CN1151404A - 取代的四氢-5-硝基-嘧啶 - Google Patents
取代的四氢-5-硝基-嘧啶 Download PDFInfo
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- CN1151404A CN1151404A CN96112278A CN96112278A CN1151404A CN 1151404 A CN1151404 A CN 1151404A CN 96112278 A CN96112278 A CN 96112278A CN 96112278 A CN96112278 A CN 96112278A CN 1151404 A CN1151404 A CN 1151404A
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- 238000002360 preparation method Methods 0.000 claims abstract description 42
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
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- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明涉及新的取代的,按照权利要求1的一种式(I)四氢-5-硝基-嘧啶,其中n,R1,R2具有说明书中给出的含义,涉及它的制备方法,涉及它的消灭牲畜害虫,特别是昆虫,蜘蛛,线虫的用途,这些害虫在农田,森林,储存产物和材料的保护和,在卫生区域遇到。
Description
本发明涉及新的四氢-5-硝基-嘧啶其制备方法和消灭牲畜害虫,特别是昆虫,蜘蛛和线虫的用途,这些害虫在农田,森林,在储存产物和材料的保护和在卫生区遇到。
业已知道某些1,2,3,6-四氢-5-硝基嘧啶衍生物具有杀虫性能(DE-A3638121,EP-A 0316843和EP-A 0316845)。然而这些化合物的活性总是不够,特别于低施用率和低浓度下。
现已发现式(I)新的取代的四氢-5-硝基-嘧啶其中n 表示0或1,R1 表示非强制性取代的吡啶基或非强制性取代的噻唑基和R2 表示下述基团之一:其中Alk 表示具有多于一个碳原子的烷基,Alk1至Alk6 各自独立地表示烷基,Hal 表示卤素,m 表示1或2,p 表示1,2或3,r和s 各自独立地表示0,1,2,3或4,R3 在各情况下表示非强制性取代的苯基,吡啶基或N-吗啉代,R4 在各情况下表示非强制性取代的苯基或噻吩基,R5 在各情况下表示非强制性取代的苯基,萘基或吡啶基和X 表示氧,硫或NAlk7基,
其中
Alk7表示烷基。
另外还发现式(I)取代的四氢-5-硝基-嘧啶可按下述方法得到:在有或无酸性催化剂存在下,在有或无稀释剂存在下,于至少两倍摩尔量甲醛存在下,如果将式(II)硝基亚甲基衍生物其中R1和n具有上述含义与式(III) 胺反应
H2N-R2 (III)其中R2 具有上述含义。
式(I)取代的四氢-5-硝基-嘧啶非强制性地具有不对称取代的碳原子并因而能从不同的光学异构体存在。本发明涉及异构体混合物和纯异构体二者。
最后,还发现式(I)新的取代的四氢-5-硝基-嘧啶具有非常显著的生物性质,特别适于消灭在农田,在森林,在储存产物和材料的保护和在卫生区域存在的牲畜害虫,特别是昆虫,蜘蛛和线虫。
按照本发明的取代的四氢-5-硝基-嘧啶的一般说明由式(I)给出。
在上述和下述中的优选的取代基和基团的范围详述如下:n 优选表示0或1,R1 优选表示非强制性地被相同或不同取代基取代1至3次的吡啶基或表示被
相同或不同取代基非强制性地取代1至2次的噻唑基,在各情况下可能的
取代基是:
卤素,氰基,硝基,C1-C4烷基,C1-C4烷氧基,C1-C4烷硫基,C1-C4卤
代烷基,C1-C4卤代烷氧基和C1-C4卤代烷硫基。R2 优选表示基团(a)至(y)。Alk 优选表示C2-C4烷基。Alk1至Alk6 各自独立地优选表示C1-C4烷基。Hal 优选表示氟,氯或溴。m 优选表示1或2。p 优选表示1,2或3。r和s 各自独立地优选表示0,1,2,3或4。R3 优选表示被相同或不同取代基非强制性地取代1至5次的苯基或表示被相
同或不同取代基非强制性地取代1至4次的吡啶基,在各情况下可能的取
代基是:
卤素,氰基,硝基,C1-C4烷基,C1-C4烷氧基,C1-C4烷硫基,C1-C4卤
代烷基,C1-C4卤代烷氧基,C1-C4卤代烷硫基,氨基,C1-C4烷基氨基
和二(C1-C4烷基)氨基;
和表示被相同或不同取代基非强制性地取代1至2次的N-吗啉代,可能的
取代基是:
卤素,C1-C4烷基,C1-C4烷氧基和C1-C4-卤代烷基。R4 优选表示被相同或不同取代基非强制性地取代1至5次的苯基或表示被相
同或不同取代基非强制性地取代1至3次的噻吩基,在各情况下可能的取
代基是:
卤素,氰基,硝基,C1-C4烷基,C1-C4烷氧基,C1-C4烷硫基,C1-C4卤
代烷基,C1-C4卤代烷氧基,C1-C4卤代 烷硫基,氨基,C1-C4烷
基氨基和二(C1-C4烷基)氨基。R5 优选表示被相同或不同取代基非强制性地取代1至5次的苯基,被相同或
不同取代基非强制性地取代1至3次的萘基或表示被相同或不同取代基非
强制性地取代1至4次的吡啶基,在各情况下可能的取代基是:
卤素,氰基,硝基,C1-C4烷基,C1-C4烷氧基,C1-C4烷硫基,C1-C4卤
代烷基,C1-C4卤代烷氧基,C1-C4卤代烷硫基,氨基,C1-C4烷基氨基
和二(C1-C4烷基)氨基。X 优选表示氧,硫或NAlk7基团,其中Alk7表示C1-C4烷基。n 特别优选表示0或1。R1 特别优选表示被相同或不同取代基非强制性地取代1至2次的吡啶基或表
示非强制性地取代1次的噻唑基,在各情况下可能的取代基是:
氟,氯,溴,氰基,硝基,甲基,乙基,甲氧基,甲硫基,三氟甲基,
三氟甲氧基和三氟甲硫基。R2 特别优选表示基团(a)至(y)。Alk 特别优选表示乙基,正丙基和异丙基。Alk1至Alk6 各自独立地特别优选表示甲基,乙基和正丙基或异丙基。Hal 特别优选表示氟和氯。m 特别优选表示1或2。p 特别优选表示1,2或3。r和s各自独立地特别优选表示0,1,2,3或4、R3 特别优选表示被相同或不同取代基非强制性地取代1至3次的苯基,或表
示被相同或不同取代基非强制性地取代1至2次的吡啶基,在各情况下可
能的取代基是:
氟,氯,溴,氰基,硝基,甲基,乙基,正丙基或异丙基,叔丁基,三
氟甲基,甲氧基,乙氧基,三氟甲氧基,三氟甲硫基,二甲基氨基,甲
基乙基氨基和二乙基氨基;
和表示被相同或不同取代基非强制性地取代1至2次的N-吗啉代,可能的
取代基是:
甲基,乙基,甲氧基和三氟甲基。R4 特别优选表示被相同或不同取代基非强制性地取代1至3次的苯基或表示
被相同或不同取代基非强制性地取代1至2次的噻吩基,各情况下可能的
取代基是:
氟,氯,溴,氰基,硝基,甲基,乙基,正丙基或异丙基,叔丁基,三
氟甲基,甲氧基,乙氧基,三氟甲氧基,三氟甲硫基,二甲基氨基,甲
基乙基氨基和二乙基氨基。R5 特别优选表示被相同或不同取代基在各情况下非强制性地被取代1至3次
的苯基和萘基或表示被相同或不同取代基非强制性地取代1至2次的吡啶
基,在各情况下可能的取代基是:
氟,氯,溴,氰基,硝基,甲基,乙基,正丙基或异丙基,叔丁基,三
氟甲基,甲氧基,乙氧基,三氟甲氧基,三氟甲硫基,二甲基氨基,甲
基乙基氨基和二乙基氨基。X 特别优选表示氧,硫,N-甲基,N-乙基,N-正丙基和N-异丙基。
在上面给出的一般范围或优选范围的基的定义和解释适用于最终产物且相应地适用于原料和中间产物。基团的这些定义按需要可相互结合,这样包括优选的相应范围间的结合。
按照本发明优选给出式(I)的化合物,其中上面给出的优选的定义结合起来。
按照本发明特别优选给出那些式(I)化合物,其中上面的给出的特别优选的定义结合起来。
上面和下面给出的基的定义中,烃基和烷基或链烯基一单独或与杂原子结合,如烷氧基或烷硫基,在各情况下可能是直链或支链的。
按照本发明的优选化合物是式(Ia)至(Id)的物质。其中R1-1 表示非强制性取代的吡啶基和R2 具有本发明定义中给出的含义。其中R1-2 表示非强制性取代的噻唑基和R2 具有本发明定义中给出的含义。其中R1-1 表示非强制性取代的吡啶基和R2 表示本发明定义中给出的含义。其中R1-2 表示非强制性取代的噻唑基和R2 具有本发明定义中给出含义。
按照本发明的优选化合物也是式(Ia-1),(Ib-1),(Ic-1)和(Id-1)的物质的基团:其中R2 表示上述一般,优选和特别优选的含义。其中R2 表示上述一般,优选和特别优选的含义。其中R2 表示上述一般,优选和特别优选的含义。其中R2 表示上述一般,优选和特别优选的含义。
在按照本发明的方法中可用作原料的硝基亚甲基衍生物一般定义在式(II)中给出。式(II)中,R1和n优选或特别优选具有上面已给出的那些含义,这些含义与本发明式(I)化合物分别对R1和n所述优选或特别优选相对应。
式(II)硝基亚甲基衍生物是已知的和/或都用已知的方法制备(见例如DE-A 2514402,EP-A 136636,EP-A 154178和EP-A 163855)。
按照本发明的方法中也用作原料的胺的一般定义由式(III)给出。在式(III)中,R2优选或最优选具有上面已经给出的含义,这些含义与本发明式(I)化合物分别对R2所述优选或特别优选相对应。
式(III)胺是通常已知的有机化合物。
用酸也可以将式(I)化合物转化为加成化合物。
可以加入的酸包括,优选,氢卤酸,例如氢氯酸和氢溴酸,特别是氢氯酸,还有磷酸,硫酸,硝酸,乙酸,草酸,丙二酸,琥珀酸,苹果酸,酒石酸,马来酸,富马酸,甲磺酸,苯甲酸,取代的苯甲酸,甲酸,氯乙酸,甲苯磺酸,苯磺酸,三氯乙酸,苯二甲酸,萘磺酸,烟酸,柠檬酸和抗坏血酸。
按照本发明制备式(I)新化合物的方法优选用稀释剂进行。在此范围的合适的稀释剂是水和有机溶剂,它们对反应是惰性的。这些溶剂优选包括脂族和芳族的,非强制性卤代的烃,例如戊烷,己烷,庚烷,环己烷,石油醚,汽油,石油英,苯,甲苯,二甲苯,二氯甲烷,二氯乙烷,氯仿,四氯化碳,氯苯和邻二氯苯,醚例如乙醚和丁醚,乙二醇二甲醚和二乙二醇二甲醚,四氢呋喃和二恶烷,醇例如甲醇,乙醇,正丙醇和异丙醇。醇和水的混合物优选使用。
本发明方法优选在酸,非氧化催化剂存在下进行。氢卤酸如氢氯酸和氢溴酸,磷酸,低级羧酸如乙酸和丙酸特别合适。
本发明的反应温度可在相对大的范围内变化。通常在-20℃和+120℃之间进行,优选0℃和+80℃之间。
本发明的方法通常在大气压下进行。在升高或降低压力下也可以工作。
为进行本发明方法每摩尔式(II)硝基亚甲基衍生物施用1至1.5摩尔,优选1至1.2摩尔式(III)胺和2至4摩尔,优选2至3摩尔甲醛。
式(III)胺可以非强制性地作为水溶液施用。
当使用式(III)气态胺时,可将这些化合物通过含有稀释剂,式(II)化合物和甲醛的混合物。对本发明方法甲醛可以水溶液使用。通常反应在合适的稀释剂中进行,于所需的特定温度下将反应混合物搅拌几小时。在本发明方法中,在各情况下反应混合物用常规方法处理。
在简单的装置中,用常规的成盐方法可以得到式(I)化合物的酸加成盐,例如将式(I)化合物溶于合适的惰性溶剂并加入酸,例如氢氯酸,并可用已知的方法分离,例如过滤,如果需要可用惰性有机溶剂洗涤进行纯化。
鉴于植物的良好的耐药性和对温血动物良好的特性,上述活性化合物适于消灭牲畜害虫,特别是昆虫,蜘蛛和线虫,这些害虫在农田,森林,储存产物和材料的保护和在卫生区遇到。优选使用它们作植物保护剂。它们对普通敏感性和抗药性种和全部或一些发育阶段都是有活性的。上述害虫包括:
等足目,例如,潮虫、平甲虫和带鼠妇。
倍足目,例如,具斑马陆。
唇足目,例如,食果地蜈蚣和蚰蜒。
综合目,例如,庭园么蚰。
缨尾目,例如,西洋衣鱼。
弹尾目,例如,具刺跳虫。
直翅目,例如,东方蜚蠊,美洲大蠊,马得拉蜚蠊,德国小蠊,家蟋蟀,蝼蛄属,热带飞蝗,长额负蝗和蚱蜢。
革翅目,例如,欧洲球螋。
等翅目,例如犀白蚁属。
虱目,例如,体虱,血虱属和颚虱属。
食毛目,例如,羽虱和啮虱。
缨翅目,例如,温室条蓟马和烟蓟马。
半翅目,例如,褐盾蝽,棉红蝽,甜菜拟网蝽,臭虫,长红蜡蝽和吸血猎蝽。
同翅目,甘蓝粉虱,棉粉虱,温室白粉虱,棉蚜,甘蓝蚜,茶鹿隐瘤额蚜,甜菜蚜,Doralis pomi,苹果蚜,苹果绵蚜,粟缢管蚜,美核桃根瘤蚜,桃大尾蚜,麦长管蚜,桃蚜属,忽布瘤额蚜,瘿绵蚜属,叶蝉属,纹叶蝉,黑尾叶蝉,李蜡蚧,揽珠蜡蚧,灰飞虱,褐飞虱,红圆蚧,春藤园盾蚧,粉蚧属和木虱属。
鳞翅目,例如,红铃虫,松矢蛾,冬天蛾,苹果细蛾,苹果巢蛾,小菜蛾,黄褐天幕毛虫,黄毒蛾,毒蛾属,棉潜叶蛾,桔潜叶蛾,地老虎属,切根虫属,褐夜蛾,实夜蛾属,棉铃虫属,甜菜夜蛾,甘蓝夜蛾,小眼夜蛾,Spodop-tera Litura,粘虫属,粉纹夜蛾,苹果蠹蛾,粉蝶属,螟属,玉米螟,地中海粉螟,大蜡螟,负袋衣蛾,织网衣蛾,褐织夜蛾,亚麻黄卷蛾,烟卷蛾,云杉卷夜蛾,葡萄果蠹蛾,茶长卷夜蛾和栎纵卷夜蛾。
鞘翅目,例如,贝斑窃蠹,谷蠹,Bruchidius obtectus,大豆象,家天牛,赤杨紫跳甲,萤叶甲,马铃薯甲虫,蜡根猿叶甲,条叶甲属,油菜跳甲,墨西哥豆瓢虫,隐金甲属,锯谷盗,花象甲属,谷象属,葡萄黑耳,象,香焦根叶甲,甘蓝荚象甲,芷蓿叶象甲,肾斑皮蠹,皮蠹属,黑皮蠹属,圆支蠹,黑毛皮蠹,粉蠹属,油菜花露尾甲,蛛甲属,金黄蛛甲,麦蛛甲,拟谷盗属,黄粉甲,叩甲属,金针虫属,金龟,六月金龟和新西兰肋翅鳃角金龟。
膜翅目,例如,松叶蜂,叶蜂属,蚁属,厨蚁和胡蜂属。
双翅目,例如,伊蚊属,按蚊属,库纹属,黄猩猩果蝇,家蝇属,厩蝇属,红头丽蝇,绿绳属,金蝇属,疽蝇属,胃蝇属,虱蝇属,螫蝇属,鼻蝇属,皮蝇属,虻属,螗蜩,花园毛蚊,瑞典麦杆蝇,麦花蝇属,甜菜潜叶蝇,地中海实蝇,油橄榄实蝇和欧洲大蚊。
蚤目,例如,东方鼠蚤和蚤。
蛛形纲,例如,蝎和盗蛛和黑寡妇球腹蛛。
蜱螨属,例如,粗脚粉螨,隐喙蜱,钝喙蜱属,鸡皮刺螨,兔瘿螨,桔锈螨,牛蜱属,头蜱属,花蜱属,璃眼蜱属,硬蜱属,痒螨属,皮痒螨属,疥螨属,附线满属,苜蓿苔属螨,全爪螨属和红叶螨属。
寄生植物线虫包括,例如,草地垫刃线虫属,似内侵线虫,双垫刃属川续断,异皮线虫属,球头线虫属,根结线虫属,滑刃线虫属,长囊线虫属,箭鱼属,和毛线虫属。
本发明式(I)化合物特别表现出高杀虫和杀螨活性。
它们特别成功地用于消灭危害植物的害虫,例如杀芥属植物甲虫的幼虫(Phaedon Cochlae riae),小猫头鹰蛾毛虫(Spodoptera frugiperda或exigua),棉铃虫(Heliothis armigera),水稻绿叶蝉(NephotettixCincticeps)和桃蚜虫(Mycus Persicae)或消灭危害植物的蜱螨,如一般的蜘蛛蜱螨或双斑纹蜱螨(Tetranychus Urticae)。
此外,它们表现出良好的土壤杀虫剂活性,例如杀条叶甲幼虫,还表现出良好的根内吸活性,例如杀豆属蚜虫。
上述活性化合物可转化为常规制剂,如溶液,乳剂,可湿性粉剂,悬浮剂,粉剂,粉尘剂,糊剂,可溶性粉剂,颗粒剂,悬浮-乳化浓缩剂,浸有活性化合物的天然和合成材料,在聚合物内的非常小的囊。
用已知的方法生产这些制剂,例如将活性化合物与填料混合,这些填料是液体溶剂和/或固体载体,非强制性地使用表面活性剂,即乳化剂和/或分散剂和/或泡沫生成剂。
用水作填料的情况下,有机溶剂,例如,也可用作辅助溶剂。作为液体溶剂,总的来说合适的有:芳族的如甲苯,二甲苯或烷基萘,氯代芳烃和氯代脂族烃如氯苯,氯乙烯,二氯甲烷,脂族烃和环己烷或链烷烃,例如矿物油馏分,矿物油和植物油,醇如丁醇或乙二醇以及它们的醚和酯,酮如丙酮,甲基乙基酮,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。
作为固体载体合适的有:
例如铵盐和磨细的天然矿物,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱石或硅藻土,和磨细的合成矿物,如高分散硅石,氧化铝和硅酸盐;适于造粒的固体载体有:例如粉碎和分级的天然矿石如方解石,浮石,海泡石,白云石,以及无机和有机粉末调制成的颗粒,和有机材料如锯屑,坚果壳和烟草杆;适于乳化和/或形成泡沫的试剂有: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水解产物;适于作分散剂的有:例如木素亚硫酸盐废液和甲基纤维素。
粘结剂例如羧甲基纤维素和粉状,粒状或乳胶状的天然和合成高分子例如阿拉伯胶,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,可用于制剂。其它添加剂可是矿物和植物油。
也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,和痕量养分如铁、锰、硼、铜、钴、钼和锌的盐。
通常,制剂含有0.1和95%重量比的活性化合物,优选0.5%和90%之间。
本发明的活性化合物在其商业上常用的制剂中和在从这些制剂制备的使用形式中可以与其它活性化合物的混合物的形式存在,这些其它活性化合物例如是杀虫剂,引诱剂,止繁殖剂,杀菌剂,杀螨剂,杀线虫剂,杀真菌剂,植物生长调节剂或除草剂。杀虫剂包括,例如,磷酸盐,氨基甲酸酯,羧酸酯,氯代烃,苯基脲,由微生物制备的物质等。
对这些混合物特别优秀的组分的实例是下述化合物: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-(4-三氟甲基苄基)苯甲酰胺,(E)-2-甲氧亚氨基-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-基氧基]苯基}-3-甲氧基丙烯酸甲酯,(E)-甲氧亚氨基[α-(0-甲苯氧基)-O-甲苯基]乙酸甲酯,2-苯基苯酚(OPP),aldimorph,ampropylfos,敌菌灵,环戊唑,
苯霜灵,麦锈灭,苯菌灵,乐杀螨,联苯,双苯三唑醇,杀稻瘟菌素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
多硫化钙,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,乙菌利,硫杂灵,Cymoxanil,环唑醇,Cyprofuram,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,甲菌定,烯酰吗啉,烯唑醇,敌螨普,二苯胺,dipyrithion,灭菌磷,二噻农,多果定,敌菌酮,克瘟散,epoxy-conazole,乙菌定,氯唑灵,异嘧菌醇,fenbuconazole,呋菌胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,乙酸三苯锡酯,氢氧化锡,福美铁,嘧菌腙,氟啶胺,fludioxonil,氟菌安,fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,fose-tyl-aluminium,四氢苯酞,麦穗宁,呋氨丙灵,furmecyclox,双胍盐,六氯苯,己唑醇,土菌消,烯菌灵,酰胺唑,亚氨基辛二烯,iprobenfos(IBP),异丙定,富士一号,
青雷霉素,铜制剂如:氢氧化铜,烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉酮和枣红的混合物,锰铜混剂,代森锰,嘧菌胺,灭锈胺,氨丙灵,metconazole,methsulfocarb,甲呋菌胺,代森联,噻菌胺,腈菌唑,二甲基二硫代氨基甲酸镍,异丙消,环菌灵,oxamocarb,氧化萎锈灵,
稻瘟酯,戊菌唑,戊菌隆,phosdiphen,四氯苯酞,多马霉素,粉病灵,聚氨基甲酸酯,多氧霉素,噻菌灵,丙氯灵,杀菌利,百维灵,丙环唑,甲基代森锌,定菌磷,啶斑肟,pyrimethanil,咯喹酮,五氯硝基苯(PCNB),
硫和硫制剂,戊唑醇,叶枯酞,四氯硝基苯,涕必灵,噻菌腈,甲基托布津,福美双,甲基立枯磷,对甲抑菌灵,唑菌酮,唑菌醇,噻菌嗪,杨菌胺,三环唑,克啉菌,氟菌唑,嗪氨灵,triticonazole,
有效霉素,烯菌酮,代森锌,福美锌。杀细菌剂:
溴硝丙二醇,双氯酚,氯定,福美镍,春雷霉素,Octhilinone,呋喃羧酸,土霉素,噻菌灵,链霉素,叶枯酞,硫酸酮和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂
齐暾螨素,AC 303 630,甲胺磷,氟酯菊酯,棉铃威,砜灭威,甲体氯氰菊酯,虫螨脒,齐墩螨素,AZ 60541,azadirachtin,谷硫磷A,谷硫磷M,唑环锡,苏云金杆菌,恶虫威,丙硫克百威,bensultap,乙体氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷A,合杀威,噻嗪酮,丁叉威,butylpyridaben,硫线磷,西维因,卡巴呋喃,三硫磷,丁硫克百威,巴丹,CGA 157419,CGA 184699,chloethocarb,chlorethoxyfos,毒虫畏,氟咪杀,氯甲磷,毒死蜱,毒死蜱M,Cis-resmethrin,clocythrin,四螨嗪,乙氰菊酯,氟氯氰菊酯,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,δ迈秋灵,一0五九M,一0五九S,甲基一0五九的硫赶式异构体,杀螨隆,二嗪农,除线灵,敌敌畏,dicliphos,百治磷,乙硫磷,氟脲杀,乐果,dimethylvinphos,敌杀磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,苯虫威,乙硫磷,醚菊酯,灭克磷,氧嘧啶磷,
克线磷,杀螨锡,杀螟松,fenobucarb,笨硫威,双氧威,分朴菊酯,fenpyrad,唑螨酯,倍硫磷,杀灭菊酯,fipronil,氟啶胺,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫磷,安果,噻唑硫磷,fubfenprox,呋线威,
HCH,庚虫磷,氟铃脲,噻螨酮,
咪蚜胺,iprobenfos,异唑磷,异丙威,异恶唑磷,齐墩螨素,
氯氟氰菊酯,lufenuron
马拉硫磷,灭蚜磷,mervinphos,mesulfenphos,蜗牛敌,methacrifog,甲胺磷,杀朴磷,灭虫威,灭多虫,metolcarb,milbemectin,久效磷,moxidectin,
二溴磷,NC 184,NI25,nitenpyram,
氧化乐果,甲氨叉威,砜吸磷,oxydeprofos,
一六0五A,一六0五M,氯菊酯,稻丰散,甲拌磷,伏杀磷,亚胺硫磷,磷胺,腈肟磷,抗蚜威,虫螨磷M,虫螨磷A,溴丙磷,猛杀威,丙苯磷,发果,pymetrozin,吡唑硫磷,pyradaphenthion,反灭虫菌,除虫菊,哒螨酮,pyrimidifen,pyriproxifen,喹噁磷,
RH 5992,
杀抗松,subufos,silafluofen,硫特普,乙丙硫磷,
tebufenozid,tebufenpyrad,tebupirimiphos,teflubenzuron,七氟菊酯,双硫磷,叔丁威,特丁磷,杀虫畏,thiafenox,硫双灭多威,特氨叉威,甲基乙拌磷,硫磷嗪,thuringiensin,四溴菊酯,三唑磷,triazu-ron,敌百虫,triflumuron,trimethacarb,
蚜灭多,XMC,Xylylcarb,YI5301/5302,Zetamethrin。
与其它已知的活性化合物如除草剂的混合物也是可以的,或者与肥料和生长调节剂构成混合物。
本发明活性化合物与增效剂的混合物还可存在于商业上常规制剂中,和存在于由这些制剂制成的使用形式中。增效剂是化合物,由于它的作用,活性化合物的活性增加了,而所加的增效剂本身不需要是具有活性的。
由一般商业制剂制成的使用形式中的活性化合物含量能在很宽范围内变化。使用形式的活性化合物浓度从0.000000l至95%(活性化合物重量),优选0.0001和1%(重间)之间。
根据使用形式用常规方法可有效施用。
当用于消灭卫生害虫和储存产物害虫时,活性化合物不能有显著的残留活性在树木和泥土内并不能有好的碱稳定性于石灰处理的物质上。
按照本发明的活性化合物不仅能杀植物害虫,卫生害虫和储存产物害虫,而且也能在兽医范围内杀牲畜寄生虫(外寄生虫)如鳞蜱,隐喙蜱,马痒螨,恙螨,蚤(螯针类和吸吮类),寄生蝇幼虫,虱,头虱,鸟蚤和跳蚤。
这些寄生虫包括:
虱目:如血虱属,长鄂虱属,头虱属,阴虱属,盲虱属…
食毛目和钝角亚目和细角亚目,如毛鸟虱属,短角鸟虱属,巨毛虱属,羽虱属,WerneCkiella SPP,lepikentron SPP.,Damalina SPP.,啮毛虱属,猫羽虱属,
双翅目和长角亚目和短角亚目,如伊蚊属,按蚊属,库蚊属,纳属,真纳属,白蛉属,Lutzomyia SPP.,库蒙属,斑虻属,Hybomitraspp.,AtylotusSPP.,虻属,麻虻属,Philipomyia SPP.,Braula SPP.,蝇属,HydrotaeaSPP.,螯蝇属,血属,Morellia SPP.,厕蝇属,舌蝇属,丽蝇属,绿蝇属,金蝇属,肉蝇属,麻蝇属,狂蝇属,皮蝇属,胃蝇属,虱蝇属,食毛属,羊虱蝇属,
蚤目,如蚤属,栉头蚤属,鼠蚤属,角叶蚤属,
异翅目,如臭虫属,猎蝽属,红腹猎蝽属,全圆蝽属,
蜚蠊目,如东方蜚蠊,美洲大蠊,德国小蠊,蠊属,
螨亚纲和后胸气门目和中气亚目,如隐喙蜱属,纯喙蜱号,Otabius SPP.,硬蜱属,花蜱属,牛蜱属,革蜱属,血蜱属,玻眼蜱属,刺皮螨属,耳螨属,肺刺螨属,胸孔螨属…
光芒虫亚目(前气门亚目)和Acaridida(Astigmata),如蜂盾螨属,姬螯螨属,禽螯螨属,肉螨属,绵羊疥螨属,脂螨属,恙螨属,螨属,粉螨属,食酷螨属,嗜木螨属,Hypodectes SPP,翼衣属,痒螨属,皮螨属,耳螨属,疥螨属,耳螨属,鸟疥螨属,鸡螨属,鸡雏螨属…
例如他们表现出显著的杀蟑螂活性,如美洲大蠊,和杀蝇如家蝇。
他们了显示出改进的抑制作用,例如杀绿蝇幼虫。
本发明式(I)活性化合物也适于消灭危害农产动物的节肢动物,如牛,绵羊,山着,马,猪,驴,骆驼,水牛,兔,鸡,火鸡,鸭,鹅和蜜蜂,和其它家禽,例如狗,猫,笼养鸟和缸养鱼,及所谓实验动物的,如腮鼠,豚鼠,大鼠和小鼠。通过消灭这些节肢动物,可以达到减少死亡数和避免减产(在肉,奶,羊毛,皮,蛋,蜂密等情况下),所以使用本发明活性化合物可以保持牲畜养殖变得更经济和容易。
用已知的方法在兽医领域使用本发明活性化合物可内服如片,胶囊,药水,兽用顿服药,颗粒,膏,boli,喂食方法,和栓剂,肠胃外用药如注射(肌肉,皮下,静脉内,腹膜内,等),植入,鼻内给药,经皮施用,如浸渍或洗浴,倒上和点样,洗和吹粉,也借助于含有活性化合物的成型的产品,如环,耳钉,尾箍,肢带,缰绳,标记装置等。
当用于牲畜,家禽,家畜等时,式(I)活性化合物可以含活性化合物的剂形(如粉剂,乳剂,可流组合物)使用,活性化合物的含量为1-80%(重量),或直接或稀释100至10000倍,或将它们用作化学浴。
另外还发现本发明的式(I)化合物具有消灭破坏工业物质的害虫的显著杀虫活性。
可以通过实例和选择提及下述害虫,但并不限于此。甲虫,如:
北美家天牛,Chlorophorus Pilosis,家俱窃蠹,Xestobiumrufovillosum,Ptilinus Pecticornis,Dendrobium Pertinex,Ernobiusmollis,Priobium Carpini,竹粉蠹,非洲粉蠹,平颈粉蠹,线粉蠹,柔毛粉蠹,Trogoxylon aequale,Minthes Rugicollis,小蠹,TryptodendronSpec僧海豹属蛾,长蠹,异形长蠹,红褐色Sinoxylon Spec竹长蠹。革翅目,如
钢青树蜂,大树蜂,泰加树蜂,augur树蜂,白蚁,如
木白蚁,短白蚁,indicola花白蚁,黄胸散白蚁,Sontonenis犀白蚁,避光白蚁,澳洲白蚁,nevadensis古白蚁,家白蚁。衣鱼,如西洋衣鱼。
在本文中将工业物质理解为无生命物质,例如优选塑料,粘合剂,胶水,纸和板,皮革,木材和木材制品,和涂复组合物。
这些应防虫害的物质特别选择木材和木材制品。
能用本发明或含本发明化合物的组合物保护的本材或木材制品应理解为例如建筑商品木,木轴,铁路枕木,桥梁构件,栈桥,木轮,箱,货架,容器,电话杆,木贴面,木窗和木门,木层,粗纸板,细木工制品或十分通常用于建筑或细木工的木制品。
活性化合物可以浓缩形式或通常剂形使用如粉剂,颗粒剂,溶液,悬浮液,乳液或膏剂。
上述制剂可用本领域领域已知的方法制备,如将活性化合物与至少一种溶剂或稀释剂,乳化剂,分散剂和/或粘结剂或固定剂,防水剂,干燥剂和UV稳定剂混合,如果需要还可加入染料,颜料和进一步加工的辅剂。
用于保护木材和木制品的杀虫组合物或浓缩物含浓度为0.0001至95%(重量)的本发明活性化合物,特别从0.001至60%(重量)。
施用的组合物或浓缩物的量取决于害虫的种类和影响行为和介质。使用的最佳量在各情况下可按用途通过一系列的试验决定。然而,通常施用0.0001至20%(重量),优选0.001至10%(重量)活性化合物就足够了,此量是基于要保护的物质计算的。
所用溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或油或类似油的有机化学溶剂或低挥发性溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水,如果希望,和乳化剂和/或润湿剂。
所施用的有机化学溶剂优选是油或具有蒸发数高于35和闪点高于30℃,优选高于45℃的类油溶剂。所用的油和不溶的低挥发性溶剂物质是合适的矿物油或它们的芳香馏份或溶剂混合物,它包含矿物油,优选石油溶剂,石油和/或烷基苯。
使用具有沸点170-220℃的矿物油,沸腾范围170至220℃的石油溶剂,沸腾范围250至350℃的锭子油,沸腾范围160至280℃的石油或芳烃,松节油醇等。
在优选实施方案中,所用物质是沸腾范围为180至210℃的液体脂族烃或沸腾范围为180至220℃的芳烃和脂族烃的高沸点混合物和/或锭子油和/或一氯萘,优选α-氯萘。
挥发数高于35和闪点高于30℃,优选高于450℃的低挥发有机油或类油溶剂部分被高或中挥发度有机化学溶剂替代,但需溶剂混合物也具有高于35的蒸发数和高于30℃,优选高于45℃的闪点,和杀虫剂/杀菌剂混合物在此溶剂混合物中是可溶的或可乳化的。
在优选实施方案中,部分有机溶剂或溶剂混合物被脂族极性有机溶剂或溶剂混合物替代。优选使用的物质是含有羟基和/或酯和/或醚基的脂族有机溶剂如乙二醇醚,酯或类似物。
本发明范围内所用的有机粘结剂是本技术领域已知的粘胶,干性油和/或合成树脂,能用水稀释和/或在所用有机溶剂中是可溶的,可分散的或可乳化的,特别粘结剂含有或由下述物质组成:丙烯酸树脂,乙烯树脂,例如聚乙酸乙烯酯,聚酯树脂,缩聚或加聚树脂,聚氨基甲酸乙酯树脂,醇酸树脂或改性醇酸树脂,酚醛树脂,烃类树脂如茚-香豆酮树脂,硅氧烷树脂,干性植物油和/或干性油和/或以天然和/或合成树脂为基的自然干燥的粘结剂。
用作粘结剂的合成树脂能以乳剂,分散剂或溶剂形式施用。也可作粘结剂施用的物质是沥清或含量高于10%(重量)的沥清物质。此外可以使用现有技术已知的染料、颜料、水拒斥剂,有气味的物质和抑制剂或抗腐蚀剂等。
该组合物或浓缩物优选含作为按本发明的有机粘结剂的是至少一种醇酸树脂或改性醇酸树脂和/或干性植物油。按照本发明,优选使用油含量高于45%(重量),优选50至68%(重量)的醇酸树脂。
上述粘结剂可全部或部分被固定剂(混合物)或增塑剂(混合物)替代。这些添加剂是防止活性化合物挥发和结晶或沉淀。优选替代0.01至30%粘结剂(以所用粘结剂100%为基)。
增塑剂是从化学类邻苯二甲酸酯衍生而来,如邻苯二甲酸二丁酯,邻苯二甲酸二辛酯或邻苯二甲酸苄酯丁酯,磷酸酯如磷酸二丁酯,己二酸酯如二-(2-乙基己基)己二酸酯,硬脂酸酯如硬脂酸丁酯或硬脂酸戊酯,油酸酯如油酸丁酯,甘油醚或较高分子量乙二醇醚,甘油酯和对甲苯磺酸酯。
固定剂化学上基于聚乙烯烷基醚,如聚乙烯甲基醚或酮,如二苯酮或亚乙基二苯酮。
其他合适的溶剂或稀释剂是特别水单独或与一种或多种上述有机溶剂或稀释剂,乳化剂和分散剂的混合物。
木材特别有效的保护是用工业范围的浸渍方法如真空,二重真空或加压方法来完成。
如果合适,备用的组合物可含其他杀虫剂,和如果需要,一种或多种其他杀菌剂。
外加的共—组分优选是WO94/29268中所提及的杀虫剂和杀菌剂。在此文献中提及的化合物可写成是本申请的一部分。
特别优选搭配的共—成分可以是杀虫剂,如毒死蜱,腈肟磷,Silafluofin,甲体氯氰菊酯,氟氯氰菊酯,氯氰菊酯,丙体氯氰菊酯,氯菊酯,咪蚜胺,NI-25,氟蛉脲,氟蛤脲,和triflumuron,和杀菌剂,如epoxyconazole,hexaconazole,aza-conazole,丙环唑,戊唑醇,环唑醇,metconatole,烯菌灵,抑菌灵,对甲抑菌灵,丁基氨基甲酸3-碘-2-丙炔酯,N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
按照本发明的活性化合物的制备和用途可从下述实施例得知。制备实施例
在室温下将1.5ml(0.02mol)37%的甲醛水溶液滴加到2.54g(0.0lmol)3-(2-氯吡啶-5-基甲基)-2-硝基亚甲基咪唑啉和2.1g(0.0lmol)2-氨基-4-甲基-4-(4-氯苯基)戊烷在90ml乙醇中的混合物中,将混合物加热回流3小时。冷至室温后,真空除去溶剂,将乙醚加到残余物中,混合物被抽滤。
得到3.2g(理论的66%),6,7-二氢-6-[4-甲基-4-(4-氯苯基)戊-2-基]-8-硝基-(5H)-1-(2-氯吡啶-5-基甲基)咪唑烷并[2,3-f]嘧啶,熔点162℃。
在室温下将4.62ml(0.0462mol)37%的甲醛水溶液滴加到5.9g(0.0231mol)3-(2-氯吡啶-5-基甲基)-2-硝基亚甲基咪唑烷和3.0g(0.0231mol)3-二甲基氨基-2,2-二甲基丙胺在120ml乙醇的混合物中,混合物被加热回流3小时。冷至室温后,真空除去溶剂,残余物与乙醚搅拌,将混合物抽滤。
得到6.9g(理论值的73%)6,7-二氢-6-(3-二甲基氨基-2,2-二甲基丙-1-基)-8-硝基-(5H)-1-(2-氯吡啶-5-基甲基)咪唑烷并[2,3-f]嘧啶,熔点136℃。
在室温下将2.0ml(0.02mol)30%的甲醛水溶液滴加到2.5g(0.01mol)3-(2-氯吡啶-5-基甲基)-2-硝基亚甲基咪唑烷和2.3g(0.01mol)2-氨基-2-甲基-4-(3,4-二氯苯基)丁-3-炔在90ml乙醇中的混合物中,混合物被加热回流3小时。冷至室温后,真空除去溶剂,残余物与乙醚搅拌,将混合物抽滤。
得到3.6g(理论值的73%)6,7-二氢-6-[2-甲基-4-(3,4-二氯苯基)丁-3-炔-2-基]-8-硝基-(5H)-1-[2-氯吡啶-5-基甲基)咪唑烷并[2,3-f]嘧啶,熔点130℃。
为了生产活性化合物的合适制剂,1份重的活性化合物与规定量的溶剂和规定量的乳化剂混合,浓缩物用水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)浸入所需浓度的活性化合物的制剂中进行处理,并且只要叶子是湿的用寄生辣根猿叶虫(Phaedon cochleariae)传染。
一定时间后,测定以%表示的消灭程度。100%表示所有的甲虫幼虫部被杀死;0%表示没有甲虫幼虫被杀死。
在此试验中,7天后,根据例如,制备实施例3,4,5,6,7,8,9,10,11,20,21,24,27,31,32,35,46,51,52,53,54,55,56,57,58,59,60,67,85和86的化合物为例的活性化合物浓度为0.1%,显示100%的消灭程度。实施例B小菜蛾试验溶剂:7份重的二甲基甲酰胺乳化剂:1份重的烷基芳基聚乙二醇醚
为了生产活性化合物的合适制剂,1份重的活性化合物与规定量的溶剂和规定量的乳化剂混合,浓缩物用水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)浸入所需浓度的活性化合物的制剂中进行处理,并在叶子还保持湿润时用小菜蛾(Plutella maculipennis)的蠋传染。
一定时间后,测定以%表示的消灭程度。100%表示所有甲虫幼虫都被杀死;0%表示没有甲虫幼虫被杀死。
在此试验中,7天后,根据例如,制备实施例1,4,6,7,8,10,11,22,26,27,28,31,33,45,46,51,56,59,62,66和86的化合物为例的活性化合物浓度0.1%时,显示100%的消灭程度。实施例C粘虫试验溶剂:7份重的二甲基甲酰胺乳化剂:1份重的烷基芳基聚乙二醇醚
为了生产活性化合物的合适制剂,将1份重的活性化合物与规定量的溶剂和规定量的乳化剂混合,浓缩物用水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)浸入所需浓度的活性化合物的制剂中进行处理,在叶子保持湿润时用草地贪夜蛾(Spodoptera frugiperda)的蠋传染。
一定时间后,测定以%表示的消灭程度。100%表示所有甲虫幼虫都被杀死;0%表示没有甲虫幼虫被杀死。
在此试验中,7天后,根据例如,制备实施例7,8,9,10,11,12,22,23,25,26,35,37,41,43,45,46,51,55,59和70的化合物为例的活性化合物浓度为0.1%时,显示100%的消灭程度。实施例D甜菜夜蛾试验溶剂:7份量的二甲酰胺乳化剂:1份重的烷基芳基聚乙二醇醚
为了生产活性化合物的合适制剂,将1份重的活性化合物与规定量的溶剂和规定量的乳化剂混合,浓缩物用水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)浸入所需浓度的活性化合物的制剂进行处理,在叶子保持湿润时用甜菜夜蛾(Spodoptera exigna)的蠋传染。
一定时间后,测定以%表示的消灭程度。100%表示所有甲虫幼虫都被杀死;0%表示没有甲虫幼虫被杀死。
在此试验中,3天后,根据例如,制备实施例27,28,32,和33的化合物为例的活性化合物浓度为0.1%时,显示100%的消灭程度。实施例E棉铃虫试验溶剂:7份量的二甲基甲酰胺乳化剂:1份重的烷基芳基聚乙二醇醚
为了生产活性化合物的合适制剂,将1份重的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓缩物用水稀释至所需浓度。
将黄豆苗(Glycine max)浸入所需浓度的活性化合物的制剂进行处理,在叶子保持湿润时用棉铃虫(Heliothis armigera)传染。
一定时间后,测定以%表示的消灭程度。100%表示所有蠋都被杀死;0%表示没有蠋被杀死。
在此试验中,3天后,根据例如,制备实施例5,27,28,32,和33的化合物为例的活性化合物浓度为0.1%时,显示100%的消灭程度。实施例F黑尾叶蝉试验溶剂:7份量的二甲基甲酰胺乳化剂:1份重的烷基芳基聚乙二醇醚
为了生产活性化合物的合适制剂,将1份重的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓缩物用水稀释至所需浓度。
将秧苗(Oryza sativa)浸入所需浓度的活性化合物的制剂进行处理,在叶子保持湿润时用黑尾叶蝉(Nephotettix cincticeps)传染。
一定时间后,测定以%表示的消灭程度。100%表示所有叶蝉都被杀死;0%表示没有叶蝉被杀死。
在此试验中,6天后,根据例如,制备实施例8,10,11,12,20,22,23,24,25,37,41,45,68,70和71的化合物为例的活性化合物浓度为0.1%时,显示100%的消灭程度。实施例G蚜虫试验溶剂:7份量的二甲基甲酰胺乳化剂:1份重的烷基芳基聚乙二醇醚
为了生产活性化合物的合适制剂,将1份重的活性化合物与规定量的溶剂和规定量的乳化剂混合,浓缩物用水稀释至所需浓度。
用桃蚜(Myzus persicae)严重传染的甘蓝叶(Brassica oleracea)浸入所需浓度的活性化合物的制剂中进行处理,
一定时间后,测定以%表示的消灭程度。100%表示所有桃蚜都被杀死;0%表示没有桃蚜被杀死。
在此试验后,6天后,根据例如,制备实施例1,6,8,9,10,12,22,25,26,27,28,29,32,46,54,59,60和86的化合物为例的活性化合物浓度为0.1%时,显示100%的消灭程度。实施例H叶螨试验(OP-耐受性/浸泡处理)溶剂:7份量的二甲基甲酰胺乳化剂:1份重的烷基芳基聚乙二醇醚
为了生产活性化合物的合适制剂,将1份重的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓缩物用含乳化剂的水稀释至所需浓度。
用所有阶段的棉叶螨(Tetranychus urticae)严重传染的豆株(Phaseolusvulgaris)浸入所需浓度的活性化合物的制剂中进行处理,
一定时间后,测定以%表示的消灭程度。100%表示所有棉叶螨都被杀死;0%表示没有棉叶螨被杀死。
在此试验中,13天后,根据例如,制备实施例13,14,15,16和17的化合物为例的活性化合物浓度为0.1%时,显示98%的消灭程度。实施例I极限浓度试验/土壤昆虫试验昆虫:Diabrotica balteata-在土壤中的幼虫溶剂:4份重的丙酮乳化剂:1份重的烷基芳基聚乙二醇醚
为了生产活性化合物的合适制剂,将1份重的活性化合物与所述量的溶剂所述混合,加入所述量的乳化剂,浓缩物用水稀释至所需浓度。在本文中,在制剂中的活性化合物的浓度不是至关重要的,只要每单位体积土壤中的活性化合物的量(ppm(mg/l))是有效的。
土壤被放入0.5r的盆中,在20℃放置。
混合后,立即将5粒预先发芽的玉米种子种在各个盆内。1天后,试验昆虫被放入处理过的土壤中。再过7天后, 活性物质的作用程度通过数死的和活的参试昆虫以%测定。当所有试验昆虫都被杀死时,作用程度为100%,当活的昆虫与未处理的对照相同时为0%。
在此试验中,根据例如,制备实施例31的化合物为例的活性化合物浓度为20ppm时,显示100%的消灭程度。实施例J极限浓度试验/根部系统作用试验昆虫:Aphis fabae溶剂:4份量的丙酮乳化剂:1份重的烷基芳基聚乙二醇醚
为了生产活性化合物的合适制剂,将1份重的活性化合物与所述量的溶剂混合,加入所述量的乳化剂,浓缩物用水稀释至所需浓度。
活性化合物的制剂立即与土壤混合。在本文中,制剂中活性化合物的浓度几乎是无关紧要的,只要每单位体积土壤中的活性化合物的量(ppm(mg/l))是有效的。处理过的土壤被放入锅中,上面种有豆子(Vicia faba)。以此途径活性化合物可被植物的根从土壤中摄取并输送到叶子上。
为了测定根部内吸效果,7天后叶子只用上述试验生物传染。再过6天后,评价通过数或估计死的生物而进行。活性化合物的根部内吸作用从杀灭图得出。如果所有试验生物都被杀死时为100%,如果活昆虫与未处理的对照相同为0%。
在此试验中,根据例如,制备实施例1,6,29,31和32的化合物为例的活性化合物浓度为20ppm时,显示100%的消灭程度。实施例K丽蝇幼虫试验/成长抑制作用试验生物:Lucilia cuprina-幼虫乳化剂:35份重的乙二醇—甲基醚
35份重的壬基苯酚聚乙二醇醚
为了生产活性化合物的合适制剂,将3份重的活性化合物与7份重的上述混合物混合,这样得到的乳油用水稀释至所需的具体浓度。
约20只Lucilia cuprina res.幼虫被装入含有约1cm3马肉和0.5ml活性化合物制剂的试管中。24小时和48小时后,活性化合物制剂的活性被测定。将该试管转移到底部用沙覆盖的烧杯中。再过2天后,拿出试管,并数出蛹。
活性化合物制剂的作用根据在未处理的对照的试样的1.5倍的成长周期之后羽化的蝇数评估。本文中,100%表示没有蝇羽化;0%表示所有的蝇都正常羽化。
在此试验中,根据例如,制备实施例1,3,5,6,7,10,12,18,119,20,22,23,24,25,26,27,28,31,32,33,34,35,37,38,39,40,41,42,43,44,51,53,55,56,58,59,60,61,62,63,64,65,66,67,69,70,71和73的化合物为例的活性化合物浓度为1000ppm时,显示100%的消灭程度。实施例L用家蝇(Musca domestica)试验试验生物:Musca domestica成虫,Reichwald系(OP,SP,氨基甲酸酯耐受性)溶剂:35份重的乙二醇一甲基醚
35份重的壬基苯酚聚乙二醇醚
为了生产合适制剂,将3份重的活性化合物与7份重的上述溶剂/乳化剂混合物混合,这样得到的乳油用水稀释至所需的具体浓度。
2ml此活性化合物制剂被吸移到合适大小的Petri盘的滤纸盘(φ9.5)中。滤纸盘干燥后,25只试验生物被转移到Petri盘中并盖上。
1,3,5和25小时后,活性化合物制剂的活性被测定。本文中,100%表示所有的蝇都被杀死; 0%表示没有蝇被杀死。
在此试验中,根据例如,制备实施例3,6,7,10,12,18,19,20,21,22,23,24,25,26,33,34,35,37,38,40,41,42,43,53,56,59,60,61,62,63,64,65,66,67,69,70,71和73的化合物为例的活性化合物浓度为1000ppm时,显示100%的消灭程度。实施例M蜚蠊试验试验生物:美洲大蠊溶剂:35份重的乙二醇一甲基醚
35份重的壬基苯酚聚乙二醇醚
为了生产合适制剂,将3份重的活性化合物与7份重的上述溶剂/乳化剂混合物混合,这样得到的乳油用水稀释至所需的具体浓度。
将2ml此活性化合物制剂吸移到合适大小的Petri盘中的滤纸盘(φ9.5cm)中。滤纸盘干燥后,5只试验生物P.americana被转移到Petri盘中并盖上。
3天后,活性化合物制剂的活性被测定。本文中,100%表示所有的蜚蠊都被杀死;0%表示没有蜚蠊被杀死。
在此试验中,根据例如,制备实施例1,5,10,23,33,和43的化合物为例的活性化合物浓度为1000ppm时,显示100%的消灭程度。
Claims (7)
2.制备按照权利要求1的式(I)取代的四氢-5-硝基-嘧啶的方法其中n 表示0或1,R1 表示非强制性取代的吡啶基或非强制性取代的噻唑基和其中Alk 表示具有多于一个碳原子的烷基,Alk1至Alk6 各自独立地表示烷基,Hal 表示卤素,m 表示1或2,p 表示1,2或3,r和s 各自独立地表示0,1,2,3或4,R3 在各情况下表示非强制性取代的苯基,吡啶基或N-吗啉代,R4 在各情况下表示非强制性取代的苯基或噻吩基,R5 在各情况下表示非强制性取代的苯基,萘基或吡啶基和X 表示氧,硫或NAlk7基,
其中
其中
R1和n 具有上面给出的含义与式(III)的胺
H2N-R2 (III)
其中
R2 具有上面给出的含义在至少两倍摩尔量甲醛存在下,在有或无酸性催化剂存在下和有或无稀释剂存在下进行反应。
3.消灭害虫的组合物,其特征在于含至少一种按照权利要求1的式(I)四氢-5-硝基-嘧啶。
4.用按照权利要求1的式(I)四氢-5-硝基嘧啶消灭害虫的用途。
5.消灭害虫的方法,其特征在于使按照权利要求1的式(I)四氢-5-硝基-嘧啶作用于害虫和/或它们的栖息地。
6.制备消灭害虫的组合物的方法,其特征在于使按照权利要求1的式(I)四氢-5-硝基嘧啶与填料和/或表面活性剂混合。
7.使用按照权利要求1的式(I)的一种四氢-5-硝基嘧啶制备消灭害虫的组合物的用途。
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DE19529411A DE19529411A1 (de) | 1995-08-10 | 1995-08-10 | Substituierte Tetrahydro-5-nitro-pyrimidine |
DE19529411.4 | 1995-08-10 |
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US (1) | US5677307A (zh) |
EP (1) | EP0758652B1 (zh) |
JP (1) | JPH09183780A (zh) |
KR (1) | KR100467976B1 (zh) |
CN (1) | CN1151404A (zh) |
BR (1) | BR9603376A (zh) |
DE (2) | DE19529411A1 (zh) |
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AUPP105497A0 (en) * | 1997-12-19 | 1998-01-15 | Schering-Plough Animal Health Limited | Aqueous insecticidal pour-on treatment |
US7297660B2 (en) * | 2001-03-28 | 2007-11-20 | Huntsman Petrochemical Corporation | Alkylene carbonate adjuvants |
EP1420644B1 (de) * | 2001-08-23 | 2006-05-31 | Bayer CropScience S.A. | Substituierte propargylamine |
EP3532630B1 (en) | 2016-10-31 | 2020-06-24 | Eastman Chemical Company | Enzymatic preparation of propamocarb |
CA3061787A1 (en) * | 2017-05-15 | 2018-11-22 | Cognition Therapeutics, Inc. | Compositions for treating neurodegenerative diseases |
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DE3638121A1 (de) * | 1986-05-30 | 1987-12-03 | Bayer Ag | 1,2,3,6-tetrahydro-5-nitro-pyrimidin-derivate |
DE3739263A1 (de) * | 1987-11-18 | 1989-06-01 | Bayer Ag | Nitrogruppenhaltige imidazolidino-1,2,3,4-tetrahydropyrimidine bzw. hexahydropyrimidino-1,2,3,4-tetrahydropyrimidine |
DE3739264A1 (de) * | 1987-11-18 | 1989-06-01 | Bayer Ag | 2-chlor-1,3-thiazol-5-yl-methyl substituierte nitrogruppenhaltige imidazolidino-1,2,3,4-tetrahydropyrimidine bzw. hexahydropyrimidino-1,2,3,4-tetrahydropyrimidine |
TW242626B (zh) * | 1992-09-01 | 1995-03-11 | Du Pont |
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1995
- 1995-08-10 DE DE19529411A patent/DE19529411A1/de not_active Withdrawn
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1996
- 1996-07-29 EP EP96112214A patent/EP0758652B1/de not_active Expired - Lifetime
- 1996-07-29 DE DE59611118T patent/DE59611118D1/de not_active Expired - Fee Related
- 1996-07-29 ES ES96112214T patent/ES2231795T3/es not_active Expired - Lifetime
- 1996-08-02 US US08/691,834 patent/US5677307A/en not_active Expired - Fee Related
- 1996-08-07 JP JP8223246A patent/JPH09183780A/ja active Pending
- 1996-08-07 KR KR1019960032865A patent/KR100467976B1/ko not_active IP Right Cessation
- 1996-08-09 BR BR9603376A patent/BR9603376A/pt not_active Application Discontinuation
- 1996-08-10 CN CN96112278A patent/CN1151404A/zh active Pending
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KR970010767A (ko) | 1997-03-27 |
US5677307A (en) | 1997-10-14 |
BR9603376A (pt) | 1998-05-12 |
KR100467976B1 (ko) | 2005-04-22 |
EP0758652A1 (de) | 1997-02-19 |
JPH09183780A (ja) | 1997-07-15 |
ES2231795T3 (es) | 2005-05-16 |
DE19529411A1 (de) | 1997-02-13 |
EP0758652B1 (de) | 2004-10-20 |
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