TW200528434A - Hexylcarboxanilides - Google Patents

Hexylcarboxanilides Download PDF

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TW200528434A
TW200528434A TW093132066A TW93132066A TW200528434A TW 200528434 A TW200528434 A TW 200528434A TW 093132066 A TW093132066 A TW 093132066A TW 93132066 A TW93132066 A TW 93132066A TW 200528434 A TW200528434 A TW 200528434A
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alkyl
group
fluorine
chlorine
formula
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TW093132066A
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Chinese (zh)
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Ralf Dunkel
Hans-Ludwig Elbe
Olaf Gebauer
Joerg Nico Greul
Benoit Hartmann
Ulrike Wachendorff-Neumann
Peter Dahmen
Karl-Heinz Kuck
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Bayer Cropscience Ag
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    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract

Novel hexylcarboxanilides of the formula (I), , in which L, R1, R3 and A are as defined in the description, a plurality of processes for preparing these compounds and their use for controlling microorganisms, and also novel intermediates and their preparation.

Description

200528434 九、發明說明： 【發明所屬之技術領域】 本發明係有關一種新穎己基醯基苯胺，及製備此等化 合物之多種方法及其於控制不要之微生物上之用途。 5 【先前技術】 已知多種醯基苯胺類具有殺真菌劑性質（參見例如： WO 03/010149、WO 02/059086、WO 02/38542、WO · 00/09482、EP-A 0 591 699、EP-A 0 589 301 與 EP-A 0 545 ίο 〇99)。因此例如：5-氟-1，3二曱基-N-[2-(l，3,3-三甲基丁基） 苯基;1-1H-吡唑-4-羧醯胺係自WO 03/010149中已知者， N-烯丙基-N-[2-(l，3二曱基丁基）苯基]-1-曱基-3-(三氟甲 基)-1Η-吡唑羧醯胺係自WO 02/059086中已知者，及 N-[2-(1,3二甲基丁基）苯基]小甲基4-(三氟甲基)-lH-吡略 15 _3_羧醯胺係自WO 02/38542中已知者。此等化合物之活 性良好；然而，有時候在低施用率下仍不令人滿意。 【發明内容】 本發明現在提供一種新穎之式(I)己基醯基笨胺 200528434 L 代表200528434 IX. Description of the invention: [Technical field to which the invention belongs] The present invention relates to a novel hexylfluorenylaniline, and various methods for preparing these compounds and their use in controlling unwanted microorganisms. 5 [Prior art] A variety of fluorenylanilines are known to have fungicide properties (see for example: WO 03/010149, WO 02/059086, WO 02/38542, WO · 00/09482, EP-A 0 591 699, EP -A 0 589 301 and EP-A 0 545 ίο 〇99). So for example: 5-fluoro-1,3 difluorenyl-N- [2- (l, 3,3-trimethylbutyl) phenyl; 1-1H-pyrazole-4-carboxamide is from WO Known from 03/010149, N-allyl-N- [2- (l, 3-difluorenylbutyl) phenyl] -1-fluorenyl-3- (trifluoromethyl) -1fluorene-pyridine Zoconazole is known from WO 02/059086, and N- [2- (1,3dimethylbutyl) phenyl] small methyl 4- (trifluoromethyl) -1H-pyrillo 15_3_ Carboxamide is known from WO 02/38542. The activity of these compounds is good; however, sometimes it is still unsatisfactory at low application rates. [Summary of the Invention] The present invention now provides a novel formula (I) hexylfluorenyl benzylamine 200528434 L represents

5 ^ 、之鍵結係附接醯胺，而標示#之鍵結則附接 燒基側鏈， R 氫、CrC8-烷基、q-cv烷基亞磺醯基、crc6-烷 石戸、醯基、烷氧基-CVCV烷基、C3-CV環烷基； 燒基、C1-C4蝻烷硫基、crc4-鹵烷基-亞磺醯 基、CrCV鹵烷基磺醯基、鹵_Ci-C4_烷氧基_Crc4i 基、C^CV鹵環烷基，其分別具有1至9個氟、氯與/ 或漠原子；甲醯基、甲醯基-CrC3-烷基、（Q-C3-烷基） 幾基-CVC3·烷基、（Cl_c3_烷氧基)羰基_Cl_c3_烷基；鹵 -(CrCV烧基）羰基-c^c3-烧基、鹵-(Crc3-烧氧基）幾 基-CVCV烧基，其分別具有丨至13個I、氯與/或溴 原子； (Crc8-烧基)幾基、（CVC8-烧氧基)幾基、（CVCr烧氧 基-CrC4-烷基）羰基、（C3-CV環烷基)羰基；（crc6-鹵 烷基)羰基、（Crc6-鹵烷氧基)羰基、（鹵-Ci-Cr烷氧基 -C1-C4-烧基)数基、（C3-C8-鹵環烧基)羰基，其分別具 有1至9個氟、氯與/或溴原子；或-C(=0)C(=0)R4、 -CONR5R6 或-ch2nr7r8， R2代表氫、氟、氯、曱基或三氟甲基， 200528434 R3代表鹵素、C卜C8-烷基、crc8-鹵烧基， R 代表鼠、CrC8-烧基、Ci-CV烧氧基、CVC^燒氣臭 -Ci-C4-炫基、C3_CV環炫基；crc6-鹵烧基、c Γ 烧氧基、鹵-CrC4_烧氧基-Ci-C4·烧基、CyC8·齒譬广 基，其分別具有1至9個氟、氯與/或溴原子， R與R分別獨立代表氬、Ci-Cg-烧基、C^-Czr烧氧基c 烷基、C3-C8-環烷基；crc8-鹵烷基、鹵-CVC4-燒氧又 -CVC4-烧基、c3-c8-鹵環炫基，其分別具有1至9二 氟、氯與/或溴原子， R5與R6亦可與其所附接之氮原子共同形成具有5至8個 環組員之飽和雜環， 其可視需要經選自i素與CrCU-烧基之相同或相異取 代基單取代或多取代，其中該雜環可另包含1或2個 選自氧、硫與NR9中之不相鄰雜原子， R7與R8分別獨立代表氫、Cl-C8-烧基、c3_c8_環烷基； Ci-C8-鹵烷基、C^CV由環烷基，其分別具有1至9個 氟、氯與/或溴原子， R與R8亦可與其所附接之氮原子共同形成具有5至8個 環原子之飽和雜環， 其可視需要經選自鹵素與C1_C4-烷基之相同或相異取 代基單取代或多取代，其中該雜環可另包含丨戒2個 選自氧、硫與NR9中之不相_原子， R 代表氳或Ci_C6_烧基， A 代表式(A1)基團 2005284345 ^, the bond is attached to fluorene, and the bond labeled # is attached to the alkynyl side chain, R hydrogen, CrC8-alkyl, q-cv alkylsulfinyl fluorenyl, crc6-alkane fluorene, fluorene Alkyl, alkoxy-CVCV alkyl, C3-CV cycloalkyl; alkyl, C1-C4 alkylsulfanyl, crc4-haloalkyl-sulfinyl, CrCV haloalkylsulfonyl, halo_Ci -C4_alkoxy_Crc4i group, C ^ CV halocycloalkyl group, which respectively have 1 to 9 fluorine, chlorine and / or desert atoms; formamyl, formamyl-CrC3-alkyl, (Q- C3-Alkyl) Isopropyl-CVC3 · alkyl, (Cl_c3_alkoxy) carbonyl_Cl_c3_alkyl; halo- (CrCV alkyl) carbonyl-c ^ c3-alkyl, halo- (Crc3-alkylene A) aryl-CVCV alkynyl, which has from 1 to 13 I, chlorine and / or bromine atoms; (Crc8- alkynyl) alkynyl, (CVC8- alkoxy) alkynyl, (CVCr alkoxy- CrC4-alkyl) carbonyl, (C3-CV cycloalkyl) carbonyl; (crc6-haloalkyl) carbonyl, (Crc6-haloalkoxy) carbonyl, (halo-Ci-Cralkoxy-C1-C4- Alkyl), (C3-C8-halocycloalkyl) carbonyl, each having 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R4, -CONR5R6 Or -ch2nr7r8, R2 represents hydrogen, , Chloro, fluorenyl or trifluoromethyl, 200528434 R3 stands for halogen, C8-C8-alkyl, crc8-halohalo, R stands for rat, CrC8-alkyl, Ci-CVoxy, CVC -Ci-C4-Hexyl, C3_CV cyclohexyl; crc6-halohalo, c Γ alkoxy, halo-CrC4_alkoxy-Ci-C4 · alkoxy, CyC8 · dentate, each of which has 1 to 9 fluorine, chlorine and / or bromine atoms, R and R each independently represent argon, Ci-Cg-carbyl, C ^ -Czr alkyloxy c alkyl, C3-C8-cycloalkyl; crc8-halo Alkyl, halo-CVC4-carboxy and -CVC4-carbyl, c3-c8-halocyclohexyl, each having 1 to 9 difluoro, chlorine and / or bromine atoms, R5 and R6 can also be attached to it The nitrogen atoms together form a saturated heterocyclic ring having 5 to 8 ring members, which may be mono- or poly-substituted with the same or different substituents selected from the group consisting of i and CrCU-alkyl, as necessary, wherein the heterocyclic ring may further include 1 or 2 non-adjacent heteroatoms selected from oxygen, sulfur and NR9, R7 and R8 each independently represent hydrogen, Cl-C8-alkyl, c3_c8_cycloalkyl; Ci-C8-haloalkyl, C ^ CV is a cycloalkyl group, which has 1 to 9 fluorine, chlorine and / or bromine atoms, and R and R8 can also be attached to it The nitrogen atoms together form a saturated heterocyclic ring having 5 to 8 ring atoms, which may be mono- or poly-substituted with the same or different substituents selected from halogen and C1-C4-alkyl, if necessary, wherein the heterocyclic ring may further include 丨Or 2 different atoms selected from oxygen, sulfur, and NR9, R represents fluorene or Ci_C6_alkyl, and A represents a group of formula (A1) 200528434

(Al)，其中 5 10 15 R1()代表氳、經基、曱醯基、氰基、氟、氯、溴、靖 基、CVC4-烧基、CVCzr烧氧基、CVC4-烧硫基、 C3_C6-環烧基、Ci-C4-_烧基、Ci-C4-|^烧氧基或 C1-C4-鹵烧硫基（其分別具有1至5個鹵原子）、胺 基羰基或胺基羰基-CrCr烷基， R11代表氳、氯、漠、蛾、氰基、CrC4-烧基、c^cv 烷氧基、cKc4·烷硫基、q-cvi烷基或cvcv 鹵烧硫基（其分別具有1至5個鹵原子），及 R12代表氫、CVC4-烷基、羥基-CrCr烷基、c2-CV 稀基、C3-C6-壞烧基、C1-C4"·烧疏基-C1-C4-烧基、 C1-C4-烧fL基-Ci_C4-烧基、Ci_Czr_ 烧基、CrCf 鹵烧硫基-CVCV烧基、Q-CVi烧氧基-CVCV烧 基(其分別具有1至5個鹵原子），或代表苯基， 或 A 代表(A2)基團(Al), where 5 10 15 R1 () represents fluorene, fluorenyl, fluorenyl, cyano, fluorine, chlorine, bromine, sulfonyl, CVC4-carbyl, CVCzr alkoxy, CVC4-sulfanyl, C3_C6- Cycloalkyl, Ci-C4-alkyl, Ci-C4- | alkyl, or C1-C4-halothio (which each have 1 to 5 halogen atoms), aminocarbonyl, or aminocarbonyl- CrCr alkyl, R11 represents pyrene, chlorine, molybdenum, moth, cyano, CrC4-alkyl, c ^ cv alkoxy, cKc4 · alkylthio, q-cvi alkyl, or cvcv halothio (which respectively have 1 to 5 halogen atoms), and R12 represents hydrogen, CVC4-alkyl, hydroxy-CrCr alkyl, c2-CV dilute group, C3-C6-bad alkyl, C1-C4 " · burner-C1-C4 -Carbonyl, C1-C4-Carbonyl-Ci_C4-Carbonyl, Ci_Czr_Carbonyl, CrCf Halothio-CVCV Carbo, Q-CVi Caroxy-CVCV Carbo (which each have 1 to 5 halogens Atom), or represents phenyl, or A represents (A2) group

(A2)，其中 R與R14分別獨立代表氫、鹵素、CrC4烷基或具有 1至5個鹵原子之CrC4』烷基， 20 200528434 或 A 代表式(A3)基團 R代表_素、氰基或q-C4烷基，或crc4鹵烷基或 crC4_鹵烧氧基（其分別具有1至$個鹵原子），(A2), wherein R and R14 each independently represent hydrogen, halogen, CrC4 alkyl group or CrC4 ′ alkyl group having 1 to 5 halogen atoms, 20 200528434 or A represents a group of formula (A3), R represents a hydrogen atom, a cyano group Or q-C4 alkyl, or crc4 haloalkyl or crC4_halohaloxy (which have 1 to $ halogen atoms, respectively),

R與R17分別獨立代表氫、鹵素、烷基或具有 Μ 1至5個鹵原子之Ci_c4_齒烷基，及 R代表氫、烷基或具有1至5個鹵原子之 CrCVi烧基， 或 A 代表式(A4)基團R and R17 each independently represent hydrogen, halogen, alkyl or Ci_c4-dental alkyl having M 1 to 5 halogen atoms, and R represents hydrogen, alkyl, or CrCVi alkyl having 1 to 5 halogen atoms, or A Representative (A4) group

R代表由素、羥基、氰基、CrCV烷基、CVCV烷氣， 基、Crc4-烧硫基、crC4__烷基、CVQ-齒烷硫 基或CVCr鹵烷氧基(其分別具有丨至5個鹵原 子）， R20代表氫、自素、氰基、CrCr烧基、CrC；4·烧‘氧基、 CrCV烷硫基、CrC：4_^烷基、ο%卣烷氧基(其 分別具有1至5個鹵原子）、及Crar烷亞磺醯基 或Ci-C4-烧續酿基， 200528434 或 A 代表式(A5)基團R represents a hydrogen atom, a hydroxyl group, a cyano group, a CrCV alkyl group, a CVCV alkane group, a Crc4-sulfanyl group, a crC4__alkyl group, a CVQ-haloalkylthio group, or a CVCr haloalkoxy group (which respectively have 丨 to 5 Halogen atoms), R20 represents hydrogen, sulfonium, cyano, CrCr alkyl, CrC; 4-alkoxy group, CrCV alkylthio group, CrC: 4- ^ alkyl, ο% alkoxy group (which has 1 to 5 halogen atoms), and Crar alkylsulfinyl or Ci-C4-burner group, 200528434 or A represents a group of formula (A5)

(A5) 或 A 代表式(A6)基團 R21 CX (A6)，其中(A5) or A represents a group of formula (A6) R21 CX (A6), where

S 10 R21代表CVCV烷基或具有1至5個鹵原子之CkC4 iS烧基， 或 A 代表式(A7)基團 15 CC (A7)，其中 R22代表〇1-(：4-烷基或具有1至5個鹵原子之（：1-€：4-鹵烧基， 20 或 A 代表式(A8)基團 (A8)，其中 200528434 R與、R分別獨立代表氫、鹵素、胺基、Ci_C4-烷基 u或具有1至5個鹵原子之Cl_C4_鹵烷基，及 R 代表氫、C1_C4-烷基或具有1至5個鹵原子之 ci_C4-自燒基， 5 或 A 代表式(A9)基團S 10 R21 represents a CVCV alkyl group or a CkC4 iS alkyl group having 1 to 5 halogen atoms, or A represents a group of formula (A7) 15 CC (A7), wherein R22 represents 〇1-(: 4-alkyl or having 1 to 5 halogen atoms (: 1- €: 4-halohalo, 20 or A represents a group (A8) of formula (A8), in which 200528434 R and R independently represent hydrogen, halogen, amine, Ci_C4 -Alkyl u or Cl_C4_haloalkyl having 1 to 5 halogen atoms, and R represents hydrogen, C1_C4-alkyl or ci_C4-self-burning group having 1 to 5 halogen atoms, 5 or A represents formula (A9 ) Group

(A9)，其中(A9), where

10 15 R與R分別獨立代表氫、鹵素、胺基、硝基、CrC4-烧基或具有1至5個鹵原子之Crc4-鹵烷基，及 28 R 代表由素、Ci-Cr烧基或具有1至5個鹵原子之 Ci-C4-鹵烧基， 或 A 代表式(A10)基團10 15 R and R each independently represent hydrogen, halogen, amine, nitro, CrC4-carbyl or Crc4-haloalkyl having 1 to 5 halogen atoms, and 28 R represents a hydrogen atom, Ci-Cr alkyl or Ci-C4-halohalo group having 1 to 5 halogen atoms, or A represents a group of formula (A10)

(A10)，其中(A10), where

29 R代表氫、鹵素、胺基、CrC4-烷基胺基、二_(Cl_C4_ 烧基)胺基、氰基、Ci-C4·炫基或具有1至5個鹵 原子之C1-C4-鹵炫基及 R代表鹵素、羥基、Cl-C4_炫基、（Vc4-烧氧基、 c3-cv環烧基、crc4 i烷基或cvc4j烷氧基(其 分別具有1至5個鹵原子）， 11 20 200528434 或 A 代表式(All)基團 529 R represents hydrogen, halogen, amine, CrC4-alkylamino, di_ (Cl_C4_alkyl) amino, cyano, Ci-C4 · xyl, or C1-C4-halogen having 1 to 5 halogen atoms Ranyl and R represent halogen, hydroxyl, Cl-C4_xanyl, (Vc4-alkyloxy, c3-cv cycloalkyl, crc4-i alkyl or cvc4j alkoxy (which each have 1 to 5 halogen atoms) , 11 20 200528434 or A represents a group of formula (All) 5

(All)，其中 R代表鼠、鹵素、胺基、C1-C4-烧基胺基、二-(C1-C4-烷基)胺基、氰基、CKC4-烷基或具有1至5個鹵 原子之crc4-i烷基及 10 R32代表鹵素、Ci-CV烷基或具有1至5個鹵原子之 Ci-Cfi 烧基’ 或 A 代表式(A12)基團 (A12)，其中 15 R33代表氫或CVCr烷基及 R34代表鹵素或CVCV烷基， 或 A 代表式(A13)基團 (A13)，其中 R35代表CrC4-烷基或具有1至5個鹵原子之Ci-CV 鹵烧基， -12- 20 200528434 或 A 代表式(A14)基團 ίΥ ^n-^r36 (A14)，其中 R36代表氬、鹵素、Q-Cr烷基或具有1至5個鹵原 子之Ci-CU鹵烷基，(All), where R represents murine, halogen, amine, C1-C4-alkylamino, di- (C1-C4-alkyl) amino, cyano, CKC4-alkyl, or has 1 to 5 halogens Crc4-i alkyl and 10 R32 of the atom represent halogen, Ci-CV alkyl or Ci-Cfi alkyl having 1 to 5 halogen atoms' or A represents a group (A12) of formula (A12), of which 15 R33 represents Hydrogen or CVCr alkyl and R34 represent halogen or CVCV alkyl, or A represents formula (A13) group (A13), wherein R35 represents CrC4-alkyl or Ci-CV haloalkyl having 1 to 5 halogen atoms, -12- 20 200528434 or A represents a group of formula (A14) Υ ^ n- ^ r36 (A14), where R36 represents argon, halogen, Q-Cr alkyl or Ci-CU haloalkane having 1 to 5 halogen atoms base,

或 A 代表式(A15)基團 10 QC (A15)，其中 R37代表鹵素、羥基、CVC4-烷基、（VCV烷氧基、 C1-C4-烧硫基、C1-C4-齒烧基、Cl-Czp鹵烧硫基、 15 cvc4鹵烷氧基(其分別具有1至5個鹵原子）， 或 A 代表式(A16) 2〇 (A16)，其中 R38代表氫、氰基、CrC4-烷基、具有1至5個鹵原 子之CrC4-鹵烷基、CrC4-烷氧基-CrC4-烷基、 羥基-CrC4-烷基、CVCV烷磺醯基、二(CrC4-烷 -13- 200528434 基)胺基磺醯基、CrC6-烷基羰基或分別可視需要 經取代之苯磺醯基或苯曱醯基， R39代表氫、鹵素、CrC4-烷基或具有1至5個鹵原 子之CrC4-鹵烷基， 5 10 15 R4G代表氳、鹵素、氰基、CrCU-烷基或具有1至5 個函原子之C1-C4-函烧基’ R41代表氩、鹵素、Q-Cr烷基或具有1至5個鹵原 子之CVCr鹵烷基， 或 A 代表式(A17)基團Or A represents the group 10 QC (A15) of formula (A15), where R37 represents halogen, hydroxyl, CVC4-alkyl, (VCV alkoxy, C1-C4-sulfanyl, C1-C4-dental, C1 -Czp halosulfanyl, 15 cvc4 haloalkoxy (which each have 1 to 5 halogen atoms), or A represents formula (A16) 20 (A16), where R38 represents hydrogen, cyano, CrC4-alkyl CrC4-haloalkyl with 1 to 5 halogen atoms, CrC4-alkoxy-CrC4-alkyl, hydroxy-CrC4-alkyl, CVCV alkylsulfonyl, di (CrC4-alk-13-200528434 group) Aminosulfonyl, CrC6-alkylcarbonyl or substituted benzenesulfonyl or phenylfluorenyl, if necessary. R39 stands for hydrogen, halogen, CrC4-alkyl or CrC4-halogen with 1 to 5 halogen atoms. Alkyl, 5 10 15 R4G represents fluorene, halogen, cyano, CrCU-alkyl or C1-C4-alkenyl having 1 to 5 function atoms' R41 represents argon, halogen, Q-Cr alkyl or has 1 CVCr haloalkyl groups of up to 5 halogen atoms, or A represents a group of formula (A17)

(A17)，其中 R42代表CVCV烷基。 若適當時，根據本發明化合物可呈多種可能之異構型 之混合物。特定言之立體異構物之混合物，如，例如：E 與Z、蘇型-與赤型，及光學異構物，及若適當時，亦包括 互變異構物。本發明包括E與Z型兩種異構物，及蘇型-與赤型，及光學異構物，此等異構物之任何混合物及可能 之互變異構物。 此外，已發現，式(I)己基醯基苯胺之製法為 a) 由式(II)羧酸衍生物 20 200528434 其中 A 如上述定義，及 X1代表鹵素或羥基， 與式(III)苯胺衍生物反應 5 ch3 CH3 (HI) 其中L、R1與R3如上述定義， 若適當時，可於觸媒之存在下，及若適當時，於縮合 ίο 劑之存在下，若適當時，於酸結合劑之存在下，及若 適當時，於稀釋劑之存在下進行， 或 b) 由式(I-a)己基醯基苯胺 15(A17), wherein R42 represents a CVCV alkyl group. Where appropriate, the compounds according to the invention may be present as a mixture of various possible isoforms. Mixtures of specific stereoisomers, such as, for example, E and Z, threo- and erythro, and optical isomers, and where appropriate, tautomers. The invention includes two isomers, E and Z, and threo- and erythro, and optical isomers, any mixtures of these isomers and possible tautomers. In addition, it has been found that the method for preparing hexylfluorenylaniline of formula (I) is a) a carboxylic acid derivative of formula (II) 20 200528434 wherein A is as defined above, and X1 represents a halogen or hydroxyl group, and an aniline derivative of formula (III) Reaction 5 ch3 CH3 (HI) where L, R1 and R3 are as defined above, if appropriate, in the presence of a catalyst, and if appropriate, in the presence of a condensation agent, if appropriate, in an acid binder In the presence of, and if appropriate, in the presence of a diluent, or b) from hexylfluorenylaniline of formula (Ia) 15

(I-a) 其中 L、A與R3如上述定義， 20 與式(IV)鹵化物反應 R1A-X2 (IV) 其中 X2代表氯、溴或碘，(I-a) wherein L, A and R3 are as defined above, and 20 reacts with a halide of formula (IV) R1A-X2 (IV) where X2 represents chlorine, bromine or iodine,

R1-A代表Ci-CV烷基、CKC6·烷基亞磺醢基、CVCV -15- 200528434 烧基續醢基、Ci-Cf烧氧基-C1-C4-烧基、C3-C8_ 環烧基；Ci-C6-_烧基、CrCfl#烧硫基、CVC4-鹵烧基-亞石黃酿基、Ci-C4-齒烧基石黃酿基、鹵 -C1-C4-烧氣基""Ci-Cf烧基、。3-(^8_鹵壤烧基，其 5 分別具有1至9個氟、氯與/或溴原子；曱醯基、 甲酿基-C1-C3-烧基、（C1-C3-烧基）幾基-Ci_C3-烧 基、（CVCV烷氧基)羰基-crc3-烷基；鹵-(Cr(V 烷基）羰基-CrCV烷基、鹵-(crc3-烷氧基）羰基 -CVCV烷基，其分別具有1至π個氟、氯與/或 10 溴原子；（CrCV烷基)羰基、（(VC8-烷氧基)羰基、 (CVCV烷氧基-crc4-烷基)羰基、（c3-c8-環烷基） 幾基，（Ci_C6_l^烧基)叛基、（Ci_C6__烧氧基)幾 基、（鹵-CVCV烷氧基-CkCV烷基)羰基、（CVCV 鹵環烷基)羰基，其分別具有1至9個氟、氣與/ 15 或溴原子；或-c(=o)c(=o)r4、CONR5R6 或 -CH2NR7R8，其中 R4、R5、R6、R7 與 R8 如上述 定義， 其係於鹼之存在下及於稀釋劑之存在下進行。 最後，發現新穎之式⑴己基醯基苯胺具有極佳之殺微 20 生物性質，可用於作物保護及原料保護中，控制不要之微 生物。 式⑴提供根據本發明己基醯基苯胺之一般定義。上文 及下文中所示化學式之較佳基團定義如下。此等定義亦適 用於式(I)之終產物及所有中間物。 200528434 L 較佳為代表L-l，其中R2分別具有一般、較佳、特別 佳、極特別佳或尤其佳之定義。 L 亦較佳為代表L-2。 L 亦較佳為代表L-3。 5 L 亦較佳為代表L-4。 L 特別佳為代表L-1，其中R2可分別具有一般、較佳、 特別佳、極特別佳或尤其佳之定義。 L 亦特別佳為代表L-2。 L 極特別佳為代表L-1，其中R2分別具有一般、較佳、 10 特別佳、極特別佳或尤其佳之定義。 R1 較佳為代表氫、CVC6-烷基、CVCV烷基亞磺醯基、 CVCV烷磺醯基、CVC3-烷氧基-CkCV烷基、C3-C6-環烷基；CVO齒烷基、CVCV鹵烷硫基、（VCr鹵烧 基亞磺醯基、Q-Crii烷基磺醯基、i|-CrC3-烷氧基 15 -CVC3-烷基、C3-C8-鹵環烷基，其分別具有1至9個 氟、氯與/或溴原子；甲醯基、甲醯基-CrC3-烷基、 (CVCV烷基）羰基-CVC3·烷基、（CKCV烷氧基）羰基 -C1-C3-烧基，_-(C!-C3-烧基）減基-C1-C3-烧基、鹵 -(CrC3-烷氧基)羰基-CKC3-烷基，其分別具有1至13 20 個氟、氯與/或溴原子；（CrC6-烷基）羰基、（CrCV烷 氧基)羰基、（CrC3-烷氧基-Q-CV烷基)羰基、（C3-C6-環烷基)羰基；（cvcvi烷基)羰基、（CVCV鹵烷氧基） 幾基、（画-C1-C3-烧氧基-C1-C3-烧基)幾基、（C3-C6-鹵 環烷基)羰基，其分別具有1至9個氟、氯與/或溴原 -17- 200528434 子；或-C(=0)C(=0)R4、-CONR5R6 或-CH2NR7R8。 R1 特別佳為代表氫、甲基、乙基、正或異丙基、正、異、 第二-或第二-丁基、戍基或己基、甲基亞績酸基、乙 基亞磺醯基、正或異丙基亞磺醯基、正-、異-、第二-5 或第三-丁基亞磺醯基、曱磺醯基、乙基磺醯基、正 或異丙基磺醯基、正-、異-、第二-或第三-丁磺醯基、 甲氧基曱基、甲氧基乙基、乙氧基曱基、乙氧基乙基、 環丙基、環戊基、環己基、三氟甲基、三氯甲基、三 氟乙基、二氟曱硫基、二氟氯甲硫基、三氟甲硫基、 10 三氟甲基亞磺醯基、三氟甲磺醯基、三氟甲氧基曱 基；曱醯基、-CHrCHO、-(CH2)2-CHO、-CH2-CC>CH3、 -CH2-CO-CH2CH3 - >CH2-CO-CH(CH3)2 - <CH2)2-CO-CH3 ' <CH2)2-CO-CH2CH3 ^ -(CH2)2-CO-CH(CH3)2 ^ -ch2-co2ch3 ' -CH2-C02CH2CH3 ^ -CH2-C02CH(CH3)2 ^ -(CH2)2-C〇2CH3 ^ 15 -(CH2)2-C〇2CH2CH3 ^ -(CH2VC〇2CH(CH3)2 > -ch2-co-cf3 ^ 麵CHrCO-CCl3、-CHrCO碼CF3、-CH2-CO <CH2)2-CO-CH2CF3 > KCH2)2-CO-CH2Ca3' -CH2-C02CH2CF3 ^ -CH2-C02CF2CF3 ^ -CH2-C02CH2CCl3 > -CH2-C02CC12CC13 ^ -(CH2VC〇2CH2CF3 ^ -(CH2)2-C〇2CF2CF3 ^ -(CH2)2-»C〇2CH2CCl3 -20 -(CH2)rC02CCl2CCl3 ; 曱基羰基、乙基羰基、正丙基羰基、異丙基羰基、第 三-丁基羰基、甲氧基羰基、乙氧基羰基、第三-丁氧 基羰基、環丙基羰基；三氟甲基羰基、三氟甲氧基羰 基或-c(=o)c(=o)r5、-CONR6R7 或-CH2NR8R9。 200528434 R1 R2 R2 R2 紐別佳為.代表氳、甲基、甲氣基甲基、甲醯美、 -CH2-CHO、偶)rCHO、CHrCacfT 丞 -ch2-co-ch(ch3)2 ^ -ce〇)CH〇 / CHrCacH2CH3' -C(=〇)C(=〇)CH2〇CH3 ^ -C(=0)C02CH3. ^Zocucn 較佳為代表氫。 ί 〇Ρ32αί2ΟΗ3。 Ji.較佳為代表氟，其中氟楚^^ A[參見上式⑴]之4_、5_或㈣替苯胺基或&位置，尤其佳為為位於位於4- 10 亦失3代表氯，其中氯龜^位於酿替苯胺基 [,見上式⑴]之5_位置。氯亦缝^位於 基之4-位置。 R2 R2 R3 R3 20 R3 R4 亦致食^代表甲基，其中甲基整^^位於醯替苯胺 基[參見上式⑴]之位置。 亦代表三氟曱基，其中三氟甲基特別佳為位於 酿替苯胺基[參見上式（I)]之4-或5-位置。 紅复1代表氟、氯、漠、碘、CVCV烧基、具有i至 13個氣、氯與/或溴原子之Cl_c6-鹵烷基。 代表氟、氯、溴、曱基、乙基、正-、異-丙 ，、正…異…第二-、第三-丁基或具有1至9個氟、 氯與/或漠原子之Ci々函烧基。 代表氟、氯或甲基、乙基或三氟甲基。 ^ 代表風、Ci-Cs-烧基、C1-C4-烧氧基、C1-C3-f基^1%-燒基、C3-C6-環烧基；（VCV鹵烷基、 1<v_燒氧基、卣KV炫氧基-Crcv烧基、c3-c6- -19- 200528434R1-A represents Ci-CV alkyl, CKC6-alkylsulfinylfluorenyl, CVCV -15- 200528434 alkylsulfonyl, Ci-Cf alkyloxy-C1-C4-alkyl, C3-C8_cycloalkyl ; Ci-C6-_burning group, CrCfl # burning sulfur group, CVC4-halogen burning group-sulfite yellow brewing group, Ci-C4-dental burning group yellow powder base, halogen-C1-C4-burning gas group " & quot Ci-Cf alkyl. 3-(^ 8_halocarbons), each of which has 1 to 9 fluorine, chlorine, and / or bromine atoms; fluorenyl, methylenyl-C1-C3-alkyl, and (C1-C3-alkyl) ) Several groups -Ci_C3-alkyl, (CVCV alkoxy) carbonyl-crc3-alkyl; halo- (Cr (V alkyl) carbonyl-CrCV alkyl, halo- (crc3-alkoxy) carbonyl-CVCV alkane Group, which respectively have 1 to π fluorine, chlorine and / or 10 bromine atoms; (CrCValkyl) carbonyl, ((VC8-alkoxy) carbonyl, (CVCValkoxy-crc4-alkyl) carbonyl, c3-c8-cycloalkyl) carbamoyl, (Ci_C6_l ^ alkyl), cisyl, (Ci_C6__alkyl) carbonyl, (halo-CVCValkoxy-CkCValkyl) carbonyl, (CVCV halocycloalkyl ) Carbonyl, which has 1 to 9 fluorine, gas and / 15 or bromine atoms; or -c (= o) c (= o) r4, CONR5R6 or -CH2NR7R8, where R4, R5, R6, R7 and R8 are as The above definition is carried out in the presence of a base and in the presence of a diluent. Finally, it was discovered that the novel formula hexylfluorenylaniline has excellent microbicidal 20 biological properties and can be used in crop protection and raw material protection. Unwanted microorganisms. Formula IX provides the generality of hexylfluorenylaniline according to the present invention. Definitions. The preferred groups of the chemical formulae shown above and below are defined as follows. These definitions also apply to the final product of formula (I) and all intermediates. 200528434 L preferably represents Ll, where R2 has general, Definitions of better, particularly good, very special, or particularly good. L is also preferably represented by L-2. L is also preferably represented by L-3. 5 L is also preferably represented by L-4. L is particularly preferably represented by L L-1, where R2 can have the definitions of general, better, particularly good, very special, or especially good. L is also particularly good for L-2. L is very particularly good for L-1, where R2 has general , Preferably, 10 is particularly good, very particularly good, or particularly good. R1 is preferably hydrogen, CVC6-alkyl, CVCV alkylsulfinyl, CVCV alkylsulfonyl, CVC3-alkoxy-CkCV alkyl Group, C3-C6-cycloalkyl group; CVO alkyl group, CVCV haloalkylthio group, (VCr haloalkylsulfinyl sulfenyl group, Q-Crii alkylsulfonyl group, i | -CrC3-alkoxy group 15- CVC3-alkyl, C3-C8-halocycloalkyl, which each have 1 to 9 fluorine, chlorine and / or bromine atoms; formamyl, formamyl-CrC3-alkyl, (CVCV alkyl) carbonyl- CVC3 · Alkyl, (CKCV alkoxy) carbonyl-C1-C3-alkyl, _- (C! -C3-alkyl) minus-C1-C3-alkyl, halo- (CrC3-alkoxy) carbonyl- CKC3-alkyl having 1 to 13 20 fluorine, chlorine and / or bromine atoms; (CrC6-alkyl) carbonyl, (CrCValkoxy) carbonyl, (CrC3-alkoxy-Q-CValkyl ) Carbonyl, (C3-C6-cycloalkyl) carbonyl; (cvcvialkyl) carbonyl, (CVCVhaloalkoxy), carbonyl, (drawing -C1-C3-alkyloxy-C1-C3-alkyl) , (C3-C6-halocycloalkyl) carbonyl, each having 1 to 9 fluorine, chlorine, and / or bromogen-17-200528434 protons; or -C (= 0) C (= 0) R4,- CONR5R6 or -CH2NR7R8. R1 is particularly preferably represented by hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, second- or second-butyl, fluorenyl or hexyl, methylsulfinyl, ethylsulfinyl , N- or isopropylsulfenylsulfonyl, n-, iso-, second-5 or third-butylsulfinylsulfenyl, sulfenylsulfenyl, ethylsulfonyl, n- or isopropylsulfonyl Fluorenyl, n-, iso-, second- or third-butanesulfonyl, methoxyfluorenyl, methoxyethyl, ethoxyfluorenyl, ethoxyethyl, cyclopropyl, cyclo Amyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluorofluorenylthio, difluorochloromethylthio, trifluoromethylthio, 10 trifluoromethylsulfinyl, Trifluoromethanesulfonyl, trifluoromethoxyfluorenyl; fluorenyl, -CHrCHO,-(CH2) 2-CHO, -CH2-CC > CH3, -CH2-CO-CH2CH3-> CH2-CO- CH (CH3) 2-< CH2) 2-CO-CH3 '< CH2) 2-CO-CH2CH3 ^-(CH2) 2-CO-CH (CH3) 2 ^ -ch2-co2ch3' -CH2-C02CH2CH3 ^ -CH2-C02CH (CH3) 2 ^-(CH2) 2-C〇2CH3 ^ 15-(CH2) 2-C〇2CH2CH3 ^-(CH2VC〇2CH (CH3) 2 > -ch2-co-cf3 ^ CHrCO -CCl3, -CHrCO code CF3, -CH2-CO < CH2) 2-CO-CH2CF3 > KCH 2) 2-CO-CH2Ca3 '-CH2-C02CH2CF3 ^ -CH2-C02CF2CF3 ^ -CH2-C02CH2CCl3 > -CH2-C02CC12CC13 ^-(CH2VC〇2CH2CF3 ^-(CH2) 2-C〇2CF2CF3 ^-(CH2) 2 -»C〇2CH2CCl3 -20-(CH2) rC02CCl2CCl3; fluorenylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, third-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, third -Butoxycarbonyl, cyclopropylcarbonyl; trifluoromethylcarbonyl, trifluoromethoxycarbonyl, or -c (= o) c (= o) r5, -CONR6R7, or -CH2NR8R9. 200528434 R1 R2 R2 R2 Niubei It is preferably represented by fluorene, methyl, methylamino, methylamidine, -CH2-CHO, even) rCHO, CHrCacfT 丞 -ch2-co-ch (ch3) 2 ^ -ce〇) CH〇 / CHrCacH2CH3 ' -C (= 〇) C (= 〇) CH2〇CH3 ^ -C (= 0) C02CH3. ^ Zocucn preferably represents hydrogen. ί 〇Ρ32αί2ΟΗ3. Ji. It is preferred to represent fluorine, in which fluorine ^^ A [see formula 上] above, 4_, 5_, or aziridinyl or & position, particularly preferably located at 4- 10 also lose 3 represents chlorine, Chlorine is located at position 5_ of anilide [, see formula 上 above]. Chlorine is located at the 4-position of the base. R2 R2 R3 R3 20 R3 R4 also causes ^ to represent methyl, in which methyl is ^^ in the position of hydratifenil [see formula 上 above]. It also represents a trifluorofluorenyl group, of which trifluoromethyl group is particularly preferably located at the 4- or 5-position of anilide [see formula (I) above]. Red compound 1 represents fluorine, chlorine, molybdenum, iodine, CVCV alkyl, Cl_c6-haloalkyl having i to 13 gas, chlorine and / or bromine atoms. Represents fluorine, chlorine, bromine, fluorenyl, ethyl, n-, iso-propyl, n -... iso ... second-, third-butyl or Ci with 1 to 9 fluorine, chlorine and / or desert atoms The letter burns the base. Represents fluorine, chlorine or methyl, ethyl or trifluoromethyl. ^ Represents wind, Ci-Cs-alkyl, C1-C4-alkyl, C1-C3-f, ^ 1% -alkyl, C3-C6-cycloalkyl; (VCV haloalkyl, 1 Carbooxy, 卣 KV oxo-Crcv alkyl, c3-c6- -19- 200528434

5 有1至9個氟、氣與/或溴原子。 汉與R6/亦可與其所附接之氮原子缝^共同代表具有5 或6個環原子之飽和雜環，其可視需要經選自齒素與 烷基中之相同或相異取代基單取代至四取代， 其中該雜環可另包含1或2個選自氧、硫與NR9中之 不相鄰雜原子。 R5與r6m^_分別獨立代表氫、曱基、乙基、正-或異 丙基、正、異_、第二-或第三-丁基、甲氧基甲基、甲 氧基乙基、乙氧基甲基、乙氧基乙基、環丙基、環戊 基、環己基；三氟甲基、三氯甲基、三氟乙基、三氟 甲氧基甲基。 R5與R6亦可與其所附接之氮原子特別佳為共同代表選自 下列各物組成之群中之飽和雜環：嗎啉、硫嗎啉與六 氫口比畊，其可視需要經選自下列各物組成之群中之相 同或相異取代基單取代至四取代：氟、氣、溴與曱基， 其中六氩吡畊之第二氮原子可經R9取代。 R7與R8較隹_各分別獨立代表氫、CV(V院基、C3-C6•環烷 -20- 200528434 C1 Q-齒燒基、環燒基，其分別具 7至9個氟、氯與/或溴原子。 R與，’亦可與其所附接之氮原子紐^共同代表具有5 或6個環原子之飽和雜環，其可視需要經選自4素與 Ci-Cr烷基中之相同或相異取代基單取代或多取代， 其中該雜環可另包含1或2個選自氧、硫與NR9中 不相鄰雜原子。 R與R8楚激隹A分別獨立代表氫、甲基、乙基、正、或異 ，基、正、異_、第二_或第三_丁基、甲氧基甲基、甲 氧基乙基、乙氧基曱基、乙氧基乙基、環丙基、環戊5 has 1 to 9 fluorine, gas and / or bromine atoms. Han and R6 / can also be attached to the nitrogen atom attached to them ^ together represent a saturated heterocyclic ring with 5 or 6 ring atoms, which can be mono-substituted with the same or different substituents selected from the group consisting of halo and alkyl To tetra-substituted, wherein the heterocyclic ring may further include 1 or 2 non-adjacent heteroatoms selected from oxygen, sulfur and NR9. R5 and r6m ^ _ each independently represent hydrogen, fluorenyl, ethyl, n- or isopropyl, n-, iso-, second- or third-butyl, methoxymethyl, methoxyethyl, Ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R5 and R6 and the nitrogen atom to which they are attached are particularly preferred to represent a saturated heterocyclic ring selected from the group consisting of morpholine, thiomorpholine, and hexahydro, which may be selected from The same or different substituents in the group consisting of the following are mono- to tetra-substituted: fluorine, gas, bromine, and fluorenyl, wherein the second nitrogen atom of hexamethylpyridine may be substituted by R9. R7 and R8 are relatively different. Each independently represents hydrogen, CV (V-based, C3-C6 • naphthenic-20- 200528434 C1 Q-dentate, cycloalkyl, which have 7 to 9 fluorine, chlorine and And / or a bromine atom. R and, 'may also represent a saturated heterocyclic ring having 5 or 6 ring atoms with the nitrogen atom to which it is attached, which may be optionally selected from the group consisting of 4 and Ci-Cr alkyl groups. The same or different substituents are mono- or poly-substituted, wherein the heterocyclic ring may further include 1 or 2 non-adjacent heteroatoms selected from the group consisting of oxygen, sulfur, and NR9. R and R8 are independently independent of hydrogen and methyl. Radical, ethyl, n-, or iso, radical, n-, iso-, second- or third-butyl, methoxymethyl, methoxyethyl, ethoxyfluorenyl, ethoxyethyl , Cyclopropyl, cyclopentyl

基、環己基；三氟甲基、三氯甲基、三氟乙基、三 甲氧基甲基。 I 15 R7與R8亦可與其所附接之氮原子特別佳為共同代表# ^ 下列各物組成之群中之飽和雜環：嗎啉、硫嗎啉與六 氫°比畊’其可視需要經選自下列各物組成之群中之相 同或相異取代基單取代至四取代··氟、氯、溴與甲基， 其中六氫吡畊之第二氮原子可經R9取代。 R9 代表氫或Cl_C4_烷基。 R 特別佳為代表氫、甲基、乙基、正或異丙基、正… 異第二-或第三-丁基。 A 鐘代表下列基團之一：如上述之Al、A2、A3、A4、 Α5、Α8、Α9、Α10、Α1 卜 Α13、Α15、Α16 或 Α17 〇 A 代表下列基團之一：如上述之A卜A2、A4、 A5、A8、A10、All、A13、A15、A16 或 A17 〇 -21- 20 200528434 A 極特別佳為代表基團A1。 A 亦極特別佳為代表基團A2。 A 亦極特別佳為代表基團A4。 A 亦極特別佳為代表基團A5。 5 A 亦極特別佳為代表基團A8。 A 亦極特別佳為代表基團A10。 A 亦極特別佳為代表基團All。 A 亦極特別佳為代表基團A13。 A 亦極特別佳為代表基團A13。 10 A 亦極特別佳為代表基團A15。 A 亦極特別佳為代表基團A17。 R10 較佳為代表氫、羥基、甲醯某、氮某、氣、1、溴、 曱基、乙基、異丙基、曱氧基、乙氧基、甲硫基、乙 硫基、環丙基、crc2-鹵烷基、cvcv齒烷氧基（其分 15 別具有1至5個氟、氯與/或溴原子）、三氟甲硫基、 二氟曱硫基、胺基羰基、胺基羰基甲基或胺基羰基乙 R10特別佳為代表氳、羥基、甲醯基、氟、氯、溴、甲基、 乙基、異丙基、曱氧基、乙氧基、單氟甲基、單氟乙 2〇 基、二氟甲基、三氟甲基、二氟氯甲基、三氣甲基、 二氯曱基、五氟乙基、環丙基、甲氧基、乙氧基、三 氟甲氧基、二氟甲氧基、三氯甲氧基、甲硫基、乙硫 基、三氟甲硫基或二氟甲硫基。 R10極特別佳為代表氫、羥基、甲醯基、氟、氯、漠、曱 -22- 200528434 基、乙基、異丙基、甲氧基、環丙基、單氟甲基、單 氟乙基、二氟曱基、二氯甲基、三氟甲基、二氟氯甲 基、三氯曱基、_chfch3或二氟甲氧基。 R10尤其佳為代表氫、羥基、甲醯基、氯、甲基、乙基、 5 甲氧基、環丙基、單氟甲基、二氟曱基、二氯甲基、 三氟甲基、-chfch3或二氟甲氧基。 R11較佳為代表氫、氯、溴、碘、曱基、乙基、曱氧基、 乙氧基、甲硫基、乙硫基、具有1至5個氟、氯與/ | 或溴原子之cvcvi烷基。 ίο R11特別佳為代表氫、氯、溴、碘、甲基或-CHFCH3。 R11極特別佳為代表氫、氯、甲基或-CHFCH3。 R12較佳為代表氫、甲基、乙基、正丙基、異丙基、具有 1至5個氟、氯與/或溴原子之CVCV鹵烷基、羥基曱 基、羥基乙基、環丙基、環戊基、環己基或苯基。 15 R12特別佳為代表氫、曱基、乙基、異丙基、三氟甲基、 二氟甲基、羥基甲基、羥基乙基或苯基。 _ R12極特別佳為代表氫、甲基、三氟甲基或笨基。 R12尤其佳為代表曱基〇 R13與R14較佳為分別獨立代表氫、氟、氯、溴、甲基、乙 2〇 基或具有1至5個氟、氯與/或溴原子之Ci-Cr鹵烷基。 R13與R14特別佳為分別獨立代表氳、氟、氯、溴、甲基、 乙基、二氟甲基、三氟甲基、二氟氯甲基或三氯曱 基。 R13與R14極特別佳為分別獨立代表氫、氟、氪、溴或甲基。 -23- 200528434 R13與R14尤其佳為分別代表氫。 R15較佳為代表氟、氮、溴、碘、氰基、甲基、乙某、CVCV 齒烧基或Ci-C2-鹵烧氧基’其分別具有1至5個氟、 氯與/或溴原子。 5 R15特別佳為代表氟、氯、溴、蛾、氰基、甲基、三氟曱 基、三氟甲氧基、二氟甲氧基、二氟氯甲氧基或三氯 甲氧基。 R15極特別佳為代表氟、氯、溴、碘、甲基、三氟曱基或| 三氟甲氧基。 ίο R15尤其佳為代表氣或甲基。 R16與R17較佳為分別獨立代表氫、氟、氯、溴、甲基、乙 基或具有1至5個氟、氯與/或溴原子iQ-Cr·鹵烷基。 R16與R17特別佳為分別獨立代表氫、氟、氯、溴、曱基、 乙基、二氟甲基、三氟曱基、二氟氯甲基或三氯曱基。 15 R16與R17極特別佳為分別獨立代表氳、氟、氣、溴戒甲某。， R16與R17尤其佳為分別代表氳。 龜 R18較佳為代表氫、甲基、乙基或具有1至5個氟、氯與 /或溴原子之CrC2-鹵烷基。 R18特別佳為代表氫、甲基或三氟甲基。 20 R18極特別佳為代表曱基。 R19較佳為代表氟、氯、溴、碘、羥基、氰基、CrC4-烷 基、甲氧基、乙氧基、甲硫基、乙硫基、二氟甲硫基、 三氟甲硫基、CrC2-鹵烷基或CrC2-齒烷氧基，其分 別具有1至5個氟、氯與/或溴原子。 -24- 200528434 R19特別佳為代表氟、氯、溴、碘、羥基、氰基、甲基、 乙基、正丙基、異丙基、正丁基、異丁基、第二-丁 基、第三-丁基、三氟甲基、二氟甲基、二氟氯曱基、 三氣甲基、甲氧基、乙氧基、曱硫基、乙硫基、二氟 5 曱硫基、三氟甲硫基、三氟甲氧基、二氟曱氧基、二 氟氯甲氧基或三氯曱氧基。 R19極特別佳為代表氟、氯、溴、碘、羥基、甲基、三氤 甲基、二氟甲基或三氯甲基。 R20較佳為代表氫、氟、氯、溴、碘、氰基、CVC4-烷基、 10 甲氧基、乙氧基、甲硫基、乙硫基、cvc2-i烷基或 C^Qz-鹵烷氧基（其分別具有1至5個氟、氯與/或溴 原子）、Ci-Cz-烧基亞續醯基或CVC2-烧續醯基。 R20特別佳為代表氫、氟、氯、溴、碘、氰基、正丙基、 異丙基、正丁基、異丁基、第二-丁基、第三-丁基、 15 三氟甲基、二氟甲基、二氟氯甲基、三氯甲基、甲氧 基、乙氧基、曱硫基、乙硫基、三氟甲氧基、二氟甲 氧基、二氟氯曱氧基、三氯甲氧基、曱基亞磺醯基或 甲磺醯基。 R20極特別佳為代表氬、敗、氣、漠、破、正丙基、異丙 20 基、正丁基、異丁基、第二-丁基、第三-丁基、三氟 曱基、二氟曱基、三氯曱基、甲基亞磺醯基或甲磺醯 基。 R20尤其佳為代表氫或三氟甲基。 R21較佳為代表甲基、乙基或具有1至5個氟、氣輿/威德 -25- 200528434 原子之q-Cr鹵烷基。 R21特別佳為代表甲基、乙基、三氟甲基、二氟甲基、二 氟氯甲基或三氯甲基。 R21極特別佳為代表甲基、三氣甲基、二氟甲基或三氯甲 5 基。 R22較佳為代表甲基、乙基、三氟甲基、二氟甲基、二氟 氯甲基或三氯甲基。 R22特別佳為代表甲基、三氟甲基、二氟甲基或三氯甲 ίο R23與R24較佳為分別獨立代表氫、氟、氯、溴、胺基、曱 基、乙基或具有1至5個氟、氯與/或溴原子之C^-CV 鹵烧基。 R23與R24特別佳為分別獨立代表氫、氟、氯、溴、甲基、 乙基、三氟甲基、二氟甲基、二氟氯甲基或三氯曱基。 15 R23與R24極特別佳為分別獨立代表氫、氟、氯、溴或甲基。 R23與R24尤其佳為分別代表氫。 R25較佳為代表氫、曱基、乙基或具有1至5個氟、氯與 /或溴原子之CrC2-鹵烷基。 R 特別佳為代表氣、甲基、乙基、二氣甲基、二氣甲基、 2〇 二氟氯甲基或三氯甲基。 R25極特別佳為代表氫、甲基、三氟甲某、二氟甲基或三 氯甲基。 R25尤其佳為代表甲基或三氟甲基。 R26與R27較佳為分別獨立代表氫、氟、氯、溴、胺基、硝 -26- 200528434 基、甲基、乙基或具有1至5個氟、氯與/或溴原子之 CVC2-鹵烷基。 R26與R27特別佳為分別獨立代表氫、氟、氯、溴、硝基、 甲基、乙基、三氟甲基、二氟甲基、二氟氯T基或三 5 氯曱基。 R26與R27極特別佳為分別獨立代表氫、氟、氣、溴或甲 基。 R26與R27尤其佳為分別代表氫。 R28較佳為代表氟、氯、溴、甲基、乙基或具有1至5個 1〇 氟、氯與/或溴原子之（VCV鹵烷基。 R28特別佳為代表氟、氯、溴、甲基、乙基、三氟甲基、 二氟曱基、二氟氯甲基或三氯甲基。 R28極特別佳為代表氟、氯、溴、甲基、三氟甲基、二 氟曱基或三氯甲基。 15 R28尤其佳為代表甲基。 R29較佳為代表氫、氟、氯、溴、胺基、CkCV烷基胺基、 二(C1-C4-烧基)胺基、氣基、甲基、乙基或具有1至5 個氟、氯與/或溴原子之crc2-鹵烷基。 R29特別佳為代表氫、氟、氯、溴、胺基、曱基胺基、二 2〇 甲基胺基、氰基、甲基、乙基、三氟甲基、二氟甲基、 二氟氯甲基或三氯曱基。 R29極特別佳為代表氫、氟、氯、溴、胺基、甲基胺基、 二甲基胺基、曱基、三氟曱基、二氟甲基或三氯甲基。 R29尤其佳為代表氫、氣、胺基、甲基胺基、二甲基胺基、 -27- 200528434 甲基或三氟甲基。 R30較佳為代表氟、氣、溴、羥基、甲基、乙基、甲氧基、 乙氧基、環丙基、具有1至5個氟、氯與/或溴原子之 CVC2-_烷基或CrC2-鹵烷氧基。 5 R30特別佳為代表氟、氯、溴、羥基、甲基、乙基、甲氧 基、乙氧基、環丙基、三氟曱基、二氟甲基、二氟氯 甲基或三氯甲基。 R30極特別佳為代表氟、氯、溴、羥基、曱基、甲氧基、 環丙基、三氟甲基、二氟曱基或三氯曱基。 10 R31較佳為代表氫、氟、氯、溴、胺基、CrCV烷基胺基、 二(C^Cr烷基)胺基、氰基、甲基、乙基或具有1至5 個氟、氯與/或溴原子之鹵烷基。 R31特別佳為代表氫、氟、氯、溴、胺基、甲基胺基、二 曱基胺基、氰基、甲基、乙基、三氟甲基、二氟曱基、 15 二氟氯曱基或三氯甲基。 R31極特別佳為代表氫、氟、氯、溴、胺基、甲基胺基、 二曱基胺基、甲基、三氟甲基、二氟甲基或三氨甲基。 R31尤其佳為代表胺基、甲基胺基、二甲某胺某、甲某或 三氟甲基。 20 R32較隹為代表氟、氯、溴、曱基、乙基或具有1至5個 氟、氯與/或溴原子之CrC2-鹵烷基。 R32特別佳為代表氟、氯、溴、甲基、乙基、三氟甲基、 二氣曱基、二敗氯甲基或三氯甲基。 R32極特別佳為代表氟、氯、溴、甲基、三氟甲基、二氟 -28- 200528434 甲基或三氯甲基。 R32尤其佳為代表曱基、三氟甲基或二氟甲某。 R33較佳為代表氫、曱基或乙基。 R33特別佳為代表甲基〇 5 R34較佳為代表氟、氯、溴、曱基或乙基。 R34特別佳為代表氟、氯或甲基。 R35較佳為代表甲基、乙基或具有1至5個氟、氯與/或溴 原子之CVC2-i烷基。 R35特別佳為代表甲基、乙基、三氟甲基、二氟曱基、二 1〇 氟氯甲基或三氯曱基。 R35極特別佳為代表甲基、三氟甲基、二氟甲基或三氣甲 基。 R35尤其佳為代表甲基或三氟甲基。 R36較佳為代表氫、氟、氯、溴、甲基、乙基、或具有1 15 至5個氟、氯與/或溴原子之CrC2-鹵烷基。 R36特別佳為代表氫、氟、氯、溴、曱基或三氟甲基。 R36極特別佳為代表氫或氮。 R37較佳為代表氟、氯、溴、碘、羥基、CrCzr烷基、甲 氧基、乙氧基、甲硫基、乙硫基、二氟甲硫基、三氟 2〇 甲硫基、CrC2-鹵烷基或CrC2-鹵烷氧基，其分別具 有1至5個氟、氯與/或溴原子。 R37特別佳為代表氟、氯、溴、碘、甲基、乙基、正丙基、 異丙基、正丁基、異丁基、第二-丁基、第三-丁基、 三氟曱基、二氟曱基、二氟氯曱基、三氯曱基。 -29- 200528434 R37極特別佳為代表說、氯、溴、碘、曱基、三氟甲基、 二氟甲基或三氯甲基。 R38較佳為代表氫、甲基、乙基、具有1至5個氟、氯與 /或溴原子之crc2-鹵烷基、crc2-烷氧基-crc2-烷 5 基、羥基曱基、羥基乙基、甲磺醯基或二甲基胺基磺 醯基。 R38特別佳為代表氳、曱基、乙基、三氟甲基、甲氧基曱 基、乙氧基甲基、羥基曱基或羥基乙基。 R38極特別佳為代表曱基或曱氧基曱基。 ίο R39較佳為代表氳、氟、氯、溴、甲基、乙基或具有1至 5個氟、氯與/或溴原子之CrC2-鹵烷基。 R39特別佳為代表氫、氟、氯、溴、甲基、乙基、三氟甲 基、二氟甲基或三氯甲基。 R39極特別佳為代表氫或曱基。 15 R40較佳為代表氫、氟、氯、溴、氰基、甲基、乙基、異 丙基或具有1至5個氟、氯與/或溴原子之CnCr鹵烷 基。 R40特別佳為代表氫、氟、氯、溴、氰基、曱基、乙基、 異丙基、三氟甲基、二氟甲基、二氟氯甲基或三氯曱 20 基。 R40極特別佳為代表氫、氟、曱基或三氟曱基。 R41較佳為代表氫、氟、氯、溴、甲基、乙基或具有1至 5個氟、氣與/或溴原子之CrC2-鹵烷基。 R41特別佳為代表氫、氟、氣、溴、碘、曱基或三氟甲基。 -30- 200528434 R41極特別佳為代表氫或三氟甲基。 R42較佳為代表甲基、乙基、正丙基或異丙基。 R42特別佳為代表甲基或乙基。 其重點在於式(I)化合物，其中L代表L-1，其中R2如 5 上述之一般定義。 其重點在於式(I)化合物，其中L代表L-1，其中R2如 上述之較佳定義。 其重點在於式(I)化合物，其中L代表L-1，其中R2如 上述之特別佳定義。 1〇 其重點在於式(I)化合物，其中L代表L-1，其中R2如 上述之極特別佳定義。 其重點在於式(I)化合物，其中L代表L-1，其中R2如 上述之尤其佳定義。 其重點在於式(I)化合物，其中L代表L-2。 15 其重點在於式(I)化合物，其中R1代表氫。 其重點在於式(I)化合物，其中R1代表曱醯基。 其重點亦在於式（I)化合物，其中 R1代表 -C(=0)C(=0)R4，其中R4如上述定義。 其重點在於式(I)化合物，其中A代表A1。 20 飽和或不飽和烴基如：烷基或烯基，可分別為直鏈或 分支，其中亦包括與雜原子之組合，例如：烷氧基。 可視需要經取代之基團可經單取代或多取代，其中若 經多取代時，其取代基可相同或相異。 經ή素取代之基團如，例如：鹵烧基，係經單鹵化或 -31 - 200528434 j化。右經多_化時’其自原子可相同或相里。此時， 齒素：表、氟:氯、演與碘，特定言之氟、氯與漠。 以而’上述之-般或較佳基團定義或朗亦可依需要 合’亦即在其個職11與較佳顧内組合。該等定 義亦適用終產物及相應之前體與中間物。 上述定義可依需要互相組合。此外，採用個別 疋義。 (I十物ί車父佳、特別佳或極特別佳定義係分別指 π有上述、特別佳或極特別佳取代基之式⑴化合物。 迪己基醯基^ 製法(a) 使用3-二氣甲基《4-甲其m 15 ® A-r AV*-土 H·^唑-4-羰基氯與[2-(U，3-三 狀顧說明 起始物’根據本㈣製法⑷可依下 20And cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, and trimethoxymethyl. I 15 R7 and R8 may also be particularly representative of the nitrogen atom to which they are attached. ^ Saturated heterocycles in the group consisting of morpholine, thiomorpholine, and hexahydro ° The same or different substituents selected from the group consisting of the following are mono- to tetra-substituted ... fluorine, chlorine, bromine, and methyl, wherein the second nitrogen atom of hexahydropyridine may be substituted by R9. R9 represents hydrogen or Cl_C4_alkyl. R is particularly preferably represented by hydrogen, methyl, ethyl, n- or iso-propyl, n -... iso-second or third-butyl. A bell represents one of the following groups: Al, A2, A3, A4, A5, A8, A9, A10, A1, A13, A15, A16, or A17 as described above. A represents one of the following groups: A as described above A2, A4, A5, A8, A10, All, A13, A15, A16 or A17 0-21-20 200528434 A Very particularly preferably represents the group A1. A is also particularly preferred as the representative group A2. A is also particularly preferred as the representative group A4. A is also particularly preferred as the representative group A5. 5 A is also particularly good as the representative group A8. A is also particularly preferred as the representative group A10. A is also particularly good as the representative group All. A is also particularly preferred as the representative group A13. A is also particularly preferred as the representative group A13. 10 A is also particularly good as the representative group A15. A is also particularly preferred as the representative group A17. R10 preferably represents hydrogen, hydroxyl, formamidine, nitrogen, gas, 1, bromine, fluorenyl, ethyl, isopropyl, fluorenyloxy, ethoxy, methylthio, ethylthio, cyclopropyl Group, crc2-haloalkyl group, cvcv alkoxy group (where 15 has 1 to 5 fluorine, chlorine and / or bromine atoms respectively), trifluoromethylthio, difluorofluorenylthio, aminocarbonyl, amine R10 is particularly preferably represented by fluorenyl, hydroxy, methylamino, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, fluorenyloxy, ethoxy, monofluoromethyl , Monofluoroethyl 20-yl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trifluoromethyl, dichloromethyl, pentafluoroethyl, cyclopropyl, methoxy, ethoxy , Trifluoromethoxy, difluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio. R10 is particularly preferably represented by hydrogen, hydroxyl, methylamino, fluorine, chlorine, molybdenum-22-200528434, ethyl, isopropyl, methoxy, cyclopropyl, monofluoromethyl, monofluoroethyl Group, difluorofluorenyl, dichloromethyl, trifluoromethyl, difluorochloromethyl, trichlorofluorenyl, _chfch3 or difluoromethoxy. R10 is particularly preferably represented by hydrogen, hydroxyl, methylamino, chlorine, methyl, ethyl, 5methoxy, cyclopropyl, monofluoromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, -chfch3 or difluoromethoxy. R11 preferably represents hydrogen, chlorine, bromine, iodine, fluorenyl, ethyl, fluorenyl, ethoxy, methylthio, ethylthio, having 1 to 5 fluorine, chlorine, and / or bromine atoms. cvcvi alkyl. ίο R11 is particularly preferably hydrogen, chlorine, bromine, iodine, methyl, or -CHFCH3. R11 is very particularly preferably represented by hydrogen, chlorine, methyl or -CHFCH3. R12 is preferably a CVCV haloalkyl group representing hydrogen, methyl, ethyl, n-propyl, isopropyl, 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxyfluorenyl, hydroxyethyl, cyclopropyl Radical, cyclopentyl, cyclohexyl or phenyl. 15 R12 is particularly preferably hydrogen, fluorenyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl. _ R12 is particularly preferably represented by hydrogen, methyl, trifluoromethyl or benzyl. R12 is particularly preferably a fluorenyl group. R13 and R14 are preferably independently hydrogen, fluorine, chlorine, bromine, methyl, ethyl 20 groups, or Ci-Cr having 1 to 5 fluorine, chlorine, and / or bromine atoms. Haloalkyl. R13 and R14 are particularly preferably independently represented by fluorene, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichlorofluorenyl. R13 and R14 are particularly preferably each independently represented by hydrogen, fluorine, arsine, bromine or methyl. -23- 200528434 R13 and R14 particularly preferably represent hydrogen, respectively. R15 preferably represents fluorine, nitrogen, bromine, iodine, cyano, methyl, ethyl, CVCV, or Ci-C2-halohaloxy, each of which has 1 to 5 fluorine, chlorine, and / or bromine. atom. 5 R15 is particularly preferably represented by fluorine, chlorine, bromine, moth, cyano, methyl, trifluorofluorenyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R15 is particularly preferably represented by fluorine, chlorine, bromine, iodine, methyl, trifluorofluorenyl or | trifluoromethoxy. ίο R15 is particularly preferably represented by gas or methyl. R16 and R17 each preferably independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or iQ-Cr · haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R16 and R17 are particularly preferably each independently represented by hydrogen, fluorine, chlorine, bromine, fluorenyl, ethyl, difluoromethyl, trifluorofluorenyl, difluorochloromethyl or trichlorofluorenyl. 15 R16 and R17 are particularly good when they independently represent tritium, fluorine, gas, bromide, or agarium. R16 and R17 particularly preferably represent 氲, respectively. Turtle R18 is preferably a CrC2-haloalkyl group which represents hydrogen, methyl, ethyl or 1-5 with fluorine, chlorine and / or bromine atoms. R18 is particularly preferably represented by hydrogen, methyl or trifluoromethyl. 20 R18 is particularly good as representative of fluorene. R19 preferably represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CrC4-alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio , CrC2-haloalkyl or CrC2-haloalkoxy, each having 1 to 5 fluorine, chlorine and / or bromine atoms. -24- 200528434 R19 is particularly preferably represented by fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second-butyl, Tert-butyl, trifluoromethyl, difluoromethyl, difluorochlorofluorenyl, trifluoromethyl, methoxy, ethoxy, fluorenylthio, ethylthio, difluoro5fluorenylthio, Trifluoromethylthio, trifluoromethoxy, difluorofluorenyloxy, difluorochloromethoxy or trichlorofluorenyloxy. R19 is particularly preferably represented by fluorine, chlorine, bromine, iodine, hydroxy, methyl, trimethyl, difluoromethyl or trichloromethyl. R20 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, CVC4-alkyl, 10 methoxy, ethoxy, methylthio, ethylthio, cvc2-i alkyl, or C ^ Qz- Haloalkoxy (which has 1 to 5 fluorine, chlorine and / or bromine atoms, respectively), Ci-Cz-alkylidenefluorenylene or CVC2-alkylidenefluorenyl. R20 is particularly preferably represented by hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, isobutyl, second-butyl, third-butyl, 15 trifluoromethyl Methyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, sulfanyl, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochlorophosphonium Oxy, trichloromethoxy, sulfenylsulfenyl or methanesulfenyl. R20 is very particularly good at representing argon, hydrogen, gas, molybdenum, n-propyl, isopropyl 20, n-butyl, isobutyl, second-butyl, third-butyl, trifluorofluorenyl, Difluorofluorenyl, trichlorofluorenyl, methylsulfinyl or methylsulfinyl. R20 is particularly preferably represented by hydrogen or trifluoromethyl. R21 is preferably a methyl group, an ethyl group, or a q-Cr haloalkyl group having 1 to 5 fluorine, gas / Weid-25-25200528434 atoms. R21 is particularly preferably represented by methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R21 is particularly preferably a methyl group, a trifluoromethyl group, a difluoromethyl group or a trichloromethyl group. R22 preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R22 is particularly preferably methyl, trifluoromethyl, difluoromethyl, or trichloromethyl. R23 and R24 are preferably each independently hydrogen, fluorine, chlorine, bromine, amine, fluorenyl, ethyl, or have 1 C ^ -CV haloalkyl groups having up to 5 fluorine, chlorine and / or bromine atoms. R23 and R24 are particularly preferably each independently represented by hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichlorofluorenyl. 15 R23 and R24 are particularly preferred when they independently represent hydrogen, fluorine, chlorine, bromine or methyl. R23 and R24 particularly preferably represent hydrogen, respectively. R25 is preferably a CrC2-haloalkyl group which represents hydrogen, fluorenyl, ethyl, or has 1 to 5 fluorine, chlorine and / or bromine atoms. R is particularly preferably represented by methyl, ethyl, ethyl, dimethyl, dimethyl, 20 difluorochloromethyl or trichloromethyl. R25 is particularly preferably represented by hydrogen, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R25 is particularly preferably a methyl group or a trifluoromethyl group. R26 and R27 are preferably independently represented by hydrogen, fluorine, chlorine, bromine, amine, nitr-26-200528434, methyl, ethyl or CVC2-halogen having 1 to 5 fluorine, chlorine and / or bromine atoms, respectively. alkyl. R26 and R27 are particularly preferably independently represented by hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloro T group, or trichlorochloromethyl group. R26 and R27 are particularly preferably each independently represented by hydrogen, fluorine, gas, bromine or methyl. R26 and R27 particularly preferably represent hydrogen, respectively. R28 preferably represents fluorine, chlorine, bromine, methyl, ethyl, or (VCV haloalkyl) having 1 to 5 10 fluorine, chlorine, and / or bromine atoms. R28 particularly preferably represents fluorine, chlorine, bromine, Methyl, ethyl, trifluoromethyl, difluorofluorenyl, difluorochloromethyl or trichloromethyl. R28 is particularly preferably represented by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluorofluorene 15 R28 particularly preferably represents methyl. R29 preferably represents hydrogen, fluorine, chlorine, bromine, amine, CkCV alkylamino, bis (C1-C4-alkyl) amine, Gas, methyl, ethyl or crc2-haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R29 is particularly preferably represented by hydrogen, fluorine, chlorine, bromine, amine, fluorenylamino, Dioxomethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichlorofluorenyl. R29 is particularly preferably represented by hydrogen, fluorine, chlorine, Bromine, amino, methylamino, dimethylamino, fluorenyl, trifluorofluorenyl, difluoromethyl or trichloromethyl. R29 is particularly preferably represented by hydrogen, gas, amine, methylamine , Dimethylamino, -27- 200528434 methyl or trifluoromethyl R30 is preferably CVC2-_ representing fluorine, gas, bromine, hydroxy, methyl, ethyl, methoxy, ethoxy, cyclopropyl, having 1 to 5 fluorine, chlorine and / or bromine atoms. Alkyl or CrC2-haloalkoxy. 5 R30 is particularly preferably represented by fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, methoxy, ethoxy, cyclopropyl, trifluorofluorenyl, difluoromethyl R30 is particularly preferably represented by fluorine, chlorine, bromine, hydroxyl, fluorenyl, methoxy, cyclopropyl, trifluoromethyl, difluoromethyl, or trichloro. 10 R31 preferably represents hydrogen, fluorine, chlorine, bromine, amine, CrCV alkylamino, bis (C ^ Cr alkyl) amino, cyano, methyl, ethyl, or has 1 to 5 Haloalkyl with fluorine, chlorine and / or bromine atoms. R31 is particularly preferably represented by hydrogen, fluorine, chlorine, bromine, amine, methylamino, diamidoamino, cyano, methyl, ethyl, Trifluoromethyl, difluorofluorenyl, 15 difluorochlorofluorenyl or trichloromethyl. R31 is particularly preferably represented by hydrogen, fluorine, chlorine, bromine, amino, methylamino, difluorenylamino, Methyl, trifluoromethyl, difluoromethyl or triaminomethyl. R31 Particularly preferred is amine, methylamino, dimethylamine, methyl or trifluoromethyl. 20 R32 is more representative of fluorine, chlorine, bromine, fluorenyl, ethyl, or has 1 to 5 fluorine CrC2-haloalkyl, chlorine and / or bromine. R32 is particularly preferably represented by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, dioxanyl, dichloromethyl or trichloromethyl. R32 is particularly preferably represented by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoro-28-200528434 methyl or trichloromethyl. R32 is particularly preferably represented by fluorenyl, trifluoromethyl or dichloro Fluoromethyl. R33 is preferably hydrogen, fluorenyl or ethyl. R33 is particularly preferably methyl. R34 is preferably fluoro, chlorine, bromine, fluorenyl or ethyl. R34 is particularly preferably represented by fluorine, chlorine or methyl. R35 is preferably a methyl, ethyl or CVC2-i alkyl group having from 1 to 5 fluorine, chlorine and / or bromine atoms. R35 is particularly preferably a methyl group, an ethyl group, a trifluoromethyl group, a difluorofluorenyl group, a di 10fluorochloromethyl group or a trichlorofluorenyl group. R35 is particularly preferably represented by methyl, trifluoromethyl, difluoromethyl or trismethyl. R35 is particularly preferably a methyl group or a trifluoromethyl group. R36 is preferably a hydrogen atom, fluorine, chlorine, bromine, methyl, ethyl, or CrC2-haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R36 is particularly preferably represented by hydrogen, fluorine, chlorine, bromine, fluorenyl or trifluoromethyl. R36 is particularly preferably represented by hydrogen or nitrogen. R37 preferably represents fluorine, chlorine, bromine, iodine, hydroxyl, CrCzr alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoro20methylthio, CrC2 -Haloalkyl or CrC2-haloalkoxy, which each have 1 to 5 fluorine, chlorine and / or bromine atoms. R37 is particularly preferably represented by fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second-butyl, third-butyl, trifluorofluorene Base, difluorofluorenyl, difluorochlorofluorenyl, trichlorofluorenyl. -29- 200528434 R37 is particularly preferably represented by chlorine, bromine, iodine, fluorenyl, trifluoromethyl, difluoromethyl or trichloromethyl. R38 preferably represents hydrogen, methyl, ethyl, crc2-haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, crc2-alkoxy-crc2-alkyl5, hydroxyfluorenyl, hydroxy Ethyl, methanesulfonyl or dimethylaminosulfonyl. R38 is particularly preferably represented by fluorenyl, fluorenyl, ethyl, trifluoromethyl, methoxyfluorenyl, ethoxymethyl, hydroxyfluorenyl, or hydroxyethyl. R38 is very particularly preferably a fluorenyl or methoxyfluorenyl group. R39 is preferably a CrC2-haloalkyl group which represents fluorene, fluorine, chlorine, bromine, methyl, ethyl, or has 1 to 5 fluorine, chlorine, and / or bromine atoms. R39 is particularly preferably represented by hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl. R39 is particularly preferably represented by hydrogen or fluorenyl. 15 R40 is preferably a CnCr haloalkyl group representing hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, or 1 to 5 fluorine, chlorine and / or bromine atoms. R40 is particularly preferably represented by hydrogen, fluorine, chlorine, bromine, cyano, fluorenyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichlorofluorene 20 group. R40 is particularly preferably represented by hydrogen, fluorine, fluorenyl or trifluorofluorenyl. R41 is preferably a CrC2-haloalkyl group representing hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or having 1 to 5 fluorine, gas, and / or bromine atoms. R41 is particularly preferably represented by hydrogen, fluorine, gas, bromine, iodine, fluorenyl or trifluoromethyl. -30- 200528434 R41 is very particularly preferably represented by hydrogen or trifluoromethyl. R42 preferably represents methyl, ethyl, n-propyl or isopropyl. R42 is particularly preferably a methyl group or an ethyl group. The focus is on compounds of formula (I), where L represents L-1, and R2 is as defined above. The focus is on compounds of formula (I), where L represents L-1, and R2 is as defined above. The focus is on compounds of formula (I), where L represents L-1, and R2 is as particularly well defined as above. 10 The focus is on compounds of formula (I), where L represents L-1, and R2 is as particularly well defined as above. The focus is on compounds of formula (I), where L represents L-1, and R2 is particularly preferably defined as described above. The focus is on compounds of formula (I), where L represents L-2. 15 The focus is on compounds of formula (I), where R1 represents hydrogen. The focus is on compounds of formula (I), where R1 represents fluorenyl. The focus is also on compounds of formula (I), where R1 represents -C (= 0) C (= 0) R4, where R4 is as defined above. The focus is on compounds of formula (I), where A represents A1. 20 Saturated or unsaturated hydrocarbon groups, such as alkyl or alkenyl, can be linear or branched, respectively, and also include combinations with heteroatoms, such as alkoxy. Substituted groups may be mono- or poly-substituted as required, and when poly-substituted, the substituents may be the same or different. Groups substituted by valences such as, for example, halogenated groups, are monohalogenated or -31-200528434 j. In the case of polymorphism in the right, the self atoms may be the same or in phase. At this time, the dentin: table, fluorine: chlorine, evolution and iodine, specifically fluorine, chlorine and desert. Therefore, 'the above-mentioned or general or better group definition or Lang can also be combined as needed', that is, in its individual position 11 and better care. These definitions also apply to end products and corresponding precursors and intermediates. The above definitions can be combined with each other as needed. In addition, individual meanings are used. (The ten definitions of "good, good or very good" are those compounds of the formula 有 with the above-mentioned, particularly good, or very good substituents, respectively. Dihexylfluorene ^ Preparation method (a) uses 3-digas Methyl "4-methyl its m 15 ® Ar AV * -Hou ^ azole-4-carbonyl chloride and [2- (U, 3-tri-suppressed description of the starting material 'according to this method, the following 20

式(11)提Γί行板據本發明製法⑷時之起始物之叛酸 衍生物二?二 式(11)中’Α之較佳、特別佳與極 特別佳疋義均如以板據本發明式⑴化合物中所分別說 -32- 200528434 明A之較佳、特別佳與極特別佳定義。χι較佳為代表氯、 演或經基。 5 大多數式(II)羧酸衍生物為已知者與/或可依已知製法 製備（參見 WO 93/11117、ΕΡ-Α0 545 099、EP-A 0589 301 與 EP-A 0589313)。 式（II_a)3-二氣曱基口比唾-4-魏酸衍生物 10Formula (11) can be used according to the invention. The acid derivative of the starting material when the method is used in the formula (11). In the compound of formula (I) of the present invention, -32-200528434 Ming A is better, particularly good, and very particularly good definition. χι is preferably represented by chlorine, carbon or hydrogen. 5 Most carboxylic acid derivatives of formula (II) are known and / or can be prepared according to known methods (see WO 93/11117, EP-A0 545 099, EP-A 0589 301 and EP-A 0589313). 3-Diaziridinyl-l-sial-4-weilic acid derivative of formula (II_a) 10

其中among them

Rl2如上述定義， X 代表齒素或羥基 >、衣法為在第一步驟中，由式（V)酮基縮醛Rl2 is as defined above, X represents tooth element or hydroxyl

15 (V)15 (V)

其中 20 R43 R44 R44 代表cvcv烷基，較佳為曱基、乙基、正丙基、異丙 基、正-、第二·、第三-丁基， 與R分別代表甲基或乙基，或 與 R45 代表-(CH2)3-或-CH2-C(CH3)2-CH2-與式(VI)原甲 酸烷基酯 -33- 200528434 HC-(OR46)3 (VI) 其中 5 R46代表CrC^r烧基，較佳為甲基、乙基、正丙基、異丙 基、正-、第二-、第三-丁基，於酸酐之存在下（例如·· 乙酸酐）反應，所得式(VII)化合物 10Wherein 20 R43 R44 R44 represents a cvcv alkyl group, preferably fluorenyl, ethyl, n-propyl, isopropyl, n-, second, third-butyl, and R respectively represent methyl or ethyl, Or R45 represents-(CH2) 3- or -CH2-C (CH3) 2-CH2- and alkyl orthoformate of formula (VI) -33- 200528434 HC- (OR46) 3 (VI) where 5 R46 represents CrC ^ r alkyl, preferably methyl, ethyl, n-propyl, isopropyl, n-, second-, third-butyl, reacted in the presence of an acid anhydride (such as acetic anhydride) to obtain Compound of formula (VII) 10

其中R43、R44、R45與R46如上述定義， 於第二步驟中，與式(VIII)肼衍生物 R12-NH-NH2 (VIII) 其中R12如上述定義， 15 於稀釋劑之存在下(例如：甲醇)反應，Wherein R43, R44, R45 and R46 are as defined above, and in the second step, the hydrazine derivative of formula (VIII) R12-NH-NH2 (VIII) wherein R12 is as defined above and 15 is in the presence of a diluent (for example: Methanol) reaction,

所得之式(IX户比唑衍生物 20Resulting formula (IX-Hubazole derivative 20

其中R12、R43、R44與R45如上述定義， 於第三步驟中，於酸之存在下(例如··鹽酸)及於稀釋劑之 存在下(例如··二啐烷)反應， 所得之式(X)3-甲醯基-111-咐^坐-4-羧酸酯 -34- 200528434R12, R43, R44, and R45 are as defined above. In the third step, the reaction is performed in the presence of an acid (for example, hydrochloric acid) and in the presence of a diluent (for example, dioxane). The obtained formula ( X) 3-Methenyl-111-methyl-4-carboxylic acid ester-34- 200528434

R12與R43如上述定義 a) 於第四步驟中，於鹼之存在下（例如：氫氧化鋰)及於 稀釋劑之存在下（例如··四氳呋喃）水解，所得之式 (XI)3-曱醯基-1H-吡唑-4-羧酸R12 and R43 are as defined above a) In the fourth step, hydrolysis in the presence of a base (for example: lithium hydroxide) and in the presence of a diluent (for example, tetramethylfuran), the resulting formula (XI) 3 -Fluorenyl-1H-pyrazole-4-carboxylic acid

ίο 其中R12如上述定義 15 或 b) 再與氯化劑（例如：五氯化磷），於稀釋之存在下（例 如：二氯甲烷)反應， 於第四步驟中，與氯化劑（例如：五氯化磷)於稀釋劑 之存在下（例如··二氯曱烧)反應， 所得之式(ΧΠ)3 -二氯曱基-1H-吡唑-4-羧酸酯ίο Wherein R12 is as defined above 15 or b) and then react with a chlorinating agent (for example: phosphorus pentachloride) in the presence of dilution (for example: dichloromethane), and in the fourth step, with a chlorinating agent (for example: : Phosphorus pentachloride) in the presence of a diluent (e.g., dichlorofluorene), the resulting formula (χΠ) 3-dichlorofluorenyl-1H-pyrazole-4-carboxylic acid ester is obtained.

其中R12與R43如上述定義 •35- 20 200528434 再於驗之存在下（例如··氬氧化鋰)及於稀釋劑之存在 下（例如：四氫呋喃）水解。 式（111)提供進行根據本發明製法（a)亦需要作為起始 物之苯胺衍生物之一般定義。此式(111)中，[、“與汉3之 車父佳 '特別佳與極特別佳定義均如上述根據本發明式⑴ =合物中所分別說明此等基團之較佳、特別佳與極特別佳 ^^義。 有些式(III)中L代表L-1之苯胺衍生物為新穎化合 物。式(III)中L代表L-1之苯胺衍生物之製法可為 c)由式(XIII)苯胺衍生物Among them, R12 and R43 are as defined above. • 35-20 200528434 Hydrolyzed in the presence of a test (such as lithium argon oxide) and in the presence of a diluent (such as tetrahydrofuran). Formula (111) provides a general definition of an aniline derivative which is also required as a starting material for carrying out the process (a) according to the invention. In this formula (111), the definitions of [, ", and Che Fu Jia of Han 3 'are particularly good and very particularly good are as described above according to the formula ⑴ = compound of the present invention. It has a very good meaning. Some aniline derivatives in which L represents L-1 in formula (III) are novel compounds. The method for preparing aniline derivatives in which L represents L-1 in formula (III) can be c) from formula ( XIII) Aniline derivative

其中R1與R2如上述定義 於第一步驟中，與式(XIV)烯反應Where R1 and R2 are as defined above in the first step and react with the ene of formula (XIV)

其中 R3如上述定義， 若適當時，於觸媒之存在下，及若適當時，於稀釋齊^ 之存在下進行， 所得之式(XV)烯苯胺類 -36- 200528434Wherein R3 is as defined above, if appropriate, in the presence of a catalyst, and if appropriate, in the presence of a diluent ^, the obtained formula (XV) enaniline -36- 200528434

於第 〜y田1 , 聊袢劑之存在下，及方 於觸媒之存在下進行氫化反應。The hydrogenation reaction was performed in the presence of ~~ y1, liao tincture, and a catalyst.

提供進行根據本發明製法⑹時作為起始物之 二—般定義。此式(χιπ)中，ri與r2之較佳、 + 广團較佺、4寸別佳與極特別佳定義。 弋(χίπ)中广：：生物為已知者或可依已知製法製備。 iL類 代表氫之苯胺衍生物製法可由式(χπ“) 15 h2n^OR2 (ΧΙΠ-a) 其中R2如上述定義 與式(IV)鹵化物反應 τ> 1-A v2 K ~Χ (IV) 其中Rk與X2如上述定義， 其係於鹼之存在下及於稀釋劑之存在下 法⑻之反應條件。） 。（可採用製 式(XIV)提供進行根據本發明製法(c)時亦需 文吓為起 20 200528434 始物之坤之一般定蓋 ,, 與極特別佳定義’R3之較佳、特別隹 別說明此基團之較佳==本發明式⑴化合物中所分 有些綱v)稀為車t〇者特別佳與極特別佳定義。 之烯ί(胺之)提根據本發明製法⑷時所製得中間物 之席錢之-般定義。此式(xv)巾，r1、r2 物 特別佳與極特別佳定義 =2佳、 中所分別朗轉基據林明式(1)化合物 有些式(XV)烯苯胺為已知者。 我 根據本發明製法(c)可依多種不同方式進行。因此，可 以先由式(XIII_a)苯胺與式(XIv)稀反應， 應苯胺衍生物， ；相Two general definitions are provided as starting materials when carrying out the method according to the present invention. In this formula (χιπ), ri and r2 are better, + wide group is better, 4 inches are better, and very good definition.弋 (χίπ) Zhongguang :: The organism is known or can be prepared according to known methods. The method for preparing aniline derivatives of type iL representing hydrogen can be represented by the formula (χπ ") 15 h2n ^ OR2 (χΙΠ-a) where R2 is as defined above and reacted with the halide of formula (IV) τ > 1-A v2 K ~ X (IV) where Rk and X2 are as defined above, which are the reaction conditions in the presence of a base and a diluent in the presence of a diluent.) (The formula (XIV) can be used to provide a method for carrying out the method (c) according to the present invention. The general fixed cover of the beginning of 20 200528434, and the very good definition of 'R3', especially the better description of this group == some outlines in the compound of formula ⑴ of the present invention v) Those who are thinner are particularly well-defined and extremely well-defined. The general definition of ene (amine) is based on the intermediate cost of the intermediate produced during the method of the present invention. This formula (xv), r1, The definition of r2 is particularly good and very special = 2 is good, according to Liming, according to the compound of formula (1), some of the formula (XV) enaniline are known. According to the preparation method (c) of the present invention, there can be a variety of It can be carried out in different ways. Therefore, the dilute reaction of aniline of formula (XIII_a) with formula (XIv) can be performed first.

(ΙΠ-a) 15 其中R2與R3如上述定義， 然後，若適當時，與式(IV)鹵化物 Rua-X2 (IV) 2〇 其中R1^與X2如上述定義 於鹼之存在下及於稀釋劑之存在下反應，產生相應之式 (III)苯胺衍生物[同樣可採用製法(b)之反應條件]。 然而，亦可與式(IV)鹵化物在式(XV)之烯苯胺類階段 反應，以後再進行氫化反應。 •38- 200528434 式(ΙΙΙ-b)苯胺衍生物(IΠ-a) 15 wherein R2 and R3 are as defined above, and then, if appropriate, with a halide of formula (IV) Rua-X2 (IV) 2〇 wherein R1 and X2 are as defined above in the presence of a base and The reaction in the presence of a diluent yields the corresponding aniline derivative of formula (III) [the reaction conditions of the manufacturing method (b) can also be used]. However, it is also possible to react with the halide of the formula (IV) at the enanilide stage of the formula (XV) and then carry out the hydrogenation reaction later. • 38- 200528434 aniline derivative of formula (III-b)

5 其中 a) RM代表氫及 R3_B代表#素、C3-C8炫基、CrC8齒烧基， 或 10 15 b) R14代表C^CV烷基、CrCV烷基亞磺醯基、Ci_C6_ 烧續醯基、CVC4-炫氧基-CrCzr燒基、c3-cv 環烧基；crc6-鹵炫基、Ci-C4-鹵烧琉基、c^-cv 鹵烷基-亞磺醯基、CrCr鹵烷基磺醯基、由 -CVC4-烧氧基-C1-C4-炫基、C3-CV齒環烧基， 其分別具有1至9個氟、氯與/或溴原子；甲醯 基、甲醯基-cvc3-烷基、（crc3·烷基）羰基 -CKCV烷基、（CVCV烷氧基)幾基-CrC3-烷基； 自-(Ci-C3-烧基)幾基-CrCV燒基、KQ-C3-烧 氧基)羰基-Ci-CV烷基，其分別具有丨至丨3個 氟、氯與/或溴原子；（CVCr烷基)羰基、（crCV 烷氧基）羰基、（Ci-Cr烷氧基-CrCr烷基）羰 基、（cvcv環烷基)羰基；（Ci_C6_自烷基)羰基、 (CVCV齒烷氧基）羰基、（由_Ci_C4_烷氧基 <VCV烷基）羰基、（C3_C8_S環烷基）羰基，其 -39- 20 200528434 分別具有1至9個氟、氯與/或溴原子；或 -C(二0)C(=0)R4、C〇NR5R6 或-CH2NR7R8，及 R 代表虱、_素、Ci_c8-烧基、crc8-齒燒基， 5 10 15 R2、R4、R5、R6、R7與R8分別如上述定義， 為新穎者，且亦成為本申請案之部份主題。 R1與R3之較佳、特別佳與極特別佳定義分別相應於 1^8與1133，其中在幻項中，總是代表氫，而R3^不 代表氳、甲基或乙基，及於b)項中，R1-B不代表氣。R2、 R R R、R與R之較佳、特別佳與極特別佳定義同 樣適用於新穎之式（ΙΠ-b)化合物。 卜其重點在於式(ΙΙΙ-b)化合物，其中尺1與R2分別代表 氫’ R3代表氟、氯、甲基、乙基、三氟甲基 中L_L_2、L_3或L_4之苯胺衍生物係已土知 者與7或可依已知方法製備（參見例如：EP-a 1 036 793盥 EP-A 0 737 682)。 ~ 式（III)中L代表L-2、L-3或L-4，R1不代 衍生物之製法可由式(III-c)苯胺類 h2n—^ r3 其中 L1 代表 L-2、L-3 或 L-4，及 L-2、L-3、L_4與r3如上述定義， 20 200528434 與式(ιν)鹵化物反應 R1a-X2 (IV) 其中以^與X2如上述定義 其係於驗之存在下與於稀釋劑之存在下進行[可採用製法 5 (b)之反應條件]。 製法〇)) 使用I，3,5-三甲基專[2-(1，3,3-三甲基丁基）苯基]_1H_n比唑 -4-羧醯胺與氯(氧代)乙酸乙酯作為起始物，根據本發明之 製法(b)之製程以下列反應圖說明：5 of which a) RM represents hydrogen and R3_B represents # prime, C3-C8 alkyl, CrC8 tooth alkyl, or 10 15 b) R14 represents C ^ CV alkyl, CrCV alkylsulfinyl, Ci_C6_ alkylene , CVC4-Hexoxy-CrCzr alkyl, c3-cv cycloalkyl; crc6-halo alkyl, Ci-C4-haloalkyl, c ^ -cv haloalkyl-sulfinyl, CrCr haloalkyl Sulfonyl, -CVC4-carboxy-C1-C4-xyl, C3-CV tooth ring alkyl, which have 1 to 9 fluorine, chlorine and / or bromine atoms, respectively; formamyl, formamyl -cvc3-alkyl, (crc3 · alkyl) carbonyl-CKCV alkyl, (CVCV alkoxy) -chic-CrC3-alkyl; from-(Ci-C3-alkyl) -chicyl-CrCV alkyl, KQ -C3-alkyloxy) carbonyl-Ci-CV alkyl, which respectively have three to three fluorine, chlorine and / or bromine atoms; (CVCr alkyl) carbonyl, (crCV alkoxy) carbonyl, (Ci- Cr alkoxy-CrCr alkyl) carbonyl, (cvcvcycloalkyl) carbonyl; (Ci_C6_self alkyl) carbonyl, (CVCV alkoxy) carbonyl, (from _Ci_C4_alkoxy < VCV alkyl ) Carbonyl, (C3_C8_S cycloalkyl) carbonyl, each of which has -39-20 200528434 having 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (di0) C (= 0) R4 C〇NR5R6 or -CH2NR7R8, and R represents lice, _ prime, Ci_c8-alkyl, crc8-dental, 5 10 15 R2, R4, R5, R6, R7 and R8 are as defined above and are novel, and It has also become part of the subject matter of this application. The better, particularly good, and very particularly good definitions of R1 and R3 correspond to 1 ^ 8 and 1133, respectively, where in the magic term, always represents hydrogen, and R3 ^ does not represent fluorene, methyl, or ethyl, and b In item), R1-B does not represent qi. The better, particularly good and very particularly good definitions of R2, R R R, R and R apply equally to the novel compounds of formula (II-b). The focus is on compounds of formula (II-I-b), in which rule 1 and R2 represent hydrogen, respectively. R3 represents fluorine, chlorine, methyl, ethyl, trifluoromethyl, and the aniline derivative of L_L_2, L_3, or L_4 has been The authors and 7 may be prepared according to known methods (see, for example, EP-a 1 036 793 and EP-A 0 737 682). ~ In formula (III), L represents L-2, L-3, or L-4, and the method for preparing R1 without a derivative can be obtained from formula (III-c) anilines h2n- ^ r3, where L1 represents L-2, L-3 Or L-4, and L-2, L-3, L_4 and r3 are as defined above, 20 200528434 reacts with the halide of formula (ιν) R1a-X2 (IV) where ^ and X2 are as defined above and they are subject to the test It is carried out in the presence and in the presence of a diluent [reaction conditions of production method 5 (b) can be used]. Production method 0)) using I, 3,5-trimethyl [[(2,1,3,3-trimethylbutyl) phenyl] _1H_n-pyrazole-4-carboxamide and chloro (oxo) acetic acid Ethyl ester is used as a starting material, and the production process according to the production method (b) of the present invention is illustrated by the following reaction diagram:

15 式(I-a)提供進行根據本發明製法_斤需起始物之己 基酿基苯胺之—般定義。此式(I·种，R2、R3與A之較佳、 =別佳與極特別佳定義均如上述根據本發明式合物 此等基團之較佳、特難與極特別佳定義。 本申請:之部:H本胺:為根據本發明化合物，亦形成 (其中氫）。 ^ w依根據本發明製法(a)中製得 化物^ - 亦作為根據本發明製法(b)之起始物之卣 tAA代表cvcv乾基、〇1<4_烷基亞磺醯基、 20 200528434 C1-C4-烧石黃酿基、C1-C3-烧氧基-C1-C3-烧基、C3-C6-環烧基，C1-C4-鹵燒基、C1-C4-鹵炫硫基、C1-C4-_烧基-亞石黃酿基、Ci-C4-鹵烧基石黃酿基、鹵-Ci-C3-烷氧基-Q-C3-烷基、c3-c8-_環烷基，其分別具有 5 1至9個氟、氯與/或溴原子；甲醯基、曱醯基-CkC3- 烷基、（CrC3-烷基)羰基-CrC3-烷基、（Ci-CV烷氧 基）羰基-CVCV烷基；鹵-(CVCV烷基）羰基-Ci-Q-烷基、鹵-(CKC3-烷氧基）羰基-CrCr烷基，其分別· 具有1至13個氟、氯與/或溴原子； 10 (CVCV烷基）羰基、（CVCV烷氧基）羰基、（CVC3-烷 氧基-Cl-C3-烷基）羰基、（C3-C6-環烷基）羰基； (C^Cr鹵烷基）羰基、（Ci-Cr鹵烷氧基）羰基、（鹵 -CrCV烷氧基-cvcv烷基)羰基、（C3-C6-鹵環烷基） 羰基，其分別具有1至9個氟、氯與/或溴原子； 15 或-C(=0)C(=0)R4、-CONR5R6 或-CH2NR7R8。 R1 A 特別佳為代表甲基、乙基、正或異丙基、正、異、· 第二-或第三-丁基、戊基或己基、甲基亞磺醯基、 乙基亞磺醯基、正或異丙基亞磺醯基、正-、異_、 第二_或第三-丁基亞磺醯基、甲磺醯基、乙基磺醢 20 基、正或異丙基磺醯基、正-、異-、第二-或第三- 丁磺醯基、甲氧基甲基、甲氧基乙基、乙氧基甲基、 乙氧基乙基、環丙基、環戊基、環己基、三氟甲基、 三氯甲基、三氟乙基、二氟甲硫基、二氟氯曱硫基、 三氟甲硫基、三氟甲基亞磺醯基、三氟甲磺醯基、 -42- 200528434 三氟甲氧基曱基；甲醯基、-CHrCHO、-(CH2)rCHO、 -CH2-CO-CH3 ^ -CH2-CO-CH2CH3 ^ -CH2-CO-CH(CH3)2 ^ -(CH2)2-CO-CH3 > -(CH2)2-CO-CH2CH3 ^ -(CH2)2-CO-CH(CH3)2 ^ -CH2-C02CH3 > -CH2-CO2CH2CH3 > -CH2-C02CH(CH3)2 ^ -CCH2)2-C02CH3 > <CH2)2-C02CH2CH3 ^ -(CH2VC02CH(CH3)2 ^ CHrCO-CF3 、-CH2-C0-CC13 、-CHrCO-CH2CF3 、 -CH2-CO-CH2CCl3 ^ -(CH2)2-CO-CH2CF3 ^ -(CH2VCO-CH2CCl3 --CHrC02CH2CF3、<HrC02CF2CF3、-CH2_C02CH2CC13、 -(^-C02CC12CC13、仰2VC02CH2CF3、仰2)rC02CF2CF3、 仰2)tC〇2ch2cci3、_(〇ί2)2<χ^α2(χι3; 甲基羰基、乙基羰基、正丙基羰基、異丙基羰基、 第三-丁基羰基、甲氧基羰基、乙氧基羰基、第三_ 丁氧基羰基、環丙基羰基;三氟甲基羰基、三氟曱 氧基羰基或-C(=0)C(=0)R5、-CONR6R7 或 -CH2NR8R9。 R1 A 極後圭為代表曱基、甲氧基甲基、甲醯基、 -CH2_CHO、(CH2VCHO、CHr CO-CH3、CH2_CO-CH2CH3、 -CHrCO_CH(CH3)2、_c(=0)CH0、-C(=0)C(=0)CH3、 -C(=O)C(=O)CH20CH3 > -C(=0)C02CH3 - -C(=0)C02CH2CH3 - X2 毯皇^代表氣或溴。 式(IV)鹵化物為已知者。 反應條件 適合進行根據本發明製法(a)之稀釋劑為所有惰性有 -43- 200528434 如，例如=脂系、脂環系或芳香系烴類， 苯、甲笨=己烧、庚烧、環己境、甲基環己烧、 -氣：：燒；由化煙類，如，例如：氯苯、 :二二：氯仿、四氣化碳、二氣乙烧或三氯乙 基第耸 /二異丙基醚、甲基第三丁基醚、f Γ2 、一、烧、四氫咬喃、二甲氧基乙炫、 ，z-—乙氧基乙烷或苯甲醚，或醯胺類， 甲醯胺、Ν，Ν·二曱基乙醯胺、N•曱基甲酸胺、二 吼嘻喷_或六曱基磷酸三醯胺。 —土 下根據本發明躲⑷若適#時，係於合㈣受體之存在 。合適酸受體為所有常狀無機或有機驗類。此等 t驗類包括驗土金屬紐金屬氳化物、魏化物、胺化15 Formula (I-a) provides a general definition of hexyl aniline for carrying out the process of the present invention. This formula (I ·, better definitions of R2, R3, and A, = best and extremely special definitions are as described above for the better, particularly difficult, and extremely special definitions of these groups of compounds according to the formula of the present invention. Application: Department: H This amine: is a compound according to the present invention, and also forms (wherein hydrogen). ^ W is prepared according to the process (a) according to the present invention ^-Also serves as the start of the process (b) according to the present invention卣 tAA stands for cvcv dry group, 〇1 < 4-alkylsulfinylfluorenyl group, 20 200528434 C1-C4-carbosulfanyl group, C1-C3-carbooxy-C1-C3-carbo group, C3- C6-Cycloalkyl, C1-C4-halothio, C1-C4-halosulfanyl, C1-C4-_alkenyl-sulfite yellow, Ci-C4-halohalyl, yellow- Ci-C3-alkoxy-Q-C3-alkyl, c3-c8-_cycloalkyl, which each have 51 to 9 fluorine, chlorine and / or bromine atoms; formamyl, fluorenyl-CkC3 -Alkyl, (CrC3-alkyl) carbonyl-CrC3-alkyl, (Ci-CV alkoxy) carbonyl-CVCV alkyl; halo- (CVCV alkyl) carbonyl-Ci-Q-alkyl, halo- ( CKC3-alkoxy) carbonyl-CrCr alkyl, which respectively have 1 to 13 fluorine, chlorine and / or bromine atoms; 10 (CVCV alkyl) carbonyl, (CVCV alkoxy) carbonyl, ( CVC3-alkoxy-Cl-C3-alkyl) carbonyl, (C3-C6-cycloalkyl) carbonyl; (C ^ Crhaloalkyl) carbonyl, (Ci-Crhalalkoxy) carbonyl, (halo- CrCV alkoxy-cvcv alkyl) carbonyl, (C3-C6-halocycloalkyl) carbonyl, each having 1 to 9 fluorine, chlorine and / or bromine atoms; 15 or -C (= 0) C (= 0) R4, -CONR5R6 or -CH2NR7R8. R1 A is particularly preferably represented by methyl, ethyl, n- or iso-propyl, n-, iso-, second- or third-butyl, pentyl or hexyl, methyl Sulfinyl sulfenyl, ethylsulfinyl sulfinyl, n- or isopropylsulfinyl sulfinyl, n-, iso-, second- or third-butylsulfinyl sulfinyl, methanesulfinyl, ethylsulfonyl醢 20-based, n- or isopropylsulfonyl, n-, iso-, second- or third-butanesulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethyl Oxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochlorofluorenylthio, trifluoromethylthio, Trifluoromethylsulfinyl, trifluoromethanesulfonyl, -42- 200528434 trifluoromethoxyfluorenyl; methylfluorenyl, -CHrCHO,-(CH2) rCHO, -CH2 -CO-CH3 ^ -CH2-CO-CH2CH3 ^ -CH2-CO-CH (CH3) 2 ^-(CH2) 2-CO-CH3 >-(CH2) 2-CO-CH2CH3 ^-(CH2) 2- CO-CH (CH3) 2 ^ -CH2-C02CH3 > -CH2-CO2CH2CH3 > -CH2-C02CH (CH3) 2 ^ -CCH2) 2-C02CH3 > < CH2) 2-C02CH2CH3 ^-(CH2VC02CH (CH3 ) 2 ^ CHrCO-CF3, -CH2-C0-CC13, -CHrCO-CH2CF3, -CH2-CO-CH2CCl3 ^-(CH2) 2-CO-CH2CF3 ^-(CH2VCO-CH2CCl3 --CHrC02CH2CF3, < HrC02CF2CF3,- CH2_C02CH2CC13,-(^-C02CC12CC13, Yang 2VC02CH2CF3, Yang 2) rC02CF2CF3, Yang 2) tC〇2ch2cci3, _ (〇ί2) 2 < χ ^ α2 (χι3; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropyl Propylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, cyclopropylcarbonyl; trifluoromethylcarbonyl, trifluorofluorenyloxycarbonyl, or -C ( = 0) C (= 0) R5, -CONR6R7 or -CH2NR8R9. R1 A pole is represented by fluorenyl, methoxymethyl, formamyl, -CH2_CHO, (CH2VCHO, CHr CO-CH3, CH2_CO-CH2CH3, -CHrCO_CH (CH3) 2, _c (= 0) CH0,- C (= 0) C (= 0) CH3, -C (= O) C (= O) CH20CH3 > -C (= 0) C02CH3--C (= 0) C02CH2CH3-X2 blanket ^ represents gas or bromine The halide of formula (IV) is known. The reaction conditions suitable for carrying out the method (a) of the present invention are all diluents of -43- 200528434 such as, for example, aliphatic, alicyclic or aromatic hydrocarbons, Benzene, methylbenzyl = hexane, heptane, cyclohexanone, methylcyclohexane, -gas :: burning; from chemical smoke, such as: chlorobenzene,: 22: chloroform, tetragasified carbon, Digas ethyl or trichloroethyl ether / diisopropyl ether, methyl tert-butyl ether, f Γ2, mono, tetrahydrofuran, dimethoxyethyl, z --- ethyl Ethoxyethane or anisole, or amidines, formamidine, N, N · dimethylacetamidoamine, N • amidoformic acid amine, dioxin or hexamethyltrimethylamine phosphate. -Under the soil when hiding in accordance with the present invention, it is due to the presence of synthetic receptors. Suitable acid receptors are all normally inorganic or organic. These t-tests include tau-tests of metal, metal, metal, and aminate.

物、醇鹽類、乙酸鹽、碳酸鹽或碳酸氫鹽，如，例如· I 15 20 巧、胺化鈉、甲醇鈉、乙醇鈉、第三丁醇卸、氫氧化納風 =乳化鉀、氫氧化銨、乙酸鈉、乙酸鉀、乙酸鈣、乙酸銨、 碳酸納、碳酸鉀、碳酸氫鉀、碳酸氳鈉或啖酸銨，與二級 2，如：三甲基胺、三乙基胺、三丁基胺、N，N·:;基 ^、邮二曱基苯甲基胺、吡啶、队甲基六氫吡啶、队 I基嗎啉、N，N-二甲基胺基吡啶、重氮雙環辛 (DABc〇)、重I雙環壬烯（DBN)或重氮雙产 (DBU)。 I卞一碳烯 根據本發明製法(a)若適當時，係於合適縮合劑之 下進行。合適縮合劑為所有此等醯胺化反應^用 子人 劑。可述及例如：酸自化物形成劑，如：€炭釀氯、 -44- 5 10 15 20 ，每莫耳 0·5 至 2 200528434 拜、二氯化磷、五氯化磷、磷醯氯或亞硫醯氯；酸酐形成 劑’如：氯甲酸乙酯、氯甲酸甲酯、氯甲酸異丙基酯、氯 甲酉欠異丁基酯或甲石黃醯氯；碳化二亞胺，如，n，n，-二環己 基反化〜亞胺(DCC) ’或其他常用之縮合劑，如：五氧化 %、聚磷酸、N，N,_羰基二咪唑、乙氧基_N_乙氧基羰基 1，2_二氫喹啉(EEDQ)、三·苯基膦/四氯化碳或溴化三吡洛 啶基鱗六氟磷酸鹽。 —根據本發明製法(a)若適當時，係於觸媒之存在下進 二田ί實例可述及4_二甲基胺基吡啶、^羥基苯并三唑或 一甲基甲醯胺。 〆 、行根據本發明製法(幻時，反應溫度 内變化。料，鱗製_於龜靴1^：^圍 較佳為〇°C至8(TC之溫度。 。之-度下進仃’ 進行根據本發明製法(a)以製備式 式_衍生物通常使用〇.2至5莫(二= 莫耳式(III)苯胺衍生物。 適合進行根據本發明製法(b) 機溶劑。較佳溶劑包括脂系、脂释齊^為所有情性有 例如:石_、己烧、庚燒、=或=!、烴類’如， 甲苯、二甲苯或萘㈠化“已：、：，己烧、苯、 苯、二氯甲烷、氯仿、四氯化碳=氯苯、二氯 _，如：乙峻、二異丙基喊、甲C三氯乙燒; 三戊基醚、二姐、四氫咬喃、、甲基第 二乙氧基乙燒或苯㈣，或酿軸，如： -45- 200528434 胺、N，N-二甲基乙醯胺、N-甲基甲酿替苯胺、N-甲基吼口各 啶酮或六曱基磷酸三醯胺。 5 10 15 20 根據本發明製法(b)係於鹼之存在下進行。合適鹼為所 有常甩之無機或有機鹼類。此等較佳鹼類包括鹼土金屬或 鹼金屏氫化物、氫氧化物、胺化物、醇鹽類、乙酸鹽、碳 酸鹽或礙酸氫發’如，例如：氫化納、胺化鈉、曱醇鈉、 乙醇鈉、第三丁醇鉀、氫氧化鈉、氳氧化鉀、氫氧化銨、 乙酸納、乙酸鉀、乙酸#5、乙酸銨、碳酸納、碳酸鉀、碳 酸氫卸、碳酸氫鈉或碳酸铯，與三級胺類，如：三曱基胺、 二乙基胺、三丁基胺、N，N-二甲基苯胺、Ν，Ν·二甲基苯甲 基胺、吨咬、Ν-甲基六氫吼咬、Ν-曱基嗎琳、Ν，Ν-二甲基 胺基u比啶、重氮雙環辛烷(DABC0)、重氮雙環壬烯(dbn) 或重氮雙環十一碳烯(DBU)。 根據本發明製法(b)之反應溫度可在相當大範圍内變 化。通常，該製法係於〇t：至150°C之溫度下進行，較佳 為20¾至ll〇°c之溫度。 進行根據本發明製法(b)以製備式(I)化合物時，每莫】 式(I-a)己基醯基苯胺通常使用〇2至5莫耳，較佳為〇 至2莫耳式(IV)鹵化物。 · 適合進行根據本發明製法(c)之第一步驟之稀釋劑為 所有惰性有機溶劑。較佳溶劑包括腈類，如：乙腈、丙腈、 正-或異丁腈或苯基氰，·或醢胺類，如：N，N_二甲基甲釀 胺、N，N-二甲基乙醯胺、N_甲基甲醢替苯胺、队甲基吡咯 咬酮或六甲基填酸三醯胺。 -46· 200528434Substances, alkoxides, acetates, carbonates, or bicarbonates, such as, for example, I 15 20, sodium amidate, sodium methoxide, sodium ethoxide, third butanol, sodium hydroxide = emulsified potassium, hydrogen Ammonium oxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium hafnium carbonate, or ammonium acetate, and the second stage 2, such as: trimethylamine, triethylamine, Tributylamine, N, N ·:; yl, diphenylbenzylamine, pyridine, hexamethylpyridine, ylmorpholine, N, N-dimethylaminopyridine, heavy Nitrobicyclooctane (DABc0), heavy I-bicyclononene (DBN), or diazobis-production (DBU). I 卞 -carbene The process (a) according to the present invention is carried out, if appropriate, under a suitable condensing agent. Suitable condensing agents are all such amination agents. It can be mentioned, for example, acid autogen forming agents, such as: charcoal, chlorine, -44- 5 10 15 20, 0.5 to 2 per mole 200528434 Bayer, phosphorus dichloride, phosphorus pentachloride, phosphorous chloride Or thionyl chloride; anhydride forming agents such as: ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, chloroformyl isobutyl ester or methotrene chloride; carbodiimide, such as , N, n, -Dicyclohexyl inversion ~ imine (DCC) 'or other commonly used condensing agents, such as:% pentoxide, polyphosphoric acid, N, N, _carbonyldiimidazole, ethoxy_N_ethyl Oxycarbonyl1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride or tripyridinylphosphonium hexafluorophosphate. -According to the production method (a) of the present invention, if appropriate, it is carried out in the presence of a catalyst. An example of Nita may be 4-dimethylaminopyridine, hydroxybenzotriazole, or monomethylformamide. (1) According to the manufacturing method of the present invention (the magic time, the reaction temperature varies. It is expected that the scale system is preferably at a temperature of 0 ° C to 8 ° C in the tortoise boots. The temperature is to be lowered to the next degree. The production process (a) according to the present invention is carried out to prepare the formula-derivatives, usually using 0.2 to 5 moles (di = mole (III) aniline derivatives. Suitable for the production process (b) organic solvents according to the present invention. Preferably Solvents include lipids, fat releases, and all emotions such as: stone, hexane, heptane, = or = !, hydrocarbons such as toluene, xylene, or naphthalene, "have:,:, Burning, benzene, benzene, dichloromethane, chloroform, carbon tetrachloride = chlorobenzene, dichloro _, such as: Ethyl, diisopropyl, methyl C trichloroethane; tripentyl ether, two sister, Tetrahydrobutan, methyl second ethoxyethene or phenylhydrazone, or stuffing axis, such as: -45- 200528434 amine, N, N-dimethylacetamide, N-methylmethanil , N-methyl methylpyridinone or hexamethylphosphonium triammonium phosphate. 5 10 15 20 The method (b) according to the present invention is carried out in the presence of a base. Suitable bases are all commonly used inorganic or organic bases. These preferred bases include alkaline earth metals Alkali metal hydride, hydroxide, amidate, alkoxide, acetate, carbonate, or hinder hydrogen generation, such as, for example, sodium hydride, sodium amine, sodium alkoxide, sodium ethoxide, third butanol Potassium, sodium hydroxide, osmium potassium oxide, ammonium hydroxide, sodium acetate, potassium acetate, acetic acid # 5, ammonium acetate, sodium carbonate, potassium carbonate, hydrogen carbonate, sodium hydrogen carbonate or cesium carbonate, and tertiary amines, Such as: trimethylamine, diethylamine, tributylamine, N, N-dimethylaniline, N, N · dimethylbenzylamine, ton bite, N-methylhexahydrorole bite, N-fluorenyl morphine, N, N-dimethylamino u-pyridine, diazobicyclooctane (DABC0), diazobicyclononene (dbn) or diazobicycloundecene (DBU). According to The reaction temperature of the manufacturing method (b) of the present invention can be varied within a relatively wide range. Generally, the manufacturing method is performed at a temperature of 0 to: 150 ° C, preferably a temperature of 20¾ to 110 ° C. When inventing the production method (b) to prepare a compound of the formula (I), hexylfluorenylaniline of the formula (Ia) is usually used in an amount of 0 to 5 moles, preferably 0 to 2 moles of a halogen compound of the formula (IV). Suitable for The diluent in the first step of the method (c) of the present invention is all inert organic solvents. Preferred solvents include nitriles, such as: acetonitrile, propionitrile, n- or isobutyronitrile or phenylcyanide, or amidines , Such as: N, N-dimethylformamide, N, N-dimethylacetamide, N_methylformamide, trimethylpyrrolidone, or hexamethyltrimethylamine. -46 · 200528434

根，上一 一1...... 受體之 驗類。 氧化物 5 如，例如··氫化鈉、胺化鈉、甲醇鈉、乙醇鈉、第三丁醇 鉀、氫氧化鈉、氫氧化鉀、氫氧化銨、乙酸鈉、乙酸鉀、 乙酸鈣、乙酸銨、碳酸鈉、碳酸鉀、碳酸氬鉀、碳酸氫鈉 或碳酸銨，與三級胺類，如··三甲基胺、三乙基胺、三丁 基胺、N，N-二曱基苯胺、N，N-二甲基苯甲基胺、吡啶、N_ 10 甲基六氬吡啶、N-曱基嗎啉、N，N-二甲基胺基吡啶、重氮 雙環辛烷(DABCO)、重氮雙環壬烯(DBN)或重氮雙環十一 碳烯(DBU) 〇 根據本發明製法(c)之第一步驟係於一種或多種觸媒 之存在下進行。 15 合適觸媒特定言之為艇鹽或複合物。適合此目的者較 佳為氯化鈀、乙酸鈀、肆（三苯基膦）鈀或雙（三苯基膦）鈀 二氯化物。亦可能在反應混合物中分開添加纪鹽與複合物 配位體，以產生飽複合物。 較佳配位體為有機磷化合物。可述及下列實例：三苯 20 基膦、三-鄰甲苯基膦、2,2’-雙(二苯基膦基)-1，1匕聯萘、二 環己基膦聯苯、1，4-雙(二苯基膦基）丁烷、雙-二苯基膦基 二茂絡鐵、二-(第三-丁基膦基）聯苯、二(環己基膦基）聯 苯、2-二環己基膦基-2’-N，N-二曱基胺基聯苯、三環己基 膦、三-第三丁基膦。然而，亦可免用配位體 0 -47- 200528434 存在3本發明製法⑷之第—步驟亦可在其他金屬鹽之 子在下進仃，如：銅鹽，例如··碘化亞銅（ι)。 在相本發明製法⑷之第—步科之反應溫度可 内變化。通常，該製法係於靴至峨之 服度:進仃’較佳為贼至15(rc之溫度。 苯胺時订明製法(c)之第一步驟以製備式(XV)婦 較佳為1幻莫;生物通常使们至5莫耳， 之稀釋劑為戶: (C)之第二步驟(氫化反應) 系烴類，Η如:石=劑 環己燒或萘燒，·_，如&庚烧、核己烧、甲基 丁基醚、甲美第H 二異丙基醚、甲基第三 氧基乙燒或f2_r 土，、二号炫、四氳咬痛、…二甲 15 20 正-蛛丙醇m燒；醇類，如：甲醇、乙醇、 -1，2-二醇、乙氧基酿或第三-丁醇、乙二醇、丙 一乙一 m抑r甘 甲氧基乙醇、二乙二醇單甲基醚、 -乙-醇早乙細、其 根據本發明製法f 〇、 成口物$純水 之存在^ w )之第二步驟（氳化反應）係於觸媒 二=適=所有氮化反應常用之觸媒。其 如，例如：活性碳上 若適當時，係於單體上進行， 根據本發明製法( 乙基魏之存在下進杆4二步驟氫化反應亦可改於三 進行根據本發明；:J替代氫與觸媒之組合。 I去（C)之第二步驟之反應溫度可在 -48- 200528434 相當大範圍内變化。通當， 度下進行，較佳為2〇。〇至=製法係於〇<t至15〇°C之溫 根據本發明製法(c)之第之溫度。 巴下，較佳為2至50巴下步驟係於氫氣壓0.5與200 5 10 15 除非另有朗，否則勤，佳為3至1G巴下進行。 壓下進行，，亦可在二=發下:製二 巴至10巴間進行。 丁 m 根據本發明物質具有強效殺微生物活性且可在作物 保護法^料賴法巾，料㈣不要之微生物，如：真 菌與細菌。 殺真菌劑可用於作物保護法中控制根腫菌 (PlaSm〇di〇Ph〇r〇mycetes)、印菌（〇〇mycetes)、壺菌 (Chytridiomycetes)、接合菌（Zyg〇mycetes)、子囊菌 (Ascomycetes)、擔子菌（Basidi〇mycetes)與半知菌 (Deuteromycetes) 〇Root, the previous one ... the type of receptor. Oxides 5 such as, for example, sodium hydride, sodium amine, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate , Sodium carbonate, potassium carbonate, potassium argon carbonate, sodium bicarbonate or ammonium carbonate, and tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline , N, N-dimethylbenzylamine, pyridine, N_10 methylhexapyridine, N-fluorenylmorpholine, N, N-dimethylaminopyridine, diazobicyclooctane (DABCO), Diazobicyclononene (DBN) or diazobicycloundecene (DBU). The first step of the method (c) according to the present invention is performed in the presence of one or more catalysts. 15 Suitable catalysts are, in particular, boat salts or complexes. Suitable for this purpose are palladium chloride, palladium acetate, (triphenylphosphine) palladium or bis (triphenylphosphine) palladium dichloride. It is also possible to add a salt and a complex ligand separately in the reaction mixture to produce a saturated complex. A preferred ligand is an organic phosphorus compound. The following examples can be mentioned: triphenyl 20-ylphosphine, tri-o-tolylphosphine, 2,2'-bis (diphenylphosphino) -1,1 dinaphthalene, dicyclohexylphosphine biphenyl, 1,4 -Bis (diphenylphosphino) butane, bis-diphenylphosphinoferrocene, bis- (third-butylphosphino) biphenyl, bis (cyclohexylphosphino) biphenyl, 2- Dicyclohexylphosphino-2'-N, N-difluorenylaminobiphenyl, tricyclohexylphosphine, tri-tert-butylphosphine. However, the ligand 0-47-200528434 can also be exempted. 3 The first step of the method of the present invention can also be carried out under the sons of other metal salts, such as: copper salts, for example, · cuprous iodide (ι) . The reaction temperature in the first step of the method of the present invention can be varied within the range. Generally, the method is based on the suitability of boots to E: the temperature of the thief is preferably thief to 15 (rc. The first step of the manufacturing method (c) is specified in the case of aniline, and the formula (XV) is preferably 1 Molar; creatures usually make them up to 5 moles. The diluent is: (C) the second step (hydrogenation reaction) is a hydrocarbon, such as: stone = cyclohexane or naphthalene, · _, such as & Heptan, nuclear hexane, methyl butyl ether, methylidene diisopropyl ether, methyl tertiary ethoxylate or f2_r soil, No. 2 xuan, tetrathion bite, ... 15 20 n-Propanol alcohol; alcohols, such as: methanol, ethanol, 1,2-diol, ethoxy alcohol or tertiary-butanol, ethylene glycol, propylene glycol methylene glycol The second step of the ethoxyethanol, diethylene glycol monomethyl ether, -ethyl-alcohol, and its preparation according to the present invention f 0, the presence of pure water $ pure water ^ w) is For catalyst two = suitable = all commonly used catalysts for nitriding reactions. Such as, for example: if appropriate on activated carbon, it is carried out on the monomer, according to the method of the present invention (in the presence of ethyl weiwei, the two-step hydrogenation reaction can also be changed to three to carry out according to the present invention; The combination of hydrogen and catalyst. The reaction temperature in the second step of I to (C) can be changed within a relatively wide range of -48- 200528434. It is generally carried out under the degree, preferably 20.0. 〇 < t to 15 ° C The temperature according to the production method (c) of the present invention. Sub-bar, preferably 2-50 bar. The steps are under hydrogen pressure 0.5 and 200 5 10 15 unless otherwise stated. Otherwise, it is preferably carried out under 3 to 1 Gbar. It can be carried out under pressure, or it can be carried out between two = hair down: between two bars and 10 bar. Ding m The substance according to the present invention has strong microbicidal activity and can be used in crops. The protection method is based on the law, and the unnecessary microorganisms, such as fungi and bacteria. Fungicides can be used in crop protection methods to control rhizobia (PlaSm0di0Ph0r0mycetes), Indian bacteria (0. mycetes), Chytridiomycetes, Zygmymytes, Ascomycetes, Basidi. mycetes) and Deuteromycetes.

殺細菌劑可用於作物保護法中控制假單胞菌 (Pseudomonadaceae)、根瘤菌（Rhizobiaceae)、腸桿菌 (Enterobacteriaceae)、白喉桿菌（Corynebacteriaceae)與鏈黴 菌（Streptomycetaceae) 〇 源自上列菌類之真菌性與細菌性病害之病原菌可述 及例如（但不限於）： 黃單胞菌屬（Xanthomonas)如，例如：野油菜黃單胞菌 稻變種(Xanthomonas campestris pv· oryzae); 假單胞菌屬（Pseudomonas)如’例如：丁香假單胞菌 -49 - 20 200528434 (Pseudomonas syringae pv. lachrymans)； 歐文氏菌屬（Erwinia)如，例如：解澱粉歐文氏菌（Erwinia amylovora); 腐黴菌屬（Pythium)如，例如：終極腐黴(Pythium ultimum); 5 疫黴屬（Phytophthora)如，例如··致病疫黴（phytophthora infestans); 假霜黴屬（Pseudoperonospora)如，例如：蘀草假霜黴 (Pseudoperonospora humuli)或 古巴你艾霜黴 (Pseudoperonospora cubensis)； ίο 單轴黴屬(Plasmopara)如，例如：葡萄生單軸黴(piasmopara viticola); 盤梗徽屬（Bremia)如，例如·萬鱼盤梗徽(Bi*ernia lactucae); 霜黴屬（Peronospora)如，例如：豌豆霜黴(peronosporapisi) 或蕓苔霜黴(Ρ· brassicae); 15 白粉菌屬（Erysiphe)如，例如：禾白粉菌（Erysiphe graminis); 單絲殼屬（Sphaerotheca)如，例如：蒼耳單絲殼 (Sphaerotheca fuliginea)； 叉絲單囊殼屬（Podosphaera)如，例如：白叉絲單囊殼 2〇 (Podosphaera leucotricha) l 黑星菌屬（Venturia)如’例如·翁果黑星菌（Venturia inaequalis); 核腔菌屬（Pyrenophora)如，例如：圓核腔菌（pyrenoph〇ra teres)或麥類核腔菌（R graminea)(分生孢子型·· -50- 200528434Bactericides can be used to control Pseudomonadaceae, Rhizobaceae, Enterobacteriaceae, Corynebacteriaceae, and Streptomycetaceae in crop protection methods Pathogens associated with bacterial diseases can be mentioned, for example (but not limited to): Xanthomonas such as, for example: Xanthomonas campestris pv. Oryzae; Pseudomonas ( Pseudomonas) such as' For example: Pseudomonas syringae -49-20 200528434 (Pseudomonas syringae pv. Lachrymans); Erwinia such as: For example: Erwinia amylovora; Pythium ) For example: Pythium ultimum; 5 Phytophthora such as ... Phytophthora infestans; Pseudoperonospora such as: (Pseudoperonospora humuli) or Pseudoperonospora cubensis; ίο Plasmopara, for example: pisamo para viticola); Bremia such as, for example, Bi * ernia lactucae; Peronospora such as: peronosporapisi or P. brassicae · Brassicae); 15 Erysiphe, such as: Erysiphe graminis; Sphaerotheca, such as: Sphaerotheca fuliginea; Forsythia (Podosphaera) such as, for example: Podsphaera leucotricha l Venturia such as' e.g. Venturia inaequalis; Pyrenophora e.g., For example: pyrenophora teres or R graminea (conidia ... -50- 200528434

Drechslera，同義字：長孺孢屬（Helminthosporium)); 抱腔菌屬（Cochliobolus)如，例如··禾抱腔菌（Cochliobolus sativus)(分生孢子型：Drechslera，同義字：長孺孢屬 (Helminthosporium))； 5 單胞銹菌屬（Uromyces)如，例如：疣頂單胞銹菌（Uromyces appendiculatus)； 柄銹菌屬（Puccinia)如’例如··隱匿柄錄菌（Puccinia recondita)； 核盤菌屬（Sclerotinia)如，例如：核盤菌（Sclerotinia 10 sclerotiorum)； 腥黑粉菌屬（Tilletia)如，例如··小麥網腥黑粉菌（Tilletia caries)； 黑粉菌屬（Ustilago)如，例如：裸黑粉菌（Ustilago nuda)或 燕麥黑粉菌（Ustilago avenae); 15 薄膜革菌屬（Pellicularia)如，例如：佐佐木薄膜革菌 (Pellicularia sasakii)； 梨孢屬（Pyricularia)如，例如：稻梨胞(pyricuiariaoryzae); 錄抱屬（Fusarium)如’例如·大刀錄抱（Fusarium culmorum); 葡萄孢屬（Botrytis)如，例如：灰葡萄孢(Botrytis cinerea); 20 殼針抱屬（Septoria)如’例如·穎枯殼針抱（；§ept〇ria nodorum)； 小球腔菌屬（Leptosphaeria)穎枯小球腔菌（Lept〇sphaeria nodorum); 尾抱屬（Cercospora)如’例如：變灰尾抱（Cercospora -51- 200528434 canescens)，· 鏈格孢屬（Altenaria)如，例如：蕓苔鏈格孢（Aitenaria brassicae);及 假尾孢屬（Pseudocercosporella)如，例如： Pseudocercosporella herpotrichoides 〇 絲核菌屬（Rhizoctonia species)，如，例如：立枯絲核菌 (Rhizoctonia solani) 〇 根據本發明活性化合物亦具有極佳之強化植物作 用。因此，適合植物内部機動控制不要之微生物侵害。 本文中，咸了解強化植物（誘發抗性)物質指彼等可刺 激植物防衛系統之物質，因此當所處理之植物以後受到不 要之微生物接種時，對此等微生物具有顯著抗性。 15 20 此時，咸了解不要之微生物指植物致病性真菌、細菌 與病毒。因此，根據本發明物質可在處理一段時間後，當 被上述病·侵害時，用於賴植物。此保㈣通常在以 活性化合物處理後為期！至1()天，以i至7天較佳。 由於控制植物病害所需濃度對植物之耐受性良好，因 此可以處理上職物之地上部、繁錄幹及種子及土壤。 此聘’根據本發明化合物對控制穀類病害之 佳，如’例如：對抗柄錄菌及葡萄與蔬果栽培上之病害， 如，例如.對抗葡萄孢、黑星菌或鏈格孢。 13 =本發明活性化合物亦適合提高作物之收率。因 此，其展現降低毒性且植物之耐受性良好。 若適當時，根據本發明活性化合物在某些漠度及施用 -52. 200528434 率下，亦可用為除草劑，調節植物生長 若適當時，亦可用為合成其他活性化合物之中間物 = 體。 所有植物與植株部份均可根據本發明處理。咸了解， 本文中之植物意指所有植物與植物族群，如：需要及 $野生植物或作物（包括天然作物）。作物可為依傳 物月種法與最適化方法或此等方法之組合所取得者，包括 基因轉殖植物’包括受植物育種者權聽護及未受保護之 植物栽培品種。亦咸了解，植株部份意指植物之所有地上 下部及器官，如：芽、葉、花與根，可述及之實例 葉、針葉、轴、莖、花、果實體、果實、種子、根、 Γ。植株部份亦包括收穫之㈣，與營養性及繁 殖性材料，例如：扦插、塊莖、根莖、_枝與種子。 15 20 根據本發明使用活性化合物處理植物與植株部份之 =依傳統處理法’直接進行處理，或使化合物作用在 八周圍環境、棲息地或庫存空間，例如：浸泡、喷灑、产 化、喷霧、撒播、塗刷，及處理繁殖材料時，特 Ρ 理種子時，亦可包覆—層或多層包衣。 " 料，料時，根據本發明化合物可用於保護工業原 村對抗不要之微生物感染及破壞。 本文中之工業原料咸了解係指工業用之無生 工举絲據本發明化合物保護免於變化或破壞之 :材枓可為膠黏劑、膠水、紙張與紙板、紡織 木材、塗料與塑膠物品、冷卻潤滑劑及其他可能被微生物 -53- 200528434 感朵及破壞之材料。生產工廠之零件，例如：可能因微生 物繁殖而受損之冷卻水循環管線亦在本發明範圍内。本發 明範圍内可述及之工業材料為膠黏劑、膠水、紙張與紙 板、皮革、木材、塗料、冷卻潤滑劑及熱傳導液體較佳， 以木材特別佳。 可分解或改變工業原料之微生物可述及例如：細菌、 真菌、酵母、藻類及黏質生物體。根據本發明化合物對抗 真菌較佳，特定言之對抗霉菌、使木材變色及破壞木材之| 真菌（擔子菌（Basidiomycetes))，及對抗黏質生物體與藻 10 15 類。 可述及例如：下列類屬之微生物： 鏈格孢(Altemaria)如：細鏈格孢(Alternaria tenuis)，Drechslera, synonym: Helminthosporium); Cochliobolus such as, for example, Cochliobolus sativus (conidia type: Drechslera, synonym: Drechslera, synonym: Helminthosporium)); 5 Uromyces such as, for example: Uromyces appendiculatus; Puccinia such as' for example · Puccinia recondita; nuclear Sclerotinia is, for example, Sclerotinia 10 sclerotiorum; Tilletia is, for example, Tilletia caries; Ustilago For example: Ustilago nuda or Ustilago avenae; 15 Pellicularia such as: Pellicularia sasakii; Pyricularia such as , For example: Pyricuiariaoryzae; Fusarium such as' for example · Fusarium culmorum; Botrytis such as: Botrytis cinerea; 20 Belong to Septoria) such as 'e.g. epteptria nodorum; Leptosphaeria Leptosphaeria nodorum; Cercospora such as' e.g. : Cercospora -51- 200528434 canescens, Altenaria, such as: Aitenaria brassicae; and Pseudocercosporella, such as: Pseudocercosporella herpotrichoides O Rhizoctonia species, such as, for example, Rhizoctonia solani. The active compounds according to the invention also have excellent plant-fortifying effects. Therefore, it is suitable for the control of unwanted microorganisms in plants. In this context, salt-reinforcing plant (induced resistance) substances refer to substances that can stimulate the plant defense system, so when the treated plants are subsequently inoculated with unwanted microorganisms, they are significantly resistant to these microorganisms. 15 20 At this time, understand that unwanted microorganisms are phytopathogenic fungi, bacteria, and viruses. Therefore, the substance according to the present invention can be used on plants after being treated for a period of time when it is affected by the above-mentioned diseases. This guarantee usually lasts after treatment with the active compound! To 1 () days, preferably i to 7 days. Because the concentration required for controlling plant diseases is well tolerated by plants, it can handle above-ground, seedlings, seeds and soil of the workforce. The compounds according to the present invention are good for controlling cereal diseases, such as, for example, against diseases such as Phytophthora, and grape and vegetable cultivation, such as, for example, against Botrytis, Nicotiana or Alternaria. 13 = The active compounds according to the invention are also suitable for increasing the yield of crops. Therefore, it exhibits reduced toxicity and is well tolerated by plants. If appropriate, the active compound according to the present invention can also be used as a herbicide to regulate plant growth under certain desertification and application rates of -52.200528434. If appropriate, it can also be used as an intermediate to synthesize other active compounds. All plants and plant parts can be treated according to the invention. It is understood that plants in this article refer to all plants and plant groups, such as: needs and wild plants or crops (including natural crops). The crops may be obtained by the conventional method of monthly seeding and optimization or a combination of these methods, including genetically-transplanted plants' including cultivars that are protected by the plant breeder's right and unprotected. It is also understood that the plant part means all the above and below parts and organs of the plant, such as: buds, leaves, flowers and roots, examples that can be mentioned leaves, needles, axes, stems, flowers, fruit bodies, fruits, seeds, Root, Γ. The plant part also includes harvested loquats, and vegetative and reproductive materials such as cuttings, tubers, rhizomes, branches and seeds. 15 20 Treatment of plants and plant parts with active compounds according to the present invention = direct treatment according to traditional treatment methods, or allowing compounds to act on eight surrounding environments, habitats or storage spaces, such as: immersion, spraying, chemical production, When spraying, spreading, brushing, and treating propagation materials, when treating seeds, they can also be coated with one or more layers. " The compound according to the present invention can be used to protect industrial villages from unwanted microbial infection and destruction. The term "industrial raw materials" in this article refers to industrially-used, non-living silk. The compounds according to the present invention are protected from changes or damage: materials can be adhesives, glues, paper and cardboard, textile wood, coatings and plastic articles. , Cooling lubricants and other materials that may be susceptible to and damaged by microorganisms -53- 200528434. Parts of the production plant, such as cooling water circulation pipelines that may be damaged due to the growth of microorganisms, are also within the scope of the present invention. Industrial materials that can be mentioned within the scope of the present invention are preferably adhesives, glues, paper and board, leather, wood, coatings, cooling lubricants and heat-conducting liquids, and wood is particularly preferred. Microorganisms that can decompose or change industrial materials can be mentioned, for example: bacteria, fungi, yeast, algae and slime organisms. The compounds according to the invention are better against fungi, in particular against fungi, wood discoloration and wood damage | fungi (Basidiomycetes), and against slime organisms and algae 10-15. Can be mentioned for example: microorganisms of the following categories: Altemaria such as: Alternaria tenuis,

曲徽(Aspergillus)如：黑曲徽(Aspergillus niger)， 毛殼（〇1&61；0111丨11111)如：球毛殼（(^11&61：0111丨11111§1〇1)0811111)， 抱格菌（(^01^0卩110以)如：粉孢革菌（(^01^0卩110以卩1^311忍）， 香蒜（1^11如113)如：虎皮香蒜（1^111^11118 1^1^11113)， 綠青徽(卩61^(^11丨11111)如：灰綠青黴(？61^(^1^1111181&11(；11111)， 多孔菌（Polyporus)如：變色多孔菌（Polyporus versicolor)， 短梗黴（Aureobasidium)如：出芽短梗黴（Aureobasidium pullulans)，Aspergillus, such as: Aspergillus niger, fur shell (〇1 &61; 0111 丨 11111), such as: ball wool shell ((^ 11 & 61: 0111 丨 11111§1〇1) 0811111), Bordetella ((^ 01 ^ 0 卩 110 to 110) such as: Mesosporin ((^ 01 ^ 0 卩 110 to 卩 1 ^ 311)), Pesto garlic (1 ^ 11 such as 113) such as tiger skin garlic (1 ^ 111 ^ 11118 1 ^ 1 ^ 11113), green and green emblems (卩 61 ^ (^ 11 丨 11111), such as: Penicillium gray green (? 61 ^ (^ 1 ^ 1111181 & 11 (; 11111), porous bacteria ( Polyporus) such as: Polyporus versicolor, Aureobasidium such as: Aureobasidium pullulans,

Sclerophoma 菌如：Sclerophoma pityophila， 木黴(Trichoderma)如：綠色木黴(Trichoderma viride)， 桿菌（Escherichia)如：大腸桿菌（Escherichia coli)， 假單胞菌（Pseudomonas)如：銅綠假單胞菌（Pseudomonas -54- 20 200528434 aeruginosa)，及 葡萄球菌（Staphylococcus)如：金黃色葡萄球菌 (Staphylococcus aureus) 〇 依活性化合物之特定物理與/或化學性質而定，其可 轉化成一般調配物’如··溶液、乳液、懸浮液、粉劑、泡 沫劑、糊劑、粒劑、氣霧劑與含於聚合物質中之微包埋劑， 及用於種子之包衣組合物，及ULV低溫與加溫霧化調配 物0 彼專調配物係依已知方法製造，例如：混合活性化合 物與補充劑，即液態溶劑、加壓液化氣體與/或固態載劑， 視需要可使用界面活性劑，即乳化劑與/或勻散劑與/或發 泡劑。若使用水作為補充劑時，亦可使用例如：有/機溶^ 作為辅助溶劑。基本上適用之液態溶劑為··芳香族如^二 15 20 =、:苯或減萘類、氯㈣香频氣化_煙類如· ，苯、氯化乙烯或二氯甲烷、脂族烴類如：環己烷嬙 類例如：石油分餾物，醇類如：丁醇或乙二醇及复醚 :類強:類如:賴、甲基乙基綱、甲基異丁基_或二 酮，強極性溶劑，如：二甲基甲醯胺或二 衣己 液化氣體補充劑或載劑咸了解係指在‘準二，。 呈氡態之液體，例如：氣霧劑推進劑如： 广/、☆壓下 丙燒、氮氣與二氧化碳。適用之固態载n或丁燒、 礦物磨粉，如··高嶺土、黏土、滑石、白要、、·例+如·天然 蒙脫土或矽藻土，及合成礦物磨粉如：言八\石英、白土、 土與矽酸鹽類。適用於粒劑之固態栽2刀散性矽石、礬 _55 為例如：粉碎與分 200528434 碎之天然礦石，如：方解石、大理石、浮石、海泡石與白 雲石’或無機與有機細粉類之合成顆粒；及有機物質之顆 粒如.鋸屑，椰子忒，玉米穗轴與煙草桿。適用之乳化劑 與/或發泡劑為例如··非離子性與陰離子性乳化劑如：聚 5 I乙烯脂肪酸賴、聚氧乙埽脂肪醇_，例如：炫芳基 聚乙二醇醚類、增酸烧基酷類、琉酸烧基醋類、石黃酸芳基 酉旨及蛋白質水解產物。適用之勻散劑為例如：木質素亞碳 酸鹽廢液與甲基纖維素。 調配物中可使用黏著劑如：竣甲基纖維素、天然及合 10 成聚合物之叔末、顆粒或膠乳，如：阿拉伯膠、聚乙稀醇 與聚乙酸乙烯醋或天然填脂如：腦碟脂與㈣脂，及合成 磷脂類。其他可用之添加物為：礦物油與蔬菜油。 可能使用染色劑如：無機色素，例如:氧也鐵，氧化 欽與普魯士藍，及有機染料’如：茜素染料，偶氮染料及 15 金屬欧花青染料及微量營養素如：鐵、μ、m 鉬與鋅之鹽類。 調配物tit常包含0.1 i 95重量％活性化合物，以 〇·5至90重量％之間較佳。 減本發明活性化合物可呈其本身❹，或形成調配 2〇 喊用，亦可與已知殺真關、殺細菌劑、殺蜱蟎劑、殺 線轰劑或殺昆蟲劑形成混合物’以擴大例如：活性範圍或 防止產生抗性。有時候，可得到增致致果，亦即，混合物 之活性高於個別成分之活性。 合適混合成分為例如下列化合物： -56· 200528434 殺真菌劑： 5 10 15 2-苯基苯酚；8-羥基喹啉硫酸鹽；艾苯拉（acibenzolar)-S-甲基；艾狄莫（aldimorph);安伏滅(amidoflumet);安伏斯 (ampropylfos);安伏斯鉀(ampropylfos-potassium);安得靈 (andoprim);安拉辛（anilazine)，·阿克嗤（azaconazole);阿 斯本（azoxystrobin);苯拉希（benalaxyl);苯諾丹 (benodanil);免賴德(benomyl);苯賽卡(benthiavalicarb)-異丙基；苯賽克(benzamacril);苯赛克（benzamacril)-異丁 基；百拉斯(bilanafos);百漫克(binapacryl);聯苯，·拜坦 諾（bitertanol);保米黴素（blasticidin)-S ;布康唑 (bromuconazole);布滅莫（bupirimate)；得滅多 (buthiobate) ; 丁基胺；多硫化；卡普黴素(capsimyein); 四氯丹（captafol);蓋普丹(captan)，·卡苯辛（carbendazim); 卡布辛（carboxin);卡普醯胺（carpropamid);卡吩 (carvone); 克滅（chinomethionat); 克本松Sclerophoma bacteria such as: Sclerophoma pityophila, Trichoderma such as: Trichoderma viride, Escherichia such as Escherichia coli, Pseudomonas such as Pseudomonas aeruginosa (Pseudomonas aeruginosa) Pseudomonas -54- 20 200528434 aeruginosa), and Staphylococcus such as: Staphylococcus aureus 〇 Depending on the specific physical and / or chemical properties of the active compound, it can be converted into a general formulation 'such as · Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulating agents contained in polymer materials, and coating compositions for seeds, and ULV low temperature and warming Atomization formulations 0 Other formulations are manufactured according to known methods, such as mixing active compounds and supplements, that is, liquid solvents, pressurized liquefied gases, and / or solid carriers. Surfactants can be used as needed, that is, emulsification Agents and / or dispersants and / or blowing agents. If water is used as a supplement, for example, you can use organic solvent as auxiliary solvent. Basically applicable liquid solvents are: · aromatics such as ^ 2 15 20 = ,: benzene or reduced naphthalene, chloroscent frequency gasification _ cigarettes such as ·, benzene, ethylene chloride or dichloromethane, aliphatic hydrocarbons Classes such as: cyclohexane, such as: petroleum fractions, alcohols such as: butanol or ethylene glycol and double ethers: class strong: class such as: Lai, methyl ethyl group, methyl isobutyl _ or di Ketones, strong polar solvents, such as: dimethylformamide or dimethylamine liquid liquefied gas supplements or carriers. Liquids in the limulus state, for example: aerosol propellants such as: guangzhou /, ☆ pressure propylene, nitrogen and carbon dioxide. Applicable solid-loaded n or sintered, mineral powders, such as kaolin, clay, talc, baiyao, etc. Example + such as natural montmorillonite or diatomaceous earth, and synthetic mineral powder such as: Yanba \ Quartz, white clay, clay and silicates. For solid granules, 2 knives of loose silica and alum _55 are for example: crushed and divided 200528434 crushed natural ore, such as: calcite, marble, pumice, sepiolite and dolomite 'or inorganic and organic fine powder Similar synthetic particles; and particles of organic substances such as sawdust, coconut tincture, corn cobs and tobacco rods. Suitable emulsifiers and / or foaming agents are, for example, non-ionic and anionic emulsifiers, such as: poly 5 I ethylene fatty acid lysine, polyoxyethyl fluorinated fatty alcohols, for example: dazzling aromatic polyethylene glycol ethers , Sodium sulfonate, sulfonyl vinegar, aryl lutein acid, and protein hydrolysates. Suitable dispersants are, for example, lignin carbonate waste liquid and methyl cellulose. Adhesives can be used in the formulation such as: methylcellulose, natural and synthetic polymers, granules or latex, such as: gum arabic, polyvinyl alcohol and polyvinyl acetate vinegar or natural fat fillings such as: Brain Dish Fat and Fat, and Synthetic Phospholipids. Other useful additives are: mineral and vegetable oils. May use dyes such as: inorganic pigments, such as: oxygen iron, oxan and Prussian blue, and organic dyes' such as: Alizarin dyes, azo dyes and 15 metal Eucyanine dyes and micronutrients such as: iron, μ, m Molybdenum and zinc salts. The formulation tit often contains 0.1 to 95% by weight of active compound, preferably between 0.5 and 90% by weight. The active compound for reducing the present invention can be used as it is, or it can be formulated to be used as a mixture, or it can be mixed with known killing agents, bactericides, acaricides, nematicides or insecticides to expand For example: range of activity or prevention of resistance. In some cases, it is possible to obtain a boosting effect, that is, the activity of the mixture is higher than that of the individual ingredients. Suitable mixing ingredients are, for example, the following compounds: -56 · 200528434 Fungicides: 5 10 15 2-phenylphenol; 8-hydroxyquinoline sulfate; acibenzolar-S-methyl; aldimorph ); Amidoflumet; ampropylfos; ampropylfos-potassium; andoprim; anilazine; azaconazole; aspen Azoxystrobin; benalaxyl; benodanil; benomyl; benthiavalicarb-isopropyl; benzacril; benzacril -Isobutyl; bilanafos; binapacryl; biphenyl, bitertanol; blasticidin-S; bromuconazole; butamol (Bupirimate); buthiobate; butylamine; polysulfide; capsimyein; captafol; captan, carbendazim; carbendazim (Carboxin); carpropamid; carvone; chimethionat;

(chlobenthiazone);克吩唑（chlorfenazole)；氯尼 (chloroneb);四氯異苯腈（chlorothalonil);氯唑内 (chlozolinate);克拉肯(cl〇Zylacon);赛發滅(Cyazofamid); 赛吩滅（cyflufenamid);西莫尼（cymoxanil);西普康唑 (cyproconazole)；西迪尼（cyprodinil);賽伏南 (cyprofuram);代格(Dagger)G ;迪布卡(debacarb);益發靈 (dichlofluanid);地克隆(dichlone);二氯吩(dichlorophen); 地克赛（diclocymet);地克美辛（diclomezine)，·地克爛 (dicloran);地吩卡（diethofencarb)；地吩康峻 -57- 20 200528434 10 15 (difenoconazole)；地伏靈（diflumetorim)；地滅利 (dimethirimol)；地滅莫（dimethomorph)；地斯本 (dimoxystrobin);地康唑（diniconazole);地康唑-Μ ;白粉 克（dinocap);二苯基胺；二吡松(dipyrithione);地塔伏斯 (ditalimfos);腈硫現（dithianon);多寧（dodine);查索農 (drazoxolon)；護粒松（edifenphos)；環氧克唑 (epoxiconazole);抑本散(ethaboxam);抑利莫（ethirimol); 抑得唑（etridiazole);芬色丹（famoxadone);芬滅酮 (fenamidone);芬普尼（fenapanil);芬利莫（fenarimol);芬 康峻（fenbuconazole);芬伏爛（fenfuram);芬赫醯胺 (fenhexamid);芬°坐本(fenitropan);芬散尼（fenoxanil);芬比(chlobenthiazone); chlorfenazole; chloroneb; chlorothalonil; chlozolinate; clogen (clOZylacon); Cyazofamid; Cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; Yifaling (dichlofluanid); dichlone; dichlorophen; dilocymet; diplomezine; dichlorolan; dithofencarb; diphenk -57- 20 200528434 10 15 (difenoconazole); diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diconazole; diconazole- Μ; dinocap; diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon; granules Edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole; fen Dan (famoxadone); fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram; fenhexamid; fen ° Fenitropan; fenoxanil; Finby

克尼（fenpiclonil);芬普定（fenpropidin);芬普福 (fenpropimorph);富爾邦（ferbam);扶吉胺（fluazinam);伏 本亞胺（flubenzimine);伏克尼（fludioxonil);伏特夫 (flumetover);伏莫（fhimorph);氟醯胺(fluoromide);伏斯 本（fluoxastrobin);伏克康嗤（fluquinconazole);伏米得 (flurprimidol);護砍得（flusilazole);護硫醢胺 (flusulphamide);護坦尼（flutolanil);護汰芬（flutriafol); 福爾培（folpet);福赛德（fosetyl)-Al ;福赛德納；伏塔唾 (fuberidazole);伏拉希（furalaxyl);福滅普（furametpyr); 護卡尼（furcarbanil);護克斯(furmecyclox);免熱淨 (guazatine);六氯苯；六康唾（hexaconazole);殺紋寧 (hymexazole);依滅列（imazalil);抑本康唾 (imibenconazole);抑康定(iminoctadine)三乙酸鹽；抑克定 -5S- 20 200528434 -三阿見酸鹽（iminoctadine tris(albesil))，·姨卡（iodocarb); 5 10 15 抑普康峻（ipconazole);丙基喜樂松(iprobenfos);依普同 (iprodione)；抑發利（iprovalicarb)；依麻黴素 (irumamycin);亞賜普醇烧（isoprothiolane);異弗二酮 (isovaledione);賜黴素（kasugamycin);克辛甲醋 (kresoxim-methyl);猛粉克（mancozeb);短乃浦（maneb); 滅芬松（meferimzone);米本靈（mepanipyrim);米普尼 (mepronil);滅達樂（metalaxyl);滅達樂-M ;滅康嗤· (metconazole);滅速卡（methasulphocarb);滅伏散 (methfuroxam)；滅得賴（metiram);滅速本 (metominostrobin);滅速發（metsulphovax);米得黴素 (mildiomycin);麥克坦尼（myclobutanil);麥克靈 (myclozolin);納坦黴素(natamycin);尼克本(nicobifen);Fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; volts Flumetover; fhimorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; thiofuran Amines (flusulphamide); flutolanil; flutriafol; folpet; fosetyl-Al; foseidner; fuberidazole; volahi (Furalaxyl); furametpyr; furcarbanil; furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazole; Imazalil; imibenconazole; iminoctadine triacetate; imoxidad-5S-20 200528434-iminoctadine tris (albesil); ); 5 10 15 ipconazole; iprobenfos; iprodione; iprovalicarb; ephedrine Irumamycin; isoprothiolane; isovaledione; kasugamycin; kresoxim-methyl; mancozeb; maneb); meferimzone; mepanipyrim; mepronil; metalaxyl; metalol-M; metconazole; metasulphocarb ); Methfuroxam; metiram; metominostrobin; metsulphovax; mildiomycin; myclobutanil; myclozolin ; Natamycin; nicobifen;

石肖基太（nitrothal)-異丙基；諾伏隆（noviflumuron);紐莫 (nuarimol);歐弗斯（ofurace);歐斯本(orysastrobin);歐殺 斯（oxadixyl);崎琳酸（oxolinic acid);今康嗤 (oxpoconazole)；嘉得信（oxycarboxin);歐芬 >、丁 (oxyfenthiin)；巴克素（paclobutrazole)；比菲嗤 (pefurazoate);本康嗤(penconazole);賓克隆(pencycuron); 伏斯定(phosdiphen);苯敌；比克斯本(picoxystrobin);比 特靈（piperalin);保粒黴素（polyoxins);保粒靈 (polyoxorim);普本嗤(probenazole);撲克拉(prochloraz); 撲滅寧（procymidone);普莫卡（propamocarb);普辛納 (propanosine-sodium);普克利（propiconazole);甲基鋅乃 -59- 20 200528434 浦（propineb) ’·普克奇（proquinazid)；普賽康唑 (prothioconazole)；普克斯本（pyraclostrobin);白粉松 (pyrazophos)，·比芬斯(pyrifenox)，·比坦尼（pyrimethanil); 百快隆（pyroquilon);普希弗（pyroxyfur);吼嘻啉 5 (pyrrolenitrine)；快康唑（quinconazole);克辛芬 (quinoxyfen);奎脫辛（quintozene);辛康口坐(simeconazole); 賜必安（spiroxamine);琉；得克利（tebuconazole);特克爛 (tecloftalam);特辛（tecnazene);特赛利（tetcyclacis);特康嗤 (tetraconazole);腐絕(1:hiabendazole);地赛芬(thicyofen);地 10 伏醯胺(thifluzamide);甲基多保淨(thiophanate-methyl);得 恩地（thiram);地歐西（tioxymid);甲基脫克松 (tolclofos-methyl)；特伏利（tolylfluanid);三泰芬 (triadimefon);總泰隆（triadimenol);三本地（triazbutil); 三唾氧（triazoxide);三環醯胺（tricyclamide);三赛唾 15 (tricyclazole)；三得芬（tridemolph);三伏素 (trifloxystrobin);三伏嗤(triflumizole);赛福寧（triforine)，· 三狄康嗤(triticonazole);優康唾(uniconazole);維利黴素 (validamycin) A ;免克寧(vinclozolin);辞乃浦(zineb);益 穗（ziram);索醯胺（zoxamide) ; (2S)-N-[2_[4-[[3-(4-氯苯 20 基)-2-丙炔基]氧]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲磺醢 基）胺基]-丁醯胺；H1-萘基MH-吡咯·2,5-二酮；2,3,5,6-四氯-4-(曱磺醯基)吡啶；2-胺基-4-曱基-Ν-苯基-5-噻唑羧 醯胺；2-氣·Ν-(2,3-二氫-U，3-三甲基-1H-茚-4-基)-3-吡啶 叛醯胺；3,4,5-三氯-2,6-吼咬甲腈；抑克定（actinovate); 200528434 順式小(4-氯苯基）-2-(1Η-1，2,4-三唑-1-基）環庚醇；1_(2,3-二氳-2,2-二曱基-1H-茚小基）-1Η-咪唑-5-羧酸甲酯；碳酸 一鉀鹽；N-(6-曱氧基-3·^比啶基)-環丙烷羧醯胺；正丁基 -8-(l，l-二甲基乙基)-1-氧雜螺[4.5]癸烷-3-胺；四硫代碳酸 5 納；與銅鹽及製劑，如，波爾多混合物(Bordeaux mixture); 氫氧化銅；萘甲酸銅；鹼性氯氧化銅；硫酸銅；庫發尼 (cufraneb);氧化銅；猛銅製劑（mancopper);快得寧 (oxine-copper) 〇 ίο 殺細菌劑： 布普諾（bronopol)、二氣吩（dichlorophen)、尼普林 (nitrapyrin)、二甲基二硫代胺曱酸鎳、賜黴素 (kasugamycin)、歐力農（octhilinone)、呋喃羧酸、氧四環 速（oxytetracyclin)、撲殺熱（probenazole)、鏈黴素 15 (streptomycin)、特可塔（tecloftalam)、硫酸銅與其他銅製 劑0 殺艮蟲劑/殺碑蜗劑/殺線蟲劑： 阿巴丁（abamectin)、ABG-9008、歐殺松(acephate)、艾克 20 尼（acequinocyl)、歐殺滅（acetamiprid)、抑特波 (acetoprole)、艾克靈（acrinathrin)、AKD-1022、AKD-3059、 AKD-3088、亞爛卡(alanycarb)、得滅克(aldicarb)、亞得卡 (aldoxycarb)、亞特靈（allethrin)、亞特靈 1R-異構物、α_亞 滅寧（cypermethrin)(alphamethrin)、安伏特(amidoflumet)、 -61 - 200528434 胺卡（aminocarb)、三亞瞒（amitraz)、艾弗定（avermectin)、 AZ-60541、查得定(azadirachtin)、查弗斯(azamethiphos)、 甲基谷速松（azinphos-methyl)、 乙基谷速松 (azinphos-ethyl)、亞環錫(azocyclotin)、日本甲蟲芽胞桿菌 5 (Bacillus popilliae)、球形芽胞桿菌（Bacillus sphaericus)、 枯草桿菌（Bacillus subtilis)、蘇雲金芽胞桿菌（Bacillus thuringiensis)、蘇雲金芽胞桿菌菌株EG_2348、蘇雲金芽 胞桿菌菌株GC-91、蘇雲金芽胞桿菌菌株NCTC-11821、 桿狀病毒、白僵菌（Beauveria bassiana)、纖細白僵菌 ίο (Beauveria tenella)、本克赛（benclothiaz)、本迪克 (bendiocarb)、本弗卡(benfuracarb)、本速塔(bensultap)、本 辛滅（benzoximate)、β-赛扶寧（cyfluthrin)、β-赛滅寧 (cypermethrin)、畢芬赛(bifenazate)、畢芬寧(bifenthrin)、 畢卡利（binapacryl)、必利靈(bioallethrin)、必利靈 15 (bioallethrin)-S-環戊基·異構物、必滅寧 (bioethanomethrin)、必普靈（biopermethrin)、必赛靈 (bioresmethrin)、必伏能（bistrifluron)、BPMC、普洛芬斯 (brofenprox)、乙基布弗斯(bromophos-ethyl)、丙酸漠、（曱 基-)溴芬斯(bromfenvinfos)、BTG-504、BTG-505、布芬卡 20 (bufencarb)、布芬辛(buprofezin)、布赛伏斯(butathiofos)、 布特卡辛(butocarboxim)、丁 氧卡辛(butoxycarboxim)、丁 基吼達本（butylpyridaben)、硫線磷（cadusafos)、克氯 (camphechlor)、加保利(carbaryl)、加保扶(carbofuran)、卡 芬松(carbophenothion)、丁基加保扶(carbosulphan)、培丹 -62- 200528434 5 10 15 (cartap)、CGA-50439、辛滅特（chinomethionat)、克丹 (chlordane)、克地風（chlordimeform)、克抑卡 (chloethocarb)、克抑伏斯（chl〇rethoxyfos)、克芬比 (chlorfenapyr)、克芬伏斯（chl〇rfenvinphos)、克伏速能 (chlorfluazuron)、克美斯（chlormephos)、氯苯烈 (chlorobenzilate)、氯必靈（chloropicrin)、氯普芬 (chlorproxyfen)、曱基陶斯松（chl〇rpyrifos-methyl)、（乙基 -)陶斯松(chlorpyrifos)、克發普靈(chlovaporthrin)、克麻赛· (chromafenozide)、順式-賽滅寧(cypermethrin)、順式-利滅 寧（resmethrin)、順式-普滅寧（permethrin)、克赛林Nitrothal-isopropyl; noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid ); Today's oxpoconazole; oxycarboxin; oxen and oxyfenthiin; pacobutrazole; pefurazoate; penconazole; peoncuron ); Phosdiphen; benzene enemy; picoxystrobin; piperalin; polyoxins; polyoxorim; probenazole; poker pull (prochloraz); Promethazine; propamocarb; propanosine-sodium; propiconazole; methyl zinc-59- 20 200528434 propineb '· Pukeki (Proquinazid); Prothioconazole; Pyraclostrobin; Pyrazophos; Pirifenox; Pirimethanil; Pyroquilon; Schiff (pyroxyfur); Glucoline 5 (pyrrolenitrine); quinconazole; quinoxyfen (quinoxyfen); Quintozene; simeconazole; spiroxamine; Rau; tebuconazole; tecloftalam; tecnazene; tetcyclacis; special Tetraconazole; 1: Hiabendazole; thicyofen; thifluzamide; thiophanate-methyl; thiram; diosi ( tioxymid); tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil; triazoxide; Tricyclamide; tricyclazole 15; tridemolph; trifloxystrobin; triflumizole; triforine; triticonazole; Uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide; (2S) -N- [2_ [ 4-[[3- (4-chlorobenzene 20yl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2-[(methylsulfonyl) Amine] -butylamidine; H1-naphthyl MH-pyrrole · 2,5-dione 2,3,5,6-tetrachloro-4- (fluorenylsulfonyl) pyridine; 2-amino-4-fluorenyl-N-phenyl-5-thiazolecarboxamide; 2-Ga · N- ( 2,3-dihydro-U, 3-trimethyl-1H-inden-4-yl) -3-pyridine benzylamine; 3,4,5-trichloro-2,6-nitrocarbonitrile; Actinovate; 200528434 cis-small (4-chlorophenyl) -2- (1Η-1,2,4-triazol-1-yl) cycloheptanol; 1_ (2,3-difluorene-2 , 2-Difluorenyl-1H-indenyl) -1′-imidazole-5-carboxylic acid methyl ester; Monopotassium carbonate; N- (6-fluorenyloxy-3 · ^ pyridinyl) -cyclopropanecarboxylate Ammonium amine; n-butyl-8- (l, l-dimethylethyl) -1-oxaspiro [4.5] decane-3-amine; 5 sodium tetrathiocarbonate; with copper salts and preparations such as Bordeaux mixture; copper hydroxide; copper naphthoate; basic copper oxychloride; copper sulfate; cuffraneb; copper oxide; mancopper; oxine-copper 〇ίο Bactericides: bronopol, dichlorophen, nitrrapyrin, nickel dimethyldithioamide, kasugamycin, octhilinone, Furan carboxylic acid, oxytetracyclin, probena zole), streptomycin 15 (streptomycin), tecloftalam, copper sulfate and other copper preparations 0 Insecticides / snail killers / nematicides: abadectin, ABG-9008, Acephate, acequinocyl, acetamiprid, acetoprole, acrithrin, AKD-1022, AKD-3059, AKD-3088, Asia Alanycarb, aldicarb, aldoxycarb, allethrin, 1R-isomer, alphamethrin, alphamethrin amidoflumet), -61-200528434 aminocarb, amitraz, avermectin, AZ-60541, azadirachtin, azamethiphos, methylglutamate ( azinphos-methyl), azinphos-ethyl, azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis Bacillus thuringiensis, Bacillus thuringiensis strain EG_2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, baculovirus, Beauveria bassiana, Beauveria tenella, benclothiaz, bendiocarb ), Benfuracarb, bensultap, benzoximate, β-cyfluthrin, β-cypermethrin, bifenazate, bifenazine bifenthrin), biapacryl, bioallethrin, bioallethrin-S-cyclopentyl · isomer, bioethanomethrin, biopermethrin, must Bioresmethrin, bistrifluron, BPMC, brofenprox, bromophos-ethyl, propionate, bromfenvinfos, BTG-504, BTG-505, Bufencarb 20, buprofezin, butathiofos, butocarboxim, butoxycarboxim, butyl Daben (butylpyridaben), cadusafos, camphechlor, warranty (carbaryl), carbofuran, carbophenothion, carbosulfan, carbosulfan-62- 200528434 5 10 15 (cartap), CGA-50439, chimethionat , Chlordane, chlordimeform, chloethocarb, chlororethoxyfos, chlorfenapyr, chlorofenapyrs, chloroform Chlorfluazuron, chlormephos, chlorobenzilate, chloropicrin, chlorproxyfen, chlórpyrifos-methyl, (ethyl-) taosson (chlorpyrifos), chlovaporthrin, chromafenozide, cis-cypermethrin, resmethrin, cis-permethrin, Kesselin

(clocythrin)、克地卡（cloethocarb)、克芬金(clofentezine)、 克赛定（clothianidin)、克赛唑本（clothiazoben)、克蒙 (codlemone)、庫麻伏斯（coumaphos)、氰芬斯 (cyanofenphos)、氰伏斯(cyanophos)、環普寧（cycloprene)、 乙氰菊醋（cycloprothrin)、蘋果蠹蛾(Cydia pomonella)、赛 扶寧（cyfluthrin)、赛洛寧（cyhalothrin)、賽、;丁（cyhexatin)、 赛滅寧（cypermethrin)、赛芬寧（cyphenothrin)( 1R-反式-異構 物）、賽麻淨(cyromazine)、DDT、第滅寧（deltamethrin)、 滅賜松（demeton)-S-甲基、滅賜松-S-甲基颯、地芬農 (diafenthiuron)、地利伏(dialifos)、大利松(diazinon)、大克 芬(dichlofenthion)、二氯松(dichlorvos)、地克發(dicofol)、 地伏斯（dicrotophos)、地赛尼(dicyclanil)、地芬速能 (diflubenzuron)、地滅伏靈（dimefluthrin)、大滅松 (dimethoate)、二曱基芬斯（dimethylvinphos)、地諾通 -63- 20 200528434 (dinobuton)、白粉克(dinocap)、地特爛（dinotefuran)、地伏 爛（diofenolan)、二硫通（disulphoton)、杜克鈉 (docusat-sodium)、杜芬比(dofenapyn)、DOWCO-439、抑 伏烈（eflusilanate)、依麻定（emamectin)、依麻定苯曱酸鹽、 依普靈(empenthrin)(lR-異構物）、恩速芬(end〇sulphan)、蟲 徽屬（Entomopthora spp·)、EPN、益化利（esfenvalerate)、抑 芬卡（ethiofencarb)、抑特普（ethiprole)、愛殺松(ethion)、 普伏松（ethoprophos)、依芬寧（etofenprox)、益特索· (etoxazole)、益多松（etrimfos)、芬伏（famphur)、芬拿伏 10 15(clocythrin), clotethocarb, clofentezine, clothianidin, clothiazoben, codlemone, coumaphos, cyanfens (cyanofenphos), cyanophos, cycloprene, cycloprothrin, Cydia pomonella, cyfluthrin, cyhalothrin, Sai, Cyhexatin, cypermethrin, cyphenothrin (1R-trans-isomer), cyromazine, DDT, deltamethrin, demeton ) -S-Methyl, Methison-S-Methylamidine, difenthiuron, dialifos, diazinon, dichlofenthion, dichlorvos, Dicofol, dicrotophos, dicyclanil, diflubenzuron, dimefluthrin, dimethoate, dimethoate dimethylvinphos), Dinobut-63- 20 200528434 (dinobuton), dinocap, dinotefu ran), diofenolan, diulphoton, docusat-sodium, dofenapyn, DOWCO-439, eflusilanate, emamectin , Emamidine benzoate, empenthrin (lR-isomer), endosulfan, Entomopthora spp ·, EPN, esfenvalerate, Ethiofencarb, ethiprole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos, Famphur, Fenav 10 15

(fenamiphos)、芬赛克（fenazaqUin)、芬佈賜（fenbutatin oxide)、芬福寧（fenfluthrin)、吩特松(fenitrothion)、芬佈卡 (fenobucarb)、芬赛卡(fenothiocarb)、芬克靈(fenoxacrim)、 芬斯卡（fenoxycarb)、芬普寧（fenpropathrin)、芬吼得 (fenpyrad)、芬°比靈（fenpyrithrin)、芬〇比赛(fenpyroximate)、 芬速隆（fensulphothion)、芬松（fenthion)、芬奇利 (fentrifanil)、芬化利（fenvalerate)、菲普尼(fipronil)、伏卡 滅(flonicamid)、伏卡靈（fluacrypyrim)、伏速能（fluazuron)、 伏本明（flubenzimine)、福本赛寧（flubrocythrinate)、福環脲 (flucycloxuron)、護赛寧（flucythrinate)、福菲靈 (flufenerim)、氟芬隆（flufenoxuron)、伏芬普斯 (flufenprox)、伏滅寧（flumethrin)、伏吡氟斯（flupyrazofos)、 福丹辛（flutenzin (flufenzine))、福化利（fluvalinate)、風伏 斯（fonofos)、福滅納（formetanate)、福滅松(formothion)、 伏滅地（fosmethilan)、扶赛特（fosthiazate)、伏本斯 -64- 20 200528434 (fubfenprox (fluproxyfen))、伏硫卡（furathiocarb)、γ-赛洛 寧（cyhalothrin)、γ-HCH、格希普（gossyplure)、格地林 (grandlure)、成粒性病毒（granulosis viruses)、海芬斯 (halfenprox)、護芬赛(halofenozide)、HCH、HCN-801、飛 5 達松（heptenophos)、六伏隆（hexaflumuron)、合赛多 (hexythiazox)、海滅能（hydramethyl none)、赫普林 (hydroprene)、IKA_2002、益達胺（imidacloprid)、益普靈 (imiprot:hrin)、英多卡(indoxacarb)、職芬斯(iodofenphos)、 丙基喜樂松（iprobenfos)、依殺松（isazofos)、抑芬斯 ίο (isofenphos)、抑普卡(isoprocarb)、抑殺隆(isoxathion)、抑 菲定（ivermectin)、亞朋利（japonilure)、卡得靈（kadethrin)、 核多角病毒（nuclear polyhedrosis viruses)、克普寧 (kinoprene)、λ-赛洛寧（cyhalothrin)、靈丹(lindane)、洛芬 隆(lufenuron)、馬拉松(malathion)、滅克班(mecarbam)、滅 15 速芬（mesulphenfos)、聚乙搭（metaldehyde)、滅丹鈉鹽 (metam-sodium)、滅克利（methacrifos)、達馬松 (methamidophos)、Metharhizium anisopliae，Metharhizium flavoviride、滅大松(methidathion)、滅賜克（methiocarb)、 納乃得(methomyl)、滅普林(methoprene)、曱氧基氯、滅芬 2〇 赛（methoxyfenozide)、滅伏特靈（metofluthrin)、滅特卡 (metolcarb)、滅達松(metoxadiazone)、滅芬斯(mevinphos)、 滅克定(milbemectin)、米本黴素(milbemycin)、MKI-245、 MON-45700、漠克伏（monocrotophos)、莫西定 (moxidectin)、MTI-800、奈尼（naled)、NC-104、NC-170、 -65- 200528434 NC-184、NC-194、NC-196、尼可醯胺（niclosamide)、尼古 丁、耐得爛（nitenpyram)、奈辛（nithiazine)、NNI-0001、 • NNI-0101、NNI-0250、NNI-9768、諾瓦隆（novaluron)、諾 伏隆（novifhmmron)、OK-5101、OK-5201、OK-9601、 5 OK-9602、OK-97(H、OK-9802、歐美特（omethoate)、歐殺 滅(oxamyl)、曱基歐得通(oxydemeton-methyl)、玫煙色擬 青黴（Paecilomyces fumosoroseus)、甲基巴拉松 (parathion-methyl)、（乙基-)巴拉松、（順式-、反式-)百滅寧 (permethrin)、石油、PH-6045、芬特寧（phenothrin)(lR-反 1〇 式異構物）、赛達松(phenthoate)、福瑞松(phorate)、裕必松 (phosalone)、益滅松(phosmet)、福賜米松(phosphamidon)、 福卡(phosphocarb)、巴赛松(phoxim)、胡椒基丁醚(piperonyl butoxide)、 比加普（pirimicarb)、 甲基亞特松 (pirimiphos-methyl)、乙基亞特松(pirimiphos-ethyl)、油酸 15 鉀、普烈靈（prallethrin)、加護松（profenofos)、普伏靈 (profluthrin)、普滅卡(promecarb)、普帕伏斯（propaphos)、 歐蜗多（propargite)、普必丹（propetamphos)、普波速 (propoxur)、普硫松(prothiofos)、飛克松(prothoate)、普奇 芬（protrifenbute)、普特辛（pymetrozine)、必克伏斯 2〇 (pyraclofos)、必滅靈（pyresmethrin)、普瑞靈（pyrethrum)、 必達本（pyridaben)、必達利（pyridalyl)、必達芬松 (pyridaphenthion)、必汰松（pyridathion)、必地芬 (pyrimidifen)、必普希芬（pyriproxyfen)、拜裕松 (quinalphos)、利滅靈（resmethrin)、RH-5849、力保靈 -66- 200528434 (ribavirin)、RU-12457、RU-15525、S-421、S-1833、殺力 松（salithion)、希伏斯（sebufos)、SI-0009、希拉芬 (silafluofen)、賜諾殺（spinosad)、速克芬（spirodiclofen)、 速滅芬（spiromesifen)、速菲滅（sulphiuramid)、速伏地 5 (sulphotep)、速普福斯（sulprofos)、SZI-121、特福化利 (tau-fluvalinate)、特布賽得（tebufenozide)、特布必得 (tebufenpyrad)、特布利伏（tebupirimfos)、特本速能 (teflubenzuron)、特伏靈（tefluthrin)、亞培松（temephos)、 特美芬斯（temivinphos)、特斑（terbam)、特布伏斯 ίο (terbufos)、四氯芬伏斯（tetraclilorvinphos)、特達芬 (tetradifon)、特滅靈(tetramethrin)、特滅靈（tetramethrin)(IR-異構物）、特速(tetrasul)、特賽滅寧(theta_cypermethrin)、 赛克普（thiacloprid)、硫滅散（thiamethoxam)、赛普尼 (thiapronil)、赛奇伏斯(thiatriphos)、赛克能(thiocyclam)、 15 草酸氩鹽、硫敵克(thiodicarb)、硫芬斯（thiofanox)、赛美 通(thiometon)、硫速達鈉鹽(thiosultap-sodium)、蘇雲金素 (thuringiensin)、特芬必（tolfenpyrad)、奇赛靈 (tralocythrin)、赛克美靈（tralomethrin)、參伏靈 (transfluthrin)、參烈恩(triarathene)、奇赛滅(triazamate)、 2〇 奇伏斯（triazophos)、奇速能（triazuron)、三氯吩啶 (trichlophenidine)、三克芬(trichlorfon)、木黴(Trichoderma atroviride)、赛伏能(triflumuron)、赛滅卡(trimethacarb)、 凡米松（vamidothion)、凡利普（vaniliprole)、菲佈汀 (verbutin)、躐蛉輪枝孢(Verticillium lecanii)、WL-108477、 -67- 200528434 5 10 15 WL-40027、YI-5201、YI-5301、Yl-5302、XMC、賽利卡 (xylylcarb)、ZA，3274、反塔賽滅寧(Zeta-cypermethrin)、索 伏斯(zolaprofos)、ZXI-8901、化合物3-曱基苯基丙基胺甲 酸酯（tsumacide Z)、化合物 3-(5-氯-3-吡啶基)-8-(2,2,2-三 氟乙基）各氮雜雙環[3.2.1]辛烷-3-曱腈（CAS-Reg. No· 185982-80-3)與相應之3-環内橋接-異構物（CAS-Reg. No· 185984-60-5)(參見 WO_96/37494, WO_98/25923)，與包含 具殺昆蟲活性之植物萃出物、線蟲、真菌或病毒之製劑。· 亦可與其他已知活性化合物如：除草劑，或與肥料及 生長調節劑、安全劑與/或化學信息物質形成混合物。(fenamiphos), fenazaqUin, fenbutatin oxide, fenfluthrin, fenitrothion, fenobucarb, fenothiocarb, fenkelin (fenoxacrim), fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fensulphothion, fenthion ), Fentrifanil, fenvalerate, fipronil, flonicamid, fluacrypyrim, fluazuron, flubenzimine , Flubrocythrinate, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flumethrin , Flupyrazofos, flutenzin (flufenzine), fluvalinate, fonofos, formetanate, formothion, voltam (Fosmethilan), fosthiazate, Fubens-64- 20 200528434 (fubfenprox (fluproxyfen)), furathiocarb, cyhalothrin, γ-HCH, gossyplure, grandlure, chengdu Granulosis viruses, halfenprox, halfofenozide, HCH, HCN-801, Hepenophos, hexaflumuron, hexythiazox, Hydramethyl none, hydroprene, IKA_2002, imidacloprid, imiprot: hrin, indoxacarb, iodofenphos, propyl joy Pine (iprobenfos), isazofos, isofenphos, isoprocarb, isoxathion, ivermectin, japonilure, card Kadethrin, nuclear polyhedrosis viruses, kinoprene, lambda-cyhalothrin, lindane, lufenuron, marathion, keban (mecarbam), mesulphenfos, metaldehyde Metam-sodium, metacrifos, metamidophos, metharhizium anisopliae, metharhizium flavoviride, methimathion, metiocarb, metomyl, metamyl Methoprene, metoxychlor, methoxyfenozide, metofluthrin, metolcarb, metoxadiazone, mevinphos, metoc (Milbemectin), milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin, MTI-800, naled, NC-104, NC -170, -65- 200528434 NC-184, NC-194, NC-196, niclosamide, nicotine, nitenpyram, nithiazine, NNI-0001, • NNI-0101 , NNI-0250, NNI-9768, novaluron, novifhmmron, OK-5101, OK-5201, OK-9601, 5 OK-9602, OK-97 (H, OK-9802, Omethoate, oxamyl, oxydemeton-methyl, Paecilomyces fumosorose us), Parathion-methyl, (Ethyl-) balaxon, (cis-, trans-) permethrin, petroleum, PH-6045, phenothrin ) (lR-trans-10 isomer), phenthoate, phorate, phosalone, phosmet, phosphamidon, foka ( phosphocarb, phoxim, piperonyl butoxide, pirimicarb, pirimiphos-methyl, pirimiphos-ethyl, oleic acid 15 Potassium, prallethrin, profenofos, profluthrin, promecarb, propaphos, propargite, propetamphos ), Propoxur, prothiofos, prothoate, protrifenbute, pymetrozine, pyraclofos, and Pyraclofos pyresmethrin), pyrethrum, pyridaben, pyridylyl, pyridaphenthion, pyrid idathion), pyrididifen, pyriproxyfen, quinalphos, resmethrin, RH-5849, ribavirin-66- 200528434 (ribavirin), RU-12457 , RU-15525, S-421, S-1833, salithion, sebufos, SI-0009, silafluofen, spinosad, spirodiclofen , Spiromesifen, sulphiuramid, sulphotep, sulprofos, SZI-121, tau-fluvalinate, tebufenozide ), Tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, temivinphos, teban ( terbam), terbufos, tetraclilorvinphos, tetradifon, tetramethrin, tetramethrin (IR-isomer), special Tetrasul, theta_cypermethrin, thiacloprid, thiamethoxam, Thiapronil, thiatriphos, thiocyclam, 15 oxalate argon, thiodicarb, thiofanox, thiometon, thiosoda sodium Salt (thiosultap-sodium), thuringiensin, tolfenpyrad, tralocythrin, tralomethrin, transfluthrin, triarathene, Qisai Triazamate, 20 triazophos, triazuron, trichlophenidine, trichlorfon, Trichoderma atroviride, triflumuron, Trimethacarb, vamidothion, vaniliprole, verbutin, Verticillium lecanii, WL-108477, -67- 200528434 5 10 15 WL- 40027, YI-5201, YI-5301, Yl-5302, XMC, xylylcarb, ZA, 3274, Zeta-cypermethrin, zolaprofos, ZXI-8901, compound 3-fluorenylphenylpropylcarbamate (tsumacide Z), compound 3- (5-chloro-3-pyridyl)- 8- (2,2,2-trifluoroethyl) each azabicyclo [3.2.1] octane-3-fluorenenitrile (CAS-Reg. No. 185982-80-3) and the corresponding 3-ring Bridge-isomers (CAS-Reg. No. 185984-60-5) (see WO_96 / 37494, WO_98 / 25923) and preparations containing plant extracts, nematodes, fungi or viruses with insecticidal activity. • Mixtures with other known active compounds such as herbicides or with fertilizers and growth regulators, safeners and / or chemical information substances.

此外，根據本發明式⑴化合物亦具有極佳之抗霉菌活 性。其特別對皮真菌與酵母、霉菌及雙相型真菌（例如··對 抗假絲酵母屬（Candida) ’如：白假絲酵母（Candida albicans)，團假絲酵母(Candida glabrata))，及絮狀表皮癬 菌(Epidermophytonfloccosum)、曲黴屬（Aspergillus)如：黑 曲黴（Aspergillus niger)與煙曲黴（Aspergillus fumigatus)、 髮癬菌屬（Trichophyton)如：鬚髮癬菌（Trichophyton mentagrophytes)，小孢黴屬（Microsporon)如：狗小孢黴 (Microsporon canis)與頭癬小孢黴(Microsporon audouinii) 具有廣譜抗霉菌活性。此等真菌絕未限制其霉菌範圍，僅 供說明用。 活性化合物可呈其本身形式使用或呈其調配物形式或 由調配物製成之形式使用，如：現成可用之溶液、懸浮液、 可濕化粉劑、糊劑、可溶性粉劑、細粉劑與粒劑。其可依 -68- 20 200528434 -般方式施用，例如：洗水、噴m、噴霧、撒播、撒粉、 ^包、散播，等等。亦可採用超低體積法施用活性化合物， 或注射活性化合物製劑或活性化合物本身至土 處理植物之種子。 展。亦可 當使用根據本發明活性化合物作為殺真菌劑時 用率可在相當大範_變化’端賴施用形式而定。處理 物種子時，活性化合物之施用率通常在〇 ι至仞㈧〇 公頃之間，較佳為10至1000克/公頃之間。包覆種 活性化合物之施用率通常在0.001至5〇 早 二，佳為謂至1G克/公斤種子之間。處‘壤時，活 二，物之施用率通常在（U至1〇，_克/公頃之間，較佳 為1至5000克/公頃之間。 15 20 _本發明可處理所有植物與其部份植株。 =佳，、體實施例中係處理野生植物品種與植物栽典〇種 ίΓ:!，生物育種法(如:交配法或原生質融合:)取 =，/、，、#份植株。另一項較佳具體實施例中，係 植f傳工程(若適料’可併用㈣方法)得到之轉殖基因 达，，部栽培品種(基因改造生物）’及其部份植株:術 。卩伤或植株部份"或”部份植株"已如上述說明。 始特別佳者，根據本發明係處理自商品取得或使 栽培品種之植物。咸了解，植物栽培品 誘變法或重組職技術得到之具有新二由; 、座）之植物。其可為生物型或基因賴培品種。 依植物品種或植物栽培品種、其位置與生長條件（土 -69- 200528434 壞、氣候、營養生長期、肥料）而異，根據本發明處理 可能產生超過加成性（”增效性”)效果。因此，可能 巧之效果為例如：降低施用率與/或擴大活性範圍 尚根據本發明所使用㈣與組合物之錄、更佳之植物生 長、提高對高溫或低溫之耐受性、提高對乾旱或對水 ΐ土^鹽含量之耐紐、提高開料、提早收成、加速成 ===高/收成產品之品質與/或提高營養價 值更域存女疋性與/或提高所收成產品之可加工性。 最好根據本發明處理之轉殖基因植物或植物 (中亦即彼等由遺傳工程取得者)包括所有於基因改造。過: :之:優點(適用於此等植物之特性)之基因材 耐受性、A 切水含量或塌鹽含量之 15 提高所收成:::品質t:: 了高收穫量、 之可加工性。其他及特別強調之此 Γ如:;ΐΓ:抗動物與微生物害產之更佳防紫 ------ 掛橘與葡萄)特;;重=菜巧^^ 之、特定特性特定言之為利用植株内所形成毒 、 ° 自踩雲金芽胞桿菌(Bacillus thuringiensis) 20 200528434 之遺傳物質（例如：基因 CrylA(a)、CrylA(b)、CrylA(c)、 CryllA、CrylllA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb 與 CrylF及其組合)於植株内所形成之毒素（下文中稱為”Bt植 物”)提高對抗昆蟲、蜱蟎、線虫與蠕蟲之防禦性。亦特別 5 強調之特性為利用後天取得之全株抗性（SAR)、系統素 (systemin)、植物抗毒素、誘發素(eiicit〇rs)與抗性基因，及 相應表現之蛋白質與毒素，提高對抗真菌、細菌與病毒之 防禦性。其他特別強調之特性為提高植物對某些除草活性| 化合物，例如：咪唑啉酮類、磺醯脲類、草甘膦(glyphosate) 〇 或膦三辛（phosphinotricin)之耐受性（例如："PAT"基因）。 此等賦與所需特性之基因亦可相互組合進入轉殖基因植 物中。nBt植物”實例可述及以下列商品名稱出售之玉米品 種、棉花品種、大豆品種與馬鈴薯品種GARD® (例 如：玉米、棉花、大豆）、Knock〇ut(g)(例如：玉米）、StarLink@ 5 (例如：玉米）、Bollgard®(棉花）、Nucotn@ (棉花）與In addition, the compound of formula (I) according to the present invention also has excellent antifungal activity. It is particularly effective against skin fungi and yeasts, molds, and biphasic fungi (eg, against Candida's such as Candida albicans, Candida glabrata), and Epidermophytonfloccosum, Aspergillus such as Aspergillus niger and Aspergillus fumigatus, Trichophyton such as Trichophyton mentagrophytes, Microspora (Microsporon) For example: Microsporon canis and Microsporon audouinii have broad-spectrum antifungal activity. These fungi in no way limit their mold range and are for illustration purposes only. The active compounds can be used in their own form or in the form of formulations or preparations, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, fine powders and granules . It can be applied in the usual manner, such as: washing water, spraying, spraying, spraying, dusting, dusting, bagging, spreading, etc. It is also possible to apply the active compound by the ultra-low-volume method, or to inject the active compound preparation or the active compound itself to the seed of a soil-treated plant. exhibition. Also when the active compound according to the invention is used as a fungicide, the rate of application can vary considerably depending on the application form. When treating seed, the application rate of the active compound is usually between 0 m and 100 ha, preferably between 10 and 1000 g / ha. Coated seeds The application rate of the active compound is usually between 0.001 and 50%, preferably between 1G g / kg of seed. In the case of soil, the application rate is usually between (U to 10, _ g / ha, preferably 1 to 5000 g / ha. 15 20 _ The present invention can treat all plants and their parts The number of plants in the example is good. In the examples, the wild plant species and plant species are treated with 0 species: Γ:!, And the biological breeding method (such as: mating method or protoplast fusion :) ==, / ,,, # parts of plants. In another preferred embodiment, the transgenic genes obtained from the plant f-transplantation project (if appropriate, 'can be used in combination with the ㈣ method), the cultivar (genetically modified organisms)' and some of the plants: surgery. Sting or plant part " or " partial plant " has been described as above. Particularly preferred, according to the present invention is the treatment of plants obtained from commercial or cultivated cultivars. It is understood that the method of mutagenesis of plant cultivation or The plant obtained by the reorganization technology has a new two reasons; it can be a biotype or a genetic Lai Pei variety. Depending on the plant variety or plant cultivar, its location and growth conditions (Earth-69-200528434 bad, climate, Vegetative growth period, fertilizer), the treatment according to the present invention may produce Exceeds the additive ("synergistic") effect. Therefore, the possible effects are, for example, reducing the application rate and / or expanding the active range. Tolerance to high or low temperature, increase resistance to drought or hydroponic soil ^ salt content, increase feed opening, early harvest, accelerated yield === high / harvest product quality and / or increase nutritional value Preservation of son-in-law and / or enhancement of the processability of the harvested product. Transgenic plants or plants that are preferably treated according to the present invention (in other words, they are obtained by genetic engineering) include all genetic modification. Over:: Advantages: Advantages (applicable to the characteristics of these plants) Genetic material tolerance, A cut water content or collapse salt content 15% Improved harvest ::: Quality t :: High harvest yield, processability. Others And especially emphasized this Γ such as: ΐΓ: better anti-violet resistance to animal and microbial damage --- hanging oranges and grapes) special; weight = vegetable skill ^^, specific characteristics and specific words are Utilizing the virulence formed in the plant, ° Bacillus thuringiensis 20 20 0528434 genetic material (for example: genes CrylA (a), CrylA (b), CrylA (c), CryllA, CryllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and combinations thereof in plants (hereinafter (Referred to as "Bt plant") to improve defenses against insects, mites, nematodes and worms. The characteristics emphasized in particular 5 are the use of acquired plant resistance (SAR), systemin, and phytoalexins , Elicitors (eiicitors) and resistance genes, and correspondingly expressed proteins and toxins, to improve defenses against fungi, bacteria and viruses. Other particularly emphasized properties are to improve the tolerance of plants to certain herbicidal activities | compounds, such as: imidazolinones, sulfonylureas, glyphosate 0 or phosphinotricin (eg: " PAT " gene). These genes imparting the desired characteristics can also be combined with each other into transgenic plants. Examples of "nBt plants" may include corn varieties, cotton varieties, soybean varieties, and potato varieties sold under the trade names GARD® (for example: corn, cotton, soybean), Knockout (g) (for example, corn), StarLink @ 5 (e.g. corn), Bollgard® (cotton), Nucotn @ (cotton) and

NewLeaf®(馬龄薯）。除草劑耐受性植物實例可述及以下列龜 商〇口名稱出售之玉米品種、棉花品種與大豆品種：R〇undUp Ready®(耐受草甘膦，例如：玉米、棉花、大豆）、Uberty Link®(耐受膦三辛(ph〇sphinotricin),例如··油菜）、IMI(g)(耐 3 乂米哇琳酮類）與STS®(耐受續醯脲類，例如··玉米)。可 述及之徐草劑抗性植物（依傳統育種法育種而耐受除草劑 之植物)包括以下列商品名稱出售之品種：clearfield⑧(例 如.玉米）。當然，此等說明亦適用於已具有此等遺傳特性 或仍待發展出此等遺傳特性之植物栽培品種，該等植物將 -71- 200528434 於未來發展與/或上市。 上列植物可依據本發明，以特別有利之方式，使用根 據本發明通式(I)化合物或活性化合物混合物處理。上述活 性化合物或混合物之較佳範圍亦適用於處理此等植物。特 5 別強調以本文中明確說明之化合物或混合物處理植物。 根據本發明活性化合物之製備與用途將於下 說明。 夕U實例中 【實施方式】 10 製備實例 實例1NewLeaf® (horse-age potato). Examples of herbicide-tolerant plants include corn varieties, cotton varieties, and soybean varieties sold under the following names: RoundUp Ready® (glyphosate-tolerant, such as corn, cotton, soybean), Uberty Link® (Phosphinotricin-tolerant, e.g., rapeseed), IMI (g) (3 tolerant to milivonones), and STS® (tolerant to diurea, such as corn) . The herbicide-resistant plants that can be mentioned (plants that have been tolerated by traditional breeding methods and are resistant to herbicides) include varieties sold under the following trade name: clearfieldclear (e.g., corn). Of course, these instructions also apply to plant cultivars that already have these genetic traits or are still developing such genetic traits, and these plants will be developed and / or marketed in the future. The plants listed above can be treated according to the invention in a particularly advantageous manner using a compound of the general formula (I) or an active compound mixture according to the invention. The preferred ranges of the above active compounds or mixtures are also suitable for treating these plants. Special emphasis should not be placed on the treatment of plants with the compounds or mixtures explicitly described herein. The preparation and use of the active compound according to the present invention will be described below. In the U example [Embodiment] 10 Preparation Example Example 1

CH CK 添加 191.3 mg n.Omrrml、I 二审 I、CH CK added 191.3 mg n. Omrrml, I second trial I,

mg (理論值之89%)3-(二氯甲基)小甲基-N-[2-(l，3,3、〜 Η2·1 丁基）苯基]-1Η-吡唑_4_羧醯胺[logP(pH=2.3)=4.〇2j。甲基mg (89% of theory) 3- (dichloromethyl) small methyl-N- [2- (l, 3,3, ~ Η2.1 · butyl) phenyl] -1Η-pyrazole_4_ Carboxamide [logP (pH = 2.3) = 4.02j. methyl

200528434 表1200528434 Table 1

①①

Ex. R1 R2 R3 A logP 2 Η Η ch3 H3V/ tk0H N CH3 ch3 3.19 4 Η Η ch3 H3C^\_/. ISJ u CH3 4.25 6 Η Η gh3 Fs(W V ch3 3.81 8 Η Η ch3 Η3°Λ/ o V CH3 3.63 10 Η Η ch3 Q ch3 4.19 12 Η Η ch3 "W ch3 4.24 14 Η Η ch3 HV NyS Cl 4.52Ex. R1 R2 R3 A logP 2 Η Η ch3 H3V / tk0H N CH3 ch3 3.19 4 Η Η ch3 H3C ^ \ _ /. ISJ u CH3 4.25 6 Η Η gh3 Fs (WV ch3 3.81 8 Η Η ch3 Η3 ° Λ / o V CH3 3.63 10 Η ch3 Q ch3 4.19 12 Η Η ch3 " W ch3 4.24 14 Η Η ch3 HV NyS Cl 4.52

Ex· R1 R2 R3 A logP 3 H H ch3 F3V/ tka 丫。丨 ch3 4.34 5 H H ch3 V。1 ch3 4.39 7 H H C2H5 F3V/ V ch3 4.13 9 H H ch3 cw V CH3 3.79 11 H H ch3 1 p ch3 F 3.81 13 H H ch3 H3V Kys ch3 3.60 15 H H C2H5 Nys Cl 4.89 -73- 200528434Ex · R1 R2 R3 A logP 3 H H ch3 F3V / tka.丨 ch3 4.34 5 H H ch3 V. 1 ch3 4.39 7 H H C2H5 F3V / V ch3 4.13 9 H H ch3 cw V CH3 3.79 11 H H ch3 1 p ch3 F 3.81 13 H H ch3 H3V Kys ch3 3.60 15 H H C2H5 Nys Cl 4.89 -73- 200528434

Ex. R1 R2 R3 A logP 16 H H ch3 底 4.27 18 H H ch3 、sAch3 4.39 20 H H c2h5 4.38 22 H H ch3 v Vs 4.40 24 H H ch3 V Vs 4.92 26 H H ch3 V 4.15 28 H H ch3 0； 3.89 30 H H ch3 :oc 3.95 32 H H ch3 FV T 4.80Ex. R1 R2 R3 A logP 16 HH ch3 Bottom 4.27 18 HH ch3 sAch3 4.39 20 HH c2h5 4.38 22 HH ch3 v Vs 4.40 24 HH ch3 V Vs 4.92 26 HH ch3 V 4.15 28 HH ch3 0; 3.89 30 HH ch3: oc 3.95 32 HH ch3 FV T 4.80

Ex· R1 R2 R3 A logP 17 H H c2h5 〔X 4.63 19 H H ch3 、〇Ach3 4.04 21 H H ch3 S^CF3 4.37 23 H H c2h5 v Vs 4.75 25 H H ch3 HaW Vs 3.84 27 H H ch3 3.97 29 H H ch3 cNr 3.97 31 H H ch3 F2HV/ ¥ CH3 4.16 -74- 200528434 式（ιι)起始物之製法 實例（ΙΙ-ΠExR1 R2 R3 A logP 17 HH c2h5 (X 4.63 19 HH ch3, 〇Ach3 4.04 21 HH ch3 S ^ CF3 4.37 23 HH c2h5 v Vs 4.75 25 HH ch3 HaW Vs 3.84 27 HH ch3 3.97 29 HH ch3 cNr 3.97 31 HH ch3 F2HV / ¥ CH3 4.16 -74- 200528434 Example of preparation method of formula (ιι) starting material (ΙΙ-Π

Vc, 10 取 300·0 mg (1.9mmol)3_曱酿基-1-曱基-111-0比嗤-4-緩 酸溶於6〇 ml二氯甲烧中’添加i.〇g (4·9 mm〇l)五氣化磁。 於室溫下L5小時後，混合物倒至冰_水中，以二氣甲 取，萃液經硫酸鎂脫水，過濾邀域厭、#^ . ^ ^ 界成壓濃縮。產生384.0 mg (理論值之86%)3-^ —氣曱基-1、甲其 T基]H-吡唑-4-羰基氯[i〇gp (pH2.3)=1.80] 15 式（VII)起始物之製法 實例 rvii-i)Vc, 10 Take 30.0 mg (1.9 mmol) of 3-pyridyl-1-pyridyl-111-0, and then dissolve it in 60 ml of dichloromethane.Add i.〇g ( 4.9 mm) 5 gasification magnetization. After 5 hours at room temperature, the mixture was poured into ice-water, taken with dichloromethane, and the extract was dehydrated with magnesium sulfate, filtered, and concentrated. Yield 384.0 mg (86% of theory) 3-^-Arylidene-1, methyl its T group] H-pyrazole-4-carbonyl chloride [iogp (pH2.3) = 1.80] 15 Formula (VII ) Example of the preparation method of the starting material rvii-i)

添加 16.0ml(170m〇l)乙酸野至含 i〇〇g(57_i)44_ 二甲氧基-3-氧代丁酸甲醋之9.〇g (85麵叫原甲酸三甲基 醋之溶液卜反舰合物回“熱16小時。反應混合物 蒸顧(彿點132·135 C ’ G·2 (理論值之56%) 4,4-二曱氧基-2-曱氧亞曱基-3、氣代丁酸甲醋。 -75* 200528434 式（ιχ)起始物之製法 實例σχ-υAdd 16.0ml (170ml) of acetic acid to a solution containing OOg (57_i) 44_ dimethoxy-3-oxobutanoic acid methyl acetate (9.0g (85 sides called trimethyl orthoformate) solution The anti-ship compound was "heated for 16 hours. The reaction mixture was steamed (Buddha 132 · 135 C'G · 2 (56% of theory)) 4,4-dioxo-2-oxofluorenylene- 3. Gas-butyric acid methyl vinegar. -75 * 200528434 Example of production method of starting material of formula (ιχ) σχ-υ

5 於-5QC下，慢慢滴加含2·0 ml (38mmol)甲基肼之340 ml甲醇溶液至7.5 g4,4-二甲氧基-2-曱氧亞曱基-3-氧代丁 酸曱酯中。滴加完畢後，反應混合物於室溫下攪拌16小 ίο 時，減壓濃縮。經管柱層析法（移動相梯度環己烷/乙酸乙 酯），產生6.5g (理論值之77% )3-二甲氧甲基小甲基-1H-吡唑-4-羧酸曱酯。 式OQ起始物之製法5 At -5QC, slowly add 340 ml of a methanol solution containing 2.0 ml (38 mmol) of methylhydrazine to 7.5 g of 4,4-dimethoxy-2-fluorenimidine-3-oxobutane. Acid ester. After the addition was completed, the reaction mixture was stirred at room temperature for 16 hours, and then concentrated under reduced pressure. Column chromatography (mobile phase gradient cyclohexane / ethyl acetate) yielded 6.5 g (77% of theory) of 3-dimethoxymethyl small methyl-1H-pyrazole-4-carboxylic acid ethyl ester . Preparation method of formula OQ starter

2〇 添加10 ml濃鹽酸至含2.1g (lOmmol) 3-二甲氧曱基-1- 甲基-1H-吡唑-4-羧酸曱酯之20 ml二崎烷溶液中，混合物 於室溫下攪拌16小時。操作時，混合物減壓濃縮，殘質 溶於200 ml二氯曱烷中，以50 ml水洗滌。有機相經硫酸 鎂脫水，過濾與濃縮。產生1.6g (理論值之94%) 3-甲醯基 -76- 200528434 -1-甲基-1H-吡唑-4讎羧酸曱酯[logP (ρΗ2·3) = 0·46] 〇 式（XI)起始物之製法 實例（ΧΙ-Π 5 ο Ο20 Add 10 ml of concentrated hydrochloric acid to a solution of 2.1 ml (10 mmol) of 3-dimethoxyfluorenyl-1-methyl-1H-pyrazole-4-carboxylic acid methyl ester in 20 ml of diazidine, and mix the mixture in a chamber. Stir at warm for 16 hours. During operation, the mixture was concentrated under reduced pressure, and the residue was dissolved in 200 ml of dichloromethane and washed with 50 ml of water. The organic phase was dehydrated over magnesium sulfate, filtered and concentrated. Yield 1.6 g (94% of theory) (XI) Example of preparation method of starting material (XΙ-Π 5 ο Ο

ch3 Η 取6.0g (35.68 mmol) 3-曱醯基小甲基-1H-吡唑-4-羧酸 ίο 甲醋溶於180 ml四氫ϋ夫喃與90 ml水中，添加0·94 g (39·25 mmol)氫氧化鋰。反應混合物於室溫下攪拌16小時，減壓 排除有機相，殘留之水相經稀鹽酸酸化，以各100 ml乙酸 乙酯洗滌3次。有機相經硫酸鎂脫水，過濾與濃縮。產生 4·28 g(理論值之78%) 3-曱醯基小曱基_1H-吡唑-4-羧酸 15 logP (pH =2·3)=-0·19 〇 式（XII)起始物之製法 -心3 Αη3 取46·1 mg (0.27 mmol) 3-曱醯基小甲基-1Η-吡唑-4-羧 酸甲酯溶於10 ml二氣甲烧中，添加142.9 mg (0·67 mmol) -77- 200528434 五氯化磷。反應混合物於室溫下攪拌15小時，加至水中， 以乙醚萃取，萃液經硫酸鎂脫水及減壓濃縮。產生53 〇mg (理論值之86%) 3-(二氯曱基）+甲基」吡唑羧酸甲 酯，logP (pH 2·3) = 1·80。 此甲酯可依一般方式水解。產生3_(二氯甲基)_丨_甲基 -1Η-吡唑-4-羧酸，其可直接與式(111)化合物偶合或在轉二 成醯基氯後偶合。 上述製備實例與列表中所示之l〇gP之測定法係依據· EEC-指令79/831 Annex V.A8，採用HPLC(高效液相層析 法），於逆相管柱(C 18)上進行。溫度·· 43t：。測定法係於 pH 2·3之酸性範圍内，使用移動相〇1%磷酸水溶液與乙腈 進行；線性梯度為10%乙腈至90%乙腈。採用已知其' 1〇获 值之未分支之烷-2-酮（3至16個碳原子）進行校正(1〇gp值 之測定法係採用兩種連續烧酮類滯留時間之間線性内插 測得）。λ-最大值係使用200 nm至400 nm之間之UV光譜 之層析訊號中所測得之最大值。 gch3 Η Take 6.0g (35.68 mmol) of 3-fluorenylmethyl-1H-pyrazole-4-carboxylic acid οο methyl acetate is dissolved in 180 ml of tetrahydrofuran and 90 ml of water, and 0.94 g ( 39.25 mmol) lithium hydroxide. The reaction mixture was stirred at room temperature for 16 hours. The organic phase was removed under reduced pressure. The remaining aqueous phase was acidified with dilute hydrochloric acid and washed three times with 100 ml of ethyl acetate each. The organic phase was dehydrated over magnesium sulfate, filtered and concentrated. Yield 4.28 g (78% of theory) 3-fluorenyl berberyl_1H-pyrazole-4-carboxylic acid 15 logP (pH = 2 · 3) =-0 · 19 〇 From formula (XII) Preparation of the starting material-Heart 3 Αη3 Take 46.1 mg (0.27 mmol) of 3-methylamino-1,1-pyrazole-4-carboxylic acid methyl ester and dissolve it in 10 ml of digassine, and add 142.9 mg (0.67 mmol) -77- 200528434 phosphorus pentachloride. The reaction mixture was stirred at room temperature for 15 hours, added to water, and extracted with ether. The extract was dehydrated with magnesium sulfate and concentrated under reduced pressure. This gave 53.0 mg (86% of theory) of 3- (dichlorofluorenyl) + methyl "pyrazolecarboxylic acid methyl ester, logP (pH 2.3) = 1.80. This methyl ester can be hydrolyzed in a general manner. 3_ (Dichloromethyl) _ 丨 _methyl-1Η-pyrazole-4-carboxylic acid is produced, which can be coupled directly to a compound of formula (111) or after conversion to a fluorenyl chloride. The measurement method of 10 gP shown in the above preparation example and list is based on EEC-Directive 79/831 Annex V.A8, using HPLC (High Performance Liquid Chromatography) on a reverse-phase column (C 18) get on. Temperature · 43t :. The measurement method is performed in the acidic range of pH 2.3, using a mobile phase of a 0.1% phosphoric acid aqueous solution and acetonitrile; a linear gradient is 10% acetonitrile to 90% acetonitrile. Calibration was performed using an unbranched alk-2-one (3 to 16 carbon atoms) with a known value of 10 (the 10 gp value was determined using a linear within the retention time of two consecutive burned ketones Measured). λ-max is the maximum measured in a tomographic signal using UV spectrum between 200 nm and 400 nm. g

應用實例： f例A 早囊殼(Podosphaera)試驗(顏果）/保護性 溶劑·· 24.5份重量比丙酮 24.5份重量比二甲基乙醯胺 乳化劑：1份重量比炫芳基聚二醇_ 製備活性化合物之合適製劑時，由丨份重量比活性化 -78- 200528434 濃縮物至所 合物與上述量溶劑及乳化劑混合，加水稀釋該 需濃度。 5 …測試保護活性時，取活性化合物之製劑，依指定施用 率喷灑植物幼苗。喷灑層乾燥後，在植物上接種蘋果 病原菌白叉絲單囊殼(Podosphaera leucotricha)之水性孢子 懸浮液。然後將植物置入約23QC，相對濕度約之溫室 中。 接種10天後，進行評估，〇%表示其效力相當於對照% 組，而100%效力表示沒有發現感染。 -79- 200528434Application example: f case A Podsphaera test (Yan Guo) / protective solvent ... 24.5 parts by weight acetone 24.5 parts by weight dimethylacetamide emulsifier: 1 part by weight xanthanyl polydiene Alcohol_ When preparing a suitable formulation of active compound, the concentration is activated from 丨 parts by weight to -78- 200528434 until the compound is mixed with the above-mentioned amount of solvent and emulsifier, and the required concentration is diluted by adding water. 5… When testing for protective activity, take the preparation of active compound and spray the plant seedlings at the specified application rate. After the spray layer was dried, the plants were inoculated with an aqueous spore suspension of the apple pathogenic pathogen Podosphaera leucotricha. The plants were then placed in a greenhouse at approximately 23 QC and approximately relative humidity. Evaluation was performed 10 days after the inoculation, and 0% indicated that the efficacy was equivalent to the control% group, while 100% indicated that no infection was found. -79- 200528434

表A 單囊殼(Podosphaera)試驗（蘋果）/保護性Table A Podsphaera Test (Apple) / Protection

-80 200528434 單囊殼(Podosphaera)試驗（蘋果）/保護性 根據本發明化合物 活性化合物施用率1 效力％ (g/ha) I η3Γ 100 1〇〇 <3 -81- 200528434-80 200528434 Podsphaera test (Apple) / Protective compound according to the invention Active compound application rate 1% efficacy (g / ha) I η3Γ 100 100 < 3 -81- 200528434

實例B 黑星菌（Venturia)試驗（蘋果）/保護性 溶劑·· 24.5份重量比丙酮 24,5份重量比二甲基乙醯胺 5 乳化劑：1份重量比烷芳基聚二醇醚 製備活性化合物之合適製劑時，由1份重量比活性化 合物與上述量溶劑及乳化劑混合，加水稀釋該濃縮物至所 需濃度。 測試保護活性時，取活性化合物之製劑，依指定施用 10 率喷灑植物幼苗。喷灑層乾燥後，在植物上接種蘋果瘡痂 病病原菌蘋果黑星菌（Venturia inaequalis)之水性分生孢子 懸浮液，然後留在約20°C與相對濕度100%培養箱中1天。 然後將植物置入約21°C，相對濕度約90%之溫室中。 接種10天後，進行評估，〇%表示其效力相當於對照 is 組，而100%效力表示沒有發現感染。 -82- 200528434Example B Venturia test (Apple) / Protective solvent · 24.5 parts by weight acetone 24,5 parts by weight dimethylacetamide 5 Emulsifier: 1 part by weight alkylaryl polyglycol ether When preparing a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the above-mentioned amount of solvent and emulsifier, and the concentrate is diluted with water to a desired concentration. When testing for protective activity, take the formulation of the active compound and spray the plant seedlings at the specified application rate. After the spray layer was dried, the plants were inoculated with an aqueous conidia suspension of Venturia inaequalis, the pathogen of apple scab, and then left in an incubator at about 20 ° C and a relative humidity of 100% for 1 day. The plants were then placed in a greenhouse at about 21 ° C and a relative humidity of about 90%. Evaluation was performed 10 days after the inoculation, and 0% indicated that the efficacy was equivalent to the control is group, while 100% indicated that no infection was found. -82- 200528434

表B 黑星菌（Venturia)試驗（蘋果）/保護性 =~根據本發明化合物~ |活性化合物施用率| 效力％ 1 (g/ha) I_Table B Venturia test (apple) / protective = ~ compound according to the invention ~ | active compound application rate | efficacy% 1 (g / ha) I_

100 96100 96

Η 100 100Η 100 100

100 100 100 93100 100 100 93

100 99100 99

100 95100 95

100 92 -83 200528434 黑星菌（Venturia)試驗（蘋果）/保護性 根據本發明化合物 丨活性化合物施用率| 效力％ 1 (g/ha) 1_100 92 -83 200528434 Venturia test (apple) / protective compound according to the invention 丨 active compound application rate | efficacy% 1 (g / ha) 1_

-84- 200528434 實例C 灰葡萄孢(Botrytis)試驗（豆類）/保護性 溶劑：24.5份重量比丙酮 5 10 24.5份重量比二甲基乙醯胺 乳化劑：1份重量比烷芳基聚二醇醚-84- 200528434 Example C Botrytis test (beans) / protective solvent: 24.5 parts by weight of acetone 5 10 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkylaryl polydiene Alcohol ether

製備活性化合物之合適製劑時，由1份重量比活性化 合物與上述量溶劑及乳化劑混合，加水稀釋該濃縮物至所 需濃度。 測試保護活性時，取活性化合物之製劑，依指定施用 率喷灑植物幼苗。喷灑層乾燥後，在各植物葉片上放置2 小片含有灰葡萄抱(Botrytis cinerea)菌落之洋菜。接種後之 植物置於約20°C與100%相對濕度之黑暗箱中培養。 接種2天後，評估葉面上感染面積大小。0%表示其效 力相當於對照組，而100%效力表示沒有發現感染。 -85- 200528434 表c 灰葡萄孢(Botrytis)試驗（豆類）/保護性 根據本發明化合物 活性化合物施用率 效力％ _1 (g/ha) I_When preparing a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above-mentioned amount of solvent and emulsifier, and the concentrate is diluted with water to a desired concentration. When testing for protective activity, take the preparation of active compound and spray the plant seedlings at the specified application rate. After the spraying layer was dried, 2 small pieces of amaranths containing Botrytis cinerea colonies were placed on the leaves of each plant. The inoculated plants were grown in a dark box at about 20 ° C and 100% relative humidity. Two days after the inoculation, the size of the infected area on the leaf surface was evaluated. 0% means that it is equivalent to the control group, while 100% means that no infection is found. -85- 200528434 Table c Botrytis test (beans) / protective compounds Compounds according to the invention Active compound application rate Effectiveness% _1 (g / ha) I_

500 100 500 500 500 500 500 500 500 95 100 88 100 100 95 97 % -86 200528434 灰葡萄孢(Botrytis)試驗（豆類）/保護性500 100 500 500 500 500 500 500 500 95 100 88 100 100 95 97% -86 200528434 Botrytis test (beans) / protective

根據本發明化合物 |活性化合物施用率 效力％ 1 (g/ha) -ICompounds according to the inventionThe active compound application rate Effectiveness% 1 (g / ha) -I

-87- 200528434-87- 200528434

實例D 柄錄囷（Puccinia)試驗（小麥）/保護性 a) 溶劑：50份重量比N，N-二曱基乙醯胺 乳化劑·· 1份重量比烷芳基聚二醇醚 b) 溶劑：25份重量比N，N-二甲基乙醯胺 乳化劑：0.6份重量比烧芳基聚二醇醚 製備活性化合物之合適製劑時，由1份重量比活性化 合物與上述量溶劑及乳化劑混合，加水稀釋該濃縮物至戶 需濃度。 斤 10 測試保護活性時，取活性化合物之製劑，依指定施用 率喷灑植物幼苗。喷灑層乾燥後，在植物幼苗上噴壤隱匿 15 柄銹菌（Puccinia recondita)之分生孢子懸浮液。植物留在 20°C與1〇〇%相對濕度培養箱中48小時。 然後將植物置入約2(TC，相對濕度80%之溫室中，促 進銹菌孢狀突起產生。 接種10天後，進行評估，0%表示其效力相當於對照 組，而100%效力表示沒有發現感染。Example D Puccinia test (wheat) / protective a) Solvent: 50 parts by weight of N, N-diethylacetamide emulsifier · 1 part by weight of alkylaryl polyglycol ether b) Solvent: 25 parts by weight of N, N-dimethylacetamide emulsifier: 0.6 parts by weight of sintered aryl polyglycol ether. A suitable preparation of the active compound is prepared from 1 part by weight of the active compound and the above-mentioned solvent and The emulsifiers are mixed and water is added to dilute the concentrate to the desired concentration. When testing for protective activity, take the preparation of active compound and spray the plant seedlings at the specified application rate. After the spray layer has dried, the plant seedlings are sprayed with a conidia suspension of 15 Puccinia recondita. The plants were left in an incubator at 20 ° C and 100% relative humidity for 48 hours. The plants were then placed in a greenhouse at about 2 ° C and 80% relative humidity to promote the generation of spore-like protrusions of rust fungi. Evaluation was performed 10 days after inoculation, 0% indicates that its efficacy is equivalent to the control group, and 100% efficacy indicates that it is not Found an infection.

-88 - 200528434-88-200528434

表D 柄銹菌（Puccinia)試驗（小麥）/保護性 根據本發明化合物 活性化合物施用率效力％ 溶劑/乳化劑 (g/ha) [ _I__Table D Puccinia test (wheat) / protective compounds according to the invention Active compound application rate efficacy% solvent / emulsifier (g / ha) [_I__

500 100 a) 500 500 500 500 500 500 100 100 100 100 100 100 a) a) a) a) a) b)500 100 a) 500 500 500 500 500 500 100 100 100 100 100 100 a) a) a) a) a) b)

-89- 200528434 柄錄菌（Puccinia)試驗（小麥）/保護性 根據本發明化合物 活性化合物施用率效力％ (g/ha) 1 溶劑/乳化劑-89- 200528434 Puccinia test (wheat) / protective properties Compounds according to the invention Active compound application rate efficacy% (g / ha) 1 solvent / emulsifier

b) 500 100b) 500 100

90- 20052843490- 200528434

實例E 單絲殼(Sphaerotheca)試驗（胡瓜）/保護性 溶劑：49份重量比Ν，Ν-二甲基甲醯胺 乳化劑·· 1份重量比烷芳基聚二醇醚 5 製備活性化合物之合適製劑時’由1份重量比活性化 合物與上述量溶劑及乳化劑混合，加水稀釋該濃縮物至所 需濃度。 測試保護活性時，取活性化合物之製劑，依指定施用· 率喷灑在胡瓜幼苗上。處理一天後，在各植物上接種蒼耳 ίο 单絲设（Sphaerotheca fuliginea)之孢子懸浮液。植物置於 70%相對濕度及23°C之溫室中。 接種7天後，進行評估。〇%表示其效力相當於對照組， 而100%效力表示沒有發現感染。 200528434Example E Sphaerotheca test (cucurbit) / protective solvent: 49 parts by weight of N, N-dimethylformamide emulsifier · 1 part by weight of alkylaryl polyglycol ether 5 Preparation of active compound In a suitable formulation, 'the active compound is mixed with the above-mentioned amount of solvent and emulsifier in 1 part by weight, and the concentrate is diluted with water to a desired concentration. When testing the protective activity, take the preparation of the active compound and spray it on the squash seedlings at the specified application rate. After one day of treatment, each plant was inoculated with a spore suspension of Sphaerotheca fuliginea. Plants were placed in a greenhouse at 70% relative humidity and 23 ° C. Evaluation was performed 7 days after the inoculation. 0% indicates that its efficacy is equivalent to the control group, while 100% indicates that no infection was found. 200528434

表E 單絲殼(Sphaerotheca)試驗(胡瓜）/保護性 ~根據本發明化合物_ |活性化合系施用率| ~效力％ (g/ha) 1__Table E Sphaerotheca Test (Squash) / Protective ~ Compounds according to the invention _ | Active chemical combination application rate | ~ Efficiency% (g / ha) 1__

750 95750 95

750 95 750 90750 95 750 90

200528434200528434

實例F 禾白粉菌（Erysiphe)試驗(大麥）/保護性 溶劑：25份重量比N，N-二甲基乙醯胺 乳化劑·· 0.6份重量比烷芳基聚二醇醚 5 製備活性化合物之合適製劑時，由1份重量比活性化 合物與上述量溶劑及乳化劑混合，加水稀釋該濃縮物至所 需濃度。 測試保護活性時，取活性化合物之製劑，依指定施用| 率喷灑在幼苗上。喷灑層乾燥後，在植物上撒上禾白粉菌 ίο (Erysiphe graminis f.sp.hordei)之抱子。 植物置於約20°C與約80%相對濕度之溫室中，以促進 黴菌孢狀突起產生。 接種7天後，進行評估。〇%表示其效力相當於對照 組，而100%效力表不沒有發現感染。Example F Erysiphe test (barley) / protective solvent: 25 parts by weight N, N-dimethylacetamide emulsifier · 0.6 parts by weight alkylaryl polyglycol ether 5 Preparation of active compound For a suitable formulation, one part by weight of the active compound is mixed with the above-mentioned amount of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. When testing for protective activity, take a formulation of the active compound and spray it on seedlings at the specified application rate. After the spray layer is dried, the plant is sprinkled with a bramble of Erysiphe graminis f.sp.hordei. Plants are placed in a greenhouse at about 20 ° C and about 80% relative humidity to promote the generation of mold-like spore protrusions. Evaluation was performed 7 days after the inoculation. 〇% indicates that its efficacy is equivalent to that of the control group, while 100% efficacy table shows no infection.

-93- 200528434-93- 200528434

表F 禾白粉菌（Erysiphe)試驗(大麥）/保護性 I 根據本發明化合物 活性化合物施用率 效力％ 1 (g/ha)Table F Erysiphe test (barley) / protective properties I Compounds according to the invention Active compound application rate Effectiveness% 1 (g / ha)

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Claims (1)

200528434 十、申請專利範圍· 1. 一種式⑴己基醯基苯胺200528434 X. Scope of applying for patents Φ ch3 ch3 其中 L 代表 10Φ ch3 ch3 where L represents 10 1-4 其中標示*之鍵結係附接醯胺，而標示#之鍵結則押 接烷基侧鏈， R] 15 代表氩、crc8_燒基、Cl-C6-烧基亞磺醯基、c「c6 烷磺醯基、cvcv烧氧基_Cl_c4_燒基、C3-(V環爲 基；CVCVi燒基、CkCV鹵烷硫基、Ci_c4_函烷邊 -亞續酿基、CrC：4__烷基磺醯基Krc4-烷氧；| CVCr烧基、CVCV齒環烧基，其分別且有丨至♦ 個氟、氯與/或演原子；甲醢基、甲酿基_ckv烧基: (CVC3-烧基)幾基_Cl_C3·烧基、（Ci_C3_烧 -CVCV烧基；由-(Cl_c3_炫基機基·Ci_C3_燒基)、^ (CrCV烷氧基)羰基_Ci_C3-烷基，其分別具有！至 13個氟、氯與/或溴原子； -95- 20 2〇〇528434 (C1-C8-烧基)羰基、（CkCV烧氧基)幾基、（CVCV烧 氧基-CrC4-烧基)幾基、(CrC8-環烧基)羰基；（crc6-鹵燒基）幾基、（CVC6-鹵燒氧基）幾基、（鹵 燒乳基"*Cl~C4-烧基)纟厌基、（C3_C8__環炫基)幾基， 其分別具有1至9個氟、氯與/或溴原子；或 2 _c(=〇)c(=o)R4、-CONR5R6 或一CH2NR7R8， ^ 代表氳、氟、氯、曱基或三氟甲基， 4代表ώ素、Ci-Cg-烧基或Ci-Cg- _烧基， R 代表氫、Ci-Cs-炫基、Ci-C8-烧氧基、Cl_c4_烧氧基 •C1-C4-烧基、C3-C8-環烧基；CVC6-_ 烧基、Ci-C6· A燒氧基、—-CVC4-烧氧基-cvcv烧基、C3-C8-鹵 5 %烷基，其分別具有1至9個氟、氯與/或溴原子， 與R分別獨立代表氫、CKC8-燒基、炫氧基 -kar烧基、c3-c8-環烷基；cvc8-i烷基、鹵 C1-CV烧氧基-C^-C4-烧基、（：3_(：8-_環燒基，其分 5別具有1至9個氟、氯與/或溴原子， R與R6亦可與其所附接之氮原子共同形成具有5炱8 個環組員之飽和雜環， 其可視需要經選自鹵素與CrC^烷基之相同戒相異 取代基單取代或多取代，其中談雜環可另包含1戒 2個選自氧、硫與NR9中之不相鄰雜原子， R與R分別獨立代表氩、CrCg-烧基、c3_c8-環嫁基； CrC8_鹵烷基、c^c：8-鹵環烷基，其分別具有1炱9 個氟、氣與/或溴原子， -96- 200528434 R7與R8亦可與其所附接之氮原子共同形成具有5至8 個環原子之飽和雜環， 其可視需要經選自鹵素與CrC4-烷基之相同或相異 取代基單取代或多取代，其中該雜環可另包含1或 5 2個選自氧、硫與NR9中之不相鄰雜原子， R9代表氳或CrC6-烷基， A 代表式(A1)基團1-4 The bond marked with * is attached to fluorenylamine, and the bond marked with # is attached to the alkyl side chain. R] 15 represents argon, crc8_alkyl, Cl-C6-alkylsulfinylsulfenyl , C "c6 alkylsulfonyl, cvcv alkoxy_Cl_c4_ alkynyl, C3- (V ring as the base; CVCVi alkynyl, CkCV haloalkylthio, Ci_c4_alkanyl-subcontinent, CrC: 4__Alkylsulfonyl Krc4-alkoxy; | CVCr alkyl, CVCV tooth ring alkyl, which have 丨 to ♦ fluorine, chlorine and / or atom atoms; methyl ethyl, methyl ethyl Group: (CVC3-carbyl) several groups_Cl_C3 · alkyl, (Ci_C3_alkyl-CVCV alkyl; from-(Cl_c3_xylyl · Ci_C3_alkyl), ^ (CrCV alkoxy) carbonyl_ Ci_C3-alkyl, which has! To 13 fluorine, chlorine and / or bromine atoms, respectively; -95-20 20200528434 (C1-C8-alkyl) carbonyl, (CkCValkyl), (CVCV Carbooxy-CrC4-carbo)), (CrC8-cyclocarbo) carbonyl; (crc6-halo)), (CVC6-halooxy), and (halogenated milk " * Cl ~ C4-alkenyl) pyridinyl, (C3_C8__cyclohexyl), and each has 1 to 9 fluorine, chlorine and / or bromine atoms; or 2_c (= 〇) c (= o) R4 , -CONR5R6 or mono-CH2NR7R8, ^ represents fluorene, fluorine, chlorine, fluorenyl, or trifluoromethyl, 4 represents free radical, Ci-Cg-alkyl or Ci-Cg-alkyl, R represents hydrogen, Ci-Cs -Hyunyl, Ci-C8-alkoxy, Cl_c4_alkoxy, C1-C4-alkyl, C3-C8-cycloalkyl; CVC6-_ alkyl, Ci-C6 · Aalkyl,- CVC4-carboxy-cvcv alkyl, C3-C8-halo 5% alkyl, which have 1 to 9 fluorine, chlorine and / or bromine atoms, respectively, and R independently represent hydrogen, CKC8-carbyl, oxo -Kar alkyl, c3-c8-cycloalkyl; cvc8-i alkyl, halo C1-CV alkyloxy-C ^ -C4-alkyl, (: 3 _ (: 8-_cycloalkyl), their 5 Don't have 1 to 9 fluorine, chlorine and / or bromine atoms. R and R6 can also form a saturated heterocyclic ring with 5 to 8 ring members together with the nitrogen atom attached to it. The same or different substituents of CrC ^ alkyl are mono- or poly-substituted. The heterocyclic ring may further include 1 or 2 non-adjacent heteroatoms selected from oxygen, sulfur and NR9. R and R each independently represent argon. , CrCg-alkyl, c3_c8-cycloalkyl; CrC8_haloalkyl, c ^ c: 8-halocycloalkyl, which each have 1.9 fluorine, And / or bromine atom, -96- 200528434 R7 and R8 can also form a saturated heterocyclic ring with 5 to 8 ring atoms together with the nitrogen atom to which it is attached, which may be the same as selected from halogen and CrC4-alkyl Or different substituents are mono- or poly-substituted, wherein the heterocyclic ring may further include 1 or 52 non-adjacent heteroatoms selected from oxygen, sulfur and NR9, R9 represents fluorene or CrC6-alkyl, and A represents the formula (A1) group R1G代表氫、羥基、曱醯基、氰基、氟、氯、溴、 硝基、CVC4-烷基、CVCV烷氧基、CVCr烷硫 基、C3-C6-環烷基、CrCr鹵烷基、CVCV鹵烷 氧基或C^Cr鹵烷硫基（其分別具有1至5個鹵 15 原子）、胺基羰基或胺基羰基-CVCV烷基， R11代表氫、氯、溴、碘、氰基、CrC4-烷基、CVCr ^ 烧氧基、C1-C4-烧硫基、C1-C4-鹵烧基或C1-C4-鹵烷硫基(其分別具有1至5個鹵原子），及 R12代表氫、CVCV烷基、羥基-CrC4-烷基、C2-C6-20 烯基、C3-C6-環烷基、CrC4-烷硫基-CrC4-烷 基、CrC4-烷氧基-CrC4-烷基、CVCViS烷基、 Ci_C4-_烧硫基-C1-C4-炫基、C1-C4-鹵院氧基 -CVCV烷基(其分別具有1至5個鹵原子），或 代表苯基， -97- 200528434 或 A 代表(A2)基團 R' R15 R(A2)，其中 R 3與R14分別獨立代表氫、鹵素、Cl_c4烷基 或具有1至5個鹵原子之Crc4_鹵烷基， R15代表鹵素、氰基或Cl_C4烷基，或Crc4鹵烷· 基或Cr(：4__烧氧基(其分別具有1至5個鹵原 子）， 或 A 代表式(A3)基團R1G represents hydrogen, hydroxyl, fluorenyl, cyano, fluorine, chlorine, bromine, nitro, CVC4-alkyl, CVCV alkoxy, CVCr alkylthio, C3-C6-cycloalkyl, CrCr haloalkyl, CVCV haloalkoxy or C ^ Cr haloalkylthio (which has 1 to 5 halo 15 atoms, respectively), aminocarbonyl or aminocarbonyl-CVCV alkyl, R11 represents hydrogen, chlorine, bromine, iodine, cyano , CrC4-alkyl, CVCroxy, C1-C4-halothio, C1-C4-halohalo, or C1-C4-haloalkylthio (which each have 1 to 5 halogen atoms), and R12 Represents hydrogen, CVCV alkyl, hydroxy-CrC4-alkyl, C2-C6-20 alkenyl, C3-C6-cycloalkyl, CrC4-alkylthio-CrC4-alkyl, CrC4-alkoxy-CrC4-alkane , CVCViS alkyl, Ci_C4-_sulfanyl-C1-C4-xyl, C1-C4-haloalkyloxy-CVCV alkyl (which each have 1 to 5 halogen atoms), or represents phenyl,- 97- 200528434 or A represents (A2) group R 'R15 R (A2), wherein R 3 and R14 each independently represent hydrogen, halogen, Cl_c4 alkyl or Crc4_haloalkyl having 1 to 5 halogen atoms, R15 Represents halogen, cyano or Cl_C4 alkyl, or Crc4 haloalkane group or Cr (: 4__alkoxy group (which has 1 to 5 halogen atoms), or A represents a group of formula (A3) (A3)，其中 15 R16與R17分別獨立代表氫、鹵素、Ci_C4_烧基或具 有1至5個鹵原子之Ci-Czr鹵烷基，及 R18代表氫、CrC4_烧基或具有1至5個卣原子之 C1-C4-鹵烧基， 或 A 代表式(A4)基團(A3), wherein 15 R16 and R17 each independently represent hydrogen, halogen, Ci_C4_alkyl or Ci-Czr haloalkyl having 1 to 5 halogen atoms, and R18 represents hydrogen, CrC4_alkyl or have 1 to 5 C1-C4-halohalo group of each fluorene atom, or A represents a group of formula (A4) (A4)，其中 -98- 20 200528434 R19代表鹵素、羥基、氰基、Cl_C4_烷基、Ci_C4_ 烧氧基、CrC4-烧硫基、crc4-鹵烷基、crc4-鹵烷硫基或CrCr鹵烷氧基(其分別具有i至5 個齒原子）， R20代表氳、i素、氰基、CrC4-烧基、Cl_C4_燒 氧基、CrC4-烧硫基、CVC4-鹵烧基、crc4卣 烷氧基（其分別具有1至5個鹵原子）、 烷亞磺醯基或CrCU-烷磺醯基， 或 10 15 A 代表式(A5)基團(A4), where -98-20 200528434 R19 represents halogen, hydroxy, cyano, Cl_C4_alkyl, Ci_C4_alkyloxy, CrC4-alkylthio, crc4-haloalkyl, crc4-haloalkylthio, or CrCr halide Alkoxy (which has i to 5 dent atoms, respectively), R20 represents fluorene, i-prime, cyano, CrC4-carbyl, Cl_C4_oloxy, CrC4-sulfanyl, CVC4-haloalkyl, crc4 卣Alkoxy (which has 1 to 5 halogen atoms, respectively), alkanesulfinyl or CrCU-alkanesulfonyl, or 10 15 A represents a group of formula (A5) (A5) 或 A 代表式(A6)基團(A5) or A represents a group of formula (A6) (A6)，其中 R21代表CrCr烷基或具有1至5個鹵原子之 鹵烷基， 14 或 A 代表式(A7)基團 (X (A7)，其中 -99- 20 W0528434 R22 JL· 代表Crcv烷基或具有1至5個鹵原子之 Ci-CV鹵烷基， 5 10 A 代表式(A8)基團 (A8) ’ 其中 R與R 4分別獨立代表氫、鹵素、胺基、烷 h基或具有1至5個鹵原子之Cl-C4_由烷基，及 代表氫、CrC4_烧基或具有1至5個鹵原子之 ci_C4-齒烧基， 或 A 代表式(A9)基團 15(A6), wherein R21 represents a CrCr alkyl group or a haloalkyl group having 1 to 5 halogen atoms, and 14 or A represents a group of formula (A7) (X (A7), wherein -99-20 W0528434 R22 JL · represents Crcv Alkyl or Ci-CV haloalkyl having 1 to 5 halogen atoms, 5 10 A represents a group of formula (A8) (A8) ′ wherein R and R 4 each independently represent hydrogen, halogen, amine, or alkyl group Or Cl-C4_alkyl having 1 to 5 halogen atoms, and represents hydrogen, CrC4_alkyl or ci_C4-dental alkyl having 1 to 5 halogen atoms, or A represents a group of formula (A9) 15 (A9)，其中 R26與R27分別獨立代表氫、齒素、胺基、确基、 CVCV烷基或具有1至5個鹵原子 处貧· η 丁 < irc4__ 20 R28代表_素、CVCV烧基或具有之CrC4-由烷基， 至5個卣原子 或 A 代表式(A10)基團 -100- 200528434(A9), in which R26 and R27 each independently represent hydrogen, halide, amine, acyl, CVCV alkyl or have 1 to 5 halogen atoms. Η Ding < irc4__ 20 R28 represents Or has CrC4- from alkyl, to 5 fluorene atoms or A represents a group of formula (A10) -100- 200528434 (A10)，其中 R代表氫、齒素、胺基、CrC4-烷基胺基、二 -(CVC4·烧基)胺基、氰基、crc4_烧基或具有i 至5個鹵原子之C!-C4-卣烧基及 R3G代表_素、羥基、crc4_燒基、GVQ-烧氧基、 c3-c6-環烧基、c「c4鹵烷基或CrCr鹵烷氧基 (其分別具有1至5個鹵原子）， 或 A 代表式(All)基團(A10), wherein R represents hydrogen, a halogen, an amine group, a CrC4-alkylamino group, a di- (CVC4-alkyl) amino group, a cyano group, a crc4-alkyl group, or a C having from 5 to 5 halogen atoms ! -C4-fluorenyl and R3G represent a sulfanyl group, a hydroxyl group, a crc4-ocalyl group, a GVQ-carbyl group, a c3-c6-cycloalkenyl group, a c4 haloalkyl group, or a CrCr haloalkoxy group, each 1 to 5 halogen atoms), or A represents a group of formula (All) (All)，其中 R 代表氩、鹵素、胺基、CrC4-烷基胺基、二 15 _(Cl_C4-烧基)胺基、氰基、CVCV烧基或具有1 至5個鹵原子之鹵烧基及 R 代表鹵素、Ci-Cf烷基或具有1至5個鹵原子 之Ci-C4-_烧基， 或 20 A 代表式(A12)基團(All), where R represents argon, halogen, amine, CrC4-alkylamino, di 15_ (Cl_C4-alkyl) amino, cyano, CVCV alkyl or halogen-containing And R represents a halogen, Ci-Cf alkyl or Ci-C4-alkyl having 1 to 5 halogen atoms, or 20 A represents a group of formula (A12) (A12) ’其中 R33代表氫或CrC4-烷基及 -101- 200528434 R34代表鹵素或CrC4-烷基， 或 A 代表式(A13)基團 5(A12) ′ wherein R33 represents hydrogen or CrC4-alkyl and -101- 200528434 R34 represents halogen or CrC4-alkyl, or A represents a group of formula (A13) 5 (A13)，其中 R35代表CkCt烷基或具有1至5個鹵原子之 Ci_C4_ _ 烧基， 或 10 15 Α 代表式(A14)基團(A13), wherein R35 represents a CkCt alkyl group or a Ci_C4__ alkyl group having 1 to 5 halogen atoms, or 10 15 A represents a group of formula (A14) (A14)，其中 R36代表氳、鹵素'CrCr烷基或具有1至5個鹵 原子之CKC4鹵烷基， 或 A 代表式(A15)基團(A14), wherein R36 represents fluorene, halogen 'CrCr alkyl, or CKC4 haloalkyl having 1 to 5 halogen atoms, or A represents a group of formula (A15) (A15)，其中 R37代表鹵素、羥基、CrC4-烷基、Ci-CV烷氧基、 C1-C4-烧硫基、Ci-C4**_烧基、C1-C4-鹵烧琉 基、CrC4鹵烷氧基(其分別具有1至5個鹵原 子）， -102- 20 200528434 或 A 代表式(A16) p40 R39(A15), wherein R37 represents halogen, hydroxy, CrC4-alkyl, Ci-CV alkoxy, C1-C4-sulfanyl, Ci-C4 **-alkynyl, C1-C4-halosulfanyl, CrC4 Haloalkoxy (which has 1 to 5 halogen atoms, respectively), -102-20 200528434 or A represents formula (A16) p40 R39 (A16)，其中(A16), where 10 15 R38代表氫、氰基、CrC4-烷基、具有1至5個鹵 原子之（VC4-鹵烷基、CrC4-烷氧基-CrC4-烷 基、羥基-CrC4-烷基、CVC4-烷磺醯基、二% (CrCV烧基)胺基磺醯基、CVC6-烧基羰基或分 別可視需要經取代之苯磺醯基或苯甲醯基， 39 ^ 代表虱、鹵素、CrCr烧基或具有1至5個齒 原子之C1-C4-鹵烧基’ r4G代表氳、鹵素、氰基、CrCV烧基或具有！至 5個鹵原子之鹵烧基， 代表氫、鹵素、crC4-烷基或具有工至5個鹵 原子之C1-C4-_娱*基， 或 _ A 代表式(A17)基團10 15 R38 represents hydrogen, cyano, CrC4-alkyl, (VC4-haloalkyl, CrC4-alkoxy-CrC4-alkyl, hydroxy-CrC4-alkyl, CVC4-alkane having 1 to 5 halogen atoms Sulfonyl, di% (CrCV alkyl) sulfonyl, CVC6-alkyl, or benzenesulfonyl or benzamidine, if necessary, respectively. 39 ^ represents lice, halogen, CrCr alkyl or C1-C4-haloalkyl group having 1 to 5 dent atoms, r4G represents fluorene, halogen, cyano, CrCV alkyl, or haloalkyl group having! To 5 halogen atoms, representing hydrogen, halogen, crC4-alkyl Or a C1-C4-_ammonium group having 5 to 5 halogen atoms, or _ A represents a group of formula (A17) (A17)，其中 R42代表CrC4-烷基。 2·根據申請專利範圍第1項之式⑴己基醯基苯胺 其中 -103- 20 200528434(A17), wherein R42 represents CrC4-alkyl. 2. According to the formula 1 of the scope of patent application, hexylfluorenylaniline where 5 10 15 20 其中標示*之鍵結係附接醯胺，而標示#之鍵結則附 接烷基侧鏈， Rl代表氫、cvcv烧基、Cl_c4_烧基亞磺醯基、CrCV 烧石黃醯基、cvcv烷氧基-Cl_c3-烷基、c3_c6_環烷· 基；CrC4-鹵烷基、q-CV鹵烷硫基、Crc4-鹵烷基 亞石黃醯基、(VC4·鹵烷基磺醯基、鹵烷氧基 -CrC3-烧基、C3-CV齒環烧基，其分別具有1至9 個氟、氯與/或溴原子；甲醯基、甲醯 基、（C「c3-烧基)幾基-CVC3-烧基、（CVCV烧氧基） 幾基_CrC3-烷基；鹵-(CVC3-烷基）羰基·CVCr烷 基、鹵烷氧基)獄基-CpCV烧基，其分別具 有1至I3個氟、氯與/或漠原子；（Cl_C6_烷基)幾基、 (Ci-C4_烧氧基)叛基、（Ci-CV烧氧基-Ci-CV烧基)羰 基、（C3-C6-環烧基）幾基；（CVC4-鹵烧基）幾基、 (Ci-CV鹵烧氧基)幾基、（鹵-CrCV烧氧基-Cl-C3.烷 基)幾基、（C3_C6_鹵環烧基)幾基，其分別具有1至 9個氟、氯與/或溴原子；或-C(=〇)C(=〇)R4、 -C〇NR5R6 或-CH2NR7R8， R2代表氫、氟、氯、甲基或三氟甲基，1 ^ 代表氟、氯、溴、碟、CkCV烧基、具有1至13個 -104- 200528434 氟、氯與/或溴原子之cKc6-鹵烷基， R4 代表氳、CrC6-烷基、CrC4-烷氧基、CrC3-烷氧基 -crc3-烷基、c3-c6-環烷基；crc4-鹵烷基、crc4-鹵烷氧基、鹵-crc3-烷氧基-crc3-烷基、c3-c6•鹵 5 環烷基，其分別具有1至9個氟、氯與/或溴原子， R5與R6分別獨立代表氫、CrC6-烷基、CrC3-烷氧基 -C1-C3-烧基、〇3_(^6-壞烧基，C1-C4-鹵烧基、_ -CVC3-烷氧基-CVC3-烷基、c3-c6-齒環烷基，其分% 別具有1至9個氟、氯與/或溴原子， 10 R5與R6亦可與其所附接之氮原子共同代表具有5或6 個環原子之飽和雜環，其可視需要經選自_素與 烷基中之相同或相異取代基單取代至四取 代，其中該雜環可另包含1或2個選自氧、硫與 NR9中之不相鄰雜原子， 15 R7與R8分別獨立代表氳、CVCV烷基、C3-C6-環烷基； CVCr鹵烷基、C3-C6-鹵環烷基，其分別具有1至9 g 個氟、氣與/或漠原子， R7與R8亦可與其所附接之氮原子共同代表具有5或6 個環原子之飽和雜環，其可視需要經選自鹵素與 20 CKC4-烷基中之相同或相異取代基單取代或多取 代，其中該雜環可另包含1或2個選自氧、硫與 NR9中之不相鄰雜原子， R9代表氩或CrCV烷基， A 代表式(A1)基團 -105- 2005284345 10 15 20 The bond marked with * is attached to fluorene, and the bond marked with # is attached to the alkyl side chain. R1 represents hydrogen, cvcv alkyl, Cl_c4_ alkylsulfinyl, CrCV pyrolite Flavoyl, cvcv alkoxy-Cl_c3-alkyl, c3_c6_ cycloalkane · yl; CrC4-haloalkyl, q-CV haloalkylthio, Crc4-haloalkylsulfenite, (VC4 · haloalkylsulfonyl Radical, haloalkoxy-CrC3-alkyl, C3-CV toothed alkyl, each having 1 to 9 fluorine, chlorine and / or bromine atoms; methylamidino, methylamido, (C "c3-alkyl Base) jikyi-CVC3-alkyl, (CVCVoxy) alkyl-CrC3-alkyl; halo- (CVC3-alkyl) carbonyl · CVCr alkyl, haloalkoxy) hexyl-CpCV alkyl, It has 1 to 13 fluorine, chlorine, and / or desert atoms, respectively; (Cl_C6_alkyl) amino, (Ci-C4_alkyloxy) alkyl, (Ci-CValkyloxy-Ci-CValkyl) ) Carbonyl, (C3-C6-cycloalkenyl) alkynyl; (CVC4-haloalkyl) chin, (Ci-CV halooxy) chin, (halo-CrCV alkoxy-Cl-C3.alkane) Base), and (C3_C6_halocycloalkyl), each having 1 to 9 fluorine, chlorine, and / or bromine atoms; or -C (= 〇) C (= 〇) R4, -CONR5R6-CH2NR7R8, R2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, 1 ^ represents fluorine, chlorine, bromine, saucer, CkCV alkyl, has 1 to 13 -104- 200528434 fluorine, chlorine and / or bromine Atomic cKc6-haloalkyl, R4 represents fluorene, CrC6-alkyl, CrC4-alkoxy, CrC3-alkoxy-crc3-alkyl, c3-c6-cycloalkyl; crc4-haloalkyl, crc4- Haloalkoxy, halo-crc3-alkoxy-crc3-alkyl, c3-c6 • halo-5 cycloalkyl, which each have 1 to 9 fluorine, chlorine and / or bromine atoms, and R5 and R6 are independently represented Hydrogen, CrC6-alkyl, CrC3-alkoxy-C1-C3-alkyl, 〇3-(^ 6-bad alkyl, C1-C4-haloalkyl, _-CVC3-alkoxy-CVC3-alkyl , C3-c6-dental cycloalkyl, each of which has 1 to 9 fluorine, chlorine and / or bromine atoms, 10 R5 and R6 can also represent 5 or 6 ring atoms together with the nitrogen atom attached to them A saturated heterocyclic ring, which may be mono- to tetra-substituted with the same or different substituents selected from the group consisting of hydrogen and alkyl, as required, wherein the heterocyclic ring may further include 1 or 2 selected from the group consisting of oxygen, sulfur, and NR9. Non-adjacent heteroatoms, 15 R7 and R8 independently represent fluorene, CVCV alkyl, C3-C6-cycloalkane ; CVCr haloalkyl, C3-C6-halocycloalkyl, which have 1 to 9 g of fluorine, gas and / or desert atoms, respectively, R7 and R8 can also represent 5 or 6 with the nitrogen atom attached to them A saturated heterocyclic ring of one ring atom, which may be mono- or poly-substituted with the same or different substituents selected from halogen and 20 CKC4-alkyl, if necessary, wherein the heterocyclic ring may further include 1 or 2 selected from oxygen, Sulfur and non-adjacent heteroatoms in NR9, R9 represents argon or CrCV alkyl, and A represents a group of formula (A1) -105- 200528434 5 10 15 R1G代表氫、羥基、甲醯基、氰基、氟、氯、溴、 碘、甲基、乙基、異丙基、曱氧基、乙氧基、 甲硫基、乙硫基、壤丙基、C1-C2-齒烧基、C1-C2-鹵烷氧基(其分別具有1至5個氟、氯與/或溴 原子）、三氟甲硫基、二氟甲硫基、胺基羰基、 胺基叛基甲基或胺基魏基乙基， R11代表氫、氯、溴、碘、曱基、乙基、甲氧基、 乙氧基、甲硫基、乙硫基、具有1至5個氟、 氯與/或溴原子之Q-Cr鹵烷基， R12代表氳、曱基、乙基、正丙基、異丙基、具有 1至5個氟、氯與/或溴原子之CVQ-鹵烷基、 羥基甲基、羥基乙基、環丙基、環戊基、環己 基或苯基， 或 A 代表(A2)基團5 10 15 R1G represents hydrogen, hydroxy, methylamido, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, Oxopropyl, C1-C2-dentyl, C1-C2-haloalkoxy (which each have 1 to 5 fluorine, chlorine and / or bromine atoms), trifluoromethylthio, difluoromethylthio, Aminocarbonyl, aminomethyl, or aminoweiylethyl, R11 represents hydrogen, chlorine, bromine, iodine, fluorenyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, and has 1 Q-Cr haloalkyl with 5 to 5 fluorine, chlorine and / or bromine atoms, R12 represents fluorenyl, fluorenyl, ethyl, n-propyl, isopropyl, 1 to 5 fluorine, chlorine and / or bromine CVQ-haloalkyl, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl, or A represents (A2) group (A2)，其中 R13與R14分別獨立代表氳、氟、氣、溴、甲基、乙 基或具有1至5個氟、氯與/或溴原子之CrC2-鹵烧基， -106- 20 200528434 R15代表氟、氯、溴、碘、氰基、甲基、乙基、q-CV 鹵烷基或CrC2-鹵烷氧基（其分別具有1至5 個氟、氯與/或溴原子）， 或 5 10 15 A 代表式(A3)基團 (A3)，其中 R16與R17分別獨立代表氫、氟、氯、溴、甲基、乙 基或具有1至5個氟、氯與/或溴原子之CKC2-鹵烷基， R18代表氳、曱基、乙基、或具有1至5個氟、氯 與/或溴原子之Ci-Cy鹵烷基， 或 A 代表式(A4)基團 R20(A2), wherein R13 and R14 each independently represent fluorene, fluorine, gas, bromine, methyl, ethyl, or CrC2-halohalo having 1 to 5 fluorine, chlorine, and / or bromine atoms, -106-20 200528434 R15 represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, q-CV haloalkyl or CrC2-haloalkoxy (which each have 1 to 5 fluorine, chlorine and / or bromine atoms), Or 5 10 15 A represents the group (A3) of formula (A3), wherein R16 and R17 each independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or have 1 to 5 fluorine, chlorine, and / or bromine atoms CKC2-haloalkyl, R18 represents fluorenyl, fluorenyl, ethyl, or Ci-Cy haloalkyl having 1 to 5 fluorine, chlorine, and / or bromine atoms, or A represents a group of formula (A4) R20 (A4)，其中 R19代表氟、氣、溴、碘、羥基、氰基、CVCV烷 基、曱氧基、乙氧基、甲硫基、乙硫基、二 氟甲硫基、三氟甲硫基、Q-Cr鹵烷基或CrC2-鹵烷氧基(其分別具有1至5個氟、氯與/或溴 原子）， R2()代表氫、氟、氯、溴、碘、氰基、CkCV烷基、 -107 - 20 200528434 5 甲氧基、乙氧基、甲硫基、乙硫基、Ci_c2_鹵 烧基或鹵烷氧基(其分別具有1至5個 氟、氯與/或溴原子）、CVCV烷基亞磺醯基或 crc2-烷磺醯基， 或 A 代表式(A5)基團(A4), wherein R19 represents fluorine, gas, bromine, iodine, hydroxyl, cyano, CVCV alkyl, fluorenyloxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio Group, Q-Cr haloalkyl or CrC2-haloalkoxy (which each have 1 to 5 fluorine, chlorine and / or bromine atoms), R2 () represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, CkCV alkyl, -107-20 200528434 5 methoxy, ethoxy, methylthio, ethylthio, Ci_c2_halohalo, or haloalkoxy (which each have 1 to 5 fluorine, chlorine and / or Bromine atom), CVCV alkylsulfinyl sulfonyl or crc2-alkylsulfonyl sulfonyl, or A represents a group of formula (A5) (A5)，其中 10 或 A 代表式(A6)基團(A5), in which 10 or A represents a group of formula (A6) (A6)，其中 15 R21代表甲基、乙基或具有1至5個氟、氯與/或溴 原子之Ci-C】-鹵烧基， 或 A 代表式(A7)基團(A6), wherein 15 R21 represents a methyl group, an ethyl group or a Ci-C] -halohalo group having 1 to 5 fluorine, chlorine and / or bromine atoms, or A represents a group of the formula (A7) (A7)，其中 R22代表甲基、乙基、三氟甲基、二氟甲基、二氟 氯甲基或三氯甲基， 或 -108 - 20 200528434 A 代表式(A8)基團 10 15(A7), wherein R22 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or -108-20 200528434 A represents a group of formula (A8) 10 15 (A8)，其中 R23與R24分別獨立代表氫、氟、氯、溴、胺基、甲 基、乙基、或具有1至5個氟、氯與/或溴原子 之基’及 R25代表氳、曱基、乙基、或具有1至5個氟、氯 與/或溴原子之CVCV鹵烷基， 或 A 代表式(A9)基團(A8), wherein R23 and R24 independently represent hydrogen, fluorine, chlorine, bromine, amine, methyl, ethyl, or a group having 1 to 5 fluorine, chlorine, and / or bromine atoms, and R25 represents 氲, Fluorenyl, ethyl, or CVCV haloalkyl having 1 to 5 fluorine, chlorine, and / or bromine atoms, or A represents a group of formula (A9) (A9)其中 R26與R27分別獨立代表氫、氟、氯、溴、胺基、靖 基、甲基、乙基、或具有1至5個氣、氯與/ 或溴原子之cvc2-鹵烷基及 R28代表氟、氯、溴、曱基、乙基、或具有1至5 個氟、氯與/或溴原子之CrC2-鹵烷基， 或 A 代表式(A10)基團 (A10)其中(A9) wherein R26 and R27 each independently represent hydrogen, fluorine, chlorine, bromine, amine, aryl, methyl, ethyl, or cvc2-haloalkyl having 1 to 5 gas, chlorine, and / or bromine atoms, and R28 represents fluorine, chlorine, bromine, fluorenyl, ethyl, or CrC2-haloalkyl having 1 to 5 fluorine, chlorine, and / or bromine atoms, or A represents a group (A10) of formula (A10) -109 - 20 200528434 5 10 15 R29代表氳、氟、氯、溴、胺基、CrC4-烷基胺基、 二-(CrC4-烷基)胺基、氰基、甲基、乙基、或 具有1至5個氟、氯與/或溴原子之CVCV鹵烷 基及 r3〇代表氟、氯、溴、羥基、甲基、乙基、甲氧基、 乙乳基、環丙基、C1-C2鹵烧基或C1-C2-函烧 氧基(其分別具有1至5個氟、氯與/或溴原子）， 或 A 代表式(All)基團 。r- (All)其中 R31代表氳、氟、氯、溴、胺基、CkCt烷基胺基、 二烷基)胺基、氰基、甲基、乙基、或 具有1至5個氟、氯與/或溴原子之CrC2-鹵烷 基及 R32代表氟、氯、溴、曱基、乙基或具有1至5個 氟、氯與/或溴原子之CrC2-鹵烷基， 或 A 代表式(A12)基團 (A12)，其中 R33代表氫、甲基或乙基及 -110--109-20 200528434 5 10 15 R29 represents fluorene, fluorine, chlorine, bromine, amine, CrC4-alkylamino, di- (CrC4-alkyl) amino, cyano, methyl, ethyl, or has CVCV haloalkyl and r3 of 1 to 5 fluorine, chlorine and / or bromine atoms represent fluorine, chlorine, bromine, hydroxy, methyl, ethyl, methoxy, ethyllactyl, cyclopropyl, C1-C2 Halohalo or C1-C2-haloalkoxy (which has 1 to 5 fluorine, chlorine and / or bromine atoms, respectively), or A represents a group of formula (All). r- (All) where R31 represents fluorene, fluorine, chlorine, bromine, amine, CkCt alkylamino, dialkyl) amino, cyano, methyl, ethyl, or has 1 to 5 fluorine, chlorine CrC2-haloalkyl and / or bromine atom and R32 represent fluorine, chlorine, bromine, fluorenyl, ethyl or CrC2-haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atom, or A represents (A12) group (A12), wherein R33 represents hydrogen, methyl or ethyl and -110- 20 200528434 R34代表氟、氯、溴、曱基或乙基， 或 A 代表式(A13)基團20 200528434 R34 represents fluorine, chlorine, bromine, fluorenyl or ethyl, or A represents a group of formula (A13) (A13)，其中 R35代表甲基、乙基或具有1至5個氟、氯與/或溴 原子之CVCV齒烷基， 或 10 15 A 代表式(A14)基團(A13), wherein R35 represents a methyl group, an ethyl group or a CVCV alkyl group having 1 to 5 fluorine, chlorine and / or bromine atoms, or 10 15 A represents a group of the formula (A14) (A14)，其中 R36代表氫、氟、氣、溴、甲基、乙基或具有1至 5個氟、氯與/或溴原子之CrC2-鹵烷基， 或 A 代表式(A15)基團(A14), wherein R36 represents hydrogen, fluorine, gas, bromine, methyl, ethyl, or CrC2-haloalkyl having 1 to 5 fluorine, chlorine, and / or bromine atoms, or A represents a group of formula (A15) (A15)，其中 R37代表氟、氯、溴、碘、羥基、CrC4-烷基、曱 氧基、乙氧基、甲硫基、乙硫基、二氟甲硫基、 三氟甲硫基、CrC2-鹵烷基或Ci-Cz鹵烷氧基 (其分別具有1至5個氟、氯與/或溴原子）， -111- 20 200528434 或 A 代表式(A16)基團 r41 (A16)，其中 5 R代表氫、甲基、乙基、具有丨至5個氣、氯與 /或溴原子之烷基、Ci_C2_烷氧基 -cvcv炫基、經基甲基、羥基乙基、甲磺醯基 或^一甲基胺基石黃酿基， 10 R39代表氫、氟、氯、溴、甲基、乙基或具有i至 4 5個氟、氯與/或溴原子之Cl_c2_鹵烷基， R4()代表氫、氟、氯、溴、氰基、甲基、乙基、異 15 丙基或具有1至5個氟、氯與/或溴原子之 cvcvi烷基， R4i代表氫、氟、氯、溴、甲基、乙基、或具有工 至5個氟、氯與/或溴原子之Ci_c2-鹵烷基， 或 A 代表式(A17) 20(A15), wherein R37 represents fluorine, chlorine, bromine, iodine, hydroxyl, CrC4-alkyl, fluorenyloxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, CrC2-haloalkyl or Ci-Cz haloalkoxy (which has 1 to 5 fluorine, chlorine and / or bromine atoms, respectively), -111-20 200528434 or A represents a group of formula (A16) r41 (A16), 5 R represents hydrogen, methyl, ethyl, alkyl having 5 to 5 gas, chlorine and / or bromine atom, Ci_C2_alkoxy-cvcv alkyl, methymethyl, hydroxyethyl, methanesulfonate Fluorenyl or ^ -methylamino sulphamyl, 10 R39 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or Cl_c2_haloalkyl having i to 45 fluorine, chlorine and / or bromine atoms R4 () represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, iso-15propyl or cvcvi alkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, R4i represents hydrogen, fluorine , Chlorine, bromine, methyl, ethyl, or Ci_c2-haloalkyl having 5 to 5 fluorine, chlorine, and / or bromine atoms, or A represents formula (A17) 20 (A17)其中 R42代表甲基、乙基、正丙基或異丙基。 •根據申請專利範圍第1或2項之式(I)己基醯基苯胺，其 中L代表L-1。 -112- 200528434 4. 根據申請專利範圍第1或2項之式(I)己基醯基苯胺，其 中L代表L-2。 5. 根據申請專利範圍第1或2項之式(I)己基醯基苯胺，其 中R1代表氫、甲醯基或-C(二0)C(=0)R4,其中R4如申 5 請專利範圍第1或2項之定義。 6. 根據申請專利範圍第1或2項之式(I)己基醯基苯胺，其 中A代表A1。 7. 根據申請專利範圍第1或2項之式(I)己基醯基苯胺，其 中R3代表鹵素。 1〇 8.根據申請專利範圍第1或2項之式(I)己基醯基苯胺，其 中R3代表CVCV烷基。 9. 根據申請專利範圍第1或2項之式(I)己基醯基苯胺，其 中R3代表CVCV鹵烷基。 10. —種製備根據申請專利範圍第1項之式（I)化合物之方 15 法，其特徵在於 a) 由式(II)羧酸衍生物 人1 ® 其中 20 A 如申請專利範圍第1項之定義，及 X1代表鹵素或羥基， 與式(III)苯胺衍生物反應(A17) wherein R42 represents methyl, ethyl, n-propyl or isopropyl. • Hexylfluorenylaniline of formula (I) according to item 1 or 2 of the scope of patent application, wherein L represents L-1. -112- 200528434 4. Hexylfluorenylaniline of formula (I) according to item 1 or 2 of the scope of patent application, wherein L represents L-2. 5. According to formula (I) hexylfluorenylaniline of item 1 or 2, wherein R1 represents hydrogen, methylamino or -C (di0) C (= 0) R4, where R4 is patented as claimed in claim 5 Definition of scope item 1 or 2. 6. Hexylfluorenylaniline according to formula (I) according to item 1 or 2 of the scope of patent application, wherein A represents A1. 7. Hexylfluorenylaniline of formula (I) according to item 1 or 2 of the scope of patent application, wherein R3 represents halogen. 10 8. Hexylfluorenylaniline of formula (I) according to item 1 or 2 of the scope of the patent application, wherein R3 represents a CVCV alkyl group. 9. Hexylfluorenylaniline of formula (I) according to item 1 or 2 of the scope of patent application, wherein R3 represents a CVCV haloalkyl group. 10. A method 15 for preparing a compound of formula (I) according to item 1 of the scope of the patent application, characterized in that a) a carboxylic acid derivative of formula (II) human 1 ® 20 A is as in item 1 of the scope of patent And X1 represents a halogen or a hydroxyl group, and reacts with an aniline derivative of the formula (III) -113- 200528434 其中L、R1與R3如申請專利範圍第1項之定義， 若適當時，可於觸媒之存在下，及若適當時，於縮 合劑之存在下，若適當時，於酸結合劑之存在下， 及若適當時，於稀釋劑之存在下進行， 5 或 b) 由式(I-a)己基酸基苯胺-113- 200528434 Among them, L, R1 and R3 are as defined in item 1 of the scope of patent application, if appropriate, in the presence of a catalyst, and if appropriate, in the presence of a condensing agent, if appropriate, in an acid In the presence of a binding agent and, if appropriate, in the presence of a diluent, 5 or b) from hexanoic acid aniline of formula (Ia) 10 其中 L、A與R3如申請專利範圍第1項之定義， 與式(IV)鹵化物反應 R1-A 一 X2 (IV) 15 其中 X2 代表氣、溴或碘， R1 A代表Ci-Cg-烧基、烧基亞石黃酿基、Ci_C6-烷基磺醯基、CrCV烷氧基-CrC4-烷基、 C3-C8-環烷基；CirCVi烷基、CVC4-鹵烷硫 基、C1-C4-鹵烧基-亞石黃酿基、C1-C4-鹵烧基續 醯基、鹵-crc4·烷氧基-crc4-烷基、c3-c8-鹵環烷基，其分別具有1至9個氟、氯與/或 溴原子；甲醯基、甲醯基-CrCy烷基、（CrCr 烷基）羰基-crc3-烷基、（crc3-烷氧基）羰基 -114- 20 200528434 烧基；_-(cvcv燒基）幾基_Ci_C3_院 基、i-(c「C3_烧氧基)幾基燒基，其分 別具有1至13個氟、氯與/或溴原子；（Ci_C8_ 烷基)羰基、（crcv烷氧基)羰基、（Ci_c4_烷氧 5 基_Cl_C4-烧基）幾基、（C3<V環燒基）幾基； (Ck(V齒烧基)羰基、（Cl_C6碥烷氧基)羰基、 dCVQ-烧氧基-CVCV燒基德基、（C3_C8_ 鹵環烷基)羰基，其分別具有丨至9個氟、氣 與/或 >臭原子；或-C(=0)C(=〇)R4、c〇nr5r6 10 或-ch2nr7r8，其中 R4、R5、R6、R7 與 r8 如 申請專利範圍第1項之定義， 其係於鹼之存在下及於稀釋劑之存在下進行。 11. 一種用於控制不要之微生物之組合物，其特徵^於其中 除了補充劑與/或界面活性劑以外，尚包含至少一種根 15 據申請專利範圍第1項之式⑴己基醯基苯胺。 12. —種以根據申請專利範圍第i項之式(1)己基醯基苯胺 於控制不要之微生物上之用途。 13· —種控制不要之微生物之方法，其特徵在於施用根據申 請專利範圍第1項之式(I)己基醢基苯胺至微生物與/或 20 其棲息地上。 14. 一種製備用於控制不要之微生物之組合物之方法，其特 徵在於混合根據申請專利範圍第1項之式(1)己基酿基 苯胺與補充劑與/或界面活性劑。 15. —種式(ΙΙΙ-b)苯胺衍生物 -115- 200528434 (ΙΠ-b) 5 其中 a) R^b 代表氳及 R^b代表鹵素、C3-C8烷基、CrC8鹵烷基， 或 b) R1^ 代表（VCV烷基、CVCV烷基亞磺醯基、CrC6- 10 1510 where L, A and R3 are as defined in item 1 of the scope of patent application, and react with a halide of formula (IV) R1-A-X2 (IV) 15 where X2 represents gas, bromine or iodine, and R1 A represents Ci-Cg- Burnt group, burnt sulfite group, Ci_C6-alkylsulfonyl, CrCV alkoxy-CrC4-alkyl, C3-C8-cycloalkyl; CirCVi alkyl, CVC4-haloalkylthio, C1- C4-halohalo-sulfite, C1-C4-halohalo, fluorenyl, halo-crc4 · alkoxy-crc4-alkyl, c3-c8-halocycloalkyl, each having 1 to 9 fluorine, chlorine and / or bromine atoms; formamyl, formamyl-CrCy alkyl, (CrCr alkyl) carbonyl-crc3-alkyl, (crc3-alkoxy) carbonyl-114- 20 200528434 alkyl ; _- (cvcv alkyl) _Ci_C3_ courtyard, i- (c "C3_alkyl oxy) alkyl, each having 1 to 13 fluorine, chlorine and / or bromine atoms; (Ci_C8_ Alkyl) carbonyl, (crcvalkoxy) carbonyl, (Ci_c4-alkoxy5yl_Cl_C4-alkyl), quinyl, (C3 < V cycloalkyl) carbonyl; (Ck (Vdentyl) carbonyl, (Cl_C6 alkoxy) carbonyl, dCVQ-alkyloxy-CVCValkyl, and (C3_C8_halocycloalkyl) carbonyl, each having丨 to 9 fluorine, gas and / or odorous atoms; or -C (= 0) C (= 〇) R4, cOnr5r6 10 or -ch2nr7r8, among which R4, R5, R6, R7 and r8 are as patented The definition of item 1 of the scope is carried out in the presence of a base and in the presence of a diluent. 11. A composition for controlling unwanted microorganisms, characterized in that excluding supplements and / or surfactants In addition, it contains at least one type of hexylfluorenylaniline according to item 1 of the scope of the patent application. 12. A kind of hexylfluorenylaniline according to formula (1) of the scope of patent application on the control of unwanted microorganisms 13. A method for controlling unwanted microorganisms, which is characterized by applying hexylfluorenylaniline of formula (I) according to item 1 of the scope of the patent application to microorganisms and / or 20 their habitats. 14. A preparation for A method for controlling a composition of unwanted microorganisms, which is characterized by mixing hexyl aniline with a supplement and / or a surfactant according to formula (1) according to item 1 of the scope of the patent application. 15. —Formula (III-b) Aniline derivative-115- 200528434 (III-b) 5 where a ) R ^ b stands for 氲 and R ^ b stands for halogen, C3-C8 alkyl, CrC8 haloalkyl, or b) R1 ^ stands for (VCV alkyl, CVCV alkylsulfinylene, CrC6- 10 15 烷磺醯基、CrC4-烷氧基-CVCV烷基、c3-c8-環烷基；crc6-i烷基、Q-cvi烷硫基、 C1-C4-鹵烧*基·"亞石黃基、C1-C4- ώ娱!*基石黃酿 基、鹵-CrQ-烷氧基-CVC4-烷基、C3-C8-鹵環 烷基，其分別具有1至9個氟、氯與/或溴原 子；甲醯基、曱醯基-CrC3-烷基、（cvcv烷 基）羰基-Q-CV烷基、（CVC3-烷氧基）羰基 -C1-C3-烧基，鹵-(C1-C3-烧基）叛基-C1-C3-烧 基、鹵-(CrCV烷氧基)羰基-CVC3-烷基，其分 別具有1至13個氟、氯與/或溴原子；（CrC8-烷基)羰基、（CVCV烷氧基)羰基、（CVC4-烷氧 基-CrC4-烷基）羰基、（C3-C8-環烷基）羰基； (CrC6-齒烷基)羰基、（CrC6-鹵烷氧基)羰基、 (鹵-CrO烷氧基-CrQ-烷基)羰基、（C3-C8-鹵環烷基)羰基，其分別具有1至9個氟、氣 -116- 20 200528434 與/或溴原子；或-C(=0)C(=0)R4、CONR5R6 或-ch2nr7r8，及 R3-b 代表氳、鹵素、CVC8-烷基、crc8-鹵烷基， 及 5 R2、R4、R5、R6、R7與R8分別如上述定義。 16. —種式（II-a)3-二氯甲基-1H-吡唑-4-羧酸衍生物 10Alkylsulfonyl, CrC4-alkoxy-CVCV alkyl, c3-c8-cycloalkyl; crc6-i alkyl, Q-cvi alkylthio, C1-C4-halohalo * " Base, C1-C4- free entertainment! * Cornerstone yellow base, halo-CrQ-alkoxy-CVC4-alkyl, C3-C8-halocycloalkyl, which each have 1 to 9 fluorine, chlorine and / or Bromine atom; formamyl, fluorenyl-CrC3-alkyl, (cvcvalkyl) carbonyl-Q-CValkyl, (CVC3-alkoxy) carbonyl-C1-C3-alkyl, halo- (C1- (C3-alkyl) -Cetyl-C1-C3-alkyl, halo- (CrCValkoxy) carbonyl-CVC3-alkyl, each having 1 to 13 fluorine, chlorine and / or bromine atoms; (CrC8-alkyl Carbonyl), (CVCV alkoxy) carbonyl, (CVC4-alkoxy-CrC4-alkyl) carbonyl, (C3-C8-cycloalkyl) carbonyl; (CrC6-haloalkyl) carbonyl, (CrC6-halo (Alkoxy) carbonyl, (halo-CrOalkoxy-CrQ-alkyl) carbonyl, (C3-C8-halocycloalkyl) carbonyl, each having 1 to 9 fluorine, -116-20 20 200528434 and / Or bromine atom; or -C (= 0) C (= 0) R4, CONR5R6 or -ch2nr7r8, and R3-b represents fluorene, halogen, CVC8-alkyl, crc8-haloalkyl, and 5 R2, R4, R5 , R6, R7 and R8 are as above Definitions. 16. —Specification (II-a) 3-dichloromethyl-1H-pyrazole-4-carboxylic acid derivative 10 其中 R12如申請專利範圍第1項之定義， X1代表齒素或羥基。 15Among them, R12 is defined as the first item in the scope of patent application, and X1 represents a tooth element or a hydroxyl group. 15 17. —種製備根據申請專利範圍第16項之式(II-a)3-二氯曱 基-1H-吡唑-4-羧酸衍生物之方法，其特徵在於 由式(XI)3-甲酿基-1H-吡唑-4-羧酸17. A method for preparing a 3-dichlorofluorenyl-1H-pyrazole-4-carboxylic acid derivative according to formula (II-a) according to item 16 of the scope of the patent application, characterized by the formula (XI) 3- Methyl-1H-pyrazole-4-carboxylic acid 其中R12如申請專利範圍第1項之定義， 與氯化劑，於稀釋劑之存在下反應。 18· —種式(XII)3-二氯曱基_ 1H-吡唑-4_羧酸酯 -117- 20 200528434Among them, R12 is as defined in the scope of patent application, and reacts with chlorinating agent in the presence of diluent. 18 · —Specification (XII) 3-dichlorofluorenyl_ 1H-pyrazole-4-carboxylic acid ester -117- 20 200528434 (ΧΠ) 5 其中 R12如申請專利範圍第1項之定義， R44代表CVQ烷基。 19. 一種製備根據申請專利範圍第18項之式(XII)3-二氯曱 基-1H-吡唑-4-羧酸酯之方法，其特徵在於 ίο 由式（X)3-曱醯基-1H-吡唑-4-羧酸酯(XΠ) 5 wherein R12 is as defined in the first item of the patent application scope, and R44 represents a CVQ alkyl group. 19. A method for preparing 3-dichlorofluorenyl-1H-pyrazole-4-carboxylic acid ester according to formula (XII) according to item 18 of the scope of patent application, characterized by -1H-pyrazole-4-carboxylic acid ester 15 其中 R12如申請專利範圍第1項之定義， R44代表CVC4烷基， 與氯化劑，於稀釋劑之存在下反應。 -118- 200528434 七、指定代表圖： (一） 本案指定代表圖為：第（ ）圖。無 (二） 本代表圖之元件符號簡單說明： 無 八、本案若有化學式時，請揭示最能顯示發明特徵的化學式：15 Among them, R12 is as defined in item 1 of the scope of patent application, R44 represents CVC4 alkyl group, and reacts with chlorinating agent in the presence of diluent. -118- 200528434 VII. Designated Representative Map: (1) The designated representative map in this case is: (). None (II) Brief description of the component symbols in this representative figure: None 8. If there is a chemical formula in this case, please disclose the chemical formula that can best show the characteristics of the invention:
TW093132066A 2003-10-23 2004-10-22 Hexylcarboxanilides TW200528434A (en)

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