Microbiocidal N-phenyl-N-[4-(4-pyridyl-2-pyrimidin-2-yl]-amine derivatives

    公开(公告)号:US07074787B2

    公开(公告)日:2006-07-11

    申请号:US10451930

    申请日:2001-12-20

    摘要: The invention relates to novel N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives of the general formula (I) wherein the sum of (m+p) together is 0, 1, 2 or 3; n and q are independently of each other 0 or 1, and the sum of (m+p+q) together is 1, 2, 3 or 4; R1 is hydrogen, halogen, alkoxy, haloalkyl, haloalkoxy or alkyl; R2 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl or C1–C6-alkoxy; R2A is hydrogen, C1–C6-alkyl, C3–C4-alkenyl or C3–C4-alkynyl; each of R3, R4, R5 and R6 is, independently of the others, hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, hydroxy-C1–C6-alkyl or C1–C6-alkoxy-C1–C6-alkyl, or the ring members CR3R4 or CR5R6 or CR2R2A are independently of each other a carbonyl group (C═O) or a group C═S; X is C═O, C═S, S═O or O═S═O; Y is O, S, C═O, CH2, —N(R8)—, —O—N(R8)—, —N(R8)—O— or NH—; R7 is hydrogen, C1–C4-alkyl, C3–C4-alkenyl, C3–C4-alkynyl, —CH2OR8, CH2SR8, —C(O)R8, —C(O)OR8, SO2R8, SOR8 or SR8; and R8 is C1–C8-alkyl, C1–C8-alkoxyalkyl, C1–C8 haloalkyl or phenylC1–C2-alkyl wherein the phenyl may be substituted by up to three groups selected from halo or C1–C4-alkyl; or a salt thereof. The invention also relates to the preparation of the compounds and to agrochemical compositions comprising at least one of those compounds as active ingredient as well as the preparation of the said compositions and to the use of the compounds or of the compositions in controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.

    Process for the preparation of substituted difluorobenzo-1,3-dioxoles
    7.
    发明授权
    Process for the preparation of substituted difluorobenzo-1,3-dioxoles 失效
    制备取代的二氟苯-1,3-二氧杂环戊烯的方法

    公开(公告)号:US5420301A

    公开(公告)日:1995-05-30

    申请号:US147617

    申请日:1993-11-05

    摘要: The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkyl-phenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 fluoroalkyl, nitro or by cyano, or is C.sub.1 -C.sub.12 acyl, or wherein R.sup.1 is a radical of formula II ##STR2## wherein R.sup.5 is --CN, --CF.sub.3, --COOR.sup.2, --CONH.sup.2, --CO--NHR.sup.2 or --CONR.sub.2.sup.2, R.sup.3 and R.sup.4 are a direct bond or each is H, or R.sup.3 is H and R.sup.4 independently has the meanings of R.sup.5, or R.sup.3 and R.sup.4 together are --CH.sub.2 --NR.sup.6 --CH.sub.2 --, --CH.sub.2 --NR.sup.6 --CO-- or --CO--NR.sup.6 --CO-- wherein R.sup.6 is the radical of a removable protecting group, or wherein further R.sup.1 is a radical of formula III ##STR3## Insecticides or fungicides can be prepared from the compounds of formula I.3-(2,2-difluorobenzodioxol-4-yl)-4-cyanopyrrole can be prepared by reacting 4-metallo-2,2-difluorobenzodioxole (III) with an unsaturated nitrile and then with a sulfonylmethyl isocyanide in a one-pot process. The compounds III are novel intermediates.

    摘要翻译: 2,2-二氟苯-1,3-二氧杂环戊烯与(a)碱金属或碱金属化合物反应,然后(b)其中Z 1为离去基团的化合物R1-Z1或与醛反应生成化合物 其中R 1是-OH,-SH,-CHO,-CN,-COOH,-B(OH)2,-COX,X是Cl或Br,或者是-COOR 2, - SiR 32或-B(OR 2)2,其中R 2是没有羟基的C 1 -C 12醇部分,其中R 1还是-C n H 2n NOR 2,n是1至4的整数,或未被取代的直链或支链C 1 -C 12羟基烷基 被-F,-CN,C 1 -C 6烷氧基,苯基,氟苯基,C 1 -C 4烷氧基 - 苯基,C 1 -C 4烷硫基 - 苯基,C 1 -C 4烷基 - 苯基,C 1 -C 4氟烷基 - 苯基,硝基苯基或氰基苯基取代,或其中R 1为 苄基醇,其未被取代或被F,C 1 -C 4烷氧基,C 1 -C 4烷硫基,C 1 -C 4烷基,C 1 -C 4氟烷基,硝基或氰基取代,或者是C 1 -C 12酰基,或其中R 1是式II基团。 (II)其中R5是-CN,-CF3,-COOR2,-CONH2,-CO-NHR 2或-CONR 22,R 3和R 4是直接键或各自为H或R 3为H且R 4独立地具有R 5的含义,或者R 3和R 4一起为-CH 2 -NR 6 -CH 2 - , - CH 2 -NR 6 -CO - 或-CO-NR 6 -CO-,其中R 6是可除去的保护基的基团,或其中R 1是式III的基团由式I化合物制备。3-(2,2-二氟苯并二氧杂环戊烯-4-基) 4-氰基吡咯可以通过4-金属-2,2-二氟苯并二氧杂环戊烯(III)与不饱和腈然后与一种磺酰基甲基异氰化物反应来制备。 化合物III是新的中间体。

    .alpha.-methyl-(6-phenoxy)-2-picolyl cyclopropanecaraboxylates having
pesticidal activity
    8.
    发明授权
    .alpha.-methyl-(6-phenoxy)-2-picolyl cyclopropanecaraboxylates having pesticidal activity 失效
    具有杀虫活性的α-甲基 - (6-苯氧基)-2-甲基吡咯烷基环丙烷甲醛

    公开(公告)号:US4822806A

    公开(公告)日:1989-04-18

    申请号:US2370

    申请日:1987-01-12

    申请人: Peter Ackermann

    发明人: Peter Ackermann

    CPC分类号: C07D213/647 A01N53/00

    摘要: The invention relates to .alpha.-methyl-(6-phenoxy)-2-picolyl cyclopropanecarboxylates of the formula ##STR1## wherein X.sub.1 is methyl or halogen,R.sub.1 is hydrogen or halogen, andR.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, nitro or cyano.The invention also relates to the preparation of these esters and to the use thereof in pest control.

    摘要翻译: 本发明涉及式(I)的α-甲基 - (6-苯氧基)-2-甲基吡咯烷基环丙烷羧酸酯,其中X 1是甲基或卤素,R 1是氢或卤素,R 2是氢,卤素,C 1 -C 4烷基 C1-C4烷氧基,C1-C4烷硫基,C1-C4卤代烷基,C1-C4卤代烷氧基,C1-C4卤代烷硫基,C2-C4链烯基,C2-C4炔基,硝基或氰基。 本发明还涉及这些酯的制备及其在害虫防治中的应用。

    Substituted benzylcyclopropylmethyl ethers
    9.
    发明授权
    Substituted benzylcyclopropylmethyl ethers 失效
    取代的苄基环丙基甲基醚

    公开(公告)号:US4786654A

    公开(公告)日:1988-11-22

    申请号:US53911

    申请日:1987-05-26

    CPC分类号: C07C43/29 A01N31/14 A01N31/16

    摘要: There are disclosed novel unsubstituted or substituted phenoxyfluorobenzyltetramethylcyclopropylmethyl ethers of formula ##STR1## wherein Y is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1 to 9 halogen atoms, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkoxy which is substituted by 1 to 9 halogen atoms, C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkylthio which is substituted by 1 to 9 halogen atoms, or is C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl and their benzyl ether intermediates of formula IV ##STR2## wherein X is halogen or p-tosyl. Also disclosed is a process for the preparation of these compounds and compositions containing them for use in pest control, especially for controlling insects that attack plants and animals, in particular their larval stages. The novel compounds are particularly effective against plant-destructive insects in rice crops.

    摘要翻译: 公开了式(I)的新的未取代或取代的苯氧基氟苄基四甲基环丙基甲基醚,其中Y是氢,卤素,C 1 -C 4烷基或被1至9个卤素原子取代的C 1 -C 4烷基,C 1 -C 4烷氧基或C 1 -C 4烷氧基, 被1至9个卤素原子取代,被1至9个卤素原子取代的C 1 -C 4烷硫基或C 1 -C 4烷硫基,或者是C 2 -C 4烯基或C 2 -C 4炔基及其式IV的苄基醚中间体其中X 是卤素或对甲苯磺酰基。 还公开了一种用于制备这些化合物和含有它们的组合物用于病虫害防治的方法,特别是用于防治攻击植物和动物,特别是其幼虫期的昆虫。 新型化合物对水稻作物中的植物性破坏性昆虫特别有效。