CN1049894C - 取代的-[1,4]-二噁烯并-[2,3-f]-苯并咪唑衍生物和制备方法及含有该化合物的农药 - Google Patents
取代的-[1,4]-二噁烯并-[2,3-f]-苯并咪唑衍生物和制备方法及含有该化合物的农药 Download PDFInfo
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- CN1049894C CN1049894C CN95192904A CN95192904A CN1049894C CN 1049894 C CN1049894 C CN 1049894C CN 95192904 A CN95192904 A CN 95192904A CN 95192904 A CN95192904 A CN 95192904A CN 1049894 C CN1049894 C CN 1049894C
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- 229960000611 pyrimethamine Drugs 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 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
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 239000004308 thiabendazole Substances 0.000 description 1
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- 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
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- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
式(Ⅰ)的新的苯并咪唑衍生物,式中,R是氰基或式(a)所示的基团,X1、X2、X3和X4是相同或不同的卤素;Y是可任选地被卤素取代的烷基、链烯基或链炔基;或者是任选取代的苯烷基或在各种情况下任选取代的环烷基和环烯基;以及Z是氢或卤素。这些物质的制法及其在防治病虫害方面的用途。用于其制备的新中间体和方法。
Description
本发明涉及新的苯并咪唑衍生物、其制备方法,及其作为农药的用途。本发明此外还涉及新的中间体及其制备方法。
现已发现,某些苯并咪唑衍生物诸如,例如,2-氰基-3-二甲氨基磺酰-6,6,7,7-四氟-[1,4]-二噁烯并(dioxino)-[2,3-f]-苯并咪唑或者2-氰基-6,6-二氟-2-二甲氨基磺酰-[1,3]-二氧杂环戊烯并-[4,5-f]-(dioxolo)苯并咪唑具有杀真菌,或杀真菌及杀螨性能(参看EP-A 0517476及DE-OS(德国公开专利说明书)4 139 950)。但是,这些现有技术化合物的效力在各种应用中,尤其低比率施用时是不完全令人满意的。
现在已经发现了式I的新的苯并咪唑衍生物式中
X1、X2、X3和X4是相同或不同的卤素;
Y 是烷基、链烯基或链炔基,各基团皆可任选地被卤素取代;或代表任选取代的苯烷基,或在各种情况下任选取代的环烷基和环烯基;以及
Z 是氢或卤素。
取决于取代基的种类,式(I)的化合物能够以几何和/或旋光异构体或者不同组成的异构体混合物形式存在。本发明涉及它们的纯异构体和异构体的混合物。
在式(I)中,折线代表两个氮原子之一和相邻碳原子间的双键,取代基R已连接在该碳原子上。在每种情况下,未参与双键的另一个氮原子已连结在-SO2-Y基团上。
Cl-SO2-Y (III)式中,R、X1、X2、X3、X4、Y及Z的含义如前所述。如有必要,上述反应可在稀释剂存在下进行,且如有必要,上述反应可在反应助剂存在下进行。
而且,已经发现,式(I)的苯并咪唑衍生物非常适于用作农药。更具体而言,它们显示出强有力的杀真菌、杀虫以及杀螨活性。
意想不到的是,按照本发明的苯并咪唑衍生物的活性高于结构很相似的现有技术化合物。
式(I)给出了按照本发明的化合物的一般定义。
X1、X2、X3和X4可以相同或不同,优选代表氟、氯或溴,
Y 优选代表C1-C6烷基、C2-C6链烯基和C2-C6链炔基,各基团可任选地被1-5个相同或不同的卤素取代基取代;或代表苯基-C1-C4烷基,其苯基部分可被1-3个相同或不同的取代基取代,该取代基可选自卤素、C1-C4烷基、含1-5个相同或不同卤原子的C1-C4卤烷基、C1-C4烷氧基和/或含1-5个相同或不同卤原子的C1-C4卤代烷氧基,或代表可被1-3个相同或不同取代基取代的C3-C7环烷基,该取代基可选自卤素、C1-C4烷基和/或含1-5个相同或不同卤原子的C1-C4卤烷基、或代表可被1-3个相同或不同取代基取代的C5-C7环烯基,该取代基可选自卤素,C1-C4烷基和/或含1-5个相同或不同卤原子的C1-C4卤烷基,
Z 优选代表氢、氟、氯或溴。
R 特别优选代表氰基或
基,
X1、X2、X3和X4可以相同或不同,特别优选代表氟、氯或溴,
Y 特别优选代表C1-C4烷基、C2-C4链烯基和C2-C4链炔基,各基团可任选地被1-5个相同或不同的氟和/或氯取代基取代;或代表其苯基部分可被1-3个相同或不同取代基取代的苯基-C1-C2烷基,该取代基可选自氟、氯、溴、C1-C4烷基、C1-C2烷氧基、含1-5个氟和/或氯原子的C1-C2卤烷基和含1-5个氟和/或氯原子的C1-C2卤代烷氧基;或代表可被1-3个相同或不同的取代基取代的C3-C7环烷基,该取代基选自氟、氯、溴、C1-C4烷基和/或含1-5个氟和/或氯原子的C1-C2卤烷基;或代表可被1-3个相同或不同取代基取代的C3-C7环烯基,该取代基选自氟、氯、溴、C1-C4烷基和/或含1-5个氟和/或氯原子的C1-C2卤烷基,
Z 特别优选的是氢、氟、氯或溴。
R 非常特别优选的也是氰基或
基,
X1、X2、X3和X4可以相同或不同,非常特别优选的是氟、氯或溴,
Y 非常特别优选的是甲基,乙基,正或异丙基,正、异、仲或叔丁基,烯丙基,正或仲丁烯基,炔丙基以及正或仲丁炔基;可被1-3个相同或不同的氟和/或氯取代基取代的甲基、乙基、烯丙基、正或仲丁烯基、炔丙基和正或仲丁炔基;或者是苄基或苯乙基,此两基的苯基部分可被1-3个相同或不同的取代基取代,该取代基可选自氟、氯、溴、甲基、乙基、甲氧基、三氟甲基和/或三氟甲氧基;或者是环丙基、环戊基、环己基、环戊烯基和环己烯基,这些基团可被1-3个相同或不同的取代基取代,该取代基可选自氟、氯、溴、甲基、正或异丙基、氯甲基、二氯甲基和/或三氟甲基,
Z 非常特别优选的是氢,氟或氯。
上述本发明化合物定义范围内的烃基,诸如烷基在所有情况下可以是直链或支链的,此外还与其它原子相连,诸如卤烷基。
按照本发明的化合物的例子列于表1-6。
表2
表2包含式(I)的化合物,其中R=CN、X1=F、X2=F、X3=Cl、X4=F以及Y具有列于表1的含义。
表3
表3包含式(I)的化合物,其中R=CN、X1=F、X2=Cl、X3=Cl、X4=F以及Y具有列于表1的含义。
表4-6
式(II)给实施本发明方法所需用作起始物质的苯并咪唑下了一般定义。在式(II)中,R、X1、X2、X3、X4及Z优选、或特别优选的是,具有前面在叙述作为优选或特别优选的式(I)化合物时已经提到的对R、X1、X2、X3、X4、R及Z所下的那些定义。
式(II)的苯并咪唑中有一些已经公开(参见EP-A 0517476或DE-OS(德国公开专利说明书)4 139 950)。这些化合物的制备方法是:使式(IV)的苯二胺与式(V)的2,2,2-三氯乙酰亚氨酸甲酯在冰醋酸存在下,于10℃~40℃的温度下起反应:式中,X1、X2、X3、X4及Z的含义如前所述,然后使所得到的式(VI)的2-三氯甲基苯并咪唑与氨水溶液在一种稀释剂(例如乙醇)存在下于0℃-40℃的温度下起反应:式中,X1、X2、X3、X4及Z的含义如前所述。然后,如有必要,使所得到的式(II-A)的苯并咪唑与硫化氢在一种稀释剂(例如乙醇)存在下于10℃-100℃之间的温度下起反应,如有必要可在一种酸结合剂(例如三乙胺)存在下起反应:式中,X1、X2、X3、X4及Z的含义如前所述。
式(VI-1)、(II-1)以及(II-2)的化合物都是新的,它们可按照上面的方法来制备,使式(IV-1)的6,7-二氨基-2,3-二氯-2,3-二氟-[1,4]-苯并二噁烯与式(V)的2,2,2-三氯乙酰亚氨酸甲酯在冰醋酸存在下于10℃-40℃的温度下起反应,然后使所得式(VI-1)的6,7-二氯-6,7-二氟-2-三氯甲基-[1,4]-二噁烯并-[2,3-f]-苯并咪唑与氨水溶液在一种稀释剂(例如乙醇)存在下于0℃-40℃的温度下起反应,然后,如有必要,可使所得式(II-1)的2-氰基-6,7-二氯-6,7-二氟-[1,4]-二噁烯并-[2,3-f]-苯并咪唑与硫化氢在一种稀释剂(例如乙醇)存在下于10℃-100℃的温度下反应,如有必要,可在一种酸结合剂(例如三乙胺)存在下起反应,
式(IV)的苯二胺中有一些已经公开(参看EP-A 0517476、DE-OS(德国公开专利说明书)4 139 950、DE-OS(德国公开专利说明书)3 621 301以及DE-OS(德国公开专利说明书)3 605 977)。这些化合物的制备方法是:使式(VII)的1,4-苯并二噁烷与硝酸和硫酸的混合物(也可含有发烟硫酸)在0℃-100℃的温度下起反应,式中,X1、X2、X3、X4及Z的含义如前所述,然后或者使所得式(VIII)的二硝基-[1,4]-苯并二噁烷在50℃-100℃的温度,例如用铁在含水盐酸和乙醇存在下还原,式中,X1、X2、X3、X4及Z的含义如前所述,或者使式VIII的化合物与单质氢在25℃-100℃的温度和1-100巴的压力下起催化反应,此时的催化剂是元素周期表第VIII副族的金属或金属化合物,特别是镍或钯(参看制备实例)。
式(IV-1)的6,7-二氨基-2,3-二氯-2,3-二氟-[1,4]-苯并二噁烷是迄今未知的,它可由上法制备,或者使式(VIII-])的2,3-二氯-2,3-二氟-6,7-二硝基-[1,4]-苯并二噁烷在50℃-100℃的温度,例如用铁在含水盐酸和乙醇的存在下还原,或者使式(VIII-1)的化合物与单质氢在25℃-100℃的温度和1-100巴的压力下起催化反应,此时的催化剂是元素周期表第VIII副族的金属或金属化合物,特别是镍或钯(参看制备实例)。
式(VIII-1)的2,3-二氯-2,3-二氟-6,7-二硝基-[1,4]-苯并二噁烷也是迄今未知的。式(VIII-1)化合物的制法是:使式(VII-1)的2,3-二氯-2,3-二氟-[1,4]-苯并二噁烷与硝酸和硫酸的混合物,如果必要可在发烟硫酸存在下,于0℃-100℃的温度下起反应。
式(VII-1)的2,3-二氯-2,3-二氟-[1,4]-苯并二噁烷是迄今未知的。此化合物的制法是:使式(VII-2)的2,2,3,3-四氯-[1,4]-苯并二噁烷与无水氢氟酸于热压器中在-10℃-+70℃温度下起反应(参看制备实例),
适合于实施本发明方法的稀释剂是惰性有机溶剂。可优选使用下列各化合物:任选卤化的脂族、脂环族或芳族烃类,例如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿或四氯化碳,醚类诸如二乙醚、二异丙醚、二噁烷、四氢呋喃、乙二醇二甲醚或乙二醇二乙醚,酮类诸如丙酮或丁酮或甲基异丁基酮,腈类诸如乙腈、丙腈或苄腈,或者酯类诸如乙酸甲酯或乙酸乙酯。
按照本发明的方法优选是在合适的反应助剂存在下进行。合适的反应助剂是所有通常的无机或有机碱类。可优选使用下列各化合物:碱土金属氢氧化物或碱金属氢氧化物,诸如氢氧化钠、氢氧化钙、氢氧化钾或氢氧化铵,碱金属碳酸盐,诸如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠,碱金属乙酸盐或碱土金属乙酸盐,诸如乙酸钠、乙酸钾或乙酸钙,以及叔胺类,诸如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一碳烯(DBU)。
当进行本发明方法时,反应温度可在相当大的范围内变化。此法通常在0℃-150℃,优选在20°-120℃的温度下进行。
本发明的方法通常在常压下进行。但也可在升压或减压下进行。
为进行本发明的方法,稀释剂中每摩尔式(II)的苯并咪唑通常使用1.0-2.0mol,优选使用1.0-1.3mol式(III)的磺酰氯以及,如果必要,可使用1.0-2.0mol,优选1.0-1.3mol的反应助剂。可按常规方法(参看制备实例)进行反应,并对反应产物进行后处理和分离。
本发明的式(I)活性化合物具有强的抗病虫害作用,且实际上可以用来防治不希望的有害微生物。该活性化合物适合用作作物保护剂,特别是作为杀真菌剂。
杀真菌剂在作物保护中用于防治根肿菌纲(Plasmodiophoromycetes),卵菌亚纲(Oomycetes),壶菌纲(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌纲(Ascomycetes),担子菌纲(Basidiomycetes)和半知菌类(Deuteromycetes)。
属于上述列出的属名的某些导致真菌病害的病原体作为例子可以提到,但不限于:
腐霉属,如甘薯白腐病菌;
疫霉属,(如蔓延疫霉);
(假霜霉属),如葎草假霜霉或古巴假霜霉;
单轴霉属,如葡萄生单轴霉;
霜霉属,如豌豆霜霉或芸苔霜霉;
白粉菌属,如禾白粉菌;
单丝壳菌属,如苍耳单丝壳菌;
柄球菌属,如苹果白粉病柄球菌;
黑星菌属,如苹果黑星菌;
核腔菌属,如园核腔菌或麦类核腔菌(分生孢子形式:Drechslera,有性繁殖:长蠕孢属);
旋孢腔菌属,如禾旋孢腔菌(分生孢子形式:Drechslera,有性繁殖:长蠕孢属);
单孢锈菌属,如菜豆单孢锈菌;
柄锈菌属,如隐匿柄锈菌;
腥黑粉菌属,如小麦网腥黑粉菌;
黑粉菌属,如裸黑粉菌或燕麦黑粉菌;
薄膜革菌属,如稻纹枯病菌(佐佐木氏薄膜革菌);
梨孢菌属,如稻梨孢菌;
镰孢属,如大刀镰孢;
葡萄孢属,如灰色葡萄孢;
壳针孢属,如麦类颖斑枯病壳针孢菌;
小球腔菌属,如Leptosphaeria nodorum;
尾孢菌属,如Cercospora canescens;
交链孢属,如甘蓝黑斑病交链孢菌;
假小尾孢菌属,如Pseudocercosporella herpotrichoides。
植物在防治其病虫害所需的浓度下对活性化合物有足够的耐药力这一事实使植物地上部分、繁殖原种和种子以及土壤的处理成为可能。
由于这个原因,本发明的活性化合物能够特别成功地用来防治果树和蔬菜生长期的病害。例如抗导致蕃茄晚疫病(Phytophthora infestants)病原体或抗导致苹果黑星病(Venturia inaequalis)病原体或抗导致葡萄霜霉病(Plasmopara viticola)病原体或用于防治水稻病害,诸如抗导致稻瘟病(Pyricularia oryzae)病原体。
而且,本发明的活性化合物具有良好的离体活性。
此外,本发明的活性化合物适用于防治在农业上、森林中、仓储保护和材料保护方面以及卫生领域中产生的动物虫害,尤其是节肢动物和线虫,特别是昆虫和蛛形纲动物。这类化合物对于通常敏感和有抗性的虫害物种及其全部或部分发育阶段均有活性。上述虫害包括:
等足纲的潮虫、鼠妇和粗潮虫。
倍足纲的具斑马陆。
唇足纲的蜈蚣和蚰蜓。
综合纲的庭院么蚰。
缨尾目的衣鱼。
弹尾目的武装棘跳虫。
直翅目的东方蠊、美洲大蠊、马德拉蠊、德国小蠊、家蟋蟀、蝼蛄属的种类、非洲飞蝗、异黑蝗和沙漠蝗
革翅目的欧洲球螋。
等翅目散白蚁属的种类。
虱目的葡萄根瘤蚜、瘿绵蚜属种类、体虱、血虱属种类和毛虱属种类。
食毛目中羽虱属和畜虱属的种类。
缨翅目的的温室纹蓟马和烟蓟马。
异翅目的扁盲蝽属种类、介中棉红蝽、方背皮蝽、温带臭虫、长红猎蝽和维猎蝽属的种类。
同翅目的甘蓝粉虱、木薯粉虱、温室粉虱、棉蚜、甘蓝蚜、茶蔗隐瘤蚜、甜菜蚜、波密一条角蚜、苹果绵蚜、梅大尾蚜、麦长管蚜、瘤蚜属的种类、忽布疣蚜、禾谷缢管蚜、小绿叶蝉属种类、二叶叶蝉、黑尾叶蝉、水木坚蚧、乌盔蚧、灰飞虱、褐飞虱、红肾圆盾蚧、常春藤圆盾蚧、粉蚧属和木虱属的种类。
鳞翅目的棉红铃虫、松尺蠖、苹细蛾、苹果巢蛾、菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属种类、棉潜蛾、桔潜蛾,地老虎属种类、切根虫属种类、夜蛾属种类、埃及金钢钻、实夜蛾属种类、甜菜夜蛾、甘蓝夜蛾、松夜蛾、斜纹夜蛾、灰翅夜蛾属种类、粉纹夜蛾、菜粉蝶属种类、禾草螟属种类、玉米螟、地中海粉斑螟、大蜡螟、幕谷蛾、袋谷蛾、褐织蛾、亚麻黄卷蛾、网织烟卷蛾、枞色卷蛾、葡萄果蠹蛾、茶长卷蛾和栎绿卷蛾。
鞘翅目的家具窃蠹、谷蠹、大豆象、Bruchidius obtectus、覆锥胸豆象、北美家天牛、桤木萤叶甲、马铃薯叶甲、辣根猿叶甲、叶甲属种类、油菜金头跳甲、墨西哥大豆瓢虫、隐食甲属种类、锯谷盗、花象属种类、谷象属种类、黑葡萄耳象、香蕉根颈象、白菜籽龟象、紫苜蓿叶象、皮蠹属的种类、斑皮蠹属种类、圆皮蠹属种类、毛皮蠹属种类、粉蠹属种类、油菜花露尾甲、蛛甲属种类。黄蛛甲、裸蛛甲、拟谷盗属种类、黄粉虫、叩头虫属种类、宽胸叩头虫属种类、西方五月鳃角金龟、马铃薯鳃角金龟和褐新西兰肋翅鳃角金龟。
膜翅目的锯角叶蜂属的种类、樱叶蜂属种类、蚁属的种类、小黄家蚁和胡蜂属的种类。
双翅目的伊蚊属种类、桉蚊属种类、库数属种类、黑尾果蝇、家蝇属种类、厕蝇属的种类、红头丽蝇、绿蝇属种类、金蝇属种类、疽蝇属种类、胃蝇属种类、厩螫蝇属种类、狂蝇属种类、皮蝇属种类、虻属的种类、园艺毛蚊、瑞曲麦杆蝇、种蝇属种类、甜菜泉蝇、地中海蜡实蝇、橄榄实蝇和欧洲大蚊。
蚤目的印鼠客蚤和角叶蚤属的种类。
蛛形纲的黑歇和毒治虾。
蜱螨目的粗脚粉螨、锐缘蜱属种类、钝缘蜱属种类、鸡皮刺螨、硬瘿螨、桔皱叶刺瘿螨、牛蜱属种类、扇头蜱属种类、花蜱属种类、璃眼蜱属种类、硬蜱属种类、瘙螨属种类、痒螨属种类、疥螨属种类、跗线螨属种类、苜蓿苔螨、金爪螨属种类和叶螨属的种类。
植物寄生线虫包括短体线虫属种类、相似穿孔线虫、起绒草茎线虫、半穿刺线虫、异皮线虫属种类、根结线虫属种类、滑刃线虫属种类、长针线虫属种类、剑线虫属种类和毛刺线虫属的种类。
本发明式(1)的活性化合物的特点是还有杰出的杀螨活性,例如抗棉红蜘蛛(Tetranychus urticae)。式(I)的化合物还具有良好的作用于叶子的杀虫活性。
根据其具体的物理和/或化学特性,活性化合物可以转化成常规剂型,如溶液,乳液,悬浮剂,粉剂,泡沫剂,膏剂,颗粒剂,气雾剂,用于种子的聚合物和涂覆组合物微胶囊,和超低容量冷和热雾剂。
这些型剂可以已知的方式生产,例如,将活性化合物与增量剂(即液体溶剂,压力下的液化气体)混合,和/或与固体载体混合,并任选使用表面活性剂。用水作填充剂的情况下,有机溶剂也可以用作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂族烃,如氯代苯类,氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮,甲乙酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水;液化气增量剂或载体是指环境温度和大气压力下是气体的液体,例如气雾喷射剂,如卤代烃以及丁烷,丙烷,氮气和二氧化碳;固体载体适合的有:研碎的天然矿物诸如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱石或硅藻土,和研碎的合成矿物质,如高分散二氧化硅,矾土和硅酸盐;用于颗粒剂的固体载体适合的有:例如压碎和分级的天然岩石如方解石,大理石,浮石,海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑,椰壳,玉米穗轴和烟茎;乳化剂和或起泡剂适合的有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白质水解产物;分散剂适合的有:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如粉状、颗粒或乳胶形式的羧甲基纤维素和天然和合成聚合物,如阿拉伯胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可以使用着色剂,如无机颜料,例如氧化铁,氧化钛和普鲁士蓝,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有0.1至95%(重量),优选0.5至90%(重量)的活性化合物。
当用作杀真菌剂时,本发明的活性化合物可以其本身或以其制剂形式,与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂的混合物的形式使用,以扩大作用谱,或为防止抗性的逐步建立。在许多情况下,可以获得增效作用,这就是说,混合物的活性超出单个组分的活性。
混合物中特别有利的组分是例如下列化合物:杀真菌剂:
2-氨基丁烷,2-苯胺基-4-甲基-6-环丙基-嘧啶;2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苯甲基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基-苯氧基)嘧啶-4-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP),Aldimorph,Ampropylfos,敌菌灵,戊环唑,苯霜灵,碘萎灵,苯菌灵,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,磺酸丁嘧啶,丁赛特,石硫合剂,敌菌丹,克菌丹,多菌灵,萎锈灵,甲基克杀螨,地茂散,氯化苦,百菌清,乙菌利,硫杂灵,霜脲氰,环唑醇,酯菌胺,防霉酚,苄氯三唑醇,抑菌灵,哒菌清,氯硝胺,乙霉威,恶醚唑,甲嘧醇,烯酰吗啉,烯唑醇,清螨普,二苯胺,dipyrithion,灭菌磷,二噻农,十二烷胍,腙菌酮,克菌散,环氧唑(epoxyconazole),乙嘧啶,氯唑灵,双氯苯嘧啶,苯氰唑,一甲呋萎灵,种衣酯,拌种咯,苯锈啶,丁苯吗啉,乙酸三苯基锡,三苯羟基锡,福美铁,嘧菌腙,氟啶胺,Fludioxonil,氟氯菌核利,fluquinconazole,氟哇唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋霜灵,拌种胺,双胍辛,六氯苯,己唑醇,甲羟异噁唑,抑霉唑,酰胺唑,双胍辛醋酸盐,异稻瘟净,异菌脲,稻瘟灵,春日霉素,铜制剂如氢氧化铜,环烷酸铜,碱式氯化铜,硫酸铜,氧化铜,喹啉铜和波尔多混合物,双代混剂,代森锰锌,代森锰,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,担菌胺,代森联,噻菌胺,腈菌唑,福镁镍,nitrothalisopropyl,氟苯嘧啶醇,甲呋酰胺,恶酰胺,oxamocarb,氧化萎锈灵,perfurazoat,戊菌唑,戊菌隆,phosdiphen,匹马菌素,哌啶宁,多氧霉素,烯丙异噻唑,咪鲜安,二甲菌核利,霜霉威,丙环唑,甲基代森锌,定菌磷,啶斑肟,pyrimethanil,咯喹酮,五氯硝基苯(BCNB),硫磺和硫制剂,戊唑醇,酞枯酸,四氯硝基苯,氟醚唑,噻菌灵,噻菌腈,甲基托布津,福美双,甲基立枯灵,对甲抑菌灵,三唑酮,三唑醇,唑菌嗪,杨菌胺,三环唑,环吗啉,氟菌唑,嗪氨灵,triticonazole,validamycin A,vinclozolin,代森锌,福美锌。杀细菌剂:
拌棉酚,防霉酚,氯定,福美镍,春日霉素,octhilinone,呋喃羧酸,土霉素,烯丙异噻唑,链霉素,酞枯酸,硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素,AC303630,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双甲脒,齐墩螨素(avermectin),AZ60541,azadirachtin,乙基谷硫磷,谷硫磷,三唑锡,苏芸金杆菌,苯噁威,丙硫克百威,杀虫螨,乙体氟氯氰菊酯,氟氯菊酯,丁苯威,溴醚菊酯(brofenprox),溴硫磷,混戊威,噻嗪酮,丁酮威,丁基哒螨酮,硫线磷,西维因,克百威,三硫磷,丁硫克百威,巴丹,CGA157419,CGA184699,除线威,chlorethoxyfos,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,顺式苄呋菊酯,三氟氯氰菊酯,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯,氯氟氰菊酯,三环锡,氯氰菊酯,灭蝇胺,溴氰菊酯,甲基内吸磷,异一○五九II,异吸磷II,杀螨隆,地亚农,氯线磷,敌敌畏,dicliphos,百治磷,乙硫磷,伏虫脲,乐果,甲基毒虫畏,二噁硫磷,乙拌磷,克瘟散,emamectin,高氰戊菊酯,除蚜威,乙硫磷,醚菊酯,丙线磷,醚菊酯,乙嘧硫磷,克线磷,喹螨醚,螨完锡,杀螟硫磷,fenobucarb,苯硫威,双氧威,甲氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,fluazinam,氟螨脲,氟氰戊菊酯,氟虫脲,氟醚菊酯(flufenprox),氟胺氰菊酯,地虫硫磷,安果,噻唑硫磷,fubfenprox,呋线威,六六六(HCH),heptenophos,氟铃脲,噻螨酮,咪蚜胺,异稻瘟净,氯唑磷,异丙胺磷,异丙威,噁唑磷,伊维菌素,λ-三氟氯氰菊酯,lufenuron,马拉硫磷,灭蚜硫磷,速灭磷,倍硫磷亚砜,蜗牛敌,虫螨畏,甲胺磷,甲噻硫磷,甲硫威,灭多威,metolcarb,米尔倍菌素,久效磷,moxidectin,二溴磷,NC184,NI 25,nitenpyram,氧乐果,草肟威,砜吸硫磷,oxydeprofos,马拉硫磷,甲基马拉硫磷,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗蚜威,甲基嘧啶硫磷,嘧啶硫磷,丙溴磷,甲丙威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,pyrachlophos,苯哒嗪硫磷,pyresmethrin,除虫菊,哒螨酮,pyrimidifen,蚊蝇醚,喹硫磷,RH5992,水杨硫磷,硫线磷,silafluofen,治螟磷,甲丙硫磷,tebufenozide,tebufenpyrad,特丁嘧啶硫磷,伏虫隆,七氟菊酯,双硫磷,叔丁威,特丁甲拌磷,杀虫畏,thiafenox,硫双灭多威,己酮肟威,甲基乙拌磷,喹线磷,苏芸金菌素,四溴菊酯,triarathen,三唑磷,triazuron,敌百虫,杀虫隆,trimethacarb,完灭硫磷,二甲威,二甲苯威,zetamethrin。
也可与其它已知活性化合物如除草剂,或与化肥和生长调节剂的混合。
当用作杀真菌剂时,活性化合物可以以其制剂或其制备的应用形式使用,所述的制备使用形式如可直接使用溶液,悬浮剂,可湿性粉剂,膏剂,可溶性粉剂,粉剂和颗粒剂。它们以常规方法使用,例如浇泼,喷雾,雾化,撒施,喷粉,起泡,涂刷等等。此外可用超低容量方法使用化合物,或将活性化合物制剂或活性化合物本身注入土壤。也可处理植物的种子。
当用作杀真菌剂处理盆栽植物时,使用形式中的活性化合物浓度可在大范围内变化:它们通常以1-0.0001%(重量),优选以0.5-0.001%(重量)的浓度使用。
当用作杀真菌剂处理种子时,通常每公斤种子需要0.001至50g,优选0.01至10g的活性化合物。
当用作杀真菌剂处理土壤时,在作用点需要活性化合物的浓度为0.00001至0.1%(重量),优选0.0001至0.02%(重量)。
当用作杀真菌剂和杀螨剂时,根据本发明的活性化合物可以其市售制剂和从上述制剂制备的应用形式,以及与其它活性化合物的混合物的形式存在,其它活性化合物如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、植物生长调节剂或除草剂。例如,杀虫剂包括:磷酸酯、氨基甲酸酯、羧酸酯、氯代烃类、苯基脲类和从微生物中生产的物质等。
可述及的有下述化合物:
氟酯菊酯、甲体氯氰菊酯、氟氯氰菊酯、氟氯菊酯、brofenprox。顺-苄呋菊酯、clocythrin、乙氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、氯氰菊酯、溴氰菊酯、高氰戊菊酯、醚菊酯、分扑菊酯、氰戊菊酯、氟氰戊菊酯、氟胺氰菊酯、λ-三氟氯氰菊酯、氯菊酯、反灭菊酯、除虫菊、silafluofen、四溴菊酯、zetamethrin,
棉铃威、噁虫威、丙硫克百威、全杀威、丁叉威、西维因、杀螟丹、苯虫威、fenobucarb、双氧威、异丙威、灭虫威、灭多威、metolcarb、甲叉丙威、抗蚜威、猛杀威、残杀威、叔丁威、硫双灭多威、特铵叉威、三甲威、二甲威、xylylcarb、乙酰甲胺磷、谷硫磷、乙基谷硫磷、溴硫磷、硫线磷、三硫磷、毒虫威、氯甲磷、毒死蜱、甲基毒死蜱、杀螟腈、内吸磷、甲基内吸磷、甲基内吸磷S赶磷酸酯、二嗪农、敌敌畏、dicliphos、除线磷、百治磷、乐果、甲基毒虫威、敌杀磷、乙拌磷、克瘟散、乙硫磷、氯嘧啶磷、杀螟松、倍硫磷、地虫磷、安果、庚虫磷、iprobenfos、异唑磷、异噁唑磷、甲拌磷、马拉硫磷、灭蚜磷、速灭磷、甲丙硫磷、虫螨威、甲胺磷、二溴磷、氧化乐果、砜吸磷、oxydeprofos、对硫磷、甲基对硫磷、稻丰散、伏杀磷、亚胺硫磷、磷胺、辛硫磷、乙基虫螨磷、虫螨磷、丙虫磷、丙硫磷、发果、吡唑硫磷、哒嗪硫磷、喹硫磷、salithion、克线丹、治螟磷、乙丙硫磷、杀虫威、双硫磷、甲基乙拌磷、治线磷、敌百虫、三唑磷、蚜灭多,
噻嗪酮、定虫隆、氟脲杀、氟螨脲、氟铃脲、氟螨脲、蚊蝇醚、tebufenozide、伏虫隆、triflumuron,
咪蚜胺、nitenpyram、N-[(6-氯-3-吡啶基)甲基]-N’-氰基-N-甲基乙烷亚胺酰胺(NI-25),
齐墩螨素(abamectin)、虫螨醚、齐墩螨素(avermectin)、azadirachtin、杀虫磺、苏云菌亚孢杆菌、灭蝇胺、杀螨隆、齐墩螨素(emamectin)、醚菊酯、fenpyrad、fipronil、flufenprox、lufenuron、多聚甲醛、milbemectin、pymetrozin、tebufenpyrad、三唑磷,
涕灭威、噁虫威、丙硫克百威、呋喃丹、丁硫克百威、chlorethoxyfos,cloethocarb、乙拌磷、ethophrophos、氯嘧啶磷、克线磷、fipronil、地虫磷、噻唑硫磷、呋线威、六六六、异唑磷、丙胺磷、灭虫威、久效磷、甲叉丙威、甲氨叉威、甲拌磷、辛硫磷、丙硫磷、吡唑硫磷、硫线磷、silafluofen、tebupirimiphos、七氟菊酯、特丁磷、硫双灭多威、thiafenox,
唑环锡、哒螨酮、四螨嗪、三环锡、杀螨隆、乙硫磷、喹螨醚、杀螨锡、螨完锡、苯硫威、甲氰菊酯、fenpyrad、唑螨酯、氟啶胺、fluazuron氟螨脲、氟虫脲、氟胺氰菊酯、fubfenprox、噻螨酮、杀扑磷、甲噻硫磷、久效磷、moxidectin、伏杀磷、溴丙磷、pyraclofos、哒螨酮、pyrimidifen、tebufenpyrad、苏云金菌素、triarathen和4-溴-2-(4-氯苯基)-1-(乙氧甲基)-5-(三氟甲基)-1H-比咯-3-腈(AC 303630)。
根据本发明的活性化合物可以其市售制剂和从上述制剂制备的应用形式,以及与增效剂的混合物的形式存在,增效剂是能够增加活性化合物活性,但加入的增效剂本身不需要有活性的化合物。
从市售制剂制备的应用形式中活性化合物的含量可在很宽的范围内变化。使用形式中活性化合物的浓度为0.0000001至95%(重量)的活性化合物,优选0.0001至1%(重量)。
本化合物以适用于使用形式的常规方法进行使用。
按照本发明的活性化合物的制法及用途可从下列各实例看出。
制 备 实 例
4.6g(15mmol)2-氰基-6,7-二氯-6,7-二氟-[1,4]-二噁烯并-[2,3-f]-苯并咪唑在室温和搅拌下分批添加到0.6g(15mmol)60%氢化钠在70ml四氢呋喃的混合物中。在室温下继续搅拌30分钟,然后添加4.6g(30mmol)甲磺酰氯,混合物回流12小时。
冷却后,将该溶液倒进400ml水中。混合物用二氯甲烷萃取三次,每次用100ml,干燥后,将合并的有机萃取液减压浓缩。所得残留物随后用20ml乙醚借助搅拌使之结晶。
这样制得4.9g(85%理论量)2-氰基-6,7-二氯-6,7-二氟-3-甲磺酰基-[1,4]-二噁烯并-[2,3-f]-苯并咪唑,熔点123-126℃。
59.7g(0.15mol)6,7-二氯-6,7-二氟-2-三氯甲基-[1,4]-二噁烯并-[2,3-f]-苯并咪唑在室温和搅拌下添加到250ml浓氨水溶液和200ml乙醇的混合物中。混合物在室温下搅拌20小时,然后用盐酸使之酸化。反应混合物用二氯甲烷萃取三次,每次用150ml。将有机萃取物干燥并浓缩。所得残留物随后用二乙醚作洗脱剂借助色谱及硅胶进行提纯。
54.0g(0.3mol)2,2,2-三氯乙酰亚胺酸甲酯在室温和搅拌下逐滴添加到54.2g(0.20mol)6,7-二氨基-2,3-二氯-2,3-二氟-[1,4]-苯并二噁烷和200ml冰醋酸的混合物中。添加完毕之后,在室温下继续搅拌20小时。然后添加300ml水,将所得的沉淀滤出、干燥。
将316g(0.95mol)2,3-二氯-2,3-二氟-6,7-二硝基-[1,4]-苯并二噁烷溶于1500ml四氢呋喃中,连同30g阮内镍放进氢化压热器中,混合物用氢气冲洗,随后在25-45℃下注入30-50巴氢进行氢化。当不再吸收氢气时,使压热器冷却、卸压。在过滤除去催化剂之后蒸出溶剂。
这样制得246g 6,7-二氨基-2,3-二氯-2,3-二氟-[1,4]-苯并二噁烷,熔点130-131℃。
将400g混合酸(33%(重量)HNO3,67%(重量)H2SO4)加入到一个20℃的搅拌装置中,在室温和搅拌下逐滴添加200g 2,3-二氯-2,3-二氟-[1,4]-苯并二噁烷。混合物在20℃下搅拌1小时,然后在40℃下搅拌1小时。然后逐滴添加100ml 20%发烟硫酸。在40℃下继续搅拌2小时,然后在50℃下搅拌3小时。在混合物冷却之后,将其转移到500g冰上,将产物溶解在二氯甲烷中。水洗之后,使溶液干燥,随后脱除其中的溶剂。
将1800ml无水氟化氢引入到氧化装置中,在-10℃下加入1300g 2,2,3,3-四氯-[1,4]-苯并二噁烷。然后封闭压热器,在搅拌下把内含物加热到60℃。在停止放出氯化氢之后(用冷凝器卸压),使混合物冷却,蒸出氟化氢,将残留物转移到冰上。在相分离之后,将有机产物干燥、蒸馏。
这样制得665g 2,3-二氯-2,3-二氟-[1,4]-苯并二噁烷,沸点82-83℃/18mbar。
实例2
在室温下将5.4g(40mmol)粉状碳酸钾添加到溶于100ml乙腈的5.4g(20mmol)2-氰基-6,6,7,7-四氟-[1,4]-二噁烯并-[2,3-f]-苯并咪唑中,然后在室温和搅拌下逐滴添加4.6g(30mmol)甲磺酰氯,添加完毕后,将混合物回流6小时。反应混合物随后冷却到室温并倒进500ml水中。混合物用二氯甲烷萃取三次,每次用150ml。合并的有机相用硫酸钠干燥,并在减压下脱除溶剂。
这样制得5.5g(79%理论量)2-氰基-3-甲磺酰基-6,6,7,7-四氟-[1,4]-二噁烯并-[2,3-f]-苯并咪唑,熔点180-183℃。
用途实例
2-氰基-3-二甲氨基磺酰基-6,6,7-三氟-7-氯(或6,7,7-三氟-6-氯)-[1,4]-二噁烯并-[2,3-f]-苯并咪唑
(全部公开在EP-A 0517476或DE-OS(德国公开专利说明书)4 139 950中)。
实例A
黑星病试验(苹果)/防护
溶剂: 4.7重量份丙酮
乳化剂:0.3重量份烷芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与上述量的溶剂及乳化剂混合,然后用水将此浓缩物稀释到所需的浓度。
为试验防护活性,用活性化合物制剂对秧苗喷雾直到滴液湿润。在喷雾涂层已干后,用苹果黑星病病原体(Venturia inaequalis)的分生孢子水悬浮液接种植物,然后在一个20℃和100%相对湿度的培育箱中停留一天。
然后把植物放在一间20℃和约70%相对湿度的温室中。
在接种12天之后进行评价。
在本试验中,式(I-1)和(I-2)的化合物在活性化合物浓度为10ppm下显示出80%以上的效力,而比较物质(A)、(B )、(C)的效力分别为43%、0%以及18%。
实例B
稻瘟病试验(水稻)/防护
溶剂: 12.5重量份丙酮
乳化剂:0.3重量份烷芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与上述量的溶剂混合,用水和上述量的乳化剂将浓缩物稀释到所需的浓度。
为试验防护活性,用活性化合物制剂对水稻秧苗喷雾直到液滴湿润。在喷雾涂层已干后,用稻瘟病病原体(Pyricularia oryzae)的孢子水悬浮液接种植物,然后把植物放在一间25℃和100%相对湿度的温室中。
在接种4天之后对病害程度进行评价。
在本试验中,式(I-2)的化合物在0.025%活性化合物浓度下显示出90%的效力,而比较物质(A)的效力为10%。
表B
稻瘟病试验(水稻)/防护
实例C
棉红蜘蛛试验(OP抗性/浸泡处理)
溶剂:7重量份丙酮
乳化剂:1重量份烷芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和上述量的乳化剂混合,用水将浓缩物稀释到所需的浓度。
受各期棉红蜘蛛(Tetranychus urticae)严重侵袭的菜豆植物(Phaseolus vulgaris)浸泡在所需浓度的活性化合物制剂中。
在所需的时限之后,测定其百分活性。100%表示全部棉红蜘蛛被杀死;0%表示棉红蜘蛛中没有一个被杀死。
在本试验中,式(I-2)的化合物在0.001%活性化合物浓度下经13天后显示出超过90%的摧毁度,而比较物质(A)造成60%的摧毁度。
表C
Claims (3)
2.按照权利要求1的式(I)的苯并咪唑衍生物的制备方法,其特征在于,使式(II)的苯并咪唑与式(III)的磺酰氯起反应,
Cl-SO2-Y (III)式中,R、X1、X2、X3、X4、Y及Z的含义如前所述,
如有必要,上述反应可在稀释剂存在下进行;
且如有必要,上述反应可在反应助剂存在下进行。
3.农药,其特征在于它们包含至少一种按照权利要求1的式(I)的苯并咪唑衍生物。
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DEP4415435.6 | 1994-05-03 | ||
DE4415435A DE4415435A1 (de) | 1994-05-03 | 1994-05-03 | Benzimidazol-Derivate |
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EP (1) | EP0758334B1 (zh) |
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EP0517476A2 (en) * | 1991-06-03 | 1992-12-09 | Sumitomo Chemical Company Limited | Benzimidazole derivatives, a method for producing the same, agricultural and horticultural fungicides containing the same as an active ingredient and intermediate compounds thereof |
EP0545204A1 (de) * | 1991-12-04 | 1993-06-09 | Bayer Ag | 2-Cyanobenzimidazole, ein Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft und neue Vorprodukte |
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DE4237564A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Fluoralkyl(en)gruppen enthaltende o-Phenylendiamine |
DE4237567A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Schädlingsbekämpfungsmittel |
DE4321206A1 (de) * | 1993-06-25 | 1995-01-05 | Bayer Ag | Fungizide Wirkstoffkombinationen |
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- 1995-04-20 DE DE59510551T patent/DE59510551D1/de not_active Expired - Fee Related
- 1995-04-20 EP EP95916679A patent/EP0758334B1/de not_active Expired - Lifetime
- 1995-04-20 JP JP7527967A patent/JPH09512282A/ja not_active Ceased
- 1995-04-20 WO PCT/EP1995/001500 patent/WO1995029918A1/de active IP Right Grant
- 1995-04-20 PL PL95316990A patent/PL316990A1/xx unknown
- 1995-04-20 CN CN95192904A patent/CN1049894C/zh not_active Expired - Fee Related
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EP0517476A2 (en) * | 1991-06-03 | 1992-12-09 | Sumitomo Chemical Company Limited | Benzimidazole derivatives, a method for producing the same, agricultural and horticultural fungicides containing the same as an active ingredient and intermediate compounds thereof |
EP0545204A1 (de) * | 1991-12-04 | 1993-06-09 | Bayer Ag | 2-Cyanobenzimidazole, ein Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft und neue Vorprodukte |
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DE59510551D1 (de) | 2003-03-13 |
US6090954A (en) | 2000-07-18 |
WO1995029918A1 (de) | 1995-11-09 |
US5648316A (en) | 1997-07-15 |
PL316990A1 (en) | 1997-03-03 |
EP0758334B1 (de) | 2003-02-05 |
DE4415435A1 (de) | 1995-11-09 |
US5792873A (en) | 1998-08-11 |
EP0758334A1 (de) | 1997-02-19 |
US5990316A (en) | 1999-11-23 |
CN1147255A (zh) | 1997-04-09 |
JPH09512282A (ja) | 1997-12-09 |
AU2308795A (en) | 1995-11-29 |
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