TW201238485A - Fluorine-containing quinazoline-derived pest-control agent for use in agriculture and horticulture - Google Patents

Abstract

The following novel fluorine-containing quinazoline derivative is useful as a pest-control agent. Formula (I-1) Formula (I-2) (In the formulas, R1 represents phenyl or the like; and R2 represents a hydrogen atom, methyl, or the like.)

Description

201238485 六、發明說明： 【發明所屬之技術領域】 本發明係提供一種有害生物防治劑，特別係適用爲農 園藝用有害生物防治劑之新穎的含氟喹唑啉衍生物。 【先前技術】 先前之各種具有有害生物防治活性之胺基嘧啶衍生物 已屬周知。例如參照下述之先前技術文獻。 然而近年來因對於有害生物防治劑之抗藥性日漸發展 ，藥劑效力降低正成爲相當嚴重的問題。因此，仍必須開 發新穎的化合物以取代先前具有有害生物防治活性之胺基 嘧啶化合物。本發明之含氟喹唑咐衍生物係新穎的化合物 ，亦未知具有農園藝之有害生物防治活性。 先前技術文件 專利文件 專利文件1 :特開平5-23 003 6號公報 專利文件2 :特開平6-25 1 87號公報 專利文件3 :特開平8- 1 1 3 5 64號公報 專利文件4 :特開平1 1 -3 0226 1號公報 專利文件5 :特開平1 1 -1 5 8 1 6 1號公報 專利文件6 :特開2006-8542號公報 專利文件 7: W0200 7/135029 專利文件 8: W02007/46809 201238485 專利文件 9: WO2006/47397 【發明內容】 [發明欲解決之課題] 本發明之課題係提供新穎的含氟唼唑啉衍生物、其製 法及以其爲有效成分之農園藝用有害生物防治劑。 [解決課題之手段] 本發明團隊爲解決前述課題專心檢討後，發現新穎化 合物種之含氟喹唑啉衍生物具有顯著的農園藝殺菌、殺蟎 、殺線蟲以及殺菌活性之事實，且依據該事實完成本發明 〇 亦即，本發明係如下。 第一發明係有關一種以下述式[1-1]以及[1-2]所示之含 氟喹唑啉衍生物： 【化1】201238485 VI. Description of the Invention: [Technical Field of the Invention] The present invention provides a pest control agent, particularly a novel fluorine-containing quinazoline derivative which is suitable as a pest control agent for agricultural and horticultural use. [Prior Art] A variety of prior aminopyrimidine derivatives having pesticidal activity have been known. For example, refer to the prior art documents below. However, in recent years, as the resistance to pest control agents has developed, the reduction in the efficacy of pharmaceutical agents has become a serious problem. Therefore, it is still necessary to develop novel compounds to replace the aminopyrimidine compounds previously having pesticidal activity. The fluorine-containing quinazolium derivative of the present invention is a novel compound, and it is not known to have pest control activity for agriculture and horticulture. PRIOR ART DOCUMENT Patent Document Patent Document 1: Japanese Patent Laid-Open No. Hei 5-23 003 No. 6 Patent Document 2: Japanese Patent Application Laid-Open No. Hei No. Hei 6-25 No. 1 87 Patent Document 3: Japanese Patent Laid-Open No. Hei 8- 1 1 3 5 No. 64 Patent Document 4: Japanese Patent Laid-Open No. Hei 1 1 - 3 0226 No. 1 Patent Document 5: Japanese Patent Laid-Open Publication No. Hei No. Hei No. Hei No. 2006-8542 Patent Document No. 7: W0200 7/135029 Patent Document 8: W02007/46809 201238485 Patent Document 9: WO2006/47397 [Problem to be Solved by the Invention] The subject of the present invention is to provide a novel fluorine-containing oxazoline derivative, a process for the preparation thereof, and agricultural and horticultural use thereof as an active ingredient. Pest control agent. [Means for Solving the Problem] After focusing on the above-mentioned problems, the present inventors discovered that the novel compound species of the fluorine-containing quinazoline derivative has significant agricultural and horticultural bactericidal, acaricidal, nematicidal and bactericidal activities, and The present invention has been accomplished in fact, that is, the present invention is as follows. The first invention relates to a fluoroquinazoline derivative represented by the following formulas [1-1] and [1-2]:

[式中’ R1係由下述（a)〜（d)選出： a)由苯基、苯甲基、噁唑基、異噁唑基、呋喃基、 苯并呋喃基、異苯并呋喃基、二氫苯并呋喃基、噻唑基、 異噻唑基、萘基、嘧啶基、吡嗪基、喹喔啉基、唾唑啉基 -6- 201238485 、吡啶基、喹啉基、異喹啉基、苯并噻唑基、苯并異噻唑 基、吡咯基、吲哚基、異吲哚基、苯并噁唑基、苯并異噁 唑基、噻吩基、苯并噻吩基、咪唑基、苯并咪唑基、吡唑 基、吡啶酮基所成之群選出，且視情況而爲含有〇〜3個雜 原子之單環式或雙環式之環， b) 碳原子數1〜6之直鏈狀或分枝狀之烷基、碳原子 數2〜8之直鏈狀或分枝狀之烯基、碳原子數2〜8之直鏈狀 或分枝狀之炔基、碳原子數3〜8之環烷基或碳原子數3〜8 之環烯基， c) — SiR5R6R7(R5、R6、R7係碳原子數1〜6之直鏈狀 或分枝狀之烷基、以1個鹵素原子取代之碳原子數1〜3之 直鏈狀或分枝狀之鹵烷基、以1個氰基取代之碳原子數 1~3之直鏈狀或分枝狀之氰基烷基、以及苯基，且其中二 者或全部可爲相同之取代基或全部相異之取代基）， d) 氫原子， 且在（a)或（b)之情況時，R1係可以下述所取代： _C(0)0R、一 C(〇)R、一 R、一 OR、一 SR、一 S02R、 —0C(0)R、一 C(0)NHR' -C(0)NR2、一NHS02R、 —NRSO2R ' 一 NHR、一 NR2 ' — NHC(0)R、一 NRC(0)R 、一NHC(0)0R、NRC(0)0R、一N(0R)C(0)0R、 —NHS02R、一 NRS02R、一 SO2NHR、_ S02NR2(此處之 R 係代表碳原子數1〜8之直鏈狀或分枝狀之烷基、碳原子數 2〜8之直鏈狀或分枝狀之烯基、碳原子數2〜8之直鏈狀或 分枝狀之炔基或碳原子數3〜8之環烷基）、一 SiR5R6R7 201238485 、一OSiR5R6R7 (R5、R6、R7係碳原子數1〜6之直鏈狀或 分枝狀之烷基、以1個鹵素原子取代之碳原子數1〜3之直 鏈狀或分枝狀之鹵烷基、以1個氰基取代之碳原子數1〜3 之直鏈狀或分枝狀之氰基烷基、以及苯基’且其中二者或 全部可爲相同之取代基或全部相異之取代基）、鹵烷基（以 相同或相異之1〜9個鹵素原子取代之碳原子數1~4之直鏈 狀或分枝狀之烷基）、鹵烯基（以相同或相異之1〜4個鹵素 原子取代之碳原子數2〜6之直鏈狀或分枝狀之烯基）、鹵 烷氧基（以相同或相異之1~9個鹵素原子取代之碳原子數 1〜4之直鏈狀或分枝狀之烷氧基）、醯基烷氧基（以（碳原子 數1〜8之直鏈狀或分枝狀之脂肪族烴基）一 CO—表示之經 1個或2個醯基取代之碳原子數1〜3之直鏈狀或分枝狀之 烷氧基）、醯氧基烷基（以（碳原子數1〜8之直鏈狀或分枝 狀之脂肪族烴基）_ CO— Ο—表示之經1個或2個醯基氧 基取代之碳原子數1~3之直鏈狀或分枝狀之烷基）、烷基 磺酸基烷基（以碳原子數1〜8之直鏈狀或分枝狀之經1個 或2個烷基磺酸基取代之碳原子數1~3之直鏈狀或分枝狀 之烷基）、矽烷氧基烷基（以（一〇SiR5R6R7 (R5、R6、R7係 碳原子數之直鏈狀或分枝狀之烷基、以1個鹵素原子 取代之碳原子數1〜3之直鏈狀或分枝狀之鹵烷基、以1個 氰基取代之碳原子數1〜3之直鏈狀或分枝狀之氰基烷基、 以及苯基，且其中二者或全部可爲相同之取代基或全部相 異之取代基）取代之碳原子數1~3之直鏈狀或分枝狀之烷 基）、羥基烷基（以1個或2個羥基取代之碳原子數1~3之 -8- 201238485 直鏈狀或分枝狀之烷基）、烷氧基烷基（以碳原子數1〜8之 直鏈狀或分枝狀之1個或2個烷氧基取代之碳原子數1〜3 之直鏈狀或分枝狀之烷基）、鹵烷氧基烷基（以相同或相異 之1〜9個齒素原子取代之碳原子數1〜4之直鏈狀或分枝狀 的經1個或2個鹵烷氧基取代之碳原子數1~3之直鏈狀或 分枝狀之烷基）、烷基硫代烷基（以碳原子數1〜8之直鏈狀 或分枝狀之經1個或2個烷基硫代基取代之碳原子數1〜3 之直鏈狀或分枝狀之烷基）、二烷氧基乙縮醛基（以碳原子 數1〜8之直鏈狀或分枝狀之烷氧基經於2個甲基位置進行 取代之二烷氧基甲基）、烷氧基烷氧基（以碳原子數1〜8之 直鏈狀或分枝狀的經1個或2個烷氧基取代之碳原子數 1〜3之直鏈狀或分枝狀之烷氧基）、氰基烷基（以1個或2 個氰基取代之碳原子數1〜3之直鏈狀或分枝狀之烷基）、 鹵素、氰基、硝基、胺基、羥基、戊鹵磺醯基、苯甲基、 苯甲基氧基、苯基、苯氧基、吡啶基、噁唑基、呋喃基、 噻唑基、萘基、嘧啶基、噻吩基、苯并噻唑基、苯并噁唑 基、苯并二噁茂基、亞胺基、甲醯基（一CHO)、羧基（一 COOH)、甲醯胺基（一NHCHO)、環狀醚以及環狀胺， R2 表示氫原子、一R、一OR、一C(0)0R、 一 C(0)NHR、一 CONR2(此處之R係碳原子數1〜8之直鏈 狀或分枝狀之烷基、碳原子數2〜8之直鏈狀或分枝狀之烯 基、碳原子數2〜8之直鏈狀或分枝狀之炔基或碳原子數 3〜8之環烷基）、羥基烷基（以1個或2個羥基取代之碳原 子數1〜3之直鏈狀或分枝狀之烷基）、烷氧基烷基（以碳原 -9- 201238485 子數1~8之直鏈狀或分枝狀之經〗個或2個烷氧基取代之 碳原子數1〜3之直鏈狀或分枝狀之烷基）、鹵烷氧基烷基（ 以相同或相異之1〜9個鹵素原子取代之碳原子數之直 鏈狀或分枝狀的經1個或2個鹵烷氧基取代之碳原子數 1〜3之直鏈狀或分枝狀之烷基）、苯基、雜芳基、鹵素、 氛基、鹵烷基（以相同或相異之1〜9個鹵素原子取代之碳 原子數1〜4之直鏈狀或分枝狀的烷基）、鹵烷氧基（以相同 或相異之1〜9個鹵素原子取代之碳原子數1〜4之直鏈狀或 分枝狀的烷氧基）。] 另外，第二發明係以式[I]所示之含氟喹唑啉衍生物 之製造方法。 進而，第三發明係含有1種或2種以上以式[I]所示 之含氟唾唑啉衍生物爲有效成分之有害生物防治劑。 [發明的效果] 本發明之以式[I]所示之新穎的含氟喹唑啉衍生物， 對於有害生物，特別對於農園藝的有害生物，具有優異的 防治效果。 【實施方式】 以下針對本發明詳細說明。 於本發明上述之含氟喹唑啉衍生物中’除了以式Π] 所示之含氟喹唑啉衍生物之外，亦包含該衍生物之鹽（鈉 鹽、鉀鹽、鎂鹽、鈣鹽、鋁鹽等）、水和物、溶劑合物、 -10- 201238485 結晶多型之物質。進而本發明化合物中存在之所有可能的 立體異構物或光學異構物，以及以任意比率包含2種類以 上之其異構物之混合物，亦包含於本發明化合物（以式[I] 所示之含氟喹唑啉衍生物）之範圍內。 上述之以化合物[I]表示之各種取代基係如下所述。 R1爲選自下述（a)〜（d)之任一種取代基： a) 構成由苯基、苯甲基、噁唑基、異噁唑基、呋喃 基、苯并呋喃基、異苯并呋喃基、二氫苯并呋喃基、噻唑 基、異噻唑基、萘基、嘧啶基、吡嗪基、喹喔啉基、唾唑 啉基、吡啶基、喹啉基、異唾啉基、苯并噻唑基、苯并異 唾唑基、吡咯基、吲哚基、異吲哚基、苯并噁唑基、苯并 異噁唑基、噻吩基、苯并噻吩基、咪唑基、苯并咪唑基、 吡唑基、吡啶酮基所成之群選出，且視情況而爲含有0〜3 個雜原子之單環式或雙環式之環之任意環原子（碳原子或 雜原子）作爲鍵結鍵之基》 i b) 碳原子數1〜6之直鏈狀或分枝狀之烷基、碳原子 數2〜8之直鏈狀或分枝狀之烯基、碳原子數2〜8之直鏈狀 或分枝狀之炔基、碳原子數3〜8之環烷基或碳原子數3〜8 之環烯基》 c) - SiR5R6R7(R5、R6、R7係碳原子數卜6之直鏈狀 或分枝狀之烷基、以1個鹵素原子取代之碳原子數1〜3之 直鏈狀或分枝狀之鹵烷基、以1個氰基取代之碳原子數 1〜3之直鏈狀或分枝狀之氰基烷基、以及苯基，且其中二 者或全部可爲相同之取代基或全部相異之取代基）。 -11 - 201238485 d)氫原子。 在（a)或（b)之情況時，R1係可以下述所取代：一 C(Ο)ΟR ' _ C(0)R ' — R、一 OR、一 SR、一 SΟ2R ' — 0C(0)R、一 C(0)NHR、一 C(0)NR2、一 NHS02R、— NRS02R ' — NHR ' —NR2、一NHC(0)R'—NRC(0)R、— NHC(0)0R、一 NRC(0)0R、一 N(0R)C(0)0R、一 NHSO2R 、一NRS02R、一 S02NHR、一 S02NR2(此處之 R 係代表碳 原子數1〜8之直鏈狀或分枝狀之烷基、碳原子數2〜8之直 鏈狀或分枝狀之烯基、碳原子數2~8之直鏈狀或分枝狀之 炔基或碳原子數 3〜8之環烷基）、一3丨尺5116尺7、一 OSiR5R6R7 (R5、R6、RM系碳原子數卜6之直鏈狀或分枝 狀之烷基、以1個鹵素原子取代之碳原子數1~3之直鏈狀 或分枝狀之鹵烷基、以1個氰基取代之碳原子數1〜3之直 鏈狀或分枝狀之氰基烷基、以及苯基，且其中二者或全部 可爲相同之取代基或全部相異之取代基）、鹵烷基（以相同 或相異之1〜9個鹵素原子取代之碳原子數1~4之直鏈狀或 分枝狀之烷基）、鹵烯基（以相同或相異之1〜4個鹵素原子 取代之碳原子數2〜6之直鏈狀或分枝狀之烯基）、鹵烷氧 基（以相同或相異之1〜9個鹵素原子取代之碳原子數1〜4 之直鏈狀或分枝狀之烷氧基）、醯基烷氧基（以（碳原子數 1〜8之直鏈狀或分枝狀之脂肪族烴基）一CO—表示之經1 個或2個醯基取代之碳原子數1~3之直鏈狀或分枝狀之烷 氧基）、醯氧基烷基（以（碳原子數1~8之直鏈狀或分枝狀 之脂肪族烴基）一 CO— Ο—表示之經1個或2個醯基氧基 -12- 201238485 取代之碳原子數1〜3之直鏈狀或分枝狀之烷基）、烷基磺 酸基烷基（以碳原子數1〜8之直鏈狀或分枝狀之經1個或 2個烷基磺酸基取代之碳原子數1~3之直鏈狀或分枝狀之 烷基）、矽烷氧基烷基（以（_〇SiR5R6R7 (R5、R6、R7係碳 原子數1~6之直鏈狀或分枝狀之烷基、以1個鹵素原子取 代之碳原子數1〜3之直鏈狀或分枝狀之鹵烷基、以1個氰 基取代之碳原子數1〜3之直鏈狀或分枝狀之氰基烷基、以 及苯基，且其中二者或全部可爲相同之取代基或全部相異 之取代基）取代之碳原子數1〜3之直鏈狀或分枝狀之烷基） 、羥基烷基（以1個或2個羥基取代之碳原子數1〜3之直 鏈狀或分枝狀之烷基）、烷氧基烷基（以碳原子數1〜8之直 鏈狀或分枝狀之經1個或2個烷氧基取代之碳原子數1〜3 之直鏈狀或分枝狀之烷基）、鹵烷氧基烷基（以相同或相異 之1〜9個鹵素原子取代之碳原子數1〜4之直鏈狀或分枝狀 的經1個或2個鹵烷氧基取代之碳原子數1〜3之直鏈狀或 分枝狀之烷基）、烷基硫代烷基（以碳原子數1〜8之直鏈狀 或分枝狀之經1個或2個烷基硫代基取代之碳原子數1〜3 之直鏈狀或分枝狀之烷基）、二烷氧基乙縮醛基（以碳原子 數1〜8之直鏈狀或分枝狀之烷氧基經於2個甲基位置進行 取代之二烷氧基甲基）、烷氧基烷氧基（以碳原子數1~8之 直鏈狀或分枝狀的經1個或2個烷氧基取代之碳原子數 1~3之直鏈狀或分枝狀之烷氧基）、氰基烷基（以1個或2 個氰基取代之碳原子數1〜3之直鏈狀或分枝狀之烷基）、 鹵素、氰基、硝基、胺基、羥基、戊鹵磺醯基、苯甲基、 -13- 201238485 苯甲基氧基、苯基、苯氧基、吡啶基、噁唑基、呋喃基、 噻唑基、萘基、嘧啶基、噻吩基、苯并噻唑基、苯并噁唑 基、苯并二噁茂基、亞胺基、甲醯基（_ CHO)、羧基（一 COOH) '甲醯胺基（_ NHCHO)、環狀醚以及環狀胺。 R2 表示氫原子、一R、一 OR、一 C(0)0R、 一 C(0)NHR、一 CONR2(此處之R係碳原子數1〜8之直鏈 狀或分枝狀之烷基、碳原子數2〜8之直鏈狀或分枝狀之烯 基、碳原子數2〜8之直鏈狀或分枝狀之炔基或碳原子數 3 ~8之環烷基）、羥基烷基（以1個或2個羥基取代之碳原 子數1~3之直鏈狀或分枝狀之烷基）、烷氧基烷基（以碳原 子數1〜8之直鏈狀或分枝狀之1個或2個烷氧基取代之碳 原子數1~3之直鏈狀或分枝狀之烷基）、鹵烷氧基烷基（以 相同或相異之1〜9個鹵素原子取代之碳原子數1〜4之直鏈 狀或分枝狀的1個或2個鹵烷氧基取代之碳原子數1〜3之 直鏈狀或分枝狀之烷基）、苯基、雜芳基、鹵素、氰基、 鹵烷基（以相同或相異之1〜9個鹵素原子取代之碳原子數 1~4之直鏈狀或分枝狀的烷基）、鹵烷氧基（以相同或相異 之1〜9個鹵素原子取代之碳原子數1〜4之直鏈狀或分枝狀 的烷氧基）。 R1中視情況而爲含有〇〜3個雜原子之單環式或雙環 式之環，可舉出苯基、苯甲基、噁唑基、異噁唑基、呋喃 基、苯并呋喃基、異苯并呋喃基、二氫苯并呋喃基、噻唑 基、異噻唑基、萘基、嘧啶基、吡嗪基、喹喔啉基、喹唑 啉基、吡啶基、喹啉基、異喹啉基、苯并噻唑基、苯并異 • 14- 201238485 噻唑基、吡咯基、吲哚基、異吲哚基、苯并噁唑基、苯并 異噁唑基、噻吩基、苯并噻吩基、咪唑基、苯并咪唑基、 吡唑基、吡啶酮基，其中以苯基、噁唑基、噻唑基、吡啶 基、噻吩基爲佳，苯基、吡啶基、噻唑基更佳。另外，取 代基可舉出例如一C(0)0R、一 C(0)R、一R、一 OR、一SR 、一S02R、一 OC(0)R、一 C(0)NHR、一 C(0)NR2、 —NHS02R、— NRSO2R ' — NHR、一 NR2、— NHC(〇)R 、一NRC(0)R' —NHC(0)0R、一NRC(0)0R、 —N(0R)C(0)0R、- NHSO2R ' - NRSO2R ' - SO2NHR 、一S02NR2(此處之R係代表碳原子數1〜8之直鏈狀或分 枝狀之烷基、碳原子數2〜8之直鏈狀或分枝狀之烯基、碳 原子數2〜8之直鏈狀或分枝狀之炔基或碳原子數3〜8之環 烷基）、一 SiR5R6R7、_ OSiR5R6R7 (R5、R6、R7 係碳原子 數1~6之直鏈狀或分枝狀之烷基、以1個鹵素原子取代之 碳原子數1〜3之直鏈狀或分枝狀之鹵烷基、以1個氰基取 代之碳原子數1〜3之直鏈狀或分枝狀之氰基烷基、以及苯 基，且其中二者或全部可爲相同之取代基或全部相異之取 代基）、鹵烷基（以相同或相異之1〜9個鹵素原子取代之碳 原子數1~4之直鏈狀或分枝狀之烷基）、鹵烯基（以相同或 相異之1〜4個鹵素原子取代之碳原子數2~6之直鏈狀或分 枝狀之烯基）、鹵烷氧基（以相同或相異之1〜9個鹵素原子 取代之碳原子數1〜4之直鏈狀或分枝狀之烷氧基）、醯基 烷氧基（以（碳原子數1〜8之直鏈狀或分枝狀之脂肪族烴基 )_ CO—表示之經1個或2個醯基取代之碳原子數1〜3之 -15- 201238485 直鏈狀或分枝狀之烷氧基）、醯氧基烷基（以（碳原子數1〜8 之直鏈狀或分枝狀之脂肪族烴基）一 CO — 0—表示之經1 個或2個醯基氧基取代之碳原子數1〜3之直鏈狀或分枝狀 之烷基）、烷基磺酸基烷基（以碳原子數1〜8之直鏈狀或分 枝狀之經1個或2個烷基磺酸基取代之碳原子數1〜3之直 鏈狀或分枝狀之烷基）、矽烷氧基烷基（以（ —OSiR5R6R7(R5、R6、R7係碳原子數1〜6之直鏈狀或分 枝狀之烷基、以1個鹵素原子取代之碳原子數1〜3之直鏈 狀或分枝狀之鹵烷基、以1個氤基取代之碳原子數1〜3之 直鏈狀或分枝狀之氰基烷基、以及苯基，且其中二者或全 部可爲相同之取代基或全部相異之取代基）取代之碳原子 數1〜3之直鏈狀或分枝狀之烷基）、羥基烷基（經以1個或 2個羥基取代之碳原子數1〜3之直鏈狀或分枝狀之烷基） 、烷氧基烷基（以碳原子數1〜8之直鏈狀或分枝狀之經1 個或2個烷氧基取代之碳原子數1〜3之直鏈狀或分枝狀之 烷基）、鹵烷氧基烷基（以相同或相異之1~9個鹵素原子取 代之碳原子數1〜4之直鏈狀或分枝狀的經1個或2個鹵烷 氧基取代之碳原子數1〜3之直鏈狀或分枝狀之烷基）、烷 基硫代烷基（以碳原子數1〜8之直鏈狀或分枝狀之經1個 或2個烷基硫代基取代之碳原子數1〜3之直鏈狀或分枝狀 之烷基）、二烷氧基乙縮醛基（以碳原子數1~8之直鏈狀或 分枝狀之烷氧基經於2個甲基位置進行取代之二烷氧基甲 基）、烷氧基烷氧基（以碳原子數1~8之直鏈狀或分枝狀的 經1個或2個烷氧基取代之碳原子數1~3之直鏈狀或分枝 -16- 201238485 狀之烷氧基）、氰基烷基（經以1個或2個氰基取代之 子數1〜3之直鏈狀或分枝狀之烷基）、鹵素、氰基、 、胺基、羥基、戊鹵磺醯基、苯甲基、苯甲基氧基、 、苯氧基、吡啶基、噁唑基、呋喃基、噻唑基、萘基 啶基、噻吩基、苯并噻唑基、苯并噁唑基、苯并二噁 、亞胺基、甲醯基（一CHO)、羧基（_COOH)、甲醯 (―NHCHO)、環狀醚以及環狀胺，但以烷基（例如甲 乙基、正丙基、異丙基）、烷氧基（例如甲氧基、乙氧 正丙氧基、異丙氧基）、醯基烷氧基（例如乙醯基甲氧 丙醯基甲氧基、乙醯基乙氧基）' 鹵素（例如氟原子、 子、溴原子）、氰基、鹵院基（例如單氟甲基、二氛甲 三氟甲基、七氟異丙基）、羥基烷基（例如羥基甲基、 乙基）、氰基烷基（例如氰基甲基、氰基乙基）、烷氧 基（甲氧基甲氧基、乙氧基甲氧基、甲氧基乙氧基）、 氧基烷基（例如單氟甲氧基甲基、二氟甲氧基甲基、 甲氧基甲基）、鹵烷氧基（例如單氟甲氧基、二氟甲氧 三氟甲氧基）、苄基氧基、苯氧基爲佳》 R1中碳原子數1~6之直鏈狀或分枝狀之烷基、 子數2〜8之直鏈狀或分枝狀之烯基、碳原子數2〜8之 狀或分枝狀之炔基、碳原子數3〜8之環烷基或碳原 3~8之環烯基係可舉出正丁基、第二丁基、第三丁基 己基、1-丙烯基、2-丙烯基、異丙烯基，但以正丁基 二丁基 '第三丁基、1-丙烯基、異丙烯基爲佳。另外 代基可舉出例如一C(0)0R、一 C(0)R、一 R、一〇R、[In the formula, R1 is selected from the following (a) to (d): a) from phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuranyl, isobenzofuranyl , dihydrobenzofuranyl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalinyl, oxazolinyl-6-201238485, pyridyl, quinolinyl, isoquinolinyl , benzothiazolyl, benzisothiazolyl, pyrrolyl, fluorenyl, isodecyl, benzoxazolyl, benzisoxazolyl, thienyl, benzothienyl, imidazolyl, benzo a group of imidazolyl, pyrazolyl, pyridone groups, and optionally a monocyclic or bicyclic ring containing 〇~3 heteroatoms, b) a linear chain having 1 to 6 carbon atoms Or a branched alkyl group, a linear or branched alkenyl group having 2 to 8 carbon atoms, a linear or branched alkynyl group having 2 to 8 carbon atoms, and 3 to 8 carbon atoms; a cycloalkyl group or a cycloalkenyl group having 3 to 8 carbon atoms, c) — SiR5R6R7 (R5, R6, and R7 are a linear or branched alkyl group having 1 to 6 carbon atoms, and 1 halogen atom; Substituted linear chain of 1 to 3 carbon atoms a branched haloalkyl group, a linear or branched cyanoalkyl group having 1 to 3 carbon atoms substituted by a cyano group, and a phenyl group, and both or all of them may be substituted by the same a radical or a completely different substituent), d) a hydrogen atom, and in the case of (a) or (b), the R1 may be substituted as follows: _C(0)0R, a C(〇)R, a R, an OR, an SR, a S02R, -0C(0)R, a C(0)NHR' -C(0)NR2, an NHS02R, -NRSO2R '-NHR, an NR2' - NHC(0)R , an NRC(0)R, an NHC(0)0R, NRC(0)0R, an N(0R)C(0)0R, -NHS02R, an NRS02R, a SO2NHR, _S02NR2 (where R is representative a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkenyl group having 2 to 8 carbon atoms, or a linear or branched carbon number of 2 to 8 An alkynyl group or a cycloalkyl group having 3 to 8 carbon atoms), a SiR5R6R7 201238485, an OSiR5R6R7 (R5, R6, and R7 are linear or branched alkyl groups having 1 to 6 carbon atoms, and 1) a linear or branched haloalkyl group having 1 to 3 carbon atoms substituted by a halogen atom, and having 1 to 3 carbon atoms substituted by one cyano group a chain or branched cyanoalkyl group, and a phenyl group and either or both of them may be the same substituent or all of the different substituents), haloalkyl (same or different from 1 to 9) a linear or branched alkyl group having 1 to 4 carbon atoms substituted by a halogen atom, or a halogenated alkenyl group (2 to 6 carbon atoms substituted by the same or different 1 to 4 halogen atoms) a chain or branched alkenyl group, a haloalkoxy group (a linear or branched alkoxy group having 1 to 4 carbon atoms substituted by the same or different 1 to 9 halogen atoms), a mercaptoalkoxy group (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms)-CO-substituted by one or two mercapto groups having a carbon number of 1 to 3 a chain or branched alkoxy group, a decyloxy group (in the form of a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) _ CO - Ο - represented by 1 or a linear or branched alkyl group having 1 to 3 carbon atoms substituted with a mercaptooxy group, or an alkylsulfonic acid alkyl group (linear or branched as a carbon number of 1 to 8) Substituted by one or two alkyl sulfonate groups a linear or branched alkyl group having 1 to 3 carbon atoms, a decyloxyalkyl group (a linear or branched alkyl group having a carbon atom number of R5, R6, and R7) a linear or branched haloalkyl group having 1 to 3 carbon atoms substituted with one halogen atom, or a linear or branched carbon number of 1 to 3 substituted with one cyano group. a cyanoalkyl group, and a phenyl group, and wherein two or all of them may be the same substituent or all of the different substituents) substituted with a linear or branched alkyl group having 1 to 3 carbon atoms), A hydroxyalkyl group (-8-201238485 linear or branched alkyl group having 1 or 3 carbon atoms substituted by 1 or 2 hydroxyl groups), an alkoxyalkyl group (having a carbon number of 1 to 8) a linear or branched alkyl or branched alkoxy group having 1 to 3 carbon atoms in a linear or branched form, or a haloalkoxyalkyl group (in the same or different a linear or branched form of 1 to 3 carbon atoms having 1 to 4 carbon atoms substituted by 1 or 9 dentate atoms substituted by 1 or 2 haloalkoxy groups Alkyl), alkylthioalkyl (by 1 carbon atom) a linear or branched linear or branched alkyl group having 1 or 3 carbon atoms substituted by 1 or 2 alkylthio groups, a dialkoxy acetal group (a linear or branched alkoxy group having 1 to 8 carbon atoms substituted by a dialkyloxymethyl group at 2 methyl positions), an alkoxyalkoxy group (having 1 carbon atom) ～8 linear or branched linear or branched alkoxy groups having 1 or 3 carbon atoms substituted by 1 or 2 alkoxy groups, and cyanoalkyl groups (1) Or 2 cyano substituted linear or branched alkyl groups having 1 to 3 carbon atoms, halogen, cyano, nitro, amine, hydroxy, pentylsulfonyl, benzyl, benzene Methyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzodioxan , an imido group, a mercapto group (a CHO), a carboxyl group (a COOH), a formamidine group (a NHCHO), a cyclic ether, and a cyclic amine, and R2 represents a hydrogen atom, an R, an OR, a C ( 0) 0R, a C(0)NHR, a CONR2 (where R is a carbon number of 1) a linear or branched alkyl group of 8 or a straight or branched alkenyl group having 2 to 8 carbon atoms; a linear or branched alkynyl group or carbon having 2 to 8 carbon atoms; a cycloalkyl group having an atomic number of 3 to 8, a hydroxyalkyl group (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), an alkoxyalkyl group (in terms of a linear or branched alkyl group having 1 or 3 carbon atoms) Carbonogen-9- 201238485 A linear or branched alkyl group of 1 to 8 or a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 2 or alkoxy groups. Haloalkoxyalkyl group (a linear or branched carbon atom having the same or different 1 to 9 halogen atoms, substituted by one or two haloalkoxy groups; a linear or branched alkyl group of 3), a phenyl group, a heteroaryl group, a halogen, an aryl group, a haloalkyl group (having 1 to 4 carbon atoms substituted with the same or different 1 to 9 halogen atoms) a linear or branched alkyl group, a haloalkoxy group (a linear or branched alkoxy group having 1 to 4 carbon atoms substituted with the same or different 1 to 9 halogen atoms) ). Further, the second invention is a method for producing a fluorine-containing quinazoline derivative represented by the formula [I]. Further, the third invention is a pest control agent containing one or more kinds of the fluorine-containing oxazoline derivatives represented by the formula [I] as an active ingredient. [Effect of the Invention] The novel fluorine-containing quinazoline derivative represented by the formula [I] of the present invention has an excellent control effect against harmful organisms, particularly pests for agriculture and horticulture. [Embodiment] Hereinafter, the present invention will be described in detail. In the above-mentioned fluorine-containing quinazoline derivative of the present invention, in addition to the fluorine-containing quinazoline derivative represented by the formula, a salt of the derivative (sodium salt, potassium salt, magnesium salt, calcium) is also included. Salt, aluminum salt, etc.), water and substance, solvate, -10- 201238485 Crystalline polytype. Further, all possible stereoisomers or optical isomers present in the compounds of the invention, and mixtures comprising more than two or more of their isomers in any ratio, are also included in the compounds of the invention (shown by formula [I] Within the range of the fluorine-containing quinazoline derivative). The various substituents represented by the compound [I] described above are as follows. R1 is a substituent selected from any one of the following (a) to (d): a) constituting a phenyl group, a benzyl group, an oxazolyl group, an isoxazolyl group, a furyl group, a benzofuranyl group, an isobenzoate group Furanyl, dihydrobenzofuranyl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalinyl, oxazolinyl, pyridyl, quinolyl, iso- sulphone, benzene Thiazolyl, benzoisosazolyl, pyrrolyl, fluorenyl, isodecyl, benzoxazolyl, benzisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazole a group formed by a pyrazole group or a pyridone group, and optionally a ring atom (carbon atom or hetero atom) of a monocyclic or bicyclic ring having 0 to 3 hetero atoms as a bond The base of the bond ib) a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkenyl group having 2 to 8 carbon atoms, and a straight carbon number of 2 to 8 a chain or branched alkynyl group, a cycloalkyl group having 3 to 8 carbon atoms or a cycloalkenyl group having 3 to 8 carbon atoms c) - SiR5R6R7 (R5, R6, R7 is a number of carbon atoms Chain or branched alkyl a linear or branched haloalkyl group having 1 to 3 carbon atoms substituted by one halogen atom, or a linear or branched cyanide having 1 to 3 carbon atoms substituted by one cyano group. An alkyl group, and a phenyl group, and wherein either or both may be the same substituent or all of the different substituents). -11 - 201238485 d) Hydrogen atom. In the case of (a) or (b), R1 may be substituted as follows: a C(Ο)ΟR ' _ C(0)R '- R, an OR, an SR, an SΟ2R ' — 0C(0 R, a C(0)NHR, a C(0)NR2, an NHS02R, - NRS02R ' - NHR ' - NR2, an NHC(0)R' - NRC(0)R, - NHC(0)0R, An NRC(0)0R, an N(0R)C(0)0R, an NHSO2R, an NRS02R, a S02NHR, a S02NR2 (where R represents a linear or branched form having 1 to 8 carbon atoms) An alkyl group, a linear or branched alkenyl group having 2 to 8 carbon atoms, a linear or branched alkynyl group having 2 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. ), a 3 ft. 5116 ft. 7, an OSiR5R6R7 (R5, R6, RM is a linear or branched alkyl group having a carbon number of 6 and a carbon atom number of 1 to 3 substituted with one halogen atom) a linear or branched haloalkyl group, a linear or branched cyanoalkyl group having 1 to 3 carbon atoms substituted by a cyano group, and a phenyl group, and both or both of them may be used. a substituent having the same substituent or all of the different substituents), a haloalkyl group (a group of 1 to 4 carbon atoms substituted with the same or different 1 to 9 halogen atoms) a branched or branched alkyl group, an alkenyl group (a linear or branched alkenyl group having 2 to 6 carbon atoms substituted by the same or different 1 to 4 halogen atoms), haloalkoxy a base (a linear or branched alkoxy group having 1 to 4 carbon atoms substituted with the same or different 1 to 9 halogen atoms), a mercaptoalkoxy group (having 1 to 8 carbon atoms) a linear or branched aliphatic hydrocarbon group; a CO—a straight or branched alkoxy group having 1 to 3 carbon atoms substituted by one or two thiol groups) Alkyl group (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) - CO - Ο - a carbon atom substituted by 1 or 2 mercaptooxy-12-201238485 a linear or branched alkyl group of 1 to 3, an alkylsulfonic acid alkyl group (linear or branched in the form of a carbon number of 1 to 8 or 1 or 2 alkylsulfonates) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by an acid group, or a decyloxyalkyl group (by 〇SiR5R6R7 (R5, R6, R7 is a linear chain having 1 to 6 carbon atoms) a branched or branched alkyl group substituted with one halogen atom a linear or branched haloalkyl group of 1 to 3, a linear or branched cyanoalkyl group having 1 to 3 carbon atoms substituted with one cyano group, and a phenyl group, and two of them Or all of the same substituent or all of the different substituents may be substituted by a linear or branched alkyl group having 1 to 3 carbon atoms, or a hydroxyalkyl group (substituted by 1 or 2 hydroxyl groups) a linear or branched alkyl group having 1 to 3 carbon atoms, an alkoxyalkyl group (1 or 2 alkoxy groups in a linear or branched form having 1 to 8 carbon atoms) a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a group, a haloalkoxyalkyl group (having 1 to 4 carbon atoms substituted with the same or different 1 to 9 halogen atoms) a linear or branched linear or branched alkyl group having 1 or 3 carbon atoms substituted by one or two haloalkoxy groups, or an alkylthioalkyl group (in terms of carbon atoms) a straight or branched linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 alkylthio groups, 1 to 8 or a dialkoxy condensate Aldehyde group (linear or branched alkoxy group having 1 to 8 carbon atoms) a substituted dialkoxymethyl group at two methyl positions, an alkoxyalkoxy group (a linear or branched one or two alkoxy groups having 1 to 8 carbon atoms) a linear or branched alkoxy group having 1 to 3 carbon atoms substituted, a cyanoalkyl group (a straight chain or a branch having 1 to 3 carbon atoms substituted by 1 or 2 cyano groups) Alkyl), halogen, cyano, nitro, amine, hydroxy, pentylsulfonyl, benzyl, -13- 201238485 benzyloxy, phenyl, phenoxy, pyridyl, evil Azyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzodioxan, imido, formyl (_CHO), carboxyl (one COOH) 'Methylamine (_NHCHO), cyclic ether and cyclic amine. R2 represents a hydrogen atom, an R, an OR, a C(0)0R, a C(0)NHR, a CONR2 (wherein R is a linear or branched alkyl group having 1 to 8 carbon atoms) a linear or branched alkenyl group having 2 to 8 carbon atoms, a linear or branched alkynyl group having 2 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, and a hydroxyl group An alkyl group (a linear or branched alkyl group having 1 or 3 carbon atoms substituted by one or two hydroxyl groups) or an alkoxyalkyl group (a linear or branched carbon number of 1 to 8) a linear or branched alkyl group having 1 or 3 carbon atoms substituted by a branched or branched alkoxy group, or a haloalkoxyalkyl group (1 to 9 halogens which are the same or different) a linear or branched alkyl group having 1 to 4 carbon atoms or 1 or 4 haloalkoxy groups substituted with one or two haloalkoxy groups having 1 to 3 carbon atoms; , heteroaryl, halogen, cyano, haloalkyl (linear or branched alkyl having 1 to 4 carbon atoms substituted by the same or different 1 to 9 halogen atoms), haloalkoxy a linear or branched group of 1 to 4 carbon atoms substituted with the same or different 1 to 9 halogen atoms Alkoxy group). R1 may, as the case may be, a monocyclic or bicyclic ring containing 〇~3 hetero atoms, and examples thereof include a phenyl group, a benzyl group, an oxazolyl group, an isoxazolyl group, a furyl group, a benzofuranyl group, and a different form. Benzofuranyl, dihydrobenzofuranyl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalinyl, quinazolinyl, pyridyl, quinolinyl, isoquinolyl Benzothiazolyl, benzoisoyl • 14- 201238485 thiazolyl, pyrrolyl, fluorenyl, isodecyl, benzoxazolyl, benzisoxazolyl, thienyl, benzothienyl, imidazole The group is a benzimidazolyl group, a pyrazolyl group or a pyridone group, wherein a phenyl group, an oxazolyl group, a thiazolyl group, a pyridyl group or a thienyl group is preferred, and a phenyl group, a pyridyl group or a thiazolyl group is more preferred. Further, the substituent may, for example, be a C(0)0R, a C(0)R, an R, an OR, an SR, a S02R, an OC(0)R, a C(0)NHR, a C. (0) NR2, -NHS02R, - NRSO2R ' - NHR, one NR2, - NHC(〇)R, one NRC(0)R' - NHC(0)0R, one NRC(0)0R, -N(0R) C(0)0R, -NHSO2R ' - NRSO2R ' - SO2NHR, a S02NR2 (wherein R represents a linear or branched alkyl group having 1 to 8 carbon atoms, and a straight carbon number of 2 to 8) a chain or branched alkenyl group, a linear or branched alkynyl group having 2 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, a SiR5R6R7, _OSiR5R6R7 (R5, R6, R7 is a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched haloalkyl group having 1 to 3 carbon atoms substituted by one halogen atom, and 1 cyanide. a linear or branched cyanoalkyl group having 1 to 3 carbon atoms, and a phenyl group, and both or all of them may be the same substituent or all of the different substituents, and a halogenated alkane a straight-chain or branched alkyl group having 1 to 4 carbon atoms substituted by the same or different 1 to 9 halogen atoms, or a halogenated alkene (linear or branched alkenyl group having 2 to 6 carbon atoms substituted by the same or different 1 to 4 halogen atoms), haloalkoxy group (1 to 9 halogens of the same or different) a linear or branched alkoxy group having 1 to 4 carbon atoms substituted by an atom, or a mercaptoalkoxy group (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) _ CO—the number of carbon atoms 1 to 3 substituted by 1 or 2 thiol groups - 201238485 linear or branched alkoxy group), decyloxyalkyl group (by carbon number) a linear or branched aliphatic hydrocarbon group of 1 to 8), CO - 0 - represents a linear or branched carbon number of 1 to 3 substituted by one or two mercaptooxy groups. Alkyl), alkyl sulfonylalkyl (linear chain having a carbon number of 1 to 3 substituted by one or two alkylsulfonic acid groups in a linear or branched form having 1 to 8 carbon atoms) a branched or branched alkyl group, a decyloxyalkyl group (by -OiR5R6R7 (R5, R6, R7 is a linear or branched alkyl group having 1 to 6 carbon atoms, and 1 halogen atom) a linear or branched halogen having 1 to 3 carbon atoms substituted a linear or branched cyanoalkyl group having 1 to 3 carbon atoms substituted with 1 fluorenyl group, and a phenyl group, and both or all of them may be the same substituent or all of them different a substituted or substituted linear or branched alkyl group having 1 to 3 carbon atoms, or a hydroxyalkyl group (a linear or branched carbon number of 1 to 3 substituted with 1 or 2 hydroxyl groups) a branched alkyl group, an alkoxyalkyl group (linear or branched in the form of a straight or branched chain having 1 to 8 carbon atoms, substituted by 1 or 2 alkoxy groups, having a linear number of 1 to 3 carbon atoms; Or a branched alkyl group, a haloalkoxyalkyl group (a linear or branched one or two carbon atoms having 1 to 4 carbon atoms substituted by the same or different 1 to 9 halogen atoms) a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a haloalkoxy group, or an alkylthioalkyl group (linear or branched having a carbon number of 1 to 8) a linear or branched alkyl group having 1 or 3 carbon atoms substituted with 1 or 2 alkylthio groups, a dialkoxy acetal group (linear chain having 1 to 8 carbon atoms) a branched or branched alkoxy group substituted at two methyl positions a dialkoxymethyl group, an alkoxyalkoxy group (a straight or branched chain having 1 to 8 carbon atoms substituted by 1 or 2 alkoxy groups and having a carbon number of 1 to 3) Chain or branched -1638, 2012 alkoxy), cyanoalkyl (linear or branched alkyl having 1 or 3 substituted by 1 or 2 cyano groups), halogen , cyano, amine, hydroxy, pentyl sulfonyl, benzyl, benzyloxy, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyridinyl, thiophene Base, benzothiazolyl, benzoxazolyl, benzodioxin, imido, formamidine (mono CHO), carboxyl (_COOH), formamidine ("NHCHO"), cyclic ethers, and cyclic amines, However, an alkyl group (e.g., methyl ethyl, n-propyl, isopropyl), an alkoxy group (e.g., methoxy, ethoxy-n-propoxy, isopropoxy), a decyl alkoxy group (e.g., an ethyl group) Methoxypropyl methoxy, ethoxymethyl ethoxy) 'halogen (eg, fluorine atom, sub, bromine atom), cyano group, halogen-based (eg, monofluoromethyl, di-trifluoromethyl, Heptafluoroisopropyl), hydroxyalkyl (for example Methyl, ethyl), cyanoalkyl (eg cyanomethyl, cyanoethyl), alkoxy (methoxymethoxy, ethoxymethoxy, methoxyethoxy) , oxyalkyl (eg monofluoromethoxymethyl, difluoromethoxymethyl, methoxymethyl), haloalkoxy (eg monofluoromethoxy, difluoromethoxytrifluoromethane) A benzyloxy group or a phenoxy group is preferred. A linear or branched alkyl group having 1 to 6 carbon atoms and a linear or branched alkenyl group having 2 to 8 carbon atoms in R1. Examples of the cycloalkenyl group having a carbon number of 2 to 8 or a branched alkynyl group, a cycloalkyl group having 3 to 8 carbon atoms or a cycloalkenyl group having 3 to 8 carbon atoms include n-butyl group and second butyl group. The third butylhexyl group, the 1-propenyl group, the 2-propenyl group, and the isopropenyl group are preferably n-butyldibutyl 't-butyl group, 1-propenyl group, or isopropenyl group. Further, for example, a C(0)0R, a C(0)R, an R, a R,

碳原 硝基 苯基 、嘧 茂基 胺基 基、 基、 基、 氯原 基、 羥基 基烷 鹵垸 三氟 基、 碳原 直鏈 子數 、正 、第 ，取 -SR -17- 201238485 、一S02R、一 0C(0)R、一 C(0)NHR、一 C(0)NR2、 —NHS02R、一 NRS02R、一 NHR、一 NR2、— NHC(0)R 、一NRC(0)R、一NHC(0)0R、一NRC(0)0R、 —N(0R)C(0)0R、一 NHS02R、一 NRS02R、— S02NHR 、一S02NR2(此處之R係代表碳原子數1〜8之直鏈狀或分 枝狀之烷基、碳原子數2〜8之直鏈狀或分枝狀之烯基、碳 原子數2〜8之直鏈狀或分枝狀之炔基或碳原子數3〜8之環 烷基）、一SiR5R6R7、一 OSiR5R6R7 (R5、R6、R7 係碳原子 數1~6之直鏈狀或分枝狀之烷基、以1個鹵素原子取代之 碳原子數1〜3之直鏈狀或分枝狀之鹵烷基、以1個氛基取 代之碳原子數1~3之直鏈狀或分枝狀之氰基烷基、以及苯 基，且其中二者或全部可爲相同之取代基或全部相異之取 代基）、鹵烷基（以相同或相異之1〜9個鹵素原子取代之碳 原子數1〜4之直鏈狀或分枝狀之烷基）、鹵烯基（以相同或 相異之1〜4個鹵素原子取代之碳原子數2〜6之直鏈狀或分 枝狀之烯基）、鹵烷氧基（以相同或相異之1〜9個鹵素原子 取代之碳原子數1〜4之直鏈狀或分枝狀之烷氧基）、醯基 烷氧基（以（碳原子數1〜8之直鏈狀或分枝狀之脂肪族烴基 )一 CO—表示之經1個或2個醯基取代之碳原子數1~3之 直鏈狀或分枝狀之烷氧基）、醯氧基烷基（以（碳原子數1〜8 之直鏈狀或分枝狀之脂肪族烴基）一 CO— 0—表示之經1 個或2個醯基氧基取代之碳原子數1〜3之直鏈狀或分枝狀 之烷基）、烷基磺酸基烷基（以碳原子數1〜8之直鏈狀或分 枝狀之經1個或2個烷基磺酸基取代之碳原子數1〜3之直 -18- 201238485 鏈狀或分枝狀之烷基）、矽烷氧基烷基（以（一OSiR5R6R7(R5 、R6、R7係碳原子數1〜6之直鏈狀或分枝狀之烷基、以1 個鹵素原子取代之碳原子數1〜3之直鏈狀或分枝狀之鹵烷 基、以1個氰基取代之碳原子數1〜3之直鏈狀或分枝狀之 氰基烷基、以及苯基，且其中二者或全部可爲相同之取代 基或全部相異之取代基）取代之碳原子數1〜3之直鏈狀或 分枝狀之烷基）、羥基烷基（經以1個或2個羥基取代之碳 原子數1〜3之直鏈狀或分枝狀之烷基）、烷氧基烷基（以碳 原子數1〜8之直鏈狀或分枝狀之經1個或2個烷氧基取代 之碳原子數1〜3之直鏈狀或分枝狀之烷基）、鹵烷氧基垸 基（以相同或相異之1〜9個鹵素原子取代之碳原子數1〜4 之直鏈狀或分枝狀的經1個或2個鹵烷氧基取代之碳原子 數1〜3之直鏈狀或分枝狀之烷基）、烷基硫代烷基（以碳原 子數1~8之直鏈狀或分枝狀之經1個或2個烷基硫代基取 代之碳原子數1〜3之直鏈狀或分枝狀之烷基）、二烷氧基 乙縮醛基（以碳原子數1〜8之直鏈狀或分枝狀之烷氧基經 於2個甲基位置進行取代之二烷氧基甲基）、烷氧基烷氧 基（以碳原子數1〜8之直鏈狀或分枝狀的經1個或2個烷 氧基取代之碳原子數1~3之直鏈狀或分枝狀之烷氧基）、 氰基烷基（經以1個或2個氰基取代之碳原子數1〜3之直 鏈狀或分枝狀之烷基）、鹵素、氰基、硝基、胺基 '羥基 、戊鹵磺醯基、苯甲基、苯甲基氧基、苯基、苯氧基、吡 啶基、噁唑基、呋喃基、噻唑基、萘基、嘧啶基、噻吩基 、苯并噻唑基、苯并噁唑基、苯并二噁茂基、亞胺基、甲 -19- 201238485 醯基（一CHO)、羧基（一COOH)、甲醯胺基（一 NHCHO)、環 狀醚以及環狀胺，但以烷氧基羧基（例如甲氧基羧基、乙 氧基羧基）、鹵素（例如氟原子、氯原子、溴原子）、氰基 、羥基烷基（例如羥基甲基、羥基乙基）、烷氧基烷基（甲 氧基甲基、.乙氧基甲基、甲氧基乙基）、鹵烷基（例如單氟 甲基、二氟甲基、三氟甲基、七氟異丙基）、鹵烷氧基（例 如單氟甲氧基、二氟甲氧基、三氟甲氧基）、鹵烷氧基烷 基（例如單氟甲氧基甲基、二氟甲氧基甲基、三氟甲氧基 甲基）' 氰基烷基（例如氰基甲基、氰基乙基）、苯基、吡 啶基、呋喃基、噻唑基、嘧啶基爲佳。 R1中一 SiR5R6R7 (R5、R6、R7係碳原子數1~6之直鏈 狀或分枝狀之烷基、以1個鹵素原子取代之碳原子數1〜3 之直鏈狀或分枝狀之鹵烷基、以1個氰基取代之碳原子數 1〜3之直鏈狀或分枝狀之氰基烷基、以及苯基，且其中二 者或全部可爲相同之取代基或全部相異之取代基）可舉出 例如三甲基矽烷基、三乙基矽烷基、三異丙基矽烷基、第 三丁基二甲基矽烷基、第三丁基二苯基矽烷基、氯甲基二 甲基矽烷基、氛基丙基二甲基矽烷基，但以三甲基矽烷基 、三乙基矽烷基爲佳。 R2以氫原子或氰基爲佳，碳原子數1〜8之直鏈狀或 分枝狀之烷基，以甲基或乙基爲佳’碳原子數2〜8之直鏈 狀或分枝狀之烯基，以乙烯基、丙烯基爲佳。 R2 可舉出一C(0)0R、一C(0)NHR、一 OCNR2(此處之 R係代表碳原子數1〜8之直鏈狀或分枝狀之烷基、碳原子 -20- 201238485 數2~8之直鏈狀或分枝狀之烯基、碳原子數2〜8之直鏈狀 或分枝狀之炔基或碳原子數3〜8之環烷基）、苯基、雜芳 基，較佳係苯基。 R2中之鹵原子可舉出氯離子、碘原子、溴原子、氟 原子，以氯離子、氟離子爲佳。 R2中之烷氧基可舉出甲氧基、乙氧基、正丙乙基、 異丙氧基，以甲氧基、乙氧基爲佳。 R2中之鹵烷基以單氟甲基、二氟甲基、三氟甲基爲 佳，鹵烷氧基以單氟甲氧基、二氟甲氧基、三氟甲氧基爲 佳。 本發明中「烷基」之用語表示碳原子數之直鏈狀 或分枝狀之烷基，可舉出例如甲基、乙基、正丙基、異丙 基、正丁基、異丁基、第二丁基、第三丁基、正戊基、異 戊基、新戊基、正己基、正庚基或正辛基等。 本發明中「烯基」之用語表示碳原子數2~8之直鏈狀 或分枝狀之烯基，可舉出例如乙烯基、丨-丙烯基、2·丙烯 基、異丙烯基、1-丁烯基、2-丁烯基或3_丁烯基。 本發明中「炔基」之用語表示碳原子數2-8之直鏈狀 或分枝狀之炔基’可舉出例如乙炔基、2-丙炔基、2-丁炔 基或3-丁炔基。 本發明中「環烷基」之用語表示碳原子數3-8之環烷 基，可舉出例如環丙基、環丁基、環戊基或環己基。 本發明中「環烯基」之用語表示碳原子數3~8之環烷 基，可舉出例如1 -環戊基、2-環戊基、3_環戊基、1 -環己 -21 - 201238485 基、2-環己基或3-環己基。 本發明中「雜原子」之用語包含氮原子、氧原子及硫 原子。 本發明中「鹵素」之用語包含氟、氯、溴及碘。 本發明中「鹵….」（例如鹵烷基）中稱爲「鹵」之用語 包含氟、氯、溴及拂。 本發明中「鹵烷基」之用語係表示經相同或相異之 1〜9個鹵素原子取代之碳原子數1〜4之直鏈狀或分枝狀之 烷基’例如可舉出單氟甲基、單氯甲基、單溴甲基、二氟 甲基、三氟甲基、五氟乙基、正七氟丙基或異七氟丙基等 〇 本發明中「鹵烯基」之用語係表示經相同或相異之 1〜4個鹵素原子取代之碳原子數2〜6之直鏈狀或分枝狀之 烯基，例如可舉出1,2 -二氟乙烯基、2，2 -二氟乙烯基、3, 3-二氟-2-丙烯基等。 本發明中「烷氧基」之用語係表示烷基部分爲上述意 義之（院基）_〇 —基’可舉出例如甲氧基、乙氧基、正丙 氧基、異丙氧基、正丁氧基、第二丁氧基或第三丁氧基。 本發明中「鹵烷氧基」之用語係表示鹵烷基部分爲上 述意義之（鹵院基）一 0—基’例如可舉出單氟甲氧基、二 氟甲氧基、三氟甲氧基、2，2-二氟乙氧基或2，2，2_三氟 乙氧基等。 本發明中「醯基」之用語或醯基烷氧基中稱爲「醯基 」之用、醯氧基垸基中稱爲「醯基」之用語及酿氧基中 -22- 201238485 稱爲「醯基」之用語之任一者均表示以（碳原子數1〜8之 直鏈狀或分枝狀之脂肪族烴基）一 CO—表示之基，例如可 舉出乙醯基、丙醯基、丁醯基或異丁醯基等。另外，本說 明書中，脂肪族烴基係意指烷基、烯基、炔基、環烷基、 環烯基、環炔基。 本發明中「醯基烷氧基」之用語係表示經上述之1個 或2個醯基取代之碳原子數1~3之直鏈狀或分枝狀之烷氧 基，例如可舉出乙醯基甲氧基、乙醯基乙氧基、乙醯基丙 氧基等。 本發明中「醯氧基」之用語係表示（碳原子數1〜8之 直鏈狀或分枝狀之脂肪族烴基）一 CO— Ο—，例如可舉出 乙醯氧基、丙醯氧基、異丙醯氧基或特戊醯氧基等。 本發明中「醯氧基烷基」之用語係表示經上述之丨個 或2個醯氧基取代之碳原子數1~3之直鏈狀或分枝狀之院 基，例如可舉出乙醯氧基甲基、乙醯氧基乙基或乙醯氧基 丙基等。 本發明中「烷基磺醯基」之用語係表示烷基部分爲上 述意義之（烷基）一S〇2—基，例如可舉出甲基磺醯基、乙 基磺醯基、正丙基磺醯基或異丙基磺醯基等。 本發明中「烷基磺醯基烷基」之用語係表示，經上述 之1個或2個院基擴醯基取代之碳原子數1〜3之直鏈狀或 分枝狀之院基’例如可舉出甲基擴酿基甲基、甲基碌醯基 乙基或甲基磺醯基丙基等。 本發明中「矽烷氧基」之用語係表示—〇SiR5R6R7 -23- 201238485 (R5、R6、R7係碳原子數1〜6之直鏈狀或分枝狀之烷基、 以1個鹵素原子取代之碳原子數1〜3之直鏈狀或分枝狀之 鹵烷基、以1個氤基取代之碳原子數1〜3之直鏈狀或分枝 狀之氰基烷基、以及苯基，且其中二者或全部可爲相同之 取代基或全部相異之取代基），可舉出例如三甲基矽烷氧 基、三乙基矽烷氧基、三異丙基矽烷氧基、第三丁基二甲 基矽烷氧基、第三丁基二苯基矽烷氧基等。 本發明中「矽烷氧基烷基」之用語係經上述之矽烷氧 基取代之碳原子數1〜3之直鏈狀或分枝狀之烷基，可舉出 例如三甲基矽烷氧基甲基、三甲基矽烷氧基乙基、三甲基 矽烷氧基丙基、三乙基矽烷氧基甲基或第三丁基二甲基矽 烷氧基等。 本發明中「羥基烷基」之用語係經1個或2個羥基取 代之碳原子數1〜3之直鏈狀或分枝狀之烷基，可舉出例如 羥基甲基、羥基乙基或羥基丙基等。 本發明中「烷氧基烷基」之用語係表示經上述1個或 2個烷氧基取代之碳原子數1〜3之直鏈狀或分枝狀之烷基 ，可舉出例如甲氧基甲基、乙氧基甲基、丙氧基甲基或異 丙氧基甲基等。 本發明中「烷硫基」之用語係表示烷基部分爲上述意 義之（院基）一 S—基’可舉出例如甲硫基、乙硫基或丙硫 基等。 本發明中「烷基硫基烷基」之用語係表示經上述1個 或2個烷硫基取代之碳原子數1〜3之直鏈狀或分枝狀之烷 -24- 201238485 基，可舉出例如甲基硫基甲基 '乙基硫基甲基、甲基硫基 乙基或乙基硫基乙基等。 本發明中「二烷氧基乙縮醛基」之用語係表示上述之 烷氧基經於2個甲基位置進行取代之二烷氧基甲基，可舉 出例如二甲氧基甲基、二乙氧基甲基或二丙氧基甲基等。 本發明中「烷氧基烷氧基」之用語係表示經上述之1 個或2個烷氧基取代之碳原子數1~3之直鏈狀或分枝狀之 烷氧基，可舉出例如甲氧基甲氧基、甲氧基乙氧基或甲氧 基丙氧基等。 本發明中「鹵烷氧基烷基」之用語係表示經上述之1 個或2個鹵烷氧基取代之碳原子數1〜3之直鏈狀或分枝狀 之烷基，可舉出例如單氟甲氧基甲基、二氟甲氧基甲基、 三氟甲氧基甲基等。 本發明中「氰基烷基」之用語係表示經上述之1個或 2個氰基取代之碳原子數1〜3之直鏈狀或分枝狀之烷基， 可舉出例如氰基甲基、氰基乙基或氰基丙基等。 本發明中「苯基」、「噻吩基」、「吡啶基」、「噁 唑基」、「呋喃基」、「噻唑基」、「萘基」、「嘧啶基 」、「苯并噻唑基」、「苯并噁唑基」、「苯并二噁茂基 」可具有相同或不同之一個以上之取代基，亦可不具有取 代基。 本發明中「苯氧基」之用語係表示包含具有可相同或 不同之一個以上之取代基之苯氧基及未經取代之苯氧基。 本發明中「苄基」之用語係表示包含具有相同或不同 -25- 201238485 之一個以上之取代基之苄基及未經取代之苄基。 本發明中「苄氧基」之用語係表示包含具有相同或不 同之一個以上之取代基之苄氧基及未經取代之苄氧基。 本發明中「丙炔基」之用語係表示包含烷末端上具有 取代基之丙炔基及未經取代之丙炔基。 本發明中「丙炔基氧基」之用語係表示包含烷末端上 具有取代基之丙炔氧基及未經取代之丙炔氧基。 本發明中「雜芳基」之用語係表示包含噁唑基、異噁 唑基、噻唑基、異噻唑基、嘧啶基、吡嗪基、喹喔啉基、 喹唑啉基、喹啉基、異喹啉基、吲哚基、異吲哚基、咪唑 基、吡唑基、吡啶基、呋喃基、噻吩基、吡咯基。該等基 可具有相同或不同之一個以上之取代基，亦可不具有取代 基。 本發明中「環狀醚」之用語係表示包含環氧、氧雜環 丁烷、四氫呋喃、四氫吡喃、二氧雜環戊烷、二噁烷。 本發明中「環狀胺」之用語係表示包含吡略啶基、咪 唑啶基、吡唑啶基、吡啶基、哌嗪基、嗎啉基。 本發明中「醯亞胺」之用語係表示包含鏈狀醯亞胺、 環狀醯亞胺。 以式Π ]所示之本發明之化合物由於具有胺基，故源 自該等之酸加成鹽亦包含於本發明中。 形成酸加成鹽之酸可舉出例如鹽酸、氫溴酸、硝酸、 硫酸、磷酸等無機酸，甲酸、草酸、富馬酸、己二酸、硬 酯酸、油酸、烏頭酸、油酸等羧酸，甲烷磺酸、苯磺酸、 -26- 201238485 對一甲苯磺酸等磺酸，或糖精等。 以式[I]所示之本發明之化合物R2爲一R、一 OR、 —C(0)0R、一 C(0)NHR、一 CONR2(此處之 R 係碳原子數 1〜8之直鏈狀或分枝狀之烷基、碳原子數2〜8之直鏈狀或 分枝狀之烯基、碳原子數2〜8之直鏈狀或分枝狀之炔基或 碳原子數3〜8之環烷基）、羥基烷基（以1個或2個羥基所 取代之碳原子數1〜3之直鏈狀或分枝狀之烷基）、烷氧基 烷基（以1個或2個碳原子數1〜8之直鏈狀或分枝狀的烷 氧基所取代之碳原子數1〜3之直鏈狀或分枝狀之烷基）、 苯基、雜芳基、鹵素、氰基、鹵烷基（經以相同或不同之 1~9個鹵素原子取代之碳原子數1〜4之直鏈狀或分枝狀之 烷基）、鹵烷氧基（經以相同或不同之1〜9個鹵素原子取代 之碳原子數1~4之直鏈狀或分枝狀之烷氧基）時所產生之 源自不對稱碳原子之各光學異構物、外消旋體或該等之混 合物之任一種均包含於本發明。 以下述式所示之本發明化合物[I]可如下述反應步驟 中所示般，藉由例如使以式[Π ]表示之氯嘧啶衍生物與以 式[瓜]所示之3-丁炔胺衍生物，在鹼（base)以及溶劑存在 下反應而製造。 【化2】Carbon nitrophenyl, pyrimidomethyl, yl, chloro, hydroxyalkyl alkanetrifluoro, carbon straight chain number, positive, first, take -SR -17- 201238485, a S02R , 0C(0)R, a C(0)NHR, a C(0)NR2, -NHS02R, an NRS02R, an NHR, an NR2, an NHC(0)R, an NRC(0)R, an NHC (0)0R, a NRC(0)0R, —N(0R)C(0)0R, an NHS02R, an NRS02R, —S02NHR, a S02NR2 (where R represents a linear chain of 1 to 8 carbon atoms) a linear or branched alkyl group, a linear or branched alkenyl group having 2 to 8 carbon atoms, a linear or branched alkynyl group having 2 to 8 carbon atoms or a carbon atom number of 3~ 8 cycloalkyl), a SiR5R6R7, an OSiR5R6R7 (R5, R6, R7 are linear or branched alkyl groups having 1 to 6 carbon atoms, and 1 to 3 carbon atoms substituted by 1 halogen atom a linear or branched haloalkyl group, a straight or branched cyanoalkyl group having 1 to 3 carbon atoms substituted with one aryl group, and a phenyl group, and both or both of them May be the same substituent or all of the different substituents), haloalkyl (in the same or phase a linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms, and a halogenated alkenyl group (having the same or different carbon atoms substituted by 1 to 4 halogen atoms) 2 to 6 linear or branched alkenyl), haloalkoxy (linear or branched with 1 to 4 carbon atoms substituted by the same or different 1 to 9 halogen atoms) Alkoxy), mercaptoalkoxy (having a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) - CO-substituted by one or two thiol groups a linear or branched alkoxy group of 1 to 3), a decyloxyalkyl group (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) - CO - 0 - a linear or branched alkyl group having 1 or 3 carbon atoms substituted by 1 or 2 mercaptooxy groups, or an alkylsulfonic acid alkyl group (linear chain having 1 to 8 carbon atoms) a linear or branched alkyl group having 1 or 3 carbon atoms substituted by 1 or 2 alkyl sulfonate groups, and a decyloxyalkyl group. An OSiR5R6R7 (R5, R6, R7 is a linear chain of 1 to 6 carbon atoms) a branched alkyl group, a linear or branched haloalkyl group having 1 to 3 carbon atoms substituted by one halogen atom, and a linear chain having 1 to 3 carbon atoms substituted by one cyano group Or a branched or branched cyanoalkyl group, and a phenyl group, and both or all of which may be the same substituent or all of the different substituents, substituted with a linear or branched carbon number of 1 to 3 Alkyl group), hydroxyalkyl group (linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), alkoxyalkyl group (having 1 to 1 carbon atom) a linear or branched linear or branched alkyl group having 1 or 3 carbon atoms substituted by 1 or 2 alkoxy groups, or a haloalkoxy fluorenyl group (in the same or a straight or branched linear or branched carbon atom having a carbon number of 1 to 4, which is substituted by 1 or 9 halogen atoms, and substituted by 1 or 2 haloalkoxy groups. a branched alkyl group), an alkylthioalkyl group (having a linear or branched carbon number of 1 to 8 and having 1 or 3 carbon atoms substituted by 1 or 2 alkylthio groups) Linear or branched alkyl), dialkoxy condensate a group (a linear or branched alkoxy group having 1 to 8 carbon atoms substituted with a dialkoxymethyl group at 2 methyl positions), an alkoxyalkoxy group (having a carbon number) a linear or branched linear or branched alkoxy group having 1 to 3 carbon atoms substituted by 1 or 2 alkoxy groups, 1 to 8 or a cyanoalkyl group 1 or 2 cyano substituted linear or branched alkyl groups having 1 to 3 carbon atoms, halogen, cyano, nitro, amine 'hydroxyl, halosulfonyl, benzyl , benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzodiazepine Oxalo, imine, A-19- 201238485 thiol (mono CHO), carboxyl (monoCOOH), formamidine (mono NHCHO), cyclic ether and cyclic amine, but with alkoxycarboxy (eg Methoxy carboxyl group, ethoxy carboxyl group), halogen (for example, fluorine atom, chlorine atom, bromine atom), cyano group, hydroxyalkyl group (for example, hydroxymethyl group, hydroxyethyl group), alkoxyalkyl group (methoxy group) Methyl, .B Methyl, methoxyethyl), haloalkyl (eg monofluoromethyl, difluoromethyl, trifluoromethyl, heptafluoroisopropyl), haloalkoxy (eg monofluoromethoxy, Difluoromethoxy, trifluoromethoxy), haloalkoxyalkyl (eg monofluoromethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl) 'cyanoalkyl (e.g., cyanomethyl, cyanoethyl), phenyl, pyridyl, furyl, thiazolyl, pyrimidinyl are preferred. a SiR5R6R7 in R1 (R5, R6, R7 is a linear or branched alkyl group having 1 to 6 carbon atoms, and a linear or branched carbon number of 1 to 3 substituted by one halogen atom. a haloalkyl group, a linear or branched cyanoalkyl group having 1 to 3 carbon atoms substituted by a cyano group, and a phenyl group, and both or all of them may be the same substituent or all The dissimilar substituent may, for example, be a trimethylsulfanyl group, a triethylsulfanyl group, a triisopropyldecylalkyl group, a tert-butyldimethylsilyl group, a tert-butyldiphenylfluorenyl group, or a chlorine. Methyl dimethyl decyl group, aryl propyl dimethyl decyl group, preferably trimethyl decyl group or triethyl decyl group. R2 is preferably a hydrogen atom or a cyano group, a linear or branched alkyl group having 1 to 8 carbon atoms, preferably a methyl group or an ethyl group, or a linear or branched carbon number of 2 to 8. The alkenyl group is preferably a vinyl group or a propylene group. R2 may be a C(0)0R, a C(0)NHR, or an OCNR2 (wherein R represents a linear or branched alkyl group having 1 to 8 carbon atoms, and a carbon atom-20- 201238485 A linear or branched alkenyl group of 2 to 8, a linear or branched alkynyl group having 2 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group, Heteroaryl, preferably phenyl. The halogen atom in R2 may, for example, be a chloride ion, an iodine atom, a bromine atom or a fluorine atom, and preferably a chloride ion or a fluoride ion. The alkoxy group in R2 may, for example, be a methoxy group, an ethoxy group, a n-propylethyl group or an isopropoxy group, and a methoxy group or an ethoxy group is preferred. The haloalkyl group in R2 is preferably a monofluoromethyl group, a difluoromethyl group or a trifluoromethyl group, and the haloalkoxy group is preferably a monofluoromethoxy group, a difluoromethoxy group or a trifluoromethoxy group. In the present invention, the term "alkyl" means a linear or branched alkyl group having a carbon number, and examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, and an isobutyl group. , a second butyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a n-hexyl group, a n-heptyl group or an n-octyl group. In the present invention, the term "alkenyl group" means a linear or branched alkenyl group having 2 to 8 carbon atoms, and examples thereof include a vinyl group, a fluorenyl-propenyl group, a 2 propylene group, an isopropenyl group, and 1 a butenyl group, a 2-butenyl group or a 3-butenyl group. The term "alkynyl" as used in the present invention means a linear or branched alkynyl group having 2 to 8 carbon atoms, and examples thereof include ethynyl group, 2-propynyl group, 2-butynyl group or 3-butyl group. Alkynyl. In the present invention, the term "cycloalkyl" means a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group. In the present invention, the term "cycloalkenyl" means a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include 1-cyclopentyl group, 2-cyclopentyl group, 3-cyclopentyl group, and 1-cyclohexyl-21. - 201238485 base, 2-cyclohexyl or 3-cyclohexyl. The term "heteroatom" as used in the present invention includes a nitrogen atom, an oxygen atom and a sulfur atom. The term "halogen" as used in the present invention includes fluorine, chlorine, bromine and iodine. The term "halogen" in "halogen...." (e.g., haloalkyl) in the present invention includes fluorine, chlorine, bromine and hydrazine. The term "haloalkyl" as used in the present invention means a linear or branched alkyl group having 1 to 4 carbon atoms which is substituted by the same or different 1 to 9 halogen atoms, and examples thereof include monofluoro Methyl, monochloromethyl, monobromomethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, n-heptafluoropropyl or isoheptafluoropropyl, etc. The term "haloalkenyl" in the present invention The present invention is a linear or branched alkenyl group having 2 to 6 carbon atoms which is substituted by the same or different 1 to 4 halogen atoms, and examples thereof include 1,2-difluorovinyl group and 2,2. - Difluorovinyl, 3, 3-difluoro-2-propenyl and the like. The term "alkoxy" as used in the present invention means that the alkyl moiety is in the above-mentioned meaning (institutional group), and the methoxy group is exemplified by, for example, a methoxy group, an ethoxy group, a n-propoxy group, or an isopropoxy group. N-butoxy, second butoxy or tert-butoxy. In the present invention, the term "haloalkoxy" means that the haloalkyl moiety is in the above-mentioned meaning (halogen-based) - 0-yl group, and examples thereof include monofluoromethoxy, difluoromethoxy, and trifluoromethyl. Oxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy. In the present invention, the term "mercapto" or "mercaptoalkyloxy" is used for the term "mercapto", and the term "fluorenyl" is used in the fluorenyl fluorenyl group and the oxy-oxyl group is referred to as -22-201238485. Any of the terms "alkyl group" means a group represented by a CO-group (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms), and examples thereof include an ethyl group and a propionyl group. Base, butyl group or isobutyl group. Further, in the present specification, the aliphatic hydrocarbon group means an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group or a cycloalkynyl group. In the present invention, the term "mercaptoalkoxy" means a linear or branched alkoxy group having 1 to 3 carbon atoms which is substituted by the above one or two mercapto groups, and examples thereof include, for example, Mercaptomethoxy, ethoxylated ethoxy, ethinylpropoxy and the like. In the present invention, the term "methoxy group" means (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) - CO - hydrazine, and examples thereof include an ethoxy group and a propylene group. Base, isopropoxy or p-pentyloxy. In the present invention, the term "nonoxyalkyl group" means a linear or branched garden group having 1 to 3 carbon atoms substituted by the above two or two decyloxy groups, and for example,醯oxymethyl, ethoxylated ethyl or ethoxypropyl propyl and the like. The term "alkylsulfonyl" as used in the present invention means an alkyl group having the above-mentioned meaning of (alkyl)-S〇2- group, and examples thereof include methylsulfonyl, ethylsulfonyl and n-propyl. Alkylsulfonyl or isopropylsulfonyl. The term "alkylsulfonylalkyl" as used in the present invention means a linear or branched hospital base having 1 to 3 carbon atoms substituted by one or two of the above-mentioned substituents. For example, a methyl extended methyl group, a methyl sulfhydryl ethyl group, a methylsulfonyl propyl group, etc. are mentioned. In the present invention, the term "decyloxy" is used to mean - 〇SiR5R6R7 -23- 201238485 (R5, R6, R7 are linear or branched alkyl groups having 1 to 6 carbon atoms, substituted by one halogen atom a linear or branched haloalkyl group having 1 to 3 carbon atoms, a linear or branched cyanoalkyl group having 1 to 3 carbon atoms substituted with one mercapto group, and a phenyl group And wherein two or all of them may be the same substituent or all of the different substituents, and examples thereof include trimethyldecyloxy group, triethyldecyloxy group, triisopropyldecyloxy group, and third member. Butyl dimethyl decyloxy, tert-butyl diphenyl decyloxy, and the like. In the present invention, the term "nonyloxyalkyl" is a straight-chain or branched alkyl group having 1 to 3 carbon atoms which is substituted by the above-described decyloxy group, and examples thereof include trimethyldecyloxy group. A benzyl group, a trimethyl decyloxyethyl group, a trimethyl decyloxy propyl group, a triethyl decyloxymethyl group or a tert-butyl dimethyl decyloxy group. In the present invention, the term "hydroxyalkyl" is a straight-chain or branched alkyl group having 1 or 3 carbon atoms which is substituted by one or two hydroxyl groups, and examples thereof include a hydroxymethyl group and a hydroxyethyl group. Hydroxypropyl and the like. In the present invention, the term "alkoxyalkyl" means a straight or branched alkyl group having 1 to 3 carbon atoms which is substituted by the above one or two alkoxy groups, and examples thereof include methoxy. Methyl, ethoxymethyl, propoxymethyl or isopropoxymethyl and the like. In the present invention, the term "alkylthio" means that the alkyl moiety has the above-mentioned meaning (hospital group) - S-group, and examples thereof include a methylthio group, an ethylthio group, a propylthio group and the like. The term "alkylthioalkyl" as used in the present invention means a linear or branched alkane-24-201238485 group having 1 to 3 carbon atoms substituted by the above one or two alkylthio groups. For example, methylthiomethyl 'ethylthiomethyl, methylthioethyl or ethylthioethyl is exemplified. In the present invention, the term "dialkoxyacetal group" means a dialkoxymethyl group in which the above alkoxy group is substituted at two methyl positions, and examples thereof include a dimethoxymethyl group. Diethoxymethyl or dipropoxymethyl and the like. In the present invention, the term "alkoxyalkoxy" means a linear or branched alkoxy group having 1 to 3 carbon atoms which is substituted by the above one or two alkoxy groups, and may be mentioned. For example, methoxymethoxy, methoxyethoxy or methoxypropoxy. The term "haloalkoxyalkyl" as used in the present invention means a linear or branched alkyl group having 1 to 3 carbon atoms substituted by the above one or two haloalkoxy groups, and examples thereof include For example, monofluoromethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl, and the like. The term "cyanoalkyl" as used in the present invention means a linear or branched alkyl group having 1 to 3 carbon atoms substituted by the above one or two cyano groups, and examples thereof include cyanomethyl group. Base, cyanoethyl or cyanopropyl group. In the present invention, "phenyl", "thienyl", "pyridyl", "oxazolyl", "furyl", "thiazolyl", "naphthyl", "pyrimidinyl", "benzothiazolyl" The "benzoxazolyl group" and the "benzodioxan group" may have one or more substituents which may be the same or different, or may have no substituent. The term "phenoxy" as used in the present invention means a phenoxy group and an unsubstituted phenoxy group having one or more substituents which may be the same or different. The term "benzyl" as used in the present invention means a benzyl group and an unsubstituted benzyl group having one or more substituents having the same or different -25 to 201238485. The term "benzyloxy" as used in the present invention means a benzyloxy group having the same or different one or more substituents and an unsubstituted benzyloxy group. The term "propynyl" as used in the present invention means a propynyl group having a substituent at the alkane terminal and an unsubstituted propynyl group. The term "propynyloxy" used in the present invention means a propynyloxy group having a substituent at the alkane terminal and an unsubstituted propynyloxy group. The term "heteroaryl" used in the present invention means oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrimidinyl, pyrazinyl, quinoxalinyl, quinazolinyl, quinolyl, Isoquinolyl, indenyl, isodecyl, imidazolyl, pyrazolyl, pyridyl, furyl, thienyl, pyrrolyl. These groups may have one or more substituents which may be the same or different, or may have no substituent. The term "cyclic ether" used in the present invention means an epoxy group, an oxetane, tetrahydrofuran, tetrahydropyran, dioxolane or dioxane. In the present invention, the term "cyclic amine" means a pyrrolidinyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a piperazinyl group or a morpholinyl group. In the present invention, the term "imine" means a chain quinone imine or a cyclic quinone imine. Since the compound of the present invention represented by the formula [] has an amine group, the acid addition salts derived therefrom are also included in the present invention. Examples of the acid forming the acid addition salt include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, and phosphoric acid; formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, aconitic acid, and oleic acid. Such as carboxylic acid, methanesulfonic acid, benzenesulfonic acid, -26- 201238485 p-sulfonic acid such as mono-toluenesulfonic acid, or saccharin. The compound R2 of the present invention represented by the formula [I] is an R, an OR, a C(0)0R, a C(0)NHR, a CONR2 (wherein the R is a carbon atom of 1 to 8). a chain or branched alkyl group, a linear or branched alkenyl group having 2 to 8 carbon atoms, a linear or branched alkynyl group having 2 to 8 carbon atoms or a carbon atom number of 3 Cycloalkyl group of -8, hydroxyalkyl group (linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), alkoxyalkyl group (1 part) Or a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched alkoxy group having 1 to 8 carbon atoms, a phenyl group, a heteroaryl group, Halogen, cyano, haloalkyl (linear or branched alkyl having 1 to 4 carbon atoms substituted by the same or different 1 to 9 halogen atoms), haloalkoxy Or an optical isomer derived from an asymmetric carbon atom, which is produced by a different linear or branched alkoxy group having 1 to 4 carbon atoms substituted by 1 to 9 halogen atoms) Any of a body or a mixture of such are included in the present invention. The compound [I] of the present invention represented by the following formula can be, for example, as shown in the following reaction step, by, for example, a chloropyrimidine derivative represented by the formula [Π] and a 3-butyne represented by the formula [瓜] The amine derivative is produced by reacting in the presence of a base and a solvent. [Chemical 2]

(式中，R1、R2係與前述同義。） -27- 201238485 溶劑種類只要是不對本反應產生直接關係者則無特別 限定，可舉出例如苯、甲苯、二甲苯、甲基萘、石油醚' 石油腦、己烷、氯苯、二氯苯、氯仿、二氯乙烷、三氯乙 烷之經氯化或未經氯化之芳香族、脂肪族或脂環式烴類， 四氫呋喃、二噁烷、二***等醚類，乙腈、丙腈等腈類， 丙酮、甲基乙基酮等酮類、N，N-二甲基甲醯胺、N，N-二 甲基乙醯胺、N-甲基吡咯啶酮等醯胺化合物，二甲基亞楓 等磺醯基化合物，N，N-二甲基咪唑啶酮等脲化合物，環 丁颯或前述溶劑之混合物等，但以N，N-二甲基甲醯胺、 N，N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺化合物較佳 〇 溶劑使用量可以使化合物[Π]成爲5〜80重量％之方式 使用，但較佳係10〜70重量％ ^ 並無特別限制鹼種類，有機及無機鹼可舉出例如三級 胺（三乙胺等）、DBU等有機鹼、鹼金屬及鹼土類金屬之氫 化物、氫氧化物' 碳酸鹽、碳酸氫鹽等無機鹼，但以三級 胺（三乙胺等）、DBU等有機鹼較佳》 鹼之使用量相對於化合物[Π ]1.0莫耳爲1 .〇〜5.0莫耳 ，以1 .2〜2.0莫耳爲佳。 原料化合物之使用量相對於化合物[Π ]1.〇莫耳，化 合物[ΠΓ ]爲1 ·0〜5.0莫耳，以1.0〜1 .2莫耳爲佳。 並未特別限定反應溫度，爲自室溫至所使用溶劑之沸 點溫度以下之溫度範圍，以60〜1 1 0°C爲佳。 反應時間依據前述之濃度、溫度而變化，但通常是 -28- 201238485 0.5〜8小時。 如上述製造之化合物[I]係在反應結束後進行萃取、 濃縮、過濾等一般的後處理，且可因應需要以再結晶、各 種層析等習知方法進行純化。 另外，如上述製造之化合物[I]爲末端炔烴時（Ι^ = Η) ，亦可利用菌頭反應（Sonogashira reaction)等導入取代基 【化3】(In the formula, R1 and R2 are synonymous with the above.) -27- 201238485 The solvent type is not particularly limited as long as it does not directly affect the reaction, and examples thereof include benzene, toluene, xylene, methylnaphthalene, and petroleum ether. ' Petroleum, hexane, chlorobenzene, dichlorobenzene, chloroform, dichloroethane, trichloroethane, chlorinated or unchlorinated aromatic, aliphatic or alicyclic hydrocarbons, tetrahydrofuran, two Ethers such as oxane and diethyl ether, nitriles such as acetonitrile and propionitrile, ketones such as acetone and methyl ethyl ketone, N,N-dimethylformamide, and N,N-dimethylacetamide. a guanamine compound such as N-methylpyrrolidone, a sulfonyl compound such as dimethyl sulfoxide, a urea compound such as N,N-dimethylimidazolidone, a mixture of cyclobutyl hydrazine or the aforementioned solvent, but N A guanamine compound such as N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone is preferably used in an amount such that the compound [Π] becomes 5 to 80% by weight. The method is preferably used in an amount of 10 to 70% by weight. The type of the base is not particularly limited, and examples of the organic and inorganic bases include tertiary amines (triethylamine, etc.). An organic base such as an organic base such as DBU, a hydride of an alkali metal or an alkaline earth metal, or an inorganic base such as a hydroxide, a carbonate or a hydrogencarbonate, but preferably an organic base such as a tertiary amine (triethylamine or the like) or DBU. The amount of use relative to the compound [Π] 1.0 mole is 1. 〇 ~ 5.0 moles, preferably 1.2 to 2.0 moles. The amount of the raw material compound used is 1.0 to 1.2 mol per mol of the compound [Π]1. 〇mol, and the compound [ΠΓ] is preferably 1.0 to 1.2 mol. The reaction temperature is not particularly limited, and is preferably from 60 to 110 ° C in a temperature range from room temperature to a boiling point of the solvent to be used. The reaction time varies depending on the aforementioned concentration and temperature, but is usually -28 - 201238485 0.5 to 8 hours. The compound [I] produced as described above is subjected to general post-treatment such as extraction, concentration, filtration, etc. after the completion of the reaction, and may be purified by a conventional method such as recrystallization or various chromatography as needed. Further, when the compound [I] produced as described above is a terminal alkyne (Ι^ = Η), a substituent may be introduced by a Sonogashira reaction or the like.

(式中X爲碘、溴或氯，R1係苯基、雜芳基、烯基，R2係 與前述同義。） 本合成法中使用之化合物[Π ]可以例如 W020 1 0/2545 1記載之方法爲準，以下式所示之方法製造 【化4】(wherein X is iodine, bromine or chlorine, R1 is a phenyl group, a heteroaryl group or an alkenyl group, and R2 is synonymous with the above.) The compound [Π] used in the present synthesis method can be described, for example, in W020 1 0/2545 1 The method is based on the method shown in the following formula.

本合成中使用之3-丁炔胺衍生物[瓜]可使用市售品， 但若需要可以下述方法爲準進行製造。然而以下所述之方 -29- 201238485 法並非限制本發明之範圍者。 (合成法1) N-(3-丁炔基）-苯二醯亞胺衍生物[VD ]，及碘化或溴 化苯、碘化、溴化或氯化雜芳基、碘化或溴化烯[IV ]進行 菌頭反應後，藉由以聯胺（hydrazine)或以驗使生成物[爾] 脫保護，可製造3-丁炔胺衍生物[ΠΙ]。 【化51Commercially available products can be used as the 3-butynylamine derivative [melon] used in the present synthesis, but if necessary, it can be produced by the following method. However, the method -29-201238485 described below is not intended to limit the scope of the invention. (Synthesis Method 1) N-(3-butynyl)-benzodiazepine derivative [VD], and iodinated or brominated benzene, iodinated, brominated or chlorinated heteroaryl, iodinated or bromine After the bacterio[4] is subjected to the bacterial head reaction, the 3-butynylamine derivative [ΠΙ] can be produced by deprotection with hydrazine or by the test product [er]. 【化51

[VII] 【IV] [VIII][VII] [IV] [VIII]

[III】 hydrazine or base[III] hydrazine or base

H2N (式中X爲碘、溴或氯，R1係苯基、雜芳基、烯基，R2係 與前述同義。） (合成法2) 自經取代之丁炔基醇[K]與苯二醯亞胺[X]藉由光延 反應（二信反應，Mitsunobu reaction)合成產物[W]，使產 物[VD]與合成法1相同，進行菌頭反應、脫保護，可製造 3·丁炔胺衍生物[m -30- 201238485 【化6】 Ο ΟH2N (wherein X is iodine, bromine or chlorine, R1 is phenyl, heteroaryl, alkenyl, and R2 is synonymous with the above.) (Synthesis 2) Self-substituted butynyl alcohol [K] and benzene The fluorene imine [X] synthesizes the product [W] by a Mitsunobu reaction, and the product [VD] is synthesized in the same manner as in the synthesis method 1, and the head reaction and deprotection are carried out to produce 3·butynylamine. Derivative [m -30- 201238485 [化6] Ο Ο

[IV] 【III] (式中X爲碘、溴或氯，R1係苯基、雜芳基、烯基，R2係 與前述同義。） (合成法3) 使末端炔烴[XI]與格蘭納試劑反應後，進而與環氧乙 烷[XII]反應，合成3-丁炔基醇衍生物[XIII]。其後，使該 醇類進行光延反應、脫保護，可製造3-丁炔胺衍生物[瓜] 【化7】 R2 R1^ [XI】[IV] [III] (wherein X is iodine, bromine or chlorine, R1 is phenyl, heteroaryl, alkenyl, and R2 is synonymous with the above.) (Synthesis 3) The terminal alkyne [XI] After the reaction of the Lanna reagent, it is further reacted with ethylene oxide [XII] to synthesize the 3-butynyl alcohol derivative [XIII]. Thereafter, the alcohol is subjected to a light delay reaction and deprotection to produce a 3-butynylamine derivative [melon] [Chemical 7] R2 R1^ [XI]

RMgXRMgX

[XII][XII]

HOHO

[XIII】 R1 hydrazine or base -^[XIII] R1 hydrazine or base -^

R1 [III]R1 [III]

Mitsunobu reaction (式中X爲碘、溴或氯，R1及R2係與前述同義。） -31 - 201238485 (合成法4) 以甲苯磺醯基保護經取代之丁炔基醇[K ]後，利用烷 «ϋ在末端炔烴碳上產生陰離子，藉由親核取代反應於末 端炔烴碳上導入取代基，製造產物[XV]。其後，於碘化鉀 存在下使其與苯二醯亞鉀胺[XVI]，獲得產物[Vi ]。其後 ’藉由進行脫保護，可製造3-丁炔胺衍生物[皿]。 【化8 ]Mitsunobu reaction (wherein X is iodine, bromine or chlorine, and R1 and R2 are synonymous with the above.) -31 - 201238485 (Synthesis Method 4) After protecting the substituted butynyl alcohol [K] with toluenesulfonyl group, use The alkane «ϋ produces an anion on the terminal alkyne carbon, and the substituent [XV] is produced by introducing a substituent on the terminal alkyne carbon by a nucleophilic substitution reaction. Thereafter, it was combined with benzodiazepine amine [XVI] in the presence of potassium iodide to obtain the product [Vi]. Thereafter, by performing deprotection, a 3-butynylamine derivative [dish] can be produced. [化8]

[IX][IX]

TsCI -> baseTsCI -> base

TsOTsO

RLi R1-X IXIV] -►RLi R1-X IXIV] -►

TsOTsO

R1 【XV】R1 [XV]

(式中X爲碘、溴或氯，R1係三烷基矽烷基，R2係與前述 同義。） (合成法5) 使以甲苯磺醯基保護經取代之丁炔基醇[XIII]之化合 物[XVII]與疊氮化鈉反應，製造疊氮化合物[XVIII]。其後 ’藉由以氫化鋁鋰使該疊氮化合物[XV III]還原，可製造 3-丁炔胺衍生物[瓜]。 -32- 201238485 【化9】(wherein X is iodine, bromine or chlorine, R1 is a trialkylsulfanyl group, and R2 is synonymous with the above.) (Synthesis Method 5) A compound which protects a substituted butynyl alcohol [XIII] with a toluenesulfonyl group [XVII] is reacted with sodium azide to produce an azide compound [XVIII]. Thereafter, the 3-butynylamine derivative [melon] can be produced by reducing the azide compound [XV III] with lithium aluminum hydride. -32- 201238485 【化9】

TsCI baseTsCI base

NaNi [XVII]NaNi [XVII]

[XV 川][XV Chuan]

LiAIH4 f ^R1 [Hi] (式中R1及R2係與前述同義。） (合成法6) 自4-戊基醯胺[XIX]藉由霍夫曼（Hofmann)轉移，可製 造3 - 丁炔胺衍生物[皿]。 【化1 0】 X ^R1 base,x2 ^ X ^R1 h2noc^^^---LiAIH4 f ^R1 [Hi] (wherein R1 and R2 are synonymous with the above.) (Synthesis 6) From 4-pentyl decylamine [XIX] by Hofmann transfer, 3 - butyne can be produced. Amine derivative [dish]. [化1 0] X ^R1 base,x2 ^ X ^R1 h2noc^^^---

[XIX] 【川I (式中R1及R2係與前述同義。） (合成法7) 自疊氮化醯[XX]藉由克提思（Curtius)轉移，可製造3-丁炔胺衍生物[瓜]。 【化1 1】 n3oc[XIX] [Chuan I (wherein R1 and R2 are synonymous with the above.) (Synthesis method 7) Self-sodium azide [XX] can be produced by Curtius transfer to produce 3-butynylamine derivatives. [melon]. [1 1] n3oc

[XX] h20 严[XX] h20 strict

R1 [III] -33 - 201238485 (式中R1及R2係與前述同義。） (合成法8) 使以甲苯磺醯基保護經取代之丁炔基醇[XIII]之化合 物[XVII]與氨水反應，可製造3-丁炔胺衍生物[瓜]。 【化1 2】R1 [III] -33 - 201238485 (wherein R1 and R2 are synonymous with the above.) (Synthesis Method 8) Reacting a compound [XVII] with a toluenesulfonyl group-protected butynyl alcohol [XIII] with aqueous ammonia A 3-butynylamine derivative [melon] can be produced. [1 2]

TsCI -► baseTsCI -► base

TsOTsO

NH4〇H [XVII ]NH4〇H [XVII ]

H2N (式中R1及R2係與前述同義。） [防治效果] 本發明中以通式[1-1] [1-2]所示之含氟衍生物對於有害 生物具有極佳之防治活性。本發明中稱爲「有害生物」之 用語包含對於農園藝用植物之所有病原菌，及對於農園藝 用植物之所有病蟲害、蟎類等。 (對於農園藝用植物之病原菌） 對於農園藝用植物之病原菌之例，包含屬於卵菌類 (Oomycetes)、子漢菌類（Ascomycetes)、不完全菌類 (Deuteromycetes)、擔子菌類（Basidiomycetes)以及細菌類 等，使用於本發明之含氟喹唑啉衍生物，可防治起因於該 等病原菌類之植物的病害。以下具體舉出菌名之例，但並 非限定於此。 -34- 201238485 農園藝病原菌可舉出例如稻瘟病（Pyricularia oryzae) 、稻胡麻葉枯病（Cochliobolus miyabeanus)、稻紋枯病 (Rhizoctonia solani)、稻馬鹿苗病（Gibberellafujikuroi)、 大麥白粉病（Erysiphe graminis f.sp. tritici)、小麥白粉病 (Erysiphe graminis f.sp. hordei) 小麥眼紋病 (Pseudocercosporella herpotrichoides)、小麥黑鏽病 (puccinia graminis)、 小麥炭疽病（Colletotrichum graminicola)、小麥枯葉病（Septoria tritici)、小麥雲形病 (Phynchosporium secalis f.sp. hordei)、馬鈴薯疫病 (Phytophthora infestans) ' 馬鈴薯夏疫病（Alternari solani) 、馬鈴薯炭疽病（Colletotrichum atramentarium )、馬鈴薯 黑枯病（Thanatephorus cucumeris)、馬鈴薯灰霉病 (Botrytis cinerea)、赤豆白粉病（Erisiphe pisi)、赤豆褐斑 病（C e r c o s p o r a c a n e s c e n s)、赤豆菌核病（S c 1 e r o t i n i a sclerotiorum)、赤豆炭疽病（Colletotrichum phaseolorum) 、菜豆褐斑病（Cercospora canescens)、菜豆菌核病 (Sclerotinia sclerotiorum)、菜豆炭疽病（Colletotrichum lindemuthiamum)、菜豆灰霉病（Botrytis cinerea)、大豆炭 疽病（Colletotrichum truncatum)、大豆紫斑病（Cercospora k i k u c h i i)、大 鏽病（P h a k o p s o r a p a c h y r h i z i)、荷薦炭疽 病（Gloeosporium conjac)、詢篛褐斑病（Septoria perillae) 、茶炭疽病（Colletotrichum theae-sinensis)、疲菜褐斑病 (Cercospora beticola)、菠菜炭疽病（Colletotrichum spinaciae)、菠菜霜霉病（Peronospora effusa)、高麗菜黑 -35- 201238485 斑病（Alternaria brassicae)、高麗菜黑斑病（Alternaria brassicicola)、高麗菜菌核病（Sclerotinia sclerotiorum)、 高麗菜灰霉病（Botrytis cinerea)、高麗菜黑腐病 (Xanthomonas campestris pv. C am p e s t r i s)、蘿蔔軟腐病 (Erwinia carotovora)、小松菜炭疽病（Colletotrichum higginsianum)、白菜菌核病（Sclerotinia sclerotiorum)、 白菜黑斑病（Alternaria brassicae 、 Alternaria brassicicola)、南瓜黑斑病（Alternaria cucumerina)、南瓜 灰霉病(Botrytis cinerea)、露菌病(Pseudoperonospora cubensis)、小黃瓜白粉病（Sphaerotheca fuliginea)、小黃 瓜疫病（Phytophthora melonis)、 小黃瓜褐斑病 (Corynespora cassiicola)、小黃瓜菌核病（Sclerotinia sclerotiorum)、小黃瓜黑斑病（Alternaria cucumerina)、小 黃瓜炭疽病（Colletotrichum lagenarium)、小黃瓜枯萎病 (Fusarium oxysporum f.sp. cucumerinum)、小黃瓜苗立枯 病（Phythium cucurbitacearum、Rhyzoctonia solani)、小黃 瓜灰霉病（Botrytis cinerea)、小黃瓜小黑點病（Phomopsis sp·)、露菌病（Pseudoperonospora cubensis)、小黃瓜菌斑 病（Pseudomonas syringae)、西瓜褐斑病（Sphaerotheca fuliginea)、西瓜疫病（Phytophthora cryptogea)、西瓜菌核 病（Sclerotinia sclerotiorum)、西瓜炭疽病（Colletotrichum orbiculare)、露菌病（Pseudoperonospora cubensis)、哈密 瓜褐斑病（Corynespora cassiicola)、哈密瓜菌核病 (Sclerotinia sclerotiorum)、哈密瓜枯萎病（Fusarium -36- 201238485 oxysporum f. sp . melonis)、露菌病(Pseudoperonospora cubensis)、春菊枯萎病（Fusarium oxysporum)、春菊菌核 病(Sclerotinia sclerotiorum)、春菊鏽病(Puccinia cnici-oleracei)、春菊炭疽病(Gloeosporium chrysanthemi、 Gloeosporium carthami)、胡蘿蔔枯萎病（Fusarium oxysporum)、胡蘿蔔白粉病（Erysipheheraclei)、胡蘿蔔菌 核病（S c 1 erotini a intermedia、Sclerotinia sclerotiorum)、 胡蘿蔔黑葉枯病（Alternaria dauci)、胡蘿蔔黑斑病 (Alternaria radicina)、辣椒·青椒枯萎病（Fusarium oxysporum)、辣椒·青椒白粉病（Oidiopsis sicula)、辣椒 •青椒疫病（Phytophthora capsici)、辣椒•青椒菌核病 (Sclerotinia sclerotiorum)、辣椒·青椒炭疽病 (Colletotrichum gloeosporioides)、辣椒.青椒灰霉病 (Botrytis cinerea)、番節枯萎病（Fusarium oxysporum f.sp. lycopersici)、番節白粉病（Oidiopsis sicula)、番節疫病 (Phytophthora infestans)、番節菌核病（S c 1 er ot inia sclerotiorum)、番節灰霉病（Botrytis cinerea)、番節葉鏽 病（Fulvia fulva)、前子疫病（Phytophthora infestans)、前 子褐斑病（Thanatephorus cucumeris)、前子褐腐病 (Phytophthora capsici) 節子菌核病（Sclerotinia sclerotiorum)、琉子褐斑病（Alternaria solani)、草莓枯黃 病（Fusarium oxysporum)、草莓枯萎病（Vertici 11 ium dahliae)、草莓白粉病（Sphaerotheca humuli)、草莓疫病 (Phytophthora nicotianae var. parasitica)、草莓果實腐敗 i? -37- 201238485 病（Pythium ultimum var. ultimum)、草莓菌核病 (Sclerotinia sclerotiorum)、草莓黑斑病（Alternaria a 11 e r n a t a)、草莓蛇目病（M y c o s p h a e r e 11 a f r a g a r i a e)、草莓 炭.疽病(Colletotrichum acutatum、Glomerella cingulata) 、草莓灰霉病（Botrytis cinerea)、蘆荀褐斑病（Cercospora asparagi)、藍荀莖枯病（Phomopsis asparagi)、蘆筍鏽病 (Puccinia asparagi-lucidi)、蘆荀炭疽病（Colletotrichum gloeosporioides)、蘆荀灰霉病（Botrytis cinerea)、洋憩疫 病（Phytophthora nicotianae)、洋惡黃斑病（Cladosporium allii-cepae)、洋憩乾腐病（Fusarium oxysporum f.sp. cerae)、洋蔥菌核病（Sclerotinia sclerotiorum)、洋菌黑點 葉枯病（Septoria alliacea)、洋菌偽黑斑病（Alternaria porri)、洋蔥鏽病（Puccinia allii)、洋菌小菌核病（Puccinia allii)、洋菌小菌核性腐敗病（Botrytis squamosa)、洋憩白 色疫病（Phytophthora parri) ' 洋菌炭疽病（Colletotrichum circinans)、洋蔥黑斑病（Alternaria sp.)、洋菌灰霉病 (Botrytis cinerea)、洋蔥灰腐病（Botrytis allii)、洋悪葉枯 病（Pleospora herbarum)、洋蔥白粉病（Peronospora destructor)、韭菜鏽病（Puccinia allii)、韭菜白斑葉枯病 (Botrytis byssoidea)、藤疫病（Phytophthora nicotianae)、 菌枯萎病 （Fusarium oxysporum) 憩疫霉病 (Mycosphaerella allicina)、菌黑點葉枯病（Septria alliacea)、蔥黑斑病（Alternaria porri)、憩小菌核病 (Sclerotinia allii)、蔥鏽病（Puccinia allii)、憩小菌核腐 -38- 201238485 病（Botrytis squamosa)、蔥白色疫病（Phythoththora parri) 、菌炭疽病（Colletotrichum circinans)、菌露菌病 (P e r ο η o s p o r a d e s t r u c t o r)、芒果炭疽病（C ο 11 e t o t r i c h u m gloeosporioides)、柿子白粉病（Phyllactinia kakikola)、柿 子污染果病（Colletotrichum ssp.、Glomerella sp·)、柿子 角斑病（Cercospora kakivora)、 柿子角斑落葉病 (Cercosporakaki)、柿子褐紋病（Macrophoma kaki)、柿子 黑星病（Fusicladium levieri)、柿子黑點病（Phomopsis kakivora)、柿子黑斑病（Pseudocercospora fuliginosa)、柿 子縮葉病（Physalospora kaki)、柿子蒂枯病（Aureobasidium p u 11 u 1 a n s 、 Capnophaeum fuliginodes 、 Cladosporium herbarum 、 Microxyphium s p. 、 Scorias communis 'H2N (wherein R1 and R2 are synonymous with the above.) [Control effect] The fluorine-containing derivative represented by the general formula [1-1] [1-2] has excellent control activity against harmful organisms in the present invention. The term "harmful organism" as used in the present invention includes all pathogens for agricultural and horticultural plants, and all pests, mites, and the like for agricultural and horticultural plants. (Pathogens for agricultural and horticultural plants) Examples of pathogenic bacteria for agricultural and horticultural plants include Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, and bacteria. The fluoroquinazoline derivative used in the present invention can prevent diseases caused by plants of the pathogenic fungi. The examples of the fungus name are specifically described below, but are not limited thereto. -34- 201238485 Agricultural and horticultural pathogens include, for example, Pyricularia oryzae, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi, and barley powdery mildew (Erysiphe) Graminis f.sp. tritici), wheat white powdery disease (Erysiphe graminis f.sp. hordei) wheat eyelid disease (Pseudocercosporella herpotrichoides), wheat black rust (puccinia graminis), wheat anthracnose (Colletotrichum graminicola), wheat dead leaf disease (Septoria Tritici), Phynchosporium secalis f.sp. hordei, Phytophthora infestans 'Alternari solani, Colletotrichum atramentarium, Thanatephorus cucumeris, potato ash Mold disease (Botrytis cinerea), Erisiphe pisi, C ercosporacanescens, S c 1 erotinia sclerotiorum, Colletotrichum phaseolorum, Bean brown Spot disease (Cercos Pora canescens), Sclerotinia sclerotiorum, Colletotrichum lindemuthiamum, Botrytis cinerea, Colletotrichum truncatum, Cercospora kikuchii, Large rust Hakopsorapachyrhizi), Gloeosporium conjac, Septoria perillae, Colletotrichum theae-sinensis, Cercospora beticola, Colletotrichum spinaciae, Spinach downy mildew (Peronospora effusa), Korean cabbage black-35- 201238485 Alternaria brassicae, Alternaria brassicicola, Sclerotinia sclerotiorum, Botrytis Cinerea), Xanthomonas campestris pv. C am pestris, Erwinia carotovora, Colletotrichum higginsianum, Sclerotinia sclerotiorum, Alternaria brass Icae, Alternaria brassicicola), Alternaria cucumerina, Botrytis cinerea, Pseudoperonospora cubensis, Sphaerotheca fuliginea, Phytophthora melonis, small Cuyne brown leaf spot (Corynespora cassiicola), Sclerotinia sclerotiorum, Alternaria cucumerina, Colletotrichum lagenarium, Cucumber wilt (Fusarium oxysporum f.sp. cucumerinum ), Cucumber seedling blight (Phythium cucurbitacearum, Rhyzoctonia solani), Botrytis cinerea, Phomopsis sp., Pseudoperonospora cubensis, Cucumber plaque Disease (Pseudomonas syringae), watermelon brown spot disease (Sphaerotheca fuliginea), watermelon Phytophthora cryptogea, Sclerotinia sclerotiorum, watermelon anthracnose (Colletotrichum orbiculare), bacterium (Pseudoperonospora cubensis), cantaloupe brown spot Disease (Corynespora Cassiicola), Sclerotinia sclerotiorum, cantaloupe wilt (Fusarium -36- 201238485 oxysporum f. sp . melonis), bacterium (Pseudoperonospora cubensis), chrysanthemum blight (Fusarium oxysporum), chrysanthemum sclerotinia ( Sclerotinia sclerotiorum), Puccinia cnici-oleracei, Gloeosporium chrysanthemi, Gloeosporium carthami, Fusarium oxysporum, Erysipheheraclei, Sc 1 erotini a intermedia , Sclerotinia sclerotiorum), Alternaria dauci, Alternaria radicina, Fusarium oxysporum, Oidopsis sicula, Chili • Green pepper blight (Phytophthora) Capsici), pepper, Sclerotinia sclerotiorum, pepper, Colletotrichum gloeosporioides, pepper, Botrytis cinerea, Fusarium oxysporum f.sp. lycopersici Powdery mildew (Oi Diopsis sicula), Phytophthora infestans, S c 1 er ot inia sclerotiorum, Botrytis cinerea, Fulvia fulva, anterior blight Phytophthora infestans), Thanatephorus cucumeris, Phytophthora capsici, Sclerotinia sclerotiorum, Alternaria solani, Fusarium oxysporum, Strawberry Futici 11 ium dahliae, Sphaerotheca humuli, Phytophthora nicotianae var. parasitica, strawberry fruit spoilage i? -37- 201238485 disease (Pythium ultimum var. ultimum), strawberry sclerotinia ( Sclerotinia sclerotiorum), Alternaria a 11 ernata, M ycosphaere 11 afragariae, strawberry charcoal, Colletotrichum acutatum, Glomerella cingulata, Botrytis cinerea, reed brown Spot disease (Cercospora asparagi), Phomopsis asparagi, Puccinia asparagi-lucidi, Colletotrichum gloeosporioides, Botrytis cinerea, Phytophthora nicotianae, Cladosporium allii-cepae, artichoke Rosar (Fusarium oxysporum f.sp. cerae), Sclerotinia sclerotiorum, Septoria alliacea, Alternaria porri, Onion rust (Puccinia allii) , Puccinia allii, Botrytis squamosa, Phytophthora parri 'Colletotrichum circinans, onion black spot (Alternaria sp .), Botrytis cinerea, Botrytis allii, Pleospora herbarum, Peronospora destructor, Puccinia allii, Amaranth leucocephala Bacterial disease (Botrytis byssoidea), Phytophthora nicotianae, Fusarium oxysporum, Mycosphaerella allic Ina), Septi alliacea, Alternaria porri, Sclerotinia allii, Puccinia allii, 憩 菌 核-38- 201238485 (Botrytis squamosa), Phythoththora parri, Colletotrichum circinans, P er ο η osporadestructor, mango anthracnose (C ο 11 etotrichum gloeosporioides), persimmon powdery mildew (Phyllactinia kakikola ), persimmon pollution fruit disease (Colletotrichum ssp., Glomerella sp.), persimmon keratosis (Cercospora kakivora), persimmon keratosis (Cercosporakaki), persimmon brown disease (Macrophoma kaki), persimmon black spot disease (Fusicladium levieri) ), Phomopsis kakivora, Pseudocercospora fuliginosa, Physalospora kaki, Persimmon blight (Aureobasidium pu 11 u 1 ans, Capnophaeum fuliginodes, Cladosporium herbarum, Microxyphium s p . , Scorias communis '

Tripospermum juglandis)、柿子蒂枯點病（Zygophiala jamaicensis)、柿子炭疽病（Gloeosporium kaki)、柿子灰霉 病（Botrytis cinerea)、柿子葉枯病（Pestalotia diospyri)、 柿子葉炭疽病（Glomerella cingulata)、柿子圓星落葉病 (Mycosphaerella nawae)、青梅白粉病（P o d o s p h a e r a tridactyla 、 Sphaerotheca pannosa)、青梅枯枝病 (Botryosphaeria dothidea)、青梅菌核病（Sclerotinia sclerotiorum)' 青梅黑星病（Cladosporium carpophilum)、 青梅白鏽病（Leucotelium pruni-persicae)、青梅白紋羽病 (Rosellinia necatrix)、青梅腐心病（Fusari.u.m lateritium)、 青梅褐斑穿孔病（Pseudocercospora circumscissa)、青梅縮 牙病（Sphaceloma pruni-domesticae)、青梅炭疽病 -39 - 201238485 (Glomerella cingulata)、青梅灰霉病（Botrytis cinerea)、 青梅灰星病（Monilinia fructicola、Monilinia laxa)、青梅 葉炭疽病（Glomerella mume)、楼桃菌核病（Sclerotinia sclerotiorum)、櫻桃白粉病（Podosphaera tridactyla)、櫻 桃黑鏽病（Rhizopus nigricans)、櫻桃炭疽病（Glomerella cingulata)、櫻桃黑霉病（Botrytis cinerea)、櫻桃灰星病 (Monilinia fructicola)、西洋梨白粉病（Phyllactinia mali) 、西洋梨疫病（Phytophthora cactorum、phytophthora syringae)、西洋梨黑星病（Venturia pirina)、西洋梨炭痕 病（C ο 11 e t o t r i c hu m gloeosporioides)、 梨 赤星病 (Gymnosporangium asiaticum)、梨白粉病（Phyllactinia pyri) ' 梨疫病(Phytophthora cactorum 、 Phytophthora syringae)、梨黑星病（Venturia nashicola)、梨黑斑病 (Alternaria kikuchiana)、梨蒂枯病（Leptothyrium pomi)、 梨炭疽病（Glomerella cingulata)、梨灰霉病（Botrytis cinerea)、梨灰星病（Monilinia fructigena)、梨葉炭疽病 (Colletotrichum gloeosporioides)、梨輪紋病（Physalospora piricola)、桃赤鏽病（Fusarium oxysporum、Gibberella zeae)、桃白粉病（Podosphaera tridactyla、Sphaerotheca pannosa)、桃菌核病（Sclerotinia sclerotiorum)、桃黑鏽病 (Rhizopus nigricans)、桃黑星病（Cladosporium carpophilum)、桃白鏽病（Leucotelium pruni-persicae)、桃 蒂枯病（Stenella sp.)、桃褐斑穿孔病（Pseudocercospora circumscissa ' Phyllosticta persicae)、 桃 炭痕病 -40- 201238485 (Gloeosporium laeticolor)、桃灰霉病（Botrytis cinerea)、 桃灰星病（Monilinia fructicola)、桃蒂枯病（Phomopsis sp·)、蘋果赤星病（Gymnosporangium yamadae)、鑛果白粉 病（P o d o s p h a e r a 1 e u c o t r i c h a)、蘋果疫病（P h y t o p h t h o r a cactorum 、 phytophthora cambi vola 、 Phy tophthor a syringae)、蘋果褐斑病（Diplocarpon mali)、鑛果環紋葉枯 病（Cristulariella moricola)、鑛果黑星病（V ent ur i a inaequalis)、鑛果蒂枯病（Zygophiala jamaicensis)、鑛果 炭疽病（Glomerella cingulata)、蘋果灰霉病（Botrytis cinerea)、蘋果斑點落葉病（Alternaria alternata)、葡萄白 粉病（Uncinula necator)、葡萄枝枯菌核病（Sclerotinia sclerotiorum)、葡萄晚腐病（Glomerella cingulata)、葡萄 褐斑病（Pseudocercospora vitis)、葡萄褐斑葉枯病（Briosia ampelophaga)、葡萄黑霉病（Elsinoe ampelina)、葡萄黑腐 病（Phyllosticta ampelicida)、葡萄枯萎病（Phomopsis viticola)、葡萄霜萎病（Plasmopara viticola)、栗子炭疽病 (Glomerella cingulata) 栗子蒂枯病（Capnodium salicinum)、栗子褐斑病（Morenoella quercina)、栗子白粉 病(Microsphaer a alphitoides)、栗子葉枯病（Monochaetia monochaeta)、相橘灰色霉病（Botrytis cinirea)、租橘褐色 腐敗病（Phytophthora citrophthora) ' 根橘黑點病 (Diaporthe citri)、根橘黃斑病（Mycosphaerella citri、 Mycosphaerella horii)、根橘瘡痂病（Elsinoe fawcettii)、 柑橘褐斑病（Mycosphaerella pinodes)、根橘炭疽病 -41 - 201238485 (Colletotrichum gloeosporioides)、 柑橘 鏽果病 (Colletotrichum gloeosporioides)^ ° (對於農園藝植物之病蟲害及蟎類等） 對於農園藝植物之病蟲害及蟎類等之例，包含屬 於半翅目（Hemiptera)、纓尾目（Thysanoptera)、鱗翅目 (Lepidoptera)、蟎蜱亞綱（Acari)等，使用於本發明之含氟 喹唑啉衍生物，可防治起因於該等病蟲害及蟎類之植物的 病害。以下具體舉出病蟲害及蟎類等之例，但並非限定於 此。 病蟲害及蟎類等可舉出例如小菜蛾（Plutella xylostella)、球菜夜蛾（Agrotis ipsilon)、無菁夜蛾 (Agrotis segetum)、番節夜蛾（Helicoverpa armigera)、薛 草夜蛾（Helicoverpa assulta)' 谷實夜蛾（Helicoverpa zea) 、薛牙夜蛾（Heliothis virescens)、甘藍夜蛾（Mamestra brassicae)、稻螺鈴（Naranga aenescens)、黑點銀紋夜蛾 (Plusia nigrisigna)、黏夜蛾（Pseudaletia separata)、甜菜 夜蛾（Spodoptera exigua)、斜紋夜蛾（Spodoptera litura)、 海飛翅夜蛾（Spodoptera littoralis) ' 草地夜蛾（Spodoptera frugiperda)、東方黑翅夜蛾（Spodoptera eridania)、薛草天 蛾（Manduca sexta)、葡萄果實駐蟲（Endopiza viteana)、青 枯葉蛾（Lyonetia prunifoliella malinella)、金紋細蛾 (Phyllonorycter ringoneella)、根橘潛夜蛾（Phyllocnistis citrella)、紅鈴蟲（Pectinophora gossypiella)、桃蛀果蛾 (Carposina niponensis)、茶小卷葉蛾(Adoxophyes orana -42 - 201238485 faciata)、棉褐帶卷蛾（Adoxophyes honmai)、卷葉蛾 (Homona magnamina)、蘋果蠹蛾（Cydla pomonella)、桃析 心蟲（Grapholita molesta) ' 二化膜（Chilosuppressalis)、 瘤野螺（Cnaphalocrocis medinalis)、菜心螟（Hellula undalis)、歐洲玉米螺（Ostrinia nubilalis) ' 大豆夜蛾 (Pseudoplusia includens)、粉紋夜蛾（Trichoplusia ni)、美 國白蛾（Hyphantria cunea)、紋白蝶（Pieris rapaecrucivora) 、直紋稻弄蝶（Parnara guttata)等鱗翅目害蟲，金剛赤龜 (Anomala cuprea)、紅銅麗金龜（Anomala rufocuprea)、日 本金龜子（Popillia japonica)、 科羅拉多金花龜 (Lepinotarsa decemlineata)、墨西哥大豆蟲（Epilachna varivestis)、金針蟲（Melanotus tamsuyensis)、薛草蟲 (Lasioderma serricorne)、出尾蟲（Epuraea domina)、前二 十八星瓢蟲（Henosepilachna vigintioctopunctata)、黃粉蟲 (Tenebrio molitor)、赤擬穀盜（Tribolium castaneum)、星 天牛（Anoplophora malasiaca)、松末天牛（Monochamus alternatus)、綠豆象（Callosobruchus chinensis)、黃守瓜 (Aulacophora femoralis)、稻泥蟲（Oulema oryzae)、黃條 葉备（Phyllotreta striolata)、甘藷蟻象（Cylasformicarius) 、墨西哥棉蛉象（Anthonomus grandis)、 稻象甲 (Ethinocnemus squameus)、苜宿象鼻蟲（Hypera postica)、 水稻水象鼻蟲（Lissorhoptrus oryzophilus)、玉米象 (Sitophilus zeamais)、獵長祿象（Sphenophrus venatus vestius)、穀象（Sitophilus granarius)、斑點黃守瓜 -43- 201238485 (Diabrotica undecimpunctata)、西方玉米根蟲（Diabrotica virgifera)、玉米食根蟲（Diabrotica barberi)、黃翅隱翅蟲 (Paederus fuscipes)鞘翅目等害蟲，甘藍菜幢（Eurydema rugosa)、白星椿象（Eysarcoris ventralis)、茶翅螓 (Halyomorpha mista)、稻綠蝽（Nezara viridula)、中華稻 綠蝽（Leptocorisa chinensis)、點峰綠幢（Riptortus clavatus)、小翅瓢簞長龜蟲（Togo hemipterus)、杜II花冠 網椿（Stephanitis pyrioides)、夜蟬（Epiacanthus stramineus)、小綠葉禪（Empoasca onukii)、馬鈴薯葉蟬 (Empoasca fabae)、黑尾葉蟬（Nephotettix cinctinceps)、 灰飛廢（Laodelphax striatellus)、褐飛蟲（Nilaparvata lugens)、白背飛蟲（Sogatella furcifera)、南非根橘木蟲 (T r i o z a e r y t r e a e)、梨木蟲（P s y 11 a p y r i s u g a)、薛草粉蟲 (Bemisia tabaci)、銀葉粉蟲（Bemisia argentifolii)、棺橘 粉廢(Dialeurodescitri) ' 溫室粉蟲(Trialeurodes vaporariorum)、種棉既（Aphis gossypii)、藤果既（Aphis pomi)、桃赔（Myzus persicae)、草履阶（Drosicha corpulenta)、吹棉介殻蟲（Icerya purchasi)、柑橘粉介殼 蟲（Planococcus citri)、康氏粉阶（Pseudococcus comstocki)、紅獵介殼蟲（Ceroplastes rubens)、箭頭介殼 蟲（Unaspis yanonensis)、溫帶臭蟲（Cimex lectularius)等 半翅目害蟲，西方花薊馬（Frankliniella occidentalis)、台 灣花薊馬（Frankliniella intonsa)、小黃前馬（Scirtothrips dorsalis)、南黃薊馬（Thrips palmi)、憩薊馬（Thrips -44- 201238485 tabaci)等纓尾目害蟲，東方果實蠅（Dacus dorsalis)、瓜 實蠅 （Dacus cucurbitae)、地中海果實蠅（Ceratitis capitata)、麥水蠅（Hydrellia griseola)、番前斑潛蠅 (Liriomyza bryoniae)、非洲菊斑蠅（Liriomyza trifolii)、 灰地種蠅（Hylemya platura)、蘋果果實蠅（Rhagoletis pomonella)、小麥癭蚊 （Mayetiola destructor)、家蠅 (Musca domestica)、願刺蠅（Stomoxys calcitrans)、羊蜱 (Melophagus ovinus)、美國牛蠅（Hypoderma 1 ineatum)、 遭牛蠅（Hypodermabovis)、羊狂蠅（Oestrus ovis)、須舌蠅 (Glossina palpalis, Glossina morsitans)、酪農血蟲 (Prosimulium yezoensis)、三角虫亡（Tabanus trigonus)、白 斑蛾蚋（Telmatoscopus albipunctatus)、日本庫螺 (Leptoconops nipponensis)、淡色庫蚊(Culex pipiens pallens)、白線斑蚊（Aedes albopicutus)、埃及斑蚊（Aedes aegypti)、牛吸血蟲（Anopheles hyracanus sinesis)等雙翅 目害蟲，秋葉蜂（Apethymus kuri)、黃翅菜葉蜂（Athalia rosae japonensis)、黃松葉蜂（Neodiprion sertifer)、布氏 游蚊（Eciton burchelli，Eciton schmitti)、日本弓背蟻 (Camponotus japonicus) ' 大胡蜂（Vespa mandarina)、公牛 蟻（Myrmecia spp.)、火犠類（Solenopsis spp·)、小黃家蟻 (Monomorium pharaonis)等膜翅目害蟲，黑胸大纖 (Periplaneta fuliginosa)、亞熱帶蛮蠊（Periplaneta japonica)、德國小蠊（Blattella germanica)等網翅目害蟲， 黃褐油葫蘆（Teleogryllus emma)、非洲螻蛄（Gryllotalpa -45- 201238485 africana)、飛幢（Locusta migratoria)、小翅稻煌（Oxya yezoensis)、癒疫沙漠媳蟲（Schistocerca gregaria)等直翅 目害蟲，赤目白犠（Coptotermes formosanus)、棲北散白蟻 (Reticulitermes speratus)、黑翅吐白犠（Odontotermes formosanus)等白蟻目害蟲，猫蛋（Ctenocephalidae felis) 、致癖蛋（Pulex irritans)、鼠备（Xenopsylla cheopis)等之 等翅目害蟲，雞體 1¾ (M e n a c a n t h u s s t r a m i n e u s)、牛 1¾ (Bovicola bovis)等之 1¾ 目害蟲，和牛 1¾ (Haematopinus e u r y s t e r n u s)、緖血蟲（H a e m a t o p i n u s s u i s)、長鼻牛 1¾ (Linognathus vituli)、小藍牛蟲（Solenopotes capillatus)等 之1¾目害蟲。觸蜱目方面、柑橘葉觸（Panonychus citri)、 蘋果葉觸（Panonychus ulmi)、神澤葉蟎（Tetranychus kanzawai)、二點葉輸（Tetranychus urticae)等之葉蟎類， 茶橙婁蟎（Acaphylla theae)、皮氏刺皮癭蠘（Aculops pelekassi)' 惹枝酕蟎（Eriophyes chibaensis)、戀金香節蟎 (Aceria tulipae)等僞足癭蟎亞科類，茶蚶線蟎 (Polyphaotarsonemus latus) 、 仙 客 來 細 礒 (S teneotarsonemus pallidus)等線輸類，腐餓酷蟎 (Tyrophagus putrescentiae)、唐菖蒲根（Rhizoglyphus robini)等恙蟲類，大蜂蛹（Varroa jacobsoni)等蟎類，微小 牛蜱（Boophilus microplus)、長角血蜱（Haemaphysalis longicornis)等壁蟲類，羊痂恙蟲（Psoroptes ovis)等恙蟎 類，济蟲屬济瘡（Sarcoptes scabiei)等济蟲類，普通球潮 蟲（Armadillidium vul g are)等甲殼類，茶園根腐恙蟲 •46 - 201238485 (Prathylenchus penetrans)、短體線蟲（Prathylenchus vulnus) ' 馬鈴薯黃金線蟲（Globodera rostochiensis)、大 豆胞囊線蟲（Heterodera glycines)、根結線蟲（Meloidogyne hapla)、南方根結線蟲（Meloidogyne incognita)、松材線蟲 (Bursaphelenchus lignicolus)等線蟲類，福壽螺（P〇nacea canaliculata)、雙線括蝓（Incilaria bilineata)、琉球球鍋 牛（Acusta despecta sieboldiana)、三條線鍋牛（Euhadra peliomphala)等軟體動物等。 [有害生物防治劑] 本發明之農園藝用有害生物防治劑，具有顯著之殺菌 效果以及殺蟲效果，係含有以式[I]所示之化合物之1種 或2種以上爲有效成分者。 以式[1-1] [1-2]所示之本發明之農園藝用有害生物防 治劑之使用，可藉由噴霧、散佈、塗布等處理，或者以有 效成分處理種子、植物周圍之土壤或播種種子之土壤、水 田、水耕栽培之水而進行。使用係可於植物遭病原菌感染 前或感染後時，或於害蟲發生前或發生後進行。 本化合物爲一般製劑之態樣，例如可作爲如例如粒劑 、粉粒劑、水溶劑 '油劑、乳液製劑、微乳液製劑、懸浮 乳液製劑、液劑、水和劑、乳劑、懸濁劑、錠劑、顆粒水 和劑、微膠囊、氣溶膠、糊劑、袋裝劑、粉劑、煙燻劑、 燻蒸劑等適用於農園藝用有害生物防治劑中作爲藥劑使用 。該等樣態可將至少一種本發明之化合物與適當的固體或 -47- 201238485 液體之載體類，以及依據期望之用於改善有效成分 性或其他性質之適當的輔助劑（例如界面活性劑、 安定劑）一起混合之一般的方法獲得。 固體載體或稀釋劑之例爲例如植物性物質（例 性纖維素、澱粉、木粉、軟木、咖啡豆殼等）、纖 質、人工可塑性粉末、黏土（例如高嶺土、膨潤土 、矽藻土、合成含水氧化矽、FUB AS AMI粘土、酸 等）、滑石及無機物（例如蛭石、蒙脫石、輕石、硫 、磷灰石、雲母、矽藻土、石英粉末、活性炭、碳 )、高分子化合物（聚氯化乙烯、石油樹脂等）、化I 例如硫安、磷安、硝安、氯安、氯化鈣、尿素等） 載體及稀釋劑爲水、醇類（例如甲醇、乙醇、異丙 己醇等等）、酮類（例如丙酮、甲基乙基酮、環己国 醚類（例如乙基溶纖素、丁基溶纖素、二噁烷等）、 烴（例如苯、甲苯、二甲苯、乙基苯、甲基萘等）、 烴（例如煤油、鏈烷等）、酯類（例如乙酸異丙酯、 酯等）、腈類、醯胺類（例如N，N—二甲基甲醯胺、 亞颯等）、鹵化苯（例如氯苯、三氯乙烯等）。 氣體狀載體，亦即噴射劑可舉出例如二氧化碳 丁烷氣體、氟碳化合物等》 界面活性劑可列舉過去用於農藥製劑領域中之 離子性界面活性劑、非離子性界面活性劑等。陰離 面活性劑可舉出例如烷磺酸、α -烯烴磺酸、木質 、烷基苯磺酸、烷基萘磺酸、萘磺酸甲醛縮合物、 之分散 溶劑、 如結晶 維狀物 、白土 性白土 磺粉末 酸鈣等 Ρ肥料（ 。液體 醇、環 同等）、 芳香族 脂肪族 乙酸苄 二甲基 氣體、 各種陰 子性界 素磺酸 磺基水 -48- 201238485 楊酸二烷酯等磺酸系界面活性劑及該等之鹽，聚氧乙烯烷 基醚硫酸酯、聚氧乙烯烷基烯丙基醚硫酸酯、聚氧乙烯苯 乙烯基苯基醚硫酸酯、聚氧乙烯苯基烷基烯丙基醚硫酸酯 、聚氧烷二醇硫酸酯、高級醇硫酸酯、脂肪酸酯硫酸酯、 苯基酚（EO)硫酸鹽等硫酸鹽系界面活性劑及該等之鹽，聚 氧乙烯烷基醚磷酸酯、聚氧乙烯烷基烯丙基醚磷酸酯、苯 基酚（EO)磷酸酯鹽、聚氧乙烯苯基烷基烯丙基醚磷酸酯、 高級醇磷酸酯、聚氧乙烯三苄基酚磷酸酯等磷酸系界面活 性劑及該等之鹽，高級脂肪酸鹽、聚碳酸型界面活性劑及 該等之鹽。上述各界面活性劑中該等之鹽包含鈉、鉀、鎂 、鈣、銨、乙醇胺、二乙醇胺、三乙醇胺及各種胺類之鹽 。非離子性界面活性劑可舉出例如聚氧乙烯烷基烯丙基醚 、聚氧乙烯苯乙烯基苯基醚、聚氧乙烯烷基醚、聚氧乙烯 苯基烷基烯丙基醚、聚氧乙烯山梨糖醇肝脂肪酸酯、聚氧 乙二醇、聚氧乙烯烷酯、聚氧乙烯聚氧丙烯嵌段共聚物、 聚氧烷二醇、烷二醇（乙炔二醇）、伸烷基聚氧乙二醇、山 梨糖醇酐脂肪酸酯、烷基芳基醚甲醛縮合物等》 安定劑可舉出例如異丙基磷酸鹽混合物、磷酸三甲$ 酯、牛油、環氧油、界面活性劑類、脂肪酸類及其酯類。 除上述化合物之外，本發明之化合物可與其他殺菌劑、@ 蟲劑、除草劑或肥料混合而製劑化。 —般上述製劑中含有1〜95重量％，1〜50重量％爲佳 之至少一種本發明化合物[I]。該等製劑可單獨使用或g 釋使用，本發明化合物[I]之使用濃度以約lg〜5kg/公頃， -49- 201238485 2g〜100g/公頃爲佳，通常爲1〜50000ppm，以5〇〜i〇〇〇ppm 爲佳。 本發明活性化合物可單獨使用或以其製劑物使用，亦 可與殺菌·殺黴劑、殺細菌劑、殺蟎劑、殺線蟲劑、殺蟲 劑、生物農藥 '除草劑、植物荷爾蒙劑、植物發育調節物 質、協同劑、誘引劑、驅避劑、色素、肥料等之混合物， 或組合選自該等有效成分之一種或二種以上而成之混合物 之製劑物作爲有害生物防治劑使用。其可實現作用、防治 對象病蟲害、擴大使用適用期或降低藥量、相乘效果，或 可期待降低抗藥性等’多數情況混合物活性超越個別活性 ，且與共同成分達成協同藥效。 混合物中共同成分中，已知有許多殺菌.殺黴劑、殺 細菌劑、殺蟎劑、殺線蟲劑、生物農藥、費洛蒙劑、天然 殺菌劑、天然殺蟲劑已開發並於市面販售，或記載於日本 植物防疫協會發行的農藥使用手冊（2009年）、同協會發行 之農藥要覽（2009年）、全國農業合作社連合會發行之合作 社農藥總覽（2009年）以及同連合會發行之 SHIBUYA INDEX(2009 年）等。 以下舉出例子，但未限定於該等物質。 殺菌劑可舉出例如阻礙SH合成活性之化合物、阻礙 核酸生合成活性之化合物、阻礙紡錘絲形成活性之化合物 、苯甲醯苯胺（benzanilide)系化合物、甲氧基丙嫌酸酯 (strobilurin)系化合物、其他阻礙電子傳遞系活性之化合 物、阻礙胺基酸生合成活性之化合物、阻礙固醇生合成活 -50- 201238485 性之化合物、阻礙細胞壁合成活性之化合物、阻礙脂質生 合成活性之化合物、阻礙葡聚醣合成活性之化合物、阻礙 黑色素合成活性之化合物、誘導宿主產生防禦反應之化合 物、具有其他或未知作用之化合物等。 阻礙 SH合成活性之化合物：四氯異苯腈 (chlorothalonil)、腈硫醌（dithianon)、蓋普丹（captan)、福 爾培（folpet)、院苯擴酸鹽（iminoctadine-albesilate)、院苯 醋酸鹽（iminoctadine-triacetate)、富爾邦（ferbam)、代森 鈉（nabam)、鐘乃浦（maneb)、鋅鍾乃浦（mancozeb)、免得 爛（metiram)、甲基幹乃浦（propineb)、代森福美辞 (polycarbamate)、得恩地（thiram)、福美鋅（ziram)、代森 鋅（zineb)、氧化銅（cupric oxide)、氫氧化銅（Copper hydroxide)、驗性氯氧化銅（copper oxychloride)、無水硫 酸銅（copper sulfate (anhydride))、硫酸銅（copper sulfate) 、硫擴（sulfur)等。 阻礙核酸生合成活性之化合物：滅達樂（metalaxyl)、 右滅達樂（metalaxyl-M)、歐殺斯（oxadixyl)、布瑞莫 (bupirimate)、殺紋寧（hymexazol)、歐索林酸（oxolinic acid)等。 阻礙紡錘絲形成活性之化合物：免賴得（benomyl)、 貝芬替（carbendazim)、乙黴威（diethofencarb)、甲基多保 淨（thiophanate-methyl)、座賽胺（zoxamide)、賓克隆 (pencycuron)、氟比來（fluopicolide)等。 苯甲醯苯胺（benzanilide)系化合物：福拉比 -51 - 201238485 (furametpyr)、卩比噻菌胺（penthiopyrad)、賽氟滅 (thifluzamide)、白克列（boscalid)、嘉保信（oxycarboxin) 、萎鏽靈（carboxin)、福派銳（fluopyram)、福多寧 (flutolanil)、滅普寧（mepronil)等。 甲氧基丙烯酸酯（strobilurin)系化合物：亞托敏 (azoxystrobin)、U定氧菌醋（picoxystrobin)、克收欣 (kresoximmethyl)、三氣敏（trifloxystrobin)、歐殺敏 (orysastrobin)、美拖敏（metominostrobin)、百克敏 (pyraclostrobin)、凡殺同（famoxadone)、咪唯菌酮 (fenamidone)、派丙威（pyribencarb)、二膜敏 (dimoxystrobin)、派羅敏（pyrametostrobin)、派稀敏 (pyraoxystrobin)等 〇 · 其他阻礙電子傳遞系活性之化合物：二氟林 (diflumetorim)、賽座滅（cyazofamid)、安美速 (amisulbrom)、消織多（meptyl dinocap)、扶吉胺 (fluazinam)、富米綜（ferimzone)等。 阻礙胺基酸生合成活性之化合物：賽普洛 (cyprodinil)、滅派林（mepanipyrim) ' 派美尼 (pyrimethanil)、保米黴素（blasticidin-S)、鏈黴素 (streptomycin)、嘉賜黴素（kasugamycin)等。 阻礙固醇生合成活性之化合物：氧環唑（azaconazole) 、比多農（bitertanol)、溴克座（bromuconazole)、環克座 (cyproconazole)、待克利（difenoconazole)、依普座 (epoxiconazole)、芬克座.（fenbuconazole)、夫菌哩 -52- 201238485 (furconazole) 、 菲克 利 (hexaconazole) 、 易 胺 座 (imibenconazole) 、克 康 那 嗤(metoconazole) 、邁 克 尼 (myclobutanil) 、 平 克 座 (penconazole) 、 普 克 利 (propiconazole) 、 矽 氟 哩 (simeconazol e) 、 得 克 利 (tebuconazole) 、 三 泰 芬 (triadimefon) 、 三 泰 隆 (triadimenol)、滅菌唑（triticonazole)、依滅歹IJ (imazalil) 、賽福座（triflumizole)、披扶座（pefurazoate)、撲克拉 (prochloraz)、芬瑞莫（fenarimol)、環醯菌胺（fenhexamid) 、芬普福（fenpropimorph)、粉病靈（piperalin)、螺環菌胺 (spiroxamine)等。 阻礙細胞壁合成活性之化合物：依普同（iprodione)、 滅克寧（myclozolin)、撲滅寧（procymidone)、免克寧 (vinclozolin)、快諾芬（quinoxyfen)、護汰寧（fludioxonil) 等。 阻礙脂質生合成活性之化合物：丙基喜樂松 (iprobenfos)、亞賜圃（isoprothiolane)、五氯硝苯 (quintozene)、普拔克（propamocarb) ' 普司克（prothicarb) 、達滅芬（dimethomorph)、纈霉威（iprovalicarb)、苯噻菌 胺（benthiavalicarb)、曼普胺（mandipropamid)等。 阻礙葡聚醣合成活性之化合物：維利黴素 (validamycin)、保粒黴素（甲）（poly〇xinB)等。 阻礙黑色素合成活性之化合物：百快隆（pyroquion)、 三賽唑（tricyclazole)、加普胺（carpropamid)、雙氯氰菌胺 (diclocymet)、芬諾尼（fenoxanil)等。 -53- 201238485 誘導宿主產生防禦反應之化合物：阿拉酸式苯-S-甲 基（acibenzolar-S-methyl)、撲殺熱（probenazole)、異噻菌 胺（isotianil)、褐藻多醣（laminarin)等。 具有其他或未知作用之化合物：克絕（cymoxanil)、福 賽得（fosetyl-Al)、***碟（triazoxide)、滅速克 (methasulfocarb)、氟硫滅（flusulfamide)、蠘離丹 (chinomethionat)、噻哩菌胺（ethaboxam)、賽芬胺 (cyflufenamid)、福多寧（flutolanil)、滅芬農（metrafenone) 、異 丁乙氧喹啉（tebufloquin)、氨基啦淀（pyridylamidine) 、醯菌醋（enestroburin)、丙氧喹啉（卩1*〇911丨1132丨(1)、8丫1^-524464、SYN- 5 20、SYF-14182、必殺分（bixafen)、福殺 銳（fluxapyroxad)、福派銳（fluopyram)、伏魔飛（flumorph) 、福來帖（valifenalate)、殺真菌劑（pyriofenone)等。 殺蟲劑·殺蟎劑·殺線蟲劑之例可舉出例如乙醯膽鹼 酯酶抑制劑、阻礙GABA依賴性氯離子通道之化合物、阻 礙鈉離子通道之化合物、阻礙尼古丁性乙醯膽鹼受器之化 合物、阻礙氯離子通道之化合物、僞返幼激素（juvenile hormone)化合物 '非選擇性阻礙化合物、阻礙選擇性攝食 之化合物、阻礙蟎類成長之化合物、Bt劑、阻礙ATP合 成之化合物、去氧化性磷酸化共軛化合物、阻礙尼古丁性 乙醯膽鹼受器通道之化合物、阻礙幾丁質（chitin)生合成 之化合物、干擾脫皮·變態之化合物、章魚胺 (octopamine)拮抗化合物、阻礙電子傳遞系化合物、阻礙 電位依賴性鈉離子通道之化合物、阻礙脂質合成之化合物 -54- 201238485 、阻礙雷阿諾定受器（ryanodine receptor)之化合物、具有 其他或未知作用之化合物等。 乙醯膽鹼酯酶抑制劑：得滅克（aldicarb)、免扶克 (benfuracarb)、加保利（carbaryl)、加保扶（carbofuran)、 丁基加保扶（carbosulfan)、丁 基滅必蟲（fenobucarb)、滅 賜克（methiocarb)、納乃得（methomyl)、毆殺滅（oxamyl)、 硫敵克（thiodicarb)等。 殿殺松（acephate)、陶斯松（chlorpyrifos)、.大利松 (diazinon)、大滅松（dimethoate)、馬拉松（malathion)、達 馬松（methamidophos) ' 亞素靈（monocrotophos)、甲基巴 拉松（parathion-methyl)、佈飛松（profenofos)、托福松 (terbufos)、密殺松（imicyafos)等。 阻礙GABA依賴性氯離子通道之化合物：安殺番 (endosulfan)、乙蟲清（ethipr〇ie)、芬普尼（fipr〇nil)、艾同 清（acetoprole)等。 阻礙鈉離子通道之化合物：畢芬寧（bifenthrin)、賽滅 寧（cypermethrin)、益化利（esfenvaierate)、迷菊酯 (ethofenprox)、賽洛寧（iambda-cyhalothrin)、貼福寧 (tefluthrin)、DDT(DDT)、甲氧 DDT (methoxychlor)等。 阻礙尼古丁性乙醯膽鹼受器之化合物：亞滅培 (acetamiprid)、可尼丁 （ c 1 o t h i an i d i η) ' 達特南 (dinote fu ran)、益達胺（imidacloprid)、稀 Π定蟲胺 (nitenpyram)、賽果培（thiac 丨 oprid)、賽速安 (thiamethoxam)等 〇 -55- 201238485 賜諾司（spinosyn)' 賜諾特（spinetoram)等。 阻礙氣離子通道之化合物：阿巴汀（abamectin)、因滅 汀（emamectin-benzoate)、密滅汀（milbemectin)、利滅汀 (lepimecti)等。 僞返幼激素（juvenile hormone)化合物：丙諾保 (k i η 〇 p r e n e)、美西保（m e t h 〇 p r e n e)、芬諾克（f e η ο X y c a r b)、 百利普芬（pyriproxyfen)等。 非選擇性阻礙化合物：溴化甲院（methyl bromide)、 氯化苦（chloropicrin)等。 阻礙選擇性攝食之化合物：派滅淨（pymetrozine)、氟 尼胺（flonicamid)等。 阻礙蟎類成長之化合物：克芬蟎（clofentezine)、合賽 多（hexythiazox)、依殺螨（etoxazole)等。Tripospermum juglandis), persimmon Zygophiala jamaicensis, Gloeosporium kaki, Botrytis cinerea, Pestalotia diospyri, Glomerella cingulata, persimmon Mycosphaerella nawae, P odosphaera tridactyla, Sphaerotheca pannosa, Botryosphaeria dothidea, Sclerotinia sclerotiorum' Cladosporium carpophilum, green plum white Rust (Leucotelium pruni-persicae), Roselle necatrix, Fusari.um lateritium, Pseudocercospora circumscissa, Sphaceloma pruni-domesticae, Ome Anthrax-39 - 201238485 (Glomerella cingulata), Botrytis cinerea, Monilinia fructicola, Monilinia laxa, Glomerella mume, Sclerotinia sclerotiorum Cherry powdery mildew Podosphaera tridactyla), Rhizopus nigricans, Glomerella cingulata, Botrytis cinerea, Monilinia fructicola, Phyllactinia mali, Pear disease (Phytophthora cactorum, phytophthora syringae), Venturia pirina, C ο 11 etotric hu m gloeosporioides, Gymnosporangium asiaticum, Phyllactinia pyri 'Pear Phytophthora cactorum, Phytophthora syringae, Venturia nashicola, Alternaria kikuchiana, Leptothyrium pomi, Glomerella cingulata, Botrytis Cinerea), Monilinia fructigena, Colletotrichum gloeosporioides, Physalospora piricola, Fusarium oxysporum, Gibberella zeae, Podosphaera tridactyla, Sphaerotheca pannosa Peach sclerotinia Sclerotinia sclerotiorum), Rhizopus nigricans, Cladosporium carpophilum, Leucotelium pruni-persicae, Stenella sp., Pleudocercospora circumscissa Phyllosticta persicae), peach charcoal scars -40 - 201238485 (Gloeosporium laeticolor), botrytis cinerea, Monilinia fructicola, Phomopsis sp., apple brown spot disease (Gymnosporangium) Yamadae), P odosphaera 1 eucotricha, apple plague (P hytophthora cactorum, phytophthora cambi vola, Phy tophthor a syringae), apple brown spot (Diplocarpon mali), orchard ring blight (Cristulariella moricola) ), V ent ur ia inaequalis, Zygophiala jamaicensis, Glomerella cingulata, Botrytis cinerea, apple spotted leaf disease (Alternaria alternata) ), grape powdery mildew (Uncinula necator), grapes Sclerotinia sclerotiorum, Glomerella cingulata, Pseudocercospora vitis, Briosia ampelophaga, Elsinoe ampelina, grape black Phyllosticta ampelicida, Phomopsis viticola, Plasmopara viticola, Glomerella cingulata, Capnodium salicinum, Morenoella quercina, chestnut Powdery mildew (Microsphaer a alphitoides), chestnut leaf blight (Monochaetia monochaeta), Botrytis cinirea, Phytophthora citrophthora 'Diaporthe citri', root orange spot Disease (Mycosphaerella citri, Mycosphaerella horii), Elsinoe fawcettii, Mycosphaerella pinodes, Anthracnose anthracis -41 - 201238485 (Colletotrichum gloeosporioides), Citrus rust disease (Colletotrichum gloeosporioides) ^ ° (For pests and diseases of agricultural and horticultural plants For example, examples of diseases, pests, mites, and the like of agricultural and horticultural plants include Hemiptera, Thysanoptera, Lepidoptera, Acari, etc., which are used in the present invention. The fluorine-containing quinazoline derivative can prevent diseases caused by plants of the pests and mites. The following are examples of pests, diseases, and the like, but are not limited thereto. Examples of diseases, insects, mites, and the like include Plutella xylostella, Agrotis ipsilon, Agrotis segetum, Helicoverpa armigera, and Helicoverpa assulta. )' Helicoverpa zea, Heliothis virescens, Mamestra brassicae, Naranga aenescens, Plusia nigrisigna, Musca domestica (Pseudaletia separata), Spodoptera exigua, Spodoptera litura, Spodoptera littoralis 'Spodoptera frugiperda, Spodoptera eridania, Xue Caotian Moth (Manduca sexta), Endopiza viteana, Lyyonetia prunifoliella malinella, Phyllonycter ringoneella, Phyllocnistis citrella, Pectinophora gossypiella, Carpoline fruit moth (Carposina niponensis), tea leaf curler (Adoxophyes orana -42 - 201238485 faciata), cotton brown belt roll Moth (Adoxophyes honmai), Homona magnamina, Cydla pomonella, Grapholita molesta 'Chilosuppressalis, Cnaphalocrocis medinalis, Chinese cabbage 螟 ( Hellula undalis), Ostrinia nubilalis 'Pseudoplusia includens, Trichoplusia ni, Hyphantria cunea, Pieris rapaecrucivora, and straight-leaved rice (Parnara) Guttata), such as Lepidoptera pests, Anomala cuprea, Anomala rufocuprea, Popillia japonica, Lepinotarsa decemlineata, Epilachna varivestis, Golden worm (Melanotus tamsuyensis), Lasioderma serricorne, Epuraea domina, Henosepilachna vigintioctopunctata, Tenebrio molitor, Tribolium castaneum, star Anoplophora malasiaca, Monochamus alternatus, Mung bean (Callosobruchus chinensis), Aulacophora femoralis, Oulema oryzae, Phyllotreta striolata, Cylasformicarius, Anthonomus grandis, Inaba A (Ethinocnemus squameus), Hypera postica, Lisorhoptrus oryzophilus, Sitophilus zeamais, Sphenophrus venatus vestius, Sitophilus granarius, Spotted yellow squash -43- 201238485 (Diabrotica undecimpunctata), western corn rootworm (Diabrotica virgifera), corn rootworm (Diabrotica barberi), yellow winged worm (Paederus fuscipes) coleoptera, etc., Eurydema Rugosa), Eysarcoris ventralis, Halyomorpha mista, Nezara viridula, Leptocorisa chinensis, Riptortus clavatus, Long-winged tortoise Togo hemipterus, Stephanitis pyrioides, night owl (Epiacanthus stramineu) s), Empoasca onukii, Emppoasca fabae, Nephotettix cinctinceps, Laodelphax striatellus, Nilaparvata lugens, Sogatella Furcifera), T riozaerytreae, P sy 11 apyrisuga, Bemisia tabaci, Bemisia argentifolii, Dialeurodescitri ' Greenhouse powder Trialeurodes vaporariorum, Aphis gossypii, Aphis pomi, Myzus persicae, Drosicha corpulenta, Icerya purchasi, citrus powder scale insects Planococcus citri), Pseudococcus comstocki, Ceroplastes rubens, Unaspis yanonensis, Cimex lectularius, and other Hemiptera pests, Frankliniella occidentalis , Frankliniella intonsa, Scirthothrips dorsalis, and Thrips palm i), Thrips -44 - 201238485 tabaci, such as the genus Diptera, Dacus dorsalis, Dacus cucurbitae, Ceratitis capitata, Hydrellia griseola Liriomyza bryoniae, Liriomyza trifolii, Hylemya platura, Rhagoletis pomonella, Mayetiola destructor, Musca domestica ), Stomoxys calcitrans, Melophagus ovinus, Hypoderma 1 ineatum, Hypodermabovis, Oestrus ovis, Glossina palpalis, Glossina morsitans ), Prosimulium yezoensis, Tabanus trigonus, Telmatoscopus albipunctatus, Leptoconops nipponensis, Culex pipiens pallens, Aedes albopicutus , Diptera pests such as Aedes aegypti and Anopheles hyracanus sinesis, Apeth Ymus kuri), Athalia rosae japonensis, Neodiprion sertifer, Eciton burchelli (Eciton schmitti), Japanese antler (Camponotus japonicus), Vespa mandarina , Meyrmecia spp., Solenopsis spp., Monoomorium pharaonis, Hymenoptera, Periplaneta fuliginosa, Periplaneta japonica, Germany Nettlem pests such as Blattella germanica, Teleogryllus emma, African cockroach (Gryllotalpa -45- 201238485 africana), Locusta migratoria, Oxya yezoensis, and plague Orthoptera pests such as the desert locust (Schistocerca gregaria), termite-like pests such as Coptotermes formosanus, Reticulitermes speratus, Odontotermes formosanus, and cat eggs (Ctenocephalidae felis) , such as quail eggs (Pulex irritans), mouse preparations (Xenopsylla cheopis), etc., chicken body 13⁄4 (M enacanthu Sstramineus), cattle 13⁄4 (Bovicola bovis) and other 13⁄4 mesh pests, and cattle 13⁄4 (Haematopinus eurysternus), Haematopinussuis, Long Nose 13⁄4 (Linognathus vituli), Small Blue Bovine (Solenopotes capillatus), etc. Target pests. Acaphylla, Acaphylla, Panonychus citri, Panonychus ulmi, Tetranychus kanzawai, Tetranychus urticae, etc. Theae), Aculops pelekassi', Eriophyes chibaensis, Aceria tulipae, and other subfamilies, Polyphaotarsonemus latus, Steneotarsonemus pallidus, such as scorpion, Tyrophagus putrescentiae, Rhizoglyphus robini, etc., larvae such as Varroa jacobsoni, tiny calves (Boophilus microplus), wall worms such as Haemaphysalis longicornis, mites such as Psoroptes ovis, worms such as Sarcoptes scabiei, and common worms ( Armadillidium vul g are) and other crustaceans, tea garden root rot mites • 46 - 201238485 (Prathylenchus penetrans), short-lived nematode (Prathylenchus vulnus) 'Globodera rostochiensis, Nematodes such as Heterodera glycines, Meloidogyne hapla, Meloidogyne incognita, Bursaphelenchus lignicolus, P〇nacea canaliculata, double-lined scorpion Incilaria bilineata), Acusta despecta sieboldiana, and mollusks such as Euhadra peliomphala. [Pest Control Agent] The pest control agent for agricultural and horticultural use of the present invention has a remarkable bactericidal effect and an insecticidal effect, and one or two or more compounds of the formula [I] are contained as an active ingredient. The use of the agricultural and horticultural pest control agent of the present invention represented by the formula [1-1] [1-2] can be treated by spraying, spreading, coating, or the like, or treating the seed, the soil around the plant with an active ingredient. It is carried out by sowing seeds of soil, paddy fields, and hydroponic cultivation water. The use can be carried out before or after the infection of the plant with the pathogen, or before or after the occurrence of the pest. The present compound is in the form of a general preparation, and can be used, for example, as, for example, granules, powder granules, aqueous solvent 'oil agent, emulsion preparation, microemulsion preparation, suspension emulsion preparation, liquid preparation, water and agent, emulsion, suspension agent , tablets, granule water and agents, microcapsules, aerosols, pastes, bagging agents, powders, fumigants, fumigants, etc. are suitable for use as pesticides in agricultural and horticultural pest control agents. Such forms can be used with at least one compound of the invention and a suitable solid or carrier of the liquid of -47 to 201238485, as well as suitable adjuvants (e.g., surfactants, depending on the desired use to improve the active ingredient or other properties). Stabilizer) is obtained by a general method of mixing together. Examples of the solid carrier or diluent are, for example, vegetable substances (for example cellulose, starch, wood flour, cork, coffee bean shell, etc.), cellulosics, artificial plastic powder, clay (for example, kaolin, bentonite, diatomaceous earth, synthesis). Aqueous cerium oxide, FUB AS AMI clay, acid, etc.), talc and inorganic substances (such as vermiculite, montmorillonite, pumice, sulfur, apatite, mica, diatomaceous earth, quartz powder, activated carbon, carbon), polymer Compounds (polyvinyl chloride, petroleum resins, etc.), chemicals I such as sulphur, phosphorus, nitrate, chloramphenicol, calcium chloride, urea, etc.) Carriers and diluents are water, alcohols (eg methanol, ethanol, isopropanol) Alcohols, etc.), ketones (such as acetone, methyl ethyl ketone, cyclohexyl ether (such as ethyl cellosolve, butyl cellosolve, dioxane, etc.), hydrocarbons (such as benzene, toluene, xylene, Ethylbenzene, methylnaphthalene, etc.), hydrocarbons (such as kerosene, alkanes, etc.), esters (such as isopropyl acetate, esters, etc.), nitriles, guanamines (such as N,N-dimethylformamidine) Amines, arbium, etc.), halogenated benzene (eg chlorobenzene, trichloroethylene) Examples of the gaseous carrier, that is, the propellant, for example, carbon dioxide butane gas, fluorocarbon, etc. The surfactants include ionic surfactants and nonionic surfactants which have been used in the field of pesticide preparations. The anionic surfactant may, for example, be an alkanesulfonic acid, an α-olefinsulfonic acid, a wood, an alkylbenzenesulfonic acid, an alkylnaphthalenesulfonic acid, a naphthalenesulfonic acid formaldehyde condensate, a dispersion solvent, such as a crystal shape. 、 Ρ Ρ 粉末 粉末 粉末 粉末 粉末 粉末 粉末 粉末 粉末 ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( Sulfonic acid-based surfactant such as alkyl ester and the like, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl allyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, polyoxygen a sulfate-based surfactant such as vinyl phenylalkyl allyl ether sulfate, polyoxyalkylene glycol sulfate, higher alcohol sulfate, fatty acid ester sulfate, phenylphenol (EO) sulfate, and the like Salt, polyoxyethylene alkyl ether phosphorus Ester, polyoxyethylene alkyl allyl ether phosphate, phenylphenol (EO) phosphate, polyoxyethylene phenyl alkyl allyl ether phosphate, higher alcohol phosphate, polyoxyethylene tribenzyl phenol a phosphate-based surfactant such as a phosphate ester, a salt thereof, a higher fatty acid salt, a polycarbonate surfactant, and the like. The salt of the above surfactants includes sodium, potassium, magnesium, calcium, ammonium. A salt of ethanolamine, diethanolamine, triethanolamine or various amines, and examples of the nonionic surfactant include polyoxyethylene alkyl allyl ether, polyoxyethylene styryl phenyl ether, and polyoxyethylene alkyl group. Ether, polyoxyethylene phenyl alkyl allyl ether, polyoxyethylene sorbitol liver fatty acid ester, polyoxyethylene glycol, polyoxyethylene alkyl ester, polyoxyethylene polyoxypropylene block copolymer, polyoxygen An alkanediol, an alkanediol (acetylene glycol), an alkylene polyoxyethylene glycol, a sorbitan fatty acid ester, an alkyl aryl ether formaldehyde condensate, etc. Salt mixture, trimethyl phosphate, tallow, epoxidized oil, surfactant, fat Fatty acids and their esters. In addition to the above compounds, the compounds of the present invention can be formulated by mixing with other fungicides, insecticides, herbicides or fertilizers. The above preparations preferably contain 1 to 95% by weight, preferably 1 to 50% by weight, based on at least one compound [I] of the present invention. These preparations may be used alone or in a g-release manner, and the use concentration of the compound [I] of the present invention is preferably about lg~5 kg/ha, -49-201238485 2 g~100 g/ha, usually 1 to 50000 ppm, and 5 〇~ I〇〇〇ppm is preferred. The active compound of the present invention can be used alone or in the form of a preparation thereof, and can also be used together with a bactericidal, fungicide, bactericide, acaricide, nematicide, insecticide, biological pesticide 'herbicide, plant hormone, plant A mixture of a developmental regulating substance, a synergistic agent, an attractant, a repellent, a pigment, a fertilizer, or the like, or a combination of one or more selected from the active ingredients, is used as a pest control agent. It can achieve the effect, control the pests and diseases of the object, expand the pot life or reduce the dose, multiply the effect, or can expect to reduce the resistance. In most cases, the mixture activity exceeds the individual activity, and synergistic effects are achieved with the common ingredients. Among the common ingredients in the mixture, many sterilizations are known. Fungicides, bactericides, acaricides, nematicides, biological pesticides, pheromones, natural fungicides, natural insecticides have been developed and marketed. Sold, or recorded in the Pesticides User Manual issued by the Japan Plant Epidemic Prevention Association (2009), the pesticides issued by the Association (2009), the cooperatives issued by the National Agricultural Cooperatives Association (2009), and the issuance of the same association SHIBUYA INDEX (2009) and so on. The following are examples, but are not limited to these substances. Examples of the bactericidal agent include a compound which inhibits SH synthesis activity, a compound which inhibits nucleic acid biosynthesis activity, a compound which inhibits spindle formation activity, a benzanilide compound, and a strobilurin system. a compound, another compound which inhibits the activity of the electron transporting system, a compound which inhibits the biosynthesis activity of the amino acid, a compound which inhibits the biosynthesis of the sterol, and a compound which inhibits the cell wall synthesis activity, a compound which inhibits the lipid biosynthesis activity, A compound which inhibits glucan synthesis activity, a compound which inhibits melanin synthesis activity, a compound which induces a defense reaction by a host, a compound which has another or unknown effect, and the like. Compounds that block the activity of SH synthesis: chlorothalonil, dithianon, captan, folpet, iminoctadine-albesilate, benzene Acimate (iminoctadine-triacetate), ferbam, nabam, maneb, mancozeb, metiram, propineb, and sensenfumei Polycarbamate, thiram, ziram, zineb, cupric oxide, copper hydroxide, copper oxychloride, anhydrous Copper sulfate (anhydride), copper sulfate, sulfur, and the like. Compounds that hinder the synthesis of nucleic acids: metalaxyl, metalaxyl-M, oxadixyl, bupirimate, hymexazol, oxalinic acid (oxolinic acid) and the like. Compounds that hinder spindle formation activity: benomyl, carbendazim, diethofencarb, thiophanate-methyl, zoxamide, benelope ( Pencycuron), fluopicolide, etc. Benzonilide compound: Furabi-51 - 201238485 (furametpyr), penthiopyrad, thifluzamide, boscalid, oxycarboxin, Carboxin, floopyram, fluolanil, mepronil, etc. Strobilurin compounds: azoxystrobin, picoxystrobin, kresoximmethyl, trifloxystrobin, oresastrobin, beauty drag Metominostrobin, pyraclostrobin, famoxadone, fenamidone, pyribencarb, dimoxystrobin, pyrametostrobin, pyridin (pyraoxystrobin), etc. Other compounds that impede the activity of electron transport systems: diflumetorim, cyazofamid, amisulbrom, meptyl dinocap, fluazinam, Fermizone and so on. Compounds that block the biosynthesis activity of amino acids: cyprodinil, mepanipyrim 'pyrimethanil, blasticidin-S, streptomycin, tribute Kasugamycin and the like. Compounds that block sterol biosynthesis activity: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, (fenbuconazole), phlegm-52-201238485 (furconazole), hexaconazole, imibenconazole, metoconazole, myclobutanil, pingke ( Penconazole), propiconazole, simeconazol e, tebuconazole, triadimefon, triadimenol, triticonazole, imazalil, Triflumizole, pefurazoate, prochloraz, fenarimol, fenhexamid, fenpropimorph, piperalin, snail Spiroxamine and the like. Compounds that block cell wall synthesis activity: iprodione, myclozolin, procymidone, vinclozolin, quinoxyfen, fludioxonil, and the like. Compounds that block lipid biosynthesis activity: iprobenfos, isoprothiolane, quintozene, propamocarb 'prothicarb, dimethomorph ), iprovalicarb, benthiavalicarb, mandipropamid, and the like. Compounds which inhibit the activity of glucan synthesis: validamycin, poly 〇xinB, and the like. Compounds that block melanin synthesis activity: pyroquion, tricyclazole, carpropamid, diclocymet, fenoxanil, and the like. -53- 201238485 A compound which induces a defense reaction in a host: acibenzolar-S-methyl, probenazole, isotianil, laminarin, and the like. Compounds with other or unknown effects: cymoxanil, fosetyl-Al, triazoxide, methasulfocarb, flusulfamide, chinomethionat , ethaboxam, cyflufenamid, flutolanil, metrafenone, tebufloquin, pyridylamidine, vinegar (enestroburin), propoxyquinoline (卩1*〇911丨1132丨(1), 8丫1^-524464, SYN-520, SYF-14182, bixafen, fluxapyroxad, Fluopyram, flumorph, valifenalate, pyriofenone, etc. Examples of insecticides, acaricides and nematicides include, for example, acetylcholine Esterase inhibitors, compounds that block GABA-dependent chloride channel, compounds that block sodium ion channels, compounds that block nicotine acetylcholine receptors, compounds that block chloride channels, and juvenile hormone compounds 'Non-selective hindering compounds, hindering Selective feeding compounds, compounds that inhibit the growth of steroids, Bt agents, compounds that block ATP synthesis, deoxidative phosphorylated conjugated compounds, compounds that block the passage of nicotine acetylcholine receptors, hinder chitin Synthetic compounds, compounds that interfere with peeling and metamorphosis, octopamine antagonist compounds, compounds that block electron transport systems, compounds that block potential-dependent sodium ion channels, and compounds that block lipid synthesis -54-201238485, hindering Raya Compounds of ryanodine receptors, compounds with other or unknown effects, etc. Acetylcholinesterase inhibitors: aldicarb, benfuracarb, carbaryl, plus Carbofuran, carbosulfan, fenobucarb, metiocarb, methodyl, oxamyl, thiodicarb Etc. acephate, chlorpyrifos, diazinon, dimethoate, malathion, da Pine (methamidophos) 'sub-pixel Spirit (monocrotophos), A Larsson Chiba (parathion-methyl), Bu Feisong (profenofos), Tuofu Song (terbufos), dense Chung killer (imicyafos) and the like. Compounds that block GABA-dependent chloride channel: endosulfan, ethipr〇ie, fipr〇nil, acetoprole, and the like. Compounds that block sodium ion channels: bifenthrin, cypermethrin, esfenvaierate, ethofenprox, iambda-cyhalothrin, tefluthrin, DDT (DDT), methoxy DDT (methoxychlor) and the like. Compounds that block nicotine acetylcholine receptors: acetamiprid, c 1 othi an idi η 'dinote fu ran, imidacloprid, dilute Nitenpyram, thiac 丨oprid, thiamethoxam, etc. 〇-55- 201238485 spinosyn's spinotoram. Compounds that block the gas ion channel: abamectin, emamectin-benzoate, milbemectin, lepimecti, and the like. A juvenile hormone compound: propylorphan (k i η 〇 p r e n e), mexi b (p e e e e), f e η ο X y c a r b, pyriproxyfen, and the like. Non-selective blocking compounds: methyl bromide, chloropicrin, and the like. Compounds that block selective feeding: pymetrozine, flonicamid, and the like. Compounds that block the growth of mites: clofentezine, hexythiazox, etoxazole.

Bt 劑：蘇力菌（Bacillus thuringiensis)等。 阻礙ATP合成之化合物：汰芬隆（diafenthiuron)、亞 環錫（azocyclotin)、錫觸丹（cyhexatin) ' 芬佈賜 (fenbutatin oxide)、殴鍋多（propargite)、得脫蟎 (tetradifon)等。 去氧化性磷酸化共軛化合物：克凡派（chlorfenapyr) 等。 阻礙尼古丁性乙醯膽鹼受器通道之化合物：免速達 (bensultap)、培丹（cartap)、硫賜安（thiocyclam)等。 阻礙幾丁質（chitin)生合成之化合物：克福隆 (chlorfluazuron)、二福隆（diflubenzuron)、氟芬隆 -56- 201238485 (flufenoxuron) 六伏隆（hexaflumuron)、祿芬隆 (lufenuron)、諾伐隆（novaluron)、得福隆（teflubenzuron) 、三福隆（triflumuron)、布芬淨（buprofezin)、雙三氟隆 (bistrifluron)等。 干擾脫皮·變態之化合物：賽滅淨（cyromazine)、可 芬諾（chromafenozide)、合芬隆（halofenozide)、滅芬諾 (methoxyfenozide)、得芬諾（tebufenozide)、諾福隆 (η 〇 v i f 1 u m u r ο η)等 0 章魚胺（octopamine)拮抗化合物：三亞蟎（amitraz)、 愛美松（hydramethylnon)、亞驅蟎（acequinocyl)等。 阻礙電子傳遞系化合物：芬殺蟎（fenazaquin)、芬普 滿（fenpyroximate)、畢汰芬（pyrimidifen)、畢達本 (pyridaben)、得芬瑞（tebufenpyrad)、脫芬瑞（tolfenpyrad) 、魚藤精（rotenone)等" 磷酸化銘（Aluminium phosphide)等。 阻礙電位依賴性鈉離子通道之化合物：因得克 (indoxacarb) 美氟綜（metaflumizone)、賜派芬 (s p i r 〇 d i c 1 〇 f e η)等。 阻礙脂質合成之化合物：螺甲觸酯（spiromesifen)、 賜派滅（spirotetramat)等。 阻礙雷阿諾定受器（ryanodine receptor)之化合物：剋 安勃（chlorantranilprole)、氟大滅（flubendiamide)、氰蟲 醯胺（cyantranilprol)等。 具有其他或未知作用之化合物：印楝素（azadirachtin) -57- 201238485 、西脫蟎（benzoximate) ' 必芬蟎（bifenazate)、蟎離丹 (chinomethionat)、大克蟎（dicof〇l)、定脫蟎（pyridalyl)、 皮羅夫（pyrifluquinazon)、福脫蟎（fiuensuifone)等。 除草劑之例可舉下述之化合物。 亦即爲苯並雙環酮（benzobicyclon)、免速隆 (bensulfuron-methyl)、四唑密磺隆（azimsulfuron)、醚磺 隆（cinosulfuron)、環磺隆（cyclosulfamuron)、百速隆 (pyrazosulfuron- ethyl)、依速隆（imazosulfuron)、節草酮 (indanofan)、丁基賽福草（cyhalofop- butyl)、噻芬草胺 (thenylchlor) ' 禾草畏（esprocarb)、乙氧苯草胺 (etobenzanid)、苯酮哩（cafenstrole)、裨草胺（clomeprop) 、排草淨（dimethametryn)、殺草隆（daimuron)、必芬諾 (bifenox)、稗草畏（pyributicarb)、喃草醚（pyriminobac-methyl)、普拉草（pretilachlor)、溴丁 醯草胺（bromobutide) 、D比草酮（benzofenap)、苯哇草嗣（topramezone)、禾丹草 (benthiocarb) 本達隆（pentoxazone)、咲草黃 (benfuresate)、苯噻草胺（mefenacet)、精嚼哩禾草靈 (fenoxaprop-P-ethyl)、甜菜寧（phenmedipham)、禾草靈 (diclofop-methyl)、甜菜安（desmedipham)、乙呋草黃 (ethofumesate)、異丙隆（isoproturon)、醯哺黃隆 (amidosulfuron)、莎禅磷（anilofos)、咲草黃（benfuresate) 、亞速隆（ethoxysulfuron)、确礎隆（iodosulfuron)、雙苯 噁唑酸（isoxadifen)、甲醯胺磺隆（foramsulfuron)、雙唑草 腈（pyraclonil)、甲磺胺磺隆（mesosulfuron)、達有隆 -58- 201238485 (diuron)、草布隆（neburon)、特樂酌（dinoterb)、卡草胺 (carbetamide)、溴苯腈（bromoxynil)、樂滅草（oxadiazon) 、嚼哩隆（dimefuron)、卩比氟草胺（diflufenican)、苯草酸 (aclonifen)、 耻 草 酮（benzofenap)、 去 稗 安 (oxaziclomefone)、異螺氟草（i sox aflutol e)、炔丙嚼吨草 (oxadiargyl)、呋草酮（flurtamone)、滅必淨（metribuzin)、 甲基苯賽隆（methabenzthiazuron)、脫葉磷（tribufos)、苯 曉草酮（metamitron)、乙曉草酮（ethiozin)、氟噻草胺 (flufenacet)、擴草酮（sulcotrion)、替呋三酮 (tefuryltrione)、四哩醯草胺（fentrazamide)、苯丙環隆 (propoxycarbazone)、氟酮擴隆（flucarbazone)、磺草哩胺 (metosulam)、胺哩草酮（amicarbazone)、草甘膦異丙胺鹽 (glyphosate-isopropyl amine)、草硫磷（惡1丫卩11〇5316-trimesium)、固殺草（glufosinate)、雙丙胺碟（bialaphos)、 丁胺磷（butamifos) ' 节草丹（prosulfocarb)、擴草靈 (asulam)、理有龍（linuron)、過氧化鈣（calcium peroxide) 、拉草（alachlor)、施德甫（pendimethalin)、三氟殘草酸 (acifluofen- sodium)、乳氟禾草靈（lactofen)、稱苯腈 (ioxynil)、禾草靈（alloxydim)、西殺草（sethoxydim)、敵 草胺（napropamide)、吡唑特（pyrazolate)、吡草醚 (pyraflufen-ethyl) ' 依滅草（imazapyr)、甲磺草胺 (sulfentrazone)、百草枯（paraquat)、敵草快（diquat)、西 碼津（simazine)、 草脫淨（atrazine)、 氟噻乙草酯 (fluthiacet-methyl)、快肤草（quizalofop-ethyl)、本達隆 -59- 201238485 (bentazone)、D比喃擴隆（triaziflam)、脫葉脲（thidiazuron) 、口比哩解草醋（mefenpyr)、益收生長素（ethephon)、環丙 酸醯胺（cyclanilide)、氟胺草哩（flupoxam)、平速爛 (penoxsulam)、硝草酮（mesotrione)、沙弗芬那斯 (saflufenacil)、乙擴隆（flucetosulfuron) ' 醯苯草酮 (bencarbazone) ' 汰草滅（dimethenamid)、異丙草胺 (propisochlor)、唑醯草胺（metamifop)、磺醯草吡唑 (pyrasulfotole)、Π比嚼沙泛（pyrimisulfan)、甲氧磺草胺 (pyroxsulam)、派羅克殺草颯（pyroxasulfon)、D惡苯颯 (fenoxasulfone)、三哩啉酮（thiencarbazone)、擴醯胺基羯 基三嗤啉酮（thiencarbazone-methyl)、 氣達曉草醋 (flufenpyr-ethyl)、喃苯胺礎隆（orthosulfamuron)、垸基三 曉（indaziflam)、曝咪哩喃擴隆（propyrisulfuron)、草胺磷 鈉（glufosinate_P-sodium)、艾分卡斑哩（Ipfencarbazone)、 双醚氯卩比喃擴隆（metazosulfuron)、 環丙II·密陡酸 (aminocyclopyrachlor)、节草丹（prosulfocarb)、氯嘧黄隆 (c h 1 o r i m u r ο η - e t h y 1)等。 (1) 生物農藥之例可舉出核型多角體病毒（Nuclear polyhedrosis virus 、NPV)、顆粒病毒（Granulosis virus 、GV)、細胞質多角體病毒（Cytoplasmic polyhedrosis virus 、CPV)等。 (2) 蟲生線蟲（Steinernema carpocapsae)、本土 蟲生線 蟲（Steinernema glaseri)、瘤捕單頂孢（Monacrosporium phymatophagum)、蟲生線蟲（Steinernema kushidai)、巴斯 -60- 201238485 德桿菌（Pasteuria penetrans)等。 (3) 放射型土 壤桿菌（Agrobacterium radiobacter)、枯 草桿菌（Bacillus subtilis)、彩色海芋軟腐細菌（Erwinia carotovora)、蛋光假單胞菌（Pseudomonas fluorescens)、 磺藍狀菌（Talaromyces flavus)、抗诘性木黴菌 (Tri choderma atroviride)等 ° (4) 蘇力菌（Bacillus thuringiensis)、布氏白彊菌 (Beauveria brongniarti i) ' 白彊菌(Beauveria bassiana)、 玫瑰色擬青黴（Paecilomyces fumosoroseus)、蠟阶輪枝菌 (Verticillium lecanii)、格蘭氏陰性菌（Xanthomonas campestris)等 0 (5) 麗既小蜂（Encarsia formosa)、槳角极小蜂 (Eretmocerus eremicus)、蒙氏槳角蚜小蜂（Eretmocerus mundus)、寄生蜂（Aphidius colemani)、瘻蠅（Aphidoletes aphidimyza)、豌豆潛繩姬小蜂（Diglyphus isaea)、潛蠅類 離顎蟲蜂（Dacnusa sibirica)、智利捕植蟎（Phytoseiulus persimilis)、黃瓜鈍綏蟎（Amblyseius cucumeris)、力卩州捕 植摘（Amblyseius californicus)、南方小黑花椿象（〇rius strigicollis)等 ° 費洛蒙劑之例可舉出€〇(116111“（（£，£)-8，10-十一碳一 烧-1-醇）、Dotoamirua B((Z)-9-十四碳稀-1-醇）、乙酸 ((Z)-ll -十四碳稀醒）、Pyrimalure(14 -甲基-1-十八碳嫌）、 Peachflure((Z)-13-二十碳嫌-10-酮）等。 天然殺菌劑·天然殺蟲劑之例可舉出機油（Machine -61 - 201238485 oils)、乙酸甲基苯醋（Methylphenyl acetate)、α·蕕嫌（α-Pinene)、蛋白質水解物（Protein hydrolysate)、（Z)-l -十四 碳嫌-1·醇、松節油（Turpentine)等。 【實施方式】 [實施例] 以下以實施例具體說明本發明。又，該等並非限制本 發明。 實施例1 [製造例] (1)通式（1-1)中Rl=2-三氟甲基苯，R2 =氫原子之化合物（表 1，化合物No. 4之化合物）之合成 階段A: 2-(4-{2-三氟甲基}苯基-3-丁炔基）異吲哚-1，3-二 酮 將2 _64 g之二（三苯基磷）鈀二氯、710 mg之碘化銅 與15 g之N-(3-丁炔基）鄰苯二甲醯亞胺於氮氣環境下， 加入200 ml之四氫呋喃、25 g之2 -碘三氯甲苯、45 ml 之三乙基胺，並於還流下攪拌2小時。攪拌後使反應液冷 卻至室溫並過濾固體。濃縮濾液後，將殘渣以管柱氣相層 析儀（Waco-Gel C-200，甲苯）純化，得1 8.4 g之鄰苯二甲 醯亞胺化合物。 階段B: 4-(2-三氟甲基苯基）-3-丁烯胺 於上階段獲得之14 g之鄰苯二甲醯亞胺體中加入140 -62- 201238485 ml之甲醇及6 ml之聯胺單水和物（80%)，於室溫下攪拌 隔夜。濃縮反應液後將殘渣懸濁於1 5 0 m 1之氯仿中，過 濾不溶物之後，濃縮濾液，於減壓下進行乾燥，得8.2 g 胺。 階段C : 6, 8-二氟-4-羥基喹唑啉 於經依據EP 12142 99記載之方法製造之2.8 g之3, 5-二氟鄰胺基苯甲酸中加入25 m丨之甲醯胺，於175度下 攪拌9小時》冷卻至室溫後，加入水並過濾析出之固體。 以水洗淨，於真空下乾燥得目的之粗生成物2g。 階段D : 4-氯-6, 8-二氟喹唑啉 將上述所得之6, 8 -二氟-4-羥基喹唑啉加入30 ml之 亞硫醯氯，並滴入10滴作爲觸媒之N，N-二甲基甲醯胺於 85度下攪拌3小時。冷卻至室溫後，加入50ml之醋酸乙 酯’過濾不溶物。濃縮殘渣後以50ml之醋酸乙酯稀釋， 於冰浴-小蘇打中緩緩注入。以50ml之醋酸乙酯進行2次 萃取’再以硫酸鈉進行乾燥。過濾硫酸鈉後，濃縮有機層 ，將殘渣懸濁於l〇〇ml之二氯甲烷-己烷（1 : 3)中，過濾 不溶物後，濃縮濾液後得1 .9g氯唾唑啉。 階段E: 4-(4-{2-三氟甲基丨苯基-3-丁炔胺）-6，8-二氟喹唑 啉 於8 ml之N，N·二甲基甲醯胺中加入於上述階段C中 -63- 201238485 所得之胺200mg、上述階段D中所得之4-氯-6，8-二氟嗤 唑啉165mg、三乙基胺0.17ml，於80 °C下攪拌2.5小時 。冷卻反應液後，加入水30ml，以50ml之醋酸乙酯進行 2次萃取。以飽和食鹽水3 0ml洗淨有機層2次後，再以 硫酸鈉進行乾燥。過濾硫酸鈉後，濃縮有機層，將殘渣以 瞬間自動純化裝置瞬間柱狀層析儀（Biotage AB公司製 /IsoleraTM)進行純化，獲得目標生成物215mg。 依相同製造方法，合成表1、化合物No. 1〜6，10~12 (2)通式（1—1)中1^=4-氯-2-三氟甲基苯，R2=甲基之化合 物（表1，化合物No. 7之化合物）之合成 階段A: 2-(1-甲基-3-丁炔基）異吲哚-1，3-二酮 於充滿氮氣的燒瓶中加入乾燥400 ml之四氫呋喃、 5.00 g之4·戊炔-2-醇、9.65g之鄰苯二甲醯亞胺、17.13g 之三苯膦，並於室溫下將30 ml之偶氮二甲酸二乙酯（4 0% 甲苯溶液）緩慢滴入此溶液中，並於室溫下攪拌1天。濃 縮反應液後，於殘渣中加入水300ml，以250ml之醋酸乙 酯進行2次萃取。以水200ml及飽和食鹽水200ml洗淨有 機層2次後，再以硫酸鎂進行乾燥。過濾硫酸鎂後，濃縮 有機層，將殘渣以管柱氣相層析儀（Waco-Gel C-200，甲 苯）純化，得2.20 g之鄰苯二甲醯亞胺化合物。 階段B: 2-(1-甲基-4-{4-氯-2-三氟甲基}苯基-3-丁烯）異吲 -64 - 201238485 哚-1，3-二酮 將209mg之二氯雙（三苯基膦）鈀、57mg之碘化銅、 於上階段獲得之1.2 7g之鄰苯二甲醯亞胺化合物於氮氣環 境下，加入50ml之四氫呋喃、2.19g之3-氯5-碘三氯甲 苯、2.5 ml之三乙基胺，並於還流下攪拌4小時。攪拌後 ，冷卻反應液至室溫，過濾固體。濃縮濾液後，將殘渣以 瞬間自動純化裝置瞬間柱狀層析儀（Biotage AB公司製 /IsoleraTM)進行純化，獲得鄰苯二甲醯亞胺化合物i.73g。 階段C: 1-甲基-4-{4-氯-2-三氟甲基}苯基-3-丁烯胺 於上階段獲得之1.73g之鄰苯二甲醯亞胺體中加入20 ml之甲醇、10 ml之甲基胺溶液（40%甲醇溶液），於60 度下攪拌4小時。濃縮反應液後，以5 0 m 1之醋酸乙酯、 5 0 m 1之二***之順序洗淨後，濃縮濾液得粗生成物之胺 8 1 7mg 〇 階段D: 4-(4-{4-氯-2-三氟甲基}苯基-3-丁烯胺）-6，8-二 氟喹唑啉 於之N，N-二甲基甲醯胺中加入於上階段獲得 之胺550mg、實施例1所合成之4 -氯-6, 8 -二氟喹唑啉 310mg、三乙基胺〇.35ml’於80。(：下攪拌2.5小時。冷卻 反應液後加入30 ml之水，以50ml之醋酸乙酯進行2次 萃取。以飽和食鹽水30ml洗淨有機層2次，再以硫酸鈉 進行乾燥。過濾硫酸鈉後，濃縮有機層，將殘渣以瞬間自 -65- 201238485 動純化裝置瞬間柱狀層析儀（Biotage AB公司製/Isolera™) 進行純化，獲得目標生成物〇.5g。 依相同製造方法，合成表1、化合物No. 7、8、9。 且4-氯-6，8-二氟喹唑啉係依據W020 1 0/2545 1記載 之方法製造。 經如上所述合成之化合物[I ]及該等化合物之物性示 於表1(表1—1〜表1-2)。另外化合物[I]之NMR數據示 於表2。且本說明書中，「表1」係指表1_1及表1一 2 之總稱（包括性的名稱）。 -66- 201238485 [表 1-1] 化合物No. 構诰 物性 1 CF3 F m.p. 17^180^: 2 F m.p. 183 〜186Ϊ： 3 c 丨 OMe F m.p. 132 〜133t： 4 Hrjjcf3 F m ·ρ. 153 〜1541 5 c 丄 OMe X* F ro .p. 157〜161*C 6 F m.p. 189 〜191t： -67- 201238485 [表 1-2] 化合物No. 構造 物性 7 HN CF3 —。 F 樹脂状物 8 racemic F m.p. 132 〜133t： 9 JL^P1 CF3 racemic F m.p. 153〜155Ϊ： 10 F 0 F 油状物 11 F ^ ¢6 F 油状物 12 0 F m.p. 130〜133Ϊ： -68- 201238485 [表2] 化合物No δ値（p pm、溶媒：CDC 1 3、内部標準物質：TMS) 1 2.89(t, 2H), 3.94(q, 2H), 5.98(brs, 1H), 7.09-7.63 (m, 6H), 8.68(s, 1H) 2 2.89(t, 2H), 3.88(q, 2H), 5.50(d, 2H), 4.58(s, 2H), 6.96-7.64 (ra, 6H), 8.55(s, 1H) 3 2.85(t, 2H), 3.37(s, 3H), 3.90(q, 2H), 4.62(s, 2H), 6.69(brs, 1H), 7. 12-7.52 (m, 6H)( 8.67(s, 1H) 4 2. 70(t, 2H), 3.84(q, 2H), 6. 10(brs, 1H), 7.28-7.62 (in, 7H), 8.60(s, 1H) 5 2.78(t, 2H), 3.31(s, 3H), 3.90(q, 2H), 4.57(s, 2H), 6.62(brs, 1H), 6.83-7.45 (m, 5H), 8. 67(s, 1H) 6 2.89(t, 2H), 3.95(q, 2H), 5.50(d, 2H), 6. 16(brs, 1H), 7.13-7. 50 (m, 6H), 8.68(s, 1H) 7 2.89(t, 2H), 3.95(q, 2H), 5.50(d, 2H), 6. 16(brs, 1H), 7.13-7. 50(m, 6H), 8.68(s, 1H) 8 1.20(d, 3H), 2.69(dd, 2H), 3.36(s, 3H), 4.61 (dd, 2H), 4. 80-4. 89 (m, 1H), 6.45(brs, 1H), 7. 12-7. 54 (m, 6H), 8.66(s, 1H) 9 1.50(d, 3H), 2.90(dd, 2H), 4.60-4.84 (m, 1H), 5.84(brs, 1H), 7.12-7.70(m, 5H), 8.67(s, 1H) 10 2.82(t, 2H), 3.40(s, 3H), 3.89(q, 2H), 4.56(s, 2H), 6. 89-7. 44 (ra, 6H). 8.67(s, 1H) 11 2.91(t，2H), 3.38(s, 3H), 3.85(q, 2H), 4.59(s, 2H), 6. 89-7. 53 (m, 6H). 8.67(s, 1H) 12 2. 90(t, 2H), 3.93(q, 2H), 5. 50(d, 2H), 6. 98-7.48 (m, 6H), 8.67(s, 1H) 使用本發明之有害生物防治組成物時，可以泛用於農 藥製劑之粉劑、粒劑、微粒劑、錠劑、液劑、乳劑、水和 劑、流動劑、氣膠劑等製劑而使用。該等使用可藉由例如 處理種子、莖葉散佈、土壤施用或水面施用等一般之施用 方法。 根據本發明之有害生物防治組成物之施用量，依對象 病害、害蟲等發生傾向 '受害程度、環境條件、所使用之 製劑型而變動，一般施用量爲每10公畝爲0.1 g〜lkg。以 -69- 201238485 水稀釋液劑、乳劑、水和劑及流動劑等後而使用時，以 1〜lOOOOppm之範圍之稀釋濃度使用。 另外，將根據本發明之有害生物防治組成物，與殺菌 •殺黴劑、殺細菌劑、殺蟎劑、殺線蟲劑、殺蟲劑、生物 農藥、除草劑、植物荷爾蒙劑、植物發育調節物質、協同 劑、誘引劑、驅避劑、色素、肥料等之混合物，或組合選 自該等有效成分之一種或二種以上而成之混合物而施用時 之施用量，依組合之有害生物防治活性化合物之種類、對 象病害、發生傾向、受害程度、環境條件、所使用之製劑 型等而變動。一般以式1-1以及1-2所示之化合物群之具 體例，可舉出記載於[表1-1]以及[表1-2]之化合物群之含 氟唾唑啉衍生物之1種以上之農園藝用殺菌以及/或殺蟲 化合物之重量混合比爲1: 0.1〜1: 100000之比例，一般 施用量爲每10公畝爲O.lg〜lkg。以水稀釋液劑、乳劑、 水和劑及可流動劑等後而使用時，以1〜lOOOOppm之範圍 之稀釋濃度使用。 將本發明使用之化合物使用爲農園藝用有害生物防治 組成物時，可因應其目的將有效成分以適當的劑型使用。 一般將有效成分以惰性液體或固體載體稀釋，並因應需要 加入界面活性劑、其他成分，以例如粉劑、水和劑、乳液 製劑、粒劑等製劑型態使用。 適合的載體可舉出例如滑石、膨潤土、粘土、高嶺土 、矽藻土、白碳、蛭石、磷灰石、矽砂、硫安、尿素等固 體載體，異丙醇、二甲苯、環己酮、甲基萘等液體載體。 -70- 201238485 界面活性劑及分散劑可舉出例如二萘甲烷磺酸鹽、醇硫酸 酯鹽、烷基芳基磺酸鹽、木質素磺酸鹽、聚氧乙二醇醚、 聚氧乙烯烷基烷基芳基醚、聚氧乙烯山梨糖醇單芳酯等。 輔助劑可舉出羧甲基纖維速等。可將該等製劑以適當濃度 稀釋後再散佈，或直接施用。 進而本發明之有害生物防治組成物，可因應需要與殺 蟲劑、其他殺菌劑、除草劑、植物生長調節劑、肥料等混 合而使用。 其次對於本發明之農園藝用有害生物防治組成物舉具 代表之實施例，具體說明製劑方法。以下說明中「％」係 表示重量百分率。 實施例2[製劑例] 製劑例1 :乳劑 將10份之本發明化合物溶解於45份之1，2-二甲基-4-乙基苯，以及35份之1-甲基-2-吡喀啶酮，再於其中添 加10份之SORPOL 3005X(東邦化學工業股份有限公司製 造之界面活性劑之商品名），經攪拌混合後，得1 〇%之乳 劑。 製劑例2 :水和劑 將1〇份之本發明化合物添加於混合2份月桂基硫酸 鈉、4份木質素磺酸鈉、20份白碳及64份之灰石之混合 物中，以果汁機攪拌混合後，得1 0%之水和劑。 -71 - 201238485 製劑例3 :粒劑 將2份十二烷基苯磺酸鈉、2份羧基甲基纖維素、2 份月桂基硫酸鈉、1 0份膨潤土及79份粘土添加於5份之 本發明化合物中經充分搅拌。再加入適量的水進而攪拌， 以造粒機造粒後通風乾燥，得5%粒劑。 製劑例4 :粉劑 將1份之本發明化合物溶解於2份之大豆油中’添加 5份白碳，0.3份酸性磷酸異丙酯（PAP)以及91.7份之粘 土’以果汁機搅拌混合後，得1 %之粉劑。 製劑例5 :可流動劑 將2 0份之本發明化合物與2 0份之包含分別爲2份、 1份、0.2份之聚氧乙烯烷基醚、二烷基硫水楊酸鈉、1， 2-苯并異噻唑-3-酮之水混合，使用代諾（Dyno)粉碎機進行 濕式粉碎後，與60份之含有分別爲8份以及0.3 2份之丙 二醇及黃二膠之水混合，獲得20%之水中懸浮液。 製劑例6 :顆粒水和劑 將2份月桂基硫酸鈉、3份烷基萘磺酸鈉、5份糊精 、2 0份白碳、5 0份粘土添加於2 0份之本發明化合物中， 且經充分混合搅拌。再加入適量的水進而攪拌，以造粒機 造粒後通風乾燥，得20%顆粒水和劑。 -72- 201238485 實施例3 [效力試驗] 其次對於本發明之農園藝用有害生物防治組成物之效 果，舉試驗例具體說明。 試驗例1 .對番茄疫病之防治效果試驗 對盆中栽植之番茄幼苗（品種：小番茄，4.5葉期）使 用噴霧槍，以每盆散佈15ml，將各[表1-1]以及[表1-2]所 示之化合物群之含氟喹唑啉衍生物、化合物α以及化合物 冷之10%水和劑調整至50ppm之藥液（以下稱作供試藥液） ，1天後，噴霧接種番節疫病菌（Phytophthora infestans) 之孢子懸浮液（孢子濃度1.0x1 04個/ml)，於21°C之濕室條 件下放置1天，進而置於溫室中放置3天，使其充分發病 後，調査各葉之發病面積率，使用下式算出防治價。 防治價計算式：防治價={(未處理之發病面積率一處 理藥劑之發病面積率）/未處理之發病面積率}Χ1〇〇 所算出之防治價依據下述標準進行判斷。結果示於表3。 A : 1 0 0 % 3 防治價 2 9 8 °/。 B : 9 8 % > 防治價 2 6 0 % C : 60°/。> 防治價 2 20% D : 2 0 % >防治價2 0 % -73- 201238485 【化1 3】Bt agent: Bacillus thuringiensis and the like. Compounds that block ATP synthesis: diafenthiuron, azocyclotin, cyhexatin 'fenbutatin oxide', propargite, tetradifon, and the like. Deoxidative phosphorylation conjugated compound: chlorfenapyr and the like. Compounds that block the passage of nicotine acetylcholine receptors: bensultap, cartap, thiocyclam, and the like. Compounds that hinder the synthesis of chitin: chlorfluazuron, diflubenzuron, flufenazone-56- 201238485 (flufenoxuron) hexaflumuron, lufenuron, Novaluron, teflubenzuron, triflumuron, buprofezin, bistrifluron, and the like. Compounds that interfere with peeling and metamorphosis: cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, η 〇vif 1 Umur ο η) et al 0 octopamine antagonist compounds: amitraz, hydramethylnon, acequinocyl and the like. Blocking electron transport system compounds: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, fish vine Rotenone, etc. " Aluminium phosphide. Compounds that block the potential-dependent sodium ion channel: indoxacarb, metaflumizone, s p i r 〇 d i c 1 〇 f e η, and the like. Compounds that block lipid synthesis: spiromesifen, spirotetramat, and the like. Compounds that block the ryanodine receptor: chlorantranilprole, flubendiamide, cyantranilprol, and the like. Compounds with other or unknown effects: azadirachtin -57- 201238485, benzoximate 'bifenazate, chinomethionat, dicof〇l, fixed Pyridalyl, pyrifluquinazon, fiuensuifone, etc. Examples of the herbicide include the following compounds. Also known as benzobicyclon, bensulfuron-methyl, azimsulfuron, cinosulfuron, cyclosulfamuron, pyrazosulfuron-ethyl ), imazosulfuron, indanofan, cyhalofop-butyl, thenylchlor 'esprocarb, acebenzamide , cafenstrole, clomeprop, dimethametryn, daimuron, bifenox, pyributicarb, pyriminobac-methyl ), pretilachlor, bromobutide, benzofenap, topramezone, benthiocarb, pentoxazone, valerian yellow (benfuresate), mefenacet, fenoxaprop-P-ethyl, phenmedipham, diclofop-methyl, desmedipham, fenfurtil Yellow (ethofumesate), isoproturon (isoproturon), scorpion huanglong (ami Dosulfuron), anilofos, benfuresate, ethoxysulfuron, iodosulfuron, isoxadifen, foramsulfuron, double Pyraclonil, mesosulfuron, dayoulong-58- 201238485 (diuron), neburon, dinoterb, carbeamide, bromoxynil (bromoxynil), oxadiazon, dimefuron, diflufenican, aclonifen, benzofenap, oxaziclomefone, snail Grass (i sox aflutol e), oxadiargyl, flurtamone, metribuzin, metabenzthiazuron, tribufos, benzene Methantron, ethiozin, flufenacet, sulcotrion, tefuryltrione, fentrazamide, benzepazine Propoxycarbazone), flucarbazone, sulphonamide (me Tosulam), amicarbazone, glyphosate-isopropyl amine, glufosinate (Evil 1丫卩11〇5316-trimesium), glufosinate, dipropylamine dish ( Bialaphos), butamifos 'prosulfocarb, asulam, linuron, calcium peroxide, alachlor, pendimethalin, Acifluofen-sodium, lactofen, ioxynil, alloxydim, sethoxydim, napropamide, pyrazol (pyrazolate), pyraflufen-ethyl 'imazapyr, sulfentrazone, paraquat, diquat, simazine, stalk Atrazine, fluthiacet-methyl, quizalofop-ethyl, binalon-59-201238485 (bentazone), D-pyramid, defidient urea (thidiazuron) ), mouth 哩 草 草 vinegar (mefenpyr), oesotropin (ethephon), cyanopropionic acid Cyclanilide, flupoxam, penoxsulam, mesotrione, saflufenacil, flucetosulfuron 'bencarbazone' 'Dimethenamid, propisochlor, metamifop, pyrasulfotole, pyrimisulfan, pyroxullam , pyroxasulfon, fenoxasulfone, thiencarbazone, thiencarbazone-methyl, flufenpyr -ethyl), orthosulfamuron, indaziflam, propyrisulfuron, glufosinate_P-sodium, Ipfencarbazone, double Etherosulfuron, aminocyclopyrachlor, prosulfocarb, ch 1 orimur ο η - ethy 1 and the like. (1) Examples of the biological pesticide include Nuclear polyhedrosis virus (NPV), Granulosis virus (GV), Cytoplasmic polyhedrosis virus (CPV), and the like. (2) Steinernema carpocapsae, Steinernema glaseri, Monacrosporium phymatophagum, Steinernema kushidai, Bass-60- 201238485 Pasteuria penetrans Wait. (3) Agrobacterium radiobacter, Bacillus subtilis, Erwinia carotovora, Pseudomonas fluorescens, Talaromyces flavus, anti-Agrobacterium radiobacteria (Bacillus subtilis) Tri choderma atroviride et al. (4) Bacillus thuringiensis, Beauveria brongniarti i 'Beauveria bassiana, Paecilomyces fumosoroseus, Verticillium lecanii, Xanthomonas campestris, etc. 0 (5) Encarsia formosa, Eretmocerus eremicus, Montessori (Eretmocerus mundus), Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus persimilis , Amblyseius cucumeris, Amblyseius californicus, Southern black scorpion (〇rius strigicol Lis) et al. Examples of pheromone can be exemplified by (〇116116"((£,£)-8,10-unde carbon-burn-1-ol), Dotoamirua B((Z)-9-ten Tetracarbon-1-ol), acetic acid ((Z)-ll - fourteen carbon awake), Pyrimalure (14-methyl-1-eight carbon), Peachflure ((Z)-13- twenty carbon -10-ketone), etc. Natural fungicides and natural insecticides can be exemplified by motor oil (Machine -61 - 201238485 oils), methyl ethyl acrylate (Methylphenyl acetate), α·莸 (α-Pinene) , protein hydrolysate, (Z)-1 -tetradecyl-1, alcohol, turpentine, etc. [Embodiment] [Examples] Hereinafter, the present invention will be specifically described by way of examples. Moreover, these do not limit the invention. Example 1 [Production Example] (1) Synthesis Stage A of the compound of the formula (1-1) wherein R1 = 2-trifluoromethylbenzene, and R2 = a hydrogen atom (Table 1, Compound No. 4): 2-(4-{2-Trifluoromethyl}phenyl-3-butynyl)isoindole-1,3-dione 2 - 64 g of bis(triphenylphosphine)palladium dichloride, 710 mg Copper iodide and 15 g of N-(3-butynyl) phthalimide in a nitrogen atmosphere, adding 200 ml of tetrahydrofuran, 25 g of 2-iodotrichlorotoluene, 45 ml of triethyl The amine was stirred and allowed to flow for 2 hours. After stirring, the reaction solution was cooled to room temperature and the solid was filtered. After concentrating the filtrate, the residue was purified by column column gas chromatography (Waco-Gel C-200, toluene) to obtain 1 8.4 g of phthalimide compound. Stage B: 4-(2-trifluoromethylphenyl)-3-butenamine is added to 14 g of phthalate imine obtained in the previous stage, 140-62-201238485 ml of methanol and 6 ml. The hydrazine monohydrate (80%) was stirred overnight at room temperature. After concentrating the reaction mixture, the residue was suspended in chloroform of 150 ml, and the insoluble material was filtered. The filtrate was concentrated and dried under reduced pressure to give 8.2 g of amine. Stage C: 6, 8-difluoro-4-hydroxyquinazoline in 2.8 g of 3,5-difluoro-o-aminobenzoic acid manufactured by the method described in EP 12142 99, 25 m of decylamine After stirring at 175 °C for 9 hours. After cooling to room temperature, water was added and the precipitated solid was filtered. It was washed with water and dried under vacuum to obtain 2 g of the desired crude product. Stage D: 4-chloro-6, 8-difluoroquinazoline The above-obtained 6,8-difluoro-4-hydroxyquinazoline was added to 30 ml of sulfinium chloride, and 10 drops were added as a catalyst. The N,N-dimethylformamide was stirred at 85 °C for 3 hours. After cooling to room temperature, 50 ml of ethyl acetate was added to filter insolubles. The residue was concentrated, diluted with 50 ml of ethyl acetate, and poured slowly in ice bath-baking. It was extracted twice with 50 ml of ethyl acetate and dried over sodium sulfate. After the sodium sulfate was filtered, the organic layer was concentrated, and the residue was suspended in methylene chloride-hexane (1:3), and filtered, and then filtrated to give 1.9 g of chloro- oxaline. Stage E: 4-(4-{2-trifluoromethylnonyl-3-butynylamine)-6,8-difluoroquinazoline in 8 ml of N,N-dimethylformamide 200 mg of the amine obtained in the above stage C-63-201238485, 165 mg of 4-chloro-6,8-difluorooxazoline obtained in the above stage D, and 0.17 ml of triethylamine were stirred at 80 ° C. hour. After cooling the reaction mixture, 30 ml of water was added, and extraction was carried out twice with 50 ml of ethyl acetate. The organic layer was washed twice with 30 ml of saturated brine and dried over sodium sulfate. After the sodium sulfate was filtered, the organic layer was concentrated, and the residue was purified by a flash column chromatography (manufactured by Biotage AB / IsoleraTM) to obtain a target product of 215 mg. According to the same production method, the synthesis of Table 1, Compound No. 1 to 6, 10 to 12 (2) in the general formula (1 - 1), 1 ^ = 4-chloro-2-trifluoromethylbenzene, R2 = methyl Synthesis Stage of Compound (Table 1, Compound No. 7) Stage A: 2-(1-Methyl-3-butynyl)isoindole-1,3-dione was added to a nitrogen-filled flask to dry 400 Mol of tetrahydrofuran, 5.00 g of 4·pentyn-2-ol, 9.65 g of phthalimide, 17.13 g of triphenylphosphine, and 30 ml of diethyl azodicarboxylate at room temperature (40% toluene solution) was slowly dropped into the solution and stirred at room temperature for 1 day. After the reaction mixture was concentrated, 300 ml of water was added to the residue, and extracted twice with 250 ml of ethyl acetate. The organic layer was washed twice with 200 ml of water and 200 ml of saturated brine, and then dried over magnesium sulfate. After filtering magnesium sulfate, the organic layer was concentrated, and the residue was purified by column chromatography (Waco-Gel C-200, toluene) to give 2.20 g of phthalimide compound. Stage B: 2-(1-Methyl-4-{4-chloro-2-trifluoromethyl}phenyl-3-butene)isoindole-64 - 201238485 哚-1,3-dione 209mg Dichlorobis(triphenylphosphine)palladium, 57 mg of copper iodide, 1.27 g of the phthalimide compound obtained in the previous stage were added to 50 ml of tetrahydrofuran and 2.19 g of 3-chloro-5 under a nitrogen atmosphere. - Iodotrichlorotoluene, 2.5 ml of triethylamine, and stirred for 4 hours while still flowing. After stirring, the reaction solution was cooled to room temperature, and the solid was filtered. After the filtrate was concentrated, the residue was purified by an instantaneous column chromatography (manufactured by Biotage AB / IsoleraTM) to obtain i-73 g of the phthalimide compound. Stage C: 1-methyl-4-{4-chloro-2-trifluoromethyl}phenyl-3-butenamine 20 ml added to the 1.73 g of phthalimin obtained in the previous stage Methanol, 10 ml of methylamine solution (40% in methanol) was stirred at 60 °C for 4 hours. After concentrating the reaction mixture, the mixture was washed with 500 ml of ethyl acetate and 50 ml of diethyl ether, and then the filtrate was concentrated to give the crude product of the amine 8 1 7 mg. Stage D: 4-(4-{4 -chloro-2-trifluoromethyl}phenyl-3-butenamine)-6,8-difluoroquinazoline to which N,N-dimethylformamide was added to the amine obtained in the previous stage 550 mg The 4-chloro-6,8-difluoroquinazoline 310 mg and triethylamine oxime.35 ml' synthesized in Example 1 were 80. (The mixture was stirred for 2.5 hours. After cooling the reaction mixture, 30 ml of water was added, and extraction was carried out twice with 50 ml of ethyl acetate. The organic layer was washed twice with saturated brine (30 ml) and dried over sodium sulfate. After that, the organic layer was concentrated, and the residue was purified by an instantaneous column chromatography (Biotage AB/IsoleraTM) from the -65-201238485 moving purification apparatus to obtain a target product of 55 g. Table 1, Compound No. 7, 8, and 9. 4-Chloro-6,8-difluoroquinazoline was produced according to the method described in W020 1 0/2545 1. The compound [I] synthesized as described above and The physical properties of the compounds are shown in Table 1 (Table 1-1 to Table 1-2). The NMR data of the compound [I] are shown in Table 2. In the present specification, "Table 1" means Table 1_1 and Table 1. A general term for a 2 (including the name of the sex). -66- 201238485 [Table 1-1] Compound No. Structured property 1 CF3 F mp 17^180^: 2 F mp 183 ～186Ϊ: 3 c 丨OMe F mp 132 ~133t: 4 Hrjjcf3 F m ·ρ. 153 ～1541 5 c 丄OMe X* F ro .p. 157~161*C 6 F mp 189 ～191t: -67- 201238485 [ 1-2] Compound No. Structural property 7 HN CF3 — F Resin 8 racemic F mp 132 ～133t: 9 JL^P1 CF3 racemic F mp 153~155Ϊ: 10 F 0 F Oil 11 F ^ ¢6 F Oil 12 0 F mp 130 to 133 Ϊ: -68- 201238485 [Table 2] Compound No δ 値 (p pm, solvent: CDC 1 3, internal standard material: TMS) 1 2.89 (t, 2H), 3.94 (q, 2H), 5.98(brs, 1H), 7.09-7.63 (m, 6H), 8.68(s, 1H) 2 2.89(t, 2H), 3.88(q, 2H), 5.50(d, 2H), 4.58(s , 2H), 6.96-7.64 (ra, 6H), 8.55(s, 1H) 3 2.85(t, 2H), 3.37(s, 3H), 3.90(q, 2H), 4.62(s, 2H), 6.69( Brs, 1H), 7. 12-7.52 (m, 6H)( 8.67(s, 1H) 4 2. 70(t, 2H), 3.84(q, 2H), 6. 10(brs, 1H), 7.28- 7.62 (in, 7H), 8.60(s, 1H) 5 2.78(t, 2H), 3.31(s, 3H), 3.90(q, 2H), 4.57(s, 2H), 6.62(brs, 1H), 6.83 -7.45 (m, 5H), 8. 67(s, 1H) 6 2.89(t, 2H), 3.95(q, 2H), 5.50(d, 2H), 6. 16(brs, 1H), 7.13-7 50 (m, 6H), 8.68(s, 1H) 7 2.89(t, 2H), 3.95(q, 2H), 5.50(d, 2H), 6. 16(brs, 1H), 7.13-7. 50 (m, 6H), 8.68(s, 1H) 8 1.20(d, 3H), 2.69(dd, 2H), 3.36(s, 3H), 4.61 (dd, 2H), 4. 80-4. 89 (m, 1H), 6.45 (brs, 1H), 7. 12-7. 54 (m, 6H), 8.66(s, 1H) 9 1.50(d, 3H), 2.90(dd, 2H), 4.60- 4.84 (m, 1H), 5.84(brs, 1H), 7.12-7.70(m, 5H), 8.67(s, 1H) 10 2.82(t, 2H), 3.40(s, 3H), 3.89(q, 2H) , 4.56(s, 2H), 6. 89-7. 44 (ra, 6H). 8.67(s, 1H) 11 2.91(t,2H), 3.38(s, 3H), 3.85(q, 2H), 4.59 (s, 2H), 6. 89-7. 53 (m, 6H). 8.67(s, 1H) 12 2. 90(t, 2H), 3.93(q, 2H), 5. 50(d, 2H) , 6. 98-7.48 (m, 6H), 8.67 (s, 1H) When using the pest control composition of the present invention, it can be widely used for powders, granules, microgranules, tablets, liquids, and pesticides of pesticide preparations. It is used as a preparation for emulsions, water and agents, flow agents, and aerosols. Such use can be by ordinary application methods such as treatment of seeds, stem and leaf spreading, soil application or surface application. The application amount of the pest control composition according to the present invention varies depending on the tendency of the target disease, pest, etc., the degree of damage, the environmental conditions, and the type of preparation used, and the general application amount is 0.1 g to 1 kg per 10 are. When using -69- 201238485 water dilution solution, emulsion, water and agent, and flow agent, use it at a dilution concentration ranging from 1 to 100 ppm. In addition, the pest control composition according to the present invention, and a bactericidal, fungicide, bactericide, acaricide, nematicide, insecticide, biological pesticide, herbicide, plant hormone, plant development regulating substance a mixture of a synergist, an attractant, a repellent, a pigment, a fertilizer, or the like, or a combination of one or more selected from the active ingredients, and the application amount according to the combined pest control activity The type of the compound, the target disease, the tendency to occur, the degree of damage, the environmental conditions, the formulation type used, and the like vary. Specific examples of the compound group represented by the formulae 1-1 and 1-2 include the fluorine-containing oxazoline derivative of the compound group described in [Table 1-1] and [Table 1-2]. The ratio of the weight ratio of the above-mentioned agricultural and horticultural bactericidal and/or insecticidal compound is 1:0.1 to 1:100000, and the general application amount is O.lg~lkg per 10 are. When it is used after being diluted with a water, an emulsion, a water, a solvent, a flowable agent, or the like, it is used in a diluted concentration in the range of 1 to 100 ppm. When the compound used in the present invention is used as a pest control composition for agriculture and horticulture, the active ingredient can be used in an appropriate dosage form depending on the purpose. The active ingredient is usually diluted with an inert liquid or a solid carrier, and if necessary, a surfactant, other ingredients are added, for example, in the form of a preparation such as a powder, a water and an agent, an emulsion preparation, or a granule. Suitable carriers include, for example, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, apatite, strontium sand, sulphur, urea, and the like, isopropanol, xylene, cyclohexanone, A liquid carrier such as methylnaphthalene. -70- 201238485 The surfactant and dispersant may, for example, be dinaphthoic acid sulfonate, alcohol sulfate salt, alkyl aryl sulfonate, lignosulfonate, polyoxyethylene glycol ether, polyoxyethylene. Alkyl alkyl aryl ether, polyoxyethylene sorbitol monoaryl ester, and the like. The adjuvant may, for example, be a carboxymethyl fiber speed or the like. These preparations may be diluted at an appropriate concentration and then dispensed or administered directly. Further, the pest control composition of the present invention can be used in combination with an insecticide, other fungicide, herbicide, plant growth regulator, fertilizer, etc., as needed. Next, a representative example of the pest control composition for agricultural and horticultural use of the present invention will be specifically described. In the following description, "%" indicates the weight percentage. Example 2 [Formulation Example] Formulation Example 1: Emulsion 10 parts of the compound of the present invention were dissolved in 45 parts of 1,2-dimethyl-4-ethylbenzene, and 35 parts of 1-methyl-2-pyridyl Acaridone, and 10 parts of SORPOL 3005X (trade name of a surfactant manufactured by Toho Chemical Industry Co., Ltd.) was added thereto, and after stirring and mixing, an emulsion of 1% by weight was obtained. Formulation Example 2: Water and Agent A 1 part portion of the compound of the present invention is added to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of white carbon and 64 parts of gray stone to prepare a juice machine. After stirring and mixing, 10% water and a solvent were obtained. -71 - 201238485 Formulation Example 3: Granules 2 parts of sodium dodecylbenzenesulfonate, 2 parts of carboxymethylcellulose, 2 parts of sodium lauryl sulfate, 10 parts of bentonite, and 79 parts of clay are added to 5 parts. The compound of the present invention is thoroughly stirred. Then, an appropriate amount of water was added and stirred, and granulated by a granulator to be ventilated and dried to obtain 5% granules. Formulation Example 4: Powder 1 part of the compound of the present invention is dissolved in 2 parts of soybean oil, '5 parts of white carbon, 0.3 parts of isopropyl acid phosphate (PAP) and 91.7 parts of clay' are stirred and mixed by a juice machine. Get 1% powder. Formulation Example 5: Flowable Agent 20 parts of the compound of the present invention and 20 parts each comprise 2 parts, 1 part, 0.2 part of polyoxyethylene alkyl ether, sodium dialkyl sulfosalicylate, 1, The 2-benzisothiazol-3-one is mixed with water, and after wet pulverization using a Dyno pulverizer, mixed with 60 parts of water containing 8 parts by weight and 0.32 parts of propylene glycol and yellow gemin respectively. , obtain 20% suspension in water. Formulation Example 6: Granule water and agent 2 parts of sodium lauryl sulfate, 3 parts of sodium alkylnaphthalene sulfonate, 5 parts of dextrin, 20 parts of white carbon, and 50 parts of clay are added to 20 parts of the compound of the present invention. And thoroughly mixed and stirred. Then, an appropriate amount of water is added and stirred, and granulated by a granulator to be ventilated and dried to obtain 20% granule water and a granule. -72-201238485 Example 3 [Efficacy test] Next, the effects of the pest control composition for agriculture and horticulture of the present invention will be specifically described by way of test examples. Test Example 1. Control effect on tomato blight The tomato seedlings (variety: small tomato, 4.5 leaf stage) planted in pots were sprayed with a spray gun, each of which was spread 15 ml, each [Table 1-1] and [Table 1 -2] The fluorine-containing quinazoline derivative of the compound group shown, the compound α, and the 10% water and the compound of the compound are adjusted to 50 ppm of the drug solution (hereinafter referred to as the test solution), and after 1 day, spray inoculation Spore suspension of Phytophthora infestans (spore concentration 1.0x1 04/ml), placed in a wet room at 21 °C for 1 day, and then placed in the greenhouse for 3 days to make it fully ill The area ratio of each leaf was investigated, and the control price was calculated using the following formula. The calculation price of the prevention price: the prevention price = {(untreated area ratio, the area ratio of the treatment agent) / the area ratio of the untreated area} Χ1〇〇 The calculated control price is judged according to the following criteria. The results are shown in Table 3. A : 1 0 0 % 3 Control price 2 9 8 °/. B : 9 8 % > Control price 2 60 % C : 60°/. > Prevention price 2 20% D : 2 0 % > Prevention price 20% -73- 201238485 【化1 3】

[表3] 對番茄疫病之防治效果 防治效果 判斷 化合物N 〇. A 1、2、3、6、7、8、9、10、11、12、 B 4、5、 C D 化合物α、化合物0 試驗例2.對小黃瓜露菌病之防治效果試驗 對盆中栽植之小黃瓜幼苗（品種：半白節成，2.5葉期 )使用噴霧槍，以每盆散佈15ml，將各[表1-1]以及[表1-2]所示之化合物群（含氟喹唑啉衍生物）、化合物α以及化 合物/3之10%水和劑調整至50ppm之藥液（以下稱作供試 藥液），1天後，噴霧接種露菌病菌（Pseudoperonospora cubensis)之分生子懸浮液（分生子濃度KOxlO4個/ml)。接 種後於21 °C之濕室條件下放置1天，進而置於溫室中放 置3天，使其充分發病後，調查各葉之發病面積與未處理 區之對比，進行與試驗例1 .相同之防治效果判斷。結果示 於表4。 -74- 201238485 [表4] 對小黃瓜露菌病之防治效果 防治效果 判斷 化合物N 〇. A 1、2、3、4、5、6、7、8、9、10、11、12、 B C D 化合物α、化合物)3 試驗例3.對小黃瓜白粉病之防治效果試驗 對盆中栽植之小黃瓜幼苗（品種：半白節成，2葉期） 使用噴霧槍，以每盆散佈15ml，將各[表1-1]以及[表1-2] 所示之化合物群（含氟喹唑啉衍生物）、化合物α以及化合 物/3之10%水和劑調整至5 Oppm之藥液（以下稱作供試藥 液），1天後，噴霧接種小黃瓜白粉病菌（Sphaerotheca fuliginea)之分生子懸浮液（分生子濃度l.OxlO5個/ml)。置 於溫室中放置14天使其充分發病後，調查各葉之發病程 度與未處理區之對比，進行與試驗例1 .相同之防治效果判 斷。結果示於表5。 [表5] 對小黃瓜白粉病之防治效果 防治效果 判斷 化合物N 〇 . A 1、2、3、4、5、6、7、8、9、1 0、1 1、 12、 B C D 化合物α、化合物|3 試驗例4.對棉蚜蟲之殺蟲效果試驗 將[表1-1]以及[表1-2]所示之化合物群（含氟喹唑啉 -75- 201238485 衍生物）、化合物α以及化合物沒之1 0 %水和劑等化合物 稀釋爲50ppm。將直徑3cm之小黃瓜葉片置於裝有0.5% 軟洋菜之塑膠杯上，並放養5隻棉蚜蟲（Aphis gossypii)雌 性成蟲。放置1晚後，移去成蟲計算產出之幼蟲數，以經 調整之藥液每次散佈〇.4ml，並於散佈2天後計算死亡蟲 數，算出死亡率。依據下述標準對照所計算之死亡率判定 殺蟲效果。結果不於表6。 A : 1 0 0 % 2 死亡率 2 9 8 % B : 9 8 % > 死亡率 2 6 0 % C : 6 0 % > 死亡率 2 2 0 % D : 2 0 % >死亡率2 0 % [表6] 對棉蚜蟲之殺蟲效果 殺蟲效果 判斷 化合物N 〇 . A 1、2、3、4、5、6、7、8、9、10、11、 12、 B C D 化合物α、化合物 試驗例5.對二點葉蟎雌成蟲之殺成蟲效果試驗 將[表1-1]以及[表1_2]所示之化合物群（含氟喹唑啉 衍生物）、化合物α以及化合物/3之1 0%水和劑等化合物 稀釋爲lOOppm。將直徑3cm之菜豆葉片置於裝有0.5 %軟 洋菜之塑膠杯上，並放養10隻二點葉蟎（Tetranychus urticae)雌性成蟲。以經調整之藥液每次散佈0.4ml，並於 散佈2天後計算死亡蟲數，算出死亡率。自所計算之死亡 -76- 201238485 率以與試驗例4相同之標準判定殺蟲效果。結果示於表7 [表7] 對二點葉蟎雌成蟲之笔成蟲效果 穀蟲效果 判斷 化合物N 〇. A 8、1 2、 B _1、 2、 3、 4、 5、 6、 7、 9、 10、 11、 C D 化合物α、化合物 試驗例6.對二點葉蟎卵之殺卵效果試驗 將[表1-1]以及[表1-2]所示之化合物群（含氟喹唑啉 衍生物）、化合物α以及化合物办之1 0%水和劑等化合物 稀釋爲lOOppm。將直徑3cm之菜豆葉片置於裝有0.5%軟 洋菜之塑膠杯上，並放養10隻二點葉觸（Tetranychus urticae)雌性成蟲。於室溫下靜置一晚使其產卵，移除放 養之雌成蟲後，以經調整之藥液每次散佈〇.4ml，並於散 佈6天後計算死亡蟲數。自所計算之死亡率以與試驗例4 相同之標準判定殺卵效果。結果示於表8。 [表8] 對二點葉蟎卵之殺卵效果 殺卵效果 判斷 化合物N 〇 . A 8、1 2、 B 1、 2、 3、 4、 5、 6、 7、 9、 10、 11、 C D 化合物α、化合物/3 試驗例7-1.對斜紋夜蛾之殺蟲效果試驗 將[表1-1]以及[表1-2]所示之化合物群（含氟喹D坐咐 -77- 201238485 衍生物）、化合物α以及化合物/9之1 ο %水和劑等化合物 稀釋爲lOOppm。將直徑3cm之白菜葉片經各藥液浸漬處 理，風乾，放置於塑膠皿中，並放養斜紋夜蛾（Spodoptera litura)3齡幼蟲10隻。計算處理2天後之死亡蟲數算出死 亡率。自所計算之死亡率以與試驗例4相同之標準判定殺 蟲效果。結果示於表9-1。 [表 9-1] 對斜紋夜蛾之殺蟲效果 殺蟲效果 判斷 化合物N 〇. A 1、2、3、4、5、6、7、8、9、10、11、12 B C D 化合物α、化合物 試驗例7-2.對西方花薊馬之殺蟲效果試驗 將[表1-Π以及[表1-2]所示之化合物群（含氟唾唑啉 衍生物）、化合物α以及化合物之1 〇%水和劑等化合物 稀釋爲500ppm。將直徑33mcm之菜豆葉片經各藥液浸漬 處理，風乾，放置於鋪有濾紙之直徑5 0mm的塑膠皿中， 並放養西方花薊馬（Frankliniella occidentalis)l, 2齡幼蟲 1〇隻。計算處理3天後之生存個體數’及計算死亡個體 數，算出死亡率。自所計算之死亡率以與試驗例4相同之 標準判定殺蟲效果。 -78- 201238485 [表 9-2] 對西方花薊馬之殺蟲效果 殺蟲效果 判斷 化合物 N o · A 1, 2, 3, 4，5, 6, 8，9, 1 0，1 1，1 2 B 7 C D 化合物a，化合物)3 試驗例8 .對小黃瓜白粉病之防治效果試驗 對盆中栽植之小黃瓜幼苗（品種：半白節成，2葉期） 使用噴霧槍，以每盆散佈1 5ml，將依製劑例爲準調製之[ 表1-1]以及[表1-2]所示之化合物群（含氟喹唑啉衍生物） ，以及[表10]所示之現有的殺菌活性化合物（以下以對應 於化合物名稱之英文字母表示），經以水稀釋調整至含有 規定濃度之有效成份之混合物散佈。風乾後，噴霧接種小 黃瓜白粉病菌（Sphaerotheca fuliginea)之分生子懸浮液。 其後於溫室中栽培14天後調查各葉之發病面積率，使用 下式算出防治價。 防治價計算式：防治價={(未處理之發病面積率-處 理藥劑之發病面積率）/未處理之發病面積率}χ1〇〇] 另外’以科爾比（Colby)的計算式求得藉由組合各活 性化合物所期待之效果。實驗値較計算値E爲大時，該組 合所得之效果顯示具有相乘效果。科爾比（Co丨by)的計算 式（Colby，S. R. 「除草劑組合之相乘性的以及拮抗性的 反應之§十算」（Calculating syner gistic and antagonistic -79- 201238485 responses of herbicide combination)， 22(1 967))係如下所示。 科爾比（Colby)的|十算式：E = A+B - E係使用濃度X之活性化合物X以：ί 合物Υ之混合物時，對未經處理之對照 價）。 Α係使用濃度X之活性化合物X時 照的預期效果（防治價）。 B係使用濃度y之活性化合物Y時 照的預期效果（防治價）。 各活性化合物之效果示於表10，才 現有之殺菌活性化合物之混合物之效果 1~表 11-8。[Table 3] Judging effect of control effect of tomato blight on compound N 〇. A 1, 2, 3, 6, 7, 8, 9, 10, 11, 12, B 4, 5, CD compound α, compound 0 test Example 2. Control effect on cucumber cucumber debride disease Test on cucumber seedlings planted in pots (variety: half-white section, 2.5 leaf stage) using a spray gun, spreading 15 ml per pot, each [Table 1-1 And the compound group (fluorinated quinazoline derivative) shown in [Table 1-2], the compound α, and the 10% water and the compound of the compound /3 are adjusted to 50 ppm (hereinafter referred to as the test liquid) After 1 day, the inoculum suspension of the bacteria (Pseudoperonospora cubensis) was sprayed (conversion concentration KOxlO4/ml). After inoculation, the cells were allowed to stand in a wet room at 21 ° C for 1 day, and then placed in a greenhouse for 3 days to allow sufficient disease to be observed. The area of the diseased area of each leaf was compared with that of the untreated area, and the same as in Test Example 1. The control effect is judged. The results are shown in Table 4. -74- 201238485 [Table 4] Judging effect of control effect of cucumber cucumber debride disease compound N 〇. A 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, BCD Compound α, compound) 3 Test Example 3. Control effect on cucumber powdery mildew test Cucumber seedlings planted in pots (variety: half-white section, 2 leaf stage) Using a spray gun, spreading 15 ml per pot, The compound group (fluorinated quinazoline derivative), the compound α, and the 10% water and the compound of the compound /3, which are shown in [Table 1-1] and [Table 1-2], are adjusted to a liquid solution of 5 Oppm (below It is called a test solution), and one day later, a meristematic suspension of Sphaerotheca fuliginea (sporozoite concentration: 1.0×x5/ml) was spray-inoculated. After placing 14 angels in the greenhouse for full incidence, the degree of onset of each leaf was compared with that of the untreated area, and the same control effect judgment as in Test Example 1 was carried out. The results are shown in Table 5. [Table 5] Judging effect of the control effect of cucumber powdery mildew on compound N 〇. A 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, BCD compound α, Compound|3 Test Example 4. Insecticidal effect against cotton aphid The compound group shown in [Table 1-1] and [Table 1-2] (fluorinated quinazoline-75-201238485 derivative), compound α And a compound such as 10% water and a compound which is not diluted with the compound is diluted to 50 ppm. A 3 cm diameter cucumber leaf was placed on a plastic cup containing 0.5% softwood and 5 adult female mites (Aphis gossypii) were stocked. After standing for 1 night, the number of larvae produced by the adult was calculated, and the adjusted liquid was dispersed for 4 ml each time, and the number of dead insects was calculated 2 days after the spread, and the mortality was calculated. The insecticidal effect was determined against the calculated mortality according to the following criteria. The results are not shown in Table 6. A : 1 0 0 % 2 Mortality 2 9 8 % B : 9 8 % > Mortality 2 60 % C : 60% > Mortality 2 2 0 % D : 2 0 % > Mortality 2 0 % [Table 6] Insecticidal effect on insecticidal effect of cotton aphid Compound N 〇. A 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, BCD compound α, compound Test Example 5. Adult larval effect on female adult mites: [Table 1-1] and [Table 1-2] compound group (fluorinated quinazoline derivative), compound α, and compound /3 A compound such as 10% water and a solvent is diluted to 100 ppm. A 3 cm diameter bean leaf was placed on a plastic cup containing 0.5% softwood and 10 female Tetranychus urticae female adults were stocked. The adjusted drug solution was dispensed with 0.4 ml each time, and the number of dead insects was counted after 2 days of spreading, and the mortality was calculated. From the calculated death -76 - 201238485 The insecticidal effect was determined by the same criteria as in Test Example 4. The results are shown in Table 7 [Table 7] The effect of the adult worm on the adult larvae of the two-spotted spider mites. The worm effect judgment compound N 〇. A 8, 1 2, B _1, 2, 3, 4, 5, 6, 7, 9 , 10, 11, CD compound α, compound test example 6. Test on the ovicidal effect of the eggs of the two-spotted leafhopper. The compound group shown in [Table 1-1] and [Table 1-2] (fluorinated quinazoline) The derivative, the compound α, and the compound such as 10% water and a compound of the compound were diluted to 100 ppm. A 3 cm diameter bean leaf was placed on a plastic cup containing 0.5% softwood and 10 female Tetranychus urticae female adults were stocked. After allowing to rest for one night at room temperature to lay eggs, after removing the stocked female adults, the adjusted liquid was dispersed at 4 ml each time, and the number of dead insects was counted after 6 days of spreading. The ovulation effect was determined from the same mortality as the test example 4 from the calculated mortality. The results are shown in Table 8. [Table 8] Judging the egg-killing effect of the egg-killing effect of the two-leaf clover eggs Compound N 〇. A 8, 1, 2, B 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, CD Compound α, Compound/3 Test Example 7-1. Insecticidal effect test against Spodoptera litura. The compound group shown in [Table 1-1] and [Table 1-2] (fluorinated quinone D sitting-77- 201238485 Derivatives), Compound α and Compound / 9% ο % Compounds such as water and agents are diluted to 100 ppm. The cabbage leaves with a diameter of 3 cm were treated by impregnation with various liquids, air-dried, placed in a plastic dish, and 10 Spodoptera litura 3rd instar larvae were stocked. The death rate was calculated by calculating the number of dead insects after 2 days of treatment. The mortality was calculated from the same mortality as in Test Example 4 from the calculated mortality. The results are shown in Table 9-1. [Table 9-1] Insecticidal effect on the insecticidal effect of Spodoptera litura. Compound N 〇. A 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 BCD compound α, Compound Test Example 7-2. Insecticidal effect test on western flower thrips [Table 1-Π and the compound group (fluorinated oxazoline derivative), compound α, and compound shown in [Table 1-2] 1 〇% water and a compound such as a solvent is diluted to 500 ppm. The leaves of 33 mcm diameter beans were impregnated with each drug solution, air-dried, placed in a plastic dish with a diameter of 50 mm coated with filter paper, and stocked with Frankliniella occidentalis l, 2nd instar larvae. The number of surviving individuals after 3 days of calculation was calculated and the number of dead individuals was counted to calculate the mortality. The insecticidal effect was determined from the same mortality as that of Test Example 4 from the calculated mortality. -78- 201238485 [Table 9-2] Judging insecticidal effect on the insecticidal effect of western flower thrips Compound N o · A 1, 2, 3, 4, 5, 6, 8, 9, 1 0,1 1, 1 2 B 7 CD Compound a, Compound) 3 Test Example 8. Control effect on cucumber powdery mildew Test on cucumber seedlings planted in pots (variety: half-white section, 2 leaf stage) Using a spray gun, each The pots were dispersed in 15 ml, and the compound group (fluorinated quinazoline derivative) shown in [Table 1-1] and [Table 1-2], and the existing ones shown in [Table 10] were prepared according to the formulation examples. The bactericidal active compound (hereinafter referred to as the English letter corresponding to the compound name) is dispersed by a mixture diluted with water to a concentration containing the active ingredient of a predetermined concentration. After air drying, the inoculum suspension of Sphaerotheca fuliginea was sprayed. Thereafter, the area ratio of each leaf was examined after 14 days of cultivation in a greenhouse, and the control price was calculated using the following formula. Control price calculation formula: prevention price = {(untreated area ratio - area ratio of treated agent) / untreated area rate} χ1〇〇] In addition, 'calculated by Colby's formula The desired effect by combining the active compounds. When the experiment 値 is larger than the calculation 値E, the effect obtained by the combination shows a multiplication effect. Cobyby's formula (Colby, SR "Calculating syner gistic and antagonistic-79-201238485 responses of herbicide combination", 22 (1 967)) is as follows. Colby's |10 formula: E = A+B - E uses the active compound X at a concentration of X to: a mixture of ί compounds, for an untreated control). The expected effect (control price) of the active compound X at a concentration of X is used. B is the expected effect (control price) of the active compound Y at a concentration of y. The effects of the respective active compounds are shown in Table 10, and the effects of the mixture of the existing bactericidal active compounds 1 to Table 11-8.

Weeds 15， 20- (AxB/1 00) L濃度y之活性化 的預期效果（防治 |對未經處理之對 ，對未經處理之對 :發明之化合物與 ，分別不於表11- -80- 201238485 [表 10] 各活性化合物之效果 供試化合物 供試濃度(ppm) 防治價 1 0· 5 42 2 0.5 51 3 0.5 48 4 0.5 53 5 0.5 40 6 0.5 39 7 0.5 38 8 0:5 46 9 0.5 46 10 0.5 38 11 0.5 40 12 0.5 39 Aa :四氯異苯腈 5 45 Nb :蟎離丹 10 38 Ab :克熱淨 2 41 Hd :賽福座 10 39 Hb :得克利 10 42 Ha :待克利 10 27 He :三泰芬 100 21 He :芬普福 100 12 Ea :亞托敏 100 21 Ed:百克敏 100 22 Ec :三氟敏 100 24 Eb :克雛 100 29 Nc :賽芬胺 1 49 Da ·.吡噻菌胺 1 51 Nd :福多寧 1 42 I a:快諾芬 1 39 Ca :甲基多保淨 2 40 F a :二氟林 1 42 Ma : acibenzolar-S-methyl 10 38 -81 - 201238485 [表 ll-ι] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 纖値 防治價 計算値 防治價(E) 1+Aa 0.5+5 91 68 1+Nb 0.5+10 89 64 1+Ab 0.5+2 85 66 1+Hd 0.5+10 91 65 1+Hb 0.5+10 84 66 1+Ha 0.5+10 70 58 1+Hc 0.5+100 71 54 1+He 0.5+100 65 49 1+Ea 0.5+100 75 54 1+Ed 0.5+100 70 55 1+Ec 0.5+1 73 56 1+Eb 0.5+100 78 59 1+Nc 0.5+1 89 70 1+Da 0.5+1 90 72 1+Nd 0.5+1 84 66 1+Ia 0.5+1 86 65 1+Ca 0.5+2 93 65 1+Fa 0.5+1 82 66 1+Ma 0.5+10 90 64 2+Aa 0.5+5 92 73 2+Nb 0.5+10 93 70 2+Ab 0.5+2 89 71 2+Hd 0.5+10 85 70 2+Hb 0.5+10 80 72 2+Ha 0.5+10 71 64 2+Hc 0.5+100 70 61 2+He 0.5+100 72 57 2+Ea 0.5+100 70 61 2+Ed 0.5+100 72 62 -82- 201238485 [表 11-2] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 防治價 計算値 防治價(E) 2+Ec 0.5+1 71 63 2+Eb 0.5+100 74 65 2+Nc 0.5+1 90 75 2+Da 0.5+1 89 76 2+Nd 0.5+1 88 72 2+la 0.5+1 91 70 2+Ca 0.5+2 92 71 2+Fa 0.5+1 90 72 2+Ma 0.5+10 92 70 3+Aa 0.5+5 92 71 3+Nb 0.5+10 87 68 3+Ab 0.5+2 85 69 3+Hd 0.5+10 91 68 3+Hb 0.5+10 89 70 3+Ha 0.5+10 75 62 3+Hc 0.5+100 73 59 3+He 0.5+100 80 54 3+Ea 0.5+100 77 59 3+Ed 0.5+100 80 59 3+Ec 0.5+1 73 60 3+Eb 0.5+100 78 63 3+Nc 0.5+1 90 73 3+Da 0.5+1 89 75 3+Nd 0.5+1 85 70 3+Ia 0.5+1 88 68 3+Ca 0.5+2 90 69 3+Fa 0.5+1 89 70 3+Ma 0.5+10 89 68 4+Aa 0.5+5 82 74 -83- 201238485 [表 11-3] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 防治價 計算値 防治價φ) 4+Nb 0.5+10 75 71 4+Ab 0.5+2 80 72 4+Hd 0.5+10 79 71 4+Hb 0.5+10 81 73 4+Ha 0.5+10 77 66 4+Hc 0.5+100 73 63 4+He 0.5+100 69 59 4+Ea 0.5+100 70 63 4+Ed 0.5+100 72 63 4+Ec 0.5+1 70 64 4+Eb 0.5+100 68 67 4+Nc 0.5.1 85 76 4+Da 0.5+1 89 77 4+Nd 0.5+1 86 73 4+Ia 0.5+1 79 71 4+Ca 0.5+2 76 72 4+Fa 0.5+1 83 73 4+Ma 0.5+10 83 73 5+Aa 0.5+5 87 67 5+Nb 0.5+10 92 63 5+Ab 0.5+2 85 65 5+Hd 0.5+10 88 63 5+Hb 0.5+10 79 65 5+Ha 0.5+10 78 56 5+Hc 0.5+100 75 53 5+He 0.5+100 74 47 5+Ea 0.5+100 72 53 5+Ed 0.5+100 79 53 5+Ec 0.5+1 77 54 -84- 201238485 [表 11-4] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 防治價 計算値 防治價(E) 5+Eb 0.5+100 78 57 5+Nc 0.5+1 89 69 5+Da 0.5+1 85 71 5+Nd 0.5+1 83 65 5+Ia 0.5+1 80 63 5+Ca 0.5+2 83 64 5+Fa 0.5+1 90 65 5+Ma 0.5+10 89 65 6+Aa 0.5+5 83 42 6+Nb 0.5+10 80 62 6+Ab 0.5+2 75 64 6+Hd 0.5+10 75 63 6+Hb 0.5+10 78 65 6+Ha 0.5+10 73 55 6+Hc 0.5+100 70 52 6+He 0.5+100 69 46 6+Ea 0.5+100 73 52 6+Ed 0,5+100 74 52 6+Ec 4 0.5+1 78 54 6+Eb 0.5+100 79 57 6+Nc 0.5+1 87 69 6+Da 0.5+1 89 70 6+Nd 0.5+1 88 65 6+Ia 0.5+1 83 63 6+Ca 0.5+2 81 63 6+Fa 0.5+1 89 65 6+Ma 0.5+10 77 65 7+Aa 0.5+5 83 66 7+Nb 0.5+10 77 62 C3 -85- 201238485 [表 11-5] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) ®驗値 防治價 計算値 防治價¢) 7+Ab 0.5+2 80 63 7+Hd 0.5+10 78 62 7+Hb 0.5+10 77 64 7+Ha 0.5+10 78 55 7+Hc 0.5+100 68 51 7+Ηθ 0.5+100 70 45 7+Ea 0.5+100 69 51 7+Ed 0.5+100 65 52 7+Ec 0.5+1 71 53 7+Eb 0.5+100 68 56 7+Nc 0.5+1 80 68 7+Da 0.5+1 85 70 7+Nd 0.5+1 79 64 7+Ia 0.5+1 81 62 7+Ca 0.5+2 79 63 7+Fa 0.5+1 85 64 7+Ma 0.5+10 79 64 8+Aa 0.5+5 90 70 8+Nb 0.5+10 89 67 8+Ab 0.5+2 85 68 8+Hd 0.5+10 91 67 8+Hb 0.5+10 93 69 8+Ha 0.5+10 80 61 8+Hc 0.5+100 71 57 8+He 0.5+100 69 52 8+Ea 0.5+100 75 57 8+Ed 0.5+100 72 58 8+Ec 0.5+1 73 59 8+Eb 0.5+100 78 62 -86- 201238485 [表 11-6] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 防治價 計算値 防治價(E) 8+Nc 0.5+1 89 72 8+Da 0.5+1 90 74 8+Nd 0.5+1 84 69 8+Ia 0.5+1 85 67 8+Ca 0.5+2 93 68 8+Fa 0.5+1 81 69 8+Ma 0.5+10 90 67 9+Aa 0,5+5 86 70 9+Nb 0.5+10 91 67 9+Ab 0.5+2 89 68 9+Hd 0.5+10 83 67 9+Hb 0.5+10 80 69 9+Ha 0.5+10 71 61 9+Hc 0.5+100 69 57 9+He 0.5+100 65 52 9+Ea 0.5+100 73 57 9+Ed 0.5+100 72 58 9+Ec 0.5+1 71 59 9+Eb 0.5+100 74 62 9+Nc 0.5+1 90 72 9+Da 0.5+1 89 74 9+Nd 0.5+1 88 69 9+Ia 0.5+1 91 67 9+Ca 0.5+2 90 68 9+Fa 0.5+1 90 69 9+Ma 0.5+10 92 67 10+Aa 0.5+5 90 66 10+Nb 0.5+10 87 62 10+Ab 0.5+2 85 63 -87- 201238485 [表 11-7] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 0驗値 防治價 計算値 防治價(E) 10+Hd 0.5+10 92 62 10+Hb 0.5+10 89 64 10+Ha 0.5+10 75 55 10+Hc 0.5+100 73 51 10+He 0.5+100 79 45 10+Ea 0.5+100 77 51 10+Ed 0.5+100 80 52 10+Ec 0.5+1 70 53 10+Eb 0.5+100 78 56 10+Nc 0.5+1 90 68 10+Da 0.5+1 89 70 10+Nd 0.5+1 85 64 10+Ia 0.5+1 89 62 10+Ca 0.5+2 90 63 10+Fa 0.5+1 89 64 10+Ma 0.5+10 89 62 11 +Aa 0.5+5 82 67 11+Nb 0.5+10 75 63 11+Ab 0.5+2 80 65 11+Hd 0.5+10 79 63 11+Hb 0.5+10 79 65 11+Ha 0.5+10 75 56 11+Hc 0.5+100 73 53 11+He 0.5+100 66 47 11+Ea 0.5+100 70 53 11+Ed 0.5+100 70 53 11+Ec 0.5+1 71 54 11+Eb 0.5+100 68 57 11+Nc 0.5+1 85 69 -88- 201238485 [表 11-8] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 防治價 計算値 防治價(E) 11+Da 0.5+1 89 71 11+Nd 0.5+1 86 65 11+Ia 0.5+1 79 63 11+Ca 0.5+2 76 64 11+Fa 0.5+1 83 65 11+Ma 0.5+10 84 65 12+Aa 0.5+5 87 66 12+Nb 0.5+10 92 62 12+Ab 0.5+2 85 64 12+Hd 0.5+10 88 63 12+Hb 0.5+10 79 65 12+Ha 0.5+10 79 55 12+Hc 0.5+100 73 52 12+He 0.5+100 74 46 12+Ea 0.5+100 75 52 12+Ed 0.5+100 79 52 12+Ec 0.5+1 77 54 12+Eb 0.5+100 78 57 12+Nc 0.5+1 89 69 12+Da 0.5+1 85 70 12+Nd 0.5+1 83 65 12+Ia 0.5+1 80 63 12+Ca 0.5+2 83 63 12+Fa 0.5+1 91 65 12+Ma 0.5+10 90 65 (注）表1 1-1〜表1 1-8中供試化合物之各2個英文字母 係與表10中各2個英文字母相同意義。 自上述表11-1〜表11-8可明顯得知，本發明化合物與 現有殺菌活性化合物之混合物，實驗値較計算値E爲大， 顯示藉由該組合之效果具有相乘效果。 試驗例9.對小黃瓜白粉病之防治效果試驗 -89- 201238485 對盆中栽植之小黃瓜幼苗（品種：半白節成，2.5葉期 )使用噴霧槍，以每盆散佈15 ml，將依製劑例爲準調製之[ 表1一 1]以及[表1 一 2]所示之化合物群（含氟喹唑啉衍生物 )，以及[表1 2]所示之現有的殺菌活性化合物（以下以對應 於化合物名稱之英文字母表示），經以水稀釋調整至含有 規定濃度之有效成份之混合物散佈。風乾後，噴霧接種露 菌病菌（Pseudoperonospora cubensis)之分生子懸浮液，並 於2 1°C濕度100%之條件下維持1天。進而於溫室中放置 3天後調查各葉之發病面積率，與以實驗例8相同，算出 防治價。另外，以科爾比（Colby)的計算式求得藉由組合 各活性化合物所期待之效果。各活性化合物之效果示於表 1 2，本發明之化合物與現有之殺菌化合物之混合物之效果 ，分別不於表13-1~表13-5。 -90- 201238485 [表 12] 各活性化合物之效果 供試化合物 供試濃度(ppm) 實驗値 防治價 1 0.05 46 2 0. 05 43 3 0.05 39 4 0. 05 42 5 0.05 40 6 0. 05 39 7 0.05 38 8 0. 05 46 9 0. 05 46 10 0.05 38 11 0. 05 36 12 0.05 39 Aa :四氯異苯腈 0.5 49 Ac :錳乃浦 1 51 Fb :賽座滅 0· 1 49 Fc :安美速 0· 1 38 Na :克絕 10 44 Eb :克收欣 1 43 Ea :亞托敏 1 44 Ba :右滅達樂 10 36 Jc :曼普胺 0.5 24 Jb : benthiavalicarb-isopropyl 0.5 15 Ja :達滅芬 5 24 -91 - 201238485 [表 13-1] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 防治僧 計算値 防治率(E) 1+Aa 0. 05+0. 5 80 72 1+Ac 0. 05+1 82 74 1+Fb 0. 05+0.1 84 72 1+Fc 0. 05+0. 1 79 67 1+Na 0. 05+10 85 70 l+Eb 0. 05+1 77 69 1+Ea 0. 05+1 79 70 1+Ba 0.05+10 75 65 l+Jc 0. 05+0. 5 73 59 1+Jb 0. 05+0. 5 75 54 1+Ja 0. 05+5 78 59 2+Aa 0. 05+0.5 80 71 2+Ac 0. 05+1 84 72 2+Fb 0. 05+0. 1 80 71 2+Fc 0. 05+0. 1 70 65 2+Na 0. 05+10 72 68 2+Eb 0. 05+1 79 68 2+Ea 0. 05+1 75 68 2+Ba 0. 05+10 70 64 2+Jc 0. 05+0.5 79 57 2+Jb 0. 05+0.5 75 52 2+Ja 0. 05+5 78 57 3+Aa 0. 05+0. 5 73 69 3+Ac 0. 05+1 89 70 3+Fb 0. 05+0.1 79 69 3+Fc 0. 05+0. 1 77 62 3+Na 0.05+10 75 66 3+Eb 0. 05+1 78 65 3+Ea 0.05+1 77 66 -92- 201238485 [表 13-2] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 防治價 計算値 防治率(E) 3+Ba 0.05+10 75 61 3+Jc 0. 05+0. 5 72 54 3+Jb 0. 05+0.5 80 48 3+Ja 0. 05+5 73 54 4+Aa 0. 05+0· 5 88 70 4+Ac 0. 05+1 90 72 4+Fb 0. 05+0.1 92 70 4+Fc 0. 05+0.1 80 64 4+Na 0. 05+10 79 68 4+Eb 0. 05+1 79 67 4+Ea 0. 05+1 80 68 4+Ba 0.05+10 79 63 4+Jc 0. 05+0. 5 77 56 4+Jb 0. 05+0- 5 77 51 4+Ja 0. 05+5 69 56 5+Aa 0. 05+0. 5 80 69 5+Ac 0. 05+1 82 71 5+Fb 0. 05+0. 1 81 69 5+Fc 0. 05+0.1 72 63 5+Na 0. 05+10 78 66 5+Eb 0. 05+1 80 66 5+Ea 0. 05+1 79 66 5+Ba 0.05+10 75 62 5+Jc 0.05+0.5 72 54 5+Jb 0. 05+0.5 74 49 5+Ja 0.05+5 69 54 6+Aa 0. 05+0.5 77 69 6+Ac 0. 05+1 82 70 6+Fb 0. 05+0. 1 84 69 -93- 201238485 [表 13-3] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 計算値 防治價 防治率¢) 6+Fc 0. 05+0. 1 79 62 6+Na 0. 05+10 77 66 6+Eb 0. 05+1 79 65 6+Ea 0. 05+1 76 66 6+Ba 0. 05+10 80 61 6+Jc 0. 05+0. 5 79 54 6+Jb 0. 05+0. 5 70 48 6+Ja 0. 05+5 74 54 7+Aa 0. 05+0. 5 80 68 7+Ac 0. 05+1 82 70 7+Fb 0. 05+0. 1 81 68 7+Fc 0. 05+0.1 83 62 7+Na 0. 05+10 85 65 7+Eb 0. 05+1 79 65 7+Ea 0. 05+1 75 65 7+Ba 0.05+10 77 60 7+Jc 0. 05+0. 5 78 53 7+Jb 0. 05+0. 5 73 47 7+Ja 0. 05+5 69 53 8+Aa 0. 05+0. 5 85 72 8+Ac 0. 05+1 89 74 8+Fb 0. 05+0. 1 90 72 8+Fc 0. 05+0. 1 80 67 8+Na 0. 05+10 85 70 8+Eb 0. 05+1 83 69 8+Ea 0. 05+1 82 70 8+Ba 0. 05+10 85 65 8+Jc 0. 05+0. 5 76 59 8+Jb 0. 05+0. 5 76 54 -94- 201238485 [表 13-4] 本發明化合物與現有; 段菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 防治價 計算値 防治率(E) 8+Ja 0.05+5 70 59 9+Aa 0. 05+0. 5 80 72 9+Ac 0. 05+1 84 74 9+Fb 0. 05+0. 1 83 72 9+Fc 0. 05+0.1 75 67 9+Na 0. 05+10 80 70 9+Eb 0. 05+1 83 69 9+Ea 0. 05+1 85 70 9+Ba 0. 05+10 75 65 9+Jc 0. 05+0. 5 70 59 9+Jb 0. 05+0. 5 74 54 9+Ja 0. 05+5 70 59 10 + Aa 0. 05+0. 5 83 68 10+Ac 0. 05+1 85 70 10+Fb 0. 05+0.1 87 68 10+Fc 0. 05+0.1 83 62 10+Na 0. 05+10 80 65 10+Eb 0. 05+1 79 65 10+Ea 0.05+1 78 65 10+Ba 0.05+10 77 60 10+Jc 0. 05+0.5 75 53 10+Jb 0. 05+0. 5 68 47 10+Ja 0.05+5 75 53 11+Aa 0. 05+0. 5 76 67 11+Ac 0.05+1 82 69 11+Fb 0. 05+0.1 75 67 11+Fc 0. 05+0. 1 79 60 ll+Na 0.05+10 74 64 11+Eb 0. 05+1 74 64 -95- 201238485 [表 13-5] 本發明化合物與現有殺菌活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 防治價 計算値 防治率(E) 11+Ea 0. 05+1 77 64 11+Ba 0. 05+10 73 59 11+Jc 0. 05+0. 5 73 51 11+Jb 0. 05+0. 5 70 46 11+Ja 0. 05+5 73 51 12+Aa 0. 05+0. 5 78 69 12+Ac 0. 05+1 85 70 12+Fb 0. 05+0. 1 80 69 12+Fc 0. 05+0. 1 78 62 12+Na 0. 05+10 74 66 12+Eb 0. 05+1 80 65 12+Ea 0. 05+1 82 66 12+Ba 0. 05+10 83 61 12+Jc 0. 05+0. 5 75 54 12+Jb 0. 05+0. 5 70 48 12+Ja 0. 05+5 75 54 (注）表13-1〜表13-5中供試化合物之各2個英文字母係與 表12中各2個英文字母相同意義。 自上述表13-1〜表13-5可明顯得知，本發明化合物與 現有殺菌活性化合物之混合物，實驗値較計算値E爲大， 顯示藉由該組合之效果具有相乘效果。 試驗例1 〇.對棉蚜蟲之殺蟲效果試驗 將[表1-1]以及[表1-2]所示之化合物群（含氟喹唑啉 衍生物）以及[表14]所示之現有的殺菌活性化合物（以下以 對應於化合物名稱之英文字母表示），經以水稀釋調整至 含有規定濃度之有效成份之混合物。將直徑3 cm之小黃 瓜葉片置於裝有0.5 %軟洋菜之塑膠杯上，並放養5隻棉 -96- 201238485 呀蟲（Aphis gossypii)雌性成蟲。放置1晚後，計算產出之 幼蟲數，以經調整之藥液每次散佈0.4ml，並於散佈2天 後計算死亡蟲數，依據實驗例4.之方法算出死蟲率。另外 ’以科爾比（Colby)的計算式求得藉由組合各活性化合物 所期待之效果。各活性化合物之效果示於表1 4，本發明 之化合物與現有之殺蟲活性化合物之混合物之效果，分別 示於表1 5-1〜表1 5-3。 [表 14] 各活性化合物之效果 供試化合物 供離度(ppm) 實驗値 死蟲蛮 1 0. 1 36 2 0.1 39 3 〇. 1 40 4 0. 1 39 5 0.1 37 6 0.1 41 7 0. 1 43 8 0. 1 44 9 0. 1 40 10 ΙΤΓ 36 11 ο. ΐ 39 12 0.1 40 P 歐殺松 Λ0 「36 y 益達胺 o.oi 39 R 脫芬瑞 0.5 41 S 阿納寧 0.1 43 ΐ 氟尼胺 1 44 u pyrifluquinazon 0. 01 40 -97- 201238485 [表 15-1] 本發明化合物與現有殺蟲活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) S驗値 死蟲率 計算値 死蟲率CE) 1 +P 0. 1+10 73 59 1 +Q 0. 1+0· 01 80 61 1 + R 0. 1+0· 5 79 62 1 + S 0. 1+0. 1 80 64 1 + T 0. 1+1 79 64 1 + U 0. 1+0. 01 78 62 2 + P 0. 1+10 73 61 2 +Q 0. 1+0.01 80 63 2 + R 0. 1+0· 5 79 64 2 + S 0. 1+0. 1 80 65 2 + T 0. 1+1 79 66 2 + U 0. 1+0. 01 73 63 3 +P 0-1+10 80 62 3 +Q 0· 1+0. 01 79 63 3 + R 0. 1+0. 5 80 65 3 + S 0. 1+0. 1 79 66 3 + T 0. 1+1 78 66 3 + U 0,1+0. 01 73 64 4 + P 0. 1+10 80 61 4 +Q 0.1+0. 01 79 63 4 + R 0.1+0. 5 80 64 4 + S 0. 1+0. 1 79 65 4 + T 0, 1+1 80 66 4 +U 0. 1+0. 01 79 63 5 + P 0. 1+10 82 60 5 +Q 0.1+0. 01 81 62 5 + R 0. 1+0. 5 82 63 5 + S 0. 1+0· 1 81 64 5 + T 0. 1+1 75 65 -98- 201238485 [表 15-2] 本發明化合物與現有殺蟲活性化合物之混合物所得效果 供試化合物 供試濃度(ppm) 實驗値 死蟲率 計算値 死蟲率(E) 5 +U 0· 1+0.01 75 62 6 + P 0· 1+10 82 62 6 +Q 0· 1+0.01 81 64 6 + R 0· 1+0.5 82 65 6 + S 0· 1+0. 1 81 . 66 6 + T 0. 1+1 75 67 6 +U 0. 1+0.01 80 65 7 +P 0. 1+10 82 64 7 +Q 0· 1+0. 01 81 65 7 + R 0· 1+0.5 82 66 7 + S 0. 1+0. 1 81 68 7 + T 0· 1+1 80 68 7 +U 0· 1+0.01 75 66 8 +P 0. 1+10 82 64 8 +Q 0· 1+0. 01 81 66 8 +R 0_ 1+0.5 82 67 8 + S 0. 1+0. 1 81 68 8 +T 0, 1+1 80 69 8 + U 0. 1+0. 01 80 66 9 +P 0. 1+10 82 62 9 +Q 0. 1+0. 01 81 63 9 + R 0· 1+0.5 82 65 9 + S 0· 1+0. 1 81 66 9 + T 0· 1+1 79 66 9 +U 0. 1+0, 01 78 64 10 + P 0· 1+10 73 59 10 + Q 0· 1+0.01 80 61 10 + R 0. 1+0.5 79 62 10 + S 0. 1+0. 1 80 64 10 + T 0· 1+1 79 64 -99- 201238485 [表 15-3] 本發明化合物與現有殺蟲活性化合物之混合物所得效果 供試化合物 供試濃度(ρρπ〇 實驗値 死蟲率 計算値 死蟲率(Ε) 10 +U 0. 1+0. 01 79 62 11 +P 0. 1+10 78 61 11 +Q 0.1+0. 01 73 63 11 +R 0. 1+0. 5 80 64 11 + S 0. 1+0, 1 79 65 11 +T 0. 1+1 80 66 11 + U 0_ 1+0. 01 79 63 12 + P 0. 1+10 78 62 12 + Q 0. 1+0. 01 73 63 12 + R 0.1+0. 5 82 65 12 + S 0.1+0. 1 81 66 12 +T 0. 1+1 75 66 12 +U 0.1+0. 01 75 64 (注）表15-1〜表1S-3中供試化合物之各2個英文字母係與 表14中各2個英文字母相同意義。 自上述表15-1〜表15-3可明顯得知，本發明化合物與 現有殺蟲活性化合物之混合物，實驗値較計算値E爲大， 顯示藉由該組合之效果具有相乘效果。 [產業上之可利用性] 本發明之含有1種或2種以上，以含氟唾唑啉衍生物 爲有效成分之農園藝用有害生物防治組成物，對於農園藝 用植物冒出之病原菌、昆蟲、蟎等有害生物顯示以低藥量 之優異的防治效果，由於對有用作物具有極高的安全性， 因此極適用爲新穎的農藥。另外，本發明之含氟喹唑啉衍 生物與現有殺菌活性化合物之混合物，以及本發明之含氟 喹唑啉衍生物與現有殺蟲活性化合物之混合物，實驗値均 -100- 201238485 顯示較依據科爾比（Colby)的計算式爲基礎之計算値E爲 大，由於顯示藉由該組合之效果具有相乘效果，因此極適 用作爲混合劑。 -101 -Weeds 15, 20- (AxB/1 00) The expected effect of the activation of L concentration y (control | against untreated pairs, on untreated pairs: invented compounds and, respectively, not in Table 11--80 - 201238485 [Table 10] Effect of each active compound Test compound concentration (ppm) Control price 1 0· 5 42 2 0.5 51 3 0.5 48 4 0.5 53 5 0.5 40 6 0.5 39 7 0.5 38 8 0:5 46 9 0.5 46 10 0.5 38 11 0.5 40 12 0.5 39 Aa : tetrachloroisophthalonitrile 5 45 Nb : 螨 丹 10 10 38 Ab : 克热净 2 41 Hd : Saifu 10 39 Hb : Dekli 10 42 Ha : Waiting for Kli 10 27 He : Santai 100 21 He : Fenpus 100 12 Ea : Atomin 100 21 Ed: Bai Kemin 100 22 Ec : Trifluoromethane 100 24 Eb : Chong 100 29 Nc : Safinamide 1 49 Da ·. pirfenamide 1 51 Nd : pentoxine 1 42 I a: vebufen 1 39 Ca : methyl valprom 2 40 F a : difluoroline 1 42 Ma : acibenzolar-S-methyl 10 38 -81 - 201238485 [Table ll-ι] Effect of the mixture of the compound of the present invention and the existing bactericidal active compound Test compound test concentration (ppm) Fibrin control price calculation 値 Control price (E) 1+Aa 0.5+5 91 68 1+Nb 0.5+10 89 64 1+Ab 0.5+2 85 66 1+Hd 0.5+10 91 65 1+Hb 0.5+10 84 66 1+Ha 0.5+10 70 58 1+Hc 0.5+100 71 54 1+He 0.5+100 65 49 1+Ea 0.5+100 75 54 1+Ed 0.5+100 70 55 1+Ec 0.5+1 73 56 1+Eb 0.5+100 78 59 1+Nc 0.5+1 89 70 1+ Da 0.5+1 90 72 1+Nd 0.5+1 84 66 1+Ia 0.5+1 86 65 1+Ca 0.5+2 93 65 1+Fa 0.5+1 82 66 1+Ma 0.5+10 90 64 2+Aa 0.5 +5 92 73 2+Nb 0.5+10 93 70 2+Ab 0.5+2 89 71 2+Hd 0.5+10 85 70 2+Hb 0.5+10 80 72 2+Ha 0.5+10 71 64 2+Hc 0.5+100 70 61 2+He 0.5+100 72 57 2+Ea 0.5+100 70 61 2+Ed 0.5+100 72 62 -82- 201238485 [Table 11-2] The effect of the mixture of the compound of the present invention and the existing bactericidal active compound is tested. Compound test concentration (ppm) Experimental 値 control price calculation 値 prevention price (E) 2+Ec 0.5+1 71 63 2+Eb 0.5+100 74 65 2+Nc 0.5+1 90 75 2+Da 0.5+1 89 76 2+Nd 0.5+1 88 72 2+la 0.5+1 91 70 2+Ca 0.5+2 92 71 2+Fa 0.5+1 90 72 2+Ma 0.5+10 92 70 3+Aa 0.5+5 92 71 3+ Nb 0.5+10 87 68 3+Ab 0.5+2 85 69 3+Hd 0.5+10 91 68 3+Hb 0.5+10 89 70 3+Ha 0.5+10 75 62 3+Hc 0 .5+100 73 59 3+He 0.5+100 80 54 3+Ea 0.5+100 77 59 3+Ed 0.5+100 80 59 3+Ec 0.5+1 73 60 3+Eb 0.5+100 78 63 3+Nc 0.5 +1 90 73 3+Da 0.5+1 89 75 3+Nd 0.5+1 85 70 3+Ia 0.5+1 88 68 3+Ca 0.5+2 90 69 3+Fa 0.5+1 89 70 3+Ma 0.5+10 89 68 4+Aa 0.5+5 82 74 -83- 201238485 [Table 11-3] Effect of the mixture of the compound of the present invention and the existing bactericidal active compound Test concentration (ppm) Test 値 Control price calculation 値 Control price φ 4+Nb 0.5+10 75 71 4+Ab 0.5+2 80 72 4+Hd 0.5+10 79 71 4+Hb 0.5+10 81 73 4+Ha 0.5+10 77 66 4+Hc 0.5+100 73 63 4 +He 0.5+100 69 59 4+Ea 0.5+100 70 63 4+Ed 0.5+100 72 63 4+Ec 0.5+1 70 64 4+Eb 0.5+100 68 67 4+Nc 0.5.1 85 76 4+Da 0.5+1 89 77 4+Nd 0.5+1 86 73 4+Ia 0.5+1 79 71 4+Ca 0.5+2 76 72 4+Fa 0.5+1 83 73 4+Ma 0.5+10 83 73 5+Aa 0.5+ 5 87 67 5+Nb 0.5+10 92 63 5+Ab 0.5+2 85 65 5+Hd 0.5+10 88 63 5+Hb 0.5+10 79 65 5+Ha 0.5+10 78 56 5+Hc 0.5+100 75 53 5+He 0.5+100 74 47 5+Ea 0.5+100 72 53 5+Ed 0.5+100 79 53 5+Ec 0.5+1 77 54 -84- 201238485 [ 11-4] Effect of the mixture of the compound of the present invention and the existing bactericidal active compound Test concentration (ppm) Test 値 Control price calculation 値 Prevention price (E) 5+Eb 0.5+100 78 57 5+Nc 0.5+1 89 69 5+Da 0.5+1 85 71 5+Nd 0.5+1 83 65 5+Ia 0.5+1 80 63 5+Ca 0.5+2 83 64 5+Fa 0.5+1 90 65 5+Ma 0.5+10 89 65 6+Aa 0.5+5 83 42 6+Nb 0.5+10 80 62 6+Ab 0.5+2 75 64 6+Hd 0.5+10 75 63 6+Hb 0.5+10 78 65 6+Ha 0.5+10 73 55 6+ Hc 0.5+100 70 52 6+He 0.5+100 69 46 6+Ea 0.5+100 73 52 6+Ed 0,5+100 74 52 6+Ec 4 0.5+1 78 54 6+Eb 0.5+100 79 57 6 +Nc 0.5+1 87 69 6+Da 0.5+1 89 70 6+Nd 0.5+1 88 65 6+Ia 0.5+1 83 63 6+Ca 0.5+2 81 63 6+Fa 0.5+1 89 65 6+Ma 0.5+10 77 65 7+Aa 0.5+5 83 66 7+Nb 0.5+10 77 62 C3 -85- 201238485 [Table 11-5] The effect of the mixture of the compound of the present invention and the existing bactericidal active compound (ppm) ® test price calculation 値 prevention price ¢) 7+Ab 0.5+2 80 63 7+Hd 0.5+10 78 62 7+Hb 0.5+10 77 64 7+Ha 0.5+10 78 55 7+Hc 0.5 +100 68 51 7+Ηθ 0.5+100 70 45 7+Ea 0.5+100 69 51 7+Ed 0.5+100 65 52 7+Ec 0.5+1 71 53 7+Eb 0.5+100 68 56 7+Nc 0.5+1 80 68 7+Da 0.5+1 85 70 7+ Nd 0.5+1 79 64 7+Ia 0.5+1 81 62 7+Ca 0.5+2 79 63 7+Fa 0.5+1 85 64 7+Ma 0.5+10 79 64 8+Aa 0.5+5 90 70 8+Nb 0.5 +10 89 67 8+Ab 0.5+2 85 68 8+Hd 0.5+10 91 67 8+Hb 0.5+10 93 69 8+Ha 0.5+10 80 61 8+Hc 0.5+100 71 57 8+He 0.5+100 69 52 8+Ea 0.5+100 75 57 8+Ed 0.5+100 72 58 8+Ec 0.5+1 73 59 8+Eb 0.5+100 78 62 -86- 201238485 [Table 11-6] The compound of the present invention and the existing sterilization Effect of mixture of active compounds Test concentration of test compound (ppm) Test 値 Control price calculation 値 Control price (E) 8+Nc 0.5+1 89 72 8+Da 0.5+1 90 74 8+Nd 0.5+1 84 69 8+Ia 0.5+1 85 67 8+Ca 0.5+2 93 68 8+Fa 0.5+1 81 69 8+Ma 0.5+10 90 67 9+Aa 0,5+5 86 70 9+Nb 0.5+10 91 67 9+Ab 0.5+2 89 68 9+Hd 0.5+10 83 67 9+Hb 0.5+10 80 69 9+Ha 0.5+10 71 61 9+Hc 0.5+100 69 57 9+He 0.5+100 65 52 9+ Ea 0.5+100 73 57 9+Ed 0.5+100 72 58 9+Ec 0.5+1 71 59 9+Eb 0.5+100 74 62 9+Nc 0.5+1 90 72 9+Da 0.5+1 89 74 9+Nd 0.5+1 88 69 9+Ia 0.5+1 91 67 9+Ca 0.5+2 90 68 9+Fa 0.5+1 90 69 9+Ma 0.5+10 92 67 10+Aa 0.5+5 90 66 10+Nb 0.5+10 87 62 10+Ab 0.5+2 85 63 -87- 201238485 [Table 11-7] Effect of the mixture of the compound of the present invention and the existing bactericidal active compound The test compound is tested at a concentration (ppm). Control price calculation 値 prevention price (E) 10+Hd 0.5+10 92 62 10+Hb 0.5+10 89 64 10+Ha 0.5+10 75 55 10+Hc 0.5+100 73 51 10+He 0.5+100 79 45 10 +Ea 0.5+100 77 51 10+Ed 0.5+100 80 52 10+Ec 0.5+1 70 53 10+Eb 0.5+100 78 56 10+Nc 0.5+1 90 68 10+Da 0.5+1 89 70 10+Nd 0.5+1 85 64 10+Ia 0.5+1 89 62 10+Ca 0.5+2 90 63 10+Fa 0.5+1 89 64 10+Ma 0.5+10 89 62 11 +Aa 0.5+5 82 67 11+Nb 0.5+ 10 75 63 11+Ab 0.5+2 80 65 11+Hd 0.5+10 79 63 11+Hb 0.5+10 79 65 11+Ha 0.5+10 75 56 11+Hc 0.5+100 73 53 11+He 0.5+100 66 47 11+Ea 0.5+100 70 53 11+Ed 0.5+100 70 53 11+Ec 0.5+1 71 54 11+Eb 0.5+100 68 57 11+Nc 0.5+1 85 69 -88- 201238485 [Table 11-8 a mixture of a compound of the invention and a conventional bactericidal active compound Effectiveness test compound concentration (ppm) test 値 control price calculation 値 prevention price (E) 11+Da 0.5+1 89 71 11+Nd 0.5+1 86 65 11+Ia 0.5+1 79 63 11+Ca 0.5 +2 76 64 11+Fa 0.5+1 83 65 11+Ma 0.5+10 84 65 12+Aa 0.5+5 87 66 12+Nb 0.5+10 92 62 12+Ab 0.5+2 85 64 12+Hd 0.5+10 88 63 12+Hb 0.5+10 79 65 12+Ha 0.5+10 79 55 12+Hc 0.5+100 73 52 12+He 0.5+100 74 46 12+Ea 0.5+100 75 52 12+Ed 0.5+100 79 52 12+Ec 0.5+1 77 54 12+Eb 0.5+100 78 57 12+Nc 0.5+1 89 69 12+Da 0.5+1 85 70 12+Nd 0.5+1 83 65 12+Ia 0.5+1 80 63 12+ Ca 0.5+2 83 63 12+Fa 0.5+1 91 65 12+Ma 0.5+10 90 65 (Note) Table 2 1-1 to Table 1 1-8 each of the two English alphabets of the test compound and Table 10 Each of the two English letters has the same meaning. It is apparent from the above Tables 11-1 to 11-8 that the mixture of the compound of the present invention and the existing bactericidal active compound has a larger experimental enthalpy than E, indicating that the effect of the combination has a multiplication effect. Test Example 9. Test on the control effect of cucumber cucumber powdery mildew-89- 201238485 Using a spray gun on a cucumber seedling planted in a pot (variety: half-white section, 2.5 leaf stage), spreading 15 ml per pot, The formulation examples are quasi-modulated [Table 1-1] and [Table 1-2] compound groups (fluorinated quinazoline derivatives), and the existing bactericidal active compounds shown in [Table 12] (below) It is distributed in a mixture which is adjusted to the concentration of the active ingredient in a predetermined concentration by water dilution in the letter corresponding to the compound name. After air drying, the meristematic suspension of the bacteria (Pseudoperonospora cubensis) was sprayed and maintained at a humidity of 100% at 21 ° C for 1 day. Further, after being placed in a greenhouse for 3 days, the area ratio of each leaf was examined, and the control price was calculated in the same manner as in Experimental Example 8. Further, the effect expected by combining the respective active compounds was determined by the calculation formula of Colby. The effects of the respective active compounds are shown in Table 12. The effects of the mixture of the compound of the present invention and the conventional bactericidal compound are not shown in Table 13-1 to Table 13-5, respectively. -90- 201238485 [Table 12] Effect of each active compound Test compound concentration (ppm) Experimental 値 control price 1 0.05 46 2 0. 05 43 3 0.05 39 4 0. 05 42 5 0.05 40 6 0. 05 39 7 0.05 38 8 0. 05 46 9 0. 05 46 10 0.05 38 11 0. 05 36 12 0.05 39 Aa : tetrachloroisophthalonitrile 0.5 49 Ac : Manganese 1 51 Fb : Saiqi 0. 1 49 Fc : Anmei speed 0· 1 38 Na : 克绝10 44 Eb : 克收欣 1 43 Ea : 托托敏 1 44 Ba : 右灭达10 13 Jc : mannamine 0.5 24 Jb : benthiavalicarb-isopropyl 0.5 15 Ja : Damoffene 5 24 -91 - 201238485 [Table 13-1] Effect of the mixture of the compound of the present invention and the existing bactericidal active compound Test compound concentration (ppm) Experimental 値 Control 僧 Calculation 値 Control rate (E) 1+ Aa 0. 05+0. 5 80 72 1+Ac 0. 05+1 82 74 1+Fb 0. 05+0.1 84 72 1+Fc 0. 05+0. 1 79 67 1+Na 0. 05+10 85 70 l+Eb 0. 05+1 77 69 1+Ea 0. 05+1 79 70 1+Ba 0.05+10 75 65 l+Jc 0. 05+0. 5 73 59 1+Jb 0. 05+0 5 75 54 1+Ja 0. 05+5 78 59 2+Aa 0. 05+0.5 80 71 2+Ac 0. 05+1 84 72 2+Fb 0. 05+0. 1 80 71 2+Fc 0 . 05+0 1 70 65 2+Na 0. 05+10 72 68 2+Eb 0. 05+1 79 68 2+Ea 0. 05+1 75 68 2+Ba 0. 05+10 70 64 2+Jc 0. 05 +0.5 79 57 2+Jb 0. 05+0.5 75 52 2+Ja 0. 05+5 78 57 3+Aa 0. 05+0. 5 73 69 3+Ac 0. 05+1 89 70 3+Fb 0 05+0.1 79 69 3+Fc 0. 05+0. 1 77 62 3+Na 0.05+10 75 66 3+Eb 0. 05+1 78 65 3+Ea 0.05+1 77 66 -92- 201238485 [Table 13-2] Effect of the mixture of the compound of the present invention and the existing bactericidal active compound Test compound concentration (ppm) Experimental 値 control price calculation 値 control rate (E) 3+Ba 0.05+10 75 61 3+Jc 0. 05 +0. 5 72 54 3+Jb 0. 05+0.5 80 48 3+Ja 0. 05+5 73 54 4+Aa 0. 05+0· 5 88 70 4+Ac 0. 05+1 90 72 4+ Fb 0. 05+0.1 92 70 4+Fc 0. 05+0.1 80 64 4+Na 0. 05+10 79 68 4+Eb 0. 05+1 79 67 4+Ea 0. 05+1 80 68 4+ Ba 0.05+10 79 63 4+Jc 0. 05+0. 5 77 56 4+Jb 0. 05+0- 5 77 51 4+Ja 0. 05+5 69 56 5+Aa 0. 05+0. 5 80 69 5+Ac 0. 05+1 82 71 5+Fb 0. 05+0. 1 81 69 5+Fc 0. 05+0.1 72 63 5+Na 0. 05+10 78 66 5+Eb 0. 05 +1 80 66 5+Ea 0. 05+1 79 66 5+Ba 0.05+10 75 62 5+Jc 0.05+0.5 72 54 5+Jb 0. 05+0.5 74 49 5+Ja 0.05+5 69 54 6+Aa 0. 05+0.5 77 69 6+Ac 0. 05+1 82 70 6+Fb 0. 05+0. 1 84 69 -93- 201238485 [ Table 13-3] Effect of the mixture of the compound of the present invention and the existing bactericidal active compound Test compound concentration (ppm) Experimental 値 Calculation 値 Control price control rate ¢) 6+Fc 0. 05+0. 1 79 62 6+ Na 0. 05+10 77 66 6+Eb 0. 05+1 79 65 6+Ea 0. 05+1 76 66 6+Ba 0. 05+10 80 61 6+Jc 0. 05+0. 5 79 54 6+Jb 0. 05+0. 5 70 48 6+Ja 0. 05+5 74 54 7+Aa 0. 05+0. 5 80 68 7+Ac 0. 05+1 82 70 7+Fb 0. 05 +0. 1 81 68 7+Fc 0. 05+0.1 83 62 7+Na 0. 05+10 85 65 7+Eb 0. 05+1 79 65 7+Ea 0. 05+1 75 65 7+Ba 0.05 5,5,5,5,5 8+Ac 0. 05+1 89 74 8+Fb 0. 05+0. 1 90 72 8+Fc 0. 05+0. 1 80 67 8+Na 0. 05+10 85 70 8+Eb 0. 05 +1 83 69 8+Ea 0. 05+1 82 70 8+Ba 0. 05+10 85 65 8+Jc 0. 05+0. 5 76 59 8+Jb 0. 05+0. 5 76 54 -94 - 201238485 [Table 13-4] The effect of the compound of the present invention and the existing; Test compound concentration (ppm) test 値 control price calculation 値 prevention rate (E) 8+Ja 0.05+5 70 59 9+Aa 0. 05+0. 5 80 72 9+Ac 0. 05+1 84 74 9+Fb 0. 05+0. 1 83 72 9+Fc 0. 05+0.1 75 67 9+Na 0. 05+10 80 70 9+Eb 0. 05+1 83 69 9+Ea 0. 05+1 85 70 9+Ba 0. 05+10 75 65 9+Jc 0. 05+0. 5 70 59 9+Jb 0. 05+0. 5 74 54 9+Ja 0. 05+5 70 59 10 + Aa 0 05+0. 5 83 68 10+Ac 0. 05+1 85 70 10+Fb 0. 05+0.1 87 68 10+Fc 0. 05+0.1 83 62 10+Na 0. 05+10 80 65 10+ Eb 0. 05+1 79 65 10+Ea 0.05+1 78 65 10+Ba 0.05+10 77 60 10+Jc 0. 05+0.5 75 53 10+Jb 0. 05+0. 5 68 47 10+Ja 0.05 +5 75 53 11+Aa 0. 05+0. 5 76 67 11+Ac 0.05+1 82 69 11+Fb 0. 05+0.1 75 67 11+Fc 0. 05+0. 1 79 60 ll+Na 0.05 +10 74 64 11+Eb 0. 05+1 74 64 -95- 201238485 [Table 13-5] Effect of the mixture of the compound of the present invention and the existing bactericidal active compound Test compound concentration (ppm) Experimental 値 control price calculation値 Control rate (E) 11+Ea 0. 05+1 77 64 11+Ba 0. 05+10 73 59 11+Jc 0. 05+0. 5 73 51 11+Jb 0. 05+0. 5 70 46 11+Ja 0. 05+5 73 51 12+Aa 0. 05+0. 5 78 69 12+Ac 0. 05+1 85 70 12+Fb 0. 05+0. 1 80 69 12+Fc 0. 05+0. 1 78 62 12+Na 0 05+10 74 66 12+Eb 0. 05+1 80 65 12+Ea 0. 05+1 82 66 12+Ba 0. 05+10 83 61 12+Jc 0. 05+0. 5 75 54 12+ Jb 0. 05+0. 5 70 48 12+Ja 0. 05+5 75 54 (Note) Each of the two English letters of the test compound in Table 13-1 to Table 13-5 and two in Table 12 The English alphabet has the same meaning. It is apparent from the above Tables 13-1 to 13-5 that the mixture of the compound of the present invention and the existing bactericidal active compound has a larger experimental enthalpy than that of 値E, indicating that the effect by the combination has a multiplication effect. Test Example 1 杀. Insecticidal effect test against cotton aphid The compound group (fluorinated quinazoline derivative) shown in [Table 1-1] and [Table 1-2] and the existing one shown in [Table 14] were tested. The bactericidal active compound (hereinafter referred to as the English letter corresponding to the compound name) is adjusted to a mixture containing the active ingredient of the specified concentration by dilution with water. The small melon leaves with a diameter of 3 cm were placed on a plastic cup containing 0.5% soft seaweed, and 5 cotton-96-201238485 female insects (Aphis gossypii) were stocked. After standing for 1 night, the number of larvae produced was calculated, 0.4 ml was dispensed each time with the adjusted liquid, and the number of dead insects was calculated after 2 days of spreading, and the mortality rate was calculated according to the method of Experimental Example 4. Further, the effect expected by combining the respective active compounds was determined by the calculation formula of Colby. The effects of the respective active compounds are shown in Table 14. The effects of the mixture of the compound of the present invention and the conventional insecticidally active compound are shown in Table 1 5-1 to Table 1 5-3, respectively. [Table 14] Effect of each active compound Test compound supply degree (ppm) Experimental cockroach cockroach 1 0. 1 36 2 0.1 39 3 〇. 1 40 4 0. 1 39 5 0.1 37 6 0.1 41 7 0. 1 43 8 0. 1 44 9 0. 1 40 10 ΙΤΓ 36 11 ο. ΐ 39 12 0.1 40 P eucalyptus 0 "36 y edamine o.oi 39 R defensin 0.5 41 S ananin 0.1 43 ΐ Flunimidide 1 44 u pyrifluquinazon 0. 01 40 -97- 201238485 [Table 15-1] Effect of the mixture of the compound of the present invention and the existing insecticidally active compound Test compound concentration (ppm) S 値 値 値 计算 calculation値 率 CE rate CE) 1 + P 0. 1+10 73 59 1 +Q 0. 1+0· 01 80 61 1 + R 0. 1+0· 5 79 62 1 + S 0. 1+0. 1 80 64 1 + T 0. 1+1 79 64 1 + U 0. 1+0. 01 78 62 2 + P 0. 1+10 73 61 2 +Q 0. 1+0.01 80 63 2 + R 0. 1 +0· 5 79 64 2 + S 0. 1+0. 1 80 65 2 + T 0. 1+1 79 66 2 + U 0. 1+0. 01 73 63 3 +P 0-1+10 80 62 3 +Q 0· 1+0. 01 79 63 3 + R 0. 1+0. 5 80 65 3 + S 0. 1+0. 1 79 66 3 + T 0. 1+1 78 66 3 + U 0 01+64 80 6 4 +Q 0.1+0. 01 79 63 4 + R 0.1+0. 5 80 64 4 + S 0. 1+0. 1 79 65 4 + T 0, 1+1 80 66 4 +U 0. 1+0. 01 79 63 5 + P 0. 1+10 82 60 5 +Q 0.1+0. 01 81 62 5 + R 0. 1+0. 5 82 63 5 + S 0. 1+0· 1 81 64 5 + T 0. 1+1 75 65 -98- 201238485 [Table 15-2] Compounds of the invention and The effect of the mixture of the existing insecticidal active compounds The concentration of the test compound (ppm) The experimental insect mortality rate is calculated as the dead insect rate (E) 5 + U 0 · 1 + 0.01 75 62 6 + P 0 · 1 + 10 82 62 6 +Q 0· 1+0.01 81 64 6 + R 0· 1+0.5 82 65 6 + S 0· 1+0. 1 81 . 66 6 + T 0. 1+1 75 67 6 +U 0. 1 +0.01 80 65 7 +P 0. 1+10 82 64 7 +Q 0· 1+0. 01 81 65 7 + R 0· 1+0.5 82 66 7 + S 0. 1+0. 1 81 68 7 + T 0· 1+1 80 68 7 +U 0· 1+0.01 75 66 8 +P 0. 1+10 82 64 8 +Q 0· 1+0. 01 81 66 8 +R 0_ 1+0.5 82 67 8 + S 0. 1+0. 1 81 68 8 +T 0, 1+1 80 69 8 + U 0. 1+0. 01 80 66 9 +P 0. 1+10 82 62 9 +Q 0. 1+ 0. 01 81 63 9 + R 0· 1+0.5 82 65 9 + S 0· 1+0. 1 81 66 9 + T 0· 1+1 79 66 9 +U 0. 1+0, 01 78 64 10 + P 0· 1+10 73 59 10 + Q 0· 1+0.01 80 61 10 + R 0. 1+0.5 79 62 10 + S 0. 1+0. 1 80 64 10 + T 0· 1+1 79 64 -99- 201238485 [Table 15-3] Effect of the mixture of the compound of the present invention and the existing insecticidally active compound The test compound was tested for concentration (ρρπ〇 experimental 値 dead rate calculation 値Dead insect rate (Ε) 10 +U 0. 1+0. 01 79 62 11 +P 0. 1+10 78 61 11 +Q 0.1+0. 01 73 63 11 +R 0. 1+0. 5 80 64 11 + S 0. 1+0, 1 79 65 11 +T 0. 1+1 80 66 11 + U 0_ 1+0. 01 79 63 12 + P 0. 1+10 78 62 12 + Q 0. 1+ 0. 01 73 63 12 + R 0.1+0. 5 82 65 12 + S 0.1+0. 1 81 66 12 +T 0. 1+1 75 66 12 +U 0.1+0. 01 75 64 (Note) Table 15 Each of the two English letters of the test compound in the range of -1 to Table 1S-3 has the same meaning as the two English letters in Table 14. It is apparent from the above Tables 15-1 to 15-3 that the mixture of the compound of the present invention and the existing insecticidally active compound has a larger experimental enthalpy than that of 値E, indicating that the effect by the combination has a multiplication effect. [Industrial Applicability] The pest control agent for agricultural and horticultural plants containing one or two or more kinds of fluorine-containing oxazoline derivatives as active ingredients, and the pathogens for agricultural and horticultural plants, Pests such as insects and cockroaches show excellent control effects with low doses, and are extremely suitable for novel pesticides because of their high safety to useful crops. In addition, the mixture of the fluorinated quinazoline derivative of the present invention and the existing bactericidal active compound, and the mixture of the fluorinated quinazoline derivative of the present invention and the existing insecticidally active compound, the experimental 値-100-201238485 Colby's calculation formula based on the calculation 値E is large, and since it is shown that the effect of the combination has a multiplication effect, it is highly suitable as a mixture. -101 -

Claims (1)

201238485 七、申請專利範圍： 式所示， 1 · 一種含氟喹唑啉衍生物，其係以下 [1-1]以及 Π-2]: 【化1】201238485 VII. Patent application scope: As shown in the formula, 1 · A fluorine-containing quinazoline derivative, which is the following [1-1] and Π-2]: [Chemical 1] [式中，R1係由下述（a)〜（d)選出： a) 由苯基、苯甲基、噁唑基、異噁 苯并呋喃基、異苯并呋喃基、二氫苯并呋 異噻唑基、萘基、嘧啶基、吡嗪基、喹喔 、吡啶基、喹啉基、異喹啉基、苯并噻唑 基、吡咯基、吲哚基、異吲哚基、苯并噁 唑基、噻吩基、苯并噻吩基、咪唑基、苯 基、吡啶酮基所成之群選出，且視情況而 原子之單環式或雙環式之環， b) 碳原子數1〜6之直鏈狀或分枝狀 數2〜8之直鏈狀或分枝狀之烯基、碳原子 或分枝狀之炔基、碳原子數3〜8之環烷基 之環烯基， c) — SiR5R6R7(R5、R6、R7 係碳原子 或分枝狀之烷基、以1個鹵素原子取代之 直鏈狀或分枝狀之鹵烷基、以1個氰基: 哩基、呋喃基、 喃基、噻唑基、 啉基、喹唑啉基 基、苯并異噻唑 唑基、苯并異噁 并咪唑基、吡唑 爲含有〇〜3個雜 之烷基、碳原子 數2〜8之直鏈狀 或碳原子數3~8 數1〜6之直鏈狀 碳原子數1〜3之 収代之碳原子數 -102- 201238485 1〜3之直鏈狀或分枝狀之氰基院基、以及苯基，且其中二 者或全部可爲相同之取代基或全部相異之取代基）， d)氫原子， 且在（a)或（b)之情況時，R1係可以下述所取代： _ C (0) 0 R ' _ C (0) R ' — R ' — OR、一 SR、一 S Ο 2 R ' -0C(0)R、一C(0)NHR、一 C(0)NR2、一NHS02R、 —NRS 02R ' _ NHR、一 NR2 ' 一 NHC(0)R、一 NRC(0)R 、一NHC(0)0R、一NRC(0)0R、一N(0R)C(0)0R、 —N H S O 2 R ' — N R S O 2 R ' — SO2NHR、~ S〇2NR_2(此處之 R 係代表碳原子數1〜8之直鏈狀或分枝狀之烷基、碳原子數 2〜8之直鏈狀或分枝狀之烯基、碳原子數2〜8之直鏈狀或 分枝狀之炔基或碳原子數3~8之環烷基）、一SiR5R6R7 、一OSiR5R6R7 (R5、R6、R7係碳原子數1〜6之直鏈狀或 分枝狀之烷基、以1個鹵素原子取代之碳原子數1~3之直 鏈狀或分枝狀之鹵烷基、以1個氰基取代之碳原子數1〜3 之直鏈狀或分枝狀之氰基烷基、以及苯基，且其中二者或 全部可爲相同之取代基或全部相異之取代基）、鹵烷基、 鹵烯基、鹵烷氧基、醯基烷氧基、醯氧基烷基、烷基磺酸 基烷基、矽烷氧基烷基、羥基烷基、烷氧基烷基、鹵烷氧 基烷基、烷基硫代烷基、二烷氧基乙縮醛基、烷氧基烷氧 基'氰基烷基、鹵素、氰基、硝基、胺基、羥基、戊鹵磺 醯基、苯甲基、苯甲基氧基、苯基、苯氧基、吡啶基、噁 唑基、呋喃基、噻唑基、萘基、嘧啶基、噻吩基、苯并噻 唑基、苯并噁唑基、苯并二噁茂基、亞胺基、甲醯基（ -103- 201238485 一 CHO)、殘基（一COOH)、甲醯胺基（-NHCHO)、環狀酸 以及環狀胺， R2 表示氫原子、一R、一 OR、一 C(0)0R、 一 C(0)NHR、一 CONR2(此處之R係碳原子數1~8之直鏈 狀或分枝狀之烷基、碳原子數2〜8之直鏈狀或分枝狀之烯 基、碳原子數2〜8之直鏈狀或分枝狀之炔基或碳原子數 3〜8之環烷基）、羥基烷基、烷氧基烷基、鹵烷氧基烷基 、苯基、雜芳基、鹵素、氰基、鹵烷基、鹵烷氧基]。 2.如申請專利範圍第1項之化合物，其中R2係氫原 子、鹵素原子 '氰基、苯基、雜芳基、一R、_C(0)0R、 -C(0)NHR(此處之R係碳原子數1〜8之直鏈狀或分枝狀 之烷基、碳原子數2〜8之直鏈狀或分枝狀之烯基、碳原子 數2〜8之直鏈狀或分枝狀之炔基或碳原子數3〜8之環烷基 )、羥基烷基、烷氧基烷基。 3 .如申請專利範圍第1項之化合物’其中R 1係由苯 基、噁唑基、呋喃基、噻唑基、萘基、嘧啶基、吡啶基、 苯并噻唑基、吡咯基、苯并噁唑基、吡嗪基、噻吩基、咪 唑基所成之群選出，且視情況而由含有〇~3個雜原子之情 況的單環式或雙環式之環選出。 4.—種如申請專利範圍第1項之式Π·1]或Π-2]所示含 氟喹唑啉衍生物之製造方法，其係使以式[n]以及[瓜]所 示之任一種化合物與以式[IV]所示之3-丁炔胺衍生物’於 鹼基存在下進行反應， -104- 201238485 【化2】Wherein R1 is selected from the following (a) to (d): a) from phenyl, benzyl, oxazolyl, isobenzobenzoyl, isobenzofuranyl, dihydrobenzofuran Isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinacrid, pyridyl, quinolyl, isoquinolinyl, benzothiazolyl, pyrrolyl, indolyl, isodecyl, benzoxazole a group selected from the group consisting of a thiophene group, a benzothienyl group, an imidazolyl group, a phenyl group, and a pyridone group, and optionally a monocyclic or bicyclic ring of atoms, b) a carbon atom number of 1 to 6 a linear or branched alkenyl group having 2 to 8 chains, a carbon atom or a branched alkynyl group, a cycloalkyl group having 3 to 8 carbon atoms, c) — SiR5R6R7 (R5, R6, R7 is a carbon atom or a branched alkyl group, a linear or branched haloalkyl group substituted by one halogen atom, and a cyano group: anthracenyl group, furyl group, methane a group, a thiazolyl group, a phenyl group, a quinazolinyl group, a benzoisothiazolyl group, a benzoisoximidazolyl group, a pyrazole is a hydrazine having 3 to 3 heteroalkyl groups, and having a carbon number of 2 to 8 Chain or carbon number 3~8 a linear or branched cyano group having a linear carbon number of 1 to 3, which is 1 to 3, and a phenyl group, and both of them Or all may be the same substituent or all of the different substituents), d) a hydrogen atom, and in the case of (a) or (b), the R1 system may be substituted as follows: _ C (0) 0 R ' _ C (0) R ' — R ' — OR, an SR, a S Ο 2 R ' -0C(0)R, a C(0)NHR, a C(0)NR2, an NHS02R, —NRS 02R ' _ NHR, one NR2 '-NHC(0)R, one NRC(0)R, one NHC(0)0R, one NRC(0)0R, one N(0R)C(0)0R, -NHSO 2 R ' — NRSO 2 R ' — SO2NHR, ~ S〇2NR_2 (wherein R represents a linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched carbon number of 2 to 8) a branched alkenyl group, a linear or branched alkynyl group having 2 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, a SiR5R6R7, an OSiR5R6R7 (R5, R6, R7 carbon atom) a linear or branched alkyl group having 1 to 6 or a linear or branched haloalkyl group having 1 to 3 carbon atoms substituted by one halogen atom; a linear or branched cyanoalkyl group having 1 to 3 carbon atoms, and a phenyl group, and both or all of them may be the same substituent or all of the different substituents, and a halogenated alkane Base, haloalkenyl, haloalkoxy, nonylalkoxy, decyloxyalkyl, alkylsulfonylalkyl, nonyloxyalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxy Alkyl, alkylthioalkyl, dialkoxyacetal, alkoxyalkoxycyanoalkyl, halogen, cyano, nitro, amine, hydroxy, pentylsulfonyl , benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl , benzodioxanyl, imido, carbenyl (-103- 201238485-CHO), residue (monoCOOH), formamidine (-NHCHO), cyclic acid and cyclic amine, R2 represents hydrogen Atom, an R, an OR, a C(0)0R, a C(0)NHR, a CONR2 (wherein R is a linear or branched alkyl group having 1 to 8 carbon atoms, a carbon atom 2 to 8 linear or branched An alkenyl group, a linear or branched alkynyl group having 2 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, a hydroxyalkyl group, an alkoxyalkyl group or a haloalkoxyalkyl group; Phenyl, heteroaryl, halogen, cyano, haloalkyl, haloalkoxy]. 2. A compound according to claim 1, wherein R2 is a hydrogen atom, a halogen atom 'cyano group, a phenyl group, a heteroaryl group, a R, _C(0)0R, -C(0)NHR (herein R is a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkenyl group having 2 to 8 carbon atoms, or a linear or branched carbon number of 2 to 8. A dendritic alkynyl group or a cycloalkyl group having 3 to 8 carbon atoms, a hydroxyalkyl group or an alkoxyalkyl group. 3. The compound of claim 1 wherein R 1 is a phenyl group, an oxazolyl group, a furyl group, a thiazolyl group, a naphthyl group, a pyrimidinyl group, a pyridyl group, a benzothiazolyl group, a pyrrolyl group, a benzoic acid group. A group of azolyl, pyrazinyl, thienyl, and imidazolyl groups is selected and, as the case may be, a monocyclic or bicyclic ring containing 〇~3 heteroatoms. 4. A method for producing a fluorine-containing quinazoline derivative as shown in the formula [1] or Π-2] of the patent application, which is represented by the formula [n] and [melon] Any one of the compounds is reacted with a 3-butynylamine derivative represented by the formula [IV] in the presence of a base, -104-201238485 [Chemical 2] [IV] [式中，R1以及R2係具有如申請專利範圍第1項記載之意 義]。 5 . —種有害生物防治劑，其係含有以如申請專利範圍 第1項之式Π-1]或[1-2]所示之含氟喹唑啉衍生物爲有效成 分之1種或2種以上而成。 6.—種農園藝用有害生物防治組成物’其係含有1種 或2種以上之以如申請專利範圍第1項之式[1-1]以及[1-2] 所示之含氟喹唑啉衍生物爲有效成分，以及含有下述 (1)〜（3 9)所示之殺菌、殺蟲化合物中之1種或2種以上爲 有效成分， (1)阻礙 SH合成活性之化合物：四氯異苯腈 (chlorothalonil)、腈硫醌（dithianon)、蓋普丹（captan)、福 爾培（folpet)、院苯礦酸鹽（iminoctadine-albesilate)、院苯 醋酸鹽（iminoctadine-triacetate)、富爾邦（ferbam)、代森 鈉（nabam)、猛乃浦（maneb)、鉢锰乃浦（mancozeb)、免得 -105- 201238485 爛（metiram)、甲基鋅乃浦（propineb)、代森福美鋅 (polycarbamate)、得恩地（thiram)、福美鋅（ziram)、代森 辟（zineb)、氧化銅（cupric oxide)、氫氧化銅（copper hydroxide)、驗性氯氧化銅（COpper oxychloride)、無水硫 酸銅（copper sulfate (anhydride))、硫酸銅（copper sulfate) 、硫擴（sulfur); (2) 阻礙核酸生合成活性之化合物：滅達樂 (metalaxyl)、右滅達樂（metalaxyl-M)、歐殺斯（oxadixyl) 、布瑞莫（bupirimate)、殺紋寧（hymexazol)、歐索林酸 (oxolinic acid)； (3) 阻礙紡錘絲形成活性之化合物：免賴得 (b e η 〇 m y 1)、貝芬替（c a r b e n d a z i m )、乙黴威（d i e t h o f e n c a r b) 、甲基多保淨（thiophanate-methyl)、座賽胺（zoxamide)、 賓克隆（pencycuron)、氟比來（fluopicolide); (4) 苯甲酿苯胺（benzanilide)系化合物：福拉比 (furametpyr)、卩比噻菌胺（penthiopyrad)、賽氟滅 (thifluzamide)、白克列（boscalid)、嘉保信（oxycarboxin) 、萎鏽靈（carboxin)、福派銳（fluopyram)、福多寧 (flutolanil)、滅普寧（mepronil); (5) 甲氧基丙烯酸酯（strobilurin)系化合物：亞托敏 (azoxystrobin)、陡氧菌酯（picoxystrobin)、克收欣 (kresoximmethyl)、三氣敏（trifloxystrobin)、歐殺敏 (orysastrobin)、美托敏（metominostrobin)、百克敏 (pyraclostrobin)、凡殺同（famoxadone)、咪嗤菌酮 -106- 201238485 (fenamidone)、派丙威（pyribencarb)、二膜敏 (dimoxystrobin)、派羅敏（pyrametostrobin)、派稀敏 (pyraoxystrobin)； (6) 其他阻礙電子傳遞系活性之化合物：二氟林 (diflumetorim)、賽座滅（cyazofamid) ' 安美速 (amisulbrom)、消蠘多（meptyldinocap)、扶吉胺 (fluazinam)、富米綜（ferimzone); (7) 阻礙胺基酸生合成活性之化合物：賽普洛 (cyprodinil)、滅派林（mepanipyrim)、派美尼 (pyrimethanil)、保米黴素（blasticidin-S)、鏈黴素 (streptomycin)、嘉賜黴素（kasugamycin); (8) 阻礙固醇生合成活性之化合物：氧環唑 (azaconazole)、 比 多 農（bitertanol)、 溴 克 座 (bromuconazole) ' 環克座（Cypr〇c〇nazole)、待克利 (difenoconazole)、依普座（epoxiconazole)、芬克座 (fenbuconazole) 、夫菌 唑 (furconazole) 、 菲 克 利 (hexaconazole) 、易胺座 (imibenconazole)、 克康 那 唑 (metoconazole) 、邁克 尼 (myclobutanil) 、 平 克 座 (penconazole) 、 普克利（propiconazole) ' 矽 氟 唑 (simeconazole) 、得克 利 (tebuconazole) 、 三 泰 芬 (triadimefon) 、 - 泰 ——« 隆 (triadimenol) 、 滅 菌 唑 (triticonazole)、 依滅列（i mazalil)、賽福座（triflumizole) 、披扶座（pefurazoate)、 撲 克拉（prochloraz) '芬 rut m 莫 (fenarimol) 、 環酿菌 胺 (fenhexamid) 、 芬 普 福 -107- 201238485 (fenpropimorph)、粉病靈（piperalin)、螺環菌胺 (spi roxamine)； (9)阻礙細胞壁合成活性之化合物：依普同 (iprodione)、滅克寧（myclozolin)、撲滅寧（procymidone) 、免克寧（vinclozolin)、快諾芬（quinoxyfen)、護汰寧 (fludioxonil)； (10) 阻礙脂質生合成活性之化合物：丙基喜樂松 (iprobenfos)、亞賜圃（isoprothiolane)、五氯硝苯 (quintozene)、普拔克（propamocarb)、普司克（prothicarb) 、達滅芬（dimethomorph)、編霉威（iprovalicarb)、苯噻菌 胺（benthiavalicarb)、曼普胺（mandipropamid); (11) 阻礙葡聚醣合成活性之化合物：維利黴素 (validamycin)、保粒黴素（甲）（p〇ly〇xinB); (12) 阻礙黑色素合成活性之化合物：百快隆 (pyroquion)、三賽哩（tricyclazole)、加普胺（carpropamid) 、雙氯氰菌胺（diclocymet)、芬諾尼（fenoxanil); (13)誘導宿主產生防禦反應之化合物：阿拉酸式苯-S -甲基（acibenzolar-S-methyl)、撲殺熱（probenazole)、異 噻菌胺（isotianil)、褐藻多醣（laminarin); (14) 具有其他或未知作用之化合物：克絕 (cymoxanil)、福賽得（fosetyl-Al)、***磷（triazoxide)、 滅速克（methasulfocarb)、氟硫滅（flusulfamide)、蟎離丹 (chinomethionat)、噻哩菌胺（ethaboxam)、賽芬胺 (cyflufenamid)、福多寧（flutlanil)、滅芬農（metrafenone) -108- 201238485 、異 丁乙氧喹啉（tebufloquin)、氣基卩比 D定（pyridylamidine) 、醯菌酯（enestroburin)、丙氧嗤咐（卩1：〇911丨11&2【£1)、3丫1<1-524464、SYN-520、BYF-14182、必殺分（bixafen)、福殺 銳（fluxapyroxad)、福派銳（fluopyram)、伏魔飛（flumorph) 、福來帖（valifenalate)、殺真菌劑（pyriofenone); (15) 生物殺菌劑：農桿菌（Agrobacterium radiobacter)、枯草桿菌（Bacillus subtilis)、彩色海芋軟腐 細菌（Erwinia carotovora)、營光假單胞菌（Pseudomonas fluorescens)、擴藍狀菌（Talaromyces flavus)、抗括性木 黴菌（Trichoderma atroviride); (16) 乙醯膽鹼酯酶抑制劑：得滅克（aldicarb)、免扶 克（benfuracarb)、加保利（carbaryl)、加保扶（carbofuran) 、丁基加保扶（carbosulfan)、丁基滅必蟲（fenobucarb)、 滅賜克（methiocarb)、納乃得（methomyl)' 毆殺滅（oxamyl) 、硫敵克（thiodicarb); (17) 殿殺松（acephate)、陶斯松（chlorpyrifos)、大利 松（diazinon)、大滅松（dimethoate)、馬拉松（malathion)、 達馬松（methamidophos)、亞素靈（monocrotophos)、甲基 巴拉松（parathion-methyl)、佈飛松（profenofos)、托福松 (terbufos)、密殺松（imicyafos); (18) 阻礙GABA依賴性氯離子通道之化合物：安殺 番（endosulfan)、乙蟲清（ethiprole)、芬普尼（fipr〇nil)、艾 同清（acetoprole)； (19) 阻礙鈉離子通道之化合物：畢芬寧（bifenthrin) -109- 201238485 、赛滅寧（cypermethrin)、益化利（esfenvalerate)、迷菊酯 (ethofenprox)、賽洛寧（lambda-cyhalothrin)、貼福寧 (tefluthrin)、DDT(DDT)、甲氧 DDT (methoxychlor); (2 0)阻礙尼古丁性乙醯膽鹼受器之化合物：亞滅培 (acetamiprid)、可尼丁 （ c 1 o t h i a n i d i η)、達特南 (dinotefuran)、益達胺（imidacloprid)、烧 D定蟲胺 (nitenpy ram)、賽果培（thiacloprid)、賽速安 (thiamethoxam)； (21) 賜諾司（spinosyn)、賜諾特（spinetoram): (22) 阻礙氯離子通道之化合物：阿巴汀（abamectin) 、因滅汀(emamectin-benzoate)、密滅汀(milbemectin)、 利滅汀（lepimectin); (23) 僞返幼激素（juvenile hormone)化合物：丙諾保 (kinoprene)、美西保（methoprene)、芬諾克（fenoxycarb)、 百利普芬（pyriproxyfen); (24) 非選擇性阻礙化合物：溴化甲烷（methyl bromide)、氯化苦（chloropicrin); (25) 阻礙選擇性攝食之化合物：派滅淨 (pymetrozine)、氟尼胺（flonicamid); (26) 阻礙蟎類成長之化合物：克芬蠘（clofentezine) '合赛多（hexythiazox)、依殺蟎（etoxazole); (27) Bt 劑：蘇力菌（Bacillus thuringiensis); (28) 阻礙 ATP 合成之化合物：汰芬隆 (diafenthiuron)、亞環錫（azocyclotin).、錫蟎丹（cyhexatin) -110- 201238485 、芬佈賜（fenbutatin oxide)、殿蟎多（propargite)、得脫蟎 (tetradifon)； (29) 去氧化性磷酸化共軛化合物：克凡派 (chlorfenapyr)； (3 0)阻礙尼古丁性乙醯膽鹼受器通道之化合物：免 速達（bensultap)、培丹（cartap)、硫賜安（thiocyclam); (31) 阻礙幾丁質（chitin)生合成之化合物：克福隆 (chlorfluazuron)、二福隆（diflubenzuron)、氟芬隆 (flufenoxuron) 六伏隆（hexaflumuron)、祿芬隆 (lufenuron)、諾伐隆（novaluron)、得福隆（teflubenzuron) 、三福隆（triflumuron)、布芬淨（buprofezin)、雙三氟隆 (bistrifluron)； (32) 干擾脫皮·變態之化合物：賽滅淨（cyromazine) 、可芬諾（chromafenozide)、合芬隆（halofenozide)、滅芬 諾（methoxyfenozide)、得芬諾（tebufenozide)、諾福隆 (noviflumuron)； (33) 章魚胺（octopamine)拮抗化合物：三亞摘 (amitraz)、愛美松（hydramethylnon)、亞醌輸 (acequinocyl)； (34) 阻礙電子傳遞系化合物：芬殺蟎（fenazaquin)、 芬普輸（fenpyroximate)、畢汰芬（pyrimidifen)、畢達本 (pyridaben)、得芬瑞（tebufenpyrad)、脫芬瑞（tolfenpyrad) 、魚藤精（rotenone); (35) 憐酸化銘（Aluminium phosphide); -111 - 201238485 (3 6)阻礙電位依賴性鈉離子通道之化合物：因得克 (indoxacarb) 美氣綜（metaflumizone)、賜派芬 (spirodiclofen)； (37) 阻礙脂質合成之化合物：螺.甲蟎酯 (spiromesifen)、賜派滅（spirotetramat); (38)阻礙雷阿諾定受器（ryanodine receptor)之化合 物：勉安勃（chlorantranilprole)、氟大滅（flubendiamide) 、訊蟲醯胺（cyantranilprol);以及 (3 9) 具有其他或未知作用之化合物：印楝素 (azadirachtin) 西脫織（benzoximate)、必芬蠘 (bifenazate)、蟎離丹（chinomethionat)、大克蟎（dicofol) 、定脫輸（pyridalyl)、皮羅夫（pyrifluquinazon)、福脫鍋 (fluensulfone) ° 7.—種農園藝用有害生物防治組成物，其特徵係含有 以如申請專利範圍第1項之式Π-1]以及Π-2]所示之含 氟喹唑啉衍生物爲有效成分之1種或2種以上，以及 由四氯異苯腈 （chlorothalonil)、 蟎離丹 (chinomethionat)、克熱淨（iminoctadine albesilate)、賽福 座（triflumizole)、得克利(tebuconazole)、待克利 (difenoconazole)、三泰芬（triadimefon)、芬普福（ fenpropimorph)、亞托敏（azoxystrobin)、百克敏 (pyraclostrobin)、三氟敏（trifloxystrobin)、克收欣 (kresoxim-methyl)、賽芬胺（cyflufenamid)、Π比噻菌胺 -112- 201238485 (penthiopyrad)、福多寧（fUtolanil)、快諾芬（quinoxyfen) 、 甲基多保淨 （thiophanate methyl) 二氟林 (diflumetorim)以及阿拉酸式苯-S-甲基（acibenzolar-S-methyl)所成之殺菌化合物群選出的1種或2種以上爲有 效成分。 8. —種農園藝用有害生物防治組成物，其特徵係含有 以如申請專利範圍第1項之式[1-1]以及[1-2]所示之含 氟喹唑啉衍生物爲有效成分之1種或2種以上，以及 由四氯異苯腈（chlorothalonil)、鐘乃浦（manzeb)、賽 座滅（cyazofamid)、安美速 （amisulbrom)、克絕 (cymoxanil) 克收欣（kresoxim-methyl)、亞托敏 (azoxystrobin)、右滅達樂（metalaxyl-M)、曼普胺 (mandipropamid)、苯噻菌胺（benthiavalicarb-isopropyl)以 及達滅芬（dimethomorph)所成之殺菌化合物群選出的1種 或2種以上爲有效成分。 9. 一種農園藝用有害生物防治組成物，其特徵係含有 以如申請專利範圍第1項之式[1-1]以及[1-2]所示之含 氟喹唑啉衍生物爲有效成分之1種或2種以上，以及 由毆殺松（acephate)、益達胺（imidacloprid)、脫芬瑞 (tolfenpyrad)、阿納寧（acrinathrin)、氟尼胺（flonicamid) 以及皮羅夫（pyrifluquinazon)所成之殺蟲化合物群選出的 1種或2種以上爲有效成分。 -113- 201238485 四 指定代表圖： (一） 本案指定代表圖為：無 (二） 本代表圖之元件符號簡單說明：無 五、本案若有化學式時，請揭示最能顯示發明特徵的化學 式：無[IV] [wherein R1 and R2 have the meanings as described in the first item of the patent application scope]. A pest control agent comprising one or two active ingredients of a fluorine-containing quinazoline derivative represented by the formula Π-1] or [1-2] of the scope of claim 1 More than one species. 6. A pest control composition for agriculture and horticulture, which contains one or more fluoroquines as shown in the formula [1-1] and [1-2] of the scope of claim 1 The oxazoline derivative is an active ingredient, and one or two or more of the bactericidal and insecticidal compounds represented by the following (1) to (39) are active ingredients, and (1) a compound which inhibits SH synthesis activity: Chlorothalonil, dithianon, captan, folpet, iminoctadine-albesilate, iminoctadine-triacetate , ferbam, nabam, maneb, mancozeb, free -105-201238485 ruin (metiram), methyl zinc genus (propineb), generation Polycarbamate, thiram, ziram, zineb, cupric oxide, copper hydroxide, COpper oxychloride , copper sulfate (anhydride), copper sulfate, sulfur; (2) Compounds that hinder the synthesis of nucleic acids: metalaxyl, metalaxyl-M, oxadixyl, bupirimate, hymexazol, Oxolinic acid; (3) Compounds that hinder the formation of spindle filaments: be η 〇my 1), carbendazim, diethofencarb, methylpreservative ( Thiophanate-methyl), zoxamide, pencycuron, fluopicolide; (4) benznilide compound: furametpyr, bismuthamide (penthiopyrad), thifluzamide, boscalid, oxycarboxin, carboxin, fluopyram, flutolanil, mepronil (5) methoxy acrylate (strobilurin) compounds: azoxystrobin, picoxystrobin, kresoximmethyl, trifloxystrobin, orysastrobin Metominostrobin , pyracostrobin, famoxadone, imipenem-106- 201238485 (fenamidone), pyrenecarb (pyribencarb), dimoxystrobin, pyrometostrobin, pyridin (pyraoxystrobin); (6) Other compounds that impede the activity of electron transport systems: diflumetorim, cyazofamid 'amisulbrom, meptyldinocap, fluazinam, Fermizone; (7) Compounds that block the synthesis of amino acid: cyprodinil, mepanipyrim, pyrimethanil, blasticidin-S , streptomycin, kasugamycin; (8) compounds that block the biosynthesis activity of sterol: azaconazole, bitertanol, bromuconazole' ring Cypre〇c〇nazole, difenoconazole, epoxiconazole, fenbuconazole, furconazole, hexaconazole, imibenconazole, Kkona Metoconazole, myclobutanil, penconazole, propiconazole 'simeconazole, tebuconazole, triadimefon, -tai—«long (triadimenol), triticonazole, i mazalil, triflumizole, pefurazoate, prochloraz, fenrumol, fenarimol (fenhexamid), Fenfen-107-201238485 (fenpropimorph), piperalin, spi roxamine; (9) compounds that block cell wall synthesis activity: iprodione, gram Myclozolin, procymidone, vinclozolin, quinoxyfen, fludioxonil; (10) compounds that block lipid biosynthesis activity: iprobenfos, Isoprothiolane, quintozene, propamocarb, prothicarb, dimethomorph, iprovalicarb Benthiavalicarb, mandipropamid; (11) Compounds that inhibit glucan synthesis activity: validamycin, granulidine (a) (p〇ly〇xinB); (12) Compounds that block melanin synthesis activity: pyroquion, tricyclazole, carpropamid, diclocymet, fenoxanil; (13) Compounds that induce host defense responses: acibenzolar-S-methyl, probenazole, isotianil, laminarin; (14) other Or unknown compounds: cymoxanil, fosetyl-Al, triazoxide, methasulfocarb, flusulfamide, chinomethionat, thiazide Ethaboxam, cyflufenamid, flutlanil, metrafenone -108- 201238485, tebufloquin, gas-based bismuth (pyridylamidine) ), fenstrocin (enestroburin), propoxy咐 (卩1:〇911丨11&2[£1), 3丫1<1-524464, SYN-520, BYF-14182, bixafen, fluxapyroxad, floopyram ), flumorph, valifenalate, fungicide (pyriofenone); (15) biocides: Agrobacterium radiobacter, Bacillus subtilis, colored sea bream soft rot bacteria Erwinia carotovora), Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride; (16) Acetylcholinesterase inhibitor: Dexter ( Aldicarb), benfuracarb, carbaryl, carbofuran, carbosulfan, fenobucarb, metiocarb, nanet (methomyl) oxa oxamyl, thiodicarb; (17) acephate, chlorpyrifos, diazinon, dimethoate, marathion ), methamidophos, azolyn (monocrotophos), parathion-methyl, profenofos, terfufos, imicyafos; (18) compounds that block GABA-dependent chloride channels: ampoules Endosulfan), ethiprole, fipr〇nil, acetoprole; (19) compounds that block sodium ion channels: bifenthrin -109- 201238485, cypermethrin ), esfenvalerate, ethofenprox, lambda-cyhalothrin, tefluthrin, DDT (DDT), methoxy DDT (methoxychlor); (20) hinder nicotine Compounds of acetylcholine receptors: acetamiprid, c 1 othianidi η, dinotefuran, imidacloprid, nitenpy ram , thiacloprid, thiamethoxam; (21) spinosyn, spinetoram: (22) compounds that block chloride channels: abamectin, Emamectin-benzoate, milbemect In), lepimectin; (23) pseudo-juvenile hormone compounds: kinoprene, metoprene, fenoxycarb, pyriproxyfen (24) Non-selective inhibitory compounds: methyl bromide, chloropicrin; (25) compounds that block selective feeding: pymetrozine, flonicamid; (26) Compounds that hinder the growth of mites: clofentezine 'hexythiazox, etoxazole; (27) Bt: Bacillus thuringiensis; (28) hinder ATP Synthetic compounds: diafenthiuron, azocyclotin, cyhexatin -110- 201238485, fenbutatin oxide, propargite, tetradifon (29) Deoxidative phosphorylation conjugated compound: chlorfenapyr; (30) compounds that block the nicotine acetylcholine receptor channel: bensultap, cartap, Thiocyclam; (31) hindering chitin (chitin) synthetic compounds: chlorfluazuron, diflubenzuron, flufenoxuron hexaflumuron, lufenuron, novaluron, Teflubenzuron, triflumuron, buprofezin, bistrifluron; (32) Compounds that interfere with peeling and metamorphosis: cyromazine, chromafenozide ), hafenofozide, methoxyfenozide, tebufenozide, noififlumuron; (33) octopamine antagonistic compounds: amitraz, amesone (amitraz) Hydramethylnon), acequinocyl; (34) compounds that hinder electron transport: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, defenyl (tebufenpyrad), tolfenpyrad, rotenone; (35) Aluminium phosphide; -111 - 201238485 (3) compounds that block potential-dependent sodium channels: (indoxacarb) Metaflumizone, spirodiclofen; (37) Compounds that block lipid synthesis: spiromesifen, spirotetramat; (38) obstruction of Rayoridine Compounds of the ryanodine receptor: chlorantranilprole, flubendiamide, cyantranilprol; and (39) compounds having other or unknown effects: azadirachtin Benzoximate, bifenazate, chinomethionat, dicofol, pyradalyl, pyrifluquinazon, fluensulfone ° 7 - a pest control composition for agriculture and horticulture, characterized by containing a fluorine-containing quinazoline derivative represented by the formula 第-1] and Π-2] as an active ingredient Species or more than two, and from chlorothalonil, chinomethionat, iminoctadine albesilate, triflumizole, tebuconazole, diknoconazol e), triadimefon, fenpropimorph, azoxystrobin, pyraclostrobin, trifloxystrobin, kresoxim-methyl, seffylamine Cyflufenamid), thiabendamine-112-201238485 (penthiopyrad), fUtolanil, quinoxyfen, thiophanate methyl diflumetorim, and arsenic benzene- One or two or more selected from the group consisting of a bactericidal compound formed by a-single-s-methyl group are active ingredients. 8. A pest control composition for agriculture and horticulture, which is characterized by containing a fluorine-containing quinazoline derivative represented by the formula [1-1] and [1-2] of the scope of claim 1 One or more of the components, and consisting of chlorothalonil, manzeb, cyazofamid, amisulbrom, cymoxanil, kresoxim-methyl ), selected from azoxystrobin, metalaxyl-M, mandipropamid, benthiavalicarb-isopropyl, and dimethomorph One type or two or more types are active ingredients. A pest control composition for agriculture and horticulture, which comprises a fluorine-containing quinazoline derivative represented by the formula [1-1] and [1-2] of the scope of claim 1 as an active ingredient. One or more of them, and acephate, imidacloprid, tolfenpyrad, acrinathrin, flonicamid, and pyrifluquinazon One or two or more selected from the group of the insecticidal compound to be formed are active ingredients. -113- 201238485 Four designated representatives: (1) The representative representative of the case is: No (2) The symbol of the representative figure is a simple description: No. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: no