TWI225046B - Phthalamide derivatives, or salt thereof agrohorticultural insecticide, and method for using the same - Google Patents

Phthalamide derivatives, or salt thereof agrohorticultural insecticide, and method for using the same Download PDF

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Publication number
TWI225046B
TWI225046B TW088120428A TW88120428A TWI225046B TW I225046 B TWI225046 B TW I225046B TW 088120428 A TW088120428 A TW 088120428A TW 88120428 A TW88120428 A TW 88120428A TW I225046 B TWI225046 B TW I225046B
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Taiwan
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alkyl
halo
group
halogen
alkoxy
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TW088120428A
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English (en)
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Masanori Tonishi
Hayami Nakao
Eiji Kohno
Tatsuki Nishida
Takashi Furuya
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Nihon Nohyaku Co Ltd
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    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/12Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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Description

u〇U46
CH2SCH3 , CH2SOCH3 ,或
Q 七,. ),2: CH2S02CH3 及R可相同或相異,表示氫原子,(V c6院基; 插入〜或 子· 5 可結合A1或R1形成5-至7-員環,其可 個相同或相異的氧原子、硫原子或氮原 可相同或相異表示鹵原子,硝基,_ c6烷基、 1¾ Q n _ 1 6 $兀基,C2-C6烯基,鹵c2-c6烯基,c2-c6炔 基 5 r^i # 國C^c6炔基,c3-C6環烷基,鹵c3-c6環烷基, 广ό院氧基,鹵(:】-(:6烷氧基,CVC6烷硫基,鹵Cr C6j:完硫基,C!-C6烷基亞磺醯基,鹵CrC6烷基亞磺醯 基’ C1-C6烷基磺醯基,鹵CrC6烷基磺醯基,或經取 代之苯氧基,其具有至少一個相同或相異之取代基 選自鹵(Vc6烷基,及1表示整數0至4;以及 或者,X可與苯基環之毗鄰碳原子共同形成一個 稠合環,且該稠合環含有至少一個相同或相異的取 代基選自鹵原子;以及 Y可相同或相異且表示鹵原子,c! -c6烷基,鹵 1225046 /、、申睛專利範圍 C】-C6烷基,羥C]_C6烷基,羥鹵Ci_c6烷基,(^乂烷 氧基鹵κ6烷基,(:^匕烷硫基鹵CVC6烷基,c3-c6 .嫌基,鹵cvc6烯基,c3-c6炔基,鹵c3-c6炔基,CV c6烷氧基,鹵(^匕烷氧基,CVC6烷氧基鹵CVC6烷 氧基’〔^(:6烷硫基鹵(VC6烷氧基,鹵CVC6烷氧基 _ G-C6烷氧基,鹵〇3-(:6烯氧基,cvc6烷硫基,鹵 C〗-C6烷硫基,鹵c]_c6烷氧基鹵Ci_C6烷硫基,鹵 C1 -C6烯硫基,c! -C6烷基亞磺醯基,鹵q -C6烷基亞 石黃醒基,(Vc6烷基磺醯基,鹵cvc6烷基磺醯基,單 q-C6烷基胺基、二(:厂匕烷基胺基(其中Cl-c6烷基可 相同或相異)、Cl_C6烷氧羰基,C3_C6環烷基,鹵c3-匸6環院基,二焼胺基擴醯基(其中CrG院基可 相同或相異),鹵C]-C6烷基磺醯氧基,二Cl-C6院胺 基羰基(其中Cl_C6烷基可相同或相異),三C^C6院基 砂烷基,鹵C^C:6烷基磺醯基胺基,苯基,經取代之 苯基,其含有至少一個相同或相異取代基選自下列 組群包含鹵原子、CrC6烷基、鹵C^c6烷基、CrC6 院氧基、鹵^-匕烷氧基、(VC6烷硫_、鹵 硫基、齒(VC6院基亞擴醯基及鹵(^〇6烷基磺醯 基’苯氧基’經取代之本氧基’其具有至少一個相 同或相異取代基選自下列組群包含鹵原子、Ci _C6火完 基、鹵C]-C6烷基、Ci-C6烷氧基、鹵c]‘c6^氧基、 &lt;^-〇6;1:兀硫基'鹵(:1-(:6:1:元硫基、鹵(:】、(^烷基亞磺醯 1225046 t、申請專利範圍 基及鹵CfC6院基磺醒基;苯基硫基,經取代之苯其 硫基,其具有至少一個相同或相異的取代基係 下列組群包含鹵原子 ' &lt;:丨-c6烷基、_ Γ W ^丨 L6 ί元基、 C】-C6烷氧基、鹵CVC6烷氧基、烷硫基、鹵c】· 烷硫基、鹵(V C6烷基亞磺醯基及鹵Γ w C L 6 /兀基石貝 醯基;經取代之苯基Cl-C6烷基,其具有至少一個相 同或相異之取代基選自鹵原子或羥基;經取代之苯鑛 基,其有至少一個相同或相異之取代基選自鹵原子或 C厂C6院基;經取代之苯基胺羰基,於其環上帶有至少 個相同或相異之取代基選自鹵原子;經取代之苯基_ N-G-C6烷基胺羰基,於其環上帶有至少一個取代基選 自鹵原子,吡啶基氧基;經取代之吡啶基氧基,其含 有至少一個相同或相異的取代基選自下列組群包含 鹵原子、cvc6烷基、鹵cvc6烷基、Cl_C6烷氧基、 m表示1至5之整數;及 鹵〔厂匕烷氧基、Ci_c6烷硫基、鹵烷硫基、鹵 C]-C6;(:完基亞磺醯基及鹵Ci_C6烷基磺醯基;吡啶基硫 基’經取代之吡啶基硫基,其含有至少一個相同或 相異的取代基選自下列組群包含鹵原子、C! - C6烷 基、齒1-(:6烷基、CrC6烷氧基、鹵(^-(:6烷氧基、 C】-C6院硫基、鹵c】_c6烷硫基、鹵烷基亞磺醯 基及鹵CrC6烷基磺醯基;或c(N = 〇- cvc6烷基)經 取代之苯基’其具有至少一個相同或相異之取代基 選自鹵原子;及 1225046 六、申請專利範圍 γ可與苯基環上毗鄰碳原子共同接合形成〜_ _ 合環,及該稠合環可含有至少一個相同或相異的取 代基選自鹵原子;以及 η表示0至2之整數。 2 ·如申請專利範圍第1項之酞醯胺衍生物或其鹽,其 中Α1表示CVh伸烷基; R1表示氫原子,(VC6烷基,鹵(VC6烷基,c r π6 烯基,C3-C6炔基,CVCJl烷基,c】-c6烷硫基, c6烷氧基cvc6烷基,CVG烷硫基(VC6烷基,c Γ 1 - 烷基羰基,單(VC6烷基胺基羰基,二院基 胺基羰基(其中h - C6烷基可相同或相異),單c _ Γ 1 16 烷基胺基硫羰基,二(^-(:6烷基胺基硫羰基(其中C1_ C6烷基可相同或相異),C】_C6烷基羰基Ci—c6烷基, C】-C6烷氧亞胺基(:丨&lt;6烷基,Cl-C6烷氧羰基(Vc6j^ 基’單c】-C6《兀基te:基叛基c】-C6院基或二c^-c^院基 胺基羰基G-C6烷基(其中c]_c6烷基可相同或相 異)·, R2及R3可相同或相異表示氫原子或C]_C6烷基; X可相同或相異表示鹵原子,硝基,Ci_C6烷基, 鹵CVC6院基,Crh烷氧基,鹵(:]-(:6烷氧基, 院硫基、鹵CVC6烷硫基、c]_c6烷基亞磺醯基,鹵 C^C:6烷基亞磺醯基、(^―匕烷基磺醯基或鹵 基feiS®基,及1表示〇至4之整數;且 1225046
六、申請專利範圍 或者,X可與苯基環之毗鄰碳原子共同接合形成 一個稠合環,且該稠合環可含有至少一個相同或相 異取代基選自鹵原子; Y可相同或相異及表示鹵原子,C】-C6烷基,鹵 C^c6烷基,(^-匕烷氧基鹵(VC6烷基,cvc6烷氧 基,鹵cvc6烷氧基,鹵(^&lt;6烷氧基鹵(VC6烷氧 基,CrC6烷硫基,鹵(^-(:6烷硫基,(^-(^烷基亞磺 醯基、鹵C^C:6烷基亞磺醯基,烷基磺醯基、齒 q-C6烷基磺醯基;經取代之苯基,其含有至少—個 相同或相異的取代基選自下列組群包含鹵原子、 c6烷基、鹵c]-c6烷基、c]-c6烷氧基、鹵〇^(:6院氧 基、院硫基、鹵院硫基、鹵C]-C6焼基亞 磺醯基及鹵C^C:6烷基磺醯基;經取代之苯氧.基,其 含有至少一個相同或相異取代基選自下列組群包含 鹵原子、C! - C6院基、鹵C! - C6院基、C】-c6院氧基、 鹵(:】-(:6烷氧基、cvc6烷硫基、鹵CVC6烷硫基、齒 h-C6烷基亞磺醯基及鹵C^C:6烷基磺醯基;或經取代 之吡啶基氧基,其含有至少一個相同或相異的取α 基選自下列組群包含鹵原子、C! - C6院基、鹵c】-c6 j:完 基、CVC6院氧基、鹵C】-C6院氧基、CVCe院硫基、 鹵C ] - C6院硫基、鹵C】-C6院基亞磺醯基及鹵c j - c 6 j:完 基磺醯基;及m表示1至5之整數;以及 γ可與苯環上毗鄰碳原子共同形成一個稠合環, 1225046 六、申請專利範圍 且該稠合環含有至少一個相同或相異的取代基選自 鹵原子;以及 η表示〇至2之整數。 3 . —種農園藝殺蟲劑,其特徵在於含有作爲其活性成 VC-N-R2 (Υ)η II ο 其中Α1表示0丨-(:6伸烷基;經取代之(:丨-匕伸烷 基,其含有至少一個相同或相異的取代基係選自下 列組群包含鹵原子,鹵烷基,烷氧基, 鹵C^-C^院氧基’ CVC^院硫基,鹵院硫基, Κ6烷基亞磺醯基,鹵(VC6烷基亞磺醯基,(VG 烷基磺醯基,鹵烷基磺醯基,羥(^-(:6烷基, 苯基,及CVC6烷硫基(VC6烷基,以及 R1表示氫原子,毓基,(VC6烷基,鹵Ci-C6烷 基,c3-c6烯基,鹵c3-c6烯基,c3-c6炔基,鹵c3-c6 炔基,C3-C6環烷基,鹵C3-C6環烷基,CVC6烷硫 基,鹵Ci-G烷硫基,羥CVC6烷基,(^(:6烷氧基 (VC6烷基,Κ6烷硫基cvc6烷基,單(VC6烷胺 基(VC6烷基,二G-C6烷胺基(VC6烷基(其中cvc6 烷基可相同或相異)’ C1 _c6烷基羰基’鹵q -C6烷基 分之一種如下通式(I)表示之酞醯胺衍生物或其鹽, (0)。 001 0 Α1- “1
1225046 六、申請專利範圍
羰基,(Vc6烷硫基羰基,Cl_c6烷氧羰基,單^ c 烷基胺基羰基,二C】-C:6烷基胺基羰基(其中c丨-c6院 基可相同或相異),單c丨-c6烷基胺基硫羰基,二c] _ C6烷基胺基硫羰基(其中c! -C6烷基可相同或相異), 丨元基鑛基Ci-C6院基,院氧亞胺基 烷基,CVC:6烷氧羰基CVC6烷基,鹵〇]&lt;6烷羰氧基 c]-c6烷基,單(VC6烷基胺基羰基(VC6烷基,二 C]-C6烷基胺基羰基c】-C6烷基(其中(:^(:6烷基可相 同或相異),苯基,經取代之苯基,其具有至少一個 相同或相異取代基係選自下列組群包含鹵原子,氰 基’硝基’ C ] - C6院基,鹵C】-C6院基,C丨-C 6院氧 基’鹵C!-C6院氧基,院硫基,鹵完硫 基’ c!-C6烷基亞磺醯基,鹵G - c6烷基亞磺醯基, (VC6烷基磺醯基,鹵cvc6烷基磺醯基,單 烷胺基,二(VC6烷胺基(其中cvc6烷基可相同或 相異)’及C ] - C 6院氧羰基;苯基C! - C 6院基,經取代 之苯基C】-C 6院基,於其環上有至少一個相同或相異 取代基選自下列組群包含鹵原子、氰基、硝基、C i、 c6烷基、鹵CVC6烷基、CVC6烷氧基、鹵(:^(:6烷氧 基、C! -C6烷硫基、鹵c! -C6烷硫基、c, -C6烷基亞_ 醯基、鹵c^c6烷基亞磺醯基、Cl-C6烷基磺醯基、 鹵Cr C6烷基磺醯基 '單c】-C6烷基胺基、二c!-c6 烷基胺基(其中C i - C6烷基可相同或相異)、及C, - C -10-
1225046 t、申請專利範圍 院氧線基;苯基羰基,經取代之苯基鑛基,其具有 至少一個相同或相異的取代基選自下列組群包含鹵 原子、氰基、硝基、C! -c6烷基、鹵C! -C6烷基、(V C6焼氧基、鹵C】-C6院氧基、c】-C6焼硫基、鹵CVC6 院硫基、C! - C6烷基亞磺醯基、鹵c] - c6烷基亞磺醯 基、cvc6烷基磺醯基 '鹵Cl_c6烷基磺醯基、單Cl-C6烷基胺基、二C】-C6烷基胺基(其中c]_c6烷基可相 同或相異)、及CrG烷氧羰基;苯基硫基;經取代 之苯基硫基,其具有至少一個相同或相異取代基選 自下列組群包含鹵原子,氰基,硝基,C^c6烷基, 鹵CVC6烷基’ CVC6烷氧基,鹵Cl_c6烷氧基,(VC6 院硫基’鹵C!-C6院硫基,院基亞擴醯基,齒 cvc6烷基亞磺醯基,cvc6烷基磺醯基,鹵cvc6烷 基磺醯基,單(:厂匕烷基胺基,二。-(^烷基胺基(其 中CrQ烷基可相同或相異),及Cl-C6烷氧羰基;吡 啶基,噻唑基,噻二唑基,苯并噻唑基,經取代之 嘧啶基,具有至少一個相同或相異之取代基選自C】-c6烷基;或 或者,R 1可結合A1形成
to
&gt; 1 1 &gt; 1225046 申睛專利範圍
CH2SCH3 , CH2SOCH3 , Q-: _ ιΟ CH2S02CH3 ; R及R3可相同或相異,表示氫原子,Ci_C6烷基; 或 或者’ R2可結合A1或R]形成5-至7-員環,其可插 入一或一個相同或相異的氧原子、硫原子或氮原子; 、X可相同或相異表示鹵原子,硝基,烷基、 鹵Cl C6蜣基,CVc6烯基,鹵c2-c6烯基,C2-C6炔 基 ® C2_C6炔基,c3-c6環烷基,鹵c3-c6環烷基, 氧基,鹵(^匕烷氧基,烷硫基,鹵c]_ C6烷硫基,Cl-C6烷基亞磺醯基,鹵CrC6烷基亞磺醯 基,C广C6烷基磺醯基,鹵c】-C6烷基磺醯基,或經取 代之本氧基’其有至少一個相同或相異之取代基選 自鹵c^c:6烷基,及丨表示整數〇至4 ;以及 或者’ X可與苯基環之毗鄰碳原子共同形成一個 稠口 ,且s亥稠合環含有至少一個相同或相異的取 代基選自鹵原子;以及 Y可相同或相異且表示鹵原子,Ci_C6院基,齒 c,-c6烷基,羥Ci-c6烷基,羥鹵C「C6烷基’ 烷 1 1225046 申請專利範圍 氧基鹵cvc6院基,(^-(:6烷硫基鹵烷基,c3-c6 烯基,鹵C3-C6烯基,CVC6炔基,鹵C3_C6炔基, C6院氧基’鹵(^-匕烷氧基,Cl-C6烷氧基鹵CrCdt 與基’(^-(1!6丨兀硫基鹵C】-C6院氧基,鹵焼氧基 齒Ci-Ce院氧基’鹵C3-C6烯氧基,(^-(:6烷硫基,鹵 C1-C6 fet硫基’鹵c! -C6烷氧基鹵c! -c6烷硫基,鹵 Ci-C6^硫基’ c】-C6丨元基亞礦釀基,鹵C j - C 6院某亞 石貝醯基’ G-C:6烷基磺醯基,鹵CrC6烷基磺醯基,單 C〗-C6烷基胺基、二CVC6烷基胺基(其中c】-c6院基可 相同或相異)、c】-C6燒氧羯基,C3-C6環燒基,鹵c3_ G環烷基’二c]-C6烷胺基磺醯基(其中Ci_c6烷基可 相同或相異),鹵cvc6烷基磺醯氧基,二c]_c6院胺 基羰基(其中C! -C6烷基可相同或相異),三c; -C6烷基 砂烷基,幽C, -c6烷基磺醯基胺基,苯基,經取代之 本基,其含有至少一個相同或相異取代基選自下列 組群包含鹵原子、(VC6烷基、鹵(VC6烷基、cvc6 院氧基、鹵(^(:6烷氧基、CVC6烷硫基、鹵(^-“烷 硫基、鹵烷基亞磺醯基及鹵烷基磺醯 基;苯氧基,經取代之苯氧基,其有至少一個相同 或相異取代基選自下列組群包含鹵原子、C! - C6烷 基、鹵c^c6烷基、CVC6烷氧基、鹵1-(:6烷氧基、 C^c6烷硫基、鹵Cl-C6烷硫基、鹵(VC6烷基亞磺醯 基及鹵C! -c6烷基磺醯基;苯基硫基,經取代之苯基 1225046 ^、申請專利範圍 硫基,其含有至少一個相同或相異的取代基係選自 下列組群包含鹵原子、eve,烷基、鹵Ci-C6院基、 cvc6烷氧基、鹵(VC6烷氧基、Ci_c6烷硫基、鹵c]_ 匸6丨兀硫基、齒c】-C6院基亞磺if基及鹵院基石黃 醯基’經取代之本基C ] - C6院基,其有至少一個相同 或相異之取代基選自鹵原子或經基,經取代之苯鑛 基,其有至少一個相同或相異之取代基選自鹵原子或 C】-C6烷基,經取代之苯基胺羰基,其於環上帶有至少 個相同或相異之取代基選自鹵原子,經取代之苯基_ N - Cl - C6院基胺羰基,其於環上帶有至少一個取代基選 自鹵原子,吡啶基氧基,經取代之吡啶基氧基,其含 有至少一個相同或相異的取代基選自下列組群包含 鹵原子、(VC6烷基、鹵CVC6烷基、(:】-(:6烷氧基、 _ ^&lt;6烷氧基、c^C6烷硫基、鹵(VC6烷硫基、鹵 CrC6院基亞磺醯基及鹵Cl_c6烷基磺醯基;吡啶基硫 基’經取代之吡啶基硫基,其含有至少一個相同或 #異的取代基選自下列組群包含鹵原子、Cl _C6烷 基 '鹵烷基、Ci-C6烷氧基、鹵1-(:6烷氧基、 C】-G燒硫基、鹵烷硫基 '鹵cvc6烷基亞磺醯 基及齒C「C6烷基磺醯基;或C(N = 0- (VC6烷基)經 取代苯基,其有至少一個相同或相異之取代基選 白鹵原子;及m表不1至5之整數,及 Y可與苯基環上毗鄰碳原子共同接合形成一個稠 1225046 六、申請專利範圍 合環’及該稠合環可含有至少一個相同或相異的取 代基選自鹵原子;以及 η表示〇至2之整數。 4 .如申請專利範圍第3項之農園藝殺蟲劑,其中Al表 示C6伸烷基; R1表示氫原子,CVC6烷基,鹵C】-C6烷基,c3-c6 燒基’ C3-C6炔基,(:346環烷基,C]-C6烷硫基, C6燒氧基(VC6烷基,cvc6烷硫基cvc6烷基,Cl_c6 院基鑛基,單c]_c6烷胺基羰基,二^-(^烷胺基羰 基(其中C^C:6烷基可相同或相異),單c】-c6烷胺基 硫缓基’二(:厂(:6烷基胺基硫羰基(其中(Vc6院基可 相同或相異),(^(:6烷基羰基Ci-C6烷基,Crh烷氧 亞月女基C]-C6;t兀基’(^-(^6火元氧羯基Ci_C6院基,單 CI-C6院基胺基羰基Cl-c6烷基或二Ci_c6烷基胺基羰 基C^C:6烷基(其中CrG烷基可相同或相異); R2及R3可相同或相異表示氫原子或Cl-C6烷基; X可相同或相異表示鹵原子,硝基,c] - c6院基, 齒C^C6院基,Ci_C6烷氧基,鹵c】-c6烷氧基,Cl-C6 丈元硫基、鹵。-(:6烷硫基、c^c6烷基亞磺醯基,鹵 h-C6院基亞磺醯基、。—(^烷基磺醯基或鹵1-(:6烷 基擴醯基;及丨表示0至4之整數;以及 或者’ X可與苯基環之毗鄰碳原子共同接合形成 〜個稠合環’且該稠合環可含有至少一個相同或相 1225046
、申請專利範圍 異取代基選自鹵原子; Y可相同或相異及表示鹵原子,G - c6烷基,鹵 c!-c6烷基,(^(:6烷氧基鹵(VC6烷基,CVC6烷氧 基’鹵C!-C6烷氧基,鹵cvc6烷氧基鹵(^-(^烷氧 基’ 烷硫基,鹵(^_〇6烷硫基,(^匕烷基亞磺 廳基、鹵烷基亞磺醯基,烷基磺醯基、鹵 C ! - C6烷基磺醯基,經取代之苯基,其含有至少一個 相同或相異的取代基選自下列組群包含鹵原子、C1 _ c6烷基、鹵(vc6烷基、cvg烷氧基、鹵&lt;vc6烷氧 基、cvc6烷硫基、鹵cvg烷硫基、鹵cvc6烷基亞 磺醯基及鹵烷基磺醯基;經取代之苯氧基,其 含有至少一個相同或相異取代基選自下列組群包含 鹵原子、cvc6烷基、鹵cvc6烷基、(^-(:6烷氧基、 國C ! - C 6院氧基、C ! - C 6焼硫基、鹵C i - C 6院硫基、鹵
Cj-C6烷基亞磺醯基及鹵CrC6烷基磺醯基;或經取代 之吡啶基氧基,其含有至少一個相同或相異的取代 基選自下列組群包含鹵原子、CrC6烷基、鹵Cl-C6;^ 基、(VC6烷氧基、鹵(:】-(:6烷氧基、(vc6烷硫基、 鹵CVC6烷硫基、鹵CVC6烷基亞磺醯基及鹵 基磺醯基;及m表示1至5之整數;以及 γ可與苯環上毗鄰碳原子共同形成一個稠合環, 且該稠合環含有至少一個相同或相異的取代基選自 鹵原子;以及 η表示0至2之整數。
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