0    20   100  95      100    100    100  10025       30      0    0    100  100     90     100    100  10026       60      0    0    100  80      100    100    100  904        250     0    10   80   50      70     95     90   705        125     0    0    10   100     100    70     90   1003        60      0    0    100  100     100    100    100  1006        60      20   30   100  100     100    100    100  957        125     50   0    95   100     100    95     100  958        60      40   0    100  100     100    95     95   1009        60      0    0    100  100     100    95     90   1001        125     0    0    100  100     100    95     100  10012       60      20   0    70   70      100    95     95   7013       60      0    0    100  100     100    70     90   10016       60      10   0    95   20      100    90     80   8017       30      0    0    100  100     100    100    100  100表B(续)幼苗长出地面以前的试验/温室活性化合 施用量     小麦  玉米   苘麻   苋属    藜属    母菊属  马齿  茄属物(合成  (克/公顷)               属                             苋属实例号)28       60         0     20     100    100     100     100     100   10029       60         0     0      100    100     100     100     100   10030       60         0     0      100    100     100     90      100   10031       60         0     0      100    100     100     100     100   10032       30         10    0      -      100     100     100     95    10033       30         10    10     95     95      100     100     100   10034       60         0     0      100    100     100     100     100   10035       60         0     0      100    100     100     90      95    10040       250        20    0      30     40      100     95      100   8041       60         20    30     100    100     100     100     100   10045       125        0     0      95     100     100     100     90    9546       60         0     70     100    100     100     100     100   10047       30         0     0      100    95      100     100     100   10048       60         0     0      100    100     100     100     100   10051       30         0     20     100    -       100     95      100   100
实施例B：
幼苗长出地面后试验：
溶剂：  5重量份丙酮
乳化剂：1重量份烷芳基聚乙二醇醚
将1重量份活性化合物与所述量的溶剂混合，加入所述量的乳化剂，并将其用水稀释至所需浓度，即可制得适用的活性化合物制剂。
将5-15cm高的被试植物用活性化合物制剂喷洒，喷洒方法是每单位面积使用特定量的所需活性化合物。三周后，将植物的损伤程度以％损伤率形式与未受处理的对照组对比。数值表示：
0％＝无作用(如末处理对照组)
100％＝完全杀死。表C幼苗长出地面后试验/温室活性化合 施用量    小麦   玉米  苘麻属 苋属    藜属    茄属   婆婆纳属物(合成  (克/公顷)实例号)19       4         5      20    95     95      95      100    10020       4         0      15    100    95      95      100    9521       4         5      60    90     100     70      100    10022       30        15     0     100    100     40      100    2023       30        0      50    95     -       90      100    10024       30        15     70    100    100     100     100    10025       15        0      50    100    100     100     100    10026       15        0      30    50     90      50      50     1005        15        10     20    100    100     100     100    1003        30        10     30    100    100     100     100    1006        8         30     50    100    100     100     100    957        60        10     50    100    100     95      100    958        60        10     30    100    100     100     100    1009        60        10     30    100    100     100     100    1001        15        10     50    100    95      95      100    10012       8         10     30    100    100     95      100    10013       15        0      30    95     100     80      100    9016       60        20     60    95     100     100     100    10017       8         10     10    100    100     95      100    100表C(续)幼苗长出地面后试验/温室活性化合 施用量   小麦   玉米  苘麻  苋属    藜属   茄属   婆婆纳属物(合成  (克/公顷)             属实例号)28       30       0      30    100   100     90     100    10029       8        5      0     70    100     90     100    9530       8        0      50    100   100     95     100    7031       8        0      70    100   100     90     100    10032       4        15     30    100   100     95     100    10033       4        20     60    100   100     100    100    10034       15       0      30    100   100     100    100    10035       30       0      25    100   100     90     100    9540       125      10     5     50    70      100    100    9041       15       20     50    100   80      90     100    9543       15       0      50    100   95      100    100    10044       8        0      15    100   100     100    95     10045       8        10     40    95    95      95     100    -46       8        15     20    100   100     95     100    10047       8        10     10    100   100     95     100    10048       8        5      60    100   100     80     100    10049       8        0      60    60    100     10     100    10050       15       5      70    100   95      80     100    9551       15       15     60    100   100     70     100    100

Claims (8)

1.通式(I)的取代芳族硫代羧酰胺：
Figure C9519395300021
其中：R1代表氢或卤素，R2代表下述基团：
                   -A1-A2-A3
其中：
A1代表一个单键，或代表-O-或基团-N-A4，其中A4代表氢或C1-C4-烷基，
A2代表一个单键，-SO2-或C1-C6-链烷二基，
A3代表羟基、氨基、卤素，或者代表任选由卤素-或C1-C4-烷氧基取代的烷基或烷氧基，其在每种情况下具有1-6个碳原子，或具有2-6个碳原子的炔基，
R3代表氢或卤素，
Z代表通式Z1、Z2、Z3、Z9、Z10和Z15中的任何一个，
Figure C9519395300031
和
Figure C9519395300033
其中
Q1表示-CO-或CS；
R6表示氢、氟、氯、溴、甲基、乙基、正-或异丙基、环丙基、二氟甲基、三氟甲基和氯二氟甲基，和
R7表示甲基、乙基、正-或异丙基，或
其中，两个相邻的基团-R6和R6或R6和R7-共同表示C1-C4-链烷二基。
2.根据权利要求1的通式(I)取代芳族硫代羧酰胺，其特征在于：R1代表氢、氟或氯，R2代表下述基团
                       -A1-A2-A3
其中：
A1代表一个单键，-O-或基团-N-A4，其中A4代表氢或甲基，
A2代表一个单键、-SO2-、亚甲基或乙烷-1，1-二基，
A3代表羟基、氟、甲基、乙基、正-或异丙基、任选地氟-或甲氧基-取代的乙氧基、正-或异丙氧基、乙氧基乙氧基甲氧基或乙炔基，
R3代表氢。
3.根据权利要求1的式(I)取代芳族硫代羧酰胺，其特征在于：
R1代表氟，
R2代表-NH-SO2C2H5，R3表氢，和Z代表
4.通式(I)取代的芳族硫代羧酰胺的制备方法：
Figure C9519395300042
其中：R1、R2、R3和Z的定义与权利要求1相同；其特征在于：
使通式(II)的取代芳族腈：其中：R1、R2、R3和Z的定义与权利要求1相同，与硫化氢(H2S)或与硫代乙酰胺，任选地在反应助剂和任选地在稀释剂存在下反应。
5.抑制不需要植物的方法，其特征在于使权利要求1-3的通式(I)的取代芳族硫代羧酰胺作用于不需要的植物和/或它们的产地。
6.权利要求1-3的通式(I)的取代芳族硫代羧酰胺用于抑制不需要植物的用途。
7.除草剂组合物的制备方法，其特征在于使用权利要求1-3的通式(I)的取代芳族硫代羧酰胺与填充剂和/或表面活性剂混合。
8.除草剂组合物，其特征在于含有至少一种选自权利要求1-3的通式(I)的取代芳族硫代羧酰胺。
CN95193953A 1994-05-04 1995-04-21 取代的芳族硫代羧酰胺及其作为除草剂的用途 Expired - Fee Related CN1113875C (zh)

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US6331507B1 (en) 2001-12-18
RU2144029C1 (ru) 2000-01-10
US6077813A (en) 2000-06-20
WO1995030661A1 (de) 1995-11-16
MX9605270A (es) 1997-10-31
EP0758324B1 (de) 2005-03-16
AU693889B2 (en) 1998-07-09
EP0758324A1 (de) 1997-02-19
PL317122A1 (en) 1997-03-17
PT758324E (pt) 2005-07-29
JPH10500943A (ja) 1998-01-27
PL182505B1 (pl) 2002-01-31
US6451736B1 (en) 2002-09-17
HK1000888A1 (zh) 2004-04-02
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