CN1209727A - 杀虫剂 - Google Patents
杀虫剂 Download PDFInfo
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- CN1209727A CN1209727A CN 95194421 CN95194421A CN1209727A CN 1209727 A CN1209727 A CN 1209727A CN 95194421 CN95194421 CN 95194421 CN 95194421 A CN95194421 A CN 95194421A CN 1209727 A CN1209727 A CN 1209727A
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Abstract
本发明涉及式(Ⅰ)的氯烟碱基杀虫剂和增效剂的混合物。式(Ⅰ)中的取代基X、A、Z和E具有说明书中所给的意义。增效剂是来自下列类别的化合物:a)异苯并二氢吡喃或苯并二氧杂环戊二烯化合物,b)炔丙基衍生物,c)烷基膦酸酯,d)磷酸酯,e)吡咯衍生物,f)蒎酮酯,g)甲酰胺,h)C12－21羧酸酯和C12－21羧酰胺,i)二芳基胺,k)环酰亚胺,l)印度楝树油。
Description
本发明涉及以氯烟碱基杀虫剂和杀虫剂的增效剂为基础的杀虫剂。
氯烟碱基杀虫剂已从EP-OS 192060中得知。
杀虫剂的增效剂是氧化酶或细胞色素P450的抑制剂或者提高细胞膜的穿透性，例如从Springer出版社1981年版植物保护剂和除虫杀菌剂化学，第7卷第3～5页，作者K.Naumann写的拟除虫菊酯杀虫剂合成化学(Chemie der pflanzenschutz-und SchdlingsbekmpfungsmittelBnd.7.K.Naumann Chemie der Synthetischen Pyrethroid-InsektizideSpringer Verlag 1981 Seiten 3-5)中已知道这些杀虫剂的增效剂。
本发明涉及式(Ⅰ)氯烟碱基杀虫剂和增效剂的混合物，所述式(Ⅰ)如下：
式中：
A 代表可被任选取代的烷基或代表双官能团，它与Z基相连接；
E 代表吸电子的基团；
X 代表-CH=或=N-基，在此-CH=基可代替氢原子与Z基相连；
Z 代表来自烷基、-O-R、-S-R和
系列的单官能团，或代表与A基或X基相连的双官能团；和
R 代表氢或烷基；
所述增效剂是来自下列类别的化合物：
a)异苯并二氢吡喃(isochroman)或苯并二氧杂环戊二烯化合物
b)炔丙基衍生物
c)烷基膦酸酯
d)磷酸酯
e)吡咯衍生物
f)蒎酮酯
g)甲酰胺
h)C12-21羧酸酯和C12-21羧酰胺
i)二芳基胺
k)环酰亚胺和
l)印度楝树油。
优选的式(Ⅰ)化合物是式中的基团具有以下意义的化合物：
A 代表可被任选取代的C1-4-烷基，或代表双官能团。可提及具有1-4个、特别是有1-2个碳原子的可被任选取代的亚烷基，其中亚烷基可被N、O和S系列的杂原子间隔。
A和Z可与其相连的原子一起形成饱和的或不饱和的杂环。此杂环可含其它一个或两个相同或不同的杂原子和/或杂基团。杂原子最好是氧，硫或氮，杂基团是N-烷基，其中N-烷基的烷基最好含有1至4个，特别是1或2个碳原子。可提及的烷基是甲基、乙基、正丙基和异丙基、正丁基、异丁基和叔丁基。此杂环含有5至7个环原子，最好含有5或6个环原子。
杂环的例子有吡咯烷、哌啶、哌嗪、六亚甲基亚胺、六氢化-1,3,5-三嗪、吗啉，它们可任选地被取代，优选被甲基取代。
E 代表吸电子的基团，其中特别是NO2或CN。
X 代表-CH=或-N=。
Z 代表可被任选取代的C1-4烷基，-OR,-SR和-NRR，其中R优选代表氢或C1-4-烷基，
Z 除上述的环之外，还可同与之相连的原子和=C-基在X位置上形成一个饱和的或不饱和的杂环。此杂环可含有另外的1个或2个相同或不同的杂原子和/或基团。作为杂原子最好是氧、硫或氮，而作为杂基团为N-烷基，在此烷基或N-烷基最好含有1至4个，特别是1或2个碳原子。作为烷基可提及甲基、乙基、正丙基、异丙基、正丁基、异丁基和叔丁基。此杂环含有5至7个环原子，最好含有5或6个环原子。
作为杂环的例子有吡咯烷、哌啶、哌嗪、六亚甲基亚胺、吗啉和N-甲基哌嗪。
作为按照本发明可特别优先选用的化合物(Ⅰ)可列出以下这些化合物：
作为优选的增效剂提出以下化合物：a)异苯并二氢吡喃衍生物，化学式如下：
在式中：R、R1和R2可相同或不同，代表氢或烷基。苯并二氧杂环戊二烯衍生物，化学式如下：
在式中：R表示氢，C1-4烷基，C2-4烯烃基，卤素或硝基，R1表示C1-4烷基或氢，R2表示芳烷基，C1-4烷基，C2-4烯烃基，C3-6环烷基或表示氢，和此外R1和R2共同代表C2-5亚烷基，例如2-(3,4-亚甲二氧基苯基)丙腈，如下式
特别是在下列文献提到的化合物：
BE-P 858254；DE-OS 2654348；DE-OS 2816475；b)来自炔丙基衍生物系列，化合物的化学式如下
其中：
Alk表示C1-4烷基和
Aryl表示苯基。
特别是在下列文献提出的化合物：
US-P 3864388；DE-OS 2235005；US-P 4020111；
NE-OS 715782 ；c)来自烷基膦酸酯系列的化合物，可特别提及在EP-OS 25179和
US-P 3338783中提到的化合物；d)来自磷酸酯系列的化学式如下的化合物：
其中：
n表示数字0或1
X和Y相互独立地代表O或S
R表示可被任选取代的烷基、芳基或芳烷基。
特别是在以下文献中已披露的化合物：US-P4 035490；JP-OS54/147927；以及下列化学式的化合物
e)来自吡咯衍生物系列的化合物，其化学式如下：
其中：Hal表示卤素Alk表示C1-4烷基，和下式的化合物
在式中：R代表烯基或炔基，和基团R1、R2、R3和R4可以相同或不同，表示氢，氰基，硝基，卤素，氨基甲酰基，单烷基氨基羰基或二烷基氨基羰基，氨基磺酰基，单烷基氨基磺酰基或二烷基氨基磺酰基，表示可任选地被卤素、氰基、烷氧基或烷硫基取代的烷基，或代表可任选地被卤素取代的烷氧基、烷硫基或烷基磺酰基，或者其中两个相邻的基团R1和R2、R2和R3或R3和R4共同代表亚烷基或苯并。
可特别提及在下列文献中提到的化合物：DE-OS 2833193；JP-OS 53/81625；f)来自蒎酮酯的化合物，化学式如下：
Alk表示C1-4烷基
和在JP-OS 673514中提到的化合物；g)来自甲酰胺类的化合物，可提及二甲基甲酰胺；h)来自羧酸酯和羧酰胺类的化合物，可提及辛基二乙基酰胺和C12-18羧酸异丙酯。特别是在下列文献提出的化合物：JP-OS 74/21068；JP-OS 73/99337；i)来自二芳基酰胺类的化合物，可提及在EO-OS 926中提出的化合物。特别可提及下列化合物：k)环酰亚胺，可提及下列化合物：
和
可将活性物质的混合物制成常规的制剂，如溶液，乳液，悬浮液，粉末，泡沫，糊剂，颗粒剂，气雾剂，活性物质浸渍的天然和合成材料，用于种子的在聚合物质中和在包衣组合物中的微细胶囊，此外还可制成带燃烧装置，例如带烟熏筒、烟熏盒、烟熏螺旋管的制剂形式以及制成ULV-冷雾和热雾的制剂形式。
这些剂型可以已知的方式生产，例如，将活性物质与稀释剂(即液态溶剂，压力下的液化气体)和/或固体载体混合，并任选使用表面活性剂，即乳化剂和/或分散剂，和/或发泡剂。用水作稀释剂的情况下，有机溶剂也可以例如用作助溶剂。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，例如矿物油馏分，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；液化的气态稀释剂或载体是指环境温度和大气压力下是气态的液体，例如气雾剂喷射剂，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：例如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，玉米穗轴和烟草茎；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，木素亚硫酸盐废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或胶乳形式的天然和合成聚合物，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)的活性物质混合物。
这些活性物质混合物适用于防治动物病害，尤其适用于消灭出现在农业、森林、贮存产品保护和材料保护以及在卫生领域中的昆虫、蜘蛛纲的动物和线虫，并具有良好的植物耐受性和对温血动物合适的毒性。这些活性混合物对通常敏感的和有抗药性的物种以及对所有或某些发育阶段都有活性。上述的害虫包括：
等足纲，例如潮虫、鼠妇和粗潮虫。
倍足纲，例如具斑马陆。
唇足纲，例如蜈蚣和蚰蜓。
综合纲，例如庭院么蚰。
缨尾目，例如衣鱼。
弹尾目，例如武装棘跳虫。
直翅目，例如东方非蠊、美洲大蠊、马德拉非蠊、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，例如欧洲球螋。
等翅目，例如散白蚁属的种类。
虱目，例如体虱、血虱属种类和毛虱属种类。
食毛目，例如羽虱属和畜虱属的种类。
缨翅目，例如温室纹蓟马和烟蓟马。
异翅目，例如扁盲蝽属种类、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，例如甘蓝粉虱、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、葡萄根瘤蚜、瘿绵蚜属种类、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，例如棉红铃虫、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，例如家具窃蠹、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、油莱金头跳甲、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，例如锯角叶蜂属的种类、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，例如伊蚊属种类、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，例如印鼠客蚤和角叶蚤属的种类。
蛛形纲，例如黑歇和毒治虾。
蜱螨目，例如粗脚粉螨、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。
本发明的活性物质混合物可以以其市售的制剂形式和以由此制剂制成的、与其它活性物质混合的使用形式存在，所述其它活性物质例如有杀虫剂、引诱剂、杀菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂和除莠剂。杀虫剂包括例如磷酸酯，氨基甲酸酯，羧酸酯，卤代烃，苯基脲，用微生物制备的物质等等。
由市售制剂制成的使用形式的活性物质的含量可在很大范围内变化。使用形式的活性物质浓度可为0.0000001至95％(重量)活性物质，最好是在0.0001和1％(重量)之间的活性物质。
以适合于使用形式的普通方法来使用本发明的活性物质混合物。
在下列的实施例中是把下式所示的Imidacloprid作为来自氯代烟碱基杀虫剂类的杀虫有效物质来使用的：
实施例A
Phaedon-幼虫-试验
溶剂：7重量份二甲基甲酰胺
乳化剂：1重量份烷基芳基聚乙二醇醚
为制备适当的活性物质制剂将1重量份的活性物质与给定量的溶剂和给定量的乳化剂混合并用水将此浓缩物稀释至所需的浓度。
将卷心菜叶子(Brassica oleracea)浸没在此所需浓度的活性物质制剂中进行处理并在叶子还潮湿时加入辣根叶甲虫-幼虫(Phaedoncochleariae)。
在所需的时间之后，该植物被辣根叶甲虫幼虫占满。在7天以后测定杀死的百分率。在此情况下100％意味着所有的甲虫幼虫都被杀死，0％表示没有甲虫幼虫被杀死。
在各试验浓度的Imidacloprid中加入0.02％的增效剂。在此试验中，例如下列混合物，显示出了增效作用：
表A(损害植物的昆虫)Phaedon-幼虫试验
实施例B
| 活性物质 | 按％计的活性物质浓度 | 按％计的杀死程度7天后 |
| Imidacloprid已知 | 0.0008 | 0 |
| DEF已知 | 0.02 | 0 |
| Imidacloprid+DEF | 0.00080.02 | 100 |
| Kitazin已知 | 0 02 | 0 |
| Imidacloprid+Kitazin | 0.00080.02 | 65 |
Plutella-试验(BLT抗性)
溶剂： 7重量份二甲基甲酰胺
乳化剂： 1重量份烷基芳基聚乙二醇醚
为制备适当的活性物质制剂，将1重量份的活性物质与给定量的溶剂和给定量的乳化剂混合并将此浓缩物用水稀释成所需的浓度。
将卷心菜叶(Brassica oleracea)通过浸没在所需浓度的活性物质制剂中进行处理，并在叶子还潮湿时放入小菜蛾的毛虫(Plutellamaculipennis,BLT抗性)。
在所需时间后测定杀死的百分率。100％表示所有的毛虫都被杀死，0％表示无毛虫被杀死。
在Imidacloprid的各试验浓度中加入0.02％的增效剂。在此试验中例如下列混合物显示出了增效作用：
表B(损害植物的昆虫)Plutella-试验(抗药性)
实施例C
| 活性物质 | 按％计的活性物质浓度 | 按％计的杀死程度7天后 |
| Imidacloprid已知 | 0.004 | 0 |
Spodoptera-试验
溶剂： 7重量份二甲基甲酰胺
乳化剂： 1重量份烷基芳基聚乙二醇醚
为制备适当的活性物质制剂，将1重量份的活性物质与给定量的溶剂和给定量的乳化剂混合并用水将此浓缩物稀释至所需浓度。
将卷心菜叶(Brassica oleracea)通过浸没在所需浓度的活性物质制剂中进行处理，趁叶子还潮湿时放入夜蛾幼虫(Spodopterafrugiperda)。
在所需时间后测定杀死百分率。100％表示幼虫全部被杀死，0％表示无幼虫被杀死。
在Imidacloprids的各试验浓度中各加入0.02％的增效剂。在此试验中例如下列混合物显示出了增效作用：
表C
(损害植物的昆虫)
Spodoptera frugiperda-试验
实施例 D
| 活性物质 | 按％计的活性物质浓度 | 按％计的杀死程度7天后 |
| Imidacloprid已知 | 0.0008 | 10 |
| DEF已知 | 0.02 | 25 |
| Imidacloprid+DEF | 0.00080.02 | 70 |
Nephotettix-试验
溶剂： 7重量份二甲基甲酰胺
乳化剂： 1重量份烷基芳基聚乙二醇醚
为制备适当的活性物质制剂，将1重量份的活性物质与给定量的溶剂和给定量的乳化剂混合并用水将此浓缩物稀释至所需浓度。
将水稻秧苗用浸没在所需浓度的活性物质制剂中进行处理并趁秧苗还潮湿时放入黑尾叶蝉的幼虫(Nephotettix cincticeps)。
在所需时间后测定杀死百分率。在此情况下100％表示所有叶蝉都被杀死，0％表示无叶蝉被杀死。
在Imidacloprids的各试验浓度中各加入0.02％的增效剂。在此试验中例如下列混合物显示出了增效作用：
表D
(损害植物的昆虫)
Nephotettix-试验
实施例E
| 活性物质 | 按％计的活性物质浓度 | 按％计的杀死程度6天后 |
| Imidacloprid已知 | 0.00000128 | 0 |
| DEF已知 | 0.02 | 0 |
| Imidacloprid+DEF | 0.000001280.02 | 100 |
Myzus-试验
溶剂： 3重量份二甲基甲酰胺
乳化剂： 1重量份烷基芳基聚乙二醇醚
为制备适当的活性物质制剂，将1重量份的活性物质与给定量的溶剂和给定量的乳化剂混合并将此浓缩液用水稀释至所需浓度。
将严重受桃蚜(Myzus persicae)侵袭过的卷心菜叶(Brassicaoleracea)通过浸没在所需浓度的活性物质制剂中进行处理。
在所需时间后测定杀死百分率。在此情况下100％表示所有的蚜都被杀死，0％表示无蚜被杀死。
表E
(损害植物的昆虫)
Myzus-试验
| 活性物质 | 按％计的活性物质浓度 | 按％计的杀死程度6天后 |
| Imidacloprid已知 | 0.00016 | 25 |
| Kitazin已知 | 0.02 | 0 |
| Imidacloprid+Kitazin | 0.000160.02 | 75 |
Claims (1)
1．式(Ⅰ)的氯烟碱基杀虫剂与增效剂的混合物，所述式(Ⅰ)如下：
式中：A 代表可被任选取代的烷基或代表双官能团，它与Z基相连接；E 代表吸电子的基团；X 代表-CH=或=N-基，在此-CH=基可代替氢原子与Z基相连；Z 代表来自烷基、-O-R、-S-R和
系列的单官能团，或代
表与A基或X基相连的双官能团；和R 代表氢或烷基；所述增效剂是来自下列类别的化合物：
a)异苯并二氢吡喃或苯并二氧杂环戊二烯化合物
b)炔丙基衍生物
c)烷基膦酸酯
d)磷酸酯
e)吡咯衍生物
f)蒎酮酯
g)甲酰胺
h)C12-21羧酸酯和C12-21羧酰胺
i)二芳基胺
k)环酰亚胺和
l)印度楝树油。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 95194421 CN1209727A (zh) | 1995-07-17 | 1995-07-17 | 杀虫剂 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 95194421 CN1209727A (zh) | 1995-07-17 | 1995-07-17 | 杀虫剂 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1209727A true CN1209727A (zh) | 1999-03-03 |
Family
ID=5082707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 95194421 Pending CN1209727A (zh) | 1995-07-17 | 1995-07-17 | 杀虫剂 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1209727A (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101014352B (zh) * | 2004-08-03 | 2011-03-02 | 植物制药有限公司 | 包含印度楝树油和金丝桃属的油提取物的、具有愈合、驱除和杀菌性能的用于处理外部伤口的组合物 |
| CN102223800A (zh) * | 2008-11-25 | 2011-10-19 | 住友化学株式会社 | 害虫防治组合物和防治害虫的方法 |
-
1995
- 1995-07-17 CN CN 95194421 patent/CN1209727A/zh active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101014352B (zh) * | 2004-08-03 | 2011-03-02 | 植物制药有限公司 | 包含印度楝树油和金丝桃属的油提取物的、具有愈合、驱除和杀菌性能的用于处理外部伤口的组合物 |
| CN102223800A (zh) * | 2008-11-25 | 2011-10-19 | 住友化学株式会社 | 害虫防治组合物和防治害虫的方法 |
| US8940777B2 (en) | 2008-11-25 | 2015-01-27 | Sumitomo Chemical Company, Limited | Pest controlling composition and method of controlling pest |
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