CN1043041C - 含有杂环基的醚类衍生物和以其作为活性成分的杀虫剂 - Google Patents
含有杂环基的醚类衍生物和以其作为活性成分的杀虫剂 Download PDFInfo
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- CN1043041C CN1043041C CN95193710A CN95193710A CN1043041C CN 1043041 C CN1043041 C CN 1043041C CN 95193710 A CN95193710 A CN 95193710A CN 95193710 A CN95193710 A CN 95193710A CN 1043041 C CN1043041 C CN 1043041C
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- compound
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- methyl
- pyrazolyl
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
公开了如下通式的新醚化合物：
其中R1，R2和R3各自为氢等；A为如下通式的基团：
B是如下通式的基团：
而X是氧或硫；和含有它们作为活性成分的有害生物体防治剂。
Description
技术领域
本发明涉及醚化合物和其用途。更具体地，本发明涉及对有害生物体具有优良防治作用的醚化合物，并涉及含有它们作为活性成分的有害生物体防治剂。
背景技术
EP 0 388 682公开了一种杀虫化合物，该化合物的Het部分是通过杂环的碳原子连接的。
发明公开
本发明人选行了深入的研究以寻找对有害生物体具有优良防治作用的化合物。结果，他们已发现如下画出的通式P-1的醚化合物对有害生物体具有优良控制作用，因而完成了本发明。
本发明提供如下通式的醚化合物(以后称作本发明化合物)： (P-1)其中R1是氢或氯
R2和R3独立地为氢或甲基；
A是如下通式的基团：
其中R4是氢，氯或甲基；而R5和R6独立地为氢或氯；
B是如下通式的基团；
其中R7和R8独立地为氢或氟；且
X是氧或硫；和含有它们作为活性成分的有害生物体防治剂。
实施发明的方案
在本发明化合物中，从有害生物体防治活性的观点看，优选的A为如下通式的基团；
(P-2)其中R4如上定义。它们之中，其中R4是氢的基团是优选的，而R1优选地为氢。
本发明化合物可以，例如，通过如下方法生产。
(生产方法a)
这个生产方法中，如下通式的酚衍生物；
(P-3)其中R1和A如前定义、与如下通式化合物：
(P-4)其中R2,R3,B和X如前定义；而L是卤素(例如，氯，溴，碘)，甲磺酰氧基或甲苯磺酰氧基。
(生产方法b)
这个生产方法中，如下通式化合物： (P-5)其中R1,R2,R3,A和X如前定义，或其碱金属盐(例如，锂盐，钠盐，钾盐)，与如下通式化合物反应：
L-B (P-6)其中B和L如前定义。
(生产方法C)
这生产方法中，如下通式化合物：
(P-7)其中R1,R2,R3,A和L如前定义，与如下通式化合物反应：
H-X-B (P-8)其中B和X如前定义，或其碱金属盐(例如，锂盐、钠盐，钾盐)。
在生产方法a,b和c中，反应优选地在碱存在下没有任何溶剂或在惰性有机溶剂中进行(然而，当通式P-5或P-8化合物的碱金属盐被用于生产方法b和c中时，不需要用碱)。
此反应通常在惰性有机溶剂中进行。作为可被使用的溶剂，可被提到的有，例如，芳香烃如苯，甲苯，二甲苯和氯苯；腈类如乙腈，丙腈和异丁腈；酮类如丙酮，甲基异丁基酮和甲基乙基酮；甲醇，乙醇，正丙醇等等；醚如甲氧基乙烷，四氢呋喃和二噁烷；极性溶剂如N,N-二甲基甲酰胺，N,N-二甲基乙酰胺，二甲基亚砜，sulforane和六甲基磷酰三酰胺；水；或其混合物。为了使反应过程更平滑，可以加入相转移催化剂，如苄基三乙基铵氯化物和溴化四正丁基铵。
作为可被使用的碱，可以提到的有，例如，碱金属如钠和钾；碱金属氢氧化物如氢氧化钠和氢氧化钾；碱金属碳酸盐如碳酸钠和碳酸钾；碱金属氢化物如氢化钠；金属醇盐如乙醇钠和甲醇钠；和有机碱如吡啶，三乙胺，N,N-二甲基苯胺和4-N,N-二甲基氨基吡啶。
在生产方法a,b和c中，尽管反应温度没有特殊限制，但反应通常在30℃至200℃或所用溶剂的沸点的范围内，优选地在20℃至110℃的范围内进行。反应时间通常为0.5至24小时。
用于生产方法a中的通式P-3的酚衍生物与通式P-4化合物的摩尔比一般是1∶0.5至2；优选地为1∶0.7至1.5。用于生产方法b中的通式P5化合物与通式P-6化合物的摩尔比通常为1∶0.5至10，优选地为1∶0.8至2。用于生产方法c中的与通式P-7化合物与通式P-8化合物的摩尔比通常为1∶1至10，优选地为1∶1.1至1.5。
用于生产方法a,b和c中，反应完成后，反应混合物进行常规后处理如用有机溶剂萃取并浓缩。这样，本发明化合物可被分离。如果需要，纯化可通过重结晶，柱色谱等进行。
本发明化合物的典型例子示于如下。
如下通式的化合物；其中R1,R2,R3和X如表1定义；
表1
和如下通式化合物：
其中R1,R2,R3和X如表2中定义。
| R1 R2 R3 X | R1 R2 R3 X |
| H H H OCl H H OH H CH3 OH CH3 H OH CH3 CH3 OCl H CH3 OCl CH3 H OCl CH3 CH3 O | H H H SCl H H SH H CH3 SH CH3 H SH CH3 CH3 SCl H CH3 SCl CH3 H SCl CH3 CH3 S |
表2
| R1 R2 R3 X | R1 R2 R3 X |
| H H H OCl H H OH H CH3 OH CH3 H OCl H CH3 OCl CH3 H O | H H H SC1 H H SH H CH3 SH CH3 H SCl H CH3 SCl CH3 H S |
用于生产本发明化合物的中间体的通式P-4,P-6和P-8化合物可购买到；然而，通式P-4化合物可以，例如，根据Synthesis,573(1980)中描述的方法生产，或通式P-8化合物可以，例如，根据JP-A-56-90059中所述的方法生产。
通式P-5和P-7化合物可以，例如，从通式P-3化合物通过如下反应图解生产： 其中R1,R2,R3,A和L如前定义；L’是卤素(例如，氯，溴，碘)；而R9是C1-4烷基(例如，甲基，乙基)。
通式P-3的酚衍生物可以，例如，通过如下方法生产。
这方法中，如下通式的酚酯衍生物：
(P-9)其中R1和A如前定义，而R9为C1-4烷基(例如甲基，乙基)或苯基，在碱性条件下水解。
此反应通常在溶剂中进行。作为可被使用的溶剂，可被提到的有，例如，醇类如甲醇，乙醇，正丙醇，乙二醇和二乙二醇；水；或其混合物。
反应通常在0℃至200℃或所用溶剂的沸点的范围内进行，优选地在20℃至120℃的范围内。反应时间通常为1至500小时。
作为用于反应中试剂的量，碱可以任何mol比1mol通式P-9的酚衍生物，优选地为1比2mol的比例。
通式P-9的酚酯衍生物可以，例如，通过如下方法生产。
这方法中，如下通式的酚酯化合物：
(P-10)
其中R1,R9和L如上定义，与如下通式化合物：
A-H (P-11)其中A如前定义，在碱存在下反应。
此反应通常在惰性有机溶剂中进行。作为可被使用的溶剂，可被提到的有，例如，芳香烃如苯，甲苯，二甲苯和氯苯；腈如乙腈，丙腈和异丁腈；酮如丙酮，甲基异丁基酮和甲基乙基酮；醇如甲醇，乙醇和正丙醇；醚如二乙醚，二异丙醚，1,2-二甲氧基乙烷，四氢呋喃和二噁烷；极性溶剂如N,N-二甲基甲酰胺，N,N-二甲基乙酰胺，二甲亚砜，sulforane，和六甲基磷酰三酰胺；或其混合物。
作为可被使用的碱，可被提到的有，例如碱金属如钠和钾；碱金属氢氧化物如氢氧化钠和氢氧化钾；碱金属碳酸盐如碳酸钠和碳酸钾；碱金属氢化物如氢化钠；碱金属醇盐(例如，C1-C4醇盐如甲醇盐和乙醇盐)如乙醇钠和甲醇钠；和有机碱如吡啶，三乙胺，N,N-二甲基苯胺和4N,N-二甲基氨基吡啶。
反应通常在0℃至200℃或所用溶剂的沸点的范围进行，优选地在20℃至120℃的范围内。反应时间通常为1至50小时。
用于反应中试剂的量通常为1比10mol的比例，优选地为1比2mol，对于各个通式P-11化合物和碱，比1mol通式P-10的酚酯化合物。
本发明化合物对有害生物体，例如，有害昆虫和有害蜱和螨显示优良的防治作用，如下所述：
半翅目(Hemiptera)有害昆虫
飞虱科(Delphacidae)稻褐飞虱(Nilaparvata lugens)，白背稻虱(Sogatella furcifera)和灰稻虱(Laodelphax strilellus)；叶蝉科(Deltocephalidae)如黑尾叶蝉(Nephotettix cincticeps)，黑尾叶蝉(Nephotettix virescens)，黑尾叶蝉(Nephotettix nigropictus)，电光叶蝉(Recilia dorsalis)，茶绿叶蝉(Empoasca onukii)和葡萄斑叶蝉(Arboridia apicalis)；蚜虫科(Aphididae)如棉蚜虫(Aphis gossypii)和桃绿蚜(Myzus persicae)；蝽科(Pentatomidae)；粉虱科(Aleyrodidae)如甘薯粉虱(Bemisia tabaci)和温室粉虱(Trialeurodesvaporiorum)；蚧科(coccidae)；网蝽科(Tingidae)；木虱科(Psyllidae)，等等。
鳞翅目(Lepidoptera)有害昆虫
螟蛾科(Pyralidae)如二化螟(Chilo suppressalis)，稻卷叶螟(Cnaphalocris medinalis)和印度谷螟(Plodia mterpunctella)；夜蛾科(Noctuidae)如黄地老虎(Spodoptera litura)，稻叶夜蛾(Spodopteraexigua)和甘蓝夜蛾(Mamestra brassicae)；粉蝶科(Pieridae)如菜粉蝶(Pieris rapae crucivora )卷蛾科(Tortricidae)如Adoxophves spp；Carposinidae；潜蛾科(Lyonetiidae)；细蛾科(Gracillariidae)；麦蛾科(Gelechiidae)；毒蛾科(Lymantriidae)；Plusiae；Agrotis spp，如地老虎(Agrotis segetum)和小地老虎(Agrotis ipsilon)；Heliothis spp；小菜蛾或菜蛾(Plutella xylostella)；袋衣蛾或织网衣蛾(Tineapellionella)；幕衣蛾或普通衣蛾(Tineola bisselleella)，等等。
双翅目(Diptera)有害昆虫
蚊科(Calicidae)如家蚊(Culex pipiens pallens)和Culestritaeniorhynchus；Aedes spp如Aedes aegypti和Aedes albopictus；Anopheles spp.如Anophelinae sinensis；摇蚊科(Chironomidae)；家蝇科(Muscidae)如家蝇(Musca domestica)和假厩刺蝇(Muscinastabulans)；Calliphoridae；Sarcophagidae；花蝇科(Anthonmyiidae)如小家厕蝇(Fannia canicularis)瓜种蝇(Hylemya platura)和葱蝇(Hylemya antique)；瘿蚊(Cecidomyiidae)；果蝇(Tephritidae)；水蝇科(Ephydridae)；小果蝇科(Drosophilidae)；毛蠓科(Psychodidae)；蚋科(Simuliidae)；Tabanidae；厩刺蝇(Stomoxyidae)，等等。
鞘翅目(Coleoptera)有害昆虫
玉米根叶甲如玉米幼芽叶甲(Diabrotica virgifera)和瓜十一星叶甲(Diabrotica undecimpunctata)金龟子科(Scaradaeidae)如大绿金龟甲(Anomala cuprea)和大豆甲虫(Anomala rufocuprea)；象虫科(Curculionidae)如玉米象(Sitophilus zeamais)，稻象甲(Lissorphoptrusoryzophilus)和一色冈绿象(Calosobruchys chinensis)；拟步甲科(Tenebrionidae)如黄粉虫(Tenebrio molitor)和赤拟谷盗(Triboliumcastaneum)；叶甲(Chrysomelidae)如曲条跳甲(Phyllotreta striolata)和黄守瓜(Aulacphora femoralis)；窃蠹科(Anobiidae)；Epilachna spp，如马铃薯瓢虫(Epilachna vigintioctopunctata)；粉蠹科(Lyctidae)；长蠹科(Bostrychidae)；天牛科(Cerambycidae)，等等。
螂目(Dictyoptera)有害昆虫
德国小蠊(Blattella germanica)，烟色大蠊(Peripoaneta fulihinosa)，美洲大蠊(Periplaneta americana)，褐色大蠊(Periplaneta brunnea)，东方蠊(Blatta orientalis)，等等。
缨翅目(Thysanoptera)有害昆虫
Thrips palmi，茶黄蓟马(Scirlothrips dorsalis)，花蓟马(Thripshawaiiensis)，等等。
膜翅目(Hymenoptera)有害昆虫
蚁科(Formicidae)；叶蜂科(Tenthredinidae)如芜菁叶蜂(Ayhaliarosaejaponensis)，等等。
有翅目(Orthoptera)有害昆虫
蝼蛄科(Gryllolalpidae)，蝗科(Acrididae)，等等。
Aphianiptera有害昆虫
Purex irritans等等
虱目(Anoplura)有害昆虫
Pediculus humanus capitis、Phthirus pubis，等等。
等翅目(Isoptera)有害昆虫
Reticulitermes speratus，家白蚁(Coptotermes formosanus)，等等。
叶螨科(Tetranychidae)
红叶螨(Tetranychus cjnnabarinus)，棉叶螨(Tetranychus urticae)，神绛叶螨(Tetranychus kazawai)，柑桔全爪螨(Panonychus citri)，苹果全爪螨(Panonychus almi)等等。
硬蜱科(Ixodidae)
Boophilus microphus等等
家尘螨
谷螨，Dermatophagoides,Cheyletid螨，Ornitonyssus，等等。
如果本发明化合物与其它杀虫剂和/或杀螨剂联合使用，由本发明化合物达到的防治作用可在更不同的地方找到实际应用，用于抗更广泛的害虫。
作为适于结合使用的杀虫剂和/或杀螨剂，可以提到的有，例如，有机磷化合物如杀螟松[0,0-二甲基0-(3-甲基-4-硝基苯基)硫代磷酸酯]，倍硫磷[0,0-二甲基0-(3-甲基-4-(甲硫基)苯基]硫代磷酸酯]，二嗪农[0,0-二乙基- 0-2-异丙基-6-甲基嘧啶-4-基硫代磷酸酯]，毒死蜱[0,0-二乙基-0-3,5,6-三氯-2-吡啶基硫代磷酸酯]，高灭磷[0,S-二甲基乙酰基氨基硫代磷酸酯]，杀扑磷[S-2,3二氢-5-甲氧基-2-氧代-1,3,4-噻二唑-3-基甲基0,0-二甲基二硫代磷酸酯]，乙拌磷[0,0-二乙基S-2-乙硫基乙基二硫代磷酸酯]，DDVP[2,2-二氯乙烯基二甲基磷酸酯]，乙丙硫磷[0-乙基0-4-(甲硫基)苯基S-丙基二硫代磷酸酯]，杀螟腈[0-4-氰基苯基0,0-二甲基硫代磷酸酯]，杀抗松[2-methoxy-4H-1,3,2-benzodioxaphosphinine-2-sulfide]，乐果[0,0-二甲基-S-(N-甲基氨基甲酰基甲基)二硫代磷酸酯]，；稻丰散[乙基2-二甲氧基膦基亚砜基硫代(苯基)乙酸酯]，马拉硫磷[二乙基(二甲氧基膦基亚砜基硫代)琥珀酸酯]，敌百虫[二甲基2,2,2-三氯-1羟乙基膦酸酯]，谷硫磷[S-3,4-二氢4-氧基-1,2,3苯并三嗪-3-基甲基0,0-二甲基二硫代磷酸酯]和久效磷[二甲基(E)-1-甲基-2-(甲基氨基甲酰基)乙烯基磷酸酯]；氨基甲酸酯化合物如BPMC[2-仲丁基苯基甲基氨基甲酸酯]，Benfuracarb[乙基N-[2,3-二氧2,2-二甲基苯并呋喃-7-基氧基羰基(甲基)氨基硫基]-N-异丙基-B-丙氨酸酯]，残杀威[2-异丙氧基苯基N-甲基氨基甲酸酯]，Carbosulfan[2,3-二氢-2,2-二甲基-7-苯并[b]呋喃基N二丁基氨基硫基N-甲基氨基甲酸酯]，西维因[1-萘基N-甲基氨基甲酸酯]，灭多虫[S-甲基-N-[(甲基氨基甲酰基)氧基]硫代乙酰亚氨化物]，苯虫威[2-(乙硫基甲基)苯基甲基氨基甲酸酯]，涕灭威[2-甲基-2-(甲硫基)丙醛0-甲基氨基甲酰基肟]和甲氨叉成[N,N-二甲基-2甲基氨基甲酰氧基亚氨基-2-(甲硫基)乙酰胺]；合成除虫菊脂化合物如Etofenptox[2-(4-乙氧基苯基)-2-甲基丙基-3-苯氧基苄基醚]，杀灭菊酯[(RS)-α-氰基-3苯氧基苄基(RS)-2-(4-氯苯基)-3-甲基丁酸酯]、Esfewalerate[(S)-α-氰基-3-苯氧基苄基(S)-2-S)-α-氰基-3-苯氧基苄基2,2,3,3-四甲基环丙烷甲酸酯]，氯氰菊酯[(RS)-α氰基-3-苯氧基苄基(1RS,3RS)-3-(2,2-二氯乙烯基)-2,2-甲基环丙烷甲酸酯]，氯菊酯[3-苯氧基苄基(1RS,3RS)-(1RS,3RS)-3-(2,2-二氯乙烯基)-2,2-甲基环丙烷甲酸酯]，Cyhalothrin[(RS)-α-氰基-3-苯氧基苄基(2)-(1RS)-3-(2-氯-3,3,3-三氟丙烯基)-2,2-二甲基环丙烷甲酸酯]，Deltamethrin [(S)-α-氰基-间苯氧基苄基(1R,3R)-3-(2,2-二溴乙烯基)-2,2二甲基环丙烷甲酸酯]和Cycloprothrin[(RS)-α氰基-3-苯氧基苄基(RS)-2,2-二氯1-(4乙氧基苯基)环丙烷甲酸酯]；噻二嗪衍生物如Buprofezin[2叔丁基亚氨基-3-异丙基5-苯基1,3,5-噻二嗪-4-酮]；硝基咪唑烷衍生物如Imidacloprld[1-(6-氯3吡啶基甲基)N-硝基咪唑烷-2-亚基胺]，Nereistoxin衍生物如巴丹[S,S’-(2-二甲基氨基三亚甲基)双(硫代氨基甲酸酯)]，硫环杀[N,N-二甲基-1,2,3-三噻烷-5-基胺]和Bensultap[S,S-2-二甲基氨基三亚甲基二(苯硫代磺酸酯)]；氯代烃化合物如硫丹[6,7,8,9,10,10，-六氯-1,5,5a,6,9,9a-六氢6,9-亚甲基-2,4,3-苯并二氧杂硫杂吖庚因氧化物]和γ-BHC[1,2,3,4,5,6-六氯环己烷]；苯甲酰基苯基脲化合物如Chlorfluazuron[1-(3,5-二氯-4-(3-氯-5-三氟甲基吡啶-2-基氧基(苯基)-3-2,6-二氟苯甲酰基)脲]，Teflubenzuron[1-(3,5-二氯-2,4-二氟苯基)-3-(2,6-二氟苯甲酰基)脲]和Fulphenoxron[1-(4(2-氯-4-三氟甲基苯氧基)-2-氟苯基)-3-(2,6-二氟苯甲酰基)脲]；甲脒衍生物如虫螨脒[N,N’[(甲基亚氨基)二甲亚基(dimethvlidine)]-二2,4-二甲代苯胺]和杀虫脒[N’(4-氯-2-甲基苯基)-N,N-二甲基甲亚胺酰胺]。
当用作有害生物体防治剂的活性成分时，本发明化合物，尽管可以没有加入任何其它成份时被使用，通常被用作制剂如油喷雾剂，可乳化的浓缩物，可湿性粉剂，用于以水为基础的悬浮液或以以水为基础的乳化液的可流动浓缩物；粒剂，尘剂，气雾剂，热熏蒸剂。例如，自燃型，化学反应型或多孔陶瓷板型熏蒸剂；ULV剂或毒饵，通过将它们与固体载体，液体载体，气体载体或毒饵混合，并且，如果需要，加入表面活性剂和其它用于制剂的佐剂。
这些制剂通常以0.001％至95％重的比例含有本发明化合物。
作为被用于制剂的固体载体，可被提到的有，例如，粘土材料(例如，高岭土，硅藻土，合成的水化二氧化硅，膨润土，Fubasami粘土，酸性粘土)，各种滑石，陶瓷和其它无机矿物(例如，丝云母，，石英，硫磺，活性炭，碳酸钙，水化硅石)和化肥(例如，硫酸铵，磷酸铵，硝酸铵，尿素，氯化铵)的细粉或颗粒。作为液体载体，可被提到的有，例如，水，醇(例如甲醇，乙醇)酮类(例如，丙酮，甲基乙基酮)，芳香烃(例如，苯，甲苯，二甲苯，乙苯，甲基萘)，脂肪烃(例如，己烷，环己烷，煤油，汽油)酯类(例如，乙酸乙酯，乙酸丁酯)，腈类(例如，乙腈，异丁腈)醚类(例如，二异丙基醚，二噁烷)，酰胺(例如，N,N-二甲基甲酰胺，N,N-二甲基乙酰胺)，卤代烃(例如，二氯甲烷，三氯乙烷，四氧化碳)、二甲亚砜和植物油(例如，豆油，棉籽油)。作为气体载体或推进剂，可被提到的有，例如flon气，丁烷气体，LPG(液化石油气)，二甲醚和二氧化碳。
作为表面活性剂，可被提到的有，例如，烷基硫酸酯，烷基磺酸酯，烷基芳基磺酸酯，烷基芳基醚及其聚环氧乙烷衍生物，聚乙二醇醚，多羟基醇酯的糖醇衍生物。
作为用于制剂中的佐剂，如固定剂或分散剂，可以提到的有，例如，酪蛋白，明胶，多糖(例如，淀粉粉末，阿拉伯胶，纤维素衍生物，藻酸)，木素衍生物，膨润土，糖和合成的水溶性聚合物(例如，聚乙烯醇，聚乙烯基吡咯烷酮，聚丙烯酸)。作为稳定剂，可被提到的有，例如，PAP(异丙基酸磷酸酯)，BHT(2,6-二叔丁基-4-甲基苯酚)，BHA(2-叔丁基-4-甲氧基苯酚的3-叔丁基-4甲氧基苯酚的混合物)，植物油，矿物油，表面活性剂，脂肪酸或其酯。
作为自燃型熏蒸剂的基质，可被提到的有，例如，燃烧热产生剂如硝酸盐，亚硝酸盐，胍盐，氯酸钾，硝基纤维素，乙基纤维素木屑，热解刺激剂如碱金属盐，碱土金属盐，重铬酸盐和铬酸盐；氧供给剂如硝酸钾；燃烧助剂如密胺和小麦淀粉；扩展剂如硅藻土；和粘合剂如合成浆糊。
作为化学反应型熏蒸剂的基础材料，可被提到的有，例如，放热剂如硫化物，多硫化物，氢硫化物和碱金属的盐水合物、和氧化钙；催化剂如含碳材料，铁碳合金和活化的粘土；有机发泡剂如偶氮二碳酰胺，苯磺酰基肼，二硝基五亚甲基四胺聚苯乙烯的聚氨基甲酸乙酯；和填充剂如天然纤维碎片和合成纤维碎片。
作为毒饵的基本材料，可被提到的有，例如，诱饵成份如谷物粉，植物油，糖和晶状纤维素；抗氧化剂如二丁基羟基甲苯和去甲二氢愈创木酸；防腐剂如脱氢乙酸；错喂预防剂如红辣椒粉；和吸引调味剂如奶酪味剂和洋葱味剂。
制剂如可流动的浓缩物(对于以水为基础的悬浮液或以水为基础的乳化液)通常通过将1-75％化合物悬浮于含0.5-15％分散剂，0.1-10％悬浮剂(例如，保护性胶体或能变传递化合物)和0-10％适当佐剂(例如，消泡剂，抗腐蚀剂，稳定化剂，伸展剂，穿透助剂，抗冻剂，抗真菌剂，抗烟剂)的水中而得到。可以用基本上不溶解本发明化合物的各种油代替水给出油基悬浮液。作为保护性胶体，可被提到的有，例如，明胶，酪蛋白，各种胶，纤维素醚的聚乙烯醇。作为触变传递化合物，可被提到的有，例如，膨润土，硅酸铝镁，黄蓍胶和聚丙烯酸。
这样得到的制剂就这样使用或用水等稀释后使用。它们可以与其它杀昆虫剂，杀线虫剂，杀螨剂，杀真菌剂，除莠剂，植物生长调节剂，协同剂，肥料，土壤调节剂，动物饲料等混合或不混合使用，
当本发明化合物被用作农业上的有害生物体防治剂时，其用量通常在每公亩0.001至500g，优选0.1g至500g的范围内。其制剂如可乳化的浓缩物，可湿性粉剂和可流动的浓缩物通常在用水稀释至应用浓度0.001至1000ppm之后使用。其制剂如粒剂和尘剂不经任何稀释而使用。当本发明化合物被用作防疫的有害生物体防治剂时，其制剂如可乳化的浓缩物，可湿性粉剂和可流动的浓缩物通常在用水稀释至应用浓度0.001至10000ppm后使用。而其制剂如油喷雾剂，气雾剂，熏蒸剂，ULV剂和毒饵就这样使用。
所有这些用量和应用浓度可随制剂类型，使用时间，使用地点，使用方法，有害生物体种类如有害昆虫，有害螨和蜱，损害程度和其它条件而变化，这它们可以不受上述范围限制而增加或减少。
实施例
本发明将通过下列生产实施例，制剂实施例和试验实施例进一步举例说明；然而，本发明不限于这些实施例。
生产实施例1
通过生产方法a生产化合物1
在搅拌下，10分钟内，往10ml无水N,N-二甲基甲酰胺和72mg氢化钠(60％油分散体)中滴加300mg 4-(1-吡唑基)甲基苯酚的无水N,N二甲基甲酰胺(5ml)溶液。室温搅拌1小时后，混合物被冷却至5℃至10℃，在30分钟内往其中滴加505mg 2-(2-吡啶氧基)乙基对苯磺酸酯的无水N,N二甲基甲酰胺(5ml)溶液。混合物在室温搅拌过夜、然后有60℃至70℃再搅拌2小时。反应混合物被倒入50ml冰水中，用30ml乙酸乙酯提取两次。合并有机层，水洗，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出208mg 4-(1-吡唑基)甲基苯基2-(2-吡啶氧基)乙基醚(化合物1)。产率，41％。
m.p.82.7℃
生产实施例2
通过方法b生产化合物2
在搅拌下，10分钟内，往10ml无水N,N-二甲基甲酰胺和96mg氢化钠(60％油分散液)中滴加500mg 2-[4-(1-吡唑基)甲基苯氧基]乙醇(在下述参考生产实施例1中生产)的N,N-二甲基甲酰胺(5ml)溶液。在60℃至70℃搅拌2小时后。混合物被冷却至5℃至10℃，在30分钟内往其中滴加288mg 2-氯嘧啶的N,N-二甲基甲酰胺(5ml)溶液。混合物在室温搅拌过夜、然后在60℃至70℃再搅拌2小时。反应混合物被倒入50ml冰水中，用30ml甲苯萃取两次。合并有机层，用水洗，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出339mg 4-(1-吡唑基)甲基苯基2-(2-嘧啶氧基)乙基醚(化合物2)。产率，50％。
m.p.81.7℃
生产实施例3
通过方法c生产化合物3
在搅拌下，10分钟内，往5ml无水N,N-二甲基甲酰胺和51mg氢化钠(60％油分散液)的混合物中滴加121mg 2-羟基吡啶的无水N,N-二甲基甲酰胺(3ml)溶液。室温搅拌1小时后，混合物被冷却至5℃至10℃，在30分钟内往其中滴加300mg 2-[-4-(2-2H-1,2,3,-三唑基)甲基苯氧基]乙基溴的无水N,N-二甲基甲酰胺(2ml)溶液。混合物然后在室温搅拌过夜。反应混合物被倒入5ml冰水中，用30ml甲苯萃取两次。合并有机层，水洗，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出4-(2-2H-1,2,3-三唑基)甲基苯基2-(2-吡啶氧基)乙基醚。
生产实施例4
通过方法b生产化合物5
在搅拌下，10分钟内，往10ml无水N,N-二甲基甲酰胺和110mg氢化钠(60％油分散液)的混合物中滴加500mg 2-[4-(1-吡唑基)甲基苯氧基]乙醇(在下述参考生产实施例1中生产)的无水二甲亚砜(5ml)溶液。在60℃至70℃搅拌2小时后。混合物被冷却至5℃至10℃，在10分钟内往其中滴加488mg 2溴噻唑的无水N,N-二甲基甲酰胺(5ml)溶液。混合物然后在室温搅拌过夜、然后在60℃至70℃再搅拌2小时。反应混合物被倒入50ml冰水中，用30ml甲苯萃取两次。合并有机层，水洗，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出280mg 4-(1-吡唑基)甲基苯基2-(2-噻唑氧基)乙基醚(化合物5)。产率，41％。
m.p.65.6℃
生产实施例5
通过方法b生产化合物8
在搅拌下，10分钟内，往10ml无水N,N-二甲基甲酰胺和24mg氢化钠(60％油分散液)的混合物中滴加500mg 2-[2-氯-4-(1吡唑基)甲基苯氧基]乙醇(在下述参考生产实施例3中生产)的无水N,N-二甲基甲酰胺(5ml)溶液。在60℃至70℃搅拌2小时后。混合物被冷却至5℃至10℃，在30分钟内往其中滴加250mg 2-氟嘧啶的无水N,N-二甲基甲酰胺(5ml)溶液。混合物在室温搅拌过夜，然后在60℃至70℃再搅拌2小时。反应完成后，反应混合物被倒入50ml冰水中，用30ml甲苯萃取两次。合并有机层，用水洗，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出595mg 2-氯-4-(1-吡唑基)甲基苯基2-(2吡啶氧基)乙基醚(化合物8)。产率，91％。
m.p.82.3℃
本发明化合物的一些典型例子以其化合物号和物理性质被示于表3中(通过定义在通式P-1化合物中的各个取代基)。
表3
如下通式的化合物： 
下面将叙述用于生产本发明化合物的起始化合物的生产实施例。
参考生产实施例1
60g 4-(1-吡唑基)甲基苯酚、54.9g氯代乙酸乙酯，95.1g碳酸钾，和500ml无水二甲基甲酰胺的混合物在50℃加热搅拌5小时，接着冷却至室温。反应混合物被倒入1升水中，用200ml乙酸乙酯提取两次。合并有机层，用水，饱和氯化铵水溶液，然后饱和氯化钠溶液洗涤，无水硫酸镁干燥，减压浓缩给出粗的4-(1-吡唑基)甲基苯氧基乙酸乙酯油状物。
在-78℃，搅拌下，30分钟内，往38g氢化铝锂在500ml无水的四氢呋喃的悬浮液中滴加溶于100ml无水四氢呋喃的上面的粗4-(1-吡唑基)甲基苯氧基乙酸乙酯。混合物在同样温度下搅拌1小时，然后在-20℃再搅拌2小时。反应混合物再冷却至-78℃，在同样温度下往其中滴加38mg水，38ml 15％氢氧化钠水溶液，然后114ml水，随后加入500ml甲苯，500ml四氢呋喃，然后200g无水硫酸钠混合物在室温下搅拌2小时。反应混合物被滤过硅藻土，滤液被减压浓缩。剩余物进行硅胶柱层析，给出64.5mg 2-[4-(吡唑基)甲基苯基]乙醇白色晶体。产率，86％(以4-(1-吡唑基)甲基苯酚为基础)。
m.p.56℃至58℃
参考生产实施例2
2-氯-4-(1-吡唑基)甲基苯酚的生产
(1)2-氯-4-甲基苯基2,2-二甲基丙酸酯的生产
在5℃至10℃，搅拌下，1小时内，往100g 2-氯-4-甲基苯酚，92.3g三乙胺和1升无水四氢呋喃的混合物中滴加93.0g新戊酰氯。然后，在同样温度下搅拌3小时，反应混合物被倒入冰水中。用二乙醚萃取两次。有机层用3％盐酸，然后用水洗涤，无水硫酸镁干燥，减压浓缩。产生的油状物被减压蒸馏，给出155,3g 2-氯-4-甲基苯基2,2二甲基丙酸酯无色清亮液体，产率，97.7％.
b.p.113.8-118℃/5mmhg；nD 21.81.4949
(2)4溴甲基-2-氯苯基2,2-二甲基丙酸酯的生产
在60℃，搅拌下，3小时内，往50.0g 2-氯-4-甲基苯基2,2-二甲基丙酸酯，23.8g无水碳酸钠和500ml四氯化碳的混合物中加入很少量的过氧化苯甲酰和滴加35.2g溴。检测反应进程(溴的红色消失)，如果需要，加入很少量的过氧化苯甲酰，继续搅拌有到反应彻底完成。
反应完成后，反应混合物被冷却至10℃，抽滤除去不溶物，接着减压浓缩，给出68.7g 4-溴甲基2-氯苯基2,2-二甲基丙酸酯浅黄色固体。表观产率，101.7％。此固体用己烷和甲苯的混合溶剂重结晶给出白色晶体。
m.p,63.3℃
(3)2-氯-4-(1-吡唑基)甲基苯基2,2-二甲基丙酸酯的生产
15.3g吡唑，89.9g氢化钠(60％油分散液)和200ml无水N,N-二甲基甲酰胺的混合物在氮气氛中于60℃至70℃搅拌2小时。氢气散发停止后，混合物被冷却至10℃，在室温搅拌下，1小时内，往此混合物中滴加68g 4-溴甲基-2-氟苯基2,2-二甲基丙酸酯的无水N,N-二甲基甲酰胺(300ml)溶液，混合物在80℃搅拌1小时。冷却后，混合物被倒入冰水中，用乙酸乙酯萃取两次。有机层用饱和氯化铵水溶液，然后用饱和氯化钠溶液洗涤，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出39.5g 2-氯4-(1-吡唑基)甲基苯基2,2-二甲基丙酸酯无色油。产率，60％。
nD 21.81.5461
(4)2氯4-(1-吡唑基)甲基苯酚的生产
20.0g 2-氯-4-(1-吡唑基)甲基苯基2,2-二甲基丙酸酯，50ml20％氢氧化钠水溶液和300ml乙醇的混合物被加热5小时。反应混合物然后被减压浓缩，往其中加入水混合物用浓盐酸调节至pH6.0。此混合物用乙酸乙酯萃取。有机层用水洗，无水硫酸镁干燥减压浓缩。剩余物进行硅胶柱层析，给出11.5g 2-氯-4-(1-吡唑基)甲基苯酚白色晶体，产率，80.7％
m.p.,152.9℃
参考生产实施例3
2-[2-氯-4-(1-吡唑基)甲基苯氧基]乙醇的生产
5.0g 2-氯-4-(1-吡唑基)甲基苯酚(在参考生产实施例2中生产)，7.6g氯代乙酸乙酯， 13.2g碳酸钾和100ml无水二甲基甲酰胺的混合物在50℃搅拌5小时。然后冷却至室温，反应混合物被倒入500ml水中，用50ml乙酸乙酯萃取两次。合并有机层，用水，饱和氯化铵水溶液，然后饱和氯化钠溶液洗涤；无水硫酸镁干燥，减压浓缩给出粗2-氯-4-(1-吡唑基)甲基苯氧基乙酸乙酯油状物。
在-78℃，搅拌下，30分钟内，往1.2g氢化铝锂的无水四氢呋喃(100ml)悬浮液中滴加上述粗2-氯-4-(1-吡唑基)甲基苯氧基乙酸乙酯溶于20ml无水四氢呋喃的溶液。混合物在同样温度搅拌1小时，并在-20℃再搅拌2小时。反应混合物再次冷却到-78℃，在同样温度下往其中滴加1.2ml水，1.2ml 15％氢氧化钠水溶液，然后3.6ml水，随后加入100ml甲苯，100ml四氢呋喃和50g无水硫酸钠，混合物在室温搅拌2小时。反应混合物被滤过硅藻土，滤液被减压浓缩。剩余物进行硅胶柱层析，给出4.48g 2-[2-氯-4-(吡唑基)甲基苯氧基]乙醇白色晶体。产率，74％(以2-氯-4(1-吡唑基)甲基苯酚为基础)。
m.p,88.7℃
参考生产实施例4
2-氯-4-(2-2H-1,2,3-三唑基)甲基苯基2,2-二甲基丙酸酯的生产
2.26g 2H-1,2,3三唑，1.31g氢化钠(60％油分散液)和100ml无水N,N-二甲基甲酰胺的混合物在氮气氛中于60℃至70℃搅拌2小时。氢气的散发停止后，混合物被冷却至10℃。在室温搅拌下，1小时内，往此混合物中滴加10g 4-溴甲基-2-氯苯基2,2-二甲基丙酸酯的无水N,N-二甲基甲酰胺(150ml)溶液，混合物在80℃搅拌1小时。冷却后，混合物被倒入冰水中，用乙酸乙酯萃取。有机层用饱和氯化铵水溶液，然后用饱和氯化钠溶液洗涤，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出2-氟-4-(2-2H-1,2,3-三吡唑基)甲基苯基2,2-二甲基丙酸酯。
(2)2-氯-4-(2-2H-1,2,3-三唑基)甲基苯酸的生产
3g 2氯-4-(2-2H-1,2,3-三唑基)甲基苯基2,2-二甲基丙酸酯，10ml 20％氢氧化钠水溶液和60ml乙醇混合物被加热回流5小时。反应混合物然后减压浓缩，往其中加入水，混合物用浓盐酸调节至pH6.0。此混合物用乙酸乙酯萃取。有机层用水洗涤，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出2-氯-4-(2-2H-1,2,3-三唑基甲基)苯酚。
参考生产实施例5
2-氯-4-(2-吡啶酮-1-基)甲基苯酚的生产
(1)2-氯-4-(2-吡啶酮-1-基)甲基苯基2,2-二甲基丙酸酯的生产
3.11 g 2-比啶酮，1.31g氢化钠(60％油分散液)和100ml无水N,N二甲基甲酰胺的混合物在在氮气氛中于60℃至70℃搅拌2小时。氢气发散停止后，混合物被冷却到10℃。在室温下，搅拌1小时内，往此混合物中滴加10g 4-溴甲基-2氟苯基2,2-二甲基丙酸酯的无水N,N-二甲基甲酰胺(150ml)溶液，混合物在80℃搅拌1小时。冷却后，混合物被倒入冰水中，用乙酸乙酯萃取。有机层用饱和氯化铵水溶液，然后用饱和氯化钠溶液洗涤，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出7.60g 2-氯-4-(2-吡啶酮-1-基)甲基苯基2,2-二甲基丙酸酯白色晶体。产率，73％。
m.p.,145.2℃
(2)2-氯-4-(2-吡啶酮-1-基)甲基苯酚的生产
7.6g 2-氯-4-(2-吡啶酮-1-基)甲基苯酚2,2-二甲基丙酸酯，19ml 20％氢氧化钠水溶液和200ml乙醇的混合物被加热回流5小时。反应混合物然后减压浓缩，往其中加入水，混合物用浓盐酸调节至pH6.0。此混合物用乙酸乙酯萃取。有机层用水洗涤，用无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱色谱，给出3.98g 2-氟-4-(2-吡啶酮-1-基)甲基苯酚白色晶体。产率，71％。
m.p.193.5℃
参考生产实施例6
2-[4-(1-吡唑基)甲基苯氧基]乙基溴的生产
在搅拌下，加热回流时，2小时内，往15g[4-(1-吡唑基)甲基苯酚，32.4g 1,2-二溴乙烷和150ml水的混合物中滴加30ml 4.1g氢氧化钠水溶液，反应混合物被倒入200ml冰水中，用100ml乙醚萃取两次。合并有机层，用5N氢氧化钠水溶液，水然后用饱和氯化钠溶液洗涤，无水硫酸镁干燥，减压浓缩。剩余物进行硅胶柱层析，给出11.44g 2-[4-(1-吡唑基)甲基苯氧基]乙基溴白色晶体。产率，47％。
m.p.63-65℃
下面将叙述用作含有本发明化合物作活性成份的有害生物体防治剂的制剂实施例，其中“份”为质量，本发明化合物由其示于表3中的化合物号表示。
制剂实施例1
可乳化的浓缩物
本发明化合物1至10各十份被溶于35份二甲苯和35份二甲基甲酰胺中，往其中加入14份聚环氧乙烷苯乙烯苯基醚和6份十二烷基苯磺酸钙，混合物被充分搅拌给出10％各个化合物的可乳化的浓缩物。
制剂实施例2
可湿性粉剂
本发明化合物1到10各二十份被加到4份月桂基硫酸钠、2份木素磺酸钙，20份合成的水化二氧化硅细粉和54份硅藻土的混合物中，混合物用一果汁混合器搅拌出各个化合物的20％可湿性粉剂。
制剂实施例3
粒剂
往本发明化合物1到10各5份中加入5份合成的水合二氧化硅细粉，5份十二烷基苯磺酸钠，30份膨润土和55份粘土，混合物被充分搅拌。然后往此混合物中加入适量水，进一步搅拌，用成粒机粒化，晾干给出各化合物的5％粒剂。
制剂实施例4
尘剂
往2份各个本发明化合物1至10中加入5份聚丙二醇，混合物被加热到高于熔点以溶解将其吸收于93份颗粒状焙烧过的硅藻土中，将其温热，给出各个化合物的2％颗粒。
制剂实施例5
尘剂
一份各个本发明化合物1到10被溶于适量丙酮中，往其中加入5份合成的水化二氧化硅细粉0.3份PAP和93.7份粘土，混合物用一果汁混合器搅拌。蒸发除去丙酮给出各个化合物的1％尘剂。
制剂实施例6
以水为基础的悬浮液
本发明化合物1至10各二十份和1.5份脱水山梨糖醇三油酸酯与28.5份含2份聚乙烯醇的水溶液混合，混合物用一砂子粉碎机磨成细粉(颗粒大小不大于3μm)，往其中加入40份含0.05份黄蓍xanthane胶和0.1份硅酸铝镁的水溶液，然后加入10份丙二醇。混合物被搅拌给出20％的各个化合物的以水为基础的悬浮液。
制剂实施例7
油喷雾剂
首先，本发明化合物1至10各0.1份被溶于5份二甲苯和5份三氯乙烷中。溶液然后与89.9份脱味煤油混合给出各个化合物的0.1％油喷雾剂。
制剂实施例8
以油为基础的气雾剂
首先，本发明化合物1至10各0.1份，0.2份tetramethrin,0.1份d-phenothin,10份三氯乙烷和59.6份脱味煤油被混合以溶解。溶液被放入气雾剂容器中，然后装上阀门。通过所说的阀门，在增压下装入30份推进剂(液化石油气)给出各个化合物的以油为基础的气雾剂。
制剂实施例9
以水为基础的气雾剂
首先，0.2份各个本发明化合物1至10,0.2份d-allethrin,0.2份d-phenothrin,5份二甲苯，3.4份脱味煤油和1份乳化剂[ATMOS300(由AtlasChemical CO.登记的商品名]被混合溶解。混合物，与50份纯水一起装入气雾剂容器中，然后装上装上阀门。通过所说的阀门，在增压下装入40份推进剂(液化石油气)给出各个化合物以水为基础的气雾剂。
制剂实施例10
蚊香
往本发明化合物1至10各0.3g中加入0.3g d-allethrin，混合物溶于20ml丙酮中。溶液在搅拌下与99.4g蚊香载体(通过以4∶3∶3的比例混合Tabu粉，除虫菊果渣粉和木屑而制备)均匀混合，往其中加入120ml水。混合物充分捏合，模塑，干燥给出各化合物的蚊香。
制剂实施例11
电蚊香片
往本发明化合物1至10各0.4g中0.4g d-allethrin和0.4g pipenylbutoxide中加入丙酮以溶解，使总体积变为10ml。此溶液以0.5ml均匀地吸收于电蚊香片的底物(通过将棉绒和浆的纤维化混合物压成片而制备)，为2.5cm×1.5cm和0.3cm厚，给出各化合物的电蚊香片。
制剂实施例12
热烟制剂
首先，本发明化合物1至10各100mg被溶于适量丙酮中，溶液然后吸收于4.0cm×4.0cm和1.2cm厚的多孔陶瓷板中给出各化合物的热熏蒸剂。
制剂实施例13
毒饵
首先，本发明化合物1至10各10mg溶于0.5ml丙酮中，此溶液被加入5g对动物的固体诱饵粉末(Breeding Solid Feed Powder CE-2,JapanClea Co.,Ltd.的商品名)，均匀混合。然后，晾干除去丙酮给出各个化合物的0.5％毒饵。
下列试验实施例将证明本发明化合物可用作有害生物体防治剂的活性成分，其中本发明化合物由其示于表3中的化合物号表示。
试验实施例1
抗家蚊的杀昆虫试验
根据制剂实施例1得到的试验化合物的可乳化浓缩物用水稀释，此稀释液以0.7ml被加入100ml离子交换水中至确定浓度。二十只家蚊(Culexpipiens pallens)的最大龄幼虫被放出，哺育毒饵8天。羽化抑制率由下面的方程1测定。结果示于表4中。
表4
| 试验化合物 | 使用浓度(ppm) | 羽化抑制率(％) |
| 112344 | 3.50.13.53.53.50.1 | 100100100100100100 |
试验买施例2
抗棉蚜的杀昆虫试验
根据制剂实施例1得到的试验化合物的可乳化的浓缩物用水稀释到预定的浓度，稀释液以10cc/l锅的比率浇在栽培在聚乙烯杯中的黄瓜靠根部的部分。处理3天后，五只棉蚜(Aphis gossypii)成虫被放在主叶上。自由饲养14天后，防治值通过方程2测定。结果示于表5中。
其中Cb是在未处理组中处理前的昆虫数；Cai是在观察期间未处理组的昆虫数；Tb是在实验组中处理前的昆虫数；而Tai是在实验组中观察期间的昆虫数。 表5
| 试验化合物 | 使用浓度(ppm) | 防治值(％) |
| 12568 | 500500500500500 | 82961009079 |
工业实用性
根据本发明，提供了对有害生物体具有优良防治作用的新的醚化合物。这些醚化合物可用作有害生物体防治剂的活性成分。
Claims (8)
1．如下通式的醚化合物： (P-1)其中R1是氢或氯；
R2和R3独立地是氢或甲基；
A是如下通式的基团：
其中R4是氢、氯或甲基；而R5和R6独立地为氢或氯；条件是A
不是二氢吡啶酮基；
B是如下通式的基团：
其中R7和R8独立地为氢或氟；而且
X是氧或硫。
2．根据权利要求1的醚化合物，其中A是如下通式的基团：
(P-2)其中R4如权利要求1定义。
3．根据权利要求2的醚化合物，其中R4是氢。
4．根据权利要求1的醚化合物，其中R1是氢。
5．4-(1-吡唑基)甲基苯基2-(2-吡啶氧基)乙基醚。
6．4-(1-吡唑基)甲基苯基2-(2-嘧啶氧基)乙基醚。
7．4-(1-吡唑基)甲基苯基2-(噻唑氧基)乙基醚。
8．一种杀虫剂，其特征在于包含权利要求1的醚化合物作活性成份。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP84683/94 | 1994-04-22 | ||
| JP8468394 | 1994-04-22 |
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| CN1043041C true CN1043041C (zh) | 1999-04-21 |
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| Country | Link |
|---|---|
| US (2) | US5883262A (zh) |
| EP (1) | EP0757048A4 (zh) |
| KR (1) | KR970702276A (zh) |
| CN (1) | CN1043041C (zh) |
| AU (1) | AU689880B2 (zh) |
| CA (1) | CA2188252A1 (zh) |
| RU (1) | RU2137767C1 (zh) |
| WO (1) | WO1995029175A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| BE1008977A5 (fr) * | 1994-12-27 | 1996-10-01 | Solvay | Adjuvants pour vaccins. |
| AU5920399A (en) * | 1998-09-15 | 2000-04-03 | Jack H. Bates | Persistent diatomaceous earth molluskicidial composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0388682A1 (de) * | 1989-03-15 | 1990-09-26 | Bayer Ag | Substituierte Heteroarylphenylether, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
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| US4329488A (en) * | 1980-12-05 | 1982-05-11 | Hoffmann-La Roche Inc. | Propionic acid esters and herbicidal use thereof |
| JPS58150559A (ja) * | 1982-03-04 | 1983-09-07 | Sumitomo Chem Co Ltd | オキシムエ−テル誘導体、その製造法およびそれを有効成分として含有する殺虫剤 |
| JPS59199673A (ja) * | 1983-04-25 | 1984-11-12 | Sumitomo Chem Co Ltd | 含窒素複素環化合物、その製造法およびそれを有効成分とする有害生物防除剤 |
| ATE66675T1 (de) * | 1985-07-18 | 1991-09-15 | Sandoz Ag | Stickstoffhaltige heterozyklische verbindungen. |
| CA1329614C (en) * | 1987-05-02 | 1994-05-17 | Rainer Buerstinghaus | N-substituted azoles |
| US5315013A (en) * | 1988-01-07 | 1994-05-24 | E. I. Du Pont De Nemours And Company | Substituted pyrazole angiotensin II antagonists |
| US5102903A (en) * | 1990-05-10 | 1992-04-07 | E. I. Du Pont De Nemours And Company | Treatment of glaucoma and ocular hypertension with pyrazole, pyrrole and triazole angiotensin-II receptor antagonists |
| IL100917A0 (en) * | 1991-02-16 | 1992-11-15 | Fisons Plc | Pyridinone and pyrimidinone derivatives,their preparation and pharmaceutical compositions containing them |
| JPH04342554A (ja) * | 1991-05-20 | 1992-11-30 | Sumitomo Chem Co Ltd | ３−（４−置換−２−クロロフェノキシ）プロピオンアルドキシム エチルエ−テル系化合物、その製造法およびそれを有効成分とする有害生物防除剤 |
| DE4129340A1 (de) * | 1991-09-04 | 1993-03-11 | Merck Patent Gmbh | 1,2-dihydro-2-oxopyridine |
-
1995
- 1995-04-19 KR KR1019960705926A patent/KR970702276A/ko not_active Application Discontinuation
- 1995-04-19 CN CN95193710A patent/CN1043041C/zh not_active Expired - Fee Related
- 1995-04-19 RU RU96122633A patent/RU2137767C1/ru active
- 1995-04-19 WO PCT/JP1995/000763 patent/WO1995029175A1/ja not_active Application Discontinuation
- 1995-04-19 EP EP95916006A patent/EP0757048A4/en not_active Withdrawn
- 1995-04-19 US US08/727,565 patent/US5883262A/en not_active Expired - Fee Related
- 1995-04-19 AU AU22667/95A patent/AU689880B2/en not_active Ceased
- 1995-04-19 CA CA002188252A patent/CA2188252A1/en not_active Abandoned
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1998
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0388682A1 (de) * | 1989-03-15 | 1990-09-26 | Bayer Ag | Substituierte Heteroarylphenylether, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
Also Published As
| Publication number | Publication date |
|---|---|
| US5972949A (en) | 1999-10-26 |
| EP0757048A1 (en) | 1997-02-05 |
| WO1995029175A1 (fr) | 1995-11-02 |
| AU2266795A (en) | 1995-11-16 |
| US5883262A (en) | 1999-03-16 |
| RU2137767C1 (ru) | 1999-09-20 |
| CN1151160A (zh) | 1997-06-04 |
| AU689880B2 (en) | 1998-04-09 |
| CA2188252A1 (en) | 1995-11-02 |
| EP0757048A4 (en) | 2000-04-12 |
| KR970702276A (ko) | 1997-05-13 |
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