公开(公告)号：US08115012B2

公开(公告)日：2012-02-14

申请号：US12513003

申请日：2007-11-02

申请人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

发明人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

IPC分类号： C07D231/10 ,  C07F7/08

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylates of the formula I in which R1 is C1-C8-alkyl, C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, etc.; and R2 is hydrogen, C1-C4-alkyl, benzyl or phenyl, wherein a) a compound of the general formula II in which X is fluorine, chlorine or bromine, R1 has one of the meanings given above and R4 is C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, benzyl or phenyl, is reacted with a silane compound of the general formula R3nSiCl(4-n) in which n is 1, 2 or 3 and the substituents R3 are independently of one another selected from the group consisting of C1-C8-alkyl and phenyl and with a metal selected from the metals of groups 1, 2, 3, 4 and 12 of the Periodic Table of the Elements having a redox potential of less than −0.7 V, based on a normal hydrogen electrode (at 25° C. and 101.325 kPa); and b) the reaction mixture from step a) is reacted with a compound of the general formula III R2HN—NH2  (III) in which R2 has one of the meanings given above.

摘要翻译： 本发明涉及制备式Ⅰ的二氟甲基取代的吡唑-4-基羧酸酯的方法，其中R 1是C 1 -C 8烷基，C 3 -C 8环烷基，C 1 -C 4烷氧基-C 1 -C 4烷基等 。 R 2是氢，C 1 -C 4 - 烷基，苄基或苯基，其中a）通式II的化合物，其中X是氟，氯或溴，R 1具有上面给出的含义之一，R 4是C 1 -C 8 - 烷基，C 3 -C 8 - 环烷基，C 2 -C 8 - 烯基，苄基或苯基与通式R 3 n SiCl（4-n）的硅烷化合物反应，其中n为1,2或3，取代基R 3独立地为 选自由C 1 -C 8 - 烷基和苯基组成的组中的一种，以及选自元素周期表第1,2,3,4和12族金属的金属，其氧化还原电位小于-0.7 V，基于正常的氢电极（在25℃和101.325kPa）; 和b）将来自步骤a）的反应混合物与通式III的化合物R2HN-NH2（III）反应，其中R2具有上述含义之一。

公开(公告)号：US20100069646A1

公开(公告)日：2010-03-18

申请号：US12513003

申请日：2007-11-02

申请人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

发明人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

IPC分类号： C07D231/10 ,  C07F7/08

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylates of the formula I in which R1 is C1-C8-alkyl, C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, etc.; and R2 is hydrogen, C1-C4-alkyl, benzyl or phenyl, wherein a) a compound of the general formula II in which X is fluorine, chlorine or bromine, R1 has one of the meanings given above and R4 is C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, benzyl or phenyl, is reacted with a silane compound of the general formula R3nSiCl(4-n) in which n is 1, 2 or 3 and the substituents R3 are independently of one another selected from the group consisting of C1-C8-alkyl and phenyl and with a metal selected from the metals of groups 1, 2, 3, 4 and 12 of the Periodic Table of the Elements having a redox potential of less than −0.7 V, based on a normal hydrogen electrode (at 25° C. and 101.325 kPa); and b) the reaction mixture from step a) is reacted with a compound of the general formula III R2HN—NH2   (III) in which R2 has one of the meanings given above.

摘要翻译： 本发明涉及制备式Ⅰ的二氟甲基取代的吡唑-4-基羧酸酯的方法，其中R 1是C 1 -C 8烷基，C 3 -C 8环烷基，C 1 -C 4烷氧基-C 1 -C 4烷基等 。 并且R 2是氢，C 1 -C 4 - 烷基，苄基或苯基，其中a）通式II的化合物，其中X是氟，氯或溴，R 1具有上面给出的含义之一，R 4是C 1 -C 8 - 烷基，C 3 -C 8 - 环烷基，C 2 -C 8 - 烯基，苄基或苯基与通式R 3 n SiCl（4-n）的硅烷化合物反应，其中n为1,2或3，取代基R 3独立地为 选自由C 1 -C 8 - 烷基和苯基组成的组中的一种，以及选自元素周期表第1,2,3,4和12族金属的金属，其氧化还原电位小于-0.7 V，基于正常的氢电极（在25℃和101.325kPa）; 和b）将来自步骤a）的反应混合物与通式III的化合物R2HN-NH2（III）反应，其中R2具有上述含义之一。

公开(公告)号：US20100174094A1

公开(公告)日：2010-07-08

申请号：US12601966

申请日：2008-05-30

申请人： Thomas Zierke ,  Joachim Rheinheimer ,  Michael Rack ,  Sebastian Peer Smidt ,  Ansgar Gereon Altenhoff ,  Joachim Schmidt-Leithoff ,  Nina Challand

发明人： Thomas Zierke ,  Joachim Rheinheimer ,  Michael Rack ,  Sebastian Peer Smidt ,  Ansgar Gereon Altenhoff ,  Joachim Schmidt-Leithoff ,  Nina Challand

IPC分类号： C07D231/18 ,  C07D231/12

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing N-substituted (3-dihalomethylpyrazol-4-yl)carboxamides of the formula (I) in which R1 is optionally substituted phenyl or C3-C7-cycloalkyl, R1a is hydrogen or fluorine, or R1a together with R1 is optionally substituted C3-C5-alkanediyl or C5-C7-cycloalkanediyl, R2 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C4-alkoxy-C1-C2-alkyl, X is F or Cl and n is 0, 1, 2 or 3; which comprises A) providing a compound of the formula (II) in which X is F or Cl, Y is Cl or Br and R2 has one of the meanings given above and B) reacting a compound of the formula (II) with carbon monoxide and a compound of the formula (III) in which R1, R1a and n have one of the meanings given above; in the presence of a palladium catalyst; to intermediates used for the preparation according to the process according to the invention, and also to processes for their preparation.

摘要翻译： 本发明涉及式（I）的N-取代的（3-二卤代甲基吡唑-4-基）甲酰胺的制备方法，其中R 1为任选取代的苯基或C 3 -C 7 - 环烷基，R 1a为氢或氟，或R 1a R 1是C 1 -C 6 - 烷基，C 2 -C 6 - 烯基，C 2 -C 6炔基或C 1 -C 4 - 烷氧基-C 1 -C 2 - 烷基，其中R 1是任选取代的C 3 -C 5 - 烷二基或C 5 -C 7 - 环烷二基， X是F或Cl，n是0,1,2或3; 其包括A）提供其中X为F或Cl，Y为Cl或Br的式（II）化合物，R 2具有上述含义之一，B）使式（II）化合物与一氧化碳 和其中R1，R1a和n具有上述含义之一的式（III）化合物; 在钯催化剂的存在下; 用于根据本发明的方法制备的中间体，以及其制备方法。

公开(公告)号：US08153820B2

公开(公告)日：2012-04-10

申请号：US12601966

申请日：2008-05-30

申请人： Thomas Zierke ,  Joachim Rheinheimer ,  Michael Rack ,  Sebastian Peer Smidt ,  Ansgar Gereon Altenhoff ,  Joachim Schmidt-Leithoff ,  Nina Challand

发明人： Thomas Zierke ,  Joachim Rheinheimer ,  Michael Rack ,  Sebastian Peer Smidt ,  Ansgar Gereon Altenhoff ,  Joachim Schmidt-Leithoff ,  Nina Challand

IPC分类号： C07D231/10

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing N-substituted (3-dihalomethylpyrazol-4-yl)carboxamides of the formula (I) in which R1 is optionally substituted phenyl or C3-C7-cycloalkyl, R1a is hydrogen or fluorine, or R1a together with R1 is optionally substituted C3-C5-alkanediyl or C5-C7-cycloalkanediyl, R2 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C4-alkoxy-C1-C2-alkyl, X is F or Cl and n is 0, 1, 2 or 3; which comprises A) providing a compound of the formula (II) in which X is F or Cl, Y is Cl or Br and R2 has one of the meanings given above and B) reacting a compound of the formula (II) with carbon monoxide and a compound of the formula (III) in which R1, R1a and n have one of the meanings given above; in the presence of a palladium catalyst; to intermediates used for the preparation according to the process according to the invention, and also to processes for their preparation.

摘要翻译： 本发明涉及式（I）的N-取代的（3-二卤代甲基吡唑-4-基）甲酰胺的制备方法，其中R 1为任选取代的苯基或C 3 -C 7 - 环烷基，R 1a为氢或氟，或R 1a R 1是C 1 -C 6 - 烷基，C 2 -C 6 - 烯基，C 2 -C 6炔基或C 1 -C 4 - 烷氧基-C 1 -C 2 - 烷基，其中R 1是任选取代的C 3 -C 5 - 烷二基或C 5 -C 7 - 环烷二基， X是F或Cl，n是0,1,2或3; 其包括A）提供其中X为F或Cl，Y为Cl或Br的式（II）化合物，R 2具有上述含义之一，B）使式（II）化合物与一氧化碳 和其中R1，R1a和n具有上述含义之一的式（III）化合物; 在钯催化剂的存在下; 用于根据本发明的方法制备的中间体，以及其制备方法。

公开(公告)号：US08299262B2

公开(公告)日：2012-10-30

申请号：US12746086

申请日：2008-11-21

申请人： Wassilios Grammenos ,  Jan Klaas Lohmann ,  Thomas Grote ,  Jochen Dietz ,  Bernd Mueller ,  Michael Puhl ,  Jens Renner ,  Sarah Ulmschneider ,  Marianna Vrettou ,  Joachim Rheinheimer

发明人： Wassilios Grammenos ,  Jan Klaas Lohmann ,  Thomas Grote ,  Jochen Dietz ,  Bernd Mueller ,  Michael Puhl ,  Jens Renner ,  Sarah Ulmschneider ,  Marianna Vrettou ,  Joachim Rheinheimer

IPC分类号： C07D213/62 ,  A61K31/44

CPC分类号： C07D213/643 ,  A01N43/40 ,  A01N43/42 ,  A01N43/54 ,  A01N43/56 ,  A01N43/58 ,  A01N43/78 ,  A01N43/80 ,  C07D213/30 ,  C07D213/69 ,  C07D213/70 ,  C07D213/71 ,  C07D213/74 ,  C07D213/79 ,  C07D217/24 ,  C07D237/14 ,  C07D237/16 ,  C07D239/34 ,  C07D239/54 ,  C07D239/60 ,  C07D261/08 ,  C07D261/12 ,  C07D277/24 ,  C07D277/34 ,  C07D401/12 ,  C07D413/12 ,  C07D417/12 ,  A01N37/34 ,  A01N43/653 ,  A01N47/04 ,  A01N47/24 ,  A01N2300/00

摘要： The present invention relates to novel pyridylmethyl-sulfonamide compounds of formula (I) where: n is 0 to 4; m is 0 to 4; R1 is halogen, CN, NO2, OH, SH, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, etc.; and/or two radicals R1 together form a fused ring; R2 is H, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C8-cycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl or benzyl; R3 is halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; Y is —O—, C1-C4-alkanediyl, —O—CH2—, —CH2—O—, —C(NORn)—, —S—, —S(═O)—, —S(═O)2— or —N(Rn)—; and the N-oxides, and salts thereof and their use for combating phytopathogenic harmful fungi, and also to compositions and seed comprising at least one such compound.

摘要翻译： 本发明涉及式（I）的新的吡啶基甲基磺酰胺化合物，其中：n为0至4; m为0〜4; R1是卤素，CN，NO2，OH，SH，C1-C4-烷基，C1-C4卤代烷基，C1-C4-烷氧基，C1-C4-卤代烷氧基等。 和/或两个基团R 1一起形成稠环; R2是H，C1-C4-烷基，C1-C4-卤代烷基，C2-C4-烯基，C2-C4-炔基，C3-C8-环烷基，C1-C4烷基-C3-C8-环烷基或苄基; R 3是卤素，CN，NO 2，C 1 -C 4烷基，C 1 -C 4卤代烷基，C 1 -C 4 - 烷氧基或C 1 -C 4卤代烷氧基; Y是-O - ， - C 1 -C 4 - 烷二基，-O-CH 2 - ， - CH 2 -O-，-C（NORn） - ， - S - ， - S（= O） - ， - S（= O）2 - 或-N（Rn） - ; 及其N-氧化物及其盐及其用于防治植物病原性有害真菌的用途，以及包含至少一种此类化合物的组合物和种子。

公开(公告)号：US20110004021A1

公开(公告)日：2011-01-06

申请号：US12876415

申请日：2010-09-07

申请人： Jochen DIETZ ,  Markus Gewehr ,  Thomas Grote ,  Wassilios Grammenos ,  Udo Hünger ,  Bernd Müller ,  Frank Schieweck ,  Anja Schwögler ,  Jan Klaas Lohmann ,  Joachim Rheinheimer ,  Jens Renner ,  Peter Schäfer

发明人： Jochen DIETZ ,  Markus Gewehr ,  Thomas Grote ,  Wassilios Grammenos ,  Udo Hünger ,  Bernd Müller ,  Frank Schieweck ,  Anja Schwögler ,  Jan Klaas Lohmann ,  Joachim Rheinheimer ,  Jens Renner ,  Peter Schäfer

IPC分类号： C07C211/52

CPC分类号： C07D277/56 ,  C07D277/587

摘要： Thiazolecarboxanilides of the formula I in which the variables are as defined below: A is X is halogen; Y is cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, methoxy or methylthio; p is 0, 1; R1 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl; R2 is hydrogen, methyl, halogen; R3 is hydrogen, methyl, ethyl; W is O, S; and processes for preparing these compounds, compositions and seed comprising them and methods for controlling harmful fungi.

摘要翻译： 式I的噻唑甲酰苯胺，其中变量如下定义：A是X是卤素; Y是氰基，硝基，C 1 -C 4烷基，C 1 -C 4卤代烷基，甲氧基或甲硫基; p为0，1; R1是氢，卤素，C1-C4-烷基，C1-C4卤代烷基; R2是氢，甲基，卤素; R3是氢，甲基，乙基; W是O，S; 以及制备这些化合物，组合物和包含它们的种子的方法以及用于控制有害真菌的方法。

公开(公告)号：US20080153707A1

公开(公告)日：2008-06-26

申请号：US11883957

申请日：2006-02-15

申请人： Markus Gewehr ,  Jochen Dietz ,  Thomas Grote ,  Carsten Blettner ,  Wassilios Grammenos ,  Udo Hunger ,  Bernd Muller ,  Frank Schieweck ,  Anja Schwogler ,  Jan Klaas Lohmann ,  Joachim Rheinheimer ,  Peter Schafer ,  Siegfried Strathmann ,  Reinhard Stierl

发明人： Markus Gewehr ,  Jochen Dietz ,  Thomas Grote ,  Carsten Blettner ,  Wassilios Grammenos ,  Udo Hunger ,  Bernd Muller ,  Frank Schieweck ,  Anja Schwogler ,  Jan Klaas Lohmann ,  Joachim Rheinheimer ,  Peter Schafer ,  Siegfried Strathmann ,  Reinhard Stierl

IPC分类号： A01N43/56 ,  C07D231/00 ,  A01N25/26

CPC分类号： C07D231/14 ,  A01N43/56

摘要： The present invention relates to pyrazolecarboxanilides I in which the variables are as defined below: n is zero or 2; m is 2 or 3; X1 is fluorine or chlorine; X2 is halogen; Y is CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, methoxy or methylthio; p is zero or 1; R1 is fluorine, chlorine, bromine, C1-C4-alkyl or C1-C4-haloalkyl; R2 is hydrogen or halogen; R3 is hydrogen, methyl or ethyl; W is O or S; with the proviso that, if a) W═O, R1=methyl and R3 is hydrogen, R2 is not fluorine, or b) W═O, n=0, m=2, p=0, R2 and R3 are hydrogen, R1 is not trifluoromethyl or difluoromethyl, to processes for preparing these compounds, to compositions comprising them and to methods for using them for controlling harmful fungi.

摘要翻译： 本发明涉及吡唑烷酰苯胺I，其中变量如下：n为0或2; m为2或3; X 1是氟或氯; X 2是卤素; Y是CN，NO 2，C 1 -C 4 - 烷基，C 1 -C 3 - 4 - 卤代烷基，甲氧基或甲硫基; p为零或1; R 1是氟，氯，溴，C 1 -C 4 - C 1-4烷基或C 1 -C 3 - 低级烷基; R 2是氢或卤素; R 3是氢，甲基或乙基; W为O或S; 条件是，如果a）WO，R 1 =甲基和R 3是氢，R 2不是氟，或b） WO，n = 0，m = 2，p = 0，R 2和R 3是氢，R 1不是三氟甲基或二氟甲基 ，制备这些化合物的方法，包含它们的组合物以及用于控制有害真菌的方法。

公开(公告)号：US20080125445A1

公开(公告)日：2008-05-29

申请号：US11885359

申请日：2006-03-01

申请人： Peter Schafer ,  Udo Hunger ,  Maria Scherer ,  Harald Kohle ,  Helmut Schiffer ,  Thomas Grote ,  Jochen Dietz ,  Wassilios Grammenos ,  Jan Klaas Lohmann ,  Bernd Muller ,  Joachim Rheinheimer ,  Frank Schieweck ,  Anja Schwogler

发明人： Peter Schafer ,  Udo Hunger ,  Maria Scherer ,  Harald Kohle ,  Helmut Schiffer ,  Thomas Grote ,  Jochen Dietz ,  Wassilios Grammenos ,  Jan Klaas Lohmann ,  Bernd Muller ,  Joachim Rheinheimer ,  Frank Schieweck ,  Anja Schwogler

IPC分类号： A01N43/90 ,  C07D487/04 ,  A01P3/00

CPC分类号： C07D487/04

摘要： 5,6-Dialkyl-7-aminoazolopyrimidines of the formula I in which the substituents are as defined below: R1 is alkyl or alkoxyalkyl, R2 is alkyl, where R1 and/or R2 may be substituted according to the description, A is N or CH, and R3 is CH3 and, if A is CH, additionally hydrogen; processes and intermediates for preparing these compounds, compositions comprising them and their use for controlling phytopathogenic harmful fungi.

摘要翻译： 其中取代基如下定义的式I的5,6-二烷基-7-氨基偶氮嘧啶：R 1是烷基或烷氧基烷基，R 2是烷基，其中R 根据描述，可以取代1和/或R 2，A是N或CH，R 3是CH 3 如果A是CH，另外是氢; 制备这些化合物的方法和中间体，包含它们的组合物及其用于控制​​植物病原性有害真菌的用途。

公开(公告)号：US08178540B2

公开(公告)日：2012-05-15

申请号：US12515138

申请日：2007-11-21

申请人： Jan Klaas Lohmann ,  Wassilios Grammenos ,  Michael Puhl ,  Jochen Dietz ,  Bernd Müller ,  Joachim Rheinheimer ,  Jens Renner ,  Marianna Vrettou ,  Sarah Ulmschneider ,  Thomas Grote

发明人： Jan Klaas Lohmann ,  Wassilios Grammenos ,  Michael Puhl ,  Jochen Dietz ,  Bernd Müller ,  Joachim Rheinheimer ,  Jens Renner ,  Marianna Vrettou ,  Sarah Ulmschneider ,  Thomas Grote

IPC分类号： C07D239/20 ,  C07D239/22 ,  C07D403/12 ,  A01N43/54

CPC分类号： C07D239/20 ,  A01N43/54 ,  A01N43/56 ,  A01N43/78 ,  C07D239/22 ,  C07D401/12 ,  C07D403/12 ,  C07D405/12 ,  C07D409/12 ,  C07D413/12 ,  C07D417/12

摘要： The present invention relates to novel pyrimidylmethyl-sulfonamide compounds and to their N-oxides, their agriculturally acceptable salts and their veterinarily acceptable salts and also to agricultural compositions comprising at least one such compound as active component, and also to their use for controlling harmful fungi. The present invention also relates to a method for controlling arthropod pests.

摘要翻译： 本发明涉及新的嘧啶基甲基 - 磺酰胺化合物及其N-氧化物，其农业上可接受的盐及其兽医学上可接受的盐，还涉及包含至少一种这样的活性成分的化合物的农业组合物，以及它们用于控制有害真菌的用途 。 本发明还涉及一种防治节肢动物害虫的方法。

公开(公告)号：US07799334B2

公开(公告)日：2010-09-21

申请号：US11919588

申请日：2006-05-10

申请人： Markus Gewehr ,  Jochen Dietz ,  Thomas Grote ,  Wassilios Grammenos ,  Udo Hünger ,  Bernd Müller ,  Frank Schieweck ,  Anja Schwögler ,  Jan Klaas Lohmann ,  Joachim Rheinheimer ,  Jens Renner ,  Peter Schäfer

发明人： Markus Gewehr ,  Jochen Dietz ,  Thomas Grote ,  Wassilios Grammenos ,  Udo Hünger ,  Bernd Müller ,  Frank Schieweck ,  Anja Schwögler ,  Jan Klaas Lohmann ,  Joachim Rheinheimer ,  Jens Renner ,  Peter Schäfer

IPC分类号： A61K31/16 ,  A01N25/00 ,  C07D231/00 ,  A01N25/26 ,  A01N37/18

CPC分类号： A01N43/56 ,  C07D231/14

摘要： The present invention relates to pyrazolecarboxamides of the formula I in which the variables are as defined below: X is trifluoromethyl; R1 is F, Cl, Br, C1-C4-alkyl or C1-C4-haloalkyl; R2 is hydrogen, halogen or C1-C4-alkyl; R3 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl; W is O or S; with the proviso that, if R3 is hydrogen and W is oxygen, a) R1 and R2 are not simultaneously methyl and F, respectively; b) R1 and R2 are not simultaneously trifluoromethyl and hydrogen or fluorine, respectively. to processes for preparing these compounds, to seeds and compositions comprising them and to methods for controlling harmful fungi.

摘要翻译： 本发明涉及式I的吡唑酰胺，其中变量如下所定义：X是三氟甲基; R1是F，Cl，Br，C1-C4-烷基或C1-C4卤代烷基; R2是氢，卤素或C1-C4-烷基; R 3是氢，C 1 -C 4 - 烷基，C 1 -C 4卤代烷基，C 2 -C 4 - 烯基，C 2 -C 4 - 炔基或C 3 -C 6 - 环烷基; W为O或S; 条件是，如果R3是氢并且W是氧，则a）R1和R2分别不同时为甲基和F; b）R1和R2分别不同时为三氟甲基和氢或氟。 制备这些化合物的方法，包括它们的种子和组合物以及用于控制有害真菌的方法。