CN87102981A - 新型硅烷衍生物,其制法,含该衍生物的制剂及其作为农药的应用 - Google Patents
新型硅烷衍生物,其制法,含该衍生物的制剂及其作为农药的应用 Download PDFInfo
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- CN87102981A CN87102981A CN87102981.2A CN87102981A CN87102981A CN 87102981 A CN87102981 A CN 87102981A CN 87102981 A CN87102981 A CN 87102981A CN 87102981 A CN87102981 A CN 87102981A
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- GBIHOLCMZGAKNG-CGAIIQECSA-N flucythrinate Chemical compound O=C([C@@H](C(C)C)C=1C=CC(OC(F)F)=CC=1)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 GBIHOLCMZGAKNG-CGAIIQECSA-N 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 231100000567 intoxicating Toxicity 0.000 description 1
- 230000002673 intoxicating effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([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])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960003536 phenothrin Drugs 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UIDUKLCLJMXFEO-UHFFFAOYSA-N propylsilane Chemical compound CCC[SiH3] UIDUKLCLJMXFEO-UHFFFAOYSA-N 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 235000021251 pulses Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Abstract
通式(I)化合物具有杀虫、杀螨及杀线虫性能:X=CH2,O;R1=(取代的)吡啶基或嘧啶基;R2,R3=烷基,烯基,或R2和R3为亚烷基;R4=H,CN,CCl3,C≡CH,烷基,F,C(S)-NH2;R5=吡啶基,呋喃基,噻吩基,邻苯二甲酰亚胺基,二(C1~C4)-烷基马来酰亚胺基,硫代邻苯二甲酰亚胺基,二氢邻苯二甲酰亚胺基,四氢邻苯二甲酰亚胺基,均可被取代,取代苯基,或R4和R5与桥联碳原子形成必要时被取代的茚基,环戊烯酰基或环戊烯基。
Description
迄今已知具有杀虫、杀螨及杀线虫作用的生物活性物质的基本结构真可谓种类繁多,仅就其中几种最重要者而谈,就有磷酸衍生物,氯代烃,N-甲基氨基甲酸酯,环丙(烷)基羧酸酯以及苯甲酰脲等。但令人惊讶的是(仅有个别例外,见日本特许公开说明书昭60-123461),目前尚未见到含有硅元素为基本骨架的具有杀虫、杀螨,杀线虫作用的化合物公开过〔C.Worthing,《农药手册》,第7版,Lavenham 1983;S.Pawlenko,《有机硅化合物》,编入《有机化学方法》(Houben-Weyl),卷ⅩⅢ/5,Georg Thieme出版社,Stuttgart 1980;R.Wegler,《植物保护剂及农药化学》,卷1,6及7,Springer出版社,Berlin 1970,1981〕。对除莠剂领域来说,这也是同一现实,而在杀菌剂研究中,迄今只发现三唑杀菌剂采用了含硅的基本结构(EP-A68813)。
现在已经发现具有含硅基本结构的新型生物活性物质,它在杀虫剂,杀螨剂及杀线虫剂领域中具有有效的应用性能。
本发明涉及通式(Ⅰ)化合物及其各种光学异构体,以及它们的可能的混合物,
式中
X=CH2或O,
R1=未被取代的或取代的吡啶基,或未被取代的或取代的嘧啶基,
R2,R3=(C1~C3)烷基,(C2~C8)烯基或R2和R3一起代表一个亚烷基链段,它们和硅原子共同形成一个未被取代的或被(C1~C4)烷基取代的四至六员杂环,
R5=吡啶基,呋喃基,噻吩基,邻苯二甲酰亚胺基,二(C1~C4)烷基马来酰亚胺基,硫代邻苯二甲酰亚胺基,二氢邻苯二甲酰亚氨基,四氢邻苯二甲酰亚氨基,它们均可被取代,取代的苯基
或者
R4和R5-它们与桥联的碳原子共同形成一个必要时被取代的茚基,环戊烯酰基或环戊烯基。
作为必要时取代的吡啶基R1或嘧啶基R1最好为通式(A)或(B)的吡啶基或嘧啶基,
式中0≤m+n+o≤3,m,n,o则为0至2的数值。R6,R7,R8及R9各自独立地代表囟素,(C1~C4)烷基,(C1~C3)烷氧基,(C1~C4)囟代烷基或(C1~C3)囟代烷氧基,或者R6,R7,R8,R9中的两个相连,如果它们在邻位相互形成一个亚甲基二氧基,亚乙基二氧基或(C3~C5)亚烷基的话。
吡啶基(例如通式A)与通式Ⅰ中Si原子的结合位置(自由价)最好在吡啶基(N=位置1)的2位或3位。嘧啶基(例如通式B)最好在2位或5位与硅原子连接。尤以m+n+o=1或2的通式(A)或(B)的单取代或双取代的吡啶基或嘧啶基为佳,其中取代基(R6~R9)最好在对位或间位与硅原子结合。
R2和R3最好为一个(C1~C3)烷基,如甲基,乙基,异丙基及正丙基,或者
R2和R3一起代表一个(C3~C5)亚烷基链段,它和硅原子共同形成一个四至六员环,诸如硅环丁烷,硅环戊烷或硅环己烷。
R2和R3尤为甲基为宜。
R4最好为氢,氰基或(C1~C4)烷基,尤以氢为宜。
R6~R9最好为F,Cl,Br,甲基,乙基,丙基,甲氧基,乙氧基,丙氧基,异丙氧基,二氟甲氧基,三氟甲氧基,1,1,2,2-四氟乙氧基,2,2,2-三氟乙氧基,1,1,2,3,3,3-六氟丙氧基,1,1,2-三氟-2-氯乙氧基,三氟甲基,1,1,2,2-四氟乙基,七氟丙基,亚甲基二氧基及亚乙基二氧基。
作为取代的苯基R5最好为通式(C)的苯基
式中R10和R11可各自独立为囟素,(C1~C4)烷基,(C1~C4)烷氧基,(C1~C4)囟代烷基,,苯基,N-吡咯基,或为通式(D)的基,
式中R12和R13也可各自独立为H,囟素,(C1~C4)烷基,(C1~C4)烷氧基以及(C1~C4)囟代烷基;U为-CH2-,
,-O-或-S-,最好为-O-;V,W为CH或N,其中V,W二者可同时为CH,但不能同时为N。对于通式(C)及(D)其它项的说明:
p,q=0至5的整数,其条件是p+q之和必须为1至5的
r,s=0,1或2,其条件是r+s之和必须为0,1或2;并且还有一个条件是,如果R10和R11对应于(D)基团,则p,q必须为0或1,并且p+q之和必须为1或2。
作为必要时取代的吡啶基R5为通式(E)的单取代的吡啶基,
式中R14=囟素(碘除外),(C1~C4)烷基,(C1~C4)烷氧基或(C1~C4)囟代烷基,Hal=囟素(尤指氟),或是氢。
作为必要时取代的噻吩基R5或呋喃基R5为通式(F)的杂环,
式中Z=O,S
R15=H,囟素,(C1~C4)烷基,(C1~C4)烷氧基,(C1~C4)囟代烷基,CN或NO2,
R16=必要时取代的苄基,炔丙基,烯丙基或苯氧基。
取代的苯基R5对本发明来说至关重要。
作为R5基典型例子给出以下基团:
五氟苯基,5-苄基-3-呋喃基,4-苯氧基苯基,3-苯氧基苯基,3-(4-氟苯氧基)苯基,3-(4-氯苯氧基)苯基,3-(4-溴苯氧基)苯基,3-(3-氟苯氧基)苯基,3-(3-氯苯氧基)苯基,3-(3-溴苯氧基)苯基,3-(2-氟苯氧基)苯基,3-(2-氯苯氧基)苯基,3-(2-溴苯氧基)苯基,3-(4-甲基苯氧基)苯基,3-(3-甲基苯氧基)苯基,3-(2-甲基苯氧基)苯基,3-(4-甲氧基苯氧基)苯基,3-(3-甲氧基苯氧基)苯基,3-(2-甲氧基苯氧基)苯基,3-(4-乙氧基苯氧基)苯基,3-(苯硫基)苯基,3-(4-氟苯硫基)苯基,3-(3-氟苯硫基)苯基,3-苯甲酰基苯基,3-苄基苯基,3-(4-氟苄基)苯基,3-(4-氯苄基)苯基,3-(3,5-二氯苯氧基)苯基,3-(3,4-二氯苯氧基)苯基,3-(4-氯-2-甲基苯氧基)苯基,3-(2-氧-5-甲基苯氧基)苯基,3-(4-氯-5-甲基苯氧基)苯基,3-(4-乙基苯氧基)苯基,3-(3-氯-5-甲氧基苯氧基)苯基,3-(2,5-二氯苯氧基)苯基,3-(3,5-二氯苯甲酰基)苯基,3-(3,4-二氯苯甲酰基)苯基,3-(4-甲基苄基)苯基,3-(4-异丙氧基苯氧基)苯基,4-氟-3-苯氧基苯基,4-氯-3-苯氧基苯基,4-溴-3-苯氧基苯基,4-氟-3-(4-氟苯氧基)苯基,4-氟-3-(4-氟苯氧基,4-氟-3-(4-溴苯氧基)苯基,4-氟-3-(4-甲基苯氧基)苯基,4-氟-3-(4-甲氧基苯氧基)苯基,4-氟-3-(3-氟苯氧基)苯基,4-氟-3-(3-氯苯氧基)苯基,4-氟-3(3-溴苯氧基)苯基,4-氟-3-(3-甲氧基苯氧基)苯基,4-氟-3-(4-乙氧基苯氧基)苯基,4-氟-3-(2-氟苯氧基)苯基,3-甲氧基-5-苯氧基苯基,2-氟-3-苯氧基苯基,2-氟-3-(4-氟苯氧基)苯基,2-氟-3-(3-氟苯氧基)苯基,2-氟-3-(2-氟苯氧基)苯基,3-氟-5-(4-氟苯氧基)苯基,3-氟-5-(3-氟苯氧基)苯基,3-氟-5-(2-氟苯氧基)苯基,4-甲基-3-苯氧基苯基,3-氟-5-(4-甲基苯氧基)苯基,3-氟-5-(3-甲氧基苯氧基)苯基,2-氟-5-(4-氟苯氧基)苯基,2-氟-5-(3-氟苯氧基)苯基,2-氟-5-(2-氟苯氧基)苯基,2-氯-3-苯氧基苯基,3-氟-5-苯氧基苯基,2-氟-5-苯氧基苯基,2-氯-5-苯氧基苯基,2-溴-5-苯氧基苯基,4-氯-3-(3-甲基苯氧基)苯基,4-氯-3-(4-氟苯氧基)苯基,3-氯-5-苯氧基苯基,3-溴-5-苯氧基苯基,4-溴-3-苯氧基苯基,4-三氟甲基-3-苯氧基苯基,4-氟-3-苯硫基苯基,4-氟-3-苄基苯基,3-(2-吡啶氧基)苯基,3-(3-吡啶氧基)苯基,4-氟-3-(2-吡啶氧基)苯基,4-氯-3-(2-吡啶氧基)苯基,4-溴-3(2-吡啶氧基)苯基,4-甲基-3-(2-吡啶氧基)苯基,4-氟-3-(3-吡啶氧基)苯基,4-氯-3-(3-吡啶氧基)苯基,4-溴-3-(3-吡啶氧基)苯基,4-甲基-3-(3-吡啶氧基)苯基,2-甲基-3-苯基苯基,2-甲基-3-(N-吡咯基)苯基,6-苯氧基-2-吡啶基,6-(4-氟苯氧基)-2-吡啶基,6-(4-氯苯氧基)-2-吡啶基,6-(4-溴苯氧基)-2-吡啶基,6-(4-甲基苯氧基)-2-吡啶基,6-(4-甲氧基苯氧基)-2-吡啶基,6-(4-乙氧基苯氧基)-2-吡啶基、6-(3-氟苯氧基)-2-吡啶基,6-(3-氟苯氧基)-2-吡啶基,6-(3-溴苯氧基-2-吡啶基,6-(3-甲氧基苯氧基)-2-吡啶基,6-(2-氟苯氧基)-2-吡啶基,6-(2-氯苯氧基)-2-吡啶基,6-(2-溴苯氧基)-2-吡啶基,5-炔丙基-3-呋喃基,N-苯邻二甲酰亚胺基,N-3,4,5,6-苯邻二甲酰亚胺基,2-甲基-5-炔丙基-3-呋喃基,4-叔丁基苯基,4-甲基苯基,4-异丙苯基,4-(2-氯-4-三氟甲基-2-吡啶氧基)苯基,4-环己基苯基,4-二氟甲氧苯基,4-联苯基及4-三甲基甲硅烷基苯基以及4-苯氧基-2-噻吩基。
2-烯丙基-3-甲基环戊-2-烯-1-酮-4-基,4-苯基-1,2-二氢化茚-2-基。
本发明也提出了通式(Ⅰ)所示化合物的制法,其中:
a)对于X=CH2的化合物,将通式(Ⅱ)所示的硅烷,
其中Y为
离核基团,如囟素或磺酸酯,与通式(Ⅲ)所示金属有机试剂反应,
式中M相当于
当量的碱金属或碱土金属,特别是Li,Na,K,Mg,X′相当于亚甲基,R4′相当于H或(C1~C4)烷基,
或者
b)将通式(Ⅳ)或(Ⅴ)所示硅烷
必要时在碱存在下与通式(Ⅵ)所示烷基化剂进行反应,
或者
c)将通式(Ⅶ)所示硅烷
与类型(Ⅷ)所示的氢囟酸(HⅩ)化合物在碱存在下进行反应,
或与类型(Ⅸ)金属有机化合物进行反应,
或者
d)对X=CH2的通式(Ⅰ)所示化合物,将通式(Ⅹ)所示硅烷
与类型(Ⅺ)化合物进行反应,
或者
e)对X=CH2的化合物,将通式(Ⅻ)硅烷,
与通式(ⅩⅢ)所示的金属有机化合物进行反应,
或者
f)将通式(ⅩⅣ)所示硅烷
与类型(ⅩⅤ)金属有机试剂进行反应,
或者
g)将通式(ⅩⅥ)所示硅烷
与类型(ⅩⅦ)金属有机试剂进行反应,
或者
h)对于X=CH2的化合物,将通式(ⅩⅩⅩ)所示硅烷
在周期表第Ⅷ副族元素络合物作为催化剂存在下,与通式(ⅩⅩⅪ)的烯烃进行反应,
或者
ⅰ)对于X≠CH2的化合物,将通式(ⅩⅩⅩⅡ)所示硅烷,
与通式(ⅩⅩⅩⅢ)烷基化剂进行反应,
作为起始化合物在a)制法中所用的通式(Ⅱ)所示硅烷,部分是新的,可按文献中已知方法制备,其中从通式(ⅩⅧ),(ⅩⅨ)或(ⅩⅩ)所示硅烷出发进行制备,对尚缺的有机基可藉助适宜的金属有机试剂导入(参见《有机化学方法》(Houben-weyl),卷ⅩⅢ/5,Georg Thieme出版社,Stuttgart,1980),
式中R,R′,R″相当于R1,R2,R3基,Y和M的定义同上。
作为起始化合物在a)制法中所用通式(Ⅲ)所示的金属有机试剂,部分是新的,可按文献中已知方法制备,其中先按Reformatskij提出的方法〔见《有机化学方法》(Houben-Weyl),卷ⅩⅢ/2a,Georg Thieme出版社,Stuttgart 1973〕制成通式(ⅩⅪ)的羰基化合物,
其中R和R的定义同上,然后再按Wittig〔见《有机化学方法》(Houben-Weyl),卷El,Georg Thieme出版社,Stuttgart 1982〕或者按Horner提出的方法〔见L.Horner,《化学研究进展》,7/1,1(1966/67)〕转化成相应的α,β-不饱和酯(ⅩⅩⅡ),
然后再按标准方法〔见《有机化学方法》(Houben-Weyl),卷4/1c及4/1d,Georg Thieme出版社,Stuttgart 1980和1981〕将其还原成为醇(ⅩⅩⅢ),
并且再按标准方法〔见《有机化学方法》(Houben-Weyl),卷5/3及5/4,Georg Thieme出版社,Stuttgart 1960和1962〕将其转化成为适宜的囟化物(ⅩⅩⅣ),
最后用碱金属或碱土金属使其转化为所需要的类型(Ⅲ)所示的金属有机试剂。
作为起始化合物在b)制法中所用的通式(Ⅳ)和(Ⅴ)所示硅烷,部分是新的,可按文献中已知方法制备〔见《有机化学方法》(Houben-Weyl),卷ⅩⅢ/5,Georg Thieme出版社,Stuttgart 1980〕,其中,
1)将通式(ⅩⅩⅤ)所示硅烷,
式中R2,R3和Y的定义同上,Hal可为Br或Cl,
与通式(ⅩⅤ)所示金属氧基试剂反应,
从而形成类型(Ⅶ)的中间产物,
然后按标准方法〔见《有机化学方法》(Houben-Weyl),卷13/3a,Georg Thieme出版社,Stuttgat 1982〕转化为硼烷(ⅩⅩⅥ),
最后按文献中已知方法〔见《有机化学方法》(Houben-Weyl),卷13/3c,Georg Thieme出版社,Stuttgart 1984〕将其裂解为所希望的化合物(Ⅳ)(X=O,S)。
2)将通式(ⅩⅩⅦ)所示硅烷,
(Houben-Weyl),卷ⅩⅢ/5,Georg Thieme出版社,Stuttgart 1980〕与碱金属反应转化为相应的金属化的硅烷,然后与甲醛反应便生成类型(Ⅳ)化合物,其中X=O。
3)将通式(ⅩⅩⅧ)所示硅烷,
式中R2,R3和Y的定义同上,Hal为氯,溴,
与通式(ⅩⅤ)所示金属有机试剂反应,
从而生成中间产物(ⅩⅩⅨ)
该中间产物与碱金属或碱土金属反应,则生成含X=CH2的类型(Ⅴ)化合物。
作为起始化合物在c)制法中所用的通式(Ⅶ)所示硅烷,
其中Y为囟素,其余定义同上,可通过硅烷(ⅩⅩⅤ)与金属氧基试剂(ⅩⅤ)与反应而制得。
含有Y为磺酸酯的化合物(Ⅶ)可由类型(Ⅳ)带有磺酸基的醇进行适宜的酯化反应来合成,该反应可按一般方法进行〔见《有机化学方法》(Houben-Weyl),卷Ⅸ,Georg Thieme出版社,Stuttgart 1955〕,
其中X=O。
作为起始化合物在制法h)中所用的通式ⅩⅩⅩ所示硅烷,部分是新的,可按文献中已知方法制备〔见《有机化学方法》(Houben-Weyl),卷ⅩⅢ/5,Georg Thieme出版社,Stuttgart 1980〕,其中,
1)将通式ⅩⅩⅩⅣ硅烷
与通式(Ⅺ)所示金属有机试剂进行反应而制得,
或者
2)将通式(Ⅱ)所示硅烷
与金属氢化物,例如与氢化钠或氢化锂铝进行反应而制得。
作为起始化合物在h)制法中所用的通式(ⅩⅩⅪ)所示烯烃可按文献中已知的方法制备,
其中可由通式ⅩⅩⅩⅤa或ⅩⅩⅩⅤb所示烯烃
与通式ⅩⅩⅩⅥa或ⅩⅩⅩⅥb所示金属有机试剂进行反应而制得,
这两种化合物可用相应的囟素化合物制得。
通式ⅩⅩⅪ所示的化合物,部分是新的。因此,本发明也涉及通式ⅩⅩⅪ化合物,其中R4为H,R5为下式所示基团:
R17为H或囟素,而囟素中尤指氟。
作为起始化合物在ⅰ)制法中所用的通式ⅩⅩⅩⅡ所示金属化硅烷,
部分是新的,可按文献中已知的方法由离析物ⅩⅩⅦ与碱金属反应而制得:
其中Y′为囟素或
作为起始化合物在制法ⅰ)中所用的烷基化剂ⅩⅩⅩⅢ,
部分也是新的,可按文献中已知的方法制得〔见,例如《有机化学方法》(Houben-Weyl),卷Ⅴ/3,Georg Thieme出版社,Stuttgart 1962〕,其中,例如在X=O时,可由通式ⅩⅩⅩⅦ所示醇与囟化剂如氢氯酸,氢溴酸或亚硫酰(二)氯在多聚甲醛存在下进行反应而制得,
其它作为起始化合物所用的通式(Ⅵ),(Ⅷ),(Ⅸ),(Ⅹ),(Ⅺ),(Ⅻ),(ⅩⅢ),(ⅩⅣ),(ⅩⅤ),(ⅩⅥ)及(ⅩⅦ)所示化合物,部分也是新的。可按上述文献中的合成步骤进行合成(参见上述引用的文献),或按有机化学标准方法合成。因此,金属有机中间产物例如可根据各种不同的合成方案通过氢/金属交换,但是最好通过囟素/金属交换制备出来。
已讲到的合成方案a),d),e),f),g)及i)最好均在稀释剂中进行,稀释剂的性能取决于所用的金属有机物的种类。作为稀释剂尤以脂肪烃和芳烃为宜,诸如戊烷,己烷,庚烷,环己烷,石油醚,汽油,石油英,苯,甲苯及二甲苯,醚类如二乙醇,二丁醚,乙二醇二甲醚,二甘醇二甲醚,四氢呋喃,二恶烷,并包括由前述溶剂组成的各种可能的混合物。
在上述合成方案中,反应温度在=75℃和+150℃之间,尤其是在-75℃和+105℃之间为宜。起始原料通常当量加入,但也可能有一种组分或其它组分过量。
对于上述其它合成方案b)和c)来说,基本上同方案a)及d)-g)。但在采用类型(Ⅳ)及(Ⅷ)离析物时,还允许采用其它稀释剂。在这种情况下适于采用下列稀释剂,酮类如丙酮,甲乙酮,甲基异丙基酮及甲基异丁基酮,酯类如乙酸甲酯及乙酸乙酯,腈类如乙腈及丙腈,酰胺类如二甲基甲酰胺,二甲基乙酰胺,以及N-甲基吡咯烷酮,二甲基亚砜,四亚甲基砜(环丁砜)和六甲基磷酸三酰胺。作为碱可用无机碱,诸如碱金属或碱土金属的氢氧化物,氢化物,碳酸盐或碳酸氢盐,但也可用有机碱,诸如吡啶,三乙胺,N,N-二异丙基乙胺或者二氮二环辛烷。
与通式(Ⅰ)化合物所有其它合成方法相反,所提到的合成方案h)最好是在无稀释剂下进行,但也适于用溶剂,如用环己烷,石油醚,苯,甲苯,二甲苯及其它反应介质。作为催化剂可用周期表第Ⅷ副族元素的络合物,如用H2PtCl6,Co2(CO)8,Rh4(CO)12,Ir4(CO)12或RhCl〔P(C6H5)3〕3〔见《有机化学方法》(Houben-Weyl),卷ⅩⅢ/5,Georg Thieme出版社,Stuttgart 1980,第51页以下及该书引用的文献〕。催化剂对反应的离析物的配比视催化剂种类而定,例如在用H2PtCl6情况下,其变化范围为1∶107至1∶106。
通式(Ⅰ)所示化合物的分离及必需时的精制可按通用方法进行。例如采用溶剂蒸发法(必要时在减压下进行)及随后的连续蒸馏法或色谱柱提纯法,或采用两相间粗产品分配以及随后的普通加工方法。
通式(Ⅰ)化合物均能很好地溶解在绝大多数有机溶剂中。
这类生物活性化合物具有良好的植物相容性以及优良的热血动物致毒性,适于防治动物侵害,特别适于防治在农业,森林,仓库及物料保存以及公共卫生领域中常出现的昆虫、蛛形纲动物和线虫。这类化合物对一般具有知觉性及具有抵抗力的生物种以及在全部或个别发育阶段的生物种均有防治效果。上述各类害虫包括:
属于等足目,例如潮虫(球鼠妇),鼠妇(Armadillidium Vulgare),Porcellio scaber。
属于倍员目:例如Blaniulus guttulatus。
属于唇足亚纲,例如地蜈蚣(Geophilus carpophagus),蚰蜒(Scutigera spec.)
属于综合纲,例如庭园么蚰。
属于缨尾目,例如西洋衣鱼。
属于弹尾目,例如刺跳虫(Onychiurus armatus)。
属于革翅目,例如欧洲球螋。
属于等翅目,例如散白蚁属。
属于虱目,例如葡萄根瘤蚜,瘿绵蚜属,体虱,盲虱属,长鄂虱属。
属于食毛目,例如羽虱属,畜虱属。
属于缨翅目,例如温室条篱蓟马,烟蓟马。
属于异翅亚目,例如扁盾蝽属,红蝽(Dysdercus intermedius),方背皮蝽,温带臭虫,长江猪蝽,猪蝽属。
属于同翅目,例如甘兰粉虱,木薯粉虱,温室粉虱,棉蚜,甘蓝蚜,茶藨隐瘤蚜,敌伏蚜,敌普蚜,苹果绵蚜,梅大尾蚜,麦长管蚜,瘤额蚜属,忽布疣蚜,缢管属,小叶蝉,诱贝蚜,艾辛蚜,水木竖蚧,乌盔蚧,灰飞虱,褐飞虱,红肾圆盾蚧,常春藤圆盾蚧,粉蚧属,木虱属。
属于鳞翅目,例如:红玲麦蛾,松尺蠖,Cheimatobia brumata蛾,苹细蛾,苹果巢蛾,菜蛾,黄褐天幕毛虫,黄毒蛾,毒蛾,棉潜蛾,桔潜蛾,夜蛾属,切根虫属,地虎属,埃及金刚钻,夜蛾属,甜菜夜蛾,甘蓝夜蛾,松夜蛾,斜纹夜蛾,夜蛾属,粉纹夜蛾,苹果小卷蛾,菜粉蝶属,螟类,玉米螟,地中海粉斑螟,六蜡螟,幕谷蛾,袋谷蛾,褐织蛾,亚麻黄卷蛾,烟卷蛾,枞色卷蛾,葡萄果蠹蛾,茶长卷蛾,栎绿卷蛾。
属于鞘翅目,例如:家具窃蠹,谷蠹,菜锥胸豆象,菜豆象,北美家天牛,杨树萤叶甲,马玲薯叶甲,辣根猿叶,叶甲属,油菜金头跳甲,大豆瓢虫,锯谷盗,花象属,谷象属,黑葡萄耳象,香蕉根颈象,白菜籽龟象,紫苜蓿叶象,皮蠹属,斑皮蠹属,圆皮蠹属,毛皮蠹属,粉蠹属,菜花露尾甲,蛛甲属,黄蛛甲,裸蛛甲,拟谷盗属,黄粉虫,叩头虫属,宽胸叩头虫属,西方五月鳃鱼角金龟,马玲薯鳃角金龟,褐新西兰助翅鳃角金龟。
属于膜翅目,例如:据角叶蜂属,叶峰属,地蚁属,法老蚁,胡蜂属。
属于双翅目,例如,伊蚊属,按蚊属,库蚊属,黑尾果蝇,象蝇属,厕蝇属,红头丽蝇,绿蝇属,金蝇属,疽蝇科,胃蝇属,赭虱属,厩螯蝇属,狂蝇属,皮蝇属,虻属,螗蜩属,毛蚊属,瑞典麦杆蝇,草种蝇属,甜菜泉蝇,地中海蜡实蝇,橄榄大实蝇,欧洲大蚊。
属于蚤目,例如:印鼠客蚤,角叶蚤属。
属于蝽科,例如:蝎蛉,黑寡妇球腹蛛。
属于蜱螨目,例如:粗脚粉螨,锐绿蜱属,钝缘蜱属,鸡皮刺螨,茶藨瘿螨,桔芸锈螨,牛蜱属,扁头蜱科,花蜱属,卉乐蜱属,硬蜱属,痒螨属,皮痒螨属,疥螨属,跗线螨属,苜蓿苔螨,全爪螨属,叶螨属。
此外,本发明提出的化合物对损害植物的线虫具有优异的抵抗作用,如防治根结线虫属,狭佈叩头虫,茎线虫,叶线虫,内侵线虫,球线虫,草地垫刃线虫属,长囊线虫,剑尾线虫。
本发明也提出一种制剂,它除含有适宜的配方助剂外还含有通式(Ⅰ)化合物。
根据本发明提出的制剂一般含有1~95%(重量)的通式(Ⅰ)生物活性物质。一般可将它们配制成可湿性粉剂,乳油,喷撒溶液,粉剂或颗粒剂加以利用。
可湿性粉剂可制成均匀分散在水中的制剂,这种制剂除含有生物活性物质及稀释剂,或惰性物质,还含有润湿剂,例如含有聚氧乙基化烷基酚,聚氧乙基化脂肪醇,烷基磺酸盐或烷基苯酚磺酸盐以及分散剂,例如木质素磺酸钠,2,2′-二萘基甲烷-6,6′-二磺酸钠,二丁基萘磺酸钠或者油酰基甲基牛磺酸钠。
乳油可在加入一种或多种乳化剂下将生物活性物质溶解在有机溶剂中制成,例如溶解在丁醇,环己酮,二甲基甲酰胺,二甲苯中,也可溶解在高沸点芳烃或烃类中。作为乳化剂可采用:烷基芳基磺酸钙盐,如十二烷基苯磺酸钙,或非离子型乳化剂,如脂肪酸聚乙二醇酯,烷基芳基聚乙二醇醚,脂肪醇聚乙二醇醚,环氧丙烷-环氧乙烷缩合产物,烷基聚醚,脱水山梨(糖)醇脂肪酸酯,聚氧乙烯脱水山梨(糖)醇脂肪酸酯或聚氧乙烯山梨酸酯。
粉剂可通过生物活性物质与细分散固体材料,例如与滑石,天然粘土,如高岭土,膨润土,斑岩或硅藻土共同研磨而制得。颗粒剂可将生物活性物质喷涂在吸附性的颗粒状惰性材料上而制得,或者借助粘合剂,例如聚乙烯醇、聚丙烯酸钠,也可借助矿物油将生物活性物质浓缩物敷在载体材料如砂,高岭土的表面上,或者敷在颗粒状惰性材料的表面上而制得。也可采用生产肥料颗粒用的普通方式,根据需要将适当的生物活性物质与肥料混合而制得。
基于本发明的生物活性物质可采用一般市售品制剂形式以及采用将这些配方与其它生物活性物质互相混合并进一步加工成的其它应用形式,例如与杀虫剂,诱饵,杀菌剂,杀螨剂,杀线虫剂,防霉剂,植物生长调节剂或除草剂互相混合。例如,所用杀虫剂特别是磷酸酯,氨基甲酸酯,碳酸酯,甲脒,锡化合物,由微生物制得的物料。优选的混合组分包括:
1.选自磷酸酯类
乙基谷硫磷(益棉磷,乙基保棉磷),甲基保棉磷,1-(4-氯苯基)-4-(O-乙基,S-丙基)磷酰氧吡唑(TIA-230),氯蜱硫磷(毒死蜱),蝇毒磷,内吸磷(一○五九),S-甲基内吸磷,二嗪农,敌敌畏,乐果,灭克磷,乙嘧硫磷,杀螟松,倍硫磷,庚烯磷,对硫磷(一六○五),甲基对硫磷,伏杀硫磷,乙基虫螨磷,甲基虫螨磷,朴吩磷(Profenfos),低毒硫磷,硫普磷(Sulprofos),三唑磷,敌百虫;
2.选自氨基甲酸酯类
涕灭威,噁虫威,BPMC(2-(-甲基丙基)苯基甲基氨基甲酸酯),甲硫基丁酮甲氨基羰基肟(Butocarboxim),丁酮肟威,西维因,虫螨威,硫泛威(Carbosulfan),氯乙威(Cloethocarb),异丙威,甲肟威,草肟威,普米威(Primicarb),甲丙威,普洛赛(Propoxur),硫双威(Thiodicarb);
3.选自羧酸酯类
丙烯菊酯,α型甲除虫菊(Alphamethrin),右旋反丙烯菊酯,右旋反苄呋菊酯,环丙除虫菊(Cycloprothrin),环氟除虫菊(Cyfluthrin),环囟除虫菊(Cyhalothrin),腈二氯苯醚菊酯,δ型甲除虫菊(Deltamethrin),2,2-二甲基-3-(2-氯-2-三氟甲基乙烯基)环丙酸(α-氰基-3-苯基-2-甲基苄基)酯(FMC54800),伐丙除虫菊(Fenpropathrin),伐氟除虫菊(Fenfluthrin),腈氯苯苯醚菊酯,氟氰除虫菊酯(Flucythrinate),氟甲除虫菊(Flumethrin),氟缬氨酸酯(Fluvalinate),全甲除虫菊,苄呋喃酯,Tralo型甲除虫菊(Tralomethrin);
4.选自甲脒类
氨山氮螨,杀虫脒基;
5.选自铝化合物类
偶氮环锡(Azocyclotin),三环锡,螨完锡;
6.其它类
α-和β-阿威麦克汀(α-和β-Auermectine),苏云金杆菌,苄硫丹,乐杀螨(Bunsultap),双氯芬芹※,布洛非辛(Buprofecin),巴丹,曲洛麦芹(Cyromecin),开乐散,硫丹,乙氧丙氧芬,伐氧威(Fenoxycarb),六噻斯(Hexythiazox),3-〔2-(4-乙氧苯基)-2-甲基-丙氧甲基〕-1,3-二苯醚(MTI-500),5-〔4-(4-乙氧苯基)-4-甲苯基〕-2-氟-1,3-二苯醚(MTI-800),3-(2-氯苯基)-3-羟基-2-(2-苯基-4-噻唑基)丙烯腈(SN 72129),硫环拉姆(Thiocyclam),开朴敌(Kernpolyederen)及克拉灵(Granuloseviren)。
※双氯芬芹(Bisclofentezin)
在一般市售品制剂基础上加工过的应用形式中,生物活性物质的含量可在宽范围内变化。在这种应用形式中生物活性物质浓度可达0.0000001至100%(重量),最好在0.00001和1%(重量)之间。
施用要采用与使用形式相适应的方式。
本发明提出的生物活性物质也适宜于防治外寄生虫和内寄生虫,特别适用于防治兽医领域及家畜领域的外寄生害虫。
使用本发明提出的生物活性物质时可采用通常的使用方式,例如采用片剂、胶囊,饮料及粒剂等口服形式,也可采用经皮肤使用的方式,例如浸泡(浸渍),喷射(喷洒),灌浇(灌淋),撒粉。
每种适宜的剂量和配方都要具体地根据被防治的动物的种类及发育阶段以及害虫侵扰程度而定,并且采用一般方法就很容易获知和确定。例如,对牛来说这种新型化合物使用剂量为0.1至100毫克/公斤体重。
用下述实例对本发明加以说明。
A.配方实例
a)粉剂由10份(重量)生物活性物质和90份(重量)滑石作为惰性材料进行混合而制得,并经锤磨机粉碎。
b)易在水中分散的可湿性粉剂由25份(重量)生物活性物质,65份(重量)含高岭土的石英作为惰性材料,10份(重量)木质素磺酸钾及1份(重量)油酰甲牛磺酸钠作为润湿剂和分散剂进行混合而制得,并经棒磨机研磨。
c)易分散于水中的分散体浓缩物由20份(重量)生物活性物质与6份(重量)烷基苯酚聚乙二醇醚((R)Triton X207),3份(重量)异十三烷醇聚乙二醇醚(8Aeo)及71份(重量)烷(属)烃矿物油(例如,沸程约从225至377℃以上)进行混合而制得,并经球磨机研磨至粒度低于5微米。
d)乳油由15份(重量)生物活性物质,75份(重量)环己酮作为溶剂以及10份(重量)氧乙基化壬基苯酚(10 Aeo)作为乳化剂而制得。
e)颗粒剂由2至15份(重量)生物活性物质及惰性粒状载体材料,如绿坡缕石,浮石粒料及/或石英砂而制得。
B.化学反应实例
制备过程
向溶于10毫升无水四氢呋喃(THF)的2.4克(0.10摩尔)镁屑中滴加由18.2克(0.09摩尔)2-乙氧基-5-溴吡啶(由2,5-二溴吡啶及甲醇钠溶于DMSO中制得),11.4克(0.12摩尔)(-)氯二甲基硅烷及50毫升无水四氢呋喃所组成的混合物,在该过程中发生强放热反应。经两小时回流煮沸即可完成这一反应。然后注水,并用正己烷萃取多次。萃取物用水及饱和食盐溶液洗涤,经干燥及蒸发,将残余物蒸馏出来。得到作为无色油状物(Kp.7=140~150℃)的7克(43%)2-乙氧基-5-二甲基甲硅烷基吡啶。
将两滴溶于异丙醇中的30%六氯铂酸溶液掺入到由3.6克(20毫摩尔)2-乙氧基-5-二甲基甲硅烷基吡啶及4.2克(20毫摩尔)3-烯丙基二苯基醚组成的混合物中。略微加热后即开始放热反应。得到的粗产品经球形管蒸馏,生成3.6克(46%)(2-乙氧基吡啶-5-基)-二甲基-3-(3-苯氧基苯基)丙基硅烷,为Kp.0.15=230℃及n20 D=1.5618的无色油状物。
按照该过程可制得下列X=CH的通式(Ⅰ)化合物。X=O的下列化合物,例如可按上述b)法制备。
表中的Et均为乙基的英文缩写。
C.生物活性试验实例
实例1
将含有1000ppm生物活性物质的用水稀释的乳液喷洒在具有大量菜豆蚜虫(豆蚜-Aphis craccivora)的农田植物菜豆(蚕豆-Vicia faba)上,喷洒量直至开始滴落为止。三天后,当采用实例1,2,3,5,8,9,10,13,19,20,30,46,52,100,101,106,107,156,161和162的生物活性物质药剂时,死亡率分别达到100%。
实例2
将用水稀释的乳液(含1000ppm生物活性物质)喷淋在具有大量粉虱(温室白粉虱-Trialeurodes vaporarium)的豆科植物(普通菜豆-Phaseolus vulgaris)上,喷淋量直至开始滴落为止。将植物置于培植室后,用显微镜观查,当采用实例2,8,9,13,19,46和101的生物活性物质药剂时,十五天后的结果是,死亡率分别达到100%。
实例3
试验过程:类似实例2
试验用动物:棉叶螨(Tetranychus urticae)
试验植物:普通菜豆
药剂用量:喷淋液中含1000ppm生物活性物质
八天后测试药效表明,当采用实例9化合物时,死亡率达到100%。
实例4
将用水稀释的乳液(喷淋液中含1000ppm生物活性物质)喷洒在具有大量桔蚜(桔粉蚧-Pseudococcus citri)的豆科植物(普通菜豆)上,喷洒量直至开始滴落为止。
在20~25℃培植室放置七天时间后检查发现:
采用实例1,2,3,5,8,9,100,101,106,107和162化合物时,死亡率达到100%。
实例5
用水稀释的乳液(喷淋液中含生物活性物质1000ppm)处理棉(臭)虫(美州脊胸长蝽-Oncopeltus fasciatus),所用生物活性物质选自实例1,2,3,5,8,9,10,13,19,20,30,46,52,100,101,106和162。
然后将棉虫在室温下放置在带有通气盖的容器中。
处理后五天发现棉虫死亡,使用每种上述生物活性物质时死亡率均达100%。
实例6
每次用3毫升含2000ppm生物活性物质的水乳液在饲料糊凝固后喷洒在用合成营养介质涂层的佩特里(Petri)培养皿的底部内侧。喷洒层干燥后,加入10只普通棉
虫(斜纹液蛾-Prodenia litura),将培养皿在21℃下保存七天,然后测定每种化合物效能(用%死亡率表示)。在该试验中,化合物2,8,9,10,18,19,30,52,100,101,106和107的效能分别为100%。
实例7
用浓度为1000ppm(以生物活性物质计)的实例68化合物的水乳液处理豆科植物(普通菜豆)的叶子,并同时在观察笼中放入墨西哥豆科甲虫(Epilachnavarivestis)幼虫。48小时后评价;被试验的动物100%死亡。用实例1,2,8和19化合物所做的试验均显示出相同的效能。
实例8
用吸移管取出1毫升浓度为1000ppm的溶于丙酮中的实例68化合物作为生物活性物质,将其均匀涂敷在佩特里培养皿顶盖及底部内侧,并且敞开培养皿直到溶剂完全蒸发。然后将10只舍蝇(家蝇-Musca domestica)放入加盖的佩特里培养皿中。3小时后,被试验的动物100%死亡。采用实例1,2,100,101,106和107化合物也显示出相同效能。
实例9
用吸移管每次取出1毫升浓度为2000ppm的溶于丙酮中的生物活性物质溶液,将其均匀涂敷在佩特里培养皿顶盖及底部内侧。溶剂完全蒸发后,向每个佩特里培养皿加入10只德国小蠊(Blatella germanica)幼虫(L4),并用盖关上培养皿。72小时后评断效能(用%死亡率表示)。在该试验中,化合物1,2,3,5,8,9,10,13,19,20,30,46,52,100,101,106和107的效能均为100%。
Claims (10)
1、通式(Ⅰ)化合物的制备方法
式中
X=CH2或O,
R1=未被取代的或取代的吡啶基,或未被取代的或取代的嘧啶基,
R2,R3=(C1~C3)烷基,(C2~C8)烯基或R2和R3一起代表一个亚烷基链段,它们和硅原子共同形成一个未被取代的或被(C1~C4)烷基取代的四至六员杂环,
R5=吡啶基,呋喃基,噻吩基,邻苯二甲酰亚胺基,二(C1~C4)烷基马来酰亚胺基,硫代邻苯二甲酰亚胺基,二氢邻苯二甲酰亚胺基,四氢邻苯二甲酰亚胺基,它们均可被取代,取代的苯基
或者
R4和R5-它们与桥联的碳原子共同形成必要时被取代的茚基,环戊烯酰基或环戊烯基,其特征在于:
a)对于X=CH2的化合物,将通式(Ⅱ)所示硅烷,
式中Y
为离核基,如囟素或磺酸酯,
与通式(Ⅲ)所示金属有机试剂进行反应,
式中M相当于
当量碱金属或碱土金属,X′相当于亚甲基,R4′相当于H或(C1~C4)烷基,
或者
b)将通式(Ⅳ)或(Ⅴ)所示硅烷,
与通式(Ⅵ)所示烷基化剂进行反应,
必需时在碱存在下进行该反应,
或者
c)将通式(Ⅶ)所示硅烷,
在碱存在下与类型(Ⅶ)的氢囟酸(HX)化合物进行反应,
或与类型(IX)所示金属有机化合物进行反应,
或者
d)对于X=CH2的化合物,将通式(X)所示硅烷,
与类型(Ⅺ)化合物进行反应,
或者
e)对于X=CH2的化合物,将通式(Ⅻ)所示硅烷,
与通式(ⅩⅢ)所示金属有机化合物进行反应,
或者
f)将通式(ⅩⅣ)所示硅烷,
与类型(ⅩⅤ)所示金属有机试剂进行反应,
或者
g)将通式(ⅩⅥ)所示硅烷,
与类型(ⅩⅦ)金属有机试剂进行反应,
或者
h)对于X=CH2的化合物,将通式(ⅩⅩⅩ)所示硅烷,
与通式(ⅩⅩⅪ)所示烯烃在周期表第Ⅷ族副族元素络合物作为催化剂存在下进行反应,
i)对X≠CH2的化合物,将通式(ⅩⅩⅩⅡ)所示硅烷,
与通式(ⅩⅩⅩⅢ)所示烷基化剂进行反应,
2、根据权利要求1所述方法,对于权利要求1提出的通式1化合物,其中R1为通式(A)或(B)所示的吡啶基或嘧啶基,
式中
m,n,o为0至2的数值,并且符合0≤m+n+o≤3,
R6,R7,R8,R9为各自独立地代表囟素,(C1~C4)烷基,(C1~C3)烷氧基,(C1~C3)囟代烷基或(C1~C3)囟代烷氧基,或R6,R7,R8,R9中的两个相连,如果它们在邻位相互形成一个亚甲基二氧基,亚乙基二氧基或(C3~C5)亚烷基的话,
R2,R3=(C1~C3)烷基,或R2和R3共同形成一个(C3~C5亚烷基链段,
R4=H,-CN或(C1~C4)烷基
R5=通式(c)所示被取代的苯基
式中R10和R11各自独立地为囟素,(C1~C4)烷基,(C1~C4)烷氧基,(C1~C4)囟代烷基,苯基,N-吡咯基或通式(D)的基团,
式中R12和R13各自独立地为H,囟素,(C1~C4)烷基,(C1~C4)烷氧基及(C1~C4)囟代烷基;U=-CH2-,
,-O-或-S-,最好为-O-;V,W=CH或N,其中V,W二者可以同时为CH,但不能同时为N,对通式(C)和(D)其它项的说明:
p,q=0至5的整数,其条件是p+q之和必须为1至5的数值,
r,s=0,1或2,条件是r+s之和必须为0,1或2,并且还有一个条件是,如果R10或R11对应于(D)基团时,则p,q必须为0或1,并且p+q之和必须为1或2,或者R5为通式(E)吡啶基,
其中R14=囟素(碘除外),(C1~C4)烷基,(C1~C4)烷氧基或(C1~C4)囟代烷基,Hal=囟素(尤指氟),或H。
5、农药组合物,其特征在于,它含有权利要求1,2,3或4所述的通式(Ⅰ)化合物。
6、杀虫剂组合物,其特征在于,它含有权利要求1,2,3或4所述的通式(Ⅰ)化合物。
7、杀螨剂组合物,其特征在于,它含有权利要求1,2,3或4所述的通式(Ⅰ)化合物。
8、杀线虫剂组合物,其特征在于,它含有权利要求1,2,3或4所述的通式(Ⅰ)化合物。
9、采用权利要求1,2,3或4所述的通式(Ⅰ)化合物作为农药。
10、防治害虫、螨类或线虫的方法,其特征在于,将有效剂量的根据权利要求1,2,3或4所述的通式(Ⅰ)化合物施用在被其浸袭的表面、植物或材质上。
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CN90108778A CN1025470C (zh) | 1986-05-31 | 1987-04-02 | 含新型硅烷衍生物的农药,杀虫剂和杀螨剂组合物 |
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DEP3618354.7 | 1986-05-31 |
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CN1025502C CN1025502C (zh) | 1994-07-20 |
Family
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CN87102981A Expired - Fee Related CN1025502C (zh) | 1986-05-31 | 1987-04-24 | 新型硅烷衍生物制备方法 |
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Country Status (25)
Country | Link |
---|---|
US (1) | US4775664A (zh) |
EP (1) | EP0249015B1 (zh) |
JP (1) | JP2598015B2 (zh) |
KR (1) | KR950001701B1 (zh) |
CN (2) | CN1025470C (zh) |
AT (1) | ATE54149T1 (zh) |
AU (1) | AU603569B2 (zh) |
BR (1) | BR8701971A (zh) |
CA (1) | CA1301154C (zh) |
CS (1) | CS268533B2 (zh) |
DD (1) | DD261737A5 (zh) |
DE (1) | DE3763412D1 (zh) |
DK (1) | DK209487A (zh) |
ES (1) | ES2017954B3 (zh) |
GR (1) | GR3000646T3 (zh) |
HU (1) | HU201557B (zh) |
IL (1) | IL82268A (zh) |
MA (1) | MA20959A1 (zh) |
MY (1) | MY100845A (zh) |
NZ (1) | NZ220063A (zh) |
PH (1) | PH24101A (zh) |
PT (1) | PT84763B (zh) |
SU (1) | SU1618274A3 (zh) |
TR (1) | TR23344A (zh) |
ZA (1) | ZA872878B (zh) |
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US4883789A (en) * | 1986-06-02 | 1989-11-28 | Fmc Corporation | Substituted phenyltrialkylsilane insecticides |
US4919935A (en) * | 1987-09-30 | 1990-04-24 | R. Maag Ag | Insecticidal compositions |
US5139785A (en) * | 1988-03-26 | 1992-08-18 | Hoechst Aktiengesellschaft | Pesticides |
DE3810379A1 (de) * | 1988-03-26 | 1989-10-12 | Hoechst Ag | Azaneophyl- und silazaneophylsulfide, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als schaedlingsbekaempfungsmittel |
DE3810378A1 (de) * | 1988-03-26 | 1989-10-05 | Hoechst Ag | Schaedlingsbekaempfungsmittel |
DE3828926A1 (de) * | 1988-08-26 | 1990-03-01 | Hoechst Ag | Verfahren zur herstellung von (aryl)-(dimethyl)-(3-arylpropyl)-silanen |
ZA903739B (en) * | 1989-05-27 | 1991-03-27 | Sumitomo Chemical Co | A poison bait for control of noxious insects |
DE4005154A1 (de) * | 1990-02-17 | 1991-08-22 | Hoechst Ag | Wasserdispergierbare granulate von neophanen und azaneophanen zur anwendung im pflanzenschutz |
DE4005155A1 (de) * | 1990-02-17 | 1991-08-22 | Hoechst Ag | Konzentrierte waessrige emulsionen von neophanen und azaneophanen zur anwendung im pflanzenschutz |
DE4005153A1 (de) * | 1990-02-17 | 1991-08-22 | Hoechst Ag | Hochkonzentrierte emulgierbare konzentrate von neophanen und azaneophanen zur anwendung im pflanzenschutz |
DE4017665A1 (de) * | 1990-06-01 | 1991-12-05 | Hoechst Ag | Pflanzenschuetzende substituierte isoxazoline, isoxazole, isothiazoline und isothiazole sowie verfahren zu ihrer herstellung und ihre verwendung |
TR24937A (tr) * | 1991-02-15 | 1992-07-01 | Hoechst Ag | BITKILERIN KORUNMASINDA KULLANILMAGA MAHSUS NEOFANLARIN VE AZANEOFANLARIN SUDA DISPERSIYONLAS GRANüLLERI |
US5178871A (en) * | 1991-06-26 | 1993-01-12 | S. C. Johnson & Son, Inc. | Stable double emulsions containing finely-divided particles |
DE4137940A1 (de) * | 1991-11-18 | 1993-05-19 | Basf Ag | 3-isoxazolylphenylverbindungen, ihre herstellung und ihre verwendung |
US6835847B2 (en) | 2001-02-06 | 2004-12-28 | Bayer Cropscience Ag | Phthalic acid diamide, method for the production thereof and the use of the same as a pesticide |
DE10115406A1 (de) * | 2001-02-06 | 2002-08-08 | Bayer Ag | Phthalsäurediamide |
PT1941798E (pt) * | 2004-12-17 | 2012-08-22 | Devgen Nv | Composições nematodicidas |
JP5286577B2 (ja) * | 2008-05-20 | 2013-09-11 | 日本曹達株式会社 | ポリシラン化合物の製造方法 |
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US3362933A (en) * | 1963-10-09 | 1968-01-09 | Dow Corning | Polymers of haloethersilanes and their quaternary salts |
US3334123A (en) * | 1963-10-09 | 1967-08-01 | Dow Corning | Haloethersilanes |
US3370790A (en) * | 1965-10-18 | 1968-02-27 | Sperry Rand Corp | Fluid shift |
DE3141860A1 (de) * | 1981-10-22 | 1983-05-05 | Bayer Ag, 5090 Leverkusen | Trifluormethyl-phenoxy-phenyl-silicium-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwuchsregulatoren |
JPS58201737A (ja) * | 1982-05-18 | 1983-11-24 | Mitsui Toatsu Chem Inc | 新規芳香族アルカン誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤 |
JPS60123491A (ja) * | 1983-12-08 | 1985-07-02 | Sumitomo Chem Co Ltd | 有機ケイ素化合物、その製造法およびその化合物を有効成分とする殺虫剤 |
JPS6187687A (ja) * | 1984-10-05 | 1986-05-06 | Yoshio Katsuta | 有機ケイ素系芳香族アルカン誘導体を含有する殺虫、殺ダニ剤及びその製法 |
JPS61263988A (ja) * | 1985-05-16 | 1986-11-21 | Shionogi & Co Ltd | シリル置換エ−テル類および殺虫・殺ダニ剤 |
US4883789A (en) * | 1986-06-02 | 1989-11-28 | Fmc Corporation | Substituted phenyltrialkylsilane insecticides |
US4709068A (en) * | 1986-06-02 | 1987-11-24 | Fmc Corporation | Substituted phenyltrialkylsilane insecticides |
-
1987
- 1987-04-02 CN CN90108778A patent/CN1025470C/zh not_active Expired - Fee Related
- 1987-04-10 US US07/036,575 patent/US4775664A/en not_active Expired - Fee Related
- 1987-04-21 AT AT87105842T patent/ATE54149T1/de not_active IP Right Cessation
- 1987-04-21 EP EP87105842A patent/EP0249015B1/de not_active Expired - Lifetime
- 1987-04-21 DE DE8787105842T patent/DE3763412D1/de not_active Expired - Fee Related
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- 1987-04-21 IL IL82268A patent/IL82268A/xx not_active IP Right Cessation
- 1987-04-22 CS CS872856A patent/CS268533B2/cs unknown
- 1987-04-23 NZ NZ220063A patent/NZ220063A/xx unknown
- 1987-04-23 ZA ZA872878A patent/ZA872878B/xx unknown
- 1987-04-24 JP JP62100172A patent/JP2598015B2/ja not_active Expired - Lifetime
- 1987-04-24 PT PT84763A patent/PT84763B/pt not_active IP Right Cessation
- 1987-04-24 TR TR283/87A patent/TR23344A/xx unknown
- 1987-04-24 SU SU874202456A patent/SU1618274A3/ru active
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- 1987-04-24 CN CN87102981A patent/CN1025502C/zh not_active Expired - Fee Related
- 1987-04-24 AU AU71947/87A patent/AU603569B2/en not_active Ceased
- 1987-04-24 DD DD87302113A patent/DD261737A5/de not_active IP Right Cessation
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- 1987-04-24 MY MYPI87000541A patent/MY100845A/en unknown
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- 1987-04-24 CA CA000535469A patent/CA1301154C/en not_active Expired - Fee Related
- 1987-04-24 DK DK209487A patent/DK209487A/da not_active Application Discontinuation
- 1987-04-25 KR KR1019870003995A patent/KR950001701B1/ko not_active IP Right Cessation
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