CN1031238C - 3-氰基-5-烷氧基-1-芳基吡唑杀虫剂 - Google Patents
3-氰基-5-烷氧基-1-芳基吡唑杀虫剂 Download PDFInfo
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- CN1031238C CN1031238C CN90101152A CN90101152A CN1031238C CN 1031238 C CN1031238 C CN 1031238C CN 90101152 A CN90101152 A CN 90101152A CN 90101152 A CN90101152 A CN 90101152A CN 1031238 C CN1031238 C CN 1031238C
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
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- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
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Abstract
本发明阐述了新颖的式(I)3-氰基-4-亚磺酰化-5-烷氧基-1-芳基吡唑(见附图),其中典型优先的取代基是:R是全部被卤(素)原子取代的C1~C4烷基;R1是C1~C4烷基、C3~C6链烯基或炔基等;R2、R3、R5和R6是氢或卤素;R4是CF3、卤素或烷基等,以及n是0,1或2。本发明进一步涉及制备化合物的中间产物及其方法以及它的组合物,本发明还涉及控制节肢动物(特别是昆虫)、线虫、蠕虫和原生动物的方法。
Description
本发明涉及一些3-氰基-4-亚磺酰化的-5-取代的氧基-1-芳基吡唑及其中间体以及制备这些化合物的方法。本发明进一步涉及对节肢动物、线虫、蠕虫及原生有害动物进行控制的组合物及方法,本发明特别涉及对叶子昆虫和土壤昆虫进行控制而不损伤作物的农用组合物及方法。
美国专利第4,770,692号阐述了将5-烷氧基吡唑用作除草剂和植物生长调节剂。欧洲专利申请第284030号和日本专利申请第63185965号也阐述了将5-取代的-烷氧基吡唑用作除草剂。日本专利申请第75126663号和第75126664号阐述了将5-烷氧基吡唑用作止痛剂和消炎剂。欧洲专利第234119号和第249033号阐述了将各种吡唑用作杀昆虫剂、杀螨剂和杀线虫剂。
其中:
R是选自未取代的C1—C4烷基或被一个或多个相同或不同的卤素原于取代至完全取代的C1—C4烷基;
R1是选自C1—C4烷基、C3—C6链烯基、C3—C6炔基、芳烷基或芳基,其中R1是非取代的或可以被一个或多个从卤素、烷基、硝基、烷氧基、烷基硫代、烷基亚硫酰基、烷基磺酰基、羟基、氰基、羧基、烷氧基羰基、氨基羰基、烷氨基羰基或二烷氨基羰基中选出来的取代基所取代,或者R1是从氨基羰基、烷氨基羰基或二烷氨基羰基中选出来的,其中所定义的R1基团的烷基和烷氧基部分各自包含1—4个碳原子,或者R1是-P(=X)OR7SR8(其中X是氧原子或硫原子);
R2、R3、R5和R6各自是氢原子或卤(素)原子;
R4从卤(素)原子或者C1—C4直链或支链烷基、烷氧基、烷基硫代、烷基亚硫酰基或烷基硫酰基中选出来的,这些基团是非取代的或被一个或多个相同或不同的卤(素)原子所取代;
R7是甲基或乙基;
R8是直链或支链C3—C4烷基;以及
n是0,1或2
其中:
R是被相同或不同卤(素)原子所完全取代的C1—C4烷基;
R1是从C1—C4烷基、C3—C6链烯基、C3—C6炔基或芳烷基中选出来的,其中R1是非取代的或是被一个或多个从卤素、烷基、氰基、烷氧基羰基或二烷氨基羰基中选出来的取代基所取代,或者R1是选自二烷氨基羰基其中所定义的R1的烷基和烷氧基部分各自包含1—4个碳原子,或者R1是-P(=X)OR7SR8(其中X是氧原子或硫原子);
R2是氢原子或卤(素)原子;
R4是从卤(素)原子、CF3、OCF3、SCF3、SOCF3、SO2CH3、OCHF2或C1—C4烷基中选出来的;
R7是甲基或乙基
R8是直链或支链的C3—C4基;以及
n是0,1或2。
本发明的一个目的是提供吡唑系列的新的化合物及其制备方法以及它的中间产物。
本发明的第二个目的是提供,例如,农艺学上和药用上可接受的组合物。
本发明的第三个目的是提供用来抵御节肢动物(特别是昆虫)、植物线虫、蠕虫和原生有害动物的高活性化合物。这些化合物因而能在例如农业作物和园艺作物、森林、兽药和家畜管理以及公共卫生中得到有利的使用。
本发明的再一个目的是提供通过土壤或叶子施用的具有广谱活性的杀昆虫剂、杀螨剂和杀线虫剂的化合物。
本发明的一个附加目的是提供对寄居土壤的昆虫(例如谷物根部的虫类)以及双翅目(蝇)类具有特别高活性的化合物。
用这里所定义的化合物可完全或部分地达到本发明的这些及其它目的。
通过各种方法可以方便地制得本发明的3-氰基-4-亚磺酰化的-5-烷氧基-1-芳基吡唑。反应流程I和II阐述了两种优选的方法,其中R′是C1—C4烷基,R、R1—R8和n的定义同上。
在反应流程I的起始原料中,乙炔二羧酸酯1可以买到,苯肼2也是市售产品,或者它们可通过下列众所周知的文献方法进行制备。中间产物苯腙3可以分离出来,或者不进行分离而用诸如三乙胺、碱金属或碱土金属的氢氧化物、烷醇盐或碳酸盐的碱处理而环合成4。可在-80℃—150℃之间,较好地在0—40℃之间进行该反应。另一个方法是,用英国专利说明第585,780号所述的方法也以制备4型的吡唑啉酮,这里列出可供参考。
在诸如氯代的烃类、烃类、醚等非质子传递的溶剂中,较好地是在二氯甲烷中,用诸如吡啶或任何叔胺的酸接受剂使吡唑啉酮4与硫基氯容易地进行反应。根据硫基卤试剂和溶剂的沸点,可以在约-20℃和约100℃之间进行该反应。
通过使羟基吡唑5与诸如硫酸二甲酯或者硫酸二乙酯的硫酸二烷酯或者与诸如甲基碘、甲基溴、乙基碘或乙基溴进行反应并使用前述的任何碱可使其烷基化成相应的醚6。该反应通常在惰性有机溶剂中,典型地在约30℃—约180℃的回流温度下进行。
用相似的方法,用苄基卤、链烯基卤和炔基卤也可制备相应的苄醚、链烯基醚和炔基醚。可以代替的是,在醚溶剂中使5与重氮甲烷反应也可以制得甲基醚6。在碱的存在的情况下吡唑啉酮5也可与α-卤代酯或-α卤代酮反应制得具有酯或羰基官能团性质的醚。
在常温和在压力下,在惰性有机溶制中,使醚6与氨反应可制得羧酰胺7。可以替换地,通过公知的化学方法将6水解成相应的酸并使之转变成酰氯化物。然后使之进一步与氨反应得到羧酰氨7。
通常在约30℃—180℃的溶剂回流温度下用诸如磷酰氯或五氧化二磷的标准脱水剂在无或有惰性溶剂时进行脱水得到腈8。常用的优选溶剂是脂族的或芳族的烃类、氯代烃类和醚。
用适当量的过乙酸或三氟过乙酸或间-氯代过苯甲酸或过氧化氢或过乙酸和过氧化氢或过氧单硫酸钾的混合物或商品名为“过硫酸氢钾制剂”使硫醚8氧化成亚砜或砜9。该反应通常在典型地具有沸点为约-30℃—约180℃的惰性有机溶剂中进行。
英国专利说明第585780号、欧洲专利申请第265305号和日本专利第75116473号中阐述了反应流程II中间体10和型13吡唑啉酮的制备,这里列出,作为参考。
将13(烃)硫基化成14以及将14烷基化成8的条件依次与所述的相关化合物,即根据反应流程I的制备中式4制得5,5制得6的反应参数范围相似。
本发明所期待的且典型性优选的且有代表性的无限制的化合物是通式(I)的化合物,其中取代基的含义如表1所示。
下列实施例阐述了本发明式(I)和(II)典型优选和代表性的化合物以及制备的中间产物及方法。化合物的熔点代表观察得化合物熔点的平均值或进一步代表若干个别熔点测定值的平均值。另外,对每种化合物采用了一种或多种光谱分析(红外、核磁共振、气相色谱/质谱等)以定出和确证其化学结构。
表1
代表性的(I)1-芳基吡唑化合物
取代基
R | n | R1 | R2 | R3 | R4 | R5 | R6 |
CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | 0001201200001001200 | CH3C2H5(CH3)2CHCH3CH3CH3CH3CH3CH3C2H5CH3C2H5CH3CH3CH3CH3CH3CH3CH3 | ClClClClClClClClHHBrBrHHClClClClCl | HHHHHHHHHHHHHHHHHHH | CF3OCF3OCF3CF3OCF3OClClClCF3CF3CF3CF3CF3CF3OCF3SCF3SOCF3SO2CF3SOCF3SO2 | HHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClCl |
表1
代表性的(I)1-芳基吡唑化合物
取代基
R | n | R1 | R2 | R3 | R4 | R5 | R6 |
CF3CFCl2CH3CH3CH3CF3CF3CF3CF3CFCl2CFCl2CF3CF3CF3CF3CFCl2CF3CF3CF3 | 1001200100101020010 | CH3CH3CH3CH3CH3NCCH2CH3SO2CH2NCCH2PhCH2HC≡C-CH2HC≡C-CH2HC≡C-CH2HC≡C-CH2H2C=CH-CH2HC≡C-CH2H2C=CH-CH2NCCH2CH2NCCH2CH2HOCH2CH2 | ClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHH | CF3SO2CF3OCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClCl |
表1
代表性的(I)1-芳基吡唑化合物
取代基
R | n | R1 | R2 | R3 | R4 | R5 | R6 |
CF3CF3CF3CFCl2CF2ClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CFCl2CFCl2CFCl2 | 0120001012000012012 | CH3O2CCH2CH3O2CCH2CH3O2CCH2C2H5O2CCH2C2H5O2CCH2(CH3)2NOCCH2(CH3)2NOCCH2CH3O2CCH(CH3)CH3O2CCH(CH3)CH3O2CCH(CH3)CH3O2CH2CH2CH3COCH2ClCH2C(OCH3)CH2CH3CH3CH3CH3CH3C2H5 | ClClClClClClClClClClClClClFFFFFF | HHHHHHHHHHHHHFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHFFFFFF | ClClClClClClClClClClClClClFFFFFF |
表1
代表性的(I)1-芳基吡唑化合物
取代基
R | n | R1 | R2 | R3 | R4 | R5 | R6 |
CF3CF3CF3CF3CF3CF3CF3CFCl2CF2CFCl2CF2CFCl2CF2CF3CF3CFCl2CF3CF3CF3CF3 | 1220100O120000000 | CH3SO2CH2CH3SO2CH2NCCH2CH3NHCOCH(CH3)CH3NHOCCH(CH3)C2H5NHOCCH(CH3)CH3NHCOCH(CH3)CH3CH3CH3(C2H5O)(sBuS)P(O)(CH3)2NOC(CH3)2NOCCH3SCH2C2H5CH3CH2=CHCHNHOCCH(CH3) | ClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHH | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CH3t-C4H9CF3 | HHHHHHHHHHHHHHHHH | ClClClClClClFClClClClClClClClClCl |
实施例1
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-甲氧基吡唑的制备:
反应流程I的方法:
中间体:1-(2,6-二氯-4-三氟甲基苯基)-3-(甲氧基羰基)-吡唑啉-5-酮的制备
在搅拌下,将18.5克(0.13摩尔)二甲基乙炔二羧酸酯溶于75毫升甲醇中的溶液滴加到30.1克(0.123摩尔)2,6-二氯-4-三氟甲基苯肼在75毫升甲醇中的溶液里。将反应混合物在10—20℃下搅拌2.5小时。在50分钟的时间里将该褐色混合物慢慢地加到搅拌着的甲醇钠溶液中,(将11.0克(0.478摩尔)钠溶于400毫升无水甲醇中制得)。另外再搅拌1.5小时后,将溶液于部分真空下浓缩并用100毫升4N盐酸酸化。过滤沉淀出来的固体,用水洗涤并在空气中干燥得到28.4克(65%收率)的棕黄色固体,熔点245—246℃,将其用甲醇重结晶得一固体,熔点249.5℃
b)中间体:1-(2,6-二氯-4-三氟甲基苯基)-3-甲氧基羰基-4-三氟甲基硫基-5-羟基吡唑的制备
将10克(0.028摩尔)1-(2,6-二氯-4-三氟甲基苯基)-3-(甲氧基羰基)-吡唑啉-5-酮在150毫升含有2.45克(0.03摩尔)的吡啶的二氯甲烷中的溶液冷却至-10℃—0℃,向内加入3.75毫升(0.04摩尔)三氟甲烷硫基氯。让反应混合物搅拌过夜,然后用乙酸乙酯稀释并用水洗涤。干燥有机层并浓缩得到13.0克棕黄色固体。用己烷∶甲基叔丁醚重结晶得到5.5克产品。熔点:217℃
C H N
C13H6Cl2F3N2O3S的计算值:34.30 1.32 6.15
测定值:34.43 1.46 6.01
c)中间产物:1-(2,6-二氯-4-三氟甲基苯基)-3-甲氧基羰基-4-三氟甲基硫基-5-甲氧基吡唑的制备
将5.8克(0.013摩尔)1-(2,6-二氯-4-三氟甲基苯基)-3-甲氧基羰基-4-三氟甲基硫基-5-羟基吡唑和0.37克(0.015摩尔)氢化钠在150毫升二噁烷中的悬浮液加热回流0.5小时,此时颜色从褐色转橙色并伴有气体逸出。向冷却的混合物中加入1.94克(0.015摩尔)稀释在10毫升二噁烷中的硫酸二甲酯。再将混合物加热回流1小时。然后将其冷却,滤去固体并将滤液浓缩。将褐色油置于二氯甲烷中并用水洗涤。干燥有机层并浓缩得到3.8克(62.4%收率)的褐色油,用硅胶柱色谱层析纯化给出固体,熔点:97.5%
C H N
C14H8Cl2F6N2O3S的计算值: 35.83 1.70 5.97
测定值: 36.40 1.75 5.86
d)中间产物:1-(2,6-二氯-4-三氟甲基苯基)-3-氨基羰基-4-三氟甲基硫基-5-甲氧基吡唑的制备
在一只耐压瓶中含有3.5克1-(2,6-二氯-4-三氟甲基苯基)-3-甲氧基羰基-4-三氟甲基硫基-5-甲氧基吡唑在100毫升甲醇中的冷溶液并将氨气通入该压力瓶内以得到饱和溶液。将瓶密封并让之在室温和初始压力6—10磅/平方英寸(psig)下静置。16小时后,在部分真空下浓缩反应混合物。色谱层析纯化后得到2.86克(84%收率)的固体,熔点150.5℃。
C H N
C13H7Cl2F6N3O2S的计算值: 34.37 1.55 9.25
测定值: 34.58 1.78 9.05
e)1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-甲氧基吡唑的制备
将3.5克1-(2,6-二氯-4-三氟甲基)-3-氨基羰基-4-三氟甲基硫基-5-甲氧基吡唑在25毫升磷酰氯中的混合物回流加热2小时。冷却后,将混合物慢慢倒入200毫升冰中。过滤得到黄色沉淀并溶于乙酸乙酯中。使有机层干燥并浓缩。用己烷及异丙醇结晶并分离得到2.88克(85.7%收率)的白色固体,熔点:84℃
C H N
C13H5Cl2F6N3OS的计算值: 35.72 1.15 9.63
测定值: 36.11 1.44 9.46
反应流程II的方法
f)中间产物:3-氰基-3-(2,6-二氯-4-三氟甲基苯基)腙丙酸乙酯的制备
重氮盐的制备:
将亚硝酸钠(6.27克,0.0909摩尔)分三部分加入正在搅拌的浓硫酸(58.3克,0.595摩尔)中。外面用冰使混合物保持冷却。将硫酸-亚硝酸钠混合物加热至80℃直至所有的固体都溶解,形成一清澄的黄色溶液。将亚硝酰-硫酸混合物冷却至室温并用57毫升冰醋酸稀释。搅拌该混合物并加入19.0克(0.0826摩尔)2,6-二氯-4-三氟甲基苯胺溶于50毫升乙酸中的溶液。将该混合物在50—65℃下加热1小时并冷却。
重氮盐与氰基琥珀酸二乙酯的反应:
将14.7克(0.0859摩尔)氰基琥珀酸二乙酯溶于115毫升乙酸和170毫升水中的溶液,进行搅拌并滴加入实施例1f中制得的重氮盐。加料完成后,将115克乙酸钠在200毫升水中的溶液加入反应混合物中并继续搅拌0.5小时。然后将反应混合物倒入1000毫升冰和水中。用300毫升一份的二氯甲烷萃取水混合物,合并有机萃取液并用230毫升氢氧化铵洗涤。弃去水萃取物。另外加入460毫升氯氧化铵并使有机层搅拌过夜。分离有机相,干燥并浓缩得到19.5克橙色油。经色谱纯化得到11.4克固体,经NMR分析知它是几何异构体混合物。质谱分析给出m/e=368(M+)。
C H N
C13H10Cl2F3N3O2的计算值: 42.11 2.73 11.41
测定值: 42.02 2.63 11.26
g)中间产物:1-(2,6-二氯-4-三氟甲基苯基)-3-氰基吡唑啉-5-酮的制备
将1.0克(0.0027摩尔)腙(在实施例1f中制得)在25毫升无水乙醇中的溶液滴加至乙醇钠溶液(将0.23克(0.01摩尔)金属钠溶于75毫升无水乙醇中)。在室温下搅拌3小时后,减压除去乙醇,使残留物溶于水中,冷却并用4N盐酸酸化至pH1。用二氯甲烷萃取油状混合物。干燥溶液并浓缩得到0.87克所需产品。用甲苯结晶给出一棕黄色固体,熔点199.5℃。
h)中间体:1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-羟基吡唑的制备
将0.25克(0.78毫摩尔)1-(2,6-二氯-4-三氟甲基苯基)-3-氰基吡唑啉-5-酮在15毫升二氯甲烷和0.069毫升(0.86毫摩尔)吡啶中的溶液冷却至-70℃并在氮气下保存。向内加入0.1毫升(1.0毫摩尔)三氟甲烷硫基氯。搅拌3小时后,将反应混合物温热至室温。除去过量的三氟甲基硫基氯,反应混合物用乙酸乙酯稀释,用水洗涤,干燥并浓缩得到橙色油。经色谱层析纯化得到0.04克白色固体,熔点325℃(分解)。
i)1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-甲氧基吡唑的制备
根据实施例1c所述的方法使1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-羟基吡唑与硫酸二甲酯进行甲基化反应。产物与实施例1e的产物相同。
实施例2
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基磺酰基-5-甲氧基吡唑的制备
将1.36克(0.0079摩尔)间一氯代过苯甲酸加入至1.57克(0.0036摩尔)1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-甲氧基吡唑在50毫升氯仿中的溶液内。将溶液加热回流3天。滤得冷却后沉淀出来的固体并弃去。用碳酸氢钠、硫代硫酸钠和盐水溶液洗涤滤液。在硫酸钠干燥有机层后,浓缩有机层使之静置时固化。色谱层析纯化得到0.29克(17.2%)产物砜,熔点151.5℃
C H N
C13H5Cl2F6N3O3S的计算值: 33.35 1.07 8.97
测定值: 32.68 1.07 8.81
实施例3
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基亚磺酰基-5-甲氧基吡唑的制备
附加地,从实施例2反应中得到0.63克(38.7%收率)的相应的\1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基亚硫酰基-5-甲氧基吡唑的第二产物,熔点136.5℃。量为(0.8克)未反应的起始原料也可被回收。
C H N
C13H5Cl2F6N3O2S的计算值: 34.53 1.11 9.29
测定值: 34.57 1.11 9.15
实施例4
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-乙氧基吡唑的制备
中间产物:1-(2,6-二氯-4-三氟甲基苯基)-3-甲氧基羰基-4-三氟甲基硫基-5-乙氧基吡唑的制备。
根据实施例1c的反应流程I的方法通过使:1-(2,6-二氯-4-三氟甲基苯基)-3-甲氧基羰基-4-三氟甲基硫基-5-羟基吡唑与硫酸二乙酯和氢化钠在二噁烷中反应而制得中间产物。得到下列光谱数据:MS,m/e=482(M+);NMR(CDCl3):δ1.43(t,J=7.0Hz,C2H5),3.75(s,OCH3),4.4(q,J=7.0,OCH2)和7.76(s,芳族的2H)。
b)1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-乙氧基吡唑的制备
跟着反应流程图I的合成方法,用与实施例1d和1e相似的方法可得到一固体.熔点108.5℃
实施例5
a)1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-二氯氟代甲基硫基-5-甲氧基吡唑的制备。
中间产物:1-(2,6-二氯-4-三氟甲基苯基)-3-甲氧基羰基-4-二氯氟(代)甲基硫基-5-羟基吡唑的制备。
根据反应流程图I方法中的实施例1b的相似方法通过使:1-(2,6-二氯-4-三氟甲基苯基)-3-(甲氧基羰基)-吡唑啉-5-酮与二氯氟代甲烷硫基氯在二氯甲烷和吡啶中反应得到中间产物,其收率为99%,熔点154.5℃。
b)中间体:1-(2,6-二氯-4-三氟甲基苯基)-3-甲氧基羰基-4-二氯氟甲基硫基-5-甲氧基吡唑的制备
将重氮甲烷在二乙醚中的饱和溶液慢慢加至4.14克1-(2,6-二氯-4-三氟甲基苯基)-3-甲氧基羰基-4-二氯氟甲基硫基-5-羟基吡唑在180毫升二乙醚中的溶液内直加到所有的起始原料均被反应为止(用薄层色谱层析(t.l.c)监测)。浓缩反应混合物并用色谱层析纯化产物得到3.5克(82%收率)的白色固体,熔点79.5℃,NMR(CDCl3):δ3.78(S,OCH3),4.3(S,CH3)和7.7(S,芳族的2H)。
c)1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-二氯氟代甲基硫基-5-甲氧基吡唑的制备
与反应流程图I的合成方法相,用实施例1d和1e相似的方法可得到一种固体,熔点94.5℃
另外合成的吡唑化合物
相似地,用实施例1-5的方法,可得到式(III)、(IV)、(V)和(VI)的化的(实施例6—75),其中的取代基含义如表2所示(III):R2=Cl;R4=CF3(IV): R2 and R4=Cl(V): R2=Cl;R4=OCF3(VI): R2=H; R4=CF3
为了进一步例举本发明化合物的制备方法,下列详细的合成方法作为制备实施例18和23化合物的方法。
实施例18
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-乙氧基羰基甲氧基吡唑的制备
将5.0克(11.8毫摩尔)羟基吡唑中间产物(从实施例1h中得到)和经磨细的氢氧化钠粉(1.42克,35.5毫摩尔)悬浮在100毫升二噁烷中并加热回流一小时。然后加入溴代乙酸乙酯(5毫升,过量)并继续加热16小时。让反应混合物冷却,并在部分真空下蒸去二噁烷,使残留物与200毫升水相混合,用2×200毫升乙酸乙酯萃取。干燥有机层并浓缩给出6.1克油状物质。让粗制品经快速硅胶(120克)色谱层析用乙酸乙酯在己烷中的溶液(乙酸乙酯量从5%增加至35%)洗脱后给出2.38克(47%收率)的固体,熔点71℃
C H N
C16H9Cl2F6N3O3S的计算值: 37.81 1.78 8.27
测定值: 37.80 1.78 8.05
实施例23
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-氨基羰基甲氧基吡唑的制备。
一个250毫升装有一干冰冷凝器和一个熔结多孔玻璃管的三颈圆底烧瓶中在氮气氛下向内加入1.0克(1.97毫摩尔)的1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-(乙氧基羰基)甲氧基吡唑溶于50毫升乙醇中的溶液。将溶液在干冰-丙酮浴中冷却。然后向内通入氨气,将冷溶液倒入压力瓶中密封。将反应混合物热至室温其对反应混合物的压力达77磅/英寸2(psig)。两天后在部分真空下浓缩溶液。所得的固体用石油醚研磨得到0.81克(86%收率)的黄色固体,熔点:157℃
C H N
C14H6Cl2F6N4O2S的计算值: 35.09 1.26 11.69
测定值: 35.19 1.36 11.46
本发明的最为优选化合物:
正如式(I)—(III),特别是式(III)所定义的,本发明的最优选化合物是这些实施例1—15的化合物,其中,
R是被相同或不同卤(素)原子全部取代的甲基,最好是CF3、CCl2F或CClF2;
R1是C1—C4烷基,最好是甲基或乙基;
R2和R6各自是一个卤(素)原子,最好是氯;以及R4是CF3。
本发明的另一些优选化合物
另一些也是优选化合物,它们是被式(I)—(V),特别是式(III)—(V)所定义的这些化合物,例如是由实施例17、18、20、22、25、40、43—46、52、53、55和56所代表的化合物,其中:
R是被相同或不同卤(素)原子完全取代的甲基,最好是CF3、CCl2F或CClF2;
R1是未取代的C1—C4烷基或被烷氧基羰基取代的C1—C4烷基,或者R1是芳烷基;
R2和R6各自是一个卤(素)原子,最好是氯,以及R4是一个卤(素)原子,最好是氯,或者R4是CF3或OCF3。
表2另外合成的式(III)、(IV)、(V)和(VI)的吡唑化合物实施例 取代基化合物 R n R1 熔点(℃)式 (III):R2=Cl;R4=CF36 CF3 1 C2H5 1577 CF3 2 C2H5 132.58 CClF2 0 C2H5 939 CCl2F 1 CH3 13710 CCl2F 2 CH3 189.511 CClF2 1 C2H5 161.512 CClF2 2 C2H5 130.513 CClF2 0 CH3 87.514 CClF2 1 CH3 139.515 CClF2 2 CH3 16716 CF3 0 CH2CN 93.517 CF3 0 CH2Ph 7318 CF3 0 CH2CO2C2H5 7119 CF3 1 CH2CO2C2H5 8020 CF3 2 CH2CO2C2H5 58.521 CF3 0 n-C4H9 Oil22 CF3 1 n-C4H9 10223 CF3 0 CH2CONH2 15724 CF3 1 CH2CONH2 Oil
表2另外合成的式(III)、(IV)、(V)和(VI)的吡唑化合物实施例 取代基化合物 R n R1 熔点(℃)式 (IV):R2 and R4=Cl25 CF3 0 CH3 10526 CF3 1 CH3 138.527 CF3 2 CH3 161.528 CClF2 0 CH3 11629 CClF2 1 CH3 14830 CClF2 2 CH3 171.5(dec.)31 CClF2 0 C2H5 9432 CClF2 1 C2H5 16133 CClF2 2 C2H5 148(dcc.)34 CCl2F 0 CH3 124.535 CCl2F 1 CH3 160.536 CCl2F 2 CH3 190(dec.)37 CCl2F 0 C2H5 120.538 CCl2F 1 C2H5 178.539 CCl2F 2 C2H5 173(dcc.)
表2另外合成的式(III)、(IV)、(V)和(VI)的吡唑化合物实施例 取代基化合物 R n R1 熔点(℃)式(V):(V):R2=Cl;R4=OCF340 CF3 0 CH3 101.541 CF3 1 CH3 104.542 CF3 2 CH3 11843 CF3 0 C2H5 80.544 CF3 1 C2H5 13745 CF3 2 C2H5 12146 CCl2F 0 CH3 12447 CCl2F 1 CH3 145.548 CCl2F 2 CH3 15249 CCl2F 0 C2H5 5250 CCl2F 1 C2H5 118.551 CCl2F 2 C2H5 15152 CClF2 0 CH3 11353 CClF2 1 CH3 124.554 CClF2 2 CH3 116.555 CClF2 0 C2H5 60.556 CClF2 1 C2H5 13657 CClF2 2 C2H5 131
表2另外合成的式(III)、(IV)、(V)和(VI)的吡唑化合物实施例 取代基化合物 R n R1 熔点(℃)式 (VI):R2=H;R4=CF358 CF3 0 CH3 70.559 CF3 1 CH3 12760 CF3 2 CH3 82.561 CF3 0 C2H5 51.562 CF3 1 C2H5 11263 CF3 2 C2H5 110.564 CClF2 0 CH3 7865 CClF2 1 CH3 113.566 CClF2 2 CH3 9267 CClF2 0 C2H5 8668 CClF2 1 C2H5 10669 CClF2 2 C2H5 12470 CCl2F 0 CH3 79.571 CCl2F 1 CH3 11572 CCl2F 2 CH3 13073 CCl2F 0 C2H5 94.574 CCl2F 1 C2H5 101.575 CCl2F 2 C2H5 115
实施例76
杀螨剂、杀昆虫剂和杀线虫剂的应用
下列试验方法是在温室里使用实施例1—75的化合物以测定本发明的化合物对螨;某些昆虫,包括蚜虫、松鸡(毛虫)、苍蝇和两种甲虫幼体(一种食叶,另一种食根);以及线虫的杀有害动物的用途和活性。试验的种类如下:
属,种 普通名 (缩写)
Tetranychus urticae 两点蜘蛛螨 TSM
Aphis naslurtil 鼠李蚜虫 BA
Spodoptera eridania 南方粘虫 SAW
Epilachna varivestis 墨西哥豆甲虫(幼体) MBB
Musca domestica 家蝇 HF
Diabrotica u.howardi 南方玉米根虫 SCRW
Meloidogyne incognita 南方根疤螨 SRKN
配方:
根据下列用于每个试验过程的方法将试验化合物(实施例1—75)配方使用。
对于螨、蚜虫、南方粘虫和墨西哥豆甲虫,须制备一种溶液或悬浮液,它通过将10毫克试验化合物加到160毫克二甲基甲酰胺、838毫克丙酮、2毫克3∶1比率的去利通(非离子型表面活性剂)X-172:去利通X-152它们依次主要是阴离子型和非离子型的低泡乳化剂,它们具有有机磺酸酯与芳烷基聚醚醇的无水混合物)、和98.99克水的溶液中而制得溶液或悬浮液。结果得到浓度为100ppm的试验化合物。
对于家蝇,开始用与上述相同的方法制备配方,但是只加16.3克水,并相应地调节其它组分,给出200ppm浓度的配方。最后用等体积的20%(重量)蔗糖水溶液稀释给出100ppm浓度的试验化合物。如果需要,对其施用声波以保证分散完全。
对于南方玉米根虫,用对于家蝇所需制得开始200ppm浓度的相同方法制得溶液或悬浮液。然后根据所需的试验浓度用水稀释以得到该200ppm配方的等分试样。
对于南方根疤螨须用储存溶液或悬浮液,通过将15毫克试验化合物加至250毫克二甲基甲酰胺、1250毫克丙酮和3毫克上述的乳化剂混合物中。然后将水加至总体积为45毫升,该试验化合物的浓度为333ppm。需要时,采用声波以保证分散完全。
试验过程
根据下列试验方法采用特定的浓度[单位ppm,即百万分之份数(重量)]来测定上述配制的试验化合物的杀有害动物的活性。
两点蜘蛛螨:在出芽期用两点蜘蛛螨的成虫和若虫感染叶子,(该螨系从储存的培养液中取得)将感染的叶子放在两株豆科植株的新叶上,该豆科植株在6厘米泥煤罐内生长。在24小时内将足量的试验用螨(150—200)转移到新鲜植物上。将种在罐内的植物(每种化合物一个罐)放在可旋转的转台上,用De Vilbiss喷雾枪在40磅/平方英寸(psig)空气压力下将100毫升100ppm的试验化合物配料喷洒到植物上。作为未处理的对照物,将不含试验化合物的100毫升水一丙酮-DMF乳化剂溶液也喷到感染的植物上。将市售的化合物,三氯杀螨或己噻唑(hexythiazox)采用相同的方法配方以定期试验作为处理对照的标准。喷洒植物六天后,数出能动的形态的死亡率。
鼠牵蚜虫:将鼠李蚜虫的成虫和若虫培养到栽种的矮小旱金莲属植物上。将用100—150个蚜虫侵袭的栽种植物(每种试验化合物一个罐)放在可旋转的转台上,用De Vilbiss喷雾枪在40psig空气压力下将100毫升100ppm的试验化合物配料喷洒到植物上。将不含试验化合物的100毫升水-丙酮-DMF-乳化剂溶液也喷洒到受侵染的植物上以作为未处理的对照。将市售的化合物马拉松(malathion)采用相同的方法配方进行定期试验作为处理对照的标准。喷洒后,将罐贮存一天,然后数出蚜虫的死亡数。
南方粘虫:将罐内种植的豆科植物放在可旋转的转台上,用DeVilbiss喷雾枪在40psig空气压力下将100毫升100ppm的试验化合物配料喷洒上去。将不含试验化合物的100毫升水-丙酮-DMF-乳化剂溶液也喷到植物上作为未处理的对照。将市售化合物沙帕梅林(Cypermethrim)或苏帕福(Sulprofos)采用相同方法配方进行定期试验作为处理对照标准。叶子干燥时,将它放在衬有湿润滤纸的塑料杯里。从第二龄期的南方粘虫幼体中任意选出五条将其导入关闭了五天的每个盘中。即使针刺幼虫也不移动身体长度的被认为已死去。
墨西哥豆甲虫:将罐内种植的植物放在可旋转的转台上,用DeVilbiss喷雾枪在40磅/英寸2(psig)空气压力下将100毫升100ppm试验化合物配料径向喷在植物上。将不含试验化合物的100毫升水-丙酮-DMF-乳化剂溶液也喷洒到植物上以作为未处理的对照。将市售的化合物,Cypermethrin或Sulprofos采用相同方法配方进行定期试验作为处理对照标准。叶子干燥时,将它放在衬有湿润滤纸的塑料杯里。从第二龄期的墨西哥豆甲虫幼体中任选出五条,将其放入关闭了五天的每个盘中。即使针刺,幼虫也不移动身体长度的被认为已死去。
家蝇:根据Chemical Specialties Manufacturing Association(Blue Book,Mc Nair-Dorland Co.纽约1954;243—244页,261页)的说明书在对照条件下培植4—6天龄的家蝇。用二氧化碳麻醉家蝇使其不活动,取出25只雄性和雌性的不动的家蝇放到笼中,该笼包括一个标准的食物筛网及绕有纸张覆盖的表面。将10毫升的100ppm试验化合物配料加到含有脱脂棉衬垫的有蛋奶酥的杯中。将10毫升不含试验化合物的水-丙酮-DMF-乳化剂-蔗糖溶液用相同的方法施用作为未处理的对照。将市售化合物,马拉松用相同的方法定期试验作为处理对照的标准。在放入麻醉的苍蝇之前将饵杯放入食物筛网中。24小时后,对刺无移动反应的苍蝇被认为已死。
南方玉米根虫:在含有60克沙沃土的罐中加入1.5毫升水配料,该配料包括200ppm试验化合物配方的等分部分它是用适量水稀释至试验化合物最终的土壤浓度、3.2毫升水和5份发芽前的玉米种子。将该罐充分振摇使试验配料分散均匀。然后将二十个南方玉米根虫卵放入土壤制成的凹穴中。然后将蛭石(1毫升)和水(1.7毫升)加到此凹穴中。用相似的方法,通过将不含试验化合物的相同等分部分的水-丙酮-DMF-乳化剂溶液制备来处理的对照。另外,用市售化合物(从terbufos、地虫磷、甲拌磷、毒死蜱、虫螨威、isazophos或灭克磷中选出来)采用相同的方法配方进行定期试验作为处理对照的标准。7天后,用众所周知的“Berlesc”漏斗萃取法数出根虫幼体的存活数。
南方根疤螨:受侵染的西红柿植物根里含有南方根疤螨的卵团,将该侵染的根从根株培养物中取出,通过震摇及用自来水洗涤来清除土壤。从根组织中分离出螨卵并用水冲洗。将卵悬浮液的样品放在架在收集碗上的细滤网上,使该收集碗中水的水平调节到能与滤肉接触的水平。从碗中的细滤网上收集得到幼螨。在圆锥形容器的底部塞上粗蛭石,然后将约200毫升体积的消毒土壤向内填至1.5cm高。然后在圆锥形土壤的中央挖个洞并向内注入333ppm试验化含物配料的等分部分。将市售化合物、fenamifos采用相似的方法配方进行定期试验以作为处理对照的标准。作为未经处理的对照是将不含试验化合物的水-丙酮-DMF-乳化剂溶液的等分部分用相似的方法时行施用。用试验化合物处理土壤后马上从每个圆锥容器的顶部加入1000个第二龄期的幼体南方根疤螨。3天后,将单个健康的西红柿幼苗种入圆锥容器内。使包含被侵袭的土壤和西红柿幼苗的圆锥容器在温室中保存3周。在试验结束时,从圆锥容器中取出种下的西红柿幼苗的根并相对于未经处理的对照对察份疤痕作出如下的评估:
1-严重损伤,等于未经处理的对照
2-中等损伤
3-轻度损伤
4-极轻度损伤
5-无损伤,即完全控制
然后将这些结果转变成ED3或ED5值(3级损伤或5级损伤所需的有效剂量)
使用结果:下面讨论了本发明的许多代表性化合物实例具有杀螨、杀昆虫和杀线虫活性,表3列出了试验的品种(BA、SAW、MBB、HF和SCRW:由普遍名缩写所定义)及其剂量比率。用死亡百分率来表示结果。本发明的化合物也可对螨(将实施例13、29、60和70的化合物施用到叶子上使TSM的死亡率达约50—100%)和土壤线虫(用实施例2和9的化合物使SRKN的ED3值依次是11和21—42)进行控制。此外,本发明的化合物可使一些有害动物,例如诸如南方粘虫和墨西哥豆甲虫的叶子害虫减少或使它们拒食。
本发明化合物即使低比率使用时也对各种有害动物有用,例如,以约50—0.5ppm的范围或更少的比率用于叶的施用是有效的;以约50—0.05ppm的范围或更少的比率作为饵的施用是有效的;以约1.0—0.01ppm的范围或更少的比率作为土壤施用是有效的。
在上述讨论和表3的报告的结果中,本发明的化合物是以不同的浓度施用的。将1ppm(施用的试验溶液的化合物的百万分中的份数浓度)溶液或悬浮液或乳液用于叶子上相当于施用1克/公顷活性组分,而根据喷雾体积来计为1000升/公顷(足够从叶子上流下)。从而在叶上施用约6.25—500ppm的喷雾剂相当于约6—500克/公顷。对于土壤施用,相对于7.5厘米土壤深度的1ppm浓度相当于100克/公顷的播洒。
表3
吡唑化合物杀有害动物活性的使用实例
死亡百分率实施例
以100ppm进行叶上施用或饵施用 土壤浓度-1.45ppm化合物 BA SAW MBB HF SCRW1 100 50 0-30 70-100 1002 100 100 70-100 70-100 1003 100 100 70-100 70-100 1004 100 90 0-30 70-100 1005 100 100 70-100 70-100 1006 100 100 70-100 70-100 1007 100 100 30-70 70-100 1008 70 100 30-70 70-100 1009 100 100 70-100 70-100 10010 0 100 0-30 70-100 10011 80 100 0-30 70-100 10012 100 100 70-100 70-100 10013 100 100 0-30 70-100 10014 0 100 0-30 70-100 10015 100 100 70-100 70-100 100
表3
吡唑化合物杀有害动物活性的使用实例
死亡百分率实施例
以100ppm进行叶上施用或饵施用 土壤浓度-1.45ppm化合物 BA SAW MBB HF SCRW17 100 50 0-30 70-100 10018 100 <30 70-100 70-100 10020 100 100 70-100 70-100 10022 100 100 0-30 70-100 10025 <30 <30 0-30 70-100 10040 100 100 0-30 70-100 10043 100 <30 0-30 70-100 10044 <70 100 0-30 70-100 10045 100 100 0-30 70-100 10046 100 >70 0-30 70-100 10052 100 >70 0-30 70-100 10053 100 100 30-70 70-100 10055 100 >70 0-30 70-100 10056 100 >70 0-30 70-100 100
方法及组合物
如前所示本发明的化合物具有明显的杀有害动物结果和用途,它们可以控制许多种包括节肢动物(特别是昆虫)、植物线虫、蠕虫和原生有害动物。这样的化合物可以有利地在实际中使用,例如在农业上和园艺作物上、森林业、兽药和畜养家畜及其公共健康方面得到使用。
本发明的一个特征是提供一种控制有害动物的方法,它包括用有效量的式(I)化合物,较好地用式(II)或式(III)—(IV)化合物,最好是用式(III)—(V)的化合物(其中的取代基定义与前面相同)对所在地进行处理(例如,采用害虫栖息地施用或喂食的方法。所在地包括,例如有害动物本身或者有害动物居留或进食的地方(植物、动物、人类、土地、建筑物、房屋、森林、果园、水路、土壤、植物或动物产品等等)。
本发明的化合物较好地用来控制土壤昆虫,例如玉米根虫、白蚁(特别要保护建筑物)、蚁、根蛆、切根虫、根象鼻虫、普通蛀茎夜蛾(stalkborers)、夜盗蛾、根蚜虫、叶甲科的甲虫和蛴螬。它们也具有抵抗植物病原线虫,例如根节疤线虫、包囊线虫、剑形线虫、损伤线虫以及球茎线虫和抵抗螨的活性。为了控制土壤有害动物,例如控制玉米根虫,可以改进性地施用化合物或者将有效比率的化合物掺到作物种植或播种或生长植物根的土壤里。
此外,通过在叶上施用或对一些节肢动物,特别是一些昆虫的全身作用而有效地控制其生长,用这些节肢动物依靠植物的地上部分进行喂食。
在公共卫生领域,化合物对于控制许多昆虫,特别是污蝇和其它双翅目的有害动物,例如家蝇、厩蝇、兵蝇、角蝇、鹿蝇、马蝇、小蚊、蠓类、黑蝇和蚊子尤为有用。
本发明的化合物可有下列用途并可作用于下列包括节肢动物(特别是昆虫)、线虫、蠕虫和原生有害动物的下列害虫。
在贮存产品,例如包括谷粒和面粉的谷类、可食块茎、动物饲料、木材和家常物品(例如地毯和纺织品)的保护中,本发明的化合物可有效地抵御节肢动物,尤其是甲虫,包括象鼻虫、蛾和螨,例如(Ephestiaspp.(面粉蛾)、Anthrenus spp(地毯甲虫)、Tribolium spp.(面粉甲虫)、Silophilus spp.(谷粒象鼻虫)和Aearus spp.(螨)的侵袭。
在受侵袭的家庭房屋和工业房屋中控制蟑螂、蚂蚁和白蚁及相似的节肢有害动物,在水路、井、水库或其它流水和贮水场所控制蚊子幼体。
对于地基、建筑物和土壤的处理是防止建筑被白蚁,例如方散白蚁、异白蚁、橡胶家白蚁所侵袭。
在农业上可抵御Lepidoplere(蝴蝶和蛾)的成体、幼体和卵,例如,诸如Heliothis viresce(西红柿芽体虫)、棉铃虫和谷实夜蛾的实夜蛾属。Spodoptera spp例如S.exempta,S.littoralis(埃及棉花虫),S.eridania(南方粘虫)和Mamestraconfigurat(宽园粘虫);螟蛉,例如E.insulana(埃及螟蛉),Pectinophora spp.例如Pectinophora gossypiella(粉江螟蛉),Ostrinia spp例如,O.nubilalis(欧洲玉米螟虫),Trichoplusiani(甘蓝尺蠖),Artogeia spp.(甘蓝虫)Laphygma spp.(粘虫),·Agrotis和Amathes spp.(夜盗蛾),Wiseana spp.(蛾),Chilo spp.(稻茎螟虫)Tryporyza spp.和Diatraea spp.(甘蔗糖钻蛀虫和稻螟虫),Sparganothis pil leriana(葡萄浆果蛀虫),胡桃小卷蛾(小苹果蛀虫)Archips spp.(果树蛀虫),Plutellaxylostella(菱纹背蛀虫),松尺蠖,Cheimatobia brumata,苹细蛾,苹果巢蛾,菜蛾,黄褐天幕毛虫,黄毒蛾,毒蛾属,棉潜蛾,秸潜蛾,切根虫属,夜蛾,松夜蛾,斜纹夜蛾,苹果小卷蛾,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,枞色夜蛾,菜长卷蛾和栎绿卷蛾。
本发明的化合物可抵御Coleoptera(甲虫)的成体和幼体,例如Hypothenemus hampei(咖啡浆果蛀虫),Hylesinus spp(黑甲虫),Anthonomus grandis(棉花螟蛉),Acalymma spp,(黄瓜甲虫),Lema spp,Psylliodes spp.,Leptinotarsa decemlineata(科罗拉多土豆甲虫),Diabrotica spp.(玉米根虫),Gonocephalumspp.(假线虫),Agriotes spp.Limonius spp.(线虫),Dermolepida,Popillia spp.Heteronychus spp.(白蛴蜡),Phaedon cochlearie(芥子甲虫),Epitrix spp.(叶甲科的甲虫),Lissorhoptrus oryzophilus(稀粥象鼻虫),Meligethes spp.(花粉甲虫),Ceutorynchus spp.,Rhynchoporus和Cosmopolitesspp.(根象鼻虫),Anobrum punctatum(家俱切蠹),Rhizoperthadominica(谷蠹),Bruchidius obtectus(锥胸豆象)Acantho-selides obtectus(大豆象),Hylotrupes baiulus(北美家天牛),Agelastica alni(杨树萤叶甲),Psylliodes chrysocephala(油类金豆跳甲),Epilachna varivestis(墨西哥大豆瓢虫)、Atomaria spp.,(隐食甲虫属),Oryzaephilus surinamensis(锯谷盗),Anthonomus spp.,(花象属),Sitophilus spp(谷象虫),Otiorrhynchus sulcatus(黑葡萄耳象),Cosmoplites sordidus(香蕉根颈象),Ceuthorrhynchus assimilis(白菜籽象),Hyperspostica(紫苜蓿叶象),Dermestes spp(皮蠹属),Trogodermaspp(谷班属蠹),Anthernus spp(园皮蠹),Attagenus spp.,(毛皮蠹属),Lyctus spp.,(粉蠹),Maligethes aeneus,Ptinus spp(蛛甲属),Niptus hololeucrus(黄珠甲),Gibbium psylloides(禅蛛甲),Tribolium spp,(拟谷盗),Tenebrio molito(黄粉虫),Conoderus spp.,Melolontha melolontha(鳃角金龟),Amphimallon solstitalis(六月金龟)和Costelytra zealandica(褐新西兰助翅鳃角金龟)。
抵御Heteroptea(半翅目)和(半翅目)例如,木虱属,伯粉虱属,粉虱,蚜属,巢亲修尾蚜,根瘤蚜,球蚜,忽布疣蚜,(蛇麻草布拉李树蚜虫)黑尾叶蝉(稻叶跳虫),小绿叶蝉属,飞虱属,蜡蝉属肾园盾蚧属(红价壳虫),软蚧,拟软蚧,Heloneltis spp.(蚊子臭虫),茸盲蝽,棉红椿属,棉兴椿属,绿椿属,扁香椿,方背皮椿,温节臭虫,长红猎蝽和锥猎蝽属,常春藤园盾蚧,甘兰蚜,莱隐瘤蚜,榆梨绵蚜,麦长管蚜,瘤蚜,忽布疣蚜,禾谷缢管蚜,抵御重要的农业上的节肢动物,诸如Acari(螨)例如.Teranychus spp;Panonychus spp和Kryobia spp,(蜘蛛螨),Ornithonyssus spp(禽螨),Eriophse spp.(五倍子螨),Polyphadotasonemus spp.
抵御缨尾目、例如衣鱼。
抵御虱目,例如葡萄根癌蚜,瘿绵蚜属,人虱,血虱属和毛虱属。
抵御羽虱,例如嚼虱和畜虱属。
抵御蚤目,例如印鼠容蚤和角叶蚤属。
抵御其它节肢动物,诸如Blaniulus spp(千足虫)Scutigerella spp(蚁客),Oniscus spp(木虱)和Triops spp(甲壳纲)。
抵御唇足目动物例如,Oniseus asellus,Armadillidiumvulgare和Porcellio scaber.
抵御唇足纲例如Geophilus capophagus和Scutigera spex
抵御侵袭重要的家业、森林和园艺上的植物和树木的螨,它是直接侵袭或通过传播植物的细菌病毒、真菌原生质或真菌疾病来侵袭植物和树木。例如,诸如Meloidogyne spp例如M.incognita的根节疤线虫,诸如Globodera spp.(G.rostochiensis)的包囊线虫,狭体叩头属(H.avenae);Radopholus spp.(例如R.similis),诸如Prathlenchus spp例如P.pratensis的损伤线虫;Belonolaimusspp.(例如B.gracillis);Tylenchulus spp(例如T.semipenertrans);Rotylenchulus spp(例如R.reniformis);Rotylenchus spp(R.robustus);Helicotylenchus spp.(例如H.multicinctus);Hemicycliophora spp.(例如H.gracillis);Criconemoides spp(例如C.similis);Trichodorus spp.(例如T.primitivus);诸如,X,inhinema spp.(例如X.diversicaudatum),Longidorus spp.(例如L.elongatus);Hoploaimus spp.(例如H.coronayus的剑形线虫;Aphelenchoides spp.(例如A.ritzema-bosi,A.besseyi);诸如Ditylenchus spp.(例如D.dipsaci)的球线虫类。
在兽药和畜牧业以及保持公共卫生的领域里本发明的化合物可抵御内部寄生或外部寄生在脊椎动物,特别是温血脊椎动物,例如人和家畜,如牛、羊、山羊、马、猪、家禽、狗和猫上的节肢动物、蠕虫或原生动物,例如,可抵御包括扁虱(例如硬蜱属,牛蜱(例如,微力牛蜱,钝眼蜱,璃眼蜱属,扇头蜱(例如,具尾扇头蜱,Haemanhysalis spp草蜱属,钝缘蜱属(例如,Ornithodorusmoubata)和螨(例如,Damalinis app.,Dermayssus gallinae疥螨(例如Sarcontes,scabiei痒螨,皮痒螨,蠕螨,犹沙螨属;双翅目(例如伊蚊属,按蚊,蝇属,皮绳,胃蝇属,蚋属翅目(例如锥蝽属,阴虱(例如啮虱属,长颚虱,蚤目(例如Ctenocenhalidesspp),Dictyontera(例如Perinlaneta spp,Blatella.spp)膜壳绦虫属,例如Monomorium pharaonis例如抵御由于寄生线虫而引起的胃肠道感染,寄生线虫的例子是下面家族的成员:毛圆线虫,日园线虫,旋毛线虫,捻转血毛线虫,蛇形毛园线虫,细颈线虫,胃线虫,毛园线虫,古柏线虫,膜壳绦虫;本发明的化合物可控制和治疗由例如,艾美球虫,例如艾免美球虫,斑形艾美球虫,扁嘴艾美球虫,锯虫,利什曼原虫,症原虫,巴贝虫,毛滴虫,组织滴虫,贾第鞭毛虫,弓形虫属,溶组织内阿米巴虫,泰累尔梨浆虫属所引起的原生动物的疾病。
如前所述,本发明提供了控制有害动物的方法,它是通过将有效量的式(I)或(II)或(III)—(VI)施用在所在地,它包括对所在地进行处理。
在控制节肢动物(特别是昆虫)、以及植物的线虫有害动物的实践中,例如,一种方法包括将有效量的本发明化合物施用到植物上或者植物生长的介质上。对于这样的方法,施用到所在地的活性化合物用量是能控制节肢动物或线虫侵袭的有效比率,即是处理所在地每公顷约0.005kg—15kg范围的活性化合物。在标准的条件下,根据被控制的有害动物,较低的用量比率也提供了足够的保持作用。另一方面,不利的气候条件、有害动物的耐受性及其它因素则要求活性组份的用量比率稍作提高。最适的用量比率通常视许多因素而定,例如,被控制的有害动物种类、侵染植物的种类及生长阶段、种植间的空间及其施用方法。活性化合物较优选的有效用量比率范围是从约0.01公斤/公顷—2公斤/公顷。
当有害动物能在土壤中生长时,通常将活性化合物配成组合物,并用任何方便的方法使之均匀地分散到被处理的地域(即,例如进行播洒或定区域处理)。如果需要,通常在田里或植物生长的地方或接近种子或作物的地方进行施用以抵御侵袭。活性组份可通过用水喷洒以洗入至土壤中或让下雨的自然作用带入。在施用期间或施用后,如果需要,配好的化合物可机械性地分散于土壤中,例如通过耕田、用圆耙耕地或用牵引链使其分散。可在种植前、种植时,种值后但发芽前或发芽后施用组合物。另外,控制方法也包括在种植前处理种子使之在种下种子后具有持续的控制作用。
控制有害动物的方法也包括对植物的叶子进行施用或处理以控制节肢动物(特别是昆虫)和线虫侵袭植物在空气中的部分。另外,用本发明化合物来控制有害动物的方法可以控制以远离施用点处植物为养料的有害动物,例如,当本发明的化合物用于植物的根部时通过活性化合物的内吸收作用使食叶昆虫得到控制。此外,本发明的化合物通过拒食或排斥作用使对植物的侵袭减少。
本发明的化合物及其控制有害动物的方法在保护田地、饲料、种植园、温室、果园、葡萄园观赏作物、种植园的作物以及森林树木方面尤为有价值,例如:保护谷类(诸如玉米、麦、稻和高梁),棉花,烟草,蔬菜(诸如豆类、油菜作物、葫芦、莴苣、洋葱、西红柿和胡椒),田地作物(诸如土豆、甜菜、落花生、大豆和油菜籽),蔗糖,草地和叶子作物(诸如玉米、高梁和苜蓿),种植物园(诸如茶、咖啡、可可、香蕉、棕榈油、椰子、橡胶和香料),果园和园林(诸如核果水果、柠檬、Kuwifiuit、鳄梨、芒果、橄栏和胡桃),葡萄,观赏作物,在草场里花园中和公园里的花、蔬菜及灌木,森林里的树木(落叶树和常青树)、种植园和苗圃。
它们在保护木材(未伐的树、砍下的树、变形的、贮存的或建筑物上的木材)不被例如叶蜂或甲虫或白蚁所侵袭方面也是有价值的。
它们被研磨或复合入整个产品中以保护贮存产品不被蛀虫、甲虫、螨如谷粒象鼻虫的侵袭。贮存产品是诸如谷类、水果、坚果和烟草。它们也保护诸如毛皮、毛状物、羊毛羽毛和皮革的天然产品或加工形式(例如毛毯或纺织品)的贮存的动物产品不被蛀虫和甲虫所侵袭,并保护贮存的肉和鱼不被甲虫、螨和蝇所侵袭。另外,本发明化合物及其使用方法在控制节肢动物、蠕虫和原生动物中特别有价值,节肢动物、蠕虫和原生动物是有害的,它们在人和家畜中传播疾病或作为疾病的媒介,例如前述本发明的化合物最好地可控制扁虱、螨、虱、蚤、蠓、小蚊、蝇蛆。本发明的化合物在控制节肢动物、蠕虫或原生动物中尤为有用,这些动物存在于家畜宿主内部或者在宿主的皮肤里或皮肤上吃或吮吸动物的血,为了达到控制目的,本发明化合物可口服、腹腔内注射、皮注或局部给药。
此外,本发明的化合物对于球虫病是有用的,球虫病是由艾美球虫属的原生动物寄生感染而引起的。由于家畜和鸟死亡,特别当家畜集居饲养时死亡增多,它就引起了极大的经济损失。例如,牛、羊、猪和兔可被侵袭,但家禽,特别是小鸡更易感染。使用少量的本发明化合物,较好地是掺在饲料中使用可有效地防止或大大降低球虫病的发病率。化合物对盲肠型和肠型的都有效。此外,本发明化合物通过大大地减少产生的孢于及卵母细胞的数量具有抑制卵囊的作用。鸟将感染源带到污染的草铺层、土地、食物和饮用水里使家禽病得以传播。疾病的症状是出血、肓肠积血、便血、虚弱和消化失调。该病常引起动物死亡,但是存活下来的家禽由于感染其售价明显降低。
下面所述的组合物可施用在生长的作用上和作物生长的地方及可对种子涂覆,一般地,这些组合物可局部用于人和动物,也可用于保护贮存产品、家用物品、普通环境的性质的地区。本发明化合物合适的使用方法包括:
对于生长中的作用使用叶子喷雾剂、粉刺、颗粒剂、雾剂和泡沫剂,也可使用分散良好的悬浮液。包入胶囊中的组合物采用液体药水、粉末剂、颗粒剂、烟剂和泡沫剂来处理土壤和根;对于作物的种子则采用液体浆液和粉末剂给种子涂覆使用。
对于被节肢动物、蠕虫或原生动物侵袭的人或动物非肠胃道使用、口服或局部使用组合物,在组合物中活性组分对抵御节肢动物、蠕虫或原生动物具有速效作用和/或在一段时间内的延续作用,使用方法是例如将药物配方掺入饲料中喂养,或口服药物、食、饵、盐渍池、规定饮食、食物供给、灌洗配方、喷洒、洗澡、浸渍、淋浴、喷射、粉末剂、油剂、香波、霜剂、蜡涂剂和家畜自身治疗系统。
对于总体环境或有害动物可能潜伏的特定场所包括储存产品木材、家常物品及家庭房屋和工厂房屋,可使用喷雾剂、雾剂、粉末剂、烟熏剂、蜡涂物、漆、颗粒剂和饵,有害动物的潜伏场所、可缓缓滴入至水路、井、水库和其它流动或静止水处使用上述组合物。
对于家畜则要控制以家畜粪便为食的蝇幼体。
在实际使用中,本发明化合物常呈组合物形式而使用。这些组合物可用来控制节肢动物(特别是昆虫)、线虫、蠕虫和原生有害动物。组合物可用该技术领域公知的任何形式在房屋里或室内或室外或者给脊椎动物内服或外用以对所需控制的有害动物进行施用。这些化合物至少含有一种如前所述的化合物作为活性组份,活性组份并与一种或多种其它适合的组份一起配成组合物,其它适合的组份是例如固体或液体载体或稀释剂、调节剂、表面活性剂等农业上或药学上可接受的适当组份。这些组合物可用现有技术中的任何方法制备,它们是本发明的一部分。
这些组合物也可含有其它种的组份,诸如保护胶体、粘着剂、增稠剂、摇溶剂、渗透剂、喷洒油(特别是用于杀螨剂中)、稳定剂、防腐剂(特别是防霉剂)、螯合剂等以及其它的具有杀有害动物性质的已知活性组份(特别是杀昆虫剂、杀螨剂、杀线虫剂或杀真菌剂)或者其它的具有植物生长调节作用性质的已知组份。更广泛地说,本发明中使用的化合物可与普通配方技术中相应的固体或液体添加物结合在一起使用。
适合在农业上和园艺上等使用的组合物配方是例如喷雾剂、粉末剂、颗粒剂、雾剂、泡沫剂、乳剂等。
适合给脊椎动物或人使用的组合物包括口服、非肠胃道给药、皮肤给药、例如灌洗给药或局部给药。
用于口服的组合物包括一种或多种通式(I)化合物及药学上可接受的载体或包衣,它包括例如片剂、丸剂、胶囊剂、糊剂、凝胶、顿服药、药用食物、药用饮水、药用规定食物、缓释大丸剂或其它在胃肠道中保持的缓释物质。这些剂型都可将活性组份掺入到微胶囊内或者用对酸不稳定或对碱不稳定或其它药学上可接受的肠包衣物质进行包衣。
含有本发明化合物的预混和浓缩饲料可用来制备药用饮食、饮水或动物消耗的其它物质,这些物质也可被使用。
非肠胃道给药的组合物包括在任何合适的药学上可接受的赋形剂和固体或半固体的皮下植入物中溶液剂、乳剂或悬浮液或者使活性物质延长释放时间的丸剂,它们用该领域已知的任何合适的方法进行制备和消毒。
用于皮肤给药或局部给药包括喷雾剂、粉末剂、洗噪、浸渍、淋浴、喷射、油脂、香波、霜剂、蜡涂物或涂覆制剂和方法(例如药物附在动物耳朵附属物上以这样的方法局部或全身性控制节肢动物)。
适合于控制节肢动物的固体或液体饵包括一种或多种通式(I)的化合物以及载体或稀释剂,该载体或稀释剂包括一种食品或一些其它诱使节肢动物消耗的物质。
本发明中使用化合物的有效剂量在很广的范围内应用,特别是要视污染有害动物的性质及侵染程度而言,例如谷类就有三种有害动物。大体上说,本发明的组合物通常含有约0.05—约95%(重量)的一种或多种本发明活性组份、约1—约95%的一种或多种固体或液体载体以及,任意地有约0.1—约50%一种或多种诸如表面活性剂等的其它可配伍的组份。
在表述方面,术语“载体”表示有机或无机组份,天然的或合成的组分,它与活性物质掺合在一起便于施用,可用于,例如对植物、种子或土壤。该载体因而通常是惰性的,它并须是可接受的(例如,农业上接受的,特别是要被待处理的植物所能接受)。
载体可以是固体,例如陶土、天然的或合成的硅酸盐、二氧化硅、树脂、蜡、固体肥料(例如铵盐)、诸如高岭土、陶土、滑石粉、白垩、石英、活性白土、蒙脱土、膨润土或硅藻土的细磨的天然矿石,以及诸如二氧化硅、矾土和较好为硅酸铝或硅酸镁的硅酸盐的细磨的合成矿石。适合于颗粒剂的固体载体如下:诸如方解石、大理石、浮石、海泡石和白云石的压碎且分级的天然岩石;无机粉末和有机粉的合成颗粒;诸如木屑、椰子壳、玉米棒子、玉米壳和烟草茎的有机物质颗粒;以及硅藻土、磷酸三钙、粉末化的软木、吸附的炭黑以及水溶性的聚合物、树脂、蜡和固体肥料。如果需要,这类固体组合物可包含一种或多种适当的湿润剂、分散剂、乳化剂或着色剂,当它是固体时,它们也可作为稀释剂。
载体也可以是液体,例如:水;醇类,较好的是丁醇或乙二醇,以及它们的醚或酯,较好地是甲基乙酸酯;酮类,较好的是丙酮、环己酮、甲乙酮、甲基异丁基酮和异佛尔酮;诸如液体石蜡或芳烃(较好的是二甲苯或烷基萘)的石油馏份,以及矿物油和植物油;氯代脂族烃,较好的是三氯乙烷或二氯甲烷,或者氯代芳烃,较好的是氯苯;诸如二甲基甲酰胺、二甲亚砜或N-甲基吡咯烷酮的水溶性或强极性溶剂;液化气体;等等或它们的混合物。
表面活性剂可以是乳化剂、分散剂或离子型或非离子的湿润剂或是这类表面活性剂的混合物。在这些中的例子是聚丙烯酸的盐、木素磺酸的盐、苯磺酸或萘磺酸的盐、环氧乙烷与脂肪醇或脂肪酸或脂肪酯或脂肪胺的缩聚物、取代的苯酚(较好地是烷基苯酚或芳基苯酚)、硫代琥珀酸酯的盐、牛磺酸衍生物(较好的是烷基牛磺酸酯)、醇类的磷酸酯或环氧乙烷与苯酚缩聚物、多元醇类的脂肪酸酯以及上述化合物的官能基团的硫酸酯、磺酸酯和磷酸酯衍生物。当活性组分和/或惰性载体微溶于水或不溶于水且组合物的载体须在水中使用时,通常需要存在至少一种表面活性剂。
本发明组合物进一步可以含有诸如粘合剂和着色剂的另外的添加物。在配方中可使用诸如羧甲基纤维以及呈粉末、颗粒或晶体形式的诸如阿拉伯胶、聚乙烯醇和聚乙烯乙酸酯的天然及合成的聚合物,诸如脑磷脂和卵磷脂的天然磷脂以及合成磷脂。可以采用的着色剂是无机色素,例如:氧化铁、二氧化钛和普鲁士蓝;有机染料,诸如茜素染料、偶氮染料和金属酞菁染料;以及诸如铁盐、镁盐、硼盐、铜盐、钴盐、钼盐和锌盐的痕量营养物质。
组合物含有可用来控制节肢动物、植物线虫、蠕虫或原生有害动物的通式(I)化合物,它也含有增效剂(例如胡椒基丁醚或芝麻)(sesames)稳定物质、其它杀昆虫剂、杀螨剂、杀植物线虫机、抗蠕虫或抗球虫剂、杀真菌剂(适合于农业和脊椎动物使用,例如苯菌灵和iprodione)、杀细菌剂、节肢动物或脊椎动物的吸引剂或防护剂或外激素、除臭剂、调味剂、染料以及辅助治疗剂,例如痕量元素。可将组合物设计成增强效用的、持久的、安全的、定向吸收的、广谱的控制有害动物,或者使组合物在同一被处理的动物和区域中执行其它有用的功能。
其它一些杀有害动物活性化合物的例子或用于本发明组合物中的例子是:高灭灵(acephat)、毒死蜱(chlorpyrifos)、地灭通-S-甲基(demeton-S-methyl)、乙拌磷(disulfoton)、灭克磷(ethoprofos)杀螟松(fenilrothion)、马拉松(malathion)、久效磷(monocrotophos)、对硫磷(parathion)、伏杀磷(phosa-lone)、抗蚜磷-甲基(puimiphos-methyl)、三唑磷、杀弗林(cyfluthrin)、沙梅涕林(cyermethrin)、待他梅涕林(deltamethrin)、番迫帕林(fenpropathrin)、番瓦雷拉(fenvalerate)、苄氯菊脂(permethrin)、涕灭威(aldicarb)、卡迫苏番(carbosulfan)、灭多虫(methomyl)、噁才梅(oxamyl)、比立米卡巴(pirimcarb)、班的卡巴(bendiocarb)、太弗苯龙(teflubenzuron)、阿凡梅丁(avermectins)、伊凡梅丁(ivermectins)、米班霉素(milbemycins)、托布津(thiophanate)、敌百虫(tmchlorfon)、敌敌畏(dichlorvos)、二氯芦嘧啶(dioveridine)、二甲硝咪唑。
对于农业上的使用,式(I)的化合物通常呈组合物的形式,它们可为各种液体或固体形式。
可使用的组合物固体形式是粉末剂[式(I)化合物的含量最高达80%]、可湿性粉末和颗粒剂(包括水中可分散的颗粒),较好地是通过挤出、压紧、浸渍于颗粒载体中或从粉末剂中制得颗粒剂来得到上述组合物形式(可湿性粉末或颗粒剂中式(I)化合物的含量是约0.5—80%之间)。在一段时间里用含一种或多种式(I)化合物的同质固体或异质固体组合物来处理死水或流水,该固体组合物是例如颗粒剂、丸剂、团块剂或胶囊剂。采用这里所述的水分散性浓缩物的一滴滴的进料或间歇进料也可得到相似的作用。
液体组合物包括,例如水和非水溶液及悬浮液(诸如可乳化的浓缩物、乳剂、流体、分散剂和溶液)以及气溶胶,液体组合物较好地也包括可乳化的浓缩物、分散液、乳剂、流体、可湿性粉末(或喷洒用的粉末)、干流体以及糊剂,它们是液体或施用时可形成液体,例如成为水质喷雾剂(包括低体级和极低体积)和雾剂以及气溶胶。
液体组合物,以可乳化的或可溶的浓缩物为例,常包括约5—80%(重量)的活性组份,当使用制备好的乳剂或溶液剂时,其中含约0.01—20%的活性物质。除溶剂外,需要时可乳化的或可溶的浓缩物可以含有约2—50%的适当添加物,诸如稳定剂、表面活性剂、渗透剂、防腐蚀剂、着色剂或粘合剂。将浓缩物用水稀释使之达到所需浓度可较好地进行使用,例如用于植物。这些组合物包含在本发明所使用组合物的范围里。乳剂可为油包水型或水包油型,它们有一定的稠度。
本发明的液体组合物除了正常地用于农业外,它们也可用来处理被节肢动物(以及被本发明化合物所控制的其它有害动物)所侵染的基地或地方,包括房屋,室内或室外贮或易于被侵染贮存物或加工地方、容器或仪器以及死水或流水。
通过合适的方法,主要是喷洒将这些水分散剂或乳剂或喷雾剂混合物用于例如作物上,其用量比率常为约100—1,200升喷洒混合物/公顷,但根据施用技术的需要可稍高或稍低(例如,低体积或超低体积)。本发明的组合物可方便地用于植被,特别是用于被消灭根或叶子的害虫。使用本发明的化合物或组合物的另一个方法是用化学灌溉,就是说,将含活性组分的配料加到灌溉的水中。该灌溉液可以喷淋在叶上以控制叶子有害动物,或它可在地上或地下灌溉用于土壤和用于内吸收杀有害动物剂。
通过喷雾使用的浓缩悬浮液可被制得,结果得到一稳定的液体产品,它不沉积(良好研磨,通常含有约10—75%(重量)的活性组份、约0.5—30%的表面活性剂、约0.1—10%的摇溶剂、约0—30%的合适添加剂,诸如消沫剂、防腐蚀剂、稳定剂、渗透剂、粘合剂以及载体、水或有机液体。活性组份在其中微溶或不溶。而一些有机固体或无机盐溶于载体中以防止沉积或防止水凝固。
通常制得的可湿性粉末(或喷洒粉末)中含有约10—80%(重量)的活性组份、约20—90%固体载体、约0—5%湿润剂、约3—10%分散剂,以及需要时,约0—80%一种或多种稳定剂和/或其它添加剂,诸如渗透剂、粘合剂、抗结块剂、着色剂等,为了得到这些可湿性的粉末,将活性组分与添加物放在合适的混合器中混合完全,它们浸渍在多孔性的填料里并用研磨或其它合适的磨器进行研磨。该可湿性粉末产品具有有利的可湿润性和悬浮性。它们可悬浮于水中给出所需的浓度,该悬浮液使用于植物叶子上时则更为有利。
“水分散性颗粒(WG)”(颗粒不断地易于分散于水中)是一种基本接近于可湿性粉末的组合物。通过如制备可湿性粉末所述的颗粒化配方来制得,颗粒化配制有湿粒法(将分散良好的活性组分与惰性载体和一些水[例如1—20%(重量)水]或分散剂溶液或掺和物溶液放在一起接触,然后干燥并过筛)或干粒法(压紧后研磨并过筛)。
配方组合物中活性组分的使用剂量(有效剂量)通常在约0.005—15公斤/公顷,较好地在约0.01—2公斤/公顷。因此根据施用的方法及所使用组合物的性质,配方组合物的比率和浓度是不同的。总的来说,用来控制节肢动物、植物线虫、蠕虫或原生有害动物的组合物含有约0.00001%—约95%,较好的是约0.00005%—50%(重量)的一种或多种(I)化合物或活性组份(就是说式(I)化合物再加上其它对节肢动物和植物线虫有毒的物质、抗蠕虫剂、抗球虫病剂、增效剂、痕量元素和稳定剂。实际使用的组合物及用量须由农民、养畜者、兽医、控制有害动物者或其它熟悉该技术领域的人员所选择。
典型地用于动物、木材、贮存产品或家常物品的固体和液体组合物通常含有约0.00005%—90%,较好地是约0.001%—10%(重量)的一种或多种式(I)化合物。对于动物口服或非肠胃道给药包括皮肤给药的固体和液体组合物它们通常含有约0.1%—90%(重量)的一种或多种式(I)化合物。药物饲料通常含有约0.001%—3%(重量)的一种或多种(I)化合物。与饲料混合的浓缩物及供给物中通常含有5—90%,较好是约5%—50%(重量)的一种或多种式(I)化合物。无机盐冲洗液通常含有约0.1—10%(重量)一种或多种式(I)化合物。
用于家畜、人、物品、房屋或室外地区的粉末和液体组合物可包含约0.001%—15%较好地是约0.005—2.0%(重量)的一种或多种式(I)化合物处理水的合适浓度为约0.0001ppm及20ppm,更好地为0.001ppm至约5ppm和一种或多种式(I)化合物,它们可通过适当的暴露时间而用于鱼业生产中。同时,食饵可含有约0.01%—5%,较好地含有约0.01%—1.0%(重量)的一种或多种式(I)化合物。
当给兽类非肠胃道给药、口服使用或皮肤给药或其它方法给药时,式(I)化合物的剂量视其种类、年龄及脊椎动物的健康状态以及被节肢动物、蠕虫或原生有害动物实际或潜在的侵染性质和程度而定。每公斤体重动物的单剂量是约0.1—约100毫克,较好的是约2.0—200毫克,或者每天剂量是相对于动物每公斤体重为约0.01—20.0毫克,较好的是约0.1—5.0毫克,它是对于持续有效性制剂而言,通常适合于口服或非肠胃道给药。由于采用了持续释放的配方或方法,动物在一次服用后就可得到每天所需的剂量合并入几个月时期的剂量。
下列组合物实施例77—88阐述了用于抵御节肢动物(尤其是昆虫)、植物线虫、蠕虫或原生有害动物的组合物,它包括式(I)的化合物,较好地是式(III)或(VI)的化合物,最好是式(III)—(IV)的化合物,如制备实施例1—75所述,较好的化合物列于表3中。实施例77—82所述的组合物均可用水稀释得到一适用于田地里浓度的可喷雾的组合物。组合物实施例77—88中使用的组分的一般化学配方(所有的百分数是重量百分数)列举如下:
商品名 化学名
Ethylan BCP 壬基酚环氧乙烷缩聚物
Soprophor BSU 三苯乙烯基酚环氧乙烷缩聚物
Arylan CA 70%(w/v)十二烷基苯磺酸钙溶液
Solvesso 150 轻质C10芳族溶剂
Arylan S 十二烷基苯磺酸钠
Darvan No2 木素磺酸钠
Celite PF 合成的硅酸镁载体
Sopropon T36 多羧酸钠盐
Rhodigel 23 多糖黄尿胶
Bentone 38 镁蒙脱士的有机衍生物
Aerosil 微细二氧化硅
实施例77
用如下的组合物制备水溶性浓缩物:
活性组分 7%
Ethylan BCP 10%
N-甲基吡咯烷酮 83%
在加热和搅拌条件下将活性组分加入Ethylan BCP溶于部分的N-甲基吡咯酮溶液内直至完全溶解为止。用剩余的溶剂将所得的溶液调整到原定体积。
实施例78
用下列组合物制备可乳化的浓缩物(EC):
活性组分 7%
Soprophor BSU 4%
Arylan CA 4%
N-甲基吡咯烷酮 50%
Solvesso 150 35%
将前三种组分溶于N-甲基吡略烷酮中,然后加入Slovesso150以得到最终的体积。
实施例79
用如下的组合物制备可湿性粉末(XP):
活性组分 40%
Arylan S 2%
Darvan No2 5%
硅藻土(Celite) PF 53%
将组分进行混合并在锤磨中研磨成颗粒小于50微米的粉末。
实施例80
用下列组合物制备水流体配方:
活性组分 40.00%
Ethylan BCP 1.00%
Sopropon T360 0.20%
乙二醇 5.00%
Rhodigel 230 0.15%
水 53.65%
将组分完全混合并在小珠磨中研磨得到平均颗粒大小低于3微米的粉末。
实施例81
用如下的组合物制备可乳化悬浮液浓缩物:
活性组分 30.0%
Ethylan BCP 10.0%
Bentone 38 0.5%
Solvesso 150 59.5%
将组分完全混合并在小珠磨中研磨得到平均粒度为低于3微米的粉末。
实施例82
用如下的组合物制备水分散性颗粒:
活性组分 30%
Darvan No2 15%
Arylan S 8%
硅藻土(Cllite) PF 47%
将组分进行混合,在流体—能量磨中微化,然后通过喷水(直至10%)在旋转成球机中制粒。使所得的颗粒在流化床中干燥以除去过量的水。
实施例83
用如下的组合物制备粉末剂:
活性组分 1—10%
优质的滑石粉 99—90%
将组分完全混合,如果需要可再作研磨以得到微细的粉末。该粉末可用于被节肢动物侵染的地方,例如垃圾堆、贮存产品或家常物品或者被节肢动物侵染的动物或有被侵染危险的动物,它通过口服摄入粉末来控制节肢动物。将粉末撒在节肢动物侵染地点的合适方法包括机器吹撒、手工撒以及家畜自身处理方法。
实施例84
用如下组合物制备食饵:
活性组分 0.1—1.0%
小麦粉 80%
糖浆 19.9—19%
将组分完全混合并形成所需的饵的形式。食饵可放在例如家庭房屋和工厂房屋,例如厨房、医院或仓库、或者室外区域的地方,它们被例如蚂蚁、蝗虫、蟑螂和蝇的节肢动物所侵染,通过吃入食饵以控制节肢动物。
实施例85
用如下的组合物制备溶液配方:
活性组分 15%
二甲亚砜 85%
将活性组分溶于二甲亚砜中,如果需要则进行混合和/或加热。该溶剂可用于被节肢动物侵染的家畜,作为灌注经皮肤使用,或者通过聚四氟乙烯膜(0.22微米孔大小)过滤除菌给予非肠胃道注射,其用量是动物的100Kg动物体重用1.2—12毫升溶液。
实施例86
用如下的组合物制备可湿性粉末:
活性组分 50%
Ethylan BCP 5%
高度分散的硅胶(Aerosil) 5%
硅藻土(Cclite) PF 40%
将Ethylan BCP吸附在高度分散的硅胶(Aerosil)上,然后与其它组分一起混合并在锤磨上研磨给出可湿性粉末,它可用水稀释到0.001%—2%(重量)活性化合物的浓度并通过喷洒施用在被例如双翅目幼虫或植物线虫的节肢动物侵染的地方,或通过喷洒或浸渍或通过在饮用水中口服施用在被节肢动物、蠕虫或原生动物侵染或有侵染危险的家畜上,以控制节肢动物、蠕虫或原生动物。
实施例87
从含下列组分的颗粒中制成缓释大丸药组合物,其百分含量视需要而定(与前述的组合物相似):
活性组分
增加密度剂
缓释剂
粘合剂
将组分完全混合形成颗粒并压成大丸剂,其密度为2或大于2。这可给反刍家畜口服以便在网状的瘤胃中保持使在长时间内保持活性物质的持续缓释,这样,可控制反刍家畜被节肢动物、蠕虫或原生动物所侵染。
实施例88
用下列合物可制得呈颗粒剂、丸剂、等形式的缓释组合物:
活性组分 0.5—25%
聚氯乙烯 75—99.5%
邻苯二甲酸二辛酯(增塑剂) 催化量
将组分掺在一起然后通过熔化挤出或成模制成合适形状的物质。对于加入静止水中或制成被侵染动物的颈圈或耳环以通过缓释来控制有害动物这些化合物是有用的。
本发明已说明及阐述了细节并叙述了优选的细节,对于熟悉该技术领域的人员来说无疑可作出改进和替换而不超出本发明的范围和精神,本发明的范围则由所述的权利要求书进行定义。
Claims (13)
2.根椐权利要求1所述的组合物,其特征在于其中:
R是完全被相同或不同卤(素)原子所取代的甲基;
R1是C1~C4烷基;
R2是卤原子;以及
R4是CF3。
3.根椐权利要求2所述的组合物,其特征在于其中:
R选自CF3、CCl2F或CClF2;
R1是甲基或乙基;以及
R2和R6各自是氯原子。
4.根据权利要求1所述的组合物,其特征在于其中:
R是CF3、CCl2F或CClF2;
R2和R6各自是氯原子;以及
R4是氯原子、CF3、或OCF3。
5.根椐权利要求1所述的组合物,其特征在于其中的活性成分是:
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-甲氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基磺酰基-5-甲氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基亚磺酰基-5-甲氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基硫基-5-乙氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-二氯氟甲基硫基-5-甲氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基亚磺酰基-5-乙氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-三氟甲基磺酰基-5-乙氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-氯代二氟甲基硫基-5-乙氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-二氯氟代甲基亚磺酰基-5-甲氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-二氯氟代甲基磺酰基-5-甲氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-氯代二氟甲基亚磺酰基-5-乙氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-氯代二氟甲基磺酰基-5-乙氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-氯代二氟甲基硫基-5-甲氧基吡唑,
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-氯代二氟甲基亚磺酰基-5-甲氧基吡唑,或者
1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-4-氯代二氟甲基磺酰基-5-甲氧基吡唑。
6.根椐权利要求1所述的组合物,其特征在于它含有0.05~95%(重量)一种或多种式(I)化合物作为活性组分以及1~95%(重量)一种或多种农业上可接受的固体或液体载体。
7.一种如权利要求1所述的组合物的农业和园艺业的使用方法,包括用权利要求1所述的组合物处理所在地区以控制有害动物的生长。
8.根椐权利要求7所述的使用方法,其中的所在地区包括植物或植物生长的介质,有害动物是植物的节肢动物或线虫有害动物,其特征在于它包括将权利要求1的组合物施用到植物或植物生长的介质中。
9.根椐权利要求7所述的方法,其特征在于以被处理地区以每公顷0.005公斤~15公斤化合物的施用比率将组合物用于所在地,使该地方的节肢动物或线虫侵染得以控制。
10.根椐权利要求9所述的方法,其特征在于其中的施用比率是每公顷0.02公斤~2公斤化合物。
11.根椐权利要求9所述的方法,其中所述的节肢动物是昆虫,所述的有害动物是昆虫和植物线虫,其特征在于它包括将组合物掺到已种植植物或将种植植物的土壤里,或者将组合物施用到植物种子上或植物根上或者在叶子上施用。
12.根椐权利要求11所述的方法,其特征在于其中所述的昆虫是甲虫类的土壤昆虫。
13.根椐权利要求12所述的方法,其特征在于其中所述的甲虫类土壤昆虫是叶甲虫。
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US07/317,722 | 1989-03-02 | ||
US07/317722 | 1989-03-02 | ||
US07/317,722 US4918085A (en) | 1989-03-02 | 1989-03-02 | Pesticidal 3-cyano-5-alkoxy-1-arylpyrazoles, compositions and use |
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CN1045262A CN1045262A (zh) | 1990-09-12 |
CN1031238C true CN1031238C (zh) | 1996-03-13 |
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US (2) | US4918085A (zh) |
EP (1) | EP0385809B1 (zh) |
JP (1) | JP2963484B2 (zh) |
KR (1) | KR0161284B1 (zh) |
CN (1) | CN1031238C (zh) |
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AU (1) | AU631605B2 (zh) |
BG (1) | BG60002A3 (zh) |
BR (1) | BR9001053A (zh) |
CA (1) | CA2010180C (zh) |
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