CN1309650A - 具有杀虫作用的取代的联苯基噁唑啉衍生物 - Google Patents
具有杀虫作用的取代的联苯基噁唑啉衍生物 Download PDFInfo
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- 238000007920 subcutaneous administration Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
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Abstract
本发明涉及式(Ⅰ)的新的噁唑啉衍生物,其中基团A,B,Q和R具有说明书中给出的定义。本发明还涉及它们的制备方法和它们在害虫防治中的用途。
Description
本发明涉及新的取代的噁唑啉衍生物,其制备方法和其防治动物害虫的用途。
已知噁唑啉衍生物具有杀虫和杀螨活性(参见,例如EP-A-0432661,EP-A-696584,WO-A95/04726,WO-A96/11190或WO-A96/22283),例如2-(2,6-二氟苯基)-4-(4’-甲氧基-或异丙氧基联苯-4-基)-1,3-噁唑啉(参见EP-A0432661)。
但是,这些已知化合物作用的效力和/或作用期,特别是抗某些有机体,或者在低施用浓度时,并不是在所有应用领域令人完全满意。
因此,本发明提供式(Ⅰ)新的取代的噁唑啉衍生物其中基团A,B,Q和R各自在下面的表1中定义:表1化合物序号 A B Q R1 F F H
2 Cl H H
3 F Cl H -CH2-C(CH3)=N-O-CH(CH3)C2H54 F Cl H -C(CH3)2-C(CH3)=N-O-C3H7-i5 Br H H -C3H7-i6 F F H -CO-NH-C3H7-i7 F F H -CF=CF-CH=CH28 F F H -CH2-CH=NOCH39 H Cl H -C3H7-n10 H Cl H
11 H Cl H -C3H7-i表1(续)化合物序号 A B Q R12 H Cl H -C4H9-n13 H Cl H
14 H Cl H -CH2-C3H7-i15 F F H -CH2CH2-CH=CF216 F F H -CH2-CH=NOC2H517 F F H
18 F F H
19 F F H
20 F F H
21 F F H
22 I H H
23 F F H
24 F F H
25 F F H
26 F F H
表1(续)化合物序号 A B Q R27 F Cl H -C3H7-i28 F F H
29 F Cl H -C3H7-n30 F Cl H -CH2-C3H7-i31 F F H
32 F F H
33 F F H
34 F Cl H -C4H9-n35 F F H -CH(CH3)-CH=NOCH336 F F H -CH(CH3)-C≡CH37 Cl H H -CH(CH3)-C≡CH38 Cl F H
39 Cl H H -CH2-C3H7-i40 Cl Cl H
41 Cl Cl H -C3H7-i42 F F H
表1(续)化合物序号 A B Q R43 F F Cl
44 F F Cl
45 Cl H Cl
46 F F H
47 F Cl H
48 F Cl H
49 F Cl H
50 F F H
51 F F H
52 F F H
53 F F H -C(CH3)2-CH=NOC2H554 F Cl H
55 F F H
56 F F H
表1(续)化合物序号 A B Q R57 F F H -C(CH3)2-CH=NOCH358 Cl H H
59 F F H
60 F F H
61 Cl H Cl
62 Cl H Cl
63 F F Cl
64 F F Cl
65 Cl Cl H -CH(CH3)-COCH366 Cl Cl H
67 Cl Cl H
68 Br H H -CH(CH3)-COCH369 Cl H H CF370 CH3O- H H CF371 CF3 H H CF372 CH3SO2- H H CF373 C2H5O- H H CF3表1(续)化合物序号 A B Q R74 i-C3H7O- H H CF375 NO2 H H CF376 CH3O- F H CF377 F NH2 H CF378 CH3S- H H CF379 i-C3H7S- H H CF380 C2H5S- H H CF381 C2H5O- F H CF382 C2H5CH(CH3)O- F H CF383 C2H5CH(CH3)O- C2H5CH(CH3)O- H CF384 i-C3H7CH2O- F H CF385 i-C3H7CH2O- i-C3H7CH2O- H CF386 C2H5 H H CF387
H H CF388 CH3O H H C3H7-i89 Br H H CF390 I H H CF391 Br H H -CH(CH3)-CH(OH)CH392 Br H H -CH(CH3)-C(CH3)=NOCH393 H H H C3H7-i表1(续)化合物序号 A B Q R94 I H H
95 Br H H -CH2-CH=CH296 Br H H -CH2-C≡CH97 F H Cl
98 F H Cl
99 F Cl H
100 F H H -CH(CH3)-COCH3101 F H H
102 F F H -C(CH3)2-CHO103 F H Cl
104 F Cl H
表1(续)化合物序号 A B Q R105 F H Cl
106 F H Cl
107 F H H -C3H7-i108 F H H -CH2-C3H7-i109 F H H
110 F H H
111 F H H
112 F Cl H -CH2-CH=NOCH3113 F Cl H -CH2-CH=NOC2H5114 F F Cl -CH2-CH=NOCH3115 F F Cl -CH2-CH=NOC2H5116 Cl H Cl -CH2-CH=NOCH3117 Cl H Cl -CH2-CH=NOC2H5118 F H Cl -CH2CF3119 F F CH3 -CH2CF3120 CF3CH2O- F CH3 -CH2CF3表1(续)化合物序号 A B Q R121 Cl H -CH2- -CH2CF3CH=CH2122 Cl H CH3 -CH2CF3123 F F C2H5 CH2CF3124 Cl H H -CH2CF3125 F F H
126 F F H -CH2-CF2-CHF2127 F F H -(CH2)3-CF2-CF3
式(Ⅰ)的取代的噁唑啉衍生物可以以旋光异构体和/或几何异构体存在,这取决于取代基。本发明提供异构体混合物和纯的各异构体两者。
M-R (Ⅲ)其中R在各种情况下如上文表1中定义,和M是离去基团。
此外发现,式(Ⅰ)的新的取代的噁唑啉衍生物高度适合防治农业,林业,贮藏品保护和材料保护以及卫生领域所遇到的动物害虫,特别是昆虫,蛛形纲和线虫。
式(Ⅰ)/表1提供了本发明的化合物的一般定义。优选的化合物在下面的表1A中列出:表1A化合物序号A B Q R1A F F H
2A Cl H H
3A F Cl H -CH2-C(CH3)=N-O-CH(CH3)C2H54A F Cl H -C(CH3)2-C(CH3)=N-O-C3H7-i5A Br H H -C3H7-i
使用,例如,2-(2,6-二氟苯基)-4-(4’-羟基联苯-4-基)-1,3-噁唑啉和4-三氟甲基苄基氯为进行本发明方法的起始物,则反应过程可以用下面的反应式描述:
式(Ⅱ)的起始物是已知的(参见例如EP-A432661和EP-A696584)和/或如本文所描述的,可以以一般公知的方法,通过下面的方法获得:在酸催化剂例如氢氟酸,硫酸,乙酸或氯化铝存在下和在稀释剂例如二氯甲烷或乙腈存在下,在0℃和80℃之间的温度下,用式(Ⅴ)的联苯衍生物与式(Ⅳ)的酰胺衍生物反应,其中A和B各自如上文表1中定义和R’代表C1-C4-烷基,优选甲基或乙基,其中
Q如上文表1中定义和
R”代表C1-C4-烷基或C1-C4-烷氧基,优选甲基,乙基,甲氧基或乙氧基;
在碱例如氢氧化钠溶液存在下,如果适当在催化剂例如铵化合物存在下,和如果适当在稀释剂例如二甲基甲酰胺存在下,在0℃和100℃之间的温度下,将得到的式(Ⅵ)的化合物环化得到式(Ⅶ)的联苯噁唑啉,其中A,B,Q和R”各自如上文定义,其中A,B,Q和R”各自如上文定义,并且在稀释剂例如甲醇存在下,在室温下,使用例如氨水以常规技术和方法水解,其中,如果适当,也可以一步反应进行环化和水解。
式(Ⅳ)的酰胺衍生物是已知的(参见例如EP-A594179)和/或可以通过本文描述的方法获得。
式(Ⅲ)提供也用作本发明方法中的起始物的化合物的一般定义。在结构式(Ⅲ)中,M代表常规离去基团,优选卤素,特别是氯或溴;烷基磺酰基氧基,特别是甲基磺酰基氧基;或者任选被取代的芳基磺酰基氧基,特别是苯基磺酰基氧基,对-氯苯基磺酰基氧基或甲苯磺酰基氧基。
式(Ⅲ)的化合物一般是已知的有机化学化合物。
用于进行本发明方法的合适的稀释剂是所有常规溶剂。优选使用任选卤化的芳香烃或脂肪烃,酮类,腈类和酰胺类。例子有甲苯,丙酮,乙腈,二甲基甲酰胺和二甲基乙酰胺。
用于进行本发明方法的合适的碱是所有常规无机和有机碱。例子有叔胺,例如三乙胺,DBN(二氮杂双环壬烯),DBU(二氮杂双环十一烯),DABCO(二氮杂双环辛烷),碱金属和碱土金属氢氧化物,例如氢氧化钠,氢氧化钾和氢氧化钙,以及碱金属和碱土金属碳酸盐,例如碳酸钠和碳酸钾。
如果适当,本发明方法在相转移催化剂存在下进行。例子有季铵盐,例如四辛基溴化铵或苄基三乙基氯化铵和三(3,6-二氧杂庚基)胺(TDA)。
当进行本发明方法时,反应温度可以在相当宽的范围内变化。一般情况下,反应在-20℃和100℃,优选0℃和60℃之间的温度下进行。
当进行本发明方法时,一般使用大约等摩尔量的物质。但是也可能使用过量的式(Ⅲ)的化合物。
用常规方法进行后处理和分离。
本发明的式(Ⅰ)的化合物也可以通过下面的反应获得:A)在第一步中,在本发明方法条件下,式(Ⅷ)的化合物与式(Ⅲ)的化合物反应其中Q如上定义,
M-R (Ⅲ)其中M和R各自如上定义;B)在第二步中,在稀释剂例如二氯甲烷或二氯乙烷存在下和在适合弗瑞德-克莱福特反应的酸或路易斯酸例如四氟硼酸或氯化铝存在下,在-20℃和+50℃之间的温度下,使得到的式(Ⅸ)化合物与乙酰氯反应其中Q和R各自如上定义;C)在第三步中,如果适当在稀释剂例如二氯甲烷或四氯化碳存在下,在-10℃和+25℃之间的温度下,对得到的式(Ⅹ)的化合物进行氯化或溴化,其中Q和R各自如上定义;D)在第四步中,在稀释剂存在下,如果适当在与水的混合物例如乙醇/水中,和如果适当在相转移催化剂例如季铵盐存在下,在50℃和150℃之间的温度下,使得到的式(Ⅺ)化合物与甲酸盐例如甲酸钠反应,其中Q和R各自如上定义,和Hal代表氯或溴;E)在第五步中,在稀释剂例如醇或醚的存在下,和如果适当在碱例如乙酸钠存在下,在0℃和60℃之间的温度下,使得到的式(Ⅻ)的化合物与O-甲基羟基胺,如果适当,以盐的形式,例如盐酸盐反应其中Q和R各自如上定义;F)在第六步中,在酸例如三氟乙酸存在下,和如果适当在稀释剂例如四氢呋喃的存在下,在0℃和120℃之间的温度下,使得到的式(ⅩⅢ)的化合物与还原剂例如硼氢化钠反应,其中Q和R各自如上定义;G)在第七步中,如果适当在碱例如三乙胺存在下,和如果适当在稀释剂例如四氢呋喃的存在下,在0℃和100℃之间的温度下,使得到的式(ⅩⅣ)的化合物与式(ⅩⅤ)的苯甲酰氯反应,其中Q和R各自如上定义,其中A和B各自如上定义;H)在第八步中,如果适当在稀释剂例如甲苯的存在下,在20℃和100℃之间的温度下,使得到的式(ⅩⅥ)的化合物与氯化试剂例如亚硫酰氯反应,其中A,B,Q和R各自如上定义;Ⅰ)在第九步中,在碱例如氢氧化钠溶液存在下,如果适当在相转移催化剂例如铵化合物存在下,和如果适当在稀释剂例如二甲基甲酰胺的存在下,在0℃和100℃之间的温度下,使得到的式(ⅩⅦ)的化合物环化,得到本发明的式(Ⅰ)的化合物,其中A,B,Q和R各自如上定义。
式(ⅩⅦ)的化合物也可以通过在酸催化剂例如氢氟酸,三氟化硼,四氯化钛或氯化铝存在下和在稀释剂例如二氯甲烷或乙腈存在下,在0℃和80℃之间的温度下,使式(Ⅳ)的酰胺衍生物与式(Ⅸ)的化合物反应而直接获得。
式(Ⅷ)的起始物是已知的和/或通过已知的方法以简单的方式制备。
式(Ⅷ)的化合物是这样得到的:例如,通过磺化任选被取代的联苯,接着与碱金属氢氧化物反应,得到羟基联苯,或者通过将氨基联苯重氮化并煮沸(参见例如Houben-Weyl,第Ⅵ/Ⅰc卷,(1976),第216和251页)。
式(ⅩⅤ)的苯甲酰氯一般是有机化学公知的化合物。
本发明活性化合物具有好的作物安全性和低的哺乳动物毒性,适于防治动物害虫,特别是昆虫,蛛形纲和线虫,它们是在农业,林业,储藏品保护和材料保护以及卫生领域所遇到的。本发明化合物优选用作农作物保护剂并且对于一般敏感性和抗性物种是有活性的,并且在害虫发育的所有阶段或部分阶段有效。上述害虫包括:等足目(Isopoda),例如Oniscus aselluse,鼠妇(Armadillidiumvulgare)和Porcellio scaber。多足纲目(Diplopoda),例如Blaniulus gutttulatus。唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.)。综合纲目(Symphyla),例如Scutigerella immaculata。缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina)。弹尾目(Collembola),例如Onychiurus armatus。直翅目(Orthoptera),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),灶马(Acheta domesticus),蝼蛄属(Gryllotalpa spp.),热带飞蝗(Locusta migratoriamigratorioides),长额负蝗(Melanoplus differentialis)和Schistocerca gregaria。革翅目(Dermaptera),例如欧洲球螋(Forficula auricularia)。等翅目(Isoptera),例如白蚁属(Reticulitermes spp.)。虱目(Anoplura),例如头虱(Pediculus humanus corporis),盲虱属(Haematopinus spp.)和长额虱(Linognathus spp.)。食毛目(Mallophaga),例如羽虱属(Trichodectes spp.)和Damalinea spp.。缨翅目(Thysanoptera),例如温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thrips tabaci)。异翅亚目(Heteroptera),例如褐盾蝽属(Eurygasterspp.),Dysdercus intermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimex lectularius),Rhodnius prolixus和吸血猎蝽属(Triatoma spp.)。同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisiatabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphisgossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphis fabae),Aphis pomi,苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterus arundinis),Phylloxera vastatrix,Pemphigus spp.,Macrosiphum avenae,瘤额蚜(Myzus spp.),忽布瘤额蚜(Phorodon humuli),粟缢管蚜(Rhopasiphum padi),叶蝉属(Empoasca spp.),Euscelisbilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecanium corni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphax striatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiella aurantii),Aspidiotus hederae,粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。鳞翅目(Lepidoptera),例如,红铃虫(Pectinophora gossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletis blancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutella maculipennis),天幕毛虫(Malacosomaneustria),Euproctis chrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrix thurberiella),Phyllocnisticitrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Feltia spp.),埃及金刚钻(Earias insulana),夜蛾属(Heliothisspp.),甜菜夜蛾(Spodoptera exigua),甘蓝夜蛾(Mamestrabrassicae),Panolis flammea,斜纹夜蛾(Spodoptera litura),夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsa pomonella),粉蝶属(Pieris spp.),螟(Chilospp.),Pyrausta nubilalis,Ephestia kuehniella,大黄螟(Galleria mellonella),袋衣蛾(Tineola bisselliella),网衣蛾(Tinea pellionella),褐织叶蛾(Hofmannophilapseudospretella),Cacoecia podana,Capua reticulana,云杉卷叶蛾(Choristoneura fumiferana),葡萄果蠹蛾(Clysiaambiguella),茶黄卷叶蛾(Homona magnanima)和栎绿卷叶蛾(Tortrix yiridana)。鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,Bruchidius obtectus,大豆象(Acanthoscelides obtectus),家天牛(Hylotrupes bajulus),Agelastica alni,甲铃薯甲虫(Leptinotarsa decemiineata),Phaedon cochleariae,叶甲属(Diabrotica spp.),油菜兰跳甲(Psylliodes chrysocephala),墨西哥豆瓢虫(Epilachnavarivestis),Atomaria spp.,锯胸谷盗(Oryzaephilussurinamens),象甲属(Anthonomus spp.),米象属(sitophilusspp.),Otiorrhynchus sulcatus,香蕉蛛基象甲(Cosmopolitessordidus),Ceuthorrhynchus assimilis,苜宿叶象甲(Hyperaposttica),皮蠹属(Dermestes spp.),皮蠹属(Trogoderma spp.),皮蠹属(Anthrenus spp.),黑皮蠹(Attagenue spp.),粉蠹(Lyctusspp.),Meligethes aeneus,蛛甲属(Ptinus spp.),金黄蛛甲(Niptus hdoleucus),麦蛛甲(Gibbium psylliodes),拟谷稻属(Tribolium spp.),黄粉甲(Tenebrio molitor),扣甲属(Agriotesspp.),金针虫属(Conoderus spp.),Melolontha meiolontha,六月金龟子(Amphimallon solstitialis)和Costelytra zealandica.膜翅属(Hymenoptera),例如锯角叶蜂属(Diprion spp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomoriumpharaonis)和胡蜂(Vespa spp.)。双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anophelesspp.),库蚊(Culex spp.),黄猩猩果蝇(Drosophila melanogaster),家蝇(Musca spp.),厩蝇(Fannia spp.),红头丽蝇(Calliphoraerythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyia spp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,螫蝇属(Stomoxys spp.),鼻蝇属(oestrus spp.),皮蝇属(Hydodermaspp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinella frit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyia hyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacus oleae)和欧洲大蚊(Tipula paludosa)。蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis)和角叶蚤属(Ceratophyllus spp.)。蛛形纲(Arachnida),例如Sciopio maurus,黑寡妇球腹蛛(Latrodectus mactans)。蜱螨目(Acarina),例如,粗脚粉螨(Acarus siro),隐喙蚍(Argasspp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssusgallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilus spp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyomma spp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptesspp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.),和红叶螨属(Tetranychus spp.)。
寄生植物线虫包括,例如短体线虫属(Pratylenchus spp.),相似穿孔线虫(Radopholus similis),起绒草茎线虫(Ditylenchusdipsaci),半穿刺线虫(Tylenchulus semipenetrans),异皮线虫属(Heterodera spp.),球异皮线虫属(Globodera spp.),根结线虫属(Meloidogyne spp.),滑刃线虫属(Aphelenchoides spp.),长针线虫属(Longidorus spp.),剑线虫属(Xiphinema spp.),毛刺线虫属(Trichodorus spp.)。
本发明式(Ⅰ)化合物特别具有出色的杀昆虫和杀螨活性。
它们被用来特别有效地防治伤害植物的害虫,例如抗棉铃虫(Heliothis armigera)毛虫,抗辣根猿叶甲(Phaedon cochleariae)幼虫,小菜蛾(Plutella xylostella)毛虫,草地粘虫或甜菜夜蛾(Spodoptera frugiperda或exigua)毛虫,或者用于防治伤害植物的螨,例如杀苹果红蜘蛛(Panonychus ulmi)或棉红蜘蛛(Tetranychusurticae)。
活性化合物可以转变成常规制剂,例如溶液、乳液、可湿性粉末、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉末、颗粒剂、混悬乳油、浸有活性化合物的天然的和合成的材料和包裹在聚合物中的细微胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与扩充剂即液体溶剂和/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/或起泡剂。
用水作扩充剂的情况下,也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂肪烃,如环己烷或石蜡,例如矿物油馏份,矿物油和植物油,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亚砜,以及水。
合适的固体载体是:
例如铵盐和磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的适合的固体载体有:例如压碎和破碎的天然矿物质如方解石、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:例如锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂有: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,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如,木素亚硫酸废液和甲基纤维素。
制剂中,可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如***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。可能的其它的添加剂是矿物油和植物油。
也可以使用染料,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。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
本发明活性化合物可以以其商售制剂存在以及由这些制剂制备的使用形式存在,作为与其它活性化合物例如杀虫剂、引诱剂、消毒剂、杀菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂的混合物。杀虫剂包括例如磷酸酯类,氨基甲酸酯类,羧酸酯类,氯代烃,苯基脲和通过微生物制备的物质。
特别有利的混合物成分的例子如下:
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)甲酰苯胺;(E)-2-甲氧基亚胺基-N-甲基-2-(2-苯氧基苯基)-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)-甲氧基亚氨基[α-(邻-甲苯基氧基)-邻-甲苯基]乙酸甲酯;2-苯基苯酚(OPP),aldimorph,氨丙磷酸,敌菌灵,戊环唑,
苯霜灵,邻碘酰苯胺,苯菌灵,乐杀螨,联苯,双苯***醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌消,乙菌利,代森锰,霜尿氰,环唑醇,酯菌胺,
双氯酚,苄氯***醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇,二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,多果定,氨噁唑酮,
克瘟散,epoxyconazole,乙嘧酚,土菌灵
氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,fludioxonil,氟氯菌核利,fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋霜灵,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双瓣醋酸盐,异稻瘟净(IBP),异菌脲,稻瘟灵,
春雷霉素,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,噻菌胺,腈菌唑,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,氧化萎锈灵,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,环丙唑,丙森锌,吡嘧磷,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,氟嘧唑,噻菌灵,噻菌腈,甲基硫菌灵,福美双,甲基立枯磷,甲基氟磺胺,***酮,***醇,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
稻纹散,乙烯菌核利,
代森锌,福美锌。
杀细菌剂:
bronopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,AC303630,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双虫脒,阿凡曼菌素,AZ60541,azadirachtin,azinphos-A,保棉磷,***锡,
苏云金杆菌,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,CGAl57419,CGAl84699,chloethocarb,chlorethoxyfos,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,顺式-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,酚线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,甲基毒虫畏,敌噁磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,氯氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,吡氟禾草灵,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,
HCH,庚烯磷,氟铃脲,噻螨酮,
吡虫啉,异稻瘟净,氯唑磷,异丙胺磷,叶蝉散,噁唑磷,异阿凡曼菌素,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,moxidectin,
二溴磷,NCl84,NI25,nitenpyram,
氧乐果,杀线威,亚砜吸磷,异砜磷,
对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,甲基嘧啶磷,嘧啶磷-A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,pyradaphenthion,pyresmethrin,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,
喹硫磷,
RH5292,
蔬果磷,sebufos,silafluofen,治螟硫磷,甲丙硫磷,
tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效磷,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,***磷,triazuron,敌百虫,杀虫隆,混灭威,
芽灭多,XMC,灭杀威,YI5301/5302,zetamethrin。
也可以是与其它已知活性化合物例如除草剂,或者与化肥和生长调节剂的混合物。
本发明活性化合物还可以以其商售制剂存在和以由这些制剂制备的作为与增效剂的混合物的使用形式存在。增效剂是提高活性化合物作用而加入的,增效剂自身不必是活性的化合物。
由商售制剂制备的使用形式的活性化合物含量可以在宽范围内变化。使用形式活性化合物的浓度是0.0000001-95%(重量)活性化合物,优选0.0001-1%(重量)。
以适于这些使用形式的常规方式应用这些化合物。
当用来杀卫生领域害虫和储存产品害虫时,这些活性化合物的对木材和粘土具有极好的有后效的作用,以及对用石灰处理过的物质上的碱的好的稳定性。
本发明活性化合物不仅对杀植物,卫生领域和储存产品害虫有活性,而且还用于兽药领域,杀动物寄生虫(外寄生虫),例如硬蜱,软蜱,马痒螨,恙螨,蝇(叮和吮),寄生蝇幼虫,虱,头虱,鸟虱和蚤。这样的寄生虫包括:
虱目(Anolpurida),例如,血虱属(Haematopinus spp.),长颚虱(Linognathus spp.),虱属(Pediculus spp.),阴虱属(Phtirusspp.),管虱属(Solenopotes spp.)。
食毛目咬虱(Mallophagida)和Amblycerina及Ischnoeerina亚目,例如毛羽虱属(Trimenopon spp.),Menopon spp.,巨羽虱属(Trinoton spp.),牛羽虱属(Bovicola spp.),Werneckiella spp.,Lepikentron spp.,Damalina spp.,Trichodectes spp.,Felcolaspp.。
双翅目(Diptera)和长角亚目(Nematocerina)和Braehycerina亚目,例如伊蚊(Aedes spp.),斑按蚊属(Anopheles spp.),库蚊(Culex spp.),蚋属(Simulium spp.),全毛真蚋(Eusimulium spp.),白蛉(Phlebotomus spp.),罗蛉属(Lutzomyia spp.),库蠓(Culicoides spp.),斑虻(Chrysops spp.),瘤虻(Hybomitra spp),Atylotus spp.,虻属(Tabanus spp.),麻虻属(Haematopotaspp.),Philipomyia spp.,Braula spp.,Musca spp.,齿股蝇属(Hydrotuea spp.),螫蝇(Stomoxys spp.),Haematobia spp.,Morellia spp.,厕蝇(Fannia spp.),Glossina spp.,Calliphoraspp.,Lucilia spp.,Chrysomyia spp.,Wohlfahrtia spp.,别麻蝇(Sarcophaga spp.),Oestrus spp.,皮蝇(Hypoderma spp.),Gasterophilus spp.,虱蝇(Hippobosca spp.),Lipoptena spp.,和Melophagus spp.。
蚤目(Siphonapterida),例如,蚤属(Pulex spp.),Ctenocephalides spp.,鼠蚤(Xenopsylla spp.),和角叶蚤(Ceratophyllus spp.)。
异翅亚目(Heteropterida),例如,臭虫属(Cimex spp.),吸血猎蝽属(Triatoma spp.),Rhodnius spp.,和全圆蝽属(Panstrongylusspp.)。
非蠊目(Blattarida),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),德国小蠊(Blattela germanica),非蠊属(Supella spp.)。
螨(Acarida)亚类,和后胸气门目(Metastigmata)和中胸气门目(Mesostigmata),例如,隐喙蜱属(Argas spp.),喙蜱属(Ornithodorus spp.),耳残喙蜱(Otabius spp.),硬蜱(Ixodesspp.),花蜱属(Amblyomma spp.),牛蜱属(Boophilus spp.),矩头蜱(Dermacentor spp.),Haemophysalis spp.,璃眼蜱(Hyalommaspp.),头蜱属(Rhipicephalus spp.),鸡皮剌螨(Dermanyssusspp.),瑞立绦虫(Raillietia spp.),Pneumonyssus spp.,Sternostoma spp.,和Varroa spp.。
Actinedida(恙螨亚目,Prostigmata)和Acaridida(Astigmata),例如Acarapis spp.,姬螯螨属(Cheyletiella spp.),Ornithocheyletia spp.,Myobia spp.,疥螨(Psorergates spp.),蠕形螨(Demodex spp.),恙螨(Trombicula spp.),Listrophorusspp.,粗脚粉螨(Acarus spp.),酪螨(Tyrophagus spp.),嗜木螨(Caloglyphus spp.),Hypodectes spp.,翼衣螨属(Pterolichusspp.),恙螨(Psoroptes spp.),恙螨(Chorioptes spp.),Octodectes spp.,疥螨(Sarcoptes spp.),Notoedres spp.,足螨(Knemidocoptes spp.,),Cytodites spp.,和Laminosioptesspp.。
本发明式(Ⅰ)活性化合物也适于杀死侵染农业生产家畜的节肢动物门,所述家畜是例如牛,绵羊,山羊,马,猪,驴,骆驼,水牛,兔子,鸡,火鸡,鸭,鹅,蜜蜂,其它宠物,例如狗,猫,笼养的鸟和鱼缸养殖鱼,和称之为实验室动物的动物,例如仓鼠,豚鼠,大鼠和小鼠。通过杀死这些节肢动物门,可以避免家畜死亡并且避免产品量的减少(产品例如肉,奶,羊毛,皮革,蛋,蜂蜜等),因此通过使用本发明活性化合物可以实现更经济更简单的动物的喂养。
在兽药领域,本发明活性化合物以已知方式通过肠给药,例如以片剂,胶囊,顿服水剂,顿服药,颗粒剂,糊剂,巨丸剂,通过进食方法和栓剂的形式;通过肠胃外给药,例如通过注射(肌内,皮下,静脉内,腹膜内等),埋入,通过鼻给药,通过以例如浸渍或浸浴,喷洒,倒施和点施,洗用和撒粉的形式皮肤使用,也可以借助于含有活性化合物的用模子做的物品,例如颈圈,耳饰,尾饰,腿带,笼头,标记物等而使用。
当对牲畜,家禽,宠物等使用时,本发明式(Ⅰ)的活性化合物可以作为以1-80%重量的量含有活性化合物的制剂(例如粉末剂,乳剂,可流动性组合物)而被使用,直接使用或者稀释100-10000倍后使用,或者可以用化学浴形式。
另外,还发现本发明式(Ⅰ)的化合物还具有强的杀破坏工业物质的昆虫的作用。
作为优选例子可以提到下面的昆虫,但是不受此限制:
甲虫,例如
家天牛(Hylotrupes bajulus),Chlprophorus pilosis,家具窃蠹(Anobinm punctatum),Xestobium rufovillosum,Ptilinuspecticornis,Dendrobium pertinex,Ernobius mollis,Priobiumcarpini,欧洲竹粉蠹(Lyctus brunneus),Lyctus africanus,平颈粉蠹(Lyctus planicollis),Lyctus linearis,Lyctuspubescens,Trogoxylon aequale,Minthes rugicollis,小蠹虫种(Xyleborus spec.),Tryptodendron spec.,Apate monachus,Bostrychus capucins,Heterobostrychus branneus,Simoxylonspec.,和竹长蠹(Dinoderus minutus)。
膜翅目(Dermapterans),例如
钢青小树蜂(Sirex juvencus),枞大树蜂(Urocerus gigas),Urocerus gigas taignus和Urocerus augur。
白蚁,例如
Kalotermes flavicollis,Cryptotermes brevis,Heterotermes indicola,Reticulitermes flavipes,Reticulitermes santonensis,Reticulitermes lucifugus,澳洲白蚁(Mastotermes darwiniensis),Zootermopsis nevadensis和台湾家白蚁(Coptotermes formosanus)。
Bristle-tail,例如西洋衣鱼(Lepisma saccharina)。
本说明书中所涉及的工业材料理解为非生命材料,例如,优选合成材料,粘合剂,胶料,纸和纸板,皮革,木材和木材加工产品以及涂料。
要非常特别地保护使之不受昆虫侵染的材料是木材和木材加工产品。
可以用本发明成分或含有这样一种成分的混合物保护的木材和木材加工产品理解为是,例如建筑木材加工品,木梁,铁轨枕木,建桥木料,码头,木制运载工具,箱子,制模板,容器,电线杆,木桶,木窗,木门,胶合板,颗粒板,接合物,或者在房屋建筑或细木工行业很普通使用的木产品。
本发明活性化合物可以以本身,以乳油形式或者一般的常规制剂使用,例如粉末剂,颗粒剂,溶液,混悬剂,乳剂或糊剂。
提到的制剂可以以本身已知的方法制备,例如通过混合活性化合物和至少一种溶剂或稀释剂,乳化剂,悬浮剂和/或粘合剂或固定剂,水驱避剂,如果合适,干燥剂和UV稳定剂和,如果合适,着色剂和颜料和其它加工助剂。
用于保护木料和木制品的杀虫剂组合物或乳油以0.0001-95%(重量)浓度含有本发明活性化合物,特别是0.001-60%(重量)。
使用的试剂或乳油的量取决于害虫的物种和发生情况,并取决于基质。施用的最佳比例每种情况下可以通过试验系列来决定。但是,一般情况下,使用以要保护的材料为基础的0.0001-20%(重量),优选0.001-10%(重量)的活性化合物足够了。
使用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或油或油型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/或水和,如果合适,乳化剂和/或湿润剂。
优选使用的有机化学溶剂是具有大于35的挥发数和高于30℃,优选高于45℃的闪点的油或油型溶剂。用作具有低挥发性并且在水中不溶解的这类油和油型溶剂的物质是合适的矿物油或其芳香烃级分,或者含有矿物油的溶剂混合物,优选石油溶剂,石油和/或烷基苯。
有利地使用的物质是沸点范围是170-220℃的矿物油,沸点范围是170-220℃的石油溶剂,沸点范围是250-350℃的锭子油,沸点范围是160-280℃的石油或芳香烃,松节油等。
在优选的实施方案中,使用沸点范围是180-210℃的液体脂肪烃或者沸点范围是180-220℃的芳香烃和脂肪烃的高沸点混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
具有大于35的挥发数和高于30℃、优选高于45℃闪点的低挥发性有机油或油型溶剂可以部分替换成高挥发性或中等挥发性的有机化学溶剂,前提是该溶剂混合物也具有大于35的挥发数和高于30℃、优选高于45℃的闪点,并且杀虫剂/杀真菌剂混合物在该溶剂混合物中是可溶解的或可乳化的。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物替换成脂肪族极性有机化学溶剂或溶剂混合物。优选使用的物质是具有羟基和/或酯基和/或醚基的脂肪族有机化学溶剂,例如乙二醇醚,酯等。
本发明范围内使用的有机化学粘合剂是本身已知的合成树脂和/或粘合干燥油,并且可以用水稀释和/或在使用的有机化学溶剂中是可溶解的或可分散的或可乳化的,特别是粘合剂由下面的物质组成或者含有下面的物质:丙烯酸树脂,乙烯树脂,例如聚乙酸乙烯酯,聚酯树脂,缩聚物或加聚物树脂,聚尿烷树脂,醇酸树脂或改性的醇酸树脂,苯酚树脂,烃类树脂,例如茚/苯并呋喃树脂,有机硅树脂,干燥植物油和/或干燥油和/或以天然和/或合成树脂为基础的物理干燥粘合剂。
作为粘合剂使用的合成树脂可以以乳液,分散液或溶液的形式使用。最多10%重量的沥青或沥青状物质也可以作为粘合剂使用。另外,可以使用本身已知的着色剂,颜料,水驱避剂,气味掩蔽物质和抑制剂或防腐蚀剂等。
根据本发明,组合物或乳油优选含有至少一种醇酸树脂或改性的醇酸树脂和/或干燥植物油作为有机化学粘合剂。根据本发明,优选使用的物质是油含量大于45%(重量),优选50-68%(重量)的醇酸树脂。
上面提到的粘合剂的所有或部分粘合剂可以替换成固定剂(混合物)或增塑剂(混合物)。这些添加剂是为了防止活性化合物的挥发和结晶或沉淀。优选替换0.01-30%的粘合剂(以使用的100%粘合剂为基础)。
增塑剂来自邻苯二甲酸酯类,例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,例如磷酸三丁酯,己二酸酯,例如己二酸二-(2-乙基己基)酯,硬脂酸酯,例如硬脂酸丁酯或硬脂酸戊酯,油酸酯,例如油酸丁酯,甘油醚或较高分子量的乙二醇醚,甘油酯和对甲苯磺酸酯。
固定剂的化学基础是聚乙烯基烷基醚,例如,聚乙烯基甲基醚,或酮类,例如二苯酮或亚乙基二苯酮。
作为溶剂或稀释剂特别合适的是水,如果合适,以与一种或几种上述有机化学溶剂或稀释剂,乳化剂和分散剂的混合物存在。
特别有效的木材保护作用是通过大规模的工业化浸渍方法实现的,例如真空,双倍真空或加压方法。
如果合适,即用型组合物可以另外含有一种或多种其它的杀昆虫剂和,如果合适,另外一种或几种杀真菌剂。
可以混合的合适的附加成分优选是WO94/29268中提到的杀昆虫剂和杀真菌剂。该文献中提到的化合物明确地引入本申请作为参考。
可以混合的非常特别优选的成分是杀昆虫剂,例如毒死稗,辛硫磷,silafluofin,甲体氯氰菊酯,氟氯氰菊酯,氯氰菊酯,溴氰菊酯,氯菊酯,吡虫啉,NI-25,氟虫脲,氟铃脲和杀虫隆,和杀真菌剂,例如epoxyconazole,己唑醇,戊环唑,环丙唑,戊唑醇,环唑醇,metconazole,抑霉唑,苯氟磺胺,甲苯氟磺胺,氨基甲酸3-碘代-2-丙炔基丁酯,N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明活性化合物的制备和应用可以从下面的实施例说明。制备实施例
70.2g(0.2mol)2-(2,6-二氟苯基)-4-(4’-羟基联苯-4-基)-1,3-噁唑啉和30.4g(0.22mol)碳酸钾悬浮于700ml乙腈中并且与0.1ml三(3,6-二氧杂庚基)胺(TDA)混合。然后回流下滴加42.8g(0.22mol)4-三氟甲基苄基氯,反应混合物在该温度下搅拌14小时。接着通过蒸馏出溶剂而浓缩混合物,并且残余物溶解于1L二氯甲烷中,用水洗涤,硫酸钠干燥并浓缩。得到82.7g(理论量的81%)2-(2,6-二氟苯基)-4-[(4’-(4”-三氟甲基苄基氧基)-联苯-4-基)-1,3-噁唑啉,熔点166℃。起始物的制备
10.9g(0.026mol)2-(2,6-二氟苯基)-4-(4’-乙氧基羰基氧基联苯-4-基)-1,3-噁唑啉悬浮于50ml甲醇中,然后在室温下滴加35.4ml(0.52mol)25%强度的氨水。室温下28小时后,吸滤过滤出沉淀并用少量甲醇洗涤。产率7.6g(理论量的97.4%),mp.180-182℃
5℃下,向120ml二甲基甲酰胺中的19.8g(0.043mol)2-(2,6-二氟苯甲酰基酰胺基)-2-(4’-乙氧基羰基氧基联苯-4-基)-1-氯乙烷中滴加4ml(0.045mol)50%强度氢氧化钠水溶液。室温下2小时后,搅拌下将混合物倒入500ml冰水中,并且吸滤出沉淀的结晶。产率:15.1g(理论量的83%)mp.:98-100℃
5℃下,经30分钟,向200ml二氯甲烷中的53g(0.213mol)2-(2,6-二氟苯甲酰基酰胺基)-2-甲氧基-1-氯乙烷,48.4g(0.2mol)4-乙氧基羰基氧基联苯和12ml冰醋酸的混合物中分批加入130.4g(0.98mol)的氯化铝。反应混合物的颜色变蓝,然后变成红紫色。反应混合物在5℃下搅拌1小时,和在10℃搅拌1小时,然后小心倒入冰中,从悬浮液中小心倾析出水,并使用旋转蒸发器浓缩。残余物与50ml乙腈混合,并吸滤出沉淀的结晶。产率42.8g(理论量的47%),mp.209℃。
通过实施例1的方法并且根据一般制备方法,获得下面表2中列出的式(Ⅰ)的化合物:表2实施例 A B Q R Mp(℃)或logP1)序号2 Cl H H
135-373 F Cl H -CH2-C(CH3)=N-O-CH(CH3)C2H5 5.90(A异构体)*5.81(B异构体)*4 F Cl H -C(CH3)2-C(CH3)=N-O-C3H7-i 6.305 Br H H -C3H7-i 95-976 F F H -CO-NH-C3H7-i 126-307 F F H -CF=CF-CH=CH2 5.018 F F H -CH2-CH=NOCH3 3.97(A异构体)*4.14(B异构体)*9 H Cl H -C3H7-n 80-8510 H Cl H
165-7011 H Cl H -C3H7-i 8012 H Cl H -C4H9-n 80-8413 H Cl H
112-1414 H Cl H -CH2-C3H7-i 87-9515 F F H -CH2CH2-CH=CF2 8316 F F H -CH2-CH=NOC2H5 4.35(A异构体)*4.53(B异构体)*表2(续)实施例 A B Q R Mp(℃)或logP1)序号17 F F H
158-6218 F F H
115-1819 F F H
155-5620 F F H
124-2621 F F H
154-5622 I H H
5.4323 F F H
86-9524 F F H
130-3525 F F H
135-3626 F F H
120-2227 F Cl H -C3H7-i 108-1028 F F -
125-2629 F Cl H -C3H7-n 130-32表2(续)实施例 A B Q R Mp(℃)或logP1)序号30 F Cl H -CH2-C3H7-i 12231 F F H
16532 F F H
88-9033 F F H
11834 F Cl H -C4H9-n 95-10535 F F H -CH(CH3)-CH=NOCH336 F F H -CH(CH3)-C≡CH 4.1537 Cl H H -CH(CH3)-C≡CH 4.4938 Cl F H
99-10239 Cl H H -CH2-C3H7-i 72-7540 Cl Cl H
193-9441 Cl Cl H -C3H7-i 122-2342 F F H
6.48(A异构体)*6.37(B异构体)*43 F F Cl
5.99(A异构体)*5.85(B异构体)*44 F F Cl
3.95(A异构体)*3.89(B异构体)*表2(续)实施例 A B Q R Mp(℃)或logP1)序号45 Cl H Cl
4.33(A异构体)*4.26(B异构体)*46 F F H
6.0047 F Cl H
6.24(A异构体)*6.10(B异构体)*48 F Cl H
6.27(A异构体)*6.13(B异构体)*49 F Cl H
6.23(A异构体)*6.09(B异构体)*50 F F H
5.99(A异构体)*5.84(B异构体)*51 F F H
5.93(A异构体)*5.79(B异构体)*52 F F H
5.94(A异构体)*5.80(B异构体)*53 F F H -C(CH3)2-CH=NOC2H5 5.0054 F Cl H
5.85(A异构体)*5.76(B异构体)*55 F F H
5.58(A异构体)*5.51(B异构体)*56 F F H
5.61(A异构体)*5.54(B异构体)*57 F F H -C(CH3)2-CH=NOCH3 4.6258 Cl H H
6.44表2(续)实施例 A B Q R Mp(℃)或序号 logP1)59 F F H
6.4360 F F H
6.3861 Cl H Cl
6.84(A异构体)*6.67(B异构体)*62 Cl H Cl
6.89(A异构体)*6.71(B异构体)*63 F F Cl
6.37(A异构体)*6.22(B异构体)*64 F F Cl
6.41(A异构体)*6.26(B异构体)*65 Cl Cl H -CH(CH3)-COCH3 108-1066 Cl Cl H
5.27(A异构体)*5.17(B异构体)*67 Cl Cl H
5.69(A异构体)*5.57(B异构体)*68 Br H H -CH(CH3)-COCH3 4.1369 Cl H H CF3 58-6070 CH3O- H H CF3 50-5471 CF3 H H CF3 63-6572 CH3SO2-H H CF3 128-3273 C2H5O- H H CF3 6874 i-C3H7O-H H CF3 8475 NO2 H H CF3 75-7776 CH3O- F H CF3 4.49表2(续)实施例 A B Q R Mp(℃)或序号 logP1)77 F NH2 H CF3 93-9578 CH3S- H H CF3 126-2779 i-C3H7S- H H CF3 98-10280 C2H5S- H H CF3 8881 C2H5O- F H CF3 98-10082 2H5CH(CH3)O- F H CF3 5.4783 2H5CH(CH3)O- C2H5CH(CH3)O- H CF3 92-9384 i-C3H7CH2O- F H CF3 5.5785 i-C3H7CH2O- i-C3H7CH2O- H CF3 93-9586 C2H5 H H CF3 5.7887
H H CF3 5.4788 CH3O H H C3H7-i 5089 Br H H CF3 52-5490 I H H CF3 80-82表2(续)实施例 A B Q R Mp(℃)或logP1)序号91 Br H H -CH(CH3)-CH(OH)CH3 3.7492 Br H H -CH(CH3)-C(CH3)=NOCH3 5.08(A异构体)*5.18(B异构体)*93 I H H C3H7-i 88-9094 I H H
172-7595 Br H H -CH2-CH=CH2 76-7996 Br H H -CH2-C≡CH97 F H Cl
4.3298 F H Cl
155-5799 F Cl H
165-67100 F H H -CH(CH3)-COCH3 3.79101 F H H
4.57102 F F H -C(CH3)2-CHO 4.08103 F H Cl
4.91表2(续)实施例 A B Q R Mp(℃)或logP1)序号104 F Cl H
5.52105 F H Cl
5.15106 F H Cl
5.57107 F H H -C3H7-i 4.65108 F H H -CH2-C3H7-i 5.34109 F H H
5.65110 F H H
4.94111 F H H
5.24112 F Cl H -CH2-CH=NOCH3 4.27113 F Cl H -CH2-CH=NOC2H5 4.65114 F F Cl -CH2-CH=NOCH3 4.33115 F F Cl -CH2-CH=NOC2H5 4.71116 Cl H Cl -CH2-CH=NOCH3 4.72表2(续)实施例 A B Q R Mp(℃)或序号 logP1)117 Cl H Cl -CH2-CH=NOC2H5 5.08118 F H Cl -CH2CF3 115119 F F CH3 -CH2CF3 4.80120 CF3CH2O- F CH3 -CH2CF3 4.91121 Cl H -CH2CH=CH2 -CH2CF3 84122 Cl H CH3 -CH2CF3 55-87123 F F C2H5 -CH2CF3 88-90124 Cl H H -CH2CF3 62-66125 F F H
5.68126 F F H -CH2-CF2-CHF2127 F F H -(CH2)3-CF2-CF3 1)logP:正辛醇/水的分配系数的以10为底的对数,通过反相HPLC分析使用水/乙腈测定*)A和B异构体:可能的几何异构体
通过实施例1的方法(参见起始物的制备)并且根据一般制备方法,获得下面化合物(Ⅱ-Ⅰ):Mp.:178-180℃。应用实施例在下面的应用实施例中使用EP-A0432661中已知的式(A)和(B)的化合物为对比物:
实施例A棉铃虫(Heliothis armigera)试验溶剂: 7份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理大豆苗(橹豆(Glycine max)),并在叶子还湿润的时候用棉铃虫(Heliothisarmigera)毛虫侵染。
一定时间后,测定以%表示的活性。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
在该项试验中,在举例的0.00016%活性化合物浓度下和在各种情况下6天后,例如制备实施例1和3的化合物表现出100%杀死率,制备实施例2的化合物为65%杀死率,而已知化合物(A)只有10%杀死率。实施例B全爪螨(Panonychus)试验(抗性)溶剂: 3份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
用期望浓度的活性化合物制剂喷雾被所有生长期苹果红蜘蛛(Panonychus ulmi)严重侵染的高大约30cm的李树(洋李(Prunusdomestica))。
一定时间后,测定以%表示的活性。100%表示所有的蜘蛛螨都已经被杀死;0%表示没有杀死一只蜘蛛螨。
在该项试验中,在举例的0.00016%活性化合物浓度下和在各种情况下14天后,例如制备实施例1的化合物引起95%杀死率,而已知化合物(A)只有50%杀死率。
实施例C猿叶甲(Phaedon)幼虫试验溶剂: 7份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用辣根猿叶甲(Phaedon cochleariae)幼虫侵染。
一定时间后,测定以%表示的杀伤率。100%表示所有的甲虫幼虫都已经被杀死;0%表示没有杀死一只甲虫幼虫。
在该项试验中,例如a)制备实施例4的化合物在举例的0.00001%活性化合物浓度时,在各种情况下7天后,引起100%杀死率,而已知化合物(A)只有55%杀死率。b)制备实施例1,2和3的化合物在举例的0.01%活性化合物浓度时,在各种情况下7天后,引起100%杀死率,而已知化合物(B)没有表现出活性。
实施例D菜蛾(Plutella)试验溶剂: 7份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用小菜蛾(Plutellaxylostella)毛虫侵染。
一定时间后,测定以%表示的活性。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
在该项试验中,在举例的0.000032%的活性化合物浓度下和各种情况下7天后,例如制备实施例1和3的化合物分别引起85%和100%杀死率,而已知化合物(B)没有表现出活性。实施例E甜菜夜蛾(Spodoptera exigua)试验溶剂: 7份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用甜菜夜蛾(Spodoptera exigua)毛虫侵染。
一定时间后,测定以%表示的杀伤率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
在该项试验中,在举例的0.000032%的活性化合物浓度下和各种情况下6天后,例如制备实施例1和2的化合物分别引起80%的杀死率,而已知化合物(A)没有表现出活性。
实施例F草地粘虫(Spodoptera frugiperda)试验溶剂: 7份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用草地粘虫(Spodoptera frugiperda)毛虫侵染。
一定时间后,测定以%表示的活性。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
在该项试验中,在举例的0.0001%的活性化合物浓度下和各种情况下7天后,例如制备实施例1,2,3和4的化合物引起100%的杀死率,而已知化合物(B)没有表现出活性和已知化合物(A)只有30%的杀死率。
实施例G红叶螨(Tetranychus)试验(OP抗性/喷雾处理)溶剂: 3份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
用期望浓度的活性化合物制剂喷雾所有发育期的棉红蜘蛛(Tetranychus urticae)严重侵染的大豆植株(菜豆(Phaseolusvulgaris))。
一定时间后,测定以%表示的活性。100%表示所有的蜘蛛螨都已经被杀死;0%表示没有杀死一只蜘蛛螨。
在该项试验中,在举例的0.000032%活性化合物浓度时,在各种情况下14天后,例如制备实施例1的化合物引起98%的杀死率,而已知化合物(A)只有50%杀死率。
实施例H蟑螂(Cockroach)试验试验动物:美洲大蠊(Periplaneta americana)溶剂:二甲亚砜
20mg活性化合物溶解于1ml二甲亚砜,通过用蒸馏水稀释来制备较低浓度。
将4只动物浸入要试验的活性化合物制剂中1分钟,将动物转移到塑料杯中并在适应气候化房间放置7天,然后测定杀死率。
100%表示所有的蟑螂都已经被杀死;0%表示没有杀死一只蟑螂。
在该项试验中,在举例的100ppm活性化合物浓度下,例如制备实施例2的化合物引起100%杀死率。
实施例Ⅰ丽蝇(blow fly)幼虫试验/抑制发育作用试验动物:丝光绿蝇(Lucilia cuprina)幼虫溶剂:二甲亚砜
20mg活性化合物溶解于1ml二甲亚砜,通过用蒸馏水稀释来制备较低浓度。
大约20只丝光绿蝇(Lucilia cuprina)幼虫放到装有约1cm3马肉和0.5ml要试验的活性化合物制剂的试管中,24小时和48小时后测定活性化合物制剂的活性。将试管转移到烧杯中,烧杯底部覆盖沙,又2天后取出试管并计数蛹。
以未处理对照物发育期的1.5倍后孵化的蝇的数目判断活性化合物制剂的活性。
100%表示没有蝇孵化;0%表示所有的蝇正常孵化。
在该项试验中,在举例的100ppm活性化合物浓度下,例如制备实施例2和5的化合物各自具有100%活性。
Claims (13)
其中基团A,B,Q和R各自在下面的表1中定义:表1化合物序号 A B Q R1 F F H
2 Cl H H
3 F Cl H -CH2-C(CH3)=N-O-CH(CH3)C2H54 F Cl H -C(CH3)2-C(CH3)=N-O-C3H7-i5 Br H H -C3H7-i6 F F H -CO-NH-C3H7-i7 F F H -CF=CF-CH=CH28 F F H -CH2-CH=NOCH39 H Cl H -C3H7-n10 H Cl H
11 H Cl H -C3H7-i表1(续)化合物序号 A B Q R12 H Cl H -C4H9-n13 H Cl H
14 H Cl H -CH2-C3H7-i15 F F H -CH2CH2-CH=CF216 F F H -CH2-CH=NOC2H517 F F H
18 F F H
19 F F H
20 F F H
21 F F H
22 I H H
23 F F H
24 F F H
25 F F H
26 F F H
表1(续)化合物序号 A B Q R27 F Cl H -C3H7-i28 F F H
29 F Cl H -C3H7-n30 F Cl H -CH2-C3H7-i31 F F H
32 F F H
33 F F H
34 F Cl H -C4H9-n35 F F H -CH(CH3)-CH=NOCH336 F F H -CH(CH3)-C≡CH37 Cl H H -CH(CH3)-C≡CH38 Cl F H
39 Cl H H -CH2-C3H7-i40 Cl Cl H
41 Cl Cl H -C3H7-i42 F F H
表1(续)化合物序号 A B Q R43 F F Cl
44 F F Cl
45 Cl H Cl
46 F F H
47 F Cl H
48 F Cl H
49 F Cl H
50 F F H
51 F F H
52 F F H
53 F F H -C(CH3)2-CH=NOC2H554 F Cl H
55 F F H
56 F F H
表1(续)化合物序号 A B Q R57 F F H -C(CH3)2-CH=NOCH358 Cl H H
59 F F H
60 F F H
61 Cl H Cl
62 Cl H Cl
63 F F Cl
64 F F Cl
65 Cl Cl H -CH(CH3)-COCH366 Cl Cl H
67 Cl Cl H
68 Br H H -CH(CH3)-COCH369 Cl H H CF370 CH3O- H H CF371 CF3 H H CF372 CH3SO2- H H CF373 C2H5O- H H CF3表1(续)化合物序号 A B Q R74 i-C3H7O- H H CF375 NO2 H H CF376 CH3O- F H CF377 F NH2 H CF378 CH3S- H H CF379 i-C3H7S- H H CF380 C2H5S- H H CF38l C2H5O- F H CF382 C2H5CH(CH3)O- F H CF383 C2H5CH(CH3)O- C2H5CH(CH3)O- H CF384 i-C3H7CH2O- F H CF385 i-C3H7CH2O- i-C3H7CH2O- H CF386 C2H5 H H CF387
H H CF388 CH3O H H C3H7-i89 Br H H CF390 I H H CF391 Br H H -CH(CH3)-CH(OH)CH392 Br H H -CH(CH3)-C(CH3)=NOCH393 I H H C3H7-i表1(续)化合物序号 A B Q R94 I H H
95 Br H H -CH2-CH=CH296 Br H H -CH2-C≡CH97 F H Cl
98 F H Cl
99 F Cl H
100 F H H -CH(CH3)-COCH3101 F H H
102 F F H -C(CH3)2-CHO103 F H Cl
104 F Cl H
表1(续)化合物序号 A B Q R105 F H Cl
106 F H Cl
107 F H H -C3H7-i108 F H H -CH2-C3H7-i109 F H H
110 F H H
111 F H H
112 F Cl H -CH2-CH=NOCH3113 F Cl H -CH2-CH=NOC2H5114 F F Cl -CH2-CH=NOCH3115 F F Cl -CH2-CH=NOC2H5116 Cl H C1 -CH2-CH=NOCH3117 Cl H Cl -CH2-CH=NOC2H5118 F H Cl -CH2CF3119 F F CH3 -CH2CF3120 CF3CH2O- F CH3 -CH2CF3表1(续)化合物序号 A B Q R121 Cl H -CH2-CH=CH2 -CH2CF3122 Cl H CH3 -CH2CF3123 F F C2H5 CH2CF3124 Cl H H -CH2CF3125 F F H
126 F F H -CH2-CF2-CHF2127 F F H -(CH2)3-CF2-CF3。
3.下式的化合物
5.下式的化合物
9.农药,特征在于,其含有至少一种权利要求1的式(Ⅰ)的化合物。
10.权利要求1的式(Ⅰ)的化合物防治害虫的用途。
11.防治害虫的方法,特征在于,将权利要求1的式(Ⅰ)的化合物施用于害虫和/或其栖生地。
12.制备农药的方法,特征在于,将权利要求1的式(Ⅰ)的化合物与扩充剂和/或表面活性剂混合。
13.权利要求1的式(Ⅰ)的化合物制备农药的用途。
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DE19717228.8 | 1997-04-24 | ||
DE19717228A DE19717228A1 (de) | 1997-04-24 | 1997-04-24 | Substituierte Oxazolin-Derivate |
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CN1309650A true CN1309650A (zh) | 2001-08-22 |
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EP (1) | EP0980361A1 (zh) |
JP (1) | JP2001521535A (zh) |
KR (1) | KR20010006197A (zh) |
CN (1) | CN1309650A (zh) |
AU (1) | AU727621B2 (zh) |
BR (1) | BR9809413A (zh) |
DE (1) | DE19717228A1 (zh) |
TW (1) | TW526197B (zh) |
WO (1) | WO1998047881A1 (zh) |
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BR0009357A (pt) * | 1999-03-26 | 2002-03-05 | Novartis Ag | Preparação e utilização de enanciÈmeros puros das oxazolinas 2,4-dissubstituìdas |
TWI275589B (en) | 2000-06-22 | 2007-03-11 | Dow Agrosciences Llc | 2-(3,5-disubstituted-4-pyridyl)-4-(thienyl, thiazolyl or arylphenyl)-1,3-oxazoline compounds |
US6573286B1 (en) | 2002-06-21 | 2003-06-03 | Dow Agrosciences Llc | 2-(2,6-disubstituted phenyl)-4-aryl-5-alkyl-1,3-oxazoline compounds |
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TW259693B (zh) * | 1993-08-04 | 1995-10-11 | Du Pont | |
TW440429B (en) * | 1994-08-12 | 2001-06-16 | Bayer Ag | Substituted biphenyloxazolines |
CZ104797A3 (en) * | 1994-10-06 | 1997-07-16 | Bayer Ag | Substituted biphenyloxazolines, process of their preparation, intermediates for their preparation, preparations in which said substances are comprised and their application |
CN1173172A (zh) * | 1995-01-20 | 1998-02-11 | 纳幕尔杜邦公司 | 杀虫和杀螨的噁唑啉和噻唑啉 |
JP2000500755A (ja) * | 1995-11-17 | 2000-01-25 | バイエル・アクチエンゲゼルシヤフト | ビフェニルエーテルオキサゾリン及びその有害生物防除剤としての使用 |
DE19548419A1 (de) * | 1995-12-22 | 1997-06-26 | Bayer Ag | Substituierte Thiazoline |
TW424089B (en) * | 1996-01-16 | 2001-03-01 | Du Pont | Oxazoline arthropodicides |
-
1997
- 1997-04-24 DE DE19717228A patent/DE19717228A1/de not_active Withdrawn
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1998
- 1998-04-10 TW TW087105396A patent/TW526197B/zh active
- 1998-04-14 BR BR9809413-0A patent/BR9809413A/pt not_active IP Right Cessation
- 1998-04-14 KR KR1019997009277A patent/KR20010006197A/ko not_active Application Discontinuation
- 1998-04-14 AU AU73351/98A patent/AU727621B2/en not_active Ceased
- 1998-04-14 EP EP98920521A patent/EP0980361A1/de not_active Withdrawn
- 1998-04-14 JP JP54495298A patent/JP2001521535A/ja active Pending
- 1998-04-14 CN CN98806571A patent/CN1309650A/zh active Pending
- 1998-04-14 WO PCT/EP1998/002182 patent/WO1998047881A1/de not_active Application Discontinuation
- 1998-04-14 US US09/402,966 patent/US6414000B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
WO1998047881A1 (de) | 1998-10-29 |
BR9809413A (pt) | 2000-06-13 |
DE19717228A1 (de) | 1998-10-29 |
JP2001521535A (ja) | 2001-11-06 |
EP0980361A1 (de) | 2000-02-23 |
AU727621B2 (en) | 2000-12-14 |
TW526197B (en) | 2003-04-01 |
AU7335198A (en) | 1998-11-13 |
US6414000B1 (en) | 2002-07-02 |
KR20010006197A (ko) | 2001-01-26 |
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