TW201240602A - Herbicidal bis-nitrogen-containing oxo heterocycles - Google Patents

Herbicidal bis-nitrogen-containing oxo heterocycles Download PDF

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TW201240602A
TW201240602A TW101106908A TW101106908A TW201240602A TW 201240602 A TW201240602 A TW 201240602A TW 101106908 A TW101106908 A TW 101106908A TW 101106908 A TW101106908 A TW 101106908A TW 201240602 A TW201240602 A TW 201240602A
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Andrew Edmund Taggi
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Du Pont
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/34One oxygen atom
    • C07D239/36One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D411/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, A is a radical selected from the group consisting of and B1, B2, B3, T, R1, R2 R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 and R13 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

Description

201240602 、發明說明: 【發明所屬之技術領域】 0X0 本發明係關於某些雙氮側氧雜環(bis_nitmgen 一^ heter〇cyde)、其鹽與組成物及其用於防治非所欲植物之 關於某些可祕製備這錢氮雜環及其 鹽之中間物與方法。 【先前技術】 非所欲植物的防治對於達成高作物產率 要。對於雜草生長達成選擇性防治(selective con_e 極為理想的,尤其是對於仏 代contr〇i)疋 玉米'馬鈴薯nr=r、黃豆、甜菜、 類有用作物巾Ml 、舰作物雜草在此 15 =降並因而導致消費者的成本提高。在非作 戶,為重要。現今有許多針對此目的= ΐ品’但對:更有效、成本較少、毒性較低、對環境車; 靜直利—八= 物仍持續有需求。 .H 第wo 2007/088876號揭示式 *之D比咬酮化合物 \201240602, invention description: [Technical field to which the invention pertains] 0X0 The present invention relates to certain bis-nitroxyl heterocyclic rings (bis_nitmgen), salts and compositions thereof, and their use for controlling undesired plants Some intermediates and methods for preparing the nitrogen heterocycle and its salts. [Prior Art] The control of unwanted plants is required to achieve high crop yields. Selective control for weed growth (selective con_e is extremely desirable, especially for deuterated contr〇i) 疋 corn 'potato nr=r, soybeans, beets, useful crop towel Ml, ship crop weeds here 15 = This reduces the cost of the consumer. It is important to be a non-user. There are many things for this purpose = ’ ’ 但 对 对 对 对 : : : : : : : : : : : : : : : 更 更 更 更 更 更 更 更 更 更 更 更 更 更 更 更.H No. 2007/088876 Revealing *D D biting ketone compound \

Ri r2 5 201240602 其中尤其是Rl為CrC6炫基;化與 基或硝基;以及A為如該公開案中所氫、氰 而作為除草劑者。 疋義之A·1至A” 本發明之雙氮含氧雜環並未揭露於該公開案中。 【發明内容】 本發明係針對式!化合物(包括所有立體異構 =)、其^氧化物及其鹽、含有其等之農該成物及其 作為除草劑之用途: 10Ri r2 5 201240602 wherein, in particular, R1 is a CrC6 leukox group; a amide group or a nitro group; and A is a herbicide as described in the disclosure of hydrogen and cyanide. A.1 to A" of the present invention The bis-nitrogen-containing heterocyclic ring of the present invention is not disclosed in the publication. SUMMARY OF THE INVENTION The present invention is directed to a compound of the formula (including all stereoisomers =), And its salt, the agricultural product containing the same, and the use thereof as a herbicide: 10

其中 A為選自由下列所組成之群組之自由基 15Wherein A is a radical selected from the group consisting of 15

201240602 B1與B3各獨立為選自由下列所組成之群組之自由 基201240602 B1 and B3 are each independently a free radical selected from the group consisting of

C-1 R20 以及 C-2 B為選自由下列所組成之群組之自由基 10C-1 R20 and C-2 B are radicals selected from the group consisting of: 10

C-5C-5

(〇)„ II C-6 以及 R20 I 八 C-7 或 15(〇)„ II C-6 and R20 I VIII C-7 or 15

Rl 為-wic(=EV4、-Wilc(=E2)r25、 WlC(=E3)LR26 ' -W1S(0)xNR-C(=0)R27 ^ ^^(0)^^0(-0)^27 、 w1s(0)xnr28s〇2lr27 或-W1CN;或 R1 為 N(R4G)R41 ;或 R1 為 _GA 或-W2GA ; 各GA為一 4-至7-員碳環,其包括選自c(=〇)、 C(:S)、C(=NR29)、C㈣视、或㈣n(r29)2 之%員,或一 6-至12_員餘和或部分飽和碳螺 20 環(Carb°SpiIOCydic)或雜螺環(heterospirocyclic) %_系,其選擇性地(optionally)包括選自 〇)、C(-S)、c(=NR29)、C(=N_OR3〇)或 <^NN(R )2之環貞,各環或環祕擇性地經至 自在碳環員上之r21與在氣環員上之 ,的取代基取代;或 部分飽和_合環系,其含有碳環員 在护a氮3衣員,該環選擇性地經至多2個選自 基:;員上之r21與在氮環員上之r22的取代 與E獨立為〇、s、服28、n〇r28、丽(π)〗、 n-cn 或 N_N〇2; 各1獨立為〇、卿31)或8; 條:是tE3為0,則L不為Ο; 匸R 、R26與R27獨立為氫;4Ci_C6烷基、 2 G烯基、C^-C:6炔基或C3_C6環烷基,各選 ^性地經一或多個取代基取代,該取代基係選 C由鹵素、CN、N02、羥基、Crc4烷氧基、Rl is -wic(=EV4, -Wilc(=E2)r25, WlC(=E3)LR26 ' -W1S(0)xNR-C(=0)R27 ^ ^^(0)^^0(-0)^ 27, w1s(0)xnr28s〇2lr27 or -W1CN; or R1 is N(R4G)R41; or R1 is _GA or -W2GA; each GA is a 4- to 7-membered carbocyclic ring including a selected from c ( =〇), C(:S), C(=NR29), C(iv), or (iv)% of n(r29)2, or a 6- to 12_ member and or partially saturated carbon snail 20 ring (Carb°SpiIOCydic Or a heterospirocyclic %_system, which optionally includes an element selected from the group consisting of 〇), C(-S), c(=NR29), C(=N_OR3〇), or <^NN(R) a ring of 2, each ring or ring is selectively substituted by a substituent on the ring member of r21 and on the ring member; or a partially saturated ring system containing a carbon ring member Protecting a nitrogen 3 coater, the ring is selectively subjected to up to 2 selected from the group: the substitution of r21 on the member and the substitution of r22 on the nitrogen ring member with E as 〇, s, 服28, n〇r28,丽(π)〗, n-cn or N_N〇2; each 1 is independently 〇, 卿31) or 8; 条: is tE3 is 0, then L is not Ο; 匸R, R26 and R27 are independently hydrogen; 4Ci_C6 Alkyl, 2 G alkenyl, C^-C: 6 alkynyl or C3_C6 cycloalkyl, each selected ^ Substituted with one or more substituents, the substituents are selected from the group C consists of halogen, CN, N02, hydroxy, alkoxy CRC4,

Cl C4烷亞磺醯基、CrC4烷磺醯基、crC4烷 胺基、C^C:8二烷胺基、c3_c6環烷胺基與(Ci_c4 ,基)cvc:6環烷胺基所組成之群組; R29獨立為H、Ci-C0烷基或Cl-C6函烷基; R =立為H、C】-C6烷基、CrC6 i烷基、Ci-C6 ,羧基、CrC6烷磺醯基或crc6齒烷磺醯基; 各Q與Q2獨立為〇、S或N(R3】); q3為C1-C4伸炫基’其選擇性地經至多4個取代基 取代’該取代基係選自CrC6烷基、C2-C6烯 基、C2-C6炔基與C3_C6環烷基之取代基取代; r30獨立為Η、Ci_C6燒基或(^-〇6鹵院基; R31獨立為Η、C「C6燒基或c]-C6 _炫•基; R32為Η或Ci-C6炫•基, 各X為0、1或2 ; W5為CrC6伸烷基; W1為CVC6伸烷基、C2-C6伸烯基或C2-C6伸炔基; 或-(CH2)2〇CH2-或-(ch2)3〇CH2-; W2為CrCdt烷基; R2為苯基或-W3(苯基)’各選擇性地在環員上經至 多五個選自R21的取代基取代;或-G或-W4G ; 或Η、氰基、羥基、胺基、硝基、_CHO、 -C(=0)0H ' -C(=0)NH2 ' -C(=S)NH2 ' -C(=0)NHCN、-C(=〇)NHOH、-SH、-S02NH2、 -S02NHCN、_S〇細OH、-SF5、-NHCHO、 -NHNH2 ' -NHOH ^ -NHCN ' -NHC(=0)NH2 ' CrC6烷基、c2-c6烯基、c2-C6炔基、crc6鹵 烷基、C2-C6 S烯基、C2_C6 -炔基、c3_c8環 烷基、C3-C8 li環烷基、c4_Ci〇烷環烷基、c4_Cl〇 環院烧基、CVC14環烷環烷基、c4-C10鹵環烷 燒基、CVCu烷環烷烷基、C3_C8環烯基、CrC8 齒環烯基、Crc8烷氧烷基、c3_Cl0烷氧烯基、 CVCh)環垸氧烷基、c3_Ci()烷氧烷氧烷基、 G-Cs烧硫烷基、c2-c8烷亞磺醯烷基、c2-c8 烧確酿炫《基、C2-Cg烧胺烧基、C3-C1G二院胺 院基、C2-C8鹵院胺院基、C4-C10環烧胺烧基、 (:2-(:8烷羰基、c2-c8鹵烷羰基、c4-c10環烷羰 基、c2-c8烷氧羰基、c4-c1()環烷氧羰基、c5-c 12 環烷烷氧羰基、c2_c8烷胺羰基、C3-C1Q二烷 胺幾基、C4-C1Q環炫《胺魏基、C2-C5氮烧基、 Ci-C6經烧基、C4-C10環稀烧基、C2-C8鹵院氧 院基、C2-C8烧氧鹵烧基、C2-C8鹵院氧鹵烧 基、C4-C10鹵環烧氧烧基、C4-C10環稀氧烧基、 c4-c10鹵環烯氧烷基、c3_c10二烷氧烷基、 C3-C1Q烷氧烷羰基、C3-CH)烷氧羰烷基、c2-c8 鹵烷氧羰基、crc6烷氧基、crc6鹵烷氧基、 c3-c8環烷氧基、C3-C8鹵環烷氧基、(:4-(:10環 烧烧氧基、C2-C6稀氧基、C2-C6鹵稀氧基、C3-C6 炔氧基、c3-c6 _炔氧基、c2-c8烷氧烷氧基、 〇2-<:8烷羰氧基、C2-C8鹵烷羰氧基、(:4-(:10環 烷羰氧基、c3_c1G烷羰烷氧基、crc6烷硫基、 C】-C6鹵院硫基、C3-C8環烧硫基、Ci_C6院亞 確酿基、Ci-C6鹵院亞確酿基、C】-C6烧續酿 基、Ci-C6鹵烧績酿基、C3_Cg壞烧石黃酿基、C3_Cs 三烷矽基、c3-c8環烯氧基、c3-c8鹵環烯氧 基、c2-c8 ii烷氧烷氧基、c2-c8烷氧鹵烷氧 基、c2-c8鹵烷氧鹵烷氧基、c3-c10烷氧羰烷 氧基、c2-c8烷基(硫羰基)氧基、c2-c8烷羰硫 基、c2_c8烷(硫羰基)硫基、c3_c8環烷亞磺醯 基、Ci-C6院胺績酿基、C2-Cg二院胺續酿基、 C3-C10 li三烷矽基、CrC6烷胺基、c2-c8二烷 胺基、Ci-C6鹵炫*胺基、C2-Cg鹵二烧胺基、C3-C8 環院胺基、C2-C8烧幾胺基、C2-C8 _院幾胺 基、Ci_C6烧績酿胺基、Ci_C6齒烧績酿胺基或 C4-C1G環烧(烧基)胺基;或Cl C4 alkylsulfinyl group, CrC4 alkanesulfonyl group, crC4 alkylamino group, C^C:8 dialkylamino group, c3_c6 cycloalkylamino group and (Ci_c4,yl)cvc:6 cycloalkylamine group Group; R29 is independently H, Ci-C0 alkyl or Cl-C6 alkyl; R = H, C] -C6 alkyl, CrC6 i alkyl, Ci-C6, carboxyl, CrC6 alkanesulfonyl Or crc6 torsansulfonyl; each Q and Q2 is independently 〇, S or N(R3)); q3 is a C1-C4 exudyl group which is selectively substituted with up to 4 substituents' Substituted from a substituent of a CrC6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group and a C3_C6 cycloalkyl group; r30 is independently hydrazine, Ci_C6 alkyl group or (^-〇6 halogen-based group; R31 is independently Η, C "C6 alkyl or c]-C6 _ Hyun• base; R32 is Η or Ci-C6 炫•基, each X is 0, 1 or 2; W5 is CrC6 alkyl; W1 is CVC6 alkyl, C2- C6 alkenyl or C2-C6 alkynyl; or -(CH2)2〇CH2- or -(ch2)3〇CH2-; W2 is CrCdt alkyl; R2 is phenyl or -W3(phenyl)' Optionally substituted with up to five substituents selected from R21 on the ring member; or -G or -W4G; or hydrazine, cyano, hydroxy, amine, nitro, _CHO, -C(=0)0H' -C(=0)NH2 ' -C (=S)NH2 '-C(=0)NHCN, -C(=〇)NHOH, -SH, -S02NH2, -S02NHCN, _S〇fine OH, -SF5, -NHCHO, -NHNH2 ' -NHOH ^ -NHCN '-NHC(=0)NH2 'CrC6 alkyl, c2-c6 alkenyl, c2-C6 alkynyl, crc6 haloalkyl, C2-C6 S alkenyl, C2_C6-alkynyl, c3_c8 cycloalkyl, C3-C8 Licycloalkyl, c4_Cidecanecycloalkyl, c4_Cl〇 ring alkyl, CVC14 cycloalkane, c4-C10 halocycloalkyl, CVCu alkanealkyl, C3_C8 cycloalkenyl, CrC8 ring Alkenyl, Crc8 alkoxyalkyl, c3_Cl0 alkoxyalkenyl, CVCh)cyclodecyloxyalkyl, c3_Ci()alkoxyalkyloxyalkyl, G-Cs sulphidealkyl, c2-c8 alkylsulfinylalkyl , c2-c8 烧烧炫" base, C2-Cg amine burning base, C3-C1G two-yard amine base, C2-C8 halogen amine amine base, C4-C10 cyclic amine burning base, (: 2- (: 8 alkylcarbonyl, c2-c8 halocarbonyl, c4-c10 cycloalkylcarbonyl, c2-c8 alkoxycarbonyl, c4-c1()cycloalkoxycarbonyl, c5-c 12 cycloalkaneoxycarbonyl, c2_c8 alkylamine Carbonyl, C3-C1Q dialkylamine, C4-C1Q cyclodextrin, amine-Wei, C2-C5, nitrogen-based, Ci-C6, alkyl, C4-C10 ring, C2-C8 Base, C2-C8 oxy-hydrogen group, C2-C8 halogen Oxyhaloalkyl, C4-C10 halocyclic oxyalkyl, C4-C10 cyclooxyalkyl, c4-c10 halocyclooxyalkyl, c3_c10 dialkyloxyalkyl, C3-C1Q alkoxycarbonyl, C3 -CH) alkoxycarbonylalkyl, c2-c8 haloalkoxycarbonyl, crc6 alkoxy, crc6 haloalkoxy, c3-c8 cycloalkoxy, C3-C8 halocycloalkoxy, (:4-( : 10 ring-burning oxy group, C2-C6-d-oxyl group, C2-C6-halooxy group, C3-C6 alkynyloxy group, c3-c6-alkynyloxy group, c2-c8 alkoxylated alkoxy group, 〇2- <:8 alkylcarbonyloxy, C2-C8 halocarbonyloxy, (: 4-(:10 cycloalkylcarbonyloxy, c3_c1G alkylcarbonyloxy, crc6 alkylthio, C]-C6 halogen sulphur Base, C3-C8 ring sulphur-based, Ci_C6 yue yue base, Ci-C6 halal yoghurt base, C]-C6 burn-and-broil base, Ci-C6 halogen calcined base, C3_Cg bad burnt yellow Stuffed base, C3_Cs trialkyl fluorenyl, c3-c8 cycloalkenyloxy, c3-c8 halocycloalkenyloxy, c2-c8 ii alkoxyalkoxy, c2-c8 alkoxyhaloxy, c2-c8 Alkoxyhaloalkoxy, c3-c10 alkoxycarbonylalkoxy, c2-c8 alkyl(thiocarbonyl)oxy, c2-c8 alkylcarbonylthio, c2_c8 alkane(thiocarbonyl)thio, c3_c8cycloalkane Sulfonyl, Ci-C6 compound amine base, C2-C g II compound continuation base, C3-C10 li trialkyl fluorenyl group, CrC6 alkylamino group, c2-c8 dialkylamino group, Ci-C6 halogenated amine group, C2-Cg halogen dialkyl amine group, C3- C8 ring amine group, C2-C8 succinylamine, C2-C8 _ s-amino group, Ci_C6 calcined amine group, Ci_C6 tooth-burning amine group or C4-C1G ring-burning (alkyl) amine group; or

R2 為 _W6C(=E4)R33 、 -W6L1C(=E5)R34 、 -\ν6ί:(=Ε6)Ι^35、-W6S(0)yNR37C(=0)R36 或 -W6S(0)yNR37C(=0)L1R36 ; 各 E、E5 與 E6獨立為 〇、S、NR37、NOR37、NN(R37)2、 N-CN 或 N-N02 ; 各L1獨立為〇、n(R38)或S ; 與R獨立為氫;或crc6烷基、 各 R33、R34、R35 C^C:6烯基、Cz-C6炔基或CVC6環烷基,各選 擇性地經一或多個取代基取代,該取代基 自由鹵素、CN、N02、Μ基、CrC4燒氧基、 Ci-C4烷亞磺醢基、CrC:4烷磺醯基、Ci-q烷 胺基、CVC8二烷胺基、環烷胺基與 烷基)CVC:6環烷胺基所組成之群組; 4 ^ R:7獨立為H、Cl_C6院基或Ci_Q _燒基,· 谷Q與Q5獨立為0、s或N(R38); Q為C「C4伸燒基’其選擇性地經至多4個選自 CVC6院基、C2-C6稀基、c2-C6快基與c3-c6 環烷基的取代基取代; R38獨立為Η、CrC6烷基或CVQ函烷基; R39為Η或CrC6烷基; 各y為0、1或2 ; W7為CrC6伸烷基; W6為CrC6伸烷基、C2-C6伸烯基或C2-C6伸炔基; 或-(CH2)2OCH2-或-(CH2)3OCH2-; W3為CrC6伸烷基、(:2-(:6伸烯基或c2-c6伸炔基; W4為crc6伸烷基; R3為H、鹵素、氰基、羥基、-0_M+、胺基、硝基、 -CHO、-C(=0)0H、-C(=0)NH2、-C(=S)NH2、 -SH、-so2nh2、-so2nhcn、-S02NH0H、 -OCN、-SCN、-SF5、-NHNH2、-NHOH、 -N=C=0、-N=C=S、Ci-Cg 院氧基、Ci_C6 鹵院 氧基、c3-c8環烷氧基、c3-c8鹵環烷氧基、 c4-c10環烷烷氧基、c2-c6烯氧基、c2-c6鹵烯 氧基、c3-c6炔氧基、c3-c6鹵炔氧基、c2-c8 燒氧烧氧基、C2-C8院截氧基、C2-C8函院羰氧 基、C4-Ch)環烷羰氧基、C3-C1G烷羰烷氧基、 Ci-C6烧硫基、C!-C6 lil烧硫基、C3.Cs環烧硫 基、CrC6烷亞磺醯基、CrC6鹵烷亞磺醯基、 Ci-C6炫(續酿基、C!-C6 _烧續酿基、C3-C8環 烷磺醯基、crc6烷磺醯氧基、crc6烷胺基、 C2_Cg 二烧胺基、Ci_C6 函烧胺基、C2-C8 iii 二 炫·胺基、CVC8環烷胺基、c2-C8烷幾胺基、c2-c8 #院羰胺基、Crc6烷磺醯胺基或crC6 _烷磺 醯胺基;或苄氧基、苯氧基、苄羰氧基、苯羰 氧基、苯磺醯氧基、苄磺醯氧基、苯硫基、苄 硫基、苯亞磺醯基、节亞磺醯基、苯磺醢基或 节磺醯基,各選擇性地在環員上經至多五個選 自R21的取代基取代; M+為一鹼金屬陽離子或一銨陽離子; R R、R與R各獨立為H、鹵素、經基、Ci_c6 院基、c2-c6烯基、c2-c6炔基、Cl_c6鹵烷基、R2 is _W6C(=E4)R33, -W6L1C(=E5)R34, -\ν6ί:(=Ε6)Ι^35, -W6S(0)yNR37C(=0)R36 or -W6S(0)yNR37C(= 0) L1R36; each E, E5 and E6 are independently 〇, S, NR37, NOR37, NN(R37)2, N-CN or N-N02; each L1 is independently 〇, n(R38) or S; Is hydrogen; or crc6 alkyl, each R33, R34, R35 C^C: 6 alkenyl, Cz-C6 alkynyl or CVC6 cycloalkyl, each optionally substituted with one or more substituents, which are free Halogen, CN, N02, fluorenyl, CrC4 alkoxy, Ci-C4 alkylsulfinyl, CrC: 4 alkanesulfonyl, Ci-q alkylamino, CVC8 dialkylamino, cycloalkylamino and alkane Group CVC: group consisting of 6 cycloalkylamino groups; 4 ^ R: 7 independently H, Cl_C6 or Ki_Q _ alkyl, · Valley Q and Q5 are independently 0, s or N (R38); Q For C "C4 extended alkyl", which is optionally substituted with up to 4 substituents selected from the group consisting of CVC6, C2-C6, c2-C6, and c3-c6 cycloalkyl; R38 is independently CrC6 alkyl or CVQ alkyl; R39 is hydrazine or CrC6 alkyl; each y is 0, 1 or 2; W7 is CrC6 alkyl; W6 is CrC6 alkyl, C2-C6 extended alkenyl or C2-C6 Extending alkynyl; or -(CH2)2OCH2- or -(CH2)3OCH2-; W3 is a CrC6 alkylene group, (: 2-(:6-alkenyl or c2-c6-alkenyl; W4 is crc6-alkyl; R3 is H, halogen, cyano, hydroxyl, -0_M+, amine group, nitro group, -CHO, -C(=0)0H, -C(=0)NH2, -C(=S)NH2, -SH, -so2nh2, -so2nhcn, -S02NH0H, -OCN , -SCN, -SF5, -NHNH2, -NHOH, -N=C=0, -N=C=S, Ci-Cg, alkoxy, Ci_C6, halo-oxyl, c3-c8 cycloalkoxy, c3- C8 halocycloalkoxy, c4-c10 cycloalkanoyloxy, c2-c6 alkenyloxy, c2-c6 haloalkenyloxy, c3-c6 alkynyloxy, c3-c6 haloalkoxy, c2-c8 Oxykoxy, oxy-C2-C8, carbonyl, C2-C8, carbonyloxy, C4-Ch)cycloalkaneoxy, C3-C1G alkylcarbonyloxy, Ci-C6, sulfur-based, C! -C6 lil sulphur-based, C3.Cs cyclosulphur-based, CrC6 alkylsulfinyl, CrC6 halosulfinyl, Ci-C6 dazzle (continued base, C!-C6 _ calcined base, C3 -C8 naphthylsulfonyl, crc6 alkanesulfonyloxy, crc6 alkylamino, C2_Cg dialkylamine, Ci_C6 functional amine, C2-C8 iii dihydro-amine, CVC8 cycloalkylamine, c2- C8 alkanoamine, c2-c8 #院carbonylamino, Crc6 alkanesulfonylamino or crC6-alkylsulfonylamino; or benzyloxy , phenoxy, benzyloxyoxy, phenylcarbonyloxy, phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio, phenylsulfinyl, sulfinyl, benzene a fluorenyl or a sulfonyl group, each optionally substituted with up to five substituents selected from R21 on the ring member; M+ is an alkali metal cation or a monoammonium cation; RR, R and R are each independently H, halogen , mercapto, Ci_c6, c2-c6 alkenyl, c2-c6 alkynyl, Cl_c6 haloalkyl,

Ci-c6烧氧基、crC6鹵烧氧基、C3-C8環院氧 基或CrC8函環烷氧基;或苯基或苄基,各選 擇性地在環員上經至多五個選自R21的取代基 取代; i 為 H、CrC6 燒基、c2-C6 稀基、C2-C6 块基、crc6 4燒基、c2-c6鹵烯基、c2-c6鹵炔基、c3_c8 環烷基或CyC8鹵環烷基;或苄基,其選擇性 地在環員上經至多五個選自R21的取代基取 代; i R9 為 Η、crc6 烷基、c2_c6 烯基、c2_c6 炔基、Ci_C6 齒燒基、CrQ函辦r基、CVC6 i块基、c3_c8 環烷基、c3-c8 _環烷基、c4_ClG烷環烷4、8 C4-C1G環烷烷基、C6_Ci4環烷環烷基、C4_Ci〇 i環燒烧基、c5-c12燒環燒烧基、c3_C8 4環‘ 基、C3_c8 _環烯基、c2_c8烷氧烷基、c4_Ci〇 環烷氧烷基、c3-c1()烷氧烷氧烷基或c2-c8烷 硫烷基;Ci-c6 alkoxy, crC6 haloalkoxy, C3-C8 cycloalkoxy or CrC8 functional cycloalkoxy; or phenyl or benzyl, each selectively up to five on the ring member selected from R21 Substituted by a substituent; i is H, CrC6 alkyl, c2-C6 dilute, C2-C6 block, crc6 4 alkyl, c2-c6 haloalkenyl, c2-c6 haloalkynyl, c3_c8 cycloalkyl or CyC8 a halocycloalkyl group; or a benzyl group, which is optionally substituted with up to five substituents selected from R21 on the ring member; i R9 is fluorene, crc6 alkyl, c2_c6 alkenyl, c2_c6 alkynyl, Ci_C6 dentate ,CrQ letter r group, CVC6 i block group, c3_c8 cycloalkyl, c3-c8 _cycloalkyl, c4_ClG alkane 4, 8 C4-C1G cycloalkyl, C6_Ci4 cycloalkane, C4_Ci〇i Ring-burning group, c5-c12 ring-burning group, c3_C8 4 ring' group, C3_c8-cycloalkenyl group, c2_c8 alkoxyalkyl group, c4_Ci〇cycloalkoxyalkyl group, c3-c1() alkoxyaloxane Or a c2-c8 alkylthioalkyl group;

Rl()為Η、鹵素、氰基、羥基、胺基、硝基、SH、 -S〇2NH2 ' -S02NHCN ' -SO2NHOH ' -OCN ' -SCN、-SF5、-NHCHO、·ΝΗΝΗ2、-N3、-NHOH、 •NHCN、-NHC(=0)NH2、-N=C=0、-N=C=S、 CrC6烷基、C2-C6烯基、C2-C6炔基、CrC6鹵 燒基、C2-C6鹵稀基、C2-C6鹵炔基、C3-C8環 烷基、C3-C8鹵環烷基、C4-C10烷環烷基、C4-C10 環烷烷基、c6-c14環烷環烷基、c4-c10鹵環烷 烷基、c5-c12烷環烷烷基、c3-c8環烯基、c3-c8 鹵環烯基、c2-c8烷氧烷基、c4-c10環烷氧烷 基、c3-c1Q烷氧烷氧烷基或c2-c8烷硫烷基; R為H、鹵素、氰基、經基、胺基、Ci-C6院基、 crc6烯基、c2-c6炔基、crc6鹵烷基、c2-c6 鹵烯基、c2-c6鹵炔基、c3-c8環烷基、c3-c8 鹵環烷基、c4-c10烷環烷基、c4-c10環烷烷基、 c4-c10鹵環烷烷基、c5-c12烷環烷烷基、c3-c8 環烯基、c3-c8函環烯基、c2-c8烷氧烷基、 C4-C1G環炫•氧烧基、C3-C1G烧氧炫>氧烧基、 c2-c8烷硫烷基、c2-c8烷亞磺醯烷基或c2-c8 烷磺醯烷基;或苯基,其選擇性地經至多五個 選自R21的取代基取代;Rl() is hydrazine, halogen, cyano, hydroxy, amine, nitro, SH, -S〇2NH2 ' -S02NHCN ' -SO2NHOH ' -OCN ' -SCN, -SF5, -NHCHO, ·ΝΗΝΗ2, -N3, -NHOH, •NHCN, -NHC(=0)NH2, -N=C=0, -N=C=S, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, CrC6 haloalkyl, C2 -C6 halogenated, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkanyl, c6-c14 cycloalkane Alkyl, c4-c10 halocycloalkyl, c5-c12 alkancycloalkyl, c3-c8 cycloalkenyl, c3-c8 halocycloalkenyl, c2-c8 alkoxyalkyl, c4-c10 cycloalkoxy Alkyl, c3-c1Q alkoxyalkoxyalkyl or c2-c8 alkylsulfanyl; R is H, halogen, cyano, thio, amino, Ci-C6, crc6, c2-c6 , crc6 haloalkyl, c2-c6 haloalkenyl, c2-c6 haloalkynyl, c3-c8 cycloalkyl, c3-c8 halocycloalkyl, c4-c10 alkanecycloalkyl, c4-c10 cycloalkane , c4-c10 halocycloalkyl, c5-c12 alkancycloalkyl, c3-c8 cycloalkenyl, c3-c8 functional cycloalkenyl, c2-c8 alkoxyalkyl, C4-C1G cyclodane Burning base, C3-C1G smoldering > oxyalkyl, c2-c8 alkylsulfanyl, c2-c8 alkylsulfinane Or a C2-c8 alkanesulfonyl group; or a phenyl group, which is optionally substituted with up to five substituents selected from R21;

Rl2為Η、鹵素、氰基、羥基、胺基、C「C6烷基、 C2-C6 烯基、c2-c6 炔基、crc6 鹵烷基、c2-c6 鹵烯基、c2-c6鹵炔基、c3-c8環烷基、c3-c8 Μ烧基、c4-Cl0燒環燒基、C4_Ci〇環院院基、 c6-c14環㈣絲、“ _親基、kb 烧環眺基、c3-c8環埽基、c3_c8齒環稀基或 C2-Cg院乳幾胺基; R13為H、齒素、氰基、羥基、胺基、硝 烷氧羰基; η為0、1或2 ; 、R、R與汉19獨立為Η、函素、氰基、經 基或CVC6院基;或 -對R14與R18 -起料伸絲或C2_C6伸稀 基; R為H'CVQ齒烧基、c2_c6鹵稀基、Ci_c6院氧 基、Cl-C6纽氧基、c3-c8環烷氧基、C!-C6 烷基、CVC6烯基、CVQ炔基或c3_Cpf烷基; τ為CrC6伸烷基或c2-c6伸烯基; 各G獨立為一 5·或6-員雜環或一 8_、9_或10•員稠 合雙環環系,各環或環系係選擇性地經至多五 個選自在碳環員上之R2]與在氮環員上之R22 的取代基取代; 各R獨立為鹵素、氰基、羥基、胺基、石肖基、_CH〇、 -C(=〇)〇H、-C(=〇)NH2、-C(=S)NH2、 -C(=〇)NHCN、-C(=0)NHOH、-SH、-S02NH2、 -S02NHCN、-S02NH0H、-OCN、-SCN、-SF5、 Ci-c6 烷基、c2-C6 烯基、C2-C6 炔基、Crc6 鹵 炫基、CrC6函稀基、C2-C6 _块基、C3-C8環 烧基、c3-c8 i環烷基、c4-c1()烷環烷基、c4-c10 201240602 環烷烷基、c3-c8環烯基、c3-c8鹵環烯基、c2-c8 烷氧烷基、c4-c1G環烷氧烷基、C3_C1G烷氧烷 氧烧基、C2-C8院硫院基、C2-C8院亞礦醯炫 基、c2-c8烷氧鹵烷基、c2-c5氰烷基、c「c6 5 羥烷基、crc6烷氧基、crc6鹵烷氧基、c3-c8 環烷氧基、c3-c8鹵環烷氧基、c4-c10環烷烷 氧基、c2-c6烯氧基、c2-c6鹵烯氧基、c2-c8 烷氧烷氧基、c2-c8烷羰氧基、crc6烷硫基、 Ci_C6鹵炫*硫基、C3-C8環烧硫基、Ci_C6烧亞 10 續酿基、C!-C6鹵烧亞確酿基、Ci-C6炫續酿 基、C!-C6 _院績酿基、C3_Cg環院續酿基、Ci-C6 院胺基、C2-C8二烧胺基、C1-C6鹵院胺基、C2-C8 鹵二烷胺基或c3-c8環烷胺基; 各R22獨立為Ci-C6烧基、C2-C6稀基、C2-C6快基、 15 Ci_C6鹵烧基、C3-C8環炫*基或C2-C8烧氧烧基; 114()為crc6烷基;以及 R41為CrC6烷基;或 R40 與 R41 — 起作為-(CH2)4-、-(CH2)5-、 -ch2ch=chch2-或-(ch2)2o(ch2)2-。 20 本發明涉及一種式1化合物(包括所有立體異構 物)、其一#氧化物或其鹽。本發明亦關於一種除草組 成物,其包含一本發明之化合物(即以一除草有效量) 與至少一種選自由界面活性劑、固體稀釋劑與液體稀釋 劑所組成之群組的成分。本發明進一步關於一種用於防 治非所欲植物之生長的方法,其包含使該植物或其環境 25 201240602 接觸一除草有效量的一本發明化合物(例如以一本文中 所述之組成物)。 本發明亦關於(a)—式1化合物與(b)至少一種額外 活性成分的一種除草混合物。 本發明亦關於一種式1Q中間化合物(包括所有立 體異構物)、其#氧化物及其鹽:Rl2 is anthracene, halogen, cyano, hydroxy, amine, C "C6 alkyl, C2-C6 alkenyl, c2-c6 alkynyl, crc6 haloalkyl, c2-c6 haloalkenyl, c2-c6 haloalkynyl , c3-c8 cycloalkyl, c3-c8 fluorenyl, c4-Cl0 pyrrolidine, C4_Ci ring, c6-c14 ring (tetra), " _ parent group, kb ring fluorenyl group, c3- C8 cyclodecyl, c3_c8 ring-dense or C2-Cg-indenylamine; R13 is H, dentate, cyano, hydroxy, amine, nitroalkoxy; η is 0, 1 or 2; , R and Han 19 are independent of Η, 素, cyano, thiol or CVC6; or - R14 and R18 - from the wire or C2_C6 stretching; R is H'CVQ tooth burning, c2_c6 halogen Dilute, Ci_c6 alkoxy, Cl-C6 neooxy, c3-c8 cycloalkoxy, C!-C6 alkyl, CVC6 alkenyl, CVQ alkynyl or c3_Cpf alkyl; τ is CrC6 alkyl or c2 -c6 is an alkenyl group; each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or ring system optionally being selected from up to five R2] on the carbocyclic member is substituted with a substituent of R22 on the nitrogen ring member; each R is independently halogen, cyano, hydroxy, amine, schiffyl, _CH〇 -C(=〇)〇H, -C(=〇)NH2, -C(=S)NH2, -C(=〇)NHCN, -C(=0)NHOH, -SH, -S02NH2, -S02NHCN, -S02NH0H, -OCN, -SCN, -SF5, Ci-c6 alkyl, c2-C6 alkenyl, C2-C6 alkynyl, Crc6 halo, CrC6, C2-C6 _block, C3-C8 Cycloalkyl, c3-c8 i cycloalkyl, c4-c1()alkylcycloalkyl, c4-c10 201240602 cycloalkyl, c3-c8 cycloalkenyl, c3-c8 halocycloalkenyl, c2-c8 alkane Oxyalkyl, c4-c1G cycloalkoxyalkyl, C3_C1G alkoxyalkane, C2-C8 Institute of Sulfur, C2-C8 Institute of sulfhydryl, c2-c8 alkoxyhaloalkyl, c2- C5 cyanoalkyl, c "c6 5 hydroxyalkyl, crc6 alkoxy, crc6 haloalkoxy, c3-c8 cycloalkoxy, c3-c8 halocycloalkoxy, c4-c10 cycloalkylalkoxy, C2-c6 alkenyloxy, c2-c6 haloalkenyloxy, c2-c8 alkoxyalkoxy, c2-c8 alkylcarbonyloxy, crc6 alkylthio, Ci_C6 halogenothiol, C3-C8 cyclosulphur Base, Ci_C6 烧亚10 continuation brewing base, C!-C6 halogen burning Yazhen brewing base, Ci-C6 dazzling brewing base, C!-C6 _ academic performance brewing base, C3_Cg ring hospital continuation base, Ci-C6 hospital Amino, C2-C8 dialkylamine, C1-C6 halogen amphotery, C2-C8 haloalkylamine or c3-c8 cycloalkylamine Each R22 is independently a Ci-C6 alkyl group, a C2-C6 dilute group, a C2-C6 fast group, a 15 Ci_C6 halogen group, a C3-C8 cyclohexyl group or a C2-C8 azepine group; 114 () is a crc6 alkane And R41 is a CrC6 alkyl group; or R40 and R41 together are -(CH2)4-, -(CH2)5-, -ch2ch=chch2- or -(ch2)2o(ch2)2-. The present invention relates to a compound of the formula 1 (including all stereoisomers), an oxide thereof or a salt thereof. The invention also relates to a herbicidal composition comprising a compound of the invention (i.e., in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents. The invention further relates to a method for controlling the growth of an unwanted plant comprising contacting the plant or its environment 25 201240602 with a herbicidally effective amount of a compound of the invention (e.g., as described herein). The invention also relates to a herbicidal mixture of (a) - a compound of formula 1 and (b) at least one additional active ingredient. The invention also relates to an intermediate compound of the formula 1Q (including all stereoisomers), its #oxide and its salts:

R1 R2 ίο 其中A'為選自由下列所組成之群組之自由基R1 R2 ίο where A' is a free radical selected from the group consisting of

1化合物所定義者,其可用於製備一式1化合物。 15 本發明亦關於一種式1R化合物(包括所有立體異 構物)、其#氧化物及其鹽: 17 201240602 Ο ΟA compound defined by the compound which can be used to prepare a compound of formula 1. 15 The present invention also relates to a compound of the formula 1R (including all stereoisomers), its #oxide and its salts: 17 201240602 Ο Ο

R1 R2 其中 R1為 5R1 R2 where R1 is 5

;或 R1 為-WiCpEbR24 、 ^LC(=E2)R25 或 -WiCpE3)!^26 ;或 ίο R1 為 N(R40)R41 ;或 R1 為 GA ; 各GA為一 5-至6-員碳環,其包括選自C(=0)、 C(=N_OR3G)或 C=NN(R29)2 的環員;或一 9-至 11 _員飽和或部分飽和碳螺環或雜螺環環系,其 is 選擇性地包括選自C(=0)、C(=N-OR3G)或 C=NN(R29)2的環員,各環或環系選擇性地經至 多三個選自在碳環員上之R21與在氮環員上之 R22的取代基取代;或 各GA為一 9-員部分飽和稠合環系,其含有碳環員 20 與2個氮環員,該環選擇性地經至多2個選自 在碳環員上之R21與在氮環員上之R22的取代 基取代; 各 E、E2 與 E3 獨立為 〇、N〇R28 或 NN(R28)2 ; L獨立為Ο或N(R31); 各R24、R2、R26獨立為氫;或crc4烧基或c3-c5 裱烷基,各選擇性地經一或多個選自由齒素、 CN、羥基、Cl<:2烷氧基、Ci_C2烷亞磺醯基 與CrC4燒磺醯基所組成之群組的取代基取 代; 各R=獨立為Η、Ci-C3烷基或crc3 ii烷基; 各R獨立為H、crc3烷基、crC3 ώ烷基、CrC3 烧幾基、CrC3烷磺醯基或Crc3 _烷磺醯基; 各Q1與Q2獨立為〇或N(R31); Q為CrC3伸烧基’其選擇性地經至多2個選自 CrC;4燒基的取代基取代; R3i獨立為Η、CrC3烷基或crC3鹵烷基; R 1獨立為H、CrC3烷基或crC3鹵烷基; R為Η或CrC3烷基; w為crc4伸院基; w^為 C2-C4 伸烷基、_(CH2)2OCH2-或-(ch2)3och2-; R為苯基或-w3(苯基),各在環員上經至多兩個選 自R21的取代基取代;或·〇 ;或CrC6烷基或 €3<:8環烧基; w3為CrC6伸烷基、CH:6伸烯基或(:2-<:6伸炔基; 各G獨立為一 5-或6-員雜環或一 8-、9-或10-員稍 σ雙%壤糸,各環或環系係選擇性地經至多五 個選自在碳環員上之R21與在氮環員上之R22 的取代基取代; 201240602 各R21獨立為鹵素、氰基、羥基、胺基、硝基、-CHO、 -C(=0)0H、-C(=0)NH2、-C(=S)NH2、 -C(=0)NHCN、-C(=0)NH0H、-SH、-S02NH2、 -S02NHCN ' -SO2NHOH ' -OCN ' -SCN ' -SF5 ' 5 C1-C6 烧基、C2-C6 稀基、C2-C6 快基、Ci-C6 _ 烧基、C2-C6鹵婦基、C2-C6鹵快基、C3-C8環 烧基、C3-C8函環烧基、C4-Ci〇烧環院基、C4-C10 環烧烧基、C3-C8環稀基、C3-C8 _環稀基、C2-C8 院氧院基、C4-C10環院氧烧基、C3-C1G烧氧烧 ίο 氧院基、C2-C8烧硫烧基、C2-C8烧亞績醯烧 基、C2-C8炫*氧鹵烧基、C2-C5氮炫•基、Ci_C6 經院基、C1-C6烧氧基、C1-C6鹵院氧基、C3-C8 環院氧基、C3-C8鹵環烧氧基、C4-C10環烧烧 氧基、〇2·〇6稀氧基、C2-C6鹵燦氧基、C2-C8 15 烷氧烷氧基、C2-C8烷羰氧基、CrC6烷硫基、 crc6鹵烷硫基、c3-c8環烷硫基、crc6烷亞 續酿基、Ci-C6鹵烧亞續酿基、C】-C6烧續酿 基、Ci-C6鹵院績酿基、C3_Cg環炫》續酿基、Ci-C6 烧胺基、C2-C8二烧胺基、C1-C6鹵烧胺基、C2-C8 20 鹵二院胺基或C3-C8環炫胺基; 各R22獨立為CVC6烷基、C2-C6烯基、C2-C6炔基、 crc6鹵烷基、c3_c8環烷基或c2-c8烷氧烷基; R40為C丨-C6烷基;以及 R41為CrC6烷基;或 25 R40 與 R41 — 起作為-(CH2)4-、-(CH2)5-、 -CH2CH=CHCH2-或-(CH2)20(CH2)2-。 20 201240602 其可用於製備一式1化合物β 本發明亦關於一種式ls化合物(包括所有立體異 構物)、其W氧化物及其鹽: ” 15 其中 R1為 R1為Or R1 is -WiCpEbR24, ^LC(=E2)R25 or -WiCpE3)!^26; or ίο R1 is N(R40)R41; or R1 is GA; each GA is a 5- to 6-membered carbocyclic ring, It comprises a ring member selected from C(=0), C(=N_OR3G) or C=NN(R29)2; or a 9- to 11-membered saturated or partially saturated carbon spiro or heterospiro ring system, Is optionally comprising a ring member selected from C(=0), C(=N-OR3G) or C=NN(R29)2, each ring or ring system selectively being selected from up to three selected from the ring member R21 is substituted with a substituent of R22 on the nitrogen ring member; or each GA is a 9-membered partially saturated fused ring system containing a carbocyclic member 20 and 2 nitrogen ring members, the ring selectively passing at most Two are selected from R21 on a carbon ring member and a substituent on R22 on a nitrogen ring member; each E, E2 and E3 is independently 〇, N〇R28 or NN(R28)2; L is independently Ο or N ( R31); each R24, R2, R26 is independently hydrogen; or crc4 alkyl or c3-c5 alkyl, each optionally one or more selected from the group consisting of dentate, CN, hydroxyl, Cl<:2 alkoxy Substituted by a group consisting of a Ci_C2 alkylsulfinyl group and a CrC4 sulfonyl group; each R = independently is hydrazine, Ci-C3 alkyl or crc3 ii Alkyl; each R is independently H, crc3 alkyl, crC3 alkyl, CrC3 alkyl, CrC3 alkanesulfonyl or Crc3 alkanesulfonyl; each Q1 and Q2 is independently 〇 or N(R31); CrCr3 is optionally substituted with up to 2 substituents selected from CrC; 4 alkyl; R3i is independently hydrazine, CrC3 alkyl or crC3 haloalkyl; R 1 is independently H, CrC3 alkyl or crC3 haloalkyl; R is hydrazine or CrC3 alkyl; w is crc4 stretching; w^ is C2-C4 alkyl, _(CH2)2OCH2- or -(ch2)3och2-; R is phenyl or - W3 (phenyl), each substituted on the ring member with up to two substituents selected from R21; or 〇; or CrC6 alkyl or €3<:8 cycloalkyl; w3 is CrC6 alkyl, CH: 6-alkenyl or (: 2-<:6-exetylene; each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered slightly sigma double % soil, each ring Or the ring system is selectively substituted with up to five substituents selected from R21 on a carbocyclic member and R22 on a nitrogen ring member; 201240602 each R21 is independently halogen, cyano, hydroxy, amine, nitro, -CHO, -C(=0)0H, -C(=0)NH2, -C(=S)NH2, -C(=0)NHCN, -C(=0)NH0H, -SH, -S02NH2, - S02NHCN ' -SO2NHOH ' -OCN ' -SCN ' -SF5 ' 5 C1-C6 alkyl, C2-C6 dilute, C2-C6 fast radical, Ci-C6 _ alkyl, C2-C6 halogenated base, C2-C6 halogen fast Base, C3-C8 cycloalkyl, C3-C8 functional ring alkyl, C4-Ci oxime ring, C4-C10 ring alkyl, C3-C8 ring, C3-C8 _ ring, C2 -C8 Institute of Oxygen, C4-C10 Ring Oxygen Burning, C3-C1G Oxygen Burning, Oxygen Base, C2-C8 Sulphur Burning Base, C2-C8 Sintering, C2-C8 Hyun* Oxyhaloalkyl, C2-C5 azafenyl, Ci_C6 trans-system, C1-C6 alkoxy, C1-C6 halogen-oxyl, C3-C8 cyclooxy, C3-C8 halo alkoxy, C4 -C10 ring-burning oxy group, 〇2·〇6-diloxy group, C2-C6 halo-butoxy group, C2-C8 15 alkoxy alkoxy group, C2-C8 alkylcarbonyloxy group, CrC6 alkylthio group, crc6 halogen Alkylthio, c3-c8 cycloalkylthio, crc6 alkane sulphate, Ci-C6 halogenated succulent, C]-C6 sinter, Ci-C6 broth, C3_Cg 》Continuous base, Ci-C6 amine group, C2-C8 diamined amine group, C1-C6 halogenated amine group, C2-C8 20 halogen II compound or C3-C8 cycloarthryl group; each R22 is independent CVC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, crc6 haloalkyl, c3_c8 naphthenic Or c2-c8 alkoxyalkyl; R40 is C丨-C6 alkyl; and R41 is CrC6 alkyl; or 25 R40 together with R41 as -(CH2)4-, -(CH2)5-, -CH2CH= CHCH2- or -(CH2)20(CH2)2-. 20 201240602 It can be used to prepare a compound of formula 1 β. The invention also relates to a compound of formula ls (including all stereoisomers), its W oxides and salts thereof: ” 15 wherein R1 is R1

、W5'R32 · 或 -W1LC(=E2)R25 或 -W1C(=E1)R24 、-W】C(=E3)LR26 ;或 R1 為 N(R40)R41;或 R1 為 GA ; 各Upt'卜員碳環,其包括選自C(=〇)、 11員飽^或c=NN(R29)2的環員,·或一 9-至 選擇==碳cr環或雜螺環環系,其 C=NNm^ 選自 C(-O)、C(=N-OR30)或 多一個貝’各環或縣選擇性地經至 多二個選自在碳環員上之r21R22的取代基取代;或 -在輯員上之 20 201240602 各G為—9-員部分飽和稠合環系,其含有碳環員 與2個氮環員,該環選擇性地經至多2個選自 在碳環員上之R2】與在氮環員上之R22的取代 基取代; 各E1、E2與E3獨立為〇、n〇r28或讲28)2; L獨立為Ο或N(R31): 各R:R25與R26獨立為氫;或烷基或ca 環烷基,各選擇性地經一或多個選自由鹵素、 10 CN、羥基、CrC2烷氧基、Cl_c2烷亞磺醯基 與CrC4院績醯基所組成之群組的取代基取 代; 各R=獨立為Η、C1-C3烷基或crc3鹵烷基; 15 各R29獨立為Η、CrC3烷基、c丨-c3 IS烷基、c丨-C3 烷羰基、Q-C3烷磺醯基或Cl_c3函烷磺醯基; 各Q1與Q2獨立為〇或n(r31); Q為eye:3伸烷基,其選擇性地經至多2個選自, W5'R32 · or -W1LC(=E2)R25 or -W1C(=E1)R24, -W]C(=E3)LR26; or R1 is N(R40)R41; or R1 is GA; each Upt'b a carbon ring comprising a ring member selected from the group consisting of C(=〇), 11 member saturated or c=NN(R29)2, or a 9-to-select==carbon cr ring or a heterospiro ring system, C=NNm^ is selected from C(-O), C(=N-OR30) or more than one shell' each ring or county is selectively substituted with up to two substituents selected from r21R22 on a carbocyclic member; or 20 on the staff member 201240602 Each G is a 9-member partially saturated fused ring system containing a carbon ring member and two nitrogen ring members, the ring selectively having up to 2 R2 selected from the carbon ring members. 】 substituted with a substituent of R22 on a nitrogen ring; each E1, E2 and E3 is independently 〇, n〇r28 or 28)2; L is independently Ο or N(R31): each R: R25 is independent of R26 Is hydrogen; or alkyl or ca cycloalkyl, each selectively consisting of one or more selected from the group consisting of halogen, 10 CN, hydroxyl, CrC 2 alkoxy, Cl_c 2 alkylsulfinyl and CrC4 Substituted substituents; each R = independently Η, C1-C3 alkyl or crc3 haloalkyl; 15 each R29 is independently Η, CrC3 alkyl, c丨-c3 IS alkyl c丨-C3 alkylcarbonyl, Q-C3 alkanesulfonyl or Cl_c3 alkylsulfonyl; each Q1 and Q2 is independently 〇 or n(r31); Q is an eye: 3 alkyl group, which selectively undergoes at most 2 selected from

CrC4烷基的取代基取代; 20 \獨立為Η、CrC3烧基或CrC3齒院基; R31獨立為Η、CrC3烷基或Cl_C3 _烷基; r32為Η或CrC3烷基; W5為CrC4伸烷基; W1 為 C2-C4伸烧基、-(ch2)2och2-或-(CH2)3〇CH2-; R為苯基或-W3(苯基),各在環員上經至多兩個選 自R21的取代基取代;或-G ;或CrC6烷基或 匕<:8環烷基; W3為Crc6伸烧基、C2-C6伸稀基或c2-C6伸炔基; 22 25 201240602 各G獨立為一 5-或6-員雜環或一 8-、9-或10-員稍 合雙環環系,各環或環系係選擇性地經至多五 個選自在碳環員上之R21與在氮環員上之R22 的取代基取代; 5 各R21獨立為鹵素、氰基、羥基、胺基、硝基、-CHO、 -C(=0)0H ' -C(=0)NH2 ' -C(=S)NH2 ' -C(=0)NHCN、-C(=0)NH0H、-SH、-S02NH2、 -S02NHCN、-S02NHOH、-OCN、-SCN、-SF5、 CVC6烷基、c2-c6烯基、c2-c6炔基、crc6鹵 10 烧基、c2-c6鹵烯基、c2-c6鹵快基、c3-c8環 炫基、C3-C8鹵環院基、C4-C10烧環炫1基、C4-C10 壤烧炫*基、C3-C8 ί哀稀基、C3-C8鹵環稀基、C2_Cg 烧氧烧基、C4-C1G環烧氧烧基、C3-CiQ烧氧炫 氧烧基、C2-C8烧硫烧基、C2-C8院亞續酿燒 15 基、c2-c8烷氧鹵烷基、c2-c5氰烷基、crc6 羥烷基、crc6烷氧基、crc6鹵烷氧基、c3_c8 環烷氧基、c3-c8鹵環烷氧基、c4-c10環烷烷 氧基、c2-c6烯氧基、c2-c6鹵烯氧基、c2-c8 烷氧烷氧基、c2-c8烷羰氧基、crc6烷硫基、 20 CVC6鹵院硫基、C3-C8環院硫基、CVC6烧亞 續酿基、鹵炫》亞續酿基、C^-Cg烧續酿 基、crc6鹵烷磺醯基、c3-c8環烷磺醯基、crc6 院胺基、C2-C8二烧胺基、C1-C6鹵烧胺基、C2-C8 鹵二烧胺基或C3-C8環烧胺基; 23 201240602 各R22獨立為Ci_C6院基、C2-C6烯基、C2-C6炔基、 CrC6函烷基、C3-C8環烷基或C2-C8烷氧烷 基;以及 R23為一選擇性地經取代之碳基團(carbon moiety); 114()為 CrC6 烷基; R41為CrC6烷基;或 R40 與 R41 —起作為 _(CH2)4-、-(CH2)5-、 CH2CH=CHCH2-或-(ch2)2o(ch2)2- 其可用於製備一式1化合物。 【實施方式】 15 20 「如本,中所使用,用語「包含」、「包括」、「具有」、 含有」、「特徵為」或其任何其他的變化,係意欲涵蓋 非排他性的涵括,並受到任何明確表示的限制U如, 匕3元素列表的組合物、混合物、製程或方法不必僅限 1 ’而是可以包括未明確列出的或該組合物、 混合物、製程或方法所固有的其他元素。 連接詞「由. * ^ ^^ ^ …、、且成」則排除任何未明確說明的元 詞將會封㈣t s t在申料職财,這樣的用 的雜質之外,使其除了在通常會與其相關 詞「由·.···.組、L括那些在列舉以外的物質。當該連接 非緊接著二成」t現在中請專利範圍主體的子句,而 元素總體上;會在該子句中提到的元素;其他 連接詞「主要I,專利範圍中被排除。 字面上所揭露以’··..·組成」用於定義包括除了那些 的材料、步驟、特徵、成分或元素的 24 25 201240602 成分或元素1上刚眚疋該等額外的材料、㈣、特徵、 含」與「由!Γ 主要由·····.組成」居於「包 — °'旦成」之間的中間地帶。 部分開放式用語如「包含」定義—發明或其 要由·····.所=非另有說明)該敘述應解讀為亦以「主 再者,;4」或「由·.···.所組成」描述該發明。 性的「咬=另有明確相反表示,「或」係指一涵括 10 15 20 種情況 ( , 成Β · Α疋真(或存在的)且Β 存在的),Α是偽(或不存在的 (或存在的),以及ΑΗ都是真(或存在的)。疋真 「一同樣^位於本發明之元素或成份之前的不定冠詞 實例數Ϊ「二個」旨在非限制性地說明該元素或成份的 個,且該元錢齡的單數詞形也 ^複數,除非該數目顯然是指單數。 或血ΐ本文中所提到,用語「幼苗」’無論是單獨使用 j其他字詞組合烟,意指從—種子胚芽發育的幼嫩 植物。 盥如本文中所指者,用語「闊葉」無論是單獨使用或 ^其他字詞組合使關如「闊葉雜草」,其意指雙子葉 或雙子葉植物,一種用於描述一群特徵為胚具有兩個子 葉之被子植物的用語。 如本文中所用者,用語「烷化劑」係指一種化合物’ 其中3奴自由基係經由一碳原子鍵結至一脫離基 25 25 201240602 如卤化物或是磺酸鹽,其可藉由鍵結一親核劑至前述之 碳原子來置換。除非另有指明,用語「烷化劑」不限制 S亥含碳自由基為院基;在院化劑中之含碳自由基包括各 式石厌鍵結取代基之自由基’其例如指定為用於Rl、R2 與R3者。用語「去烷化劑」係指裂解碳_碳或碳_氧鍵的 試劑。 在上述說明中,用語「烷基」無論是單獨使用或在 複合詞如「烷硫基」或「齒烷基」中使用,皆包括直鏈 或支鏈烷基,諸如甲基、乙基、正丙基、異丙基或不同 之丁基、戊基或己基異構物。「烯基」包括直鏈或支鏈 烯烴如乙烯基、1-丙稀基、2-丙稀基與不同之丁稀基、 戊烯基與己烯基異構物。「烯基」亦包括多烯如丨,2_丙 二烯基與2,4_己二烯基。「炔基」包括直鏈或支鏈炔烴 如乙炔基、1-丙炔基、2·丙快基與不同之丁快基、戊快 基與己炔基異構物。「炔基」亦可包括含複數叁鍵的部 分(moieties)如2,5·己二炔基。「伸烷基」表示一直鏈或 支鏈烷二基。「伸烷基」的實例包括CH2、CH2CH2、 CH(CH3)、CHKI^CH2、CH2CH(CH3)與不同之伸丁基 異構物。「伸烯基」表示含有一個烯鍵的直鏈或支鏈烯 二基。「伸烯基」的實例包括CH=CH、CH2CH=CH、 CH=C(CH3)與不同之伸丁烯基異構物。當所提供之實例 表示兩個變項係「一起作為一 烯基」時,這些 實例並未對連接點作出限制。例如當rh與Ri8 一起作 為-CH=CHCH2-時,此例示性基團的連接點係解讀為連 接至該R14或R18變項的其中一者(即等同 於-CH2CH=CH_)。「伸炔基」表示一直鏈或支鏈炔二 26 201240602 基,其含有一個叁鍵。「伸炔基」之實例包括ceC、 CHzOC、C^CCH2與不同之伸丁炔基異構物。 「烷氧基」包括例如曱氧基、乙氧基、正丙氧基、 異丙氧基與不同之丁氧基、戊氧基與己氧基異構物。「烷 5 氧烷基」表示烷基上有烷氧基取代。「烷氧烷基」的實 例包括 CH3〇CH2、CH3OCH2CH2、CH3CH2OCH2、 CH3CH2CH2CH2OCH2 ^ CH3CH2OCH2CH2 基」表示在烷氧基上有烷氧基取代。「烯氧基」包括直 鏈或支鏈烯氧基部分。「烯氧基」的實例包括 10 H2C=CHCH20 、 (CH3)2C=CHCH20 、 (CH3)CH=CHCH20 . (CH3)CH=C(CH3)CH20 與 CH2=CHCH2CH2〇。「炔氧基」包括直鏈或支鏈炔氧基部 分。「炔氧基」的實例包括HOCCH20、ch3c=cch2o 與CH3〇CCH2CH2〇。「烷氧烯基」包括經烷氧基基團 15 取代之直鏈或支鏈烯基。「烷氧烯基」的實例包括 CH3OCH=CH 、 CH3C(OCH3)=CH 與 CH3CH2〇CH=CHCH2。「婕氧烷氧烷基」表示在烷基上 有烷氧烷氧基取代。「烷氧烷氧烷基」的實例包括 CH3OCH2OCH2 、 CH3OCH2OCH2CH2 、 20 CH3CH2OCH2OCH2 與 CH3OCH3CH2OCH2CH2。「烷硫 基」包括支鏈或直鏈烷硫基部分,諸如甲硫基、乙硫基 與不同之丙硫基、丁硫基、戊硫基與己硫基異構物。「烷 亞續醯基」同時包含一炫亞續醯基基團之兩種鏡像異構 物。「烷亞磺醯基」的實例包括CH3S(0)_、 25 ch3ch2s(o)-、CH3CH2CH2S(0)-、(CH3)2CHS(0)-與不 同之丁亞磺醢基、戊亞磺醯基與己亞磺醯基異構物。「烷 27 201240602 磺醯基」的實例包括CH3S(0)2-、CH3CH2S(0)2-、 CH3CH2CH2S(0)2·、(CH3)2CHS(0)2-與不同之 丁磺醯 基、戊確醯基與己續醯基異構物。用語「環院亞項醯基」 與「環烷磺醯基」之定義係與上述用語「烷亞磺醯基」 5 及「烷磺醯基」類似。 「院硫燒基」表示在烧基上有烧硫基取代。「烧硫 烷基」的實例包括ch3sch2、ch3sch2ch2、 CH3CH2SCH2 、 CH3CH2CH2CH2SCH2 與 CH3CH2SCH2CH2 ;「烷亞磺醯烷基」與「烷磺醯烷基」 10 分別包括對應之亞砜與砜。「烷胺基」包括一經直鏈或 支鏈烷基取代之NH自由基。「烷胺基」的實例包括 CH3CH2NH、CH3CH2CH2NH 與(CH3)2CHCH2NH。「二 烷胺基」的實例包括(CH3)2N、(CH3CH2CH2)2N與 CH3CH2(CH3)N。「烷胺烷基」表示在烷基上有烷胺基取 15 代。「烷胺烷基」的實例包括CH3NHCH2、 ch3nhch2ch2 、 ch3ch2nhch2 、 CH3CH2CH2CH2NHCH2 與 CH3CH2NHCH2CH2。「二烷胺 烷基」的實例包括((ch3)2ch)2nch2 、 (CH3CH2CH2)2NCH2 與 CH3CH2(CH3)NCH2CH2。用語「烷 20 羰胺基」表示鍵結至一 C(=0)NH基團的烷基。「烷羰胺 基」 的實例包括 ch3ch2c(=o)nh 與 ch3ch2ch2c(=o)nh。 「烷羰硫基」表示一連接至一硫原子與經由一硫原 子連結之直鏈或支鏈烷羰基。「烷羰硫基」的實例包括 25 ch3c(=o)s、ch3ch2ch2c(=o)s 與(CH3)2CHC(=0)S。 用語「烷基(硫羰基)氧基」表示一鍵結至一硫羰基基團 28 201240602 (連接至一氧原子與經由一氧原子連結)的烷基基團。 「烷基(硫羰基)氧基」的實例包括ch3ch2c(=s)o與 CH3CH2CH2C(=S)0。用語「烷基(硫羰基)硫基」係指一 鍵結至一硫原子的烷基基團。「烷基(硫羰基)硫基」的實 例包括 CH3CH2C(=S;)S。 「二燒碎基」包括3個連接至一碎原子與經由一碎 原子連結的支鏈與/或直鍵院基自由基,諸如三甲石夕 基、三乙矽基與三級丁基二甲矽基。「鹵三烷矽基」的 實例包括 CF3(CH3)2Si-、(CF3)3Si-與 CH2Cl(CH3)2Si-。「羥 10 15 20 烷基」表示一經一個羥基基團取代之烷基基團。「羥烷 基」的實例包括HOCH2CH2、CH3CH2(OH)CH與 HOCH2CH2CH2CH2。「氰烷基」表示一經一個氰基基團 取代之烷基基團。「氰烷基」的實例包括NCCH2、 ncch2ch2 與 ch3ch(cn)ch2。 「環烷基」包括例如環丙基、環丁基、環戊基與環 己基。用语「烷環烷基」表示在一環烷基基團上有烷基 取代並包括例如乙環丙基、異丙環丁基、3_曱環戊基與 =甲環己基。用語「環院絲」表示在—烧基基團上有 %燒基取代。「被院院基」的實例包括環丙曱基、環戍 乙基與其他鍵結至直鏈或支鏈燒基基團的環烧基基 ▲團。用語「概氧基」表示經由—氧原子連結的環烧基, =如%戊氧基與環己氧基。用語「燒環烧基」 表不在一 t燒基基團上找絲H魏基」的實例包括曱 2丙基、乙壞縣與其倾結至環絲基團的直鍵或支 =基基團。絲「料魏基」表示在—賴基基團 烧氧基取代。、燒氧環烧基」的實例包括甲氧環丙 29 25 201240602 基、乙氧環絲與其他鍵結至魏基基團的直鍵或支鍵 烧氧基基團。「環狀氧基」表示經由—氧料連結的 環院院基,該氧原子係連接至該烧基鏈。「環院院氧基」 的實例包括環Μ氧基、環紅氧基與其他鍵結至直鏈 5 或支鏈烷氧基基團的環烷基基團。「氰環烷基」的實例 包括4-氰%己基與3-氰環戊基/環烯基」包括諸如環 戊烯基與環己烯基的基團,以及具有超過一個雙鍵的基 團’諸如1,3-與1,4-環己二烯基。 用語「函素」無論是單獨使用或在複合詞如「鹵烷 10 基」中使用,或者當使用於如「經齒素取代之院基」的 描述中時,其包括氟、氣、溴或碘。再者,當使用於複 合詞如「鹵烷基」中時,或者當使用於如「經鹵素取代 之烷基」之描述中時,該烷基可經相同或不同的鹵素原 子予以部分或全部取代。「齒烧基」或「經鹵素取代之 15 院基」的實例包括 F3C-、C1CH2-、CF3CH2-與 CF3CC12-。 用語「鹵環烷基」、「鹵烷氧基」、「鹵烷硫基」、鹵烷亞 磺醯基、函烷磺醯基、「鹵烯氧基」、「鹵炔氧基」「鹵烯 基」、「鹵炔基」,「鹵烷氧烷基」、「鹵烷氧烷氧基」「鹵 烷氧齒烷氧基」,「鹵烷氧鹵烷基」、「鹵烷胺基」、「鹵 20 烷胺烷基」「函環烷氧基」、「齒環烷氧烷基」、「鹵環烷 烷基」,「鹵環烯基」、「鹵環烯氧基」、「鹵環烯氧基」, 「函環稀氧院基」、「烧氧1¾院氧基」、烧氧函院基、鹵 烷羰氧基與類似者的定義係與用語「||烷基」類似。「鹵 烷氧基」的實例包括 cf3o-、cci3ch2o-、hcf2ch2ch2o- 25 與CF3CH20-。「鹵烷硫基」的實例包括CC13S-、CF3S-、 CC13CH2S-與C1CH2CH2CH2S-。「鹵烷亞磺醯基」的實 30 201240602 例包括 cf3s(o)·、CC13S(0)-、cf3ch2s(o)-與 cf3cf2s(o)-。「鹵烷磺醯基」的實例包括CF3S(0)2-、 cci3s(o)r、cf3ch2s(o)2•與 cf3cf2s(o)2-。「鹵烯基」 的實例包括(C1)2C=CHCH2-與 CF3CH2CH=CHCH2-。「_ 5 炔基」的實你J 包括 HC=CCHC1-、CF3CeC-、CC13C=C-與FCH2〇CCH2-。「鹵烷氧烷氧基」的實例包括 CF30CH20-、C1CH2CH20CH2CH20-、C13CCH20CH20-, 以及支鏈院基衍生物。「鹵烧胺基」的實例包括 CF3(CH3)CHNH、(CF3)2CHNH 與 CH2C1CH2NH。用語 1〇 「ii二烷基」無論是單獨使用或在複合詞如「i二烷胺 基」中使用,意指該兩個烷基基團的至少一者係經至少 一個鹵素原子取代,並且各齒化烷基基團可獨立為經相 同或不同的函素原子予以部分或全部取代。「齒二烷胺 基」 的實例包括 (BrCH2CH2)2N 與 15 BrCH2CH2(ClCH2CH2)N。 「烷羰基」表示一鍵結至一 c(=o)基團的直鏈或支 鏈烷基基團。「烷羰基」的實例包括CH3C(=0)-、 CH3CH2CH2C(=0)-與(CH3)2CHC(=0)-。「烷氧羰基」的 實例包括 ch3oc(=o)- 、ch3ch2oc(=o)-、 20 ch3ch2ch2oc(=o)_、(ch3)2choc(=o),與不同的丁氧 基-或戊氧羰基異構物。用語「豳烷羰基」、「鹵烷氧羰 基」、「烷氧烷羰基」、「環烷氧羰基」、「環烷烷氧羰基」 與「環烷胺羰基」的定義皆類似。 用語「烷氧羰胺基」表示一鍵結至一羰胺基基團之 25 C(=0)基團的直鏈或支鏈烷氧基基團。「烷氧羰胺基」的 實例包括 ch3oc(=o)nh_與 CH3CH20C(=0)NH-。「烷胺 31 201240602 羰基」的實例包括 ch3nhc(=o)、ch3ch2nhc(=〇)、 ch3ch2ch2nhc(=o)、(ch3)2chnhc(=o)與不同之丁胺 -或戊胺羰基異構物。「二烷胺羰基」的實例包括 (CH3)2NC(=0) 、 (ch3ch2)2nc(=o) 、 5 CH3CH2(CH3)NC(=0) 、 (CH3)2CH(CH3)NC(=0)與 CH3CH2CH2(CH3)NC(=0)。用語「烷羰氧基」代表鍵結 至一 c(=o)o基團之直鏈或支鏈烷基。「烷羰氧基」的 實例包括 CH3CH2C(=0)0 與(CH3)2CHC(=0)0。用語「烷 羰烷氧基」表示鍵結至一烷氧基基團的烷羰基。「烷羰 10 烷氧基」的實例包括CH3C(=0)CH2CH20與 CH3CH2C(=0)CH20。「烷氧羰氧基」的實例包括 CH3CH2CH20C(=0)0 與(CH3)2CH0C(=0)0。用語「環 烷羰氧基」表示一鍵結至氧的環烷羰基基團。「環烷羰 氧基」的實例包括環丙基-c(0)0-與環己基-c(0)0-。 15 「烷磺醯胺基」表示一經烷磺醯基取代的NH自由 基。「烷磺醯胺基」的實例包括CH3CH2S(=0)2NH-與 (CH3)2CHS(=0)2NH-。用語「鹵烧磺醯氧基」表示一鍵 結至一氧原子的烧續醢基基團。「烧續醯氧基」的實例 包括 ch3s(=o)2o- 、 CH3CH2S(=0)20-、 20 ch3ch2ch2s(=o)2o-、(ch3)2chs(=o)2o-與不同之丁磺 醯氧基、戊磺醯氧基與己磺醯氧基異構物。 用語「環烷氧烷基」表示在一烷基基團上有環烷氧 基取代。「環烷氧烷基」的實例包括環丙氧甲基、環戊 氧乙基與其他鍵結至直鏈或支鏈烷基基團的環烷氧基 25 基團。用語「環烷硫基」表示連接至一硫原子與經由一 硫原子連結的環烷基,諸如環丙硫基與環戊硫基;「環 32 201240602 烷磺醯基」包括其對應之砜。「烷環烷烷基」表示一經 烧環烧基取代之燒基基團。「烧環烧烧基」的實例包括 卜、2-、3·或4·甲基或_乙基環己基甲基。用語「環烷氧 烷氧烷基」表示連接至一烷氧烷基基團之烷氧基基團的 5 環烷氧基基團。用語「環烷氧烷氧烷基」的實例包括(環 丙基)OCH2OCH2-、(環丁基)OCH2CH2〇CH2_ 或(環己 基)OCH2〇CH2CH2_。用語「環烷環烷基」表示在另一環 烷基環上有環烷基取代,其中各環烷基環獨立具有3至 7個碳原子環員。「環烷環烷基」之實例包括環丙環丙 ίο 基(例如雙環丙基-1-基、1,1,-雙環丙基-2-基)、環 己環戊基(例如4-環戊環己基)與環己環己基(例如 U'-雙環己基-1-基)與不同之順式_及反式-環烷基環烷 基異構物,(例如(1尺2办1,1’-雙環丙基-2-基與 (1足2及)-1,Γ-雙環丙基_2_基)。 15 「二院氧烧基」表示兩個在該院基基團之相同碳上 取代的獨立烷氧基基團。「二烷氧烷基」的實例包括 (ch3o)2ch-與 ch3ch2o(ch3o)ch-。「環烷胺基」表示 一經%院基取代的NH自由基。「環烧胺基」的實例包 括環丙胺基與環己胺基。「環烷基(烷基)胺基」意指一環 20 烧胺基基團’其中氫原子係由一烧基自由基置換。「環 烷基(烷基)胺基」的實例包括諸如環丙基(甲基)胺基、 環丁基(丁基)胺基、環戊基(丙基)胺基、環己基(曱基) 胺基等。用語「環烧胺炫《基」表示在一烧基基團上有環 烷胺基取代。「環烷胺烷基」的實例包括環丙胺甲基、 25 環戊胺乙基與其他鍵結至直鏈或支鏈烷基基團的環燒 胺基基團。 33 201240602 「環烷羰基」表示鍵結至一 c(=〇)基團的環烧基, 其包括例如環丙羰基與環戊羰基。用語Γ環烷氧羰基」 意指鍵結至一 c(=o)基團的環烷氧基,例如環丙氧羰基 與%:戊氧幾基。「環院胺幾基」表示鍵結至一 c(=o)基 5 團的環烷胺基,例如環戊胺羰基與環己胺羰基。「環烷 烷氧羰基」表示鍵結至一 c(=o)基團的環烷烷氧基。「環 院燒氧叛基」的實例包括環丙乙氧幾基與環戊曱氧幾 基。「環院毅氧基」表示連接至一氧原子與經由一氧原 子連結的環烷羰基。「環烷羰氧基」的實例包括環己羰 10 氧基與環戊羰氧基。 用語「環稀烧基」表示在一烧基基團上有環稀基取 代。「環烯烷基」的實例包括環丁烯曱基、環戊稀乙基 與其他鍵結至直鏈或支鏈烷基基團的環烯基基團。用語 「環烯氧基」表示經由一氧原子連結的環烯基,諸如環 15 戊烯氧基與環己烯氧基。用語「環烯氧烷基」表示在一 烷基基團上有環烯氧基取代。「環烯氧烷基」的實例包 括環丁烯氧曱基、環戊烯氧乙基與其他鍵結至直鏈或支 鏈烷基基團的環烯氧基基團。 用語「烧胺績醯基」表示一鍵結至一續酿基基團的 20 直鍵或支鏈烧胺基基團。一「烧胺續醯基」基團的實例 包括 CH3NHS(0)2-或 CH3CH2CH2NHS(0)2-。用語「二 烷胺磺醯基」表示一鍵結至一磺醯基基團的直鏈或支鍵 二烷胺基基團。一「二烷胺磺醯基」基團的實例包括 (CH3)2NS(0)2-或(CH3CH2CH2)2NS(0)r。 25 一取代基基團中之碳原子總數係以「Ci-Cj」前綴語 來指示,其中i與j為1至14之數字。例如,CrC4院 34 201240602 磺醯基表示甲磺醯基到丁磺醯基;c2烷氧烷基表示 CH3OCH2- ; c3烷氧烷基表示例如CH3CH(OCH3)-、 CHsOCHzCH2·或 CH3CH2OCH2-;而 C4 烷氧烷基表示一 經一含總共四個碳原子之烷氧基基團取代之烷基基團 的各種異構物,實例包括ch3ch2ch2och2-與 CH3CH2OCH2CH2-。 當一化合物係經一取代基取代且該取代基帶有下 標(指示該取代基之數目可超過1個)時,該些取代基 (當它們超過1個)係獨立選自所界定取代基之群組, 10 15 20 例如(Rv)r,在展示3之U-1中!·為1、2、3、4或5。當 一基團含有一可為氫之取代基時,例如R2、R3、r4、 R5、R6、R7、r8、r9、ri〇、rii、Ru、r13、r14、r15 R _、R19或R2q,則當採用此取代基為氫時,即認為此 等同於該基團係未經取代。當—可變基_示為選擇性 地連接至一位置時,例如在展示2之中的(RV)r, 則氫可在該位置(即當F為G),即使該可變基gj之定義 中未有此敘述。當描述基團上的—或多個位置為「未經 取或未取代」時,則氫原子係連接以佔據任何自 非另有指明,否則作為-式1成分之-「環」或 ,、」例如取代基GA)係碳環或雜環。用語「環系」 志,:、一f夕個铜核。用語「雙環系」與「稠合雙環系」 立L 個㈣所組成的環系’並且除非另有說明, :二ΐ可為飽和、部分不飽和或完全不飽和。用語 '、不哀’、」表示兩個裯合在單一原子 為碳螺環或雜蟬環。用这「产旨h心並且了 哚衣用b J衣員」係指形成一環或環系 35 25 201240602 主鏈之原子或其他基團(例如c(=o)、c(=s)、s(o)或 S(〇)2) 0 s =語「碳環」、「碳環化合物」或「碳環系」表示一 %或環系,其中形成環主鏈的原子僅選自碳。除非另有 說明,一奴環可以為飽和、部分不飽和或完全不飽和 %。當一完全不飽和碳環滿足休克耳定則(Httcke丨,s rule) 時’則該環亦稱為-「芳環」。「飽和碳環」係指一其主 鏈由彼此以單鍵連接之碳原子所域的環;除非另有指 明,其餘碳價係由氫原子佔據。 用語「雜環」或「雜環系」表示一環或環系,其中 至》-個形成該環主鍵的原子不為碳,例如為氮、氧或 硫。一雜環典型含有不超過4個氮原子、不超過2個氧 原子且不超過2個硫原子。除非另有說明,雜環可以為 77不飽和或完全不飽和環。當—完全不飽和雜 %滿足休克耳定則時’則該環亦稱為一「雜芳環」或「芳 ^雜環」。除非另有指明,雜環與環系可藉由置換該碳 或氮上之氫而經由任何可用碳或氮連接。 芳族」意指各個環原子基本上在同一平面上並有 一個執域垂直於該環平面,並且(4η + 2)π個電子(其 ^ 11為正整數)與該環聯結以射休克耳㈣。用語「芳Substituted by a substituent of CrC4 alkyl; 20\independently fluorene, CrC3 alkyl or CrC3 dentate; R31 is independently hydrazine, CrC3 alkyl or Cl_C3 _alkyl; r32 is hydrazine or CrC3 alkyl; W5 is CrC4 alkylene W1 is C2-C4 alkyl, -(ch2)2och2- or -(CH2)3〇CH2-; R is phenyl or -W3(phenyl), each of which is selected from two at most Substituted by a substituent of R21; or -G; or CrC6 alkyl or hydrazine <:8 cycloalkyl; W3 is Crc6 alkyl, C2-C6 stretching or c2-C6 alkynyl; 22 25 201240602 each G Independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered slightly bicyclic ring system, each ring or ring system optionally having up to five R21 selected from a carbon ring member Substituted by a substituent of R22 on a nitrogen ring member; 5 each R21 is independently halogen, cyano, hydroxy, amine, nitro, -CHO, -C(=0)0H '-C(=0)NH2 ' - C(=S)NH2 ' -C(=0)NHCN, -C(=0)NH0H, -SH, -S02NH2, -S02NHCN, -S02NHOH, -OCN, -SCN, -SF5, CVC6 alkyl, c2- C6 alkenyl, c2-c6 alkynyl, crc6 halo 10 alkyl, c2-c6 haloalkenyl, c2-c6 halo fast radical, c3-c8 cyclodextrin, C3-C8 halo ring, C4-C10 ring Hyun 1 base, C4-C10 soil burnt * , C3-C8 ί 稀, C3-C8 halo ring, C2_Cg oxyalkyl, C4-C1G ring oxyalkyl, C3-CiQ oxynitride, C2-C8 sulphur-burning, C2-C8 Institute is continuously brewed with 15 bases, c2-c8 alkoxyhaloalkyl, c2-c5 cyanoalkyl, crc6 hydroxyalkyl, crc6 alkoxy, crc6 haloalkoxy, c3_c8 cycloalkoxy, c3 -c8 halocycloalkoxy, c4-c10 cycloalkanoyloxy, c2-c6 alkenyloxy, c2-c6 haloalkenyloxy, c2-c8 alkoxyalkoxy, c2-c8 alkoxycarbonyl, crc6 Alkylthio, 20 CVC6 halogen thiol, C3-C8 ring thiol, CVC6 sinter sulphate, halogen sulphide, subcontinental, C^-Cg calcined, crc6 halosulfonyl, C3-c8 cycloalkanesulfonyl, crc6 amphoteric, C2-C8 dialkylamine, C1-C6 haloalkyl, C2-C8 haloalkylamine or C3-C8 cycloalkylamine; 23 201240602 R22 is independently Ci_C6, C2-C6 alkenyl, C2-C6 alkynyl, CrC6 alkyl, C3-C8 cycloalkyl or C2-C8 alkoxyalkyl; and R23 is a selectively substituted carbon a carbon moiety; 114() is a CrC6 alkyl group; R41 is a CrC6 alkyl group; or R40 and R41 together are _(CH2)4-, -(CH2)5-, CH2CH=CHCH2- or -(ch2 ) 2o(ch2) 2- It can be used to prepare a compound of formula 1. [Embodiment] 15 20 "As used herein, the terms "including", "including", "having", "including", "characteristic" or any other variation thereof are intended to cover non-exclusive. And any composition, mixture, process, or method that is not specifically limited to 1 ', but may be included in the composition, mixture, process Other elements. The conjunction "by . * ^ ^^ ^ ..., and into" excludes any unspecified meta-words that will be sealed (four) t st in the application for financial resources, such as the use of impurities, in addition to the usual And the related words "by ·····. group, L include those substances other than enumerated. When the connection is not followed by 20%", the clause of the subject of the patent scope is now requested, and the elements are generally; The elements mentioned in the clause; the other conjunctions "main I, excluded from the scope of the patent. The literal disclosure of '··..·" is used to define materials, steps, features, components or elements other than those defined. 24 25 201240602 The composition or element 1 is just like these extra materials, (4), features, inclusions and "by! Γ mainly consists of ·····." The middle ground. Some open-ended terms such as "contains" are defined as - inventions or their stipulations are not otherwise stated.) The narrative should be interpreted as "master again,; 4" or "by ···· ". Composition" describes the invention. Sexual bite = otherwise expressly stated to the contrary, "or" means a case involving 10 15 20 (, Β Β Α疋 Α疋 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 Α ( ( ( ( ( ( ( (or exist), and ΑΗ are all true (or exist). 疋 「 一 一 一 一 位于 位于 位于 位于 之前 之前 之前 之前 之前 之前 之前 之前 之前 旨在 旨在 旨在 旨在 旨在 旨在 旨在 旨在 旨在 旨在 旨在 旨在 旨在 旨在 旨在An element or a component, and the singular form of the dollar is also plural, unless the number is obviously singular. Or bloody, as mentioned in the article, the term "seedling" is used alone. Smoke, which means a young plant that develops from the seed germ. For example, the term "broad leaf" is used alone or in combination with other words to make it "broad weed", which means A dicotyledonous or dicotyledonous plant, a term used to describe a group of angiosperms characterized by two cotyledons of the embryo. As used herein, the term "alkylating agent" refers to a compound in which three free radicals are passed through a Carbon atom bonding to a detachment base 25 25 201240602 a halide or a sulfonate which can be replaced by bonding a nucleophilic agent to the aforementioned carbon atom. Unless otherwise indicated, the term "alkylating agent" does not limit the carbon radical of Shai as a hospital base; The carbon-containing radicals in the oxidizing agent include various radicals of the ruthenium-bonding substituents, which are designated, for example, for R1, R2 and R3. The term "dealkylating agent" means pyrolysis of carbon-carbon or carbon. _ Oxygen-bonding reagent. In the above description, the term "alkyl" is used alone or in compound words such as "alkylthio" or "dentate alkyl", and includes straight-chain or branched alkyl groups, such as Base, ethyl, n-propyl, isopropyl or different butyl, pentyl or hexyl isomers. "Alkenyl" includes straight or branched olefins such as vinyl, 1-propenyl, 2-propenyl The dilute group and the different butylon, pentenyl and hexenyl isomers. "Alkenyl" also includes polyene such as anthracene, 2-propadienyl and 2,4-hexadienyl. Included are straight-chain or branched alkyne such as ethynyl, 1-propynyl, 2-propanyl and the different butyl, pentyl and hexynyl isomers. "Alkynyl" may also include The moieties of the plural oxime bond are, for example, 2,5·hexadiynyl. "Alkylene" means a straight chain or a branched alkanediyl group. Examples of "alkylene group" include CH2, CH2CH2, CH(CH3), CHKI^CH2, CH2CH(CH3) and different butyl isomers. "Extend alkenyl" means a straight or branched olefinic diyl group containing an ethylenic bond. Examples of "alkenyl" include CH=CH, CH2CH=CH, CH=C(CH3) and different butenyl isomers. When the examples provided indicate that the two variants are "along together as a alkenyl group", these examples do not limit the point of attachment. For example, when rh and Ri8 together act as -CH=CHCH2-, the point of attachment of this exemplary group is interpreted as being attached to one of the R14 or R18 variants (ie, equivalent to -CH2CH=CH_). "Extend alkynyl" means a straight chain or branched alkyne 2 26 201240602 group which contains a hydrazone bond. Examples of "alkynyl" include ceC, CHzOC, C^CCH2 and different butynyl isomers. "Alkoxy" includes, for example, decyloxy, ethoxy, n-propoxy, isopropoxy and various butoxy, pentyloxy and hexyloxy isomers. "Alkane 5 oxyalkyl" means an alkoxy group substituted on the alkyl group. Examples of the "alkoxyalkyl group" include CH3〇CH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2^CH3CH2OCH2CH2 group" means that an alkoxy group is substituted on the alkoxy group. "Alkenyloxy" includes a straight or branched alkenyloxy moiety. Examples of the "alkenyloxy group" include 10 H2C=CHCH20, (CH3)2C=CHCH20, (CH3)CH=CHCH20. (CH3)CH=C(CH3)CH20 and CH2=CHCH2CH2〇. "Alkynyloxy" includes a straight or branched alkynyloxy moiety. Examples of "alkynyloxy" include HOCCH20, ch3c=cch2o and CH3〇CCH2CH2〇. "Alkoxyalkenyl" includes a straight or branched alkenyl group substituted with an alkoxy group 15. Examples of "alkoxyalkenyl" include CH3OCH=CH, CH3C(OCH3)=CH and CH3CH2〇CH=CHCH2. "Alkoxyalkyloxyalkyl" means an alkoxyalkoxy group substituted on the alkyl group. Examples of the "alkoxyalkyloxyalkyl group" include CH3OCH2OCH2, CH3OCH2OCH2CH2, 20CH3CH2OCH2OCH2 and CH3OCH3CH2OCH2CH2. "Alkylthio" includes branched or straight chain alkylthio moieties such as methylthio, ethylthio and propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylene" also contains two mirror image isomers of a sulfhydryl group. Examples of "alkylsulfinyl" include CH3S(0)_, 25ch3ch2s(o)-, CH3CH2CH2S(0)-, (CH3)2CHS(0)- and different sulfinyl, sulfinamide Base and hexylsulfinyl isomer. Examples of "alkane 27 201240602 sulfonyl" include CH3S(0)2-, CH3CH2S(0)2-, CH3CH2CH2S(0)2., (CH3)2CHS(0)2- and different butasulfonyl, pentane It is confirmed that the sulfhydryl group and the hydrazine isomer. The definitions of "circulating sub-items" and "cycloalkylsulfonyl" are similar to the above terms "alkylsulfinyl" 5 and "alkylsulfonyl". "Ceramic sulfur base" means that there is a sulfur-substituted group on the base. Examples of the "sulfur-saturated alkyl group" include ch3sch2, ch3sch2ch2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2; "alkylsulfinylalkyl" and "alkylsulfonylalkyl" 10 respectively include corresponding sulfoxide and sulfone. The "alkylamino group" includes an NH radical substituted with a linear or branched alkyl group. Examples of the "alkylamino group" include CH3CH2NH, CH3CH2CH2NH and (CH3)2CHCH2NH. Examples of the "dialkylamino group" include (CH3)2N, (CH3CH2CH2)2N and CH3CH2(CH3)N. "Alkylaminoalkyl" means that the alkylamine group has 15 alkyl groups on the alkyl group. Examples of the "alkylaminoalkyl group" include CH3NHCH2, ch3nhch2ch2, ch3ch2nhch2, CH3CH2CH2CH2NHCH2 and CH3CH2NHCH2CH2. Examples of the "dialkylamine alkyl group" include ((ch3)2ch)2nch2, (CH3CH2CH2)2NCH2 and CH3CH2(CH3)NCH2CH2. The term "alkane 20 carbonylamino" denotes an alkyl group bonded to a C(=0)NH group. Examples of the "alkylcarbonylamino group" include ch3ch2c(=o)nh and ch3ch2ch2c(=o)nh. "Alkylcarbonylthio" means a straight or branched alkylcarbonyl group attached to a sulfur atom and bonded via a sulfur atom. Examples of the "alkylcarbonylthio group" include 25 ch3c(=o)s, ch3ch2ch2c(=o)s and (CH3)2CHC(=0)S. The term "alkyl(thiocarbonyl)oxy" denotes an alkyl group bonded to a thiocarbonyl group 28 201240602 (attached to an oxygen atom and bonded via an oxygen atom). Examples of the "alkyl(thiocarbonyl)oxy group" include ch3ch2c(=s)o and CH3CH2CH2C(=S)0. The term "alkyl (thiocarbonyl)thio" refers to an alkyl group bonded to a sulfur atom. Examples of the "alkyl (thiocarbonyl)thio group" include CH3CH2C(=S;)S. "二烧烧基" includes three branched and/or straight-bonded radicals linked to a broken atom and linked via a broken atom, such as trimethyl sulfanyl, triethyl decyl and tert-butyl dimethyl矽基. Examples of the "halotrialkylsulfonyl group" include CF3(CH3)2Si-, (CF3)3Si- and CH2Cl(CH3)2Si-. "Hydroxyl 10 15 20 alkyl" means an alkyl group substituted with one hydroxy group. Examples of "hydroxyalkyl" include HOCH2CH2, CH3CH2(OH)CH and HOCH2CH2CH2CH2. "Cyanoalkyl" means an alkyl group substituted by a cyano group. Examples of "cyanoalkyl" include NCCH2, ncch2ch2 and ch3ch(cn)ch2. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "alkylcycloalkyl" denotes an alkyl group substituted on a cycloalkyl group and includes, for example, ethylcyclopropyl, isopropylcyclobutyl, 3-indolecyclopentyl and =methylcyclohexyl. The term "rings" means that there is a % alkyl group substitution on the alkyl group. Examples of "households" include cyclopropenyl, cyclohexylethyl and other cycloalkyl groups which are bonded to a straight or branched alkyl group. The term "alkoxy" means a cycloalkyl group bonded via an oxygen atom, such as a pentyloxy group and a cyclohexyloxy group. The term "burning ring-burning group" means not finding a silk H-based group on a t-alkyl group. Examples of the fluorene-based group include a fluorenyl group, a butyl group, and a straight bond or a branch group which is condensed to a ring group. . The silk "material Wei" means that the lysyl group is substituted with an alkoxy group. Examples of the aerobic cycloalkyl group include a methoxycyclopropane 29 25 201240602 group, an ethoxycyclohexane, and other straight or branched alkoxy groups bonded to a weiyl group. The "cyclic oxy group" means a ring-yard base to which an oxygen atom is bonded, and the oxygen atom is bonded to the alkyl chain. Examples of the "aristocratic oxy group" include a cyclodecyloxy group, a cycloerythroxy group, and other cycloalkyl groups bonded to a linear 5- or branched alkoxy group. Examples of the "cyanocycloalkyl group" include 4-cyanohexyl and 3-cyanocyclopentyl/cycloalkenyl groups including groups such as a cyclopentenyl group and a cyclohexenyl group, and a group having more than one double bond. 'such as 1,3- and 1,4-cyclohexadienyl. The term "fun" is used either alone or in compound words such as "haloalkyl 10" or when used in the description of "passage substituted by dentate", including fluorine, gas, bromine or iodine. . Furthermore, when used in a compound such as "haloalkyl" or when used in the description of "alkyl substituted by halogen", the alkyl group may be partially or completely substituted with the same or different halogen atoms. . Examples of "dental base" or "halogen substituted by halogen" include F3C-, C1CH2-, CF3CH2- and CF3CC12-. The terms "halocycloalkyl", "haloalkoxy", "haloalkylthio", haloalkylsulfinyl, alkanesulfonyl, "haloenyloxy", "haloalkoxy", "halogen" Alkenyl", "haloalkynyl", "haloalkoxyalkyl", "haloalkoxyalkoxy", "haloalkanooxyalkoxy", "haloalkoxyhaloalkyl", "haloalkylamino" "Homo 20 alkylaminoalkyl", "cycloalkoxy", "dental cycloalkyloxyalkyl", "halocycloalkylalkyl", "halocycloalkenyl", "halocycloalkenyloxy", "halocycloalkenyloxy", "ring ring oxygenation base", "burning oxygen 13⁄4 courtyard oxygen", oxygen-burning functional group, haloalkylcarbonyloxy and the like are defined by the term "||alkyl "similar. Examples of "haloalkoxy" include cf3o-, cci3ch2o-, hcf2ch2ch2o-25 and CF3CH20-. Examples of "haloalkylthio" include CC13S-, CF3S-, CC13CH2S- and C1CH2CH2CH2S-. The example of "haloalkyl sulfinyl" is cf3s(o)·, CC13S(0)-, cf3ch2s(o)- and cf3cf2s(o)-. Examples of "haloalkylsulfonyl" include CF3S(0)2-, cci3s(o)r, cf3ch2s(o)2• and cf3cf2s(o)2-. Examples of "haloalkenyl" include (C1)2C=CHCH2- and CF3CH2CH=CHCH2-. The "_ 5 alkynyl group" actually includes HC=CCHC1-, CF3CeC-, CC13C=C- and FCH2〇CCH2-. Examples of the "haloalkoxyalkoxy group" include CF30CH20-, C1CH2CH20CH2CH20-, C13CCH20CH20-, and a branched-chain derivative. Examples of the "halogenated amine group" include CF3(CH3)CHNH, (CF3)2CHNH and CH2C1CH2NH. The phrase "ii dialkyl", whether used alone or in a compound such as "i dialkylamino", means that at least one of the two alkyl groups is substituted with at least one halogen atom, and each The dentate alkyl group can be independently substituted partially or completely by the same or different functional atom. Examples of the "dentate dialkylamino group" include (BrCH2CH2)2N and 15BrCH2CH2(ClCH2CH2)N. "Alkylcarbonyl" means a straight or branched alkyl group bonded to a c(=o) group. Examples of "alkylcarbonyl" include CH3C(=0)-, CH3CH2CH2C(=0)- and (CH3)2CHC(=0)-. Examples of "alkoxycarbonyl" include ch3oc(=o)-, ch3ch2oc(=o)-, 20ch3ch2ch2oc(=o)_, (ch3)2choc(=o), and different butoxy- or pentyloxycarbonyl groups Isomer. The terms "decanecarbonyl", "haloalkoxycarbonyl", "alkoxycarbonyl", "cycloalkoxycarbonyl", "cycloalkaneoxycarbonyl" and "cycloalkylaminecarbonyl" are all similar. The term "alkoxycarbonylamino" denotes a straight or branched alkoxy group bonded to the 25 C (=0) group of a monoamino group. Examples of the "alkoxycarbonylamino group" include ch3oc(=o)nh_ and CH3CH20C(=0)NH-. Examples of the "alkylamine 31 201240602 carbonyl group" include ch3nhc (=o), ch3ch2nhc (=〇), ch3ch2ch2nhc (=o), (ch3)2chnhc (=o) and different butylamine- or pentylamine carbonyl isomers. Examples of the "dialkylaminecarbonyl group" include (CH3)2NC(=0), (ch3ch2)2nc(=o), 5CH3CH2(CH3)NC(=0), (CH3)2CH(CH3)NC(=0) With CH3CH2CH2(CH3)NC (=0). The term "alkylcarbonyloxy" denotes a straight or branched alkyl group bonded to a c(=o)o group. Examples of the "alkylcarbonyloxy group" include CH3CH2C(=0)0 and (CH3)2CHC(=0)0. The term "alkanoalkoxy" denotes an alkylcarbonyl group bonded to an alkoxy group. Examples of the "alkylcarbonyl 10 alkoxy group" include CH3C(=0)CH2CH20 and CH3CH2C(=0)CH20. Examples of the "alkoxycarbonyloxy group" include CH3CH2CH20C(=0)0 and (CH3)2CH0C(=0)0. The term "cycloalkylcarbonyloxy" means a cycloalkylcarbonyl group bonded to an oxygen. Examples of the "cycloalkylcarbonyloxy group" include cyclopropyl-c(0)0- and cyclohexyl-c(0)0-. 15 "Alkylsulfonylamino" means an NH radical substituted by an alkanesulfonyl group. Examples of the "alkylsulfonylamino group" include CH3CH2S(=0)2NH- and (CH3)2CHS(=0)2NH-. The term "halo sulfonyloxy" means a thiol group bonded to an oxygen atom. Examples of "burning oxime" include ch3s(=o)2o-, CH3CH2S(=0)20-, 20ch3ch2ch2s(=o)2o-, (ch3)2chs(=o)2o- and different butyrene Alkoxy, pentylsulfonyloxy and hexapyloxyl isomers. The term "cycloalkoxyalkyl" denotes a cycloalkoxy group substituted on an alkyl group. Examples of the "cycloalkoxyalkyl group" include a cyclopropoxymethyl group, a cyclopentyloxyethyl group and other cycloalkoxy 25 groups bonded to a linear or branched alkyl group. The term "cycloalkylthio" denotes a cycloalkyl group attached to a sulfur atom and bonded via a sulfur atom, such as a cyclopropylthio group and a cyclopentylthio group; "ring 32 201240602 alkanesulfonyl group" includes its corresponding sulfone. "Alkylcycloalkyl" means a group which is substituted with a cycloalkyl group. Examples of the "ring-burning group" include a 2-, 3- or 4-methyl group or an ethylcyclohexylmethyl group. The term "cycloalkoxyalkyloxyalkyl" denotes a 5-cycloalkoxy group attached to an alkoxy group of an alkoxyalkyl group. Examples of the "cycloalkoxyalkyloxyalkyl group" include (cyclopropyl)OCH2OCH2-, (cyclobutyl)OCH2CH2〇CH2_ or (cyclohexyl) OCH2〇CH2CH2_. The term "cycloalkanecycloalkyl" denotes a cycloalkyl substitution on the other cycloalkyl ring wherein each cycloalkyl ring independently has from 3 to 7 carbon atoms. Examples of the "cycloalkanecycloalkyl group" include a cyclopropylcyclopropyl group (e.g., a bicyclopropyl-1-yl group, a 1,1,-dicyclopropyl-2-yl group), a cyclohexylcyclopentyl group (e.g., a 4-ring group). Pentocyclohexyl) and cyclohexylcyclohexyl (for example U'-dicyclohexyl-1-yl) with different cis- and trans-cycloalkylcycloalkyl isomers (for example (1 foot 2, 1) 1'-bicyclopropyl-2-yl and (1 foot 2 and)-1, fluorene-bicyclopropyl-2-yl). 15 "Secondary oxyalkyl" means the same in the base of the compound a separate alkoxy group substituted on carbon. Examples of "dialkoxyalkyl" include (ch3o)2ch- and ch3ch2o(ch3o)ch-. "Cycloalkylamino" means a NH radical substituted by a phenolic group. Examples of the "cycloalkylamino group" include a cyclopropylamino group and a cyclohexylamino group. "Cycloalkyl (alkyl)amino group means a ring of 20 aromatized groups wherein the hydrogen atom is derived from a radical Examples of "cycloalkyl (alkyl) amine groups include, for example, cyclopropyl (methyl) amine groups, cyclobutyl (butyl) amine groups, cyclopentyl (propyl) amine groups, cyclohexyl groups ( Alkyl group, etc. The term "ring-burning amine "base" means a base The group has a cycloalkylamino group substituted. Examples of "cycloalkylaminoalkyl" include cyclopropylaminomethyl, 25-cyclopentylaminoethyl and other cyclic aminino groups bonded to a linear or branched alkyl group. 33 201240602 "Cycloalkylcarbonyl" means a cycloalkyl group bonded to a c(=〇) group, which includes, for example, cyclopropylcarbonyl and cyclopentylcarbonyl. The term "cycloalkoxycarbonyl" means bonded to a cycloalkoxy group of a c(=o) group, such as cyclopropoxycarbonyl and %: pentoxy. "cyclohexylamine" means a cycloalkane bonded to a c(=o) group of 5 An amine group such as a cyclopentylamine carbonyl group and a cyclohexylamine carbonyl group. "Cycloalkaneoxycarbonyl group" means a cycloalkylalkoxy group bonded to a c(=o) group. The present invention includes a cyclopropyloxymethyl group and a cyclopentanyloxy group. "Alkoxy" means a cycloalkylcarbonyl group bonded to an oxygen atom and bonded via an oxygen atom. Examples of "cycloalkaneoxy" include a ring. Hexacarbonyl 10 oxy and cyclopentylcarbonyl. The term "cycloalkyl" means a ring-substituent substitution on a group. "Cycloalkenyl" examples include cyclobutenyl and cyclopentane. dilute Ethyl and other cycloalkenyl groups bonded to a straight or branched alkyl group. The term "cycloalkenyloxy" means a cycloalkenyl group bonded via an oxygen atom, such as a ring 15 penteneoxy group and a ring. Hexenyloxy. The term "cycloalkenyloxyalkyl" means a cycloalkenyloxy group substituted on an alkyl group. Examples of "cycloalkenyloxyalkyl" include cyclobutenyloxy, cyclopenteneoxy a cycloalkenyloxy group bonded to a straight or branched alkyl group. The term "alkylamine" means a 20-bond or branched-chain bond bonded to a continuation group. Amino group. An example of an "alkali thiol" group includes CH3NHS(0)2- or CH3CH2CH2NHS(0)2-. The term "dialkylamine sulfonyl" denotes a straight or branched dialkylamino group bonded to a monosulfonyl group. Examples of a "dialkylamine sulfonyl" group include (CH3)2NS(0)2- or (CH3CH2CH2)2NS(0)r. The total number of carbon atoms in the 25-substituent group is indicated by the prefix "Ci-Cj", where i and j are numbers from 1 to 14. For example, CrC4 Institute 34 201240602 Sulfonyl represents methanesulfonyl to butasulfonyl; c2 alkoxyalkyl represents CH3OCH2-; c3 alkoxyalkyl represents, for example, CH3CH(OCH3)-, CHsOCHzCH2. or CH3CH2OCH2-; The alkoxyalkyl group means various isomers of an alkyl group substituted by an alkoxy group having a total of four carbon atoms, and examples include ch3ch2ch2och2- and CH3CH2OCH2CH2-. When a compound is substituted with a substituent and the substituent bears a subscript (indicating that the number of such substituents may exceed one), the substituents (when they exceed one) are independently selected from the defined substituents. Group, 10 15 20 For example (Rv)r, in the U-1 of the show 3! · is 1, 2, 3, 4 or 5. When a group contains a substituent which may be hydrogen, such as R2, R3, r4, R5, R6, R7, r8, r9, ri〇, rii, Ru, r13, r14, r15 R _, R19 or R2q, Then, when the substituent is hydrogen, it is considered that the group is unsubstituted. When the -variable base_ is shown as being selectively coupled to a position, such as (RV)r in display 2, then hydrogen may be at that position (ie, when F is G), even if the variable base is gj This statement is not included in the definition. When the - or a plurality of positions on the group are described as "untaken or unsubstituted", the hydrogen atom is attached to occupy any of the "rings" or "," For example, the substituent GA) is a carbocyclic or heterocyclic ring. The term "ring system" is:, a nucleus of copper. The terms "bicyclic" and "fused bicyclic" form a ring system consisting of L (d) and unless otherwise stated: diterpenes may be saturated, partially unsaturated or fully unsaturated. The term ', no mourning', means that the two bonds are in a single atom as a carbon spiro or a heterocyclic ring. The use of this "production of the heart and the use of b J-clothes" refers to the formation of a ring or ring system 35 25 201240602 main chain of atoms or other groups (such as c (= o), c (= s), s (o) or S(〇)2) 0 s = "Carbon ring", "carbocyclic compound" or "carbocyclic ring" means a % or ring system in which the atoms forming the ring backbone are selected only from carbon. Unless otherwise stated, a slave ring can be saturated, partially unsaturated or fully unsaturated. When a fully unsaturated carbon ring satisfies the Httcke丨, s rule, the ring is also referred to as the "aromatic ring". "Saturated carbocycle" means a ring in which the main chain is in the domain of a carbon atom which is bonded to each other by a single bond; unless otherwise indicated, the remaining carbon valence is occupied by a hydrogen atom. The term "heterocycle" or "heterocycle" means a ring or ring system wherein the atom forming the primary bond of the ring is not carbon, such as nitrogen, oxygen or sulfur. A heterocyclic ring typically contains no more than 4 nitrogen atoms, no more than 2 oxygen atoms and no more than 2 sulfur atoms. Unless otherwise stated, a heterocyclic ring can be a 77 unsaturated or fully unsaturated ring. When the "completely unsaturated impurity % meets the shock formula" then the ring is also referred to as a "heteroaryl ring" or "aryl heterocycle". Unless otherwise indicated, a heterocyclic ring and a ring system can be attached via any available carbon or nitrogen by replacing the hydrogen on the carbon or nitrogen. "Aromatic" means that each ring atom is substantially in the same plane and has a domain perpendicular to the plane of the ring, and (4η + 2) π electrons (which are positive integers) are associated with the ring to emit shock (4). The word "fang"

環系」表示-碳環系或雜環系,其中該環系的 環為芳族。 U 如本文中所用者,下列定義應適用於本文中,除非 另有^明。賴「轉性地經取代」係與詞組「經 或未經取代」互換制。除非另有指明,—選擇性地經 36 201240602 取代之基團可在該基團的各個可取代位置具有一取代 基,並且各取代係互相獨立。 如上所述,G可為(尤其)一 6_至12_員飽和或部 分飽和碳螺環或雜螺環環系(選擇性地包括環員),各 環或環系選擇性地經至多五個如發明内容所定義的取 代基取代(即R21或R22)。6-至12-員飽和或部分飽和 碳螺環或雜螺環環系(選擇性地包括選自c(=〇)、 C(=S)、C(=NR29)、C(=N-OR3°)或 〇NN(R29)2 的環員並 且選擇性地經至多五個取代基取代)的實例包括說明於 展示1中之環%1至%104,其中y為任何如發明内容 中針對GA所定義之取代基(即或r22),並且1>典 型為0至4之整數。值得注意的是當將該v基團上的連 接點繪示成浮動時,則該V基團可藉由置換一氫原子而 經由該V基圑的任何可用碳或氮連接至式1之其餘部"Ring system" means a carbocyclic or heterocyclic ring wherein the ring of the ring system is aromatic. U As used herein, the following definitions shall apply to this document unless otherwise stated. Lai's "replacement by substitution" is interchangeable with the phrase "via or without substitution". Unless otherwise indicated, a group optionally substituted by 36 201240602 may have a substituent at each substitutable position of the group, and each substituent is independent of each other. As noted above, G can be, in particular, a 6- to 12-membered saturated or partially saturated carbon spiro or hetero-spirocyclic ring (optionally including a ring member), each ring or ring system selectively passing up to five Substituents substituted as defined in the Summary of the Invention (i.e., R21 or R22). 6- to 12-membered saturated or partially saturated carbon spiro or heterospiro ring systems (optionally selected from the group consisting of c(=〇), C(=S), C(=NR29), C(=N-OR3 Examples of °) or 环NN(R29)2 ring members and optionally substituted with up to five substituents include rings %1 to %104 as illustrated in Exhibit 1, where y is any as described in the Summary of the Invention for GA The substituents defined (i.e., or r22), and 1> are typically integers from 0 to 4. It is worth noting that when the point of attachment on the v group is depicted as floating, the V group can be attached to the remainder of Formula 1 via any available carbon or nitrogen of the V group by replacing a hydrogen atom. unit

201240602 (RV)rUl V-10 K V-13 p V-ll201240602 (RV)rUl V-10 K V-13 p V-ll

V-12 V-15V-12 V-15

V-17V-17

,0 V-20, 0 V-20

s-S-

(RV)r (RV)r(RV)r (RV)r

Si V-23 N-V-24Si V-23 N-V-24

V-27V-27

V-26V-26

V-29V-29

V-32V-32

38 )120124060238)1201240602

V-34V-34

V-39V-39

(RV)r(RV)r

(RV)r(RV)r

39 201240602 (RV)r39 201240602 (RV)r

(Rv)r(Rv)r

V-56 (RV)rV-56 (RV)r

V-61 (Rv)rV-61 (Rv)r

N* V-62N* V-62

(RV)r(RV)r

V-64 (Rv)rV-64 (Rv)r

V-65V-65

V-66 N*V-66 N*

V-67 (Rv)rV-67 (Rv)r

(RV)r(RV)r

V-69V-69

V-70V-70

V-71 N*V-71 N*

V-72V-72

V-73 (Rv)rV-73 (Rv)r

V-75V-75

40 201240602 V-7640 201240602 V-76

V-82V-82

O v 〇 V-77O v 〇 V-77

V-78V-78

V-81V-81

V-86V-86

V-91V-91

(Rv)r Q(Rv)r Q

V-101V-101

41 20124060241 201240602

以及 (RV)rAnd (RV)r

V-104 5 當GA為一 9-員部分餘和稍合且含有碳環員與2個 氮環員之環系時,該環選擇性地經至多2個選自在碳環 員上之R21與在氮環員上之R22的取代基取代。展示1A 顯示含有碳環員與2個氮環員之9_員部分飽和稠合環 系的實例並且其係選擇性地經Rv(即R21或R22)取代。 值得注意的是當將該T基團上的連接點繪示成浮動 時,則該T基團可藉由置換一氫原子經由該T基團的任 何可用碳或氮連接至式1之其餘部分。 10V-104 5 When GA is a 9-membered part and a slightly enclosed ring system containing a carbon ring member and 2 nitrogen ring members, the ring selectively passes through at most 2 R21 selected from the carbon ring member. Substituted by a substituent of R22 on the nitrogen ring member. Show 1A shows an example of a 9-member partially saturated fused ring system containing a carbocyclic member and two nitrogen ring members and which is optionally substituted with Rv (i.e., R21 or R22). It is worth noting that when the point of attachment on the T group is depicted as floating, the T group can be attached to the remainder of Formula 1 by replacing one hydrogen atom via any available carbon or nitrogen of the T group. . 10

當G為一 5_或6-員雜環時,其可經由任何可用碳 或氮環原子連接至式1之其餘部分,除非另有描述。當 G為(尤其)一 5-或6-員雜環時,其可為飽和或不飽和, 15 選擇性地經一或多個選自由如發明内容中所定義之取 代基群組的取代基取代。一選擇性地經一或多個取代基 取代之5-或6-員雜環的實例包括展示2中說明之環Q-1 42 201240602 ^ 其中R為该選擇性取代基並且為任何如發明 ^谷中針對在碳環員上之R21或在氮環員上之R22所定 的取代基,並且!*為〇至4之整數,此係限於各q基 團上可用位置數目。因為q-29、Q 3〇、Q 36、Q 37、 Q-38、Q-39、Q-40、Q-41、Q-42 與 Q-43 僅具有一個可 用位置,針對這些Q基團Γ係限於整數0或1,並且r 為〇意指該Q基團係未經取代並且一氫係出現在由(RV) 所指示的位置。 ^When G is a 5- or 6-membered heterocyclic ring, it can be attached to the remainder of Formula 1 via any available carbon or nitrogen ring atom unless otherwise stated. When G is (especially) a 5- or 6-membered heterocyclic ring, it may be saturated or unsaturated, 15 optionally via one or more substituents selected from the group of substituents as defined in the Summary of the Invention. Replace. Examples of 5- or 6-membered heterocyclic rings which are optionally substituted by one or more substituents include ring Q-1 42 201240602, which is illustrated in Figure 2, wherein R is the selective substituent and is any such as the invention ^ In the valley, the substituents for R21 on the carbon ring member or R22 on the nitrogen ring member, and! * is an integer from 〇 to 4, which is limited to the number of available positions on each q group. Because q-29, Q 3〇, Q 36, Q 37, Q-38, Q-39, Q-40, Q-41, Q-42 and Q-43 have only one available position for these Q groupsΓ It is limited to the integer 0 or 1, and r is 〇 means that the Q group is unsubstituted and a hydrogen is present at the position indicated by (RV). ^

Q-1 (Rv 〇 Q-6Q-1 (Rv 〇 Q-6

Q-16Q-16

Q-26 展示2 3 (RV)r Ti; 4 (RV)r 、公 Q-2 Q-3 (RV)r (Rv)r '—N Q-7 Q-8 Xi; Q-12 Q-13 (Rv)r Q-17 Q-18 4 (Rv)r W N—S 3 (RV)r Q-22 Q-23 3 (RV)r s'—N 4 (R\ 、YV N—N Q-27 Q-28 3 (RV)rQ-26 shows 2 3 (RV)r Ti; 4 (RV)r, male Q-2 Q-3 (RV)r (Rv)r '-N Q-7 Q-8 Xi; Q-12 Q-13 (Rv)r Q-17 Q-18 4 (Rv)r WN—S 3 (RV)r Q-22 Q-23 3 (RV)r s'—N 4 (R\ , YV N—N Q-27 Q-28 3 (RV)r

Q-9 4 (RV)rQ-9 4 (RV)r

Q-19 4 (RV)r Q-14 4 (Rv)rQ-19 4 (RV)r Q-14 4 (Rv)r

、YV S一N Q-24, YV S-N Q-24

Q-29 Q-25Q-29 Q-25

43 201240602 •N \=N Q-31 (RV)r Q-3643 201240602 •N \=N Q-31 (RV)r Q-36

(RV)r Q-41(RV)r Q-41

N—N (RV)r NN-N (RV)r N

Q-51 XN/? Q-56 n—n Q-32 Ν/Γ (Rv)r I N—N Q-33 (R\ N=( Q-37Q-51 XN/? Q-56 n-n Q-32 Ν/Γ (Rv)r I N-N Q-33 (R\ N=( Q-37

N (Rv>r N Q-42 Q-38 N.N (Rv>r N Q-42 Q-38 N.

N (RV)r Q-43N (RV)r Q-43

、严 (Rv N—N Q-47Strict (Rv N-N Q-47

Q-52Q-52

,NT 6 Q-57 N=N Q-48, NT 6 Q-57 N=N Q-48

Q-53Q-53

XT N Q-58XT N Q-58

以及 Q-59 Q-60 值得4意的疋§ G為—選擇性地經—或多個選自 如發明内料針對R21所定義之取代基群_取代基取 代之所5·或6·員雜環時,該雜環之—或兩個碳環員可選 擇性地為在一羰基部分之氧化形式。 一 5-或6-員雜環的實例包括如展示3中所說明的環 U-1至U-36。值得注意的是當將該1;基團上的連接點 繪示成浮動時’則該U基團可藉由置換一氫原子而經由 該U基團的任何可用碳或氮連接至式i之其餘部分。該 44 201240602 對應於Rv之選擇性取代基可藉由置換一氫原子而連接 至任何可用碳或氮。針對這些U環,r典型為〇至4之 整數,其限於各U基團上可用位置的數目。 時,5=的是當G包含一選自⑽至叫6之環 :氮。值得注意的是當U2為N時, 内容H或該對應於取代基(如二 内令中針對⑽定義者,即杓取_補滿^如子ζ明 展示3 ^V(R\And Q-59 Q-60 is worthy of 4 G § G is - selectively - or a plurality of substituents selected from the substituents defined in R21 for the replacement of R21, or 5 In the ring, the heterocyclic ring or the two carbocyclic members may optionally be in the oxidized form of a carbonyl moiety. Examples of a 5- or 6-membered heterocyclic ring include the rings U-1 to U-36 as illustrated in the scheme 3. It is worth noting that when the 1; linkage point on the group is depicted as floating, then the U group can be attached to the formula i via any available carbon or nitrogen of the U group by replacing a hydrogen atom. The rest. The 44 201240602 selective substituent corresponding to Rv can be attached to any available carbon or nitrogen by displacement of a hydrogen atom. For these U rings, r is typically an integer from 〇 to 4, which is limited to the number of available positions on each U group. When 5 = is when G contains a ring selected from (10) to 6: nitrogen. It is worth noting that when U2 is N, the content H or the corresponding to the substituent (such as the definition in the second order for (10), that is, _ _ 满 ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^

U-7U-7

U-5U-5

U-6U-6

U-16 (RV)rU-16 (RV)r

U-12 ^V)r υ'8 υ-9 ττ° Ν U·】0 υ·13 U-14 τ〇 , 2U-12 ^V)r υ'8 υ-9 ττ° Ν U·]0 υ·13 U-14 τ〇 , 2

(R\ Ν U-18 U-15 (RV)r U-π (RV)r U-19 (Rv), 、i) U-20 (Rv)r xV、,/;π θ β U'29 U-30 45 201240602(R\ Ν U-18 U-15 (RV)r U-π (RV)r U-19 (Rv), , i) U-20 (Rv)r xV,,/;π θ β U'29 U -30 45 201240602

U-31 以及U-31 and

U-36U-36

U-33U-33

U-34U-34

U-35 如上所說明者,G可為(尤其)一 8_、9_或1〇_員 稠合雙環環系,其選擇性地經—或多個選自如發明内容 中所定義之取代基群組的取代基取代(即R2】或R22)。 選擇性地經一或多個取代基取代之8_、9_或1〇_員稠合 雙環環系的實例包括展示4所說明之環q_81至 Q-123,其中Rv為任何如發明内容中針對G所定義之取 代基(即R21或R22),並且r典型為〇至4之整數。U-35 As described above, G may be, in particular, an 8-, 9- or 1 fluorene-fused bicyclic ring system optionally substituted with one or more substituent groups selected from the group of the invention as defined in the Summary of the Invention. The substituents of the group are substituted (ie R2) or R22). Examples of 8-, 9- or 1-membered fused bicyclic ring systems optionally substituted with one or more substituents include the rings q_81 to Q-123 illustrated in Figure 4, wherein Rv is any as specified in the Summary of the Invention The substituent defined by G (i.e., R21 or R22), and r is typically an integer from 〇 to 4.

Q-81Q-81

展示4Show 4

)r 义V V)r )r 江L Q-85 Q-86 Q-89 Q-90 Q-93)r V V)r )r Jiang L Q-85 Q-86 Q-89 Q-90 Q-93

v^-y i 、0:^ Q-95v^-y i , 0:^ Q-95

Q-84Q-84

Q'92 N (Rv)rQ'92 N (Rv)r

Q-96 (Rv)r 46 201240602Q-96 (Rv)r 46 201240602

Q-121 Q-122Q-121 Q-122

雖然R基團已示於結構Q-l至Q-60及Q-81至 Q-123,但值得注意的是其不必需存在因為它們為選擇 性(optional)取代基。需要取代以填補其原子價的氮原子 係經Η或Rv取代。值得注意的是當(RV\與該q基團間 之連接點係繪示成浮動時,(RV)r可連接至該q基團的 任何可用碳原子或氮原子。值得注意的是當將該Q基團 上的連接點繪示成浮動時,則該Q基團可藉由置換一氫 原子而經由該Q基團的任何可用碳或氮連接至式i之其 餘。卩为。值付注意的是某些Q基團僅可經少於4個RV 47 201240602 基團取代(例如Q-1至Q-5,Q-7至Q-48以及Q-52至 Q-60 ) 〇 已知在該項技術中有廣泛各式合成方法能夠製備 芳族與非芳族雜環及環系,相關方法的大量回顧請參見 八卷集之 Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, PergamonAlthough the R group has been shown in the structures Q-1 to Q-60 and Q-81 to Q-123, it is worth noting that it is not necessarily present because they are optional substituents. The nitrogen atom that needs to be substituted to fill its valence is replaced by hydrazine or Rv. It is worth noting that when (the point of attachment between RV\ and the q group is depicted as floating, (RV)r can be attached to any available carbon or nitrogen atom of the q group. It is worth noting that when When the point of attachment on the Q group is depicted as being floating, the Q group can be attached to the remainder of formula i via any available carbon or nitrogen of the Q group by displacement of a hydrogen atom. Note that certain Q groups can only be substituted with fewer than 4 RV 47 201240602 groups (eg Q-1 to Q-5, Q-7 to Q-48 and Q-52 to Q-60) 〇known There are a wide variety of synthetic methods in the art for the preparation of aromatic and non-aromatic heterocyclic rings and ring systems. For a review of the relevant methods, please refer to the Comprehensive Heterocyclic Chemistry, AR Katritzky and CW Rees editors-in-chief , Pergamon

Press, Oxford,1984 ’ 以及十二卷集之Press, Oxford, 1984 ’ and the 12-volume collection

Heterocyclic Chemistry //, A. R. Katritzky, C. W. Rees 10 20 and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford,1996。 本發明的化合物可以存在有一或多種立體異構 物。各種立體異構物包括鏡像異構物、非鏡像異構物、 阻轉異構物和幾何異構物。熟習該項技術者將明瞭,一 種立體異構物當相對於其他立體異構物為經濃化或當 從其他立體異構物分離出時,其可能活性更高及/戈可 能展不出有益的效果。此外,熟習該項技術者知道如何 分離、濃化及/或選擇性(selectivdy)製備所述立體異構 物。本發明的化合物可以存在為立體異構物的混合物、 個別立體異構物或光學活性形式。 熟習 战孭筏術者將會認知到,許多本發明化合物以 及用於其製備之中間化合物係以多個互變 式存在。例如’當-式1化合物係以A標示為^ ^ 或A-3,並且該R3變項為羥基或〇_Μ+時,即該式1化 合物可存在為-「三酮⑻ketGne)」互變異構物或工一「二 酮烯醇」互變異構物或其組合物。同樣地,备一 合物係以A標示為Μ、A_2或A_3,並且該“ 48 25 201240602 仙時’則該式“匕合物 異構物「二酮硫c-醇」互變異構物或其組合變異構物或一「酮硫鲖烯 化合物(其中A,為:。作為-進-步實例,-r 、或A’-3)可存在為 二嗣硫嗣」互變 式 二酮」互變異構物或兩個可^或A’-3)可 物或其組合物。再者,犯的「酮烯醇」互變異構 片段Μ可存在為具有C變項A定義中之 本發明的上下文中,石傲,、2組_的互變異構物。在 種,並且H種互變^ =餘官能性等效的物 該化合物财可_互_物標===為指涉 與鹽的化合物血型為=變異構物、心化物 :包括式.所二 15 20 體實施例諸如物二:二施: =她體。結晶形式包括基本上代表一單晶類型 的每U及代表一多形體(即不同的結晶類型)混合物 的只施例。用語「多形體」意指—種化合物的特定結晶 形式,該化合物可以不同結晶形式結晶,這些形式在晶 格内具有不同的分子排列與/或構形。雖然多形體可有 相同的化學組成,它們亦可因為共結晶水或其他分子的 存在或不存在而在組成上有所不同,該共結晶水或其他 分子可弱或強地結合在晶格内。多形體可以在化學、物 理和生物特性有所不同’像是晶體形狀、密度、硬度、 顏色、化學穩定性、熔點、吸濕性、懸浮率、溶解速率 和生物利用度。熟習該項技術者將瞭解到,式1化合物 之一種多形體相較於相同式1化合物之另一種多形體 49 25 201240602 或多形體混合物,可顯示出有利效果(例如適於製備有 用的製劑、改善生物性表現)。可藉由熟習該項技術者 已知的方法製備及分離式1化合物之一種特定多形 體,該些方法包括例如利用選定的溶劑及溫度進行結 5 晶。 熟習該項技術者會瞭解到,並非所有的含氮雜環皆 可形成,氧化物,因為氮需要一個可用的孤電子對以 氧化成為氧化物,熟習δ亥項技術者將能辨別出那些可形 成7V-氧化物的含氮雜環。熟習該項技術者亦會瞭解到, 10 三級胺可形成氧化物6製備雜環與三級胺之沁氧化 物的合成方法為熟習該項技術者所極為熟知,包括以過 氧酸如過氧乙酸與間氣過氧苯甲酸(MCPBA)、過氧化 氫、過氧化院基如過氧化三級丁基、過硼酸納及雙環氧 乙烧如二甲基雙環氧乙烷來氧化雜環及三級胺。這些製 15 備氧化物的方法已在文獻中廣泛描述及回顧,例如 · T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press ; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. 2〇 McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press ; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. 25 Boulton, Eds.,Academic Press ;以及 G. W. H_ Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic 50 201240602Heterocyclic Chemistry //, A. R. Katritzky, C. W. Rees 10 20 and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996. The compounds of the invention may exist in one or more stereoisomers. Various stereoisomers include mirror image isomers, non-image isomers, atropisomers, and geometric isomers. It will be apparent to those skilled in the art that a stereoisomer may be more active when it is concentrated relative to other stereoisomers or when isolated from other stereoisomers and may not be beneficial. Effect. Moreover, those skilled in the art know how to separate, concentrate, and/or selectively prepare the stereoisomers. The compounds of the invention may exist as a mixture of stereoisomers, individual stereoisomers or optically active forms. Those skilled in the art will recognize that many of the compounds of the present invention, as well as the intermediate compounds used in their preparation, exist in multiple tautomeric forms. For example, when the compound of formula 1 is designated as A or A-3 by A, and the R3 variable is hydroxy or 〇_Μ+, the compound of formula 1 may exist as - "trione (8) ketGne)". A construct or a "diketoenol" tautomer or a combination thereof. Similarly, the preparation is identified by A as Μ, A_2 or A_3, and the "48 25 201240602 sen" is the formula "the oxime isomer "diketosulfo-c-ol" tautomer or A combination of an isomer or a "ketothiononene compound (wherein A, is: as an example of -in-step, -r or A'-3) may exist as a dithiol" interconversion diketone" Tautomers or two or A'-3) ketones or combinations thereof. Further, the "ketoenol" tautomeric fragment 犯 which is exemplified may exist as a tautomer of the present invention in the context of the present invention having the definition of C variant A. In the species, and H species interconversion ^ = residual functional equivalents of the compound _ _ _ _ = = = = refers to the salt-related compounds blood type = meta isomers, heart compounds: including Two 15 20 body examples such as two: two applications: = her body. The crystalline form includes only the examples which substantially represent a single crystal type of U and a mixture of a polymorph (i.e., different crystal types). The term "polymorph" means a specific crystalline form of a compound which crystallizes in different crystalline forms which have different molecular arrangements and/or configurations within the crystal lattice. Although polymorphs may have the same chemical composition, they may also differ in composition due to the presence or absence of co-crystallized water or other molecules that may be weakly or strongly bound in the crystal lattice. . Polymorphs can differ in chemical, physical, and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate, and bioavailability. Those skilled in the art will appreciate that a polymorph of a compound of Formula 1 may exhibit advantageous effects (e.g., suitable for preparing a useful formulation, as compared to another polymorph 49 25 201240602 or a mixture of polymorphs of a compound of Formula 1). Improve biological performance). A particular polymorph of a compound of formula 1 can be prepared and isolated by methods known to those skilled in the art, including, for example, crystallization using selected solvents and temperatures. Those skilled in the art will understand that not all nitrogen-containing heterocycles can form oxides because nitrogen requires a usable electron pair to oxidize to form oxides. Those skilled in the art will be able to discern those A nitrogen-containing heterocycle of 7V-oxide is formed. Those skilled in the art will also appreciate that the synthesis of 10 tertiary amines to form oxides 6 to prepare heterocyclic and tertiary amine cerium oxides is well known to those skilled in the art, including peroxyacids. Oxyacetic acid and m-peroxybenzoic acid (MCPBA), hydrogen peroxide, peroxides such as tributyl butyl peroxide, sodium perborate and diethylene oxide such as dimethyl dioxirane Ring and tertiary amine. These methods for preparing oxides have been extensively described and reviewed in the literature, for example, TL Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, SV Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, AJ Boulton and A. 2〇 McKillop, Eds., Pergamon Press; MR Grimmett and BRT Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, AR Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, AR Katritzky and AJ 25 Boulton, Eds., Academic Press; and GW H_ Cheeseman and ESG Werstiuk in Advances in Heterocyclic 50 201240602

Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. j.Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. j.

Boulton, Eds·,Academic Press。 熟習該項技術者會瞭解到,gj為化合物的鹽與它們 ^的非鹽形式在環境和生理條件下會處於平衡狀 ^,所以鹽會分享雜形式的生物制。因此式ι化合 f'乏各式鹽類係可用於防治非所欲植物彳即農業上 ° ^ 式1之鹽包括與無機或有機酸之酸加成鹽,如 風演酸、鹽酸、硝酸、璘酸、硫酸、醋酸、丁酸、反丁 ,二酸、乳酸、順丁烯二酸、丙二酸、草酸、丙酸、水 =酉=/酉石酸、4·曱苯確酸或戊酸。當式工化合物含有 生諸如羧酸或酚’則鹽亦包括那些以有機或無 舞/if,諸如0比咬、三乙胺或氨,或鋼、卸、鐘、 鎮或鋇之_、氫化物、氫氧化物或碳酸鹽。因此、 15 20 化=包含選自式ι其^氧化物與農業上適用之鹽的 容中所述的本發明實施例亦包括(其中如 下列實施例中之式1包括其#·氧化物及其趟). 實施例1.如發明内容中所述之式1化合物 1,其中 A 為 A-1、A-3、A-4、A-5 或 α·6。 實施例2,實施例i之化合物,其中八為 A-5 或 a_6。 實施例3_實施例2之化合物,其中A為a-卜 或 A-5。 實施例4.實施例3之化合物,其中A為八^ A-3。 實施例5.實施例4之化合物,其中八為八^。 25 201240602 實施例6.實施例4之化合物,其中A為A-3。 實施例7.式1或實施例1至4其中任一者之化合 物,其中A不為A-1。 實施例8,式1或實施例丨至7其中任一者之化合 物,其中B1為C-1。 實施例9. Si或實施例1至7其中任一者之化合 物’其中B1為C-2。 實施例10.式1或實施例丨至9其中任一者之化合 物’其中B2為C-3。 ° 10 實施例11.式1或實施例其中任―者之化合 物’其中Β2為C-4。 15 實施例12·式1或實施例1 合物’其中Β3為CM。 實施例I3·式1或實施例1 合物’其中B3為c-2。 至U其中任一者之化 至11其中任一者之化 實施例14. 4 1或實施例 合物,其中R1為 至13其中任一者之化Boulton, Eds, Academic Press. Those skilled in the art will appreciate that gj is a salt of a compound and that its non-salt form will be in equilibrium under environmental and physiological conditions, so that the salt will share the biological form of the heteroform. Therefore, the compound of the formula l's various salts can be used to control undesired plants, that is, agriculture. The salt of formula 1 includes acid addition salts with inorganic or organic acids, such as wind acid, hydrochloric acid, nitric acid, Tannic acid, sulfuric acid, acetic acid, butyric acid, trans-butyl, diacid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, water = 酉 = / tartaric acid, 4 · benzoic acid or pentane acid. When the formula compound contains raw such as carboxylic acid or phenol' then the salt also includes those with organic or no dance / if, such as 0 bite, triethylamine or ammonia, or steel, unloading, bell, town or hydrazine, hydrogenation a substance, a hydroxide or a carbonate. Thus, the embodiment of the invention as described in the inclusion of a salt selected from the group consisting of the oxides of the formula and the agriculturally applicable salts also includes (wherein the formula 1 in the following examples includes the oxides thereof Further, Example 1. Compound 1 of Formula 1 as described in the Summary of the Invention, wherein A is A-1, A-3, A-4, A-5 or α·6. Embodiment 2, a compound of Embodiment i, wherein eight is A-5 or a_6. Embodiment 3. The compound of Embodiment 2 wherein A is a- or A-5. Embodiment 4. A compound of Embodiment 3 wherein A is 八^A-3. Embodiment 5. A compound of Embodiment 4 wherein eight are eight. 25 201240602 Embodiment 6. The compound of Embodiment 4 wherein A is A-3. Embodiment 7. The compound of Formula 1 or any one of Embodiments 1 to 4 wherein A is not A-1. The compound of any one of the above formulas, wherein B1 is C-1. Embodiment 9. The compound of Si or any one of Embodiments 1 to 7 wherein B1 is C-2. Embodiment 10. The compound of Formula 1 or any one of Examples 9 to 9 wherein B2 is C-3. ° 10 Embodiment 11. Formula 1 or an embodiment wherein any of the compounds is 'C 2 '. 15 Example 12·Formula 1 or Example 1 ' wherein Β3 is CM. Embodiment I3. Formula 1 or Example 1 wherein B3 is c-2. To any of the above, to any of the examples of Embodiment 14.4 1 or the embodiment, wherein R1 is from 13 to 13

R 為-W】 -^C卜E3)LR26 ;或 R1 為-GA 或-w2GA。 -ν^ΙΧ(=Ε2)ί125 或 20 201240602 實施例15.式1或實施例1至14其中任一者之化 合物,其中R1為R is -W] -^CBu E3)LR26; or R1 is -GA or -w2GA. - ν ΙΧ Ε Ε Ε Ε Ε Ε Ε Ε Ε Ε Ε Ε Ε Ε Ε Ε 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 , ,

實施例16.實施例15之化合物,其中各Q1與Q2 獨立為Ο或N(R31)。 實施例17.實施例16之化合物,其中各Q1與Q2 為Ο。 ίο 實施例18.式1或實施例1至17其中任一者之化 合物,其中Q3為C2_C3伸烷基,其選擇性地經 至多4個選自CrC4烷基的取代基取代。 實施例19.實施例18之化合物,其中Q3為C2-C3 伸烷基,其選擇性地經至多2個選自CrC2烷 15 基的取代基取代。 實施例20.實施例19之化合物,其中Q3為C2-伸 烷基,其選擇性地經至多2個選自CrC2烷基 的取代基取代。 實施例21.實施例20之化合物,其中Q3為C2-伸 20 烷基,其選擇性地經至多2個選自甲基的取代 基取代。 實施例22.式1或實施例1至21其中任一者之化 合物,其中W5為CrC4伸烷基。 53 201240602 實施例22A.式1或實施例1至22其中任一者之 化合物,其中W5為C2-C3伸烷基。 實施例22B.實施例22之化合物,其中w5為C2 伸烷基或C3伸烷基。 實施例23.式1或實施例1至22其中任一者之化 合物,其中R32為Η或CrC3烷基。 實施例23A.實施例23之化合物,其中R32為H 或甲基。 實施例24_實施例23之化合物,其中r32為η。 實施例25.實施例23之化合物,其中R32為cpc3 烷基。 實施例26.實施例25之化合物,其中R32為甲基。 實施例26A.式1或實施例1至14其中任一者之 化合物,其中 R1為-WipE1)!^4、 -WtCpEqR25 或-WiCpEiLR26。 實例27.實施例26A之化合物,其中ri為 -WWEbR24。 實例28.實施例26A之化合物,其中Ri為 -WlC^E2^25。 實例29.實施例26A之化合物,其中Ri為 -WiCpE3)!^26。 實施例29A.式1或實施例1至13其中任一者之 化合物,其中R1不為-N(R40)R41。 實例30.式1或實施例1至14或26A至29其中 任一者之化合物,其中各E1、E2與E3獨立為 0、NOR28 或 NN(R28)2。 54 201240602 實例31.實施例27之化合物,其中E1為0。 實例32.實施例27之化合物,其中Ε1為NOR28。 實例33·實施例27之化合物,其中E1為NN(R28)2。 實例34.實施例28之化合物,其中E2為Ο。 5 實例35.實施例28之化合物,其中E2為NOR28。 實例36.實施例28之化合物,其中E2為NN(R28)2。 實例37.實施例29之化合物,其中E3為Ο。 實例38.實施例29之化合物,其中E3為NOR28。 實施例39.實施例29之化合物,其中E3為 ίο NN(R28)2 〇 實施例39A.式1或實施例1至39其中任一者之 化合物,其中各R28獨立為Η、CrC3烷基或 C1-C3鹵烧基。 實施例40.式1或實施例26A、28、29或34至39 15 其中任一者之化合物,其中各L獨立為Ο或 N(R31);其限制條件是當E3為0,則L不為0。 實施例41.實施例40之化合物,其中L為Ο。 實施例42.實施例40之化合物,其中L為N(R31)。 實施例42A.實施例40或42其中任一者之化合 2〇 物,其中R31獨立為Η、CrC3烷基或Ci-C3鹵 烧基。 實施例42B.式1或實施例1至42其中任一者之化 合物,其中W1為C2-C4伸烷基、-(CH2)2OCH2-或-(ch2)3och2_。 25 實施例43.實施例42B之化合物,其中W1為CrC4 伸院基。 55 實施例43B.式1或實施例i至42其中任一者之化 合物,其中W2為Crc3伸烷基。 實施例44·式1或實施例1至14或27至39其中 任一者之化合物’其中各R24、R25與R26獨立 為氫;或CrC4烷基或C3-C5環烷基,各選擇 性地經一或多個選自由鹵素、CN、羥基、CrC2 院氧基、〇ν〇ν坑亞確醢基與(^_(^4烧續醯基所 組成之群組的取代基取代。 實施例45.實施例44之化合物,其中各R24、R25 與r26獨立為氫;或CrC2烷基或C3-C4環烷 基,各選擇性地經一或多個選自由鹵素、、 羥基與CrC2烷氧基所組成之群組的取代基取 代。 實施例46.式1或實施例i至14其中任一者之化 合物,其中R1為_(^。 實施例47.式1或實施例i至14其中任一者之化 合物,其中R1為-W2GA。 實施例47A.實施例46或47其中任一者之化合 物’其中各GA為一 4_至7_員碳環,其包括選 自 C(==〇)、C(=N-〇R30)或 C,(R29)2 之環員; 或- 6_至12-員飽和或部分飽和碳螺環或雜嫘 環環系,其選擇性地包括選自、 C(=N-0R,或C,(r29)2之環員,各環或環 系,性地經至多三個在碳環員上之R2i與在 氮裱員上之R22的取代基取代。 201240602 實施例47B.實施例46或47其中任一者之化合 物,其中各GA為一 4-至6-員碳環,其包括選 自 C(=0)、C(=N-0R3())或 C=NN(R29)2 之環員; 或一 9-至11 -員飽和或部分飽和碳螺環或雜螺 5 環環系,其選擇性地包括選自C(=0)、 C(=N-OR3Q)或C=NN(R29)2之環員,各環或環 系選擇性地經至多三個在碳環員上之R21與在 氮環員上之R22的取代基取代。 實施例48.實施例47A之化合物,其中GA為一 4-1〇 至7-員碳環,其包括選自C(=0)、C(=N-OR3Q) 或C=NN(R29)2的環員,各環選擇性地經至多 三個選自R21的取代基取代。 實施例49.實施例48之化合物,其中GA為一 5-或6-員碳環,其包括選自C=0、C(=N-OR3()) 15 或C=NN(R29)2的環員,各環選擇性地經至多 三個選自R21的取代基取代。 實施例49A.實施例47A至49其中任一者之化合 物,其中各R29獨立為Η、Q-Q烷基、CrQ 鹵烷基、CrC3烷羰基、CrC3烷磺醯基或Q-C3 20 _院續醢基。 實施例49B.實施例49A之化合物,其中各R29獨 立為C1-C6烧基、C1-C6鹵烧基或C1-C6烧叛基。 實施例49C.實施例47A至49其中任一者之化合 物,其中R3G獨立為Η、CrC3烷基或CVC3鹵 25 烧基。 57 201240602 實施例50·式1或實施例47A < 為一 6-至12-員飽和或部分s物,其中Ga 環環系,其選擇性地包和碳螺環或雜螺 C(=N-〇R3。)或 〇刪(R29)的 選自 C(=〇)、 選擇性地經至多三個選自=員,各環或環系 在氮環員上之R、取代基上之R21與 實施例5〇A.實施例50之化合物,其中GA為一 9-至11-員飽和或部分飽和碳螺環或雜螺環環 系,其選擇性地包括選自c(=〇)、c(=n_〇r3〇) 或C-NN(R29)的環員,各環或環系選擇性地經 至多三個選自在碳環員上之R2〗與在氮環員上 之R22的取代基取代。 實施例50B.實施例50之化合物,其中R3〇獨立為 Η、Ci-C3烷基或CrC3 4烷基。 15 實施例50C.實施例5〇之化合物,其中各r29為 CrC6烷基、CrC6 _烷基、Crc6烷羰基。 實施例51.實施例50之化合物,其中ga係選自Embodiment 16. The compound of Embodiment 15, wherein each Q1 and Q2 is independently hydrazine or N (R31). Embodiment 17. The compound of Embodiment 16, wherein each Q1 and Q2 is deuterium. The compound of any one of the above formulas, wherein Q3 is a C2_C3 alkylene group, which is optionally substituted with up to 4 substituents selected from the group consisting of CrC4 alkyl groups. Embodiment 19. The compound of Embodiment 18 wherein Q3 is a C2-C3 alkylene group which is optionally substituted with up to 2 substituents selected from the group consisting of CrC2 alkane. Embodiment 20. The compound of Embodiment 19, wherein Q3 is C2-alkylene, which is optionally substituted with up to two substituents selected from the group consisting of CrC2 alkyl. Embodiment 21. The compound of Embodiment 20, wherein Q3 is C2-extended 20 alkyl, which is optionally substituted with up to 2 substituents selected from methyl. Embodiment 22. The compound of Formula 1 or any one of Embodiments 1 to 21 wherein W5 is a CrC4 alkylene group. 53. The compound of any one of the above formulas, wherein W5 is a C2-C3 alkylene group. Embodiment 22B. The compound of Embodiment 22 wherein w5 is C2 alkyl or C3 alkyl. Embodiment 23. The compound of Formula 1 or any one of Embodiments 1 to 22 wherein R32 is hydrazine or CrC3 alkyl. Embodiment 23A. The compound of Embodiment 23 wherein R32 is H or methyl. Embodiment 24. The compound of Embodiment 23, wherein r32 is η. Embodiment 25. The compound of Embodiment 23 wherein R32 is cpc3 alkyl. Embodiment 26. The compound of Embodiment 25 wherein R32 is methyl. The compound of Formula 1 or any one of Embodiments 1 to 14, wherein R1 is -WipE1)!^4, -WtCpEqR25 or -WiCpEiLR26. Example 27. The compound of Embodiment 26A wherein ri is -WWEbR24. Example 28. The compound of Embodiment 26A wherein Ri is -WlC^E2^25. Example 29. The compound of Embodiment 26A wherein Ri is -WiCpE3)!^26. The compound of any one of Formula 1 or Embodiments 1 to 13, wherein R1 is not -N(R40)R41. Embodiment 30. A compound of Formula 1 or any one of Embodiments 1 to 14 or 26A to 29 wherein each of E1, E2 and E3 is independently 0, NOR28 or NN(R28)2. 54. The compound of embodiment 27, wherein E1 is 0. Example 32. The compound of Embodiment 27 wherein Ε1 is NOR28. Embodiment 33. The compound of Embodiment 27 wherein E1 is NN(R28)2. Example 34. The compound of Embodiment 28 wherein E2 is hydrazine. 5. The compound of embodiment 28, wherein E2 is NOR28. Example 36. The compound of Embodiment 28 wherein E2 is NN(R28)2. Embodiment 37. The compound of Embodiment 29 wherein E3 is hydrazine. Example 38. The compound of Embodiment 29 wherein E3 is NOR28. The compound of Embodiment 29, wherein E3 is ίο NN(R28)2, 。 。 。 。 。 。 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或C1-C3 halogenated group. Embodiment 40. The compound of Formula 1 or Embodiment 26A, 28, 29 or 34 to 39 15 wherein each L is independently Ο or N(R31); the limitation is that when E3 is 0, then L is not Is 0. Embodiment 41. The compound of Embodiment 40 wherein L is hydrazine. Embodiment 42. The compound of Embodiment 40 wherein L is N(R31). Embodiment 42A. The compound of any one of embodiments 40 or 42, wherein R31 is independently hydrazine, CrC3 alkyl or Ci-C3 halo. The compound of Formula 1 or any one of Embodiments 1 to 42 wherein W1 is C2-C4 alkylene, -(CH2)2OCH2- or -(ch2)3och2_. The compound of Embodiment 42B wherein W1 is a CrC4 stretching base. The compound of any one of the above formulas, wherein W2 is a Crc3 alkylene group. Embodiment 44. The compound of Formula 1 or any one of Embodiments 1 to 14 or 27 to 39 wherein each of R24, R25 and R26 is independently hydrogen; or CrC4 alkyl or C3-C5 cycloalkyl, each selectively Substituting one or more substituents selected from the group consisting of halogen, CN, hydroxyl, CrC2, 〇ν〇ν 亚 醢 与, and (^_(^4) 醯 醯 group. 45. The compound of embodiment 44, wherein each R24, R25 and r26 are independently hydrogen; or CrC2 alkyl or C3-C4 cycloalkyl, each optionally one or more selected from the group consisting of halogen, hydroxyl and CrC2 alkoxy The compound of any one of Formula 1 or Embodiments i to 14 wherein R1 is _(^. Example 47. Formula 1 or Examples i to 14 The compound of any one of Embodiment 46 or 47 wherein each GA is a 4- to 7-membered carbocyclic ring comprising a group selected from C (==). 〇), C(=N-〇R30) or C, (R29)2 ring members; or - 6_ to 12-membered saturated or partially saturated carbon spiro or heterocyclic ring systems, optionally including From, C (= N-0R, or C, (r29) 2 Ring members, rings or ring systems, are suitably substituted with up to three R2i on a carbon ring member and a substituent on R22 on a nitrogen member. 201240602 Example 47B. Example 46 or 47 a compound wherein each GA is a 4- to 6-membered carbocyclic ring comprising a ring member selected from C(=0), C(=N-0R3()) or C=NN(R29)2; or a 9 a to a 11-membered saturated or partially saturated carbon spiro or heterospiro-5 ring ring system, optionally comprising a ring selected from the group consisting of C(=0), C(=N-OR3Q) or C=NN(R29)2 Optionally, each ring or ring system is substituted with up to three substituents of R21 on the carbocyclic member and R22 on the nitrogen ring member. Embodiment 48. The compound of Example 47A wherein GA is a 4- a 1 to 7-membered carbocyclic ring comprising a ring member selected from C(=0), C(=N-OR3Q) or C=NN(R29)2, each ring optionally being selected from up to three selected from R21 The compound of Embodiment 48, wherein GA is a 5- or 6-membered carbocyclic ring comprising a group selected from C=0, C(=N-OR3()) 15 or C=NN a ring member of (R29) 2, each ring optionally substituted with up to three substituents selected from R21. Embodiment 49A. Combination of any of Examples 47A to 49 , wherein each R29 is independently hydrazine, QQ alkyl, CrQ haloalkyl, CrC3 alkylcarbonyl, CrC3 alkanesulfonyl or Q-C3 20 _ 醢 醢. Example 49B. The compound of Example 49A, wherein each R29 Independently C1-C6 alkyl, C1-C6 halogenated or C1-C6 burnt. The compound of any one of embodiments 47A to 49, wherein R3G is independently hydrazine, CrC3 alkyl or CVC3 halo. 57 201240602 Embodiment 50·Formula 1 or Example 47A < is a 6- to 12-membered saturated or partially s species, wherein a Ga ring ring system selectively encapsulates a carbon spiro or a heterospiro C (=N) - 〇R3.) or 〇(R29) selected from C(=〇), optionally via up to three members selected from the group consisting of R, each ring or ring system on the nitrogen ring member, R21 on the substituent The compound of Embodiment 50, wherein the GA is a 9- to 11-membered saturated or partially saturated carbon spiro or hetero-spirocyclic ring system, optionally comprising a group selected from the group consisting of c(=〇), a ring member of c(=n_〇r3〇) or C-NN(R29), each ring or ring system optionally having up to three R2 selected from the ring member and R22 on the ring member Substituent substitution. Embodiment 50. The compound of Embodiment 50 wherein R3 is independently hydrazine, Ci-C3 alkyl or CrC3 alkyl. 15C. The compound of Example 5 wherein each r29 is a CrC6 alkyl group, a CrC6-alkyl group, or a Crc6 alkylcarbonyl group. Embodiment 51. The compound of Embodiment 50, wherein ga is selected from the group consisting of

58 20124060258 201240602

其中r為0至3 ;以及Rv係選自r2i。 實施例52.實施例51之化合物,其中ga係選 GA-1、GA-2、GA-3、GA-7、G'8 與 ga-9。自 實施例53.實施例52之化合物,其中ga係選 GA_2 與 GA-3。 、自 實施例53A·實施例53之化合物’其中qA為2 實施例53B.式1或實施例1至53A其中任—者之 化合物,其中各GA不為-9·員部分飽和稠合 10 且含碳環員與2個氮環員之環系,該環選擇二 地經至多2個選自在碳環員上之rZ1與在氮環 員上之R22的取代基取代。 衣 實施例53C.式1或實施例丨至”其中任一者之化 ’其中各GA為一 9-員部分飽和稠合且含 石反%員與2個氮環員之環系,該環經丨個選自 在氮環員上之R22的取代基取代。 實施例53D.實施例53c之化合物,其中各為 59 15 201240602Wherein r is from 0 to 3; and Rv is selected from the group consisting of r2i. Embodiment 52. The compound of Embodiment 51 wherein ga is selected from the group consisting of GA-1, GA-2, GA-3, GA-7, G'8 and ga-9. The compound of Embodiment 52, wherein ga is selected from the group consisting of GA_2 and GA-3. The compound of Example 53A. The compound of Example 53 wherein qA is 2, the compound of Example 53B. Formula 1 or Examples 1 to 53A, wherein each GA is not a -9 moiety saturated fused 10 A ring system comprising a carbocyclic ring member and two nitrogen ring members, the ring being substituted with up to two substituents selected from the group consisting of rZ1 on a carbocyclic member and R22 on a nitrogen ring member. PCT Example 53C. Formula 1 or Example 丨 to "any of them" wherein each GA is a 9-member partially saturated fused and containing a ring of 2 members and 2 nitrogen ring members, the ring Substituted by a substituent selected from R22 on a nitrogen ring member. Embodiment 53D. The compound of Example 53c, each of which is 59 15 201240602

其中向左伸出之鍵代表連接至式1化合物之其 餘部分的連接點。 ' 實施例53E_實施例53D之化合物,其中各gaThe bond extending to the left represents the point of attachment to the remainder of the compound of Formula 1. 'Example 53E - the compound of Example 53D, wherein each ga

實施例54.式1或實施例1至53E其中任一者«匕 ίο 合物,其中R2為苯基或-W3(苯基),各選择性 地在環員上經至多五個選自R21的取代基取 代;或-G ;或Ci-C6院基、C2-C6稀基、 快基、C1-C6鹵院基、C2-C6鹵稀基、C2-C;6鹵 炔基、C3-C8環燒基、C3-C8 ii環燒基、c4_c1Q 15 院環烧基、CVCiq環烧烧基、CVCi4環燒環烧 基、C4-C1G _環烧烧基、C5-C12燒環燒燒基、 C3-C8環稀基、C3-Cs鹵環稀基、C2_Cg燒氧烧 基、Cs-Cio烧氧烯基、C4-C1G環烧氧燒基、c4-C1() 環院氧烧氧烧基、C3-Ci()烧氧烧氧烧基、c2-C8 20 燒硫烧基、C2_C8烧亞橫醢院基、C2-C8院項醯 燒基、C2-Cg烧幾基、C4-C10環埽烧基、C2-C8 鹵烷氧烷基、C2-C8烷氧鹵烷基、C2-C8鹵烷氧 鹵烷基、C4_C10鹵環烷氧烷基、c4-c10環烯氧 院基、C4-C10函環稀氧炫基、C3_C10二燒氧烧 60 201240602 基、CrG烷氧基、CVC6鹵烷氧基、c3-c8環 烷氧基、CrC8齒環烷氧基、C4-C1Q環烷烷氣 基、c2-c6烯氧基、c2-c6 i稀氧基、C3_c6块 氧基、C3-C6鹵炔氧基、c2-c8烷氧烷氧基、c2-c8 5 烧幾氧基、C2_Cs鹵烧幾氧基、CU-Cio環燒緩 氧基、C3-C1G烷羰烷氧基、CrC6烷硫基、(:,<:6 鹵烧硫基、C3-C8環炫·硫基、Ci_C6烧亞石夤酿 基、CrC6鹵烧亞績醯基、CrC6院確醯基、CrC6 鹵烧續酿基、C3-C8環烧續酿基、C3-Cs三炫*碎 ίο 基、C3-C8環稀氧基、C3-C8鹵環稀氧基、C2-C8 鹵烧氧院氧基、CVCs院氧鹵院氧基、c2-C8鹵 烷氧鹵烷氧基、C3-C10烷氧羰烷氧基、c2-c8 烷基(硫羰基)氧基、C3-C8環烷亞磺醯基或 C3-C10 ii|三院石夕基;或 15 R2 為·W6C(=E4)R33、_w6l1c(=e5)r34 或 -\ν6(:(=Ε6)ΐ/ΐ135。 實施例54Α.實施例54之化合物,其中R2為苯基 或-W3(苯基)的取代基取代’各選擇性地在環員 上經至多兩個選自R21 ;或_G ;或CrC6烷基 20 或C3-C8環院基。 實施例55.實施例54之化合物,其中r2為 -W6C(=E4)R24 、 -\ν6Ι^(:(=Ε5)Ι125 或 -ν^ΡΕ6)!^26。 實例56實施例55之化合物,其中R2為 25 -W6C(=E4)R24。 61 201240602 實施例57·實施例55之化合物,其中R2為 -\νν<:(=Ε5)Ι125。 實施例58.實施例55之化合物,其中R2為 5 實施例59.式1或實施例1至58其中任一者之化 合物’其中Ε4、Ε5與Ε6獨立為〇、N〇R37或 NN(R37)2 〇 實施例60·式1或實施例1至56其中任一者之化 合物,其中E4為Ο。 ίο 實施例61·式1或實施例1至56其中任一者之化 合物,其中E4為NOR37。 實施例62_式1或實施例1至56其中任一者之化 合物,其中E4為NN(R37)2。 實施例63.式1或實施例1至55或57其中任一者 15 之化合物,其中E5為Ο。 實施例64.式1或實施例1至55或57其中任一者 之化合物’其中E5為NOR37。 實施例65.式1或實施例1至55或57其中任一者 之化合物,其中E5為NN(R37)2。 20 實施例66.式1或實施例1至55或58其中任一者 之化合物,其中E6為〇。 實施例67.式1或實施例丨至55或% 之化合物’其中E6為NOR37。 、 實施例68.式1或實施例丨至^或“其中任一者 25 之化合物,其中E6為NN(R37)2。 62 201240602 實施例68A.式1或實施例1至68其中任一者之 化合物,其中W6為C2-C4伸烷基、-(CH2)2OCH2-或 _(CH2)3〇CH2_ 0 實施例69_式1或實施例1至68其中任一者之化 合物,其中\¥6為C2-C4伸烷基。 實施例70.式1或實施例1至55或57至59或63 至69其中任一者之化合物,其中各L1獨立為 Ο 或 N(R38)。 實施例70A.實施例59、61、64至65或68其中 任一者之化合物,其中各R37獨立為Η、CrC3 炫基或C1-C3鹵烧基。 實施例71.式1或實施例1至70其中任一者之化 合物,其中各R33、R34與R35獨立為氫;或Q-C6 烧基或C3-C6環烧基,各選擇性地經一或多個 選自由鹵素、CN、N〇2、經基、Q-C4院氧基、 C1-C4烧亞績醢基與C1-C4院確酿基所組成之 群組的取代基取代。 實施例71B.實施例71之化合物,其中各r33、r34 與R35獨立為氫;或CrC4烷基、C3-C5環烷基, 各選擇性地經一或多個選自由鹵素、CN、經 基、Ci-C2烧氧基、Ci-C2垸亞續酿基與Q-C2 烷磺醯基所組成之群組的取代基取代。 實施例72·實施例71B之化合物,其中各R33、R34 與R35獨立為氫;或CrC2燒基或c3-C4環烧 基,各選擇性地經一或多個選自由_素、CN、 羥基與CrC2烷氧基的取代基取代。 63 201240602 實施例73.式1或實施例1至72其中任一者之化 合物,其中R2為苯基或-W3(苯基),各選擇性 地在環員上經至多兩個選自R21的取代基取 代;或-G ;或CrC6烷基或C3-C8環烷基。 5 實施例74.實施例73之化合物,其中R2為苯基, 其選擇性地在環員上經至多兩個選自R21的取 代基取代;或-G ;或CrC6烷基或C3-C8環烷 基。 實施例74A.實施例73之化合物,其中R2為苯基; ίο 或-G ;或C3-C8環烷基。 實施例74B.實施例74A之化合物,其中R2為苯 基、2-。塞吩基5-氣-2-°比咬基或壤丙基。 實施例74C.實施例74A之化合物,其中R2為苯 基、3-σ塞吩基或環丙基。 15 實施例75.實施例74之化合物,其中R2為苯基、 2_甲基苯基、3_甲基苯基、4-氣苯基、3-氟苯 基或3,5-二氟苯基。 實施例76.實施例74之化合物,其中R2為苯基、 3-溴苯基、3-氣苯基或2-曱基苯基。 2〇 實施例76Α.實施例74Α之化合物,其中R2為5- 氣-2-°tb咬基。 實施例77.實施例74之化合物,其中R2為苯基。 實施例78.式1或實施例1至76其中任一者之化 合物,其中R2不為苯基。 25 實施例79.實施例74之化合物,其中R2為3-噻吩 基、2-。塞吩基或3-°比咬基。 64 201240602 實施例79A.實施例79之化合物,其中R2為2_噻 吩基。 實施例80.實施例79之化合物,其中R2為3-吡啶 基。 5 實施例81.實施例76之化合物,其中R2為正丙 基、正丁基或環丙基。 實施例81A.實施例81之化合物,其中R2為環丙 基。 實施例82.式1或實施例1至75其中任一者之化 ίο 合物,其中W3為-CH2-。 實施例83.式1或實施例1至75其中任一者之化 合物,其中W4為-CH2-。 實施例84.式1或實施例1至83其中任一者之化 合物,其中R3為羥基、-0_M+、C2-C8烷羰氧 15 基、C2-C8鹵烧幾氧基、C4-C10環院幾氧基或 c3-c1()烷羰烷氧基;或苄氧基、苯氧基、苄羰 氧基、苯羰氧基、苯磺醯氧基或苄磺醯氧基, 各選擇性地在環員上經至多兩個選自R21的取 代基取代。 2〇 實施例85.實施例84之化合物,其中R3為羥基、 -0_M+或C2-C8烷幾氧基;或苯磺醯氧基,其選 擇性地經至多兩個選自R21的取代基取代。 實施例86.實施例85之化合物,其中M+為一鈉或 卸金屬陽離子。 25 實施例87.實施例86之化合物,其中R3為羥基或 C2-Cg烧毅氧基。 65 201240602 實施例88.實施例87之化合物,其中r3為經基或 -oc(=o)ch2ch(ch3)2。 實施例89.式1或實施例卜7與14至88其中任 一者之化合物,其中r4、R5、R6與R7各獨立 為Η或CrC6烷基。 實施例90.式1或實施例丨或7其中任一者之化合 物,其中R為Ci-C;6院基或C3_C8環燒基。 實施例91 _實施例90之化合物,其中R8為CH、 CH2CH3或環丙基。 實施例92.式1或實施例1至3或14至91其中任 一者之化合物,其中R9為CrC6烷基。 實施例93.實施例92之化合物,其中R9為 CH2CH3。 、 '、、 實施例94.式1或實施例1至3或14至93其中任 一者之化合物,其中R10為H、齒素或Ci_Q 烧基。 實施例95.實施例94之化合物,其中尺1〇為H或 CH3 〇 一 實施例96.式1或實施例1、2或14至95装Φ/工 -者之化合物,其中R"為Η或以=任 實施例97.實施例96之化合物,其中Rii為H。 實施例98·式1或實施例1、2或14至97其中任 一者之化合物’其中R12為H、鹵素、氰基、 經基、胺基或CVCg烧基。 實施例99.實施例98之化合物,其中為H、 鹵素、氰基、CrC6烷基或CrC8環烷基。 66 201240602 實施例1〇〇·實施例99之化合物,其中Rn為CH、 CH2CH3或環丙基。 實施例101.式1或實施例1或14至1〇〇其中任一 者之化合物’其中Rl3為Η、i素、氰基或硝 基。 實施例102·實施例1〇1之化合物,其中r13為氮 基或硝基。 ' 實施例103·式1或實施例1至其中任一者之 化合物,其中當將R14與R1S的例子單獨考量 時(即R14與R18並非一起作為伸烷基或伸烯 基),則該R14與R18之例子獨立為Η或Ci_C6 烧基。 實施例104_實施例103之化合物,其中當將Rl々 與R〗8的例子單獨考量時’則汉“與…8的例子 獨立為Η或CH3。Embodiment 54: Formula 1 or any one of Embodiments 1 to 53E, wherein R 2 is phenyl or -W 3 (phenyl), each selectively up to five selected from ring members a substitution of a substituent of R21; or -G; or a Ci-C6 group, a C2-C6 dilute group, a fast group, a C1-C6 halogen compound, a C2-C6 halogen group, a C2-C; a 6-haloalkynyl group, a C3 group -C8 cycloalkyl, C3-C8 ii cycloalkyl, c4_c1Q 15 ring alkyl, CVCiq ring calcination, CVCi4 cycloalkyl, C4-C1G _ ring calcination, C5-C12 calcination Base, C3-C8 ring dilute base, C3-Cs halo ring dilute base, C2_Cg alkoxy burnt group, Cs-Cio alkoxyalkylene group, C4-C1G ring oxyalkylene group, c4-C1() ring hospital oxygen-burning oxygen Burning base, C3-Ci() aerobic oxygen-burning base, c2-C8 20 sulfur-burning base, C2_C8-burning yam-yield base, C2-C8-situ simmering base, C2-Cg burning base, C4- C10 cycloalkyl, C2-C8 haloalkoxy, C2-C8 alkoxyhaloalkyl, C2-C8 halohalooxyalkyl, C4_C10 halocycloalkane, c4-c10 cycloalkoxy , C4-C10, Cyclooxyxanthene, C3_C10, Di-Oxygen, 60, 201240602, CrG alkoxy, CVC6 haloalkoxy, c3-c8 cycloalkoxy, CrC8 dentate alkoxy, C4-C1Q ring Alkane gas , c2-c6 alkenyloxy, c2-c6 i diloxy, C3_c6 siloxy, C3-C6 haloalkoxy, c2-c8 alkoxyalkoxy, c2-c8 5 decyloxy, C2_Cs halogen a oxy group, a CU-Cio ring-terminated oxy group, a C3-C1G alkylcarbonyl alkoxy group, a CrC6 alkylthio group, (:, <:6 halogenated sulfur group, C3-C8 cyclodextryl group, Ci_C6 burnt) The sub-stone brewing base, the CrC6 halogen-fired sub-base, the CrC6 yard, the CrC6, the halogen-burning base, the C3-C8 ring-burning, the C3-Cs, the three-color, the C3-C8 ring Dilute oxy, C3-C8 halocyclooxyl, C2-C8 halooxynoxy, CVCs, oxyhaloxy, c2-C8 haloalkoxy alkoxy, C3-C10 alkoxycarbonyl alkoxy Base, c2-c8 alkyl (thiocarbonyl)oxy, C3-C8 cycloalkylsulfinyl or C3-C10 ii|Sanyuan Shiheji; or 15 R2 is · W6C (=E4)R33, _w6l1c (= And e.g., r. Up to two members are selected from R21; or _G; or CrC6 alkyl 20 or C3-C8 ring. The compound of Example 54 wherein r2 is -W6C(=E4)R24, -\ Ι6Ι^(:(= 5) Ι125 or -ν ^ ΡΕ6)! ^ 26. Embodiment 56 The compound of Embodiment 55, wherein R2 is 25-W6C(=E4)R24. 61. The compound of Embodiment 57, wherein R2 is -\νν<:(=Ε5)Ι125. Embodiment 58. The compound of Embodiment 55, wherein R2 is 5. Embodiment 59. Compound of Formula 1 or Embodiments 1 to 58 wherein Ε4, Ε5 and Ε6 are independently 〇, N〇R37 or NN (R37 The compound of any one of Embodiment 1 or Embodiment 1 to 56 wherein E4 is hydrazine. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。. Embodiment 62. The compound of Formula 1 or any one of Embodiments 1 to 56 wherein E4 is NN(R37)2. The compound of any one of Formula 1 or any one of Embodiments 1 to 55 or 57, wherein E5 is hydrazine. Embodiment 64. Compound 1 of Formula 1 or Embodiment 1 to 55 or 57 wherein E5 is NOR37. Embodiment 65. A compound of Formula 1 or any one of Embodiments 1 to 55 or 57 wherein E5 is NN(R37)2. The compound of any one of Formula 1 or any one of Embodiments 1 to 55 or 58 wherein E6 is hydrazine. Embodiment 67. Compound of Formula 1 or Example 丨 to 55 or %' wherein E6 is NOR37. The compound of Formula 1 or Embodiment 丨 to ^ or " any of 25, wherein E6 is NN(R37) 2. 62 201240602 Example 68A. Formula 1 or Examples 1 to 68 A compound of the formula C-C4 alkyl, -(CH2)2OCH2- or _(CH2)3〇CH2_0, wherein the compound of any one of the embodiments 69 or 1 to 68, wherein 6 is a C2-C4 alkylene group. Embodiment 70. The compound of any one of Formula 1 or Embodiment 1 to 55 or 57 to 59 or 63 to 69, wherein each L1 is independently Ο or N(R38). 70A. The compound of any one of embodiments 59, 61, 64 to 65 or 68, wherein each R37 is independently hydrazine, CrC3 danyl or C1-C3 halogen. Example 71. Formula 1 or Examples 1 to 70 a compound according to any one, wherein each R33, R34 and R35 are independently hydrogen; or a Q-C6 alkyl or C3-C6 cycloalkyl, each optionally one or more selected from the group consisting of halogen, CN, N〇2 Substituted by a group consisting of a group of Q-C4, an alkyl group, a C1-C4 alkyl group, and a C1-C4 group. Example 71B. The compound of Example 71, wherein each r33 , r34 and R35 are independently hydrogen; or CrC4 alkyl, C3-C a 5-cycloalkyl group, each optionally one or more selected from the group consisting of halogen, CN, a mercapto group, a Ci-C2 alkoxy group, a Ci-C2 fluorene group, and a Q-C2 alkanesulfonyl group Substituting a substituent of the group. Embodiment 72. The compound of Embodiment 71B wherein each R33, R34 and R35 are independently hydrogen; or CrC2 alkyl or c3-C4 cycloalkyl, each optionally selected from one or more selected from _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Each of which is optionally substituted on the ring member with up to two substituents selected from R21; or -G; or a CrC6 alkyl group or a C3-C8 cycloalkyl group. Embodiment 74. The compound of Embodiment 73, wherein R2 is a phenyl group which is optionally substituted on the ring member with up to two substituents selected from R21; or -G; or a CrC6 alkyl group or a C3-C8 cycloalkyl group. Embodiment 74A. The compound of Embodiment 73, wherein R2 is phenyl; ίο or -G; or C3-C8 cycloalkyl. Embodiment 74B. The compound of Embodiment 74A wherein R2 is phenyl, 2-. Or soil propyl. 74C. The compound of Embodiment 74A, wherein R2 is phenyl, 3-σ-septenyl or cyclopropyl.. The compound of Embodiment 74, wherein R2 is phenyl, 2-methylphenyl, 3 _Methylphenyl, 4-phenylphenyl, 3-fluorophenyl or 3,5-difluorophenyl. Embodiment 76. The compound of Embodiment 74 wherein R2 is phenyl, 3-bromophenyl, 3-phenylphenyl or 2-nonylphenyl. 2) The compound of Embodiment 74, wherein R 2 is a 5-gas-2-°tb bite. Embodiment 77. The compound of Embodiment 74 wherein R2 is phenyl. Embodiment 78. The compound of Formula 1 or any one of Embodiments 1 to 76 wherein R2 is not phenyl. The compound of Embodiment 74, wherein R2 is 3-thienyl, 2-. The thiophene or 3-° ratio bite base. 64. The compound of Embodiment 79, wherein R2 is 2-thiophenyl. Embodiment 80. The compound of Embodiment 79 wherein R2 is 3-pyridyl. The compound of Embodiment 76, wherein R2 is n-propyl, n-butyl or cyclopropyl. Embodiment 81A. The compound of Embodiment 81 wherein R2 is cyclopropyl. Embodiment 82. The compound of Formula 1 or any one of Embodiments 1 to 75, wherein W3 is -CH2-. Embodiment 83. The compound of Formula 1 or any one of Embodiments 1 to 75 wherein W4 is -CH2-. Embodiment 84. The compound of any one of Formula 1 or Embodiments 1 to 83, wherein R3 is hydroxy, -0-M+, C2-C8 alkoxycarbonyl-15, C2-C8 halooxy, C4-C10 ring a oxy or a c3-c1()alkylcarbonylalkoxy group; or a benzyloxy group, a phenoxy group, a benzylcarbonyloxy group, a phenylcarbonyloxy group, a benzenesulfonyloxy group or a benzylsulfonyloxy group, each selectively Substituted at most two substituents selected from R21 on the ring member. The compound of Embodiment 84, wherein R3 is hydroxy, -0_M+ or C2-C8 alkyloxy; or phenylsulfonyloxy, which is optionally substituted with up to two substituents selected from R21. . Embodiment 86. The compound of Embodiment 85 wherein M+ is monosodium or metal cation. The compound of Embodiment 86, wherein R3 is hydroxy or C2-Cg oximeoxy. 65. The compound of Embodiment 87, wherein r3 is a trans group or -oc(=o)ch2ch(ch3)2. Embodiment 89. The compound of any one of Formula 1 or Embodiment 7 and 14 to 88, wherein r4, R5, R6 and R7 are each independently hydrazine or CrC6 alkyl. The compound of any one of the above formulas, wherein R is Ci-C; 6 or C3_C8 cycloalkyl. Embodiment 91 The compound of Embodiment 90, wherein R8 is CH, CH2CH3 or cyclopropyl. Embodiment 92. A compound of Formula 1 or any one of Embodiments 1 to 3 or 14 to 91 wherein R9 is CrC6 alkyl. Embodiment 93. The compound of Embodiment 92 wherein R9 is CH2CH3. The compound of Formula 1 or any one of Embodiments 1 to 3 or 14 to 93, wherein R10 is H, dentate or Ci_Q alkyl. Embodiment 95. The compound of Embodiment 94, wherein the ruler 1 is H or CH3. Example 96. Formula 1 or Example 1, 2 or 14 to 95 is a compound of Φ/工-, wherein R" Or the compound of Embodiment 96, wherein Rii is H. Embodiment 98. The compound of Formula 1 or any one of Embodiment 1, 2 or 14 to 97 wherein R12 is H, halogen, cyano, thiol, amine or CVCg. Embodiment 99. A compound of Embodiment 98 which is H, halo, cyano, CrC6 alkyl or CrC8 cycloalkyl. 66. The compound of Embodiment 99, wherein Rn is CH, CH2CH3 or cyclopropyl. Embodiment 101. Compound 1 of Formula 1 or Embodiment 1 or 14 to 1 wherein Rl3 is hydrazine, imine, cyano or nitro group. Embodiment 102. The compound of Embodiment 1 wherein r13 is a nitrogen group or a nitro group. The compound of any one of the above formulas, wherein the R14 and the R1S are individually considered (i.e., R14 and R18 are not taken together as an alkylene group or an alkenyl group), then the R14 Independent of the example of R18, it is a hydrazine or a Ci_C6 alkyl group. Embodiment 104 - The compound of Embodiment 103, wherein when the examples of R1々 and R8 are taken into consideration separately, the examples of "Han" and "8" are independently Η or CH3.

實施例105.實施例104之化合物,其中當將rM 與R18的例子單獨考量時’則rm與κ1Γ的例子 獨立為Η。 實施例106.式1或實施例1至1〇5其中任一者之 化合物’其中當將R14與W的例子一起考量 時,則Rl^Rl8的例子一起作為偶CH2CH2-或-ch=chch2-。 實施例107.式1或實施例1至l〇s其中任一者之 化合物’其中的所有例子單獨考 量。 67 25 201240602 實施例108.式1或實施例1至106其中任一者之 化合物’ ·其中各R15與R19獨立為Η或Cl_C6 统基。 實施例109.實施例108之化合物’其中各與 R19獨立為Η或CH3。 實施例110.實施例109之化合物,其中各與 R19獨立為Η。 實施例110Α.實施例104至109其中任一者之化 合物,其中各R14、R15、R18與R19為Η或CH3。 實施例11 〇Β·實施例110A之化合物,其中各r14、 R15、R18 與 R19為 Η。 實施例111.式1或實施例1至110Β其中任一者之 化合物,其中R20為Η、CrC6烷基、Crc6稀 基或C3-Cpf&lt;烷基。 實施例112_實施例111之化合物,其中尺2〇為H 或 CH3。 實施例113•式1或實施例1至4、6、10、Η與 14至51其中任一者之化合物,其中τ為 或-CH=CH- 〇 實施例114.實施例113之化合物,其中τ為 -CH2CH2-。 實施例115.式1或實施例1至54、75或84至114 其中任一者之化合物,其中各G獨立為一 5_ 或6-員雜環,其選擇性地經至多五個選自在碳 環員上之R21與在氮環員上之R22的取代基取 代。 68 201240602 實施例116.實施例115之化合物,其中g為Embodiment 105. The compound of Embodiment 104, wherein when the examples of rM and R18 are individually considered, the example of rm and κ1Γ is independently Η. Embodiment 106. The compound of Formula 1 or Embodiment 1 to 1〇5, wherein when R14 and W are taken together, the examples of R1^Rl8 are taken together as even CH2CH2- or -ch=chch2- . Embodiment 107. All of the examples of the compound of Formula 1 or Examples 1 to 10's are considered separately. 67 25 201240602 Embodiment 108. Compound of Formula 1 or any of Embodiments 1 to 106' wherein each of R15 and R19 is independently hydrazine or Cl_C6. Embodiment 109. The compound of Embodiment 108 wherein each of R19 is independently hydrazine or CH3. Embodiment 110. The compound of Embodiment 109, wherein each independently of R19 is hydrazine. The compound of any one of embodiments 104 to 109, wherein each of R14, R15, R18 and R19 is deuterium or CH3. Embodiment 11 The compound of Embodiment 110A wherein each of r14, R15, R18 and R19 is hydrazine. Embodiment 111. A compound of Formula 1 or any one of Embodiments 1 to 110, wherein R20 is hydrazine, CrC6 alkyl, Crc6 or C3-Cpf&lt;alkyl. Embodiment 112 - The compound of Embodiment 111, wherein the rule 2 is H or CH3. </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; τ is -CH2CH2-. The compound of Formula 1 or any one of Embodiments 1 to 54, 75 or 84 to 114, wherein each G is independently a 5- or 6-membered heterocyclic ring, which is selectively selected from up to five selected from carbon R21 on the ring member is substituted with a substituent of R22 on the nitrogen ring member. 68. The compound of embodiment 115, wherein g is

G-16 G-17 G-18 G-19 其中r為0、1、2或3。 實施例117_實施例116之化合物’其中G為G_2、 G-3 或 G-15 0 實施例118·實施例117之化合物’其中〇為〇_2 或 G-3。 實施例119_實施例118之化合物,其中〇為G_2。 實施例120.實施例118之化合物’其中g為。 實施例120A.實施例116之化合物,其中〇為 G-15。 實施例121.式1或實施例1至120其中任—者之 化合物’其中各R21獨立為鹵素、氰基、羥基、 69 201240602 硝基、-CHO、-SH、Ci-C6 烷基、C2-C6 烯基、 C2-C6 炔基、CVC6 _ 烷基、C2-C6 i 烯基、c2-c6 鹵炔基、C3-C8環烷基、C;rC8鹵環烷基、C4-C10 烷環烷基、C4-C1G環烷烷基、c3-c8環烯基、 C3-C8齒環稀基、C2-C8烧氧烧基、C4-C10環院 氧烧基、C3-C10烧乳烧氧院基、C2-Cg烧硫炫* 基、C2-C8烧亞續醯烧基、C2-Cs烧氧S烧基、 c2-c5氰烷基、crc6羥烷基、crc6烷氧基、 CrC6鹵烷氧基、C3-C8環烷氧基、C3-C8鹵環 烷氧基、C4-C1G環烷烷氧基、c2-c6烯氧基、 c2-c6鹵烯氧基、c2-c8烷氧烷氧基、c2-c8烷 幾·氧基、Ci-C6烧硫基、Ci_C6鹵院硫基、C3-C8 環燒硫基、C!-C6烧亞續酿基、Ci_C6 _院亞績 酿基、Ci-C6烧續酿基、Ci_C6鹵烧確酿基或 C3-C8環院續醯基。 實施例121A.實施例121其中任一者之化合物, 其中各R21獨立為鹵素、硝基、CrC6烷基、 Ci-C6鹵院基、Ci-C6烧氧基、C!-C6鹵烧氧基 或crc6烷硫基。 實施例122.實施例121A之化合物,其中R21獨立 為氟、氣、溴、CH3、CF3、och3、〇cf3 或 SCH3。 實施例123.式1或實施例1至122之化合物,其 中各R22獨立為Ci-C6院基或Ci-C6鹵院基。 實施例124.實施例123之化合物’其中各R22獨 立為 CH3 或 CH2CF3。 70 201240602 實施例124A.實施例124之化合物,其中R22為 CH3。 實施例124B.式1或實施例1至124A之化合物, 其中R4G為乙基或異丙基。 實施例124C·式1或實施例1至124A之化合物, 其中R41為乙基或異丙基。 實施例124D.式1或實施例1至124A之化合物, 其中R40與R41 —起作為-(CH2)5-、 •CH2CH=CHCH2-或-(CH2)20(CH2)2-。 實施例124E.實施例124D之化合物,其中R40與 R41 —起作為-(CH2)5-或-((:ί12)20((:ϋ2)2-。 實施例124F.實施例124Ε之化合物,其中R40與 R 起作為-(CH2)2〇(CH2)2-。 15 20 本發明亦包括一除草混合物,其包含(幻一選自式 1、其,氧化物及其鹽之化合物,以及(b)至少一種額外 活性成分,其選自(bi)光系統π抑制劑、(b2)乙醢羥酸 合成酶(HAS)抑制劑、(b3)乙醯C()Am化酶(ACCase)抑 制劑、(b4)生長素模擬物、(b5) 5_烯醇-丙酮醯莽草酸_3_ 磷酸(EPSP)合成酶抑制劑、⑽光系統〗電子轉向劑 (diverters)、(b7)原紫元氧化酶(pp〇)抑制齊卜&amp;嶋醢胺 ^ 口成酶(GS)抑制劑、㈣極長鍵脂肪酸延長 劑、(M0)生長素傳輸抑制劑、八氫番茄紅 = = = 抑制劑、_4_絲基·丙酮酸二氧合 s#(hppd)抑制劑、R + 劑、_其他除草劑(,=、尿^尼轉移酶(腹)抑制 亞速爛、燕麥枯、二分裂干擾劑、有機坤劑、 吴不泰、抑草丁、環庚草醚、苄草隆、 25 201240602 邁隆、汰草龍、甲基汰草龍、乙氧苯草胺、殺木膦、殺 木膦知、威百故、。惡嗪草嗣、油酸、壬酸(pelarg〇nic acid) 稗草畏與(M5)除草劑保護劑;以及(bl)至(bl5)化合物之 鹽。 實施例125. —種除草混合物,其包含(0式1或實 施例1至125E其中任一者之化合物,以及(b) 至少一種選自(bl)、(b2)、(b3)、(bl2)、(bl3) 與(M5)。 實施例126.實施例125之除草混合物,其中成分 (b)包含至少一種選自(bl)、(bl2)、(bl3)與(bl5) 的額外活性成分。 實施例127.實施例126之除草混合物,其中成分 (b)包含至少一種選自(bl)的額外活性成分。 實施例128.實施例127之除草混合物,其中成分 (b)包含溴苯腈(bromoxynil)。 實施例129.實施例127之除草混合物,其中成分 (b)包含愛落殺(dimethametryn)。 實施例130.實施例126之除草混合物,其中成分 (b)包含至少一種選自(bl3)的額外活性成分。 實施例131.實施例130之除草混合物,其中成分 (b)包含氟咬草(haloxydine)。 實施例132_實施例126之除草混合物,其中成分 (b)包含至少一種選自(bl5)的額外活性成分。 實施例133.實施例132之除草混合物,其中成分 (b)包含至少一種額外活性成分,其選自草毒 死、解草嗪、1-溴-4-[(氣甲基)磺醯基]苯、解 72 201240602 毒喹、苄草隆、解草胺腈、啶醯菌胺、殺草隆、 一亂丙烯胺、二環隆g同(Cyc丨〇n〇n)、4_(二氣乙 醯基)-1-氧雜-4-偶氮螺[4 5]癸烷(M〇N 4660)、2-(二氯甲基)_2_甲基_13_二氧雜環戊烧 (MG 191)、哌草丹、解草唑、解草啶、解草胺、 氟草聘、解草惡唾、雙苯嚼唾酸、唾解草酯、 美伏耐(mephenate)、苯草酮、萘二甲酸酐與8解 草腈。 、 實施例134.實施例133之除草混合物,其中成分 (b)包含至少一種額外活性成分,其選自解草 °桊、解毒喹、β定醯菌胺、殺草隆、解草唾、唑 解草酯、美伏耐與解草腈。 實施例135.實施例134之除草混合物,其中成分· (b)包含至少一種額外活性成分,其選自解毒 喹、唑解草酯與解草腈。 實施例136.實施例135之除草混合物,其中成分 (b)包含至少一種選自解毒喹的額外活性成分。 實施例137.實施例135之除草混合物,其中成分 (b)包含至少一種選自解草腈的額外活性成分。 本發明之實施例(包括以上實施例1-124F以及任 何其他本文中所述之實施例)可以任何方式組合,並且 實施例中之變項的描述不僅適用於式1化合物,亦適用 於其起始化合物與中間化合物(包括式1Q、1R與1S 之化合物),其可用於製備式1化合物。此外,本發明 的實施例(包括上述實施例1至124E或125至137以 73 201240602 及任何其他本文中所述之實施例,與任何其組合)均適 用於本發明之組成物與方法。 實施例1至124F的組合係藉由以下來說明: 實施例A. —種式1之化合物,其中 A 為 Α·1、A-3、A-4、A-5 或 Α·6 ; R1為G-16 G-17 G-18 G-19 where r is 0, 1, 2 or 3. Embodiment 117 - The compound of Example 116 wherein G is G_2, G-3 or G-15 0 Example 118. Compound of Example 117 wherein 〇 is 〇_2 or G-3. Embodiment 119 - The compound of Embodiment 118, wherein hydrazine is G_2. Embodiment 120. The compound of Example 118 wherein g is. Embodiment 120A. The compound of Embodiment 116, wherein hydrazine is G-15. Embodiment 121. The compound of Formula 1 or Embodiments 1 to 120 wherein each R21 is independently halogen, cyano, hydroxy, 69 201240602 nitro, -CHO, -SH, Ci-C6 alkyl, C2- C6 alkenyl, C2-C6 alkynyl, CVC6-alkyl, C2-C6 i alkenyl, c2-c6 haloalkynyl, C3-C8 cycloalkyl, C; rC8 halocycloalkyl, C4-C10 alkane Base, C4-C1G cycloalkyl, c3-c8 cycloalkenyl, C3-C8 ring-and-ring, C2-C8 azepine, C4-C10 ring oxyalkyl, C3-C10 calcined oxygen plant Base, C2-Cg sulphur sulphur*, C2-C8 sinter sinter, C2-Cs alkoxy S, c2-c5 cyano, crc6 hydroxyalkyl, crc6 alkoxy, CrC6 halane Oxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C1G cycloalkanoyloxy, c2-c6 alkenyloxy, c2-c6 haloenyloxy, c2-c8 alkoxylated Oxygen, c2-c8 alkoxy, Ci-C6 sulphur, Ci_C6 halogen thiol, C3-C8 cyclosulphur thio, C!-C6 sinter, Ci_C6 , Ci-C6 burned the brewing base, Ci_C6 halogen burning or brewing base or C3-C8 ring hospital continued. The compound of any one of Embodiment 121, wherein each R21 is independently halogen, nitro, CrC6 alkyl, Ci-C6 halogen-based, Ci-C6 alkoxy, C!-C6 halogenated alkoxy Or crc6 alkylthio. Embodiment 122. The compound of Embodiment 121A wherein R21 is independently fluoro, ethane, bromo, CH3, CF3, och3, 〇cf3 or SCH3. Embodiment 123. A compound of Formula 1 or Embodiments 1 to 122 wherein each R22 is independently a Ci-C6 or a Ci-C6 halogen. Embodiment 124. Compound of Embodiment 123 wherein each R22 is independently CH3 or CH2CF3. 70. The compound of Embodiment 124, wherein R22 is CH3. Embodiment 124B. A compound of Formula 1 or Embodiments 1 to 124A wherein R4G is ethyl or isopropyl. Embodiment 124C. A compound of Formula 1 or Embodiments 1 to 124A wherein R41 is ethyl or isopropyl. Embodiment 124D. A compound of Formula 1 or Embodiments 1 to 124A wherein R40 and R41 together are -(CH2)5-, -CH2CH=CHCH2- or -(CH2)20(CH2)2-. The compound of Embodiment 124D, wherein R40 and R41 together are as -(CH2)5- or -((:ί12)20((:ϋ2)2-. Example 124F. The compound of Example 124, wherein R40 and R are taken as -(CH2)2〇(CH2)2-. 15 20 The present invention also encompasses a herbicidal mixture comprising (a compound selected from Formula 1, its oxides and salts thereof, and (b) At least one additional active ingredient selected from the group consisting of (bi) photosystem π inhibitors, (b2) acetate synthase (HAS) inhibitors, (b3) acetamidine C () Amase (ACCase) inhibitors , (b4) auxin mimetic, (b5) 5-enol-acetone oxalic acid _3_phosphoric acid (EPSP) synthetase inhibitor, (10) photosystem 〗 electronic diverters (diverters), (b7) primary violet oxidation Enzyme (pp〇) inhibits Qib &amp; indoleamine (GS) inhibitor, (iv) very long bond fatty acid extender, (M0) auxin transport inhibitor, octohydrochlorin = = = inhibitor, _4_ silk-pyruvate dioxygen s# (hppd) inhibitor, R + agent, _ other herbicides (, =, urinary transfer enzyme (abdominal) inhibits sub-speed rotten, oats, two splitting interfering agents , organic Kunming, Wu Butai, grass Ding, cycloheptyl ether, benzalkonium, 25 201240602 Mailon, T. chinensis, Methylidene, acetophene, chlorpyrifos, chlorpyrifos, Weibai, oxazin , oleic acid, pelarg〇nic acid oxadicarb and (M5) herbicide protectant; and (bl) to (bl5) a salt of the compound. Example 125. A herbicidal mixture comprising (0) 1 or a compound of any of embodiments 1 to 125E, and (b) at least one selected from the group consisting of (bl), (b2), (b3), (bl2), (bl3) and (M5). The herbicidal mixture of embodiment 125, wherein component (b) comprises at least one additional active ingredient selected from the group consisting of (bl), (bl2), (bl3) and (bl5). Embodiment 127. The herbicidal mixture of Example 126, wherein the ingredients (b) comprises at least one additional active ingredient selected from (bl). Embodiment 128. The herbicidal mixture of embodiment 127, wherein component (b) comprises bromoxynil. Example 129. Herbicidal mixture of Example 127 The ingredient (b) comprises a dimethametryn. Embodiment 130. The herbicidal mixture of embodiment 126, wherein component (b) comprises at least one selected from the group consisting of An additional active ingredient of bl3). Embodiment 131. The herbicidal mixture of embodiment 130, wherein component (b) comprises haloxydine. Embodiment 132 - the herbicidal mixture of embodiment 126, wherein component (b) comprises at least one An additional active ingredient selected from (bl5). Embodiment 133. The herbicidal mixture of embodiment 132, wherein component (b) comprises at least one additional active ingredient selected from the group consisting of chlorpyrifos, chlorpyrifos, 1-bromo-4-[(methylmethyl)sulfonyl] Benzene, solution 72 201240602 toxic quinquin, benzalkon, acetochloronitrile, pyridine azide, chlorpyrifos, a random propylene amine, two ring ang g (Cyc丨〇n〇n), 4_ (two gas B Mercapto)-1-oxa-4-azospiro[4 5]decane (M〇N 4660), 2-(dichloromethyl)_2_methyl_13_dioxolane (MG) 191), piperidan, oxazolidine, oxadiazepine, oxalic acid, flubendiate, chlorpyrifos, diphenyl chelate, salivary, mephenate, benzophenone, Naphthalic anhydride and 8 oxalic acid. 134. The herbicidal mixture of embodiment 133, wherein component (b) comprises at least one additional active ingredient selected from the group consisting of chlorpyrifos, detoxified quinine, beta-fixamidine, chlorpyrifos, sulforaphane, oxazole Herbicide, Mevoto and oxalic acid. Embodiment 135. The herbicidal mixture of Embodiment 134, wherein the component (b) comprises at least one additional active ingredient selected from the group consisting of detoxified quinoxaline, zoresin and oxaliconitrile. Embodiment 136. The herbicidal mixture of embodiment 135, wherein component (b) comprises at least one additional active ingredient selected from the group consisting of detoxified quinoxanes. Embodiment 137. The herbicidal mixture of embodiment 135, wherein component (b) comprises at least one additional active ingredient selected from the group consisting of oxaliconitrile. Embodiments of the invention (including the above Examples 1-124F and any other embodiments described herein) may be combined in any manner, and the description of the variations in the examples applies not only to the compound of Formula 1, but also to Starting compounds and intermediate compounds (including compounds of Formulas 1Q, 1R and 1S) which are useful in the preparation of compounds of Formula 1. Furthermore, the embodiments of the present invention (including the above-described Examples 1 to 124E or 125 to 137 to 73 201240602 and any other embodiments described herein, in combination with any of them) are applicable to the compositions and methods of the present invention. The combinations of Examples 1 to 124F are illustrated by the following: Example A. The compound of Formula 1, wherein A is Α·1, A-3, A-4, A-5 or Α·6; R1 is

或 ίο R1 為-WtpE1)!^24 、 -WlLC(=E2)R25 或 -WtpEiLR26 ;或 R1 為 N(R4Q)R41 ;或 R1 為 GA 或-W2GA ; GA為一 9-至11-員飽和或部分飽和碳螺環或雜螺環 is 環系,其選擇性地包括選自C(=0)、C(=N-0R3(&gt;) 或C=NN(R29)的環員,各環或環系選擇性地經 至多三個選自在碳環員上之R21與在氮環員上 之R22的取代基取代;或 各GA為一 9-員部分飽和稠合且含碳環員與2個氮 20 環員之環系,該環經1個選自在氮環員上之 R22的取代基取代; 各 E1、E2 與 E3 獨立為 Ο、NOR28 或 NN(R28)2; L獨立為Ο或N(R31); 74 201240602 與11獨立為氫;或CrC4烷基或C3-C5 %烷基,各選擇性地經一或多個選自由函素、 CN、羥基、Cl_C2烷氧基、Ci_c2烷亞磺醯基 與匚广^烷續醯基所組成之群組的取代基; 各R28獨立為Η、CrC3烷基或Cl_C3鹵烷基; 各R獨立為Η、CrC3烷基、CrC3 4烷基、crC3 烷羰基、CV-C:3烷磺醯基或crC3鹵烷磺醯基; 各Q1與Q2獨立為〇或N(R31); Q為C^-C3伸烧基,其選擇性地經至多2個選自 Ci-C4烧基的取代基取代; R30獨立為Η、CrC3烷基或CrC3齒烷基; R31獨立為Η、CrC3烷基或CrC3齒烷基; R32為Η或crc3烷基; W1 為 c2-c4 伸烷基、-(CH2)2OCH2^_(CH2)3〇CH2_; W2為Crc3伸烷基; W為C1-C4伸院基; R2為苯基或-w3(苯基),各選擇性地在環員上經至 多五個選自R21 ;或-G ;或CrC6烷基、C2-C6 稀基、C2_C6快基、Ci_C6鹵院基、C2_C6函烯 基、c2-c6鹵炔基、c3-c8環烷基、c3-c8鹵環 烷基、c4-c1G烷環烷基、c4-c1G環烷烷基、c6-c14 環烷環烷基、c4-c10函環烷烷基、c5-c12烷環 燒烧基、C3-C8環稀基、C3-C8鹵環稀基、C2-C8 烷氧烷基、CrC1G烷氧烯基、C4-C1G環烷氧烷 基、C4-C1Q環烷氧烷氧烷基、c3_c1G烷氧烷氧 烷基、CrC8烷硫烷基、C2-C8烷亞磺醯烷基、 75 201240602 〇2_匸8炫&gt;續酿院基、匚2_匚8烧無·基、C4-C1Q環彿 烧基、C2-C8齒院氧院基、C2_C8烧氧函炫基、 c2-c8鹵烷氧函烷基、c4-c10鹵環烷氧烷基、 CrC10環烯氧烷基、C4-C10鹵環烯氧烷基、 C3-C10二烷氧烷基、CrC6烷氧基、CVQ鹵烷 氧基、C3-C8環烧氧基、C3-C8 ill環院氧基、 c4-c10環烷烷氧基、c2-c6烯氧基、c2-c6鹵烯 氧基、c3-c6炔氧基、c3-c6鹵炔氧基、c2-c8 烷氧烷氧基、c2-c8烷羰氧基、c2-c8 ii烷羰氧 基、C4-C10環烧艘氧基、C3-C1G烧幾院氧基、 院硫基、Cl-Cg .烧硫基、C3-C8環;^硫 基、CVC6烷亞磺醯基、CVC6鹵烷亞磺醯基、 CrC6烷磺醯基、CVC6鹵烷磺醯基、c3-c8環 炫》續酿基、C3-C8三院發基、C3-C8環稀氧基、 C3-C8函環烯氧基、C2-C8函烷氧烷氧基、c2-c8 烷氧鹵烷氧基、c2-c8鹵烷氧鹵烷氧基、c3-c1() 烷氧羰烷氧基、C2-C8烷基(硫羰基)氧基、c3-c8 環烷亞磺醯基或c3-c1G _三烷矽基的取代基 取代;或 R2 為-W6C(=E4)R33 、 -^/6LlC(=E5)RM 或 -W6C(=E6)L1R35 ; 各 E4、E5 與 E6 獨立為 ο、NOR37 或 NN(R37)2 ; 各L1獨立為o或N(R38); 各R 、R與R獨立為氫;或Ci_C4院基、C3_C5 環烷基,各選擇性地經一或多個選自由齒素、 CN、經基、crc2烷氧基、crc2烷亞續醯基 76 201240602 與Crc2烷磺醯基所組成之群組的取代基取 代; 各R37獨立為Η、CrC3烷基或crc3鹵烷基 28 獨立為Η、C1-C3院基或C1-C3鹵烧基; W3 為 _CH2-; ]〇 w6 為 C2-C4 伸烷基、-(CH2)2〇CH2-或-(ch2)3och2-; R3為經基、、c2-c8烷羰氧基、c2-c8鹵烷羰 氧基、c4-c1G環烷羰氧基或c3-c1G烷羰烷氧 基;或苄氧基、苯氧基、苄羰氧基、苯羰氧基、 苯磺醯氧基或节磺醯氧基,各選擇性地在環員 上經至多兩個選自R21的取代基取代; M+為一鈉或钟金屬陽離子; R為Ci-C6烧基;Or ίο R1 is -WtpE1)!^24, -WlLC(=E2)R25 or -WtpEiLR26; or R1 is N(R4Q)R41; or R1 is GA or -W2GA; GA is a 9- to 11-member saturated or a partially saturated carbon spiro or heterospirois is ring system, optionally comprising a ring member selected from C(=0), C(=N-0R3(&gt;) or C=NN(R29), each ring or The ring system is selectively substituted with up to three substituents selected from R21 on a carbocyclic member and R22 on a nitrogen ring member; or each GA is a 9-membered partially saturated fused and carbocyclic ring member and 2 a ring of nitrogen 20 ring members substituted by a substituent selected from R22 on a nitrogen ring; each of E1, E2 and E3 is independently Ο, NOR28 or NN(R28)2; L is independently Ο or N (R31); 74 201240602 and 11 are independently hydrogen; or CrC4 alkyl or C3-C5% alkyl, each optionally one or more selected from the group consisting of a functional element, a CN, a hydroxyl group, a Cl_C2 alkoxy group, and a Ci_c2 alkane a substituent of a group consisting of a sulfonyl group and a fluorene group; each R28 is independently a fluorene, a CrC3 alkyl group or a Cl_C3 haloalkyl group; each R is independently a hydrazine, a CrC3 alkyl group, a CrC3 4 alkyl group, crC3 alkylcarbonyl, CV-C: 3 alkanesulfonyl or crC3 halosulfonyl; each Q1 and Q2 are independently 〇 or N(R31); Q is a C^-C3 extended alkyl group which is optionally substituted with up to two substituents selected from the group consisting of Ci-C4 alkyl; R30 is independently hydrazine, CrC3 alkyl or CrC3 dentate R31 is independently hydrazine, CrC3 alkyl or CrC3 dentate; R32 is hydrazine or crc3 alkyl; W1 is c2-c4 alkyl, -(CH2)2OCH2^_(CH2)3〇CH2_; W2 is Crc3 An alkyl group; W is a C1-C4 stretching group; R2 is a phenyl group or a -w3 (phenyl group), each selectively having up to five members selected from R21; or -G; or CrC6 alkyl group, C2; -C6 dilute group, C2_C6 fast group, Ci_C6 halogen compound group, C2_C6 alkenyl group, c2-c6 haloalkynyl group, c3-c8 cycloalkyl group, c3-c8 halocycloalkyl group, c4-c1G alkane cycloalkyl group, c4 -c1G cycloalkane, c6-c14 cycloalkylcycloalkyl, c4-c10 functional cycloalkylalkyl, c5-c12 alkanealkyl, C3-C8 cycloaliphatic, C3-C8 halocyclo, C2 -C8 alkoxyalkyl, CrC1G alkoxyalkenyl, C4-C1G cycloalkoxyalkyl, C4-C1Q cycloalkoxyalkyl, c3_c1G alkoxyalkyl, CrC8 alkylthio, C2-C8 Alkylsulfinylalkyl, 75 201240602 〇2_匸8 Hyun&gt; Continued Brewing Base, 匚2_匚8 Burning No Base, C4-C1Q 环佛烧基, C2-C8 牙院氧院, C2_C8 Oxygen , c2-c8 haloalkoxyalkyl, c4-c10 halocycloalkoxyalkyl, CrC10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkyloxyalkyl, CrC6 alkoxy , CVQ haloalkoxy, C3-C8 cycloalkoxy, C3-C8 ill ring oxime, c4-c10 cycloalkanoxy, c2-c6 alkenoxy, c2-c6 haloenyloxy, c3 -c6 alkynyloxy, c3-c6 haloalkoxy, c2-c8 alkoxyalkoxy, c2-c8 alkylcarbonyloxy, c2-c8 ii alkylcarbonyloxy, C4-C10 cyclopentyloxy, C3 -C1G burns several oxy groups, thiol groups, Cl-Cg. sulphur-based, C3-C8 rings; thiol, CVC6 alkylsulfinyl, CVC6 halosulfinyl, CrC6 alkanesulfonyl, CVC6 haloalkylsulfonyl, c3-c8 cyclodextrin, C3-C8 three-yard base, C3-C8 cycloaliphatic, C3-C8 functional cycloalkenyloxy, C2-C8 alkoxylated oxygen Base, c2-c8 alkoxyhaloalkoxy, c2-c8 haloalkoxyhalooxy, c3-c1() alkoxycarbonylalkoxy, C2-C8 alkyl(thiocarbonyl)oxy, c3-c8 Substituted with a cycloalkylsulfinyl or a c3-c1G-trialkylsulfonyl substituent; or R2 is -W6C(=E4)R33, -^/6LlC(=E5)RM or -W6C(=E6)L1R35; E4, E5 and E6 are independent of ο, NOR37 or NN(R37)2; each L1 is independent Is o or N(R38); each R, R and R are independently hydrogen; or Ci_C4, C3_C5 cycloalkyl, each optionally one or more selected from the group consisting of dentate, CN, thiol, crc2 alkoxy Substituted by a group consisting of a group consisting of a group consisting of a Crc2 alkanesulfonyl group; each of R37 is independently a fluorene, a CrC3 alkyl group or a crc3 haloalkyl group 28 independently as a fluorene, a C1-C3 courtyard group. Or C1-C3 haloalkyl; W3 is _CH2-; ]〇w6 is C2-C4 alkyl, -(CH2)2〇CH2- or -(ch2)3och2-; R3 is a trans group, c2-c8 Alkylcarbonyloxy, c2-c8 halocarbonyloxy, c4-c1Gcycloalkaneoxy or c3-c1G alkylcarbonyloxy; or benzyloxy, phenoxy, benzylcarbonyloxy, phenylcarbonyloxy a benzenesulfonyloxy or a sulfonyloxy group, each optionally substituted with up to two substituents selected from R21 on the ring member; M+ is a monosodium or a metal cation; R is a Ci-C6 alkyl group;

RlG為Η、鹵素或CiC6_烷基; 15RlG is hydrazine, halogen or CiC6_alkyl; 15

Rl1 為 Η 或 CrCVJ^基; 12 R為H、鹵素、氰基、羥基、胺基或c〗-C6烷基; 各 R14、R15、R18 與 R19 為 Η 或 CH3 ; r2Q 為 Η 或 CH3 ; T 為-CH2CH2-或-CH=CH-; 20 各G為G-1至G-20 (如實施例116中所描述者); r為 〇、ι、2或3; 各R21獨立為鹵素、氰基、羥基、硝基、-CHO、-SH、Rl1 is Η or CrCVJ^; 12 R is H, halogen, cyano, hydroxy, amine or c-C6 alkyl; each R14, R15, R18 and R19 is Η or CH3; r2Q is Η or CH3; Is -CH2CH2- or -CH=CH-; 20 each G is G-1 to G-20 (as described in Example 116); r is 〇, ι, 2 or 3; each R21 is independently halogen, cyanide Base, hydroxyl, nitro, -CHO, -SH,

Ci-C6 院基、C2-C6 稀基、C2-C6 快基、Ci-C6 鹵 烷基、c2-c6鹵烯基、C2-C6鹵炔基、C3-C8環 燒基、C3-C8鹵環烧基、C4-C10烧環燒基、C4-C10 環烷烷基、(:3-(:8環烯基、C3-C8鹵環烯基、c2-c8 77 25 201240602 烷氧烷基、CVCn)環烷氧烷基、c3-C1G烷氧烷 氧炫•基、C2-Cg烧硫燒基、C2_Cg燒亞確酿炫》 基、c2-c8烷氧鹵烷基、c2-C5氰烷基、crc6 羥烷基、CrC6烷氧基、crC6 li烷氧基、c3-c8 5 環烷氧基、C3_c8 環烷氧基、c4-c1G環烷烷 氧基、C2-C6稀氧基、c2-c6鹵烯氧基、c2-c8 烷氧烷氧基、C2-C8烷羰氧基、crc6烷硫基、 Ci_C6鹵烧硫基、C3-C8環烧硫基、Ci_C6院亞 磺醯基、crc6鹵烷亞磺醯基、crc6烷磺醯 10 基、Crc6 4烷磺醯基或C3-C8環烷磺醯基; 各R22獨立為CrC6烷基或CrC6 _烷基; R40為乙基或異丙基;以及 R為乙基或異丙基;或 R40 與 r41 —起作為-(CH2)5-、-CH2CH=CHCH2-或 15 -(CH2)2〇(CH2)2-。 實施例Β·實施例a之化合物,其中 A 為 A-1、A-3 或 A-5 ; B1 為 C-1 ; B2 為 C-3 ; 20 β 為 C-1 ; R1 為-GA ; 各 GA 係選自 GA-1、GA-2、GA-3、GA-7、GA-8 與 GA-9 ;或 各GA為Ci-C6, C2-C6 dilute, C2-C6 fast radical, Ci-C6 haloalkyl, c2-c6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halo Cycloalkyl, C4-C10 alkyl group, C4-C10 cycloalkyl, (3-(:8-cycloalkenyl, C3-C8 halocycloalkenyl, c2-c8 77 25 201240602 alkoxyalkyl, CVCn) cycloalkoxyalkyl, c3-C1G alkoxy alkoxy, C2-Cg sulphur-burning, C2_Cg sulphide, c2-c8 alkoxyhalo, c2-C5 cyano , crc6 hydroxyalkyl, CrC6 alkoxy, crC6 li alkoxy, c3-c8 5 cycloalkoxy, C3_c8 cycloalkoxy, c4-c1G cycloalkanoxy, C2-C6 dioxy, c2 -c6 haloenyloxy, c2-c8 alkoxyalkoxy, C2-C8 alkoxycarbonyl, crc6 alkylthio, Ci_C6 halogenated thio, C3-C8 cyclosulphonyl, Ci_C6 sulfinyl, Crc6 haloalkyl sulfinyl, crc6 alkanesulfonyl 10, Crc6 4 alkanesulfonyl or C3-C8 cycloalkylsulfonyl; each R22 is independently CrC6 alkyl or CrC6-alkyl; R40 is ethyl or different a propyl group; and R is an ethyl group or an isopropyl group; or R40 and r41 together as -(CH2)5-, -CH2CH=CHCH2- or 15-(CH2)2〇(CH2)2-. a compound of example a, Wherein A is A-1, A-3 or A-5; B1 is C-1; B2 is C-3; 20β is C-1; R1 is -GA; each GA is selected from GA-1, GA- 2. GA-3, GA-7, GA-8 and GA-9; or each GA is

7S 25 2012406027S 25 201240602

R2為苯基或_W3(苯基),各選擇性地在環員上經至 多兩個選自R21的取代基取代;或-G ;或CrC6 5 院基或〇3~(^8環燒基; R3為羥基或CVC8烷羰氧基; R9 為 CH2CH3 ; R1G 為 Η 或 CH3 ; T 為-CH2CH2-; 10 G 為 G-2、G-3 或 G-15 ;以及 r21獨立為齒素、硝基、CrC6烷基、CrC6齒烷基、R2 is phenyl or _W3 (phenyl), each optionally substituted with up to two substituents selected from R21 on the ring member; or -G; or CrC6 5 or 〇3~(^8 ring-burning R3 is hydroxy or CVC8 alkoxycarbonyl; R9 is CH2CH3; R1G is Η or CH3; T is -CH2CH2-; 10G is G-2, G-3 or G-15; and r21 is independently dentate, Nitro, CrC6 alkyl, CrC6 aldentyl,

CrC6燒氧基、Ci_C6 i烷氧基或CrC6烷硫基; 各R22獨立為CH3或CH2CF3 ;以及 r4〇 與 r41 一 起作為_(CH2)5-、-CH2CH=CHCH2-或 15 -(CH2)2〇(CH2)2-。 實施例C.實施例B之化合物,其中 A 為 A-1 或 A-3 ; 各GA係選自GA-2與ga-3 ;或 各GA為CrC6 alkoxy, Ci_C6 i alkoxy or CrC6 alkylthio; each R22 is independently CH3 or CH2CF3; and r4〇 together with r41 as _(CH2)5-, -CH2CH=CHCH2- or 15-(CH2)2 〇(CH2)2-. Embodiment C. A compound of Embodiment B wherein A is A-1 or A-3; each GA is selected from the group consisting of GA-2 and ga-3; or each GA is

,苯^ ;或-G ;或(:3-(:8環烧基;以及 R ~作為_(CH2)5-或-(CH2)20(CH2)2-。 79 201240602 實施例D.實施例c之化合物,其中 A 為 A-1 ; 各〇4為, benzene^; or -G; or (: 3-(:8 cyclization; and R~ as _(CH2)5- or -(CH2)20(CH2)2-. 79 201240602 Example D. Examples a compound of c, wherein A is A-1; each 〇4 is

R2為苯基; r3G為Η或曱基; R21為鹵素或(:丨-(:3烷基;以及 R22 為 CH3。 實施例E.實施例b之化合物,其中 A 為 A-1 ; GA 為 GA-2 ; R2為苯基、2-噻吩基、5-氯-2-吡啶基或環丙基; R3為經基;以及 各 R14、R15、R18 與 R19為 H。 實施例F.實施例B之化合物,其中 A 為 A-3 ; GA 為 GA-2 ; R2為苯基、2-噻吩基5-氯·2-吡啶基或環丙基;以 及 R3為經基。 實施例G·實施例Α之化合物,其中 A 為 A-1 ; R1為 80 25 201240602R2 is phenyl; r3G is fluorenyl or fluorenyl; R21 is halogen or (: 丨-(:3 alkyl; and R22 is CH3. Example E. The compound of Example b, wherein A is A-1; GA is GA-2; R2 is phenyl, 2-thienyl, 5-chloro-2-pyridyl or cyclopropyl; R3 is a trans group; and each of R14, R15, R18 and R19 is H. Example F. Examples A compound of B, wherein A is A-3; GA is GA-2; R2 is phenyl, 2-thienyl 5-chloro-2-pyridyl or cyclopropyl; and R3 is a trans group. A compound of the formula wherein A is A-1; R1 is 80 25 201240602

各Q1與Q2為Ο ; 5 Q3為C2_伸烧基; R32為Η或曱基; W5為C2-C3伸烷基; R2為苯基、2-曱基苯基、3_甲基苯基、3-溴苯基、 3-氣苯基、4_氣苯基、3-氟苯基、3,5-二氟苯基、 ίο 3-嗟吩基或2-嗟吩基, R3 為羥基或-0C(=0)CH2CH(CH3)2;以及 各 R14、R15、R18 與 R19 為 Η 或 CH3。 實施例H.實施例G化合物,其中 W5為C2伸烷基或C3伸烷基; is R2為苯基、3-噻吩基或環丙基;以及 R3為羥基。 具體實施例包括一選自下列之式1化合物: 3-(1,4-二氧雜螺[4.5]癸-8-基)-5·[(2_羥基-6-側氧基 _1· ί哀己稀-1-基)叛基]-2-苯基β密咬酉同 2〇 (3-(l,4-dioxaspiro[4.5]dec-8-yl)-5-[(2-hydroxy- 6-oxo-l-cyclohexen-l-yl)carbonyl]-2-phenyl-4(3 //)-pyrimidinone)(化合物 1)、 5-[(2-羥基-6-側氧基-1-環己烯-1-基)羰基]-6-側氧基 -2-苯基-1(6//)-嘴咬乙酸· 1-(0-曱基肪) 201240602 (5-[(2-hydroxy-6-oxo-l-cyolohexen-l-yl)carbony l]-6-oxo-2-phenyl-l(6//)-pyrimidineacetaldehyd e l-(C)-methyloxime))(化合物 2)、 2-(5-氣-3-吼啶基)-3-(1,4-二氧雜螺[4.5]癸-8-5 基)-5-[(2-經基-6-側氧基-1- J哀己稀-1-基)幾 基 ]-4(3//)- 嘧啶酮 (2-(5-chloro-3-pyridinyl)-3-(l,4-dioxaspiro[4.5] dec-8-yl)-5-[(2-hydroxy-6-oxo-l-cyclohexen-l-y l)carbonyl]-4(3//)-pyrimidinone)(化合物 7)、 ίο 2-ί哀丙基-3-(l,4-二氧雜螺[4.5]癸-8-基)-5-[(2_經基 -6-側氧基-1-環己稀-1-基)幾基]-4(3//)-喊咬綱 (2-cyclopropyl-3-(i,4-dioxaspiro[4.5]dec-8-yl)-5-[(2-hydroxy-6-oxo-l-cyclohexen-l-yl)carbonyl ]-4(3//)-pyrimidinone)(化合物 10)、 15 3-(1,4-二氧雜螺[4.5]癸-8_基)-5_[(2-羥基-4-側氧基 雙環[3.2.1]辛-2-烯-3-基)羰基]-2-(2·噻吩 基 )-4(3//)- 嘧啶酮 (-(l,4-dioxaspiro[4.5]dec-8-yl)-5-[(2-hydroxy-4 -oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl]-2-(2-2〇 thienyl)-4(3ii)-pyrimidinone)(化合物 15 )與 5-[(2-經基-6-側氧基-1-環己稀-1-基)幾基]-2·苯基 -3-(4,5,6,7-四氫-2-甲基-2//-吲唑-5-基)-4(3//)-嘴咬酮 (5-[(2-hydroxy-6-oxo-l-cyclohexen-l-yl)carbony 25 l]-2-phenyl-3-(4,5,6,7-tetrahydro-2-methyl-2//-i ndazol-5_yl)-4(3//)-pyrimidinone)(化合物 19)。 82 201240602 如發明内容中所述之本發明實施例亦包括(其中如 用於下列實施例中之發明内容的式1Q包括其沁氧化物 及其鹽): 實施例1Q·式1Q之化合物,其中A'為A'-l、A’-3 5 或 A'-5。 實施例2Q.實施例1Q之化合物,其中A為Α··1 或 Α,-3。 實施例3Q.實施例2Q之化合物,其中Α·為A’-l。 實施例4Q.實施例2Q之化合物,其中A·為A'-3。 ίο 實施例5Q.式1Q或實施例1Q至4Q其中任一者 之化合物,其中B1為C-1。 實施例6Q.式1Q或實施例1Q至4Q其中任一者 之化合物,其中B1為C-2。 實施例7Q.式1Q或實施例1Q至6Q其中任一者 15 之化合物,其中B2為C-3。 實施例8Q.式1Q或實施例1Q至6Q其中任一者 之化合物,其中B2為C-4。 實施例9Q.式1Q或實施例1Q至8Q其中任一者 之化合物,其中.B3為C-1。 20 實施例10Q.式1Q或實施例1Q至8Q其中任一者 之化合物,其中B3為C-2。 實施例11Q.式1Q或實施例1Q至10Q其中任一 者之化合物,其中R1為 83 201240602Each Q1 and Q2 is Ο; 5 Q3 is C2_stretching base; R32 is fluorene or fluorenyl; W5 is C2-C3 alkyl; R2 is phenyl, 2-mercaptophenyl, 3-methylphenyl , 3-bromophenyl, 3-phenylphenyl, 4-p-phenyl, 3-fluorophenyl, 3,5-difluorophenyl, ίο 3-nonyl or 2-nonyl, R3 is hydroxy Or -0C(=0)CH2CH(CH3)2; and each of R14, R15, R18 and R19 is Η or CH3. Embodiment H. The compound of Embodiment G wherein W5 is C2 alkyl or C3 alkyl; is R2 is phenyl, 3-thienyl or cyclopropyl; and R3 is hydroxy. Specific examples include a compound of formula 1 selected from the group consisting of 3-(1,4-dioxaspiro[4.5]dec-8-yl)-5.[(2-hydroxy-6-o-oxyl_1. ί 己 -1- ) ] ] ] ] ] ] ] ] -2- -2- -2- -2- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- - 6-oxo-l-cyclohexen-l-yl)carbonyl]-2-phenyl-4(3 //)-pyrimidinone) (Compound 1), 5-[(2-hydroxy-6-sideoxy-1- Cyclohexene-1-yl)carbonyl]-6-sideoxy-2-phenyl-1(6//)-mouth bite acetic acid · 1-(0-曱 base fat) 201240602 (5-[(2- Hydroxy-6-oxo-l-cyolohexen-l-yl)carbony l]-6-oxo-2-phenyl-l(6//)-pyrimidineacetaldehyd e l-(C)-methyloxime)) (Compound 2), 2 -(5-aza-3-acridinyl)-3-(1,4-dioxaspiro[4.5]dec-8-5yl)-5-[(2-carbyl-6-sideoxy- 1-(5-//)-pyrimidinone (2-(5-chloro-3-pyridinyl)-3-(l,4-dioxaspiro[4.5] dec- 8-yl)-5-[(2-hydroxy-6-oxo-l-cyclohexen-lyl)carbonyl]-4(3//)-pyrimidinone) (Compound 7), ίο 2-ί哀propyl-3 -(l,4-dioxaspiro[4.5]dec-8-yl)-5-[(2_carbyl-6-o-oxy-1-cyclohex-1-yl)yl]-4 (3//) - shouting (2-cyclopropyl-3-(i,4-dioxas) Piro[4.5]dec-8-yl)-5-[(2-hydroxy-6-oxo-l-cyclohexen-l-yl)carbonyl]-4(3//)-pyrimidinone) (Compound 10), 15 3 -(1,4-Dioxaspiro[4.5]dec-8-yl)-5-[(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl] -2-(2·thienyl)-4(3//)-pyrimidinone (-(l,4-dioxaspiro[4.5]dec-8-yl)-5-[(2-hydroxy-4 -oxobicyclo[3.2 .1]oct-2-en-3-yl)carbonyl]-2-(2-2〇thienyl)-4(3ii)-pyrimidinone) (Compound 15) and 5-[(2-Pheptyl-6-side) Oxy-1-cyclohexyl-1-yl)methyl]-2-phenyl-3-(4,5,6,7-tetrahydro-2-methyl-2//-carbazole-5- Base)-4(3//)- ketone (5-[(2-hydroxy-6-oxo-l-cyclohexen-l-yl)carbony 25 l]-2-phenyl-3-(4,5, 6,7-tetrahydro-2-methyl-2//-i ndazol-5_yl)-4(3//)-pyrimidinone) (Compound 19). 82 201240602 The embodiments of the invention as described in the Summary of the Invention also include (wherein Formula 1Q as used in the Summary of the Examples below includes its cerium oxide and salts thereof): Example 1Q. Compound of Formula 1Q, wherein A' is A'-l, A'-3 5 or A'-5. Embodiment 2Q. The compound of Embodiment 1Q wherein A is Α··1 or Α,-3. Embodiment 3Q. The compound of Embodiment 2Q wherein Α· is A’-1. Embodiment 4Q. A compound of Embodiment 2Q wherein A. is A'-3. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。. Embodiment 6Q. A compound of Formula 1Q or any one of Embodiments 1Q to 4Q, wherein B1 is C-2. Embodiment 7Q. A compound of Formula 1Q, or any one of Embodiments 1Q to 6Q, wherein B2 is C-3. Embodiment 8Q. A compound of Formula 1Q or any one of Embodiments 1Q to 6Q, wherein B2 is C-4. Embodiment 9Q. A compound of Formula 1Q or any one of Embodiments 1Q to 8Q, wherein .B3 is C-1. The compound of the formula 1Q or any one of the embodiments 1Q to 8Q, wherein B3 is C-2. Embodiment 11Q. A compound of Formula 1Q or any of Embodiments 1Q to 10Q, wherein R1 is 83 201240602

R1 為-WiCpEbR24 、-\¥士(:(=丑2)1125 或 -W^pEiLR26 ;或 R1 為-GA 或-W2GA。 實施例12Q.式1Q或實施例1Q至11Q其中任一 者之化合物,其中R1為 10R1 is -WiCpEbR24, -\¥士(:(= ugly 2)1125 or -W^pEiLR26; or R1 is -GA or -W2GA. Example 12Q. Compound of Formula 1Q or any of Examples 1Q to 11Q , where R1 is 10

實施例13Q.實施例12Q之化合物,其中各Q1與 Q2 為 Ο。 15 實施例14Q.實施例12Q之化合物,其中Q3為C2-伸烷基,其選擇性地經至多2個選自CrC2烷 基的取代基取代。 實施例15Q.實施例14Q之化合物,其中Q3為C2· 伸烷基,其選擇性地經至多2個選自曱基的取 代基取代。 實施例16Q.式1Q或實施例1Q至15Q其中任一 者之化合物,其中W5為CrC4伸烷基。 實施例17Q.式1Q或實施例1Q至16Q其中任一 者之化合物,其中R32為Η或CrC3烷基。 84 201240602 實施例17QA·實施例17Q之化合物,其中R32為 Η或甲基。 實施例18Q.實施例17Q之化合物,其中R32為甲 基。 5 實施例19Q·式1Q或實施例1Q至11Q其中任一 者之化合物,其中R1為-WtpEbR24、 -WtceE^R25 或 _W1C(=E3)LR26。 實施例12QA.式1Q或實施例1Q至19Q其中任一 者之化合物,其中W1為C2-C4伸烷基、 ίο -(CH2)2OCH2-或-(CH2)3OCH2-。 實施例20Q.式1Q或實施例1Q至11Q或19Q其 中任一者之化合物,其中各E1、E2與E3獨立 為 Ο、NOR28 或 NN(R28)2。 實施例20QA.式1Q或實施例1Q至20Q其中任一 15 者之化合物,其中R28獨立為H、CrC3烷基或 C1-C3 1¾ 院基 實施例20QB.式1Q或實施例1Q至10Q其中任一 者之化合物,其中R1不為-N(R4G)(R41)。 實施例21Q.式1Q或實施例1Q至11Q或19Q其 2〇 中任一者之化合物,其中各L獨立為Ο或 N(R31); 其限制條件是當E3為0,則L不為0 ; 實施例22Q.式1Q或實施例1Q至21Q其中任一 者之化合物,其中W1為CrC4伸烷基。 25 實施例23Q.式1Q或實施例1Q至11Q或19Q其 中任一者之化合物,其中各R24、R25與R26獨 85 201240602 立為氫;或CrC2烷基或CVc:4環烷基,各選 擇性地經一或多個選自由_素、CN、羥基與 CrC2烷氧基所組成之群組的取代基取代广、 實施例24Q.式1Q或實施例1Q至其中任— 者之化合物,其中R1為-GA。 、 實施例25Q.實施例24Q之化合物,其中#為— 5·至6-員碳環,其包括選自O〇、 或C=NN(R29)2的環員,各環選擇性地經至多 兩個選自R21的取代基取代。 實施例26Q.實施例25Q之化合物,其中R29獨立 為Η、CrC3烷基、CrC3 _烷基或Ci_C3烷羰 基。 實施例26QA.實施例25Q之化合物,其中r3〇獨 立為Η、CrC3烷基或CVQ齒烷基。 實施例27Q.實施例24Q之化合物’其中ga為— 9-至10-員飽和雜螺環環系,其選擇性地包括 選自C(=0)或C(=N-OR3())的環員,各環或環系 選擇性地經至多兩個選自在碳環員上之R21與 在氮環員上之R22的取代基取代; 實施例28Q.實施例27Q之化合物,其中R30獨立 為Η、C1-C3院基或C1-C3鹵烧基; 實施例29Q.實施例27Q或28Q之化合物’其中 GA係選自 GM、GA-2、GA-3、GA-7、GA-8 與 GA-9 (如實施例51中所述者)。 實施例30Q_實施例29Q之化合物,其中GA係選 自 GA-2 與 GA-3。 86 201240602 實施例30QA.實施例30Q之化合物, GA-2。 其中 GA為 實施例30QB.式1Q或實施例至 -者之化合物4中各為1員部:: 和稠合且含碳環員與2個氮環員之環系,士班 選擇性地經至多2個選自在碳環員上之二 在氮環員上之R22的取代基取代。 與 實施例30QC·式1或實施例iq至24q其中任— 者之化合物,其中各#為一 9-員部分飽^稠 合且含碳環員與2個氮環員之環系,該環經i 個選自在氮環員上之R22的取代基取代。 實施例30QD.實施例30QC之化合物,其中各gA 為 15Embodiment 13Q. The compound of Embodiment 12Q wherein each of Q1 and Q2 is hydrazine. The compound of Embodiment 12Q wherein Q3 is a C2-alkylene group which is optionally substituted with up to two substituents selected from the group consisting of CrC2 alkyl groups. Embodiment 15Q. The compound of Embodiment 14Q wherein Q3 is C2.alkylene, which is optionally substituted with up to 2 substituents selected from thiol. Embodiment 16Q. A compound of Formula 1Q or any one of Embodiments 1Q to 15Q wherein W5 is a CrC4 alkylene group. Embodiment 17Q. A compound of Formula 1Q or any one of Embodiments 1Q to 16Q wherein R32 is hydrazine or CrC3 alkyl. 84201240602 Embodiment 17QA. The compound of Embodiment 17Q wherein R32 is hydrazine or methyl. Embodiment 18Q. The compound of Embodiment 17Q wherein R32 is methyl. The compound of any one of the above formulas 1Q or 1Q to 11Q, wherein R1 is -WtpEbR24, -WtceE^R25 or _W1C(=E3)LR26. Embodiment 12QA. A compound of Formula 1Q or any one of Embodiments 1Q to 19Q wherein W1 is C2-C4 alkyl, ίο-(CH2)2OCH2- or -(CH2)3OCH2-. Embodiment 20Q. A compound of Formula 1Q or any one of Embodiments 1Q to 11Q or 19Q, wherein each of E1, E2 and E3 is independently Ο, NOR28 or NN(R28)2. Embodiment 20QA. A compound of Formula 1Q or any one of Embodiments 1Q to 20Q, wherein R28 is independently H, CrC3 alkyl or C1-C3 13⁄4. Courtamentally Example 20QB. Formula 1Q or Examples 1Q to 10Q A compound of the formula wherein R1 is not -N(R4G)(R41). Embodiment 21Q. The compound of any one of Formula 1Q or Embodiment 1Q to 11Q or 19Q, wherein each L is independently Ο or N(R31); the limitation is that when E3 is 0, L is not 0. Embodiment 22Q. A compound of Formula 1Q or any one of Embodiments 1Q to 21Q, wherein W1 is a CrC4 alkylene group. </ RTI> </ RTI> </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> </ RTI> <RTIgt; Substituting one or more substituents selected from the group consisting of _, CN, hydroxy and CrC 2 alkoxy, compound of Example 24Q. Formula 1Q or Example 1Q to any of them, wherein R1 is -GA. The compound of Embodiment 24Q, wherein # is a 5- to 6-membered carbocyclic ring comprising a ring member selected from O〇, or C=NN(R29)2, each ring optionally being at most Two substituents selected from R21 are substituted. Embodiment 26Q. The compound of Embodiment 25Q wherein R29 is independently hydrazine, CrC3 alkyl, CrC3-alkyl or Ci_C3 alkylcarbonyl. Embodiment 26QA. The compound of Embodiment 25Q wherein r3〇 is independently hydrazine, CrC3 alkyl or CVQ dentate. Embodiment 27Q. The compound of Embodiment 24Q wherein ga is a 9- to 10-membered hetero-spirocyclic ring system, optionally comprising a moiety selected from C(=0) or C(=N-OR3()) a ring member, each ring or ring system is optionally substituted with up to two substituents selected from R21 on a carbocyclic member and R22 on a nitrogen ring member; Embodiment 28Q. A compound of Embodiment 27Q wherein R30 is independently Η, C1-C3, or C1-C3 halogen; Example 29Q. Compound of Example 27Q or 28Q' wherein GA is selected from the group consisting of GM, GA-2, GA-3, GA-7, GA-8 and GA-9 (as described in Example 51). Embodiment 30Q. The compound of Embodiment 29Q wherein the GA is selected from the group consisting of GA-2 and GA-3. 86 201240602 Example 30QA. Compound of Example 30Q, GA-2. Wherein GA is the compound of Example 30QB. Formula 1Q or the compound of Example to 4 is a member:: and a ring system which is fused and contains a ring member and two nitrogen ring members. Up to two substituents selected from R22 on the ring member of the nitrogen ring member are substituted. And a compound of any one of the embodiments 30QC·Formula 1 or Examples iq to 24q, wherein each # is a 9-membered partially fused ring system comprising a carbocyclic ring member and 2 nitrogen ring members, the ring Substituted by i substituents selected from R22 on a nitrogen ring member. Embodiment 30QD. The compound of Example 30QC wherein each gA is 15

22 其中向左伸出之鍵代表連接至式1化合物之其 餘部分的連接點。 實施例30QE.實施例30QD之化合物,其中各22 wherein the key extending to the left represents the point of attachment to the remainder of the compound of Formula 1. Embodiment 30QE. The compound of Example 30QD, wherein each

87 201240602 實施例31Q.式1Q或實施例1Q至30Q其中任一 者之化合物,其中R2為苯基或-W3(苯基),各 選擇性地在環員上經至多兩個選自R21的取代 基取代;或-G;或CrC6烷基或C3-C8環烷基。 5 實施例32Q.實施例31Q之化合物,其中R2為苯 基,其選擇性地在環員上經至多兩個選自R21 的取代基取代;或-G ;或CrC6烷基或C3-C8 環烧基。 實施例32QA.實施例32Q之化合物,其中R2為苯 ίο 基;或-G ;或C3-C8環烷基。 實施例32QB.實施例32QA之化合物,其中R2為 苯基、2-σ塞吩基5-氣-2-°比咬基或環丙基。 實施例32QC.實施例32QA之化合物,其中R2為 苯基、3 塞吩基或環丙基。 15 實施例33Q.實施例32Q之化合物,其中R2為苯 基、2-曱基苯基、3-曱基苯基、3-溴苯基、3-氣苯基、4-氯苯基、3-氟苯基或3,5-二氟苯基。 實施例33QA.實施例32Q之化合物,其中R2為苯 基、3-。塞吩基或環丙基。 2〇 實施例34Q.實施例33Q之化合物,其中R2為苯 基。 實施例35Q.式1Q或實施例1Q至31Q其中任一 者之化合物,其中R2不為苯基。 實施例36Q.實施例35Q之化合物,其中R2為3-25 °塞吩基、2-°塞吩基或3-°比咬基。 88 201240602 實施例36Qa·實施例36Q之化合物,其中R2為3-0比咬基。 實施例37Q.式1Q或實施例1Q至36Q其中任一 者之化合物,其中W3為-CH2·。87. The compound of any one of the above formulas, wherein R 2 is phenyl or -W 3 (phenyl), each selectively having up to two selected from R 21 on the ring member. Substituent substitution; or -G; or CrC6 alkyl or C3-C8 cycloalkyl. The compound of Embodiment 31Q, wherein R 2 is phenyl, which is optionally substituted with up to two substituents selected from R 21 on the ring member; or -G; or CrC6 alkyl or C3-C8 ring Burning base. Embodiment 32QA. The compound of Embodiment 32Q wherein R2 is benzyl hydrazide; or -G; or C3-C8 cycloalkyl. Embodiment 32 QB. The compound of Embodiment 32QA wherein R2 is phenyl, 2-σ-saltyl 5-a-2-one ratio dimethyl or cyclopropyl. Embodiment 32 QC. The compound of Embodiment 32QA wherein R 2 is phenyl, 3 exemplyl or cyclopropyl. 15. The compound of Embodiment 32Q wherein R 2 is phenyl, 2-nonylphenyl, 3-mercaptophenyl, 3-bromophenyl, 3-phenylphenyl, 4-chlorophenyl, 3 - fluorophenyl or 3,5-difluorophenyl. Embodiment 33QA. The compound of Embodiment 32Q wherein R2 is phenyl, 3-. Queenyl or cyclopropyl. The compound of Embodiment 33Q wherein R2 is phenyl. Embodiment 35. A compound of Formula 1Q, or any one of Embodiments 1Q to 31Q, wherein R2 is not phenyl. Embodiment 36. The compound of Embodiment 35Q wherein R2 is 3-25 ° thiophene, 2-° thiophene or 3-° ratio thiol. 88 201240602 Embodiment 36Qa. The compound of Embodiment 36Q wherein R2 is a 3-0 ratio to a bite group. Embodiment 37. A compound of Formula 1Q or any one of Embodiments 1Q to 36Q, wherein W3 is -CH2.

5 實施例38Q.式1Q或實施例1Q至3Q、7Q與11Q 至37Q其中任一者之化合物,其中119為CrC6 烧基。 實施例39Q.實施例38Q之化合物,其中R9為 CH2CH3。 10 實施例40Q.式1Q或實施例1Q或11Q至39Q其 中任一者之化合物,其中R1Q為H、鹵素或CrC6 烧基。 實施例41Q.實施例40Q之化合物,其中R1G為Η 或 CH3。 15 實施例42Q.式1Q或實施例1Q至41Q其中任一 者之化合物,其中當將R14與R18的例子單獨 考量時(即R14與R18並非一起作為伸烷基或 伸烯基),則該R14與R18之例子獨立為Η或 CrC6烷基。 2〇 實施例43Q.實施例42Q之化合物,其中當將R14 與R18的例子單獨考量時,則R14與R18的例子 獨立為Η或CH3。 實施例44Q.實施例43Q之化合物,其中當將R14 與R18的例子單獨考量時,則R14與R18的例子 25 獨立為Η。 89 201240602 實施例45Q·式1Q或實施例1Q至44Q其中任— 者之化合物,其中各R15與R19獨立為Η或 CH3。 實施例46Q.實施例45Q之化合物,其中各R!5與 5 R19獨立為H。 實施例47Q.式1Q或實施例1Q至46Q其中任— 者之化合物,其中R2G為Η、CrC6烷基、Ch:6 烯基或(:3-(:8環烷基。 實施例48Q.實施例47Q之化合物,其中為H 10 或 CH3 0 實施例49Q.式1Q或實施例1Q、2Q、4Q、7Q、 8Q與11Q至48Q其中任一者之化合物,其中 T 為-CH2CH2-或-CH=CH- 〇 實施例50Q.實施例49Q之化合物,其中τ為 15 -CH2CH2-。 實施例51Q.式1Q或實施例1Q至50Q其中任一 者之化合物’其中G為G-2、G-3或G-15 (如 實施例51中所述者)。 實施例52Q.實施例51Q之化合物,其中G為G_2 20 (如實施例51中所述者)。 實施例53Q.實施例51Q之化合物,其中G為G_3 (如實施例51中所述者)。 實施例54Q.式1Q或實施例iq至54q其中任一 者之化合物,其中各R21獨立為齒素、硝基、 25 Crc6烷基、CrC6自烷基、crc6烷氧基、Ci_c6 鹵烷氧基或crc6烷硫基。 16 90 201240602 a你此如54Q之化合物,其中R獨立 f施例55Q.實施例5 貫 ^ 噃、CH3、CF3、OCH3、OCF3 或 盔氣、氟、/兴 SCH3 ° 實施例56Q.式1Q或實 其中各R22獨立為C1-C6炫*基或Ci-C6鹵炫*基。 實施例57Q.實施例之化合物,其中各R22獨 立為CH3或CHeh ° 實施例58Q.式1Q或實施例iQ至57Q之化合物, 其中R40為乙基或異丙基。 實施例59Q.式1Q或實施例1Q至58Q之化合物, 其中R41為乙基或異丙基。 實施例60Q·式1Q或實施例1Q至57Q之化合物, 其中R40與R41 —起作為-(CH2)5-、 -CH2CH=CHCH2-或 _(CH2)2〇(CH2)2_。 15 實施例61Q.實施例60Q之化合物,其中R4G與R41 一起作為-(CH2)5,或 _(CH2)2〇(CH2)2·。 實施例62Q·實施例61Q之化合物,其中R40與R41 一起作為-(ch2)2o(ch2)2-。 如發明内容中所述之本發明實施例亦包括(其中如 2〇 用於下列實施例中之發明内容的式1R包括其ΛΑ-氧化物 及其鹽): 實施例1R.式1R化合物,其中Ri為 201240602 各Q1與Q2為Ο ; Q3為C2-伸烷基; R32為Η或甲基; 5 W5為c2-c3伸烷基; R2為苯基、2-曱基苯基、3-曱基苯基、3-溴苯基、 3-氣苯基、4_氣苯基、3-氟苯基、3,5·二氟苯基、 3-噻吩基、2-噻吩基或3-吡啶基;以及 各 R14、R15、R18 與 R19為 Η。 ίο 實施例1RA.式1R或實施例1之化合物,其中R1 不為-N(R,(R41)。 實施例1RB.式1R化合物,其中R2為苯基;或-G; 或(:3-(:8環烷基。 實施例1RC.實施例1RB之化合物,其中R2為苯 15 基、2-°塞吩基5-氯-2-°比咬基或環丙基。 實施例1RD.實施例1RB之化合物,其中R2為苯 基、3-β塞吩基或環丙基。 實施例2R.實施例1R之化合物,其中R2為苯基、 2- 甲基苯基、3-曱基苯基、4-氣苯基、3-氟苯 2〇 基或3,5-二氟苯基。 實施例3R.實施例1R之化合物,其中R2為苯基、 3- t»塞吩基或環丙基。 實施例3RA.實施例1R之化合物,其中R2為苯 基、3-溴苯基、3-氣苯基或2-曱基苯基。 25 實施例4R.實施例1R之化合物,其中R2為3-噻 吩基、2-嘆吩基或3-°比咬基。 92 201240602 實施例5R.實施例1R之化合物,其中R2為苯基。 實施例6R.式1R之化合物,其中 R1 為-WkpEbR24 ; E1 為 NOR28 ; 5 R28為Η或曱基;以及 R2為苯基、2-甲基苯基、3-甲基苯基、3-溴苯基、 3-氣苯基、4-氯苯基、3-氟苯基、3,5-二氟苯基、 3-°塞吩基、2-°塞吩基或3-。比咬基。 實施例7R.實施例6R之化合物,其中R2為苯基、 ίο 2-曱基苯基、3-曱基苯基、4-氯苯基、3-氟苯 基或3,5-二氟苯基。 實施例8R.實施例6R之化合物,其中R2為苯基、 3-溴苯基、3-氯苯基或2-甲基苯基。 實施例9R.實施例6R之化合物,其中R2為3-噻 is 吩基、2-嗟吩基或3-吨咬基。 實施例10R.實施例6R之化合物,其中R2為苯基。 實施例11R.式1R之化合物,其中 R1 為-GA ; 各GA為一 5-至6-員碳環,其包括選自C(=0)或 2〇 C(=N_OR3())的環員;或一 9-至10-員飽和雜螺 環環系,其選擇性地包括選自C(=0)或 C(=N-OR3())的環員,各環或環系選擇性地經至 多兩個選自在碳環員上之R21與在氮環員上之 R22的取代基取代; 25 R3()為Η或甲基; R21為鹵素或CrC3烷基; 93 201240602 1122為crc3烷基。 實施例12R.實施例11R之化合物,其中GA係選 自 GA-卜 G'2、GA-3、GA-7、GA-8 與 GA-9 (如 實施例51中所述者),並且 5 R2為苯基、2-曱基苯基、3-曱基苯基、3-溴苯基、 3-氯苯基、4-氯苯基、3-氟苯基、3,5-二氟苯基、 3-σ塞吩基2-。塞吩基或3-°比咬基; 實施例13R.實施例11R之化合物,其中R2為苯 基、2_甲基苯基、3-曱基苯基、4-氯苯基、3_ ίο 氟苯基或3,5-二氟苯基。 實施例14R.實施例11R之化合物,其中R2為苯 基、3-溴苯基、3-氣苯基或2-甲基苯基。 實施例15R.實施例11R之化合物,其中R2為3· σ塞吩基、2-。塞吩基或3-°比咬基。 is 實施例16R.實施例11R之化合物,其中R2為苯 基。 實施例16RA.式1R之化合物,其中各GA為5 Embodiment 38Q. A compound of Formula 1Q or any of Embodiments 1Q to 3Q, 7Q and 11Q to 37Q, wherein 119 is a CrC6 alkyl group. Embodiment 39. The compound of Embodiment 38Q wherein R9 is CH2CH3. The compound of any one of Formula 1Q or Embodiment 1Q or 11Q to 39Q wherein R1Q is H, halogen or CrC6 alkyl. Embodiment 41. The compound of Embodiment 40Q wherein R1G is Η or CH3. The compound of any one of the formulas 1Q or 1Q to 41Q, wherein when the examples of R14 and R18 are considered separately (ie, R14 and R18 are not taken together as an alkylene group or an alkenyl group), Examples of R14 and R18 are independently hydrazine or CrC6 alkyl. 2. The compound of Embodiment 42Q wherein, when the examples of R14 and R18 are individually considered, the examples of R14 and R18 are independently hydrazine or CH3. Embodiment 44Q. The compound of Embodiment 43Q wherein, when the examples of R14 and R18 are considered separately, then Example 25 of R14 and R18 is independently oxime. 89 201240602 Embodiment 45Q. A compound of the formula 1Q or any of the examples 1Q to 44Q wherein each of R15 and R19 is independently hydrazine or CH3. Embodiment 46. The compound of Embodiment 45Q wherein each R!5 and 5R19 are independently H. Embodiment 47Q. A compound of Formula 1Q or any of Embodiments 1Q to 46Q wherein R2G is hydrazine, CrC6 alkyl, Ch: 6 alkenyl or (: 3-(:8 cycloalkyl). Example 48Q. The compound of any one of the compounds of the formula 47Q, wherein is H 10 or CH 3 0, or a compound of the formula 1Q, 2Q, 4Q, 7Q, 8Q and 11Q to 48Q, wherein T is -CH2CH2- or -CH The compound of Example 49Q, wherein τ is 15-CH2CH2-. Example 51Q. Compound of Formula 1Q or any of Examples 1Q to 50Q wherein G is G-2, G- 3 or G-15 (as described in Example 51). Embodiment 52Q. The compound of Example 51Q wherein G is G 2 20 (as described in Example 51). Example 53Q. Example 51Q A compound, wherein G is G_3 (as described in Example 51). Embodiment 54Q. A compound of Formula 1Q or any of Examples iq to 54q, wherein each R21 is independently dentate, nitro, 25 Crc6 alkane a group, CrC6 from an alkyl group, a crc6 alkoxy group, a Ci_c6 haloalkoxy group or a crc6 alkylthio group. 16 90 201240602 a you as a compound of 54Q, wherein R is independent of the example 55Q. Example 5 ^^ 噃, CH3 , CF3, OCH3, OCF3 or Helmet Gas, Fluorine, / Schöning SCH3 ° Example 56Q. Formula 1Q or each of R22 independently is C1-C6 Hyun* or Ci-C6 Halogen*. Example 57Q. Example And a compound of the formula QQ. A compound wherein R41 is ethyl or isopropyl. Embodiment 60Q. A compound of Formula 1Q or Examples 1Q to 57Q, wherein R40 and R41 together are -(CH2)5-, -CH2CH=CHCH2- or _(CH2 2〇(CH2)2_. 15 Embodiment 61. The compound of Embodiment 60Q wherein R4G together with R41 is -(CH2)5, or _(CH2)2〇(CH2)2. Example 62Q. A compound of 61Q, wherein R40 and R41 together act as -(ch2)2o(ch2)2-. Embodiments of the invention as described in the Summary of the Invention also include (wherein, for example, the formula for the invention in the following examples) 1R includes its ruthenium-oxide and its salts): Example 1R. A compound of formula 1R wherein Ri is 201240602 each Q1 and Q2 are oxime; Q3 is C2-alkylene; R32 is oxime or methyl; 5 W5 is c2 -c3 alkylene R2 is phenyl, 2-mercaptophenyl, 3-mercaptophenyl, 3-bromophenyl, 3-phenylphenyl, 4-p-phenyl, 3-fluorophenyl, 3,5·difluoro Phenyl, 3-thienyl, 2-thienyl or 3-pyridyl; and each of R14, R15, R18 and R19 is deuterium. Ίο Embodiment 1RA. A compound of Formula 1R or Example 1, wherein R1 is other than -N(R, (R41). Embodiment 1 RB. A compound of Formula 1R wherein R 2 is phenyl; or -G; or (: 3- (8 Cycloalkyl. Example 1 RC. The compound of Example 1 RB, wherein R 2 is phenyl 15 yl, 2-° thiophene 5-chloro-2-° ratio dimethyl or cyclopropyl. Example 1 RD. The compound of Example 1 RB, wherein R 2 is phenyl, 3-β-thenyl or cyclopropyl. Embodiment 2R. The compound of Example 1R wherein R 2 is phenyl, 2-methylphenyl, 3-mercaptobenzene , 4-phenylphenyl, 3-fluorophenyl-2-indenyl or 3,5-difluorophenyl. Embodiment 3R. The compound of Example 1R wherein R 2 is phenyl, 3-t»septenyl or cyclic The compound of Example 1R, wherein R2 is phenyl, 3-bromophenyl, 3-phenylphenyl or 2-mercaptophenyl. 25 Example 4R. The compound of Example 1R, wherein R2 is 3-thienyl, 2-thinyl or 3-octyl. 92 201240602 Embodiment 5R. The compound of Embodiment 1R, wherein R2 is phenyl. Embodiment 6R. A compound of Formula 1R wherein R1 is -WkpEbR24 ; E1 is NOR28; 5 R28 is hydrazine or fluorenyl; and R2 is phenyl, 2- Phenylphenyl, 3-methylphenyl, 3-bromophenyl, 3-phenylphenyl, 4-chlorophenyl, 3-fluorophenyl, 3,5-difluorophenyl, 3-°-septyl , a compound of the formula 6R, wherein R 2 is phenyl, ίο 2-decylphenyl, 3-mercaptophenyl, 4-chlorobenzene. a compound of the compound of Example 6R wherein R 2 is phenyl, 3-bromophenyl, 3-chlorophenyl or 2-methylbenzene. The compound of Embodiment 6R, wherein R2 is 3-thiaisyl, 2-nonyl or 3-ton. The compound of Example 6R, wherein R2 is phenyl. Embodiment 11R. A compound of Formula 1R wherein R1 is -GA; each GA is a 5- to 6-membered carbocyclic ring comprising a ring member selected from C(=0) or 2〇C(=N_OR3()) Or a 9- to 10-membered saturated heterospiro ring system optionally comprising a ring member selected from C(=0) or C(=N-OR3()), each ring or ring system selectively Substituted by at least two substituents selected from R21 on a carbocyclic member and R22 on a nitrogen ring member; 25 R3() is hydrazine or methyl; R21 is halogen or CrC3 alkyl; 93 201240602 1122 is crc3 Embodiment 12. R. The compound of Embodiment 11R, wherein the GA is selected from the group consisting of GA-Bu G'2, GA-3, GA-7, GA-8, and GA-9 (as described in Example 51), And 5 R2 is phenyl, 2-mercaptophenyl, 3-mercaptophenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 3,5-di Fluorophenyl, 3-σsecenyl 2-. The compound of Example 11R, wherein R 2 is phenyl, 2-methylphenyl, 3-mercaptophenyl, 4-chlorophenyl, 3_ ίο fluoro Phenyl or 3,5-difluorophenyl. Embodiment 14R. The compound of Embodiment 11R wherein R2 is phenyl, 3-bromophenyl, 3-phenylphenyl or 2-methylphenyl. Embodiment 15 R. The compound of Embodiment 11R wherein R 2 is 3 σ thiophene, 2-. The thiophene or 3-° ratio bite base. Is a compound of Embodiment 11R wherein R2 is phenyl. Embodiment 16RA. A compound of Formula 1R wherein each GA is

其中向左伸出之鍵代表連接至式1R化合物之 其餘部分的連接點。 實施例16RB.實施例16RA之化合物,其中各Ga 94 201240602The bond extending to the left represents the point of attachment to the remainder of the compound of formula 1R. Embodiment 16 RB. The compound of Example 16RA, wherein each Ga 94 201240602

其中向左伸出之鍵代表連接至式1化合物之其餘 部分的連接點。 實施例17R.式1R或實施例1R至16R之化合物, 其中R4G為乙基或異丙基。 實施例18R.式1R或實施例1R至16R之化合物, 其中R41為乙基或異丙基。 10 15 實施例19R.式1R或實施例1R至16R之化合物, 其中R4()與R41 —起作為-(CH2)5-、 -CH2CH=CHCH2_或-(CH2)20(CH2)2-。 實施例20R.實施例19R之化合物,其中R4G與R41 一起作為-(CH2)5-或-(&lt;:Η2)20((:Η2)2-。 實施例21R.實施例20R之化合物,其中R4G與R41 一起作為-(CH2)20(CH2)2-。 如發明内容中所述之本發明實施例亦包括(其中如 用於下列實施例中之發明内容的式1S包括其,氧化物 及其鹽): 實施例1S.式1S之化合物,其中 R1為The bond extending to the left represents the point of attachment to the remainder of the compound of Formula 1. Embodiment 17R. A compound of Formula 1R or Embodiments 1R to 16R wherein R4G is ethyl or isopropyl. Embodiment 18R. A compound of Formula 1R or Embodiments 1R to 16R wherein R41 is ethyl or isopropyl. 10 15 Embodiment 19R. A compound of Formula 1R or Embodiments 1R to 16R, wherein R4() is taken together with R41 as -(CH2)5-, -CH2CH=CHCH2_ or -(CH2)20(CH2)2-. Embodiment 20R. The compound of Embodiment 19R, wherein R4G together with R41 is -(CH2)5- or -(&lt;:Η2)20((:Η2)2-. Example 21R. The compound of Example 20R, wherein R4G together with R41 is -(CH2)20(CH2)2-. Embodiments of the invention as described in the Summary of the Invention also include (wherein Formula 1S as used in the following examples includes, oxides and Its salt): Example 1S. A compound of formula 1S, wherein R1 is

各Q1與Q2為〇 ; 95 201240602 Q3為C2_伸烷基; R32為Η或甲基; W5為C2-C3伸烷基; R2為苯基、2-曱基苯基、3-曱基苯基、3_溴苯基、 5 3-氣苯基、4-氣苯基、3·氟苯基、3,5-二氟苯基、 3-°塞吩基、2-β塞吩基或3-σ比咬基, 各 R14、R15、R18 與 R19 為 Η ;以及 R23為曱基或乙基。 實施例1SA.式1S或實施例1S之化合物,其中 ίο R1 不為-N(R4°)(R41)。 實施例1SB.式1S或實施例1S之化合物,其中 R2為苯基;或-G ;或C3-C8環烷基。 實施例1SC.實施例1SB之化合物,其中R2為苯 基、2-σ塞吩基5-氣-2-α比咬基或環丙基。 is 實施例1SD.實施例1SB之化合物,其中R2為苯 基、3-。塞吩基或環丙基。 實施例2S.實施例1S之化合物,其中R2為苯基、 2-甲基苯基、3-曱基苯基、4-氣苯基、3·氟苯 基或3,5-二氟苯基。 2〇 實施例2SA.實施例1S之化合物,其中R2為苯基、 3 -0塞吩基或環丙基。 實施例3S.實施例1S之化合物,其中R2為苯基、 3·溴苯基、3-氣苯基或2_甲基苯基。 實施例4S.實施例1S之化合物,其中R2為3-噻吩 25 基、2-。塞吩基或3-°比咬基。 實施例5S.實施例1S之化合物,其中R2為苯基。 96 201240602 實施例6S.式IS之化合物,其中 R1 為-WtpEbR24 ; E1 為 NOR28 ; R28為Η或甲基;以及 5 R2為苯基、2-曱基苯基、3-曱基苯基、3-溴苯基、 3-氯苯基、4-氯苯基、3-氟苯基、3,5-二氟苯基、 3-噻吩基、2-噻吩基或3-吡啶基。 實施例7S.實施例6S之化合物,其中R2為苯基、 2- 曱基苯基、3-甲基苯基、4-氣苯基、3-氟苯 ίο 基或3,5-二氟苯基。 實施例8S.實施例6S之化合物,其中R2為苯基、 3- 溴苯基、3-氯苯基或2_甲基苯基。 實施例9S.實施例6S之化合物,其中R2為3-噻吩 基、2 -π塞吩基或3 -α比咬基。 is 實施例9SA.實施例6S之化合物,其中R2為2-噻 吩基。 實施例10S.實施例6S之化合物,其中R2為苯基。 實施例11S.式1S之化合物,其中 R1 為-GA ; 20 各GA為一 5-至6·員碳環,其包括選自C(=0)或 C(=N-OR3())的環員;或一 9-至10·員飽和雜螺 環環系,其選擇性地包括選自C(=0)或 C(=N-OR3())的環員,各環或環系選擇性地經至 多兩個選自在碳環員上之R21與在氮環員上之 25 R22的取代基取代;或 R3()為Η或甲基; 97 201240602 R21為鹵素或CrC3烷基; R22為Ci-Q烷基。 實施例12S.實施例11S之化合物,其中GA係選 自 GA-1、GA_2、GA-3、GA-7、GA-8 與 GA-9 ; 以及 R2為苯基、2-甲基苯基、3-曱基苯基、3_溴苯基、 3-氣苯基、4-氣苯基、3-氟苯基、3,5-二氟苯基、 3-°塞吩基、2-°塞吩基或3-°比咬基。 10 實施例12SA.實施例12S之化合物,其中GA係選 自GA-2 ;以及 R2為苯基或2-噻吩基。 實施例13S.實施例11S之化合物,其中R2為苯 基、2-甲基苯基、3-甲基苯基、4_氯苯基、3_ 氟苯基或3,5-二氟苯基。 15 實施例14S.實施例11S之化合物,其中R2為苯 基、3-溴苯基、3-氯苯基或2-甲基苯基。 實施例15S.實施例11S之化合物,其中R2為3-嗟吩基、2-。塞吩基或3-°比咬基。 實施例16S.式1S之化合物,其中各GA為 20Each Q1 and Q2 is 〇; 95 201240602 Q3 is C2_alkylene; R32 is hydrazine or methyl; W5 is C2-C3 alkyl; R2 is phenyl, 2-mercaptophenyl, 3-mercaptobenzene Base, 3-bromophenyl, 5-trioxophenyl, 4-phenylphenyl, 3-fluorophenyl, 3,5-difluorophenyl, 3-°-septyl, 2-β-septenyl or The 3-σ ratio bite group, each of R14, R15, R18 and R19 is Η; and R23 is a fluorenyl group or an ethyl group. Embodiment 1 SA. A compound of Formula 1S or Embodiment 1S, wherein ίο R1 is not -N(R4°) (R41). Embodiment 1SB. A compound of Formula 1S or Embodiment 1S wherein R2 is phenyl; or -G; or C3-C8 cycloalkyl. Embodiment 1SC. The compound of Embodiment 1SB wherein R2 is phenyl, 2-σ-saltyl 5-a-2-α ratio dimethyl or cyclopropyl. Is the compound of Example 1 SB, wherein R2 is phenyl, 3-. Queenyl or cyclopropyl. Embodiment 2S. The compound of Embodiment 1S wherein R2 is phenyl, 2-methylphenyl, 3-mercaptophenyl, 4-phenylphenyl, 3-fluorophenyl or 3,5-difluorophenyl . 2A. The compound of Embodiment 1S wherein R2 is phenyl, -3-cyano or cyclopropyl. Embodiment 3S. The compound of Embodiment 1S wherein R2 is phenyl, tribromophenyl, 3-phenylphenyl or 2-methylphenyl. Embodiment 4S. The compound of Embodiment 1S wherein R2 is 3-thiophene 25, 2-. The thiophene or 3-° ratio bite base. Embodiment 5S. The compound of Embodiment 1S wherein R2 is phenyl. 96 201240602 Example 6S. A compound of formula IS wherein R1 is -WtpEbR24; E1 is NOR28; R28 is hydrazine or methyl; and 5R2 is phenyl, 2-mercaptophenyl, 3-mercaptophenyl, 3 - bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 3,5-difluorophenyl, 3-thienyl, 2-thienyl or 3-pyridyl. Embodiment 7S. The compound of Embodiment 6S wherein R 2 is phenyl, 2-nonylphenyl, 3-methylphenyl, 4-phenylphenyl, 3-fluorophenyl ε or 3,5-difluorobenzene base. Embodiment 8S. The compound of Embodiment 6S wherein R2 is phenyl, 3-bromophenyl, 3-chlorophenyl or 2-methylphenyl. Embodiment 9S. The compound of Embodiment 6S wherein R2 is 3-thienyl, 2-π-thenyl or 3-alpha ratio. Is a compound of Embodiment 6S wherein R2 is 2-thienyl. Embodiment 10S. The compound of Embodiment 6S wherein R2 is phenyl. Embodiment 11S. A compound of Formula 1S wherein R1 is -GA; 20 each GA is a 5- to 6-membered carbocyclic ring comprising a ring selected from C(=0) or C(=N-OR3()) Or a 9- to 10-membered saturated spirocyclic ring system optionally comprising a ring member selected from C(=0) or C(=N-OR3()), each ring or ring system selective The ground is substituted with at most two substituents selected from R21 on a carbocyclic ring and 25 R22 on a nitrogen ring member; or R3() is a hydrazine or a methyl group; 97 201240602 R21 is a halogen or a CrC3 alkyl group; R22 is a Ci -Q alkyl. Embodiment 12S. The compound of Embodiment 11S wherein the GA is selected from the group consisting of GA-1, GA_2, GA-3, GA-7, GA-8, and GA-9; and R2 is phenyl, 2-methylphenyl, 3-decylphenyl, 3-bromophenyl, 3-phenylphenyl, 4-phenylphenyl, 3-fluorophenyl, 3,5-difluorophenyl, 3-°-septyl, 2-° The thiophene or 3-° ratio bite base. 10 Embodiment 12. The compound of Embodiment 12S wherein the GA is selected from the group consisting of GA-2; and R2 is phenyl or 2-thienyl. Embodiment 13S. The compound of Embodiment 11S wherein R2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl. The compound of Embodiment 11S wherein R2 is phenyl, 3-bromophenyl, 3-chlorophenyl or 2-methylphenyl. Embodiment 15S. The compound of Embodiment 11S wherein R2 is 3-nonyl, 2-. The thiophene or 3-° ratio bite base. Embodiment 16S. A compound of Formula 1S wherein each GA is 20

其中向左伸出之鍵代表連接至式1S化合物之 其餘部分的連接點。 25 實施例17S.實施例16S之化合物,其中各GA為 98 201240602The key extending to the left represents the point of attachment to the remainder of the compound of formula 1S. 25 Embodiment 17S. The compound of Embodiment 16S wherein each GA is 98 201240602

其中向左伸出之鍵代表連接至式1化合物之其 5 餘部分的連接點。 實施例17SA.式1S或實施例1S至16S之化合物, 其中R4()為乙基或異丙基。 實施例18S.式1S或實施例1S至16S之化合物, 其中R41為乙基或異丙基。 ίο 實施例19S.式1S或實施例1S至16S之化合物, 其中R4G與R41 —起作為-(CH2)5-、 -CH2CH=CHCH2-或-(CH2)20(CH2)2-。 實施例20S.實施例19S之化合物,其中R4G與R41 一起作為-(ch2)5-或-(ch2)2o(ch2)2-。 15 實施例21S.實施例20S之化合物,其中R4G與R41 一起作為-(CH2)20(CH2)2-。 .本發明亦針對式1P化合物(包括所有立體異構 物)、其,氧化物與鹽、含有它們之農業組成物及其作 為除草劑之用途:The bond extending to the left represents the point of attachment to the remainder of the compound of Formula 1. Embodiment 17 SA. A compound of Formula 1S or Embodiments 1S to 16S wherein R4() is ethyl or isopropyl. Embodiment 18S. A compound of Formula 1S or Embodiments 1S to 16S wherein R41 is ethyl or isopropyl. Ίο Embodiment 19S. A compound of Formula 1S or Embodiments 1S to 16S, wherein R4G and R41 together are -(CH2)5-, -CH2CH=CHCH2- or -(CH2)20(CH2)2-. Embodiment 20S. The compound of Embodiment 19S wherein R4G together with R41 is -(ch2)5- or -(ch2)2o(ch2)2-. The compound of Embodiment 20S wherein R4G together with R41 is taken as -(CH2)20(CH2)2-. The invention is also directed to compounds of formula 1P (including all stereoisomers), their oxides and salts, agricultural compositions containing them, and their use as herbicides:

1P 其中 99 201240602 A為選自由下列所組成之群組之自由基1P where 99 201240602 A is a free radical selected from the group consisting of

以及as well as

B1與B3各獨立為選自由下列所組成之群組之自由 基B1 and B3 are each independently a free radical selected from the group consisting of

RR

1515

C-l C-2 B2為選自由下列所組成之群組之自由基 15C-l C-2 B2 is a radical selected from the group consisting of 15

C-3 C-4 C-5 C-6 C-7 R1為C-3 C-4 C-5 C-6 C-7 R1 is

或 201240602 R1 為-w;C(,〆、-w1lc(=e2)r25 _W如的lr26、_w1s(qxnr28c 7 ^^(0)^^0(=0)^27 wls(0)xNR28so邮7 或_wiCN;或 R1 為 _GA 或-W2GA ; 各GA為一 4—至7_員碳環,其包括選自c(=〇)、 C(-S)^' C(-NR ) . C(=N-OR30)^ C=NN(R29)2 10 之環員,或6-至i2_員飽和或部分飽和碳螺 裱或雜螺環環系,其選擇性地包括選自 C(-〇) ' C(-S) ' C(=nr29) &gt; C(=N-OR30) ^ C=NN(R29)2之環員’各環或環系選擇性地經至 多五個選自在碳環員上之R2i與在氮環員上之 R22的取代基取代; 15 各 E、E2 與 E3 獨立為 〇、s、NR28、NOR28、NN(R28)2、 N-CN 或 N-N〇2 ; 各L獨立為〇、NR31或S ; 其限制條件是當E3為〇,則l不為〇 ; 20 各R24、R25、R26與R27獨立為氫;或CrC6烷基、 C2_C6烯基、C2-C6炔基或C3-C6環烷基,各選 擇性地經一或多個取代基取代,該取代基係選 自由鹵素、CN、N〇2、經基、CrC4炫氧基、 C1-C4院亞續醯基、C1-C4院續醮基、C1-C4燒 胺基、c2_c8二烷胺基、c3-c6環烷胺基與(C! -c4 烷基)c3-c6環烷胺基所組成之群組; 各R28獨立為Η、CrC6烷基或CrC6鹵烷基; 101 25 R29獨立為Η、CrC6烷基、CrC6鹵烷基、CrQ 烷羰基、CrC6烷磺醯基或ci-c6齒烷磺醯基; 各Q1與Q2獨立為0、S或-NR31 ; Q3為CrC4伸烷基,其選擇性地經至多4個取代基 取代,該取代基係選自Ci-C6烧基、C2-C6婦 基、c2-c6炔基與c3-c6環烷基之取代基取代; R30獨立為Η、C】-C6烧基或Ci-C6 _烧基; R31獨立為Η、C]-C6烷基或CrC6 _烷基; R32為Η或CrQ烷基; 各X為〇、1或2 ; W5為C〗-C6伸院基; W1為C「C6伸烷基、c2-C6伸烯基或c2-c6伸炔基; 或-(CH2)2〇CH2-或-(CH2)3〇CH2-; W2為crc6伸烷基; R2為苯基或-W3(苯基),各選擇性地在環員上經至 多五個取代基取代,該取代基係選自R21 ;或 -G或-W4G ;或Η、氰基、羥基、胺基、硝基、 CHO、-C(=〇)〇H、_C(=0)NH2、_C(=S)NH2、 -C(=0)NHCN、-C(=0)NH0H、-SH、-S02NH2、 -S02NHCN、_S02NH0H、-SF5、-NHCHO、 -NHNH2、-NHOH、-NHCN、-NHC(=0)NH2、 CrC6院基、C2-C6烯基、C2-C6炔基、crC6鹵 院基、c2-c6自烯基、CrC6 -块基、C3_C8環 院基、c3-c8 1¾環烧基、c4_Cl〇燒環坑基、c4_Ci〇 裱烷烷基、CVc!4環烷環烷基、c4-c10齒環烷 烷基、CVC】2烷環烷烷基、C3_C8環烯基、C3_C8 鹵環稀基、C2-Cg烧氧烧基、C3-C10烧氧稀基、 c4-c1G環烷氧烷基、C3-C1G烷氧烷氧烷基、 烧硫烧基.、。2-。8烧亞續酿烧基、 烧續酿烧基、C2-Cg院胺烧基、C3-C1G二烧胺 烷基、c2-c8鹵烷胺烷基、c4-c10環烷胺烷基、 C2-C8烧幾基、C2-C8鹵炫i幾基、C4-Ci〇環烧幾 基、c2-c8烷氧羰基、c4-c 1G環烷氧羰基、c5-c 12 環烷烷氧羰基、c2-c8烷胺羰基、C3_C1G二烷 胺幾基、C4-C1G環烧胺幾基、C2-C5氰烧基、 Cl-C6經炫•基、C4-C10環婦烧基、C2-C8鹵烧氧 烧基、C2~C8烧氧鹵烧基、C2-C8 1¾烧氧鹵烧 基、c4-cK, ii環烷氧烷基、c4-c1G環烯氧烷基、 C4-C10鹵環婦氧烧基、C3-C10二烧氧烧基、 C3-C1G烧氧烧幾基、C3-C1G烧氧幾院基、C2-C8 鹵烷氧羰基、crc6烷氧基、crc6鹵烷氧基、 c3-c8環烷氧基、C3-C8鹵環烷氧基、(:4_(:10環 烷烷氧基、c2-c6烯氧基、c2-c6鹵烯氧基、c2-c6 炔氧基、c3-c6鹵炔氧基、c2-c8烷氧烷氧基、 c2-c8烷羰氧基、c2_c8 _烷羰氧基、c4-c10環 烷羰氧基、c3-c1G烷羰烷氧基、crc6烷硫基、 crc6鹵烷硫基、c3-c8環烷硫基、crc6烷亞 確酿基、Ci-C6鹵烧亞確酿基、Ci-C6烧續酿 基、Ci-C6鹵烧續酿基、C3-C8環炫&gt;確酿基、C3_Cs 三烷矽基、c3-c8環烯氧基、c3-c8鹵環烯氧 基、c2-c8鹵烷氧烷氧基、c2-c8烷氧鹵烷氧 基、c2-c8鹵烷氧鹵烷氧基、c3-c10烷氧羰烷 氧基、C2-Cg烧基(硫幾基)氧基、C2-Cg烧幾硫 基、C2-C8烧基(硫幾基)硫基、C3-C8環院亞續 醯基、CVC6烷胺磺醯基、C2-C8二烷胺磺醯 基、c3_c10鹵三烷矽基、crc6烷胺基、c2-c8 二院胺基、C1-C6鹵院胺基、C2_Cg函二院胺 基、c3-c8環烷胺基、c2-c8烷羰胺基、c2-c8 鹵烷羰胺基、crc6烷磺醯胺基、crc6函烷磺 醯胺基或c4-c1G環烷基(烷基)胺基;或Or 201240602 R1 is -w; C(, 〆, -w1lc(=e2)r25 _W such as lr26, _w1s(qxnr28c 7 ^^(0)^^0(=0)^27 wls(0)xNR28so post 7 or _wiCN; or R1 is _GA or -W2GA; each GA is a 4- to 7-member carbon ring, which includes a group selected from c(=〇), C(-S)^'C(-NR). C( =N-OR30)^ C=NN(R29)2 10 ring member, or 6- to i2_ member saturated or partially saturated carbon thread or heterospinal ring system, optionally comprising a group selected from C (-〇) ) 'C(-S) ' C(=nr29) &gt; C(=N-OR30) ^ C=NN(R29)2 ring members' rings or ring systems selectively up to five selected from carbon rings R2i on the member is substituted with a substituent of R22 on the nitrogen ring member; 15 each E, E2 and E3 is independently 〇, s, NR28, NOR28, NN(R28)2, N-CN or NN〇2; Independently 〇, NR31 or S; the restriction is that when E3 is 〇, then l is not 〇; 20 each R24, R25, R26 and R27 are independently hydrogen; or CrC6 alkyl, C2_C6 alkenyl, C2-C6 alkynyl Or a C3-C6 cycloalkyl group, each optionally substituted by one or more substituents selected from the group consisting of halogen, CN, N〇2, thiol, CrC4 methoxy, C1-C4 Base, C1-C4 Institute 醮 、, C1-C4 amine group, c2_c8 a group consisting of an alkylamino group, a c3-c6 cycloalkylamino group and a (C!-c4 alkyl)c3-c6 cycloalkylamino group; each R28 is independently a hydrazine, a CrC6 alkyl group or a CrC6 haloalkyl group; R29 is independently hydrazine, CrC6 alkyl, CrC6 haloalkyl, CrQ alkylcarbonyl, CrC6 alkanesulfonyl or ci-c6 alkane sulfonyl; each Q1 and Q2 is independently 0, S or -NR31; Q3 is CrC4 An alkyl group optionally substituted with up to 4 substituents selected from the group consisting of Ci-C6 alkyl, C2-C6, c2-c6 alkynyl and c3-c6 cycloalkyl; R30 is independently Η, C]-C6 alkyl or Ci-C6 _ alkyl; R31 is independently Η, C]-C6 alkyl or CrC6 _alkyl; R32 is hydrazine or CrQ alkyl; each X is 〇, 1 Or 2; W5 is C--C6-extension base; W1 is C"C6 alkyl, c2-C6-alkenyl or c2-c6-alkenyl; or -(CH2)2〇CH2- or -(CH2) 3〇CH2-; W2 is crc6 alkyl; R2 is phenyl or -W3(phenyl), each optionally substituted with up to five substituents on the ring member, the substituent being selected from R21; G or -W4G; or hydrazine, cyano, hydroxy, amine, nitro, CHO, -C(=〇)〇H, _C(=0)NH2, _C(=S)NH2, -C(=0) NHCN, -C(=0)NH0H, -SH, -S02NH2 -S02NHCN, _S02NH0H, -SF5, -NHCHO, -NHNH2, -NHOH, -NHCN, -NHC(=0)NH2, CrC6, C2-C6 alkenyl, C2-C6 alkynyl, crC6 halogen, c2 -c6 from alkenyl, CrC6-block, C3_C8 ring, c3-c8 13⁄4 cycloalkyl, c4_Cl oxime, c4_Ci decane, CVc! 4 cycloalkane, c4-c10 Cycloalkylalkyl, CVC]2alkylcycloalkanyl, C3_C8 cycloalkenyl, C3_C8 halocycloalkyl, C2-Cg alkoxyalkyl, C3-C10 oxynitride, c4-c1G cycloalkoxyalkyl , C3-C1G alkoxyalkoxyalkyl, sulfur-burning base. 2-. 8 烧 烧 烧 烧 烧 , , , , , , , , , , , , , , , , , , -C8 calcined, C2-C8 halo, c4-Ci anthracenyl, c2-c8 alkoxycarbonyl, c4-c 1G cycloalkoxycarbonyl, c5-c 12 cycloalkaneoxycarbonyl, C2-c8 alkylamine carbonyl, C3_C1G dialkylamine group, C4-C1G cycloalkamine group, C2-C5 cyanocarbyl group, Cl-C6 group, C4-C10 ring group, C2-C8 halide Oxygen-burning base, C2~C8 oxy-halogen group, C2-C8 13⁄4 oxy-halogen group, c4-cK, ii cycloalkoxyalkyl, c4-c1G cycloalkenyloxy, C4-C10 halogen ring Oxygen group, C3-C10 di-oxygen group, C3-C1G alkoxypyrazine, C3-C1G alkoxy group, C2-C8 haloalkoxycarbonyl group, crc6 alkoxy group, crc6 haloalkoxy group, C3-c8 cycloalkoxy, C3-C8 halocycloalkoxy, (: 4_(:10 cycloalkylalkoxy, c2-c6 alkenyloxy, c2-c6 haloalkenyloxy, c2-c6 alkynyloxy) , c3-c6 haloalkoxy, c2-c8 alkoxyalkoxy, c2-c8 alkylcarbonyloxy, c2_c8-alkylcarbonyloxy, c4-c10 cycloalkaneoxy, c3-c1G alkylcarbonyl alkoxy , crc6 alkylthio, crc6 haloalkylthio, c3-c8 naphthenic Base, crc6 alkane, brewing base, Ci-C6 halogenated arsenic, Ci-C6 calcined base, Ci-C6 halogen calcined base, C3-C8 ring dazzle &gt; exact brewing base, C3_Cs trioxane Mercapto, c3-c8 cycloalkenyloxy, c3-c8 halocycloalkenyloxy, c2-c8 haloalkoxy alkoxy, c2-c8 alkoxyhaloxy, c2-c8 halohalo alkoxy , c3-c10 alkoxycarbonyl alkoxy, C2-Cg alkyl (thiol)oxy, C2-Cg thiol, C2-C8 alkyl (thio)thio, C3-C8 ring Sulfhydryl group, CVC6 alkylamine sulfonyl group, C2-C8 dialkylamine sulfonyl group, c3_c10 halotrialkyl fluorenyl group, crc6 alkylamino group, c2-c8 amphoteric amine group, C1-C6 halogen compound amine group, C2_Cg letter II compound amine group, c3-c8 cycloalkylamino group, c2-c8 alkylcarbonylamino group, c2-c8 haloalkylcarbonylamino group, crc6 alkanesulfonylamino group, crc6 alkanesulfonylamino group or c4-c1G a cycloalkyl (alkyl) amine group; or

R2 為-W6C(=E4)R33 、 -W6L1C(=E5)R34 、 -\ν6(:(=Ε6)1^35、-w6s(o)xnr37c(=o)r36 或 -W6S(0)xNR37C(=0)L1R36 ; 各 E4、E5 與 E6獨立為 o、s、nr37、nor37、nn(r37)2、 N-CN 或 N-N02 ; 各L1獨立為0、NR38或s ; 各R33、R34、R35與R36獨立為氫;或CrC6烷基、 Q-C6烯基、CrC6炔基或C3-C6環烷基,各選 擇性地經一或多個取代基取代,該取代基係選 自由鹵素、CN、N02、羥基、CrC4烷氧基、 C1-C4院亞崎酿基、C1-C4院績酿基、C1-C4燒 胺基、C2-C8二烷胺基、C3-C6環烷胺基與(CrC4 烷基)Cs-C:6環烷胺基所組成之群組; 201240602 各R37獨立為Η、CrC6烷基或C〗-C6鹵烷基; 各Q4與Q5獨立為〇、s或NR38 ; Q6為Crc4伸烷基,其選擇性地經至多4個選自 Ci-C6 燒基、C2-C6 稀基、C2-C6 快基與 C3-C6 環烷基的取代基取代; R38獨立為H、CrC6烷基或Crc6鹵烷基; R39為Η或CrC6烷基; 各X為0、1或2 ; W7為crc6伸烷基; 10 W為crC6伸烧基、C2-C6伸稀基或C2-C6伸块基; 或-(ch2)2〇ch2-或·(CH2)3〇CH2-; w3為CrC6伸烷基、c2-c6伸烯基或c2_c6伸炔基; W4為crC6伸烷基; 15 R3為Η、鹵素、氰基、羥基、_〇_M+、胺基、硝基、 -CHO、-C(=0)0H、-C(=〇)NH2、-C(=S)NH2、 -SH ' -S02NH2 ' -SO2NHCN ' -SO2NHOH ' 20 •OCN、_SCN、-SF5、_NHNH2、-NHOH、 -N=C=0、-N=C=S、CrC6 烷氧基、CrC6 鹵烷 氧基、CVC8環烷氧基、C3_C8 環烷氧基、 G-Cio環烧院氧基、C2-C6烯氧基、C2-C6鹵稀 氧基、c2-c6快氧基、c3-c6鹵炔氧基、c2-c8 院氧烧氧基、C2-C8炫》幾氧基、C2-C8鹵烧幾·氧 基、C4-C1G環烷羰氧基、C3-C]G烷羰烷氧基、 CrC6烷硫基、CrC6鹵烷硫基、c3-C8環烷硫 基、Ci-C6炫》亞㈣酿基、Ci_Cg鹵烧亞續酿基、 CrC6烷磺醯基、crc6鹵烷磺醯基、c3-c8環 105 25 烧橫酿基、C!-C6院確酿氧基、C!-C6烧胺基、 匸2_匚8二烧胺基、Ci_C6鹵院胺基、C2-C8鹵二 烧胺基、C3-C8環烧胺基、C2-C8烧叛胺基、C2_Cg 鹵烷羰胺基、CrQ烷磺醯胺基或crc6鹵烷磺 醯胺基;或苄氧基、苯氧基、苄羰氧基、苯羰 氧基、苯績酸氧基、节確醯氧基、苯硫基、节 硫基、苯亞續醢基、节亞續酿基、苯續醯基或 苄磺醯基,各選擇性地在環員上經至多五個選 自R21的取代基取代; M+為一鹼金屬陽離子或一銨陽離子; R4、R5、R6與R7各獨立為Η、鹵素、羥基、CrC6 院基、〇2·〇6稀基、C2-C6快基、C1-C6鹵院基、 CrC6烷氧基、CrC6鹵烷氧基、CrC8環烷氧 基或C3-C8鹵環烷氧基;或苯基或苄基,各選 擇性地在環員上經至多五個選自R21的取代基 取代; R8 為 Η、Q-C6 烷基、C2-C6 烯基、C2-C6 炔基、Q-C6 函院基、C2_C6 _稀基、C2-C6鹵快基、C3-C8 環烷基或c3-c8鹵環烷基;或苄基,其選擇性 地在環員上經至多五個選自R21的取代基取 代; R9 為 Η、Q-G 烷基、C2-C6 烯基、C2-C6 炔基、Q-C6 鹵院基、〇2·〇6鹵烯基、C2-C6鹵快基、C3-C8 環烷基、c3-c8鹵環烷基、c4_c10烷環烷基、 c4-c1()環烷烷基、c6-c14環烷環烷基、c4-c10 鹵環烷烷基、c5-c12烷環烷烷基、c3-c8環烯 基、c3-c8鹵環烯基、c2-c8烷氧烷基、c4-C1() 環烧氧烷基、CVCh)烧氧烧氧烷基或C2-C8燒 硫烷基; R1G為Η、鹵素、氰基、羥基、胺基、硝基、SH、 so2nh2、-so2nhcn、-so2nhoh、-OCN、 -SCN、-SF5、-NHCHO、-NHNH2、-N3、-ΝΗΟΗ、 -NHCN、_NHC(=0)NH2、-N=C=〇、_N=C=S、 crc6烷基、c2-c6烯基、C2-C6炔基、crc6鹵 烧基、C2-C6 _烯基、C2-C6 1¾炔基、C3-C8環 烷基、CrC8鹵環烷基、c4-c10烷環烷基、C4-C1() 環烷烷基、cvcH環烷環烷基、c4_ClG _環境 烷基、Cg-Cn烷環烷烷基、C3-C8環烯基、c3-c8 鹵環烯基、C^C:8烷氧烷基、c4-C10環烷氧烷 基、C3-C1G烷氧烷氧炫基或c2-c8烧硫烷基; R11為Η、i素、氰基、羥基、胺基、Cl-c6烷基、 c2-c6 烯基、C2-C6 炔基、crc6 齒烷基、c2-c6 齒烯基、C2-C6自快基、C3-C8環烧基、c3-c8 鹵環烷基' C4-C10烷環烷基、c4-c10環烷烷基、 C4-C10鹵環烷烷基、C5-Ci2烷環烧烷基、c3-C8 環稀基、CVC8 ii環稀基、c2-C8烧氧烧基、 C^Cio環烧氧院基、C3_C1()烧氧院氧烧基、 C2_Q烷硫烷基、CrC8烷亞磺醯烷基或c2-C8 烧確醯烷基;或苯基’其選擇性地經至多五個 選自R21的取代基取代; 12 R為Η、鹵素、氰基、羥基、胺基、Cl_c6烷基、 c2-c6 烯基、(:2-(:6炔基、CVC6 鹵烷基、C2-C6 鹵烯基、C2-C6鹵炔基、c3-C8環烷基、c3-c8 鹵環烷基、CVC10烷環烷基、C4-C10環烷烷基、 C6-C14環烧環院基、c4_ClG齒環烧院基、c5_Ci2 烷環烷烷基、C3_C8環烯基、c3-c8鹵環烯基或 C2-C8烷氧羰胺基; R13為Η、鹵素、氰基、羥基、胺基、硝基或c2_c8 烷氧羰基; η為0、1或2 ; 各R14、R15、R18與Ri9獨立為Η、鹵素、氰基、羥 基或Ci_C6院基;或 一對R14與R18 —起作為C2-C6伸烷基或C2-C6伸烯 基; 20 R為H、CrC6鹵烷基、&lt;:2_(:6鹵烯基、CrC6烷氧 基、crc6自烷氧基、C3_C8環烷氧基、CrC6 烧基、C2-C6烯基、C2-C6炔基或〇3-(:8環烷基; T為Ci-C:6伸烷基或c2_cd_烯基; 各G獨立為一 5-或6·員雜環或一 8·、9-或10-員稠 合雙環環系,各環或環系係選擇性地經至多五 個選自在碳環員上之r2】與在氮環員上之R22 的取代基取代; 各&amp;獨立為_素、氰基、經基、胺基、硝基、-CHO、 -C(=0)0H ^ -C(=0)NH2 ^ -C(=S)NH2 ^ -C(=0)NHCN、-C(=0)NH0H、-SH、-S02NH2、 _S02NHCN、-S02NH0H、-OCN、-SCN、_SF5、 C1-C6 烷基、c2-C6 烯基、C2-C6炔基、crC6 鹵 院基、(VQ i稀基、CVC6齒炔基、c3-C8環 201240602 炫•基、C3-C8鹵環烧基、C4-C10院環烧基、C4_Cl〇 環烷烷基、c3-c8環烯基、c3-c8鹵環烯基、c2-c8 烧氧烧基、C4-C1G環院氧燒基、C3-C1G烧氧炫 氧烷基、c2-c8烷硫烷基、c2-c8烷亞磺醯烷 5 基、crc8烷氧ii烷基、c2-c5氰烷基、crc6 羥烷基、crc6烷氧基、crc6 i烷氧基、c3-c8 環烷氧基、c3_c8鹵環烷氧基、c4-c10環烷烷 氧基、C2-C6稀氧基、C2-C6鹵稀氧基、C2-C8 烷氧烷氧基、c2-c8烷羰氧基、crc6烷硫基、 10 Crc6鹵烷硫基、C3-C8環烷硫基、CVC6烷亞 磺醯基、CrC6函烷亞磺醯基、CrC6烷磺醯 基、Ci-C6鹵院石黃醢基、C3-C8環院續醯基、Ci-C6 烷胺基、c2-c8二烷胺基、crc6鹵烷胺基、c2-c8 鹵二院胺基或C3-Cg環院胺基;以及 15 各R22獨立為crc6烷基、c2-c6烯基、c2-c6炔基、R2 is -W6C(=E4)R33, -W6L1C(=E5)R34, -\ν6(:(=Ε6)1^35, -w6s(o)xnr37c(=o)r36 or -W6S(0)xNR37C( =0) L1R36 ; Each E4, E5 and E6 are independently o, s, nr37, nor37, nn(r37)2, N-CN or N-N02; each L1 is independently 0, NR38 or s; each R33, R34, R35 and R36 are independently hydrogen; or CrC6 alkyl, Q-C6 alkenyl, CrC6 alkynyl or C3-C6 cycloalkyl, each optionally substituted by one or more substituents selected from halogen, CN, N02, hydroxy, CrC4 alkoxy, C1-C4 Institute Yasaki, C1-C4 Institute, C1-C4 amine, C2-C8 dialkylamine, C3-C6 cycloalkylamine a group consisting of (CrC4 alkyl) Cs-C: 6 cycloalkylamine groups; 201240602 each R37 is independently hydrazine, CrC6 alkyl or C--C6 haloalkyl; each Q4 and Q5 are independently 〇, s or NR38; Q6 is a Crc4 alkylene group which is optionally substituted with up to 4 substituents selected from the group consisting of Ci-C6 alkyl, C2-C6, C2-C6, and C3-C6 cycloalkyl; R38 independent Is H, CrC6 alkyl or Crc6 haloalkyl; R39 is hydrazine or CrC6 alkyl; each X is 0, 1 or 2; W7 is crc6 alkyl; 10 W is crC6 alkyl, C2-C6 stretching Or C2-C6 stretch Or: (ch2)2〇ch2- or ·(CH2)3〇CH2-; w3 is a CrC6 alkylene group, a c2-c6 extended alkenyl group or a c2_c6 alkynyl group; W4 is a crC6 alkylene group; 15 R3 is Η, halogen, cyano, hydroxy, _〇_M+, amine, nitro, -CHO, -C(=0)0H, -C(=〇)NH2, -C(=S)NH2, -SH ' -S02NH2 ' -SO2NHCN ' -SO2NHOH ' 20 •OCN, _SCN, -SF5, _NHNH2, -NHOH, -N=C=0, -N=C=S, CrC6 alkoxy, CrC6 haloalkoxy, CVC8 ring Alkoxy, C3_C8 cycloalkoxy, G-Cio cycloalkyloxy, C2-C6 alkenoxy, C2-C6 halooxy, c2-c6 oxy, c3-c6 haloalkoxy, c2 -c8 oxy-alkoxy, C2-C8 hexaoxy, C2-C8 aryloxy, C4-C1G cycloalkaneoxy, C3-C]G alkylcarbonyloxy, CrC6 alkyl sulphide Base, CrC6 haloalkylthio, c3-C8 cycloalkylthio, Ci-C6 Hyun sub (four) brewing base, Ci_Cg halogen calcination, CrC6 alkanesulfonyl, crc6 halosulfonyl, c3-c8 Ring 105 25 burnt broth, C!-C6 Institute indeed oxy, C!-C6 amine group, 匸2_匚8 bisamine group, Ci_C6 halogen compound amine, C2-C8 halogen diamine , C3-C8 ring-burning amine group, C2-C8 burnt amine group, C2_Cg haloalkylcarbonyl group, CrQ alkane Amino or crc6 halosulfonylamino; or benzyloxy, phenoxy, benzylcarbonyloxy, phenylcarbonyloxy, phenyl acid oxy, decyloxy, phenylthio, thiol, a phenyl sulfonium group, a hydrazine group, a benzoindolyl group or a benzylsulfonyl group, each optionally substituted with up to five substituents selected from R21 on the ring member; M+ is an alkali metal cation or a Ammonium cation; R4, R5, R6 and R7 are each independently fluorene, halogen, hydroxy, CrC6, 〇2·〇6, C2-C6, C1-C6 halogen, CrC6 alkoxy, CrC6 a haloalkoxy group, a CrC8 cycloalkoxy group or a C3-C8 halocycloalkoxy group; or a phenyl or benzyl group, each optionally substituted with up to five substituents selected from R21 on the ring member; R8 is hydrazine , Q-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, Q-C6 functional group, C2_C6-thyl, C2-C6 halo, C3-C8 cycloalkyl or c3-c8 halo ring An alkyl group; or a benzyl group, which is optionally substituted with up to five substituents selected from R21 on the ring member; R9 is fluorene, QG alkyl, C2-C6 alkenyl, C2-C6 alkynyl, Q-C6 Halogen-based, 〇2·〇6-haloenyl, C2-C6 halo-based, C3-C8 cycloalkyl, c3-c 8-halocycloalkyl, c4_c10 alkylcycloalkyl, c4-c1()cycloalkyl, c6-c14 cycloalkylcycloalkyl, c4-c10 halocycloalkyl, c5-c12 alkanealkyl, c3 a -c8 cycloalkenyl group, a c3-c8 halocycloalkenyl group, a c2-c8 alkoxyalkyl group, a c4-C1() cycloalkyloxyalkyl group, a CVCh) an alkoxy oxyalkyl group or a C2-C8 sulphur alkyl group; R1G is hydrazine, halogen, cyano, hydroxy, amine, nitro, SH, so2nh2, -so2nhcn, -so2nhoh, -OCN, -SCN, -SF5, -NHCHO, -NHNH2, -N3, -ΝΗΟΗ, -NHCN , _NHC (=0) NH2, -N=C=〇, _N=C=S, crc6 alkyl, c2-c6 alkenyl, C2-C6 alkynyl, crc6 haloalkyl, C2-C6-alkenyl, C2 -C6 13⁄4 alkynyl, C3-C8 cycloalkyl, CrC8 halocycloalkyl, c4-c10 alk cycloalkyl, C4-C1() cycloalkyl, cvcH cycloalkane, c4_ClG _ environmental alkyl, Cg-Cn alk cycloalkylalkyl, C3-C8 cycloalkenyl, c3-c8 halocycloalkenyl, C^C:8 alkoxyalkyl, c4-C10 cycloalkoxyalkyl, C3-C1G alkoxyalkoxy Hyun or c2-c8 sulphide; R11 is hydrazine, i, cyano, hydroxy, amine, Cl-c6 alkyl, c2-c6 alkenyl, C2-C6 alkynyl, crc6 dentate, c2 -c6 tooth alkenyl, C2-C6 self-fasting group, C3-C8 cycloalkyl, c3-c8 Halocycloalkyl 'C4-C10 alkylcycloalkyl, c4-c10 cycloalkylalkyl, C4-C10 halocycloalkyl, C5-Ci2 alkoxyalkyl, c3-C8 cycloaliphatic, CVC8 ii ring Base, c2-C8 calcined oxygen base, C^Cio ring oxygenated hospital base, C3_C1() oxygenated oxygenate, C2_Q alkylsulfanyl, CrC8 alkylsulfinyl or c2-C8 Or a phenyl group which is optionally substituted with up to five substituents selected from R21; 12 R is hydrazine, halogen, cyano, hydroxy, amine, Cl_c6 alkyl, c2-c6 alkenyl, (: 2 -(:6 alkynyl, CVC6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, c3-C8 cycloalkyl, c3-c8 halocycloalkyl, CVC10 alkanecycloalkyl, C4-C10 a cycloalkylalkyl group, a C6-C14 ring-ring ring, a c4_ClG ring-ring, a c5_Ci2 alk cycloalkanyl group, a C3_C8 cycloalkenyl group, a c3-c8 halocycloalkenyl group or a C2-C8 alkoxycarbonylamino group; R13 is fluorene, halogen, cyano, hydroxy, amine, nitro or c2_c8 alkoxycarbonyl; η is 0, 1 or 2; each R14, R15, R18 and Ri9 are independently hydrazine, halogen, cyano, hydroxy or Ci_C6 Or a pair of R14 and R18 together as a C2-C6 alkylene group or a C2-C6 alkylene group; 20 R is H, a CrC6 haloalkyl group, &lt; 2_(: 6 haloalkenyl, CrC6 alkoxy, crc6 to alkoxy, C3_C8 cycloalkoxy, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or 〇3-(:8 cycloalkyl T is Ci-C: 6 alkyl or c2_cd-alkenyl; each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or The ring system is selectively substituted with up to five substituents selected from the group consisting of r2 on the carbocyclic ring member and R22 on the nitrogen ring member; each &amp; independently is _ s, cyano, thiol, amine, nitro Base, -CHO, -C(=0)0H ^ -C(=0)NH2 ^ -C(=S)NH2 ^ -C(=0)NHCN, -C(=0)NH0H, -SH, -S02NH2 , _S02NHCN, -S02NH0H, -OCN, -SCN, _SF5, C1-C6 alkyl, c2-C6 alkenyl, C2-C6 alkynyl, crC6 halogen compound, (VQ i dilute, CVC6 alkynyl, c3- C8 ring 201240602 Hyun • base, C3-C8 halocycloalkyl, C4-C10 ring cycloalkyl, C4_Cl〇 cycloalkyl, c3-c8 cycloalkenyl, c3-c8 halocycloalkenyl, c2-c8 oxygenated Alkyl, C4-C1G ring oxyalkyl, C3-C1G oxyalkyloxy, c2-c8 alkylsulfanyl, c2-c8 alkylsulfinyl 5, crc8 alkoxy ii alkyl, c2- C5 cyanoalkyl, crc6 hydroxyalkyl, crc6 alkoxy, crc6 i Oxy, c3-c8 cycloalkoxy, c3_c8 halocycloalkoxy, c4-c10 cycloalkanoxy, C2-C6 diloxy, C2-C6 halooxy, C2-C8 alkoxyalkoxy , c2-c8 alkylcarbonyloxy, crc6 alkylthio, 10 Crc6 haloalkylthio, C3-C8 cycloalkylthio, CVC6 alkylsulfinyl, CrC6 sulfinyl, CrC6 alkanesulfonyl, Ci-C6 brothel, C3-C8 ring thiol, Ci-C6 alkylamine, c2-c8 dialkylamine, crc6 haloalkylamine, c2-c8 haloamine or C3-Cg a ring amine group; and 15 each R22 is independently a crc6 alkyl group, a c2-c6 alkenyl group, a c2-c6 alkynyl group,

CrC6 _烷基、(:3-(:8環烷基或C2-C8烷氧烷基。 式1P化合物之實施例包括: 實施例 PA 為 A-1、A-3、A-4、A-5 或 A-6 ; R1為 20CrC6-alkyl, (: 3-(:8-cycloalkyl or C2-C8 alkoxyalkyl. Examples of the compound of formula 1P include: Example PA is A-1, A-3, A-4, A- 5 or A-6; R1 is 20

R1 為-WkpEbR24 、 -W^C^E^R25 或 V^CpE3)!^26 ;或 R1 為 GA 或-w2GA ; 各GA為- 5_至6.員碳環, =2rNN(R29)2 的環 ^ 或。至 分飽和碳螺環或雜螺環環系,其 之擇性=包括選自c(=0)、c(=n_or30)或 雇(R )2的環員’各環或環系選擇性地經至 夕三個選自在碳環員上之r2i與在氮環員上之 R的取代基取代; 各 E、E 與 E 獨立為 〇、N〇R28 或 nn(r28)2 ; L獨立為〇或nr31 ; 各R24、R25與R26獨立為氫;或C]_C4院基或GA 環烷基,各選擇性地經一或多個選自由齒素、 CN、羥基、crC2烷氧基、CrC2烷亞磺醯基 與CrC4烷磺醯基所組成之群組的取代基取 代; 各R28獨立為Η、CrC3烷基或Cl-C3齒烷基; R獨立為Η、C1-C3烧基、C1-C3鹵烧基、C】-C3 院羰基、CrC3度礦醯基或CrQj鹵院續醢基; 各Q1與Q2獨立為0或N(R31); Q為C2_c;3伸炫基,其選擇性地經至多2個選自 crc4烷基的取代基取代; R3G獨立為Η、CrC3烷基或CrC3鹵烷基; R31獨立為Η、(:】-(:3烷基或CrC3鹵烷基; R32為Η或CrC3烷基; W1 為 C2-C4伸院基、-(CH2)2OCH2-或-(CH2)3OCH2-; ~2為CrC3伸烷基 201240602 W5為crc4伸烷基; R2為苯基或-W3(苯基),各選擇性地在環員上經至 多五個取代基取代,該取代基係選自R21 ;或 -G ;或CrC6烷基、C2-C6烯基、C2-C6炔基、 5 Ci_C6鹵烧基、C2-C6鹵稀基、C2-C6鹵炔基、 C3-Cgi哀院基、C3-C8鹵環烧基、C4-C10院環烧 基、C4-C1G環烧院基、C6-C14環烧環院基、C4_Ci〇 鹵環烷烷基、c5-c12烷環烷烷基、c3_c8環烯 基、C3-C8鹵環稀基、C2-C8院氧烧基、C3-C10 10 烷氧烯基、C4-C10環烷氧烷基、C4-C10環烷氧 烷氧烷基、c3-c1G烷氧烷氧烷基、c2-c8烷硫 炫》基、C2-C8烧亞石黃酿炫》基、C2_C8炫》續酿烧 基、c2-c8烷羰基、c4-c10環烯烷基、c2-c8鹵 烷氧烷基、c2-c8烷氧鹵烷基、c2_c8鹵烷氧鹵 15 烧基、C4-C10鹵環烧氧院基、C4-C10環稀氧烧 基、C4-C10鹵環稀氧烧基、C3-C10二烧氧院基、 CVC6烷氧基、crc6鹵烷氧基、c3-c8環烷氧 基、c3-c8鹵環烷氧基、c4-cl0環烷烷氧基、 c2-c6烯氧基、C2-C6鹵烯氧基、02-(:6炔氧基、 20 c3-c6鹵快氧基、c2-c8炫氧烧氧基、c2-c8烧 羰氧基、c2-c8鹵烷羰氧基、c4-c10環烷羰氧 基、C3-C1G烷羰烷氧基、CrC6烷硫基、Q-C6 鹵院硫基、C3-C8環烧硫基、Ci-C6烧亞績酿 基、Ci-C6鹵炫》亞石黃酿基、Ci_C6 $完續酿基、Ci-C6 25 _烧續酿基、C3-C8環烧續酿基、C3-C8二院碎 基、c3-c8環烯氧基、c3_c8鹵環烯氧基、c2-c8 111 鹵烷氧烷氧基、c2-c8烷氧鹵烷氧基、c2-c8鹵 烷氧il烷氧基、C3-CiG烷氧羰烷氧基、C2-C8 烷基(硫羰基)氧基、QrCs環烷亞磺醯基或 C3-C10鹵三烷矽基;或 r2 為-W6C(=E4)R33 、 -W6L1C(=E5)R34 或 -W6C(=E6)L1R35 ; 各 E4、E5 與 E6 獨立為 ο、NOR37 或 NN(R37)2 ; 各L1獨立為〇或nr38 ; 各R33、R34與R35獨立為氫;或Cl-C4烷基、C3_C5 環烷基’各選擇性地經一或多個選自由函素、 CN、羥基、CrC2烷氧基、CrC2烷亞磺醯基 或CrC2烷續醯基所組成之群組的取代基取 代; 各3R37獨立為Η、CrC3烷基或CrC3齒烷基; R獨立為Η、C〗-C3烧基或Ci-Cs函院基; W3 為-CH2-; W6 為 c2-c4 伸烷基、-(Ch2)2〇CH2_ 或 _(Ch2)3〇CH2_ ; R3為羥基、-0·Μ+、c2-c8烷羰氧基、c2_c8鹵烷羰 氧基、CVCh)環烷羰氧基或c3_Cig烷羰烷氧 基;或苄氧基、苯氧基、苄羰氧基、苯羰氧基、 苯磺醯氧基或f磺醯氧基,各選擇性地在環員 上經至多兩個選自的取代基取代; M+為一鈉或鉀金屬陽離子; R為crc6院基;R1 is -WkpEbR24, -W^C^E^R25 or V^CpE3)!^26; or R1 is GA or -w2GA; each GA is -5_ to 6. Member carbon ring, =2rNN(R29)2 Ring ^ or. To a saturated carbon spiro or heterospiro ring system, the selectivity of which includes a ring member selected from c(=0), c(=n_or30) or hired (R)2, each ring or ring system selectively After the third, three substituents selected from r2i on the carbon ring member and R on the nitrogen ring member are substituted; each E, E and E is independently 〇, N〇R28 or nn(r28)2; L is independently 〇 Or nr31; each R24, R25 and R26 are independently hydrogen; or C]_C4 or GA cycloalkyl, each optionally one or more selected from the group consisting of dentate, CN, hydroxyl, crC2 alkoxy, CrC2 alkane Substituted by a group consisting of a sulfinyl group and a CrC4 alkanesulfonyl group; each R28 is independently a fluorene, a CrC3 alkyl group or a Cl-C3 dentate alkyl group; R is independently a fluorene, a C1-C3 alkyl group, and C1- C3 halogenated group, C]-C3 yard carbonyl, CrC3 degree orthoquinone or CrQj halogen sulfonate; each Q1 and Q2 is independently 0 or N (R31); Q is C2_c; 3 extensible, its selectivity The ground is substituted with up to 2 substituents selected from the group consisting of crc4 alkyl; R3G is independently hydrazine, CrC3 alkyl or CrC3 haloalkyl; R31 is independently hydrazine, (:]-(: 3 alkyl or CrC3 haloalkyl; R32 Is Η or CrC3 alkyl; W1 is C2-C4 stretching, -(CH2)2OCH2- or -(CH2)3OCH2-; ~2 is CrC 3 alkylene 201240602 W5 is crc4 alkyl; R2 is phenyl or -W3 (phenyl), each optionally substituted with up to five substituents on the ring member, the substituent is selected from R21; or - G; or CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, 5 Ci_C6 haloalkyl, C2-C6 halo, C2-C6 haloalkynyl, C3-Cgi mournyl, C3-C8 halo Cycloalkyl, C4-C10 ring cycloalkyl, C4-C1G ring furnace base, C6-C14 ring-burning ring base, C4_Ci〇 halocycloalkyl, c5-c12 alkanealkyl, c3_c8 cycloalkenyl , C3-C8 halocycloalkyl, C2-C8 alkoxyalkyl, C3-C10 10 alkoxyalkenyl, C4-C10 cycloalkoxyalkyl, C4-C10 cycloalkoxy alkoxy, c3-c1G alkane Oxyalkoxyalkyl, c2-c8 alkane sulphonyl, C2-C8 sulphide sulphate, C2_C8 炫, continuous calcination, c2-c8 alkylcarbonyl, c4-c10 cycloalkenyl, c2 -c8 haloalkyloxyalkyl, c2-c8 alkoxyhaloalkyl, c2_c8 haloalkyloxyhalo 15 alkyl, C4-C10 halocyclooxylate, C4-C10 cyclooxyalkyl, C4-C10 halo ring Dilute oxygen, C3-C10 di-Oxygen, CVC6 alkoxy, crc6 haloalkoxy, c3-c8 cycloalkoxy, c3-c8 halocycloalkoxy, c4-cl0 cycloalkaneoxy , c2-c6 Oxy, C2-C6 haloenyloxy, 02-(:6 alkynyloxy, 20 c3-c6 halooxy, c2-c8 oxooxy, c2-c8 carbonyloxy, c2-c8 Alkylcarbonyloxy, c4-c10 cycloalkaneoxy, C3-C1G alkylcarbonyloxy, CrC6 alkylthio, Q-C6 halogen thio, C3-C8 cyclosulphur, Ci-C6 Stuffed base, Ci-C6 halogen Hyun" Asian stone yellow brewing base, Ci_C6 $ continuous brewing base, Ci-C6 25 _ burned brewing base, C3-C8 ring burning brewing base, C3-C8 second courtyard broken base, c3 -c8 cycloalkenyloxy, c3_c8 halocycloalkenyloxy, c2-c8 111 haloalkoxy alkoxy, c2-c8 alkoxyhalooxy, c2-c8 haloalkoxy il alkoxy, C3-CiG alkane Oxycarbonyl alkoxy group, C2-C8 alkyl (thiocarbonyl)oxy group, QrCs cycloalkyl sulfinyl group or C3-C10 halotrialkyl fluorenyl group; or r2 is -W6C(=E4)R33, -W6L1C(= E5) R34 or -W6C(=E6)L1R35; each E4, E5 and E6 are independently ο, NOR37 or NN(R37)2; each L1 is independently 〇 or nr38; each R33, R34 and R35 are independently hydrogen; or Cl -C4 alkyl, C3_C5 cycloalkyl' each selectively via one or more groups selected from the group consisting of a hydroxyl group, a CN, a hydroxyl group, a CrC2 alkoxy group, a CrC2 alkylsulfinyl group or a CrC2 alkane group Substituent 3R37 is independently hydrazine, CrC3 alkyl or CrC3 dentate; R is independently Η, C 〖-C3 alkyl or Ci-Cs comon; W3 is -CH2-; W6 is c2-c4 alkyl , -(Ch2)2〇CH2_ or _(Ch2)3〇CH2_ ; R3 is hydroxy, -0·Μ+, c2-c8 alkylcarbonyloxy, c2_c8 halocarbonyloxy, CVCh)cycloalkaneoxy or a c3_Cig alkylcarbonyl alkoxy group; or a benzyloxy group, a phenoxy group, a benzyloxyoxy group, a phenylcarbonyloxy group, a benzenesulfonyloxy group or an sulfonyloxy group, each selectively having up to two Substituted for a substituent selected; M+ is a monosodium or potassium metal cation; R is a crc6 hospital base;

RlG為Η、鹵素或Clc6•烷基; R11為Η或crc6烷基; 201240602 R12為Η、鹵素、氰基、羥基、胺基或Cl_c6烷基; 各 R14、R15、R18 與 R19 為 Η 或 CH3 ; D 1 4 μ | g κ 與R —起作為 _CH2CH2CH2^_CH=CHCH2_; R20 為 Η 或 CH3 ; τ 為-CH2CH2-或-CH=CH-; 各G為G-l至G-20 (如實施例116中所描述者); r為 0、1、2 或 3 ; 各R21獨立為鹵素、氰基、羥基、硝基、-CHO、-SH、RlG is hydrazine, halogen or Clc6•alkyl; R11 is hydrazine or crc6 alkyl; 201240602 R12 is hydrazine, halogen, cyano, hydroxy, amine or Cl_c6 alkyl; each R14, R15, R18 and R19 is Η or CH3 D 1 4 μ | g κ and R together as _CH2CH2CH2^_CH=CHCH2_; R20 is Η or CH3; τ is -CH2CH2- or -CH=CH-; each G is G1 to G-20 (as in the example (described in 116); r is 0, 1, 2 or 3; each R21 is independently halogen, cyano, hydroxy, nitro, -CHO, -SH,

CrC6 烷基、C2_C6 烯基、C2_C6 炔基、Ci_C6 鹵 燒基、C2-C6 _稀基、C2-C6齒炔基、C3-C8環 烧基、C;j-C8鹵ί哀烧基、C4-C10烧環院基、C:rCi〇 環院燒基、(:3_(:8環烯基、C3-C8鹵環烯基、C2-C8 垸氧院基、CVC1()環烷氧烷基、C3-C1G烷氧烷 氧院基、CrC8烷硫烷基、c2-c8烷亞磺醯烷 基' C2_c8烷氧_烷基、c2_c5氰烷基、Crc6 經燒基、crc6烷氧基、Crc6 _烷氧基、c3-c8 環燒氧基、C3-C8鹵環烷氧基、CrC10環烷烷 氧基、C2-C6稀氧基、crC6 ^烯氧基、c2-c8 炫氧燒氧基、C2-C8烷羰氧基、Crc6烷硫基、 C1-C6 -烧硫基、c3_c8環烧硫基、Ci_c6烷亞 石黃酿基、CVC6 li烷亞磺醯基、crc6烷磺醯 基、CrC6鹵烷磺醯基或(:3-(:8環烷磺醯基;以 及 各R22獨立為CrQ烷基或crc6 ii烷基。 實施例PB.實施例PA之化合物’其中 A 為 A-1、a-3 或 A-5 ; 113 201240602 B1 為 C-l ; B2 為 C-3 ; B3 為 C-l ; R2為苯基或-w3(苯基),各選擇性地在環員上經至 多兩個選自R21的取代基取代;或_G;或(:1_(:6 院基或C3-C8環烧基; R3為羥基或c2-c8烷羰氧基; R9 為 ch2ch3 ;CrC6 alkyl, C2_C6 alkenyl, C2_C6 alkynyl, Ci_C6 haloalkyl, C2-C6-dilute, C2-C6 alkynyl, C3-C8 cycloalkyl, C; j-C8 halo, C4 -C10 烧环院基, C:rCi〇环院, (:3_(:8-cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 oxime, CVC1()cycloalkoxyalkyl , C3-C1G alkoxy alkoxy group, CrC8 alkylsulfanyl, c2-c8 alkylsulfinyl' C2_c8 alkoxy-alkyl, c2_c5 cyanoalkyl, Crc6 alkyl, crc6 alkoxy, Crc6 Alkoxy, c3-c8 cycloalkoxy, C3-C8 halocycloalkoxy, CrC10 cycloalkanoxy, C2-C6 dioxy, crC6^enyloxy, c2-c8 aerobic alkoxy , C2-C8 alkylcarbonyloxy, Crc6 alkylthio, C1-C6-sulfuryl, c3_c8 cycloalkylthio, Ci_c6 alkyl sulfite, CVC6 lialkylsulfinyl, crc6 alkanesulfonyl, CrC6 haloalkylsulfonyl or (: 3-(:8-cycloalkanesulfonyl; and each R22 is independently CrQ alkyl or crc6 ii alkyl. Example PB. Compound of Example PA' wherein A is A-1 , a-3 or A-5; 113 201240602 B1 is Cl; B2 is C-3; B3 is Cl; R2 is phenyl or -w3 (phenyl), each selectively on the ring member Up to two substituents selected from R21; or _G; or (:1_(:6) or C3-C8 cycloalkyl; R3 is hydroxy or c2-c8 alkylcarbonyloxy; R9 is ch2ch3;

RlG 為 Η 或 CH3 ; G 為 G-2、G-3 或 G-15 ;以及 R21獨立為鹵素、硝基、CrC6烷基、crc6鹵烷基、 Ci-C6烧氧基、Ci-C6鹵烧氧基或crc6烧硫基。 實施例PC.實施例PB之化合物,其中 A 為 A-1 ; R1為RlG is Η or CH3; G is G-2, G-3 or G-15; and R21 is independently halogen, nitro, CrC6 alkyl, crc6 haloalkyl, Ci-C6 alkoxy, Ci-C6 halogen Oxyl or crc6 burns sulfur. Embodiment PC. A compound of Embodiment PB wherein A is A-1; R1 is

各Q1與Q2為Ο ; Q3為c2-伸烷基; R32為η或甲基; W為C3-C4伸院基; 201240602 R2為苯基、2-曱基苯基、3-曱基苯基、3-溴苯基、 3-氯苯基、4·氣苯基、3-氟苯基、3,5·二氟苯基、 3 -塞吩基或2 -σ塞吩基, R3 為羥基或-〇C(=0)CH2CH(CH3)2 ; 5 各 R14、R15、R18 與 R19 為 Η 或 CH3。 實施例PD.實施例B之化合物,其中 A 為 A_1 ; R1 為-WtpE1)!^4 ; E1 為 NOR28 ; ίο R28為Η或曱基; R2為苯基、2-甲基苯基、3-甲基苯基、3-溴苯基、 3_氯苯基、4_氯苯基、3-氟苯基、3,5-二氟苯基、 3-噻吩基、2-噻吩基或2-吡啶基; R3 為羥基或-0C(=0)CH2CH(CH3)2;以及 15 各 R14、R15、R18 與 R19為 Η。 實施例ΡΕ.實施例ΡΒ之化合物,其中 Α 為 Α-1 ; R1 為-GA ; 各GA為一 5-至6-員碳環,其包括選自C(=0)或 2〇 C(=N-OR3G)的環員;或一 9-至10-員飽和雜螺 環環系,其選擇性地包括選自C(=0)或 C(=N_OR3G)的環員,各環或環系選擇性地經至 多兩個選自在碳環員上之R21與在氮環員上之 R22的取代基取代; 25 R3G為Η或甲基; R21為鹵素或CrC3烷基; 115 201240602 烷基; 實施例PF·實施例pE之化合物,其中ga係選自 GA-1、GA-2、GA-3、GA-7、GA_8 與 GA-9。 R2為苯基、2·甲基苯基、3-曱基苯基、4-氣苯基、 3-氟苯基或3,5-二氟苯基; R3為經基;以及 各 R14、R15、R18 與 R19為 Η。 具體實施例包括一選自下列之式1Ρ化合物: 3_(丨,4-二氧雜螺[4 5]癸_8_基)_5_[(2羥基_6側氧基 1 %己稀-l-基)幾基]-2-苯基-4(3//)-喷咬酮(化 合物1 )與 5_[(2-經基_6_側氧基小環己烯小基)羰基]_6_側氧基 _2_苯基-1(6//)-鳴啶乙醛1-(0·甲基肟)(化合物 2)〇 本發明亦關於一種用於防治非所欲植物之生長的 方法,其包含向該植物之所在地施用一除草有效量的一 本發明化合物(例如以一本文中所述之組成物)。值得 注意且關於使用方法之實施例為涉及上述實施例之化 合物者。 如上所提及者,本發明亦包括一除草混合物,其包 含(a)—選自式1、其氧化物及其鹽之化合物,以及邙) 至少一種額外活性成分,其選自(bl)光系統II抑制劑、 (b2)乙醯羥酸合成酶(AHAS)抑制劑、(b3)乙醯CoA羧化 酶(ACCase)抑制劑、(b4)生長素模擬物、(b5)5-烯醇-丙 酮醯莽草酸-3-磷酸(EPSP)合成酶抑制劑、(b6)光系統I 電子轉向劑、〇7)原紫元氧化酶(PPO)抑制劑、(b8)麵醯 201240602 胺酸合成酶(GS)抑制劑、_極長鍵脂肪酸(VLCFA)延 長酶抑制劑、_)生長素傳輸抑制劑、(bu)八氮番祐 紅素去飽和酶(PDS)抑制劑、(b丨2) 4_羥苯基_丙酮酸二氧 合酶(HPPD)抑制劑、(b丨3)黑尿酸茄尼轉移酶(HST)抑制 5 劑、(Μ4)其他除草劑,包括有絲分裂干擾劑、有機砷劑、 亞速爛、燕麥枯、溴布泰、抑草丁、環庚草醚、苄草隆、 邁隆、汰草龍、甲基汰草龍、乙氧苯草胺、殺木膦、殺 木膦銨、威百畝、噁嗪草酮、油酸、壬酸與稗草畏及(bl5) 除草劑保護劑;以及(bl)至(bl5)化合物之鹽。 10 「光系統11抑制劑」(bl)為在QB結合位置 (QB-bindingniche)結合至該d-1蛋白質的化學化合物, 並且因而在葉綠體類囊體膜(chl〇r〇piast thylakoid membrane)中阻斷電子由qa傳輸至qb。經阻斷而無法 穿過光系統II的電子係經由一系列的反應轉移而形成 15 毒性化合物,其會破壞細胞膜並造成葉綠體膨潤、膜滲 漏並且最後細胞破壞。該qb結合位置具有三個不同的 結合點:結合點A結合三。秦(triazine)如草脫淨 (atrazine)、三嗓鲷(triazinone)如菲殺淨(hexazinone)與尿 嘧啶如克草(bromacil),結合點B結合苯脲(phenylurea) 20 如達有龍(diuron),而結合點C結合苯并嗟二嗤如本達 隆(bentazon)、腈如溴苯腈(bromoxynil)與苯基-»荅嗓 (phenyl-pyridazine)如必汰草(pyridate)。光系統 II 抑制 劑的實例包括草殺淨(ametryn)、草脫淨(atrazine)、氰乃 淨(cyanazine)、敵草淨(desmetryne)、愛落殺 25 (dimethametryn)、撲滅通(prometon)、佈滅淨 (prometryne)、普拔根(propazine)、草滅淨(simazine)、 117 201240602 西草淨(simetryn)、甲氧去草净(terbumeton)、特丁津 (terbuthylazine)、投布淨(terbutryne)、草達津 (trietazine)、菲殺淨(hexazinone)、苯唤草酮 (metamitron)、滅必淨(metribuzin)、氨唑草酮 5 (amicarbazone)、克草(bromacil)、環草定(lenacil)、特草 定(terbacil)、氣草敏(chloridazon)、甜菜安 (desmedipham)、甜菜寧(phenmedipham)、滅落寧 (chlorobromuron)、綠麥隆(chlorotoluron)、枯草龍 (chloroxuron)、惡唑隆(dimefuron)、達有龍(diuron)、續 ίο 噻隆(ethidimuron)、非草隆(fenuron)、伏草隆 (fluometuron)、異丙隆(iSOpr〇turon)、愛速隆(isouron)、 理有龍(Hnuron)、甲草苯隆(methabenzthiazuron)、漠谷 隆(metobromuron)、甲氧隆(metoxuron)、綠谷隆 (monolinuron)、草不隆(neburon)、環草隆(siduron)、丁 15 噻隆(tebuthiuron)、除草靈(propanil)、蔬草滅 (pentanochlor)、漠紛肪(bromofenoxim)、漠苯腈 (bromoxynil)、碳塞尼爾(ioxyni卜本達隆(bentazon)、必 汰草(pyridate)與啶蟲丙醚(pyridafol)。 「AHAS抑制劑」(b2)為抑制乙醯羥酸合成酶 2〇 (AHAS)之化學化合物,亦稱為乙醯乳酸合成酶 (acetolactate synthase,ALS),並且因而藉由抑制支鏈脂 族胺基酸如纈胺酸、白胺酸與異白胺酸的產生而殺死植 物’前述胺基酸為DNA合成與細胞生長所需者。AHAS 抑制劑的實例包括酿嘴續隆(amidosulfuron)、四嗤喊確 25 隆(azimsulfuron)、免速隆(bensulfuron-methyl)、氣嘯續 隆(chlorimuron-ethyl)、氣磺隆(chlorsulfuron)、西速隆 201240602 (cinosulfuron)、環確隆(cyclosulfamuron)、胺苯橫隆 (ethametsulfuron-methyl)、亞速隆(ethoxysulfuron)、伏 速隆(flazasulfuron)、氟啶嘧續隆(flupyrsulfuron-methyl) (包括納鹽)、雙氣續草胺(foramsulfuron)、合速隆 5 (halosulfuron-methyl)、依速隆(imazosulfuron)、甲基磁 續隆(iodosulfuron-methyl)(包括鈉鹽)、甲績胺項隆 (mesosulfuron-methyl)、雙醚氣 α比癌續隆 (metazosulfuron)、曱續隆(metsulfuron-methyl)、煙《密續 隆(nicosulfuron)、環氧喷礦隆(oxasulfuron)、氟》密續隆 ίο (primisulfuron-methyl)、咪唾嘴績隆(propyrisulfuron)、 氟確隆(prosulfuron)、百速隆(pyrazosulfuron-ethyl)、玉 嘴續隆(rimsulfuron)、甲鳴續隆(sulfometuron-methyl)、 石黃醯續隆 (sulfosulfuron)、嗟吩續隆 (thifensulfuron-methyl)、驗苯確隆(triasulfuron)、苯續隆 is (tribenuron-methyl)、三氟咬石黃隆(trifloxysulfuron)(包 括納鹽)、氟胺罐隆(triflusulfuron-methyl)、三氟甲續隆 (tritosulfuron)、曱味0坐煙酸(imazapic)、咪草酯 (imazamethabenz-methyl)、曱氧11米草煙(imazamox)、依 滅草(imazapyr)、滅草喧(imazaquin)、味草煙 2〇 (imazethapyr)、氣酯績草胺(cloransulam-methyl)、雙氣 石黃草胺(diclosulam)、雙氟續草胺(florasulam)、°坐*&gt;密續草 胺(flumetsulam)、確草唾胺(metosulam)、平速爛 (penoxsulam)、雙草醚(bispyribac-sodium)、嘴咬肪草趟 (pyribenzoxim)、環醋草趟(pyriftalid)、喊草硫醚 25 (pyrithiobac-sodium)、喊草it(pyriminobac-methyl)、酮 脲磺草吩酯(thiencarbazone)、 氟酮磺隆 201240602 (flucarbazone-sodium) 與丙 苯續隆 (propoxycarbazone-sodium) ° 「ACCase抑制劑」(b3)為抑制乙醯c〇A羧化酶的 化學化合物,該酶在植物中負責催化一脂質與脂肪酸合 5 成中的早期步驟。脂質為細胞臈的必需成分,若無脂質 則無法產生新細胞。乙醯CoA綾化酶的抑制與其所造 成的脂質產生缺乏會導致細胞膜失去完整性,特別是在 活性生長區域如分生組織。最終芽體(sh〇〇t)與根莖 (rhizome)停止生長,並且芽體分生組織與根莖芽開始枯 ίο 萎。ACCase抑制劑的實例包括炔草酸(ci〇dinafop)、赛 伏草(cyhalofop)、禾草靈(did〇f〇p)、芬殺草 (fenoxaprop)、伏寄普(fluazifop)、合氣氟(hal〇xyf〇p)、 普拔草(propaquizafop)、快伏草(quizal〇f〇p)、亞汰草 (alloxydim)、丁 苯草酮(butr〇xydim)、剋草同 15 (clethodim)、環殺草(cydoxydim)、唑啉草酯 (pinoxaden)、氣苯嗟草 _ (pr〇f〇Xydim)、西殺草 (sethoxydim)、得殺草(teprai〇xydim)與肟草酮 (tralkoxydim),包括經解析形式如芬殺草_p、伏寄普_p、 合氯氟-P與快伏草-P,以及酯形式如炔丙基炔草酸、丁 20 基赛伏草、曱基禾草靈與乙基芬殺草·ρ。 &gt; 生長素為一種植物激素,其調節許多植物組織的生 長。「生長素模擬物」(b4)為模擬植物生長激素生長素的 化學化合物,因而造成不受調控及混亂的生長,導致易 受影響之植物物種的死亡。生長素模擬物的實例包括但 25 不限於胺比克(aminocyclopyrachlor)、氯氨基°比咬酸 (aminopyralid)、乙基草除靈(benaz〇Hn_ethyi)、克攔本 201240602 (chloramben)、克普草(ci〇mepr〇p)、畢克草(ci〇pyraiid)、 麥草畏(dicamba)、2,4-D、2,4-DB、滴丙酸(dichlorprop)、 氟氣比(fluroxypyr)、甲氯丙酸(mec〇pr〇p)、mcpa、 MCPB、2,3,6-TBA、毒莠定(picloram)、三氯比 (triclopyr)、快克草(quinci〇rac)與氣甲喹琳醆 (quinmerac)。 10 20 「EPSP (5-烯醇·丙酮醯莽草酸_3_磷酸)合成酶抑制 劑」(b5)為抑制5-烯醇_丙酮醯莽草酸_3_磷酸合成酶之 化學化合物’該酶涉及芳族胺基酸之合成,諸如酪胺 酸、色胺酸與苯丙胺酸。Epsp抑制劑除草劑係經由植 物葉子迅速吸收並且在韌皮轉位至生長點。嘉磷塞 (Glyphosate)對不具選擇性(n〇nsdective)的萌後除草 劑。嘉磷塞包括酯與鹽如銨鹽、異丙銨鹽、鉀鹽、鈉鹽 (包括倍半納鹽(sesquisodium))與三曱基硫鹽 (tdmesium)(又稱為草硫膦(sulf〇sate))。 孤Each Q1 and Q2 is Ο; Q3 is c2-alkylene; R32 is η or methyl; W is C3-C4 stretching; 201240602 R2 is phenyl, 2-mercaptophenyl, 3-mercaptophenyl , 3-bromophenyl, 3-chlorophenyl, 4·oxyphenyl, 3-fluorophenyl, 3,5·difluorophenyl, 3-deseptenyl or 2-σsecenyl, R3 is hydroxy Or -〇C(=0)CH2CH(CH3)2; 5 Each R14, R15, R18 and R19 is Η or CH3. Embodiment PD. The compound of Example B, wherein A is A_1; R1 is -WtpE1)!^4; E1 is NOR28; ίο R28 is fluorenyl or fluorenyl; R2 is phenyl, 2-methylphenyl, 3- Methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 3,5-difluorophenyl, 3-thienyl, 2-thienyl or 2- Pyridyl; R3 is hydroxy or -0C(=0)CH2CH(CH3)2; and 15 each R14, R15, R18 and R19 are hydrazine. Example 化合物. The compound of Example ,, wherein Α is Α-1; R1 is -GA; each GA is a 5- to 6-membered carbocyclic ring comprising a group selected from C(=0) or 2〇C (= a ring member of N-OR3G); or a 9- to 10-membered saturated heterospiro ring system optionally comprising a ring member selected from C(=0) or C(=N_OR3G), each ring or ring system Optionally substituted with up to two substituents selected from R21 on a carbocyclic member and R22 on a nitrogen ring member; 25 R3G is hydrazine or methyl; R21 is halogen or CrC3 alkyl; 115 201240602 alkyl; Example PF. The compound of Example pE wherein ga is selected from the group consisting of GA-1, GA-2, GA-3, GA-7, GA_8 and GA-9. R2 is phenyl, 2-methylphenyl, 3-mercaptophenyl, 4-phenylphenyl, 3-fluorophenyl or 3,5-difluorophenyl; R3 is a trans-group; and each R14, R15 , R18 and R19 are Η. Specific examples include a compound of the formula 1 selected from the group consisting of: 3_(丨,4-dioxaspiro[4 5]fluorene_8-yl)_5_[(2 hydroxy-6 oxo 1 hexyl-l- Alkyl]-2-phenyl-4(3//)-pilotone (compound 1) with 5-[(2-carbyl-6-oxylcyclohexene)carbonyl]_6_ Sideoxy_2_phenyl-1(6//)-alkidineacetaldehyde 1-(0.methylhydrazine) (Compound 2) The present invention also relates to a method for controlling the growth of unwanted plants And comprising administering to the locus of the plant a herbicidally effective amount of a compound of the invention (e.g., as described herein). It is worth noting that the examples relating to the method of use are those relating to the compounds of the above examples. As mentioned above, the present invention also encompasses a herbicidal mixture comprising (a) - a compound selected from the group consisting of Formula 1, its oxides and salts thereof, and hydrazine) at least one additional active ingredient selected from the group consisting of (bl) light System II inhibitor, (b2) acetaminolate synthase (AHAS) inhibitor, (b3) acetoin CoA carboxylase (ACCase) inhibitor, (b4) auxin mimetic, (b5) 5-enol - Acetone oxalic acid-3-phosphate (EPSP) synthetase inhibitor, (b6) Photosystem I electron diverting agent, 〇7) Proto-violet oxidase (PPO) inhibitor, (b8) 醯201240602 Amino acid synthesis Enzyme (GS) inhibitor, _ very long bond fatty acid (VLCFA) elongase inhibitor, _) auxin transport inhibitor, (bu) octanitrocoumarin desaturase (PDS) inhibitor, (b丨2 4_hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor, (b丨3) black uric acid solanide transferase (HST) inhibition 5, (Μ4) other herbicides, including mitotic interference agents, organic Arsenic, sub-speed rotten, oatmeal, bromobutene, chlorpyrifos, cycloheptyl ether, benzalkon, melon, ticlopron, methyl chlorpyrifos, acetochlor, chlorpyrifos, Killing phospha-ammonium Mu, oxazine metribuzin, oleic acid, pelargonic acid and pyributicarb and (BL5) herbicide protecting agent; and (BL) to the salt (BL5) of the compound. 10 "Photosystem 11 inhibitor" (bl) is a chemical compound that binds to the d-1 protein at the QB binding site (QB-bindingniche), and thus is in the chloroplast thylakoid membrane (chl〇r〇piast thylakoid membrane) Blocking electrons are transmitted from qa to qb. Electrons that are blocked and unable to pass through photosystem II form a toxic compound via a series of reaction shifts that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cell destruction. The qb binding site has three different binding sites: binding site A binds three. Triazine such as atrazine, triazinone such as hexazinone and uracil such as bromacil, binding point B to phenylurea 20 Diuron), while binding point C binds benzopyrene such as bentazon, nitrile such as bromoxynil and phenyl-pyridazine such as pyridate. Examples of photosystem II inhibitors include ametryn, atrazine, cyanazine, desmetryne, dimethametryn, prometon, Prometryne, propazine, simazine, 117 201240602 simetryn, terbumeton, terbuthylazine, cast net ( Terbutryne), trietazine, hexazinone, metamitron, metribuzin, amicarbazone, bromacil, cycloheximidine (lenacil), terbacil, chloridazon, desmedipham, phenmedipham, chlorobromuron, chlorotoluron, chloroxuron, Dimefuron, diuron, continuation ίο thiomeron, fenuron, fluometuron, iSOpr〇turon, isouron ), Hnuron, methabenzthiazuron, Moglong (m Etobromuron), metoxuron, monolinuron, neburon, siduron, tebuthiuron, propanil, pentanochlor ), bromofenoxim, bromoxynil, carbonisir (bentazon), pyridate and pyridafol. "AHAS inhibitor" (b2) a chemical compound that inhibits acetamidine synthase 2 〇 (AHAS), also known as acetolactate synthase (ALS), and thus inhibits branched aliphatic amino acids such as valine, The production of leucine and isoleucine kills plants. The aforementioned amino acids are required for DNA synthesis and cell growth. Examples of AHAS inhibitors include amidosulfuron and scorpion sacred 25 s Azimsulfuron), bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, sagitar 201240602 (cinosulfuron), cyclosulfamuron, ethametsulfuron -methyl), ethoxysulfuron, voltose (flazasulfuron), flupyrsulfuron-methyl (including sodium salt), foramsulfuron, halosulfuron-methyl, imazosulfuron, methyl magnetic continuation Iodosulfuron-methyl (including sodium salt), mesosulfuron-methyl, diether gas alpha than metazosulfuron, metsulfuron-methyl, and smoke Nicosulfuron), oxasulfuron, fluorine, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, jade Mimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl ), trifloxysulfuron (including sodium salt), triflusulfuron-methyl, tritosulfuron, imazapic, imazethide Imazamethabenz-methyl), 曱 oxygen 11 m grass smoke (imazamox), 灭Grass (imazapyr), imazaquin, imazethapyr, cloransulam-methyl, diclosulam, florasulam , ° sitting * &gt; flumetsulam, metosulam, penoxsulam, bispyribac-sodium, pyribenzoxim, vinegar Pyrifalid, pyrithiobac-sodium, pyriminobac-methyl, thiencarbazone, flucarbazone-sodium and propylbenzene (propoxycarbazone-sodium) ° "ACCase inhibitor" (b3) is a chemical compound that inhibits acetamidine c〇A carboxylase, which is responsible for the early steps in catalyzing the synthesis of a lipid and a fatty acid in plants. Lipids are essential components of cell rafts and cannot produce new cells without lipids. Inhibition of acetamidine CoA catalyzed enzymes and the lack of lipid production by them can result in loss of integrity of the cell membrane, particularly in active growth areas such as meristematic tissues. Eventually, the buds (sh〇〇t) and rhizome stopped growing, and the bud meristems and rhizome buds began to wither. Examples of ACCase inhibitors include ci〇dinafop, cyhalofop, did〇f〇p, fenoxaprop, fluazifop, aerated fluorine ( Hal〇xyf〇p), propaquizafop, quizal〇f〇p, alloxydim, butyl ketone (butr〇xydim), clethodix, Cydoxydim, pinoxaden, benzoquinone _ (pr〇f〇Xydim), sethoxydim, teprai〇xydim and tralkoxydim , including analytical forms such as fennelicide _p, voltazone _p, chlorofluoro-P and valprox-P, and ester forms such as propargyl acetyl oxalic acid, butyl 20 keisin, sulfhydryl Cao Ling and Ethyl Fenicide·ρ. &gt; Auxin is a plant hormone that regulates the growth of many plant tissues. The auxin mimetic (b4) is a chemical compound that mimics the auxin auxin, resulting in unregulated and chaotic growth, leading to the death of susceptible plant species. Examples of auxin mimetics include, but are not limited to, aminocyclopyrachlor, aminopyralid, benzazin Hn_ethyi, chlorampen 201240602 (chloramben), Kappa (ci〇mepr〇p), ci〇pyraiid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, A Chlorpropionic acid (mec〇pr〇p), mcpa, MCPB, 2,3,6-TBA, picloram, triclopyr, quinci〇rac and oxyquinoline (quinmerac). 10 20 "EPSP (5-enol-acetone oxalic acid_3_phosphate) synthase inhibitor" (b5) is a chemical compound that inhibits 5-enol-acetone shikimic acid_3_phosphate synthase It relates to the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. Epsp inhibitor herbicides are rapidly absorbed through the leaves of the plant and translocated at the bast to the point of growth. Glyphosate is a non-selective (n〇nsdective) post-emergence herbicide. Carbophosphonates include esters and salts such as ammonium salts, isopropylammonium salts, potassium salts, sodium salts (including sesquisodium) and trisylsulfate (tdmesium) (also known as sulforaphane). Sate)). solitary

光系統I電子轉向劑」(b6)為接受來自光系統I 之電子的化學化合物,並且在數個循環後產生羥基自由 基。這些自由基極具反應性並且迅速破壞不飽和脂質, 包括膜脂肪酸與葉綠素。此會破壞細胞膜完整性,因此 造成細胞與胞器滲漏,導致葉片快速凋萎與乾化,最終 4成植物死亡。此第二型光合成抑制劑的實例包括百草 枯(paraquat)與敵草快(diquat)。 PPO抑制劑」(b7)為抑制原紫元氧化酶之化學化 合物,其在植物中迅速導致高度反應性而會破壞細胞膜 之化合,的生成,造成細胞液漏失。PPO抑制劑的實例 包括亞吾芬鈉(acifluorfen_sodium)、;台草喊(bifem)x)、 121 25 201240602 曱氧基護谷(chlomethoxyfen)、乙幾·氟草醚 (fluoroglycofen_ethyl)、氟項胺草謎(fomesafen)、鹵胺草 醚(halosafen)、乳氟禾草靈(lactofen)、復祿芬 (oxyfluorfen)、異丙》比草酯(fluazolate)、0比草醚 10 15 20 (pyraflufen-ethyl)、吲哚酮草酯(cinidon-ethyl)、丙炔氟 草胺(flumioxazin)、氟烯草酸(flumiclorac-pentyl)、氟噻 曱草酯(fluthiacet-methyl)、代森環(thidiazimin)、樂滅草 (oxadiazon)、快噁草酮(oxadiargyl)、嘧啶肟草醚 (saflufencil)、草芬定(azafenidin)、唑草酮 (carfentrazone)、乙唑草酮(carfentrazone_ethy丨)、曱磺草 胺(sulfentrazone)、環戊惡草 _ (pent〇xazone)、雙苯 σ密草 酮(benzfendizone)、氟丙嘧草酯(butafenacil)、雙唑草腈 (pyraclonil)、氟唑草胺(pr〇fluaz〇1)與氟噠嗪草酯 (flufenpyr-ethyl)。 「GS (麵酿胺*合成酶)抑制劑」⑽)為抑制麵醯胺 酸合成酶活性之化學化合物,植_用簡將I轉化為 麩醯胺酸。因此,氨會累積而麩醯胺酸水準降低。 —* (phosphinothricin)衍生物、草録鱗 (bilanaphos) ° 氨毒性與其他代謝過程所需之胺基酸缺乏的纩人神 應,可能對植物造成傷害。…,劑包括;;膦 (gl—i她)與其醋及鹽如草銨膦銨鹽及 : fnhrKnliirmthriniri、么;丄·ι# 以. 叙單 與畢拉草 VLCFA (極長鏈脂肪酸)延長酶 有廣泛各式化學結構之除草劑’其抑制為具 為位於葉綠體中或附近之酶的苴中一酶。延長酶 —的生物合成。在植物中’極長鍵二酸其為= 122 25 201240602 性聚合物的主要成分’其防止葉片表面乾化並且為花粉 粒提供穩定性。此類除草劑包括乙草胺(acetochk)r)、拉 草(alachlor)、丁 基拉草(butachlor)、二甲草胺 (dimethachlor)、汰草滅(dimethanamid)、滅草胺 5 (metazachl〇r)、莫多草(metolachlor)、浠草胺 (pethoxamid)、普拉草(pretilachlor)、雷蒙得 (propachlor)、異丙草胺(pr〇pisochi〇r)、派羅克殺草硬 (pyroxasulfone)、欣克草(thenylchlor)、大芬滅 (diphenamid)、滅落脫(napr〇painide)、萘丙胺 ίο (naProanilide)、異口惡苯石風(fenoxasuif〇ne)、。塞草胺 (flufenacet)、扣卓酮(indanofan)、滅芬草(mefenacet)、 四嗤草胺(fentrazamide)、莎稗磷(anilofos)、苯酮唑 (cafenstrole)、β底草磷(piper〇ph〇s)包括經解析形式如s_ 莫多草與亂乙酿胺(chl〇r〇acetamide)與氧乙醯胺 15 (oxyacetamide) ° 「生長素傳輪抑制劑」(b 10)為抑制生長素在植物中 之傳輸的化學物質,諸如藉由與一生長素載體蛋白質結 合。生長素傳輸抑制劑的實例包括但不限於鈉得爛 (naptalam)(亦已知為沁(1•萘基)鄰胺曱醯苯甲酸與 20 2_[(1_萘基胺基)羰基]苯甲酸)與二氟《比隆 (diflufenzopyr) ° 「PDS (八氫番茄紅素去飽和酶抑制劑)」(bl 1)為抑 制八氫番#紅素去飽和酶步驟之類胡蘿蔔素生物合成 途徑的化學化合物。PDS抑制劑的實例包括氟草敏 25 (norflurzon)、吡氟草胺(diflufenican)、氟吡醯草胺 (picolmafen)、氟 丁草胺(beflubutamide)、氟咬草酮 123 201240602 (fluridone)、氟草 °比酮(flurochloridone)與咬草酮 (flurtamone) ° 「HPPD (4-羥苯基-丙酮酸-二氧合酶)抑制劑」(b 12) 為抑制4-羥基-苯基·丙酮酸-二氧合酶合成之生物合成 5 的化學物質。HPPD抑制劑的實例包括但不限於硝草酮 (mesotrione)、續草酮(sulcotrione)、苯 °比 σ坐草 _ (topramezone)、特夫三酮(tefuryltrione)、環續 g同 (tembotrione)、異 °惡氯草 _ (isoxachlortole)、異嗯唾草酉同 (isoxaflutole)、°比草 S同(benzofenap)、。比硫草酉同 ίο (pyrasulfatole)、苄草 〇坐(pyrazolynate)、普芬草 (pyrazoxyfen)、二環吡草酮(bicyclopyrone)與苯並雙環 西同(benzobicyclon) 〇 「HST」(黑尿酸%尼轉移酶)抑制劑(bl3)干擾植 物將黑尿酸轉化為2-甲基·6-茄尼基·ι,4_苯并_ 15 (2-methyl-6-solanyl-l,4-benzoquinone)的能力,從而干摄 類胡蘿蔔素生物合成。HST抑制劑的實例包括敦咬草 (haloxydine)、三氯吡啶酚(pyriclor)與式a、B與c之化 合物Photosystem I Electron Diverting Agent (b6) is a chemical compound that accepts electrons from photosystem I and produces hydroxyl radicals after several cycles. These free radicals are highly reactive and rapidly destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This will destroy the integrity of the cell membrane, thus causing leakage of cells and organelles, leading to rapid wilting and drying of the leaves, and eventually 40% of the plants die. Examples of this second type photosynthetic inhibitor include paraquat and diquat. The PPO inhibitor (b7) is a chemical compound which inhibits the proto-puron oxidase, which rapidly causes high reactivity in plants and destroys the formation of a combination of cell membranes, resulting in loss of cell fluid. Examples of PPO inhibitors include acifluorfen-sodium, bifem x, 121 25 201240602 chlomethoxyfen, fluoroglycofen_ethyl, flucarbazone Fomesafen, halosafen, lactofen, oxyfluorfen, isopropyl fluazolate, 0 oxalic acid 10 15 20 (pyraflufen-ethyl ), cinidon-ethyl, flumioxazin, flumiclorac-pentyl, fluthiacet-methyl, thidiazimin, Le Oxadizon, oxadiargyl, saflufencil, azafenidin, carfentrazone, oxazolone (carfentrazone_ethy丨), acesulfame ( Sulfentrazone), pent〇xazone, benzfendizone, butafenacil, pyraclonil, flurazepam 1) with flufenpyr-ethyl. "GS (facetamine * synthetase) inhibitor" (10)) is a chemical compound that inhibits the activity of the face glutamate synthase, and is converted to glutamic acid by a simple method. Therefore, ammonia will accumulate and the level of glutamic acid will decrease. —* (phosphinothricin) derivatives, bianaphos ° Ammonia toxicity and the lack of amino acids required for other metabolic processes should cause damage to plants. ..., the agent includes;; phosphine (gl-i her) and its vinegar and salt such as glufosinate ammonium salt and: fnhrKnliirmthriniri, 么; 丄·ι# to. 素单 and Bila grass VLCFA (very long chain fatty acid) elongase A herbicide having a wide variety of chemical structures is inhibited as an enzyme in the sputum having an enzyme located in or near the chloroplast. Prolong the enzyme - biosynthesis. In plants, 'very long bond diacids are = 122 25 201240602 main component of the polymer' which prevents the surface of the leaves from drying out and provides stability to the pollen grains. Such herbicides include acetochk r), alachlor, butachlor, dimethachlor, dimethanamid, and methamphetamine 5 (metazachl〇). r), metolachlor, pethoxamid, pretilachlor, propachlor, prasepisochi〇r, pyrocene Pyroxasulfone), thenylchlor, diphenamid, napr〇painide, naproanilide, fenoxasuif〇ne. Flufenacet, indanofan, mefenacet, fentrazamide, anilofos, cafenstrole, and piper Ph〇s) includes analytical forms such as s_ modal and chl〇r〇acetamide and oxyacetamide ° auxin inhibitor (b 10) for growth inhibition A chemical substance that is transmitted in a plant, such as by binding to an auxin carrier protein. Examples of auxin transport inhibitors include, but are not limited to, naptalam (also known as hydrazine (1 • naphthyl) o-amine benzoic acid and 20 2 —[(1-naphthylamino)carbonyl]benzene Formic acid) and difluoro "diflufenzopyr ° ° "PDS (octahydrolyser desaturase inhibitor)" (bl 1) is a carotenoid biosynthesis pathway for the inhibition of octahydroparaffin desaturase Chemical compound. Examples of PDS inhibitors include norflurzon 25, diflufenican, picolmafen, beflubutamide, flucarbazone 123 201240602 (fluridone), fluoride Flurochloridone and flurtamone ° "HPPD (4-hydroxyphenyl-pyruvate-dioxygenase) inhibitor" (b 12) to inhibit 4-hydroxy-phenyl-pyruvate - Chemical synthesis of biosynthesis 5 of dioxygenase synthesis. Examples of HPPD inhibitors include, but are not limited to, mesotrione, sulcotrione, benzene, topramezone, tefuryltrione, tembotrione, Isoxachlortole, isoxaflutole, benzofenap.硫 酉 酉 ί ί py py py py py py ο ο ο ο ο ο ο ο Inhibitors (bl3) interfere with plants to convert black uric acid to 2-methyl-6-solanyl-l,4-benzoquinone The ability to dry up for carotenoid biosynthesis. Examples of HST inhibitors include haloxydine, pyridol and compounds of formulas a, B and c.

HST抑制劑亦包括式D與E化合物 201240602HST inhibitors also include compounds of formula D and E 201240602

其中 Rdl 為 Η、Cl 或 CF3 ; Rd2 為 Η、Cl 或 Br ; Rd3 為 Η 或 Cl ; Rd4 為 Η、Cl 或 CF3 ; Rd5 為 CH3、CH2CH3 或 CH2CHF2 ;以及 Rd6 為 OH 或-OC(=〇)·卜Pr ;以及 為 Η、F、α、CH3 或 CH2CH3 ; Re2 為 H 或 CF3 ; Re3 為 Η、 CH3 或 CH2CH3 ; Re4 為 Η、F 或 Br ; Re5 為 c卜 CH3、 CF3、OCF3 或 CH2CH3 ; Re6 為 Η、CH3、CH2CHF2 或 OCH ; Re7 為 OH、-0C(=0)Et、-〇C(=〇H-Pr 或 -0C(=0)小Bu ;以及 Ae8 為 N 或 CH。 其他除草劑(bl4)包括經由各式不同作用模式作用 的除草劑’諸如有絲分裂干擾劑(例如高效麥草伏曱酯 (flamprop-M-methyl)與高效麥草伏丙酯 (flampiOp-M-isopropyi))、有機砷劑(例如 DSMA 與 MSMA)、7,8-二氫葉酸合成酶(7,8-dihydropteroate SynthaSe)抑制劑、葉綠體類異戊二烯(isoprenoid)合成抑 制劑與細胞壁生物合成抑制劑。其他除草劑包括具有未 知作用模式或不屬於(bl)至(M2)所列出之特定分類的 除草劑’或經由上列作用模式之組合而作用的除草劑。 其他除草劑的實例包括苯草醚(aclonifen)、亞速爛 125 201240602 (asulam)、殺草強(amitrole)、可滅蹤(domezone)、伏草 隆(fluometuron)、燕麥枯(difenzoquat)、溴布泰 (bromobutide)、抑草丁(flurenol)、環庚草醚 (cinmethylin)、苄草隆(cumyluron)、邁隆(dazomet)、汰 草龍(dymron)、甲基汰草龍(methyldymr〇n)、異噁噻草 醚(methiozolon)、艾分卡斑唑(ipfencarbazone)、乙氧苯 草胺(etobenzanid)、殺木膦(f0samine)、殺木膦銨 (fosamine-ammonium)、威百畝(metam)、噁嗪草酮 (oxaziclomefone)、油酸、壬酸與稗草畏(pyributicarb)。 「除草劑保護劑」(bl5)為添加至除草劑製劑中以消 除或減輕该除草劑對某些作物之植物毒性效果的物 質。這些化合物會保護作物免受除草劑傷害,但典型不 會防止該除草劑防治非所欲植物。除草劑保護劑的實例 包括但不限於草毒死(allidochlor)、解草嗓(benoxacor)、 1-溴-4-[(氣甲基)磺醯基]苯、解毒喹 (cloquintocet-mexyl)、苄草隆(cumyluron)、解草胺腈 (cyometrinil)、咬醯菌胺(Cyprosuifamide)、殺草隆 (daimuron)、二氣丙烯胺(dichlorniid)、二環隆酮 (dicyclonon)、4-(二氣乙醯基)·ι_氧雜·4_偶氮螺[4 5]癸烷 (ΜΟΝ 4660)、2-(二氣曱基)_2甲基-1,3-二氧雜環戊烷 (MG 191)、η底草丹(dimepiperate)、解草 β坐 (fenchlorazole-ethyl)、解草啶(fenci〇rim)、解草胺 (flurazole)、乱草肪(fluxofenim)、解草惡吐(furilazole)、 雙苯°惡β坐酸(isoxadifen-ethyl)、吐解草酯 (mefenpyr-diethyl)、美伏耐、苯草綱(meth〇xyphenone)、 萘二甲酸針與解草腈(oxabetrinil)。 126 201240602 以下如方案1至18中所述之一或多種方法及變型 可用於製備式1化合物。A、B1、B2、B3、R1、R2、R3、 1^4、115、1^、117、118、]19、1^、1112與1113在以下式1 至34化合物之定義係如以上發明内容中所定義者除 非另有註明。式la_lh化合物為式1化合物之子集合, 並且式la-lh之所有取代基係如以上針對式j所定義 者。 式la、lb或lc化合物(其中R3為羥基)可分別 經由方案1a、115與“所示之兩步驟方法製備。中間物 知、4b或4c可藉由使二酮2與中間物3 (其中Gl為一 親核反應脫離基者,例如Gi為一齒素、烷氧羰基、鹵 氧基鹵炫•氧幾氧基、β比咬基或咪u坐基(imidazoyl) 基團)反應而製備。使中間物4a、4b或4c與適當氰基 =合物(例如丙酮氰醇、氰化鉀、氰化鈉)於鹼如三乙 胺或吡啶存在下反應,生成一式la、lb或lc化合物。 或者一氟化物陰離子來源如氟化鉀或氟化铯(選擇性地 於相轉移催化劑如四丁基溴化銨等存在下)可用於此轉 ,。一溶劑如二甲亞砜、#,#·二甲基甲醯胺、乙腈或二 氣甲烷(在環境溫度至該溶劑之回流溫度)可生成一式 la、lb或ic化合物。(式la為其中a為a_i之式1 ; 式lb為其中A為A·2之式1 ;式lc為其中A為A-3 之式1 ° )或者’式la、lb或lc可藉由方法2 (分別 在方案la、11)與lc中)製備,此係藉由使二酮2a、2b 或€與中間物3於一氣基化合物或一氟化物陰離子來 源及一鹼存在下反應。關於此一般偶合方法之額外反應 條件’請參見Edmunds, A· in ⑽CVc?;?尸_論《 127 201240602Where Rdl is Η, Cl or CF3; Rd2 is Η, Cl or Br; Rd3 is Η or Cl; Rd4 is Η, Cl or CF3; Rd5 is CH3, CH2CH3 or CH2CHF2; and Rd6 is OH or -OC(=〇) · Pr; and Η, F, α, CH3 or CH2CH3; Re2 is H or CF3; Re3 is Η, CH3 or CH2CH3; Re4 is Η, F or Br; Re5 is c, CH3, CF3, OCF3 or CH2CH3; Re6 is Η, CH3, CH2CHF2 or OCH; Re7 is OH, -0C(=0)Et, -〇C(=〇H-Pr or -0C(=0) small Bu; and Ae8 is N or CH. Other weeding Agent (bl4) includes herbicides acting through various modes of action, such as mitotic disruptors (eg, flamprop-M-methyl and flampiOp-M-isopropyi), organically Arsenic agents (eg DSMA and MSMA), 7,8-dihydropteroate SynthaSe inhibitors, chloroplast isoprenoid synthesis inhibitors and cell wall biosynthesis inhibitors. Other weeding Agents include herbicides with unknown mode of action or specific classifications not listed in (bl) to (M2) or via the above listed mode of action Combining herbicides. Examples of other herbicides include alexifen, sub-altered 125 201240602 (asulam), amitrol (atomole), domezone, fluometuron, Difenzoquat, bromobutide, flurenol, cinmethylin, cumyluron, dazome, dymron, methyl Methyldymr〇n, methiozolon, ipfencarbazone, etobenzanid, f0samine, fosamine- Ammonium), metam, oxaziclomefone, oleic acid, citric acid and pyributicarb. "herbicide protectant" (bl5) is added to the herbicide preparation to eliminate or A substance that mitigates the phytotoxic effects of the herbicide on certain crops. These compounds protect crops from herbicides, but typically do not prevent the herbicide from controlling unwanted plants. Examples of herbicide protectants include, but are not limited to, allidochlor, benoxacor, 1-bromo-4-[(methylmethyl)sulfonyl]benzene, cloquintocet-mexyl, Cuyluron, cyometrinil, cyprosuifamide, daimuron, dichlorniid, dicyclonon, 4-(di) Gas oxime)·ι_oxater·4_azospiro[4 5]decane (ΜΟΝ 4660), 2-(di-mercapto)_2methyl-1,3-dioxolane ( MG 191), dimepiperate, fenchlorazole-ethyl, fenci〇rim, flurazole, fluxofenim, and grass vomiting Furilazole), isoxadifen-ethyl, mefenpyr-diethyl, mefrica, meth〇xyphenone, naphthalene dicarboxylic acid needle and oxabetrinil . 126 201240602 One or more of the methods and variations described below in Schemes 1 through 18 can be used to prepare a compound of Formula 1. A, B1, B2, B3, R1, R2, R3, 1^4, 115, 1^, 117, 118, ]19, 1^, 1112 and 1113 are defined in the following formulas 1 to 34 as in the above summary. Defined in the text unless otherwise stated. The compound of formula la-1h is a subset of the compound of formula 1, and all substituents of formula la-lh are as defined above for formula j. Compounds of formula la, lb or lc (wherein R3 is hydroxy) may be prepared via the two-step process shown in Schemes 1a, 115, respectively. Intermediates, 4b or 4c may be obtained by reacting diketone 2 with intermediate 3 (wherein Gl is prepared by nucleophilic reaction detachment, for example, Gi is a dentate, an alkoxycarbonyl group, a halooxyhalo-oxyoxy group, a β-bite group or an imidazoyl group. The intermediate 4a, 4b or 4c is reacted with a suitable cyano group (e.g., acetone cyanohydrin, potassium cyanide, sodium cyanide) in the presence of a base such as triethylamine or pyridine to form a compound of formula la, lb or lc. Alternatively, a source of a fluoride anion such as potassium fluoride or cesium fluoride (optionally in the presence of a phase transfer catalyst such as tetrabutylammonium bromide, etc.) can be used for this conversion. A solvent such as dimethyl sulfoxide, #,# • dimethylformamide, acetonitrile or di-methane (at ambient temperature to the reflux temperature of the solvent) to form a compound of formula la, lb or ic. (Formula la is a formula 1 wherein a is a_i; A is a formula of A.2; where lc is a formula in which A is A-3; or 'formula la, lb or lc can be obtained by method 2 (in each case) La, 11) and lc) are prepared by reacting a diketone 2a, 2b or an intermediate 3 with a gas-based compound or a monofluoride anion source and a base. Additional to this general coupling method Reaction conditions 'See Edmunds, A· in (10) CVc?; 尸 _ on 127 201240602

Compounds ; Kramer, W. and Schirmer, U.5 Eds. ; Wiley, Weinheim,2007; Chapter 4.3與其中所引用之參考文獻。 方案laCompounds; Kramer, W. and Schirmer, U.5 Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein. Scheme la

方案lb π ηScheme lb π η

3,氰基化合物或氟化物陰離子來源與鹼 ίο 方案lc rv r\3, cyano compound or fluoride anion source and base ίο scheme lc rv r\

3,氮基化合物或氟化物陰離子來源與鹼 式la、lb或lc化合物亦可如方案2中所示製備, 此係藉由使二酮2a、2b或2c與中間物3a於一鹼或路 128 201240602 易斯酸存在下反應。關於此一般偶合方法之反應條件, 請參見 Edmunds,A. in3. A source of a nitrogen-based compound or a fluoride anion and a compound of the formula la, lb or lc may also be prepared as shown in Scheme 2 by using a diketone 2a, 2b or 2c with an intermediate 3a in a base or a route. 128 201240602 Reaction in the presence of Lewis acid. For the reaction conditions for this general coupling method, see Edmunds, A. in

Compounds ; Kramer, W. and Schirmer, U., Eds. ; Wiley, Weinheim,2007; Chapter 4.3與其中所引用之參考文獻。 方案2Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein. Scenario 2

如方案3所示,中間物4a、4b或4c可藉由下列方 式製備,即使二酮2a、2b或2c與酸6於一脫水縮合劑 如2-氣·1·碳。比咬(亦稱為Mukaiyama偶合劑)、二環己 基碳二亞胺(DCC)或類似者存在下並且選擇性地於一鹼 存在下反應。關於此一般烯醇酯偶合方法之額外反應條 件,請參見Edmunds,A. in Crop尸⑺纪⑼⑽As shown in Scheme 3, the intermediate 4a, 4b or 4c can be produced by the following method, even if the diketone 2a, 2b or 2c and the acid 6 are in a dehydrating condensing agent such as 2-gas·1·carbon. It is reacted in the presence of a bite (also known as Mukaiyama coupling agent), dicyclohexylcarbodiimide (DCC) or the like and optionally in the presence of a base. For additional reaction conditions for this general enol ester coupling method, see Edmunds, A. in Crop (7) (9) (10)

Compounds ; Kramer, W. and Schirmer, U., Eds. ; Wiley, Weinheim,2007; Chapter 4.3與其中所引用之參考文獻。 方案3Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein. Option 3

R2 脫水縮合劑 4a,4b 或 4c 129 20 201240602 中間物4a、4b或4c亦可藉由使一式7化合物於二 酮2a、2b或2c存在下進行鈀催化羰基化反應而製得(方 案4)。關於此一般烯醇酯生成方法之額外反應條件, 請參見 Edmunds,A. in Crop Pro/eciiowR2 dehydrating condensing agent 4a, 4b or 4c 129 20 201240602 Intermediate 4a, 4b or 4c can also be obtained by palladium-catalyzed carbonylation of a compound of formula 7 in the presence of diketone 2a, 2b or 2c (Scheme 4) . For additional reaction conditions for this general enol ester formation process, see Edmunds, A. in Crop Pro/eciiow

Compounds ; Kramer, W. and Schirmer, U., Eds. ; Wiley,Compounds ; Kramer, W. and Schirmer, U., Eds. ; Wiley,

Weinheim,2007; Chapter 4.3與其中所引用之參考文獻。 方案4Weinheim, 2007; Chapter 4.3 and references cited therein. Option 4

式la、lb或lc化合物(其中r3係經由氧鍵結) 係藉由使式la、lb或lc化合物與中間物8 (其中X為 一親核反應脫離基,亦稱為一離核體(nucleofuge))於一 鹼存在下反應而製備,如方案5所示。或者,式la、 lb與lc化合物(其中R3係經由氮、硫或碳鍵結)可使 用適當il化劑接著進行親核加成而製備。關於此一般官 月&amp;化方法之反應條件’請參見Edmunds, A. or Almisick A. V. in Modern Crop Protection Compounds \ Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 or Chapter 4_4,與其中所引用之參考文獻。 201240602 1)鹵化劑 la,lb 或 lc R3係經由氮、 硫或碳而鍵結 2)親核劑A compound of formula la, lb or lc (wherein r3 is bonded via oxygen) by derivatizing a compound of formula la, lb or lc with an intermediate 8 (wherein X is a nucleophilic reaction, also referred to as a nucleofuge) )) Prepared by reaction in the presence of a base, as shown in Scheme 5. Alternatively, the compounds of formula la, lb and lc (wherein R3 is bonded via nitrogen, sulfur or carbon) can be prepared by subsequent nucleophilic addition using a suitable ilifying agent. For the reaction conditions of this general month &amp; method, see Edmunds, A. or Almisick AV in Modern Crop Protection Compounds \ Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 or Chapter 4_4, with references cited therein. 201240602 1) Halogenating agent la, lb or lc R3 is bonded via nitrogen, sulfur or carbon 2) nucleophile

方案5 X-R3 la,lb 或 lc —-~► 驗 R3 為 OH X 為 Cl, Br 或 I la,lb 或 lc R3係經由氧鍵結 如方案6所示,式Id化合物(即其中A為A-4與 R3為OH之式1)可藉由使中間物9與中間物3於一路 易斯鹼例如正丁基鋰或二異丙基醯胺鋰存在下在一適 當溶劑如四氳呋喃或二乙醚中反應而製備。關於此類轉 換之反應條件,請參見JP 2003327580。 10Scheme 5 X-R3 la, lb or lc —-~► Verify that R3 is OH X is Cl, Br or I la, lb or lc R3 is via an oxygen bond as shown in Scheme 6, a compound of formula I (ie where A is Formula 1) wherein A-4 and R3 are OH can be obtained by allowing intermediate 9 and intermediate 3 in the presence of a Lewis base such as n-butyllithium or lithium diisopropylamide in a suitable solvent such as tetrahydrofuran or Prepared by reaction in diethyl ether. See JP 2003327580 for reaction conditions for such conversions. 10

方案6Option 6

式le化合物(即其中A為A-5且R3為OH之式1) 15 可經由一兩步驟方法而製備,如方案7所示。中間物 12可藉由使吡唑11與中間物3(其中G1為一親核反應 脫離基,即G1為一鹵素原子、烷氧羰基、鹵烷羰氧基、 苯甲醯氧基、°比啶基或咪唑基基團)反應而製備。使中 簡物12與適當氰基化合物於一鹼存在下反應會生成一 2〇 式le化合物。或者,一式le化合物可藉由使中間物11 與中間物3 (方法2,方案7)於一氰基化合物或一氟 131 201240602 化物陰離子來源及一鹼存在下反應而直接製備。關於此 一般偶合方法之反應條件,請參見Almisick A. V. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4,與其中所引用之參考文獻。The compound of formula le (i.e., Formula 1 wherein A is A-5 and R3 is OH) can be prepared via a two-step process as shown in Scheme 7. The intermediate 12 can be deactivated by the pyrazole 11 and the intermediate 3 (wherein G1 is a nucleophilic reaction, that is, G1 is a halogen atom, an alkoxycarbonyl group, a halocarbonyloxy group, a benzamidineoxy group, a pyridine group) The base or imidazolyl group is prepared by reaction. Reaction of the intermediate product 12 with a suitable cyano compound in the presence of a base produces a compound of the formula le. Alternatively, a compound of the formula can be prepared directly by reacting the intermediate 11 with the intermediate 3 (Method 2, Scheme 7) in the presence of a cyano compound or a monofluoro 131 201240602 anion source and a base. For the reaction conditions of this general coupling method, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

丨R 2r 10 式If化合物(即其中A為A-5且R3係經由氧鍵結 之式1)可藉由使一式le與中間物8(其中X為一親核 反應脫離基,亦稱為離核體)於一鹼存在下反應而製 備,如方案8所示。或者,式If (其中R3係經由氮、 硫或碳鍵結)可使用適當鹵化劑接著進行親核置換而製 15 備。關於此一般官能化方法之反應條件,請參見The compound of the formula R 2r 10 (wherein A is A-5 and the R 3 is bonded via oxygen) can be obtained by deriving a formula le and an intermediate 8 (wherein X is a nucleophilic reaction, The core is prepared by reacting in the presence of a base, as shown in Scheme 8. Alternatively, Formula If (wherein R3 is bonded via nitrogen, sulfur or carbon) can be prepared by subsequent nucleophilic displacement using a suitable halogenating agent. For the reaction conditions of this general functionalization method, see

Almisick A. V. in Modern Crop Protection Compounds \ Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4,與其所引用之參考文獻。 132 201240602 方案8Almisick A. V. in Modern Crop Protection Compounds \ Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, references cited therein. 132 201240602 Option 8

R3係經由氮、 硫或碳而鍵結R3 is bonded via nitrogen, sulfur or carbon

式17化合物可藉由使中間物3與一式财一適當 溶劑中於-驗存在下反應而製備。因此中間物17可重 組為式lg化合物(即其中A為A_7之式1),此係於一 氰基化合物與一鹼存在下進行,如方案9所示。關於此 一般偶合方法之反應條件’請參見Almisick A. V. in Modern Crop Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4,與其中所引用之參考文獻。 方案9The compound of the formula 17 can be produced by reacting the intermediate 3 with a monovalent solvent in the presence of a solvent. Thus, the intermediate 17 can be recombined into a compound of the formula lg (i.e., Formula 1 wherein A is A_7), which is carried out in the presence of a cyano compound and a base, as shown in Scheme 9. For the reaction conditions of this general coupling method, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein. Option 9

式19化合物可由式lg之對應化合物(其中r〗3為 一烧氧叛基)於一酸如氣化氫、硫酸或乙酸存在下並且 選擇性地於一溶劑如四氫呋喃、二乙醚或二氣曱燒存在 20 下製備,如方案10所示。中間物19而後與一原曱酸酿 133 201240602 (orthoformate ester)或二曱基甲醯胺二甲縮酸 (DMF-DMA)於一酸存在下反應以獲得中間物20。使中 間物20與羥胺鹽酸鹽於一溶劑如乙醇、乙腈、水或乙 酸中反應,會提供式lh之異°惡°坐(isoxazole)化合物(即 5 其中A為A-6並且R11為Η之式1)。關於此一般環化 方法之反應條件,請參見Almisick A. V. in Μθί/erw Protection Compounds ; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim,2007; Chapter 4.4,與其中所引用 之參考文獻。 ίο 方案10The compound of the formula 19 can be obtained from the corresponding compound of the formula lg (wherein r is 3 a calcination group) in the presence of a monoacid such as hydrogenated hydrogen, sulfuric acid or acetic acid and optionally in a solvent such as tetrahydrofuran, diethyl ether or dioxane. The burn was prepared in the presence of 20 as shown in Scheme 10. The intermediate 19 is then reacted with an ortho-acidic acid 133 201240602 (orthoformate ester) or dimethylformamide (DMF-DMA) in the presence of a monoacid to obtain an intermediate 20. Reacting the intermediate 20 with hydroxylamine hydrochloride in a solvent such as ethanol, acetonitrile, water or acetic acid provides an isoxazole compound of the formula lh (i.e., 5 wherein A is A-6 and R11 is Η Equation 1). For reaction conditions for this general cyclization process, see Almisick AV in Μθί/erw Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein . Ίο Scheme 10

如方案11所說明’式1之亞砜與砜(其中R2為一 15 經由一亞砜或砜自由基鍵結之取代基)可藉由氧化式直 化合物(其中R為一經由一硫喊自由基鍵結之取代基) 而製備。在一典型製程中,根據所欲產物的氧化態;&quot;將 數量為1到4當量的氧化劑加入至溶於一溶劑中的式工 化合物溶液中。有用的氧化劑包括〇x〇ne® (過氧單硫 20 酸氫鉀)、過氧化氫、過碘酸鈉、過氧乙酸及3·氣過^ 苯曱酸。選擇的溶酬與使用的氧化劑有關。乙醇水溶 液或丙酮水溶液較佳為與過氧單硫酸氫鉀一起使用,/二 氣曱院則通常較佳為與3.氯過氧苯甲酸—起使用。有^ 134 201240602 的反應溫度通常在〇至9(TC之範圍。可用於將硫化物 氧化為亞砜與砜之特定程序係描述於Brand et 1 jgnc· C/^w· 1984, 32, 221-226 與其中所引用之參 考文獻。As described in Scheme 11, 'sulfoxide of formula 1 and sulfone (wherein R 2 is a substituent bonded via a sulfoxide or sulfone radical) can be oxidized by a straight compound (wherein R is a sulphur-free radical) Prepared by the substituent of the base bond). In a typical process, depending on the oxidation state of the desired product; &quot; an amount of 1 to 4 equivalents of the oxidizing agent is added to the solution of the compound compound dissolved in a solvent. Useful oxidizing agents include 〇x〇ne® (peroxymonosulfate potassium hydrogen hydride), hydrogen peroxide, sodium periodate, peracetic acid, and tris-benzoic acid. The choice of refining is related to the oxidant used. The aqueous ethanol solution or aqueous acetone solution is preferably used together with potassium peroxymonohydrogen monosulfate, and the second gas broth is usually preferably used in combination with 3. chloroperoxybenzoic acid. The reaction temperature of ^ 134 201240602 is usually in the range of 〇 to 9 (TC). The specific procedure used to oxidize sulfides to sulfoxides and sulfones is described in Brand et 1 jgnc· C/^w· 1984, 32, 221- 226 and references cited therein.

方案11Option 11

或硪而鍵結 熟省该項技術者會認知到,式3d之酿氣(即其中 10 G為C1之式3)可由式6之酸(方案12)藉由眾多熟 知的方法而輕易製備。例如使該酸與一氣化試劑如草醯 氯或亞硫醯氣在一溶劑如二氣甲烷或甲苯中並且選擇 性地於一催化量的二曱基曱醯胺存在下反應,可提 供式3d之對應醯氯。 15Alternatively, it will be appreciated that those skilled in the art will recognize that the brewing gas of Formula 3d (i.e., where 10 G is C1 Formula 3) can be readily prepared by a variety of well-known methods from the acid of Formula 6 (Scheme 12). For example, the acid can be reacted with a gasification reagent such as chloroform or sulfoxide in a solvent such as di-methane or toluene and optionally in the presence of a catalytic amount of dimethyl decylamine to provide Formula 3d. Corresponding to chlorine. 15

氩化劑 方案12Argonizer Scheme 12

3d 式6化合物可由式23之酯藉由眾多熟知的方法(例 如使用鹼水溶液如u〇H、Na〇H或K〇H之標準皂化程 序)在一溶劑如甲醇或乙醇中而製備,如方案13所述。 135 20 201240602 或者,可於一鹼存在下在一溶劑如吡啶或乙酸乙酯中使 用一去院化劑如埃化經或三f石夕蜗。用於去酯化之額外 反應程序可發現於PCT專利公開案第WO 2006/133242 號中。或者可使用三溴化硼(ΒΒγ3)在一溶劑如二氣甲烷 5 中以由一式23化合物製備一式6化合物。使用三溴化 硼之程序可發現於历⑻rg. ά MW. 2009, 19(16),4733-4739。 方案13 0 0 6 L^™SI Aik. 1 或 ΒΒγ3 An-r, MOH 鹼 ] C人2 -► 溶劑 6 10 Aik為C丨-06烷基 23 M 為 Li,Na 或 Κ 15 式23a之嘧啶酮酯(即其中Aik為乙基,χ為CH 並且Y為C(O)之式23)係如方案14中所說明者製備, 此係藉由使式26之対酮與藥劑如院基函化物進行沁 烷化反應,並且於一鹼如氫化鈉或碳酸鉀存在下在一溶 劑如—曱基曱酿胺、四氫咬喃或二乙趟中進行。 Ο 03d The compound of formula 6 can be prepared from the ester of formula 23 by a number of well-known methods (for example using standard aqueous saponification procedures such as u〇H, Na〇H or K〇H) in a solvent such as methanol or ethanol, as in the scheme 13 stated. 135 20 201240602 Alternatively, a de-farming agent such as Aihua or Sanf can be used in the presence of a base in a solvent such as pyridine or ethyl acetate. Additional reaction procedures for deesterification can be found in PCT Patent Publication No. WO 2006/133242. Alternatively, boron tribromide (??) can be used to prepare a compound of formula 6 from a compound of formula 23 in a solvent such as dioxane methane 5. The procedure using boron tribromide can be found in calendar (8) rg. ά MW. 2009, 19(16), 4733-4739. Scheme 13 0 0 6 L^TMSI Aik. 1 or ΒΒγ3 An-r, MOH base] C person 2 -► Solvent 6 10 Aik is C丨-06 alkyl 23 M is Li, Na or Κ 15 Pyridine of formula 23a Ketoesters (i.e., formula 23 wherein Aik is ethyl, hydrazine is CH and Y is C(O)) are prepared as described in Scheme 14, by making the fluorenone of formula 26 and the agent The compound is subjected to a decaneization reaction and is carried out in the presence of a base such as sodium hydride or potassium carbonate in a solvent such as hydrazine, tetrahydroanion or diethyl hydrazine. Ο 0

方案14 0 〇Option 14 0 〇

R1 R2 提供R1 之坑化劑 鹼、溶劑 式23a之嘴咬酮酿可藉由方案15之方法而製得。 在此方法中’將—式28之丙二酸亞曱酯(methylene 136 20 201240602 malonate)以一式29之脒鹽(其中χ為一鹵素或磺酸鹽 相對離子)於過剩驗如燒氧化納或碳酸卸存在下在一適 當溶劑如乙醇中環化(通常在該溶劑之回流溫度),以 k供式3f之對應部咬目同。此合成方法之實例係記述於 PCT專利公開案第WO 2006/133242號與⑽ 2001, 57, 2689 中。 C02Et EtO^jjA^COjEt 28 + 方案15R1 R2 provides the pitting agent of R1. Alkali Solvents of the formula 23a can be obtained by the method of Scheme 15. In this method, 'methylene 136 20 201240602 malonate' is a salt of the formula 29 (wherein the hydrazine is a halogen or a sulfonate relative ion) in excess of the test such as sodium oxide or The cyclization in a suitable solvent such as ethanol in the presence of carbonic acid (usually at the reflux temperature of the solvent) is the same as the counterpart of formula 3f. Examples of such synthetic methods are described in PCT Patent Publication Nos. WO 2006/133242 and (10) 2001, 57, 2689. C02Et EtO^jjA^COjEt 28 + Scheme 15

Rk,人 X N 、NH Η 29 ΗΧ 鹼、溶劑 23a 15 式26之嘧啶_酯可藉由方案16之方法而製得。在 此方法中,,將-式28之丙二酸伸乙酯(ethyiene malonate)以-式29a之脒鹽(其巾χ為一函素或續酸 鹽相對離子)於過嶋城氧仙或碳酸鉀存在下在一 適^溶劑Μ料環化(通常在該溶劑之喊溫度), 之對應嘧啶酮。此合成程序之實例係記述 知專利公開案第wo 2006/133242號與巧⑽ 2001,57, 2689 中。 方案16 + R2 29a 驗、溶劑 137 26 28 201240602 式23-X1之嘧啶酮酯可藉由方案17之方法轉換為 式23-X3與23-X4之嘧啶酮酯。在此方法中,23-X1係 與一酸如HC1或H2S04在一非質子性溶劑如二噁烷 (dioxane)或一質子性溶劑如甲醇或乙醇中在介於0°C與 5 該溶劑沸點間之溫度接觸,以產出式23-X2之醛或酮。 接著或同時,式23-X2之醛或酮可與經取代之羥胺或肼 於一酸催化劑如HC1或H2S04存在下在一非質子性溶 劑如二噁烷或一質子性溶劑如甲醇或乙醇中在介於〇°C 與該溶劑沸點間之溫度接觸,以產出式23-X3與23-X4 ίο 化合物,其可進一步以方案1 - 16所述之方法進行反 應。熟習該項技術者會認知到,圖23-X2之醛與酮可藉 由化學文獻中已知的各式方法進一步轉化為許多其他 官能基。 方案17 0 0 0 0Rk, human X N , NH Η 29 ΗΧ base, solvent 23a 15 The pyrimidine ester of formula 26 can be obtained by the method of Scheme 16. In this method, the ethyiene malonate of the formula 28 is obtained by the sulfonium salt of the formula 29a (the scorpion is a physin or a sulphonate relative ion) In the presence of potassium carbonate, it is cyclized in a suitable solvent (usually at the temperature of the solvent), corresponding to pyrimidinone. An example of such a synthetic procedure is described in the patent publications No. WO 2006/133242 and Qiao (10) 2001, 57, 2689. Scheme 16 + R2 29a, solvent 137 26 28 201240602 The pyrimidone ester of formula 23-X1 can be converted to the pyrimidone ester of formula 23-X3 and 23-X4 by the method of Scheme 17. In this method, the 23-X1 system is combined with an acid such as HCl or H2S04 in an aprotic solvent such as dioxane or a protic solvent such as methanol or ethanol at a temperature between 0 ° C and 5 The temperature is contacted to produce an aldehyde or ketone of the formula 23-X2. Next or simultaneously, the aldehyde or ketone of formula 23-X2 can be combined with a substituted hydroxylamine or a hydrazine catalyst such as HCl or H2S04 in an aprotic solvent such as dioxane or a protic solvent such as methanol or ethanol. Contact is made at a temperature between 〇 ° C and the boiling point of the solvent to yield compounds of the formula 23-X3 and 23-X4 ί, which can be further reacted as described in Schemes 1-16. Those skilled in the art will recognize that the aldehydes and ketones of Figure 23-X2 can be further converted to a number of other functional groups by various methods known in the chemical literature. Option 17 0 0 0 0

23-X3 23-X4 15 式29之脒可依據許多方法由式29X之胺與式29Y 之腈製備,包括但不限於描述於下列文獻中者: 138 20124060223-X3 23-X4 15 The formula 29 can be prepared from the amine of the formula 29X and the nitrile of the formula 29Y according to a number of methods including, but not limited to, those described in the following literature: 138 201240602

European Patent Application EP 80592; J. Org. Chem. 2010, 75, 945-947 &gt; Chemistry - A European Journal 2009, 15, 7292-7296; Organic Process Research &amp; Development 2008, U 1201-1208 ; Og. I故,2008,川,445-448。European Patent Application EP 80592; J. Org. Chem. 2010, 75, 945-947 &gt; Chemistry - A European Journal 2009, 15, 7292-7296; Organic Process Research & Development 2008, U 1201-1208 ; Og. I Therefore, 2008, Sichuan, 445-448.

、nh2 29X,nh2 29X

方案18 R2‘N - 29YOption 18 R2‘N - 29Y

N HN H

2929

NH 人們會認知到,上述用於製備式1化合物的一些試 10 劑及反應條件可能與某些存在於中間物的官能基不相 容。在這些例子中,將保護/去保護序列或官能基相互 轉換結合至該合成中,將有助於獲得所欲產物。該保護 基的使用及選擇對於熟習化學合成之人士將是顯而易 見的(請參見如 Greene, T_ W.; Wuts,P. G. M. iVoiecizve 15 Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991)。熟習該項技術者會認知到,在一些情況下,在 引入一特定試劑(如同在任何個別方案中所述者)後, 其可能必須進行未詳述之額外常規步驟以完成式t之 合成。熟習s亥項技術者亦會認知到,可能必須以不同於 2〇 所呈現之特定順序所意味的次序,來進行以上方案中所 說明步驟之組合以製備式1化合物。 熟習該項技術者亦會認知到,式1化合物與本文中 所述之中間物可經過各式親電子、親核、自由基、有機 139 201240602 f、氧化與還原反應以加人取代基或修飾現有取代 基0 即使沒有進-步的_,相信使用 5 15 域具有通常知識者仍能夠最大程度地利用ί發日Γ因 二以I實㈣為綱之用,於限制本發明之 揭路内谷。下列實例的步驟說明一整體合 驟的-種程序’且用於每個步驟的起始材料不必缺需J ί由一歡製備性試絲製備,該特定製触試驗的程 序係描述於其他實例或步驟中。百分比為以重量計,除 了層析溶航合物或另有指明者j麵職出,則層 析溶劑混合物係赠積份及_百分比計。加廬光 譜係以在CDC13中偏移自四甲基残且在锡_之 低場ppm來記述,除非另有註日月;「s」意指單峰,「m」 意指多峰’「br s」意指寬單峰,「d」意指雙峰,「如」 意指雙雙峰,「t」意指三峰,「td」意指三雙峰,「出」 意指雙三峰而「q」意指四峰。 實例1 3-(1,4-二氧雜螺[4.5]癸冬基)_5_[(2_經基_6_側氧基小環己稀 小基)羰基]-2-苯基_4(3/f&gt;嘧啶酮(化合物丨)的製備 步驟 A · 1-(1,4_二氧雜螺[4.5]癸-8-基)-1,6·二氫-6-側 氧基-2-苯基-5-嘧啶羧酸甲酯的製備 於本甲亞胺酸乙g旨鹽酸鹽(ethy丨benzimidate hydrochloride) (l.i g,5.9 mmol)(溶於 15 ml 的甲醇) 中加入込4-二氧雜-螺[4.5]癸-8-基胺(1.0 g,6.8 mmol)。 將混合物在環境溫度攪拌16小時,之後加入25% w/w 201240602 的甲氧鈉(1.3 g,6.1 mmol)溶液,並且持續擾拌20分 鐘。將混合物濃縮至乾燥,並且將殘餘二氧雜螺 [4.5]癸-8-基苯幾酿亞胺醢胺鹽酸鹽 (7V-1,4-dioxaspiro[4.5]dec-8-ylbenzenecarboximidamide 5 hydrochloride)懸浮於20 ml乙腈中,並且以二曱基甲氧 基丙二酸亞甲酯(dimethyl methoxymethylenemalonate) (1.13 g,6.5 mmol)處理,接著以 dbu (0.9 g,5.9 mmol) 處理。將反應混合物回流16小時,之後在減壓下濃縮 並以中壓液相層析術(在石夕膠上’以3〇〇/〇至1〇〇〇4在己 10 炫中之乙酸乙醋洗提)純化’以提供1.2 g呈油液的標 題化合物。 lH NMR (CDC13) δ 8.61 (d, 1H), 7.49-7.61 (m, 3 H), 7.42-7.48 (m,2H),3.98-4.08 (m,ih),3.86-3.94 (m, 7H), 3.09 (m,2H),1.76 (d, 2H), 1.64 (d,2H), 1.27-1.34 (m, 15 2H)。 ’ 步驟B : 1-(1,4-二氧雜螺[4 5]癸各基)_16_二氮各側 氧基-2-苯基-5-嘧啶羧酸的製備 於(1-(1,4-二氧雜螺[4.5]癸基)_16_二氮各側氧 20 基苯基-5_嘧啶羧酸曱酯(實例1,步驟A之產物)(0.40 g,1.1 mmol)在10 m丨乙酸乙酯中之溶液中加入碘化鋰 (0.43 g,3 _2 mmol)。將反應混合物回流丨6小時而後冷卻 至環境溫度並以水_ 〇以1Ν Ηα使混合物成為酸性 並以乙酸乙酯萃取二次。而後以1N Na〇H萃取合併之 25 有機層。以濃縮HC1使所得水性層成為酸性並以二氣甲 201240602 烧萃取三次。而後以MgS〇4乾燥合併之有機層、過濾、 並在減壓下濃縮以產出0.39 g呈固體之標題化合物。 lU NMR (CDCI3) δ 8.95 (s, 1H), 7.59 (m, 3H), 7.51 (s, 2H), 4.19 (m, 1H), 3.99 (s, 2H), 3.92 (s, 2H), 3.06 (m, 5 2H),1.82 (d, 2H),1.73 (d,2H),1.34 (m,2H)。 步驟C : 3-(1,4-二氧雜螺[4·5]癸-8-基)-5-[2-羥基-6-側 氧基小環己烯-1-基]羰基]-2-苯基-4(3H)-嘧 啶酮(化合物1)的製備 ίο 將1-(1,4-二氧雜螺[4.5]癸-8-基)_1,6·二氫-6-側氧基 -2-苯基-5-嘧啶羧酸(實例1,步驟b之產物)(0.39 g,1.1 mmol)在10 ml二氣甲烷中之溶液以草醯氣(196μ1,2.3 mmol)與1滴况,二曱基曱醯胺處理。將反應攪拌1小 時而後濃縮並再度溶於10 ml二氣曱烷中。將1,3-環己 15 二酮(0.14 g,1.2 mmol)與三乙胺(310 μΐ,2.2 mmol)加入 並將反應混合物在環境溫度攪拌20分鐘,而後以額外 三乙胺(310 μΐ,2.2 mmol)接者以2滴丙酮氰醇處理。將 反應混合物在環境溫度攪拌丨6小時而後在減壓下濃 縮,並以中壓液相層析術(在矽膠上,以〇%至3%在氯 20 仿中之甲醇)純化以產出0.060 g的標題化合物,即一 本發明之化合物。 ]H NMR (CDCI3) δ 16.58 (s, 1H), 7.98 (s5 1H), 7.50 (m, 5H), 3.99 (s, 1H), 3.89 (m, 4H), 2.95 (d, 2H), 2.72 (t, 2H), 2.50 (m, 2H), 2.08 (m5 2H), 1.72 (m, 4H)S 1.29 (m, 25 2H)。 142 201240602 實例2 5-[(2-羥基-6-側氧基_ι·環己烯小基)羰基]_6_側氧基_2•苯基 _1(6//)-鳴咬乙醛丨_(〇-甲基肟)(化合物2)的製備 步驟A : Ν·(2,2·二曱氧乙基)苯羰醯亞胺醯胺 5 (N-(2,2-dimethoxyethyl)benzenecarboximida mide)的製備 將曱氧納(0.75 g, 14.56 mmol)在氮氣氛中在室溫分 批加入至苯曱腈(15.0 g,145.6 mmol)在 MeOH (150 mL) 中之經攪拌溶液中並攪拌12小時。將乙酸(0.5 mL)加 10 入,將所得混合物攪拌20分鐘,接著加入2,2_二曱氧 乙胺(18.34 g, 174.75 mmol) 〇將反應混合物攪拌整夜, 在減壓下濃縮’將殘餘物溶於二氣甲烷中並以水洗滌。 將有機層乾燥並在減壓下濃縮以提供呈白色固體之標 題化合物(15.5 g)。 15 lH NMR (CDC13) δ 7.49-7.61 (m, 5H), 4.64 (m, 1H), 3.55 (m,2H),3.44 (s,6H)。 步驟B : 1_(2,2-二曱氧乙基)·ι,6_二氫_6·側氧基_2·苯 基-5-喊咬叛酸曱醋的製備 20 於Ν_(2,2·二甲氧乙基)苯碳亞胺醯胺(15 g5 72.1 mmol)在乙腈(150 mL)中之經攪拌溶液中加入甲氧基亞 甲基丙二酸二曱基酯(dimethyl methoxymethylenemelonate) (13.8 g, 79·3 mmol)接著加 入DBU (3.28 g,21.6 mmol)。將反應混合物在i20°C加 25 熱6小時’冷卻至室溫並在減壓下濃縮。以管柱層析術 143 201240602 (60〇/〇在己院中之乙酸乙醋)純化殘餘物以提供標題產 物(6 g)。 ]H NMR (CDC13) δ 8.73 (s, 1H), 7.49-7.57 (m, 5H), 4.87 (m,1H),4·16 (m, 2H),3.94 (s,3H),3.3! (s,6H)。 步驟C : 二氫小[2-(甲氧亞胺基)乙基]_6•側氧基 -2-苯基-5-嘧啶羧酸甲酯的製備 於1-(2,2-二甲氧乙基;H,6-二氫側氧基_2_苯基_5_ 嘧啶羧酸甲酯(3.5 g,11.0 mmol)在乙醇(1〇 mL)中之經 擾拌/谷液中加入催化量的對甲苯確酸與鄰甲基經胺鹽 酸鹽(2.0 g,24.2 mmol)。將反應混合物加溫以回流4小 時而後在減壓下濃縮。將殘餘物溶於二 中並簡和賴氫麟摩mL_ 15 (MgS04)並在減壓下濃、缩,並且以管柱層析術(励%在 己烧中之㈣乙自旨)純化殘餘物以提供標題產物(1 〇g)。 H NMR (CDCI3) δ 8.65 (s, 1Η), 7.40-7.51 (m, 5H), 6.72 (m, 1H), 4.73 (m5 1H), 4.61 (m5 1H), 3.86 (s, 3H), 3.72 (s,3H) 〇 2〇 步驟D . l6-:氫·1识曱氧亞胺基)乙基]-6-側氧基 苯基-5-嘧啶羧酸的製備 於丨,6-二氫小[2-(甲氧亞胺基)乙基]_6_側氧基_2_苯 f ·5·喊錢酸甲_.8 g,2.6 m_在乙酸乙醋(10 mL) 之=攪拌溶液中加入蛾化轉⑽g,6 6麵。丨)。將反 25 =&amp;物加溫以喊並_4小時。將反應混合物濃縮 ?餘物洛於水中,並且加入1N鹽酸直到= 4, 201240602 而後以二氣甲烷(100 mL)萃取。將有機層乾燥(MgS04) 並在減壓下濃縮以提供呈白色固體之標題化合物(0.7 g)。 巾 NMR (CDC13) δ 8.93 (s,1H),7.45-7.55 (m,5H), 5 6.72 (m, 1H),4.84 (m,1H), 4.22 (m,1H), 3.68 (s,3H)。 步驟E: 3-側氧基-1-環己烯-1-基1,6-二氫-丨-[2-(甲氧 亞胺基)乙基]6-側氧基-2-苯基-5·β密咬緩酸 酯的製備 1〇 於16-二氫小[2-(甲氧亞胺基)乙基]-6-側氧基-2-苯 基-5-嘧啶羧酸(〇·25 g, 0.87 mmol)在二氣甲烷(1〇 mL)中 之經攪拌溶液中加入沁曱基2-氯碘吡啶(A^methyl 2-chloropyridimnium iodide) (0.33 g,1.3 mmol)並將所得 混合物在室溫攪拌15分鐘。將環己二酮(〇,14 g,1 3 15 mmo1)接著三乙胺(0.21 g,2.17 mmol)加入並將反應混合 物在室溫攪拌12小時。以二氣甲烷(30 mL)稀釋反應混 合物並以冰水(20 mL)洗滌,將二氣甲烧層分開並以鹽 水(20mL)洗滌,以MgS〇4乾燥並在減壓下濃縮,並以 管柱層析術(75%在己烷中之乙酸乙酯)純化殘餘物以提 2〇 供標題化合物(0·2 g)。LCMS: 382 (M +1) 〇 步驟F : 5-[(2-經基-6-側氧基-1-環己缚-1-基)幾基]_6_ 側氧基-2-苯基-1(6//)-喊咬乙酸 1·(〇_甲基肪) 的製備 25 於側氣基小壤己歸-1-基1,6-二氮-1-[2·(曱氧亞胺 基)乙基]-6-側氧基-2-苯基-5-嘧啶羧酸酯(0.2 g,0.52 145 201240602 mmol)在乙腈(5 mL)中之經攪拌溶液中加人三乙胺(〇 〇7 g,0.78mmol)’接著加入丙_氰醇(3滴,⑽)並在室 溫攪拌6小時。在減壓下濃縮反應現合物並以氣化甲院 (30 mL)稀釋殘餘物並以水(20 mL)洗滌。以MgS〇4乾燥 5 二氣甲烧層並在減壓下濃縮’並且以管柱層析術(100% 在己院中之乙酸乙S旨)純化殘餘物以提供標題化合物 (20 mg)。 *HNMR(CDC13) 6 8.93 (s, IH), 7.45-7.59 (m, 5H) 6.68 (m, 1H),4.70 (m,1H),4.57 (m,1H),3.68 (s,3H): io 2.96 (m, 2H), 2.49 (m, 2H),0.94 (m,2H)。 ’ 實例3 2-環丙基-5-[(2-羥基·6·側氧基小環己烯小基)羰基]_3_(4_嗎 啉基)·4(3//)·嘧啶g同(化合物22)的製備 15 步驟A : 2·環丙基-1,6-二氫小(4·嗎啉基)_6_側氧基_5_ σ 密咬叛酸甲酯 將尽胺基嗎啉(1.37 g,13.4 mmol)加入至環丙基醯 亞胺乙酯(ethyl cyclopropylimidate)鹽酸鹽(2.〇 g ^ 4 mmol)在甲醇(19 mL)中之溶液中,而後將其在室溫攪拌 2〇 16小時。將甲氧鈉溶液(25%w/w在甲醇中,3 18g, 14.7 mmol)加入並將溶液攪拌30分鐘。將溶液在真空 中濃縮並溶於乙腈(20 mL)。將二甲基甲氧基丙二酸^ 甲酯(2.56 g, 14.7 mmol)與 1,8-二氮雙環[5.4.0]十一_7_ 稀(0.83 g,5.3 mmol)加入並將混合物加熱以回流4小 25 時,之後在減壓下濃縮並以中壓液相層析術(在石夕膠 201240602 上’以0至100%在己烷中之乙酸乙酯)以提供114 g 呈黃色油液的標題化合物。 !H NMR (500 MHz) δ ppm 8.46 (s, 1H), 4.31 (td, 2H)? 3.97 (m, 2H), 3.89 (s, 3H), 3.71 (td, 2H), 2.97 (m, 5 1H),2 83 (m, 2H),1.25 (s,2H),1.17 (m, 2H)。 步驟B : 2-環丙基-1,6-二氫_ι·(4_嗎啉基)_6_側氧基_5· 嘧啶羧酸的製備 將2-環丙基-1,6-二氫-1-(4-嗎啉基)-6-側氧基-5-嘧啶 1〇 鲮酸酯(即來自步驟A之產物)(i_i4g,4.1 mmol)溶於 乙腈(2%水,以體積計)並以溴化鋰(粉末,丨77 g, 20.4 mmol)與三乙胺(0.63 g,6.1 mmol)處理,並在常溫 授拌16小時。以鹽酸水溶液(1N,2〇niL)稀釋粗反應混 合物並以二氯甲烷(2 X 40 mL)萃取水性層◊將有機層合 15 併、乾燥(Na2S〇4)、過濾並在減壓下濃縮,生成0.942 g 呈白色固體的標題化合物。 NMR (500 MHz) δ ppm 12.68 (br s, 1H), 8.71 (s, 1H),4.25 (td,2H),4.02 (m,2H),3.74 (d,2H),3.02 (m, 1H),2.91 (m, 2H),1.34 (d,2H),1.27 (d,2H)。 20 步驟C : 2-環丙基-5-[(2-羥基_6_側氧基小環己烯小基) 羰基]-3-(4-嗎啉基)_4(3//)-嘧啶酮(化合物 22)的製備 於2-環丙基-1,6-二氫·1·(4·嗎啉基側氧基-5-嘧啶 25 叛酸(即來自步驟Β之產物)(0.5 g,1.9 mmol)(在6 mL 一氣甲院中)中加入2-氣-1-曱基硤比咬(θ α g, 2 8 147 201240602 mmol)與環己二酮(0.32 g,2.8 mmol)。將三乙胺(〇48 g 4.7 mmol)逐滴加入並將溶液在A氣氛中攪拌16小時。 而後以一氣甲烧(50 mL)稀釋溶液並以蒸館水與鹽水洗 滌。將有機層乾燥(NaAO4)、過濾並在真空中濃縮。使 5 粗材料通過石夕膠塞過濾並以乙酸乙醋洗提。在真空中濃 縮有機層。將粗材料置於乙腈(10 mL)與2-羥基-2-曱基_ 丙腈(0_015 g,0.15 mmol)中並且將三乙胺(0 48 g,47 mmol)加入。將溶液在環境溫度攪拌16小時。而後在減 壓下濃縮反應混合物並以中壓液相層析術(在碎膠上, ίο 以〇至在二氣曱烧中之甲醇洗提)純化以提供〇 95 g 呈固體之標題化合物。 咕 NMR (500 ΜΗζ) δ ppm 16.47 (s,1H),7.88 (s 1H), 4.19 (m, 2H), 3.95 (dd5 2H), 3.71 (m, 2H), 2.94 (m 1H), 2.87 (d, 2H), 2.69 (t, 2H), 2.48 (t, 2H), 2.06 (m, 2H), 15 1.22 (m, 2H),1.12 (m,2H)。 ’ 實例4 2-環丙基-5_[(2_羥基-4-側氧基雙環[3 2 辛_2_烯_3_基)羰 基]士(4-嗎啦基)-4(3咖密啶_(化合物23)的製備 20 釋A: 2_環丙基_5低輕基-4-側氧基雙環[3.2.1]辛 稀3基)&amp;基]-3-(4-嗎琳基)-4(3//)-嘴咬酮 (化合物23)的製備 於2-環丙基-1,6-二氫-κ⑷嗎淋基)_6_側氧基·5_嚷咬 羧酸(即來自實例3,步驟Β之產物)(〇 5 g,i 9咖 μ (在6灿二氯甲射)中加入2-氣-i-甲基心比咬(〇 72 g,2.8 mmol)與雙環[3.2·η辛烷_24_二酮(〇39 g, 201240602 mmol)。將二乙胺(〇 48 g,4.7 mmol)逐滴加入並將溶液 在氮氣氛下攪拌16小時。而後以二氣曱烷(5〇mL)稀釋 溶液並以蒸餾水與鹽水洗滌。將有機層乾燥(Na2S〇4)、 過濾並在真空中濃縮。使粗材料通過矽膠塞過濾並以乙 5 酸乙酯洗提。在真空中濃縮有機層。將粗材料置於乙腈 (10 mL)與2-羥基-2·甲基-丙腈(0 015 g,〇 15 mm〇i)中並 且將三乙胺(0.481 g, 4.7 mmol)加入。將溶液在環境溫度 攪拌16小時。而後在減壓下濃縮反應混合物並以中壓 液相層析術(在矽膠上,以〇至5〇/〇在二氯曱烷中之甲 10 醇洗提)純化以提供0.199 g呈固體之標題化合物。 lU NMR (500 MHz) δ ppm 16.64 (s, 1H), 7.82 (s, 1H), 4.21 (m, 2H), 3.96 (dd, 2H), 3.71 (m, 2H), 3.07 (m5 1H), 2.93 (m, 2H), 2.88 (d, 2H), 2.22 (d, 1H), 2.13 (m, 2H), 2.00 (m, 1H), 1.85 (m, 1H), 1.71 (m, 1H), 1.20 (m, is 2H),1.11 (m, 2H)。 藉由本文中所述程序以及該技術中習知的方法,可 製備出下列表1到表12的化合物。下列縮寫係用於表 中如下:Me意指曱基,Et意指乙基,n-Pr意指正丙基, z’-Pr意指異丙基,c-Pr意指環丙基,《-Bu意指正丁基, 20 /-Bu意指異丁基,s-Bu意指二級丁基,c-Bu意指環丁 基,/-Bu意指三級丁基,《-pent意指正戊基,c-Pent意 指環戊基,《-Hex意指正己基,hept意指庚基,c-Hex 意指環己基,Ph意指苯基,OMe意指曱氧基,OEt意 指乙氧基,SMe意指甲硫基,SEt意指乙硫基’ thp意 25 指四氫0底0南,thtp 意指四氫硫0辰喃 (tetrahydrothiopyran),thf 意指四氫吱喃,-CN 意指氰 149 201240602 基,-N02意指硝基,S(0)Me意指甲亞磺醢基,S02意 指磺醯基並且S(0)2Me意指甲磺醯基。 表1NH will recognize that some of the above-mentioned reagents and reaction conditions for the preparation of the compound of formula 1 may be incompatible with certain functional groups present in the intermediate. In these examples, the incorporation of a protecting/deprotecting sequence or functional group into the synthesis will aid in obtaining the desired product. The use and selection of such protecting groups will be readily apparent to those skilled in the art of chemical synthesis (see, e.g., Greene, T_W.; Wuts, P. G. M. iVoiecizve 15 Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). Those skilled in the art will recognize that, in some instances, after introducing a particular reagent (as described in any of the individual schemes), it may be necessary to perform additional conventional steps not detailed to complete the synthesis of formula t. Those skilled in the art will also recognize that a combination of the steps set forth in the above schemes may be carried out in an order different from that which is presented in a particular order to produce a compound of formula 1. Those skilled in the art will also recognize that the compounds of Formula 1 and the intermediates described herein can undergo various types of electrophilic, nucleophilic, free radical, organic 139 201240602 f, oxidation and reduction reactions to add human substituents or modifications. Existing substituents 0, even if there is no further step-by-step, it is believed that those who have the usual knowledge of using the 5 15 domain can still make the best use of the fact that I use the real (four) as the key to limit the invention. Valley. The steps of the following examples illustrate an overall procedure - and the starting materials for each step are not necessarily required to be prepared by a preparative test strip, the procedure of which is described in other examples. Or step. Percentages are by weight, except for the chromatographic solution or otherwise indicated, the solvent mixture is given as a percentage and percentage. The twisted spectrum is described as offset from the tetramethyl residue in CDC13 and in the low field ppm of tin, unless otherwise noted; "s" means a single peak and "m" means a multi-peak '" "br s" means wide single peak, "d" means double peak, "如" means double peak, "t" means three peaks, "td" means triplet, "out" means double triple and " q" means the four peaks. Example 1 3-(1,4-Dioxaspiro[4.5]anthracene)_5_[(2_carbyl-6-o-oxycyclohexanyl)carbonyl]-2-phenyl_4 ( 3/f&gt; Preparation of pyrimidinone (compound oxime) Step A · 1-(1,4-dioxaspiro[4.5]dec-8-yl)-1,6-dihydro-6-sideoxy-2 Preparation of methyl phenyl-5-pyrimidinecarboxylate 込4 was added to ethy丨benzimidate hydrochloride (li g, 5.9 mmol) (dissolved in 15 ml of methanol). - Dioxa-spiro[4.5]dec-8-ylamine (1.0 g, 6.8 mmol). The mixture was stirred at ambient temperature for 16 h then added 25% w/w 201240602 of sodium methoxide (1.3 g, 6.1 mmol The solution, and continued to scramble for 20 minutes. The mixture was concentrated to dryness, and the residual dioxaspiro[4.5]dec-8-ylbenzene succinimide hydrochloride (7V-1,4-dioxaspiro [ 4.5] dec-8-ylbenzenecarboximidamide 5 hydrochloride) was suspended in 20 ml of acetonitrile and treated with dimethyl methoxymethylenemalonate (1.13 g, 6.5 mmol) followed by dbu (0.9 g) , 5.9 mmol) treatment. The reaction mixture was refluxed for 16 hours before decompression Concentrate and purify by medium pressure liquid chromatography (extracted from 3 〇〇 / 〇 to 1 〇〇〇 4 in acetonitrile in acetonitrile) to provide 1.2 g of oil The title compound. lH NMR (CDC13) δ 8.61 (d, 1H), 7.49-7.61 (m, 3 H), 7.42-7.48 (m, 2H), 3.98-4.08 (m, ih), 3.86-3.94 (m , 7H), 3.09 (m, 2H), 1.76 (d, 2H), 1.64 (d, 2H), 1.27-1.34 (m, 15 2H). 'Step B: 1-(1,4-Dioxaspiro) [4 5 ] 癸 ) ) _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Addition of lithium iodide to each of the dioxo-oxo 20-phenyl-5-pyrimidinecarboxylate (Example 1, product of Step A) (0.40 g, 1.1 mmol) in 10 mL of ethyl acetate (0.43) The reaction mixture was refluxed for 6 hours and then cooled to ambient temperature. The combined 25 organic layers were then extracted with 1N Na〇H. The resulting aqueous layer was made acidic by concentration of HC1 and was extracted three times with a second gas 201240602. The combined organic layers were dried with EtOAc (EtOAc)EtOAc. lU NMR (CDCI3) δ 8.95 (s, 1H), 7.59 (m, 3H), 7.51 (s, 2H), 4.19 (m, 1H), 3.99 (s, 2H), 3.92 (s, 2H), 3.06 ( m, 5 2H), 1.82 (d, 2H), 1.73 (d, 2H), 1.34 (m, 2H). Step C: 3-(1,4-Dioxaspiro[4·5]indole-8-yl)-5-[2-hydroxy-6-oxooxycyclohexen-1-yl]carbonyl]- Preparation of 2-phenyl-4(3H)-pyrimidinone (Compound 1) ίο 1-(1,4-Dioxaspiro[4.5]癸-8-yl)_1,6·dihydro-6-side A solution of oxy-2-phenyl-5-pyrimidinecarboxylic acid (Example 1, product of step b) (0.39 g, 1.1 mmol) in 10 mL of di-methane methane (1⁄4, 2.3 mmol) Drip conditions, dimercaptoamine treatment. The reaction was stirred for 1 hour and then concentrated and re-dissolved in 10 mL of dioxane. 1,3-Cyclohexyl 15dione (0.14 g, 1.2 mmol) and triethylamine (310 μM, 2.2 mmol) were added and the reaction mixture was stirred at ambient temperature for 20 min then with additional triethylamine (310 μM, 2.2 mmol) was treated with 2 drops of acetone cyanohydrin. The reaction mixture was stirred at ambient temperature for 6 hours and then concentrated under reduced pressure and purified by medium pressure liquid chromatography (on a silica gel, 〇% to 3% methanol in chloro 20) to yield 0.060. The title compound of g, a compound of the invention. ]H NMR (CDCI3) δ 16.58 (s, 1H), 7.98 (s5 1H), 7.50 (m, 5H), 3.99 (s, 1H), 3.89 (m, 4H), 2.95 (d, 2H), 2.72 ( t, 2H), 2.50 (m, 2H), 2.08 (m5 2H), 1.72 (m, 4H)S 1.29 (m, 25 2H). 142 201240602 Example 2 5-[(2-Hydroxy-6-oxooxy_ι·cyclohexene small)carbonyl]_6_sideoxy_2•phenyl_1(6//)-biting acetaldehyde Preparation of 丨_(〇-methyloxime) (Compound 2) Step A: 2·(2,2·Dioxaxyethyl)phenylcarbonylindolamine 5 (N-(2,2-dimethoxyethyl)benzenecarboximida Preparation of mide) Deuterium (0.75 g, 14.56 mmol) was added portionwise to a solution of benzoquinone (15.0 g, 145.6 mmol) in MeOH (150 mL) and stirred in a nitrogen atmosphere at room temperature and stirred. 12 hours. Acetic acid (0.5 mL) was added and the mixture was stirred for 20 min, then 2,2-dioxyethylamine (18.34 g, 174.75 mmol) was added and the mixture was stirred overnight and concentrated under reduced pressure. The residue was dissolved in di-methane and washed with water. The organic layer was dried <RTI ID=0.0> 15 lH NMR (CDC13) δ 7.49-7.61 (m, 5H), 4.64 (m, 1H), 3.55 (m, 2H), 3.44 (s, 6H). Step B: Preparation of 1_(2,2-dioxaxyethyl)·ι,6-dihydro-6·sideoxy-2·phenyl-5-spoken bite tartare vinegar 20 Ν Ν(2, 2. Dimethoxyethyl) phenylcarbimimine decylamine (15 g5 72.1 mmol) in acetonitrile (150 mL) was added to a stirred solution of dimethyl methoxymethylenemelonate. (13.8 g, 79·3 mmol) followed by DBU (3.28 g, 21.6 mmol). The reaction mixture was heated to 25 °C for 6 hours at i20 ° C and cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; ]H NMR (CDC13) δ 8.73 (s, 1H), 7.49-7.57 (m, 5H), 4.87 (m, 1H), 4·16 (m, 2H), 3.94 (s, 3H), 3.3! (s , 6H). Step C: Preparation of methyl dihydro[2-(methoxyimino)ethyl]-6•oxo-2-phenyl-5-pyrimidinecarboxylate in 1-(2,2-dimethoxy Ethyl; H,6-dihydro-oxyl-2-phenyl-5-pyrimidinecarboxylate methyl ester (3.5 g, 11.0 mmol) in ethanol (1 mL) p-Toluene acid and o-methyl-amine hydrochloride (2.0 g, 24.2 mmol). The reaction mixture was warmed to reflux for 4 hours and then concentrated under reduced pressure. The residue was purified by column chromatography (M.sub.2) (m.). NMR (CDCI3) δ 8.65 (s, 1Η), 7.40-7.51 (m, 5H), 6.72 (m, 1H), 4.73 (m5 1H), 4.61 (m5 1H), 3.86 (s, 3H), 3.72 (s ,3H) 〇2〇Step D. l6-: Hydrogen·1 曱 曱 oxyimino)ethyl]-6-oxophenyl-5-pyrimidinecarboxylic acid was prepared in ruthenium, 6-dihydrogen small [ 2-(methoxyimino)ethyl]_6_sideoxy_2_benzene f ·5· shout acid A.8 g, 2.6 m_ in acetic acid ethyl acetate (10 mL) = stirring solution Add moth to (10) g, 6 6 faces.丨). Heat the anti 25 =&amp; to shout and _4 hours. The reaction mixture was concentrated. The residue was taken from water, and then 1N hydrochloric acid was added until </ RTI> 4, 201240 602 and then extracted with di-methane (100 mL). The organic layer was dried (MgSO4). NMR (CDC13) δ 8.93 (s, 1H), 7.45-7.55 (m, 5H), 5 6.72 (m, 1H), 4.84 (m, 1H), 4.22 (m, 1H), 3.68 (s, 3H) . Step E: 3-Sideoxy-1-cyclohexen-1-yl 1,6-dihydro-indole-[2-(methoxyimino)ethyl]6-oxo-2-phenyl -5·Preparation of β-Carmeline Acidate 1〇16-Dihydro-sodium [2-(methoxyimino)ethyl]-6-oxooxy-2-phenyl-5-pyrimidinecarboxylic acid ( 〇·25 g, 0.87 mmol) A 2-methylpyridinium iodide (0.33 g, 1.3 mmol) was added to a stirred solution of di-methane (1 mL) and The resulting mixture was stirred at room temperature for 15 minutes. Cyclohexanedione (〇, 14 g, 1 3 15 mmol) followed by triethylamine (0.21 g, 2.17 mmol) was added and the mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with EtOAc (EtOAc) (EtOAc)EtOAc. The residue was purified by column chromatography (EtOAc EtOAc) LCMS: 382 (M +1) 〇 Step F: 5-[(2-amino-6-o-oxy-1-cyclohexan-1-yl)-yl]-6- oxo-2-phenyl- Preparation of 1(6//)- shouting acetic acid 1·(〇_Methyl fat) 25 in the side gas-based small soil, -1-yl 1,6-diaza-1-[2·(曱氧亚Amino)ethyl]-6-oxo-2-phenyl-5-pyrimidinecarboxylate (0.2 g, 0.52 145 201240602 mmol) in triethylamine in acetonitrile (5 mL) (〇〇7 g, 0.78 mmol) ' Then cyanohydrin (3 drops, (10)) was added and stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure and the residue was evaporated and evaporated. The residue was purified by EtOAc (EtOAc): *HNMR(CDC13) 6 8.93 (s, IH), 7.45-7.59 (m, 5H) 6.68 (m, 1H), 4.70 (m, 1H), 4.57 (m, 1H), 3.68 (s, 3H): io 2.96 (m, 2H), 2.49 (m, 2H), 0.94 (m, 2H). 'Example 3 2-Cyclopropyl-5-[(2-hydroxy·6· pendant oxy small cyclohexene small)carbonyl]_3_(4-morpholinyl)·4(3//)·pyrimidine g Preparation of (Compound 22) 15 Step A: 2·Cyclopropyl-1,6-dihydro-small (4·morpholinyl)_6_sideoxy_5_ σ Methylene-based morpholine (1.37 g, 13.4 mmol) was added to a solution of ethyl cyclopropylimidate hydrochloride (2. 〇g^4 mmol) in methanol (19 mL) and then at room temperature Stir for 2 to 16 hours. A solution of sodium methoxide (25% w/w in methanol, 3 18 g, 14.7 mmol) was added and the solution was stirred for 30 min. The solution was concentrated in vacuo and dissolved in EtOAc (20 mL). Methyl dimethyl methoxymalonate (2.56 g, 14.7 mmol) and 1,8-diazabicyclo [5.4.0] eleven _7_ dilute (0.83 g, 5.3 mmol) were added and the mixture was heated After refluxing for 4 hours, it was concentrated under reduced pressure and was subjected to medium pressure liquid chromatography (on 0 to 100% ethyl acetate in hexane on 201240602) to provide 114 g of yellow. The title compound of the oil. !H NMR (500 MHz) δ ppm 8.46 (s, 1H), 4.31 (td, 2H)? 3.97 (m, 2H), 3.89 (s, 3H), 3.71 (td, 2H), 2.97 (m, 5 1H ), 2 83 (m, 2H), 1.25 (s, 2H), 1.17 (m, 2H). Step B: Preparation of 2-cyclopropyl-1,6-dihydro-ι·(4-morpholinyl)-6-sideoxy-5-pyrimidinecarboxylic acid 2-Cyclopropyl-1,6-di Hydrogen-1-(4-morpholinyl)-6-oxo-5-pyrimidine monodecanoate (ie product from step A) (i_i4g, 4.1 mmol) dissolved in acetonitrile (2% water in volume) It was treated with lithium bromide (powder, 丨77 g, 20.4 mmol) and triethylamine (0.63 g, 6.1 mmol), and was stirred at room temperature for 16 hours. The crude reaction mixture was diluted with aq. EtOAc (EtOAc (EtOAc) (EtOAc (EtOAc) Yield 0.942 g of the title compound as a white solid. NMR (500 MHz) δ ppm 12.68 (br s, 1H), 8.71 (s, 1H), 4.25 (td, 2H), 4.02 (m, 2H), 3.74 (d, 2H), 3.02 (m, 1H), 2.91 (m, 2H), 1.34 (d, 2H), 1.27 (d, 2H). 20 Step C: 2-cyclopropyl-5-[(2-hydroxy-6-oxyl small cyclohexene small) carbonyl]-3-(4-morpholinyl)-4(3//)-pyrimidine Preparation of a ketone (Compound 22) in 2-cyclopropyl-1,6-dihydro·1·(4·morpholinyloxy-5-pyrimidine 25 tarenic acid (ie from the product of the step) (0.5 g , 1.9 mmol) (in 6 mL of a gas hospital) was added 2-gas-1-mercaptopyrene (θ α g, 2 8 147 201240602 mmol) and cyclohexanedione (0.32 g, 2.8 mmol). Triethylamine (〇48 g 4.7 mmol) was added dropwise and the solution was stirred for 16 hours in atmosphere A. The solution was then diluted with a gas (50 mL) and washed with brine and brine. NaAO 4), filtered and concentrated in vacuo. The crude material was filtered and washed with ethyl acetate. The organic layer was concentrated in vacuo. The crude material was placed in acetonitrile (10 mL) and 2-hydroxy- 2-mercapto-propanenitrile (0-015 g, 0.15 mmol) and triethylamine (0 48 g, 47 mmol) was added. The solution was stirred at ambient temperature for 16 h. Pressure liquid chromatography (on the broken glue, ίο to the second gas smoldering Purification by alcohol elution to provide the title compound as a solid. NMR (500 ΜΗζ) δ ppm 16.47 (s, 1H), 7.88 (s 1H), 4.19 (m, 2H), 3.95 (dd5 2H), 3.71 (m, 2H), 2.94 (m 1H), 2.87 (d, 2H), 2.69 (t, 2H), 2.48 (t, 2H), 2.06 (m, 2H), 15 1.22 (m, 2H), 1.12 (m, 2H). 'Example 4 2-Cyclopropyl-5_[(2-hydroxy-4-oxobicyclo[3 2 oct-2-ene]-3-yl)carbonyl](4- morphaki Preparation of 4-(3-camididine-(Compound 23) 20 Release A: 2_cyclopropyl-5 low-oxyl-4-oxobicyclo[3.2.1]octyl 3) &amp; Preparation of -3-(4-morphinyl)-4(3//)-mouth ketone (Compound 23) in 2-cyclopropyl-1,6-dihydro-κ(4) hydrazino)_6_ side oxygen ·5_嚷 bit carboxylic acid (ie from the product of Example 3, step )) (〇5 g, i 9 咖μ (in 6 candichloromethane) added 2-gas-i-methyl heart than bite (〇72 g, 2.8 mmol) with bicyclo [3.2·n-octane_24_dione (〇39 g, 201240602 mmol). Diethylamine (〇48 g, 4.7 mmol) was added dropwise and the solution was applied to nitrogen Stir for 16 hours under the atmosphere. The solution was then diluted with dioxane (5 〇 mL) and washed with distilled water and brine. The organic layer was dried (Na2SO 4) filtered and concentrated in vacuo. The crude material was filtered through a pad of Celite and eluted with ethyl acetate. The organic layer was concentrated in vacuo. The crude material was taken up in acetonitrile (10 mL) and 2-hydroxy-2-methyl-propanenitrile (0 015 g, 〇 15 mm 〇i) and triethylamine (0.481 g, 4.7 mmol) was added. The solution was stirred at ambient temperature for 16 hours. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography (eluent eluted with hydrazine to 5 〇 / 甲 in methylene chloride in dichloromethane) to provide 0.199 g as solid. Title compound. lU NMR (500 MHz) δ ppm 16.64 (s, 1H), 7.82 (s, 1H), 4.21 (m, 2H), 3.96 (dd, 2H), 3.71 (m, 2H), 3.07 (m5 1H), 2.93 (m, 2H), 2.88 (d, 2H), 2.22 (d, 1H), 2.13 (m, 2H), 2.00 (m, 1H), 1.85 (m, 1H), 1.71 (m, 1H), 1.20 ( m, is 2H), 1.11 (m, 2H). The compounds of Tables 1 to 12 below can be prepared by the procedures described herein and by methods well known in the art. The following abbreviations are used in the table: Me means thiol, Et means ethyl, n-Pr means n-propyl, z'-Pr means isopropyl, c-Pr means cyclopropyl, "-Bu Means n-butyl, 20 /-Bu means isobutyl, s-Bu means secondary butyl, c-Bu means cyclobutyl, /Bu means tributyl, "-pent means n-pentyl c-Pent means cyclopentyl, "-Hex means n-hexyl, hep means heptyl, c-Hex means cyclohexyl, Ph means phenyl, OMe means decyloxy, OEt means ethoxy, SMe Is a nail thiol, SEt means ethylthio 'thp meaning 25 means tetrahydro 0 bottom 0 south, thtp means tetrahydrothiopyran, thf means tetrahydrofuran, -CN means cyanide 149 201240602, -N02 means nitro, S(0)Me means sulfinyl, S02 means sulfonyl and S(0)2Me means sulfonyl. Table 1

R2 為 PhR2 is Ph

201240602201240602

R1 R1 R1 ΓΛ ΓΛ ΓΛ S. NH '(CH2)2 h 、S NH (CH2)3 h 、s (CH2)4 h ΓΛ ΓΛ ΓΛ 、〇 NH ch2、ch3 、〇 NH (CH2)2 CHi 、0 NH (CH〇)^ CH-i r\ r\ ΓΛ 0 NH (ch2)4、ch3 、S NH ch2、ch3 (ch2)2、ch3 ΓΛ 、s測 (ch2)3、ch3 ΓΛ 、sXm (ch2)4、ch3 /CH3 、〇X〇 、ch2 h /CH3 ΓΛ 、X〇 (CH2)2 h /CH3 、°x〇 ^2)3 H /ch3 、°x〇 /CH3 、sxs 、ch2 h /CH3 \SXS ^2)2 H /CH3 、sxs /CH3 \SXS ^2)4 H 尸3 r\ 、X〇 ch2 ch3 /CH3 (ch2)2、ch3 /CH3 r\ 尸3 /~\ /CH3 ΓΛ 、X (CH2&gt;3、ch3 、〇X〇 (CH2)4、ch3 、sxs ch2、ch3 /CH3 (CH2)2XCH3 ch3 /ch3 (CH2CXCH3 h3c ΓΛ h3c /~~\ h3c ΓΛ 、0 KH ch2 h 、〇 NH (CH2)2 h 、0 NH (CH2)3 H 151 201240602R1 R1 R1 ΓΛ ΓΛ ΓΛ S. NH '(CH2)2 h , S NH (CH2)3 h , s (CH2)4 h ΓΛ ΓΛ 〇 , 〇 NH ch2, ch3 , 〇NH (CH2)2 CHi , 0 NH (CH〇)^ CH-i r\ r\ ΓΛ 0 NH (ch2)4, ch3, S NH ch2, ch3 (ch2)2, ch3 ΓΛ, s test (ch2)3, ch3 ΓΛ, sXm (ch2)4 , ch3 /CH3, 〇X〇, ch2 h /CH3 ΓΛ , X〇(CH2)2 h /CH3 , °x〇^2)3 H /ch3 , °x〇/CH3 , sxs , ch2 h /CH3 \SXS ^2)2 H /CH3 , sxs /CH3 \SXS ^2)4 H Corpse 3 r\ , X〇ch2 ch3 /CH3 (ch2)2, ch3 /CH3 r\ Corpse 3 /~\ /CH3 ΓΛ , X ( CH2&gt;3, ch3, 〇X〇(CH2)4, ch3, sxs ch2, ch3 /CH3 (CH2)2XCH3 ch3 /ch3 (CH2CXCH3 h3c ΓΛ h3c /~~\ h3c ΓΛ , 0 KH ch2 h , 〇NH (CH2 ) 2 h , 0 NH (CH2)3 H 151 201240602

R1 R1 R1 h3c r\ 、0 NH (CH2)4 h H3C S NH 、ch2 h h3c 、S NH nTch2)TS'h h3c 、S NH '(CH2CSH h3c S NH ^ch2)T^h H3C ΓΛ 、0 NH ch2 、ch3 H3C ΓΛ H3Cv f\ H3Cv f\ 、0 NH (ch2)2、ch3 、0 NH (ch2)3、ch3 0 NH (ch2)4、ch3 h3c NH CH2 CH3 H3C 、SQh (ch2)2、ch3 H3C (ch2)3、ch3 h3c 、S NH /CH3 /( 、0xm ch2 h /CH3 、0 NH /CH3 (CH2)3 h /CH3 、0 NH /CH3 /( 、s π ch2 h yCH3 S NH /CH3 /( 、S NH (CH2)3 h /CH3 、S NH ^2)4 H /CH3 、0 NH ch^^ch3 /CH3 /( 、0 NH (CH2)2、ch3 /CH3 、0 NH vTch2^sch3 yCH3 /( (CH2)4、ch3 /CH3 ri CH2 CH3 yCH3 、S NH 152 201240602 R1 R1 R1R1 R1 R1 h3c r\ , 0 NH (CH2)4 h H3C S NH , ch2 h h3c , S NH nTch2)TS'h h3c , S NH '(CH2CSH h3c S NH ^ch2)T^h H3C ΓΛ , 0 NH Ch2, ch3 H3C ΓΛ H3Cv f\ H3Cv f\ , 0 NH (ch2)2, ch3, 0 NH (ch2)3, ch3 0 NH (ch2)4, ch3 h3c NH CH2 CH3 H3C, SQh (ch2)2, ch3 H3C (ch2)3, ch3 h3c, S NH /CH3 /( , 0xm ch2 h /CH3 , 0 NH /CH3 (CH2)3 h /CH3 , 0 NH /CH3 /( , s π ch2 h yCH3 S NH /CH3 /( , S NH (CH2)3 h /CH3 , S NH ^2)4 H /CH3 , 0 NH ch^^ch3 /CH3 /( , 0 NH (CH2)2, ch3 /CH3, 0 NH vTch2^sch3 yCH3 /( (CH2)4, ch3 /CH3 ri CH2 CH3 yCH3 , S NH 152 201240602 R1 R1 R1

-(CH2)2CH=NOH -ch2c(ch3)=noh-(CH2)2CH=NOH -ch2c(ch3)=noh

-(CH2)4C(CH3)=NOH -(CH2)4CH=NOCH3-(CH2)4C(CH3)=NOH -(CH2)4CH=NOCH3

-(CH2)3C(CH3)=NOH -(CH2)3CH=NNH2 -(ch2)2c(ch3)=nnh2 -(CH2)2CH=NNHCH3 -CH2C(CH3)=NNH2-(CH2)3C(CH3)=NOH -(CH2)3CH=NNH2 -(ch2)2c(ch3)=nnh2 -(CH2)2CH=NNHCH3 -CH2C(CH3)=NNH2

•(ch2)4c(ch3)=nnh2 -(CH2)2C(CH3)=NOH -(CH2)2CH=NOCH3 •ch2c(ch3)=noch3• (ch2)4c(ch3)=nnh2 -(CH2)2C(CH3)=NOH -(CH2)2CH=NOCH3 •ch2c(ch3)=noch3

-(CH2)4C(CH3)=NOH »(CH2)4CH=NNH2 -(CH2)3C(CH3)=NNH2 •(ch2)3ch=nnhch3 -(CH2)2C(CH3)=NNH2 -(CH2)2CH=NN(CH3)2-(CH2)4C(CH3)=NOH »(CH2)4CH=NNH2 -(CH2)3C(CH3)=NNH2 •(ch2)3ch=nnhch3 -(CH2)2C(CH3)=NNH2 -(CH2)2CH= NN(CH3)2

-(CH2)4CH=NOH-(CH2)4CH=NOH

-(CH2)3C(CH3)=NOH -(CH2)3CH=NOCH3 -(ch2)2c(ch3)=noh -(CH2)2CH=NNH2 -CH2C(CH3)=NNH2 -(CH2)4C(CH3)=NNH2 -(CH2)4CH=NNHCH3 -(CH2)3C(CH3)=NNH2 -(CH2)3CH=NN(CHj)2 153 201240602 R1 R1 R1 -(CH2)4CH=NN(CH3)2 -CH2C(CH3)=NN(CH3)2 -(CH2)2C(CH3)=NN(CH3)2 -(CH2&gt;3C(CH3)=NN(CH3)2 -(CH2)3C(CH3)=NN(CH3)2 •(ch2)4c(ch3)=nn(ch3)2 -(CH2)2CH=NS02CH3 •(ch2)3ch=nso2ch3 -(CH2)4CH=NS02CH3 -CH2C(CH3)=NS〇2CH3 -(ch2)2c(ch3)=nso2ch3 -(CH2)3C(CH3)=NS02CH3 -(ch2)4c(ch3&gt;=nso2ch3 *(CH2)2CH=NCOCH3 -(CH2)3CH=NCOCH3 -(CH2)4CH=NCOCH3 -CH2C(CH3)=NCOCH3 *(CH2)2C(CH3)=NCOCH3 -(CH2)3C(CH3)=NCOCH3 •(ch2)4c(ch3)=ncoch3 -ch=chch2ch=noch3 -(CH2)2CH=CHCH=NOCH3 -ch2ch=chc(ch3)=noch3 -(CH2)2ch=CHC(CH3)=NOCH3 -ch2conh2 -(CH2)2CONH2 -(CH2)3CONH2 -ch2conhch3 -(CH2)3CONHCH3 -ch2con(ch3)2 -(CH2)2CON(CH3)2 -(ch2)3con(ch3)2 -ch2coch3 -(CH2)2COCH3 -(CH2)3COCH3 -ch2coch2ch3 -(CH2)2COCH2CH3 -(ch2)3coch2ch3 -(CH2)2OCH2CN •(ch2)3och2cn _(ch2)2och2conh2 -ch2och2conh2 -&lt;^y^=NOH —^&gt;=noch3 —^^&gt;=NOCH2CH3 -\=NNH2 —&lt;^^=nnhch3 —&lt;^&gt;=nnhch2ch3 —&lt;^&gt;=NN(CH3)2 —&lt;(^&gt;=nso2ch3 —\=ncoch3 NOH NOCH3 NOCH2CH3 nnh2 ^nnhch3 nnhch2ch3 、nn(ch3)2 /—\ nso2ch3 厂 V ^ncoch3 -( V=NOH —ί \=noch3 -( \=NOCH2CH3 —1 \=nnh2 —〈 ^=nnhch3 —〈 nnhch2ch3 —&gt;=nn(ch3)2 —〈^=nso2ch3 —〈 ^=ncoch3 麵 \ V=noch3 ^ NOCH2CH3 154 201240602 R1 R1 R1-(CH2)3C(CH3)=NOH -(CH2)3CH=NOCH3 -(ch2)2c(ch3)=noh -(CH2)2CH=NNH2 -CH2C(CH3)=NNH2 -(CH2)4C(CH3)= NNH2 -(CH2)4CH=NNHCH3 -(CH2)3C(CH3)=NNH2 -(CH2)3CH=NN(CHj)2 153 201240602 R1 R1 R1 -(CH2)4CH=NN(CH3)2 -CH2C(CH3) =NN(CH3)2 -(CH2)2C(CH3)=NN(CH3)2 -(CH2&gt;3C(CH3)=NN(CH3)2 -(CH2)3C(CH3)=NN(CH3)2 •( Ch2)4c(ch3)=nn(ch3)2 -(CH2)2CH=NS02CH3 •(ch2)3ch=nso2ch3 -(CH2)4CH=NS02CH3 -CH2C(CH3)=NS〇2CH3 -(ch2)2c(ch3) =nso2ch3 -(CH2)3C(CH3)=NS02CH3 -(ch2)4c(ch3&gt;=nso2ch3 *(CH2)2CH=NCOCH3 -(CH2)3CH=NCOCH3 -(CH2)4CH=NCOCH3 -CH2C(CH3)=NCOCH3 *(CH2)2C(CH3)=NCOCH3 -(CH2)3C(CH3)=NCOCH3 •(ch2)4c(ch3)=ncoch3 -ch=chch2ch=noch3 -(CH2)2CH=CHCH=NOCH3 -ch2ch=chc( Ch3)=noch3 -(CH2)2ch=CHC(CH3)=NOCH3 -ch2conh2 -(CH2)2CONH2 -(CH2)3CONH2 -ch2conhch3 -(CH2)3CONHCH3 -ch2con(ch3)2 -(CH2)2CON(CH3)2 -(ch2)3con(ch3)2 -ch2coch3 -(CH2)2COCH3 -(CH2)3COCH3 -ch2coch2ch3 -(CH2)2COCH2CH3 -(ch2)3coch2ch3 -(CH2)2OCH2CN •(ch2)3och2cn _(ch2)2och2conh2 -ch2och2conh2 -&lt;^y^=NOH —^&gt;=noch3 —^^&gt;=NOCH2CH3 -\ =NNH2 —&lt;^^=nnhch3 —&lt;^&gt;=nnhch2ch3 —&lt;^&gt;=NN(CH3)2 —&lt;(^&gt;=nso2ch3 —\=ncoch3 NOH NOCH3 NOCH2CH3 nnh2 ^nnhch3 nnhch2ch3 , Nn(ch3)2 /—\ nso2ch3 Factory V ^ncoch3 -( V=NOH — ί \=noch3 -( \=NOCH2CH3 —1 \=nnh2 —< ^=nnhch3 —< nnhch2ch3 —&gt;=nn(ch3)2 —<^=nso2ch3 —< ^=ncoch3 face \ V=noch3 ^ NOCH2CH3 154 201240602 R1 R1 R1

2 NN(CH3)22 NN(CH3)2

NNHCH3NNHCH3

\=nso2ch3\=nso2ch3

\=nnhch2ch3\=nnhch2ch3

NCOCH3NCOCH3

NN(CH3)2 )=nhoch3 y )=nnhch3 y )=nso2ch3 yNN(CH3)2 )=nhoch3 y )=nnhch3 y )=nso2ch3 y

155 201240602155 201240602

156 201240602156 201240602

157 201240602 R1 R1 R1157 201240602 R1 R1 R1

158 201240602 本揭露亦包括表1A至101A,各表係如同上表1 者建構,除了表1中之列標題(即「R2為Ph」)係以下 示之列標題置換。例如在表1A中,其列標題為「R2為 Me」,並且R1係如同上表1所定義者。因此,表1A中 5 之第一項具體揭示式1化合物,其中R1為 ΓΛ 、X0 ch2 η ; R2 為 Me ; R3 為 OH ; Α 為 A-l ; Β1 為 C_1 ; Β2 為 ίο C-3 ; Β3 為 C-l ;以及各 R14、R15、R18 與 R19 為 Η。表 2Α至101Α係以類似方式架構。 表 列標題 表 列標題 1A R2 為 Me 19A R2 為 Ph(4-F) 2A R2 為 Et 20A R2 為 OMe 3A R2 為《-Pr 21A R2 為 OEt 4A R2 為 c-Pr 22A R2 為 CH2Ph 5A R2 為 SMe 23A R2為2-°比啶基 6A R2 為 S〇2Me 24A R2為3-&quot;比啶基 7A R2 為 CF3 25A R2為4-&quot;比啶基 8A R2 為 Ph(2-Cl) 26A R2為Η 9A R2 為 Ph(3-Cl) 27A R2 為 Ph(3,5-二-F) 10A R2 為 Ph(4-Cl) 28A R2 為 Ph(3,4-二-F) 11A R2 為 Ph(2-Me) 29A R2 為 Ph(3,4,5-三-F) 12A R2 為 Ph(3-Me) 30A R2 為 Ph(2,3-二-F) 13A R2 為 Ph(4-Me) 31A R2 為 Ph(3-CF3) 14A R2 為 Ph(2-OMe) 32A R2 為 Ph(4-CF3) 15A R2 為 Ph(3-OMe) 33A R2 為 Ph(3,5-二-CF3) 16A R2 為 Ph(4-OMe) 3.4 A R2 為 w-Bu 17A R2 為 Ph(2-F) 35A R2 為 CH2OCH3, 18A R2 為 Ph(3-F) 36A R2 為 CH2CH2OCH3 159 201240602 表 列標題 表 列標題 37A R2 為 CH2CH2CF3 71A R2為4-異噁唑啉基 38A R2 為 CH2CF3 72A R2為5-Me-3-吡啶基 39A R2 為 w-pent 73A R2為5-C1-2-吡啶基 40A R2 為 c-pent 74A R2 為 Ph(3,4-二-OMe) 41A R2 為 c-Hex 75A R2 為 Ph(3,5-二-OMe) 42A R2 為&quot;-Hex 76A R2 為 Ph(3-OEt) 43A R2 為 thp-4-基 77A R2 為 Ph(4-OEt) 44A R2 為 Ph(2-CN) 78A R2 為 Ph(3,4-二-OEt) 45A R2 為 Ph(3-CN) 79A R2 為 Ph(3,5-二-OEt) 46A R2 為 Ph(4-CN) 80A R2 為 Ph(3,4-二-Me) 47A R2 為 Ph(2-OCH) 81A R2 為 Ph(3,5-二-Me) 48A R2 為 Ph(3-OCH) 82A R2 為 Ph(3,4,5-三-OEt) 49A R2 為 Ph(4-OCH) 83A R2 為 Ph(3-OCH2CH=CH2) 50A R2 為 Ph(3-Me,2-F) 84A R2 為 Ph(4-OCH2CH=CH2) 51A R2 為 Ph(3-Me,4-F) 85A R2 為 3,5-(MeO)2-嘧啶基 52A R2 為 Ph(3-Me, 5-F) 86A R2 為 3,5-(EtO)2-嘧啶基 53A R2 為 Ph(3-Me,6-F) 87A R2 為 3,5-(MeO)2-三嗪基 54A R2 為 Ph(3-F,2-Me) (triazinyl) 55A R2 為 Ph(3-F,4-Me) 88A R2 為 3,5-(EtO)2-三嗪基 56A R2 為 Ph(3-F,5-Me) 89A R2 為-CH2CH=NOCH3 57A R2 為 Ph(3-F,6-Me) 90A R2 為-(CH2)2CH=NOCH3 58A R2 為 i-Pr 91A R2 為-(CH2)3CH=NOCH3 R2為 -CH=CHCH2CH=NOCH3 59A R2 為 i-Bu 92A 60A R2為2-噻吩基 93A R2為 61A R2為3-噻吩基 -(CH2)2CH=CHCH=NOCH3 62A R2為2-呋喃基 94A R2 為-CH2C(CH3)=NOCH3 63A R2為3-呋喃基 95A R2為 64A R2為2-異噁唑啉基 (2-isoxazolinyl) 96A -(ch2)2c(ch3)=noch3 R2 為-CH2CONHCH3 65A R2為2-噁唑啉基 97A R2 為-(CH2)2CONHCH3 66A R2為l-Me-3-吡唑基 98A R2 為-(CH2)3CONHCH3 67A R2為3-噻唑基 99A R2 為-CH2CON(CH3)2 68A R2為2-噻唑基 100A R2 為-(CH2)2CON(CH3)2 69A 70A R2為2-噻唑啉基 (2-thiazolinyl) R2為2-噁唑基 101A R2 為-(CH2)3CON(CH3)2 201240602 表2 表2係如同表1者建構,除了以下列置換其結構 ΟΗ Ο Ο158 201240602 The disclosure also includes Tables 1A to 101A, each of which is constructed as in Table 1, except that the headings in Table 1 (ie, "R2 is Ph") are the column headings replaced below. For example, in Table 1A, the column heading is "R2 is Me", and R1 is as defined in Table 1 above. Thus, the first item of 5 in Table 1A specifically discloses a compound of formula 1, wherein R1 is ΓΛ, X0 ch2 η; R2 is Me; R3 is OH; Α is Al; Β1 is C_1; Β2 is ίο C-3; Β3 is Cl ; and each of R14, R15, R18 and R19 is Η. Tables 2 to 101 are structured in a similar manner. Table headings Table column headings 1A R2 is Me 19A R2 is Ph(4-F) 2A R2 is Et 20A R2 is OMe 3A R2 is "-Pr 21A R2 is OEt 4A R2 is c-Pr 22A R2 is CH2Ph 5A R2 is SMe 23A R2 is 2-° pyridine group 6A R2 is S〇2Me 24A R2 is 3-&quot; pyridine group 7A R2 is CF3 25A R2 is 4-&quot; pyridine group 8A R2 is Ph(2-Cl) 26A R2 is Η 9A R2 is Ph(3-Cl) 27A R2 is Ph(3,5-di-F) 10A R2 is Ph(4-Cl) 28A R2 is Ph(3,4-di-F) 11A R2 is Ph(2-Me) 29A R2 is Ph(3,4,5-tri-F) 12A R2 is Ph(3-Me) 30A R2 is Ph(2,3-di-F) 13A R2 is Ph(4- Me) 31A R2 is Ph(3-CF3) 14A R2 is Ph(2-OMe) 32A R2 is Ph(4-CF3) 15A R2 is Ph(3-OMe) 33A R2 is Ph(3,5-di-CF3 16A R2 is Ph(4-OMe) 3.4 A R2 is w-Bu 17A R2 is Ph(2-F) 35A R2 is CH2OCH3, 18A R2 is Ph(3-F) 36A R2 is CH2CH2OCH3 159 201240602 Table heading table Column heading 37A R2 is CH2CH2CF3 71A R2 is 4-isoxazolinyl 38A R2 is CH2CF3 72A R2 is 5-Me-3-pyridyl 39A R2 is w-pent 73A R2 is 5-C1-2-pyridyl 40A R2 For c-pent 74A R2 is Ph(3,4-di-OMe) 41A R2 is c-Hex 75A R2 is Ph(3,5-di-OMe) 42A R2 is &quot;-Hex 76A R2 is Ph(3-OEt) 43A R2 is thp-4-yl 77A R2 is Ph(4-OEt) 44A R2 is Ph (2-CN) 78A R2 is Ph(3,4-di-OEt) 45A R2 is Ph(3-CN) 79A R2 is Ph(3,5-di-OEt) 46A R2 is Ph(4-CN) 80A R2 is Ph(3,4-di-Me) 47A R2 is Ph(2-OCH) 81A R2 is Ph(3,5-di-Me) 48A R2 is Ph(3-OCH) 82A R2 is Ph(3, 4,5-Tri-OEt) 49A R2 is Ph(4-OCH) 83A R2 is Ph(3-OCH2CH=CH2) 50A R2 is Ph(3-Me,2-F) 84A R2 is Ph(4-OCH2CH= CH2) 51A R2 is Ph(3-Me,4-F) 85A R2 is 3,5-(MeO)2-pyrimidinyl 52A R2 is Ph(3-Me, 5-F) 86A R2 is 3,5-( EtO)2-pyrimidinyl 53A R2 is Ph(3-Me,6-F) 87A R2 is 3,5-(MeO)2-triazinyl 54A R2 is Ph(3-F,2-Me) (triazinyl) 55A R2 is Ph(3-F,4-Me) 88A R2 is 3,5-(EtO)2-triazinyl 56A R2 is Ph(3-F,5-Me) 89A R2 is -CH2CH=NOCH3 57A R2 Is Ph(3-F,6-Me) 90A R2 is -(CH2)2CH=NOCH3 58A R2 is i-Pr 91A R2 is -(CH2)3CH=NOCH3 R2 is -CH=CHCH2CH=NOCH3 59A R2 is i- Bu 92A 60A R2 is 2-thienyl 93A R2 is 61A R2 is 3-thienyl-(CH2)2CH=CHCH=NOCH3 62A R2 is 2-furyl 94A R2 is -CH2C(CH3)=NOCH3 63A R2 is 3-furyl 95A R2 is 64A R2 is 2-isooxazolinyl 96A -(ch2)2c(ch3 ==noch3 R2 is -CH2CONHCH3 65A R2 is 2-oxazolinyl 97A R2 is -(CH2)2CONHCH3 66A R2 is 1-Me-3-pyrazolyl 98A R2 is -(CH2)3CONHCH3 67A R2 is 3-thiazole 99A R2 is -CH2CON(CH3)2 68A R2 is 2-thiazolyl 100A R2 is -(CH2)2CON(CH3)2 69A 70A R2 is 2-thiazolinyl (R) is 2-oxazolyl 101A R2 is -(CH2)3CON(CH3)2 201240602 Table 2 Table 2 is constructed as in Table 1, except that the structure is replaced by the following: Ο Ο

本揭露亦包括表1B至101B,其R2之列標題係與 表1A至101A中者相同。 表3 ίο 表3係如同表1者建構,除了以下列置換其結構The disclosure also includes Tables 1B to 101B, the columns of which are the same as those in Tables 1A to 101A. Table 3 ίο Table 3 is constructed as in Table 1, except that the structure is replaced by the following

本揭露亦包括表1C至101C,其R2之列標題係與 15 表1A至101A中者相同。 表4 表4係如同表1者建構,除了以下列置換其結構 161 201240602The disclosure also includes Tables 1C to 101C, the column of which is the same as that of Tables 1A to 101A. Table 4 Table 4 is constructed as in Table 1, except that the structure is replaced by the following: 161 201240602

R1 R2 表 5 10 本揭露亦包括表1D至101D,其R2之列標題係與 1A至101A中者相同。 表5 表5係如同表1者建構,除了以下列置換其結構 ΟΗ Ο ΟR1 R2 Table 5 10 The present disclosure also includes Tables 1D to 101D, and the column headings of R2 are the same as those in 1A to 101A. Table 5 Table 5 is constructed as in Table 1, except that the structure is replaced by the following ΟΗ Ο Ο

本揭露亦包括表1E至101E,其R2之列標題係與 1A至101A中者相同。 表6 15 表 表6係如同表1者建構,除了以下列置換其結構 OH 0 0The disclosure also includes Tables 1E to 101E, the column of which is the same as that of 1A to 101A. Table 6 15 Table Table 6 is constructed as in Table 1, except that the structure is replaced by the following OH 0 0

R1 R2。 20 表 本揭露亦包括表1F至101F,其R2之列標題係與 1A至101A中者相同。 162 201240602 表7 表7係如同表1者建構,除了以下列置換其結構R1 R2. The table disclosure also includes Tables 1F to 101F, and the column headings of R2 are the same as those of 1A to 101A. 162 201240602 Table 7 Table 7 is constructed as in Table 1, except that the structure is replaced by the following

本揭露亦包括表1G至101G,其R2之列標題係與 表1A至ι〇ιΑ中者相同。 表8係如同表1者建構,除了以下列置換其結構The disclosure also includes Tables 1G to 101G, and the column headings of R2 are the same as those in Tables 1A to ι〇ι. Table 8 is constructed as in Table 1, except that the structure is replaced by the following

本揭露亦包括表1H至ιοίΗ,其R2之列標題係與 表1A至】01A中者相同。 表9 表9係如同表1者建構,除了以下列置換其結構 163 201240602The disclosure also includes Tables 1H to ιοίΗ, and the column headings of R2 are the same as those in Tables 1A to 01A. Table 9 Table 9 is constructed as in Table 1, except that the structure is replaced by the following: 163 201240602

R1 R2 本揭露亦包括表11至1011,其R2之列標題係與表 1A至101A中者相同。 表10 表10係如同表1者建構,除了以下列置換其結構R1 R2 This disclosure also includes Tables 11 through 1011, the columns of which are the same as those in Tables 1A to 101A. Table 10 Table 10 is constructed as in Table 1, except that the structure is replaced by the following

本揭露亦包括表1J至101J,其R2之列標題係與表 1A至101A中者相同。 15 表 11 表11係如同表1者建構,除了以下列置換其結構The disclosure also includes Tables 1J to 101J, and the column headings of R2 are the same as those in Tables 1A to 101A. 15 Table 11 Table 11 is constructed as in Table 1, except that the structure is replaced by the following

164 201240602 本揭露亦包括表1K至101K,其R2之列標題係與 表1A至101A中者相同。 表12 表12係如同表1者建構,除了以下列置換其結構164 201240602 The disclosure also includes Tables 1K to 101K, and the column headings of R2 are the same as those in Tables 1A to 101A. Table 12 Table 12 is constructed as in Table 1, except that the structure is replaced by the following

本揭露亦包括表1L至101L,其R2之列標題係與 ίο 表1A至101A中者相同。 表13 表13係如同表1者建構,除了以下列置換其結構 Ο 0The disclosure also includes Tables 1L to 101L, the column heading of which is the same as that of ίο Tables 1A to 101A. Table 13 Table 13 is constructed as in Table 1, except that the structure is replaced by the following Ο 0

本揭露亦包括表1M至101M,其R2之列標題係與 表1A至101A中者相同。 2〇 表 14 表14係如同表1者建構,除了以下列置換其結構 165 201240602 Ο ΟThe disclosure also includes Tables 1M through 101M, the columns of which are the same as those in Tables 1A through 101A. 2〇 Table 14 Table 14 is constructed as in Table 1, except that the structure is replaced by the following 165 201240602 Ο Ο

本揭露亦包括表IN至101Ν,其R2之列標題係與 表1A至101A中者相同。 5 製劑/效用 本發明之式1化合物將通常使用來作為一組成物 (即製劑)中的除草活性成分,並伴隨有至少一種選自 由界面活性劑、固體稀釋劑及液體稀釋劑所組成之群組 10 的額外成分以作為載體之用。此製劑或組合物成分係經 選擇,以配合活性成分之物理性質、施用型態與土壤種 類、濕度和溫度等環境因素。 可用的製劑包括液體及固體組合物。液體組成物包 括溶液(包括可乳化濃縮物)、懸浮液、乳液(包括微 15 乳液與/或懸浮乳液(suspoemulsion))與類似者,並可選 擇性地將其增稍成凝膠。水性液體組成物的一般類型為 可溶濃縮物(soluble concentrate)、懸浮浪縮物 (suspension concentrate)、膠囊懸浮液(capsule suspension)、濃縮乳液、微乳液和懸浮乳液。非水性液 2〇 體組合物的一般類型為可乳化濃縮物、可微乳化濃縮 物、可分散性濃縮物(dispersible concentrate)及油分散液 (oil dispersion) ° 固體組成物的一般類型為塵粉(dust)、粉劑、粒劑、 丸劑(pellet)、珠劑(prill)、錠劑(pastille)、片劑、包膜(filled 166 201240602 與類似者,其可具有水分散性 成的膜和塗由成膜溶液或可流動懸浮液形 (微)朦舂/在處理上特別有用。活性成分可以緩 性成分之整2進—步形成懸浮液或固體製劑;或者活 以防、劑可歸囊化(或「被覆」)。膠囊化可 二或缺活性成分的職。可乳化粒舰合了可 /辰、、’ S物與乾粒狀製劑的優點。高強度組成物 進一步製劑的中間物。 邛 可喷灑配方通常在喷灑前會先在適合的介質中擴 展。此類液體及固體製劑係配製為可迅速稀釋於噴灑介 質(通常是水)中。喷灑的量可從每公頃約一到數千公 升但更通常為從每公頃約十到數百公升。可喷灑製劑 可在桶中與水或其他適合介 質混合’藉由空中或地面施 用而運用於葉處理,或施用於植物的生長介質。液體製 15 劑與乾製劑可在播種時,直接計量加入滴流灌溉系統或 犁溝。 一 該製劑通常含有有效量的活性成分、稀釋劑和界面 活性劑,其落於下列概略範圍中且重量加起來會等於百 分之百。 20 重量百分比 水分散性粒劑及水溶性粒 成分 0.001-90 稀釋劑 0-99.999 界面活性劑 0-15 劑、片劑及粉劑 油分散液、懸浮液、乳液、 1-50 40-99 0-50 溶液(包括可乳化濃縮物) 塵粉 1-25 70-99 0-5 粒劑與丸劑 0.001-99 5-99.999 0-15 尚強度組成物 90-99 0-10 0-2 167 201240602 固體稀釋劑包括例如,黏土如膨土、微晶高嶺石、 厄帖浦石與高嶺土、石膏、纖維素、二氧化鈦、氧化鋅、 澱粉、糊精、糖(例如乳糖、嚴糖)、二氧化石夕、滑石、 雲母、矽藻土、尿素、碳酸鈣、碳酸鈉與碳酸氫鈉及硫 酸鈉。典型固體稀釋劑係描述於Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed_,Dorland Books,Caldwell,New Jersey 中。 液體稀釋劑包括例如水、A^V-二甲基院醯胺(例如 一甲基甲酿胺)、葶稀、二甲亞石風、院基α比η各咬 酮(例如,TV-甲基°比洛咬酮)、乙二醇、三乙二醇、丙 二醇、二丙二醇、聚丙二醇、碳酸伸丙酯、碳酸伸丁酯、 石蠟(例如’白礦油、正構烷烴、異烷烴)、院基苯、 院基蔡、甘油、三乙酸甘油酯(glycerol triacetate)、山梨 糖醇、方烴、脫芳香脂族、烧基苯、院基萘、如環己酮、 2-庚酮、異佛酮及4_經基-4-甲基-2-戊酮的酮、如乙酸 異戊酯、乙酸己酯、乙酸庚酯、乙酸辛酯、乙酸壬酿、 乙酸十三酯及乙酸異莰酯的醋酸酯、如烷化乳酸醋 (alkylated lactate ester)、二元酯及γ_丁内酯的其他西旨 類、以及醇類,其可為線性、分支、飽和或不飽和,如 甲醇、乙醇、正丙醇、異丙醇、正丁醇、異丁醇、正己 醇、2-乙基己醇、正辛醇、癸醇、異癸醇、異十八醇、 鯨蠟醇、月桂醇、十三醇、油醇、環已醇、四氫糠醇、 二丙酮醇及苯曱醇。液體稀釋劑亦包括飽和以及不飽和 脂肪酸的甘油酯類(典型為C6_C22),諸如植物種子和 水果油(例如橄欖、蓖麻、亞麻仁、芝麻、玉米、花生、 168 201240602 向曰葵、葡萄軒、紅花、棉軒、黃豆、油菜耔、椰子和 棕櫚仁的油)、動物源性脂肪(例如牛油、豬肉脂、豬 油、鱈魚肝油、魚油)及其混合物。液體稀釋劑也包括 院化脂肪酸(例如甲基化、乙基化、丁基化),其中該 5 脂肪酸可藉由水解來自植物和動物來源的甘油酯而獲 得,並可用蒸餾純化。典型的液體稀釋劑係描述於 Marsden, Solvents Guide, 2nd Ed., Interscience, New York,1950 中。 本發明的固體和液體組成物通常包括一或多種界 10 面活性劑。當加入至液體中時,界面活性劑(也已知為 「界面活性劑」)通常會改變(最常為減少)液體的表 面張力。取決於界面活性劑分子中覩水性和親油性基的 性質,界面活性劑可用作為潤濕劑、分散劑、乳化劑或 消泡劑。 15 界面活性劑可以分類為非離子性、陰離子性或陽離 子性。可用於本發明組成物的非離子界面活性劑包括但 不限於:醇烷氧化物如基於天然及合成醇(其可為分枝 或線性)並從該醇類製備出的醇烷氧化物、及環氧乙 烷、環氧丙烷、環氧丁烷及其混合物;乙氧基胺、燒醇 20 醯胺及乙氧基化烷醇醯胺;烷氧基化三酸甘油酯如乙氧 基化黃豆、藥麻和油菜籽油;烷基酚烷氧化物如辛苯盼 乙氧化物(octylphenol ethoxylate)、壬苯酚乙氧化物、二 壬苯酚乙氧化物及十二烷苯酚乙氧化物(由苯酚及環氧 乙烷、環氧丙烷、環氧丁烷或其混合物所製備);由環 25 氧乙烷或環氧丙烷所製備的嵌段聚合物以及其中的終 端嵌段由環氧丙烷所製備的反向嵌段聚合物;乙氧基化 169 201240602 脂肪酸;乙氧基化脂肪酯和油;乙氧基化甲酯;乙氧基 化三苯乙烯苯酚(包括由環氧乙烷、環氧丙烷、環氧丁 烷或其混合物所製備者);脂肪酸酯、甘油酯、羊毛脂 為基礎的衍生物、聚乙氧基化g旨如聚乙氧基化山梨醇針 5 脂肪酸酯、聚乙氧基化山梨糖醇脂肪酸酯及聚乙氧基化 甘油脂肪酸酯;其他山梨醇酐衍生物如山梨醇酐酯;像 是聚合性界面活性劑如隨機共聚物、嵌段共聚物、醇酸 peg (聚乙二醇)、接枝或梳形聚合物及星形聚合物;聚 乙二醇(peg);聚乙二醇脂肪酸酯;聚矽氧為基礎的界面 ίο 活性劑;以及糖衍生物如蔗糖酯、烷基聚葡萄糖苷和烷 基多醣。 有用的陰離子界面活性劑包括但不限於:烷芳基磺 酸以及其鹽;羧基化醇或烷基酚乙氧化物;二苯基磺酸 鹽衍生物,木質素以及木質素衍生物,例如木質績酸 15 鹽;順丁烯二酸或琥珀酸或其酐;烯烴磺酸鹽;磷酸酯 如醇烷氧化物之墙酸酯、烷基苯酚烧氧化物之填酸酯與 苯乙烯基苯酚乙氧化物之磷酸酯;蛋白質為基礎的界面 活性劑;肌胺酸衍生物;苯乙烯紛鱗硫酸酯;油和脂肪 酸的硫酸鹽和磺酸鹽;乙氧基化烷基酚的硫酸鹽和磺酸 20 鹽,醇類的硫酸鹽;乙氧基化醇類的硫酸鹽;胺和酿胺 的續酸鹽如院牛確酸醋;苯、異丙苯、甲苯、二曱 苯及十二苯和十三苯的磺酸鹽;縮合萘的磺酸鹽;萘及 烷基萘的磺酸鹽;分餾石油的磺酸鹽;磺琥珀醯胺酸鹽 (sulfosuccinamate);及磺琥珀酸鹽(suifosuccinate)及其 25 衍生物如二烷基磺琥珀酸鹽。 201240602 可用之陽離子界面活性劑包括但不限於:醯胺及乙 氧基化醮胺;胺如iV-烧基丙二胺、三伸丙三胺及二伸 丙四胺,及乙氧基化胺、乙氧基化二胺以及丙氧基化胺 (從胺及環氧乙烷、環氧丙烷、環氧丁烷或其混合物製 5 備者);胺鹽,如胺乙酸鹽及二胺鹽;四級銨鹽如四級 鹽、乙氧基化四級鹽及雙四級鹽;以及胺氧化物如烷基 二曱基胺氧化物及雙-(2-羥乙基)_烷基胺氧化物。 亦可用於本發明組成物者為非離子界面活性劑與 陰離子界面活性劑的混合物,或非離子界面活性劑與陽 10 離子界面活性劑的混合物。非離子、陰離子及陽離子界 面活性劑及其建議用法係揭露於各式公開參考文獻,包 括 McCutcheon s Emuhifiers and Detergents,annual American and International Editions published by McCutcheon s Division, The Manufacturing Confectioner 15 Publishing Co.» Sisely and Wood, Encyclopedia of SurfaceThe disclosure also includes tables IN to 101, and the column headings of R2 are the same as those in Tables 1A to 101A. 5 Formulation / Utility The compound of the formula 1 of the present invention will generally be used as a herbicidal active ingredient in a composition (i.e., a preparation) accompanied by at least one selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent. The additional ingredients of Group 10 are used as carriers. The formulation or composition ingredients are selected to match the physical properties of the active ingredient, the type of application and the environmental factors such as soil type, humidity and temperature. Useful formulations include liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including micro 15 emulsions and/or suspoemulsions) and the like, and are optionally added to a gel. Typical types of aqueous liquid compositions are soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, and suspension emulsions. The general types of non-aqueous liquid 2 steroid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates and oil dispersions. The general type of solid compositions is dust powder. (dust), powders, granules, pellets, prills, pastilles, tablets, envelopes (filled 166 201240602 and the like, which may have a water-dispersible film and coating It is particularly useful for the formation of a film-forming solution or a flowable suspension (micro) 朦舂 / in the treatment. The active ingredient can be formed into a suspension or a solid preparation by a tempering component; or (or "covered"). Capsules can be used in the presence or absence of active ingredients. The emulsifiable particles combine the advantages of ke, s, and S and dry granules.邛 Sprayable formulations are usually extended in a suitable medium prior to spraying. These liquid and solid formulations are formulated to be rapidly diluted in a spray medium (usually water). The amount sprayed can be from each hectare. About one to several thousand liters but more From about ten to several hundred liters per hectare. The sprayable formulation can be mixed with water or other suitable medium in a bucket for application to the leaf treatment by aerial or ground application, or to the growth medium of the plant. The agent and the dry preparation can be directly metered into the drip irrigation system or furrow at the time of sowing. The preparation usually contains an effective amount of the active ingredient, a diluent and a surfactant, which fall within the following general range and the weight will add up. Equal to 100%. 20% by weight water-dispersible granules and water-soluble granules 0.001-90 Thinner 0-99.999 Surfactant 0-15, tablet and powder oil dispersion, suspension, emulsion, 1-50 40- 99 0-50 solution (including emulsifiable concentrate) dust powder 1-25 70-99 0-5 granules and pills 0.001-99 5-99.999 0-15 still strength composition 90-99 0-10 0-2 167 201240602 Solid diluents include, for example, clay such as bentonite, microcrystalline kaolinite, eucalyptus and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugar (eg lactose, Yan sugar), dioxide Shi Xi, talc Mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed_, Dorland Books, Caldwell, New Liquid diluents include, for example, water, A^V-dimethyl decylamine (such as monomethyl amide), hydrazine, dimethyl sulphur, and hospital-based alpha to η each biting ketone (for example, TV-methyl pirone, ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propyl carbonate, butyl carbonate, paraffin (eg 'white mineral oil, normal paraffin, Isoalkane, phenyl, ketone, glycerol, glycerol triacetate, sorbitol, quaternary hydrocarbon, dearomatized, phenyl, naphthyl, such as cyclohexanone, 2- Heptanone, isophorone and 4-keto-4-methyl-2-pentanone ketone, such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, acetic acid, tridecyl acetate And an acetate of isodecyl acetate, such as an alkylated lactate ester, a dibasic ester, and γ_ Other esters of lactones, and alcohols, which may be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-hexanol, 2- Ethylhexanol, n-octanol, decyl alcohol, isodecyl alcohol, isostearyl alcohol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol and benzofuranol . Liquid diluents also include glycerides of saturated and unsaturated fatty acids (typically C6_C22), such as plant seeds and fruit oils (eg olives, ramie, linseed, sesame, corn, peanuts, 168 201240602 to hollyhock, grape vine , safflower, cotton stalk, soybean, rapeseed, coconut and palm kernel oil), animal-derived fat (such as butter, pork fat, lard, cod liver oil, fish oil) and mixtures thereof. Liquid diluents also include hospitalized fatty acids (e.g., methylated, ethylated, butylated) wherein the 5 fatty acids are obtained by hydrolysis of glycerides from plant and animal sources and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. The solid and liquid compositions of the present invention typically comprise one or more interfacial surfactants. Surfactants (also known as "surfactants") typically change (most often reduce) the surface tension of a liquid when added to a liquid. Depending on the nature of the hydrophobic and lipophilic groups in the surfactant molecule, the surfactant can be used as a wetting, dispersing, emulsifying or antifoaming agent. 15 Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful in the compositions of the present invention include, but are not limited to, alcohol alkoxides such as alcohol alkoxides based on natural and synthetic alcohols which may be branched or linear and prepared from the alcohols, and Ethylene oxide, propylene oxide, butylene oxide and mixtures thereof; ethoxylated amine, decyl alcohol 20 decylamine and ethoxylated alkanolamine; alkoxylated triglyceride such as ethoxylated Soybean, medicinal and rapeseed oil; alkylphenol alkoxides such as octylphenol ethoxylate, phenol ethoxylate, dinonyl phenol ethoxylate and dodecyl phenol ethoxylate (from phenol And ethylene oxide, propylene oxide, butylene oxide or a mixture thereof; a block polymer prepared from cyclooxyethylene or propylene oxide and a terminal block thereof prepared from propylene oxide Reverse block polymer; ethoxylated 169 201240602 fatty acid; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrene phenol (including ethylene oxide, epoxy Prepared from propane, butylene oxide or a mixture thereof; fatty acid esters, Oleate, lanolin-based derivatives, polyethoxylated g such as polyethoxylated sorbitol needle 5 fatty acid ester, polyethoxylated sorbitan fatty acid ester and polyethoxylated glycerol Fatty acid esters; other sorbitan derivatives such as sorbitan esters; such as polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol), grafted or comb polymers And star polymers; polyethylene glycol (peg); polyethylene glycol fatty acid ester; polyoxyl-based interface ίο active agent; and sugar derivatives such as sucrose esters, alkyl polyglucosides and alkylpolysaccharides . Useful anionic surfactants include, but are not limited to, alkylaryl sulfonic acids and salts thereof; carboxylated alcohols or alkylphenol ethoxylates; diphenyl sulfonate derivatives, lignin and lignin derivatives, such as wood Acid 15 salt; maleic acid or succinic acid or its anhydride; olefin sulfonate; phosphate ester such as alcohol alkoxide wall acid ester, alkyl phenol oxide oxide acid ester and styryl phenol Phosphate oxides; protein-based surfactants; sarcosine derivatives; styrene sulfates; sulfates and sulfonates of oils and fatty acids; sulfates and sulphates of ethoxylated alkylphenols Acid 20 salt, alcohol sulfate; ethoxylated alcohol sulfate; amine and brewing amine continuous acid salt such as vinegar; benzene, cumene, toluene, diphenylbenzene and dodecene And sulfonate of triphenylbenzene; sulfonate of condensed naphthalene; sulfonate of naphthalene and alkylnaphthalene; fraction of petroleum sulfonate; sulfosuccinamide; and sulfosuccinate (suifosuccinate) And its 25 derivatives such as dialkyl sulfosuccinate. 201240602 Useful cationic surfactants include, but are not limited to, decylamine and ethoxylated decylamine; amines such as iV-alkyl propylene diamine, triexamine propylene and dipropylene propylene tetraamine, and ethoxylated amines , ethoxylated diamines and propoxylated amines (from amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts a quaternary ammonium salt such as a quaternary salt, an ethoxylated quaternary salt, and a quaternary salt; and an amine oxide such as an alkyl decylamine oxide and a bis-(2-hydroxyethyl)alkylamine Oxide. Also useful in the compositions of the present invention is a mixture of a nonionic surfactant and an anionic surfactant, or a mixture of a nonionic surfactant and a cationic surfactant. Nonionic, anionic, and cationic surfactants and their suggested uses are disclosed in various published references, including McCutcheon s Emuhifiers and Detergents, annual American and International Editions published by McCutcheon s Division, The Manufacturing Confectioner 15 Publishing Co.» Sisely and Wood, Encyclopedia of Surface

Active Agents, Chemical Publ. Co., Inc., New York, 1964,與 A S. Davidson and B. Milwidsky,办咐Active Agents, Chemical Publ. Co., Inc., New York, 1964, with A S. Davidson and B. Milwidsky, Office

Detergents, Seventh Edition, John Wiley and Sons, New York, 1987。 2〇 本發明組合物亦可包含製劑輔助劑及添加劑,及熟 悉該項技術領域者熟知之製劑助劑(其中部分亦可視為 提供固體稀釋劑、液體稀釋劑或界面活性劑之功能 該配方輔助劑及添加劑可調控pH (緩衝溶液)、處理期 間的發泡(抗發泡劑如聚有機矽氧烷)、活性成份的沉 25 積(懸浮劑)、黏滯性(觸變增稠劑)、容器中之微生物 生長(抗菌劑)、產物凍結(抗凍劑)、顏色(染料/顏 171 201240602 料分散液)、洗除(成膜劑或黏著劑)、蒸發(蒸發阻滯 劑)以及其他製劑特性賦予者。成膜劑包括例如聚乙酸 乙烯、聚乙酸乙烯共聚物、聚乙烯吡咯烷酮_乙酸乙烯 酯共聚物、聚乙烯醇、聚乙烯醇共聚物及蠟。製劑輔助 劑及添加劑之實例包括列示於以下文獻者: McCutcheon^s Volume 2: Functional Materials, annualDetergents, Seventh Edition, John Wiley and Sons, New York, 1987. 2 The compositions of the present invention may also contain formulation adjuvants and additives, and formulation auxiliaries well known to those skilled in the art (some of which may also be considered to provide a solid diluent, a liquid diluent or a surfactant). Agents and additives can regulate pH (buffer solution), foaming during treatment (anti-foaming agent such as polyorganosiloxane), precipitation of active ingredients (suspension), viscosity (thixotropy thickener) , microbial growth (antibacterial agent) in the container, product freezing (antifreeze), color (dye/yan 171 201240602 dispersion), washing (film former or adhesive), evaporation (evaporation blocker), and Other formulation characteristics include, for example, polyvinyl acetate, polyvinyl acetate copolymer, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohol, polyvinyl alcohol copolymer, and wax. Examples of formulation adjuvants and additives Includes those listed in the following literature: McCutcheon^s Volume 2: Functional Materials, annual

International and North American editions published byInternational and North American editions published by

McCutcheon s Division, The Manufacturing ConfectionerMcCutcheon s Division, The Manufacturing Confectioner

Publishing Co.;以及 PCT 公開第 w〇 03/024222 號。 式1化合物以及任何其他活性成分,典型為藉由在 溶劑中溶解活性成分或在一液體或乾性稀釋劑中磨 碎,而結合至本發明組成物中。藉由簡單混合成分可製 備出液劑,包括可乳化濃縮物。若打算用作為可乳化濃 縮物之液體组成物的溶劑與水不互溶,則通常會在用水 稀釋時,加入乳化劑以乳化該含活性成分之溶劑。粒徑 向達2,000 μιτι的活性成分漿液可使用介質研磨機濕 磨,以獲得平均直徑在3 μπι以下的粒子。水性漿液可 製成為成品懸浮濃縮物(請參見如u s 3,〇6〇,〇84)或 藉由喷霧乾燥進一步加工成水分散性粒劑。乾式製劑通 常需要乾磨製程,其產生的平均粒徑在2到10 μΐΏ的範 圍内。塵粉及粉劑可藉由摻合以及通常加上研磨(如以 鐘磨或液3b研磨機)而製備。粒劑及丸劑係經由將活性 材料喷灑於預成形之粒狀載體或以黏聚技術製成。請參 見 Browning,Agglomeration”,CTze/mca/ Ewgzweer/wg, December 4, 1967, pp 147-48, Perry's ChemicalPublishing Co.; and PCT Publication No. 04/024222. The compound of formula 1 as well as any other active ingredient is typically incorporated into the compositions of the invention by dissolving the active ingredient in a solvent or grinding in a liquid or dry diluent. The liquid extracting agent, including the emulsifiable concentrate, can be prepared by simply mixing the ingredients. If the solvent intended to be used as the liquid composition of the emulsifiable concentrate is immiscible with water, an emulsifier is usually added to dilute the solvent containing the active ingredient when diluted with water. The slurry of the active ingredient having a particle size of up to 2,000 μm can be wet-milled using a media mill to obtain particles having an average diameter of 3 μm or less. The aqueous slurry can be made into a finished suspension concentrate (see, e.g., u s 3, 〇6〇, 〇84) or further processed into a water-dispersible granule by spray drying. Dry formulations typically require a dry milling process that produces an average particle size in the range of 2 to 10 μΐΏ. Dust and powder can be prepared by blending and usually by grinding (e.g., by a clock mill or a liquid 3b mill). Granules and pills are prepared by spraying the active material onto a preformed particulate carrier or by cohesive techniques. See Browning, Agglomeration", CTze/mca/ Ewgzweer/wg, December 4, 1967, pp 147-48, Perry's Chemical

Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 172 201240602 1963, pages 8-57與以下’以及WO 91/13546。丸劑可如 U.S_ 4,172,714中所述者製備。水分散性與水溶性粒劑 可如 U.S· 4,144,050、U.s. 3,920,442 與 DE 3,246,493 中 所教示者製備。錠劑可如U.S. 5,180,587、U.S. 5,232,701 5 與U.S. 5,208,030所教示者製備。膜衣可如GB 2,095,558 與U.S. 3,299,566所教示者製備。 有關製劑技術之進一步資訊,請參見T. S. Woods, “The Formulator’s Toolbox - Product Forms for Modern Agriculture” in PeWic/i/e 万/asc^nce, 77?e ίο Food-Environment Challenge, T. Brooks and T. R.Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 172 201240602 1963, pages 8-57 and below, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. The water-dispersible and water-soluble granules can be prepared as taught in U.S. Patent No. 4,144,050, U.S. Patent No. 3,920,442, the entire disclosure of which is incorporated herein by reference. Lozenges can be prepared as taught by U.S. Patent No. 5,180,587, U.S. 5,232,701, and U.S. Patent No. 5,208,030. Film coats can be prepared as taught by GB 2,095,558 and U.S. Patent 3,299,566. For further information on formulation techniques, see T. S. Woods, “The Formulator’s Toolbox - Product Forms for Modern Agriculture” in PeWic/i/e million/asc^nce, 77?e ίο Food-Environment Challenge, T. Brooks and T. R.

Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society ofRoberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of

Chemistry, Cambridge, 1999, pp. 120-133。亦請參見 U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and 15 Examples 10-41 ; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41,52, 53, 58, 132,138-140,162-164,166,167 and 169-182 ; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John 2〇 Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbooks 8th Ed., Blackwell Scientific Publications,Oxford,1989 ;以及 Deve/op所州b h formulation technology, PJB Publications, Richmond, UK, 2000。 25 在下面的實例中,所有的百分比均為按重量計且所Chemistry, Cambridge, 1999, pp. 120-133. See also US 3,235,361, Col. 6, line 16 through Col. 7, line 19 and 15 Examples 10-41; US 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; US 2,891, 855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John 2〇Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbooks 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Deve /op state bh formulation technology, PJB Publications, Richmond, UK, 2000. 25 In the example below, all percentages are by weight and

有的製劑均以常規方式製備。化合物編號參照索引表A 173 201240602 至B中的化合物。即使沒有進一步的闡述,相信使用上 述說明的本領域具有通常知識者仍能夠最大程度地利 用本發明。因此,以下實例僅為說明之用,而絕非用於 限制本發明之揭露内容。除非另有說明,百分比為按重 量計。Some formulations are prepared in a conventional manner. The compound number refers to the compound in Index Table A 173 201240602 to B. Even without further elaboration, it is believed that those of ordinary skill in the art in the <RTIgt; Therefore, the following examples are for illustrative purposes only and are not intended to limit the disclosure of the invention. Percentages are by weight unless otherwise stated.

實例A 98.5% 0.5% 1.0% 高強度濃縮物 化合物1 二氧化矽氣凝膠 合成非晶質細二氧化矽Example A 98.5% 0.5% 1.0% High Strength Concentrate Compound 1 Cerium Oxide Aerogel Synthesis of amorphous fine cerium oxide

實例B 可濕性粉末 化合物1 65.0% 十二烷基酚聚乙二醇醚 2.0% 木質磺酸鈉 4.0% 矽鋁酸鈉 6.0% 蒙脫土(經煅燒) 23.0%Example B Wettable powder Compound 1 65.0% Dodecylphenol polyglycol ether 2.0% Sodium lignosulfonate 4.0% Sodium strontium aluminate 6.0% Montmorillonite (calcined) 23.0%

實例C 粒劑 化合物1 10.0% 厄帖浦石粒劑(低揮發性物質,0.71/0.30 mm ; 90.0% U.S.S. No. 25 至 50 篩)Example C Granules Compound 1 10.0% Eituprite granules (low volatiles, 0.71/0.30 mm; 90.0% U.S.S. No. 25 to 50 sieves)

實例D 擠出丸劑 化合物1 25.0% 無水硫酸納 10.0% 粗木質磺酸鈣 5.0% 院基萘績酸納 1.0% 鈣/鎂膨潤土 59.0% 174 201240602Example D Extrusion Pills Compound 1 25.0% anhydrous sodium sulphate 10.0% calcium crude lignosulfonate 5.0% phthalocyanine sodium 1.0% calcium/magnesium bentonite 59.0% 174 201240602

實例E 可乳化濃縮物 化合物1 10.0% 20.0% 70.0% 5.0% 30.0% 30.0% 15.0% 20.0% 聚,乙,山梨糖醇己油酸(polyoxyethylene sorbitol hexoleate) C^-Cio脂肪酸甲醋Example E Emulsifiable Concentrate Compound 1 10.0% 20.0% 70.0% 5.0% 30.0% 30.0% 15.0% 20.0% Poly, sorbitol hexoleate C^-Cio fatty acid methyl vinegar

實例FExample F

微乳液 J 化合物1 聚乙烯吡咯啶酮-乙酸乙烯共聚物 烧基,葡萄糖苷(alkylp〇lyglyc〇side) 甘油單油酸酯(g丨yceryl m〇n〇〇丨eate) 水 這些化合物通常對於早期萌後雜草防治 後雜草幼笛仍為幼嫩時施用)與萌前雜°田二 草幼苗由土壌萌發前施用)顯示出最高活 全防治所有植物的區域,諸如在燃料儲擗、工 = 域、停車場、露天汽車電影院、機場、“、J = 他水道、看板與高速公路及鐵路設施周圍,許多言此、 合對於廣大麵之萌前或碰雜草防治具有效 這些本發明化合物經由下列方式而可·選擇性防= (selective control)作物/雜草混生中的禾草與闊葉^ 15 草,包括在作物中進行對抗雜草的選擇性代謝,或者對 於作物與雜草中的生理抑制位點具有選擇性活性, 在作物與雜草混生的環境上或中進行選擇性施故j或者 該項技術者會認知到,在一化合物或化合物群組熱習 些選擇性因子(selectivity factor)的較佳組合可藉中,這 常規生物與/或生化檢定而迅速決定。重要曲由實施 文展藝作物可 175 201240602 15 20 對於本發明化合物顯示财受性,包括但不限於苜蓿草、 $麥、棉花、小麥、油菜、甜菜、玉米、高粱、黃豆、 稻米、燕麥、花生、蔬菜、番茄、馬鈴薯、多年生栽植 作物包括咖啡、可可、油粽櫚、橡膠、甘蔗、柑橘、葡 萄、果樹、堅果樹、香蕉、芭蕉、鳳梨、乾啤酒花、茶 與=木如桉樹及針葉樹(例如火炬松)與草坪物種(二 如肯塔基藍草、聖奥古斯丁草、高狐草與百慕達草)。 本發明化合物對於選擇性防治小麥、大麥尤其是玉米、 黃丑、棉花與多年生栽植作物如甘蔗與柑橘中的雜草特 別有用。本發明化合物可用於經基因改造或選殖以導入 除草劑抗性的作物、表現對無脊椎動物害蟲具有毒性之 蛋白質(如蘇力菌(五⑽細•吻⑽⑷毒素)與/或表 現其他有用特徵。熟習該項技術者會瞭解到、,並非二有 化合物對所有雜草皆具有㈣效果。或者, 於改變植物生長。 ^ 由於本發明化合物同時具有萌後與萌前除草活 藉由殺除或毒傷非所欲植物或降低其生長以防治 ^物’可藉由各式方法_地_合物 法涉及使一除草有效量才 二万 化人物與至+ —本發魏合物,或—包含該 #丨^ # ^劑、@體稀釋劑或液體稀釋 =:,接觸該非所欲植物之葉子 = 該環境或該環境係圍繞^水,該非所欲植物係生長於 殖體(pr〇pa_。 4非所欲植物之種子或其他繁 定匕:物之除草有效量係考慮多種因素而決 疋。运些因素包括.所選用之製劑、施用方法、出現的 &gt;76 25 201240602 植物數量與種類、生長條件等。一 &amp; 物之除草有效量為約〇 〇〇1至2 一般而言,本發明化合 在約0.004至1 kg/ha。熟習, g/ha ’而典型的範圍 所欲雜草防雜度所需的^^^者可㈣決定達到 本發明化合物亦可與一式里 物或藥劑混合以形成—多成其他生β物活性化合 農業保護,包括除草劑、除二=’而提供更廣泛的 蟲劑、殺線蟲劑、、知保護劑、殺真菌劑、殺 蝕削叙踝蝨Μ殺菌劑、殺蟎 10 15 20 蜆皮抑侧與生__、化學滅蟲 驅蟲劑、誘引劑、費洛蒙、激食因子、植物營^素素其 =生物活性化合物錢生纟^錢真菌。本發明化 a物與其鎌草狀混合物可擴朗抗額外雜草物種 活性的範® ’並且壓抑任何抗性生物型的增生。因此本 發明亦適用於—包含—式1化合物(以除草有效量)以 及至少一種額外生物活性化合物或藥劑之組成物,並可 進一步包含至少一種界面活性劑、固體稀釋劑或液體稀 釋劑。其他生物活性化合物或藥劑可配製於組成物中, s亥組成物包含至少一種界面活性劑、固體或液體稀釋 劑。針對本發明混合物,可將一或多種其他生物活性化 合物或藥劑與式1化合物一同配製,以形成一預混物, 或可將一或多種其他生物活性化合物或藥劑與式j化 合物分開配製’並在施用前將製劑組合在一起(例如在 一喷灑槽中),或者接續施用。 一或多種下列除草劑與本發明化合物之混合物對 於雜草防治尤其有用:乙草胺(acet〇cW〇r)、亞喜芬 (acifluorfen)與其鈉鹽、苯草醚(aci〇nifen)、丙烯醛 177 25 201240602 (acrolein, 2-propenal)、拉草(alachlor)、亞汰草 (alloxydim)、草殺淨(ametryn)、氨唾草酮 (amicarbazone)、醯嘧續隆(amidosulfuron)、胺環吡克 (aminocyclopyrachlor)與其酯(例如曱酯、乙酯)及鹽(例 5 如鈉鹽、鉀鹽)、4-胺基-3-氣-6-(4-氣-2-氟-3-甲氧苯 基)-2-吡啶羧酸與其酯(例如甲酯)及鹽(例如鈉鹽、 _鹽)、氣氨基β比咬酸(aminopyralid)、殺草強(amitrole)、 氨基續酸敍(ammonium sulfamate)、莎稗填(anilofos)、 亞速爛(asulam)、草脫淨(atrazine)、四坐喊續隆 ίο (azimsulfuron)、氟 丁草胺(beflubutamid)、草除靈 (benazolin)、草除靈乙酯(benazolin-ethyl)、醯苯草酮 (bencarbazone)、倍尼芬(benfluralin)、呋草黃 (benfuresate)、免速隆(bensulfuron-methyl)、地散鱗 (bensulide)、本達隆(bentazone)、苯並雙環酮 is (benzobicyclon)、吡草酮(benzofenap)、二環吡草酮 (bicyclopyrone)、治草醚(bifenox)、畢拉草(bilanafos)、 雙草醚(bispyribac)與其鈉鹽、克草(bromacil)、溴布泰 (bromobutide)、漠酴肪(bromofenoxim)、漠苯腈 (bromoxynil)、漠苯腈辛酸g旨(bromoxynil octanoate)、丁 2〇 基拉草(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷 (butamifos)、比達寧(butralin)、丁 苯草酮(butroxydim)、 拔敵草(butylate)、苯 _ 〇坐(cafenstrole)、草長滅 (carbetamide)、乙0坐草 i同(carfentrazone-ethyl)、兒茶素 (catechin)、曱氧基護谷(chlomethoxyfen)、克攔本 25 (chloramben)、滅落寧(chlorbromuron)、氣甲丹 (chlorflurenol-methyl)、氣草敏(chloridazon)、氣喊續隆 178 201240602 (chlorimuron-ethyl)、綠麥隆(chlorotoluron)、克普芬 (chlorpropham)、氣磺隆(chlorsulfuron)、大克草 (chlorthal-dimethyl)、草克樂(chlorthiamid)、吲《朵酮草酯 (cinidon-ethyl)、環庚草醚(cinmethylin)、西速隆 5 (cinosulfuron)、環苯草酮(clefoxydim)、剋草同 (clethodim)、炔草 g旨(clodinafop-propargyl)、可滅蹤 (clomazone)、克普草(clomeprop)、畢克草(clopyralid)、 畢克草醇胺(clopyralid-olamine)、氯酯續草胺 (cloransulam-methyl)、苄草隆(cumyluron)、氰乃淨 ίο (cyanazine)、草滅特(cycloate)、環磺隆 (cyclosulfamuron)、環殺草(cycloxydim)、丁基赛伏草 (cyhalofop-butyl)、2,4-D 與其丁氧乙酯(butotyl ester)、 丁酯、異辛酯(isoctyl ester)與異丙酯及其二甲銨鹽、二 乙醇胺(diolamine)鹽與三乙醇胺(trolamine)鹽、殺草隆 is (daimuron)、得拉本(dalapon)、得拉本鈉 (dalapon-sodium)、邁隆(dazomet)、2,4-DB 與其二甲敍 鹽、卸鹽及納鹽、甜菜安(desmedipham)、敵草淨 (desmetryn)、麥草畏(dicamba)與其二乙二醇敍 (diglycolammonium)鹽、二曱銨鹽、鉀鹽及鈉鹽、二氣 2〇 達龍(dichlobenil)、滴丙酸(dichlorprop)、禾草靈 (diclofop-methyl)、雙氣磺草胺(diclosulam)、燕麥括硫 酸甲酯(difenzoquat metilsulfate)、吡氟草胺 (diflufenican)、二氟 η比隆(diflufenzopyr)、惡唾隆 (dimefuron)、α底草丹(dimepiperate)、二曱草胺 25 (dimethachlor)、愛落殺(dimethametryn)、汰草滅 (dimethenamid)、汰草滅-p、穫萎得(dimethipin)、二甲 179 201240602 胂酸(dimethylarsinic acid)與其納鹽、敵樂胺 (dinitramine)、特樂紛(dinoterb)、大芬滅(diphenamid)、 敵草快(diquat dibromide)、汰硫草(dithiopyr)、達有龍 (diuron)、DNOC、茵多酸(endothal)、EPTC、戊草丹 5 (esprocarb)、乙丁 烯氟靈(ethalfluralin)、胺苯磺隆 (ethametsulfuron-methyl)、乙嗪草酮(ethiozin)、乙氧呋 草黃(ethofumesate)、氣氟草醚(ethoxyfen)、亞速隆 (ethoxysulfuron)、乙氧苯草胺(et〇benzanid)、芬殺草 (fenoxaprop-ethyl)、芬殺草-p(fen0xapr0p_p_ethyl)、異噁 ίο 苯砜(fenoxasulfone)、四唑草胺(fentrazamide)、非草隆 (fenuron)、非草隆-TCA(fenuron-TCA)、高效麥草伏 (flamprop-methyl)、 高效麥草伏丙酯 (flamprop-M-isopropyl)、高效麥草伏曱酯 (flamprop-M-methyl)、伏速隆(flazasuifuron)、雙氟磺草 15 胺(florasulam)、伏寄普(fluazifop-butyl)、伏寄普 •P(fluazifop-P-butyl)、異丙吡草酯(fluazolate)、氟酮磺 隆(flucarbazone)、氟吡磺隆(flucetosulfuron)、氟吡磺隆 (fluchloralin)、《,塞草胺(flufenacet)、氟噠嗪草 (flufe叩yr)、氟噠嗪草酯(fiufenpyr-ethyi)、唑嘧磺草胺 2〇 (flumetsulam)、氟烯草酸(flumiclorac-pentyl)、丙炔氟草 胺(flumioxazin)、伏草隆(fluometuron)、乙羧氟草醚 (fluoroglycofen-ethyl)、氟胺草唑(flupoxam)、氟啶嘧磺 隆(flupyrsulfuron-methyl)與其鈉鹽、抑草丁(fluren〇i)、 芴丁 S旨(flurenol-butyl)、氟咬草酮(fluridone)、氟比酮 25 (flurochloridone)、氟氣比(fluroxypyr)、呋草酮 (flurtamone)、氟噻曱草酯(fluthiacet-methyl)、氟磺胺草 201240602 醚(fomesafen)、雙敗續草胺(foramsulfuron)、殺木膦敍 (fosamine-ammonium)、草錢膦(glufosinate)、草銨膦敍 (glufosinate-ammonium)、嘉填塞(glyphosate)與鹽如敍 鹽、異丙銨鹽、鉀鹽、鈉鹽(包括倍半鈉鹽)及三甲基 5 硫鹽(亦稱為草硫膦(sulfosate))、合速隆 (halosulfuron-methyl)、乙氧乙基合氯氟 (haloxyfop-etotyl)、甲基合氣氟(haloxyfop-methyl)、菲 殺淨(hexazinone)、咪草醋(imazamethabenz-methyl)、甲 氧°米草煙(imazamox)、甲味嗤煙酸(imazapic)、依滅草 ίο (imazapyr)、滅草口奎(imazaquin)、滅草0轰敍 (imazaquin-ammonium) 、 indaziflam 、味 草煙 (imazethapyr)、咪草煙錢(imazethapyr-ammonium)、依速 隆(imazosulfuron)、茚草鋼(indanofan)、甲基峨續隆 (iodosulfuron-methyl)、蛾塞尼爾(ioxynil)、峨塞尼爾辛 15 酿酯(ioxynil octanoate)、蛾塞尼爾納(ioxynil-sodium)、 艾分卡斑嗤(ipfencarbazone)、IR6396、異丙隆 (isoproturon)、愛速隆(isouron)、異噁草胺(isoxaben)、 異0惡β坐草酮(isoxaflutole)、異°惡氣草晒(isoxachlortole)、 乳氟禾草靈(lactofen)、環草定(lenacil)、理有龍 2〇 (linuron)、順丁烯二酿肼(maleic hydrazide)、MCPA 及 其鹽(例如MCPA·二甲銨鹽、MCPA-鉀鹽與MCPA-鈉 鹽)、酯(例如MCPA-2-乙基己酯、MCPA-丁氧乙酯與 硫酯(例如MCPA-硫乙酯)、MCPB及其鹽(例如MCPB-鈉鹽)及S旨(例如MCPB-乙S旨)、甲氯丙酸(mecoprop)、 25 甲氯丙酸-P(mecoprop-P)、滅芬草(mefenacet)、美福泰 (mefluidide)、甲續胺績隆(mesosulfuron-methyl)、硝草Microemulsion J Compound 1 Polyvinylpyrrolidone-vinyl acetate copolymer alkyl, glucoside (alkylp〇lyglyc〇side) glycerol monooleate (g丨yceryl m〇n〇〇丨eate) water These compounds are usually for early stage After the post-emergence weed control, the weed flute is still applied when it is young) and the pre-emergence weeds are applied before the germination of the soil, showing the highest area for all plants, such as fuel storage and work. = domain, parking lot, open-air car cinema, airport, ", J = his waterway, kanbans and highways and railway facilities, many of these, for the vast majority of the surface of the pre-emergence or weed control is effective Selective control of grasses and broadleaf grasses in crops/weeds, including selective metabolism of weeds in crops, or in crops and weeds Physiological inhibition sites have selective activity, selective or selective in the environment of crops and weeds, or the skilled person will recognize that a compound or group of compounds is hot A preferred combination of selectivity factors can be quickly determined by this conventional biological and/or biochemical assay. The important curves are shown by the implementation of the article 175 201240602 15 20 for the compounds of the invention, including But not limited to alfalfa, wheat, cotton, wheat, rape, beet, corn, sorghum, soybeans, rice, oats, peanuts, vegetables, tomatoes, potatoes, perennial plantings including coffee, cocoa, oil palm, rubber, sugar cane , citrus, grapes, fruit trees, nut trees, bananas, plantains, pineapples, dried hops, teas and = woody eucalyptus and conifers (such as Pinus taeda) and lawn species (such as Kentucky bluegrass, St. Augustine, fox grass and Bermuda compounds. The compounds of the invention are particularly useful for the selective control of weeds in wheat, barley, especially corn, yellow ugly, cotton and perennial planting crops such as sugar cane and citrus. The compounds of the invention may be used for genetic modification or colonization. To introduce herbicide-resistant crops and to express proteins that are toxic to invertebrate pests (eg, sclerotium (five) (10) Fine • Kiss (10) (4) Toxins) and/or other useful characteristics. Those skilled in the art will appreciate that not all compounds have a (four) effect on all weeds. Or, that alter plant growth. ^ Due to the compounds of the present invention At the same time, there is a post-emergence and pre-emergence herbicidal activity by killing or poisoning undesired plants or reducing their growth to prevent and control the 'object' can be achieved by various methods_ground method to make a herbicidal effective amount only 20,000 Characters and to + - this hair, or - containing the #丨 ^ # ^ agent, @ body thinner or liquid dilution =:, contact with the leaves of the unintended plant = the environment or the environment around the water The undesired plant grows in the colon (pr〇pa_. 4 seeds of undesired plants or other complex herbicides: the herbicidal effective amount is determined by considering various factors. These factors include the formulation selected, the method of application, the number and type of plants present, and the growth conditions. The herbicidal effective amount of a &amp; matter is about 〇〇 至 1 to 2. In general, the present invention is compounded at about 0.004 to 1 kg/ha. Familiar with g/ha' and the typical range of weeds required for weed control (4) can be determined to achieve the compound of the present invention can also be mixed with a formula or agent to form - more other beta activity Combined agricultural protection, including herbicides, in addition to two = 'and provide a wider range of insecticides, nematicides, known protective agents, fungicides, chlorpyrifos, fungicides, killing 10 15 20 mink Inhibition of side and raw __, chemical insecticides, insecticides, attractants, pheromones, stimulating factors, plant succulents, bioactive compounds, granules, and fungi. The a composition of the invention and its valerian mixture expands against the activity of additional weed species and suppresses the proliferation of any resistant biotype. The invention is therefore also applicable to the inclusion of a compound of formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or composition of a pharmaceutical agent, and may further comprise at least one surfactant, solid diluent or liquid diluent. Other biologically active compounds or agents may be formulated in the composition, and the composition of the invention comprises at least one surfactant, solid or liquid diluent. For the mixtures of the invention, one or more other biologically active compounds or agents may be formulated with a compound of formula 1 to form a premix, or one or more other biologically active compounds or agents may be formulated separately from the compound of formula j. The formulations are combined together (e.g., in a spray tank) prior to administration, or successively. Mixtures of one or more of the following herbicides with the compounds of the invention are especially useful for weed control: acetochlor (acet〇cW〇r), acifluorfen and its sodium salt, aci〇nifen, propylene Aldehyde 177 25 201240602 (acrolein, 2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, amine ring Aminocyclopyrachlor and its esters (eg, oxime esters, ethyl esters) and salts (eg, 5, such as sodium, potassium), 4-amino-3- gas-6-(4-gas-2-fluoro-3- Methoxyphenyl)-2-pyridinecarboxylic acid and its esters (such as methyl ester) and salts (such as sodium salt, _salt), aminopyralid (aminopyralid), amitrelation (amitrole), amino acid (ammonium sulfamate), anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin , benzallin-ethyl, bencarbazone, benfluralin, benfuresate, free speed (ben Sulson-methyl), bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox Bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, indiprozil octanoic acid g (bromoxynil octanoate), butachlor, butafenacil, butamifos, butralin, butroxydim, diquat (butylate), benzene_cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, gram stop 25 (chloramben), chlorbromuron, chlorflurenol-methyl, chloridazon, qi sheng continued 178 201240602 (chlorimuron-ethyl), chlorotoluron, kepufen (chlorpropham), chlorsulfuron, chlorthal-dimethyl, grass Chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clefoxydim, clethodim, acetylene CG (clodinafop-propargyl), clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl , cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2, 4-D with butotyl ester, butyl ester, isoctyl ester and isopropyl ester and its dimethylammonium salt, diethanolamine salt and triethanolamine (trolamine) salt, herbicide Dai (daimuron), dalapon, dalapon-sodium, dazome, 2,4-DB and its dimethyl salt, unsalted salt and sodium salt, beet amp (desmedipham ), desmetryn, dicamba and its diglycolammonium, diammonium, potassium and sodium salts, Dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenic acid (difenzoquat metilsulfate) Diflufenican), diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, Dimethicin-di, dimethipin, dimethyl 179 201240602 dimethylarsinic acid and its sodium salts, dinitramine, dinoterb, diphenamid, diquat Diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, amine benzene Ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etoxbenzan , fenoxaprop-ethyl, fennel-p (fen0xapr0p_p_ethyl), heterosexual ο fenoxasulfone, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop- M-isopropyl), high-efficiency flamprop-M-methyl, flazasuifuron, florasulam, fluazifop-butyl, voltapril • P ( fluazifop-P-butyl), fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, fluoride Flufe叩yr, fiufenpyr-ethyi, flumetsulam, flumiclorac-pentyl, flumioxazin, volt Fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, fluren〇i, 芴丁Flurenol-butyl, fluridone, flurochloridone, fluroxypyr, furosterone Amone), fluthiacet-methyl, sulfamethoxazole 201240602 ether (fomesafen), foramsulfuron, fosamine-ammonium, glufosinate, grass Glufosinate-ammonium, glyphosate and salts such as salt, isopropylammonium, potassium, sodium (including sesquisulfate) and trimethylsulfonate (also known as grass sulphur) Sulfosate, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazeth vinegar Imazamethabenz-methyl), imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium , indaziflam, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, iodosulfuron-methyl, moth sin Ioxynil), ioxynil octanoate, ioxynil-sodium, acicle Ip (ipfencarbazone), IR6396, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, milk Lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (eg MCPA·dimethylammonium salt, MCPA-) Potassium salt and MCPA-sodium salt), esters (eg MCPA-2-ethylhexyl ester, MCPA-butoxyethyl ester and thioester (eg MCPA-thioethyl ester), MCPB and its salts (eg MCPB-sodium salt) And S (for example, MCPB-B), mecoprop, 25 mecoprop-P, mefenacet, mefluidide, methylamine Mesosulfuron-methyl, nitriceps

181 S 201240602 酮(mesotrione)、威百故(metam-sodium)、惡唾醯草胺 (metamifop)、苯嗓草 g同(metamitron)、滅草胺 (metazachlor)、雙轉氣吼《密績隆(metazosulfuron)、甲草 苯隆(methabenzthiazuron)、甲胂酸(methylarsonic acid) 5 與其鈣鹽、單銨鹽、單鈉鹽及二鈉鹽)、甲基汰草龍 (methyldymron)、。比喝隆(metobenzuron)、溴谷隆 (metobromuron)、莫多草(metolachlor)、S-莫多草 (S-metolachlor)、續草 口坐胺(metosulam)、甲氧隆 (metoxuron)、滅必淨(metribuzin)、甲續隆 ίο (metsulfuron-methyl)、稻得壯(molinate)、綠谷隆 (monolinuron)、萘丙胺(naproanilide)、滅落脫 (napropamide)、納得爛(naptalam)、草不隆(neburon)、 煙嘴績隆(nicosulfuron)、說草敏(norflurazon)、 (orbencarb)、痛苯胺續隆(orthosulfamuron)、氨續樂靈 15 (oryzalin)、快°惡草嗣(oxadiargyl)、坪草丹樂滅草 (oxadiazon)、環氧嘴續隆(oxasulfuron)、β惡嗪草酉同 (oxaziclomefone)、復祿芬(oxyfluorfen)、巴拉刈二氣鹽 (paraquat dichloride)、克草猛(pebulate)、壬酸(pelargonic acid)、施得圃(pendimethalin)、平速爛(penoxsulam)、蔬 2〇 草滅(pentanochlor)、環戊惡草酮(pentoxazone)、佈福松 (perfluidone)、烯草胺(pethoxamid)、苯草胺 (pethoxyamid)、甜菜寧(phenmedipham)、毒莠定 (picloram)、毒莠定鉀(picloram-potassium)、氟0比醮草胺 (picolinafen)、°坐啦草酯(pinoxaden)、α底草填 25 (piperophos)、普拉草(pretilachlor)、氟喊確隆 (primisulfuron-methyl)、氨氟樂靈(prodiamine)、氣苯隹 201240602 草酿I (profoxydim)、撲滅通(prometon)、撲草淨 (prometryn)、雷蒙得(propachlor)、除草靈(propanil)、普 拔草(propaquizafop)、普拔根(propazine)、苯胺靈 (propham)、異丙草胺(propisochlor)、丙苯項隆 5 (propoxycarbazone)、戊炔草胺(propyzamide)、苄草丹 (prosulfocarb)、氟石黃隆(prosulfuron)、雙唾草腈 (pyraclonil)、D比草越(pyraflufen-ethyl)、續醯草 *»比嗤 (pyrasulfotole)、雙 σ坐草晴(pyrazogyl)、苄草吐 (pyrazolynate)、普芬草(pyrazoxyfen)、百速隆 ίο (pyrazosulfuron-ethyl)、口密咬拆草 iiE(pyribenzoxim)、稗 草畏(pyributicarb)、必汰草(pyridate)、4-胺基-3-氣-6-(4-氣-2-氟-3-甲氧苯基)-2-吡啶羧酸(CAS編號 943832-60-8)、4-胺基-3-氯-6-(4-氣-2·氟-3-甲氧苯基)-2-吡啶羧酸甲酯(CAS編號943831-98-9)、環酯草醚 is (pyriftalid)、σ密草鍵(pyriminobac-methyl)、嘴咬硫蕃 (pyrimisulfan)、嘴草硫鍵(pyrithiobac)、喊草硫醚納 (pyrithiobac-sodium)、派羅克殺草礙(pyroxasulfone)、咬 確草胺(pyroxsulam)、快克草(quinclorac)、氯甲啥淋酸 (quinmerac)、莫克草(quinoclamine)、快伏草 2〇 (quizalofop-ethyl)、快伏草-P(quizalofop-P-ethyl)、啥禾 糠酯(quizalofop-P-tefuryl)、玉 °密續隆(rimsulfuron)、喊 咬聘草謎(saflufenacil)、西殺草(sethoxydim)、環草隆 (siduron)、草滅淨(simazine)、西草淨(simetryn)、續草 酮(sulcotrione)、曱續草胺(sulfentrazone)、曱癌續隆 25 (sulfometuron-methyl)、確醯續隆(sulfosulfuron)、 2,3,6-TBA、TCA、TCA-鈉、牧草胺(tebutam)、丁噻隆 183 201240602 (tebuthiuron)、特夫三酮(tefuryltrione)、環確酮 (tembotrione)、得殺草(tepraloxydim)、特草定(terbacil)、 曱氧去草净(terbumeton)、特丁津(terbuthylazine)、去草 淨(terbutryn)、欣克草(thenylchlor)、嘆草定(thiazopyr)、 5 酮腺續草吩酯(thiencarbazone)、嗟吩續隆 (thifensulfuron-methyl)、殺丹(thiobencarb)、仲草丹 (tiocarbazil)、苯。比 °坐草酮(topramezone)、肪草酮 (tralkoxydim)、野燕畏(tri-allate)、醚苯績隆 (triasulfuron)、三 β坐命(triaziflam)、苯續隆 ίο (tribenuron-methyl)、三氯比(triclopyr)、丁氧乙基三氯 比 (triclopyr-butotyl)、 三氯比 三乙錄 (triclopyr-triethylammonium)、三地芬(tridiphane)、草達 津(trietazine)、三氟咬續隆(trifloxysulfuron)、三福林 (trifluralin)、氟胺績隆(triflusulfuron-methyl)、三氟甲續 15 隆(tritosulfuron)與萬隆(vernolate)。其他除草劑亦包括 生物除草劑如損毀鍵格抱菌(J/化 Simmons)、刺盤孢炭殖菌(Co//e⑹nc/zwm (Penz.) Penz. &amp; Sacc.)、稗内臍·螺孢菌(ZVec/wiem wowocer似,MTB-951)、疣孢漆斑菌(Myro认echw 2〇 (Albertini &amp; Schweinitz) Ditmar: Fries)、棕櫚 疫病菌(/&gt;/如〇/?/^〇^2/?0//^0^*&lt;3(丑111;1.)81^1.)與遏藍菜 柄鐘菌(Pwcc/m’a Schub·)。 本發明化合物亦可與下列物質組合使用,包括植物 生長調節素如艾維激素(aviglycine)、#-(苯基甲基)-1//-25 °票吟-6-胺、丙醯芸苔素内酯(ep〇ch〇leone)、吉貝素 (gibberellic acid)、吉貝素(gibberellin) A4 與 A7、超敏蛋 184 201240602 白(harpin protein)、縮節胺(mepiquat chloride)、調環酸 屢弓(prohexadione calcium) 、 茉莉酸丙酯 (prohydrojasmon)、復石肖盼納(sodium nitrophenolate)與抗 倒酯(trinexapac-methyl)及植物生長修改生物如仙人掌 桿菌 CBacz/ZMs cerews)菌株 BP01。 農業用保護劑(除草劑、除草劑保護劑、殺蟲劑、 殺真菌劑、殺線蟲劑、殺蟎劑與生物劑)的一般參考文181 S 201240602 Ketone (mesotrione), metam-sodium, metamifop, benzoquinone g (metamitron), metazachlor (metazachlor), double-turn gas (metazosulfuron), methabenzthiazuron, methylarsonic acid 5 and its calcium, monoammonium, monosodium and disodium salts, and methyldymron. Metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, extinction Meribuzin, metsulfuron-methyl, rice, mololinuron, naproanilide, napropamide, naptalam, grass Neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, ping Oxadizon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, gram grass Pebulate), pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, acetochlor Pethoxamid), pethoxyamid, phenmedipham, poison Picloram, picloram-potassium, picolinium, picoxaden, piperophos, pretilachlor, fluoride Primisulfuron-methyl, prodiamine, benzoquinone 201240602 profoxydim, prometon, prometryn, propachlor, herbicide (propanil), propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyzamide, benzyl Prosulfocarb, prosulfuron, pyraclonil, D pyraflufen-ethyl, sorghum*»pyrasulfotole, pyrazogyl ), pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, 4-Amino-3-gas-6-(4-Gas-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid (CAS number 943832-60 -8), 4-amino-3-chloro-6-(4-a-2,fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid methyl ester (CAS No. 943831-98-9), ring Iridium (isriftalid), pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyrocide Pyroxasulfone, pyroxulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quick grass -P(quizalofop-P-ethyl), quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, cyclopsone (siduron), simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron ), 2,3,6-TBA, TCA, TCA-sodium, forage (tebutam), butyl thiol 183 201240602 (tebuthiuron), tefuryltrione, tembotrione, tepraloxydim Special grass (terb Acil), terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, 5 ketone gland (thiencarbazone) , thifensulfuron-methyl, thiobencarb, tiocarbazil, benzene. Topazone, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl , triclopyr, triclopyr-butotyl, triclopy-triethylammonium, tridiphane, trietazine, trifed bite Trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron and vernolate. Other herbicides also include biological herbicides such as J. sylvestris (J/Simmons), C. sinensis (Co//e(6)nc/zwm (Penz.) Penz. &amp; Sacc.) Helicobacter spp. (ZVec/wiem wowocer, MTB-951), Myro echw 2〇 (Albertini &amp; Schweinitz Ditmar: Fries), palm plague (/&gt;/如〇/?/ ^〇^2/?0//^0^*&lt;3(Ugly 111;1.)81^1.) and T. sinensis (Pwcc/m'a Schub·). The compounds of the present invention can also be used in combination with the following substances, including plant growth regulators such as aviglycine, #-(phenylmethyl)-1//-25 ° 吟-6-amine, propyl chlorite Endoester (ep〇ch〇leone), gibberellic acid, gibberellin A4 and A7, hypersensitive egg 184 201240602 white (harpin protein), mepiquat chloride, ring Prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Cactus bacillus/ZMs cerews strain BP01. General reference for agricultural protective agents (herbicides, herbicide protectants, insecticides, fungicides, nematicides, acaricides and biological agents)

獻么括 The Pesticide Manual, 13th Edition,C. Ό SThe Pesticide Manual, 13th Edition, C. Ό S

Tomlin, Ed., British Crop Protection Council, Farnham, 10 15 20 以mey,\j.K_,2Q03 反 The BioPesticide Manual,2ndTomlin, Ed., British Crop Protection Council, Farnham, 10 15 20 by mey, \j.K_, 2Q03 Anti The BioPesticide Manual, 2nd

Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2001 〇 對於其中使用一或多種這些各式混合伙伴藥劑的 實施例而言,這些各式混合伙伴藥劑(總計)對式卫化 合物之重量比例典型為介於約1:3000與約3〇〇〇:1。值 得注意的是介於約1:3GG至約3GG:1間之重量比例(例 如&quot;於約1:30至約30:1間之比例)。熟習該項技術者可 經由簡單實驗’迅速決定活性成分達成所需生物活性範 圍必要之生物有效量,然地,相較於單獨使用式ι或 化合物所能防治的範圍’包括這些額外成分可能擴大對 於雜草的防治範圍。 、 表A1列出成分⑷與成分(b)之具體組合其可說明 混合物、組成物與方法。成分⑷攔位中的化合 杰八:、標不於索引表A中。表A1的第二欄列出具體之 成刀(b)化合物(例如第一行的「2,4〇」)。表的第三、 第四與第五攔列出在針對田間生長作物的典型施用一率 185 25 201240602 時’成分(b)化合物對成分(a)的重量比例範圍。因此, 例如表A1第一行具體揭露成分(a)(即索引表a中的化 合物1)與2,4-D之組合物典型為以介於丨Η]至&amp; 的重量比例施用。表A1其餘行以類似方式架構。-1Edition, LG Copping, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2001 〇 For examples in which one or more of these various mixed partner agents are used, these various mixed partner agents (total) pairs The weight ratio of the hydrazine compound is typically between about 1:3000 and about 3 〇〇〇:1. The value to be noted is a weight ratio between about 1:3 GG to about 3 GG:1 (e.g., &quot; ratio between about 1:30 and about 30:1). Those skilled in the art can quickly determine the biologically effective amount necessary for the active ingredient to achieve the desired range of biological activity via a simple experiment. However, the range that can be controlled by the use of the formula or compound alone may include an expansion of these additional ingredients. For the control range of weeds. Table A1 lists the specific combinations of component (4) and component (b) which illustrate the mixture, composition and method. Composition (4) in the block of the combination of Jie eight:, marked in the index table A. The second column of Table A1 lists the specific compound of the knife (b) (for example, "2, 4" in the first row). The third, fourth and fifth bars of the table list the range of weight ratios of the component (b) compound to the component (a) at a typical application rate for field growing crops 185 25 201240602. Thus, for example, the first row of Table A1 specifically discloses that the composition of component (a) (i.e., Compound 1 in Index Table a) and 2,4-D is typically applied in a weight ratio of from 丨Η] to &amp; The remaining rows of Table A1 are structured in a similar manner. -1

186 201240602 成分(a) 成分(b) 典型 重量比例 更典型 重量比例 最典型 重量比例 化合物1 二環吡草酮 (Bicyclopyrone) 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 化合物1 治草驗(Bifenox) 1:257 至 5:1 1:85 至 2:1 1:32 至 1:4 化合物1 雙草醚 (Bispyribac-sodium) 1:10 至 1 12:1 1:3 至 38:1 1:1 至 7:1 化合物1 克草(Bromacil) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 漠布泰(Bromobutide) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 溴苯腈(Bromoxynil) 1:96 至 12:1 1:32 至 4:1 1:12 至 1:2 化合物1 丁 基拉草(Butachlor) 1:768 至 2:1 1:256 至 1:2 1:96 至 1:11 化合物1 氟丙0^ 草 S旨(Butafenacil) 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 化合物1 拔敵草(Butylate) 1:1542 至 1:2 1:514 至 1:5 1:192 至 1:22 化合物1 苯 。坐(Carfenstrole) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 乙唑草酮 (Carfentrazone-ethyl) 1:128 至 9:1 1:42 至 3:1 1:16 至 1:2 化合物1 氯嘧磺隆 (Chlorimuron-ethyl) 1:8 至 135:1 1:2 至 45:1 1:1 至 9:1 化合物1 綠麥隆(Chlorotoluron) 1:768 至 2:1 1:256 至 1:2 1:96 至 1:11 化合物1 氯確隆(Chlorsulfuron) 1:6 至 168:1 1:2 至 56:1 1:1 至 11:1 化合物1 西速隆(Cincosulfuron) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 吲哚酮草酯 (Cinidon-ethyl) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 環庚草鍵(Cinmethylin) 1:34 至 34:1 1:11 至 12:1 1:4 至 3:1 化合物1 対草同(Clethodim) 1:48 至 24:1 1:16 至 8:1 1:6 至 2:1 化合物1 炔丙基炔草酸 (Clodinafop-propargyl) 1:20 至 56:1 1:6 至 19:1 1:2 至 4:1 化合物1 可滅縱(Clomazone) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 克普草(Clomeprop) 1:171 至 7:1 1:57 至 3:1 1:21 至 1:3 化合物1 畢克草(Clopyralid) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 氯酯磺草胺 (Cloransulam-methyl) 1:12 至 96:1 1:4 至 32:1 1:1 至 6:1 化合物1 苄草隆(Cumyluron) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 氰乃淨(Cyanazine) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 環績隆(Cyclosulfamuron) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 環殺草(Cycloxydim) 1:96 至 12:1 1:32 至 4:1 1:12 至 1:2 化合物1 賽伏草(Cyhalofop) 1:25 至 45:1 1:8 至 15:1 1:3 至 3:1 化合物1 殺草隆(Daimuron) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 甜菜安(Desmedipham) 1:322 至 4:1 1:107 至 2:1 1:40 至 1:5 化合物1 麥草畏(Dicamba) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 二氣達龍(Dichlobenil) 1:1371 至 1:2 1:457 至 1:4 1:171 至 1:20 187 201240602 成分(a) 成分(b) 典型 重量比例 更典型 重量比例 最典型 重量比例 化合物1 滴丙酸(DichlcKprop) 1:925 至 2:1 1:308 至 1:3 1:115 至 1:13 化合物1 曱基禾草靈 (Diclofop-methyl) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 雙氣項草胺(Diclosulam) 1:10 至 112:] 1:3 至 38:1 1:1 至 7:1 化合物1 燕麥枯(Difenzoquat) 1:288 至 4:1 1:96 至 2:1 1:36 至 1:4 化合物1 。比敗草胺(Diflufenican) 1:857 至 2:1 1:285 至 1:3 1:107 至 1:12 化合物1 二氣 °比隆(Diflufenzopyr) 1:12 至 96:1 1:4 至 32:1 1:1 至 6:1 化合物1 二曱草胺(Dimethachlor) 1:768 至 2:1 1:256 至 1:2 1:96 至 1:11 化合物1 愛落殺(Dimethametryn) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 汰草滅 -P(Dimethenamid-P) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 汰硫草(Dithiopyr) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 達有龍(Diuron) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 EPTC 1:768 至 2:1 1:256 至 1:2 1:96 至 1:1] 化合物1 戊草丹(Esprocarb) 1:1371 至 1:2 1:457 至 1:4 1:171 至 1:20 化合物1 乙丁 稀氟靈(Ethalfluralin) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 胺苯磺隆 (Ethametsulfuron-methyl) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 氯氟草越(Ethoxyfen) 1:8 至 135:1 1:2 至 45:1 1:1 至 9:1 化合物1 亞速隆(Ethoxysulfuron) 1:20 至 56:1 1:6 至 19:1 1:2 至 4:1 化合物1 乙氧苯草胺(Etobenzanid) 1:257 至 5:1 1:85 至 2:1 1:32 至 1:4 化合物1 乙基芬殺草 (Fenoxaprop-ethyl) 1:120 至 10:1 1:40 至 4:1 1:15 至 1:2 化合物1 異 α惡苯礙(Fenoxasulfone) 1:85 至 14:1 1:28 至 5:1 1:10 至 1:2 化合物I 四0坐草胺(Fentrazamide) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 伏速隆(Flazasulfuron) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 雙氟績草胺(Florasulam) 1:2 至 420:1 1:1 至 140:1 2:1 至 27:1 化合物1 丁基伏寄普 (Fluazifop-butyl) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 氟酿1績隆(Flucarbazone) 1:8 至 135:1 1:2 至 45:1 1:1 至 9:1 化合物1 氟11比磺隆 (Flucetosulfuron) 1:8 至 135:1 1:2 至 45:1 1:1 至 9:1 化合物1 疼草胺(Flufenacet) 1:257 至 5:1 1:85 至 2:1 1:32 至 1:4 化合物1 唑嘧磺草胺 (Flumetsulam) 1:24 至 48:1 1:8 至 16:1 1:3 至 3:1 化合物1 氟烯草酸 (Flumiclorac-pentyl) 1:10 至 112:1 1:3 至 38:1 1:1 至 7:1 化合物1 丙炔氟草胺(Flumioxazin) 1:25 至 45:1 1:8 至 15:1 1:3 至 3:1 化合物1 伏草隆(Fluometuron) 1:384 至 3:1 1:128 至 1:1 1:48 至]:6 化合物1 氟啶嘧磺隆 1:3 至 336:1 1:1 至 112:1 2:1 至 21:1 188 201240602 成分(a) 成分(b) 典型 重量比例 更典型 重量比例 最典型 重量比例 (Flupyrsulfuron-methyl) 化合物1 氟咬草酮(Fluridone) ]:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 氟氣比(Fluroxypyr) 1:96 至 12:1 1:32 至 4:1 1:12 至 1:2 化合物1 口夫草 _(Flurtamone) 1:857 至 2:1 1:285 至 1:3 1:107 至 1:12 化合物1 氟噻曱草酯 (Fluthiacet-methyl) 1:48 至 42:1 1:16 至 14:1 1:3 至 3:1 化合物1 氟續胺草謎(Fomesafen) 1:96 至 12:1 1:32 至 4:1 1:12 至 1:2 化合物1 雙氟磺草胺 (Foramsulfuron) 1:13 至 84:1 1:4 至 28:1 1:1 至 6:1 化合物1 草敍膦(Glufosinate) 1:288 至 4:1 1:96 至 2:1 1:36 至 1:4 化合物1 嘉难塞(Glyphosate) 1:288 至 4:1 1:96 至 2:1 1:36 至 1:4 化合物1 合速隆 (Halosulfuron-methyl) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 甲基合氣氟 (Haloxy fop-methyl) 1:34 至 34:1 1:11 至 12:1 1:4 至 3:1 化合物1 菲殺淨(Hexazinone) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 甲氧0米草煙(Imazamox) 1:13 至 84:1 1:4 至 28:1 1:1 至 6:1 化合物1 曱味。坐煙酸(Imazapic) 1:20 至 56:1 1:6 至 19:1 1:2 至 4:1 化合物1 依滅草(Imazapyr) 1:85 至 14:1 1:28 至 5:1 1:10 至 1:2 化合物1 滅草噎(Imazaquin) 1:34 至 34:1 1:11 至 12:1 1:4 至 3:1 化合物1 咪草酯 (Imazethabenz-methyl) 1:171 至 7:1 1:57 至 3:1 1:21 至 1:3 化合物1 咪草煙 1:24 至 48:1 1:8 至 16:1 1:3 至 3:1 化合物1 依速隆(Imazosulfuron) 1:27 至 42:1 1:9 至 14:1 1:3 至 3:1 化合物1 茚草闕(Indanofan) 1:342 至 4:1 1:114 至 2:1 1:42 至 1:5 化合物1 Indaziflam 1:25 至 45:1 1:8 至 15:1 1:3 至 3:1 化合物1 曱基碘磺隆 (Iodosulfuron-methyl) 1:3 至 336:1 1:1 至 112:1 2:1 至 21:1 化合物1 峨塞尼爾(Ioxynil) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 艾分卡斑唑 (Ipfencarbazone) 1:85 至]4:1 1:28 至 5:1 1:10 至 1:2 化合物1 異丙隆(Isoproturon) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 異°惡草胺(Isoxaben) 1:288 至 4:1 1:96 至 2:1 1:36 至 1:4 化合物1 異嗔唾草 _ (Isoxaflutole) 1:60 至 20:1 1:20 至 7:1 1:7 至 2:1 化合物1 乳氟禾草靈(Lactofen) 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 化合物1 環草定(Lenacil) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 理有龍(Linuron) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 MCPA 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 MCPB 1:288 至 4:1 1:96 至 2:1 1:36 至 1:4 189 201240602 成分(a) 成分(b) 典型 重量比例 更典型 重量比例 最典型 重量比例 化合物1 曱氣丙酸(Mecoprop) 1:768 至 2:1 1:256 至 1:2 1:96 至 1:11 化合物1 滅芬草(Mefenacet) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 美福泰(Mefluidide) 1:192 至 6:1 ]:64 至 2:1 1:24 至 1:3 化合物1 曱磺胺磺隆 (Mesosulfuron-methyl) 1:5 至 224:1 1:1 至 75:1 1:1 至 14:1 化合物1 硝草嗣(Mesotrione) 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 化合物1 惡〇坐醯草胺(Metamifop) 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 化合物1 滅草胺(Metazachlor) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 雙醚氣吡嘧磺隆 (Metazosulfuron) 1:25 至 45:] 1:8 至 15:1 1:3 至 3:1 化合物1 曱草苯隆 (Methabenzthiazuron) 1:768 至 2:1 1:256 至 1:2 1:96 至 1:11 化合物1 莫多草(Metolachlor) 1:768 至 2:1 1:256 至 1:2 1:96 至 1:11 化合物1 績草°坐胺(Metosulam) 1:8 至 135:1 1:2 至 45:1 1:1 至 9:1 化合物1 滅必淨(Metribuzin) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 曱磺隆 (Metsulfuron-methyl) 1:2 至 560:1 1:1 至 187:1 3:1 至 35:1 化合物1 稻得壯(Molinate) 1:1028 至 2:1 1:342 至 1:3 1:128 至 1:15 化合物1 滅落脫(Napropamide) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 納得爛(Naptalam) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 煙啦墙隆(Nicosulfuron) 1:12 至 96:1 1:4 至 32:1 1:1 至 6:1 化合物1 氟草敏(Norflurazon) 1:1152 至 1:1 1:384 至 1:3 1:144 至 1:16 化合物1 坪草丹(Orbencarb) 1:1371 至 1:2 1:457 至 1:4 1:171 至 1:20 化合物1 嘧苯胺磺隆 (Orthosulfamuron) 1:20 至 56:1 1:6 至 19:1 1:2 至 4:1 化合物1 氨項樂靈(Oryzalin) 1:514 至 3:1 1:171 至 1:2 1:64 至 1:8 化合物1 快0惡草酮(Oxadiargyl) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 樂滅草(Oxadiazon) 1:548 至 3:1 1:182 至 1:2 1:68 至 1:8 化合物1 環氧嘴墙隆(Oxasulfuron) 1:27 至 42:1 1:9 至 14:1 1:3 至 3:1 化合物1 β惡17秦草酮 (Oxaziclomefone) 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 化合物1 復祿芬(Oxyfluorfen) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 百草枯(Paraquat) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 施得圃(Pendimethalin) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 平速爛(Penoxsulam) 1:10 至 112:1 1:3 至 38:1 1:1 至 7:1 化合物1 苯草胺(Penthoxamid) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 環戊惡草酿I (Pentoxazone) 1:102 至 12:1 1:34 至 4:1 1:12 至 1:2 化合物1 甜菜寧(Phenmedipham) 1:102 至 12:1 1:34 至 4:1 1:12 至 1:2 化合物1 毒莠定(Picloram) 1:96 至 12:1 1:32 至 4:1 1:12 至 1:2 190 201240602 成分(a) 成分(b) 典型 重量比例 更典型 重量比例 最典型 重量比例 化合物1 氟0比醯草胺(Picolinafen) 1:34 至 34:1 1:11 至 12:1 1:4 至 3:1 化合物1 σ坐琳草醋(pinoxaden) 1:25 至 45:1 1:8 至 15:1 1:3 至 3:1 化合物1 普拉草(Pretilachlor) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 氟嘧磺隆 (Primisulfuron-methyl) 1:8 至 135:1 1:2 至 45:1 1:】至9:1 化合物1 敦氟樂靈(Prodiamine) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 氯苯嘆草酮(Profoxydim) 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 化合物1 撲草淨(Prometryn) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 雷蒙得(Propachlor) 1:1152 至 1:1 1:384 至 1:3 1:144 至 1:16 化合物1 除草靈(Propanil) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 普拔草(Propaquizafop) 1:48 至 24:1 1:16 至 8:1 1:6 至 2:1 化合物1 丙苯項隆 (Propoxycarbazone) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 咪唑嘧磺隆 (Propyrisulfuron) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 戊炔草胺(Propyzamide) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 苄草丹(Prosulfocarb) 1:1200 至 1:2 1:400 至 1:4 1:150 至 1:17 化合物1 氣確隆(Prosulfuron) 1:6 至 168 1 1:2 至 56:1 1:1 至 11:1 化合物1 雙°坐草腈(Pyraclonil) 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 化合物1 °比草謎(Pyraflufen-ethyl) 1:5 至 224:1 1:1 至 75:1 1:1 至 14:1 化合物1 續酿草σ比σ坐 (Pyrasulfotole) 1:13 至 84:1 1:4 至 28:1 1:1 至 6:1 化合物1 苄草嗤(Pyrazolynate) 1:857 至 2:1 1:285 至 1:3 1:107 至 1:12 化合物1 百速隆 (Pyrazosulfuron-ethyl) 1:10 至 112:1 1:3 至 38:1 1:1 至 7:1 化合物1 普芬草(Pyrazoxyfen) 1:5 至 224:1 1:1 至 75:1 1:1 至 14:1 化合物1 嘧啶肟草醚 (Pyribenzoxim) 1:10 至 112:1 1:3 至 38:1 1:1 至 7:1 化合物1 稗草畏(pyributicarb) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 必汰草(Pyridate) 1:288 至 4:1 1:96 至 2:1 1:36 至 1:4 化合物1 環 S旨草醚(Pyriftalid) 1:10 至 112:1 1:3 至 38:1 1:1 至 7:1 化合物1 嘧草醚 (Pyriminobac-methyl) 1:20 至 56:1 1:6 至 19:1 1:2 至 4:1 化合物1 喊咬硫蕃(Pyrimisulfan) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 喊草硫謎(Pyrithiobac) 1:24 至 48:1 1:8 至 16:1 1:3 至 3:1 化合物1 派羅克殺草礙 (Pyroxasulfone) 1:85 至 14:1 1:28 至 5:1 1:10 至 1:2 化合物1 咬績草胺(Pyroxsulam) 1:5 至 224:1 1:1 至 75:1 1:1 至 14:1 化合物1 快克草(Quinclorac) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 乙基快伏草 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 191 201240602 成分(a) 成分(b) 典型 重量比例 更典型 重量比例 最典型 重量比例 (Quizalofop-ethyl) 化合物1 玉 0密績隆(Rimsulfuron) 1:13 至 84:1 1:4 至 28:1 1:1 至 6:1 化合物1 略咬肪草驗(Saflufenacil) 1:25 至 45:1 1:8 至 15:1 1:3 至 3:1 化合物1 西殺草(Sethoxydim) 1:96 至 12:1 1:32 至 4:1 1:12 至 1:2 化合物1 草滅淨(Simazine) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 罐草酮(Sulcotrione) 1:120 至 10:1 1:40 至 4:1 1:15 至 1:2 化合物1 曱確草胺(Sulfentrazone) 1:147 至 8:1 1:49 至 3:1 1:18 至 1:3 化合物] 甲嘧磺隆 (Sulfometuron-methyl) 1:34 至 34:1 1:11 至 12:1 ]:4 至 3:1 化合物1 續酿項隆(Sulfosulfuron) 1:8 至 135:1 1:2 至 45:1 1:1 至 9:1 化合物1 丁嗟隆(Tebuthiuron) 1:384 至 3:1 1:128 至 1:1 1:48 至]:6 化合物1 Tefuryltrione 1:42 至 27:1 1:14 至 9:1 1:5 至 2:1 化合物1 環項嗣(Tembotrione) 1:31 至 37:1 1:10 至 13:1 1:3 至 3:1 化合物1 得殺草(Tepraloxydim) 1:25 至 45:1 1:8 至 15:1 1:3 至 3:1 化合物1 特草定(Terbacil) 1:288 至 4:1 1:96 至 2:1 1:36 至 1:4 化合物1 Terbuthylatrazine 1:857 至 2:1 1:285 至 1:3 1:107 至 1:12 化合物1 去草淨(Terbutryn) ]:192 至 6:1 1:64 至 2:1 1:24 至]:3 化合物1 欣克草(Thenylchlor) 1:85 至 14:1 1:28 至 5:1 1:10 至]:2 化合物1 嗟草定(Thiazopyr) 1:384 至 3:1 1:128 至 1:1 1:48 至 1:6 化合物1 酮脲磺草吩酯 (Thiencarbazone) 1:3 至 336:] 1:1 至]12:1 2:1 至 21:1 化合物1 噻吩磺隆 (Thifensulfuron-methyl) ]:5 至 224:1 1:1 至 75:1 1:1 至 14:1 化合物1 殺丹(Thiobencarb) 1:768 至 2:1 1:256 至 1:2 1:96 至 1:11 化合物1 苯吡唑草酮 (Topramazone) 1:6 至 168:1 1:2 至 56:1 1:1 至 11:1 化合物1 肪草嗣(Tralkoxydim) 1:68 至]7:1 1:22 至 6:1 1:8 至 2:1 化合物1 野燕畏(Triallate) 1:768 至 2:1 1:256 至 1:2 1:96 至 1:11 化合物1 謎苯績隆(Triasu丨furon) 1:5 至 224:1 1:1 至 75:1 1:1 至 14:1 化合物1 三0坐命(Triaziflam) 1:171 至 7:1 1:57 至 3:1 1:21 至 1:3 化合物1 苯墙隆(Tribenuron) 1:3 至 336:1 1:1 至 112:1 2:1 至 21:1 化合物1 三氣比(Triclopyr) 1:192 至 6:1 1:64 至 2:1 1:24 至 1:3 化合物1 三氟啶磺隆 (Trifloxysulfuron) 1:2 至 420:1 1:1 至 140:1 2:1 至 27:1 化合物] 三福林(Trifluralin) 1:288 至 4:1 1:96 至 2:1 1:36 至 1:4 化合物1 氟胺績隆 (Triflusulfuron-methyl) 1:17 至 68:1 1:5 至 23:1 1:2 至 5:1 化合物1 三氟曱磺隆 (Tritosulfuron) 1:13 至 84:1 1:4 至 28:1 1:1 至 6:1 192 201240602 表A2係如同上表Ai者建構,除了「成分(a)」欄標題下 方的項目係以下示各別成分(a)攔項目置換。成分(a)襴 中之化合物2係標示於索引表A。因此,例如在表A2 5 中,「成分(a)」攔標題全部皆敘述「化合物2」(即標示 於索引表A中之化合物2),並且表A2之欄標題下方的 第一行具體揭露化合物2與2,4-D之混合物。表A3至 A34係以類似方式架構。 表編號 成分(a)棚項目 A2 化合物2 A3 化合物3 A4 化合物4 A5 化合物5 A6 化合物6 A7 化合物7 A8 化合物8 A9 化合物9 A10 化合物10 All 化合物11 A12 化合物12 A13 化合物13 A14 化合物14 A15 化合物15 A16 化合物16 A17 化合物17 A18 化合物18 表編號 成分(a)攔項目 A19 化合物19 A20 化合物20 A21 化合物21 A22 化合物22 A23 化合物23 A24 化合物24 A25 化合物25 A26 化合物26 A27 化合物27 A28 化合物28 A29 化合物29 A30 化合物30 A31 化合物31 A32 化合物32 A33 化合物33 A34 化合物34 在一些例子中,本發明化合物與其他生物活性(特 別是除草性)化合物或藥劑(即活性成分)的組合物對 於雜草可造成大於相加(greater-than-additive)(即協同) 的效果,並且/或者對於作物或其他欲保留植物可造成 193 201240602 小於相加(iess-th㈣備ive)(即保護)的效果。理相蛐 是降低活性成分於放量,_確保有效之^ 防治效果,用較大量活性成分以提供有效雜草防二且 不會造成多餘作物傷害的能力亦為理想的。t除草活性 成分對於雜草產生協同作用時(在提供農藝:令人滿竟 之雜草防治程度的施用率下),此類組合“ 物生產成本與減少環境負擔可帶來益處。當除草活性成 分對於作物產生保護作用時,此類組合物藉由減少雜草 競爭而可帶來提高作物保護作用的益處。 值得注意者為本發明化合物與至少一種其他除草 活性成分的組合物。值得特別注意者為其他除草活性成 分的作用位置與本發明化合物不同的組合物。在一些例 子中,結合至少一種防治範圍相仿但作用位置不同:其 他除草活性成分的組合物,其在抗性管理方面尤具益 處。因此,本發明組成物可進一步包含至少一種額外除 草活性成》(以-除草有效量),Α此成分具有相仿防 治範圍但不同作用位置。 本發明化合物亦可與除草劑保護劑組合以提高對 於某些作物的t全性,諸如草毒死(aiiid〇chl〇r)、解草嗓 (ben〇XaC〇r)、BCS (1·溴-4-[(氣f基)磺醯基]苯)、解毒喹 (cloquintocet-mexyl)、解草胺腈(cy〇metrinil)、環丙磺醯 胺(cyprosulfonamide)、二氣丙烯胺(dichl〇rmid)、4仁 氣乙醯基)-1-氧雜-4-偶氮螺[4 5]癸烷(M〇N466〇)、2_(二 氣曱基)-2-曱基-1,3-二氧雜環戊烷(MG 191)、 二環隆酮 (dicydonon)、增效磷(dieth〇丨批)、解草唑 (fenchlorazole-ethyl)、解草啶(fend〇rim)、解草胺 201240602 (flurazole)、氟草柄·(fluxofenim)、解草惡嗤(furilazole)、 雙苯°惡嗤酸(isoxadifen-ethyl)、嗤解草醋 (mefenpyr-diethyl)、美伏耐、苯草酮(methoxyphenone) ((4-甲氧基-3 -甲基苯基)(3-曱基苯基)曱酮)、萘二曱酸軒 (naphthalic anhydride (1,8-萘二曱酸酐)與解草猜 10 15 20 (oxabetrinil)。解毒有效量之除草劑保護劑可與本發明化 合物同時施用,或作為種子處理施用。因此,本發明之 一態樣涉及一種除草混合物,其包含一本發明化合物與 解毒有效量之除草劑保護劑。種子處理對於雜草之選擇 性防治尤為有用,因為其物理上將解毒作用限制在作物 植物上。因此,一種尤其有用之本發明實施例為一種用 於選擇性防治作物中之非所欲植物生長的方法,其包含 使該作物的所在地接觸一除草有效量的一本發明化合 物,其中該作物之種子(作物係由其生長)係以一解毒 有效量的保護劑處理。保護劑的解毒有效量歹 項技術者經由簡單實驗而輕易決定。 ‘ ' Λ 表Β1列出成分(a)與成分(b)之具體組合,其可說明 本發明之混合物、組成物與方法。表B1的第二棚列出 具體之成分(b)化合物(例如第一行的「草毒死 (AUidoch㈣」)。表B i的第三、第四與第五搁列出在針 對田間生長作物㈣魏料時,成分(b)化合物對成分 ⑻的重量比例範圍。因此,例如表B1第一行具體揭露 成分⑻(即索引表A中所標示的化合物^與草毒死之 組合物典型為以介於1:48至6:1的重量比例施用。表 Β1其餘行以類似方式架構。 195 25 201240602 表 成分(a) 化合物 化合物1 化合物1 化合物1 化合物1 化合物1 化合物1 化合物 化合物1 化合物1 化合物1 化合物 化合物 化合物1 化合物1 化合物 化合物 化合物1 化合物1 化合物1 化合物 化合物 化合物 化合物1 化合物1 成分(b) 草毒死(Allidochlor) 解草嗓(Benoxacor) 解毒喧 (Cloquintocet-mexyl) 苄草隆(Cumyluron) 解草胺腈(Cyometrinil) 咬酿菌胺(Cyprosu丨famide) 殺草隆(Diamuron) 氣丙稀胺(Dichlormid) •環隆酮(Dicyclonon) 增效峨(Dietholate) 略草丹(Dimepiperate) 解草°坐 (Fenchlorazole-ethyl) 解草咬(Fenclorim) 解草胺(Flurazole) 氟草肪(Fluxofenim) 解草惡 °i(Furilazole) 雙笨噁唑酸 (Isoxadifen-ethyl) 唑解草酯 (Mefenpyr-diethyl) 美伏时(Mephenate) 苯草酮(Methoxyphenone) 蔡二曱酸Sf (Naphthalic _anhydride) 解草腈(Oxabetrinil) 氣曱基)-2-甲基-1,: 二氧雜環戊烷(MG-191) 1-(氧雜-4-氮-螺[4.5]癸-4-基)-乙酮(AD-67) 1,6·二氫-1-(2-甲氧苯 基)-6-側氧基-2-苯基-5-嘧 啶羧酸乙酯 _重量比例 1:48 至 6:1 取典型 liiZl 17:1 1:6 至 168:1 iil至 3:1 1:48 至 12:1 1:48 至 12:1186 201240602 Ingredient (a) Ingredient (b) Typical weight ratio More typical weight ratio Most typical weight ratio Compound 1 Bicyclopyrone 1:42 to 27:1 1:14 to 9:1 1:5 to 2 :1 Compound 1 Bifenox 1:257 to 5:1 1:85 to 2:1 1:32 to 1:4 Compound 1 Bispyribac-sodium 1:10 to 1 12:1 1 :3 to 38:1 1:1 to 7:1 Compound 1 Bromacil 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Bromobutide 1 :384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Bromoxynil 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 1 Butachlor 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 1 Fluorine 0^ Grass S (Butafenacil) 1:42 to 27:1 1: 14 to 9:1 1:5 to 2:1 Compound 1 Butylate 1:1542 to 1:2 1:514 to 1:5 1:192 to 1:22 Compound 1 Benzene. Carfenstrole 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Carfentrazone-ethyl 1:128 to 9:1 1:42 to 3:1 1:16 to 1:2 Compound 1 Chlorimuron-ethyl 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 1 Chlorotoluron 1:768 To 2:1 1:256 to 1:2 1:96 to 1:11 Compound 1 Chlorsulfuron 1:6 to 168:1 1:2 to 56:1 1:1 to 11:1 Compound 1 West Cincosulfuron 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 1 Cinidon-ethyl 1:384 to 3:1 1:128 to 1 :1 1:48 to 1:6 Compound 1 Cinmethylin 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 1 Clethodim 1:48 To 24:1 1:16 to 8:1 1:6 to 2:1 Compound 1 Propdinafop-propargyl 1:20 to 56:1 1:6 to 19:1 1:2 to 4: 1 Compound 1 can be eliminated (Clomazone) 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Clomeprop 1:171 to 7:1 1:57 to 3 :1 1:21 to 1:3 Compound 1 Clopiralid 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Chlororanium-methyl 1:12 to 96:1 1:4 to 32:1 1:1 to 6:1 Compound 1 Benzene Cumyluron 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Cyanazine 1:384 to 3:1 1:128 to 1:1 1: 48 to 1:6 Compound 1 Cyclosulfamuron 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 1 Cycloxydim 1:96 to 12:1 1 :32 to 4:1 1:12 to 1:2 Compound 1 Cyhalofop 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 1 Daimuron 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Desmedipham 1:322 to 4:1 1:107 to 2:1 1:40 to 1:5 Compound 1 Dicamba 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Dichlobenil 1:1371 to 1:2 1:457 to 1:4 1:171 to 1:20 187 201240602 Ingredient (a) Ingredient (b) Typical weight ratio More typical weight ratio Most typical weight ratio Compound 1 DicklcKprop 1:925 to 2:1 1:308 to 1:3 1:115 to 1:13 Compound 1 曱基禾草灵(Diclofop-methyl) 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Diclosulam 1:10 to 112:] 1:3 to 38:1 1:1 to 7:1 Compound 1 Difenzoquat 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 1. Diflufenican 1:857 to 2:1 1:285 to 1:3 1:107 to 1:12 Compound 1 Diflufenzopyr 1:12 to 96:1 1:4 to 32 :1 1:1 to 6:1 Compound 1 Dimethachlor 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 1 Dimethametryn 1:192 To 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Dimethenamid-P 1:384 to 3:1 1:128 to 1:1 1:48 to 1: 6 Compound 1 Dithiopyr 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 has a Diuron 1:384 to 3:1 1:128 to 1 :1 1:48 to 1:6 Compound 1 EPTC 1:768 to 2:1 1:256 to 1:2 1:96 to 1:1] Compound 1 Esprocarb 1:1371 to 1:2 1 :457 to 1:4 1:171 to 1:20 Compound 1 Ethalfluralin 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Amisulfuron (Ethametsulfuron-methyl) 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 1 Ethoxyfen 1:8 to 135:1 1:2 to 45:1 1 :1 to 9:1 Compound 1 Ethoxysulfuron 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 Compound 1 Etobenzanid 1:257 to 5:1 1:85 to 2:1 1:32 to 1:4 Compound 1 Ethylpropanate (Fenoxaprop-ethyl) 1:120 to 10:1 1:40 to 4:1 1:15 to 1:2 Compound 1 Fenoxasulfone 1:85 to 14:1 1:28 to 5:1 1:10 to 1:2 Compound I Fentrazamide 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 1 Flazasulfuron 1:17 to 68:1 1:5 to 23: 1 1:2 to 5:1 Compound 1 Florasulam 1:2 to 420:1 1:1 to 140:1 2:1 to 27:1 Compound 1 Fluazifop-butyl ) 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Flucarbazone 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 1 Fluorotosulfuron 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 1 Flufenacet 1:257 to 5:1 1 :85 to 2:1 1:32 to 1:4 Compound 1 Flumetsulam 1:24 to 48:1 1:8 to 16:1 1:3 to 3:1 Compound 1 Fluoric acid ( Flumiclorac-pentyl) 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 compound 1 Flumioxazin 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 1 Fluometuron 1:384 to 3:1 1:128 to 1 :1 1:48 to::6 Compound 1 Flunarsulfuron 1:3 to 336:1 1:1 to 112:1 2:1 to 21:1 188 201240602 Composition (a) Composition (b) Typical weight ratio More typical weight ratio most typical weight ratio (Flupyrsulfuron-methyl) Compound 1 Fluridone]: 384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Fluorine ratio (Fluroxypyr ) 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 1 Flurtamone 1:857 to 2:1 1:285 to 1:3 1:107 to 1 :12 Compound 1 Fluthiacet-methyl 1:48 to 42:1 1:16 to 14:1 1:3 to 3:1 Compound 1 Fomesafen 1:96 to 12 :1 1:32 to 4:1 1:12 to 1:2 Compound 1 Diamsulfuron 1:13 to 84:1 1:4 to 28:1 1:1 to 6:1 Compound 1 Grass Glufosinate 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 1 Glyphosate 1:288 to 4:1 1:96 to 2:1 1: 36 to 1:4 Compound 1 Halosulfuron-methyl 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 1 Haloxy fop-methyl 1:34 to 34:1 1:11 To 12:1 1:4 to 3:1 Compound 1 Hexazinone 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 methoxy 0 rice straw (Imazamox ) 1:13 to 84:1 1:4 to 28:1 1:1 to 6:1 Compound 1 Astringency. Imazapic 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 Compound 1 Imazapyr 1:85 to 14:1 1:28 to 5:1 1 :10 to 1:2 Compound 1 Imazaquin 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 1 Imazethabenz-methyl 1:171 to 7 :1 1:57 to 3:1 1:21 to 1:3 Compound 1 Imazamox 1:24 to 48:1 1:8 to 16:1 1:3 to 3:1 Compound 1 Izozosulfuron 1:27 to 42:1 1:9 to 14:1 1:3 to 3:1 Compound 1 Indanofan 1:342 to 4:1 1:114 to 2:1 1:42 to 1:5 Compound 1 Indaziflam 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 1 Iodosulfuron-methyl 1:3 to 336:1 1:1 to 112:1 2:1 to 21:1 Compound 1 Ioxynil 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Ipfencarbazone 1:85 To]4:1 1:28 to 5:1 1:10 to 1:2 Compound 1 Isoproturon 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Isoxaben 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 1 Isomalt _ (Isoxaflutole) 1:60 to 20:1 1:20 to 7:1 1:7 to 2:1 Compound 1 Lactofen 1:42 to 27:1 1:14 to 9:1 1: 5 to 2:1 Compound 1 Lenacil 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 has a dragon (Linuron) 1:384 to 3:1 1 :128 to 1:1 1:48 to 1:6 Compound 1 MCPA 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 MCPB 1:288 to 4:1 1:96 To 2:1 1:36 to 1:4 189 201240602 Composition (a) Ingredient (b) Typical weight ratio More typical weight ratio Most typical weight ratio Compound 1 Hecoprop 1:768 to 2:1 1: 256 to 1:2 1:96 to 1:11 Compound 1 Mefenacet 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Mefluidide 1 :192 to 6:1 ]:64 to 2:1 1:24 to 1:3 Compound 1 Mesosulfuron-methyl 1:5 to 224:1 1:1 to 75:1 1:1 to 14 :1 Compound 1 Mesotrione 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 1 tam 〇 Me Me Me (Metamifop) 1:42 to 27:1 1 :14 to 9:1 1:5 to 2:1 Compound 1 Metazamide (Metazachlo r) 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Diether gas Metazosulfuron 1:25 to 45:] 1:8 to 15:1 1 :3 to 3:1 Compound 1 Methabenzthiazuron 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 1 Metolachlor 1:768 to 2: 1 1:256 to 1:2 1:96 to 1:11 Compound 1 Mesosulam 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 1 Metribuzin 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Metsulfuron-methyl 1:2 to 560:1 1:1 to 187:1 3 :1 to 35:1 Compound 1 Molinate 1:1028 to 2:1 1:342 to 1:3 1:128 to 1:15 Compound 1 Napropamide 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Naptalam 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Nicosulfuron 1:12 to 96:1 1:4 to 32:1 1:1 to 6:1 Compound 1 Norflurazon 1:1152 to 1:1 1:384 to 1:3 1:144 to 1: 16 Compound 1 Orbencarb 1:1371 to 1:2 1:457 to 1:4 1:171 to 1:20 Compound 1 Orthosulfamuron 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 Compound 1 Oryzalin 1:514 to 3:1 1:171 To 1:2 1:64 to 1:8 Compound 1 Fast 0 Oxadiargyl 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Oxadiazon 1:548 to 3:1 1:182 to 1:2 1:68 to 1:8 Compound 1 Oxasulfuron 1:27 to 42:1 1:9 to 14:1 1:3 to 3 :1 Compound 1 βoxa 17 oxolone (Oxaziclomefone) 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 1 Oxyfluorfen 1:384 to 3:1 1 :128 to 1:1 1:48 to 1:6 Compound 1 Paraquat 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Pendimethalin 1:384 To 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Penoxsulam 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 1 Benzene Penthoxamid 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Pentoxazone 1:102 to 12:1 1:34 to 4: 1 1:12 to 1:2 Compound 1 Behenedipham 1:102 to 12: 1 1:34 to 4:1 1:12 to 1:2 Compound 1 Picloram 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 190 201240602 Composition (a) Composition (b) Typical weight ratio More typical weight ratio Most typical weight ratio Compound 1 Fluorophene (Picolinafen) 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 1 σ sit Pinoxaden 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 1 Pretilachlor 1:192 to 6:1 1:64 to 2:1 1 :24 to 1:3 Compound 1 Primisulfuron-methyl 1:8 to 135:1 1:2 to 45:1 1:] to 9:1 Compound 1 Prodiamine 1:384 To 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Profoxydim 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 1 Prometryn 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Propachlor 1:1152 to 1:1 1:384 to 1:3 1:144 to 1:16 Compound 1 Propanil 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Propaquizafop 1:48 to 24:1 1:16 to 8:1 1:6 to 2:1 Compound 1 Propoxycarbazone 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 1 Propyrisulfuron 1:17 to 68:1 1:5 to 23: 1 1:2 to 5:1 Compound 1 Propyzamide 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Prosulfocarb 1:1200 to 1:2 1:400 to 1:4 1:150 to 1:17 Compound 1 Prosulfuron 1:6 to 168 1 1:2 to 56:1 1:1 to 11:1 Compound 1 Double sitting Pyraclonil 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 1 ° Pyraflufen-ethyl 1:5 to 224:1 1:1 to 75: 1 1:1 to 14:1 Compound 1 Continued σ σ (Pyrasulfotole) 1:13 to 84:1 1:4 to 28:1 1:1 to 6:1 Compound 1 Pyrazolynate 1 :857 to 2:1 1:285 to 1:3 1:107 to 1:12 Compound 1 Pyrazosulfuron-ethyl 1:10 to 112:1 1:3 to 38:1 1:1 to 7: 1 Compound 1 Pyrazoxyfen 1:5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 1 Pyrybenzoxim 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 1 pyributicarb 1 :384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Pyridate 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 1 Ring Syrup (Pyriftalid) 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 1 Pyryminobac-methyl 1:20 to 56:1 1:6 Until 19:1 1:2 to 4:1 Compound 1 Shouting Pyrimisulfan 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 1 Shyrithiobac 1:24 to 48:1 1:8 to 16:1 1:3 to 3:1 Compound 1 Pyroxasulfone 1:85 to 14:1 1:28 to 5:1 1:10 to 1:2 Compound 1 Pyroxsulam 1:5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 1 Quinclorac 1:192 to 6:1 1: 64 to 2:1 1:24 to 1:3 Compound 1 Ethyl fast-moving grass 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 191 201240602 Composition (a) Composition (b) Typical weight ratio more typical weight ratio most typical weight ratio (Quizalofop-ethyl) Compound 1 Jade 0 Rimsulfuron 1:13 to 84:1 1:4 to 28:1 1:1 to 6:1 Compound 1 Saflufenacil 1:25 to 45: 1 1:8 to 15:1 1:3 to 3:1 Compound 1 Sethoxydim 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 1 Simazine) 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Sulcotrione 1:120 to 10:1 1:40 to 4:1 1:15 to 1 :2 Compound 1 Sulfentrazone 1:147 to 8:1 1:49 to 3:1 1:18 to 1:3 Compound] Sulfometuron-methyl 1:34 to 34:1 1:11 to 12:1 ]:4 to 3:1 Compound 1 Sulfosulfuron 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 1 Tebuthiuron 1:384 to 3:1 1:128 to 1:1 1:48 to]:6 Compound 1 Tefuryltrione 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 1 Ring 嗣(Tembotrione) 1:31 to 37:1 1:10 to 13:1 1:3 to 3:1 Compound 1 Depraloxydim 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 1 Terbacil 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 1 Terbuthylatrazine 1:857 to 2:1 1:285 to 1:3 1 :107 to 1:12 Compound 1 Terbutryn ]: 192 to 6:1 1:64 2:1 1:24 to]:3 Compound 1 Thenylchlor 1:85 to 14:1 1:28 to 5:1 1:10 to]:2 Compound 1 Thiazopyr 1:384 To 3:1 1:128 to 1:1 1:48 to 1:6 Compound 1 Thiencarbazone 1:3 to 336:] 1:1 to 12:1 2:1 to 21: 1 Compound 1 Thifensulfuron-methyl ]: 5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 1 Thiobencarb 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 1 Topramazone 1:6 to 168:1 1:2 to 56:1 1:1 to 11:1 Compound 1 Tralkoxydim 1 :68 to]7:1 1:22 to 6:1 1:8 to 2:1 Compound 1 Triallate 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 1 Triasu丨furon 1:5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 1 Triaziflam 1:171 to 7:1 1: 57 to 3:1 1:21 to 1:3 Compound 1 Tribenuron 1:3 to 336:1 1:1 to 112:1 2:1 to 21:1 Compound 1 Triclopyr 1 :192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 1 Trifloxys Ulfuron) 1:2 to 420:1 1:1 to 140:1 2:1 to 27:1 Compound] Trifluralin 1:288 to 4:1 1:96 to 2:1 1:36 to 1 :4 Compound 1 Triflusulfuron-methyl 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 1 Tritosulfuron 1:13 to 84: 1 1:4 to 28:1 1:1 to 6:1 192 201240602 Table A2 is constructed as shown in the above table Ai, except that the items below the heading of the “Component (a)” column are the following components (a) Replacement. The compound 2 in the component (a) 襕 is shown in the index table A. Therefore, for example, in Table A2 5, the "Component (a)" block headers all describe "Compound 2" (ie, Compound 2 indicated in Index Table A), and the first line below the heading of Table A2 is specifically disclosed. Mixture of Compound 2 with 2,4-D. Tables A3 through A34 are structured in a similar manner. Table No. Component (a) Shed Item A2 Compound 2 A3 Compound 3 A4 Compound 4 A5 Compound 5 A6 Compound 6 A7 Compound 7 A8 Compound 8 A9 Compound 9 A10 Compound 10 All Compound 11 A12 Compound 12 A13 Compound 13 A14 Compound 14 A15 Compound 15 A16 Compound 16 A17 Compound 17 A18 Compound 18 Table No. Component (a) Block A19 Compound 19 A20 Compound 20 A21 Compound 21 A22 Compound 22 A23 Compound 23 A24 Compound 24 A25 Compound 25 A26 Compound 26 A27 Compound 27 A28 Compound 28 A29 Compound 29 A30 Compound 30 A31 Compound 31 A32 Compound 32 A33 Compound 33 A34 Compound 34 In some instances, a combination of a compound of the present invention with other biologically active (especially herbicidal) compounds or agents (i.e., active ingredients) may cause greater than weeds The effect of greater-than-additive (ie, synergy) and/or for crops or other plants to be preserved may result in an effect of 193 201240602 being less than additive (iess-th). Rationality is the ability to reduce the amount of active ingredient in the dose, to ensure effective control, and to use a larger amount of active ingredient to provide effective weed control without causing damage to unwanted crops. When the herbicidal active ingredient produces a synergistic effect on weeds (under the application of agronomics: the rate of application of the level of weed control), the combination of such production costs and environmental burden can bring benefits. When weeding activity When the ingredients have a protective effect on the crop, such a composition can bring about the benefit of enhancing crop protection by reducing weed competition. It is noted that the composition of the present invention and at least one other herbicidal active ingredient are worthy of special attention. A composition which is different from the compound of the present invention in the action of other herbicidal active ingredients. In some examples, at least one composition having a similar control range but different action positions: a composition of other herbicidal active ingredients, which is particularly useful in resistance management Benefits. Accordingly, the compositions of the present invention may further comprise at least one additional herbicidal active ingredient (with a herbicidally effective amount) which has a similar range of control but different positions of action. The compounds of the invention may also be combined with a herbicide protectant Improve the completeness of certain crops, such as grass poisoning (aiiid〇chl〇r), solution Grasshopper (ben〇XaC〇r), BCS (1·bromo-4-[(gas f)sulfonyl]benzene), cloquintocet-mexyl, cy〇metrinil, ring Cyprosulfonamide, dixypropylamine (dichl〇rmid), 4-mercaptoethyl)-1-oxa-4-azospiro[4 5]decane (M〇N466〇), 2_ (dioxamethyl)-2-mercapto-1,3-dioxolane (MG 191), dicyclodonone (dicydonon), synergistic phosphorus (dieth〇丨), fenchlorazole -ethyl), fend 〇rim, oxalic acid 201240602 (flurazole), flusofenim, furilazole, isoxadifen-ethyl, hydrazine Mefenpyr-diethyl, mefrica, methoxyphenone ((4-methoxy-3-methylphenyl)(3-mercaptophenyl)fluorenone), naphthalene dinonanoate Naphthalic anhydride (1,8-naphthalene dicarboxylic anhydride) and oxabetrinil. A detoxifying effective amount of the herbicide protecting agent can be applied simultaneously with the compound of the present invention or as a seed treatment. One aspect of the invention relates to a herbicidal mixture comprising a hair A compound and a detoxifying effective amount of a herbicide protectant. Seed treatment is particularly useful for the selective control of weeds because it physically limits detoxification to crop plants. Thus, a particularly useful embodiment of the invention is a A method for selectively controlling the growth of an undesired plant in a crop, comprising contacting the locus of the crop with a herbicidally effective amount of a compound of the invention, wherein the seed of the crop (the crop line is grown therefrom) is effective as a detoxification Amount of protective agent treatment. The detoxifying effective amount of the protective agent is easily determined by a simple experiment. ‘ ' Λ Table 1 lists specific combinations of component (a) and component (b), which illustrate the mixtures, compositions and methods of the present invention. The second shed of Table B1 lists the specific component (b) compounds (for example, the first row of "Aidoch (A)"). The third, fourth and fifth of Table B i are listed for growing crops in the field. (4) The range of the weight ratio of the component (b) to the component (8) in the case of the Wei material. Therefore, for example, the first line of Table B1 specifically discloses the component (8) (that is, the compound indicated by the index table A and the herbicide composition is typically Apply in a weight ratio of 1:48 to 6:1. The remaining rows of Table 1 are structured in a similar manner. 195 25 201240602 Table ingredients (a) Compound 1 Compound 1 Compound 1 Compound 1 Compound 1 Compound 1 Compound 1 Compound 1 Compound 1 Compound Compound 1 Compound 1 Compound Compound 1 Compound 1 Compound 1 Compound Compound Compound 1 Compound 1 Ingredient (b) Allidochlor Benoxacor Detoxification (Cloquintocet-mexyl) Beclozil (Cloquintocet-mexyl) Cumyluron) Cyometrinil Cyprosu丨famide Diamuron Dichlormid • Dicyclonon Synergistic (Diethpipe) Dimepiperate, Fenchlorazole-ethyl, Fenburrim, Flurofenim, Furilazole, Bismuth oxalate Isoxadifen-ethyl) Mefenpyr-diethyl Mephenate Methotone Sodium (Naphthalic _anhydride) Oxabetrinil -2--methyl- 1, dioxolane (MG-191) 1-(oxa-4-nitro-spiro[4.5]indol-4-yl)-ethanone (AD-67) 1,6·dihydro-1 -(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate ethyl ester _ weight ratio 1:48 to 6:1 take typical liiZl 17:1 1:6 to 168: 1 iil to 3:1 1:48 to 12:1 1:48 to 12:1

1:12 至]68:1 1:4 至 1:1 至 6: 表B2係如同上表B1者建構’除了「成分(a)」攔標題下 方的項目係以下示各別成分⑷欄項目置換。因此,例如 196 201240602 在表B2中,「成分⑻」欄標題全部皆敘述「化合物2」 (即標示於索引表A中之化合物2),並且表B2之欄標 題下方的第一行具體揭露化合物2與草毒死之混合 物。表B2至B34係以類似方式架構。 表編號 成分(a)爛項目 B2 化合物2 B3 化合物3 B4 化合物4 B5 化合物5 B6 化合物6 B7 化合物7 B8 化合物8 B9 化合物9 B10 化合物10 B11 化合物11 B12 化合物12 B13 化合物13 B14 化合物14 B15 化合物15 B16 化合物16 B17 化合物17 B18 化合物18 表編號 成分(a)欄項目 B19 化合物19 B20 化合物20 B21 化合物2] B22 化合物22 B23 化合物23 B24 化合物24 B25 化合物25 B26 化合物26 B27 化合物27 B28 化合物28 B29 化合物29 B30 化合物30 B31 化合物31 B32 化合物32 B33 化合物33 B34 化合物34 值得注意者為包含下列之組成物,即一本發明化合 物(以一除草有效量)、至少一種選自由其他除草劑與 除草劑保護劑(以一有效量)所組成之群組的額外活性 10 成分以及至少一種選自由界面活性劑、固體稀釋劑與液 體稀釋劑所組成之群組的成分。 對於較佳防治非所欲植物(例如由於諸如協同作用 而造成的較低使用率、更廣泛的雜草防治範圍或增進作 物安全)或防止抗性雜草之發展較佳者為一本發明化合 197 201240602 物與一除草劑之混合物,該除草劑係選自由2,4-D、草 殺淨(ametryne)、胺環β比克(aniinocyclopyrachlor)、氣氨 基0比咬酸(aminopyralid)、草脫淨(atrazine)、克草 (bromacil)、漠苯腈(bromoxynil)、漠苯腈辛酸醋 5 (br〇moxynil octanoate)、乙唾草酮(carfentrazone-ethyl)、 氣嘴續隆(chlorimuron-ethyl)、氣續隆(chlorsulfuron)、 畢克草(clopyralid)、畢克草醇胺(clopyralid-olamine)、 麥草畏(dicamba)與其二乙二醇銨鹽、二甲銨鹽、鉀鹽與 鋼鹽、°比氣草胺(diflufenican)、汰草滅(dimethenamid)、 10 汰草滅-P(dimethenamid-P)、達有龍(diuron)、雙氟磺草 胺(florasulam)、噻草胺(flufenacet)、唑嘧磺草胺 (flumetsulam)、丙炔氟草胺(flumioxazin)、氟啶嘧磺隆 (flupyrsulfuron-methyl)、 氟咬嘴續隆納 (flupyrsulfuron-methyl-sodium)' 氟氣比(fluroxypyr)、嘉 15 磷塞(glyphosate)(尤其是嘉磷塞異丙銨、嘉磷塞鈉、嘉 磷塞鉀、嘉填塞三甲基硫鹽)、菲殺淨(hexazinone)、σ米 草酯(imazamethabenz-methyl)、滅草啥(imazaquin)、咪 草煙(imazethapyr)、曱基碘磺隆(iodosulfuron-methyl)、 乳氟禾草靈(lactofen)、環草定(lenacil)、理有龍 2〇 (linuron)、MCPA與其二甲銨鹽、鉀鹽與鈉鹽、MCPA- 異辛基、MCPA-硫乙基、甲磺胺磺隆 (mesosulfuron-methyl)、S·莫多草(S-metolachlor)、滅必 淨(metribuzin)、曱項隆(metsulfuron-methyl)、煙嘴續隆 (nicosulfuron)、復祿芬(oxyfluorfen)、施得圃 25 (pendimethalin)、唾啦草酯(pinoxaden)、拿草特 (pronamide)、氟續隆(prosulfuron)、派羅克殺草石風 201240602 (pyroxasulfone)、咬石黃草胺(pyroxsulam)、快克草 (quinclorac)、玉喊績隆(rimsulfuron)、喊咬特草驗 (saflufenacil)、甲確草胺(sulfentrazone)、喧吩續隆 (thifensulfuron-methyl)、醚苯續隆(triasulfuron)、苯確隆 (tribenuron-methyl)、三氣比(triclopyr)、丁氧乙基三氣 比(triclopyr-butotyl)與三氣比三乙基錢 (triclopyr-triethylammonium)。 10 15 20 下列試驗展現了本發明化合物對特定雜草的除草 效果。然而,該化合物所提供的雜草防治不限於所試驗 的植物物種。請參見索引表A以取得化合物說明。下列 縮寫係用於索引表中如下:「Cmpd」意指化合物,吣 為甲基’ Ph為苯基,噻吩意指噻吩而c_pr意指環丙美 屮NMR光譜係以在CDC13中偏移自四甲基石夕燒^在 400 MHz之低場ppm來記述,除非另有註明;「s音 單峰,「m」意指多峰’rbr s」意指寬單峰,: 雙峰,「dd」意指雙雙峰,「t」意指三峰,「td ^j 雙峰,「dt」意指雙三峰而「q」意指四重峰。縮」寫^二 表示「實例」,且其後之數字意指該化合 ^ 中製備。在下列索引表中: 實例 「二氧雜螺[4.5]癸_8-基」意指1:12 to]68:1 1:4 to 1:1 to 6: Table B2 is constructed as shown in Table B1 above. Except for the component (a), the item below the title is the following item (4). . Thus, for example, 196 201240602 In Table B2, the headings of the "Component (8)" column all describe "Compound 2" (ie, Compound 2 indicated in Index Table A), and the first row below the heading of Table B2 specifically discloses the compound. 2 mixture with grass poison. Tables B2 through B34 are structured in a similar manner. Table No. Component (a) Rotten Item B2 Compound 2 B3 Compound 3 B4 Compound 4 B5 Compound 5 B6 Compound 6 B7 Compound 7 B8 Compound 8 B9 Compound 9 B10 Compound 10 B11 Compound 11 B12 Compound 12 B13 Compound 13 B14 Compound 14 B15 Compound 15 B16 Compound 16 B17 Compound 17 B18 Compound 18 Table No. Component (a) Column Item B19 Compound 19 B20 Compound 20 B21 Compound 2] B22 Compound 22 B23 Compound 23 B24 Compound 24 B25 Compound 25 B26 Compound 26 B27 Compound 27 B28 Compound 28 B29 Compound 29 B30 Compound 30 B31 Compound 31 B32 Compound 32 B33 Compound 33 B34 Compound 34 It is noted that the composition comprises a compound of the invention (in a herbicidally effective amount), at least one selected from the group consisting of other herbicides and herbicides. An additional active 10 component of the group of agents (in an effective amount) and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents. For better control of undesired plants (eg, due to lower usage rates such as synergistic effects, broader range of weed control or improved crop safety) or prevention of development of resistant weeds, a combination of the invention is preferred. 197 201240602 A mixture of a herbicide and a herbicide selected from the group consisting of 2,4-D, ametryne, aninocyclopyrachlor, aminopyralid, and turf Atrazine, bromacil, bromoxynil, br〇moxynil octanoate, carfentrazone-ethyl, chlorimuron-ethyl , chlorsulfuron, clopyralid, clopyralid-olamine, dicamba and its diethylene glycol ammonium salt, dimethylammonium salt, potassium salt and steel salt, °Diflufenican, dimethenamid, 10 dimethenamid-P, diuron, florasulam, flufenacet , flumetsulam, flomioxazin, fluoride Flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium's fluroxypyr, glyphosate (especially jiaphosphine isopropylammonium, jiaphos) Sodium, Jiaphosate potassium, Jiachao trimethylsulfate), hexazinone, imazamethabenz-methyl, imazaquin, imazethapyr, sulfhydryl Iodosulfuron-methyl, lactofen, lenacil, linuron, MCPA and its dimethylammonium salt, potassium and sodium salts, MCPA-iso Octyl, MCPA-thioethyl, mesosulfuron-methyl, S-metolachlor, metribuzin, metsulfuron-methyl, cigarette holder Nicosulfuron), oxyfluorfen, pendimethalin, pinoxaden, pronamide, prosulfuron, pyroxasulfone, 201240602 (pyroxasulfone), Bitroxsulam, quinclorac, rimsulfuron, shouting (saflu) Fenacil), sulfentrazone, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triclopyr, butoxyethyl The triclopyr-butotyl and trigaster (trilopyr-triethylammonium). 10 15 20 The following test demonstrates the herbicidal effect of the compounds of the invention on specific weeds. However, the weed control provided by the compound is not limited to the plant species tested. See index table A for a description of the compound. The following abbreviations are used in the index table as follows: "Cmpd" means a compound, 吣 is methyl 'Ph is phenyl, thiophene means thiophene and c_pr means ciprofloxacin NMR spectroscopy to shift from CDC13 The base stone Xi burning ^ is described in the low field ppm of 400 MHz, unless otherwise noted; "s sound single peak, "m" means multi-peak 'rbr s" means wide single peak,: double peak, "dd" It means double peaks, "t" means three peaks, "td ^j double peaks, "dt" means double triplets and "q" means quadruple peaks. Shrinking "writes two" means "instance", and the following number means that the compound is prepared in ^. In the following index table: Example "Dioxaspiro[4.5]癸_8-yl" means

「四氫-2-甲基·吲唑_5•基」意指 199 25 201240602"Tetrahydro-2-methyl-carbazole _5•yl" means 199 25 201240602

「A-1A」意指: Ο"A-1A" means: Ο

οο

「Α-1Β」意指: ο"Α-1Β" means: ο

15 「Α-3Α」意指 ο15 “Α-3Α” means ο

201240602 1-(1,3-二乳雜環戍烧-2-基)丙-3-基」意指201240602 1-(1,3-Di-heterocyclic pyridin-2-yl)propan-3-yl" means

;以及 5 「2_(1,3_二氧雜環戊烷-2_基)戊-5-基」意指; and 5 "2_(1,3_dioxol-2-yl)pent-5-yl" means

10 索引表A 〇 〇 化合物 Ν R1 、R2 R2 A m.p.(°C) 1 (Ex. 1) 二氧雜螺[4.5]癸-8-基 Ph A-1A 氺 2 (Ex. 2) -CH2CH=NOCH3 Ph A-1A 氺 3 二氧雜螺[4.5]癸-8-基 Ph(3-F) A-1A 氺氺 4 二氧雜螺[4.5]癸-8-基 Ph(3-F) A-3A * * 5 二氧雜螺[4.5]癸-8-基 Ph(3-Me) A-1A 本氺 6 二氧雜螺[4.5]癸-8-基 Ph(3-Me) A-3A 氺氺 7 二氧雜螺[4.5]癸-8-基 5-C1-3-吡啶基 A-1A 本本 8 二氧雜螺[4.5]癸-8-基 3-d比咬基 A-1A 本氺 9 二氧雜螺[4.5]癸-8-基 Ph A-3A 氺氺 10 二氧雜螺[4.5]癸-8-基 c-Pr A-1A 氺氺 11 二氧雜螺[4.5]癸-8-基 c-Pr A-3A 本氺 12 二氧雜螺[4.5]癸-8-基 Ph(3-OMe) A-1A 本氺 201240602 13 二氧雜螺[4.5]癸-8-基 Ph(3-OMe) A-3A 本氺 14 二氧雜螺[4.5]癸-8-基 2-噻吩基 A-1A * * 15 二氧雜螺[4.5]癸-8-基 2-喧吩基 A-3A 本本 16 二氧雜螺[4.5]癸-8-基 2-噻吩基 A-1B * * 17 二氧雜螺[4.5]癸-8-基 3-售吩基 A-1A 18 二氧雜螺[4.5]癸-8-基 3-噻吩基 A-1A 19 四氫-2-曱基-吲。坐-5-基 Ph A-1A 20 1-嗎啉基 Ph A-1A 21 1-嗎啉基 Ph A-3A 22 (Ex. 3) 1-嗎啉基 c-Pr A-1A 本氺氺 23 (Ex. 4) 1-嗎啉基 c-Pr A-3A 5 24 1-嗎啉基 Ph(3-F) A-1A *本 25 1-嗎啉基 Ph(3-F) A-3A * * 26 1-(3-二氧雜環戊烷-2-基)丙-3-基 c-Pr A-1A * * 27 1-(3-二氧雜環戊烷-2-基)丙-3-基 Ph A-1A * * 28 1-(3-二氧雜環戊烷-2-基)丙-3-基 Ph A-3A 本本 29 1-(3-二氧雜環戊烷-2-基)丙-3-基 c-Pr A-3A 本氺 30 1-(3-二氧雜環戊烷-2-基)丙-3-基 3-噻吩基 A-1A * * 31 1-0,3-二氧雜環戊烷-2-基)丙-3-基 3-噻吩基 A-1B 本本 32 1-(1,3-二氧雜環戊烷-2-基)丙-3-基 3-°g吩基 A-3A 33 2-(1,3-二氧雜環戊烷-2-基)戊-5-基 Ph A-3A * * 34 2-(1,3-二氧雜環戊烷-2-基)戊-5-基 Ph A-1A *氺 *請參見合成實例以取得1H NMR數據》請參見索引表E以取得咕 NMR數據10 Index Table A 〇〇Compound Ν R1 , R2 R2 A mp(°C) 1 (Ex. 1) Dioxaspiro[4.5]癸-8-yl Ph A-1A 氺2 (Ex. 2) -CH2CH= NOCH3 Ph A-1A 氺3 Dioxaspiro[4.5]癸-8-yl Ph(3-F) A-1A 氺氺4 Dioxaspiro[4.5]癸-8-yl Ph(3-F) A -3A * * 5 Dioxaspiro[4.5]癸-8-yl Ph(3-Me) A-1A Benzo 6 Dioxaspiro[4.5]癸-8-yl Ph(3-Me) A-3A氺氺7 Dioxaspiro[4.5]癸-8-yl 5-C1-3-pyridyl A-1A Ben 8 Dioxaspiro[4.5]癸-8-yl 3-d ratio bite A-1A氺9 dioxaspiro[4.5]癸-8-yl Ph A-3A 氺氺10 dioxaspiro[4.5]癸-8-yl c-Pr A-1A 氺氺11 dioxaspiro[4.5]癸-8-based c-Pr A-3A 氺12 dioxaspiro[4.5]癸-8-yl Ph(3-OMe) A-1A 本氺201240602 13 Dioxaspiro[4.5]癸-8-yl Ph(3-OMe) A-3A Ben 氺14 Dioxaspiro[4.5]癸-8-yl 2-thienyl A-1A * * 15 Dioxaspiro[4.5]癸-8-yl 2- porphin Base A-3A Ben16 Dioxaspiro[4.5]dec-8-yl 2-thienyl A-1B**17 Dioxaspiro[4.5]癸-8-yl 3-supplemental A-1A 18 II Oxaspiro[4.5]dec-8-yl 3-thienyl A-1A 19 tetrahydro-2-indenyl-indole. Sodium-5-yl Ph A-1A 20 1-morpholinyl Ph A-1A 21 1-morpholinyl Ph A-3A 22 (Ex. 3) 1-morpholinyl c-Pr A-1A 氺氺23 (Ex. 4) 1-morpholinyl c-Pr A-3A 5 24 1-morpholinyl Ph(3-F) A-1A *本25 1-morpholinyl Ph(3-F) A-3A * * 26 1-(3-dioxol-2-yl)propan-3-yl c-Pr A-1A * * 27 1-(3-dioxol-2-yl)propene- 3-based Ph A-1A * * 28 1-(3-dioxol-2-yl)propan-3-yl Ph A-3A The present 29 1-(3-dioxolane-2 -yl)prop-3-yl c-Pr A-3A 氺30 1-(3-dioxol-2-yl)propan-3-yl 3-thienyl A-1A * * 31 1- 0,3-dioxol-2-yl)propan-3-yl 3-thienyl A-1B 32 1-(1,3-dioxolan-2-yl)propane-3 -yl 3-g phenyl A-3A 33 2-(1,3-dioxolan-2-yl)pent-5-yl Ph A-3A * * 34 2-(1,3-two Oxol-2-yl)pent-5-yl Ph A-1A *氺* See Synthesis Examples for 1H NMR Data. See Index Table E for 咕 NMR Data

索引表BIndex table B

化合物 _____A' m.p. (°〇 7Q 二氧雜螺[4.5]癸-8-基 5-C1-3-吡啶基 Α·-1 ** 201240602 8Q 二氧雜螺[4.5]癸-8-基 3-°比咬基 A' 19Q 四氮-2 -曱基-α弓|β坐-5-基 Ph A, 22Q 1-嗎啉基 c-Pr A, 24Q 1-嗎啉基 Ph(3-F) A, 26Q 1-(3-二氧雜環戍烧-2·基)丙-3-基 c-Pr A, 請參見合成實例以取得1H NMR數據。Compound _____A' mp (°〇7Q dioxaspiro[4.5]癸-8-yl 5-C1-3-pyridyl Α·-1 ** 201240602 8Q Dioxaspiro[4.5]癸-8-yl 3 -° ratio bite A' 19Q tetrazo-2-indolyl-α bow|β sit-5-yl Ph A, 22Q 1-morpholinyl c-Pr A, 24Q 1-morpholinyl Ph (3-F A, 26Q 1-(3-dioxanthracen-2-yl)propan-3-yl c-Pr A, see Synthesis Examples for 1H NMR data.

索引表CIndex table C

化合物 R1 R2 m.p. (°C) 1R (Ex. 1) 二氧雜螺[4.5]癸-8-基 Ph 本 2R (Ex. 2) -CH2CH=NOCH3 Ph 本 7R 二氧雜螺[4.5]癸-8-基 5-C1-3-吡啶基 本本 8R 二氧雜螺[4.5]癸-8-基 3-°比咬基 * 1 HR 二氧雜螺[4.5]癸-8-基 c-Pr 氺本 14R 二氧雜螺[4.5]癸-8-基 2-噻吩基 氺本 17R 二氧雜螺[4.5]癸-8-基 3-噻吩基 19R 四氮-2 -曱基-〇引〇坐-5 -基 Ph ** 22R 1-嗎啉基 c-Pr 本水 25R 1-嗎啉基 Ph(3-F) 本本 26R 1二(3-二乳雜環戍烧-2_基)丙-3_基 c-Pr 本本 3 OR 1-(3-二氧雜環戊烷-2-基)丙-3-基 3-噻吩基 氺1 33R 2·(3-二氧雜環戍烧-2-基)-戍_5·基 Ph 氺本 10 1Compound R1 R2 mp (°C) 1R (Ex. 1) Dioxaspiro[4.5]癸-8-yl Ph This 2R (Ex. 2) -CH2CH=NOCH3 Ph Ben 7R Dioxaspiro[4.5]癸- 8-based 5-C1-3-pyridine basic 8R dioxaspiro[4.5]癸-8-yl 3-° ratio bite base * 1 HR dioxaspiro[4.5]癸-8-yl c-Pr 氺The 14R dioxaspiro[4.5]dec-8-yl 2-thienyl sulfonyl 17R dioxaspiro[4.5]dec-8-yl 3-thienyl 19R tetrazir-2-yl-yl-anthracene -5 -yl Ph ** 22R 1-morpholinyl c-Pr water 25R 1-morpholinyl Ph(3-F) Ben 26R 1 bis(3-di-heterocyclic oxime-2_yl)- 3_based c-Pr, 3 OR 1-(3-dioxol-2-yl)propan-3-yl-3-thienylindole 1 33R 2·(3-dioxanthene-2 -基)-戍_5·基P 氺本10 1

請參見合成實例以取得1H NMR數據。2請參見索引表E以取得1H 2 NMR數據 201240602See Synthesis Examples for 1H NMR data. 2 See index table E for 1H 2 NMR data 201240602

索引表D ο ο 化合物 R1 R2 R23 m.p. (°C) IS (Ex. 1) 二氧雜螺[4.5]癸-8-基 Ph Me ♦ 2S (Ex. 2) -CH2CH=NOCH3 Ph Me * 7S 二氧雜螺[4.5]癸-8-基 5-C1-3-吡啶基 Me 木氺 8S 二氧雜螺[4.5]癸-8-基 3·°比咬基 Me 氺氺 11S 二氧雜螺[4.5]癸-8-基 c-Pr Me 19S 四氫-2-曱基-0引。坐-5-基 Ph Me 木本 22S 1-嗎啉基 c-Pr Me 25S 1-嗎啉基 Ph(3-F) Me * * 26S 1-(3-二氧雜環戊烷-2-基)丙-3-基 c-Pr Me * * 30S 1-(3_二氧雜環戊院-2-基)丙-3-基 3-嘆吩基 Me 氺本Index Table D ο ο Compound R1 R2 R23 mp (°C) IS (Ex. 1) Dioxaspiro[4.5]癸-8-yl Ph Me ♦ 2S (Ex. 2) -CH2CH=NOCH3 Ph Me * 7S II Oxyspiro[4.5]癸-8-yl 5-C1-3-pyridyl Me 氺8S Dioxaspiro[4.5]癸-8-yl 3·° ratio biting base Me 氺氺11S dioxaspiro[ 4.5] 癸-8-yl c-Pr Me 19S tetrahydro-2-indenyl-0. Sodium-5-based Ph Me woody 22S 1-morpholinyl c-Pr Me 25S 1-morpholinyl Ph(3-F) Me * * 26S 1-(3-dioxol-2-yl )prop-3-yl c-Pr Me * * 30S 1-(3_dioxolan-2-yl)propan-3-yl 3-thinyl Me 氺

Κ ^R2 5 *請參見合成實例以取得1HNMR數據。Κ ^R2 5 * Please refer to the synthesis example to obtain 1H NMR data.

索引表EIndex table E

Cmpd.咕NMR數據或M.S.數據‘_ 3 469 4 495 5 465 6 491 δ 16.42 (s, 1H), 8.68 (d, 1H), 8.58 (s, 1H), 7.86 (s, 1H), 7.79 (s, 1H), 7 3.85-3.82 (m, 5H), 2.96-2.81 (m, 2H), 2.66 (t, 2H), 2.42 (t, 2H), 2.03-2.00 (m, 2H), 1.76-1.59 (m, 4H), 1.28 (td, 2H) δ 16.46 (br s, 1H), 8.72 (br s, 2H), 7.89 (s, 1H), 7.77 (d, 1H), 7.43-7.34 (m, 1H), 3.92-3.67 (m, 5H), 2.89 (d, 2H), 2.65 (br s, 2H), 2.54 (t, 2H), 2.43 (br s, 2H), 2.05-1.86 (m, 2H), 1.76-1.53 (m, 2H), 1.29-1.18 (m, 2H) 9 477 10 415 11 441 204 201240602 12 481 13 507 14 457 (AP+) 15 483 (AP+) 16 485 (AP+) 17 457 (AP+) 18 483 (AP+) δ 16.54 (br s,1H),8.05 (s,1H),7.49 (m,5H),7.01 (s,1H),4.36 (m, 19 1H), 3.77 (s, 3H), 3.70 (m, 1H), 3.10 (m, 1H), 2.85 (dd, 1H), 2.73 (m, 2H), 2.64 (dd, 1H), 2.50 (m, 2H), 2.42 (m, 1H), 2.07 (m, 3H) 20 396 21 422 22 360 ESI+ 23 386 ESI+ 24 414 25 440 26 375 27 413 ESI+ 28 437 ESI+ 29 401 30 417 31 445 32 443 33 465 34 439 δ 8.72 (s, 1H), 8.63-S.48 (m, 2H), 7.78 (s, 1H), 5.93 (s, 1H), 3.99-3.71 7Q (m, 5H), 3.02-2.88 (m, 2H), 2.61 (t, 2H), 2.38 (t, 2H), 2.05 (m, 2H), 1.74 (d, 2H), 1.62 (d, 2H), 1.31 (td, 2H) δ 8.77 (d, 1H), 8.71 ( s, 1H), 8.61 (s, 1H), 7.77 (d, 1H), 7.48-7.38 (m, n 1H), 5.93 (s, 1H), 3.99-3.76 (m, 5H), 3.08-2.84 (m, 2H), 2.61 (t, 2H), ^ 2.42-2.28 (m, 2H), 2.10-1.97 (m, 2H), 1.72 (d, 2H), 1.66-1.57 (m, 2H), 1.33-1.20 (m, 2H) δ 8.73 (s, 1H), 7.52 (m, 5H), 7.02 (s, 1H), 6.02 (s, 1H), 4.42 (m, 1H), 19Q 3.82 (m, 1H), 3.78 (s, 3H), 3.22 (m, 1H), 2.88 (m, 1H), 2.69 (m, 2H), 2.61 (m, 1H), 2.45 (s, 3H), 2.12 (m, 2H), 2.07 (m, 1H) 22Q 360 ESI + 26Q 375 δ 8.87 (s, 1H), 8.75 (d, 1H), 8.59 (d, 1H), 7.83 (t, 1H), 4.07-3.98 (m, 7R 1H), 3.94-3.90 (m, 2H), 3.88-3.82 (m, 2H), 3.06-2.94 (m, 2H), 1.79 (d, 2H), 1.68 (d, 2H), 1.35 (td, 2H) 205 201240602Cmpd.咕NMR data or MS data '_ 3 469 4 495 5 465 6 491 δ 16.42 (s, 1H), 8.68 (d, 1H), 8.58 (s, 1H), 7.86 (s, 1H), 7.79 (s , 1H), 7 3.85-3.82 (m, 5H), 2.96-2.81 (m, 2H), 2.66 (t, 2H), 2.42 (t, 2H), 2.03-2.00 (m, 2H), 1.76-1.59 ( m, 4H), 1.28 (td, 2H) δ 16.46 (br s, 1H), 8.72 (br s, 2H), 7.89 (s, 1H), 7.77 (d, 1H), 7.43-7.34 (m, 1H) , 3.92-3.67 (m, 5H), 2.89 (d, 2H), 2.65 (br s, 2H), 2.54 (t, 2H), 2.43 (br s, 2H), 2.05-1.86 (m, 2H), 1.76 -1.53 (m, 2H), 1.29-1.18 (m, 2H) 9 477 10 415 11 441 204 201240602 12 481 13 507 14 457 (AP+) 15 483 (AP+) 16 485 (AP+) 17 457 (AP+) 18 483 (AP+) δ 16.54 (br s,1H), 8.05 (s,1H), 7.49 (m,5H),7.01 (s,1H), 4.36 (m, 19 1H), 3.77 (s, 3H), 3.70 ( m, 1H), 3.10 (m, 1H), 2.85 (dd, 1H), 2.73 (m, 2H), 2.64 (dd, 1H), 2.50 (m, 2H), 2.42 (m, 1H), 2.07 (m , 3H) 20 396 21 422 22 360 ESI+ 23 386 ESI+ 24 414 25 440 26 375 27 413 ESI+ 28 437 ESI+ 29 401 30 417 31 445 32 443 33 465 34 439 δ 8.72 (s, 1H), 8.63-S.48 (m, 2H), 7.78 (s, 1H), 5.93 (s, 1H), 3.99-3.7 1 7Q (m, 5H), 3.02-2.88 (m, 2H), 2.61 (t, 2H), 2.38 (t, 2H), 2.05 (m, 2H), 1.74 (d, 2H), 1.62 (d, 2H) ), 1.31 (td, 2H) δ 8.77 (d, 1H), 8.71 ( s, 1H), 8.61 (s, 1H), 7.77 (d, 1H), 7.48-7.38 (m, n 1H), 5.93 (s , 1H), 3.99-3.76 (m, 5H), 3.08-2.84 (m, 2H), 2.61 (t, 2H), ^ 2.42-2.28 (m, 2H), 2.10-1.97 (m, 2H), 1.72 ( d, 2H), 1.66-1.57 (m, 2H), 1.33-1.20 (m, 2H) δ 8.73 (s, 1H), 7.52 (m, 5H), 7.02 (s, 1H), 6.02 (s, 1H) , 4.42 (m, 1H), 19Q 3.82 (m, 1H), 3.78 (s, 3H), 3.22 (m, 1H), 2.88 (m, 1H), 2.69 (m, 2H), 2.61 (m, 1H) , 2.45 (s, 3H), 2.12 (m, 2H), 2.07 (m, 1H) 22Q 360 ESI + 26Q 375 δ 8.87 (s, 1H), 8.75 (d, 1H), 8.59 (d, 1H), 7.83 (t, 1H), 4.07-3.98 (m, 7R 1H), 3.94-3.90 (m, 2H), 3.88-3.82 (m, 2H), 3.06-2.94 (m, 2H), 1.79 (d, 2H), 1.68 (d, 2H), 1.35 (td, 2H) 205 201240602

8R 11R 14R 17R 19R 22R 25R 26R 3 OR 33R 7S 8S 11S 19S 22S 25S 26S 30S 34S 323 345 5 8.70 δ 8.88 (s,1H),8,0 (s,1H),8.74 (s,1H),7.81 (d im 7 47 m、 4.11-3.99 (m, 1H), 3.96-3.78 (m, 4H), 3.〇8-2 Q〇 vl om i \ λ (m, 4H), 1.31 (t, 2H) 川(m, 2H), 1.81-1.62 321 377 377 δ 8.98 (s,1H),7.54 (m,5H),7.05 (s,1H),4.56 3.78 (m, 1H), 3.18 (m, 1H), 2.93 (m, 1H), 2.67 2.09 (m, 1H) ih), 2.48 (m, 1H), 266 ESI+ 320 (500 MHz) δ 13.09 (br s,1H),8.76 (S, 1H),Μ】 4.01 (m, 2H), 3.89 (m, 2H), 2.23 (m, 2H), 2.15 ^ ^ * 1.30 (m, 2H) 1H), 1.44 (m, 2H), (s, 1H), 8.58-8.49 (m, 2H), 7.77 (S) lHx , Q8 , 70 , , nu, 3.01 (d, 2H), 1.73 (d, 2H), 1.29 (br s, 2H) )&gt; 3.98-3.72 (m, 10H), δ 8.75 (dd, 1H),8.70 (d,1H), 8.53 (S,1H),7 1H),3.88-3.78 (m,8H),3.07-2.95 (m,2H),l 7l ^ 1.25 (td, 2H) (d, 2H), 1.59 (d, 2H), 335 δ 8.66 (s,1H),7.49 (m,5H),7.01 (s,1H),4.39 ( 3.80 (m, 1H), 3.77 (s, 3H), 3.23 (m, 1H), 2.87 m * 2.44 (m, 1H), 2.04 (m, 1H) Vms 1H), 2.59 (dd, 1H), 280 ESI+ 334 295 295 359 所有M.S.數據皆表示為AP+,除非另有社明 本發明生物實例8R 11R 14R 17R 19R 22R 25R 26R 3 OR 33R 7S 8S 11S 19S 22S 25S 26S 30S 34S 323 345 5 8.70 δ 8.88 (s,1H),8,0 (s,1H),8.74 (s,1H),7.81 ( d im 7 47 m, 4.11-3.99 (m, 1H), 3.96-3.78 (m, 4H), 3.〇8-2 Q〇vl om i \ λ (m, 4H), 1.31 (t, 2H) (m, 2H), 1.81-1.62 321 377 377 δ 8.98 (s, 1H), 7.54 (m, 5H), 7.05 (s, 1H), 4.56 3.78 (m, 1H), 3.18 (m, 1H), 2.93 (m, 1H), 2.67 2.09 (m, 1H) ih), 2.48 (m, 1H), 266 ESI+ 320 (500 MHz) δ 13.09 (br s,1H), 8.76 (S, 1H), Μ 4.01 ( m, 2H), 3.89 (m, 2H), 2.23 (m, 2H), 2.15 ^ ^ * 1.30 (m, 2H) 1H), 1.44 (m, 2H), (s, 1H), 8.58-8.49 (m , 2H), 7.77 (S) lHx , Q8 , 70 , , nu, 3.01 (d, 2H), 1.73 (d, 2H), 1.29 (br s, 2H) )&gt; 3.98-3.72 (m, 10H), δ 8.75 (dd, 1H), 8.70 (d, 1H), 8.53 (S, 1H), 7 1H), 3.88-3.78 (m, 8H), 3.07-2.95 (m, 2H), l 7l ^ 1.25 (td , 2H) (d, 2H), 1.59 (d, 2H), 335 δ 8.66 (s, 1H), 7.49 (m, 5H), 7.01 (s, 1H), 4.39 ( 3.80 (m, 1H), 3.77 ( s, 3H), 3.23 (m, 1H), 2.87 m * 2.44 (m, 1H), 2.04 (m, 1H) Vms 1H), 2.59 (dd , 1H), 280 ESI+ 334 295 295 359 All M.S. data are expressed as AP+ unless otherwise stated.

試驗A 將選自稗草cms-ga//,·)、大(Lg)馬唐草 (crabgrass) (D/gziana Siawgwzmz/b)、法氏狗尾草(giant 201240602 foxtail) («Setoziz /Mer&quot;)、牵牛花(morninggi〇ry) spp.)、反枝莧reiro/Zexwj)、苘麻 (velvetleaf) (Abutilon theophrasti)、小麥(7H&quot;cww aeWzvwm)與玉米(Ζβ0 mays)之植物物種的種子栽植於壤 5 土與沙之摻合物中,並且以定向土壤噴霧進行萌前處 理’該噴霧係使用配製於不具植物毒性溶劑混合物中之 試驗化學物質,該混合物包括一界面活性劑。同時這些 物種亦以試驗化合物進行萌後施用處理,該試驗化合物 係以相同方式配製。 10 使用高度範圍在2至10 cm且在一葉至二葉階段的 植物來進行萌後處理。經處理之植物與未經處理之防治 組係在溫室中養護約10天’之後將所有經處理植物與 未經處理之防治組比較並目視評估損傷程度。歸納於表 A中之植物反應評級係基於〇至1〇〇的標度,其中〇為 15 無效果而為完全防治。顯示為破折號(-)之反應意指 無試驗結果。 表A 化合物 表A 化合物 500 g ai/ha 1 125 g ai/ha 29 30 31 32 33 34 萌後 萌後 稗草 100 稗草 80 90 70 100 90 80 玉米 80 玉米 20 30 40 50 10 0 大馬唐草 100 大馬唐草 80 90 90 100 80 90 法氏狗尾草 100 法氏狗尾草 70 80 80 100 70 50 牽牛花 100 牽牛花 100 100 100 100 90 20 反枝莧 100 反枝莧 100 100 90 100 100 90 苘麻 100 Μ麻 100 100 100 100 100 100 小麥 20 小麥 0 20 30 10 0 0 207 201240602 表A 化合物 125 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 萌後 稗草 100 60 90 100 100 100 100 90 90 90 100 90 70 100 玉米 40 10 70 40 60 30 40 20 10 20 20 30 0 20 大馬唐草 100 80 90 90 90 90 100 90 90 90 90 90 50 100 法氏狗尾草 100 30 100 100 90 90 100 90 90 80 90 100 100 100 牽牛花 100 50 100 90 100 100 100 100 90 90 100 100 100 100 反枝莧 100 90 100 100 100 100 100 100 100 100 100 100 100 100 筒麻 100 100 100 100 100 100 100 100 90 100 100 100 100 100 小麥 10 0 0 0 20 20 0 10 0 0 20 0 0 20 表A 化合物 125 g ai/ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28 萌後 稗草 100 50 90 100 100 90 100 70 50 90 100 90 60 100 玉米 30 20 30 40 10 20 50 0 0 50 50 50 20 30 大馬唐草 100 90 90 80 100 90 90 90 90 80 90 90 90 90 法氏狗尾草 100 90 100 100 90 90 100 60 40 - - 70 80 100 牵牛花 100 100 100 100 90 100 90 90 90 100 100 100 80 100 反枝莧 100 100 100 100 100 100 100 90 90 100 100 100 100 100 苘麻 100 100 100 100 100 100 100 - - 100 100 100 100 100 小麥 40 0 10 20 20 0 10 - - 10 0 0 0 0 表A 化合物 31 g ai/ha 2 3 4 5 6 7 8 9 10 11 12 13 14 15 萌後 稗草 10 90 90 100 100 100 30 20 80 90 20 10 30 70 玉米 0 30 20 10 10 10 0 0 10 10 20 0 10 10 大馬唐草 50 90 80 80 70 80 80 70 70 70 50 20 90 80 法氏狗尾草 10 100 90 90 90 90 70 70 60 70 100 50 100 100 牽牛花 10 90 90 80 100 90 100 80 90 100 80 70 100 100 反枝莧 60 100 100 100 90 100 100 90 90 100 100 80 100 100 筒麻 100 100 100 100 100 100 100 70 100 100 100 80 100 100 小麥 0 0 0 0 0 0 0 0 0 0 0 0 0 0 208 201240602 表A 化合物 31 g ai/ha 16 17 18 19 20 21 22 23 24 25 26 27 28 29 萌後 稗草 20 60 90 80 70 90 30 10 80 90 70 20 30 30 玉米 10 20 30 0 10 10 0 0 0 0 0 0 30 0 大馬唐草 70 70 50 60 50 70 70 50 70 70 70 90 70 50 法氏狗尾草 80 90 90 80 70 90 10 0 - - 30 60 90 40 牵牛花 100 100 100 90 90 90 90 70 100 100 100 70 90 100 反枝莧 100 90 80 100 100 80 80 50 100 100 90 100 90 80 麻 100 100 80 100 90 100 - - 90 90 100 100 100 100 小麥 0 0 0 0 0 0 - - 0 0 0 0 0 0 表A 化合物 表A 化合物 31 g ai/ha 30 31 32 33 34 500 g ί ai/ha 1 萌後 萌前 稗草 60 20 90 80 60 稗草 90 玉米 10 20 20 0 0 玉米 0 大馬唐草 70 70 60 60 70 大馬唐草 100 法氏狗尾草 70 70 90 40 30 法氏狗尾草 100 牵牛花 100 100 100 70 10 牽牛 化 90 反枝莧 90 80 100 90 70 反枝莧 100 筒麻 100 100 100 90 100 筒麻 100 小麥 0 0 0 0 0 小麥 10 表A 化合物 125 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 萌前 稗草 60 10 70 50 50 60 90 50 40 90 90 20 10 60 玉米 0 0 0 0 0 0 0 0 0 0 0 0 0 0 大馬唐草 90 70 60 50 60 70 ]00 70 70 90 80 70 70 100 法氏狗尾草 60 0 80 40 80 60 100 50 60 60 70 90 60 90 牵牛花 60 0 40 - 50 60 80 10 20 70 70 20 0 90 反枝莧 100 90 90 100 90 80 100 90 100 60 30 90 90 100 苘麻 80 80 80 60 60 50 60 30 70 70 50 80 40 90 小麥 0 0 0 0 0 0 0 0 0 0 0 10 0 0 209 201240602 表A 125 g ai/ha 15 16 17 18 萌前 鞞草 0 10 50 100 玉米 0 0 0 0 大馬唐草 30 40 50 80 法氏狗尾草 70 20 50 70 牽牛花 70 30 10 20 反枝莧 90 80 80 90 麻 50 50 50 70 小麥 0 0 0 - 表A 化合物 125 g ai/ha 29 30 31 32 萌前 稗草 50 70 40 50 玉米 0 0 0 0 大馬唐草 60 90 80 30 法氏狗尾草 10 20 50 20 牽牛花 10 0 10 10 反枝莧 90 90 100 90 筒麻 70 90 70 70 小麥 0 0 0 - 表A 31 g ai/ha 2 3 4 5 萌前 稗草 0 0 10 0 玉米 0 0 0 0 大馬唐草 10 10 10 10 法氏狗尾草 0 40 10 20 牵牛花 0 0 20 0 反枝莧 0 60 40 50 麻 0 50 40 50 小麥 0 0 0 0 化合物 20 21 22 23 24 25 26 27 28 70 50 70 80 80 70 70 50 40 0 0 0 0 0 20 0 0 0 70 30 90 100 90 90 80 60 60 50 30 50 30 60 20 20 30 40 10 30 80 80 70 80 70 10 10 70 80 100 100 100 90 90 90 90 60 40 90 90 100 80 90 80 70 0 0 0 10 0 0 0 0 0 表A 化合物 34 31 g ai/ha 30 31 32 33 34 萌前 30 稗草 10 0 10 0 0 0 玉米 0 0 0 0 0 70 大馬唐草 40 50 10 10 10 0 法氏狗尾草 0 10 0 0 0 0 牽牛花 0 0 0 0 0 60 反枝莧 50 50 70 - 10 70 4麻 70 50 50 10 30 0 小麥 0 0 0 0 0 化合物 7 8 9 10 11 12 13 14 15 10 0 10 20 40 0 0 10 0 0 0 0 0 0 0 0 0 0 70 60 40 40 50 60 10 90 30 80 30 20 40 40 60 10 50 10 20 0 0 0 10 0 0 20 10 90 40 30 30 0 90 20 90 40 50 0 40 60 10 20 0 60 20 0 0 0 0 0 0 0 0 0 210 201240602 表A 31 g ai/ha 16 17 18 萌前 稗草 0 10 10 玉米 0 0 0 大馬唐草 10 20 30 法氏狗尾草 0 20 0 牵牛花 0 0 0 反枝莧 10 0 60 苘麻 20 40 20 小麥 0 0 0 化合物 19 20 21 22 23 24 25 26 27 28 29 0 10 0 40 10 20 0 10 10 10 0 0 0 0 0 0 0 0 0 0 0 0 10 10 0 50 60 30 20 40 20 10 10 - 0 0 0 0 10 0 0 10 0 0 0 0 - 50 10 50 10 0 30 0 0 40 30 10 80 50 70 70 20 40 40 10 30 20 10 70 50 40 10 80 60 50 10 0 0 0 0 0 0 0 0 0 0 0Test A will be selected from the group consisting of valerian cms-ga//, ), large (Lg) crabgrass (D/gziana Siawgwzmz/b), and foxtail (giant 201240602 foxtail) («Setoziz /Mer&quot;), Seeds of plant species of morning glory (morning 〇ry spp.), religios reiro/Zexwj), velvetleaf (Abutilon theophrasti), wheat (7H&quot;cww aeWzvwm) and corn (Ζβ0 mays) In the blend of soil 5 and sand, and pre-emergence treatment with a directional soil spray, the spray uses a test chemistry formulated in a non-phytotoxic solvent mixture, the mixture comprising a surfactant. At the same time, these species were also subjected to post-emergence treatment with test compounds which were formulated in the same manner. 10 Post-emergence treatment is carried out using plants with a height ranging from 2 to 10 cm and in the leaf to bilobal stage. The treated plants were compared with the untreated control group for about 10 days in the greenhouse. After treatment, all treated plants were compared with the untreated control group and the degree of damage was visually evaluated. The plant response ratings summarized in Table A are based on a scale of 〇 to 1〇〇, where 〇 15 is ineffective and is completely controlled. The reaction shown as a dash (-) means no test results. Table A Compounds Table A Compound 500 g ai/ha 1 125 g ai/ha 29 30 31 32 33 34 Post-emergence and post-emergence Valerian 100 Valerian 80 90 70 100 90 80 Corn 80 Corn 20 30 40 50 10 0 100 Great Horsegrass 80 90 90 100 80 90 French foxtail 100 French foxtail 70 80 80 100 70 50 Morning Glory 100 Morning Glory 100 100 100 100 90 20 Anti-branches 100 Anti-branches 100 100 90 100 100 90 Ramie 100 Ramie 100 100 100 100 100 100 Wheat 20 Wheat 0 20 30 10 0 0 207 201240602 Table A Compound 125 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Post-emergence valerian 100 60 90 100 100 100 100 90 90 90 100 90 70 100 Corn 40 10 70 40 60 30 40 20 10 20 20 30 0 20 Large horse grass 100 80 90 90 90 90 100 90 90 90 90 90 50 100 French foxtail 100 30 100 100 90 90 100 90 90 80 90 100 100 100 Morning Glory 100 50 100 90 100 100 100 100 90 90 100 100 100 100 Anti-branches 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 100 100 100 100 100 Wheat 10 0 0 0 20 20 0 10 0 0 20 0 0 20 Table A Compound 125 g ai/ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28 Post-emergence valerian 100 50 90 100 100 90 100 70 50 90 100 90 60 100 Corn 30 20 30 40 10 20 50 0 0 50 50 50 20 30 Great horse grass 100 90 90 80 100 90 90 90 90 80 90 90 90 90 French foxtail 100 90 100 100 90 90 100 60 40 - - 70 80 100 Morning glory 100 100 100 100 90 100 90 90 90 100 100 100 80 100 Inverse branches 100 100 100 100 100 100 100 90 90 90 100 100 100 100 100 Ramie 100 100 100 100 100 100 100 - - 100 100 100 100 100 Wheat 40 0 10 20 20 0 10 - - 10 0 0 0 0 Table A Compound 31 g ai/ha 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Post-emergence valerian 10 90 90 100 100 100 30 20 80 90 20 10 30 70 Corn 0 30 20 10 10 10 0 0 10 10 20 0 10 10 Great horse grass 50 90 80 80 70 80 80 70 70 70 50 20 90 80 French foxtail 10 100 90 90 90 90 70 70 60 70 100 50 100 100 Morning glory 10 90 90 80 100 90 100 80 90 100 80 70 100 100 Inverse branches 60 100 100 100 90 100 100 90 90 100 100 80 100 100 tube hemp 100 100 100 100 100 100 100 70 100 100 100 80 100 100 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 208 201240602 Table A Compound 31 g ai/ha 16 17 18 19 20 21 22 23 24 25 26 27 28 29 萌萌稗20 60 90 80 70 90 30 10 80 90 70 20 30 30 Corn 10 20 30 0 10 10 0 0 0 0 0 0 30 0 大马唐草70 70 50 60 50 70 70 50 70 70 70 90 70 50 foxtail sage 80 90 90 80 70 90 10 0 - - 30 60 90 40 Morning Glory 100 100 100 90 90 90 90 70 100 100 100 70 90 100 Anti-branches 100 90 80 100 100 80 80 50 100 100 90 100 90 80 Hemp 100 100 80 100 90 100 - - 90 90 100 100 100 100 Wheat 0 0 0 0 0 0 - - 0 0 0 0 0 Table A Compounds Table A Compound 31 g ai/ha 30 31 32 33 34 500 g ί ai/ha 1 After the germination of the geranium 60 20 90 80 60 稗草 90 corn 10 20 20 0 0 corn 0 马马唐草70 70 60 60 70 大马唐草100 法氏狗草70 70 90 40 30 French foxtail 100 Morning Glory 100 100 100 70 10 Morning vine 90 Anti-branches 90 80 100 90 70反 苋 100 筒 100 100 100 100 90 100 麻麻 100 Wheat 0 0 0 0 0 Wheat 10 Table A Compound 125 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Pre-emergence 60 10 70 50 50 60 90 50 40 90 90 20 10 60 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 Big horse grass 90 70 60 50 60 70 ]00 70 70 90 80 70 70 100 Phnom Penh 60 0 80 40 80 60 100 50 60 60 70 90 60 90 Morning Glory 60 0 40 - 50 60 80 10 20 70 70 20 0 90 Anti-branches 100 90 90 100 90 80 100 90 100 60 30 90 90 100 Ramie 80 80 80 60 60 50 60 30 70 70 50 80 40 90 Wheat 0 0 0 0 0 0 0 0 0 0 0 10 0 209 201240602 Table A 125 g ai/ha 15 16 17 18 Before the germination 0 10 50 100 Corn 0 0 0 0 大马唐草30 40 50 80 法氏狗草70 20 50 70 Morning Glory 70 30 10 20 反 苋 90 80 80 90 Hemp 50 50 50 70 Wheat 0 0 0 - Table A Compound 125 g ai/ha 29 30 31 32 Pre-emergence valerian 50 70 40 50 Corn 0 0 0 0 Large horse grass 60 90 80 30 French foxtail 10 20 50 20 Morning glory 10 0 10 10 Anti-branches 9 0 90 100 90 Cannabis 70 90 70 70 Wheat 0 0 0 - Table A 31 g ai/ha 2 3 4 5 Before the germination 0 0 10 0 Corn 0 0 0 0 Large horse grass 10 10 10 10 French foxtail 0 40 10 20 Morning Glory 0 0 20 0 Anti-branches 0 60 40 50 Hemp 0 50 40 50 Wheat 0 0 0 0 Compound 20 21 22 23 24 25 26 27 28 70 50 70 80 80 70 70 50 40 0 0 0 0 0 20 0 0 0 70 30 90 100 90 90 80 60 60 50 30 50 30 60 20 20 30 40 10 30 80 80 70 80 70 10 10 70 80 100 100 100 90 90 90 90 60 40 90 90 100 80 90 80 70 0 0 0 10 0 0 0 0 0 Table A Compound 34 31 g ai/ha 30 31 32 33 34 Pre-emergence 30 Valerian 10 0 10 0 0 0 Corn 0 0 0 0 0 70 Big horse Tang grass 40 50 10 10 10 0 Lawn's foxtail 0 10 0 0 0 0 Morning Glory 0 0 0 0 0 60 Anti-branches 50 50 70 - 10 70 4 Ma 70 50 50 10 30 0 Wheat 0 0 0 0 0 Compound 7 8 9 10 11 12 13 14 15 10 0 10 20 40 0 0 10 0 0 0 0 0 0 0 0 0 0 70 60 40 40 50 60 10 90 30 80 30 20 40 40 60 10 50 10 20 0 0 0 10 0 0 20 10 90 40 30 30 0 90 20 90 40 50 0 40 60 10 20 0 60 20 0 0 0 0 0 0 0 0 0 210 201240602 Table A 31 g ai/ha 16 17 18 Pre-emergence valerian 0 10 10 Corn 0 0 0 Large horse grass 10 20 30 French foxtail 0 20 0 Morning glory 0 0 0苋10 0 60 ramie 20 40 20 wheat 0 0 0 compound 19 20 21 22 23 24 25 26 27 28 29 0 10 0 40 10 20 0 10 10 10 0 0 0 0 0 0 0 0 0 0 0 10 10 0 50 60 30 20 40 20 10 10 - 0 0 0 0 10 0 0 10 0 0 0 0 - 50 10 50 10 0 30 0 0 40 30 10 80 50 70 70 20 40 40 10 30 20 10 70 50 40 10 80 60 50 10 0 0 0 0 0 0 0 0 0 0 0

試驗B 將選自 黑草(blackgrass) {Alopecurus mjoswro We*s)、毛白露草(downy bromegrass) (Bromws 5 ieciorww)、莠草(green foxtail) 、義大利 黑麥草(Italian ryegrass) (Zo//wm mw/iz//orw7«)、冬小麥 (7W&quot;cwm 0以伽《所)、野生燕麥/加⑽)、八仙草 (galium) (catchweed bedstraw, G^f/zww 、百慕達 草i/&lt;2C*(y/o«)、蘇利南草 i〇 decumbens)、蒼耳(cocklebur) (common cocklebur,Test B will be selected from blackgrass {Alopecurus mjoswro We*s), downy bromegrass (Bromws 5 ieciorww), green foxtail, Italian ryegrass (Zo// Wm mw/iz//orw7«), winter wheat (7W&quot;cwm 0 aga", wild oatmeal/plus (10)), galium (catchweed bedstraw, G^f/zww, Bermuda grass i/ &lt;2C*(y/o«), Suriname grass i〇decumbens), cocklebur (common cocklebur,

Jianihitim strumarium)、玉米(Zea mays)、大馬唐萆 (Digitaria sanguinalis)、烏利杯草(woolly cupgrass) (Eriochha villosa)、法氏拘 1 尊(Setaria faberii)、牛筋 草(goosegrass)(五/ew幻&gt;ze z«i//c&lt;3)、強生草(johnsongrass) is (Sorghum halepense)、地 $ (kochio) (Kochia scoparia)、 藜(lambsquarters) (Chenopodium a!bum)、牽牛花^ (Ipomoea coccinea) ' ^ (nightshade) (eastern black nightshade,Wammz 〆少所)、油莎草(yellow 211 201240602 nutsedge) {Cyperus esculentus)、反枝览(nightshade) (Amaranthus retroflexus)、諸草(ragweed) (common ragweed, Ambrosia elatior) ' 3. {Glycine max) ' ( /¾ # )Jianihitim strumarium), Zea mays, Digitaria sanguinalis, woolly cupgrass (Eriochha villosa), Setaria faberii, goosegrass (five /ew illusion&gt;ze z«i//c&lt;3), Johnsongrass is (Sorghum halepense), $ (kochio) (Kochia scoparia), lam (lambsquarters) (Chenopodium a!bum), morning glory ^ (Ipomoea coccinea) ' ^ (nightshade) (eastern black nightshade, Wammz 〆 所), sedge (yellow 211 201240602 nutsedge) {Cyperus esculentus), anti-twig (nightshade) (Amaranthus retroflexus), grazing ) (common ragweed, Ambrosia elatior) ' 3. {Glycine max) ' ( /3⁄4 # )

向曰蔡(Z/e/ί⑽、俄國薊(&amp;/奶/a k//)與苘麻 5 (Abutilon theophrasti) JiH 沙之摻合物中,並且以配製於不具植物毒性溶劑混合物 中之試驗化學物質進行萌前處理,該混合物包括一界面 活性劑。 同時將選自這些作物與雜草物種之植物以及冬大 10 麥(Hordeum \m丨gare)、金絲、雀萆(cmarygrass) (Phalaris 、繁縷(chickweed) (common chickweed, //ark 、風剪草(chickweed) 似/)與寶蓋草 (deadnettle) (henbit deadnettle,Low/ww 栽 植於含 Redi-Earth®栽植介質(Scotts Company, 14111 15 Scottslawn Road, Marysville,Ohio 43041)之罐中,該栽 植介質含泥炭蘚抑3§111111111口6&amp;1|11055)、經石、潤濕劑與 起始營養素’並且以一些試驗化學物質(以相同方式配 製)進行萌後施用處理。使用高度範圍在2至18 cm ( 1 至4葉階段)的植物來進行萌後處理·。 20 改沒式水田s式驗中的植物物種係由稻米 如&quot;⑽)、輪傘草(umbrella sedge) 、異 藥 t (duck salad) (Ι^βηιηώβρα Iimosa)與稗草 (barnyardgrass^fc/^ijc/z/i^cms-^///)所組成,其已長 成為2葉階段以供試驗。在處理時,使試驗罐浸沒至高 !5 於土壤表面3公分’其處理係將試驗化合物直接施用至 田水中,並且在試驗期間維持在此水深。 212 201240602 經處理之植物與防治組係在溫室中養護13至15 天,之後將所有物種與防治組比較並目視評估。歸納於 表B中之植物反應評級係基於0至100的標度,其中0 為無效果而100為完全防治。顯示為破折號(-)之反應意 指無試驗結果。 表B 化合物 250 g ai/ha 浸沒 1 2 3 4 5 6 7 8 9 10 11 12 13 14 稗草 80 0 85 85 80 65 - 40 40 75 80 50 40 65 異藥花 80 0 95 95 80 85 90 85 95 90 90 85 70 85 稻米 80 0 85 15 65 30 15 40 20 50 50 40 35 80 輪傘草 95 0 90 75 75 80 85 100 95 75 90 85 80 80 表B 化合物 250 g ai/ha 浸沒 15 16 17 18 19 20 21 22 23 24 25 26 27 28 稗草 40 30 20 0 60 55 60 80 75 75 0 .60 0 0 異藥花 80 75 70 50 95 60 80 95 80 100 0 85 75 50 稻米 0 60 0 10 20 45 0 80 75 90 0 25 0 0 輪傘草 85 70 75 65 85 30 30 90 85 100 30 80 75 75 表B 化合物 250 g ai/ha 浸沒 29 30 31 32 33 34 稗草 0 20 30 15 0 30 異藥花 60 60 70 0 40 90 稻米 0 10 20 15 0 0 輪傘草 75 100 80 30 30 90 表B 化合物 125 g ai/ha 浸沒 1 2 3 4 5 6 7 8 9 10 11 12 13 14 稗草 60 0 30 0 0 20 - 0 0 65 65 15 15 40 213 201240602 異藥花 75 0 65 30 80 85 75 75 85 85 80 80 40 75 稻米 20 0 0 10 20 0 10 0 0 15 0 40 20 60 輪傘草 85 0 80 30 60 65 80 80 70 75 80 80 75 75To the blend of Z/e/ί(10), Russian 蓟 (&amp;/奶/ak//) and ramie 5 (Abutilon theophrasti) JiH sand, and prepared in a mixture of non-phytotoxic solvents The chemical is pre-emerged and the mixture comprises a surfactant. At the same time, plants selected from these crops and weed species, as well as Hordeum \m丨gare, gold silk, and cmarygrass (Phalaris) , chickweed (common chickweed, //ark, chickweed/) and deadnettle (henbit deadnettle, Low/ww planted in Reddi-Earth® containing medium (Scotts Company, 14111) 15 Scottslawn Road, Marysville, Ohio 43041), the planting medium contains peat moss 3§111111111 mouth 6&amp;1|11055), warp, wetting agent and starting nutrients' and with some test chemicals ( Prepared in the same manner) for post-emergence treatment. Plants with a height range of 2 to 18 cm (1 to 4 leaf stage) are used for post-emergence treatment. 20 The plant species in the modified paddy field test is from rice. &quot;(10)), Umbrella (umbrel) La sedge), a different drug t (duck salad) (Ι^βηιηώβρα Iimosa) and 稗草 (barnyardgrass^fc/^ijc/z/i^cms-^///), which has grown into a 2-leaf stage For testing. When processing, immerse the test tank to a high level! 5 on the soil surface 3 cm. The treatment is applied directly to the field water and maintained at this water depth during the test. 212 201240602 Treated plant and control group The plants were maintained in the greenhouse for 13 to 15 days, after which all species were compared and visually evaluated. The plant response ratings summarized in Table B were based on a scale of 0 to 100, with 0 being ineffective and 100 being complete. The reaction shown as a dash (-) means no test results. Table B Compound 250 g ai/ha Immersion 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Valerian 80 0 85 85 80 65 - 40 40 75 80 50 40 65 Heterophylla 80 0 95 95 80 85 90 85 95 90 90 85 70 85 Rice 80 0 85 15 65 30 15 40 20 50 50 40 35 80 Round umbrella 95 0 90 75 75 80 85 100 95 75 90 85 80 80 Table B Compound 250 g ai/ha Immersion 15 16 17 18 19 20 21 22 23 24 25 26 27 28 40 30 20 0 60 55 60 80 75 75 0 .60 0 0 Heterophyllum 80 75 70 50 95 60 80 95 80 100 0 85 75 50 Rice 0 60 0 10 20 45 0 80 75 90 0 25 0 0 85 70 75 65 85 30 30 90 85 100 30 80 75 75 Table B Compound 250 g ai/ha Immersion 29 30 31 32 33 34 Valerian 0 20 30 15 0 30 Isolate 60 60 70 0 40 90 Rice 0 10 20 15 0 0 omnivorous grass 75 100 80 30 30 90 Table B Compound 125 g ai/ha Immersion 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Herborist 60 0 30 0 0 20 - 0 0 65 65 15 15 40 213 201240602 Heterophylla 75 0 65 30 80 85 75 75 85 85 80 80 40 75 Rice 20 0 0 10 20 0 10 0 0 15 0 40 20 60 Umbrella 85 0 80 30 60 65 80 80 70 75 80 80 75 75

表B 125 g ai/ha 浸沒 15 16 17 18 19 稗草 0 0 15 0 15 異藥花 75 70 70 40 75 稻米 0 0 0 0 0 輪傘草 80 30 70 60 80 化合物 20 21 22 23 24 25 26 27 28 40 0 75 60 60 0 30 0 0 40 0 85 80 75 0 65 70 50 25 0 75 60 35 0 15 0 0 30 0 90 75 75 0 75 40 50 化合物Table B 125 g ai/ha Immersion 15 16 17 18 19 Valerian 0 0 15 0 15 Heterophylla 75 70 70 40 75 Rice 0 0 0 0 0 Umbrella 80 30 70 60 80 Compound 20 21 22 23 24 25 26 27 28 40 0 75 60 60 0 30 0 0 40 0 85 80 75 0 65 70 50 25 0 75 60 35 0 15 0 0 30 0 90 75 75 0 75 40 50 Compound

表B 125 g ai/ha 浸沒 29 30 稗草 0 0 異藥花 0 0 稻米 0 0 輪傘草 0 80 31 32 33 34 0 0 0 10 0 0 0 0 0 0 0 0 30 0 0 70Table B 125 g ai/ha Immersion 29 30 稗草 0 0 异药花 0 0 Rice 0 0 车草草 0 80 31 32 33 34 0 0 0 10 0 0 0 0 0 0 0 30 0 0 70

表B 62 g ai/ha 浸沒 1 2 3 4 5 鞞草 0 0 0 0 0 異藥花 70 0 40 0 45 稻米 0 0 0 0 0 輪伞草 85 0 80 0 50 化合物 6 7 8 9 10 11 12 13 14 0 _ 0 0 50 0 0 0 20 75 50 50 80 80 75 60 20 75 0 0 0 0 10 0 20 0 20 30 70 60 0 60 70 70 50 75Table B 62 g ai/ha Immersion 1 2 3 4 5 Valerian 0 0 0 0 0 Heterophyllum 70 0 40 0 45 Rice 0 0 0 0 0 Round Umbrella 85 0 80 0 50 Compound 6 7 8 9 10 11 12 13 14 0 _ 0 0 50 0 0 0 20 75 50 50 80 80 75 60 20 75 0 0 0 0 10 0 20 0 20 30 70 60 0 60 70 70 50 75

表B 62 g ai/ha 浸沒 15 16 17 18 19 稗草 0 0 0 0 0 異藥花 75 30 50 0 60 稻米 0 0 0 0 0 輪伞草 70 0 50 0 70 化合物 20 21 22 23 24 25 26 27 28 0 0 55 40 20 0 0 0 0 0 0 75 50 50 0 30 20 0 10 0 45 25 20 0 10 0 0 0 0 80 50 30 0 60 20 30 5 201240602 表B 化合物 62 g ai/ha 29 30 31 32 33 34 浸沒 稗草 0 0 0 0 0 0 異藥花 0 0 0 0 0 0 稻米 0 0 0 0 0 0 輪傘草 0 30 0 0 0 70 表B 化合物 31 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 浸沒 稗草 0 0 0 0 0 0 -0 0 0 0 0 0 20 異藥花 70 0 0 0 0 0 0 0 0 80 50 50 0 70 稻米 0 0 0 0 0 0 0 0 0 0 0 10 0 20 輪傘草 70 0 40 0 0 0 0 0 0 40 0 0 0 45 表B 化合物 31 g ai/ha 浸沒 15 16 17 18 19 20 21 22 23 24 25 26 27 28 稗草 0 0 0 0 0 0 0 30 0 20 0 0 0 0 異藥花 65 30 0 0 40 0 0 45 0 40 0 20 0 0 稻米 0 0 0 0 0 0 0 20 20 10 0 0 0 0 輪伞草 65 0 0 0 60 0 0 0 0 0 0 20 0 0 表B 化合物 31 g ai/ha 浸沒 29 30 31 32 33 34 稗草 0 0 0 0 0 0 異藥花 0 0 0 0 0 - 稻米 0 0 0 0 0 0 輪傘草 0 0 0 0 0 - 表B 化合物 250 g ai/ha 萌後 1 3 4 5 6 8 12 14 15 16 18 19 20 21 大麥 80 50 5 10 5 50 15 50 5 35 5 80 5 0 百慕達草 85 90 85 85 65 98 65 90 95 90 90 95 95 90 215 201240602 黑草 85 85 55 40 5 70 80 15 60 5 70 80 55 10 毛白露草 - 5 5 35 35 90 35 70 70 10 40 95 - 15 金絲雀草 100 85 85 85 40 100 90 55 60 90 70 100 40 10 繁縷 100 100 100 100 100 100 100 100 100 100 100 100 100 100 蒼耳 - 100 98 98 100 100 100 100 100 100 100 - 100 100 玉米 80 85 80 90 65 80 85 75 60 50 60 90 75 80 馬唐草,Large 98 90 90 85 95 98 80 100 98 98 75 100 95 95 烏利杯草 98 90 95 90 95 98 95 100 100 100 100 98 100 95 寶蓋草 - 100 100 100 100 100 100 100 100 100 100 100 100 100 法氏狗尾草 100 90 95 95 95 98 95 98 98 85 98 95 98 95 莠草 95 100 100 95 90 90 90 98 60 70 98 100 95 100 八仙草 - 95 95 60 - 85 85 95 85 90 80 95 70 90 牛筋草 95 85 90 - 85 98 90 95 98 85 95 90 98 85 強生草 95 95 98 95 98 100 90 98 100 85 100 - 85 98 地膚 90 85 75 15 65 100 65 100 80 75 98 100 100 100 藜 100 100 100 100 100 100 100 100 100 100 100 100 100 - 牵牛花 100 100 100 100 100 100 100 100 100 100 100 100 100 100 油莎草 80 85 80 85 45 85 85 85 75 65 65 85 80 80 野生燕麥 90 95 85 60 35 98 90 95 55 85 70 95 20 5 反枝莧 100 100 100 100 100 100 100 100 100 100 100 100 100 100 豬草 100 100 100 100 100 100 100 100 100 100 100 100 100 100 義大利黑麥草 45 35 40 5 5 35 20 10 10 20 20 95 5 5 黃豆 100 98 98 98 98 100 98 100 100 100 100 100 95 98 蘇利南草 90 85 95 75 85 98 85 95 98 85 98 100 85 85 筒麻 100 95 85 85 80 98 100 100 95 90 90 100 100 95 小麥 35 0 0 5 5 40 5 20 30 0 30 95 20 20 風剪草 95 85 90 45 55 98 65 90 80 65 85 100 80 85 表B 化合物 250 g ai/ha 萌後 22 23 24 25 26 28 29 30 31 32 大麥 80 55 35 30 10 35 35 20 50 5 百慕達草 98 95 98 98 95 100 95 95 85 95 黑草 25 30 80 40 30 65 85 50 35 40 毛白露草 35 80 80 10 10 45 35 45 40 55 金絲雀草 80 95 90 60 50 40 50 50 80 45 繁縷 100 100 100 100 100 100 100 100 100 100 蒼耳 100 98 100 100 100 - - 100 98 98 216 201240602 玉米 80 90 85 100 35 85 80 55 75 65 大馬唐草 98 100 95 98 90 100 98 95 85 98 烏利杯草 90 98 98 100 80 100 98 85 80 98 寶蓋草 100 100 100 100 100 100 100 100 100 100 法氏狗尾草 90 95 95 95 100 100 95 90 90 98 莠草 90 98 100 100 70 100 95 95 70 95 八仙草 95 98 95 90 90 85 90 95 95 90 牛筋草 95 98 98 95 85 100 95 75 85 95 強生草 80 100 100 100 75 98 95 75 80 100 地膚 98 100 98 98 95 100 100 100 55 95 藜 100 100 98 100 100 100 100 100 98 100 牽牛花 100 100 100 100 100 100 100 100 98 100 油莎草 90 90 90 55 85 45 85 80 60 100 野生燕麥 60 95 85 45 15 50 40 50 45 50 反枝莧 98 98 100 100 100 100 100 100 98 100 豬草 100 100 100 100 100 100 100 100 95 100 義大利黑麥草 30 35 5 5 40 10 30 45 30 30 黃豆 98 98 95 98 98 100 100 100 98 98 蘇利南草 85 95 95 98 70 95 80 85 85 95 筒麻 98 98 100 98 100 100 100 100 95 98 小麥 90 90 30 35 25 50 40 40 40 60 風剪草 90 80 100 80 55 80 70 80 60 80 表B 化合物 125 g ai/ha 1 3 4 5 6 8 10 12 14 15 16 18 19 20 萌後 大麥 70 30 5 5 0 15 0 5 5 0 20 0 55 5 百慕達草 85 85 80 80 50 98 90 35 75 85 85 85 95 95 里箪 85 85 40 35 5 35 10 70 15 15 0 20 75 40 毛白露草 - 0 5 0 0 90 10 20 50 45 10 20 90 - 金絲雀草 100 80 85 65 35 65 20 70 30 60 60 50 100 40 繁縷 100 100 100 98 100 100 100 100 100 100 100 100 100 98 蒼耳 100 100 98 95 100 100 100 100 100 100 100 100 - 100 玉米 75 85 80 80 65 65 65 80 75 25 35 45 85 70 大馬唐草 95 90 90 85 90 95 95 60 98 85 98 70 98 85 烏利杯草 90 90 95 85 90 98 65 95 98 100 98 98 98 98 寶蓋草 -100 100 100 100 100 100 100 100 100 100 100 85 100 法氏狗尾草 98 85 90 90 90 98 85 90 95 95 85 95 95 95 217 201240602 莠草 95 95 95 八仙草 -85 90 牛筋草 95 85 85 強生草 90 95, 98 地膚 85 65 60 藜 100 100 100 牵牛花 100 100 100 油莎草 75 80 65 野生燕麥 90 90 80 反枝莧 100 100 100 豬草 100 100 100 義大利黑麥草 45 35 35 黃豆 100 95 98 蘇利南草 85 80 90 筒麻 100 95 75 小麥 30 0 0 風剪草 85 75 80 表B 125 g ai/ha 21 22 萌後 大麥 0 60 百慕達草 90 98 黑草 10 25 毛白露草 5 35 金絲雀草 5 70 繁縷 98 100 蒼耳 100 95 玉米 80 80 大馬唐草 85 98 烏利杯草 85 85 寶蓋草 100 100 法氏狗尾草 95 85 莠草 100 85 八仙草 85 90 牛筋草 80 90 強生草 95 70 地膚 90 95 90 90 70 90 85 55 70 90 98 90 80 70 90 60 85 85 90 75 90 70 80 95 85 85 95 90 85 85 90 90 90 100 65 85 95 98 80 98 - 75 10 98 100 45 98 75 65 65 100 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 25 80 90 80 85 60 40 60 65 80 35 95 15 70 90 50 50 65 95 20 100 100 100 100 100 100 100 100 100 98 100 100 100 100 100 100 100 100 100 98 0 30 5 20 10 10 20 5 70 5 98 100 100 98 100 100 100 100 100 95 80 95 50 85 95 95 80 90 100 80 75 80 85 95 100 80 80 80 100 95 5 30 5 0 15 5 0 0 90 5 30 95 60 65 65 75 60 65 100 75 24 化合物 25 26 28 29 30 31 32 35 15 5 15 35 5 35 0 98 98 90 100 95 90 85 90 80 30 10 50 70 45 30 40 50 10 5 40 10 35 30 35 75 45 45 15 45 35 55 45 100 98 100 98 100 100 100 100 98 100 - - - 100 95 95 85 95 20 75 70 50 65 45 95 98 85 100 98 90 85 85 98 100 75 100 90 75 70 95 100 100 98 100 - 100 85 100 95 95 100 100 95 80 85 95 98 100 40 90 90 85 70 90 85 90 85 85 90 85 90 90 95 95 75 100 90 65 80 85 98 100 55 75 75 70 70 95 95 95 95 100 100 80 45 95 218 201240602 藜 - 100 牽牛花 100 100 油莎草 65 90 野生燕麥 5 60 反枝莧 95 1 98 豬草 100 100 義大利黑麥草 0 30 黃豆 98 95 蘇利南草 80 80 苘麻 80 1 98 小麥 10 1 90 風剪草 45 60 表B 62 g ai/ha 1 3 4 萌後 大麥 50 5 0 百慕達草 85 60 75 黑草 60 70 30 毛白露草 55 0 5 金絲雀草 95 80 75 繁縷 100 100 100 蒼耳 -100 98 玉米 75 70 80 大馬唐草 95 80 85 烏利杯草 85 85 90 寶蓋草 60 95 100 法氏狗尾草 95 85 85 莠草 75 90 95 八仙草 90 60 90 牛筋草 85 75 80 強生草 85 85 95 地膚 75 25 50 藜 100 100 100 牽牛花 100 100 100 油莎草 75 80 50 野生燕麥 85 85 60 反枝莧 100 100 100 98 100 100 100 100 100 98 100 100 100 95 100 100 100 98 100 90 45 80 20 70 70 40 95 60 40 10 45 30 45 45 45 100 98 100 100 100 100 95 100 100 100 100 100 100 100 95 100 5 5 30 10 15 30 20 10 90 98 90 100 100 98 98 98 95 98 65 95 75 85 75 85 90 95 100 100 100 100 95 98 15 35 0 35 35 40 35 40 98 80 50 10 50 55 60 60 化合物 6 7 8 10 11 12 14 15 16 17 0 35 5 0 0 0 0 0 0 0 45 85 95 85 80 5 75 75 80 75 5 70 30 5 55 65 10 5 0 20 0 - 60 5 30 10 40 45 5 15 35 80 55 15 35 60 20 45 40 30 100 100 100 100 100 100 100 100 100 100 95 - 100 98 100 100 95 100 98 100 45 90 10 20 20 65 35 25 10 60 75 100 95 85 85 60 90 75 90 80 85 100 90 60 85 85 98 90 95 98 100 85 100 100 100 100 100 100 100 100 85 98 90 80 90 85 85 90 80 85 85 100 60 50 85 50 80 50 50 80 55 85 50 70 85 60 85 60 50 80 65 100 75 85 80 75 75 80 85 45 90 100 90 25 85 60 80 98 65 70 5 100 75 95 70 10 75 25 20 98 98 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 95 100 100 100 25 85 75 85 75 80 80 50 25 90 30 90 85 5 20 60 90 50 50 60 100 100 98 100 100 100 100 100 100 100 219 201240602 豬草 100 100 100 義大利黑麥草 40 25 30 黃豆 100 95 98 蘇利南草 85 75 90 筒麻 95 85 70 小麥 20 0 0 風剪草 70 45 60 表Β 62 g ai/ha 18 19 20 萌後 大麥 0 35 0 百慕達草 70 95 90 黑草 5 65 40 毛白露草 5 90 - 金絲雀草 40 95 35 繁縷 100 100 98 蒼耳 100 - 100 玉米 35 85 25 大馬唐草 65 95 85 烏利杯草 98 95 95 寶蓋草 100 70 100 法氏狗尾草 85 95 95 莠草 50 95 85 八仙草 65 80 - 牛筋草 70 85 85 強生草 85 - 75 地膚 65 100 98 藜 100 100 98 牵牛花 100 100 100 油莎草 55 65 75 野生燕麥 45 80 10 反枝莧 100 100 98 豬草 100 100 98 義大利黑麥草 0 70 0 黃豆 100 98 85 蘇利南草 85 100 80 苟麻 75 100 90 100 100 100 100 100 100 100 100 75 100 0 20 10 0 50 10 5 5 15 0 98 100 100 98 98 98 100 98 100 100 75 100 80 35 40 75 75 80 75 80 70 95 75 85 65 90 90 80 75 90 5 30 25 0 35 0 5 0 0 0 5 60 70 25 60 50 55 55 40 50 22 23 化合物 24 25 26 28 29 30 31 32 35 10 20 5 0 5 15 0 10 0 95 95 95 95 80 100 95 90 70 90 20 10 30 15 5 40 50 35 10 30 30 15 40 5 5 30 10 5 15 10 50 45 60 30 10 10 25 35 30 20 98 95 98 98 98 98 100 100 100 100 90 - 70 98 - - - 100 85 95 65 20 65 95 15 55 65 25 35 25 98 98 90 95 75 80 95 80 75 75 85 95 90 98 70 95 85 45 65 95 90 80 98 100 98 100 90 70 75 100 85 90 80 95 100 85 90 75 75 95 70 90 90 100 35 65 90 65 70 90 90 90 75 90 85 80 85 80 90 85 85 90 85 90 70 85 90 55 65 80 65 80 98 98 50 75 65 45 70 80 85 98 85 85 90 98 100 75 15 75 100 100 98 98 100 100 100 98 95 100 98 90 100 100 95 100 100 100 80 100 90 70 80 45 75 15 70 50 35 80 60 40 30 30 0 15 15 25 35 20 95 95 98 95 100 100 100 100 90 100 100 95 95 100 100 100 100 100 65 98 25 5 0 0 0 5 10 10 20 0 95 95 85 95 85 100 100 95 95 98 80 75 85 95 60 75 70 75 70 75 95 95 80 90 100 80 98 100 95 95 220 201240602 小麥 0 85 0 風剪草 50 98 60 表Β 31 g ai/ha 1 3 4 萌後 大麥 - 0 0 百慕達草 70 55 60 黑草 45 40 20 毛白露草 55 0 5 金絲雀草 85 45 60 繁縷 100 100 100 蒼耳 - 98 98 縠物 45 40 60 大馬唐草 85 75 80 烏利杯草 75 75 75 寶蓋草 45 95 70 法氏狗尾草 95 80 70 莠草 70 80 85 八仙草 85 60 80 牛筋草 80 75 65 強生草 75 85 80 地膚 40 10 20 藜 100 100 98 牽牛花 100 85 98 油莎草 65 70 45 野生燕麥 80 55 45 反枝莧 100 100 95 豬草 98 100 100 義大利黑麥草 15 25 30 黃豆 100 95 95 蘇利南草 75 75 75 〶麻 85 75 60 小麥 20 0 0 風剪草 55 25 50 表B 31 g ai/ha 18 19 20 55 55 15 25 0 10 15 35 25 35 50 30 85 70 10 10 40 50 40 30 化合物 6 7 8 10 11 12 14 15 16 17 0 20 0 0 0 0 0 0 0 0 35 85 95 80 70 5 55 75 70 25 5 60 10 5 50 - 5 0 0 5 0 - 25 5 20 10 35 40 5 10 5 45 25 5 30 35 5 35 35 20 98 100 100 100 98 100 100 100 98 100 90 - 98 98 100 95 95 98 80 100 20 80 5 10 15 65 15 5 5 15 65 98 80 80 70 15 75 65 65 75 75 100 75 45 55 70 80 85 95 95 60 85 80 100 100 100 100 100 100 100 75 95 80 70 85 80 75 75 75 80 45 100 35 25 60 50 40 40 35 40 45 70 25 70 50 50 75 40 50 80 65 100 75 75 75 75 65 65 70 40 85 90 80 20 65 60 75 95 60 70 5 85 70 75 60 5 50 10 5 75 80 100 98 100 100 100 100 98 90 100 95 98 90 98 100 98 95 100 85 100 10 75 75 80 70 75 75 40 15 85 10 45 40 0 5 40 45 40 45 50 95 100 80 100 90 98 100 95 95 190 98 100 100 100 100 100 100 100 60 100 0 5 0 0 15 10 5 5 10 0 90 100 95 98 98 98 98 98 98 100 70 100 75 25 20 60 70 75 70 65 70 90 60 80 60 80 80 65 70 80 0 30 15 0 10 0 5 0 0 0 0 60 60 5 50 30 45 55 30 25 化合物 22 23 24 25 26 28 29 30 31 32 221 201240602 萌後 大麥 0 30 0 百慕達草 70 85 75 黑草 0 60 10 毛白露草 5 80 - 金絲雀草 35 95 5 繁縷 100 100 90 蒼耳 98 - - 穀物 5 - 15 大馬唐草 55 90 75 烏利杯草 90 95 75 寶蓋草 100 70 98 法氏狗尾草 85 90 75 莠草 10 75 80 八仙草 45 80 70 牛筋草 70 80 85 強生草 75 - 60 地膚 15 98 90 藜 100 100 98 牽牛花 100 - 100 油莎草 40 55 75 野生燕麥 40 60 5 反枝莧 100 100 90 豬草 100 100 98 義大利黑麥草 0 55 0 黃豆 100 95 80 蘇利南草 80 100 75 筒麻 70 98 75 小麥 0 70 0 風剪草 30 95 35 表Β 化合物 16 g ai/ha 10 11 萌後 大麥 0 0 百慕達草 75 65 黑草 5 50 毛白露草 0 5 10 0 0 0 0 0 5 0 0 0 90 95 80 95 75 80 85 80 65 85 5 10 10 10 0 30 15 35 5 0 5 10 10 0 0 10 5 5 5 5 45 25 10 10 0 5 10 30 30 10 98 95 55 95 98 85 100 100 85 100 90 - 0 - - - - 98 80 85 35 5 5 85 5 55 65 10 25 25 95 95 60 80 70 75 95 75 65 65 75 85 75 95 60 25 65 25 60 85 90 70 95 95 80 80 90 70 75 85 80 80 55 95 100 75 85 65 65 75 50 70 85 90 20 55 90 60 50 75 80 85 50 85 70 70 85 55 85 85 85 85 75 85 65 70 85 50 55 75 55 75 80 80 45 65 65 45 50 80 80 95 5 70 75 50 100 45 10 65 100 100 90 98 85 85 98 95 85 95 98 85 100 98 80 95 100 85 80 80 80 60 55 5 65 0 60 40 20 80 35 35 5 10 0 5 10 10 10 15 95 80 98 85 90 80 98 98 85 98 100 90 85 98 100 98 100 80 65 95 20 0 0 0 0 5 10 0 5 0 85 80 70 75 75 95 95 95 85 85 75 75 70 75 45 60 65 60 65 70 95 90 65 75 98 80 95 95 90 95 40 50 0 5 0 10 5 15 25 25 30 10 40 30 0 5 30 30 30 30 表B 化合物 8 g ai/ha 11 17 萌後 大麥 0 0 百慕達草 55 5 黑草 0 0 毛白露草 5 5 222 201240602 金絲雀草 0 15 繁縷 98 95 蒼耳 95 90 玉米 5 5 大馬唐草 70 60 烏利杯草 20 55 寶蓋草 95 100 法氏狗尾草 65 75 莠草 10 40 八仙草 30 50 牛筋草 75 60 強生草 5 45 地膚 75 55 藜 100 85 牽牛花 65 85 油莎草 70 60 野生燕麥 0 0 反枝莧 85 85 豬草 100 98 義大利黑麥草 0 5 黃豆 95 95 蘇利南草 15 0 筒麻 80 15 小麥 0 5 風剪草 5 10 表B 化合物 250 g ai/ha 7 14 萌前 百慕達草 100 100 黑草 85 5 毛白露草 15 45 蒼耳 100 100 玉米 25 25 大馬唐草 100 100 烏利杯草 95 98 法氏狗尾草 100 100 莠草 100 70 金絲雀草 5 5 繁縷 50 ]00 蒼耳 90 100 玉米 0 0 大馬唐草 45 55 烏利杯草 15 75 寶蓋草 90 100 法氏狗尾草 70 70 莠草 25 10 八仙草 50 45 牛筋草 35 5 強生草 10 60 地膚 55 25 藜 85 100 牽牛花 85 85 油莎草 45 80 野生燕麥 0 40 反枝莧 85 100 諸草 90 65 義大利黑麥草 0 0 黃豆 85 90 蘇利南草 0 25 筒麻 10 75 小麥 0 0 風剪草 5 5 表B 化合物 125 g ai/ha 7 14 25 萌前 百慕達草 100 100 100 黑草 25 0 0 毛白露草 0 5 0 蒼耳 100 98 - 玉米 20 20 0 大馬唐草 100 100 100 烏利杯草 95 85 85 法氏狗尾草 95 100 25 莠草 98 40 0 223 201240602 八仙草 95 98 90 八仙草 95 95 牛筋草 100 100 100 牛筋草 100 100 強生草 98 95 100 強生草 80 90 地膚 98 100 100 地膚 95 100 藜 100 100 100 藜 100 100 牵牛花 98 100 - 牵牛花 80 100 顛茄 100 100 98 顛% 100 100 油莎草 95 95 70 油莎草 95 90 野生燕麥 10 55 0 野生燕麥 0 0 反枝莧 100 100 100 反枝莧 .100 100 豬草 100 100 100 豬草 100 100 俄國莉 95 100 90 俄國莉 90 90 義大利黑麥草 30 5 0 義大利黑麥草 0 0 黃豆 95 98 90 黃豆 85 95 向曰蔡 98 98 98 向曰蔡 95 95 蘇利南草 95 100 98 蘇利南草 90 80 筒麻 100 100 - 筒麻 100 100 小麥 0 0 0 小麥 0 0 90 98 60 98 100 98 45 0 90 100 90 0 75 90 80 0 表B 化合物 表B 化合物 62 g ai/ha 7 14 25 31 g ai/ha 7 14 萌前 萌前 百慕達草 100 98 100 百慕達草 100 95 黑草 0 0 0 黑草 0 0 毛白露草 0 5 0 毛白露草 0 5 蒼耳 100 65 - 蒼耳 100 45 玉米 20 20 0 玉米 0 5 大馬唐草 98 100 45 大馬唐草 95 95 烏利杯草 75 75 75 烏利杯草 45 30 法氏狗尾草 80 95 5 法氏狗尾草 75 75 莠草 90 5 0 莠草 55 5 八仙草 85 90 85 八仙草 80 65 牛筋草 100 98 95 牛筋草 98 95 強生草 20 65 25 強生草 0 15 地膚 90 80 90 地膚 85 70 藜 100 100 100 藜 100 100 牵牛花 65 98 - 牵牛花 0 5 顛茄 100 100 98 顛茄 100 98 25 98 0 0 0 5 70 0 0 85 75 0 70 98 224 95 201240602 油莎草 95 85 5 油莎草 95 65 0 野生燕麥 0 0 0 野生燕麥 0 0 0 反枝莧 100 100 85 反枝莧 100 100 75 豬草 100 100 100 豬草 100 100 85 俄國薊 90 90 85 俄國薊 85 85 80 義大利黑麥草 0 0 0 義大利黑麥草 0 0 0 黃豆 80 80 60 黃豆 5 75 0 向曰葵 85 85 80 向曰葵 60 65 70 蘇利南草 90 60 40 蘇利南草 45 45 0 问麻 85 100 - 苘蔚: 50 75 - 小麥 0 0 0 小麥 0 0 0 試驗c 將選自百慕達草、蘇利南草 (Brachiaria decumbens)、大馬唐草(Digitaria 5 sanguinalis)、赛專(Setaria viridis)、牛筋草(Eleusine indica)、強支草(Sorghum haiepeme)、地 $ (Kochia scoparia)、牵牛花(pitted morningglory, Ipomoea 、香附子(purple nutsedge) rotundus)' ^ (common ragweed, Ambrosia elatior)' M, 10 (Brassica nigra)、大利草(guineagrass) (Panicum maximum)、辑草(Echinochloa cms-galli)、猿緣草 (sandbur) (southern sandbur, Cenchrus echinatus) ' 花稳(prickly sida) 、義大利黑麥草 multiflorum)、馬齒莧(purslane) (common purslane, 15 Portulaca oleracea)、信號草(broadleaf signalgrass, 万nae/nar/a 、歐洲黃菀(groundsel) (common groundsel, Senecio vulgaris) ' (common chickweed, 、鴨 草(dayflower) (Virginia (VA) 225 201240602 dayflower, Commelina virginica)、藍草(bluegrass) (annual bluegrass,Poa annua)、羅氏草(itchgrass) (及coc/nwc/nwewsh)、魁克麥草(quackgrass) 則)、田旋花(field bindweed) (Cowvo/vw/ws iarvew·?/5)、鬼針草(spanishneedles) (B/i/e/w 、 錦葵(mallow) (common mallow, Μα/να 與俄國 薊(Russian thistle) (5W⑽/α紿/ί)之植物物種的種子栽植 於壤土與沙之掺合物中,並且以配製於不具植物毒性溶 劑混合物中之試驗化學物質進行萌前處理,該混合物包 括一界面活性劑。同時來自這些雜草物種的植物以試驗 化學物質進行萌後施用處理,該試驗化學物質係以相同 方式配製。使用高度範圍在2至18 cm ( 1至4葉階段) 的植物來進行萌後處理。 經處理之植物與防治組係在溫室中養護14至21 天’之後將所有物種與防治組比較並目視評估。歸納於 表C中之植物反應評級係基於0至100的標度,其中0 為無效果而1〇〇為完全防治。顯示為破折號(_)之反應意 指無試驗結果。 表C 化合物 250 g ai/ha 萌後 25 稗草 90 百慕達草 95 黑芥 95 藍草 70 繁縷 95 大馬唐草 鴨56草 80 表C 化合物 125 g ai/ha 19 25 萌後 禆草 90 80 百慕達草 90 90 黑芥 95 95 藍草 75 60 繁縷 100 95 大馬唐草 75 80 鴨路草 90 226 201240602 田旋花 75 田旋花 60 70 莠草 90 莠草 90 80 牛筋草 70 牛筋草 70 70 歐洲黃菀 100 歐洲黃菀 95 100 大利草 90 大利草 80 80 羅氏草 85 羅氏草 70 75 強生草 85 強生草 85 80 地膚 70 地膚 70 50 錦葵 60 錦葵 70 50 牵牛花 90 牽牛花 90 90 香附子 10 香附子 60 0 刺黃花稳 40 刺黃花稳 50 40 馬齒莧 60 馬齒莧 60 60 魁克麥草 40 魁克麥草 75 30 豬草 95 豬草 90 95 義大利黑麥草 0 俄國莉 95 95 蒺藜草 85 義大利黑麥草 50 0 信號草 90 蒺藜草 85 75 蘇利南草 90 信號草 90 85 鬼針草 - 90 蘇利南草 90 85 表C 化合物 表C 化合物 62 g ai/ha 19 25 31 g ai/ha 19 25 萌後 萌後 稗草 85 80 稗草 85 75 百慕達草 80 75 百慕達草 70 75 黑芥 80 85 黑芥 80 50 藍草 70 30 藍草 50 10 繁縷 95 80 繁縷 95 75 大馬唐草 70 75 大馬唐草 70 60 鴨路草 70 鴨瓶草 60 田旋花 50 70 田旋花 50 - 莠草 85 70 莠草 80 - 牛筋草 70 60 牛筋草 65 50 歐洲黃菀 95 100 歐洲黃绝 90 95 大利草 60 80 大利草 50 55 羅氏草 65 65 羅氏草 50 40 227 201240602 強生草 70 80 強生草 60 75 地膚 60 40 地膚 50 30 錦葵 70 50 錦蔡 50 50 牽牛花 90 80 牽牛花 85 75 香附子 60 0 香附子 50 0 刺黃花德 30 20 刺黃花稳 30 20 馬齒莧 50 50 馬齒莧 50 40 魁克麥草 70 10 魁克麥草 50 5 豬草 90 90 豬草 80 90 俄國薊 90 70 俄國韵 20 - 義大利黑麥草 30 0 義大利黑麥草 15 - 蒺藜草 75 70 蒺藜草 70 60 信號草 90 80 信號草 80 75 鬼針草 95 85 鬼針草 85 - 蘇利南草 80 80 蘇利南草 80 75Table B 62 g ai/ha Immersion 15 16 17 18 19 Valerian 0 0 0 0 0 Heterophylla 75 30 50 0 60 Rice 0 0 0 0 0 Round Umbrella 70 0 50 0 70 Compound 20 21 22 23 24 25 26 27 28 0 0 55 40 20 0 0 0 0 0 0 75 50 50 0 30 20 0 10 0 45 25 20 0 10 0 0 0 0 80 50 30 0 60 20 30 5 201240602 Table B Compound 62 g ai/ha 29 30 31 32 33 34 Immersion 稗 0 0 0 0 0 0 异药花 0 0 0 0 0 0 稻 0 0 0 0 0 0 轮草草 0 30 0 0 0 70 Table B Compound 31 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Immersion 稗草 0 0 0 0 0 0 -0 0 0 0 0 0 20 Ivory flower 70 0 0 0 0 0 0 0 0 80 50 50 0 70 Rice 0 0 0 0 0 0 0 0 0 0 0 10 0 20 omnivorous straw 70 0 40 0 0 0 0 0 0 40 0 0 0 45 Table B Compound 31 g ai/ha Immersion 15 16 17 18 19 20 21 22 23 24 25 26 27 28 稗草0 0 0 0 0 0 0 30 0 20 0 0 0 0 异药花65 30 0 0 40 0 0 45 0 40 0 20 0 0 Rice 0 0 0 0 0 0 0 20 20 10 0 0 0 0 65 0 0 0 60 0 0 0 0 0 0 20 0 0 Table B Compound 31 g ai/ha Immersion 29 30 31 32 33 34 稗草0 0 0 0 0 0 异药花0 0 0 0 0 - Rice 0 0 0 0 0 0 轮草草0 0 0 0 0 - Table B Compound 250 g ai/ha After the sprout 1 3 4 5 6 8 12 14 15 16 18 19 20 21 Barley 80 50 5 10 5 50 15 50 5 35 5 80 5 0 Bermuda grass 85 90 85 85 65 98 65 90 95 90 90 95 95 90 215 201240602 Black grass 85 85 55 40 5 70 80 15 60 5 70 80 55 10 Buttercup - 5 5 35 35 90 35 70 70 10 40 95 - 15 Canary grass 100 85 85 85 40 100 90 55 60 90 70 100 40 10 Traditional 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Xanthium - 100 98 98 100 100 100 100 100 100 100 - 100 100 Corn 80 85 80 90 65 80 85 75 60 50 60 90 75 80 Horse Grass, Large 98 90 90 85 95 98 80 100 98 98 75 100 95 95 Ulivia 98 90 95 90 95 98 95 100 100 100 100 98 100 95 Komgrass - 100 100 100 100 100 100 100 100 100 100 100 100 100 Phnom Penh 100 90 95 95 95 98 95 98 98 85 98 95 98 95 Valerian 95 100 100 95 90 90 90 98 60 70 98 100 95 100 Eight Grasses - 95 95 60 - 85 85 95 85 90 80 95 70 90 Goosegrass 95 85 90 - 85 98 90 95 98 85 95 90 98 85 Johnson grass 95 95 98 95 98 100 90 98 100 85 100 - 85 98 Kochia 90 90 75 15 65 100 65 100 80 75 98 100 100 100 藜100 100 100 100 100 100 100 100 100 100 100 100 100 - Morning Glory 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Papyrus 80 85 80 85 45 85 85 85 75 65 65 85 80 80 Wild oats 90 95 85 60 35 98 90 95 55 85 70 95 20 5 Anti-branches 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Italian ryegrass 45 35 40 5 5 35 20 10 10 20 20 95 5 5 Soybean 100 98 98 98 98 100 98 100 100 100 100 100 95 98 Suriname grass 90 85 95 75 85 98 85 95 98 85 98 100 85 85 Cannula 100 95 85 85 80 98 100 100 95 90 90 100 100 95 Wheat 35 0 0 5 5 40 5 20 30 0 30 95 20 20 Wind-cut grass 95 85 90 45 55 98 65 90 80 65 85 100 80 85 Table B Compound 250 g ai/ha After the attack 22 23 24 25 26 28 29 30 31 32 Barley 80 55 35 30 10 35 35 20 50 5 Bermuda grass 98 95 98 98 95 100 95 95 85 95 Black grass 25 30 80 40 30 65 85 50 35 40 毛白草草 35 80 80 10 10 45 35 45 40 55 Canary grass 80 95 90 60 50 40 50 50 80 45 Traditional 100 100 100 100 100 100 100 100 100 100 Xanthium 100 98 100 100 100 - - 100 98 98 216 201240602 Maize 80 90 85 100 35 85 80 55 75 65 Da Ma Tang Cao 98 100 95 98 90 100 98 95 85 98 Wu Li Cup Grass 90 98 98 100 80 100 98 85 80 98 Bao Gai Grass 100 100 100 100 100 100 100 100 100 100 foxtail sage 90 95 95 95 100 100 95 90 90 98 莠草90 98 100 100 70 100 95 95 70 95 八仙草95 98 95 90 90 85 90 95 95 90 牛草草95 98 98 95 85 100 95 75 85 95 Johnson grass 80 100 100 100 75 98 95 75 80 100 Kochia 98 100 98 98 95 100 100 100 55 95 藜100 100 98 100 100 100 100 100 98 100 Morning glory 100 100 100 100 100 100 100 100 98 100 sedges 90 90 90 55 85 45 85 80 60 100 wild oats 60 95 85 45 15 50 40 50 45 50 prune 98 98 100 100 100 100 100 100 98 100 ragweed 100 100 100 100 100 100 100 100 95 100 Italian ryegrass 30 35 5 5 40 10 30 45 30 30 Soybeans 98 98 95 98 98 100 100 100 98 98 Suriname Grass 85 95 95 98 70 95 80 85 85 95 Tubes 98 98 100 98 100 100 100 100 95 98 Wheat 90 90 30 35 25 50 40 40 40 60 Wind shears Grass 90 80 100 80 55 80 70 80 60 80 Table B Compound 125 g ai/ha 1 3 4 5 6 8 10 12 14 15 16 18 19 20 Post-emergence barley 70 30 5 5 0 15 0 5 5 0 20 0 55 5 Bermuda grass 85 85 80 80 50 98 90 35 75 85 85 85 95 95 Lane 85 85 40 35 5 35 10 70 15 15 0 20 75 40 Mao Bailu - 0 5 0 0 90 10 20 50 45 10 20 90 - Canary grass 100 80 85 65 35 65 20 70 30 60 60 50 100 40 繁繁 100 100 100 98 100 100 100 100 100 100 100 100 100 98 Xanthium 100 100 98 95 100 100 100 100 100 100 100 100 - 100 Maize 75 85 80 80 65 65 65 80 75 25 35 45 85 70 Large horse grass 95 90 90 85 90 95 95 60 98 85 98 70 98 85 Uli cup grass 90 90 95 85 90 98 65 95 98 100 98 98 98 98盖盖草-100 100 100 100 100 100 100 100 100 100 100 85 100 foxtail foxtail 98 85 90 90 90 98 85 90 95 95 85 95 95 95 217 20124060 2 莠草95 95 95 八仙草-85 90 牛草草 95 85 85 Johnson grass 90 95, 98 地肤85 65 60 藜100 100 100 Morning glory 100 100 100 sedge 75 80 65 Wild oats 90 90 80 Twigs 100 100 100 ragweed 100 100 100 Italian ryegrass 45 35 35 Soybeans 100 95 98 Suriname grass 85 80 90 Casing 100 95 75 Wheat 30 0 0 Wind-cut grass 85 75 80 Table B 125 g ai/ha 21 22 Post-emergence barley 0 60 Bermuda grass 90 98 Black grass 10 25 Hairy white grass 5 35 Canary grass 5 70 Traditional 98 100 Xanthium 100 95 Corn 80 80 Large horse grass 85 98 Uli cup grass 85 85 100 100 French foxtail 95 85 莠草100 85 八仙草85 90 牛筋草80 90 强生草95 70 地肤90 95 90 90 70 90 85 55 70 90 98 90 80 70 90 60 85 85 90 75 90 70 80 95 85 85 95 90 85 85 90 90 90 100 65 85 95 98 80 98 - 75 10 98 100 45 98 75 65 65 100 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 25 80 90 80 85 60 40 60 65 80 35 95 15 70 90 50 50 65 95 20 100 100 100 100 100 100 100 10 0 100 98 100 100 100 100 100 100 100 100 100 98 0 30 5 20 10 10 20 5 70 5 98 100 100 98 100 100 100 100 100 95 80 95 50 85 95 95 80 90 100 80 75 80 85 95 100 80 80 80 100 95 5 30 5 0 15 5 0 0 90 5 30 95 60 65 65 75 60 65 100 75 24 Compound 25 26 28 29 30 31 32 35 15 5 15 35 5 35 0 98 98 90 100 95 90 85 90 80 30 10 50 70 45 30 40 50 10 5 40 10 35 30 35 75 45 45 15 45 35 55 45 100 98 100 98 100 100 100 100 98 100 - - - 100 95 95 85 95 20 75 70 50 65 45 95 98 85 100 98 90 85 85 98 100 75 100 90 75 70 95 100 100 98 100 - 100 85 100 95 95 100 100 95 80 85 95 98 100 40 90 90 85 70 90 85 90 85 85 90 85 90 90 95 95 75 100 90 65 80 85 98 100 55 75 75 70 70 95 95 95 100 100 100 80 95 95 218 201240602 藜- 100 Morning Glory 100 100 Oil Sedge 65 90 Wild Oats 5 60 Anti-branches 95 1 98 Ragweed 100 100 Italian ryegrass 0 30 Soybean 98 95 Suriname Grass 80 80 Castor 80 1 98 Wheat 10 1 90 Wind Cut Grass 45 60 Table B 62 g ai/ha 1 3 4 Post-emergence Barley 50 5 0 Bermuda Grass 85 60 75 Black Grass 60 70 30 White Dew 55 0 5 Canary Grass 95 80 75 Traditional 100 100 100 Xanthium - 100 98 Corn 75 70 80 Large Horse Grass 95 80 85 Uli Cup 85 85 90 60 95 100 foxtail sage 95 85 85 valerian 75 90 95 october grass 90 60 90 tendon grass 85 75 80 strong grass 85 85 95 terracotta 75 25 50 藜100 100 100 morning glory 100 100 100 sedge 75 80 50 Wild oats 85 85 60 Anti-branches 100 100 100 98 100 100 100 100 100 98 100 100 100 95 100 100 100 98 100 90 45 80 20 70 70 40 95 60 40 10 45 30 45 45 45 100 98 100 100 100 100 95 100 100 100 100 100 100 100 95 100 5 5 30 10 15 30 20 10 90 98 90 100 100 98 98 98 95 98 65 95 75 85 75 85 90 95 100 100 100 100 95 98 15 35 0 35 35 40 35 40 98 80 50 10 50 55 60 60 Compound 6 7 8 10 11 12 14 15 16 17 0 35 5 0 0 0 0 0 0 0 45 85 95 85 80 5 75 75 80 75 5 70 30 5 55 65 10 5 0 20 0 - 60 5 30 10 40 45 5 15 35 80 55 15 35 60 20 45 40 30 100 100 100 100 100 100 100 100 100 100 95 - 100 98 100 100 95 100 98 100 45 9 0 10 20 20 65 35 25 10 60 75 100 95 85 85 60 90 75 90 80 85 100 90 60 85 85 98 90 95 98 100 85 100 100 100 100 100 100 100 100 85 98 90 80 90 85 85 90 80 85 85 100 60 50 85 50 80 50 50 80 55 85 50 70 85 60 85 60 50 80 65 100 75 85 80 75 75 80 85 45 90 100 90 25 85 60 80 98 65 70 5 100 75 95 70 10 75 25 20 98 98 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 95 100 100 100 25 85 75 85 75 80 80 50 25 90 30 90 85 5 20 60 90 50 50 60 100 100 98 100 100 100 100 100 100 100 219 201240602 猪草100 100 100 Italian ryegrass 40 25 30 Soy 100 95 98 Suriname grass 85 75 90 tube stalk 95 85 70 Wheat 20 0 0 Wind cut grass 70 45 60 Table Β 62 g ai/ha 18 19 20 Post-emergence barley 0 35 0 Bermuda grass 70 95 90 Black grass 5 65 40 White dew 5 90 - Canary grass 40 95 35 Traditional 100 100 98 Xanthium 100 - 100 Corn 35 85 25 Large horse grass 65 95 85 Uli Cup Grass 98 95 95 baocai 100 70 100 foxtail sage 85 95 95 sedge 50 95 85 october 65 80 - tendon grass 70 85 85 Grass 85 - 75 Kochia 65 100 98 藜100 100 98 Morning Glory 100 100 100 Papyrus 55 65 75 Wild Oats 45 80 10 Anti-branches 100 100 98 Rag 100 100 98 Italian Ryegrass 0 70 0 Soybeans 100 98 85 Suriname grass 85 100 80 ramie 75 100 90 100 100 100 100 100 100 100 100 75 100 0 20 10 0 50 10 5 5 15 0 98 100 100 98 98 98 100 98 100 100 75 100 80 35 40 75 75 80 75 80 70 95 75 85 65 90 90 80 75 90 5 30 25 0 35 0 5 0 0 0 5 60 70 25 60 50 55 55 40 50 22 23 Compound 24 25 26 28 29 30 31 32 35 10 20 5 0 5 15 0 10 0 95 95 95 95 80 100 95 90 70 90 20 10 30 15 5 40 50 35 10 30 30 15 40 5 5 30 10 5 15 10 50 45 60 30 10 10 25 35 30 20 98 95 98 98 98 98 100 100 100 100 90 - 70 98 - - - 100 85 95 65 20 65 95 15 55 65 25 35 25 98 98 90 95 75 80 95 80 75 75 85 95 90 98 70 95 85 45 65 95 90 80 98 100 98 100 90 70 75 100 85 90 80 95 100 85 90 75 75 95 70 90 90 100 35 65 90 65 70 90 90 90 75 90 85 80 85 80 90 85 85 90 85 90 70 85 90 55 65 80 65 80 98 98 50 75 65 45 70 80 85 98 85 85 90 98 100 75 15 75 100 100 98 98 100 100 100 98 95 100 98 90 100 100 95 100 100 100 80 100 90 70 80 45 75 15 70 50 35 80 60 40 30 30 0 15 15 25 35 20 95 95 98 95 100 100 100 100 90 100 100 95 95 100 100 100 100 100 65 98 25 5 0 0 0 5 10 10 20 0 95 95 85 95 85 100 100 95 95 98 80 75 85 95 60 75 70 75 70 75 95 95 80 90 100 80 98 100 95 95 220 201240602 Wheat 0 85 0 Wind-cut grass 50 98 60 Table Β 31 g ai/ha 1 3 4 Post-emergence barley - 0 0 Bermuda grass 70 55 60 Black grass 45 40 20 hair白露草55 0 5 Canary grass 85 45 60 繁繁 100 100 100 Xanthium - 98 98 縠物45 40 60 大马唐草85 75 80 乌利杯草75 75 75 宝盖草45 95 70 法氏草草95 80 70 莠草70 80 85 八仙草85 60 80 牛草草80 75 65 健生草75 85 80 地肤40 10 20 藜100 100 98 Morning Glory 100 85 98 sedge 65 70 45 Wild oats 80 55 45 100 100 95 ragweed 98 100 100 Italian ryegrass 15 25 30 soybean 100 95 95 Suriname grass 75 75 75 ramie 85 75 60 wheat 2 0 0 0 Wind cut grass 55 25 50 Table B 31 g ai/ha 18 19 20 55 55 15 25 0 10 15 35 25 35 50 30 85 70 10 10 40 50 40 30 Compound 6 7 8 10 11 12 14 15 16 17 0 20 0 0 0 0 0 0 0 0 35 85 95 80 70 5 55 75 70 25 5 60 10 5 50 - 5 0 0 5 0 - 25 5 20 10 35 40 5 10 5 45 25 5 30 35 5 35 35 20 98 100 100 100 98 100 100 100 98 100 90 - 98 98 100 95 95 98 80 100 20 80 5 10 15 65 15 5 5 15 65 98 80 80 70 15 75 65 65 75 75 100 75 45 55 70 80 85 95 95 60 85 80 100 100 100 100 100 100 100 75 95 80 70 85 80 75 75 75 80 45 100 35 25 60 50 40 40 35 40 45 70 25 70 50 50 75 40 50 80 65 100 75 75 75 75 65 65 70 40 85 90 80 20 65 60 75 95 60 70 5 85 70 75 60 5 50 10 5 75 80 100 98 100 100 100 100 98 90 100 95 98 90 98 100 98 95 100 85 100 10 75 75 80 70 75 75 40 15 85 10 45 40 0 5 40 45 40 45 50 95 100 80 100 90 98 100 95 95 190 98 100 100 100 100 100 100 100 60 100 0 5 0 0 15 10 5 5 10 0 90 100 95 98 98 98 98 98 98 100 70 100 75 25 20 60 70 75 70 65 70 90 60 80 60 80 80 65 70 80 0 30 15 0 10 0 5 0 0 0 60 60 5 50 30 45 55 30 25 Compound 22 23 24 25 26 28 29 30 31 32 221 201240602 Post-emergence barley 0 30 0 Bermuda grass 70 85 75 Black grass 0 60 10 毛白草草5 80 - Canary grass 35 95 5 Traditional 100 100 90 Xanthium 98 - - Cereal 5 - 15 Large horse grass 55 90 75 Uli cup grass 90 95 75 Komgrass 100 70 98 Pharis sylvestris 85 90 75 莠草10 75 80 八仙草45 80 70 牛草草70 80 85 恒生草75 - 60 地面15 98 90 藜100 100 98 Morning Glory 100 - 100 sedge 40 55 75 Wild Oats 40 60 5 Anti Twigs 100 100 90 ragweed 100 100 98 Italian ryegrass 0 55 0 Soybean 100 95 80 Suriname grass 80 100 75 Cannabis 70 98 75 Wheat 0 70 0 Wind-cut grass 30 95 35 Table Β Compound 16 g ai/ha 10 11 post-emergence barley 0 0 Bermuda grass 75 65 black grass 5 50 hair white dew 0 5 10 0 0 0 0 0 5 0 0 90 90 80 95 75 80 85 80 65 85 5 10 10 10 0 30 15 35 5 0 5 10 10 0 0 10 5 5 5 5 45 25 10 10 0 5 10 30 30 10 98 95 55 95 98 85 100 100 85 100 90 - 0 - - - - 98 80 85 35 5 5 85 5 55 65 10 25 25 95 95 60 80 70 75 95 75 65 65 75 85 75 95 60 25 65 25 60 85 90 70 95 95 80 80 90 70 75 85 80 80 55 95 100 75 85 65 65 75 50 70 85 90 20 55 90 60 50 75 80 85 50 85 70 70 85 55 85 85 85 85 75 85 65 70 85 50 55 75 55 75 80 80 45 65 65 45 50 80 80 95 5 70 75 50 100 45 10 65 100 100 90 98 85 85 98 95 85 95 98 85 100 98 80 95 100 85 80 80 80 60 55 5 65 0 60 40 20 80 35 35 5 10 0 5 10 10 10 15 95 80 98 85 90 80 98 98 85 98 100 90 85 98 100 98 100 80 65 95 20 0 0 0 0 5 10 0 5 0 85 80 70 75 75 95 95 95 85 85 75 75 70 75 45 60 65 60 65 70 95 90 65 75 98 80 95 95 90 95 40 50 0 5 0 10 5 15 25 25 30 10 40 30 0 5 30 30 30 30 Table B Compound 8 g ai/ha 11 17 Post-emergence barley 0 0 Bermuda grass 55 5 Black grass 0 0 White dew 5 5 222 201240602 Canary grass 0 15 Traditional 98 95 Xanthium 95 90 Corn 5 5 Large horse grass 70 60 Uli cup grass 20 55 Pomgrass 95 100 French foxtail 65 75 Alfalfa 10 40 Eight grass grass 30 50 cattle Rista 75 60 Johnson Grass 5 45 Ground 75 55 藜100 85 Morning Glory 65 85 Oil sedge 70 60 Wild oats 0 0 Anti-branches 85 85 Ragweed 100 98 Italian ryegrass 0 5 Soy 95 95 Suriname grass 15 0 Tubes 80 15 Wheat 0 5 Wind-cut grass 5 10 Table B Compound 250 g ai/ha 7 14 Pre-emergence Bermuda 100 100 Black Grass 85 5 Mao Lulu 15 45 Xanthium 100 100 Maize 25 25 Large Horsegrass 100 100 Uli Cup Grass 95 98 Fascia 100 100 莠草100 70 Canary grass 5 5 繁繁 50 ]00 Xanthium 90 100 Corn 0 0 Big horse grass 45 55 Uli cup grass 15 75 Kombu 90 100 Phnom Penh 70 70 莠草25 10 八仙草50 45 Goosegrass 35 5 Johnson grass 10 60 Kochia 55 25 藜85 100 Morning glory 85 85 Oil sedge 45 80 Wild oats 0 40 Anti-branches 85 100 Herbs 90 65 Italian ryegrass 0 0 Soybeans 85 90 Suriname Grass 0 25 Tube 10 10 Wheat 0 0 Wind Cut Grass 5 5 Table B Compound 125 g ai/ha 7 14 25 Pre-emergence Bermuda 100 100 100 Black Grass 25 0 0 White Dew 0 0 0 Xanthium 100 98 - Corn 20 20 0 Large唐草100 100 100 乌利杯草95 85 85 氏草草 95 100 25 莠草98 40 0 223 201240602 八仙草95 98 90 八仙草95 95 牛筋草100 100 100 牛筋草100 100 强生草98 95 100 Johnson Grass 80 90 Kochia 98 100 100 Koto 95 100 藜100 100 100 藜100 100 Morning Glory 98 100 - Morning Glory 80 100 Belladonna 100 100 98 %% 100 100 Oil sedge 95 95 70 Oil sedge 95 90 Wild oats 10 55 0 Wild oats 0 0 Anti-branches 100 100 100 Anti-branches. 100 100 Ragweed 100 100 100 Ragweed 100 100 Russian Li 95 100 90 Russian Li 90 90 Italian ryegrass 30 5 0 Italian ryegrass 0 0 Soybean 95 98 90 Soybean 85 95 Xiang Yu Cai 98 98 98 Xiang Yu Cai 95 95 Suriname Grass 95 100 98 Suriname Grass 90 80 Tube 100 100 - Tube 100 100 Wheat 0 0 0 Wheat 0 0 90 98 60 98 100 98 45 0 90 100 90 0 75 90 80 0 Table B Compound Table B Compound 62 g ai/ha 7 14 25 31 g ai/ha 7 14 Pre-emergence Bermuda 100 98 100 Bermuda 100 95 Black Grass 0 0 0 Black Grass 0 0 White Dew 0 0 0 White Dew 0 5 Cang 100 65 - Xanthium 100 45 Corn 20 20 0 Corn 0 5 Large horse grass 98 100 45 Large horse grass 95 95 Uli grass 75 75 75 Uri grass 45 30 French foxtail 80 95 5 French foxtail 75 75 莠Grass 90 5 0 莠草 55 5 八仙草85 90 85 八仙草80 65 牛筋草100 98 95 牛筋草98 95 强生草20 65 25 Johnson Grass 0 15 地肤90 80 90 地肤85 70 藜100 100 100藜100 100 Morning Glory 65 98 - Morning Glory 0 5 Belladonna 100 100 98 Belladonna 100 98 25 98 0 0 0 5 70 0 0 85 75 0 70 98 224 95 201240602 Oil sedge 95 85 5 Oil sedge 95 65 0 Wild oats 0 0 0 Wild oats 0 0 0 Anti-branches 100 100 85 Anti-branches 100 100 75 Ragweed 100 100 100 Ragweed 100 100 85 Russian 蓟90 90 85 Russian 蓟85 85 80 Italian ryegrass 0 0 0 Italian ryegrass 0 0 0 Soybean 80 80 60 Soybean 5 75 0 To the hollyhock 85 85 80 To the hollyhock 60 65 70 Suriname grass 90 60 40 Suriname grass 45 45 0 Ask Ma 85 100 - 苘蔚: 50 75 - Wheat 0 0 0 Wheat 0 0 0 Test c will be selected from the group consisting of Bermuda grass, Brachiaria decumbens, and great horse grass (Digitaria 5 sanguinalis), Setaria viridis, Eleusine indica, Sorghum haiepeme, Kochia scoparia, pitted morningglory, Ipomoea, purple nutsedge ) rotundus)' ^ (common ragweed, Ambrosia elatior)' M, 10 (Brassica nigra), guineagrass (Panicum maximum), Echinochloa cms-galli, sandbur (southern sandbur) Cenchrus echinatus) 'prickly sida, Italian ryegrass multiflorum, purslane (common purslane, 15 Portulaca oleracea), signal grass (broadleaf signalgrass, 10,000 nae/nar/a, European jaundice ( Groundsel) (common groundsel, Senecio vulgaris) ' (common chickweed, , dayflower (Virginia (VA) 225 201240602 dayflower, Commelina virginica), bluegrass (annual bluegrass, Poa annua), Roche grass (itchgrass) (and coc/nwc/nwewsh), quackgrass, field bindweed (Cowvo/vw/ws iarvew·?/5), spanishneedles (B/i/) Seeds of plant species of e/w, mallow (common mallow, Μα/να and Russian tle (Russian thistle) (5W(10)/α绐/ί) are planted in a blend of loam and sand and formulated The pre-emergence treatment is carried out on a test chemistry in a non-phytotoxic solvent mixture comprising a surfactant. At the same time, plants from these weed species were treated with a test chemical for post-emergence treatment, which was formulated in the same manner. Post-emergence treatment is carried out using plants ranging in height from 2 to 18 cm (1 to 4 leaf stage). All treated species and control groups were maintained in the greenhouse for 14 to 21 days&apos; after which all species were compared to the control group and visually assessed. The plant response ratings summarized in Table C are based on a scale from 0 to 100, where 0 is no effect and 1 is full control. The reaction shown as a dash (_) means no test results. Table C Compound 250 g ai/ha Post-emergence 25 Valerian 90 Bermuda Grass 95 Black Mustard 95 Blue Grass 70 Traditional 95 Large Horse Grass Duck 56 Grass 80 Table C Compound 125 g ai/ha 19 25 Post-emergence Valerian 90 80 Bermuda Grass 90 90 Black Mustard 95 95 Blue Grass 75 60 Traditional 100 95 Large Horse Grass 75 80 Duck Road Grass 90 226 201240602 Field Spin Flower 75 Field Spin Flower 60 70 Valerian 90 Valerian 90 80 Beetle Grass 70 Beef Grass 70 70 European Astragalus 100 European Astragalus 95 100 Big grass 90 Big grass 80 80 Roche grass 85 Roche grass 70 75 Johnson grass 85 Johnson grass 85 80 Koto 70 Kochia 70 50 Mallow 60 Mallow 70 50 Morning Glory 90 Morning Glory 90 90 Aconite 10 Aromatic Aconite 60 0 Yellow flower steady 40 Yellow flower steady 50 40 Purslane 60 Purslane 60 60 Quaker wheat grass 40 Quaker wheat 75 30 Rag grass 95 Ragweed 90 95 Italian ryegrass 0 Russian Li 95 95 Valerian 85 Italian Ryegrass 50 0 Signal Grass 90 Valerian 85 75 Suriname Grass 90 Signal Grass 90 85 Bidens - 90 Suriname Grass 90 85 Table C Compound Table C Compound 62 g ai/ha 19 25 31 g ai/ha 19 25 Post-emergence and post-emergence Valerian 85 80 Valerian 85 75 Bermuda grass 80 75 Bermuda grass 70 75 Black mustard 80 85 Black mustard 80 50 Blue grass 70 30 Blue grass 50 10 Traditional 95 80 Traditional 95 75 Malaysia Tang Cao 70 75 Da Ma Tang Cao 70 60 Duck Road Grass 70 Duckweed 60 Field Convolvulus 50 70 Field Convolvulus 50 - Valerian 85 70 Valerian 80 - Goosegrass 70 60 Goosegrass 65 50 European Jaundice 95 100 Europe Yellow 90 95 Big grass 60 80 Big grass 50 55 Roche grass 65 65 Roche grass 50 40 227 201240602 Johnson grass 70 80 Johnson grass 60 75 Kochia 60 40 Kochia 50 30 Mallow 70 50 Jin Cai 50 50 Morning glory 90 80 Morning Glory 85 75 Aromatic Aconite 60 0 Aconite 50 0 Aesculus 30 20 Aesculus 30 20 Purslane 50 50 Purslane 50 40 Quaker Wheat 70 70 Quaker Wheat 50 5 Ragweed 90 90 Ragweed 80 90 Russian 蓟90 70 Russian rhyme 20 - Italian ryegrass 30 0 Italian ryegrass 15 - 蒺藜草75 70 蒺藜草70 60 Signal grass 90 80 Signal grass 80 75 Bidens grass 95 85 Bidens grass 85 - Suriname grass 80 80 Suriname Grass 80 75

試驗D 將選自鳥眼婆婆納(bird’s-eye speedwell) (Feromca 、藍草(annual bluegrass,尸⑽wwa)、黑草 5 (Alopecurus myosuroides)、金絲、雀草(Phalaris minor)、 繁縷(common chickweed,*SVe//an&lt;3 wei/ζύτ)、八仙草 (catchweed bedstraw,、毛白露草(downy bromegrass)(价ieciorww)、原野鬼馨粟(field poppy) (Pizpaver 、原野紫羅蘭(field violet) (F/o/&lt;3 ίο 、莠草(Se/ar/a WWiZ/s)、寶蓋草(henbit deadnettle,Test D will be selected from the bird's-eye speedwell (Feromca, blue grass (annual bluegrass), Alopecurus myosuroides, gold silk, Phalaris minor, common chickweed , *SVe//an&lt;3 wei/ζύτ), catchweed bedstraw, downy bromegrass (ie ieororww), field poppy (Pizpaver, field violet) F/o/&lt;3 ίο, 莠草(Se/ar/a WWiZ/s), 盖bit grass (henbit deadnettle,

Lamium amplexicaule)、敎大利黑麥草(Lo丨ium multiflorum)、也濱(Kochia scoparia)、緣(Chenopodium a/6ww)、油菜籽(oilseed rape)(万广似幻〜mz/?w5)、反枝莧 reir〇y7ejcw5)、俄國莉AeWca)、白夏 is 菊(scentless chamomile) (A/air/caWa 、春大麥 (Hordeum vu!gare)、春小麥(Triticum aestivum)、野支秦 201240602 麥(Polygonum cowo/vw/⑽)、野生芥菜(公 恤)、野生燕麥(yve似加㈣、野生蘿蔔π叩办⑽似 raphanistmm)、風^萆(Apera spica_ventf}、冬大麥 (Hordeum vulgare)與冬麥(Triticum aestivum)之植物物種 5 的種子進行栽植,並且以配製於不具植物毒性溶劑混合 物中之試驗化學物質進行萌前處理,該混合物包括一界 面活性劑。同時來自這些作物與雜草物種的植物以部分 試驗化學物質進行萌後施用處理,該試驗化學物質係以 相同方式配製。植物的而度範圍在2至18 cm ( 1至4 1〇 葉階段)。 經處理之植物與防治組係在受控生長環境中養護 14至21天’之後將所有物種與防治組比較並目視評 估。歸納於表D中之植物反應評級係基於〇至1〇()的標 度’其中〇為無效果而100為完全防治。顯示為破折號 15 (-)之反應意指無試驗結果。 表D 125 g ai/ha 3 4 5 7 萌後 春大麥 30 25 10 80 冬大麥 40 30 35 35 黑草 100 60 50 80 藍草 85 85 75 90 毛白露草 35 25 40 65 野生蕎麥 55 70 90 100 金絲雀草 100 100 95 100 白夏菊 100 100 100 100 繁縷 100 100 98 100 寶蓋草 100 100 100 100 原野鬼罌粟 85 100 70 70 原野紫羅蘭 100 100 100 100 化合物 21 24 25 26 28 29 30 31 32 0 20 20 10 10 20 20 35 25 10 25 10 10 5 10 20 30 20 25 35 20 30 40 15 80 30 40 40 30 30 20 60 10 45 50 30 15 10 35 10 20 10 40 35 50 80 75 80 100 35 100 85 85 75 20 40 30 10 20 10 70 90 70 100 100 100 100 98 100 100 90 100 85 100 90 100 90 95 100 95 85 100 95 100 98 100 100 100 90 90 90 40 85 95 100 60 90 70 100 80 100 95 100 100 100 85 70 229 201240602 莠草 100 95 八仙草 90 85 地膚 50 45 藜 95 98 野生芥菜 100 90 野生燕麥 100 100 油菜籽 100 95 反枝莧 100 95 野生蘿葡 100 100 俄國薊 75 40 義大利黑麥草 35 40 婆婆納 100 100 春小麥 35 25 冬小麥 35 25 風剪草 90 90 100 100 75 90 80 80 40 90 85 100 85 75 75 75 90 75 75 85 90 90 95 80 95 85 95 85 100 85 85 95 100 90 100 90 98 85 100 98 85 95 100 85 90 85 95 80 75 100 95 95 90 20 20 60 10 25 15 65 60 30 100 90 80 80 100 85 95 100 80 100 100 85 100 95 100 90 100 80 75 75 100 80 75 80 98 90 80 100 85 100 90 80 95 .90 90 90 100 80 70 100 40 10 0 0 10 15 10 25 50 10 100 100 85 100 90 100 100 100 100 100 15 10 20 10 10 45 15 40 45 50 20 15 10 10 10 25 10 40 60 60 85 55 85 75 35 30 15 60 35 75 表D 62 g ai/ha 萌後 3 4 春大麥 25 20 冬大麥 30 20 黑草 95 60 藍草 75 80 毛白露草 35 20 野生蕎麥 35 40 金絲雀草 100 100 白夏菊 100 98 繁縷 98 100 寶蓋草 100 90 原野鬼罌粟 40 98 原野紫羅蘭 100 100 莠草 90 85 八仙草 85 85 地膚 30 25 藜 95 90 野生芥菜 98 80 野生燕麥 98 85 油菜籽 100 80 化合物 7 21 24 25 26 28 29 30 31 32 10 0 15 10 0 5 10 10 15 10 25 5 10 5 0 0 10 0 20 5 50 5 20 10 5 20 5 40 20 20 70 15 15 20 15 20 10 35 40 20 35 15 10 25 10 20 5 40 25 40 98 80 75 75 95 25 80 85 80 50 90 10 20 20 5 10 5 40 70 50 100 95 90 90 100 90 95 100 90 100 98 80 100 90 90 75 95 90 75 85 100 98 95 95 98 90 70 98 80 90 70 85 40 80 85 98 50 80 60 100 100 70 100 75 95 - 95 80 80 60 100 90 70 80 65 70 40 80 80 95 85 70 60 70 80 75 60 85 85 85 85 50 85 80 90 75 100 80 95 95 100 90 100 80 98 85 100 85 85 85 100 80 80 75 90 80 60 95 65 95 90 15 10 20 10 20 5 30 20 25 100 75 75 75 85 80 80 95 75 75 230 201240602 反枝莧 85 100 95 100 85 100 90 95 80 100 95 75 野生蘿蔔 100 80 100 100 60 70 70 90 90 75 100 75 俄國薊 75 40 80 75 70 75 90 85 85 100 60 50 義大利黑麥草 25 20 10 40 0 0 0 5 10 0 10 30 婆婆納 100 100 100 100 100 65 100 30 100 75 95 100 春小麥 20 15 10 15 10 10 5 5 25 15 25 35 冬小麥 25 20 10 10 10 5 5 5 25 5 30 30 風剪草 60 55 40 60 35 65 35 10 20 5 35 35 75 85 90 10 100 40 35 35 表D 化合物 31 g ai/ha 3 5 7 21 24 25 26 28 29 30 31 32 萌後 春大麥 15 5 10 0 10 5 0 0 0 0 10 0 冬大麥 30 10 15 0 5 0 0 0 0 0 5 0 黑草 70 30 30 5 0 0 0 10 0 20 10 15 藍草 70 30 40 0 10 10 5 10 10 10 20 20 毛白露草 30 20 20 10 10 5 0 15 0 20 15 30 野生蕎麥 25 60 80 75 40 75 85 15 70 75 75 30 金絲雀草 90 60 70 0 15 10 0 10 0 20 50 30 白夏菊 98 85 100 90 85 60 100 75 90 100 - 98 繁縷 90 85 95 70 95 90 85 65 90 80 70 80 寶蓋草 100 100 100 85 90 80 85 80 70 85 70 80 原野鬼罌粟 50 60 60 85 40 60 80 85 50 80 60 95 原野紫羅蘭 100 90 100 70 95 60 95 - 90 80 40 - 莠草 85 70 98 75 50 20 35 60 40 75 65 80 八仙草 85 60 80 60 50 65 75 75 55 80 80 85 地膚 25 30 75 25 70 75 85 50 100 50 35 70 藜 85 90 90 85 75 70 95 80 90 90 75 85 野生芥菜 95 90 100 50 50 65 80 80 50 90 45 85 野生燕麥 90 10 30 5 10 10 5 15 0 15 10 10 油菜籽 80 80 100 70 50 70 85 50 75 85 50 60 反枝莧 80 85 98 70 95 80 95 70 100 75 70 65 野生蘿蔔 98 95 100 60 35 70 90 65 60 95 70 85 俄國莉 60 80 65 30 75 80 80 75 80 40 50 70 義大利黑麥草 20 0 10 0 0 0 0 10 0 0 20 0 婆婆納 100 100 100 100 60 90 20 75 60 95 100 100 春小麥 15 5 10 0 10 0 0 10 5 10 5 25 冬小麥 15 5 5 5 5 0 0 10 0 15 10 15 風剪草 50 20 35 15 40 25 0 10 0 20 10 25 231 201240602 化合物 3 4 5 7 21 24 25 26 28 29 30 31 32 10 5 5 5 0 0 0 0 0 0 0 5 0 0 5 10 5 0 0 0 0 0 0 0 0 0 60 5 10 30 0 0 0 0 0 0 5 0 0 60 35 20 15 0 10 0 0 0 0 10 10 5 20 10 10 15 0 10 0 0 0 0 10 5 10 20 20 50 50 70 25 75 85 20 40 50 45 20 70 70 25 25 0 15 0 0 5 0 10 30 10 90 90 50 100 90 85 50 80 60 80 100 70 90 80 85 85 85 60 95 70 85 50 80 70 60 75 95 85 95 100 85 90 60 85 75 60 85 65 75 10 85 60 60 85 40 50 70 85 40 40 50 90 100 90 85 95 60 90 50 80 - 75 80 40 50 80 0 55 80 75 0 10 5 55 20 75 55 70 80 65 60 75 60 50 60 75 60 50 75 80 80 20 10 20 55 20 70 75 65 45 90 40 20 50 75 80 85 70 85 60 70 80 75 75 85 75 80 95 60 95 98 50 30 60 75 50 20 60 30 65 55 40 10 10 0 10 0 0 5 0 5 0 5 75 70 75 98 50 50 60 80 40 75 75 20 30 80 70 85 90 70 95 80 90 70 90 65 70 65 85 80 90 100 40 30 35 85 35 50 80 40 50 50 30 50 55 30 75 40 .75 60 60 35 50 50 10 0 0 0 0 0 0 0 5 0 0 0 0 100 100 100 100 100 30 90 20 70 50 80 85 100 0 5 0 5 0 0 0 0 5 0 0 5 5 10 10 0 5 0 0 0 0 0 0 5 5 5 20 35 20 25 0 25 10 0 0 0 10 5 15Lamium amplexicaule), Lo丨ium multiflorum, Kochia scoparia, Chenopodium a/6ww, oilseed rape (Wanguang illusion~mz/?w5), anti-branches苋reir〇y7ejcw5), Russian AeWca), scentless chamomile (A/air/caWa, spring barley (Hordeum vu!gare), spring wheat (Triticum aestivum), wild branch Qin 201240602 wheat (Polygonum cowo/ Vw/(10)), wild mustard (public shirt), wild oats (yve like (four), wild radish π叩 (10) like raphanistmm), wind 萆 (Apera spica_ventf), winter barley (Hordeum vulgare) and winter wheat (Triticum aestivum Seeds of plant species 5 are planted and pre-emerged with test chemicals formulated in a mixture of non-phytotoxic solvents, the mixture comprising a surfactant. Meanwhile, plants from these crops and weed species are tested in part. The chemical is subjected to post-emergence application, and the test chemicals are formulated in the same manner. The plants range from 2 to 18 cm (1 to 41 〇 leaf stage). The treated plants and control groups are All species were compared with the control group and evaluated visually in a controlled growth environment for 14 to 21 days. The plant response ratings summarized in Table D are based on a scale of 〇 to 1〇() where 〇 is ineffective and 100 For complete control, the reaction shown as dash 15 (-) means no test results. Table D 125 g ai/ha 3 4 5 7 Post-emergence spring barley 30 25 10 80 Winter barley 40 30 35 35 Black grass 100 60 50 80 Blue Grass 85 85 75 90 White Buckwheat 35 25 40 65 Wild Buckwheat 55 70 90 100 Canary Grass 100 100 95 100 White Chrysanthemum 100 100 100 100 Traditional 100 100 98 100 Baogao Grass 100 100 100 100 Wild Ghost Poppy 85 100 70 70 Wilderness Violet 100 100 100 100 Compound 21 24 25 26 28 29 30 31 32 0 20 20 10 10 20 20 35 25 10 25 10 10 5 10 20 30 20 25 35 20 30 40 15 80 30 40 40 30 30 20 60 10 45 50 30 15 10 35 10 20 10 40 35 50 80 75 80 100 35 100 85 85 75 20 40 30 10 20 10 70 90 70 100 100 100 100 98 100 100 90 100 85 100 90 100 90 95 100 95 85 100 95 100 98 100 100 100 90 90 90 40 85 95 100 60 90 70 100 80 100 95 100 100 100 85 70 229 201240602 莠草100 95 八仙草90 85 地肤50 45 藜95 98 Wild mustard 100 90 Wild oats 100 100 Rapeseed 100 95 Inverse 苋100 95 Wild radish 100 100 Russian 蓟75 40 Italian black Wheat straw 35 40 Pomna 100 100 Spring wheat 35 25 Winter wheat 35 25 Wind cut grass 90 90 100 100 75 90 80 80 40 90 85 100 85 75 75 75 90 75 85 90 90 95 80 95 85 95 85 100 85 85 95 100 90 100 90 98 85 100 98 85 95 100 85 90 85 95 80 75 100 95 95 90 20 20 60 10 25 15 65 60 30 100 90 80 80 100 85 95 100 80 100 100 85 100 95 100 90 100 80 75 75 100 80 75 80 98 90 80 100 85 100 90 80 95 .90 90 90 100 80 70 100 40 10 0 0 10 15 10 25 50 10 100 100 85 100 90 100 100 100 100 100 15 10 20 10 10 45 15 40 45 50 20 15 10 10 10 25 10 40 60 60 85 55 85 75 35 30 15 60 35 75 Table D 62 g ai/ha Post-emergence 3 4 Spring barley 25 20 Winter barley 30 20 Black grass 95 60 Blue grass 75 80 White dew 35 20 wild buckwheat 35 40 canary grass 100 100 white chrysanthemum 100 98 繁缕 98 100 baocai 100 90 original Wild Ghost Poppy 40 98 Wilderness Violet 100 100 Valerian 90 85 Eight Immortals 85 85 Kochia 30 25 藜95 90 Wild Mustard 98 80 Wild Oats 98 85 Rapeseed 100 80 Compound 7 21 24 25 26 28 29 30 31 32 10 0 15 10 0 5 10 10 15 10 25 5 10 5 0 0 10 0 20 5 50 5 20 10 5 20 5 40 20 20 70 15 15 20 15 20 10 35 40 20 35 15 10 25 10 20 5 40 25 40 98 80 75 75 95 25 80 85 80 50 90 10 20 20 5 10 5 40 70 50 100 95 90 90 100 90 95 100 90 100 98 80 100 90 90 75 95 90 75 85 100 98 95 95 98 90 70 98 80 90 70 85 40 80 85 98 50 80 60 100 100 70 100 75 95 - 95 80 80 60 100 90 70 80 65 70 40 80 80 95 85 70 60 70 80 75 60 85 85 85 85 50 85 80 90 75 100 80 95 95 100 90 100 80 98 85 100 85 85 85 100 80 80 75 90 80 60 95 65 95 90 15 10 20 10 20 5 30 20 25 100 75 75 75 85 80 80 95 75 75 230 201240602 Anti-branches 85 100 95 100 85 100 90 95 80 100 95 75 Wild radish 100 80 100 100 60 70 70 90 90 75 100 75 Russian 蓟75 40 80 75 70 75 90 85 85 100 60 50 Italian ryegrass 25 20 10 40 0 0 0 5 10 0 10 30 Po Po Na 100 100 100 100 100 65 100 30 100 75 95 100 Spring Wheat 20 15 10 15 10 10 5 5 25 15 25 35 Winter Wheat 25 20 10 10 10 5 5 5 25 5 30 30 Wind Cut Grass 60 55 40 60 35 65 35 10 20 5 35 35 75 85 90 10 100 40 35 35 Table D Compound 31 g ai/ha 3 5 7 21 24 25 26 28 29 30 31 32 Spring after spring 15 5 10 0 10 5 0 0 0 0 10 0 Winter Barley 30 10 15 0 5 0 0 0 0 5 0 Black Grass 70 30 30 5 0 0 0 10 0 20 10 15 Blue Grass 70 30 40 0 10 10 5 10 10 10 20 20 White Dew 30 20 20 10 10 5 0 15 0 20 15 30 Wild buckwheat 25 60 80 75 40 75 85 15 70 75 75 30 Canary grass 90 60 70 0 15 10 0 10 0 20 50 30 White chrysanthemum 98 85 100 90 85 60 100 75 90 100 - 98繁繁 90 85 95 70 95 90 85 65 90 80 70 80 baocai 100 100 100 85 90 80 85 80 70 85 70 80 Wilderness Ghost Poppy 50 60 60 85 40 60 80 85 50 80 60 95 Wilderness Violet 100 90 100 70 95 60 95 - 90 80 40 - 莠草85 70 98 75 50 20 35 60 40 75 65 80 八仙草85 60 80 60 50 65 75 75 55 80 80 85 地肤25 30 75 25 70 75 85 50 100 50 35 70 藜85 90 90 85 75 70 95 80 90 90 75 85 Wild mustard 95 90 100 50 50 65 80 80 50 90 45 85 Wild oats 90 10 30 5 10 10 5 15 0 15 10 10 Rapeseed 80 80 100 70 50 70 85 50 75 85 50 60 反 苋 80 85 98 70 95 80 95 70 100 75 70 65 Wild radish 98 95 100 60 35 70 90 65 60 95 70 85 Russian Li 60 80 65 30 75 80 80 75 80 40 50 70 Italian ryegrass 20 0 10 0 0 0 0 10 0 0 20 0 婆婆纳100 100 100 100 60 90 20 75 60 95 100 100 Spring wheat 15 5 10 0 10 0 0 10 5 10 5 25 Winter wheat 15 5 5 5 5 0 0 10 0 15 10 15 Wind cut grass 50 20 35 15 40 25 0 10 0 20 10 25 231 201240602 Compound 3 4 5 7 21 24 25 26 28 29 30 31 32 10 5 5 5 0 0 0 0 0 0 0 5 0 0 5 10 0 0 0 0 0 0 0 0 0 0 60 5 10 30 0 0 0 0 0 0 5 0 0 60 35 20 15 0 10 0 0 0 0 10 10 5 20 10 10 15 0 10 0 0 0 0 10 5 10 20 20 50 50 70 25 75 85 20 40 50 45 20 70 70 25 25 0 15 0 0 5 0 10 30 10 90 90 50 100 90 85 50 80 60 80 100 70 90 80 85 85 85 60 95 70 85 50 80 70 60 75 95 85 95 100 85 90 60 85 75 60 85 65 75 10 85 60 60 85 40 50 70 85 40 40 50 90 100 90 85 95 60 90 50 80 - 75 80 40 50 80 0 55 80 75 0 10 5 55 20 75 55 70 80 65 60 75 60 50 60 75 60 50 75 80 80 20 10 20 55 20 70 75 65 45 90 40 20 50 75 80 85 70 85 60 70 80 75 75 85 75 80 95 60 95 98 50 30 60 75 50 20 60 30 65 55 40 10 10 0 10 0 0 5 0 5 0 5 75 70 75 98 50 50 60 80 40 75 75 20 30 80 70 85 90 70 95 80 90 70 90 65 70 65 85 80 90 40 30 35 85 35 50 80 40 50 50 30 50 55 30 75 40 .75 60 60 35 50 50 10 0 0 0 0 0 0 0 5 0 0 0 0 100 100 100 100 100 30 90 20 70 50 80 85 100 0 5 0 5 0 0 0 0 5 0 0 5 5 10 10 0 5 0 0 0 0 0 0 5 5 5 20 35 20 25 0 25 10 0 0 0 10 5 15

表D 16 g ai/ha 萌後 春大麥 冬大麥 黑草 藍草 毛白露草 野生蕎麥 金絲雀草 白夏菊 繁縷 寶蓋草 原野鬼罌粟 原野紫羅蘭 莠草 八仙草 地膚 藜 野生芥菜 野生燕麥 油菜籽 反枝莧 野生蘿蔔 俄國莉 義大利黑麥草 婆婆納 春小麥 冬小麥 風剪草Table D 16 g ai/ha Post-emergence spring barley winter barley black grass blue grass hair white dew wild buckwheat canary grass white chrysanthemum prosperous treasure cover grassland wild ghost poppy wilderness violet valerian eight grassland grass skin wild mustard wild oats rapeseed苋Wild radish Russian Lily Italian rye grass mother-in-law spring wheat winter wheat wind cut grass

試驗E 將選自玉米(Zefl 、黃豆(Gfyczwe wax)、苘麻 5 (Abutilon iheophrasti)、緣(Chenopodium album)、後後草Test E will be selected from the group consisting of corn (Zefl, Gfyczwe wax, ramie 5 (Abutilon iheophrasti), rim (Chenopodium album), and later grass

Cfi'wpb叻b //e化、反枝莧(palmer pigweed) 232 201240602 (Jmizrawi/mspa/merz·)、莧菜藤子(common waterhemp) (d/warflwi/zws rwi/b)、抗性寬菜藤子(ALS &amp; HPPD resistant,Jwariz«认ws rwi//*s)、春蓼(ladysthumb smartweed) {Polygonum persicaria)、蘇利南草(Brachiaria 5 decumbens)、大馬唐萆(Digitafia sanguinalis)、巴西馬 唐草(DzgzYizrifii /zorzzowia/b)、洋野黍(fall panicum) (Panicum dichotomiflorum)、法氏狗尾草 faberii)、赛尊(Setaria vifidis)、年筋尊(Eleusine indica)、 !k (Sorghum halepense)、豬草(common ragweed, 10 Ambrosia elaiior)、稗萆(Echinochloa crus-galli)、讓緣 草(southern sandbur, Cenchrus echinatus) ' # ^ M⑽ό%/ζ·(3)、義大利黑麥草(ZWwm 、 鴨 56 草(Virginia (VA) dayflower, (?〇/?2騰&quot;&gt;2&lt;3 WrgWcYz)、 田旋花(Co«v6&gt;/vw/ws arve/wb)、蒼耳(common cocklebur, 15 尤训认如所、牽牛花[⑺cc/脱a)、顛 祐(eastern black nightshade,、地膚 (Kochia scoparia)、治莎草(Cyperus esculentus)與咸豐草 (hairy beggarticks)(执办似川/osa)之植物物種的種子栽 植於泥質壤土中,並且以配製於不具植物毒性溶劑混合 2〇 物中之試驗化學物質進行萌前處理,該混合物包括一界 面活性劑。同時來自這些作物與雜草物種的植物以部分 試驗化學物質進行萌後施用處理,該試驗化學物質係以 相同方式配製。使用高度範圍在2至18 cm (丄至4葉 階段)的植物來進行萌後處理。 25 經處理之植物與防治組係在溫室中養護14至21 天,之後將所有物種與防治組比較並目視評估。歸納於 233 201240602 表E中之植物反應評級係基於0至100的標度,其中0 為無效果而100為完全防治。顯示為破折號(-)之反應意 指無試驗結果。 表Ε 化合物 表E 化合物 250 g ai/ha 15 125 g ai/ha 15 萌後 萌後 稗草 98 鞞草 98 咸豐草 100 咸豐草 100 玉米 50 玉米 35 巴西馬唐草 95 巴西馬唐草 80 鴨路草 鴨跖草 田旋花 85 田旋花 80 洋野黍 95 洋野黍 90 反枝莧 100 反枝莧 100 猩猩草 100 猩猩草 95 義大利黑麥草 0 義大利黑麥草 0 蒺藜草 75 蒺藜草 60 金午時花 98 金午時花 95 黃豆 98 黃豆 98 莧菜藤子 100 莧菜藤子 98 抗性莧菜藤子 95 抗性莧菜藤子 95 表E 化合物 表E 化合物 62 g ai/ha 1 15 31 g ai/ha 1 15 萌後 萌後 稗草 80 95 稗草 70 90 咸豐草 90 98 咸豐草 80 95 玉米 30 15 玉米 25 5 巴西馬唐草 65 80 巴西馬唐草 60 60 鴨55草 75 鴨55草 65 田旋花 70 60 田旋花 60 50 洋野黍 95 75 洋野黍 95 75 反枝莧 100 100 反枝莧 95 98 猩猩草 80 85 猩猩草 80 - 義大利黑麥草 20 0 義大利黑麥草 10 0 234 201240602 蒺藜草 50 35 蒺藜草 45 0 金午時花 80 90 金午時花 65 80 春蓼 100 - 春蓼 95 - 黃豆 100 95 黃豆 95 95 莧菜藤子 98 98 莧菜藤子 90 98 抗性莧菜藤子 80 85 抗性莧菜藤子 80 75 表E 化合物 表Ε 化合物 16 g ai/ha 1 15 8 g ai/ha 1 萌後 萌後 稗草 50 75 稗草 30 咸豐草 75 75 咸豐草 60 玉米 20 0 玉米 5 巴西馬唐草 50 50 巴西馬唐草 40 鴨55草 15 鴨路草 田旋花 40 50 田旋花 40 洋野黍 75 35 洋野黍 60 反枝莧 95 95 反枝莧 95 猩猩草 70 75 猩猩草 50 義大利黑麥草 10 0 義大利黑麥草 0 蒺藜草 40 0 蒺藜草 30 金午時花 60 70 金午時花 50 春蓼 90 - 春蓼 70 黃豆 95 95 黃豆 95 莧菜藤子 85 95 莧菜藤子 75 抗性莧菜藤子 60 70 抗性莧菜藤子 50 表E 化合物 表E 化合物 4 g ai/ha 1 4 g ai/ha 1 萌後 萌後 稗草 20 猩猩草 30 咸豐草 55 義大利黑麥草 0 玉米 0 蒺藜草 20 巴西馬唐草 30 金午時花 50 鴨ίδ草 春蓼 60 田旋花 30 黃豆 85 洋野黍 40 莧菜藤子 70 反枝莧 85 抗性莧菜藤子 50 235 201240602 表E 化合物 表E 化合物 250 g ai/ha 14 25 125 g ai/ha 14 25 萌前 萌前 稗草 65 0 稗草 - 0 蒼耳 100 98 蒼耳 - 95 玉米 0 0 玉米 0 0 巴西馬唐草 98 95 巴西馬唐草 98 90 大馬唐草 100 95 大馬唐草 100 20 鴨ίδ草 25 鴨56草 - 田旋花 100 65 田旋花 35 5 法氏狗尾草 - 30 法氏狗尾草 0 20 莠草 20 20 莠草 15 20 牛筋草 98 98 牛筋草 80 98 強生草 98 85 強生草 70 85 地膚 98 65 地膚 98 35 藜 100 98 藜 100 98 牵牛花 95 90 牽牛花 90 65 顛茄 100 100 顛% 100 100 油莎草 95 50 油莎草 85 10 洋野黍 - 98 洋野黍 100 75 反枝莧 100 100 反枝莧 100 100 猩猩草 98 75 猩猩草 95 0 豬草 100 98 豬草 100 90 義大利黑麥草 0 0 義大利黑麥草 0 0 蒺藜草 90 0 蒺藜草 50 0 金午時花 10 0 金午時花 0 0 黃豆 90 60 黃豆 70 50 蘇利南草 98 95 蘇利南草 75 50 麻 95 35 清麻 85 0 莧菜藤子 100 100 莧菜藤子 100 100 表Ε 化合物 表E 化合物 62 g ai/ha 14 25 31 g ai/ha 14 25 萌前 萌前 稗草 0 0 稗草 0 0 蒼耳 10 50 玉米 0 0 玉米 0 0 巴西馬唐草 25 10 236 201240602 巴西馬唐草 90 大馬唐草 90 鴨Jffi草 - 田旋花 0 法氏狗尾草 - 莠草 10 牛筋草 80 強生草 40 地膚 50 藜 100 牽牛花 70 顛茄 100 油莎草 70 洋野黍 50 反枝莧 100 猩猩草 60 豬草 100 義大利黑麥草 0 蒺藜草 0 金午時花 0 黃豆 30 蘇利南草 20 @麻 80 莧菜藤子 100 表E 化合物 16 g ai/ha 萌前 14 稗草 0 蒼耳 - 玉米 0 巴西馬唐草 0 大馬唐草 25 鴨路草 0 田旋花 0 法氏狗尾草 0 莠草 0 牛筋草 0 大馬唐草 90 0 鴨55草 - 0 田旋花 0 0 法氏狗尾草 0 0 莠草 10 0 牛筋草 65 5 強生草 5 20 地膚 0 0 藜 98 98 牵牛花 70 5 顚% 100 0 油莎草 10 5 洋野黍 0 0 反枝莧 100 100 猩猩草 10 - 豬草 70 60 義大利黑麥草 0 0 蒺藜草 0 0 金午時花 0 0 黃豆 20 0 蘇利南草 10 0 清麻 65 0 莧菜藤子 0 0 表E 化合物 16 g ai/ha 14 25 萌前 顛茄 95 - »1 **· rLt 油沙草 0 0 洋野黍 0 0 反枝莧 100 - 猩猩草 0 0 豬草 - 10 義大利黑麥草 0 0 蒺藜草 0 0 金午時花 0 0 黃豆 20 0 237 201240602 強生草 0 0 蘇利南草 0 0 地膚 0 0 苘麻 10 0 藜 98 98 莧菜藤子 0 0 牵牛花 50 5Cfi'wpb叻b //e, palm pigweed 232 201240602 (Jmizrawi/mspa/merz·), common waterhemp (d/warflwi/zws rwi/b), resistant broad-leaved vine (ALS &amp; HPPD resistant, Jwariz «ww rwi//*s), springsthumb smartweed {Polygonum persicaria), Brachiaria 5 decumbens, Digitafia sanguinalis, Brazilian crabgrass ( DzgzYizrifii /zorzzowia/b), fall panicum (Panicum dichotomiflorum), foxtail faberii, Setaria vifidis, Eleusine indica, !k (Sorghum halepense), ragweed ( Common ragweed, 10 Ambrosia elaiior), Echinochloa crus-galli, southern sandbur (Cenchrus echinatus) ' # ^ M(10)ό%/ζ·(3), Italian ryegrass (ZWwm, duck 56 grass ( Virginia (VA) dayflower, (?〇/?2Teng&quot;&gt;2&lt;3 WrgWcYz), Tianxuanhua (Co«v6&gt;/vw/ws arve/wb), Xanthium (common cocklebur, 15 Such as, the morning glory [(7) cc / off a), the blessing (eastern black nightshade, koto (Kochia sc Seeds of plant species of oparia), Cyperus esculentus and hairy beggarticks (like Chuan/osa) are planted in muddy loam and formulated in a mixture of non-phytotoxic solvents. The test chemistry is pre-emerged and the mixture comprises a surfactant. At the same time, the plants from these crops and weed species are treated with a portion of the test chemistry for post-emergence treatment. The test chemistry is formulated in the same manner. Plants ranging from 2 to 18 cm (丄 to 4 leaf stage) are used for post-emergence treatment. 25 Treated plants and control groups are maintained in the greenhouse for 14 to 21 days, after which all species are compared with the control group and visually evaluated. . The plant response ratings summarized in Table 233 201240602 are based on a scale of 0 to 100, where 0 is no effect and 100 is complete control. The reaction shown as a dash (-) means no test results. Table Ε Compound Table E Compound 250 g ai/ha 15 125 g ai/ha 15 Post-emergence post-emergence Valerian 98 Valerian 98 Salty grass 100 Salty grass 100 Corn 50 Corn 35 Brazilian crabgrass 95 Brazilian crabgrass 80 Duckling duck跖草田旋花85 田旋花80 洋野黍95 洋野黍90 反枝苋100 苋枝苋100 Orangutan grass 100 Orangutan grass 95 Italian ryegrass 0 Italian ryegrass 0 蒺藜草75 蒺藜草60 金午时花98 Golden Noon Flower 95 Soybean 98 Soybean 98 Amaranth vine 100 Amaranth vine 98 Resistant amaranth vine 95 Resistant amaranth vine 95 Table E Compound Table E Compound 62 g ai/ha 1 15 31 g ai/ha 1 15 After germination Grass 80 95 稗草70 90 咸丰草90 98 咸丰草80 95 corn 30 15 corn 25 5 Brazilian crabgrass 65 80 Brazilian crabgrass 60 60 duck 55 grass 75 duck 55 grass 65 field convolvulus 70 60 field convolvulus 60 50 ocean黍95 95 野野黍95 75 反 苋100 100 反 苋 95 98 猩 草 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80 80蒺藜草50 35 蒺藜草45 0 Golden afternoon flower 80 90 Golden afternoon flower 65 80 Spring 蓼100 - Spring 蓼95 - Soybean 100 95 Soy bean 95 95 苋菜藤子 98 98 苋菜藤子90 98 Resistant 苋菜藤子80 85 Resistant 苋菜藤子80 75 Table E Compounds Ε Compound 16 g ai/ha 1 15 8 g ai/ha 1 Post-emergence geranium 50 75 稗草30 咸丰草75 75 咸丰草60 Corn 20 0 Corn 5 Brazilian crabgrass 50 50 Brazil Matangcao 40 Duck 55 grass 15 Duck road grass field Convolvulus 40 50 Field convolvulus 40 Ocean field 75 35 Ocean field 60 Anti-branches 95 95 Inversion 苋 95 Orangutan 70 75 Orangutan grass 50 Italian ryegrass 10 0 Yida Ryegrass 0 蒺藜草40 0 蒺藜草30 金午时花60 70 金午时花50 春蓼90 - 春蓼70 豆豆95 95 豆豆95 苋菜藤子85 95 苋菜藤子75 Resistant 苋菜藤子60 70 Resistant 苋菜藤子50 Table E Compounds Table E Compounds 4 g ai/ha 1 4 g ai/ha 1 Post-emergence geranium 20 Orangutan 30 Xianfengcao 55 Italian ryegrass 0 Maize 0 Valerian 20 Brazilian crabgrass 30 Golden afternoon flower 50 Δδ草春蓼60 田旋花30 Soybean 85 洋野黍40 苋菜藤子70 苋枝苋85 Resistant 苋菜藤子50 235 201240602 Table E Compound Table E Compound 250 g ai/ha 14 25 125 g ai/ha 14 25前萌前稗草65 0 稗草 - 0 Xanthium 100 98 Xanthium - 95 Corn 0 0 Corn 0 0 Brazilian horse grass 98 95 Brazilian horse grass 98 90 Large horse grass 100 95 Large horse grass 100 20 Duck ίδ grass 25 Duck 56 草 - 田旋花100 65 田旋花 35 5 法氏狗草草 - 30 法氏尾草0 20 莠草20 20 莠草15 20 牛牛草98 98 牛草草80 98 Johnson Grass 98 85 Johnson Grass 70 85 Ground Skin 98 65 Kochia 98 35 藜100 98 藜100 98 Morning Glory 95 90 Morning Glory 90 65 Belladonna 100 100 %% 100 100 Oil sedge 95 50 Oil sedge 85 10 Ocean 黍 - 98 洋野黍100 75反 苋 100 100 反 苋 100 100 100 草 98 75 75 75 75 75 95 95 95 95 95 95 95 95 95 95 95 95 95 95 95 0 95 95 95 95 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 100 100 0 金午时花0 0 Soybean 90 60 Soybean 70 50 Suli South Grass 98 95 Suriname Grass 75 50 Hemp 95 35 Qing Ma 85 0 Amaranth vine 100 100 Amaranth vine 100 100 Table Ε Compound Table E Compound 62 g ai/ha 14 25 31 g ai/ha 14 25 Pre-emergence 稗草0 0 稗草0 0 Xanthium 10 50 Maize 0 0 Maize 0 0 Brazilian crabgrass 25 10 236 201240602 Brazilian crabgrass 90 Da Ma Tang Cao 90 Duck Jffi grass - Tianxuanhua 0 French foxtail - 莠草10 牛筋草80 Johnson Grass 40 Kochia 50 藜100 Morning Glory 70 Belladonna 100 Oil sedge 70 Ocean 黍 50 Inverse 苋 100 Orangutan 60 Truffle 100 Italian ryegrass 0 蒺藜草 0 Golden afternoon flower 0 Soybean 30 Suriname grass 20 @麻80 苋菜藤子100 Table E Compound 16 g ai/ha Pre-emergence 14 Valerian 0 Xanthium - Corn 0 Brazilian crabgrass 0 Large horse grass 25 Acacia grass 0 Field squid 0 French foxtail 0 莠草 0 牛筋草0大马唐草90 0 Duck 55 草 - 0 田旋花0 0 法氏尾草0 0 莠草10 0 牛筋草65 5 强生草5 20 地肤0 0 藜98 98 Morning Glory 70 5 顚% 100 0 Oil Sedge 10 5 洋野黍 0 0苋100 100 Orangutan grass 10 - ragweed 70 60 Italian ryegrass 0 0 蒺藜草0 0 Golden afternoon flower 0 0 Soybean 20 0 Suriname grass 10 0 Qingma 65 0 Amaranth vine 0 0 Table E Compound 16 g ai/ha 14 25 萌前颠茄 95 - »1 **· rLt 油沙草0 0 野野黍0 0 苋枝苋100 - Orangutan 0 0 猪草 - 10 Italian ryegrass 0 0 蒺藜草0 0 金午时花0 0 Soybean 20 0 237 201240602 Johnson Grass 0 0 Suriname Grass 0 0 Kochi 0 0 Ramie 10 0 藜98 98 Amaranth vine 0 0 Morning Glory 50 5

試驗F 5 10 15 將每種施用率三個塑膠罐(約16-cm直徑)部分填 充經殺菌之Tama泥質壤土,其包含35:50:15比例的 沙、泥沙與黏土及2.6%有機物質。將各組之三個塑膠 罐分別進行栽植如下。每種施用率將來自鴨舌草(U.S. of monochoria) vag/wfir/’X)、小花輪傘草 、水毛花(ricefield bulrush) (Scirpus mucronatus)與水莧菜(purple redstem) (Ammannia 的種子栽植於一個16-cm罐中。每種施用率將 來自碎米莎草(rice flatsedge) /r/a)、粗毛千金 子(bearded sprangletop) /⑽:/⑶化咕)的種 子、一束9或10枝水種稻米幼苗(〇〇;Zfl cv ‘Japonica - M2〇r)與兩束3或4枝移植稻米幼苗(仏卿 種施用率將稗草cn//〇與水稗草(丨ate waterg膽)(五咖晴;^ 〇〇;价也)的種子栽植於一個 16-cm罐中1植為循序邊行所以作物與雜草物種在處 理時為2.0至2.5葉階段。 。「廿μ物係H室中生長且日/夜溫度設定為: ,、且提供補充平衡光照以 驗罐維持在溫室中直到試驗結束。光門期 238 20 201240602 在處理時,使試驗罐浸沒至高於土壤表面3公分, 其處理係將試驗化合物直接施用至田水中,並且在試驗 期間維持在此水深。在21天後,藉由與未經處理防治 組比較以目視評估稻米與雜草的處理效果。歸納於表F 中之植物反應評級係基於0至1⑽的標度,其中0為無 效果而100為完全防治。顯示為破折號㈠之反應竟於益 試驗結果。Test F 5 10 15 Three plastic cans (about 16-cm diameter) of each application rate were partially filled with sterilized Tama mud loam containing 35:50:15 ratio of sand, silt and clay and 2.6% organic substance. Three plastic cans of each group were planted as follows. Each application rate will come from the US of monochoria vag/wfir/'X), the sylvestris sylvestris, the ricefield bulrush (Scirpus mucronatus) and the purple redstem (the seed planting of Ammannia). In a 16-cm jar, each application rate will be from a seed of rice flatsedge /r/a), bearded sprangletop /(10):/(3) sputum, a bunch of 9 or 10 seedlings of rice seedlings (〇〇; Zfl cv 'Japonica - M2〇r) and two bundles of 3 or 4 transplanted rice seedlings (the application rate of the 仏 种 cn//〇 and 稗 water waterg The seeds of the gallbladder) are planted in a 16-cm jar and the plants are sequenced so that the crop and weed species are treated at the 2.0 to 2.5 leaf stage. The growth in the room H is set and the day/night temperature is set to: , and supplemental balanced illumination is provided to maintain the tank in the greenhouse until the end of the test. Photogate period 238 20 201240602 During processing, the test tank is immersed above the soil surface 3 cm, its treatment applied the test compound directly to the field water, and during the test period Here, the water depth. After 21 days, the treatment effect of rice and weeds was visually evaluated by comparison with the untreated control group. The plant response ratings summarized in Table F are based on a scale of 0 to 1 (10), where 0 is No effect and 100 is complete control. The reaction shown as a dash (1) is actually the result of the benefit test.

表F 500 g ai/ha 浸沒 稗草 水毛花 碎米莎草 鴨舌草 水莧菜 移植稻米 水種稻米 輪傘草 粗毛千金子 水稗草Table F 500 g ai/ha Immersion 稗草水毛花 碎 米 鸭 鸭 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水 水

表F 125 g ai/ha 浸沒 稗草 水毛花 碎米莎草 鴨舌草 水荒菜 移植稻米 水種稻米 輪傘草 粗毛千金子 水稗草 化合物 7 19 100 85 100 100 100 85 90 100 90 100 100 40 100 70 90 100 100 - 75 80 化合物 7 19 40 0 75 100 75 85 75 95 0 0 20 0 25 0 85 95 100 - 20 0Table F 125 g ai/ha Immersion 稗草水毛花碎米草草鸭草水荒菜Transplantation Rice Water species Rice Round Umbrella 粗毛千金水稗草化合物7 19 100 85 100 100 100 85 90 100 90 100 100 40 100 70 90 100 100 - 75 80 Compound 7 19 40 0 75 100 75 85 75 95 0 0 20 0 25 0 85 95 100 - 20 0

表F 250 g ai/ha 浸沒 稗草 水毛花 碎米莎草 鴨舌草 水莧菜 移植稻米 水種稻米 輪傘草 粗毛千金子 水稗草Table F 250 g ai/ha Immersion 稗草水毛花碎米草草鸭草水苋 Transplanted rice Water-type rice Round umbrella grass Thick-brown gold Water sedge

表F 64 g ai/ha 浸沒 稗草 水毛花 碎米莎草 鴨舌草 水莧菜 移植稻米 水種稻米 輪傘草 粗毛千金子 水稗草 化合物 7 19 85 55 85 100 80 85 80 100 75 100 45 20 60 25 85 100 100 30 0 化合物 7 19 35 0 40 95 40 85 20 85 0 0 0 0 0 0 75 90 75 201240602 【圖式簡單說明】 無 【主要元件符號說明】 無 5Table F 64 g ai/ha Immersion 稗草水毛花碎米草草鸭草水苋菜 transplant rice water rice 轮草草粗毛千金水草草化合物7 19 85 55 85 100 80 85 80 100 75 100 45 20 60 25 85 100 100 30 0 Compound 7 19 35 0 40 95 40 85 20 85 0 0 0 0 0 0 75 90 75 201240602 [Simple description of the diagram] No [Main component symbol description] None 5

Claims (1)

201240602 七、申請專利範圍: 1. 一種選自式1、其#·氧化物及其鹽之化合物,201240602 VII. Patent application scope: 1. A compound selected from the group consisting of formula 1, its #· oxide and its salt, 其中 A為選自由下列所組成之群組之自由基Wherein A is a free radical selected from the group consisting of ίο B1與B3各獨立為選自由下列所組成之群組之自由基 B2為選自由下列所組成之群組之自由基 241 15 20 201240602 乂9,又 C-3 C-4Ίο B1 and B3 are each independently a radical selected from the group consisting of: B2 is a radical selected from the group consisting of 241 15 20 201240602 乂9, and C-3 C-4 C-5 C-6 C-7 R1為C-5 C-6 C-7 R1 is 或 R1 為-WtpE1)!^24、-V^LCpE2)!^5、-WtpE3)!^26、 ^^(0)^^0(=0)^7 、 -W1S(0)xNR28C(=0)LR27 ' -W^CO^NR^SOzLR27 ίο 或-WtN ;或 R1 為 N(R4G)R41 ;或 R1 為-GA 或-W2GA ; 各GA為一 4-至7-員碳環,其包括選自C(=0)、C(=S)、 C(=NR29)、C(=N-OR30)或 C=NN(R29)2 之環員;或 15 一 6-至12-員飽和或部分飽和碳螺環或雜螺環環 系,其選擇性地包括選自c(=o)、c(=s)、 C(=NR29)、C(=N-OR30)或 C=NN(R29)2 之環員,各 環或環系選擇性地經至多五個選自在碳環員上之 R21與在氮環員上之R22的取代基取代;或 2〇 各GA為一 9-員部分飽和稠合且含有碳環員與2個氮環 員之環系,該環選擇性地經至多2個選自在碳環 員上之R21與在氮環員上之R22的取代基取代; 242 201240602 各E〗、E2與E3獨立為〇 N-CN 或 ν-νο2 ; s、NR28、NOR28、NN(R28)2、 各L獨立為〇、N(R3i)或s,· 其限制條件是當E3為〇,貝'i L不為〇 ; 各 R 4、R25、p26 版及27 Λ &amp; K R與尺獨立為氫;或CrC6烷基、CK:6 烯基、CVC6炔基或C:3_C6環烷基,各選擇性地經 10 一或多個取代基取代,該取代基係選自由齒素、 CN、N02、羥基、crC4烷氧基、crC4烷亞磺醯 基、Crc4烷磺醯基、Cl_c4烷胺基、C2_C8二烷胺 基、CVC6環烷胺基與(crC4烷基)c3-c6環烷胺基 所組成之群組; 各R獨立為Η、C】-C6烧基或Ci-C6 _燒基; 各R29獨立為Η、CVC6烷基、Ci-Q _烷基、crC6烷 羰基、CrC6烷磺醯基或CkQ齒烷磺醯基; 各Qi與Q2獨立為0、S或N(R31); Q為CrC4伸烧基,其選擇性地經至多4個選自crC6 燒基、C2_C:6稀基、C2_C:6炔基與C3-C6環烧基之 取代基取代; R3G獨立為Η、crc6烷基或crc6齒烷基; R31獨立為η、crc6烷基或crc6 ii烷基; R32為Η或CrC6烷基; 各X為0、1或2 ; w5為crc6伸烷基; wl為CrQ伸烷基、C2-C6伸烯基或(:2-(:6伸炔基;或 -(CH2)2OCH2-或,(CH2)3OCH2-; W2為crc6伸烷基; 243 25 2〇124〇6〇2 為笨基或-w (苯基)’各選擇性地在環員上經至多五 個選自R”的取代基取代;或_G 4_W4G ;或H、 氰基、羥基、胺基、硝基、_CHO、-C(=〇)〇H、 5 -C(=〇)NH2 ' -C(=S)NH2 &gt; -C(=0)NHCN &gt; •C(=〇)NHOH、-SH、-S〇2NH2、-S02NHCN、 -S02NH0H、-SF5、-NHCHO、-NHNH2、-NHOH、 -NHCN、-NHC(=0)NH2、CrC6 烷基、C2-C6 烯基、 C2-C6 炔基、Ci-C6 基、C2-C6 ii 稀基、C2-C6 10 _坱基、C3-C8環院基、c3-c8 _環烧基、c4-C1C) 烷環烷基、C4-C1G環烷烷基、C6-C14環烷環烷基、 CVCio鹵環烧烧基、CVCi2院環院院基、c3-Cg環 烯基、C3-C8鹵環稀基、C2-C8烧氧院基、c3-C1q 院氧稀基、C^-ClQ環院氧院基、C3-C1Q院氧院氧院 基、C2-C8烧硫烧基、〇2-〇8燒亞磺醯烷基、c2-c8 15 烧績醯炫•基、G-C8烧胺院基、C3-Ci〇二燒胺烧基、 C2_C8 ii炫胺院基、C4_C10環燒胺院基、c2-C8烧 羰基、C2-C8鹵烷羰基、c4-c10環烷羰基、c2-C8 烧氧幾基、G-Cig環烧氧叛基、C5-C12環院烧氧幾 基、C2-C8烷胺羰基、c3-c1()二烷胺羰基、c4_Ci〇 20 環烷胺羰基、c2-c5氰烷基、Crc6羥烷基、c4-c10 環烯烷基、c2-c8 ii烷氧烷基、crc8烷氧函烷基、 C2-C8函烷氧il烷基、C4_C10齒環烷氧烷基、c4_cl〇 環稀氧燒基、C4_Ci〇齒環稀氧燒基、C3-Ci〇二燒氧 烷基、C3-C1G烷氧烷羰基、C3-C1G烷氧羰烷基、 25 C2-Cs函炫•乳幾·基、Cl-C6燒氧基、C丨-C6函院氧 基、C3-C8環烷氧基、C3-C8鹵環烷氧基、c4_Ci〇 244 201240602 環烷烷氧基、C2_C6烯氧基、c2-c6鹵烯氧基、c3-c6 炔氧基、C3_(〕6鹵炔氧基、c2-c8烷氧烷氧基、c2-c8 烧罗反乳基、C2_Cs鹵烧艘氧基、C4_Ci〇環院緩氧基、 C;3-C10院幾烧氧基、CrC6统硫基、CrC6鹵院硫 5 基、C3-C8環燒硫基、Ci-C6烧亞確醯基、Ci-C6 鹵炫亞磺醯基、C1-C6烧礦醯基、Ci-C6鹵燒確醯 基、C3-C8環院礦醯基、c3-c8三烷矽基、c3-c8 環烯氧基、CVC8齒環稀氧基、C2-C8鹵院氧燒氧 基、C^-C:8烷氧鹵烷氧基、c2-c8鹵烷氧鹵烷氧基、 10 C3_C10烷氧羰烷氧基、c2-c8烷基(硫羰基)氧基、 。2-。8烧幾硫基、C2_Cg烧基(石危幾基)硫基、C3-C8 環烷亞磺醯基、crc6烷胺磺醯基、c2-c8二烷胺 磺醯基、C3_C10鹵三烷矽基、crc6烷胺基、c2_c8 一烧胺基、Ci_C6 _烧胺基、C2_Cs鹵二烧胺基、 15 C3-C8環烷胺基、c2-c8烷羰胺基、c2-c8鹵烷羰胺 基、crc6烷磺醯胺基、crc6 _烷磺醯胺基或 c4_c1()環烷(燒基)胺基;或Or R1 is -WtpE1)!^24, -V^LCpE2)!^5, -WtpE3)!^26, ^^(0)^^0(=0)^7, -W1S(0)xNR28C(=0 ) LR27 ' -W^CO^NR^SOzLR27 ίο or -WtN ; or R1 is N(R4G)R41 ; or R1 is -GA or -W2GA; each GA is a 4- to 7-membered carbocyclic ring, including From C (=0), C (= S), C (= NR29), C (= N-OR30) or C = NN (R29) 2 ring members; or 15 a 6- to 12-member saturation or part a saturated carbon spiro or heterospiro ring system, optionally comprising a member selected from the group consisting of c(=o), c(=s), C(=NR29), C(=N-OR30), or C=NN(R29) 2 ring members, each ring or ring system is selectively substituted with up to five substituents selected from R21 on a carbon ring member and R22 on a nitrogen ring member; or 2 〇 each GA is a 9-member partial saturation a ring system which is fused and contains a carbocyclic ring member and two nitrogen ring members, the ring optionally being substituted with up to two substituents selected from R21 on a carbocyclic member and R22 on a nitrogen ring member; 242 201240602 E, E2 and E3 are independently 〇N-CN or ν-νο2; s, NR28, NOR28, NN(R28)2, each L is independently 〇, N(R3i) or s, · The constraint is when E3 is 〇, 贝'i L is not 〇; each R 4, R25, p26 version and 27 Λ &amp; KR The ruler is independently hydrogen; or a CrC6 alkyl group, a CK:6 alkenyl group, a CVC6 alkynyl group or a C:3_C6 cycloalkyl group, each optionally substituted with 10 or more substituents selected from the group consisting of dentate, CN, N02, hydroxy, crC4 alkoxy, crC4 alkylsulfinyl, Crc4 alkanesulfonyl, Cl_c4 alkylamino, C2_C8 dialkylamino, CVC6 cycloalkylamino and (crC4 alkyl) c3-c6 ring a group consisting of alkylamine groups; each R is independently Η, C]-C6 alkyl or Ci-C6 _ alkyl; each R29 is independently hydrazine, CVC6 alkyl, Ci-Q-alkyl, crC6 alkylcarbonyl, CrC6 alkanesulfonyl or CkQ-dentanesulfonyl; each Qi and Q2 is independently 0, S or N (R31); Q is a CrC4 extender, which is selectively subjected to up to 4 selected from the group consisting of crC6, C2_C :6, a C2_C:6 alkynyl group substituted with a C3-C6 cycloalkyl group; R3G is independently fluorene, crc6 alkyl or crc6 dentate; R31 is independently η, crc6 alkyl or crc6 ii alkyl; R32 is fluorene or CrC6 alkyl; each X is 0, 1 or 2; w5 is crc6 alkyl; wl is CrQ alkyl, C2-C6 extended alkenyl or (: 2-(:6) alkynyl; -(CH2)2OCH2- or (CH2)3OCH2-; W2 is crc6 alkyl; 243 25 2〇124〇6 〇2 is a strepyl or -w(phenyl)' each optionally substituted with up to five substituents selected from R" on the ring member; or _G 4_W4G; or H, cyano, hydroxy, amine, Nitro, _CHO, -C(=〇)〇H, 5 -C(=〇)NH2 ' -C(=S)NH2 &gt; -C(=0)NHCN &gt; •C(=〇)NHOH,- SH, -S〇2NH2, -S02NHCN, -S02NH0H, -SF5, -NHCHO, -NHNH2, -NHOH, -NHCN, -NHC(=0)NH2, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkyne Base, Ci-C6 group, C2-C6 ii, C2-C6 10 坱, C3-C8 ring, c3-c8 _ ring alkyl, c4-C1C) alk cycloalkyl, C4-C1G ring Alkylalkyl, C6-C14 cycloalkanecycloalkyl, CVCio haloalkyl, CVCi2 ring, c3-Cg cycloalkenyl, C3-C8 halocyclo, C2-C8 oxygenated base, c3-C1q hospital oxygenated base, C^-ClQ ring courtyard oxygen base, C3-C1Q courtyard oxygen institute oxygen base, C2-C8 burnt sulfur base, 〇2-〇8 sulfinyl alkyl, c2- C8 15 calcination • • • base, G-C8 burnt amine base, C3-Ci 〇 diamine amine base, C2_C8 ii hexamine base, C4_C10 ring burn amine base, c2-C8 burn carbonyl, C2-C8 Haloalkylcarbonyl, c4-c10 cycloalkanecarbonyl, c2-C8 aerobic acid group, G-Cig ring-burning oxygen , C5-C12 ring alkoxy group, C2-C8 alkylamine carbonyl, c3-c1() dialkylamine carbonyl, c4_Ci〇20 cycloalkylamine carbonyl, c2-c5 cyanoalkyl, Crc6 hydroxyalkyl, c4 -c10 cycloalkenyl, c2-c8 ii alkoxyalkyl, crc8 alkoxyalkyl, C2-C8 alkoxy il alkyl, C4_C10 dental alkoxyalkyl, c4_cl anthracene oxygen, C4_Ci 〇 环 ring dilute oxygen, C3-Ci 〇 di- oxyalkyl, C3-C1G alkoxycarbonyl, C3-C1G alkoxycarbonyl, 25 C2-Cs 炫 • 乳 乳, Cl-C6 Alkoxy, C丨-C6 halooxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, c4_Ci〇244 201240602 cycloalkaneoxy, C2_C6 alkenyloxy, c2-c6 haloolefin Oxyl, c3-c6 alkynyloxy, C3_(]6 haloalkoxy, c2-c8 alkoxyalkoxy, c2-c8 calcined thiolate, C2_Cs halogenated alkoxy, C4_Ci〇 ringhouse Base, C; 3-C10 Institute alkoxy group, CrC6 system sulfur group, CrC6 halogen compound sulfur 5 group, C3-C8 ring-burning sulfur group, Ci-C6 pyrene sulfhydryl group, Ci-C6 halogen sulfoximine Base, C1-C6 burnt ruthenium, Ci-C6 halogenated ruthenium, C3-C8 ring sulphate base, c3-c8 trialkyl fluorenyl, c3-c8 cycloalkenyloxy, CVC8 dentate , C2- C8 halogen courtyard oxygen alkoxy, C^-C: 8 alkoxyhalo alkoxy, c2-c8 haloalkoxy alkoxy, 10 C3_C10 alkoxycarbonyl alkoxy, c2-c8 alkyl (thiocarbonyl) Oxygen, . 2-. 8 sulphur-based, C2_Cg alkyl (stone dangerous) thio, C3-C8 cycloalkyl sulfinyl, crc6 alkyl sulfonyl, c2-c8 dialkylamine sulfonyl, C3_C10 halotrioxane Base, crc6 alkylamino, c2_c8 monoamine, Ci_C6 _ acrylamine, C2_Cs haloalkylamine, 15 C3-C8 cycloalkylamine, c2-c8 alkylcarbonylamine, c2-c8 haloalkylamine a group, a crc6 alkanesulfonylamino group, a crc6-alkylsulfonylamino group or a c4_c1()cycloalkane (alkyl)amine group; R2 為-W6C(=E4)R33 、 -W6L]C(=E5)R34 、 -WtO^E6)!^35 、 -W6S(0)yNR37C(=0)R36 或 -W6S(0)yNR37C(=〇)L1R36 ; 245 201240602 各 E4、E5 與 E6 獨立為 Ο、S、NR37、NOR37、NN(R37)2、 N-CN 或 N-N02 ; 各L1獨立為〇、N(R38)或S ; 各R33、R34、R35與R36獨立為氫;或CrC6烷基、C2_C6 5 稀基、C2_C6炔基或CrC6環烧基,各選擇性地經 一或多個取代基取代,該取代基係選自由齒素、 CN、N02、經基、CrC4烷氧基、CVCU燒亞磺醯 基、C1-C4烧續酿基、C1-C4院胺基、C2-C8二院胺 基、Q-C6環烷胺基與(CrC4烷基)c3-c6環烷胺基 10 所組成之群組; 各R37獨立為Η、CVC6烷基或crc6鹵烷基; 各Q4與Q5獨立為0、S或N(R38); Q6為Q-C4伸烧基,其選擇性地經至多4個選自crC6 院基、C2_C:6烯基、(VC6炔基與C3-C6環烧基的 15 取代基取代; R38獨立為Η、CrC6烷基或CrC6鹵烷基; R39為Η或Q-C6烷基; 各y為0、1或2 ; W7為CrC6伸烷基; 20 W為Ci-C6伸院基、C2_C;6伸稀基或C2-C6伸炔基;或 -(CH2)2OCH2-或-(CH2)3OCH2-; W3為CrC6伸烷基、CVC6伸烯基或c2-c6伸炔基; W4為crc6伸烷基; R3為H、鹵素、氰基、羥基、-0·Μ+、胺基、硝基、-CHO、 25 -C(=0)0H、-C(=0)NH2、-C(=S)NH2、-SH、 -S02NH2' -S02NHCN' -S02NH0H' -OCN &gt; -SCN ' 246 201240602 _SF5、·ΝΗΝΗ2、_NHOH、-N=C=0、-N=C=S、CrC6 烷氧基、CVC6鹵烷氧基、c3-c8環烷氧基、c3-c8 鹵環烷氧基、c4-c10環烷烷氧基、c2_c6烯氧基、 c2-c6鹵烯氧基、c3-c6炔氧基、c3-c6鹵炔氧基、 5 c2-c8烷氧烷氧基、c2_c8烷羰氧基、c2-c8鹵烷羰 氧基、C4-CiG環烧幾氧基、C3-C1G烧幾炫氧基、 Ci_C6烧硫基、Ci_C6 _烧硫基、C3-C8環烧硫基、 C1-C0焼亞項醯基、鹵炫i亞續醯基、 烷磺醯基、CrG鹵烷磺醯基、C3-C8環烷磺醯基、 1〇 Ci_C6烧石黃酿氧基、C!-C6炫&gt; 胺基、C2-C8二烧胺 基、Ci-C6鹵院胺基、C2-C8 1¾二院胺基、C3-C8 環烷胺基、c2-c8烷羰胺基、c2-c8鹵烷羰胺基、 CrG烷磺醯胺基或CrC6鹵烷磺醯胺基;或苄氧 基、苯氧基、苄羰氧基、苯羰氧基、苯磺醯氧基、 15 节續酿氧基、苯硫基、节硫基、苯亞續酿基、节 亞磺醯基、苯磺醢基或¥磺醯基,各選擇性地在 環員上經至多五個選自R21的取代基取代; M+為一驗金屬陽離子或一敍陽離子; R4、R5、R6與R7各獨立為Η、鹵素、羥基、CrC6烷 2〇 基、C2-C6烯基、C2-C6炔基、CrC6鹵烷基、CrC6 烷氧基、CrC6鹵烷氧基、C3_C8環烷氧基或C3_C8 鹵環烷氧基;或苯基或节基,各選擇性地在環員 上經至多五個選自R21的取代基取代; R8 為 Η、CrC6 烷基、C2_C6 烯基、C2-C6 炔基、CA 25 鹵烧基、〇2·〇6鹵稀基、C2-C6 _快基、C3-Cg環烧 247 201240602 基或C;3-C8函環烷基;或苄基,其選擇性地在環員 上經至多五個選自R21的取代基取代; R9 為 Η、CrC6 烧基、C2-C6 烯基、C2-C6 炔基、CrC6 鹵炫基、CrC6鹵烯基、C2-C6鹵块基、C3-C8環院 基、c3-c8鹵環烷基、C4-C10烷環烷基、C4-C10環 炫炫基、C^-C】4 J衣院環燒基、C4-C10齒環院院基、 CVCi2烷環烷烷基、c3-c8環烯基、c3-c8鹵環烯 基、C2-C8烷氧烷基、C4-C1()環烷氧烷基、c3-c10 烷氧烷氧烷基或c2-c8烷硫烷基; R10為H、鹵素、氰基、羥基、胺基、硝基、sh、-S02NH2、 -SO2NHCN ' -SO2NHOH ' -OCN ' -SCN ' -SF5 ' -NHCHO、·ΝΗΝΗ2、-N3、-ΝΗΟΗ、-NHCN、 -NHC(=0)NH2、-N=C=0、-N=C=S、CrC6 烷基、 C2-C6 稀基、C2-C6 炔基、C1-C6 1¾ 炫》基、C2-C6 鹵 烯基、C2-C6鹵炔基、(:3-(:8環烷基、c3-c8鹵環烷 基、c4-c1Q烷環烷基、c4-c1G環烷烷基、c6-c14 環烷環烷基、C4-C10 i環烷烷基、c5-c12烷環烷烷 基、Crc8環烯基、c3-c8鹵環稀基、c2-c8烷氧烷 基、c4-c1Q環烷氧烷基、c3-c1G烷氧烷氧烷基或 C2_c8烷硫烷基; R11為Η、鹵素、氰基、羥基、胺基、Crc6烷基、c2_c6 烯基、C2-C6炔基、crC6鹵烷基、c2-c6鹵烯基、 C2-C6鹵炔基、C3-C8環炫基、c3-c8鹵環院基、 C4-C〖G烧環烧基、c4-Cig環烧院基、C4-C10 _環院 院基、C5-C12燒環烧院基、C3-C8環稀基、C3-C8 li環烯基、c2_c8烷氧烷基、c4-c1G環烷氧烷基、 248 201240602 C3_CiG烷氧烷氧烷基、C2_C8烷硫烷基、c2-c8烷 亞磺醢烷基或C2_C8烷磺醯烷基;或苯基,其選擇 性地經至多五個選自R21的取代基取代; R12為Η、鹵素、氰基、羥基、胺基、CVC6烷基、c2-c6 烯基、c2-c6炔基、crc6鹵烷基、c2-c6 i烯基、 C2-C6 _炔基、C3-C8環烧基、C3-C8 _環炫&gt;基、 c4-c1G烷環烷基、C4C1G環烷烷基、c6-c14環烷環 烷基、CrC10 ii環烷烷基、c5_c12烷環烷烷基、 CVC8環烯基、c3-c8 4環烯基或c2-c8烷氧羰胺 基; 13 R為Η、鹵素、氰基、羥基、胺基、硝基或(^-(^烷 氧幾基; η 為 0、1.或 2 ; 各R14、R15、R18與R19獨立為Η、鹵素、氰基、羥基 或Crc6烷基;或 一對R14與R18 —起作為C2_C6伸烷基或C2_C6伸烯基; p 20 或 lt 八马烷基、C2-C6鹵烯基、CrC6烷氧基、 Ci-C6 _烷氧基、C3-C8環烷氧基、crC6烷基、C2-C6 稀基、C2_C6炔基或(:3-(:8環烷基; T為CVC6伸烷基或C2-C6伸烯基; 各G獨立為一 5_或6_員雜環或一 8_、9_或ι〇_員稠合 雙環環系,各環或環系係選擇性地經至多五個選 自在碳環員上之R21與在氮環員上之R22的取代基 取代; 各R21獨立為鹵素、氰基、羥基、胺基 '確基、_CH0、 -C(==0)0H 、-C(=〇)NH2 、-C(=S)NH2 、 249 201240602 -C(=〇)NHCN、_c(=0)NH0H、-SH、_S02NH2、 -S02NHCN、_s〇2NHOH、_OCN、-SCN、-SF5、 10 20 Cl_C6院基、C2-C6烯基、C2-C6炔基、CrC6鹵烷 基、c2-c6鹵烯基、c2_c6鹵炔基、c3-c8環烷基、 C3-C8 i環烷基、C4_CiG;^環烧基、c4_Ci(^f院燒 基、匚3-(:8環烯基、c3-c8鹵環烯基、c2-c8烷氧烷 基、C4-C1G環烷氧烷基、c3_CiG烷氧烷氧烷基、 CH:8院硫烷基、C2_C8烷亞磺醯烷基、c2_c8烷氧 S燒•基、c2-c5氰烷基、CVC6羥烷基、CVC6烷氧 基、c丨-C:6鹵烷氧基、c3-c8環烷氧基、c3-c8鹵環 炫·氧基、C4-C1Q環烷烷氧基、(:2-(:6烯氧基、c2-c6 i稀氧基、C2-C8烷氧烷氧基、c2-c8烷羰氧基、 CrC6烷硫基、Ci_c6鹵烷硫基、c3_c8環烷硫基、 Ci-C6烷亞磺醯基、Ci_c6函烷亞磺醯基、Q-C6 燒續酿基、CVC6鹵烷磺醯基、c3-c8環烷磺醯基、 C1-C6烷胺基、c2_c8二烷胺基、Ci_c6齒烷胺基、 CH:8 _二烷胺基或c3-c8環烷胺基; 各R22獨立為c rc6烷基、c2-c6烯基、c2-c6炔基、c rc6 δ燒基、(:3-(:8環烷基或C2-C8烷氧烷基; p4〇 為crC6燒基;以及 R為crc6燒基;或 R 〇與 r41 -起作為-(ch2)4-、_(ch2)5_、_ch2ch=chch2_ 或-(CH2)2〇(CH2)2-。 25 2·如印求J員1所述之化合物,其中 A 為 A-1、A-3、A-4、Α·5 或 A-6 ; 201240602 R1為R2 is -W6C(=E4)R33, -W6L]C(=E5)R34, -WtO^E6)!^35, -W6S(0)yNR37C(=0)R36 or -W6S(0)yNR37C(=〇 ) L1R36 ; 245 201240602 Each E4, E5 and E6 are independently Ο, S, NR37, NOR37, NN(R37)2, N-CN or N-N02; each L1 is independently 〇, N(R38) or S; each R33 R34, R35 and R36 are independently hydrogen; or a CrC6 alkyl group, a C2_C6 5 dilute group, a C2_C6 alkynyl group or a CrC6 cycloalkyl group, each optionally substituted by one or more substituents selected from the group consisting of dentate , CN, N02, thiol, CrC4 alkoxy, CVCU, sulfinyl, C1-C4, aryl, C1-C4, amine, C2-C8, amine, Q-C6, cycloalkanamine a group consisting of (CrC4 alkyl)c3-c6 cycloalkylamino group 10; each R37 is independently hydrazine, CVC6 alkyl or crc6 haloalkyl; each Q4 and Q5 are independently 0, S or N (R38); Q6 is a Q-C4 extended alkyl group which is optionally substituted with up to 4 substituents selected from the group consisting of a crC6, a C2_C:6 alkenyl group, a (156 substituent of a VC6 alkynyl group and a C3-C6 cycloalkyl group; , CrC6 alkyl or CrC6 haloalkyl; R39 is hydrazine or Q-C6 alkyl; each y is 0, 1 or 2; W7 is CrC6 alkyl; 20 W is Ci-C6 stretching, C2_ C; 6 stretching or C2-C6 alkynyl; or -(CH2)2OCH2- or -(CH2)3OCH2-; W3 is CrC6 alkyl, CVC6 extended alkenyl or c2-c6 alkynyl; W4 is Crc6 alkyl; R3 is H, halogen, cyano, hydroxy, -0·Μ+, amine, nitro, -CHO, 25 -C(=0)0H, -C(=0)NH2, -C (=S)NH2, -SH, -S02NH2' -S02NHCN' -S02NH0H' -OCN &gt; -SCN ' 246 201240602 _SF5, ·ΝΗΝΗ2, _NHOH, -N=C=0, -N=C=S, CrC6 alkane Oxy, CVC6 haloalkoxy, c3-c8 cycloalkoxy, c3-c8 halocycloalkoxy, c4-c10 cycloalkanoyloxy, c2_c6 alkenyloxy, c2-c6 haloenyloxy, c3- C6 alkynyloxy, c3-c6 haloalkoxy, 5 c2-c8 alkoxyalkoxy, c2_c8 alkylcarbonyloxy, c2-c8 halocarbonyloxy, C4-CiG cycloalkyloxy, C3-C1G A few oxy groups, Ci_C6 sulphur group, Ci_C6 _ sulphur group, C3-C8 ring sulphur group, C1-C0 焼 subunit thiol group, halogen saponin, alkane sulfonyl group, CrG halane Sulfonyl, C3-C8 naphthylsulfonyl, 1〇Ci_C6 pyroxenyloxy, C!-C6 dazzle &gt; Amine, C2-C8 dialkylamine, Ci-C6 halogen amine, C2 -C8 13⁄4 II Amine, C3-C8 cycloalkylamino, c2-c8 alkylcarbonyl, c 2-c8 haloalkylcarbonylamino, CrG alkanesulfonylamino or CrC6 halosulfonylamino; or benzyloxy, phenoxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy, 15 a phenolic oxy group, a phenylthio group, a sulfhydryl group, a phenyl sulfonyl group, a sulfinyl group, a benzenesulfonyl group or a sulfonyl group, each selectively having up to five selected from ring members Substituted by a substituent of R21; M+ is a metal cation or a cation; R4, R5, R6 and R7 are each independently hydrazine, halogen, hydroxy, CrC6 alkane 2 fluorenyl, C2-C6 alkenyl, C2-C6 alkynyl , CrC6 haloalkyl, CrC6 alkoxy, CrC6 haloalkoxy, C3_C8 cycloalkoxy or C3_C8 halocycloalkoxy; or phenyl or a benzyl group, each selectively up to five selected on the ring member Substituted from a substituent of R21; R8 is anthracene, CrC6 alkyl, C2_C6 alkenyl, C2-C6 alkynyl, CA 25 haloalkyl, 〇2·〇6 halo, C2-C6 _ fast radical, C3-Cg Cyclo Burn 247 201240602 or C; 3-C8 functional cycloalkyl; or benzyl, which is optionally substituted on the ring member with up to five substituents selected from R21; R9 is fluorene, CrC6 alkyl, C2- C6 alkenyl, C2-C6 alkynyl, CrC6 halogen , CrC6 haloalkenyl, C2-C6 halo block, C3-C8 ring, c3-c8 halocycloalkyl, C4-C10 alkanecycloalkyl, C4-C10 cyclodextrin, C^-C]4 J clothing ring alkyl, C4-C10 tooth ring yard base, CVCi2 alkanecycloalkyl, c3-c8 cycloalkenyl, c3-c8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C1 ( a cycloalkoxyalkyl group, a c3-c10 alkoxyalkoxyalkyl group or a c2-c8 alkylsulfanyl group; R10 is H, halogen, cyano, hydroxy, amine, nitro, sh, -S02NH2, -SO2NHCN' -SO2NHOH ' -OCN ' -SCN ' -SF5 ' -NHCHO, ·ΝΗΝΗ2, -N3, -ΝΗΟΗ, -NHCN, -NHC(=0)NH2, -N=C=0, -N=C=S, CrC6 Alkyl, C2-C6, C2-C6 alkynyl, C1-C6 13⁄4, C2-C6 haloalkenyl, C2-C6 haloalkynyl, (3-(8-cycloalkyl), c3- C8 halocycloalkyl, c4-c1Q alkanecycloalkyl, c4-c1G cycloalkylalkyl, c6-c14 cycloalkylcycloalkyl, C4-C10 i cycloalkylalkyl, c5-c12 alkanecycloalkyl, Crc8 Cycloalkenyl, c3-c8 halocycloalkyl, c2-c8 alkoxyalkyl, c4-c1Q cycloalkoxyalkyl, c3-c1G alkoxyalkoxyalkyl or C2_c8 alkylthioalkyl; R11 is hydrazine, halogen , cyano, hydroxy, amine, Crc6 alkyl, c2_c6 alkenyl, C2-C6 alkyne ,crC6 haloalkyl, c2-c6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cyclodextrin, c3-c8 halo ring, C4-C, G ring, c4-Cig ring Burning base, C4-C10 _ ring yard base, C5-C12 burnt ring base, C3-C8 ring thin base, C3-C8 li cycloalkenyl, c2_c8 alkoxyalkyl, c4-c1G cycloalkoxy Base, 248 201240602 C3_CiG alkoxyalkoxyalkyl, C2_C8 alkylsulfanyl, c2-c8 alkylsulfinyl or C2_C8 alkanesulfonyl; or phenyl, optionally up to five selected from R21 Substituted by a substituent; R12 is anthracene, halogen, cyano, hydroxy, amine, CVC6 alkyl, c2-c6 alkenyl, c2-c6 alkynyl, crc6 haloalkyl, c2-c6 i alkenyl, C2-C6 Alkynyl, C3-C8 cycloalkyl, C3-C8-cyclohexanyl, c4-c1G alkanealkyl, C4C1G cycloalkane, c6-c14 cycloalkylcycloalkyl, CrC10 ii cycloalkyl , c5_c12 alk cycloalkylene, CVC8 cycloalkenyl, c3-c8 4 cycloalkenyl or c2-c8 alkoxycarbonylamino; 13 R is hydrazine, halogen, cyano, hydroxy, amine, nitro or (^ -(^ alkoxy group; η is 0, 1. or 2; each R14, R15, R18 and R19 are independently oxime, halogen, cyano, hydroxy or Crc6 alkyl; A pair of R14 and R18 together with C2_C6 alkyl or C2_C6 alkylene; p20 or lt octaalkyl, C2-C6 haloalkenyl, CrC6 alkoxy, Ci-C6-alkoxy, C3-C8 Cycloalkoxy, crC6 alkyl, C2-C6 dilute, C2_C6 alkynyl or (: 3-(:8 cycloalkyl; T is CVC6 alkyl or C2-C6 extended alkenyl; each G is independently 5 a 6-membered heterocyclic ring or an 8_, 9- or ι〇_ member fused bicyclic ring system, each ring or ring system selectively passing up to five R21 selected from a ring member and a nitrogen ring member Substituted by a substituent of R22; each R21 is independently halogen, cyano, hydroxy, amine '', _CH0, -C(==0)0H, -C(=〇)NH2, -C(=S) NH2, 249 201240602 -C(=〇)NHCN, _c(=0)NH0H, -SH, _S02NH2, -S02NHCN, _s〇2NHOH, _OCN, -SCN, -SF5, 10 20 Cl_C6, C2-C6 alkenyl , C2-C6 alkynyl, CrC6 haloalkyl, c2-c6 haloalkenyl, c2_c6 haloalkynyl, c3-c8 cycloalkyl, C3-C8 i cycloalkyl, C4_CiG; ^cycloalkyl, c4_Ci(^f Alkyl, 匚3-(:8-cycloalkenyl, c3-c8 halocycloalkenyl, c2-c8 alkoxyalkyl, C4-C1G cycloalkoxyalkyl, c3_CiG alkoxyalkoxy, CH:8 hospital Alkyl, C2_C8 alkylsulfinyl, c2_c8 alkoxy S, c2-c5 cyano, CVC6 hydroxyalkyl, CVC6 alkoxy, c丨-C: 6 haloalkoxy, c3-c8 Cycloalkoxy, c3-c8 halocyclohexyloxy, C4-C1Q cycloalkanoxy, (2-(:6-alkenyloxy), c2-c6 i-dioxyoxyl, C2-C8 alkoxylated alkoxy Base, c2-c8 alkoxycarbonyl, CrC6 alkylthio, Ci_c6 haloalkylthio, c3_c8 cycloalkylthio, Ci-C6 alkylsulfinyl, Ci_c6 sulfinyl, Q-C6 Base, CVC6 haloalkylsulfonyl, c3-c8 cycloalkylsulfonyl, C1-C6 alkylamino, c2_c8 dialkylamino, Ci_c6 dentate, CH:8-dialkylamino or c3-c8 An alkylamino group; each R22 is independently c rc6 alkyl, c2-c6 alkenyl, c2-c6 alkynyl, c rc6 δ alkyl, (3-(:8-cycloalkyl or C2-C8 alkoxyalkyl; P4〇 is a crC6 alkyl group; and R is a crc6 alkyl group; or R 〇 and r41 are -(ch2)4-, _(ch2)5_, _ch2ch=chch2_ or -(CH2)2〇(CH2)2- . 25 2. If the compound described in J, 1 is printed, where A is A-1, A-3, A-4, Α·5 or A-6; 201240602 R1 is ' -WlLC(=E2)R25 ^-w^^E^LR26; R1 為 N(R4())R41 ;或 R1 為 ga 或-w2ga ; ίο 怎巴和或部分飽和碳螺環或雜螺環j矛 系—,其,性地包括選自c(=〇)、C(=N视30)或 C-NN(R )的環員,各環或環系選擇性地經至多三 個選自在碳環員上之r21與在氣環員上之r22的^ 代基取代;或 15 各Μ為班一 9_員部分飽和稠合且含碳環員與2個氮環員 之環系,該環經i個選自在氣環員上之r22 基取代; % 各 E1、E2 與 E3 獨立為 〇、N〇R28 或 nn(r28)2 L獨立為〇或n(R3i); 20 G為一 9-至11-員 各R24、R25與r26獨立為氫;或心心烧基或ca環 磽基,各選擇性地經一或多個選自由鹵素、cN、 羥基、CrC2烷氧基、Q-C2烷亞磺醯基與crc4 烧磺醯基所組成之群組的取代基取代; 各R28獨立為Η、CrC3烷基或CVC3 _烷基; 251 201240602 各R29獨立為Η、(VC3烷基、CrC3鹵烷基、Cl_C3烧 基、C1-C3院確酿基或C1-C3鹵烧續酿基; 各Q1與Q2獨立為0或N(R31); Q為c^C3伸院基,其選擇性地經至多2個選自crc4 烷基的取代基取代; R3G獨立為Η、CrC3烷基或CrC3鹵烷基; R31獨立為Η、CVC3烷基或CrC3鹵烷基; R32為Η或crc3烷基; W1 ^ C2-C4&gt;it^* ' -(CH2)2OCH2-^-(CH2)3〇CH2-; ~2為CVC3伸烷基; w5為crc4伸烷基; R2為苯基或-w3(苯基),各選擇性地在環員上經至多五 個選自R21的取代基取代;或-G;或CrC6烷基、 C2-C6 稀基、C2-C6 块基、Ci_C6 ΐ 院基、C2-C6 鹵 稀基、C2-C6鹵炔基、C3-Cs環烧基、C3-C8鹵環院 基、C4-C1Q烧環烧基、C4-C1Q環院燒基、C6-Ci4 環烷環烷基、C4-C10鹵環烷烷基、(:5-(:12烷環烷烷 基、c3-c8環烯基、c3_c8鹵環烯基、c2-c8烷氧烷 基、C3-C1G烷氧烯基、C4-C1G環烷氧烷基、c4-c10 環烷氧烷氧烷基、C3-C1G烷氧烷氧烷基、(:2-(:8烷 硫烷基、c2-c8烷亞磺醯烷基、c2-c8烷磺醯烷基、 C2_Cg烧叛基、C4_C!〇環稀炫(基、C2_C8齒烧氧炫· 基、c2-c8烷氧鹵烷基、c2-c8鹵烷氧鹵烷基、c4-c10 鹵環烷氧烷基、C4-C10環烯氧烷基、C4-C i〇 i環烯 氧烷基、c3-c1()二烷氧烷基、crc6烷氧基、crc6 鹵烷氧基、c3-c8環烷氧基、C3-C8 i環烷氧基、 252 201240602 C4_C10環烧烧氧基' c2_c6烯氧基、C2_C6鹵烯氧 基、CH:6炔氧基、c3-c6鹵炔氧基、c2-c8烷氧烷 氧基、C2-C8烧幾氧基、C2_C8 4烷幾氧基、c4_Ci〇 環烷羰氧基、C3-C1G烷羰烷氧基、Ci_Cr^硫基、 5 CrC6鹵垸硫基、C3-C8環烧硫基、crC6烷亞磺醯 基、Crc6自烷亞磺酿基、Crc6烷磺醯基、Ci_c6 鹵烷磺醯基、CrC8環烷磺醯基、c3_c8三烷矽基、 C3_c:8環稀氧基、cvq鹵環烯氧基、c2-c8 ii烷氧 院氧基、CH:8院氧幽烷氧基、C2_C8鹵烷氧鹵烷 10 氧基、C3_Cl()烷氧羰烷氧基、crc8烷基(硫羰基) 氧基、OH:8環烷亞磺醯基或c3_Ci〇鹵三烷矽基; 或 R2 為-W6C(=E4)R33 、 -W6L1C(=E5)R34 或 ^W6C(=E6)LlR35 ; 15 各 E4、E5 與 E6 獨立為 ο、NOR37 或 NN(R37)2 ; 各L1獨立為o或N(R38); 各R33、R34與R3·’獨立為氫;或CrC4烷基、(^^環 烷基,各選擇性地經一或多個選自由鹵素、CN、 羥基、CrC2烷氧基、crC2烷亞磺醯基與crc2 20 烧磺醯基所組成之群組的取代基取代; 各R37獨立為Η、CrC3烷基或CrC3鹵烷基; R獨立為Η、C1-C3院基或C1-C3 ώ烧基; W3 為-CH2-; W6 為 C2-C4 伸烷基、-(CH2)2OCH2-或-(CH2)3OCH2-; 25 R3為羥基、-〇·Μ+、c2-c8烷羰氧基、c2-c8鹵烷羰氧基、 C4_C1()環烷羰氧基或C3_Cl()烷羰烷氧基;或苄氧 253 201240602 基、苯氧基、苄羰氧基、苯羰氧基、苯磺醯氧基 或节續酿氧基,各選擇性地在環員上經至多兩個 +選自R21的取代基取代; =為一鈉或鉀金屬陽離子; r9為CrC6烷基; ϋ 10 v. U為Η、鹵素或CiC6烷基; Rl1為Η或CrC6烷基; 10 20 R為H、鹵素、氰基、羥基、胺基或^心烷基; 各 R14、R15、R18 與 R19 為 Η 或 ch3 ; r2Q 為 Η 或 CH3 ; τ 為-CH2CH2-或·CH=CH·; 各G為G-1至G-20 (如實施例116中所描述者); r為0、卜2或3 ; 各R21獨立為鹵素、氰基、羥基、硝基、-CHO、-SH、 Q-Q院基、C2-C6稀基、C2-C6炔基、CrC6齒烷 基、c2-c6鹵烯基、c2_c6鹵炔基、c3-C8環烷基、 CH:8 4環烷基、C4_Cl〇烷環烷基、c4_Ci〇環烷烷 基、c3-c8環烯基、c3-c8 i環烯基、c2_c8烷氧燒 基、C4-C1G環烷氧烷基、c3-C1G烷氧烷氧烷基、 CrC8烷硫烷基、Qj-C:8烷亞磺醯烷基、C2_C8烷氧 鹵烷基、CH:5氰烷基、Ci-C:6羥烷基、CrC6烷氧 基、Crc6 i烷氧基、c3-c8環烷氧基、c3_c8鹵環 院氧基、C4-C1G環烷烷氧基、c2-C6稀氧基、C2-C6 i烯氧基、crc8烷氧烷氧基、crc8烷羰氧基、 CrC6烷硫基、crC6 ii烷硫基、C3-C8環烷硫基、 254 25 201240602 CrC6烷亞磺醯基、crC6鹵烷亞磺醯基、CrC6 烷磺醯基、CrQ函烷磺醯基或C3-C8環烷磺醯基; 各R22獨立為CrC6烷基或CrC6鹵烷基; R4G為乙基或異丙基;以及 R41為乙基或異丙基;或 R40 與 R41 — 起作為 _(CH2)5_、-CH2CH=CHCH2-或 -(CH2)2〇(CH2)2-。 3.如請求項2所述之化合物,其中 A 為 A-1、A-3 或 A-5 ; B1 為 C-1 ; B2 為 C-3 ; B3 為 C-1 ; R1 為-GA ; 各 GA 係選自 GA-卜 GA-2、GA-3、GA-7、GA-8 與 GA-9 ; 或 各GA為' -WlLC(=E2)R25 ^-w^^E^LR26; R1 is N(R4())R41; or R1 is ga or -w2ga; ίο how and or partially saturated carbon or heteroscrew a spear system, which, in nature, comprises a ring member selected from the group consisting of c(=〇), C(=N30) or C-NN(R), each ring or ring system being selectively selected from up to three selected from carbon The r21 on the ring member is replaced with the ^2 base of the r22 on the ring member; or 15 each is a partially saturated and fused ring with a ring ring member and two nitrogen ring members. Substituted by r22 groups selected from gas ring members; % E1, E2 and E3 are independently 〇, N〇R28 or nn(r28)2 L is independently 〇 or n(R3i); 20 G is a 9- To each of 11-members R24, R25 and r26 are independently hydrogen; or a heart-burning group or a ca-ring group, each optionally one or more selected from the group consisting of halogen, cN, hydroxy, CrC2 alkoxy, Q-C2 alkane Substituted by a group consisting of a sulfinyl group and a crc4 sulfonyl group; each R28 is independently hydrazine, CrC3 alkyl or CVC3 _alkyl; 251 201240602 Each R29 is independently Η, (VC3 alkyl, CrC3 halogen Alkyl, Cl_C3 alkyl, C1-C3, or C1-C3 halogen calcined base; each Q1 and Q2 is independently 0 Or N(R31); Q is a C^C3 stretching group which is optionally substituted with up to two substituents selected from a crc4 alkyl group; R3G is independently hydrazine, CrC3 alkyl or CrC3 haloalkyl; R31 is independently Η, CVC3 alkyl or CrC3 haloalkyl; R32 is hydrazine or crc3 alkyl; W1 ^ C2-C4&gt;it^* ' -(CH2)2OCH2-^-(CH2)3〇CH2-; ~2 is CVC3 Alkyl; w5 is crc4 alkyl; R2 is phenyl or -w3(phenyl), each optionally substituted on the ring member with up to five substituents selected from R21; or -G; or CrC6 alkyl , C2-C6 dilute base, C2-C6 block base, Ci_C6 ΐ courtyard base, C2-C6 halogenated base, C2-C6 haloalkynyl group, C3-Cs cycloalkyl, C3-C8 halogen ring base, C4-C1Q Burning cycloalkyl, C4-C1Q ring alkyl, C6-Ci4 cycloalkylcycloalkyl, C4-C10 halocycloalkyl, (5-(: 12 alkancycloalkyl, c3-c8 cycloalkenyl) , c3_c8 halocycloalkenyl, c2-c8 alkoxyalkyl, C3-C1G alkoxyalkenyl, C4-C1G cycloalkoxyalkyl, c4-c10 cycloalkoxyalkyloxy, C3-C1G alkoxyalkoxy Alkyl, (: 2-(:8 alkylsulfanyl, c2-c8 alkylsulfinyl, c2-c8 alkanesulfonyl, C2_Cg burnt, C4_C! anthracene ring (base, C2_C8 tooth) Burning oxygen base, c2- C8 alkoxyhaloalkyl, c2-c8 halohalooxyhaloalkyl, c4-c10 halocycloalkoxyalkyl, C4-C10 cycloalkoxyalkyl, C4-C i〇i cycloalkoxyalkyl, c3- C1() dialkoxyalkyl, crc6 alkoxy, crc6 haloalkoxy, c3-c8 cycloalkoxy, C3-C8 i cycloalkoxy, 252 201240602 C4_C10 cycloalkyloxy' c2_c6 alkenyloxy , C2_C6 haloenyloxy, CH: 6 alkynyloxy, c3-c6 haloalkoxy, c2-c8 alkoxyalkoxy, C2-C8 decyloxy, C2_C8 4 alkoxy, c4_Ci 〇 naphthenic Carbonyloxy, C3-C1G alkylcarbonyl alkoxy, Ci_Cr^thio, 5 CrC6 halosulfonyl, C3-C8 cycloalkylthio, crC6 alkylsulfinyl, Crc6 from alkylsulfinyl, Crc6 alkane Sulfonyl, Ci_c6 halosulfonyl, CrC8 cycloalkylsulfonyl, c3_c8 trialkylsulfonyl, C3_c: 8 cycloaliphaticoxy, cvq halocycloalkenyloxy, c2-c8 ii alkoxyoxy, CH : 8 oxyhexyloxy, C2_C8 halohalo oxahalo 10 oxy, C3_Cl() alkoxycarbonyl alkoxy, crc8 alkyl (thiocarbonyl)oxy, OH: 8 cycloalkyl sulfinyl or c3_Ci 〇halotrialkyl fluorenyl; or R2 is -W6C(=E4)R33, -W6L1C(=E5)R34 or ^W6C(=E6)LlR35; 15 each E4, E5 and E6 independent ο, NOR37 or NN(R37)2; each L1 is independently o or N(R38); each R33, R34 and R3·' is independently hydrogen; or CrC4 alkyl, (^^cycloalkyl, each selectively One or more substituents selected from the group consisting of halogen, CN, hydroxy, CrC2 alkoxy, crC2 alkylsulfinyl and crc2 20 sulfonyl sulfonyl; each R37 is independently hydrazine, CrC3 alkyl or CrC3 haloalkyl; R is independently Η, C1-C3 or K1-C3 fluorenyl; W3 is -CH2-; W6 is C2-C4 alkyl, -(CH2)2OCH2- or -(CH2)3OCH2 - 25 R3 is hydroxy, -〇·Μ+, c2-c8 alkylcarbonyloxy, c2-c8 halocarbonyloxy, C4_C1()cycloalkaneoxy or C3_Cl() alkanoalkoxy; or benzyl Oxygen 253 201240602, phenoxy, benzylcarbonyloxy, phenylcarbonyloxy, benzenesulfonyloxy or alkoxy, each selectively having up to two substituents selected from R21 on the ring member Substituted; = is a sodium or potassium metal cation; r9 is a CrC6 alkyl group; ϋ 10 v. U is hydrazine, halogen or CiC6 alkyl; Rl1 is hydrazine or CrC6 alkyl; 10 20 R is H, halogen, cyano, a hydroxyl group, an amine group or a cardinyl group; each of R14, R15, R18 and R19 is Η or c H3; r2Q is Η or CH3; τ is -CH2CH2- or ·CH=CH·; each G is G-1 to G-20 (as described in Example 116); r is 0, 2 or 3; Each R21 is independently halogen, cyano, hydroxy, nitro, -CHO, -SH, QQ, C2-C6, C2-C6 alkynyl, CrC6-dentyl, c2-c6-haloenyl, c2_c6 Alkynyl, c3-C8 cycloalkyl, CH: 8 4 cycloalkyl, C4_Cl noncycloalkyl, c4_Ci 〇 cycloalkanyl, c3-c8 cycloalkenyl, c3-c8 i cycloalkenyl, c2_c8 alkoxy Alkyl, C4-C1G cycloalkoxyalkyl, c3-C1G alkoxyalkyloxy, CrC8 alkylsulfanyl, Qj-C: 8 alkylsulfinyl, C2_C8 alkoxyhaloalkyl, CH: 5 Cyanoalkyl, Ci-C: 6 hydroxyalkyl, CrC6 alkoxy, Crc6 i alkoxy, c3-c8 cycloalkoxy, c3_c8 halocyclooxy, C4-C1G cycloalkanoxy, c2- C6 diloxy, C2-C6 i-alkenyl, crc8 alkoxyalkoxy, crc8 alkoxycarbonyl, CrC6 alkylthio, crC6 ii alkylthio, C3-C8 cycloalkylthio, 254 25 201240602 CrC6 Sulfosyl group, crC6 haloalkyl sulfinyl group, CrC6 alkanesulfonyl group, CrQ alkanesulfonyl group or C3-C8 cycloalkanesulfonyl group; each R22 is independently a CrC6 alkyl group or a CrC6 haloalkyl group R4G is ethyl or isopropyl; and R41 is ethyl or isopropyl; or R40 and R41 together as _(CH2)5_, -CH2CH=CHCH2- or -(CH2)2〇(CH2)2 -. 3. The compound of claim 2, wherein A is A-1, A-3 or A-5; B1 is C-1; B2 is C-3; B3 is C-1; and R1 is -GA; GA is selected from GA-Bu GA-2, GA-3, GA-7, GA-8 and GA-9; or each GA is R2為苯基或-w3(苯基),各選擇性地在環員上經至多兩 個選自R21的取代基取代;或-G;或Cl_c6统基或 C3-C8環院基; R3為羥基或C2-C8烷羰氧基; R9 為 ch2ch3 ; 255 25 201240602 R1G 為 Η 或 CH3 ; τ 為-ch2ch2·; G 為 G-2、G-3 或 G-15 ;以及 R21獨立為鹵素、確基、Crc6院基、CrC6 院基、CrC6 5 院氧基、Ci-C6鹵烷氧基或crC6烷硫基; 各R22獨立為ch3或CH2CF3 ;以及 R40 與 R41 — 起作為 _(CH2)5-、-CH2cH=CHCH2-或 -(CH2)2〇(CH2)2-。 10 4.如請求項3所述之化合物,其中 A 為 A-1 ; 各G、R2 is phenyl or -w3(phenyl), each optionally substituted with up to two substituents selected from R21 on the ring member; or -G; or Cl_c6 or C3-C8 ring; R3 is Hydroxy or C2-C8 alkylcarbonyloxy; R9 is ch2ch3; 255 25 201240602 R1G is Η or CH3; τ is -ch2ch2·; G is G-2, G-3 or G-15; and R21 is independently halogen, indeed Base, Crc6, KirC6, CrC6 5 oxime, Ci-C6 haloalkoxy or crC6 alkylthio; each R22 is independently ch3 or CH2CF3; and R40 and R41 together as _(CH2)5- , -CH2cH=CHCH2- or -(CH2)2〇(CH2)2-. 10. The compound of claim 3, wherein A is A-1; each G, R2為苯基; R3()為Η或甲基; R21為i素或crc3烷基,·以及 R22 為 ch3。 5·如請求項3所述之化合物,其中 A 為 1, GA 為 GA-2 ; R2為苯基、2-噻吩基、5·氯-2-吡啶基或環丙基; R3為羥基;以及 256 201240602 各 R14、R15、R18 與 R19為 Η。 6.如請求項3所述之化合物,其中 Α 為 Α·1 ; 5 Α 為 Α·3, GA 為 GA-2 ; R2為苯基、2-噻吩基5-氯-2-吼啶基或環丙基;以及 R3為羥基。 ίο 7.如請求項2所述之化合物,其中 A 為 A_1 ; R1為R2 is phenyl; R3() is hydrazine or methyl; R21 is i or crc3 alkyl, and R22 is ch3. 5. The compound according to claim 3, wherein A is 1, GA is GA-2; R2 is phenyl, 2-thienyl, 5·chloro-2-pyridyl or cyclopropyl; and R 3 is hydroxy; 256 201240602 Each R14, R15, R18 and R19 is Η. 6. The compound according to claim 3, wherein Α is Α·1; 5 Α is Α·3, GA is GA-2; R2 is phenyl, 2-thienyl 5-chloro-2-acridinyl or Cyclopropyl; and R3 is hydroxy. Ίο 7. The compound of claim 2, wherein A is A_1; R1 is 各Q1與Q2為0 ; Q3為C2-伸烷基; R32為Η或甲基; W5為C2-C3伸烷基; 2〇 R2為苯基、2-甲基苯基、3-曱基苯基、3-溴苯基、3- 氣苯基、4-氣苯基、3-氟苯基3,5-二氟苯基、3-噻 吩基或2-嗔吩基; R3 為羥基或-〇C(=0)CH2CH(CH3)2;以及 各 R14、R15、R18 與 R19 為 Η 或 CH3。 257 201240602 8. 如請求項7所述之化合物,其中 W5為(:2伸烷基或C3伸烷基; R2為苯基、3-噻吩基環丙基;以及 5 R3為羥基。 9. 一種請求項1中之式1化合物,其選自 3-(1,4-二氧雜螺[4.5]癸-8-基)-5-[(2-羥基-6-側氧基-1-環 己稀-1-基)毅基]-2-苯基-4(3//)-°¾咬酮、 ίο 5_[(2_經基-6_側氧基-1-環己稀-1-基)叛基]-6-側氧基-2- 苯基- 1(6//)-嘧啶乙醛1-(0_甲基肟) 2-(5-氯-3-。比啶基)_3-(1,4-二氧雜螺[4.5]癸-8-基)_5_[(2_ 經基-6-側氧基-1-環己稀-1-基)裁基]-4(3//)-嘴咬 15 酮、 2- 環丙基-3-(1,4-二氧雜螺[4.5]癸-8-基)-5-[(2-羥基-6-側 氧基-1-環己烯-1-基)羰基]-4(3//)-嘧啶酮、 3- (1,4-二氧雜螺[4.5]癸-8-基)-5_[(2-羥基-4-側氧基雙環 P.2.1]辛-2-烯-3-基)羰基]-2-(2-噻吩基)-4(3//)-嘧 20 咬酮與 5-[(2-經基-6-側乳基-1-壤己稀-1-基)幾基]-2-苯基 -3-(4,5,6,7-四氫-2-曱基-2//,吲唑-5-基)-4(3//)_嘧 咬酮。 25 10. —種除草混合物,其包含(a) —式1化合物與(b)至少一種 額外活性成分,該成分選自(M)光系統II抑制劑、(b2) 258 201240602 AHAS抑制劑、㈣ACCase抑制劑 (= 抑制劑,光系統…轉i=P〇 二;L==、(b8) GS (麵胺酸合成酶)抑制 =:i 、(bll)PDS(八氫番r°紅素去飽和酶) t ::12) _ (4·經苯基·丙暖二氧合酶)抑制 3) HST (黑尿料尼轉移酶)抑制劑、_其他 =草十包括有絲分裂干擾劑、有機坤劑、亞速爛、益 =、演布泰、抑草丁、環庚草醚、㈣隆、邁隆、汰 =龍、曱基汰草龍、乙氧苯草胺、殺木膦、殺木鱗敍、 威百故、触草酮、油酸、均㈣草畏及(Μ5)除草劑 保護劑;以及(bl)至(bl5)化合物之鹽。 15 11_如請求項1G所述之除草混合物,其包含⑻—請求項i 之化合物與⑻至少-種選自(bl)光系統„抑制劑之額外 活性成分。 12.請求項U所述之除草混合物,其中(b)為溴苯腈。 20 I3·如請求項10所述之除草混合物,其包含(a)—請求項i 之化合物與(b)至少一種選自(bl5)除草劑保護劑之額外 活性成分。 M. —種除草組成物,其包含一請求項^之化合物虛至少一 種選自由界面活性劑、固體稀釋劑與液體稀釋劑 之群組的成分。 259 25 201240602 15. —種用於防治非所欲植物之生長的方法,其包含使該植 物或其環境接觸一除草有效量的一請求項1之化合物。 201240602 四、 指定代表圖: (一) 本案指定代表圖為:第(無)圖。 (二) 本代表圖之元件符號簡單說明: 五、 本案若有化學式時,請揭示最能顯示發明特徵的化 學式:Each Q1 and Q2 is 0; Q3 is C2-alkylene; R32 is hydrazine or methyl; W5 is C2-C3 alkyl; 2〇R2 is phenyl, 2-methylphenyl, 3-mercaptobenzene , 3-bromophenyl, 3-phenylphenyl, 4-phenylphenyl, 3-fluorophenyl 3,5-difluorophenyl, 3-thienyl or 2-nonyl; R3 is hydroxy or - 〇C(=0)CH2CH(CH3)2; and each of R14, R15, R18 and R19 is Η or CH3. The compound of claim 7, wherein W5 is (: 2 alkyl or C3 alkyl; R2 is phenyl, 3-thienylcyclopropyl; and 5 R3 is hydroxy. The compound of formula 1 in claim 1 which is selected from the group consisting of 3-(1,4-dioxaspiro[4.5]dec-8-yl)-5-[(2-hydroxy-6-o-oxy-1-cyclo) Benzene-1-yl)yiji]-2-phenyl-4(3//)-°3⁄4 ketone, ίο 5_[(2_-carbyl-6-sideoxy-1-cyclohexene-1 -yl) keto]-6-o-oxy-2-phenyl- 1(6//)-pyrimidine acetaldehyde 1-(0-methylindole) 2-(5-chloro-3-.pyridyl ) 3-(1,4-dioxaspiro[4.5]dec-8-yl)_5_[(2_ylamino-6-o-oxy-1-cyclohex-1-yl) base]-4( 3//)-mouth bite 15 ketone, 2-cyclopropyl-3-(1,4-dioxaspiro[4.5]dec-8-yl)-5-[(2-hydroxy-6-sideoxy) 1-cyclohexen-1-yl)carbonyl]-4(3//)-pyrimidinone, 3-(1,4-dioxaspiro[4.5]dec-8-yl)-5-[(2- Hydroxy-4-sided oxybicyclic P.2.1]oct-2-en-3-yl)carbonyl]-2-(2-thienyl)-4(3//)-pyrimidine ketone with 5-[( 2-carbyl-6-side lactyl-1-ylide-1-yl)monoyl]-2-phenyl-3-(4,5,6,7-tetrahydro-2-indenyl-2 //, carbazole-5-yl)-4(3//)-pyrimidinone. 25 10. A herbicidal mixture comprising (a) - a compound of formula 1 and (b) at least one additional active ingredient selected from the group consisting of (M) photosystem II inhibitors, (b2) 258 201240602 AHAS inhibitors, (iv) ACCase inhibition Agent (= inhibitor, photosystem...transfer i=P〇2; L==, (b8) GS (flanderine synthase) inhibition=:i, (bll)PDS (octahydrofuran desaturation) Enzyme) t ::12) _ (4. phenyl-propanol-dioxygenase) inhibition 3) HST (black urine nematic transferase) inhibitor, _ other = grass 10 including mitotic interference agents, organic nucleating agents , 亚速烂,益=, 演布泰, inhibition of grass, cycloheptyl ether, (four) 隆, 迈隆, ti _ 曱, 曱 汰 草 、, acetophene, chlorhexidine, killing wood scales Syrian, Weibai, cetophenone, oleic acid, (4) grass and (Μ5) herbicide protectant; and (bl) to (bl5) compound salt. 15 11_ The herbicidal mixture according to claim 1 , which comprises (8) - a compound of claim i and (8) at least one additional active ingredient selected from the group consisting of (bl) photosystems </ RTI> inhibitors. a herbicidal mixture, wherein (b) is bromoxynil. 20 I3. The herbicidal mixture of claim 10, comprising (a) - a compound of claim i and (b) at least one selected from the group consisting of (bl5) herbicide protection Additional active ingredient of the agent M. A herbicidal composition comprising a compound of claimant at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent. 259 25 201240602 15. A method for controlling the growth of an unintended plant comprising contacting the plant or its environment with a herbicidally effective amount of a compound of claim 1. 201240602 IV. Designated representative figure: (1) The representative representative of the case is: (No) Figure (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 44
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CN103271054B (en) * 2013-02-01 2014-09-24 张德健 Complex formulation herbicide for protective cultivation of corn field
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Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891855A (en) 1954-08-16 1959-06-23 Geigy Ag J R Compositions and methods for influencing the growth of plants
US3235361A (en) 1962-10-29 1966-02-15 Du Pont Method for the control of undesirable vegetation
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3309192A (en) 1964-12-02 1967-03-14 Du Pont Method of controlling seedling weed grasses
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
GB2095558B (en) 1981-03-30 1984-10-24 Avon Packers Ltd Formulation of agricultural chemicals
IT1211138B (en) 1981-12-01 1989-09-29 Ausonia Farma Srl ANTI-HYPERTENSIVE COMPOUND PROCEDURE FOR ITS PREPARATION AND RELATED PHARMACEUTICAL COMPOSITIONS.
DE3246493A1 (en) 1982-12-16 1984-06-20 Bayer Ag, 5090 Leverkusen METHOD FOR PRODUCING WATER-DISPERSIBLE GRANULES
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
EP0777964B1 (en) 1989-08-30 2001-11-14 Kynoch Agrochemicals (Proprietary) Limited Preparation of a dosage device
BR9106147A (en) 1990-03-12 1993-03-09 Du Pont GRANULES OF PESTICIDES DISPERSABLE IN WATER OR SOLUBLE IN WATER MADE FROM THERMO-ACTIVATED BINDERS
EP0480679B1 (en) 1990-10-11 1996-09-18 Sumitomo Chemical Company Limited Pesticidal composition
CA2094949A1 (en) * 1992-04-28 1993-10-29 Eiki Nagano Pyrimidone derivatives and their use
TWI283164B (en) 2001-09-21 2007-07-01 Du Pont Anthranilamide arthropodicide treatment
JP2003327580A (en) 2002-05-10 2003-11-19 Kureha Chem Ind Co Ltd 2-(substituted benzoyl)thiazine derivative, method for producing the same and herbicide
CN101212969B (en) 2005-06-07 2013-08-07 药典公司 Azinone and diazinone V3 inhibitors for depression and stress disorders
US8076487B2 (en) * 2006-02-02 2011-12-13 Kumiai Chemical Industry Co., Ltd. Pyridone derivative and herbicide

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