CN87103168A - 取代的嘧啶类化合物 - Google Patents
取代的嘧啶类化合物 Download PDFInfo
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- CN87103168A CN87103168A CN198787103168A CN87103168A CN87103168A CN 87103168 A CN87103168 A CN 87103168A CN 198787103168 A CN198787103168 A CN 198787103168A CN 87103168 A CN87103168 A CN 87103168A CN 87103168 A CN87103168 A CN 87103168A
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Classifications
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- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
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- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
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- 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
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- A—HUMAN NECESSITIES
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Abstract
本发明所涉及的是式(I)的新化合物及其盐,其制备方法及有关各中间体的制法,以及可用于防治昆虫及蜱螨目中有代表性的害虫,尤其是危害植物的食草昆虫及危害动物的体外寄生虫的含有这些化合物的组合物。式I中各符号的含义见说明书。
Description
本发明涉及新的取代2,4-二氨基-5-氰基嘧啶类化合物及其盐和中间体、这类化合物的制备及其在防治害虫和体外寄生虫方面的应用。
这类新化合物有如下的结构通式,并可成盐:
式中
R1为氢、C1-C6烷基、C2-C6链烯基或C2-C6炔基,
R2为氢、C1-C10烷基或C3-C6环烷基,
或者R1和R2一起构成选自-(CH2)3-、-(CH2)4-和-(CH2)5-中的一个基团,
R5为氢或基团-CO-R5或-SO2-R6,
R4为选自-NH2、-NH-CO-R5、-NH-SO2-R6、
和-NH-CH=N-R10中的一
个基团,
R6为C1-C6烷基,
R7为氢或C1-C6烷基,
R8和R9各自独立地代表氢或C1-C6烷基,或一起构成基团-(CH2)3-、-(CH2)4-或-(CH2)5-,
R10为基团-SO2-R13或
R11和R12各自独立地代表氢或C1-C6烷基,或一起构成基团-(CH2)3-、-(CH2)4-、或-(CH2)5-,
R13为C1-C10烷基、被可达10个卤素原子取代的C1-C10烷基,或者是C3-C6环烷基,
R14和R15各自独立地代表C1-C10烷基,
X和Y各自独立地代表氧或硫,
在本发明的范围内,卤素原子和卤素取代基的含义是氟、氯、溴或碘,优选的是氟及氯。
由于其性能优良,分别满足以下a)和b)两条件的式Ⅰ化合物及其盐是本发明优选的化合物:
a)
R1为氢或C1-C6烷基,
R2为C1-C4烷基或C3-C6环烷基,或
R1与R2一起构成基团-(CH2)4-、或-(CH2)5-,
R3为氢,
R4为基团-NH2或-NH-CO-R5,
R5为C1-C4烷基或全卤C1-C3烷基;
b)
R1为氢、甲基或乙基,
R2为C1-C4烷基或环丙基,
R3为氢,
R4为基团-NH2或-NH-CO-R5,
R5为C1-C3烷基。
由于其杀虫性能优良,特别优选的式Ⅰ化合物及其盐满足:
R1为氢、甲基或乙基,
R2为环丙基,
R3为氢,
R4为基团-NH2或-NH-CO-C2H5。
所谓式Ⅰ化合物的盐指的是式Ⅰ化合物与无机酸或者有机酸形成的生理上可耐受的盐。无机酸的例子有盐酸、氢溴酸、氢碘酸、硫酸、磷酸、亚磷酸及硝酸。有机酸例如三氟乙酸、三氯乙酸、甲酸、草酸、琥珀酸、马来酸、乳酸、乙醇酸、乌头酸、柠檬酸、苯甲酸、苯磺酸及甲磺酸。
式Ⅰ化合物可按下述方法制备:
a)使式Ⅱ化合物与氨反应,或
b)使式Ⅲ化合物与式Ⅳ的胺反应,
并在需要时,按已知方法,将由此得到的R3为氢、R4为基团-NH2的式Ⅰ化合物(化合物Ⅰa)
转变为满足下述的式Ⅰ化合物:R3为-CO-R5或-SO2-R6,并且(或者)R4为:-NH-CO-R5、-NH-SO2-R6、
或-NH-CH=N-R10,
其中,R1~R15、X及Y的意义同上,n为0、1或2,并在需要时,将这样得到的式Ⅰ化合物转变为它的盐。
关于方法a),式Ⅱ的磺酰基化合物(n=2)与氨的反应一般是在10~100℃的温度下,在有机溶剂如乙腈、四氢呋喃、二氧杂环己烷或溶剂/水混合物中进行的。同样的反应条件也适用于使式Ⅲ的2-氯-4,6-二氨基-5-氰基嘧啶与式Ⅳ的胺反应的方法b)。当采用方法a),以甲硫基化合物(n=0)作为原料时,则最好在压力釜中于高压下,使之与氨反应,反应温度为100~170℃,通常为约160℃。
将R4为-NH2的式Ⅰ化合物转变为R4具有其它本文中所给含义的化合物的过程中可以这样进行:使嘧啶环的6位氨基与合适的已知反应物反应。例如,式Ⅰ的6-氨基嘧啶可以与Hal-CO-R5、Hal-SO2-R6、(R5-CO)2O或R6O-CH=N-R10反应,得到6位有合适取代基的式Ⅰ化合物;这里Hal为卤原子,最好是氯原子,R5、R6及R10的意又同上。如欲制备R4为基团
的式Ⅰ化合物,可以使6-NH2与例如式
的缩醛反应,此处R6、R7、R8及R9的含义同上。按照相似的方法,采用合适的反应物,可由R3为氢的式Ⅰ的4-氨基嘧啶类化合物制得R3为基团-COR5或-SO2-R6的式Ⅰ化合物。上述酰化反应是在常压及有碱存在下,在惰性溶剂或稀释剂中进行的,反应温度为0~120℃,最好是40~80℃。适宜溶剂及稀释剂的例子有:链烷烃,例如正戊烷及其同系物,包括直到正十七烷的各种异构体;醚类,例如***、丙醚、丁醚、二甲氧基乙烷、二氧杂环己烷或四氢呋喃;氯代烃类,如氯仿、二氯甲烷、四氯化碳或氯苯;芳香烃类,如苯、甲苯或二甲苯。本发明方法也可以使用其它适宜的溶剂及稀释剂。于这些反应中可用的适当的碱例如有烷基胺,如三乙胺或二异丙基乙胺,还有吡啶或N-甲基吡咯烷酮。
式Ⅱ的起始化合物是新的化合物,并且同样是本发明的发明内容,尤其是因为它们也具有农药性质,特别是杀虫性质。它们可按下述方法制备:
a)例如,n=0的式Ⅱ化合物可按以下反应式制备:
在以上反应过程中用作原料的、式Ⅴ的N-氰基二硫代碳亚胺酸二甲酯及其与丙二腈反应生成的式Ⅵ的盐都是已知化合物(参看Rec.Trav.Ch.90/1971,463;J.Chem.Soc.,Chem.Comm.1974,350)。n=0的式Ⅱ化合物可以这样制得:用5N HCl将式Ⅵ的盐环化,然后使所得到的式Ⅶ的嘧啶化合物与式Ⅳ的相应胺反应。
b)n=0的式Ⅱ化合物还可以按以下反应式制得:
在以上反应式中,式Ⅷ盐的钠盐、式Ⅸ的脲和式Ⅹ的尿嘧啶都是已知化合物(参看J.Chem.Soc.,Chem.Comm.1974,350;Helv.Chem.Act.1985,1155)。式Ⅺ及Ⅻ的新的取代嘧啶类化合物都是按已知方法制备的。使式Ⅻ化合物与氨反应,可得到n=0的式Ⅱ化合物。
c)n=1或2的式Ⅱ起始化合物可以按照已知方法,通过将n=0的式Ⅱ化合物氧化而制得(参看“The Chemistry of Heterocyclic Compounds”,Vol.16:Pyrimidines,Intersc.Publ.Inc.,N.Y.1959)。
根据Chem.Ber.1968,1244,式Ⅲ的起始化合物,即2-氯-4,6-二氨基-5-氰基嘧啶是已知化合物,但它也可以这样制得:将上述的式Ⅶ化合物氧化为砜,再使后者与氨反应,从而将-SO2CH3替换为-NH2,反应式如下:
根据欧洲专利申请0084,758,具有农药性质,尤其是杀虫性质的氨基可被取代的2,4,6-三氨基-5-硝基嘧啶类化合物是已知的。而本发明的式Ⅰ及式Ⅱ化合物的结构在实质上不同于这些已知化合物,因为它们在5位上都有一个氰基。
出人意料的是,本发明的式Ⅰ及式Ⅱ化合物及其盐作为杀虫剂具有优良的特性,同时对植物无害,而且对温血动物低毒。它们特别适用于防治危害植物及动物的各种昆虫以及蜱螨目中有代表性的虫类。
尤其是,本发明的式Ⅰ及式Ⅱ化合物适用于防治下述各目属的昆虫:鳞翅目、鞘翅目、同翅目、异翅亚目、双翅目、缨翅目、直翅目、虱目、蚤类、食毛目、缨尾目、等翅目、啮虫目和膜翅目,以及用于防治蜱螨目有代表性的以下科属的螨类:硬螨科、软螨科、叶螨科和皮刺螨科。
本发明化合物除对苍蝇〔例如家蝇〕和蚊子幼虫有杀伤作用外,还适用于防治以下述植物类为食的植物害虫:装饰用植物,及有用植物作物,尤其是棉花〔例如可防治绿盲蝽象(Spodoptera littoralis)和烟芽夜蛾〕、果类以及疏菜〔例如可防治小菜蛾、苹蠹蛾、马铃薯甲虫和墨西哥豆
〕。式Ⅰ及式Ⅱ的化合物对防治水稻害虫也是有效的。式Ⅰ及式Ⅱ化合物还对昆虫的卵,特别是对其幼虫尤其是对有害的取食性昆虫(feeding insects)的幼虫具有显著的杀伤作用。对于许多种昆虫的成虫,尤其是鞘翅目昆虫(例如棉铃象),在它们吞食了含有本发明的活性化合物的食物后,都可以观察到产卵减少和(或)孵化率降低的现象。
式Ⅰ及式Ⅱ的化合物还可用于防治家养动物以及商品家畜(productive livestock)身上的体外寄生虫(如丝光绿蝇),例如,可用这些化合物对上述动物、牛棚、饲料棚、马厩等等以及牧场进行处理。
本发明化合物对于动物皮毛的附着能力出人意料地强,所以在使用例如浸湿、淋洗或喷雾(spray races)方法用这些活性物质对放养动物进行处理后,它们对体外寄生虫(例如双翅目害虫)的毒性作用能持续很久。这种强的附着能力,还能使已依附在商品家畜的皮或毛上的活性物质,在雨水淋到动物身上并流走时,不致被过早地洗去或冲走。
将本发明的化合物给商品家畜口服具有特殊的优点。应用这种方法时,这些活性成分显示出有效而且作用时间更持久的杀虫活性,尤其是在从消化道出来的***物中。这样,有害昆虫,特别是双翅目害虫的感染,在害虫在所饲养牲畜的附近,例如在家畜的饲养房、圈养处以及放养地出现之前就可以得到预防,这是因为双翅目害虫的幼虫-从产在***物上的卵中孵化出来就被杀死了。这种特殊应用方式所依据的一个极为重要的事实是:由于其结构特点,本发明的式Ⅰ及式Ⅱ化合物在生理上对温血动物无害。与常用的、大规模处理家畜饲养房和圈养处的方法相比较,上述有选择性地控制昆虫繁殖的方法要有效得多,同时经济得多。
有优良杀虫活性的式Ⅰ及式Ⅱ化合物能杀死至少50~60%的上述各种害虫。
将其它杀虫剂和(或杀螨剂)与本发明化合物或含有本发明化合物的各种组合物合用,可使其作用范围更广,更适合于各种具体情况。适宜的添加剂举例有:有机磷化合物、硝基酚类及其衍生物、甲脒类化合物、脲类化合物、氨基甲酸酯类、拟除虫菊酯类、卤代烃以及苏云金芽孢杆菌制剂。
本发明的化合物可以单独使用,但最好是与制剂技术中常用的各种辅助剂一起,用已知方法配制成可乳化的浓缩物、可直接喷洒或可稀释后使用的溶液、稀释乳液、可湿性粉剂、可溶性粉剂、粉尘剂、颗粒剂,也可以包入用例如聚合物做成的胶囊。根据组合物的性质,并根据所需达到的目的以及当时当地的具体情况及条件,可选择使用喷洒、喷雾、喷粉、播撒或浇灌等施用方法。
含有作为活性成分的式Ⅰ或式Ⅱ化合物,或还含有其它杀虫剂或杀螨剂,以及在适当的时候添加的固体或液体辅助剂的各种制剂,即各种组合物、液体制剂或混合物,都是用已知方法制成的,例如可将活性成分与各种补充剂,例如溶剂、固体载体,有时还与表面活性化合物(即表面活性剂)一起均匀混合并且(或)一起磨碎。
适宜的溶剂有:芳香烃,最好是含8~12个碳原子的芳香烃,例如二甲苯混合物或取代的萘类;酞酸酯,如酞酸二丁酯或酞酸二辛酯;脂肪烃,如环己烷或石蜡;醇和二醇以及其醚和酯,如乙醇、乙二醇、乙二醇单甲醚或单***;酮,如环己酮;强极性溶剂,如N-甲基-2-吡咯烷酮、二甲亚砜或二甲基甲酰胺;以及植物油或环氧化植物油(如环氧化可可油或豆油)或者水。
用于例如粉尘剂和可分散粉剂中的固体载体通常是天然矿物掺入物,如方解石、滑石、高岭土、蒙脱石或硅镁土。为改善物理性质,还可以添加高度分散的硅酸或高度分散的吸附聚合物。适宜的颗粒状吸附载体是多孔型材料,例如浮石、碎砖、海泡石或斑脱土;而适宜的非吸收性载体有方解石或沙子等材料。此外,还可以使用为数众多的经事先造粒的无机或有机材料,特别是例如白云石或粉碎的植物残体。
根据配制剂时所用活性成分或它们与其它杀虫剂或杀螨剂的混合物的性质,适宜的表面活性剂可采用具有良好乳化、分散和湿润性能的非离子型、阳离型和(或)阴离型的表面活性化合物。“表面活性剂”一词的含义亦应理解为各种表面活性化合物的混合物。
适宜的阴离子型表面活性剂既可以是各种水溶的肥皂,也可以是水溶性的合成表面活性化合物。
适宜的肥皂有:高级脂肪酸(C10-C22)的碱金属盐、碱土金属盐或未取代或取代的铵盐,例如油酸或硬脂酸的钠盐或钾盐,或可由例如可可油或动物脂油制得的天然脂肪酸混合物的钠盐或钾盐。其它适宜表面活性剂还有脂肪酸甲基牛胆碱盐以及经改性或未经改性的磷酯类。
但所说的表面活剂更常采用的尤其是脂肪磺酸盐、脂肪硫酸盐、磺化的苯并咪唑衍生物或烷芳基磺酸盐。
上述的脂肪磺酸盐或脂肪硫酸盐通常是碱金属盐、碱土金属盐或者取代或未取代的铵盐等形式的盐;这类盐含有C8-C22烷基,此烷基也包括含酰基的烷基部分在内;这类盐举例有:木素磺酸的钠盐或钙盐、十二烷基硫酸的钠盐或钙盐或者由天然脂肪酸制得的各种脂肪醇硫酸酯的钠盐或钙盐。这些化合物还包括硫酸化的和磺化的脂肪醇与环氧乙烷加成物的盐。磺化的苯并咪唑衍生物最好含有2个磺酸基和一个含有8-12个碳原子的脂肪酸基。烷芳磺酸盐的实例有:十二烷基苯磺酸及二丁基萘磺酸的钠盐、钙盐或三乙醇胺盐,以及萘磺酸与甲醛的缩合物的钠盐、钙盐或三乙醇胺盐。适宜的还有相应的磷酸盐,例如磷酸与对壬基苯酚和4-14摩尔的环氧乙烷之间形成的加成物所成的磷酸氢酯的相应盐类。
非离子型表面活性剂最好是脂肪醇或环状脂肪醇的聚乙二醇醚衍生物,或是饱和或不饱和脂肪酸与烷基酚的聚乙二醇醚衍生物。上述衍生物含有3至30个醚基,(脂肪)烃部分含有6~18个碳原子,而烷基酚的烷基部分含有6~18个碳原子。
其它适宜的非离子型表面活性剂有聚环氧乙烷与下列各物质的水溶性加成物:聚丙二醇、乙二氨基聚丙二醇以及烷基链中含1~10个碳原子的烷基聚丙二醇。这类加合物含有20~250个乙二醇醚基团以及10~100个丙二醇醚基团。在这些化合物中,乙二醇单元与丙二醇单元的数量比通常为1~5∶1。
非离子型表面活性剂的典型例子有:壬基苯酚聚乙氧基乙醇类、蓖麻油聚乙二醇醚类、聚丙烯/聚乙烯氧加成物、三丁基苯氧基聚乙氧基乙醇、聚乙二醇以及辛基苯氧基聚乙氧基乙醇。聚氧乙烯山梨糖醇的脂肪酸酯(例如聚氧乙烯山梨糖醇三油酸酯)也是适宜的非离子型表面活性剂。
阳离子型表面活性剂最好是季铵盐,这种季铵盐的氮原子上至少有一个C8-C22烷基,其它取代基有未取代或卤代的低级烷基、苄基或低级羟烷基。这类盐最好是氢卤酸盐、甲基硫酸盐或乙基硫酸盐的形式,例如氯化十八烷基三甲铵或溴化苄基二(2-氯乙基)乙铵。
关于制剂技术中常用的各种表面活性剂,可参看下面两份资料:“McCutcheon ′s Detergents and Emulsifiers Annual”,MC Publishing Corp.,Ridgewood,New Jersey,1979;Dr.Helmut Stache,“Tensid Taschenbuch”(Handbook of Surfactants)。Carl Hanser Verlag,Munich/Vienna 1981。
本发明的杀虫组合物通常含有0.1~99%,最好是0.1~95%的活性成分或该类活性成分与其它杀虫剂或杀螨剂的混合物、1~99.9%的固体或液体辅助剂以及0~25%,最好是0.1~20%的表面活性剂。
但作为商品出售的产品最好是配制成浓缩物的形式,而使用时一般采用浓度低得多的稀释制剂。
上述组合物也可以含有其它成分,例如稳定剂、消泡剂、粘度调节剂、粘合剂、增粘剂以及肥料或其它活性成分,这样的组合物具有特殊效果。
实施例1
a)起始化合物-2-环丙氨基-4-氨基-5-氨基-6-甲硫基嘧啶的制备:
ⅰ)在用冰水冷却下,把650毫升浓盐酸滴加到93克2-氰基-3-氰氨基-3-甲硫基丙烯腈,钠酸,在425毫升水中的溶液中。然后在室温下搅拌混合物约12小时。滤出沉淀,用碳酸钠水溶液处理。把20克所得到的2-氯-4-氨基-5-氰基-6-甲硫基嘧啶(熔点268℃)放在250毫升乙腈中搅拌成混悬液,然后在激烈搅拌和回流下于混悬液内滴加11.4克环丙胺。再搅拌混合物12小时,然后加入水。滤出沉淀,得到下式的标题化合物,熔点215~218℃(化合物3.1):
ⅱ)把20克N,N-二乙基苯胺缓慢滴加到18.3克5-氰基-6-甲硫基尿嘧啶和80毫升磷酰氯二者的混合物中。将混合物回流1.5小时,随后浓缩。将残余物与200毫升冰水相混合,搅拌,过滤收集所得物,水洗。干燥后,粗产品用硅胶柱层析法提纯(以6∶3∶1的甲苯/氯仿/乙酸乙酯混合液洗脱)。把22克所得到的2,4-二氯-5-氰基-6-甲硫基嘧啶(熔点118~120℃)溶于200毫升乙腈中,然后在-10℃向该溶液中加入11.4克环丙胺在40毫升乙腈中的溶液。室温下搅拌反应混合物2小时,再将其倾入2升冰水中。吸滤出沉淀物。把所得26.1克下式的2-环丙氨基-4-氯-5-氰基-6-甲硫基嘧啶(熔点139~141℃)加到100毫升乙腈中搅拌:
然后在所得混悬液内加入300毫升30%的氨水,再在室温下搅拌约10小时,随后在回流下搅拌约5小时。吸滤出混合液冷却后析出的固体残余物,用水洗涤。用150毫升甲基溶纤剂重结晶后,得到其结构式在以上ⅰ)的后面已经给出的标题化合物,熔点215~218℃。
b)2-环丙氨基-4,6-二氨基-5-氰基吡啶的制备
使33.7克按照以上a)中所述制得的2-环丙氨基-4-氨基-5-氰基-6-甲硫基嘧啶与150克氨在150℃于压力釜中反应15~20小时。将反应产物放入水中反复搅拌,然后过滤分离,得到下式的标题化合物,熔点249~751℃(化合物1.1)(见下左):
实施例2
a)起始化合物-2-二乙氨基-4-氨基-5-氰基-6-甲磺酰基嘧啶的制备:
在反应容器中放入47.5克2-二乙氨基-4-氨基-5-氰基-6-甲硫基嘧啶和650毫升二氯甲烷。向混合物中加入88.7克3-氯过苯甲酸,无须进行冷却。搅拌反应混合物2小时,然后过滤。蒸发浓缩滤液,把残余物悬浮于***中,吸滤,得到上式的标题化合物(化合物3.2)(熔点170~172℃)(见上右)。
b)2-二乙氨基-4,6-二氨基-5-氰基嘧啶的制备:
把26.9克按照以上a)中所述制得的2-二乙氨基-4-氨基-5-氰基-6-甲磺酰基嘧啶加到300毫升30%的氨水和100毫升乙腈二者的混合液中。将混合物回流12小时,然后冷却,滤出沉淀物。把沉淀物放入水中搅拌,吸滤,得到下式的标题化合物(化合物1.2,熔点222~224℃):
实施例3
2-二乙氨基-4-氨基-5-氰基-6-异丁酰氨基嘧啶的制备
把7克三乙胺加到10.3克2-二乙氨基-4,6-二氨基-5-氰基嘧啶(按实施例2方法制得)在90毫升四氢呋喃中的溶液内。然后在60℃于此溶液内滴入8.5克异丁酸酐。加热回流反应混合物48小时,蒸发浓缩,残余物用***洗,得到下式的标题化合物(化合物1.3,熔点151~152℃):
实施例4
N,N-二甲基-N′-(2-氰基丙氨基-4-氨基-5-氰基嘧啶-6-基)甲脒
在45~50℃,把3.7克二甲基甲酰胺缩二乙醇滴加到3.8克2-环丙氨基-4,6-二氨基-5-氰基嘧啶在100毫升二氧杂环己烷中的溶液内。在45~50℃搅拌反应混合物8小时。蒸去溶剂,粗产品用乙醇重结晶,得到下式的标题化合物(化合物1.4,熔点192~195℃):
实施例5
起始化合物-2-氯-4,6-二氨基-4-氨基-5-氰基-6-甲硫基嘧啶的制备
在0℃时,把50克细粉状2-氯-4-氨基-5-氰基-6-甲硫基嘧啶在750毫升二氧杂环己烷和250毫升水中的混悬液加到反应容器内。在搅拌及不予冷却的条件下,于此混悬液内通入一股强氯气流。约20分钟后,得一清澈溶液。再过30分钟后,停止通入氯气,搅拌反应液1/2小时。蒸发浓缩反应混合液,把残余物混悬于600毫升冰水中,过滤所得混悬液。把46.4克滤渣,即2-氯-4-氨基-5-氰基-6-甲磺酰基嘧啶〔熔点253℃(分解)〕,以及25克30%的氨水加到1000毫升乙腈中,并在室温下搅拌2小时,蒸发浓缩反应混合物,把残余物混悬于水中,过滤所得混悬液,得到下式的标题化合物(化合物5.1,熔点>260℃):
按照上述方法还制得了下列各通式Ⅰ化合物:
下列各通式Ⅰ化合物的盐是通过与相应酸的反应制得的:
下列各式Ⅰ化合物也可按上述方法制得:
下列各式Ⅱ中间体是按前述方法制得的:
下列各式Ⅱ中间体可以按照前述方法制得:
下列各式Ⅸ中间体是按前述方法制得的:
下列各式Ⅺ中间体是按前述方法制得的:
实施例6
用实施例1至3的活性成分或这些活性成分与其它杀虫剂或杀螨剂的混合物配制而成的各种制剂
(在本说明书中,所有百分比都是指重量百分比)
1.可湿性粉剂
a) b) c)
活性成分式其与别种杀虫
或杀螨剂的混合物 25% 50% 75%
木素磺酸钠 5% 5% -
十二烷基硫酸钠 3% - 5%
二异丁基萘磺酸钠 - 6% 10%
辛基酚聚乙二醇醚
(7~8摩尔环氧乙烷) - 2% -
高度分散的硅酸 5% 10% 10%
高岭土 62% 27% -
将活性成分或其与别种杀虫剂或杀螨剂的混合物同以上各辅助剂一起混匀,所得混合物用适宜的研磨机彻底粉碎,得到可湿性粉剂;此粉剂可用水稀释而制得所需浓度的混悬液。
2.可乳化的浓缩物
活性成分或其与别种杀虫或杀螨
剂的混合物 10%
辛基酚聚乙二醇醚
(4~5摩尔环氧乙烷) 3%
十二烷基苯磺酸钙 3%
蓖麻油聚乙二醇醚
(36摩尔环氧乙烷) 36%
环己酮 30%
二甲苯混合物 50%
用水将此浓缩物稀释可得到任何所需浓度的乳状液。
3.粉尘剂
活性成分或其与别种杀虫或杀螨 a) b)
剂的混合物 5% 8%
滑石 95% -
高岭土 - 92%
将以上活性成分与载体混合后用合适的研磨机研细,从而制得一种可直接使用的粉尘剂。
4.挤制颗粒剂
活性成分或其与别种杀虫或杀螨剂
的混合物 10%
木素磺酸钠 2%
羧甲基纤维素 1%
高岭土 87%
将活性成分或其与别种杀虫或杀螨剂的混合物同上述辅助剂相混合后磨碎,然后加水使混合物变湿。把所得混合物挤制成粒,并用空气流干燥之。
5.覆盖颗粒剂
活性成分或其与别种杀虫或
杀螨剂的混合物 3%
聚乙二醇(分子量为200) 3%
高岭土 94%
使用混合机,把磨得很细的活性成分或其与别种杀虫或杀螨剂的混合物均匀地敷到用聚乙二醇弄湿的高岭土颗粒上。用这种方法可制得无粉尘的覆层颗粒剂。
6.悬浮浓缩物
活性成分或其与别种杀虫或
杀螨剂的混合物 40%
乙二醇 10%
壬基酚聚乙二醇醚
(15摩尔环氧乙烷) 6%
木素磺酸钠 10%
羧甲基纤维素 1%
37%甲醛水溶液 0.2%
75%的硅油在水中的乳状液 0.8%
水 32%
将磨得很细的活性成分或其与别的杀虫或杀螨剂同上述各辅助剂一起混匀,得到一种混悬液;用水稀释此混悬液可得到所需浓度的各种混悬液。
7.喷散溶液
活性成分 30.00克
二辛基磺基琥珀酸钠 3.00克
苯甲醇 35.46克
乙二醇单甲醚 35.46克
103.92克=100毫升
在激烈搅拌下,把活性成分溶于以上两种溶剂的混合液内。然后将二辛基磺基琥珀酸钠溶于所得到的溶液中,必要时进行加热,然后补加所剩下的混合溶剂。
实施例7:防治家蝇的活性
在若干个烧杯中,每杯中都装入50克新配制成的CMSA营养基,用于蛆的培养。用移液管,将一定量含有1%(重量百分比)试验化合物的丙酮溶液加到各烧杯中的营养基内,使活性成分的浓度为800ppm,然后充分搅拌营养基,再用至少20小时时间让丙酮挥发掉。
然后在含已按上述处理过的营养基的烧杯中每杯放入25条一日龄的家蝇蛆,以供在给定浓度下对每种活性成分进行试验。在家蝇蛆成蛹后,从营养基中用水洗法将蛹分离出来,并放入各容器中,用带孔的盖子盖紧。
对每批冲洗出来的蛹进行计数,以测定试验化合物对家蝇蛆发育的毒性作用。10天后对蛹化成的苍蝇的数目进行计数。
在本试验中,实施例1~3的式Ⅰ及Ⅱ化合物显示出良好的活性。
实施例8:防治丝光绿蝇的活性
在50℃,把1毫升含0.5%试验化合物的含水制剂加到9毫升培养基中。然后把大约30条丝光绿蝇幼虫放到培养基上,在48小时和96小时后,用统计死亡率的方法测定杀虫活性。
在本试验中,实施例1~3的式Ⅰ及式Ⅱ化合物显示出优良的防治丝光绿蝇活性。
实施例9:防治铜绿蝇的活性
在若干只试管中,每管中都放入少量(30~50粒)新产下的丽蝇(铜绿蝇)卵,每一试管内都盛有4毫升营养基与1毫升试验溶液的混合物。培养基上接种虫卵后,试管用棉塞塞上,再放入培养箱中于30℃培养4天。在含未用试验溶液处理的营养基的对照试管中,在4天的培养时间结束时,幼虫虫体已发育到1厘米长(3期)。而试管中试验溶液所含的物质具有活性时,则在4天培养结束时,幼虫或已死亡,或即将死亡。
试验物质的活性也包括驱逐作用在内,因为这种作用能使幼虫从培养基中爬走而饿死。
在本试验中,实施例1~3的式Ⅰ及式Ⅰ化合物显示出十分有效的防治铜绿蝇的作用。
实施例10:
防治埃及伊蚊的作用
在烧杯内的150毫升水中,用移液管引入一定量的1%试验化合物丙酮溶液,从而使试验化合物的浓度达到800ppm。丙酮挥发后,于该含有试验化合物的烧杯中放入30~40只2日龄的埃及伊蚊幼虫。分别在1、2、5天后统计死亡率。
在本试验中,实施例1~3的式Ⅰ及式Ⅱ化合物显示出优良的防治埃及伊蚊的作用。
实施例11:防治取食性昆虫的杀虫活性
对盆载的25厘米高的棉花植株喷以含有浓度分别为
100ppm、200ppm和400ppm的试验化合物的水乳化液。棉植株上的喷洒层干燥后,在植株上授放L3期的绿盲蝽象和烟芽夜虫的幼虫。试验在24℃和60%的相对湿度下进行。2天后统计幼虫的死亡百分率。
在上述试验中,化合物1.1和1.2分别在200ppm和400ppm的浓度下可杀死80~100%的绿盲蝽象幼虫。化合物1.1和1.2分别在100ppm和400ppm的浓度下可杀死80~100%的烟芽夜虫。
实施例12:对棉铃象(成虫)的防治作用
对每棵6叶期的盆栽棉花植株喷以含400ppm试验化合物的可湿性含水乳剂。棉植株上的喷药层干燥后(约1.5小时后),在每棵植株上授放10只甲虫(野棉象)成虫。在塑料圆筒的一端包上纱网,然后用这些圆筒把经过喷药处理并授放了试验昆虫的各个植株罩起来,以防止甲虫逃离这些植株。然后把经过上述处理的植株保持在温度为25℃,相对湿度为约60%的环境中。在第2、3、4、5天后统计甲虫的死亡百分比(在远轴部位的百分比),同时与未经处理的对照植株比较以测定抗取食作用。
在本试验中,实施例1~3的化合物显示出优良的活性作用。
实施例13:防治蜱的作用
A)希伯来钝眼蜱
数出50只若虫,放入试管中,在2毫升水乳化液中浸泡1到2分钟;该乳化液是经一系列稀释制得的,含有400ppm的试验化合物。然后用标准棉塞塞住试管,并将试管倒置使棉花吸收该乳化液。1周后评价试验结果。对每种试验化合物都要进行一次重复试验。
B)微小牛蜱(幼虫)
使用同试验A中所用相似的系列稀释液,对20只OP敏感(OP-sensitive)和20只OP抗性(OP-resistant)的幼虫进行试验。(抗性是指能耐受二嗪农的作用)。在本试验中,实施例1~3的式Ⅰ及式Ⅱ化合物都有非常有效的防治希伯来钝眼碑和微小牛蜱这两种蜱的若虫和幼虫的作用。
实施例14:对稻褐飞虱的杀虫作用
对水稻植株喷以含400ppm试验化合物的溶液。所喷药层干燥后,在植株上授放N2或N3期的稻褐飞虱若虫。对每种试验化合物和每种试验水稻,都用两株植株试验。6天后统计死亡率。试验在26℃及60%相对湿度的条件下进行。在本试验中,化合物1.1对稻褐飞虱若虫有80~100%的防治效果。
实施例15:防治土壤昆虫(黄瓜条叶甲)的作用
把5棵高度为1~3厘米的玉米苗和一张圆滤纸浸入含有约4%(体积比)丙酮的试验化合物水溶液中。将浸过的圆滤纸铺在200毫升塑料杯的底部。然后把一张圆形干滤纸与上述玉米苗以及10条L2或L3期黄瓜条叶甲幼虫一起放在第一张圆滤纸上。试验在温度24℃、相对湿度为40~60%和日光照射的条件下进行。6天后,与未处理的对照物比较,对试验结果进行评价。
在本试验中,化合物1.15在400ppm的浓度下可杀死80~100%的害虫。
实施例16:对黑尾叶蝉(若虫)的防治作用
试验是对正在生长的植物进行。为此;在一些小盆(直径5.5厘米)中,每盆种入已生长了20天、高约15厘米的水稻植株。
在旋转工作台上,对每盆中的植株喷以100毫升含4ppm试验化合物的丙酮溶液。在喷药层干后,在每株植物上授放20只2或3期的黑尾叶蝉若虫。为防止蝉若虫逃离,将顶部有纱网封闭的普列克斯玻璃圆筒罩在每棵植株上。使上述若虫在已处理的植株上呆5天其间必须再喷至少一次药。试验在温度为23℃和55%相对湿度的条件下进行。每天光照试验植株16小时。
在本试验中,实施例1的化合物1.1的效果为80~100%。
实施例17:对小菜蛾的消化道毒性杀虫作用
对4叶期的盆栽大白菜植株(盆直径:10厘米)喷以含有浓度为3~400ppm的试验化合物的水乳化液,让喷上的乳液在植物上干燥。
2天后,在每棵大白菜植株上授放10条L2期小菜蛾幼虫。试验在24℃、60%相对湿度、弱光照下进行。在第2和第5天后统计幼虫的死亡百分比。
在本试验中,实施例1~4的式Ⅰ化合物的杀虫率为80~100%。
Claims (16)
1、通式如下的化合物或其盐:
式中:
R1为氢、C1-C6烷基、C2-C6链烯基或C2-C6炔基,
R2为氢、C1-C10烷基或C3-C6环烷基,或者
R1和R2一起形成下列基团之一:-(CH2)3-、-(CH2)4-及-(CH2)5-,
R5为氢或基团-CO-R5或-SO2-R6,
R4为下列基团之一:
-NH2、-NH-CO-R5、-NH-SO2-R6、
R5为氢、C1-C12烷基、C3-C6环烷基、C1-C6烷氧基、全氯C1-C6烷基或基团
R6为C1-C6烷基,
R7为氢或C1-C6烷基,
R8和R9各自独立地代表氢或C1-C6烷基,或二者一起代表下列基团之一:-(CH2)3-、-(CH2)4-以及-(CH2)5-,
R10为基团-SO2-R13或
R11和R12各自独立地代表氢或C1-C6烷基,或二者一起代表下列基团之一:-(CH2)3-、-(CH2)4-和-(CH2)5-,
R13为C1-C10烷基、被可达10个卤原子取代的C1-C10烷基,或为C3-C6环烷基,
R14,R15各自独立地代表C1-C10烷基,而X和Y各自独立地代表氧或硫。
2、根据权利要求1的式Ⅰ化合物或其盐,其中
R1为氢或C1-C4烷基,
R2为C1-C4烷基或C3-C6环烷基,或
R1和R2一起形成基团-(CH2)4-或-(CH2)5-,
R3为氢,
R4为基团-NH2或-NH-CO-R5,
R3为C1-C4烷基或全氯C1-C3烷基。
3、根据权利要求2的式Ⅰ化合物或其盐,其中
R1为氢、甲基或乙基,
R2为C1-C4烷基或环丙基,
R3为氢,
R4为基团-NH2或-NH-CO-R5,
R5为C1-C3烷基。
4、根据权利要求3的式Ⅰ化合物或其盐,其中
R1为氢、甲基或乙基,
R2为环丙基,
R3为氢,而
R4为基团-NH3或-NH2-CO-C2H5。
7、根据权利要求4的下式化合物:
12、一种杀虫组合物,其中含有作为活性成分的权利要求1至8以及10中任一权项所述的式Ⅰ或式Ⅱ化合物或其盐,以及适宜的载体和(或)其它辅助剂。
13、权利要求1至8以及10中任一项所述的化合物或其盐在防治危害动物及植物的昆虫及蜱螨目中有代表性的虫类方面的用途。
14、根据权利要求13所述的、在防治危害植物的昆虫之幼虫方面的用途。
15、根据权利要求13所述的、在防治驯化动物及商品家畜的体外寄生虫方面的用途。
16、防治昆虫以及蜱螨目中有代表性的虫类的方法,包括用杀虫有效量的、根据权利要求1至8及10中任一项所述的式Ⅰ化合物或其盐处理所说的害虫或使害虫接触该类化合物或其盐,或用含有杀虫有效量该类化合物的组合物处理所说害虫或使害虫接触该组合物,此组合物中除含有该化合物之外,还含有适用于该组合物中的辅助剂以及载体。
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CH1772/86-6 | 1986-04-30 |
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US (1) | US4783468A (zh) |
EP (1) | EP0244360B1 (zh) |
JP (1) | JPH0688981B2 (zh) |
KR (1) | KR870010011A (zh) |
CN (1) | CN87103168A (zh) |
AR (1) | AR247389A1 (zh) |
AT (1) | ATE79614T1 (zh) |
AU (1) | AU598254B2 (zh) |
BR (1) | BR8702106A (zh) |
CA (1) | CA1292231C (zh) |
CS (1) | CS271471B2 (zh) |
DD (1) | DD270907A5 (zh) |
DE (1) | DE3781196D1 (zh) |
DK (3) | DK165690C (zh) |
ES (1) | ES2051771T3 (zh) |
GR (1) | GR3005856T3 (zh) |
HK (1) | HK11694A (zh) |
HU (3) | HU204396B (zh) |
IL (1) | IL82343A0 (zh) |
NZ (1) | NZ220132A (zh) |
PH (1) | PH24337A (zh) |
PT (1) | PT84774B (zh) |
SG (1) | SG135993G (zh) |
SU (2) | SU1657061A3 (zh) |
TR (1) | TR22942A (zh) |
ZA (1) | ZA873082B (zh) |
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Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2941794A (en) * | 1956-04-13 | 1960-06-21 | Geddes Edith Bel | Building structures |
ATE139769T1 (de) * | 1991-04-11 | 1996-07-15 | Lonza Ag | Verfahren zur herstellung von 4-amino-2-chlor-5- cyan-6-(methylthio)pyrimidin |
RU95113597A (ru) * | 1992-12-02 | 1997-06-10 | ФМК Корпорейшн (US) | Инсектицидная композиция, способы борьбы с насекомыми |
US5344955A (en) * | 1993-02-19 | 1994-09-06 | Ciba-Geigy Corporation | Preparation of 1-amino-cyan-amido-2,2-dicyanoethylene, sodium salt |
DE4311901A1 (de) * | 1993-04-10 | 1994-10-13 | Huels Chemische Werke Ag | Neue Azeomethine, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
HUT73357A (en) * | 1993-07-26 | 1996-07-29 | Ciba Geigy Ag | Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidine derivatives |
ATE245356T1 (de) * | 1996-04-29 | 2003-08-15 | Syngenta Participations Ag | Pestizidzusammensetzungen |
ATE273286T1 (de) * | 1997-08-27 | 2004-08-15 | Novartis Pharma Gmbh | Dicyclanyl polymorphen und hydrate und deren herstellung |
AU2007202548B1 (en) * | 2007-06-01 | 2007-11-01 | Zoetis Services Llc | Pesticide Composition |
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AU2010100438B4 (en) * | 2009-05-08 | 2012-02-02 | Jurox Pty Ltd | Veterinary composition |
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JP5731205B2 (ja) * | 2011-01-14 | 2015-06-10 | 株式会社エス・ディー・エス バイオテック | 農園芸用の有害生物防除剤としてのピリミジン誘導体 |
JP2015003900A (ja) * | 2013-05-23 | 2015-01-08 | 宮崎みどり製薬株式会社 | ワクモ防除剤 |
PL239600B1 (pl) * | 2018-09-20 | 2021-12-20 | Icb Pharma Tomasz Swietoslawski Pawel Swietoslawski Spolka Jawna | Nowa sól dicyclanilu, sposób otrzymywania takiej soli, kompozycje zawierające taką sól oraz zastosowanie takiej soli do zwalczania i kontrolowania pasożytów, a zwłaszcza larw muchówek |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH376115A (de) * | 1957-12-06 | 1964-03-31 | Ciba Geigy | Verfahren zur Herstellung neuer substituierter Pyrimidine |
CH574206A5 (zh) * | 1972-11-16 | 1976-04-15 | Ciba Geigy Ag | |
GB1523274A (en) * | 1974-08-05 | 1978-08-31 | Ici Ltd | Herbicidal compositions containing substituted pyrimidine |
US4092150A (en) * | 1976-08-27 | 1978-05-30 | Fmc Corporation | Herbicidal 5-pyrimidinecarbonitriles |
CA1072556A (en) * | 1976-08-27 | 1980-02-26 | Fmc Corporation | Herbicidal 5-pyrimidinecarbonitriles |
DD157192A1 (de) * | 1981-03-13 | 1982-10-20 | Rainer Evers | Verfahren zur synthese von 2-funktionalisierten 4-alkylthio-6-amino-pyrimidin-5-carbonitrilen |
CH652396A5 (de) * | 1981-12-07 | 1985-11-15 | Ciba Geigy Ag | Amino-5-nitropyrimidin-derivate. |
DE3205638A1 (de) * | 1982-02-17 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Trisubstituierte pyrimidin-5-carbonsaeuren und deren derivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
-
1987
- 1987-04-22 US US07/041,163 patent/US4783468A/en not_active Expired - Lifetime
- 1987-04-24 DE DE8787810262T patent/DE3781196D1/de not_active Expired - Lifetime
- 1987-04-24 ES ES87810262T patent/ES2051771T3/es not_active Expired - Lifetime
- 1987-04-24 AT AT87810262T patent/ATE79614T1/de not_active IP Right Cessation
- 1987-04-24 EP EP87810262A patent/EP0244360B1/de not_active Expired - Lifetime
- 1987-04-27 IL IL82343A patent/IL82343A0/xx not_active IP Right Cessation
- 1987-04-28 PT PT84774A patent/PT84774B/pt unknown
- 1987-04-28 AR AR87307408A patent/AR247389A1/es active
- 1987-04-28 CA CA000535755A patent/CA1292231C/en not_active Expired - Lifetime
- 1987-04-29 SU SU874202490A patent/SU1657061A3/ru active
- 1987-04-29 AU AU72194/87A patent/AU598254B2/en not_active Expired
- 1987-04-29 DK DK217787A patent/DK165690C/da not_active IP Right Cessation
- 1987-04-29 HU HU873977A patent/HU204396B/hu not_active IP Right Cessation
- 1987-04-29 CN CN198787103168A patent/CN87103168A/zh active Pending
- 1987-04-29 HU HU871953A patent/HU201651B/hu unknown
- 1987-04-29 BR BR8702106A patent/BR8702106A/pt unknown
- 1987-04-29 DD DD87302257A patent/DD270907A5/de not_active IP Right Cessation
- 1987-04-29 PH PH35196A patent/PH24337A/en unknown
- 1987-04-29 NZ NZ220132A patent/NZ220132A/xx unknown
- 1987-04-29 ZA ZA873082A patent/ZA873082B/xx unknown
- 1987-04-29 HU HU9203430A patent/HU9203430D0/hu unknown
- 1987-04-30 KR KR870004197A patent/KR870010011A/ko not_active Application Discontinuation
- 1987-04-30 TR TR291/87A patent/TR22942A/xx unknown
- 1987-04-30 CS CS873075A patent/CS271471B2/cs unknown
- 1987-04-30 JP JP62107947A patent/JPH0688981B2/ja not_active Expired - Lifetime
-
1988
- 1988-06-28 SU SU884355955A patent/SU1711672A3/ru active
-
1992
- 1992-05-12 DK DK92616A patent/DK61692D0/da not_active Application Discontinuation
- 1992-05-12 DK DK92617A patent/DK61792D0/da not_active Application Discontinuation
- 1992-10-01 GR GR920401774T patent/GR3005856T3/el unknown
-
1993
- 1993-12-21 SG SG135993A patent/SG135993G/en unknown
-
1994
- 1994-02-08 HK HK116/94A patent/HK11694A/xx not_active IP Right Cessation
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CN104130197A (zh) * | 2014-07-29 | 2014-11-05 | 华中农业大学 | 2,4,6-三氨基-5-氰基嘧啶的化学合成方法 |
CN104649982A (zh) * | 2015-02-26 | 2015-05-27 | 齐鲁晟华制药有限公司 | 一种地昔尼尔的制备方法 |
CN104649982B (zh) * | 2015-02-26 | 2016-12-07 | 齐鲁晟华制药有限公司 | 一种地昔尼尔的制备方法 |
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