TW200533665A - Substituted 4-(4-trifluoromethylpyrazolyl)pyrimidines - Google Patents
Substituted 4-(4-trifluoromethylpyrazolyl)pyrimidines Download PDFInfo
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- TW200533665A TW200533665A TW094107020A TW94107020A TW200533665A TW 200533665 A TW200533665 A TW 200533665A TW 094107020 A TW094107020 A TW 094107020A TW 94107020 A TW94107020 A TW 94107020A TW 200533665 A TW200533665 A TW 200533665A
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- Prior art keywords
- halogen
- hhh
- compound
- cf2h
- ome
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- NMTKMKXIUOZQQH-UHFFFAOYSA-N 4-[4-(trifluoromethyl)-1h-pyrazol-5-yl]pyrimidine Chemical class FC(F)(F)C1=CNN=C1C1=CC=NC=N1 NMTKMKXIUOZQQH-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 99
- 150000001875 compounds Chemical class 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 37
- -1 S (0) nR8 Chemical group 0.000 claims description 36
- 230000002363 herbicidal effect Effects 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 101100134929 Gallus gallus COR9 gene Proteins 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 244000038559 crop plants Species 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 2
- RPDUDBYMNGAHEM-UHFFFAOYSA-N PROXYL Chemical group CC1(C)CCC(C)(C)N1[O] RPDUDBYMNGAHEM-UHFFFAOYSA-N 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 19
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 239000000460 chlorine Substances 0.000 description 253
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 57
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION 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
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Description
200533665 ⑴ 九、發明說明 【發明所屬之技術領域】 以選 芳基 唑基 ,WO K 6- 吡啶 系基 芳香 系基 的多 題硏 ), 其並 嘧、n 定 除草 本發明係屬於除草劑之技術領域,特別是屬於可 擇性控制有用植物農作物之闊葉類雜草及雜草類之雜 吡唑類除草劑之技術領域。
W 4 【先前技術】 Φ 從多種文獻中人們已知由唑系基團如吡唑基、脒 及三唑基等取代之吡啶及嘧啶具有除草性質。例如 99/2 8 3 0 1號揭示於第2-位置具有唑系基團及於第4-] 位置具有透過碳原子依附之芳香族或雜芳香族基團之 及嘧啶。於WO 98/4 03 79號則揭示於第2-位置具有唑 團及於第4-或6-位置具有透過氧、氮或硫原子依附之 族或雜芳香族基團之吡啶及嘧啶。位於第2-位置的唑 團可再經多種基團所取代。此文獻還揭示了吡唑基團 φ 種取代基,其皆位於吡唑之第3-位置上。於ACS專 討系列(2002 ),800類(農業化學品之合成及化學 第76頁中則揭示於第4-位置攜有唑系基團之嘧啶,
«I 不具有除草活性。此等化合物都是前述文獻中已知的 化合物之區域異構物(regioisomers)。 然而在前述文獻中所提到的習知化合物所展現之 活性往往不足。據此,本發明之目的係在提供較習知技術 之化合物具有更佳活性之有效除草化合物。 200533665 (2) 【發明內容】 本發明現在已發現特定的4· ( 4-三氟甲基吡唑基)嘧 啶特別適合作爲除草劑。據此,本發明係在提供一種如下 式(I )化合物,其N-氧化物及其鹽類,
其中該等基團及標記具有如下意義: Y爲一種選自如下Y1到Y9之基團:
其中R1及R2彼此獨立且各別爲氫、鹵素、氰基、異 氰酸基、OH、COOR9、 COR9、 CH2OH ' CH2SH、 CH2NH2、N〇2、CSNH2、CONH2、 ( c! - C 4 )烷基、鹵素- -6 - 200533665 (3) (C 1 - C 4 )院基、(C3-C6) 5哀院基、(C1-C4)院氧基 素-(C1-C4)院氧基、(C1-C2)院氧基-(C1-C2)院 (c2-c4 )烯基、(c2-c4 )炔基、(c3-c4 )烯氧: (C3-C4)快氧基、(C1-C2)院硫基-(C1-C2)院 S(0)nR8、 ((^-(:2 )烷磺醯基-(Ci-C^ )烷基、胺 ()烷胺基、()烷羰胺基、(Ci-Q )烷 胺基或二-(CKC4 )烷胺基,或 R1 及 R2 共同形成 CH2-CH2-CH2,CH2-CH2-CH2 或 och2-ch2-ch2o ; R3及R4彼此獨立且各別爲氫、鹵素、氰基、 C4 )烷基、鹵素-(C】-C4 )烷基、()烷氧基 素·( C ! - C 4 )烷氧基; R5爲鹵素、氰基、烷基、鹵素- (Cr 烷基、(C】-C4 )烷氧基、鹵素-(C!-C4 )烷氧基、㈣ (c]-c4)烷硫基、(c3-c5 )環烷基、鹵素-(c3-c5 烷基、SF5、S(0)nR8、(C2-C4)烯基或(C2-C4)炔基 R6爲氫、鹵素、氰基、(Κ4)烷基、鹵素-C4)烷基、(CrG)烷氧基、鹵素- (C^Q)烷氧 S(0)nR8 ; R7爲(C】-C4 )烷基; R8爲氫、(CkQ)烷基或鹵素-(C^Ca)烷基; R9爲氫或(C】-C4 )烷基; η爲0、1或2。 、鹵 基、 基、 基、 基、 磺醯 -ch2 (c!- 或鹵 c4) _素-)環 :; (C 1 - 基或 200533665 (4) 【實施方式】 於式(I )及所有後續的結構式中,分別具有兩個或 三個以上碳原子之烷基、烯基及炔基可爲直鏈或分支。烷 基爲甲基、乙基、正丙基或異丙基、正丁基、異丁基、第 三丁基或2-丁基。據此,烯基可爲乙烯基、1-丙烯基、2_ 丙烯基及不同的丁烯基異構物。炔基可爲乙炔基、1 -丙炔 基、2 -丙炔基及不同的丁炔基異構物。於所述定義中所使 用的名詞如烷氧基、豨氧基、炔氧基及硫氧基等可類似地 來理解。所以例如炔氧基可爲 HC三CCH20、CH3C三 CCH20 及 CH3C^ CCH2CH20。 環烷基可爲環丙基、環丁基、環戊基或環己基。 於二取代胺基如二烷胺基之例中,此兩個取代基可相 同或不同。 鹵素爲氟、氯、溴或碘。鹵烷基爲部份或全部被鹵素 如氟、氯及/或溴,特別是氟或氯取代之烷基,如CF3、 chf2、ch2f、CF3CF2、CH2FCHCI、CCI3、CHC12、 CH2CH2CI ;鹵烷氧基可爲例如 ocf3、ochf2、och2f、 cf3cf20 > OCH2CF3 R 〇CH2CH2Cl;此等定義對應地掛在 其它鹵素取代的基團。 視此等取代基的本質及鍵結而定,本發明之式(I ) 化合物可呈立體異構物的形式存在。若有雙鍵,則可能存 在非對映異構物。例如,當分子中有一或多個不對稱碳原 子時,則可能存在對映異構物及非對映異構物。立體異構 物可從所製成的混合物中藉著標準分離法如層析分離技術 -8- 200533665 (5) 來取得。類似地’立體異構物可使用立體選擇性反應及光 學活性起始物及/或助劑來選擇性地製造出來。本發明亦 包括所有式(I )化合物之立體異構物及其混合物,其係 包括在通式(I )的範圍內不過並沒有特別地界定。 式(I )化合物原則上可以形成N -氧化物。N -氧化物 " 可根據熟悉此技術者習知的方法與氧化劑如過酸、過氧化 < 氫及過硼酸鈉反應而製得。此等方法係述於例如T · L. • Gilchrist,Comprehensive Organic Synthesis, Volume 7? 弟 748-750 頁,S.V· Ley,Ed.,Pergamon Press。 原則上式(I )化合物可藉由添加以下物質來形成鹽 類,其可爲: a )酸如氫氯酸、氫溴酸、硝酸、磷酸、硫酸、醋 酸、草酸等,或 b )鹼如吡啶、氨、三乙胺、碳酸鈉、碳酸鉀、氫氧 化鈉、氬氧化鉀。 • 除非另有說明,否則本發明化合物之較佳具體例亦包 括其N-氧化物及鹽類。 已發現到以如下式(I )化合物較佳,其中: • R1及R2彼此獨立且各別爲氫、鹵素、氰基、羥基、 甲醯基、乙烯基、(κ4)烷基、鹵素- (CrD烷基或 (C ] - C 4 )院氧基; 或者 R1 及 R2 共同形成 CH2-CH2-CH2, R3及R4彼此獨立且各別爲氫、鹵素、甲基或甲氧 200533665 (6)
Y 爲 Yl、γ2、Υ3、Υ6、Υ7、Y8 或 Y9 之基團, 且其它的取代基及標記則具有如上所述之意義。 更讓人感到興趣的是如下式(I )化合物,其中:
Ri爲氫、鹵素、羥基、氰基、三氟甲基、甲氧基、甲 基或乙基, < R2爲氫、羥基、甲基、乙基、甲氧基或乙氧基; _ 或 R1 及 R2 共同形成 ch2-ch2-ch2, R3及R4彼此獨立且各別爲氫或甲基, 且其它的取代基及標記則具有如上所述之意義。 較佳的式(I)化合物爲其中·· R爲鹵素、氰基、鹵素-(C1-C2)院基、鹵素·(Ci-C2 )烷氧基或鹵素-(c 1 _ c 2)烷硫基且其它的取代基及標 記則具有如上所述之意義。 φ 更佳的式(I )化合物爲其中: R2及R6各爲氫; Y爲Yl、Y2、Y7、Y8或Y9之基團, 且其它的取代基及標記則具有如上所述之意義。 % 除非另有定義,否則所有如下結構式之取代基及符號 皆具有如式(ί )所述同樣的定義。 本發明之化合物可採用例如如下方案所示之方法來製 備: 於方案1中,式(I )化合物可藉著使式(111 )之羥 -10- (7) (7)200533665 基化合物與式(Ha )之嘧啶進行鹼催化之親核性取代反應 來製備。於式(Ila )中,E2爲離基如鹵素、甲基磺醒基 或甲苯磺醯基。此等親核性取代反應爲熟悉此技術之人士 所習知。
式(11 a )化合物其中E2爲鹵素,可依照例如方案2 的方法使式(IV )之嘧啶其中E1及E2爲鹵素與式(V ) 之吡唑進行鹼催化之取代反應來製備。在此,亦可能會形 成個別的區域異構物(lib );該區域異構物可藉著例如層 析被分離出來。明瞭此技術之技藝人士對此等反應係十分 熟悉的。 -11 - 200533665
式(Ila )化合物其中E2爲甲基磺醯基可採用例如方 案 3的方法把式(lie )化合物用間位-氯過苯甲酸 (MCPA )或Oxone®氧化來製成。此等反應爲熟悉此技術 者所習知,可參考例如 J. March, Advanced Organic Chemistry, John Wiley, New York, 200 1, 5th ed.5 第 1541-1 5 4 2 頁。
-12- 200533665
式(II c )化合物可採用例如方案4的方法使式(v I ) 之嘧啶其中E 1爲離基如鹵素與式(v )之吡唑進行鹼催化 反應來製備。 方案4
式(VI )化合物其中E1爲離基如鹵素可以例如把2 -硫甲基-4-羥基嘧啶與P〇Cl3反應來製得。此等方法爲熟悉 此技術者所習知,其係述於例如Houben-Weyl,Methods of Organic Chemistry,V o 1. E 9b,Part 1,1998,第 209-210 頁。經取代之2-硫甲基-4·羥基嘧啶可使用熟悉此技術者 習知的方法來製備,像是述於例如Η 〇 u b e 11 - W e y 1,M e t h 〇 d s of Organic Chemistry, V o 1. E 9b,Part 1 ? 1998,第 46,47, 49及50頁之方法。 類似地,式(V )之吡唑可使用熟悉此技術者習知的 方法來製備。4-三氟甲基吡唑的製備係述於例如 丁 etrahedron Letters, 37; 1 996,第 1 8 2 9- 1 8 3 0 頁。 3 -甲基-4 -三氟甲基毗唑(V a )可採用方案5來製備。 - 13- 200533665 (10)
h2n-nh2
NIH va 本發明之式(I)化合物對於會嚴重影響經濟收益之 多種單子葉及雙子葉雜草植物具有除草活性。此等活性物 質同樣地可有效防治多年生雜草,其可從根狀莖、地下莖 或其它多年生器官長出芽來故而不容易防治。關於此點, 一般來說本發明之活性物質係在播種前、雜草出土前或雜 草出土後施用都可以。使用本發明化合物可以防治之單子 葉植物及雙子葉植物雜草群之某些代表性物種可當作實例 般個別地列舉出來,不過其並非意圖把本發明之效能限制 在此等特定的物種範圍裡。本發明化合物可以良好防治之 單子葉植物的雜草有例如燕麥(Aveiia ),黑麥草 (Lolium),看麥娘(Alopecurus) ,Phalaris,稱 (Echinochloa),馬唐(Digitaria),狗尾草(Setaria) 及莎草(Cyperus )等屬之一年生物種,以及鵝觀草 (Agropyron),狗牙根(Cynodon),茅草(Imperata ) 及高梁(Sorghum )等屬之多年生物種。於雙子葉植物之 雜草物種之例中,除草活性有效的範圍則擴展到例如豬殃 -14 - 200533665 (11)
狹(Galium) ’堇菜(Viola),婆婆納(Veronica),完 麻(Larnium) ’繁縷(Stellaria),寛(Amaranthus), 芥(Sinapis),番薯(ipomoea),金午時花(sida), Matricaria及麻(Abutilon)等屬之一年生物種,及旋花 (Convolvulus ),蘇(Cirsiuni),酸模(Rum ex)及蒿 (Artemisia )等屬之多年生物種。在水稻之特殊生長環境 下可發現的有害植物如稗(Echinochloa ),野慈姑 (Sagittaria ),澤瀉(Alisma),藺草(Eleocharis), 大菅草(Scirpus )及莎草(Cyperus )等在使用本發明之 活性物質後亦可以極有效地加以防治。如果本發明之化合 物係在雜草出土前就施用在土壤表面,有時便可以徹底地 防止雜草發芽生長。即使雜草萌發了,但是在長出子葉以 後便會停滯在此狀態且經過3到4週以後最後植物還是會 徹底死亡。當活性物質係在雜草萌發後才施用在植物的綠 色部份時,在施藥後雜草很快就會停止生長且停留在施藥 時的生長階段,或者再經過一段時間以後雜草就會徹底死 亡,如此一來就能在極早的階段以持續的方式除去嚴重威 脅農作物生長之雜草的競爭作用。更詳言之,本發明化合 物對於反枝莧 (A m a r a n t h u s r e t r 〇 f 1 e X u s ),燕麥類 (Avena sp.),稗類(Echinochloa sp.),水莎草 (Cyperus serotinus ) ,多花黑麥草(Lolium multiflorum ),狗尾草(Setaria viridis),瓜皮草 (Sagittaria pygmaea),大菅草(Scirpus j υ n c o i d e s ), 芥類(Sinapis sp.)及繁縷(Stellaria media)都具有極佳 -15- (12) (12)200533665 的防治效果。 雖然本發明化合物對於單子葉及雙子葉雜草具有優越 的除草活性,不過對於重要的經濟作物如小麥、大麥、裸 麥、水稻、玉米、甜菜、棉花及大豆則最多僅有些微的損 害。特別地,小麥、大麥、玉米、水稻及大豆皆能良好地 耐受此等化合物。這是爲什麼本發明化合物特別適合用在 農作物或觀賞植物上以選擇性地防治雜草植物。 由於該等活性物質之除草活性,所以也可以把這些物 質用在已知作物或未來發展出的基因改造作物上以防.治有 害植物。原則上,轉基因植物係以其具有特殊有利的特性 而更爲優異,此等特性有例如對於特定的殺蟲劑,特別是 特定的除草劑具有耐受性,對於某些植物疾病或導致植物 生病的致病生物如特定的昆蟲或微生物如真菌、細菌或病 毒等具有耐受性。其它特性則與例如收穫的產量.、品質、 上架壽命、組成及特殊組成等有關。所以,習知的轉基因 植物有的具有較高的澱粉含量,或者其澱粉品質已有所調 整,或者於收穫產物中所含之脂肪酸種類有所不同等。 本發明之式(1 )化合物或其鹽類特別適合用在極具 經濟價値之轉基因農作物及觀賞植物上,此等植物有例如 穀類如小麥、大麥、裸麥、燕麥、雜糧、水稻、木薯及玉 米,或者其它作物如甜采、棉花、大、油菜、馬鈴薯、 蕃茄、豌豆及其它蔬菜等。式(I )化合物較佳地係用在 可以耐受除草劑的作物,或者用在經基因改造過、對於除 草劑危害植物的特性具有耐受性之作物上。 - 16 - 200533665 (13) 可用來產生與現存植物具有不同性質之新穎植物之習 知途徑有例如傳統的雜交法及產生突變株等。另外,具有 已變更之不同特性的新穎植物亦可藉助重組技術(參考例 如 EP-A-0221044 , EP-A-0131624)來產生。例如,如下 已舉出多個實例: ’ -改變植物體內澱粉之合成之重組改造農作物(例如 w WO 92/13 76,WO 92/14827,WO 91/19806), 0 -對於糖佛思奈特(glufosinat) e型(WEP-A-024223 6,EP-A-242246 ),鎭草寧型(WO 92/003 77 )或 磺醯脲型(EP-A-025 7993,US-A- 5 0 1 3 65 9 )之特定除草劑 具有耐受性之轉基因作物, -例如可以製造桿菌 Bacillus thuringiensis毒素(Bt 毒素)以抵抗特定害蟲之轉基因棉花作物(£?-八-0142924 , EP-A-0193259), -具有已變更之脂肪酸種類之轉基因作物(WO ❿ 91/13972) ° 已知許多分子生物學的技術可用來產生具有已變更之 不同特性之新穎轉基因作物;可參考例如Samb rook et a 1·, 1 9 8 9, Molecular Cloning, A Laboratory Manual, 2nd ed.5 1
Cold Spring Harbor Laboratory Press,Cold Spring Harbor, NY ;或 Win li acker “Gene und Klone” [Genes and Clones], VCH Weinheim 2nd Edition 1996 或 Christou,“Trends i η Plant Science” 1 ( 1996) 423-431。 爲了進行此等重組操作要把核酸分子引入質體中’如 -17- 200533665 (14) 此可形成突變或藉由DNA序列的重組來變更序列。藉助 於前述的標準方法就可以進行鹼基取代、移除部份序列或 加入天然或合成的序列。此等片段也可用來作爲把諸DNA 片段彼此串連起來的連接物或接頭片段。 製造具有低活性基因產物之植物細胞則可藉由例如表 ‘ 現至少一段對應的反義RNA,表現具有共抑制作用之有義 4 RNA,或者表現至少一種適當構築之能特殊地剪切前述基 g 因產物之轉錄物的核糖酶來達成。 爲了達到此目的,一方面可以利用含有所有基因產物 之編碼序列及可能存在之旁側序列之DNA分子,還可以 使用僅含有編碼序列的部份,不過此等部份的長度必需長 到足以在細胞內引起反義效果。另一種可能性係使用與基 因產物之編碼序列具有高度同質性但並不完全一樣的DNA 序歹U。 當植物之核酸分子表現時,所合成的蛋白質可以位在 φ 植物細胞內任何所需的隔室內。然而,爲了要使蛋白質位 在某一特殊的隔室內,可以把編碼區例如連接到可確保蛋 白質位於某一特殊隔室之DNA序列上。此等序列爲熟練 之技術人士所習知(參考例如 B r a u n e t a 1.,Ε Μ Β Ο J . 4 11(1992),3219-3227; Wolter et al·,Proc. Natl. Acad. Sci. USA 85(1988), 846-850 ; Sonnewald et a] . ? Plant J. 1 ( 1 9 9 1 ), 95 - 1 06 ) 〇 轉基因之植物細胞可用習知技術再生以移至原始植物 的體內。原則上,轉基因植物可爲任何需要之植物物種, -18- 200533665 (15) 不論是單子葉植物或雙子葉植物皆可。 所以’表現出已變更之不同性質之轉基因植物可以藉 由同源(即天然的)基因或基因序列的過度表現、壓抑或 抑制作用或者異源(即外來的)基因或基因序列的表現來 製得。 在轉基因作物上使用本發明之活性物質時,除了在其 它作物上所觀察到的防治有害植物的效果以外經常還可以 觀察到其它效果,此等效果爲施用在所硏究之轉基因作物 上時才會產生,例如所能防治之雜草物種可能有所不同或 者更爲寬廣,所採用的施藥量會有所不同,較佳地與該轉 基因作物可耐受的除草劑具有良好的倂用能力,且對於轉 基因作物的生長及產量會有所影響。所以本發明亦關於在 轉基因作物上施用本發明之化合物作爲除草劑以防治有害 植物生成。 本發明之物質還對作物具有優異的生長調節作用。它 們會以調節的方式介入植物的代謝作用且因而可以對植物 體的構件進行瞄準性防治並可增進收穫量例如促進乾燥及 在發育不良時刺激發育。再者,它們也很適合用來對雜草 作一般性防治並抑制其生長且在此過程中並不會損毀植 物。對於許多單子葉及雙子葉作物而言抑制雜草的生長十 分重要,因爲雜草可以減少或徹底地防止作物被風吹倒。 本發明之化合物可採用習知製劑中的可加水粉末、可 乳化濃縮液、可噴灑溶液、殺蟲藥粉或顆粒的形式來使 用。所以本發明進一步地係關於含有式(I )化合物之除 -19- 200533665 (16) 草組成物。本發明式(1 )化合物可用多種不同的方式來 配方,視其主要的生物性及/或化學-物理性參數而定。適 當的調合物之實例有:可加水粉末(WP )、水溶性粉末 (SP )、水溶性濃縮液、可乳化濃縮液(’EC )、乳液 (E W )如水包油乳液或油包水乳液、可噴灑溶液、懸浮 濃縮液(S C )、油-基質或水-基質分散液、油-可溶混性 溶液、膠囊懸浮液(CS )、殺蟲藥粉(DP )、種籽-澆淋 產物、散佈及土壤施藥顆粒、微粒形式之顆粒(GR)、噴 霧顆粒、塗層顆粒及附著顆粒、水-可分散顆粒(W G )、 水溶性顆粒(SG ) 、ULV調合物、微膠囊及蠟等。此等 個別的調合物類型原貝1J上已習知且係述於例如Winnacker-
Kuchler, “Chemisehe Technologie” [Chemical Technology] ? Volume 7,C. Hauser Verlag Munich, 4th Ed. 1986, Wade van V alkenburg, “Pesticide Formulations’、Marcel Dekker, N.Y·,1 9 7 3 ; K· Martens,“Spray Drying” Handbook,3rd Ed. 1979,G. Goodwin Ltd. London (倫享夕)。 類似地所需之配方助劑如惰性物質、界面活性劑、溶 劑及額外的添加劑爲習知的且係述於例如:Watkins,
Handbook of Insecticide Dust Diluents and Carriers’’,2
Ed·, Darland Books, Caldwell N. J., H. v. Olphen, “Introduction to Clay Colloid Chemistry' 2nd Ed·,J. Wiley & Sons, N.Y.; C. Marsden, u So] vents Guide 55 5 2 nd
Ed” Interscience,Ν·Υ. 1963 ; McCutclieon’s “Detergents and Emulsifiers Annual”,MC Pub]· Corp.,Ridgewood N· - 20- 200533665 (17) J. i Sisley and Wood, “Encyclopedia of Surface Active Agents55 5 Che m. Publ. Co. Inc., N. Y. 1964; Schonfeldt, ccGrenzflachenaktive Athylenoxidaddukte “ [Surface-active ethylene oxide adducts], W i s s. Verlagsgesell” Stuttgart 1 9 7 6 ; Winnacker-Kiichler, “Chemise he Technologie’’,
Volume 7 ? C. Hauser Verlag Munich 4th Ed. 1986。 可加水粉末爲可均勻地分散在水中之製劑,其內除了 活性物質以外,還可含有離子及/或非離子界面活性劑 (溼化劑、分散劑),例如聚氧化乙烯烷基苯酚、聚氧化 乙烯脂肪醇、聚氧化乙烯脂肪胺、脂肪醇聚二醇醚硫酸 鹽、烷基磺酸鹽、烷基苯磺酸鹽、2 5 2 二萘甲烷-6,6 二 磺酸鈉、木質磺酸鈉、二丁基萘磺酸鹽或其它油醯甲基牛 磺酸鈉,以及稀釋劑或惰性物質等。爲了製備可加水粉 末,要把具有除草活性之物質用例如習知設備像是錘式粉 碎機、鼓風碾磨機及空氣-噴射碾磨機等磨得粉碎,且同 時或接著與該等配方助劑混合在一起。 可乳化濃縮液係把活性物質以及其它一或多種離子及 /或非離子界面活性劑(乳化劑)溶於有機溶劑如丁醇、 環己酮、二甲基甲醯胺、二甲苯或其它高沸點的芳香族或 烴類或此等有機溶劑之混合物來製成的。可採用之乳化劑 的實例有:烷芳基磺酸鈣鹽類如十二烷基苯磺酸鈣,或者 非離子乳化劑如脂肪酸聚二醇酯、烷芳基聚二醇醚、脂肪 醇聚二醇醚、環氧丙烷/環氧乙烷濃縮液、烷基聚醚、山 梨聚糖酯類如山梨聚糖脂肪酸酯或聚氧化乙烯山梨聚糖酯 -21 - 200533665 (18) 類如聚氧化乙烯山梨聚糖脂肪酸酯等。 殺蟲藥粉可藉著把活性物質與細分 天然黏土如高嶺土、皂土及葉蠟石,或 來製得。 懸浮濃縮液可爲水基質或者油基質。 知的珠磨機,若適合還可加入上述其它調 及之界面活性劑進行濕式碾磨而製得。 乳液如水包油乳液(EW )例如可使 碾磨機及/或靜力混合器把活性物質與水 適合還可加入上述其它調合物類型中已携 一起混合來製得。 顆粒可藉著把活性物質噴在具有吸附 質上或把活性物質濃縮液藉由黏附劑如聚 酸鈉或其它礦物油的幫助來施加到載體如 它粒狀惰性物質的表面上而製得。適當的 用製造肥料顆粒的習知方式來造粒,若需 起製成混合物。 水可分散顆粒一般係在無固體惰性物 如噴乾、流化床造粒、盤式造粒、高速攪 而製成。 爲了製備盤式顆粒、流化床顆粒、擠 粒可以參考例如” s P r a y - D r y i n g H a η d b ο 〇 k ” G ο o d w i n L t d .,倫敦;J . E · B ι· o w n i n g,
Chemical and Engineering 1 9 6 7, pages 體物質如滑石, 藻土等一起碾磨 它們可用例如習 合物類型中已提 用攪拌器、膠體 性有機溶液,若 及之界面活性劑 性之粒狀惰性物 乙烯醇、聚丙烯 砂、高嶺石或其 活性物質亦可使 要還可與肥料一 質下用習知方法 袢器混合及擠製 製顆粒及噴乾顆 3rd ed· 1 9 7 9,G· ‘Agglomeration,,, 14 7 e t s e q .; -22- 200533665 (19) “Perry’s Chemical Engineer’s Handbook’’, 5th Ed··
McGraw-Hill, New York 1 9 7 3,pp. 8-57。 對於調配該等作物之保護產物的詳細細節可以參考例 如 G. C. Klin gman,“Weed Control as a science,,,John Wiley and Sons, Inc·,New York, 1961,pages 81-96 及 J. D. Freyer, S.A. Evans ? “Weed Control Handbook”,5th Ed., , Blackwell Scientific Publications, Oxford, 1968, pages • 101-103 〇 原則上,該農業化學製劑係含有〇 . 1到9 9重量%之式 (I )活性物質,更詳細地爲到95重量%之式(I )之 活性物質。於可加水粉末中’該活性物質濃度爲例如約1 0 到9 〇重量%,可用習知的配方成份把重量補足成1 〇 〇重量 %。於可乳化濃縮液中’活性物質的濃度份量爲約1到90 中量%,較佳爲5到80重量%。於殺蟲藥粉形式的調合物 中則含有1到3 0重量%之活性物質,較佳爲5到| 2 0重量 ^ %之活性物質;且於可噴灑溶液中則含有約0.05到80重 量%,較佳爲2至5 G重量%之活性物質。於水可分散顆粒 之例中,活性物質的份量部份將由該活性化合物係呈液體 或固髒的形式來決定’且部份將由所用之造粒助齊!Γ、塡料 • 等_丨央定。於水可分散顆粒之例中,該活性物質的含量係 介於丨到95重量%之間’較佳爲介於10到80重量%的範 圍內。 it匕夕f,如上所述之活性物質之調合物’若適當,可包 含增稠劑、濕化劑、分散劑、乳化劑、穿透劑、保存劑' -23- 200533665 (20) 抗東J ί容;4 料、載體、色料、消泡劑、揮發抑制 劑’及pH與黏度調節劑,此等各項成份皆已爲人習知。 此等調合物亦可組合其它殺害蟲活性物質如殺昆蟲 月ϋ、殺壁$1劑、除草劑、殺真菌齊g,以及毒性減輕劑、肥 料及/或生長調節劑,例如以預拌混合物或槽裝混合物的 形式來製造。 b等可用在混曰式§周合物或槽裝混合物中與本發明之 • 活性物質一起使用之活性物質爲例如述於Weed Research 26,441-4 4 5 (1986)或” The Pesticide Manual”,1Γ11 版,the British Crop Protection Council and the Royal Soc. of
Chemistry,1 997及其內所引用之文獻等之已知活性物質。 可與本發明式(I )化合物組合且必需提及之除草劑有例 如如下之物質(註:該等化合物或者係用國際標準化學會 (International Organization for Standardization(ISO)) 所用之俗名’或者使用其化學名,若適當以及其慣用編號 φ 來表示): 乙醯氯(acetochlor);艾西氟芬(acifluorfen);艾 寇尼芬(aclonifen ) ; A KH 7 0 8 8,即[[[1 - 5 - [ 2 -氯-4 -(三氟 甲基)-苯氧基卜2-硝苯基]-2_甲氧基亞乙基]胺基]氧基]醋 酸及其甲酯;草不綠;艾羅定(alloxydim );莠滅淨;醯 胺磺隆(amidosulfuron );殺草強;A M S,即胺基磺酸 銨;艾尼羅福司(anilofos );黃草靈;莠去津;阿芮磺 隆(azimsulfuroiie) ( DPX-A 8 94 7 );疊氮津;燕麥靈; B A S 5 1 6 Η,即5 -氟-2 -苯基-4 Η - 3-苯倂噁嗪-4 -酮;草除 -24- 200533665 (21)
靈;氟草胺;苯福塞特(benfuresate ):苯磺隆甲酯 (bensulfuro n methyl );地散磷;苯達松;苯芬耐帕 (benzofenap);苯氟(benzofluo】·);苯甲酸基丙-乙醋 (benzoylprop-ethyl);噻草隆;拜拉憐(bialaphos); 治草醚;除草定;溴丁泰(b r 〇 m 〇 b u t i d e );殺草全;溴苯 腈;溴目隆(bromuron);布米奈福司(buminafos);布 沙辛農 (busoxinone); 去草胺;布它米福司 (butamifos ) ; 丁 嫌那氯(butenachlor) ; 丁噻塔 _ (buthidazole);步挫林(butralin);蘇達滅;咖芬史 挫 (cafenstrole) ( CH-900 ) •,長殺草;咖芬挫隆 (cafentrazone ) (ICI-A005 1 ) ; CDAA,即 2-氯-Ν,Ν-二- 2-丙烯基乙醯胺;CDEC,即2-氯烯丙基二乙基二硫胺基甲 酸酯;氯甲氧芬(chlomethoxyfen );草滅平;氯利福-丁 酯(chlorazifop-butyl );氯麥賽隆(chlormesulon ) (ICI-A005 1 ); 氯溴隆;氯草靈;氯芬奈 (chlorfenac);氯甲丹;胺基氯噠嗪酮;氯梨目隆乙酯 (chlorimuron ethyl) ,·氯尼挫芬(chlorniti'ofen);綠麥 隆;枯草隆;氯苯胺靈;氯磺隆(chlorsulfuron );敵草 索;草克樂;辛甲林(c inmethyl in );辛諾磺隆 (cinosulfuron);克立梭定(clethodim)克羅 丁福帕 (clodinafop )及其酯衍生物(例如克羅丁福帕炔丙 酯);克羅麥丙 (clomeprop ):克羅丙氧定 (c 1 ο p r ο X y d i m );克羅必雷里得(c 1 〇 p y r a 1 i d );枯麥盧 隆(c u m y 1 u r ο n ) ( J C 9 4 0 );草淨津;草滅特;環磺目隆 -25- 200533665 (22) (cyclosulfa muron ) ( AC 104 ) ;環氧定 (c y c 1 o x y d i m ) •,環盧隆(c y c 1 u r ο n );塞鹵福帕 (cyhalofop)及其酯衍生物(如丁酯,DEH-112);塞迫闊 特(cyperquat);環草津;塞拍挫(cyprazole);代目隆 (daimuron ) ; 2 5 4 - D B ; 茅草枯;敵麥代份
(desmedipham) ;敵草淨;燕麥敵;麥草畏;二氯苯尼 (dichlobenil);二氯丙(dichlorprop);二氯苯氧基苯 氧基丙酸及其酯如其甲酯;二乙涕(diethatyl );枯莠 隆;二芬闊特 (difenzoquat ); 二福芬尼肯 (diflufenican);二麥福隆(dime furon ):紋枯利;二 甲麥淨( dimethametryn);二甲耐米德( dimethenamid) (SAN- 5 82H );二甲隆(dimethazone ),克羅馬隆 (clomazon) •,二麥塞賓(dimethipin) ;二麥挫磺隆 (d i m e t r a s u 1 f u r ο n ) ?二硝基胺(d i n i t r a m i n e );二諾塞 伯(dinoseb);二諾泰伯(dinoterb);草乃敵;殺草 淨;敵草快;dithiopyr;敵草隆;DNOC; eglinazine-乙 酯;EL 77,即5-氰基-1- ( 1,1-二甲基乙基)-N-甲基·1Η-吡 唑-4-羧醯胺;草多索;EPTC ;艾司丙卡(esprocarb ); 乙氟林(ethalfluralin);乙麥磺隆(ethametsulfuron) -甲酯;乙代目隆(ethidimuron ) •,乙歐林(ethiozin ); 乙福麥塞特(ethofumesate) ; F5231,即 N- [2 -氯-4-氟- 5-[4- ( 3-氟丙基)-4,5-二氫-5·酮基·1Η-四唑-1-基]苯基]乙 磺醯胺;乙氧芬(ethoxyfen )及其酯(如乙酯,ΗΝ-252);艾托苯尼得(etobenzanid) ( HW 52 ) ; 2,4,5 -涕 -26- (23) 200533665
丙酸;芬諾森(fenoxan),芬氧丙(fenoxaProP)及芬氧 丙-P及其酯如芬氧丙乙酯及芬氧丙-乙酯;芬氧定 (f e η ο X y d i m );非草隆;福納丙(f 1 a m p r ο p )-甲醋·,福 拉納5黃隆(flaza sul fur on );福盧利扶帕(f 1 u a z i f o p )及 福盧利扶帕-P及其酯,如福盧利扶帕-丁酯及福盧利扶帕-p-丁酯;氟消草;福麥沙蘭(flumetsulam );福麥土隆 (flumeturon );福米克羅雷(flumiclorac )及其酯(如 戊酯,S-2 3 03 1 );福米氧辛(flumioxazin ) ( S-4 82 ); 福米丙聘(flumipropyn );福珀森(flupoxam ) ( KN W- 7 3 9 );消草醚;氟糖芬(『111〇1<〇§1}’〇(^€11)-乙酯;氟丙希 (flupropacil) (UBIC-4243 );氟黎同(fluridone); 氟氣黎同(flurochloridone);氟氧比(fluroxypyr);氟 它盟(flurtamone ) •,佛麥沙芬( fomesafen);佛沙胺 ( fosamine);呋喃氧芬(furyloxyfen);糖佛思奈特 (glufosinate);鎭草寧;鹵沙芬(halosafen);鹵磺隆 (halosulfuron)及其酯(如甲酯,NC-319);鹵氧福帕 (haloxyfop)及其酯;鹵氧福帕-P(=R·鹵氧福帕)及其 酯;環己基二甲胺甲基三嗪二酮;依瑪拉皮爾 (imazapyr ):依瑪拉甲苯(imazamethabenz)-甲酯;依 瑪拉金(i ni a z a q u i η )及其鹽如銨鹽;碘苯腈;依瑪拉薩甲 皮爾 (i m a z e t h a m e t h a p y r ) ; 依瑪拉薩皮爾 (imazethapyr );依瑪磺隆(iniazosulfuron );異卡米德 (isocarbamid);異樂靈;異丙土隆(isoproturon);異 索隆(isouron );異氧苯(i s o x ab e η );異氧比服帕 -27- (24) 200533665 (isoxapyrifop);卡靈草;乳糖芬(lactofen);環草 定;里奴隆(linuron) ; MCPA; MCPB; 2,4 -甲氯丙酸; 麥芬納司特(m e f e η a c e t );麥福敵(m e f 1 u i d i d );麥它 米舂(metamitron);麥它氯(metazachlor);威百畝; 噻Π坐隆;滅草B定;去草酮;甲怠隆(m e t h y 1 d y m r ο η );間 苯隆(metabenzuron),甲苯隆(methobenzuron);莠谷 隆;麥脫氯(nietolachlor );麥脫沙瀾(meto su 1 am )
(XRD 5 1 1 );甲氧隆;塞克津;麥磺隆(metsulfuron )-甲酯;ΜΗ ;草達滅;殺草利;綠穀隆;滅草隆;單脲二 氫硫酸酯;ΜΤ 128,即6-氯-Ν- ( 3-氯-2-丙烯基)-5-甲基-Ν-苯基-3-噠嗪胺;ΜΤ 5950,即Ν·[3-氯·4-(1-甲基乙基) 苯基]-2-甲基戊烷醯胺;萘氧基苯基丙醯胺;草萘胺;抑 草生;NC 310,即 4-(2,4 -二氯苯甲醯基).-1-甲基-5-苯甲 氧基吡唑;除莠劑;尼寇磺隆(nicosulfuron );尼彼克 羅芬(nipyraclophen);尼挫林(nitralin) ;除草醚;硝 芬(nitrofluorfen );達草滅;歐苯卡(orbencarb) ; 黃草消;氧代阿己(oxadiargyl ) ( RP · 0 2 0 6 3 0 );惡草 靈;氧氟芬(oxyfluorfen );百草枯;克草猛;賓二甲林 (pendimethalin );全氟同(perf 1 ui d οne );分尼索份 (phenisopham ) ;分咪代份(p h e n m e d i p h a m ) ;毒莠 定;皮諾登(pinoxaden);派羅磷(piperophos);皮黎 丁卡(piributicarb) •,皮黎分諾(pirifenop) ·丁酯;匹 泰氯(pretilachlor);匹米磺隆(primisulfuron)-甲醋; IS 氰奈(procyanine);原二胺(prodiamine);卡樂 -28- (25) 200533665
施;叵隔耐辛(prog 1 in azine ) ·乙酯;撲滅通·,撲草淨; 毒草定;二氯丙醒苯胺;回帕奎拉福帕(propaquizafop) 及其酯;撲滅津;苯胺靈;回皮索氯(propisochlor); 巨匹醯胺(propyzamide);叵磺林(prosulfalin);叵磺 卡(prosulfocarb);巨磺隆(pros ulfuron) ( CGA-1 5 2 0 0 5 );廣草胺;匹克羅尼(p y r a c 1 ο n i 1 );卩比卩坐啉 酸;匹拉隆(pyrazon );匹磺隆(pyrazosulfuron)-乙 酯;匹氧芬(pyrazoxyfen );匹雷代特(pyridate );皮 黎硫巴克 (pyrithiobac ) ( KIH-203 1 );皮氧福帕 (pyroxofop )及其酯(如炔丙基酯);奎克羅雷克 (quinclorac ) •,奎米雷克(quinmerac);奎諾福帕 (quinofop)及其酯衍生物;奎羅福帕(quizalofop)及奎 羅福帕-P及其酯衍生物如奎羅福帕-乙酯;奎羅福帕-P-tefuryl酯及乙酯;雷黎督隆(renriduron );黎磺隆 (rimsulfuron) ( DPX-E 9636) ; S 275,即 2-[4 -氯-2-氟- 5- ( 2-丙炔氧基)苯基]-4,5,6,7-四氫-2 吲唑;密草通; s ethoxy dim ;環草隆;西瑪三嗪;西草淨;SN 1 062 7 9,即 2-[[7-[2-氯-4-(三氟甲基)苯氧基]-2-萘烯基]氧基]丙酸 及其甲酯;沙芬挫隆(sulfentrazon ) ( F M C - 9 7 2 8 5 , F- 6 2 8 5 ):沙法蘆隆 (sulfazuron ):磺麥土隆 (sulfometuron) ·甲酯;磺福塞特(sulfosate) (ICI-A0224 ) ; TCA ;泰布坦(tebutam ) ( GCP-5 5 44 );泰 布塞勿隆(tebuthiuron );特草定;芽根靈;特布氯 (terbuchlor ) ; 甲氧去草淨;特 丁拉辛 -29- 200533665 (26) (terbuthylazine);去草淨;TFi-I 4 5 0,即 N,N-二乙基-3-[(2·乙基-6-甲苯基)磺釀基]-1Η·1,2,4 -三卩坐-1-殘醯胺; 噻吩甲氯(thenylchlor ) ( NSK- 8 5 0 ):硫氮雜氟隆 (thiazafluron );硫偶氮皮爾(thiazopyr) (Mon-1 3200 );塞代兒立蜜(thidiazimin ) ( SN-240 8 5 );硫
苯卡(thiobencarb );塞芬磺隆(thifensulfuron )-甲 酯;泰歐卡本利 (tiocarbazil ); 磋烷氧定 (tralkoxy dim );參·艾來特(tri - a 11 ate );參擴隆 (triasulfuron );三偶氮芬醯胺(triazofenamide);參 苯隆(tribenuron ) -甲酯;參環皮爾(triclopyr );三代 份 (tridiphane );草達津;氟樂靈;參氟磺隆 (Uiflusulfuron )及其酯(如甲酯,DPX-6603 7 );三甲 隆;慈陀疊(tsitodef ) ·;斑鳩菊酸;WL 1 1 05 47,即 5-苯 氧基三氟甲基)苯基]-1H·四唑;UBH-509; D- 4 89 ; LS 82- 5 5 6 ; KP P - 3 0 0 ; N C - 3 2 4 ; N C - 3 3 0 ; K Η - 2 1 8 ; DPX-N8189 ; SC-0774 ; DOWCO- 5 3 5 ; DK-8910 ; V- 5 3482 ; PP-600 ; MBH-001 ; KIH- 92 0 1 ; ET-751 ; KIH-6127 及 KIH-2023 。 在使用時,把以商業可用形式存在之調合物用習知方 式來稀釋如可加水粉末、可乳化濃縮液、分散液及水-可 分散顆粒之例中就可用水來稀釋。殺蟲藥粉、土壤顆粒、 散佈用顆粒及可噴灑溶液等形式之製劑在使用前則無需再 用其它惰性物質來稀釋。施用式(I )化合物所需之用藥 量將隨著外在條件如特別是溫度、濕度及所用除草劑之本 -30- 200533665 (27) 質等條件而有所不同。該用藥量具有極寬廣的變化範圍如 可爲從0.001到1.0 kg/ha或更高之活性物質用藥量,但 較佳地係在0.005到7 5 0 g/ha的範圍。 如下實施例係用以顯示本發明: A.化學實施例 6-乙基-4- ( 4-三氟甲基-1H-1-吡唑基)-2· ( 2-三氟甲基批 D疋-4 -基氧基)赠卩疋(弟1.25號)之製備 把 〇·4 g ( 1.2 5 mmol)之 6-乙基-4- (4-三氟甲基-1H- 1 - 〇比D坐基)-2 -甲基石貝釀基赠呢’ 0.2 g(1.25 m m ο 1 )之4 » 經基-2-三氟甲基卩比D定及0.345 g(2.5 mmol)之碳酸鉀於 2 0 ml乙腈之混合物於回流下攪拌8小時,然後於室溫下 靜置隔夜。把混合物加到40 ml水中且用20 ml CH2C12萃 取.四次。合倂有機相且用硫酸鈉脫水且濃縮。於矽凝膠上 用庚烷/醋酸乙酯(1 : 1 )作爲溶析液來層析純化且生成 0 · 3 3 g ( 6 5 % )之6 -乙基-4 - ( 4 -三氟甲基-1 Η -1 -吡唑基)-2- ( 2-三氟甲基舭啶-4-基氧基)嘧啶。 ]H-NMR : 5[CDC13] 1 · 3 5 ( t,3 Η ),2 · 8 5 ( q 5 2 Η ),7 · 4 5 (dd5lH) 5 7.7 0 ( s?2H) 9 7.9 5 ( s? 1Η) ? 8.00 ( d?lH) ? 8.70 ( s51H ) ° 6-甲基-4- ( 4·三氟甲基-1H-1-吡唑基)-2- ( 2-三氟甲基吡 啶-4 -基氧基)嘧啶(第1 . 1 3號)之製備 把 〇·63 g(2.4 mmol)之 6 -甲基-4-(4-三氟甲基-111- -31 - 200533665 (28) 卜舭嗤基)-2 -氯喷Π定,0 · 3 9 g ( 2 · 4 m m ο 1 )之4 -經 氟甲基吡啶及〇 · 6 6 g ( 4 · 8 m m ο 1 )之碳酸鉀於2 0 之混合物於回流下攪拌8小時,然後於室溫下靜價 把混合物倒到4 0 m 1水中且用2 0 m 1 C H 2 C 12萃取2 倂有機相且用硫酸鈉脫水且濃縮。於矽凝膠上用 酸乙酯(7 : 3 )作爲溶析液來層析純化且生成 (8 5%)之 6-甲基-4- ( 4-三氟甲基-1Η-1-吡唑基) 二氣·甲基卩比Π定-4 -基氧基)嗦D定。 ]H-NMR : 5[CDC13] 2.60 ( t?3H) ? 7.43 ( dd?lH; (d,lH),7.70 ( s,1H),7·98 ( S,1H),8·70 ( 8·80 ( d,lH) 〇 6-甲氧基-4- ( 4-三氟甲基-1Η·1-吡唑基)-2- ( 1-甲 氟甲基吡唑-5-基氧基)嘧啶(第9.37號)之製備 把0.35§(1.09 111111〇1)之6-甲氧基-4-(4-三 1H-1-吡唑基)-2-甲基磺醯基嘧啶,0.18 g ( 1.09 之 1-甲基-3 -三氟甲基-2 -毗唑啉-5 -酮及 0.3 ί mmol )之碳酸鉀於5 ml乙腈之混合物於回流下攪 時,然後於室溫下靜置隔夜。把混合物倒到4 0 ml 用20 ml CH2C12萃取四次。合倂有機相且用硫酸鈉 濃縮。於矽凝膠上用庚烷/醋酸乙酯(1 : 1 )作爲 來層析純化且生成0.38 g(82%)之6-甲氧基-4-( 甲基-1Η·1-吡唑基)-2-(卜甲基-3·三氟甲基吡唑 基)畴D定。 基-2-三 ml乙腈 【隔夜。 3次。合 庚烷/醋 ;0.8 g -2-(2- » ? 7.68 s,lH), 基-3 -二 氟甲基-mmol ) ? ( 2.17 拌8小 水中且 I脫水且 溶析液 4-三氟 _ 5 _基氧 -32 - 200533665 (29) - NMR : 5[CDC13] 3 . 8 5 ( s,3 Η ),4 · 0 0 ( s,3 Η ),6,2 4 (s51H),7.15(s,1H),7.95(s,1H),8.65(s,1H)。 3-甲基-4-三氟甲基吡唑之製備 把 1 5 g ( 1 19 mmol )之 4,4,4-三氟·丁烷-2-酮及 2 8.3 g ( 2 3 8 mmol )之N,N-二甲基甲醯胺二甲基縮醛於100 ml 甲苯之溶液於回流下攪拌8小時,然後把混合物揮發至 乾。粗產物用100 ml乙醇來溶解,加入18·45 ml肼水合 物’然後把混合物於回流下攪拌8小時且再濃縮。於砂凝 膨上用庚烷/醋酸乙酯(3 : 7 )作爲溶析液來層析純化且 生成5.4 g ( 31%)之3-甲基-4-三氟甲基吡唑。 'H^NMR : 6[CDC13] 2.40 ( s,3H ),7.75 ( S,1H )。 於下表中所列示的實施例係以類似於如上詳細說明之 方法來製備或以類似於如上詳細說明之方法來取得。. 在此所用之縮寫符號具有如下意義: 乙基 0 E t =乙氧基 M e =甲基 0 Vl e =甲氧基 EA =醋酸乙酯 m . p .=熔點 滯留 i-Pr=異丙基 n-Pr =正丙基 室溫 -33 (30) 200533665 表1 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = Y1 R6 = Η
No. R1 R2 R3 R4 R5 物理數據 1.1 Η H H H cf3 1H-NMR: δ [CDCI3] 7.43 (dd, 1H), 7.67 (d, 1H), 7.82 (d, 1H), 7.98 (s, 1H), 8.75 (d, 1H), 8.78 (s, 1H)8.80 (d, 1H) 1.2 Η H Me H cf3 1.3 Η H H Me cf3 1.4 Η H H H Cl 1.5 Η H Me H Cl 1.6 Η H H Me Cl 1.7 Η H H H CN 1.8 Η H Me H CN 1.9 Η H H Me GN 1.10 Η H H H OCF2H 1.11 Η H Me H ocf2h 1.12 Η H H Me 〇cf2h 1.13 Me H H H cf3 1H-NMR: δ [CDCI3] 2.60 (s, 3H), 7.43 (dd, 1H), 7.68 (d, 1H), 7.70 (s, 1H), 7.98 (s, 1H), 8.70(s, 1H), 8.80(d, 1H) 1.14 Me H Me H cf3 1H-NMR: δ [CDGI3] 2.45 (s, 3H), 2.59 (s, 3H), 7.40 (dct, 1H), 7.60 (s, 1H), 7.66 (d, 1H), 8.60 (st1H), 8.78 (d, 1H) 1.15 Me H H Me cf3 1.16 Me H H H Cl 1H-NMR: δ [CDCI3] 2.60 (s, 3H), 7.16 (dd, 1H), 7.32 (d, 1H), 7.66 (s, 1H), 7.95 (s, 1H), 8.45(d, 1H),8.70(s, 1H) 1.17 Me H Me H Cl -34- (31)200533665
No. R1 R2 R3 R4 R5 物理數據 1.18 Me H H Me Cl 1.19 Me H H H CN 1.20 Me H Me H CN 1.21 Me H H Me CN 1.22 Me H H H OCF2H 1H-NMR: δ [CDCI3] 2.60 (s, 3H), 6.82 (d, 1H)t 7.03 (dd, 1H), 7.53 (t, 1H), 7.65 (s, 1H), 7.95 (s, 1H), 8.25 (d, 1H), 8.70 (s, 1H) 1.23 Me H Me H ocf2h 1.24 Me H H Me ocf2h 1.25 Et H H H cf3 1H-NMR: δ [CDCI3] 2.35 (t, 3H), 2.85 (q, 2H), 7.45 (dd, 1H), 7.70 (s, 2H), 7.95 (s, 1H), 8.00 (d, 1H), 8.70 (s, 1H) 1.26 Et H Me H cf3 1H-NMR: δ [CDCi3] 1.35 (t, 3H), 2.45 (s, 3H), 2.84 (q, 2H), 7.41 (dd, 1H), 7.60 (s, 1H), 7.70 (d,1H),8.60(s,1H),8.78(d, 1H) 1.27 Et H H Me cf3 1.28 Et H H H Cl 1H-NMR: δ [CDCI3] 1.40 (t, 3H), 2.92 (q, 2H), 7.23 (dd, 1H), 7.38 (d, 1H), 7.72 (s, 1H), 8.02 (s,1H), 8.50 (d, 1H), 8.88 (s, 1H) 1.29 Et H Me H Cl 1.30 Et H H Me Cl 1.31 Et H H H CN 1.32 Et H Me H CN 1.33 Et H H Me CN 1.34 Et H H H ocf2h 1.35 Et H Me H 〇cf2h 1.36 Et H H Me ocf2h 1.37 〇Me H H H cf3 1H-NMR: δ [CDCI3] 4.00 (s, 3H), 7.15 (s, 1H), 7.42 (dd, 1H), 7.70 (d, 1H), 7.92 (s, 1H), 8.60 (s, 1H), 8.80 (d, 1H) -35- 200533665(32)
No. R1 R2 R3 R4 R5 物理數據 1.38 〇Me H Me H cf3 1H-NMR: δ [CDCI3] 2.40 (s, 1H), 3.98 (s, 3H), 7.08 (s, 1H), 7.42 (dd, 1H), 7.70 (d, 1H), 8.50 (st 1H), 8.80 (d, 1H) 1.39 〇Me H H Me cf3 1.40 〇Me H H H Cl 1H-NMR: δ [CDCI3] 4.00 (s, 3H), 7.13 (s, 1H), 7.18 (dd, 1H), 7.34 (d, 1H), 7.94 (s, 1H), 8.45 (d, 1H), 8.60 (s, 1H) 1.41 〇Me H Me H Cl 1.42 OMe H H Me Cl 1.43 OMe H H H CN 1.44 OMe H Me H CN 1.45 OMe H H Me CN 1.46 OMe H H H 〇CF2H 1H-NMR: δ [CDCI3] 4.00 (s, 3H), 6.85 (d, 1H), 7.05 (dd, 1H)} 7.12 (s, 1H), 7.55 (t, 1H), 7.92 (s, 1H), 8.25 (d, 1H), 8.60 (s, 1H) 1.47 OMe H Me H 〇cf2h 1.48 OMe H H Me ocf2h 1.49 Cl H H H cf3 1.50 Cl H Me H cf3 1.51 Cl H H Me cf3 1.52 Cl H H H Cl 1.53 Cl H Me H Cl 1.54 Cl H H Me Cl 1.55 Cl H H H CN 1.56 C! H Me H CN 1.57 Cl H H Me CN 1.58 Cl H H H 〇CF2H 1.59 Cl H Me H 〇cf2h 1.60 Cl H H Me 〇cf2h -36- 200533665 (33)
No. R1 R2 R3 R4 R5 物理數據 1.61 CN H H H cf3 1.62 CN H Me H cf3 1.63 CN H H Me cf3 1.64 CN H H H Cl 1.65 CN H Me H Cl 1.66 CN H H Me Cl 1.67 CN H H H CN 1.68 GN H Me H CN 1.69 CN H H Me CN 1.70 CN H H H OCF2H 1.71 CN H Me H ocf2h 1.72 CN H H Me ocf2h 1.73 H H H H cf2h 1.74 Me H Me H cf2h 1.75 Me H H Me cf2h 1.76 Me H H H cf2h 1.77 Et H H H cf2h 1H-NMR: δ [CDCI3] 1.35 (t, 3H), 2.86 (q, 2H), 6.70 (t, 1H), 7.35 (dd, 1H), 7.65 (d, 1H), 7.70 (s, 1H)f 7.98 (s, 1H), 8.70 (s, 1H), 8.72 (d, 1H) 1.78 Et H Me H cf2h 1H-NMR: δ fCDCIs] 1.35 (t, 3H), 2.45 (s, 3H), 2.84 (q, 2H), 6.70 (t, 1H), 7.35 (dd, 1H), 7.60 (s, 1H), 7.65 (d, 1H), 8.60 (s, 1H), 8.70 (d, 1H) 1.79 Et H H Me cf2h 1.80 OMe H H H cf2h 1.81 OMe H Me H cf2h 1.82 OMe H H Me cf2h 1.83 OH H H H cf3 -37- (34) 200533665
No. R1 R2 R3 R4 R5 物理數據 1.84 OH H Me H cf3 1.85 OH H H Me cf3 1.86 OH H H H 〇cf2h 1.87 OH H Me H ocf2h 1.88 OH H H Me ocf2h 1.89 OH H H H cf2h 1.90 OH H Me H cf2h 1.91 OH H H Me cf2h 1.92 n-Pr H H H cf3 1H-NMR: δ [CDCI3] 1.00 (t, 3H), 1.80 (m, 2H), 2.80 (t, 2H), 7.42 (dd, 1H), 7.70 (s, 1H), 7.72 (d, 1H), 7.95 (s, 1H), 8.70 (s, 1H), 8.80 (d, 1H) 1.93 n-Pr H H H Cl 1H-NMR: δ [CDCI3] 1.00 (t, 3H), 1.80 (m, 2H), 2.80 (t, 2H), 7.18 (dd, 1H), 7.30 (d, 1H), 7.68 (s, 1H), 7.95 (s, 1H), 8.45 (d, 1H), 8.70 (s, 1H) 1.94 cf3 H H H cf3 ’H-NMR: δ [CDCI3] 7.50 (dd, 1H), 7.72 (d, 1H), 8.05 (s, 1H), 8.15 (s, 1H), 8.75 (s, 1H), 8.83 (d, 1H) 1.95 ch2ch2ch2 H H cf3 1H-NMR: δ [CDCy 2.25 (m, 2H), 3.05 (t, 2H), 3.40 (t, 2H), 7.40 (dd, 1H), 7.65 (d, 1H), 7.95 (s, 1H),8.72 (s,1H), 8.78 (s,1H) 表2 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = 丫2 R2 = H R6 = Η -38- 200533665 (35)
No. R1 R2 R3 R4 R5 R6 物理數據 2.1 H H H H cf3 H 1H-NMR: δ [CDCI3] 7.42 (m, 1H), 7.55 (m, 1H), 7.70 (d, 1H), 7.95 (s, 1H), 8.65 (d, 1H), 8.70 (s, 1H) 2.2 H H Me H cf3 H 2.3 H H H Me cf3 H 2.4 H H H H Cl H 2.5 H H Me H Cl H 2.6 H H H Me Cl H 2.7 H H H H CN H 2.8 H H Me H CN H 2.9 H H H Me CN H 2.10 H H H H OCF2H H 2.11 H H Me H 〇cf2h H 2.12 H H H Me 〇cf2h H 2.13 Me H H H cf3 H 1H-NMR: δ [CDCI3] 2.60 (s, 3H), 7.28 (s, 1H), 7.45 (m, 1H), 7.60 (m, 3H), 7.95 (s, 1H), 8.60 (s, 1H) 2.14 Me H Me H cf3 H 2.15 Me H H Me cf3 H 2.16 Me H H H Cl H 2.17 Me H Me H Cl H 2.18 Me H H Me Cl H 2.19 Me H H H CN H 2.20 Me H Me H CN H 2.21 Me H H Me CN H 2.22 Me H H H 〇CF2H H 2.23 Me H Me H 〇cf2h H 2.24 Me H H Me 〇cf2h H -39- (36)200533665
No· R1 R2 R3 R4 R5 R6 物理數據 2.25 Et H H H cf3 H 2.26 Et H Me H cf3 H 1H-NMR: δ [CDCI3] 1.30 (t, 3H), 2.41 (s, 3H), 2.80 (q, 2H), 7.42 7.58 (m,3H), 8.50 (s, 1H) 2.27 Et H H Me cf3 H 2.28 Et H H H Cl H 2.29 Et H Me H Cl H 2.30 Et H H Me Cl H 2.31 Et H H H CN H 2.32 Et H Me H CN H 2.33 Et H H Me CN H 2.34 Et H H H ocf2h H 2.35 Et H Me H ocf2h H 2.36 Et H H Me ocf2h H 2.37 〇Me H H H cf3 H 1H-NMR: δ [CDCI3] 3.85 (s, 3H), 6.97 (s, 1H), 7.35 (m, 1H), 7.50 (m, 3H),7.80 (s, 1H), 8.44 (s, 1H) 2.38 OMe H Me H cf3 H 1H-NMR: δ [CDCI3] 2.40 (s, 3H), 3.94 (s, 3H), 7.00 (s, 1H), 7.42 (m, 1H),7.56 (m,3H),8.43 (s, 1H) 2.39 OMe H H Me cf3 H 2.40 OMe H H H Cl H 2.41 OMe H Me H Cl H 2.42 OMe H H Me Cl H 2.43 OMe H H H CN H 2.44 OMe H Me H CN H 2.45 OMe H H Me CN H 2.46 OMe H H H OCF2H H 2.47 OMe H Me H 〇cf2h H -40- 200533665 (37)
No. R1 R2 R3 R4 R5 R6 物理數據 2.48 OMe H H Me 〇cf2h H 2.49 Cl H H H cf3 H 2.50 Cl H Me H cf3 H 2.51 Cl H H Me cf3 H 2.52 Cl H H H Cl H 2.53 Cl H Me H Cl H 2.54 Cl H H Me Cl H 2.55 Cl H H H CN H 2.56 Cl H Me H CN H 2.57 Cl H H Me CN H 2.58 Cl H H H OCF2H H 2.59 Cl H Me H ocf2h H 2.60 Cl H H Me ocf2h H 2.61 CN H H H cf3 H 2.62 CN H Me H cf3 H 2.63 CN H H Me cf3 H 2.64 CN H H H Cl H 2.65 CN H Me H Cl H 2.66 CN H H Me Cl H 2.67 CN H H H CN H 2.68 CN H Me H CN H 2.69 CN H H Me CN H 2.70 CN H H H 〇CF2H H 2.71 CN H Me H 〇cf2h H 2.72 CN H H Me 〇cf2h H 2.73 cf3 H H H cf3 H 1H-_R: δ [CDCI3] 7.45 (m,1H), 7.60 (m, 3H)t 7.70 (d, 1H), 8.00 (s, 1H), 8.05 (s, 1H), 8.63 (s, 1H) -41 - 200533665 (38)
No. R1 R2 R3 R4 R5 R6 物理數據 2.74 n-Pr H H H cf3 H 1H-NMR: δ [CDCI3] 1.00 (t, 3H), 2.80 (m, 2H), 2.78 (t, 2H), 7.42 (m, 1H), 7.58 (m, 3H), 7.95 (s, 1H), 8.60 (s, 1H) 2.75 n-Pr H H H cf3 4-F 1H-NMR: δ [CDCI3] 1.00 (t, 3H), 2.80 (m, 2H), 2.76 (t, 2H), 7.28 (m, 1H), 7.42 (m, 1H), 7.53 (m, 1H), 7.60 (s, 1H), 7.95 (s, 1H), 8.63 (s, 1H) 2.76 Et H H H cf3 4-F 1H-NMR: δ [CDCI3] 1.30 (t, 3H), 2.80 (q, 4H), 7.30 (m, 1H), 7.42 (m, 1H), 7.52 (m, 1H), 7.60 (s, 1H), 7.94 (s, 1H) 2.77 Et H Me H cf3 4-F 1H-NMR: δ [CDCI3] 1.30 (t, 3H), 2.42 (s, 3H), 2.80 (q, 2H), 7.28 (m, 1H), 7.40 (m, 1H), 7.55 (m, 1H), 7.55 (s, 1H), 8.55 (s, 1H) 2.78 ch2ch2ch2 H H cf3 H 1H-NMR: δ [CDCI3] 2.20 (m, 2H), 3.00 (t, 2H), 3.40 (t, 2H), 7.42 (m, 1H), 7.55 (m, 3H), 7.92 (s, 1H), 8.60 (s,1H)
-42- 200533665 (39) 表3 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = Y3 R2 = H R6 = Η
No· R1 R3 R4 R5 物理數據 3.1 Η H H cf3 3.2 Η Me H cf3 3.3 Η H Me cf3 3.4 Η H H Cl 3.5 Η Me H Cl 3.6 Η H Me Cl 3.7 Η H H CN 3.8 Η Me H CN 3,9 Η H Me CN 3.10 Η H H 〇CF2H 3.11 Η Me H 〇cf2h 3.12 Η H Me ocf2h 3.13 Me H H cf3 3.14 Me Me H cf3 1H-NMR: δ [CDCI3] 2.55 (s, 3H), 7.35 (d, 1H), 7.63 (d, 1H), 7.65 (s, 1H), 7.95 (s, 1H), 8.03 (dd, 1H),8.62 (s, 1H) 3.15 Me H Me cf3 3.16 Me H H Cl 3.17 Me Me H Cl 3.18 Me H Me Cl 3.19 Me H H CN 3.20 Me Me H CN 3.21 Me H Me CN 3.22 Me H H OCF2H -43- (40)200533665
No. R1 R3 R4 R5 物理數據 3.23 Me Me H 〇cf2h 3.24 Me H Me 〇cf2h 3.25 Et H H cf3 3.26 Et Me H cf3 3.27 Et H Me cf3 3.28 Et H H Cl 3.29 Et Me H Cl 3.30 Et H Me Cl 3.31 Et H H CN 3.32 Et Me H CN 3.33 Et H Me CN 3.34 Et H H OCF2H 3.35 Et Me H ocf2h 3.36 Et H Me 〇cf2h 3.37 OMe H H cf3 3.38 〇Me Me H cf3 3.39 OMe H Me cf3 3.40 OMe H H Cl 3.41 OMe Me H Cl 3.42 OMe H Me Cl 3.43 OMe H H CN 3.44 OMe Me H CN 3.45 OMe H Me CN 3.46 OMe H H 〇CF2H 3.47 OMe Me H 〇cf2h 3.48 OMe H Me 〇cf2h 3.49 Cl H H cf3 -44- (41)200533665
No· R1 R3 R4 R5 物理數據 3.50 Cl Me H cf3 3.51 Cl H Me cf3 3.52 Cl H H Cl 3.53 Cl Me H Cl 3.54 Cl H Me Cl 3.55 Cl H H CN 3.56 Cl Me H CN 3.57 Cl H Me CN 3.58 Cl H H OCF2H 3.59 Cl Me H ocf2h 3.60 Cl H Me ocf2h 3.61 CN H H cf3 3.62 CN Me H cf3 3.63 CN H Me cf3 3.64 CN H H Cl 3.65 CN Me H Cl 3.66 CN H Me Cl 3.67 CN H H CN 3.68 CN Me H CN 3.69 CN H Me CN 3.70 CN H H OCF2H 3.71 CN Me H 〇cf2h 3.72 CN H Me ocf2h -45- 200533665 (42) 表4 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = Y4 R2 = H R6 = Η
No. R1 R3 R4 R5 物理數據 4.1 Η H H cf3 4.2 Η Me H cf3 4.3 Η H Me cf3 4.4 Η H H Cl 4.5 Η Me H Cl 4.6 Η H Me Cl 4.7 Η H H CN 4.8 Η Me H CN 4.9 Η H Me CN 4.10 Η H H 〇CF2H 4.11 Η Me H 〇cf2h 4.12 Η H Me 〇cf2h 4.13 Me H H cf3 4.14 Me Me H cf3 4.15 Me H Me cf3 4.16 Me H H Cl 4.17 Me Me H Cl 4.18 Me H Me Cl 4.19 Me H H CN 4.20 Me Me H CN 4.21 Me H Me CN 4.22 Me H H 〇CF2H 4.23 Me Me H ocf2h 4.24 Me H Me 〇cf2h 4.25 Et H H cf3 4.26 Et Me H cf3 4.27 Et H Me cf3 4.28 Et H H Cl - 46- (43)200533665
No· R1 R3 R4 R5 物理數據 4.29 Et Me H Cl 4.30 Et H Me Cl 4.31 Et H H CN 4.32 Et Me H CN 4.33 Et H Me CN 4.34 Et H H OCF2H 4.35 Et Me H ocf2h 4.36 Et H Me 〇cf2h 4.37 OMe H H cf3 4.38 OMe Me H cf3 4.39 OMe H Me cf3 4.40 OMe H H Cl 4.41 OMe Me H Cl 4.42 OMe H Me Cl 4.43 OMe H H CN 4.44 OMe Me H CN 4.45 OMe H Me CN 4.46 OMe H H OCF2H 4.47 OMe Me H ocf2h 4.48 OMe H Me ocf2h 4.49 Cl H H cf3 4.50 Cl Me H cf3 4.51 Cl H Me cf3 4.52 Cl H H Cl 4.53 Cl Me H Cl 4.54 Cl H Me Cl 4.55 Cl H H CN 4.56 Cl Me H CN 4.57 Cl H Me CN 4.58 Cl H H OCF2H 4.59 Cl Me H ocf2h 4.60 Cl H Me ocf2h -47- 200533665 (44)
No. R1 R3 R4 R5 物理數據 4.61 CN H H cf3 4.62 CN Me H cf3 4.63 CN H Me cf3 4.64 CN H H Ci 4.65 CN Me H Cl 4.66 CN H Me Cl 4.67 CN H H CN 4.68 CN Me H CN 4.69 CN H Me CN 4.70 CN H H OCF2H 4.71 CN Me H ocf2h 4.72 CN H Me ocf2h
表5 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = Y5 R2 = Η
No· R1 R3 R4 物理數據 5.1 H H H 5.2 H Me H 5.3 H H Me 5.4 H H H 5.5 H Me H 5.6 H H Me 5.7 H H H 5.8 H Me H 5.9 H H Me 5.10 H H H 5.11 H Me H 5.12 H H Me -48 - 200533665 (45)
No. R1 R3 R4 物理數據 5.13 Me H H 1H-NMR: δ [CDCI3] 2.58 (s, 3H), 7.03 (m, 2H), 7.15 (m, 1H), 7.60 (s, 1H), 7.92 (s, 1H), 8.62 (s, 1H) 5.14 Me Me H 5.15 Me H Me 5.16 Me H H 5.17 Me Me H 5.18 Me H Me 5.19 Me H H 5.20 Me Me H 5.21 Me H Me 5.22 Me H H 5.23 Me Me H 5.24 Me H Me 5.25 Et H H 5.26 Et Me H 5.27 Et H Me 5.28 Et H H 5.29 Et Me H 5.30 Et H Me 5.31 Et H H 5.32 Et Me H 5.33 Et H Me 5.34 Et H H 5.35 Et Me H 5.36 Et H Me 5.37 〇Me H H 5.38 〇Me Me H 5.39 OMe H Me 5.40 OMe H H 5.41 OMe Me H 5.42 OMe H Me 5.43 OMe H H >49- (46)200533665
No. R1 R3 R4 物理數據 5.44 〇Me Me H 5.45 〇Me H Me 5.46 〇Me H H 5.47 〇Me Me H 5.48 〇Me H Me 5.49 Cl H H 5.50 Cl Me H 5.51 Cl H Me 5.52 Cl H H 5.53 Cl Me H 5.54 Cl H Me 5.55 Cl H H 5.56 Cl Me H 5.57 Cl H Me 5.58 Cl H H 5.59 Cl Me H 5.60 Cl H Me 5.61 CN H H 5.62 CN Me H 5.63 CN H Me 5.64 CN H H 5.65 CN Me H 5.66 CN H Me 5.67 CN H H 5.68 CN Me H 5.69 CN H Me 5.70 CN H H 5.71 CN Me H 5.72 CN H Me -50- (47) 200533665 表6 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = Y6 R2, R6 = H R7 = Et
No. R1 R3 R4 R5 物理數據 6.1 Η H H cf3 6.2 Η Me H cf3 6.3 Η H Me cf3 6.4 Η H H Cl 6.5 Η Me H Cl 6.6 Η H Me Cl 6.7 Η H H CN 6.8 Η Me H CN 6.9 Η H Me CN 6.10 Η H H 〇CF2H 6.11 Η Me H ocf2h 6.12 Η H Me ocf2h 6.13 Me H H cf3 6.14 Me Me H cf3 6.15 Me H Me cf3 6.16 Me H H Cl 6.17 Me Me H Cl 6.18 Me H Me Cl 6.19 Me H H CN 6.20 Me Me H CN 6.21 Me H Me CN 6.22 Me H H OCF2H 6.23 Me Me H ocf2h 6.24 Me H Me ocf2h 6.25 Et H H cf3 6.26 Et Me H cf3 6.27 Et H Me cf3 -51 - (48)200533665
No. R1 R3 R4 R5 物理數據 6.28 Et H H Cl 6.29 Et Me H Cl 6.30 Et H Me Cl 6.31 Et H H CN 6.32 Et Me H CN 6.33 Et H Me CN 6.34 Et H H OCF2H 6.35 Et Me H ocf2h 6.36 Et H Me 〇cf2h 6.37 OMe H H cf3 6.38 〇Me Me H cf3 6.39 OMe H Me cf3 6.40 OMe H H Cl 6.41 OMe Me H Cl 6.42 OMe H Me Cl 6.43 OMe H H CN 6.44 OMe Me H CN 6.45 OMe H Me CN 6.46 OMe H H ocf2h 6,47 OMe Me H 〇cf2h 6.48 OMe H Me ocf2h 6.49 Cl H H cf3 6.50 Cl Me H cf3 6.51 Cl H Me cf3 6.52 Cl H H Cl 6.53 Cl Me H Cl 6.54 Cl H Me Cl 6.55 Cl H H CN 6.56 Cl Me H CN 6.57 Cl H Me CN 6.58 Cl H H 〇CF2H 6.59 Cl Me H ocf2h -52- (49) 200533665
No. R1 R3 R4 R5 物理數據 6.60 Cl H Me 〇cf2h 6.61 CN H H cf3 6.62 CN Me H cf3 6.63 CN H Me cf3 6.64 CN H H Cl 6.65 CN Me H Cl 6.66 CN H Me Cl 6.67 CN H H CN 6.68 CN Me H CN 6.69 CN H Me CN 6.70 CN H H OCF2H 6.71 CN Me H ocf2h 6.72 CN H Me 〇cf2h 6.73 Me H H cf2h 1H-NMR: δ [CDCl3] 1.50 (t, 3H, 2.58 (s,3H), 4.25 (q, 2H), 6.25 (s, 1H), 6.75 (t, 1H), 7.59 (s,1H), 7.95 (s, 1H), 8.70 (s, 1H)
表7 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = Y7 R6 = Η
No· R1 R2 R3 R4 R5 物理數據 7.1 H H H H cf3 7.2 H H Me H cf3 7.3 H H H Me cf3 7.4 H H H H Cl 7.5 H H Me H Cl 7.6 H H H Me Cl 7.7 H H H H CN -53- 200533665 (50)
No. R1 R2 R3 R4 R5 物理數據 7.8 H H Me H CN 7.9 H H H Me CN 7.10 H H H H 〇CF2H 7.11 H H Me H ocf2h 7.12 H H H Me ocf2h 7.13 Me H H H cf3 1H-NMR: δ [CDCI3] 2.60 (s, 3H), 7.36 (d, 2H), 7.45 (m, 1H), 7.60 (st 1H), 7.92 (s, 1H), 8.70 (s, 1H) 7.14 Me H Me H cf3 7.15 Me H H Me cf3 7.16 Me H H H Cl 7.17 Me H Me H Cl 7.18 Me H H Me Cl 7.19 Me H H H CN 7.20 Me H Me H CN 7.21 Me H H Me CN 7.22 Me H H H OCF2H 7.23 Me H Me H 〇cf2h 7.24 Me H H Me ocf2h 7.25 Et H H H cf3 1H-NMR: δ [CDCI3] 1.35 (t, 3H), 2.87 (q, 2H), 7.37 (d, 1H), 7.48 (m, 1H), 7.60 (s, 1H), 7.92 (s, 1H), 8.70 (s, 1H) 7.26 Et H Me H cf3 1H-NMR: δ [CDCI3] 1.35 (t, 3H), 2.43 (s, 2H), 2.83 (q, 2H), 7.36 (d, 1H), 7.46 (m, 1H), 7.57 (s,1H), 8.60 (s, 1H) 7.27 Et H H Me cf3 7.28 Et H H H Cl 7.29 Et H Me H Cl 7.30 Et H H Me Cl -54 - 200533665 (51)
No. R1 R2 R3 R4 R5 物理數據 7.31 Et H H H CN 7.32 Et H Me H CN 7.33 Et H H Me CN 7.34 Et H H H 〇CF2H 7.35 Et H Me H 〇cf2h 7.36 Et H H Me 〇cf2h 7.37 〇Me H H H cf3 1H-NMR: δ [CDCI3] 4.00 (s, 3H), 7.05 (s, 1H), 7.30 (d,; 1H), 7.45 (m, 1H), 7.90 (s, 1H), 8.60 (s, 1H) 7.38 OMe H Me H cf3 7.39 〇Me H H Me cf3 7.40 OMe H H H Cl 7.41 OMe H Me H Cl 7.42 OMe H H Me Cl 7.43 OMe H H H CN 7.44 OMe H Me H CN 7.45 OMe H H Me CN 7.46 OMe H H H 〇CF2H 7.47 OMe H Me H 〇cf2h 7.48 OMe H H Me 〇cf2h 7.49 Cl H H H cf3 7.50 Cl H Me H cf3 7.51 Cl H H Me cf3 7.52 Cl H H H Cl 7.53 Cl H Me H Cl 7.54 Cl H H Me Cl 7.55 Cl H H H CN 7.56 Cl H Me H CN -55- (52)200533665
No. R1 R2 R3 R4 R5 物理數據 7.57 Cl H H Me CN 7.58 Cl H H H 〇CF2H 7.59 Cl H Me H 〇cf2h 7.60 Cl H H Me 〇cf2h 7.61 CN H H H cf3 7.62 CN H Me H cf3 7.63 CN H H Me cf3 7.64 CN H H H Cl 7.65 CN H Me H Cl 7.66 CN H H Me Cl 7.67 CN H H H CN 7.68 CN H Me H CN 7.69 CN H H Me CN 7.70 CN H H H 〇CF2H 7.71 CN H Me H 〇cf2h 7.72 CN H H Me 〇cf2h 7.73 n-Pr H H H cf3 1H-NMR: δ [CDCI3] 1.00 (t, 3H), 2.43 (s, 1H), 2.80 (t, 2H), 7.38 (d, 1H), 7.46 (m,1H),7.60 (s, 1H),7.93 (s,1H),8.72 (s,1H) 7.74 ch2ch2ch2 Me cf3 1H-NMR: δ [CDCI3] 2.20 (m,2H),3.06 (t, 2H), 3.40 (t, 2H), 7.32 (d, 1H), 7.43 (mf 1H), 7.97 (s, 1H), 8.73 (s, 1H) -56- (53) 200533665 表8 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = Y8 R2 = H R6 = Η
No. R1 R3 R4 R5 物理數據 8.1 Η H H cf3 8.2 Η Me H cf3 8.3 Η H Me cf3 8.4 Η H H Cl 8.5 Η Me H Cl 8.6 Η H Me Cl 8.7 Η H H CN 8.8 Η Me H CN 8.9 Η H Me CN 8.10 Η H H 〇CF2H 8.11 Η Me H 〇cf2h 8.12 Η H Me ocf2h 8.13 Me H H cf3 8.14 Me Me H cf3 8.15 Me H Me cf3 8.16 Me H H Cl 8.17 Me Me H Cl 8.18 Me H Me Cl 8.19 Me H H CN 8.20 Me Me H CN 8.21 Me H Me CN 8.22 Me H H 〇CF2H 8.23 Me Me H 〇cf2h 8.24 Me H Me 〇cf2h 8.25 Et H H cf3 8.26 Et Me H cf3 8.27 Et H Me cf3 8.28 Et H H Cl -57- 200533665 (54)
No· R1 R3 R4 R5 物理數據 8.29 Et Me H Cl 8.30 Et H Me Cl 8.31 Et H H CN 8.32 Et Me H CN 8.33 Et H Me CN 8.34 Et H H 〇CF2H 8.35 Et Me H 〇cf2h 8.36 Et H Me 〇cf2h 8.37 OMe H H cf3 8.38 OMe Me H cf3 8.39 OMe H Me cf3 8.40 OMe H H Cl 8.41 OMe Me H Cl 8.42 OMe H Me Cl 8.43 OMe H H CN 8.44 OMe Me H CN 8.45 OMe H Me CN 8.46 OMe H H OCF2H 8.47 OMe Me H ocf2h 8.48 OMe H Me ocf2h 8.49 Cl H H cf3 8.50 Cl Me H cf3 8.51 Cl H Me cf3 8.52 Cl H H Cl 8.53 Cl Me H Cl 8.54 Cl H Me Cl 8.55 Cl H H CN 8.56 Cl Me H CN 8.57 Cl H Me CN 8.58 Cl H H ,OCF2H 8.59 Cl Me H ocf2h 8.60 Cl H Me 〇cf2h -58- (55) 200533665
No. R1 R3 R4 R5 物理數據 8.61 CN H H cf3 8.62 CN Me H cf3 8.63 CN H Me cf3 8.64 CN H H Cl 8.65 CN Me H Cl 8.66 CN H Me Cl 8.67 CN H H CN 8.68 CN Me H CN 8.69 CN H Me CN 8.70 CN H H OCF2H 8.71 CN Me H ocf2h 8.72 CN H Me ocf2h
表9 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = Y9 R6 = H R7 = Me
No. R1 R2 R3 R4 R5 物理數據 9.1 H H H H cf3 1H-NMR: δ fCDCI3] 3.85 (s, 3H), 6.46 (s, 1H), 7.83 (d, 1H), 8.00 (s, 1H), 8.70 (d, 1H), 8.80 (s,1H) 9.2 H H Me H cf3 1H-NMR: δ [CDCI3] 2.45 (s, 3H), 3.85 (s, 3H), 6.45 (s, 1H), 7.78 (d, 1H), 8.65 (d, 1H), 8.70 (s, 1H) 9.3 H H H Me cf3 9.4 H H H H Cl 9.5 H H Me H Cl 9.6 H H H Me Cl 9.7 H H H H CN 9.8 H H Me H CN -59- 200533665 (56)
No. R1 R2 R3 R4 R5 物理數據 9.9 H H H Me CN 9.10 H H H H 〇CF2H 9.11 H H Me H 〇cf2h 9.12 H H H Me 〇cf2h 9.13 Me H H H cf3 1H-NMR: δ [CDCI3] 2.60 (s, 3H), 3.85 (s, 3H), 6.47 (s, 1H), 7.95 (d, 1H), 8.75 (d, 1H) 9.14 Me H Me H cf3 1H-NMR: δ [CDCI3] 2.40 (s, 3H), 2.60 (s, 3H), 3.85 (s, 3H), 6.45 (s, 1H), 7.60 (s, 1H), 8.60 (s, 1H) 9.15 Me H H Me cf3 1H-NMR: δ [CDCI3] 2.52 (s, 3H), 2.60 (s, 3H), 3.80 (s, 3H), 6.35 (s, 1H), 7.72 (s, 1H), 7.82 (s, 1H) 9.16 Me H H H Cl 9.17 Me H Me H Cl 9.18 Me H H Me Cl 9.19 Me H H H CN 9.20 Me H Me H CN 9.21 Me H H Me CN 9.22 Me H H H OCF2H 9.23 Me H Me H 〇cf2h 9.24 Me H H Me ocf2h 9.25 Et H H H cf3 1H-NMR: δ [CDCI3] 1.35 (t, 3H), 2.90 (q, 2H), 3.86 (s, 3H), 6.47 (s, 1H), 7.70 (s, 1H), 7.96 (s, 1H), 8.75 (s, 1H) 9.26 Et H Me H cf3 1H-NMR: δ [CDCI3] 1.34 (t, 3H), 2.45 (s, 3H), 2.80 (q, 2H), 3.95 (s, 3H), 6.50 (s, 1H), 7.53 (s, 1H), 8.60 (s, 1H) 9.27 Et H H Me cf3 9.28 Et H H H Cl 9.29 Et H Me H Cl 9.30 Et H H Me Cl 9.31 Et H H H CN -60- 200533665 (57)
No. R1 R2 R3 R4 R5 物理數據 9.32 Et H Me H CN 9.33 Et H H Me CN 9.34 Et H H H 〇CF2H 9.35 Et H Me H 〇cf2h 9.36 Et H H Me 〇cf2h 9.37 OMe H H H cf3 1H-NMR: δ [CDCI3] 3.85 (s,3H),4.00 (s, 3H), 6.42 (s, 1H), 7.15 (s, 1H), 7.95 (s, 1H), 8.65 (s, 1H) 9.38 OMe H Me H cf3 9.39 OMe H H Me cf3 9.40 OMe H H H Cl 9.41 OMe H Me H Cl 9.42 OMe H H Me Cl 9.43 OMe H H H CN 9.44 OMe H Me H CN 9.45 OMe H H Me CN 9.46 OMe H H H 〇CF2H 9.47 OMe H Me H 〇cf2h 9.48 OMe H H Me 〇cf2h 9.49 Cl H H H cf3 9.50 Cl H Me H cf3 9.51 Cl H H Me cf3 9.52 Cl H H H Cl 9.53 Cl H Me H Cl 9.54 Cl H H Me Cl 9.55 Cl H H H CN 9.56 Cl H Me H CN 9.57 Cl H H Me CN 9.58 Cl H H H OCF2H 9.59 Cl H Me H 〇cf2h 9.60 Cl H H Me 〇cf2h 9.61 CN H H H cf3 -61 - 200533665 (58)
No· R1 R2 R3 R4 R5 物理數據 9.62 CN H Me H cf3 9.63 CN H H Me cf3 9.64 CN H H H Cl 9.65 CN H Me H Cl 9.66 CN H H Me Cl 9.67 CN H H H CN 9.68 CN H Me H CN 9.69 CN H H Me CN 9.70 CN H H H 〇CF2H 9.71 CN H Me H ocf2h 9.72 CN H H Me ocf2h 9.73 H Et H H cf2h 1H-NMR: δ [CDCI3] 1.35 (t, 3H), 2.90 (q, 2H), 3.82 (s, 3H), 6.40 (s, 1H), 6.63 (t, 1H), 7.70 (s, 1H), 7.98 (s, 1H), 8.75 (s, 1H) 9.74 H Et Me H cf2h 1H-NMR: δ [CDCIs] 1.35 (t, 3H), 2.43 (s, 3H), 2.85 (q, 2H), 3.80 (s, 3H), 6.40 (s, 1H), 6.61 (t, 1H), 7.60 (s, 1H), 8.60 (s, 1H) 9.75 H H H H c-Pr 1H-NMR: δ [CDCI3] 0.75 (m, 2H), 0.93 (m, 2H), 1.93 (m, 1H), 3.68 (s, 3H), 5.80 (s, 1H), 7.79 (d, 1H), 7.98 (s, 1H), 8.68 (d, 1H), 8.00 (s, 1H) 9.76 H Me H H c-Pr 1H-NMR: δ [CDCI3] 0.75 (m, 2H)t 0.92 (m, 2H), 1.92 (m, 1H), 2.60 (s, 3H), 3.70 (s, 3H), 5.80 (s, 1H), 7.60 (s, 1H), 7.95 (s, 1H), 8.70 (s, 1H) 9.77 ch2ch2ch2 H H cf3 1H-NMR: δ [CDCI3] 2.20 (m, 2H), 3.05 (t, 2H), 3.40 (t, 2H), 3.97 (s, 3H), 6.50 (s, 1H), 7.95 (s, 1H), 8.80 (s, 1H) -62- (59) 200533665 表10 :本發明之式(I)化合物其諸取代基及符號定義如下: Y = Y9 R2, R4, R6 = H R7 = Et
No. R1 R" R5 物理數據 9.78 Me H cf2h 1H-NMR: δ [CDCI3] 2,60 (s, 3H), 3.80 (s, 3H), 6.40 (s, 1H), 6.64 (tf 1H), 7.68 (s, 1H), 7.98 (s, 1H), 8.75 (s, 1H) 9.79 〇Me Me cf2h 1H-NMR: δ [CDCI3] 2.43 (s, 3H), 3.85 (s, 3H), 4.00 (s, 3H), 6.42 (s, 1H), 7.08 (s, 1H), 8.55 (s, 1H) 9.80 〇Me H cf2h 1H-NMR: δ [CDCI3] 1.45 (t, 3H), 4.00 (s, 3H), 4.15 (q, 2H), 6,35 (s, 1H), 6.62 (t, 1H), 7.15 (st 1H), 7.95 (s, 1H), 8.65 (s, 1H) 9.81 Et H cf2h 1H-NMR: δ [CDCI3] 1.40 (t, 3H), 1.55 (t, 3H), 2.90 (q, 2H), 4.30 (q, 2H), 6.42 (s, 1H), 6.80 (t, 1H), 7.64 (s, 1H), 8.00 (s, 1H), 8.78 (st 1H) 9.82 Me H cf3 'H-NMR: δ [CDCIa] 1.48 (t, 3H), 2.60 (s, 3H), 4.20 (q, 2H), 6.42 (s, 1H), 7.70 (s, 1H), 7.98 (s, 1H), 8.75 (s, 1H)
B .調合物實例 1 .殺蟲藥粉 殺蟲藥粉可藉著把10重量份之式(I )化合物與90 重量份作爲惰性物質之滑石混合在一起且用錘式粉碎機弄 得粉碎而製得。 2 .可分散粉末 可輕易分散到水中的可加水粉末可藉著把2 5重量份 式(I )化合物,64重量分作爲惰性物質之含高嶺土石 英,1 〇重量份木質素磺酸鉀以及1重量份作爲濕化劑及分 散劑之油醯甲基牛磺酸鈉混合在一起,且將混合物置於銷 栓盤粉碎機中碾磨而製得。 -63- 200533665 (60) 3 .可分散濃縮液 可輕易分散在水中的分散濃縮液可藉著把2 0重量份 的式(Ϊ )化.合物,6重量份之烷基苯酚聚二醇醚 (®Triton X 2 07 ) ,3重量份異十三烷醇聚二醇醚(8 ’ Ε Ο )及7 1重量份烷屬烴礦物油(沸點範圍例如在約2 5 5 4 到高2 7 7 °C )混合在一起,且於球磨機中將混合物磨到粒 φ 度低於5微米而製得。 4 .可乳化濃縮液 可乳化濃縮液可用1 5重量份之式(I )化合物,75重 量份作爲溶劑之環己酮及1 0重量份作爲乳化劑之環乙基 化壬基苯酣來製成。 5 ·水·可分散顆粒 φ 水-可分散顆粒可藉著混合: 7 5重量份式(I )化合物, 1 〇重量份木質素磺酸鈣, 5重量份硫酸月桂酯鈉, 3重量份聚乙醯醇及 7重量份高嶺土, 將混合物置於銷栓盤粉碎機中碾磨且於流體化床中噴 入水作爲造粒液體來把粉末製成顆粒。 水·可分散顆粒亦可藉著把如下混合物置於膠體碾磨 -64- 200533665 (61) 機中均質化且預粉碎,該混合物包括: 25重量份式(I)化合物, 5重量份2,2’-二萘甲烷- 6,6’-二磺酸鈉, 2重量份油酸甲基牛磺酸鈉, 1重量份聚乙烯醇, 1 7重量份碳酸鈣及 5 〇重量份水, 接著把混合物置於珠磨機中碾磨,且把所製成的懸浮 液置於噴乾塔中用單一物質噴嘴霧化及乾燥。 C.生物性實施例 1 .在有害植物出土前防治有害植物長出之除草作用 把單子葉及雙子葉有害植物的種籽置於扁硬盆器的砂 壤土中且上面用土覆蓋。將配方成可加水粉末或可乳化濃 縮液之本發明化合物製成水性懸浮液或乳液且以不同劑量 施藥於土壤表面上而其用藥量爲 600到800公升/公頃 (換算後)。施藥後,把花盆移到溫室中且保持在適合雜 草生長的良好狀態下。經過3到4週的測試期後與未經處 理之對照組比較,以視覺評估測試植物萌發後對於植物損 害或發芽損害的程度。在此,例如本發明實施例1.13, 1.14,1.25,1.26,1.39及1.46之化合物在以每公頃施用 1 〇 〇 〇克及低於1 〇 〇 〇克劑量之活性物質的情況下顯現出能 100%防治反枝莧(Amaranth us retroflexus),多花黑麥草 (Li lium multi fl o rum ),狗尾草(S e t a ι· i a v i r i d i s )及繁 -65- (62) (62)200533665 縷(S t e 11 a r i a m e d i a )。於同樣劑量下,例如本發明實施 例7.13,9.13及9.14之化合物亦展現出能100 %防治反枝 寛(Amaranth us retro flexus),狗尾草(Setaria viridis) 及繁縷(Stellaria media)。 2 ·在有害植物出土後的除草作用 把單子葉及雙子葉有害植物的種籽置於扁硬盆器的砂 壤土中,上面用土覆蓋且置於溫室中令其在良好的生長條 件下生長。在播種兩至三週後,測試植物係在長有三枚葉 子的狀態下施藥。將配方成可加水粉末或可乳化濃縮液之 本發明化合物以不同劑量噴灑在綠色植物的表面上而其用 藥量爲600到800公升/公頃(換算後)。然後把測試植 物置於溫室中在適合生長的良好狀態培育3到4週,然後 評估諸化合物的作用。在此,例如本發明實施例1 .4 6及 9 · 2 5之化合物在以每公頃施用1 〇 〇 〇克及低於1 〇 〇 〇克劑量 之活性物質的情況下顯現出能1 0 0 °/。防治反枝莧 (Amaranthus retroflexus ),里予燕麥(A vena fatus ),野 歐白芥(Sinapis a rvensis)及繁縷(stellaria media)。 -66-
Claims (1)
- (1) 200533665 十、申請專利範圍 1 . 一種如下之式(I )化合物、其N-氧化物或其鹽 類:R1其中該等基團及標記具有如下意義: Y爲一種選自如下Y1到Y9之基團:丫 5 丫 6 Y7 丫 8 丫 9 R1及R2彼此獨立且各別爲氫、鹵素、氰基、異氰酸 基、OH、COOR9、COR9、CH2OH、CH2SH、CH2NH2、 N02、CSNH2、C0NH2、 (CrCd)烷基、鹵素- (c]-c4) 院基、(C3-C6)環院基、(C]-C4)丨先氧基、鹵素-(c】_ -67- (2) (2)200533665 C4)院氧基、(C1-C2)院氧基-(CI-C2)院基、(C2-c4)烯基、(c2-c4)炔基、(c3-c4)烯氧基、(c3-c4) 炔氧基、(c】-c2 )烷硫基-(C丨-C2 )烷基、S(0)nR8、 (匕-(:2 )烷磺醯基-()烷基、胺基、()烷 胺基、(c丨-C 3 )烷羰胺基、(C】-C 4 )烷磺醯胺基或二-(CKC4 )烷胺基,或 R1 及 R2 共同形成 ch2_ch2-ch2,ch2-ch2-ch2-ch2 或 och2-ch2-ch2o ; R3及R4彼此獨立且各別爲氫、鹵素、氰基、(c!-C4)院基、鹵素-(C1-C4)院基、(C1-C4)院氧基或鹵 素-(Ci-C# )烷氧基; R5爲鹵素、氰基、(CrC^)烷基、鹵素- (CPC4) 院基、(C1-C4)院氧基、鹵素-(C1-C4)院氧基、鹵素-(CKC4 )烷硫基、(c3-c5)環烷基、鹵素-(c3-c5)環 烷基、SF5、S(0)nR8、(C2-C4)烯基或(C2-C4)炔基; R6爲氫、鹵素、氰基、(C^Q)院基、鹵素- (C】-C4)院基、(C1-C4)院氧基、鹵素-(Ci-C4)院氧基或 S(0)nR8 ; R7 爲(Ci-CU )烷基; R8爲氫、(C】-C4)烷基或鹵素- (C]-C4)烷基; R9爲氫或(CkQ )烷基; η爲0、1或2。 2 .如申請專利範圍第1項所述之化合物,其中 R1及R2彼此獨立且各別爲氫、鹵素、氰基、羥基、 -68- 200533665 (3) 甲醯基、乙烯基、(c】-c4)烷基、鹵素-(c】-c4)烷基或 (C】-C4)院氧基; 或者 R1及R2共同形成CH2CH2CH2 ;R3及R4彼此獨立且各別爲氫、鹵素、甲基或甲氧 且 Y 爲 Yl、Y2、Y3、Y6、Y7、Y8 或 Y9 之基團。 3 .如申請專利範圍第1項或第2項所述之化合物,其 R1爲氫、鹵素、羥基、氰基、三氟甲基、甲氧基、甲 基或乙基; R2爲氫、羥基、甲基、乙基、甲氧基或乙氧基; 或 R】及R2共同形成CH2-CH2-CH2,且 R3及R4彼此獨立且各別爲氫或甲基。 4.如申請專利範圍第1項或第2項所述之化合物,其 中: R5爲鹵素、氰基、鹵素烷基、鹵素- (C^ C2 )烷氧基或鹵素-()烷硫基。 5 .如申請專利範圍第1項或第2項所述之化合物,其 中112及116各爲氫且丫爲丫1、丫2、丫7、丫8或丫9之基 團。 6. —種除草組成物,其含有除草有效份量之至少一種 »69- 200533665 (4) 如申請專利範圍第1項到第5項中任一項之式(1 )化合 物。 7 ·如申請專利範圍第6項之除草組成物,其係與配方 助劑呈混合物。 8 · —種用於控制非所要植物的方法,該方法包含對該 植物或該非所要植物生長的地方施予有效份量之至少一種 如申請專利範圍第1項到第5項中任一項之式(I )化合 物或如申請專利範圍第6項或第7項之除草組成物。 9 · 一種如申請專利範圍第1項到第5項中任一項之式 (I )化合物或如申請專利範圍第6項或第7項之除草組 成物於控制非所要植物的用途。 1 〇 ·如申請轉利範圍第9項之用途,其中該式(Π化 合物係用來控制有用植物農作物理非所要的植物。 1 1 .如申請專利範圍第1 0項之用途,其中該有用植物 爲經轉基因處理的有用作物。 -70- 200533665 七、指定代表圖: (一) 、本案指定代表圖為:第()圖 (二) 、本代表圖之元件代表符號簡單說明:八、本案若有化學式時,請揭示最能顯示發明特徵的化學 式:_ 4 -
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AR099092A1 (es) | 2014-01-15 | 2016-06-29 | Monsanto Technology Llc | Métodos y composiciones para el control de malezas utilizando polinucleótidos epsps |
US11091770B2 (en) | 2014-04-01 | 2021-08-17 | Monsanto Technology Llc | Compositions and methods for controlling insect pests |
AU2015280252A1 (en) | 2014-06-23 | 2017-01-12 | Monsanto Technology Llc | Compositions and methods for regulating gene expression via RNA interference |
EP3161138A4 (en) | 2014-06-25 | 2017-12-06 | Monsanto Technology LLC | Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression |
CA2955842A1 (en) | 2014-07-29 | 2016-02-04 | Monsanto Technology Llc | Compositions and methods for controlling insect pests |
CN108064288B (zh) | 2015-01-22 | 2021-11-26 | 孟山都技术公司 | 用于控制叶甲属的组合物和方法 |
CN107750125A (zh) | 2015-06-02 | 2018-03-02 | 孟山都技术有限公司 | 用于将多核苷酸递送至植物中的组合物和方法 |
WO2016196782A1 (en) | 2015-06-03 | 2016-12-08 | Monsanto Technology Llc | Methods and compositions for introducing nucleic acids into plants |
WO2020169509A1 (de) | 2019-02-20 | 2020-08-27 | Bayer Aktiengesellschaft | Herbizid wirksame 4-(4-trifluormethyl-6-cycloropylpyrazolyl)pyrimidine |
Family Cites Families (5)
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AU725548B2 (en) * | 1997-03-11 | 2000-10-12 | E.I. Du Pont De Nemours And Company | Heteroaryl azole herbicides |
JPH10251255A (ja) * | 1997-03-14 | 1998-09-22 | Nissan Chem Ind Ltd | アジン誘導体 |
AU9809698A (en) | 1997-12-03 | 1999-06-16 | E.I. Du Pont De Nemours And Company | Substituted pyrimidine and pyridine herbicides |
DE10234875A1 (de) | 2002-07-25 | 2004-02-05 | Bayer Cropscience Gmbh | 4-Trifluormethylpyrazolyl substituierte Pyridine und Pyrimidine |
DE10234876A1 (de) | 2002-07-25 | 2004-02-05 | Bayer Cropscience Gmbh | 4-Trifluormethylpyrazolyl substituierte Pyridine und Pyrimidine |
-
2004
- 2004-03-10 DE DE102004011705A patent/DE102004011705A1/de not_active Withdrawn
-
2005
- 2005-02-26 WO PCT/EP2005/002049 patent/WO2005089551A1/de active Application Filing
- 2005-02-26 CN CNA2005800075717A patent/CN1929738A/zh active Pending
- 2005-02-26 EA EA200601659A patent/EA200601659A1/ru unknown
- 2005-02-26 EP EP05707643A patent/EP1725103A1/de not_active Withdrawn
- 2005-02-26 AU AU2005223983A patent/AU2005223983A1/en not_active Abandoned
- 2005-02-26 CA CA002559097A patent/CA2559097A1/en not_active Abandoned
- 2005-02-26 KR KR1020067018421A patent/KR20060132932A/ko not_active Application Discontinuation
- 2005-02-26 JP JP2007502228A patent/JP2007527879A/ja not_active Abandoned
- 2005-02-26 BR BRPI0507438-0A patent/BRPI0507438A/pt not_active IP Right Cessation
- 2005-03-08 TW TW094107020A patent/TW200533665A/zh unknown
- 2005-03-08 AR ARP050100887A patent/AR048749A1/es not_active Application Discontinuation
- 2005-03-10 US US11/077,110 patent/US7312180B2/en not_active Expired - Fee Related
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EP1725103A1 (de) | 2006-11-29 |
KR20060132932A (ko) | 2006-12-22 |
US7312180B2 (en) | 2007-12-25 |
JP2007527879A (ja) | 2007-10-04 |
EA200601659A1 (ru) | 2007-04-27 |
AR048749A1 (es) | 2006-05-24 |
US20050209106A1 (en) | 2005-09-22 |
CA2559097A1 (en) | 2005-09-29 |
BRPI0507438A (pt) | 2007-07-03 |
AU2005223983A1 (en) | 2005-09-29 |
CN1929738A (zh) | 2007-03-14 |
WO2005089551A1 (de) | 2005-09-29 |
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