TW308589B - - Google Patents
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- TW308589B TW308589B TW084112144A TW84112144A TW308589B TW 308589 B TW308589 B TW 308589B TW 084112144 A TW084112144 A TW 084112144A TW 84112144 A TW84112144 A TW 84112144A TW 308589 B TW308589 B TW 308589B
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- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000013603 viral vector Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- NRINZBKAERVHFW-UHFFFAOYSA-L zinc;dicarbamate Chemical compound [Zn+2].NC([O-])=O.NC([O-])=O NRINZBKAERVHFW-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
308589 經濟部中央標準局員工消費合作社印製 A7 ___ B7____ 五、發明説明(1 ) 本發明係有關式I之2-[(2-烷氧基-6-三氟甲基嘧咬_4_基)_ 氧亞甲基]苯基乙酸衍生物
o=c—V—ch3 式中標記及取代基具下列意義: U爲CH或N ; V爲〇或NH ; R爲cvcv烷基; R爲泉基、鹵素、CrC4-坑基、Cj-C^-鹵燒基、c^-c^ 烷氧基、Ci-Cf鹵烷氧基或苯基; π爲0或1至4之整數’若η之値大於l’R1基可爲不同 〇 此外,本發明係有關製備此等化合物之方法及中間物, 及含其之組合物,及其用途。 α-雜芳氧亞甲苯基-0-甲氧基丙烯酸甲酯於文獻中記述 爲殺眞菌劑(歐洲專利ΕΡ-Α 178 826,ΕΡ·Α 278 595,ΕΡ-Α 350 691)。ΕΡ-Α 407 873另記述對應之α -[2-(6-三氟甲基嘧 啶-4-基)氧亞甲苯基卜甲氧基丙晞酸甲酯,具殺蟎及殺 昆蟲之作用。 另外揭示具殺眞菌(Ερ·Α 253 213,ΕΡ-Α 254 426,ΕΡ-Α -4- 本紙張尺度適用中國國家樣準(CNS ) Α4規格(210Χ2(>7公釐) I- ^1-^1 nn flu^ nil ^flali ϋ ml— ml mfl m- m· nn I At { (請先閱讀背面之注意事項再填寫本頁) 308589 A7 B7 五、發明説明(2 ) 299 694 ’ EP-A 363 818)及殺昆蟲或殺虫禹作用(EP-A 407 873) 之λ -[2-(雜芳氧亞甲基)苯基]_α_甲氧亞胺基乙酸甲醋。 此外’該文獻記述具殺眞菌(ΕΡ-Α 396 692)及殺昆蟲或 殺瞒作用(ΕΡ-Α 477 631)之Λ -[2-(雜芳氧亞甲基)苯基] 甲氧亞胺基-Ν-甲基乙醯胺。 然而,那裏所述之化合物抗動物害蟲之作用,於許多情 形並不令人滿意。 本發明之目的爲提供於控制有害眞菌及動物害蟲,尤其 有害眞菌、昆蟲、線蟲及蟎,尤其昆蟲及蟎具改良性質之 化合物。 吾等現已發現此目的藉開始所定義之化合物I可達成。 此外’吾等已發現其製備方法及中間物、含其之組合物及 其使用方法。 以類似於開始所提之文獻中所述方法製備化合物I於此 ’化合物1之製得,藉將式II之嘧啶-4-醇以本身已知之方 法’於惰性有機溶媒中,於鹼存在下與式m之苄基衍生物 反應。 經濟部中央棣準局員工消費合作社印製
+ II
Rln^X 0=
C I :C-V III ch2x u一och3 •ch3 ^^1 ^^^1 HI 1^1 n m m —a— IT— ik. c 喊 , ί (請先閱讀背面之注意事項再填寫本頁)
OR 〇=c—v—-ch3 5- - - 你 0- ί
" IN 祕 釐 公 經濟部中央標準局員工消費合作社印製 A7 _B7_ 五、發明説明(3 ) 於式III中,X爲親核性可取代之游離基如鹵素(例如氣、 溴或琪)或坑基或芳確酿基(例如甲確醯基、三氟曱;6^醯基 、苯磺醯基或4-甲苯磺醯基)。 此反應習用上於0°C至80°C,較佳20°C至60°C下進行。 適宜溶媒爲芳烴如甲苯、鄰-、間-及對二曱苯,自烴如 二氣甲烷、氣仿及氣苯,醚如乙醚、二異丙醚、第三丁基 甲基醚、二哼烷、茴香醚及四氫呋喃,腈如乙腈及丙腈, 醇如甲醇、乙醇、正丙醇、異丙醇、正丁醇及第三丁醇, 酮如丙酮及甲基乙基明,及二曱亞颯、二曱基甲酿胺、二 甲基乙醯胺、1,3-二甲基咪唑啶-2-酮及1,3-二甲基四氫_ 2(1 H)-嘧啶酮,特佳爲二氣甲烷、丙酮及二甲基甲醯胺。 亦可用所述之溶媒之混合物。 適宜之鹼一般爲無機化合物如鹼金屬及鹼土金屬氫氧化 物如LiOH、NaOH、KOH、Ca(0H)2,驗金屬及驗土金屬氧 化物如氧化鋰、氧化鈉、氧化鈣及氧化鎂,鹼金屬及鹼土 金屬氫化物如LiH、NaH、KH、CaH2,驗金屬胺基化物如 胺基化鋰、胺基化鈉及胺基化鉀及鹼金屬與鹼土金屬碳酸 鹽如K2C03、及CaC03及鹼金屬碳酸氫鹽如NaHC03,有機 金屬化合物,特別是鹼金屬烷基物如曱基鋰、丁基鋰及苯 基鋰、烷基鎂由化物如氣化甲基鎂及鹼金屬與鹼土金屬醇 鹽如甲醇鈉、乙醇鈉、乙醇鉀、第三丁醇鉀及二曱氧基鎂 ,另外,有機鹼例如三級胺如三甲胺、三乙胺、二異丙基 乙胺及N-甲基六氫ρ比喊、比咬、取代之,,比淀如可力丁、二 甲基吡啶及4-二甲胺基吡啶及二環胺。 -6- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公f ) 1^1 ii— n n In - j. I! 1 HI 1 I i— m m —^n . «3^ * 、言 , 潑 « ^ (請先閱讀背面之注意事項再填寫本頁)
II 經濟部中央標隼局員工消費合作社印製 A7 B7 五、發明説明(4 ) 檢一般以等莫耳量’以過量或若適當作爲溶媒使用。 反應物中加催化量之冠醚如18-冠-6或15-冠-5可能有利 〇 反應亦可以由驗金屬或鹼土金屬氫氧化物或鹼金屬或鹼 土金屬碳酸鹽於水中之溶液及有機相如由煙之兩相系統中 進行。所用之相轉移觸媒可爲南化銨及四氟硼酸鹽如氣化 节基二乙基接、溪化卞基三丁基按、氣化四丁基錄、漠化 十六基三甲基銨或四氟硼酸四丁基銨及由化燐如氣化四丁 基鳞或溴化四苯基燐。 對於反應首先以驗處理化合物Η及將所得之鹽與化合物 III反應爲有利的。 化合物II可以類似已知方法[參見J Chem. Soc 1946, 5]之 方法’將二氟乙酸醋VI與〇-坑基異脉vii之縮合而得。
F3C-C0-CH2-C02Rb + HN-C(NH2)-OR 式VI中之Rb爲C丨-C4_燒基’尤其是甲基或乙基。 反應習慣上於0C至120C ’較好2(TC至80°C,特別是溶 媒之滞點下進行。所用溶媒習用爲醇,尤其甲醇或乙醇。 式VII之0-烷基異脲習慣上以其鹽尤其是氫鹵化物(例如 鹽酸鹽及氫溴酸鹽)之形式使用。當使用鹽時,推薦於鹼 (例如鹼土金屬或鹼金屬醇鹽或氫氧化物如甲醇鈉、乙醇 鈉' 第二丁醇绅、NaOH、KOH或Ca(0H)2)之存在下進行 本紙張尺度適用中國國家標準(CNS > Α4規格(210Χ297公箱;) IJ-------—裝------ 訂 - - . (請先閱讀背面之注意事項再填寫本頁) 線 308589 五、發明説明(5 ) 反應。替代地,化合物!亦藉由將式IV之颯衍生物以本身 已知疋方法[參見 j. Med Chem. g (1984, 1621 ; CH-A 649 068]於鹼之存在下與式v之醇反應而得。
0 = :C—V——CH3 IV
•R
OR 0= :C—V一ch3 經濟部中央標準局員工消費合作社印製 式iv中之烷基,尤其是甲基。 適宜之鹼爲尤其是NaH、第三丁醇鉀及K2C〇3。 反應一般於惰性偶極非質子溶媒(尤其二甲亞颯、二甲 基甲酿胺或1,3-二甲基四氫-2(1 H)-嘧啶酮)中進行。 反應所須之式iv之颯衍生物自對應之硫化物νιπ藉由氧 化開始製得。
〇: C一Vch3
VIII -8- 本紙張尺度適用中國國家標隼(CNS ) A4規格(210X 297公釐) 五、發明説明( 6
I o=c—-V—-ch3 IV A7 B7
=u — och3 例如用過氧化氫於濃 氧化根據自文獻已知之方法進行 乙酸中[參見Chem. Pharm. Bull U (1978),183]或用次氣酸 鈉於水中[參見 J. Prakt. Chem_ 巧(1966), 165]。 式III之苄基衍生物其中V爲氧者爲自開始時所引用之文 獻中已知者。苄基衍生物II其中U爲N及V爲NH者記述於德 國專利DE-A 43 05 502中。 替代地,通式I中U爲N及V爲NH之化合物藉由對應之酯 (V=0)之胺解作用可得(參見 Houben-Weyl Vol. E5, p_ 983 ff_)
or 〇= :C-OCH3 R1, $ ch2〇 C= NOCH3 I 〇=C-NHCH3 cf3
II-------—裝-------訂-------: 線 I- .. (請先閱讀背面之注意事^再填寫本頁) 經濟部中央標準局員工消費合作杜印製 lb
Ic 此反應習慣上於〇°C至60°C,較佳地10°C至30°C下,於 惰性溶媒中進行。 曱胺可以氣體加入或以水溶液計量。 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(7 ) 適宜溶媒爲芳烴如甲苯、鄰-、間-及對二甲苯,卣烴如 二氣甲拔氣仿及氣苯,醚如乙鍵、二異丙鍵、第三丁基甲 基链、一 B号坑、四氫吱喃及菌香駿,醇如甲醇、乙醇、正 丙醇、異丙醇、正丁醇及第三丁醇,特佳地甲醇、甲苯及 四氫呋喃。亦可用所提溶媒之混合物。 於上式中所指示之符號之定義中,使用集合名詞,其一 般爲下列取代基之代表: .齒素:氟、氣、溴及碘; 霉基具1至6個碳原子之飽和、直鏈或分支烴基,如甲 基 '乙基、丙基' 1-甲基乙基、丁基、丨-甲基丙基、2·甲 基丙基、1,1-二甲基乙基、戊基、丨_甲基丁基、2_甲基丁 基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、 1,卜二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戍 基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、L2-二甲 基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁 基、3,3-二甲基丁基、乙基丁基、2·乙基丁基、112_三 曱基丙基、1,2,2-三曱基丙基、乙基-1-甲基丙基及〗_乙 基-2-甲基丙基; .庳娱》基··_具1至4個碳原子(如上述)之直鏈或分支燒基, 於此等基中氫原子可部分或完全由上述之由素原子取代, 例如CrC2-鹵烷基如氣甲基、二氣甲基、三氣甲基、氟甲 基、二氟甲基、三氟甲基、氣氟甲基、二氣氟甲基 '氯二 氟甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氣 乙基、2-氣-2-氟乙基、2-氣-2,2-二氟乙基、2,2-二氣-2-氟 _ -10- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X__297公釐j I H - I I In ^^1 i --8 1- 11- .^n HI HI f ^^1 --1-1 1^1 ^ f ' ! (請先閱讀背面之注意事項再填寫本頁) A7
經濟部中央標準局員工消費合作社印家 乙基、2,2,2-三氣乙基及五氟乙基; 具1至4個碳原子(如上述)之直鏈或分支烷基, 其經由戰原子(-〇_)結合於結構; 鱼具I至4個碳原子(如上述)之直鏈或分支由烷 基’其.纟ϋ由乳原子(·〇_)鍵結於結構。 有關彼等之生物活性,以那些其中尺爲C2_C5_烷基,尤其 是CrC4_燒基之化合物丨特佳。 另外較佳之化合物〗爲其中„爲〇或1,尤其是〇。 於η不爲0之情形,化合物丨中…具下列意義;氰基、氟、 氣、甲基、三氟甲基或甲氧基爲佳。 另外較佳之化合物丨爲其中一個Rl基爲鍵結於苯基環之3_ 、4 -或5 -位。 特別地’有關其用途,編列於下表中之化合物j爲佳。述 於表中之取代基之基,本身額外地認爲(分別爲其中彼等 被提及者之組合)是有關取代基之較佳具體實施例。 表1 式Ϊ中U爲CH及v爲〇之化合物(Ξ ia)及化合物之取代基 與R之组合相當於表Α之—列。 表2 式I中U爲:N及V爲〇之化合物(ξ ib)及化合物之取代基Rlr 與R之組合相當於表A中之一列。 表3 式I中U爲Ν及V爲ΝΗ之化合物(ξ ic)及化合物之取代基 尺、與艮之組合相當於表A中之一列。 -11- 本紙張又度適用中ϋ·ϋΤ^)Α4規格(2l0x297公缝) ^ - I裝------訂-----Μ線 f , ^ (請先閱讀背面之注意事項再填寫本頁) 308589 五、發明説明(9 ) A7
o=c — V— ch3
No. RXn R 01 Η ch3 02 Η CH2CH3 03 3-C1 CH2CH3 04 4-OCH3 CH2CH3 05 Η ch2ch2ch3 06 3-C1 ch2ch2ch3 07 Η CH(CH3)2 08 3-C1 CH(CH3)2 09 4-OCH3 CH(CH3)2 10 5-C(CH3>3 CH(CH3)2 11 Η ch2ch2ch2ch3 12 Η CH2CH(CH3)2 I 13 Η CH(CH3)CH2CH3 I (請先閲讀背面之注意事啰再填寫本頁) 經濟部中央標隼局員工消費合作社印製 根據本發明之式I化合物適宜控制昆蟲、蟎及線蟲類之 動物害蟲,特別是昆蟲,尤其是蟎。彼等可用爲作物保護 及衛生、貯存之材料保護及獸醫分脈中之殺眞菌劑及殺蟲 劑。 -12- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) 經濟部中央標孪局員工消費合作杜印製 A7 B7 五、發明説明(1Q) 有害昆蟲包括: 鱗翅目(Lepidoptera),例如,茶小捲葉蛾、小地老虎、 黃地老虎、Alabama argillacea、黎豆夜蛾、顏實巢蛾、γ 纹夜蛾、Cacoecia murinana、Capua reticulana、雲杉捲葉 蛾、玉米千樓、西方雲杉捲葉蛾、美洲黏蟲、稻縱捲嗅 、Crocidolomia binotalis,蘋果蠹蛾、歐洲松毛蟲、瓜野 螟、巨座玉米螟、埃及金鋼鑽、小玉米螟、Eupoecilia ambiguella、粒膚地老虎、李小食心蟲、Grapholitha molesta、棉鈴蟲、美洲於夜蛾、玉米穗夜蛾、菜填、 Hibernia defoliaria、美國白蛾、蘋果巢蛾、番祐蠢蛾、 西部櫟尺蠖、甜菜夜蛾、旋紋潛夜蛾、Lith〇c〇lletis blancardella、Lobesiabotrana、黃綠條螺、舞毒蛾、僧尼 毒蛾 '窄翅潛蛾、烟草天蛾、天幕毛蟲、甘藍夜蛾、 Mocis repanda ' 殘冬尺蝮、Orgyia pseudotsugata、歐洲玉 米螺、木槿捲葉蛾、Panolis flammea、紅铃蟲、 Phthorimaea operculella、Phyllocnistis citrella、大菜粉壤 、首猜綠葉蛾、Platynota stultana、小菜蛾、福花巢蛾、 Prays oleae、Prodenia sunia、黃條枯蟲、大豆夜蛾、松 梢捲葉蛾、Scrobipalpula absoluta、大填、葡萄長讀捲葉 蛾、草地枯蟲、Spodoptera littoralis、斜紋夜蛾、棉大捲 葉填、 Synanthedon myopaeformis、 Thaumatopoea pityocampa、櫟綠捲葉蛾、Trichoplusia ni、三化填、雲 杉小捲葉蛾、大峨樓、及麥蛾、Ephestia cautella、袋衣 蛾; -13- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) I.------3 I裝------ 訂 ------:線 气 . I (請先閱讀背面之注意事哼再填寫本頁) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(11 ) 輔翅目(Coleoptera),例如,具條 PP 甲、Agriotes obscurus、野棉象甲、韻果花象甲、Apion vorax、 Atomaria linearis、大松小囊、Cassida nebulosa、豆葉甲 、甘藍莢象甲' Ceuthorhynchus napi、甜菜脛甲、烟草 金針蟲、天門冬葉甲、Dendroctonus refipennis、長角葉 甲、Diabrotica 12-punctata、玉米根葉甲、墨西哥豆瓢蟲 、烟草 5兆甲、Eutinobothrus brasiliensis、Hylobius abietis 、埃及苜蓿象甲、埃及苜蓿葉象甲、Ips typographus、 Lema bilineata、Lema melanopus、馬龄薯甲蟲、甜菜金 針蟲、稻象甲、Melanotus communis、Meligethes aeneus 、Melolontha hippocastani、Melolontha melolontha、稻頁 泥蟲、Otiorrhynchus sulcatus、草毒根象甲、Phaedon cochleariae、庭園麗金龜、Phyllophaga sp.,Phyllotreta chrysocephala、蕪菁淡足跳甲、黃曲條跳甲、日本麗金 龜、Psylliodes napi、Scolytus intricatus、碗豆葉象甲、 及蚕豆象、Bruchus pisorum、Bruchus lentis、谷象、烟草 竊蠹、鋸(胸)谷盜、谷蠹、米象、赤擬谷盜、谷斑皮蠹、 Zabrotes subfasciatus ; 雙翅目(Diptera)昆蟲,例如墨西哥橘實蠅、地中海實 蠅、高染癭蚊、瓜實蠅、油橄欖實蠅、蕓苔莢癭蚊、 Delia coarctata、Delia radicum、大麥水繩、種繩、 Liriomyza sativae、Liriomyza trifolii、Mayetiola destructor 、Orseolia oryzae、瑞典(麥杆)繩、甜菜潛葉花繩、 Phorbia antiqua、Phorbia brassicae、Phorbia coarctata、櫻 -14- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公嫠) ί ί 1^1 m n I n ml 1^1 ^ϋ· --eJml n^i ^^^1 In ^ i _ .一 (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局貝工消費合作社印裝 A7 B7 五、發明説明(12) 桃實繩 ' 顏果實蠅、Tipula oleracea、歐洲大蚊、及 Aedes aegypti、Aedes vexans、五斑按蚊、Chrysomya bezziana、Chrysomya hominivorax、Chrysomya macellaria、 Cordylobia anthropophaga、五帶淡色庫蚊、黃腹廐繩、 大馬胃繩、Glossina morsitans、騷擾角繩、Haplodiplosis equestris、紋皮繩、Lucilia caprina、Lucilia cuprina、 Lucilia sericata、家繩、廐腐繩、半鼻蠅、Tabanus bovinus、Simulium damnosum ; 櫻翅目(Thysanoptera)例如,烟草褐薊馬、苜猜薊馬、 花薊馬、小麥皮薊馬、橘實莉馬、稻薊馬、Thrips palmi 、Thrips tabaci ; 膜翅目(Hymenoptera)之昆蟲,例如新疆菜葉蜂、Atta cephalotes、Atta sexdens、得克薩斯洲切菜蟻 '蘋果葉蜂 、阿根廷議、Iridomyrmex purpureus、廚蟻、火蛾、外引 紅火蟻、黑火蛾: 異翅亞目,例如春綠蝽、多毛長蝽、烟草黑斑盲蝽、 棉紅蜂、Dysdercus intermedius ' Eurygaster integriceps、 棉褐蜂、葉足緣蝽、豆莢盲、牧草盲*春(Lygus lineolaris) 、牧草盲蝽(Lygus pratensis)、稻綠蝽、甜菜擬綱蝽、 Solubea insularis、Thyanta perditor : 同翅目(Homoptera)之吸植物昆蟲,例如Acyrthosiphon onobrychis '疏豆虫牙、落葉松球虫牙、紅圓螃、Aphidula nasturtii、蚕豆*牙、棉对、蘋果*牙、馬鈐薯長鬚*牙、棉粉 風、薊短尾 *牙、甘藍虫牙、Dalbulus maidis、Dreyfusia -15- 本紙張尺度適用中國國家棟準(CNS ) A4規格(210X297公釐) n 1^1 I ^^^1 1^1 n nn ^^^1 n^i ^^^1 —.1 ^ i (請先閲讀背面之注意事項4填寫本頁) 經濟部中央標率局員工消費合作杜印製 A7 B7_ 五、發明説明(13) nordmannianae、Dreyfusia piceae、Dysaphis radicola、蚕 豆微葉蟬、蘋果綿蚜、稻灰飛虱麥長管蚜、大戟長管蚜 、Macrosiphon rosae、蚕豆修尾*牙、薔薇麥*牙、桃赤对 、櫻桃黑瘤額蚜、黑尾葉蟬、稻褐飛虱、蔗飛虱、薄荷 瘤額*牙、橘粉价、蘋木虱、Psylla piri、梨黃木虱、 Quadraspidiotus perniciosus ' 玉米經管 *牙、Saissetia oleae ' 麥二叉 4牙、Selenasidus articulatus、Sitobion avenae、 白背飛虱、橘二又蚜、結翅粉虱、溫室白粉虱、葡萄根 瘤*牙; 等翅目,例如 Calotermes flavicollis、Leucotermes flavipes 、 Macrotermes subhyalinus、 Odontotermes、 formosanus、 Reticulitermes lucifugus、Termes natalensis ; 直翅目(Orthoptera)昆蟲,例如歐洲縷姑、東亞飛*皇、 雙帶蚱蜢、赤腿蚱蜢、墨西哥蚱蜢、遷徙蚱蜢、落磯山 坤猛、紅翅虫皇、美洲蚱猛、Schistocerca peregrina、 Stauronotus maroccanus、Schistocerca gregaria,及家穩蟀 、東方緋蠊、德國小嫌、美洲大蠊; 蛛形綱例如草食性蜗如番祐葉剌皮癭蛾、Aculops pelekassi、顏刺癭虫禹、Brevipalpus phoenicis、苜裔苔虫高 、鶴耳橛東方葉蜗、得克薩斯州橘眞葉蛾、Eriophyes sheldoni、草地小爪蜗、蘋果紅蜘蛛、橘全爪絲、橘鋒虫某 、側多食跌線虫甚、Tarsonemus pallidus、朱砂葉虫某、 Tetranychus kanzawai、太平洋紅葉喊、棉紅物蛛、蜱如 美洲花蜱、Amblyomma variegatum、波斯隱喙蜱、具環 -16- 本紙張尺度適用中國國家梯準·( CNS ) Λ4規格(210X297公釐) ~ I-;-------—裝-----ί、1τ------A ~ - I (諳先閱讀背面之注意事^'再填寫本頁) 經濟部中央標準局員工消費合作社印製 308589 A7 B7 五、發明説明(14) 方頭蜱、Boophilus decoloratus、微小牛蜱、Dermacentor silvarum、Hyalomma truncatum、羊硬碑、Ixodes rubicundus 、Ornithodorus moubata、耳殘喙蜱、Rhipicephalus appendiculatus及 Rhipicephalus evertsi及動物寄生之蜗如 雞皮剌蟎、羊癢蟎、及疥蟎; 線蟲綱例如根結蟲癭線蟲,例如花生根結線蟲 (Meloidogyne hapla)、胡蘿蔔根結線蟲(Meloidogyne incognita)、棉花根線蟲,胞囊形成線蟲,例如Globodera pallida、Globodera rostochiensis、Heterodera avenae ' 大 豆線蟲、Heterodera schachtii,遷移性内寄生蟲及半内寄 生蟲線蟲,例如 Heliocotylenchus multicinctus ' Hirschmanniella oryzae、 Hoplolaimus spp., Pratylenchus brachyurus、Pratylenchus fallaax、根腐線蟲、Pratylenchus vulnus、 Radopholus similis、 Rotylenchus reniformis、 Scutellonema bradys、甚橘根結線蟲、莖及葉線蟲,例如 小麥粒線蟲、稻乾尖線蟲、Ditylenchus angustus、甘薯 莖線蟲,病毒載體例如Longidorus spp.,Trichodorus christei、Trichodorus viruliferus、Xiphinema index、Xiphinema mediterraneum ° 化合物I另外地適宜爲殺眞菌劑。 化合物I藉由抗廣範圍之植物病原眞菌特別是子囊菌及擔 子菌綱之顯著活性而區別。於一些情形,彼等對具系統活 性且可用爲葉及土壤殺眞菌劑。 彼等對於控制眞菌對於各種作物植物如小麥、裸麥、大 -17- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐〉 II-------- I裝-----it-------線 < - _ (請先閱讀背面之注意事孑再填寫本頁) Α7 Β7 經濟部中央標準局員工消費合作社印製 五、發明説明(15 ) 臀、橡樹 、一 …坑稱、葡萄 /樹及裝飾植物及蔬菜植物如黃瓜、豆類、及_及此 等植物之種子之多重性特別重要。 彼等尤其適宜控制下列植物病:穀類之麥類白粉病葫遼 之甜菜白粉病及赤豆白粉病,蘋果之蘋果白粉病、葡=之 葡萄白粉病、穀類之銹病 '棉及草之水稻苗立枯病、浐類 及甘藏之黑粉病、镇果之蘋果黑猩病、穀類之茄黑腐='、 小麥之小麥穎枯病、草莓及葡萄之甘薯灰霉僵腐病、花生 之花生褐斑病、小麥及大麥之Pseud〇cerc〇sp〇 herp〇tricholdes'稻之稻瘟病、馬鈐薯及番茄之馬鈴薯晚疫 =各種植物之枯萎病及黃萎病、„之葡萄霜霉病及蔬 菜與水果之黑斑病。 化合物I之應用藉由以殺眞菌上具活性量之活性化人物 處理眞菌或植物、種予、材料或待保護免受眞菌侵襲:地 。在被眞菌感染材料、植物或種子以前或以後進行施用。 彼等可轉化成習用之調配物如溶液、乳液、懸浮液撒 粉劑、散劑、糊劑及顆粒劑。應用形式依特定所要之用途 而定;於各情形中’應保證2_[(2_烷氧基_6 咬-4-基)氧亞甲基]苯基乙酸衍生物之細且均勾之分散哺 = 万?製備,例如藉由使用溶媒及/或載劑擴 ㈣.^要使用乳化劑及分散劑,若用水爲稀 釋劑料料他有_媒爲輔助料。供此目的之適宜之 輔二主爲··溶媒如芳系物(例如二甲苯)、氣化芳系物(例 如氣秦)、鏈垸烴(如石油館份)、醇(如甲醇丁醇卜嗣( H. — 11 n ^^1 1^1 ^^1 I id ^^1 1 I -II «II 11 Τ» —Lr I . • 0¾ i --錄 f - /, (請先閱讀背面之注意事if再填寫本頁) •18
A7 五、發明説明(16 經濟部中央標準局員工消費合作社印製 :nL、胺(如乙醇胺、二甲基甲酿胺)及水;載劑如 人’、' 碾物(如陶土、氧化鋁 '滑石、白堊)及研磨之 二..確物(如高度分散碎酸、秒酸鹽);⑧化劑如非離子及 :離子乳化劑(如聚氧乙烯脂肪醇醚、烷基磺酸酯及芳基續 酯)及分散劑如木質素_亞硫酸鹽廢液及甲基纖維素。 殺眞菌組合物—般含0.1至95,較佳地0.5至9 〇%重量 比之活性化合物。 、所4之作用%定,應用比例由每公頃〇 〇 1至2 之活性化合物。 · 方、種子之處理中,一般須要活性化合物之量由每公斤 子0001至01克’較佳地0.01至0.05克。 活性化合物可以原樣使用,以其調配物形式或自其製備 ,藉由噴霧 '霧化、撒粉、散播或澆水之使用形式,例 以可直接喷霧之溶液、粉末、懸浮液或分散液' 乳液、 刀散液、糊劑、撒粉組合物、散播組合或顆粒之形式使 。使用形式冗全依所要之用途而定;於各情形中,若可 彼等應保證根據本發明之活性化合物之最細之分散。 彼等可轉化成習用之調配物如溶液、乳液、懸浮液、 粉劑 '散劑、糊劑或顆粒。此使用形式依特別所要之用 而定;於各情形中,若可能其應保證活性化合物之最細 散。 以已知方式製備調配物,例如藉由溶媒及/或載劑擴凡 活性化合物’若須要用乳化劑及分散劑,且若用水爲稀釋 劑則亦可用有機溶媒爲輔助溶媒。 斤 種 如 油 用 能 撒 途 分 充 I:------ 1^------、玎------F ▲ 概 岸 (請先閲讀背面之注意事ΪΓ再填寫本頁) -19- 308589
五、發明説明(17 ) 經濟部中央標準局員工消費合作社印繁 供此目的用之適宜輔助劑主爲: '溶媒如芳系物(例如二甲苯)、氣化芳系物(如氣苯) '鏈烷烴(如石油餾份)、醇(如甲醇'丁醇)、酮( 如環己網)、胺(如乙醇胺)、二曱基甲酿胺及水; •載劑如研磨之天然礦物(如陶土、氧化鋁、滑石、 白堊)及研磨之合成礦物(如高度分散二氧化矽矽 酸鹽), -乳化劑如非離子及陰離子乳化劑(如聚氧乙烯脂肪 醇醚,嫁基續酸酯及芳基續酸酯)及 '分散劑如木質素-亞硫酸廢液及甲基纖維素。 適宜之界面活性物質爲芳系磺酸,例如木質磺酸、酚磺 酸、莕磺酸及二丁基莕酸及脂肪酸、烷基及烷芳基磺酸酯 '燒基、十二基酸及脂醇硫酸酯之鹼金屬、鹼土金屬及銨 鹽,及硫酸化十六、十七及十八醇及脂醇二醇醚之鹽,磺 化茶及其衍生物與甲搭之縮合產物、莕或莕磺酸與酚及甲 醛心縮合產物、聚氧乙烯辛基酚醚、乙氧基化異辛基-、 辛基-或壬基驗、烷基酚或三丁苯基聚二醇醚、烷芳基聚 醜醇、異十三基醇'脂醇氧化乙晞縮合物、乙氧基化蓖麻 油、聚氧乙晞或聚氧丙烯烷基醚、十二基醇聚二醇醚乙酸 鹽、山梨醇醋、木質素-亞硫酸廢液或甲基纖維素。 水性使用形式可自乳液濃縮物、分散液、糊劑、可潤濕 粉末或水可分散之顆粒藉由加水製備。爲製備乳液、糊劑 或油分散液’可將物質於水中使均勻化或溶於油或溶媒, 藉由潤濕劑、黏著劑、分散劑或乳劑。然而,由活性物質 -20- 本紙張又度通/JT國國家標準(CNS ) M規格(2mx297公着 -II - - ϋ - —f I - I I I - L—訂- ---T 線 (請先閲讀背面之注意事iF^填寫本頁) Α7
經濟部中央標準局員工消费合作社印裝 成潤=劑、㈣劑、分散劑或乳劑且可能地溶媒或 成<濃縮物亦可製備,其適合以水稀釋。 、·'且 入:劑散佈及撒粉組合物可藉由活性物質與固體載劑混 »或一起研磨而製備。
顆粒,例如經塗你,湯^啬日h I ^ 怖I /貝且均勻又顆粒,可藉由將活性 化合物結合於固體載劑而製備。 固體載劑爲礦土如矽膠、矽酸、矽酸鹽、滑石、陶土、 石灰石、石灰、白堊、紅玄武土、黃土、黏土、白雲石、 矽藻土、硫酸鈣及硫酸鎂、氧化鎂、研磨之合成物質、肥 料如硫酸銨、磷酸銨、硝酸銨、脲及植物產物如穀粉、樹 皮粉、木粉及堅果殼粉、纖維素粉或其他固體載劑。於即 刻可用之製劑中之活性化合物濃度可在相當寬之範圍内變 化。 —般地,組合物含0.0001至95%重量比之活性化合物。 含大於95。/。重量比之活性化合物之調配物可高度成功地 應用於超低體積方法(ULV),甚至可無添加物地使用活性 化合物。 供對抗動物害蟲用,調配物含0 0001至10%重量比,較好 〇.〇 1至1 %重量比之活性化合物爲適宜的。 活性化合物一般以90%至100%純,較好95%至100%(根據 NMR光譜)之純度使用。 此等製劑之實例爲: I. 90份重量之根據本發明化合物1及1〇份重量之N-甲基-α -吡咯啶酮之溶液,其適宜以很小液滴之形式應用 -21 本紙張尺度適用中國國家標準(CNS ) A4規格(2丨0X297公嫠) - 1^1 ^^1 I I ....... —J I - - - - —i 1 1^— ILT -1 In I ^^1 4 (請先閲讀背面之注意事碩再填寫本頁j A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明(19 ) Π 20份重量之根據本發明化合物I於80份重量之烷基化 苯’〗〇份重量之8至1〇莫耳環氧乙烷與丨莫耳油酸N_ 乙醇醯胺之加成產物,5份重量之十二基苯磺酸鈣,5 份重量之40莫耳環氧乙烷與1莫耳蓖麻油之加成產物 之混合物中之溶液;藉將所調配物細分散於水中而得 分散液。 20份重量之根據本發明化合物I於4〇份重量之環己酮 ,30份重量之異丁醇’ 2〇份重量之7莫耳環氧乙烷與i 莫耳異辛基酚之加成產物及10份重量之4〇莫耳氧乙燒 與1莫耳蕙麻油之加成產物之混合物中之溶液;藉將 此碉配物細分散於水中得分散液。 IV. 20份重量之根據本發明化合物丨於25份重量之壤己綱, 65份重量之沸點由21〇至28(rc之石油餾份及】〇份重量 之40莫耳環氧乙烷與1莫耳蓖麻油之加成產物之混合 物中之水分散液;藉將此調配物細分散於水中得分散 液。 V. 20份重量之根據本發明化合物I,3份重量之二異丁 基萘《 -磺酸鈉,丨7份重量之木質素磺鈉(得自亞硫 酸廢液)及60份重量之矽膠粉之於錘磨機中研磨之混 合物’藉將此混合物細分散於水中得喷霧液; VI. 3份重量之根據本發明化合物I及9 7份重量之細分陶 土之緊密混合物;此撒粉組合物含3 %重量比之活性 化合物; H - - 1 n^i HI n nn -1- I ml m m L—w,一oiIn In 1^1 * (請先閱讀背面之注意事項再填寫本頁) -22- 經濟部中央標準局員工消費合作社印製 A7 ___________B7 五、發明说明(20) VII. 30份重量之根據本發明化合物I,92份重量之梦膠粉 及8份重量之已噴霧於此矽膠表面之液體石蟻之緊密 混合物;此製劑提供活性化合物良好之黏附; VIII. 40份重量之根據本發明化合物丨,1〇份重量比之酚磺 酸/脲/甲醛縮合物之鈉鹽,2份重量之矽膠及48份重量 之水之穩定水分散液,其可進一步稀釋; IX. 2份重量之根據本發明之化合物I,2份重量之十二基 苯績酸鈣’ 8份重量之脂醇聚二醇醚,2份重量之酚 續酸鈉/脲/甲搭縮合物及68份重量之鏈烷烴系礦油之 穩定之油分散液; X· 1〇份重量之根據本發明化合物I,4份重量之二異丁 基莕α -續酸納,20份重量之得自亞硫酸廢液之木質 素磺酸鈉,38份重量之矽膠及38份重量之陶土之於錘 磨機中研磨之混合物。藉由將此混合物細分散於 10,000份重量之水中,得噴霧混合物含〇」%重量比之 活性化合物。化合物丨之應用藉由以活性量之活性化 β物處理害蟲或有害之眞菌或種子、植物、材料或待 保護免除害蟲或有害之眞菌之土地。 彼等在材料、植物或種子受有害眞菌感染之前或之後應 用。 依所須之作用類型而定,應用比例由每公頃〇 02至3公斤 之活性化合物;較佳地0· 1至1公斤。 於種子處理中,一般須每公斤種子由0.001至50克,較好 爲〇.〇1至10克之活性化合物之量。 _______ -23- 本紙張尺度賴( CNS )从驗(2!Gx297公廣) '-- - --- --. - n - I (請先閱讀背面之注意事If再填寫本頁) 、^ 線 五、發明説明(21) 供户外條件下控制害蟲或有害之眞菌用 應用比例爲〇.〇2至10,較佳地〇丨至2 〇公 化广物< 合物。 丨,A頃之活性化 化合物!可單用或與除草劑或殺眞菌劑併用, 之:物保護劑—起混合使用’例如與生長調節劑或與 害蟲或細菌用之劑混合。亦關注與用來消除營養及稀^ 素缺乏用之肥料或礦鹽之相容性^ 儿 作物保護劑及肥料可以】:難1G:1之重量比加至报據本 發明之組合物,若適字甚至於臨用前加人(桶中混幻與殺 眞菌劑或殺昆蟲劑混合後,於許多情形可得殺眞菌之作 範圍之增加。 根據本發明之化合物可一起應用之下列之殺眞菌劑,用 來證明組合可能性而非對彼等之限制: 經濟部中央標準局員工消費合作社印製 硫、一硫代胺基甲酸酯及其衍生物,如二〒基二硫代 胺基甲酸鐵、二甲基二硫代胺基甲酸鋅、伸乙基雙二硫 代胺基甲酸鋅、伸乙基雙二硫代胺基甲酸錳、乙二胺雙 二硫代胺基甲酸鋅、二硫化四甲基秋蘭姆、N,N_伸乙基 雙二硫代 '胺基甲酸鋅之氨錯合物、N,N,_伸丙基雙二硫 代胺基甲鋅之氨錯合物。n,n,-伸丙基雙二硫代胺基甲酸 鋅、Ν,Ν·-聚伸丙基-雙(硫代胺甲醯基)化二硫;硝基衍生 物如巴豆酸二硝基(1-甲基庚基)_苯酯、3,3_二甲基丙烯酸 2_第二丁基-4,6-二硝基苯酯、異丙基碳酸2-第二丁基-4,6-二硝苯醋、5-硝基異酞酸二異丙酯; 雜環物質,如2-十七基-2-咪唑啉乙酸酯、2,4-二氣-6-( _ -24- 本紙張尺度適用中國國家標準(CNs ) A4規格(210>< 297公釐) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(22 ) 鄰氣笨胺基)-S-三畊、酞醯亞胺基膦酸基代酸〇,〇-二乙酯 、5·胺基_[雙_(二甲胺基)膦基]_3_苯基_124,-三唑、 2,3 -—氛基-1,4 -二硫惠酿、2-硫-1,3-二ρ 塞茂並-/? -[4,5-b]峻 p号啉、Ν,Ν-伸乙基雙硫代胺甲酸鋅之氨錯合物、Ν,Ν1-伸 丙基雙二硫代胺基甲酸鋅之氨錯合物、Ν,Ν,-伸丙基雙二 硫代胺基甲酸鋅、Ν,Ν'-聚伸丙基雙(硫代胺甲醯基)化二 硫;硝基衍生物如巴豆酸二硝基(1 -甲基庚基)苯酯、3,3-二甲基丙烯酸2·第二丁基-4,6-二硝苯酯、異苯基碳酸2-第 二丁基-4,6-二硝苯酯、5-硝基異酞酸二異丙酯; 雜環物質,如2-十七基-2-咪唑啉乙酸酯、2,4-二氣-6-( 鄰-氣苯胺基)-s-三畊、酞醯亞胺基膦酸基硫代酸0,0-二乙 酯、5-胺基-1-々-[雙-(二甲胺基)-膦基]-3-苯基-1,2,4-三唑 、2,3-二氰基-1,4-二硫代蒽醌、2-硫-1,3-二嘧茂並-卢-[4,5-b]喹咩啉、1-(丁基胺甲醯基)-2-苯並咪唑胺基甲酸甲 酯、2-甲氧羰胺基苯並咪唑、2-(呋喃-2-基)苯並咪唑、2-( 口塞唑-4-基)苯並咪唑、N-(l,1,2,2-四氣乙硫基)四氫酞醯亞 胺、N -三氣甲硫基四氫酞醯亞胺、N -三氣甲硫基酞醯亞 胺、N-二氣氟甲硫基-Ν·,Ν·-二曱基-N-苯基磺胺、5-乙氧 基-3-三氣甲基-1,2,3-嘧二唑、2-氰硫甲硫基苯並嘧唑、 1,4-二氣-2,5-二曱氧基苯、4-(2-氣苯基亞胼基)-3-甲基-5-異崎唑酮、2-硫吡啶1-化氧、8-羥基喹啉或其銅鹽、2,3-二氫-5-羧醯苯胺基-6-曱基-1,4-崎沙辛(〇父3比丨丨11)、2,3-二 氫-5-羧醯苯胺基-6-甲基-1,4-哼沙辛4,4-化二氧、2-甲基-5,6-二氧-4H-吡喃-3-羧醯苯胺、2-甲基呋喃-3-羧醯苯胺、 -25- 本紙張尺度適用中國國家標準(CNS ) A4規格(2丨0X297公釐) (請先閱讀背面之注意事ϊί再填寫本頁) -裝. 、ys S〇S589 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明(23) 2,5-二甲基吱喃-3-羧酿苯胺、2,4,5_三甲基呋喃_3•羧醯苯 胺、N-環己基-2,5-二甲基呋喃_3_幾醯胺、队環己基A·甲 氧基-2,5-二甲基呋喃·3_羧醯胺、2_甲基苯醯苯胺、2_碘苯 醯苯胺、Ν-甲醯基·Ν·嗎啉_2 2 2_三氣乙基縮醛 '六氫吡 畊-I,4-二基-雙(1-(2,2,2-三氣乙基))甲醯胺、^(34-二氣苯 胺基)-1-甲醯胺基-2,2,2-三氣乙烷、2,6-二甲基_N_十三基 嗎琳或其鹽、2,6-—曱基_n-環十二基嗎〇林或其鹽、n-[3-( 對第二丁苯基)-2-甲基-丙基]•順_2,6-二甲基嗎琳、n-[3-( 對弟二丁基幕基)-2-甲基丙基]六氫u比唆、ι_[2_(2,4_二氣苯 基)-4-乙基-1,3-二氧雜戊環_2_基乙基]_iH-l,2,4-三唑、1-[2-(2,4-二氣苯基)-4-正丙基-1,3-二氧雜戍環·2_基-乙基]_ 1Η-1,2,4-三唑、Ν-(正丙基)_Ν_(2,4,6-三氣苯氧乙基)·Ν,_咪 唑基脲、1-(4-氣苯氧基)_3,3-二甲基-1-(1Η-1,2,4-三唑-1-基) -2-丁酮、1-(4-氣苯氧基)·3,3-二甲基-1-(1Η-1,2,4-三唑-1-基)-2-丁醇、α -(2-氣苯基-(4-氣苯基)-5-喊咬甲醇、5-丁基-2-二甲胺基-4-羥基-6-甲基嘧啶、雙-(對氣苯基)_3·吡 啶甲醇、1,2-雙(3-乙氧羰基-2-硫脲基)苯、1,2-雙(3-甲氧 羰基-2-硫脲基)苯, 及各種殺眞菌劑如十二基胍乙酸酯、3-[3-(3,5-二甲基-2-氧環己基)-2-羥乙基]戊二醯亞胺、六氣苯、DL-N-(2,6-二甲苯基)-N-2-吱喃酿基丙胺酸甲醋、DL-N-(2,6-二甲苯 基)-Ν-(2·-曱氧乙醯基)丙胺酸甲酯、N-(2,6-二甲苯基)-N-氣乙醯基-D,L-2-胺基丁内酯、DL-N-(2,6-二甲苯基)-N-(苯 乙醯基)丙胺酸甲酯、5-甲基-5-乙烯基-3-(3,5-二氣苯基)- -26- 本纸張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) (請先閲讀背面之注意事ir再填寫本頁) .裝· 訂 線 經濟部中央橾準局員工消費合作杜印製 A7 B7 五、發明説明(24) 2.4- 二氧_1,3_哼唑啶、3-(3,5-二氣苯基)_5_甲基-5-甲氧甲 基-1,3-哼唑啶-2,4-二酮、3-(3,5-二氣苯基)-1-異丙基胺甲 酿基海因、N-(3,5-二氣苯基二甲基環丙烷二羧 醯亞胺、2-氰基-N-乙基胺羰基_2_甲氧亞胺基乙醯胺、卜 [2(2,4-二氣苯基)戊基]-1H-1,2,4-三唑、2,4-二氟 _ a -(1H- 1.2.4- 三唑基-1-甲基)二笨甲基醇、!^_(3_26_二硝基_4_三氟 甲苯基)-5-三氟甲基-3-氣-2-胺基吡啶、丨_((雙(4_氟苯基)甲 矽烷基)曱基)-1Η-1,2,4-三唑。 合成實例 用下面合成實例中所提供之方法,以適當修飾之起始 化合物或中間物得另外之化合物I。如此所得之化合物列 於下表中並列物理數據。 實例1 2 -異丙氧基-6-三氟甲基-4-幾基响淀 將465克之30。/。強度之甲醇鈉甲醇溶液於室溫滴加至 357_8克0-異丙基異脲鹽酸鹽(或氣化〇_異丙基錁)於9〇6毫 升無水乙醇中之溶液。另10分後,將475 2克三氟乙醯基 乙酸乙醋滴加至此混合物稍有放熱反應。於迴流下加熱 12小時混合物於旋轉蒸發器中濃縮,殘留物溶於1升水中 。以HC1使水相爲弱酸性;再以甲基第三丁基醚抽。合併 之醚相以水洗’於Nap。4上乾燥,最後濃縮至乾。殘留 物與石油醚攪拌,以吸氣過濾並乾燥。 得294.5克標題化合物爲無色晶體。
M.p. 126-127〇C -27 本紙張尺度適用中國國家標準(CNS〉A4規格(210X297公釐) — i — n n —訂 L / (請先閱讀背面之注意事tr再填寫本頁) 第84112144號專利申請案 中文說明書修正頁(86年1月) + Λ «修.止 福充; •J · 1 _丨丨"丨 卷 ___ 五、發明説明(25 ) iH-NMRCCDCl〗,β 以 ppm表示): 1.4 (6H) ; 5.9 (1H) ; 6.5 (1H) ; 12.2 (1H) 實例2 3-曱氧基-2-[2-(2-甲確醯基-6-三氟曱基嘧淀-4-基氧甲基)笨 基]丙缔酸甲酯(表1.04) 將0.15克鎢酸二納‘21^2〇加至3_9克3-甲氧基-2-[2-(2-甲 硫基-6_三氟甲基嘧啶-4-基氧甲基)苯基]丙烯酸甲酯於19毫 升冰乙酸中之懸浮液,並於20-30°C下慢慢滴加2.8毫升 30%強度之H2〇2水溶液。混合物於1小時内澄清,再於室 溫攪拌另12小時。逐步處理將其例於1 〇〇毫升冰水上,約 3 0分後倒去上清液,留下之黏性固體溶於乙酸乙酯。有機 相以水洗,於Na2S04上乾燥,最後濃縮。留下4 〇克標題 化合物爲淡黃色油。 h-NMRCCDCl〗,β 以 ppm表示): 3.3 (3H) : 3.65 (3H) : 3.85 (3H) ; 5.5 (2H) ; 7.15 (1H) ; Ί.1 (1H) ; 7.4 (2H) : 7.55 (1H) ; 7.6 (1H) 表2 cf3 (請先閲讀背面之注意事項-#填寫本頁) -° 經濟部中央標準局員工消費合作社印製 N OR No. R M.p. [°C] 11.01 ch3 142-143 11.02 ch2ch3 102-106 Π.03 CH(CH3)2 126-127
II • 28· 本纸張尺度適用中國國家標孪(CNS ) A4規格(2丨0X297公釐) A7 B7 經濟部中央標準局負工消費合作社印製 五、發明説明(26 ) 實例3 3-甲氧基-2-[2-(2-異丙氧基_6_三氟甲基嘧啶_4_基氧甲基)苯 基]丙烯酸甲酯(1.03) 自實例1製備羥基嘧啶之鈉鹽,將222克羥基化合物溶於 855毫升乙醇並滴加至56克KOH於855毫升乙醇中之溶液。 於迴流下加熱3小時後,濃縮混合物,殘留物溶於2升N N_ 二甲基甲醯胺。將280克3-甲氧基-2-[2·溴甲苯基]丙烯酸甲 酯加至此鈉鹽溶液’再將其於60。(:攪拌丨2小時。逐步處理 將其倒於冰水上並再以甲基第三丁基醚抽。合併之醚相以 水洗,於Na2S04上乾燥,最後濃縮。爲除去^烷基化之副 產物,將殘留物溶於1升甲醇中並以250毫升水處理。以吸 氣濾下結晶性沈澱,以石油醚洗並乾燥。得2〗丨克標題化 合物。
M.p. 107°C ^-NMR (CDC13 ’(ί 以 ppm表示): 1_4 (6H) ; 3.7 (3H) ; 3.8 (3H) ; 5.3 (1H) ; 5.35 (2H) ; 6.65 (1H) ; 7.2 (1H) ; 7.4 (2H) ; 7.5 (1H) ; 7.55 (1H) 實例4 2 -甲乳亞胺基-2-[3-氣- 2-(2-異丙氧基-6-三氟甲基w密咬-4-基 氧甲基)苯基]乙酸甲酯(1.08) 將3.3克2-異丙氧基-4-輕基-6-三氟甲基喊淀及2.4克碳酸 鉀於室溫(約25°C )於100毫升二甲基甲醯胺中攪拌30分,混 合物再於1小時之過程中以4.8克2-甲氧亞胺基-2-[2-溴甲基 -29- 本紙張尺度適用中國國家標準(CNS ) A4規格(21〇X 297公釐) 1. -- - 1 I I n i I (請先閲讀背面之注意事可再填寫本頁) 、-0 A7 B7 五、發明説明(27)
-3-氣苯基]乙酸甲酯於30毫升二甲基曱醯胺中之溶液滴加 處理。於室溫另8小時後,反應混合物加至冰水,用第三 丁基曱基醚抽產物。合併之醚相乾燥、濃縮。如此所得之 粗產物以層析法(矽膠/甲苯)純化。得4.2克標題化合物。 M.p. 106-108〇C 【H-NMR (CDC13 ’ 以 ppm表示): 1.4 (6H) ; 3.85 (3H) ; 4.0 (3H) ; 5.35 (1H) : 5.45 (1H) ; 6.6 (1H) ; 7.1 (1H) ; 7.4 (1H) ; 7.55 (1H) 實例5 2-曱氧亞胺基-2-[3-氣-2-(2-異丙氧基-6-三氟曱基嘧啶_4-基 氧甲基)苯基]-N-甲基乙醯胺(1.11) 將2.0克之實例4甲酯及70毫升四氫呋喃之混合物以2毫升 40%強度之曱胺水溶液處理。室溫(約25°C)下8小時後,於 反應混合物中加100毫升第三丁基甲基醚。如此所得之混 合物以2 0 %強度之檸檬酸洗3次並以水洗3次。乾燥並濃縮 有機相。所得粗產物以層析法[矽膠/甲苯:乙酸乙酯(9: j)] 純化。得1 · 0克標题化合物。
M.p. 116-118〇C 經濟部中央標準局員工消費合作杜印製 (請先閲讀背面之注意事項再填寫本頁) 【H-NMR (CDC13,β 以 ppm表示): 14 (6H); 2.95 (3H) ; 3.9 (3H) ; 5.35 (1H) ; 5.45 (1H); 6.6 (1H) ; 6.8 (NH) ; 7.1 (1H) ; 7.35 (1H) ; 7.5 (1H) 本紙張尺度遑用中國國家橾準(CNS ) M規格(urn97公釐
7 B A7 經濟部中央標準局員工消費合作社印製 五 、發明説明(28) 表1 Rln-CX 工 丁 CH20 N OR C=U— OCH3 1 o=c—V—ch3 No. U V R 物理數據IM.P. (°c>, IR (ca-i), iH-MMR (ppm)] I.01 CH 0 H ch3 3.65 (3H); 3.75 (3H); 4.0 (3H); 5.4 (2H); 6.65 (1H); 7.1-7.6 (5H) 1.02 CH 0 H ch2ch3 66-68 1.03 CH 0 H CH(CH3)2 107 1.04 CH 0 3-C1 CH(CH3)2 1.4 (6H); 3.7 (3H)? 3.85 (3H); 5·35 (1H); 5.5 (2H) Ko. U V R 物理數據丨Μ·|>. <°C>, IR (cm-1), 1H-NMR (ppm)] 1.05 N 0 H ch3 65-72 1.06 N - 〇 H CH2CH3 72-75 1.07 N 0 H CH(CH3)2 84-88 1.08 N 0 3-Cl ch(ch3)2 106-108 1.09 N NH H CH2CH3 88-90 1.10 N NH H CH(CH3)2 86—88 1.11 N NH 3 - Cl CH(CH3)2 116-118 對抗動物害蟲之作用之實例 藉由下列實驗可顯示通式I化合物對抗動物害蟲之作用: 製備活性化合物爲: a) 於丙酮中之0· 1 %強度之溶液或 b) 於70%重量比之環己酮,20%重量比之Nekanil® LN -31 - --^-------^ |裝------^訂l·----〆 線 (請先閱讀背面之注意事啰再填寫本頁) 本紙張尺度適用中國國家標準(CNS ) A4規格(210Χ 297公釐) 經濟部中央標隼局員工消費合作杜印製 308589 A7 B7 五、發明説明(29 ) (Lutensol® AP6,具基於乙氧基化之燒驗之乳化劑 及分散劑作用之潤濕劑)及1 0%重量比之Emulphor® EL(Emulan® EL,基於乙氧基化之脂醇之乳化劑) 之混合物中之10°/。強度之乳液。 並於a)之情形以丙酮,於b)之情形以水適當地稀釋成所 須之濃度。 於實驗之結束後,測定化合物產生與未經處理之對照實 驗比較仍具80-100%抑制或死亡率之最低濃度(作用閾或最 小濃度)。 紅缺I蛛虫某(Tetranychus telarius),接觸作用 顯示第二對成長葉之經嚴重感染之盆栽矮豆以水性活性 製劑處理。於溫室中5日後,藉由雙眼顯微鏡測定控制之 成功。於此試驗中,化合物1.01-1.07及I.09-1.11顯示2至400 ppm之作用閾。 黑尾葉蟬(Nephotettix cincticeps),接觸作用 以水性活性化合物製劑處理圓形濾器,再令5隻長大之 葉彈佔有。24小時後評估死亡率。 於此試驗中,化合物1.07及1.08顯示0.4毫克之作用閾。 對有害之眞菌之作用實例。 藉由下面實驗可顯示通式I化合物之殺眞菌之作用: 將活性化合物製備爲於70%重量比之環己酮、20%重量 比之Nekanil® LN (Lutensol® AP6,具基於乙氧基化之燒酴之 乳化劑及分散劑作用之潤濕劑)及10%重量比之Emulphor® EL (Emulan® EL,基於乙氧基化之脂醇之乳化劑)之混合物 _-32-_ 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) --------.—良------Γ T L_____象 (請先閲讀背面之注意事if再填寫本頁) 經濟部中央標準局員工消費合作社印聚 A7 __B7 五、發明説明(30 ) 中之20%強度之乳液,並依所須濃度以水稀釋。 所用之比較化合物爲活性化合物A(實例編號25,EP-A 407 872之表 I)。 對葡萄生單軸黴(Vine Peronospora)之作用 盆栽之葡萄(變種:Miiller Thurgau)以活性化合物製劑噴至 滴濕。8日後,植物以眞菌葡萄生單軸黴之游動孢子懸浮 液噴植物並維持於20-30°C,高大氣濕度下5天,評估以前 ’再將植物維持於高大氣濕、度下16小時 以目視進行評估 〇 於此試驗中以250 ppm之根據本發明之化合物1.01-1.〇7、 I_ 1 〇及I. Π處理之植物顯示5%以下之侵襲,而以相同量之 已知活性化合物A處理之植物被侵襲至25%。未經處理(對 照組)之植物被侵襲至75%。 對稻瘟病(Rice blast)之作用 將稻苗(變種:台農(Tai Nong)67以活性化合物製劑喷至滴 濕。24小時後,植物以眞菌稻瘟菌之孢子水懸浮液喷並維 持於相對大氣濕度95-99%、22-24°C下6天。以目視進行評 估。 於此試驗中,植物以250 ppm之根據本發明化合物1.01、 Ι·〇2、Ι·〇4、1.064 〇8、Ι·1〇及 1.11處理,顯示 25%以下之侵 襲’而以同量之已知活性化合物Α處理之植物被侵襲至 6〇% °未處理(對照組)之植物被侵襲至85 %。 33- 丰雄尺度適财酬家縣(CNS > M規格(21GX297公瘦) {請先閲讀背面之注意事啰再填寫本頁} ] —裂 卜訂'
Claims (1)
- 44號專利申請案 六、申請專利範圍 S3S 氧基―6-…基…-基)… R1, CF3Jj\ I ch2。’ n \〇r C=u—OCH, 0== c-V- •ck3 經濟部中央標準局員工消費合作社印裝 式中標記及取代基具下面之意義: U 爲CH或N ; V 爲0或NH ; R 爲(^-(:6-烷基; Rl 爲鹵素、crc4-烷基、crc4-烷氧基; n 爲ο或1至2之整數,若η値大於1,則Rl基可爲不 同。 2.根據申請專利範圍第1項之式I化合物,其中^爲CH& v 爲0 3 3·根據申請專利範圍第1項之式I化合物,其中U爲N及v爲0。 4·根據申請專利範圍第1項之式ϊ化合物’其中U爲N&v爲 ΝΗ 〇 5·—種製備根據申請專利範圍第1項之式I化合物之方法, ^ I裝--------訂I-----1 線 (請先閲讀背面之注意事項再填寫本頁) 41772.DOC 本紙浪尺度適用中國國家標準(CNS ) Μ現格(210Χ297公釐)D8 其包括將式II之嘧啶-4-醇 cf3N /入 KO N OR II 以本身已知之方法,於楕性有機溶媒中,於鹼存在下與 式III之苄基衍生物反應 R1,CH2X C=u-OCH-) I - 〇== c — v— ςπ3 III (請先閲讀背面之注意Ϋ項再填寫本頁) -a 經濟部中央標準局貝工消费合作社印裝 式中X爲親核性可取代之游離基。 6.—種製備根據申請專利範圍第丨項之式〖化合物之方法 其中將式IV之域衍生物〇= C— V— CH3 IV 式中尺3爲crC4_淀基,於絵存在下,與式v之醇反應 2- 41772.DOC 本紙張尺度遑用中國國家標準(CNS ) A4規格(210X297公釐) 申請專利範圍 . 1Kpk AS 一样 d D8 a- HO-R 7. —種式II之嘧啶-4-醇 V cf3HO N 〇R II 其中尺爲(^-0:6-烷基= 8. 根據申請專利範圍第7項中所述之式II之嘧啶-4-醇 係用爲中間物。 9. 一種式I V之颯衍生物 其 R1,IV 經濟部中央標準局爲工消費合作社印裝 C—U—〇ch3 I 0—C—V— ch3 式中標記及取代基具下面之意義: U 爲C Η或N ; V 爲0或ΝΗ ; ~ R1 爲鹵素、CVCV烷基、Crh-烷氧基; η 爲0或1至2之整數,若η値大於1,則R1基可爲不 41772.DOC -3- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) i^i —^HK vn fl^i n^f ml Jw m I n mr 0 一 ,---^. ^^—flc I m^i I (請先閲讀背面之注意事項再填寫本頁) ""Γ1"1™""*-.丨 _ _丨···、!^丨 |_ A 8 B8 ;7C8 p D8 . v _9告伞 ' «HIM 、申請專利範圍 同;且 #爲Crc4-烷基。 .根據申請專利範圍第9項之式IV之戚衍生物,其係用爲φ 間物3 T μ種適且控制動物害蟲或有害之眞菌之組合物,其含固 随或液體載劑及根據申請專利範圍第丨項之式丨化合物。 12.種控制動物害蟲或有害之眞菌之方法,其包括以有效 量 < 根據申請專利範圍第1項之式I化合物處理害蟲或有 害疋眞菌或待保護之材科、植物、土壤或種子。 13·根據申請專利範圍第1项之式1化合物’ Λ係用來供製備 適S控制動物害蟲或有害之眞菌之組合物。 R根據巾請專利範圍第1項之式1化合物,其係用於供控制 動物害蟲或有害之眞菌。 --^ -裝-- (請先閲讀背面之注意事項再填寫本頁) 银 經濟部中央揉準局負工消費合作社印製 41772.DOC - 4 - 本紙伕尺度逋用中國國家標準(CNS ) Α4規格(210X297公釐)第八四一^一二一四四號專利申請案 中文補充説明書(八十五年九月)_No. U V R 物理數_ Imp (吒);1!!-!^ (ppm)] 1.12 CH 〇 4-OCH3 CH2CH3 98 1.13 CH 〇 5-C(CH3)2 CH2CB3 1,3 (9H); 1,4 (3H)·; 3,65 (3H); 3,8 (3H); 4,45 (2H); 5,3 (2H); 6,65 (1H); 7,2 (1H); 7,4 (2H); 7,55 (1H)
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DE102007045922A1 (de) * | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
US20110124588A1 (en) * | 2008-05-07 | 2011-05-26 | Bayer Cropscience Ag | Synergistic active ingredient combinations |
EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
CN101875639B (zh) * | 2009-04-29 | 2012-07-25 | 中国中化股份有限公司 | 取代嘧啶醚类化合物及其应用 |
CN101906075B (zh) * | 2009-06-05 | 2012-11-07 | 中国中化股份有限公司 | 含取代苯胺基嘧啶基团的e-型苯基丙烯酸酯类化合物及其应用 |
EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
CN103563904B (zh) * | 2013-11-11 | 2015-12-02 | 陕西农心作物科技有限公司 | 一种含嘧螨胺和吡螨胺的杀螨组合物 |
CN108314656B (zh) | 2018-02-27 | 2020-10-27 | 浙江工业大学 | 不饱和烃嘧啶硫醚类化合物及其制备方法与应用 |
CN114605386B (zh) * | 2022-04-11 | 2023-12-12 | 青岛科技大学 | 一种含氟嘧啶硫醚芳香酯类杀虫杀螨剂 |
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NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
DE3623921A1 (de) * | 1986-07-16 | 1988-01-21 | Basf Ag | Oximether und diese enthaltende fungizide |
GB8617648D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
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EP0270252A3 (en) * | 1986-11-11 | 1990-04-04 | Imperial Chemical Industries Plc | Derivatives of propenoic acids used in agriculture |
DE3875748T3 (de) * | 1987-02-09 | 2000-08-31 | Zeneca Ltd., London | Fungizide |
YU47288B (sh) * | 1987-07-11 | 1995-01-31 | Schering Agrochemicals Limited | Akrilatni fungicidi i postupak za njihovo dobijanje |
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DE3823991A1 (de) * | 1988-07-15 | 1990-02-15 | Basf Ag | Heterocyclisch substituierte (alpha)-aryl-acrylsaeureester und fungizide, die diese verbindungen enthalten |
DE3835028A1 (de) * | 1988-10-14 | 1990-04-19 | Basf Ag | Oximether-derivate, verfahren zu ihrer herstellung und diese enthaltende fungizide |
NL8802710A (nl) * | 1988-11-04 | 1990-06-01 | Tno | Werkwijze voor het bepalen van een enzym en daarvoor geschikte kit en stof. |
DE3923068A1 (de) * | 1989-07-13 | 1991-01-24 | Basf Ag | Verfahren zur bekaempfung von schaedlingen mittels substituierter pyrimidine |
DE4030038A1 (de) * | 1990-09-22 | 1992-03-26 | Basf Ag | Ortho-substituierte phenylessigsaeureamide |
DE4116090A1 (de) * | 1991-05-17 | 1992-11-19 | Basf Ag | (alpha)-phenylacrylsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen und schadpilzen |
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