CN1164228A - 2-[(2-烷氧基-6-三氟甲基嘧啶-4-基)氧亚甲基]苯基乙酸衍生物、其制备和中间体以及应用] - Google Patents
2-[(2-烷氧基-6-三氟甲基嘧啶-4-基)氧亚甲基]苯基乙酸衍生物、其制备和中间体以及应用] Download PDFInfo
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- CN1164228A CN1164228A CN95196288A CN95196288A CN1164228A CN 1164228 A CN1164228 A CN 1164228A CN 95196288 A CN95196288 A CN 95196288A CN 95196288 A CN95196288 A CN 95196288A CN 1164228 A CN1164228 A CN 1164228A
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- methyl
- phenyl
- alcohol
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- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
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- VENACLKEZSTSMY-UHFFFAOYSA-N n-cyclohexyl-2,5-dimethyl-n-phenylfuran-3-carboxamide Chemical compound O1C(C)=CC(C(=O)N(C2CCCCC2)C=2C=CC=CC=2)=C1C VENACLKEZSTSMY-UHFFFAOYSA-N 0.000 description 1
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003924 oil dispersant Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
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Abstract
本发明描述了式I的2-[(2-烷氧基-6-三氟甲基嘧啶-4-基)氧亚甲基]苯基乙酸衍生物、其制备方法和中间体,其中的符号和取代基具有下列含意:U是CH或N;V是O或NH;R是C1-C6烷基;R1是氰基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基或苯基;n是0或从1至4的整数。
Description
本发明涉及式I的2-〔(2-烷氧基-6-三氟甲基嘧啶-4-基)氧亚甲基〕苯基乙酸衍生物其中的符号和取代基具有下列含意:U是CH或N;V是O或NH;R是C1-C6-烷基;R1是氰基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基或苯基;n是0或从1至4的整数,如果n大于1,则R1可以不同。
此外,发明还涉及制备这些化合物的方法和中间体,含有它的组合物和其应用。
α-杂芳氧基亚甲基-β-甲氧基丙烯酸甲酯已作为杀真菌剂描述于文献中(EP-A 178826、EP-A 278595、EP-A 350691)。另外EP-A 407873描述了相应的α-〔2-(6-三氟甲基嘧-4-基)-氧亚甲基苯基〕-β-甲氧基丙烯酸甲酯具有杀螨和杀虫作用。
此外,还公开了α-〔2-(杂芳氧基亚甲基)苯基]-α-甲氧基亚氨基乙酸甲酯具有杀真菌作用(EP-A 253213、EP-A 254426、EP-A 299694)和杀虫或杀螨作用(EP-A 407873)。
此外,文献中描述了α-〔2-(杂芳氧基亚甲基)苯基]-α-甲氧基亚氨基-N-甲基乙酰胺具有杀真菌作用(EP-A 396692)和杀虫或杀螨作用(EP-A 477631)。
然而,在许多情况下,这些文献中描述的化合物对动物害虫的作用是不能令人满意的。
本发明的目的是提供这样的化合物,所述的化合物在防治有害真菌和动物害虫方面,特别是在防治有害真菌、昆虫、线虫和螨方面,尤其是在防治昆虫和螨方面,具有改善的性能。
我们现已发现,此目的通过本文开头所定义的化合物I实现。此外,我们发现其制备方法和中间体、含有它们的组合物及其用途。
在式III中,X是可被亲核置换的离去基团如卤素(例如氯、溴或碘)或烷基或芳磺酰基(例如甲磺酰基、三氟甲基磺酰基、苯磺酰基或4-甲基苯磺酰基)。
此反应通常在0℃至80℃下,优选在20℃至60℃下进行。
适合的有机溶剂是芳烃如甲苯,邻、间和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚类如乙醚、二异丙基醚、叔丁基甲基醚、二恶烷、苯甲醚和四氢呋喃,腈类如乙腈和丙腈,醇类如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,酮类如丙酮和甲乙酮,以及二甲亚砜、二甲基甲酰胺、二甲基乙酰胺、1,3-二甲基咪唑烷-2-酮和1,3-二甲基四氢-2(1H)-嘧啶酮,特别优选二氯甲烷、丙酮和二甲基甲酰胺。
也可以使用所提到的溶剂的混合物。
适合的碱一般是:无机化合物,如碱金属和碱土金属氢氧化物如氢氧化锂、氢氧化钠、氢氧化钾、氢氧化钙,碱金属和碱土金属氧化物如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氨化物如氨化锂、氨化钠和氨化钾,碱金属和碱土金属碳酸盐如碳酸钾和碳酸钙,以及碱金属碳酸氢盐如碳酸氢钠;有机金属化合物,特别是烷基碱金属如甲基锂、丁基锂和苯基锂,烷基镁卤化物如氯化甲基镁,以及碱金属或碱土金属醇化物如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲醇镁;此外还有有机碱,例如,叔胺如三甲胺、三乙胺、二异丙基乙胺和N-甲基哌啶,吡啶,取代的吡啶如可力丁、二甲基吡啶和4-二甲基氨基吡啶,以及双环胺类。
特别优选的是氢氧化钠、氢化钠、碳酸钾和叔丁醇钾。
碱一般使用等摩尔的量、过量,或如果适宜作为溶剂使用。
加入催化量的冠醚如18-冠-6或15-冠-5-醚,对反应会是有利的。
反应也可以在两相体系中进行,所述的两相体系由碱金属或碱土金属氢氧化物或碱金属或碱土金属碳酸盐的水溶液和有机相如卤代烃组成。可以采用相转移催化剂卤化铵和四氟硼酸盐如氯化苄基三乙基铵、溴化苄基三丁基铵、氯化四丁基铵、溴化十六烷基三甲基铵或四氯硼酸四丁基铵,以及鏻卤化物如氯化四丁基鏻或溴化四苯基鏻。
首先用碱处理化合物II,并且将所得的盐与化合物III反应,对反应会是有利的。
化合物II可以通过将三氟乙酸酯VI与O-烷基异脲VII以相似于已知方法缩合而得到(参见《化学会志)》(J.Chem.Soc)1946,5)。式VI中的Rb是C1-C4-烷基,特别是甲基或乙基。
反应通常在0℃至120℃下进行,优选在20℃至80℃下进行,特别是在溶剂的沸点下进行。所用的溶剂是常规的醇,特别是甲醇或乙醇。
式VII的O-烷基异脲通常采用是其盐的形式,特别是其氢卤酸盐(例如盐酸盐或氢溴酸盐)。当有采用盐时,建议在碱(如碱土金属或碱金属醇化物或氢氧化物如甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾或氢氧化钙)存在下进行此反应。
另外,化合物I也可以通过将式IV的砜衍生物以本身已知的形式(参见例如《药物化学杂志》(J.Med.Chem.)27(1984),1621;CH-A 649068),在碱存在下与式V的醇反应来获得。式IV中的Ra是C1-C4-烷基,特别是甲基。
适合的碱特别是氢化钠、叔丁醇钾和碳酸钾。
反应一般是在惰性极性非质子传递溶剂(特别是二甲亚砜、二甲基甲酰胺或1,3-二甲基四氢-2(1H)-嘧啶酮)中进行的。
氧化作用是根据文献已知的方法,例如在浓乙酸中用过氧化氢(参见Chem.Pharm.Bul1.27(1978),183)或在水中用次氯酸钠(参见J.Prakt.Chem.33(1966),165)来进行的。
其中V是氧的式III苄基衍生物是在本文开头所引述的文献中已知的。其中U是N且V是NH的苄基衍生物II描述于DE-A 4305502中。
另外,其中U是N且V是NH的通式I化合物是通过氨解相应的醚(V=O)来获得的(参见,Houben-Weyl Vol.E5,p.98 3ff.)。
该反应是惰性溶剂中在0℃至60℃下,优选在10℃至30℃下常规地进行的。
可以将甲胺以气体导入或以液体溶液计量加入。
适合的溶剂是,芳烃如甲苯,邻、间和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚类如乙醚、二异丙基醚、叔丁基甲基醚、二恶烷、四氢呋喃和苯甲醚,醇类如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,特别优选的是甲醇、甲苯和四氢呋喃,也可以使用这些溶剂的混合物。
上述结构式中所指符号的定义中,采用的是集合名词,这些集合名词一般代表下列取代基:卤素:氟、氯、溴和碘;烷基;具有1至6个碳原子的饱和直链或支链烃基,如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基;卤代烷基:(如上所述的)具有1至4个碳原子的直链或支链烷基,这些基团的氢原子可以部分或全部被如上所述的卤原子取代,例如C1-C2-卤代烷基,如一氯甲基、二氯甲基、三氯甲基、一氟甲基、二氟甲基、三氟甲基、一氯一氟甲基、二氯一氟甲基、一氯二氟甲基、1-乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基和五氟乙基;烷氧基:(如上所述的)具有1至4个碳原子的直链或支链烷基,其经由氧原子(-O-)键合于主结构上;卤代烷氧基(如上所述的)具有1至4个碳原子的直链或支链卤代烷基,它经由氧原子(-O-)键合于主结构上。
考虑到其生物活性,哪些其中R是C2-C5-烷基,特别是C2-C4-烷基的化合物I是特别优选的。
此外,式中n是0或1,特别是0的化合物I是优选的。
在其中n不是0的情况下,式中R1具有下列含意的化合物I是优选的:氰基、氟、氯、甲基、三氟甲基或甲氧基。
此外,式中一个R1基是键合于苯环的3-、4-或5-位上的化合物I是优选的。
具体的说,考虑到其用途,收集于下列表中的化合物I是优选的。在表中提到的作为取代基的基团此外本身(独立于它们所提到的组合)也作为所涉及的取代基的特别优选的实施方案。表1
式I化合物,其中U是CH和V是O(=Ia),且取代基R1 n与R的组合相应于表A中一行。表2
式I化合物,其中U是N和V是O(=Ib),且取代基R1 n与R的组合相应于表A中一行。表3
式I化合物,其中U是N和V是NH(=Ic),且取代基R1 n与R的组合相应于表A中一行。表A
No. | R1 n | R |
01 | H | CH3 |
02 | H | CH2CH3 |
03 | 3-Cl | CH2CH3 |
04 | 4-OCH3 | CH2CH3 |
05 | H | CH2CH2CH3 |
06 | 3-Cl | CH2CH2CH3 |
07 | H | CH(CH3)2 |
08 | 3-Cl | CH(CH3)2 |
09 | 4-OCH3 | CH(CH3)2 |
10 | 5-C(CH3)3 | CH(CH3)2 |
11 | H | CH2CH2CH2CH3 |
12 | H | CH2CH(CH3)2 |
13 | H | CH(CH3)CH2CH3 |
根据本发明的式I化合物适合于防治昆虫、螨和线虫类的动物害虫,尤其是昆虫,特别是螨。它们可以用作作物保护和卫生、贮藏材料保护和兽医方面的杀真菌剂和杀虫剂。有害昆虫包括:鳞翅目,例如,棉褐带卷蛾(Adoxophyes orana)、小地老虎(Agrotisypsilon)、芜菁夜蛾(Agrotis segetum)、棉叶波纹夜蛾(Alabamaargillacea)、黎豆夜蛾(Anticarsia gemmatalis)、苹果银蛾(Argyresthis conjugella)、汉马夜蛾(Autographa gamma)、卷叶蛾(Cacoecia murinana)、卷蛾(Capua reticulana)、枞色卷蛾(Choristoneura fumiferana)、玉米螟(Chilo partellus)、西方云杉卷蛾(Choristoneura occidentalis)、一点粘虫(Cirphosunipuncta)、稻纵卷叶螟(Cnaphalocrocis medinalis)、Crocidolomiabinotalis、苹蠹蛾(Cydia pomonella)、欧洲松毛虫(Dendrolimuspini)、瓜野螟(Diaphania nitidalis)、巨座玉米螟(Diatraeagrandiosella)、棉斑实蛾(Earias insulana)、非洲蔗螟(Elasmopalpus lignosellua)、Eupoecilia ambiguella、粒肤地虎(Feltia subterranea)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothisarmigera)、烟芽夜蛾(Heliothis virescens)、棉铃虫(Heliothiszea)、菜心野螟(Hellula undalis)、Hibernia defoliaria、美国白蛾(Hyphantria cunea)、苹果巢蛾(Hyponomeuta malinellus)、番茄蠹蛾(Keiferia lycopersicella)、铁杉尺蛾(Lambdinafiscellaria)、甜菜夜蛾(Laphygma exigua)、旋纹夜蛾(Leucopterascitella)、细蛾(Lithocolietis blancardella)、小卷蛾(Lobesiabotrana)、草地螟(Loxostege sticticalis)、舞毒蛾(Lymantriadispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetiaclerkella)、烟草天蛾(Manduca sexta)、天幕毛虫(Malacosomaneustria)、甘蓝夜蛾(Mamestra brassicae)、稻毛胫夜蛾(Mocisrepanda)、鸦胆子尺蛾(Operophthera brumata)、花旗舞毒蛾(Orgyia pseudotsugata)、玉米螟(Ostrinia nubilalis)、苹褐卷蛾(Pandemis heparana)、小眼夜蛾(Panolis flammea)、棉红铃虫(Pectinophora gossypiella)、马铃薯毒蛾(Phthorimaeaoperculella)、桔叶潜蛾(Phyllocnistis citrella)、大菜粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、荷兰石竹小卷蛾(Platynota stultana)、小菜蛾(Plutella xylostella)、桔花巢蛾(Prays citri)、油橄榄巢蛾(Prays oleae)、斜纹夜蛾(Prodenia sunia)、斜纹夜蛾(Prodenia ornithogalli)、大豆夜蛾(Pseudoplusia includens)、二三针松小卷蛾(Rhyacioniafrustrana)、Scrobipalpula absoluta、大螟(Sesamia inferens)、葡萄长须卷蛾(Sparganothis pilleriana)、草地贪夜蛾(Spodopterafrugiperda)、埃及棉卷虫(Spodoptera littoralis)、斜纹叶蛾(Spodoptera litura)、棉卷叶螟(Syllepta derogata)、红带透翅蛾(Synanthedon myopaeformis)、Thaumatopoea pityocampa、栎绿卷蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusia ni)、三化螟(Tryporyza incertulas)、加拿大小卷螟(Zeirapheracanadensis)、以及蜡螟(Galleria mellonella)、麦蛾(Sitotrogacerealella)、稻子豆粉螟(Ephestia cautella)、幕衣蛾(Tineolabisselliella);鞘翅目,例如,直条叩甲(Agriotes lineatus)、晦暗叩甲(Agriotesobscurus)、野棉象(Anthonomus grandis)、梨花象(Anthonomuspomorum)、象甲(Apion vorax)、甜菜隐食甲(Atomaria linearis)、大松小蠹(Blastophagus piniperda)、甜菜大龟甲(Cassidanebulosa)、豆叶甲(Cerotoma trifurcata)、甘蓝荚象甲(Ceuthorhynchus assimilis)、象甲(Ceuthorhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis)、烟金针虫(Conoderusvespertinus)、天门冬叶甲(Crioceris asparagi)、云杉红翅小蠹(Dendroctonus refipennis)、长角叶甲(Diabroticalongicornis)、十二斑叶甲(Diabrotica 12-punctata)、玉米芽根叶甲(Diabrotica virgifera)、墨西哥豆甲(Epilachna varivestis)、烟草跳甲(Epitrix hiripennis)、棉籽灰象甲(Eutinibothrusbrasiliensis)、松大象甲(Hylobius abietis)、埃及苜蓿象甲(Hyperabrunneipennis)、苜蓿叶象甲(Hypera postica)、云杉八齿小蠹(Ipstypographus)、烟负泥虫(Lema bilineata)、橙足负泥虫(Lemamelanopus)、马铃薯甲虫(Lepttinotarsa decamlineata)、加州金针虫(Limoniua californicus)、美洲稻象甲(Lissorhoptrusoryzophilus)、玉米叩甲(Melanotus communis)、油菜花露尾甲(Meligethes aeneus)、Melolontha hippocastani、西方五月鳃角金龟(Melolontha melolontha)、稻负泥虫(Oulema oryzae)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、草莓耳喙象(Otiorrhynchusovatus)、辣根猿叶虫(Phaedon cochleariae)、庭园丽金龟(Phyllopertha horticola)、鳃角金龟(Phyllophaga sp.)、条跳甲(Phyllotreta chrysocephala)、芜菁淡足跳甲(Phyllotretanemorum)、曲条跳甲(Phyllotreta striolata)、日本丽金龟(Popilliajaponica)、跳甲(Psylliodes napi)、栎黑小蠹(Scolytusintricatus)、豌豆叶象甲(Sitona lineatus)、以及蚕豆象(Bruchusrufimanus)、豌豆象(Bruchus pisorum)、豆象(Bruchus lentis)、谷象(Sitophilus granaria)、烟草甲(Lasioderma serricorne)、锯谷盗(Oryzaephilus surinamensis)、谷蠹(Rhyzoperthadominica)、米象(Sitophilus oryzae)、赤拟谷盗(Triboliumcastaneum)、谷斑皮蠹(Trogoderma granarium)、墨西哥豆象(Zabrotes subfasciatus);双翅目,例如,墨西哥桔实蝇(Anastrepha ludens)、地中海实蝇(Ceratitis capitata)、高梁瘿蚊(Contarinia sorghicola)、瓜实蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、甘蓝瘿蚊(Dasineura brassicae)、Delia coarctata、Delia radicum、大麦水蝇(Hydrellia griseola)、种蝇(Hylemyia platura)、Liriomyza sativae、美洲斑潜蝇(Liriomyza trifolii)、小麦瘿蝇(Mayetiola destructor)、Orseolia oryzae、瑞典麦杆蝇(Oscinella frit)、菠菜叶花蝇(Pegomya hyoscyami)、Phorbiaantiqua、甘蓝花蝇(Phorbia brassicae)、Phorbia coarctata、樱桃实蝇(Rhagoletis cerasi)、菜实蝇(Rhagoletis pomonella)、大蚊(Tipula oleracea)、沼泽大蚊(Tipula paludosa),以及埃及伊蚊(Aedes aegypti)、骚扰伊蚊(Aedes vexans)、五斑按蚊(Anopheles maculipennis)、倍氏金蝇(Chrysomya bezziana)、金蝇(Chrysomya hominivorax)、腐败金蝇(Chrysomyamacellaria)、嗜人瘤蝇(Cordylobia anthropophaga)、尖音库蚊(Culex pipiens)、黄腹厕蝇(Fannia canicularis)、肠胃蝇(Gasterophilus intestinalis)、舌蝇(Glossina morsitans)、扰血蝇(Haematobia irritans)、Haplodiplosis equestris、纹皮蝇(Hypoderma lineata)、绿蝇(Lucilia caprina)、丝光绿蝇(Lucilia sericata)、家蝇(Musca domestica)、厩腐蝇(Muscinastabulans)、羊狂蝇(Oestrus ovis)、牛虻(Tabanus bovinus)、蚋(Simulium damnosum);缨翅目,例如,烟褐蓟马(Frankliniella fusca)、西方蓟马(Frankliniella occidentalis)、小麦蓟马(Frankliniellatritici)、小麦管蓟马(Haplothrips tritici)、桔实蓟马(Scirtothrips citri)、稻蓟马(Thrips oryzae)、棕黄蓟马(Thripspalmi)、棉蓟马(Thrips tabaci);膜翅目,例如,菜叶蜂(Athalia rosae)、热带切叶蚁(Attacephalotes)、切叶蚁(Atta sexdens)、得州切叶蚁(Atta texana)、叶蜂(Hoplocampa minuta)、苹果叶蜂(Hoplocampa testudinea)、阿根廷蚁(Iridomyrmex humilis)、虹蚁(Iridomyrmex purureus)、小家蚁(Monomorium pharaonis)、火蚁(Solenopsis geminata)、红外来火蚁(Solenopsis invicta)、黑外来火蚁(Solenopsisrichteri);半翅目,例如,喜绿蝽(Acrosternum hilare)、多毛长蝽(Blissusleucoperus)、烟草黑斑盲蝽(Cyrtopetis notatus)、棉红蝽(Dysdercus cingulatus)、中红蝽(Dysdercus intermedius)、盾蝽(Eurygaster integriceps)、棉褐蝽(Euschistusimipictiventris)、叶喙缘蝽(Leptoglossus phyllopus)、豆荚盲蝽(Lugus hesperus)、牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lyguspratensis)、黄肩绿蝽(Nezara viridula)、甜菜拟网蝽(Piesmaquadrata)、Solubea insularis、Thyanta perditor;同翅目,例如,无网长管蚜(Acyrthosiphon onobrychis)、豌蚜(Acyrthosiphon pisum)、落叶松球蚜(Adelges laricis)、红圆蚧(Aonidiella aurantii)、蚜茧蜂(Aphidula nasturtii)、甜菜蚜(Aphis fabae)、棉蚜(Aphis gossypii)、苹果蚜(Aphispomi)、茄沟无网蚜(Aulacorthum solani)、甘薯粉虱(Bemisiatabaci)、蓟短尾蚜(Brachycaudus cardui)、甘蓝蚜(Brevicorynebrassicae)、Dalbulus maidis、Dreyfusia nordmanninianae、Dreyfusia piceae、圆尾蚜(Dysaphis radicola)、蛋豆微叶蝉(Empoasca fabae)、苹果绵蚜(Eriosoma lanigerum)、灰稻虱(Laodelphaxs triatella)、麦长管蚜(Macrosiphum avenae)、马铃薯长管蚜(Macrosiphum euphorbiae)、蔷薇长管蚜(Macrosiphonrosae)、蚕豆修尾蚜(Megoura viciae)、蔷薇麦蚜(Metopolophiumdirhodum)、桃蚜(Myzus persicae)、樱桃瘤蚜(Myzus cerasi)、黑尾叶蝉(Nephotettix cincticeps)、稻褐飞虱(Nilaparvatalugens)、蔗飞虱(Perkinsiella saccharicida)、忽布疣额蚜(Phorodon humuli)、桔粉蚧(Planococcus citri)、苹木虱(Psyllamali)、梨木虱(Psylla piri)、梨黄木虱(Psylla pyricol)、梨笠圆蚧(Quadraspidiotus perniciosus)、玉米缢管蚜(Rhopalosiphummaidis)、油榄黑盔蚧(Saissetia oleae)、草间裂蚜(Schizaphisgraminum)、西印度红圆盾蚧(Selenaspidus articulatus)、麦长管蚜(Sitobion avenae)、白背飞虱(Sogatella furcifera)、桔蚜(Toxoptera citricida)、结翅粉虱(Trialeurodes abutilonea)、温室粉虱(Trialeurodes vaporariorum)、葡萄根瘤蚜(Viteusvitifolii);等翅目,例如,Calotermes flavicollis、白蚁(Leucotermesflavipes)、大白蚁(Macrotermes subhyalinus)、黑翅土白蚁(Odontotermes formosanus)、散白蚁(Reticulitermes lucifugus)、白蚁(Termes natalensis);来自直翅目昆虫(直翅目),例如欧洲蝼蛄(Gryllotalpagryllotalpa)、蝗虫(Locusta migratoria)、双带蚱蜢(Melanoplus bivittatus)、赤腿蚱蜢(Melanoplus femur-rubrum)、墨西哥蚱蜢(Melanoplusmexicanus)、迁徙蚱蜢(Melanoplus sanguinipes)、落矶山蚱蜢(Melanoplus spretus)、红翅蝗(Nomadacris septemfasciata)、美洲蝗(Schistocerca americana)、蚱蜢(Schistocerca peregrina)、Stauronotus maroccanus、沙漠蝗(Schistocerca gregaria),还有家蟋蟀(Acheta domestica)、东方蠊(Blatta orientalis)、德国小蠊(Blattella germanica)、美洲大蠊(Periplaneta americana);蛛形纲,例如,植食性的螨类,如蕃茄叶刺皮瘿螨(Aculopslycopersicae)、Aculops pelekassi、苹刺瘿螨(Aculusschlechtendali)、紫红短须螨(Brevipalpus phoenicis)、苜蓿苔螨(Bryobia praetiosa)、鹅耳枥始叶螨(Eotetranychus carpini)、斑氏真叶螨(Eutetranychus banksii)、桔瘿螨(Eriophyes citri)、草地小爪螨(Oligonychus pratensis)、苹果全爪螨(Panonychusumli)、桔全爪螨(Panonychus citri)、柑桔锈螨(Phyllocoptrutaoleivora)、侧多食跗线螨(Polyphagotarsonemus latus)、淡跗线螨(Tarsonemus pallidus)、朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychuspacificus)、二点叶螨(Tetranychus urticae),蜱如美国花蜱(Amblyomma americanum)、Amblyomma variegatum、波斯锐缘蜱(Argas persicus)、环形牛蜱(Boophilus annulatus)、褪色牛蜱(Boophilus decoloratus)、微小牛蜱(Boophilus microplus)、森林革蜱(Dermacentor silvarum)、平头璃眼蜱(Hyalommatruncatum)、蓖子硬蜱(Ixodes ricinus)、Ixodes rubicundus、非洲钝缘蜱(Ornithodorus moubata)、耳剌残喙啤(Otobiusmegnini)、非洲扇头蜱(Rhipicephalus appendiculatus)和Rhipicephalus evertsi和动物寄生螨如鸡刺皮螨(Dermanyssusgallinae)、绵羊疮螨(Psoroptes ovis)和疥螨(Sarcoptesscabibei);线虫,例如,根结线虫,例如根瘤线虫(Meloidogyne hapla)、黄麻根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogynejavanica),囊线虫,例如Globodera pallida、Globoderarostochiensis、异皮线虫(Heterodera avenae)、异皮线虫(Heterodera glycines)、史氏轭囊线虫(Heterodera schachtii),迁移性内寄生线虫和半内寄生线虫,例如,Heliocotylenchusmulticinctus、Hircshmanniella oryzae、Hoplolaimus spp.、Rotylenchus penetrans、短尾垫刃线虫(Pratylenchusbrachyurus)、Pratylenchus fallax、Pratylenchus penetrans、Pratylenchus vulnus、毕肖穿孔线虫(Radopholus similis)、Rotylenchus reniformia、Scutellonema bradys、Tylenchulussemipenetrans,茎和叶线虫,例如,Anguina tritici、稻白端滑刃线虫(Aphelenchoides besseyi)、Ditylenchus angustus、Di tylenchus dipsaci,病毒媒介,例如,Longidorua spp.、克氏髦根线虫(Trichodorus chistei)、Trichodorus viruliferus、Xiphinema index、地中海剑线虫(Xiphinema mediterraneum)。
此外,化合物I适合作为杀真菌剂。
化合物I的突出特点是其对广谱的致病真菌,特别是对子囊菌纲和担子菌纲的真菌有活性。在某些情况下,它们具有内吸活性,且可以用作叶面和土壤杀真菌剂。
它们在防治各种作物如小麦、黑麦、大麦、燕麦、稻、玉米、草、棉花、大豆类、咖啡、甘蔗、葡萄、水果、观赏植物和蔬菜(例如,黄瓜、豆和胡瓜)以及这些作物的种子上的许多真菌方面特别重要。
它们特别适合于防治下列植物病原真菌:禾谷类上的禾白粉菌(Erysiphe graminia)、胡瓜上的二孢白粉菌(Erysiphecichoracearum)和苍耳单丝壳菌(Sphaerotheca fuliginea)、苹果上的苹果白粉病柄球菌(Podosphaera leucotricha)、葡萄上的葡萄白粉病钩丝壳菌(Uncinula necatar)、禾谷类上的柄锈菌(Puccinia)、棉花和草坪上的丝核菌(Rhizoctonia)、禾谷类和甘蔗上的黑粉菌(Ustilago)、苹果上的苹果黑星菌(Venturia Inaequalis)、禾谷类上的长蠕孢菌(Helminthosporium)、小麦上的颖枯病菌(Septorianodorum)、草莓和葡萄上的灰霉病菌(Botrytis cinera)、花生上的花生尾孢菌(Cercospora arachidicola)、小麦和大麦上的眼斑病菌(Pseudocercospora herpotophthora)、稻上的稻梨孢(Pyriculariaoryzae)、马铃薯和蕃茄上的蔓延疫霉(Phytophthora infestans)、各种作物上的镰刀菌(Fusarium)和轮枝孢菌(Verticillium)、葡萄上的葡萄生单轴霉(Plasmopara viticola)、蔬菜和水果上的链格孢菌(Alternaria)。
化合物I是通过用此化合物的杀真菌有效量来处理真菌或意欲得到保护使之不受真菌侵害的植物、种子、材料或土地来施用的。施用在材料、植物或种子被真菌感染前或后进行的。
它们可以转换成常规制剂如溶液、乳剂、悬浮剂、粉剂、粗粉剂、膏剂和颗粒剂。施用形式取决于特定的使用;在各种情况下,须保证2-〔(2-烷氧基-6-三氟甲基嘧啶-4-基)氧亚甲基〕苯基乙酸衍生物的分散尽可能的细微和均匀。这些制剂可以用已知的方式制备,例如通过将活性化合物用溶剂和/或载体来稀释,如果需要可采用乳化剂和分散剂。如果用水作稀释剂,也可以用其它的有机溶剂作助溶剂。适合用于此目的的助溶剂主要是:溶剂如芳族化合物(例如二甲苯)、氯代芳族化合物(例如氯苯)、石蜡(例如石油馏份)、醇类(例如甲醇、丁醇)、酮类(例如环己酮)、胺类(例如乙醇胺、二甲基甲酰胺)和水;载体如研碎的天然矿物质(例如高岭土、矾土、滑石、白垩)和研碎的合成矿物质(例如高分散的硅酸、硅酸盐);乳化剂如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)和分散剂如木素亚硫酸盐废液和甲基纤维素。
杀真菌剂组合物通常含有按重量计0.1至9 5%、优选0.5至9 0%的活性化合物。
取决于所需的效果,施用量为0.01至2.0kg活性化合物/公顷。
在处理种子时,活性化合物的用量通常为0.001-0.1g、优选0.01-0.05g/kg种子。
活性化合物可以以其本身的形式、或以其制剂的形式或由之制备的使用形式,例如以可直接喷雾水溶液、粉剂、悬浮剂或分散液、乳剂、油分散液、膏剂、喷粉组合物、撒施组合物或颗粒剂的形式,通过喷雾、弥雾、喷粉、撒施或浇泼使用。施用形式取决于使用的目的;在每一种情况下,应确保本发明的活性化合物的分散尽可能的细微和均匀。
它们可以转换成常规的制剂如溶液、乳剂、悬浮剂、粉剂、粗粉剂、膏剂或颗粒剂。施用形式取决于使用的目的;在每一种情况下,应确保本发明的活性化合物的分散尽可能的细微和均匀。
这些制剂可以用已知的方式制备,例如通过将活性化合物用溶剂和/或载体来稀释,如果需要可采用乳化剂和分散剂,如果用水作稀释剂,也可以用其它的有机溶剂作助溶剂。
适合用于此目的的助溶剂主要是:- 溶剂如芳族化合物(例如二甲苯)、氯代芳族化合物(例如氯苯)、
石蜡(例如石油馏份)、醇类(例如甲醇、丁醇)、酮类(例如环己
酮)、胺类(例如乙醇胺)、二甲基甲酰胺和水;- 载体如研碎的天然矿物质(例如高岭土、矾土、滑石、白垩)和研碎
的合成矿物质(例如高分散的硅酸、硅酸盐);- 乳化剂如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸
盐和芳基磺酸盐)和- 分散剂如木素亚硫酸盐废液或甲基纤维素。
适合的表面活性物质是芳族磺酸(例如木素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸)和脂肪酸的碱金属、碱土金属和铵盐,烷基磺酸盐和烷基芳基磺酸盐,烷基硫酸盐、月桂基醚硫酸和脂肪醇硫酸盐,以及硫酸化的十六-、十七-和十八醇以及脂肪醇醚的盐,磺化萘和其衍生物与甲醛的的缩合产物,萘或萘磺酸与苯酚和甲醛的缩合产物,聚氧乙烯辛基酚醚、乙氧基烷化的异辛基-、辛基-或壬基酚,烷基苯酚或三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异三癸基醇、脂肪醇环氧乙烷缩合物,乙氧基化蓖麻油,聚氧乙烯-或聚氧丙烯烷基醚,月桂醇聚乙二醇醚乙酸酯、失水山梨醇酯,木素亚硫酸盐废液或甲基纤维素。
含水的施用形式可以通过加水,由乳油、分散液、膏剂、可湿性粉剂或水可分散颗粒剂制备。制备乳剂、膏剂或油分散液时,通过加入润湿剂、粘合剂、分散剂或乳化剂,将物质于水中均化或溶于油或溶剂中。而且,也可以制备由活性物质、润湿剂、粘合剂、分散剂或乳化剂和可能的溶剂或油组成的浓缩物,该浓缩物适合于用水稀释。
粉剂、撒施和喷粉组合物可以通过将活性物质与固体载体混合或一起研磨而生产。
颗粒剂(例如,涂敷、浸渍或均质颗粒剂)可以通过将活性化合物粘合到固体载体上而制备。
固体载体是矿石土如硅胶、硅酸、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、陶土、白云石、硅藻土、硫酸钙和硫酸镁、氧化镁,研碎的合成材料、化肥,如硫酸铵、磷酸铵、硝酸铵、尿素和植物产物如面粉、树皮粉、木粉和坚果壳粉、纤维素粉和其它固体载体。在直接可用制剂中的活性化合物浓度可以在相对宽的范围内变化。
通常,组合物含有按重量计0.0001至95%的活性化合物。
含有大于按重量计95%的活性化合物的制剂可以成功地用在超低体积方法(ULV)中,甚至可能直接使用活性化合物而无须添加剂。
防治动物害虫时,制剂含有按重量计0.0001至10%,优选按重量计0.01至1%的活性化合物是适宜的。
活性化合物一般采用90至100%,优选95至100%的纯度(根据NMR谱)。
这些制剂的实例是:
I.90份重量的本发明化合物I和10份重量N-甲基-α-吡咯烷酮的溶液,它适合以非常小的雾滴的形式施用。
II.20份重量的本发明化合物I在如下混合物中的溶液:80份重量的烷基化苯、10份重量的8至10摩尔环氧乙烷与1摩尔油酸N-单乙醇酰胺的加成物、5份重量的十二烷基苯磺酸钙盐和5份重量的40摩尔环氧乙烷与1摩尔蓖麻油的加成物。将此制剂细分散于水中,获得分散液。
III.20份重量的化合物I在如下混合物中的溶液:40份重量的环己酮、30份重量的异丁醇、20份重量的7摩尔环氧乙烷与1摩尔异辛基苯酚的加成物和10份重量的40摩尔环氧乙烷与1摩尔蓖麻油的加成物。将此制剂细分散于水中,获得分散液。
IV.20份重量的本发明化合物I在如下混合物中的水分散液:25份重量的环己酮、65份重量沸点为210至280℃的矿物油馏份和10份重量的40摩尔环氧乙烷与1摩尔蓖麻油的加成物。将此制剂细分散于水中,获得分散液。
V.20份重量的本发明化合物I、3份重量的二异丁基萘-α-磺酸钠盐、17份重量的来源于亚硫酸废液的木素硫酸钠盐和60份重量的粉状硅胶在锤磨中磨碎的混合物。将此制剂细分散于水中,获得喷雾液。
VI.3份重量的本发明化合物I与97份重量细分散的高岭土的均匀混合物。此喷粉含有按重量计0.3%(重量)活性化合物。
VII.30份重量的本发明化合物I、92份重量的粉状硅胶和8份重量已喷雾到硅胶的表面的石蜡之均匀混合物。此制剂赋予活性化合物以良好的粘性。
VIII.40份重量的本发明化合物I、10份重量的苯酚磺酸钠/尿素/甲醛缩合物、2份重量的硅胶和48份重量的水的稳定水分散液。它可以进一步稀释。
IX.20份重量的本发明化合物I与2份重量的十二烷基苯磺酸钙盐、8份重量的脂肪醇聚乙二醇醚、2份重量的苯酚磺酸钠/脲/甲醛缩合物和68份重量的石蜡矿物油的稳定的油分散剂。
X.10份重量的本发明化合物I、4份重量的二异丁基萘-α-磺酸钠盐、20份重量的来源于亚硫酸废液的木素硫酸钠盐、38份重量的硅胶和38份重量的高岭土在锤磨中磨碎的混合物。将此制剂细分散于10.000份重量的水中,获得含按重量计0.1%的活性化合物的喷雾混合物。
化合物I是通过用活性量的此化合物来处理害虫或有害真菌或意欲得到保护使之不受害虫或真菌侵害的植物、种子、材料或土地来施用的。
施用在材料、植物或种子被有害真菌感染前或后进行的。
根据所需的效果类型,施用量是0.02g至3kg活性化合物/公顷,优选0.1至1kg/公顷。
在处理种子时,活性化合物的一般需要量是0.001至50g,优选0.01g至10g/kg种子。
在室外条件下防治害虫或有害真菌的活性化合物施用量是0.02至10,优选0.1至2.0kg活性化合物/ha。
化合物I,可以单独使用或与除草剂或杀真菌剂组合,也可以与其它的作物保护剂一起混合,例如与生长调节剂或与防治害虫或细菌的试剂混合。同样感兴趣的是与化肥或与采用来消除营养和微量元素缺乏的矿物盐溶液的可混合性。
作物保护剂和化肥可以以1∶10至10∶1的重量比加入本发明组合物中,如果适宜甚至可以在马上使用前加入(桶混)。与杀真菌剂或杀虫剂混合时,在许多情况下,杀真菌谱增宽。
下列杀真菌剂可与本发明组合物一起施用,列出它们旨在说明组合的可能性,而非旨在限定之:硫、二硫代氨基甲酸盐及其衍生物,如二甲基二硫代氨基甲酸铁、二甲基二硫代氨基甲酸锌、乙撑双二硫代氨基甲酸锌、乙撑双二硫代氨基甲酸锰、乙二氨双二硫代氨基甲酸锰锌、二硫化四甲基秋兰姆、N,N-乙撑双二硫代氨基甲酸锌的铵配合物、 N,N′-丙撑双二硫代氨基甲酸锌、N,N′-丙撑双(硫化氨基甲酰)二硫化物;硝基衍生物,如二硝基(1-甲基庚基)苯基巴豆酸酯、3,3-二甲基丙烯酸2-仲丁基-4,6-二硝基-苯基酯、2-仲丁基-4,6-二硝基-苯基异丙基碳酸酯、5-硝基间苯二甲酸二异丙基酯;杂环物质,如2-十七烷基-2-咪唑啉乙酸酯、2,4-二氯-6-(邻氯苯胺基)-均三嗪、O,O-二乙基苯二酰亚氨基硫代膦酸酯、5-氨基-1-β-〔双-(二甲基氨基)-氧膦基〕-3-苯基-1,2,4-三唑、2,3-二氰基-1,4-二硫代蒽酮、2-硫代-1,3-二硫并(thiolo)-β-〔4,5-b〕喹喔啉、1-(丁基氨基甲酰基)-2-苯并咪唑氨基甲酸甲酯、2-甲氧基羰基氨基苯并咪唑、2-(呋喃-2-基)苯并咪唑、2-(噻唑-4-基)苯并咪唑、N-(1,1,2,2-四氯乙硫基)四氢苯邻二甲酰亚胺、N-三氯甲硫基四氢苯邻二甲酰亚胺、N-三氯甲硫基苯邻二甲酰亚胺、N-二氯氟甲硫基-N,N-二甲基-N-苯基硫酰胺、5-乙氧基-3-三氯甲基-1,2,3-噻二唑、2-氰硫基甲硫基苯并噻唑、1,4-二氯-2,5-二甲氧基苯、4-(2-氯苯基亚肼基)-3-甲基-5-异恶唑酮、2-硫代吡啶1-氧化物,8-羟基喹啉或其铜盐、2,3-二氢-5-酰替苯胺基-6-甲基-1,4-氧硫杂环己二烯、2,3-二氢-5-酰替苯胺基-6-甲基-1,4-氧硫杂环己二烯4,4-二氧化物、2-甲基-5,6-二氢-4H-吡喃-3-酰替苯胺、2-甲基呋喃-3-酰替苯胺、2,5-二甲基呋喃基-3-酰替苯胺、2,4,5-三甲基呋喃-3-酰替苯胺、N-环己基-2,5-二甲基呋喃-3-酰替苯胺、N-环己基-N-甲氧基-2,5-二甲基呋喃-3-酰替苯胺、2-甲基苯甲酰苯胺、2-碘苯甲酰苯胺、N-甲酰-N-吗啉-2,2,2-三氯乙基乙缩醛、哌啶-1,4-二基双(1-(2,2,2-三氯乙基))甲酰胺、1-(3,4二氯苯胺基)-1-甲酰氨基-2,2,2-三氯乙烷、2,6-二甲基-N-十三基吗啉或其盐、2,6-二甲基-N-环十二吗啉或其盐、N-〔3-(对叔丁基苯基)-2-甲基丙基〕-顺-2,6-二甲基吗啉、N-〔3-(对叔丁基苯基)-2-甲基丙基〕哌啶、1-〔2-(2,4-二氯苯基)-4-乙基-1,3-二氧杂戊环-2-基乙基〕-1H-1,2,4-三唑、1-〔2-(2,4-二氯苯基)-4-正丙基-1,3-二氧杂戊环-2-基乙基〕-1H-1,2,4-三唑、N-(正丙基)-N-(2,4,6-三氯苯氧基乙基)-N-咪唑基脲、1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁酮、1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)2-丁醇、α-(2-氯苯基)-α-(4-氯苯基)5-嘧啶甲醇、5-丁基-2-二甲基氨基-4-羟基-6-甲基嘧啶、双(对氯苯基)-3-吡啶甲醇、1,2-双(3-乙氧羰基-2-硫脲基)苯、1,2-双(3-甲氧羰基-2-硫脲基)苯;以及各种杀真菌剂,如十二烷基胍乙酸盐、3-〔3-(3,5-二甲基-2-氧基环己基)-2-羟乙基〕戊二酰胺、六氯苯、DL-甲基N-(2,6-二甲基苯基)-N-2-呋喃酰氨基丙酸酯、DL-N-(2,6-二甲基苯基)-N-(2-甲氧基乙酰基)氨基丙酸甲酯、N-(2,6-二甲基苯基)-N-氯乙酰基-D,L-2-氨基-丁内酯、DL-N-(2,6-二甲基苯基)-N-(苯基乙酰基)氨基丙酸甲酯、5-甲基-5-乙烯基-3-(3,5-二氯苯基)-2,4-二氧代-1,3-恶唑烷、3-(3,5-二氯苯基)-5-甲基-5-甲氧基甲基-1,3-恶唑烷-2,4-二酮、3-(3,5-二氯苯基)-1-异丙基氨基甲酰基乙内酰脲、N-(3,5-二氯苯基)-1,2-二甲基环丙烷-1,2-二甲酰胺、2-氰基-N-乙基氨基羰基-2-甲氧亚氨基乙酰胺、1-〔2-(2,4-二氯苯基)戊基〕-1H-1,2,4-三唑、2,4-二氟-α-(1H-1,2,4-三唑基-1-甲基)二苯基甲醇、N-(3-氯-2,6-二硝基-4-三氟甲基苯基)-5-三氟甲基-3-氯-2-氨基吡啶、1-((双(4-氟苯基)甲基-硅基)甲基)-1H-1,2,4三唑。合成实施例
采用下面的合成实施例中呈示的方法,对原料化合物或中间体作适宜的修改,得到其它的式I化合物。由此得到的化合物与其物理数据一起列于下列表中。实施例12-异丙氧基-6-三氟甲基-4-羟基嘧啶
在室温下,将465g的30%浓度甲醇钠的甲醇溶液滴加到906m1无水乙醇中的357.8g O-异丙基异脲盐酸盐(或氯化O-异丙基脲铵)中。再过10分钟后,随微放热反应,向此混合物中加入475.2g三氟乙酰乙酸乙酯。加热回流12小时后,在旋转蒸发器中浓缩混合物,并将残留物溶于1升水中。向水相中加入盐酸,使之呈微酸性,之后用甲基叔丁基醚萃取。合并的有机相用水洗涤,经硫酸钠干燥,最后浓缩至干。残留物与石油醚一起搅拌,抽吸滤出,并干燥之。
得到294.5g标题化合物,为无色晶体。M.P.126-127℃。1H-NMR(CDCl3,δ以ppm计):1.4(6H);5.9(1H);6.5(1H);12.2(1H)实施例23-甲氧基-2-〔2-(2-甲磺酰基-6-三氟甲基嘧啶-4-基氧甲基)苯基〕丙烯酸甲酯(表I.04)
在20-30℃下,将0.15g钨酸二钠·2H2O加到3.9g 3-甲氧基-2-〔2-(2-甲硫基-6-三氟甲基嘧啶-4-基氧甲基)苯基〕丙烯酸甲酯的19ml冰乙酸悬浮液中,并缓慢滴加入2.8ml 30%浓度的H2O2水溶液。混合物在1小时内变清澈,并在室温下再搅拌12小时。分离时,将它倒入100ml冰水中,约30分钟后,滗析除去上清液,将残留的粘稠固体收集于乙酸乙酯中。此有机相用水洗涤,经硫酸钠干燥,最后浓缩至干。残留物与石油醚一起搅拌,抽吸滤出,并干燥之。
得到4.0g标题化合物,为淡黄色油状物。1H-NMR(CDCl3,δ以ppm计):3.3(3H);3.65(3H);3.85(3H);5.5(2H);7.15(1H);7.2(1H);7.4(2H);7.55(1H);7.6(1H)表2
实施例33-甲氧基-2-〔2-(2-异丙氧基-6-三氟甲基嘧啶-4-基氧甲基)苯基〕丙烯酸甲酯(表I.03)
No. | R | M.p.[℃] |
II.01 | CH3 | 142-143 |
II.02 | CH2CH3 | 102-106 |
II.03 | CH(CH3)2 | 118-120 |
制备由实施例1得到的羟基嘧啶的钾盐时,将222g羟基化合物溶于855ml乙醇中,并滴加到56g氢氧化钾的855ml乙醇溶液中。加热回流3小时后,将混合物浓缩,并将残留物用2升N,N-二甲基甲酰胺处理。向此钾盐的溶液中加入280g 3-甲氧基-2-〔2-溴甲基苯基〕丙烯酸甲酯,之后在60℃下搅拌12小时。收集时,将它倒入冰水中,再用甲基叔丁基醚萃取。将合并的有机相用水洗涤,经硫酸钠干燥,最后浓缩。除去N-烷基化的副产物时,将残留物溶于1升甲醇中,并用250ml水处理。晶体沉淀物通过抽吸滤出,用石油醚洗涤,并干燥之。
得到211g标题化合物。M.P.107℃。1H-NMR(CDCl3,δ以ppm计):1.4(6H);3.7(3H);3.8(3H);5.3(1H);5.35(2H);6.65(1H);7.2(1H);7.4(2H);7.5(1H);7.55(1H)实施例42-甲氧基亚氨基-2-〔3-氯-2-(2-异丙氧基-6-三氟甲基嘧啶-4-基氧甲基)苯基〕乙酸甲酯(表I.08)
在100ml二甲基甲酰胺中将3.3g 2-异丙氧基-4-羟基-6-三氟甲基嘧啶和2.4g碳酸钾在室温(约25℃)下搅拌30分钟,之后将此混合物经1小时用在30ml二甲基甲酰胺中的4.8g 2-甲氧基亚氨-基2-〔2-溴甲基-3-氯苯基〕乙酸甲酯处理。在室温下再过8小时后,将此反应混合物加入冰水中,并将产物用叔丁基甲基醚萃取。干燥合并的醚相,并浓缩之。由此获得的粗产物用色谱纯化(硅胶/甲苯)。得到4.2g标题化合物。M.P.106-108℃。1H-NMR(CDCl3,δ以ppm计):1.4(6H);3.85(3H);4.0(3H);5.35(1H);5.45(1H);6.6(1H);7.1(1H);7.4(1H);7.55(1H)实施例52-甲氧基亚氨基-2-〔3-氯-2-(2-异丙氧基-6-三氟甲基嘧啶-4-基氧甲基)苯基〕-N-甲基乙酰胺(表I.11)
将2.2g由实施例4得到的甲酯和70ml四氢呋喃的混合物用2ml的40%浓度的甲胺水溶液处理。在室温(约25℃)下保持8小时后,将100ml甲基叔丁基醚加入此反应混合物中。由此得到的混合物用20%浓度的柠檬酸洗涤3次,用水洗涤2次。干燥有机相,并浓缩之。由此获得的粗产物用色谱纯化〔硅胶/甲苯∶乙酸乙酯(9∶1)〕。得到1.0g标题化合物。M.P.116-118℃。1H-NMR(CDCl3,δ以ppm计):1.4(6H);2.95(3H);3.9(3H);5.35(1H);5.45(1H);6.6(1H);6.8(NH);7.1(1H);7.35(1H);7.5(1H)表I
对动物害虫作用的实施例
No. | U | V | R1 n | R | 物理数据[M.p.(℃),IR(cm-1),1H-NMR(ppm)] |
I.01 | CH | O | H | CH3 | 3.65(3H);3.75(3H);4.0(3H);5.4(2H);6.65(1H);7.1-7.6(5H) |
I.02 | CH | O | H | CH2CH3 | 66-68 |
I.03 | CH | O | H | CH(CH3)2 | 107 |
I.04 | CH | O | 3-Cl | CH(CH3)2 | 1.4(6H);3.7(3H);3.85(3H);5.35(1H);5.5(2H) |
I.05 | N | O | H | CH3 | 65-72 |
I.06 | N | O | H | CH2CH3 | 72-75 |
I.07 | N | O | H | CH(CH3)2 | 84-88 |
I.08 | N | O | 3-Cl | CH(CH3)2 | 106-108 |
I.09 | N | NH | H | CH2CH3 | 88-90 |
I.10 | N | NH | H | CH(CH3)2 | 86-88 |
I.11 | N | NH | 3-Cl | CH(CH3)2 | 116-118 |
通过下列实验可以显示通式I化合物对动物害虫的作用:
如下制备成:a)0.1%活性化合物浓度在丙酮中的溶液或b)10%活性化合物浓度在下列混合物中的乳剂 70%(重量)的环己酮、20%(重量)的Nekanil LN(LutensolRAP6,基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)和10%(重量)的EmulphorREL(EmulanREL,基于乙氧基化脂肪酸的乳化剂)并在a)的情况下用丙酮、在b)的情况下用水适当地稀释至所需浓度。
在实验结束时,确定在每一种情况下的最低浓度(活性极限值或最小浓度),在所述的最低浓度下,与未处理对照实验相比,化合物仍产生8 0-1 00%的抑制率或死亡率。对棉叶螨(Tetranychus telarius)的接触作用试验
将虫害严重的已长出第二对真叶的盆载矮化大豆用活性化合物的水制剂处理。在温室内保持5天后,用双目显微镜确定防治的成功性。
在此试验中,化合物I.01-I.07和I.09-I.11显示出为2至400ppm的活性极限值。对黑尾叶蝉(Nephotettix cincticeps)的接触作用试验
将圆形滤纸用活性化合物的水制剂处理,之后放上5只黑尾叶蝉成虫。24小时后,评价死亡率。在此试验中,化合物I.07和I.08显示出0.4mg的活性极限值。对有害真菌作用的实施例通过下列实验可以显示通式I化合物的杀真菌活性:
将活性化合物如下制备成20%浓度的在下列混合物中的乳剂:70%(重量)的环己酮、20%(重量)的NekanilRLN(Lutensol R AP6,基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)和10%(重量)的EmulphorREL(EmulanREL,基于乙氧基化脂肪酸的乳化剂)并根据所需浓度用水稀释。
对比化合物使用活性化合物A(EP-A 407872之表I,实施例25)对葡萄霜霉病(Plasmopara viticola)的作用
将盆载葡萄(品种:Muller Thurgau)用活性化合物制剂喷雾直至向下滴流。8天后,将植物用真菌葡萄生单轴霉的游动孢子悬浮液喷雾,并在20-30℃高湿下保持5天。评价前,在高湿下再保持16小时。评价用目测进行。
在此试验中,用250ppm的本发明化合物I.01-I.08、I.10和I.11处理的植物显示出5%或更低的侵染率,而用同样量的已知活性化合物A处理的植物的侵染率为25%。未处理(对照)植物的侵染率为75%。对稻瘟病(Pyricularia oryzae)的作用
将稻稠品种:Tai Nong 61)用活性化合物制剂喷雾直至向下滴流。24小时后,将植物用真菌稻梨孢的孢子水悬浮液喷雾,并在22-24℃相对湿度95-99%下保持6天。评价用目测进行。
在此试验中,用250ppm的本发明化合物I.01、I.02、I.04、I.06-I.08、I.10和I.11处理的植物显示出25%或更低的侵染率,而用同样量的已知活性化合物A处理的植物的侵染率为60%。未处理(对照)植物的侵染率为85%。
Claims (14)
1.式I的2-〔(2-烷氧基-6-三氟甲基嘧啶-4-基)氧亚甲基〕苯基乙酸衍生物其中的符号和取代基具有下列含意:U是CH或N;V是O或NH;R是C1-C6-烷基;R1是氰基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基或苯基;n是0或从1至4的整数,如果n大于1,R1可以不同。
2.根据权利要求1所要求的式I化合物,其中U是CH和V是O。
3.根据权利要求1所要求的式I化合物,其中U是N和V是O。
4.根据权利要求1所要求的式I化合物,其中U是N和V是NH。
6. 一种制备权利要求1所要求的式I化合物的方法,其中使式IV的砜衍生物
其中Ra是C1-C4-烷基在碱存在下与式V的醇反应。
HO-R V。
7.权利要求5中给出的式II所示嘧啶-4-醇。
8.权利要求5中给出的式II所示嘧啶-4-醇作为中间体的应用。
9.权利要求6中给出的式IV所示砜衍生物。
10.权利要求6中给出的式IV所示砜衍生物作为中间体的应用。
11.一种适合于防治动物害虫和有害真菌的组合物,它含有固体或液体载体和权利要求1中所要求的式I化合物。
12.一种防治动物害虫和有害真菌的方法,它包含用有效量的权利要求1中所要求的式I化合物来处理害虫或有害真菌或意欲保护使之不受侵害的材料、植物、土壤或种子。
13.权利要求1中所要求的式I化合物用于制备适合于防治动物害虫或有害真菌的组合物的应用。
14.权利要求1中所要求的式I化合物用于防治动物害虫或有害真菌的应用。
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CN95196288A Expired - Fee Related CN1100764C (zh) | 1994-11-17 | 1995-11-06 | 2-[(2-烷氧基-6-三氟甲基嘧啶-4-基)氧亚甲基]苯基乙酸衍生物、其制备和中间体以及应用 |
Country Status (26)
Country | Link |
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US (1) | US5935965A (zh) |
EP (1) | EP0792267B1 (zh) |
JP (1) | JP3973230B2 (zh) |
KR (1) | KR100421400B1 (zh) |
CN (1) | CN1100764C (zh) |
AR (1) | AR001048A1 (zh) |
AT (1) | ATE172196T1 (zh) |
AU (1) | AU698417B2 (zh) |
BG (1) | BG63499B1 (zh) |
BR (1) | BR9509786A (zh) |
CA (1) | CA2204039C (zh) |
CO (1) | CO4650142A1 (zh) |
CZ (1) | CZ288259B6 (zh) |
DE (1) | DE59503946D1 (zh) |
DK (1) | DK0792267T3 (zh) |
ES (1) | ES2124597T3 (zh) |
HU (1) | HU215791B (zh) |
IL (1) | IL115899A (zh) |
NZ (1) | NZ295382A (zh) |
PL (1) | PL183426B1 (zh) |
RU (1) | RU2166500C2 (zh) |
SK (1) | SK281783B6 (zh) |
TR (1) | TR199501451A2 (zh) |
TW (1) | TW308589B (zh) |
UA (1) | UA50725C2 (zh) |
WO (1) | WO1996016047A1 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101668748B (zh) * | 2007-05-25 | 2011-08-10 | 中国中化集团公司 | 取代嘧啶醚类化合物及其应用 |
CN103563904A (zh) * | 2013-11-11 | 2014-02-12 | 陕西农心作物科技有限公司 | 一种含嘧螨胺和吡螨胺的杀螨组合物 |
CN114605386A (zh) * | 2022-04-11 | 2022-06-10 | 青岛科技大学 | 一种含氟嘧啶硫醚芳香酯类杀虫杀螨剂 |
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KR19990072128A (ko) * | 1995-12-14 | 1999-09-27 | 스타르크, 카르크 | 2-(o-[피리미딘-4-일]메틸렌옥시)페닐 아세트산 유도체 및 유해 진균 및 동물 해충 억제를 위한 그의 용도 |
DE19609618A1 (de) * | 1996-03-12 | 1997-09-18 | Basf Ag | Pyrimidylphenyl- und -benzylether, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung |
CA2199899C (en) * | 1996-03-26 | 2004-05-11 | Beat Schmidt | Process for the preparation of a 2-alkoxy-6-(trifluoro-methyl)pyrimidin-4-ol |
DE10209145A1 (de) * | 2002-03-01 | 2003-09-04 | Bayer Cropscience Ag | Halogenbenzole |
KR101079544B1 (ko) | 2002-11-12 | 2011-11-02 | 바스프 에스이 | 글리포세이트-저항성 콩과식물의 수량 개선 방법 |
WO2004066905A2 (en) * | 2003-01-31 | 2004-08-12 | Lonza Ltd | Process for preparation of 2-alkoxy-6-(trifluoromethyl)pyrimidin-4-ol |
EP2039248A1 (de) * | 2007-09-21 | 2009-03-25 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102007045922A1 (de) * | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
MX2010012024A (es) * | 2008-05-07 | 2010-12-07 | Bayer Cropscience Ag | Combinaciones sinergicas de compuestos activos. |
EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
CN101875639B (zh) * | 2009-04-29 | 2012-07-25 | 中国中化股份有限公司 | 取代嘧啶醚类化合物及其应用 |
CN101906075B (zh) * | 2009-06-05 | 2012-11-07 | 中国中化股份有限公司 | 含取代苯胺基嘧啶基团的e-型苯基丙烯酸酯类化合物及其应用 |
EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
CN108314656B (zh) | 2018-02-27 | 2020-10-27 | 浙江工业大学 | 不饱和烃嘧啶硫醚类化合物及其制备方法与应用 |
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NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
DE3623921A1 (de) * | 1986-07-16 | 1988-01-21 | Basf Ag | Oximether und diese enthaltende fungizide |
GB8617648D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
DE3788928T2 (de) * | 1986-11-11 | 1994-05-19 | Zeneca Ltd | Chemische Verbindungen. |
EP0270252A3 (en) * | 1986-11-11 | 1990-04-04 | Imperial Chemical Industries Plc | Derivatives of propenoic acids used in agriculture |
GB2201152B (en) * | 1987-02-09 | 1991-08-14 | Ici Plc | Fungicidal propenoic acid derivatives |
IL87020A (en) * | 1987-07-11 | 1996-09-12 | Schering Agrochemicals Ltd | History of acrylic acid and their use as pesticides |
US5194438A (en) * | 1988-07-15 | 1993-03-16 | Basf Aktiengesellschaft | α-arylacrylates substituted by a trifluoromethylpyrimidinyloxy radical, fungicidal compositions and methods |
DE3823991A1 (de) * | 1988-07-15 | 1990-02-15 | Basf Ag | Heterocyclisch substituierte (alpha)-aryl-acrylsaeureester und fungizide, die diese verbindungen enthalten |
DE3835028A1 (de) * | 1988-10-14 | 1990-04-19 | Basf Ag | Oximether-derivate, verfahren zu ihrer herstellung und diese enthaltende fungizide |
NL8802710A (nl) * | 1988-11-04 | 1990-06-01 | Tno | Werkwijze voor het bepalen van een enzym en daarvoor geschikte kit en stof. |
DE3923068A1 (de) * | 1989-07-13 | 1991-01-24 | Basf Ag | Verfahren zur bekaempfung von schaedlingen mittels substituierter pyrimidine |
DE4030038A1 (de) * | 1990-09-22 | 1992-03-26 | Basf Ag | Ortho-substituierte phenylessigsaeureamide |
DE4116090A1 (de) * | 1991-05-17 | 1992-11-19 | Basf Ag | (alpha)-phenylacrylsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen und schadpilzen |
-
1995
- 1995-11-06 IL IL11589995A patent/IL115899A/en not_active IP Right Cessation
- 1995-11-06 CN CN95196288A patent/CN1100764C/zh not_active Expired - Fee Related
- 1995-11-07 WO PCT/EP1995/004375 patent/WO1996016047A1/de active IP Right Grant
- 1995-11-07 DE DE59503946T patent/DE59503946D1/de not_active Expired - Lifetime
- 1995-11-07 HU HU9702012A patent/HU215791B/hu not_active IP Right Cessation
- 1995-11-07 RU RU97110060/04A patent/RU2166500C2/ru not_active IP Right Cessation
- 1995-11-07 JP JP51650196A patent/JP3973230B2/ja not_active Expired - Fee Related
- 1995-11-07 EP EP95937877A patent/EP0792267B1/de not_active Expired - Lifetime
- 1995-11-07 AT AT95937877T patent/ATE172196T1/de active
- 1995-11-07 AU AU38714/95A patent/AU698417B2/en not_active Ceased
- 1995-11-07 SK SK576-97A patent/SK281783B6/sk not_active IP Right Cessation
- 1995-11-07 DK DK95937877T patent/DK0792267T3/da active
- 1995-11-07 BR BR9509786A patent/BR9509786A/pt not_active IP Right Cessation
- 1995-11-07 US US08/836,255 patent/US5935965A/en not_active Expired - Lifetime
- 1995-11-07 CZ CZ19971466A patent/CZ288259B6/cs not_active IP Right Cessation
- 1995-11-07 PL PL95320286A patent/PL183426B1/pl not_active IP Right Cessation
- 1995-11-07 ES ES95937877T patent/ES2124597T3/es not_active Expired - Lifetime
- 1995-11-07 KR KR1019970703297A patent/KR100421400B1/ko not_active IP Right Cessation
- 1995-11-07 NZ NZ295382A patent/NZ295382A/xx not_active IP Right Cessation
- 1995-11-07 UA UA97062851A patent/UA50725C2/uk unknown
- 1995-11-07 CA CA002204039A patent/CA2204039C/en not_active Expired - Fee Related
- 1995-11-16 TW TW084112144A patent/TW308589B/zh not_active IP Right Cessation
- 1995-11-16 CO CO95054216A patent/CO4650142A1/es unknown
- 1995-11-16 AR AR33425595A patent/AR001048A1/es unknown
- 1995-11-17 TR TR95/01451A patent/TR199501451A2/xx unknown
-
1997
- 1997-05-06 BG BG101461A patent/BG63499B1/bg unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101668748B (zh) * | 2007-05-25 | 2011-08-10 | 中国中化集团公司 | 取代嘧啶醚类化合物及其应用 |
CN103563904A (zh) * | 2013-11-11 | 2014-02-12 | 陕西农心作物科技有限公司 | 一种含嘧螨胺和吡螨胺的杀螨组合物 |
CN103563904B (zh) * | 2013-11-11 | 2015-12-02 | 陕西农心作物科技有限公司 | 一种含嘧螨胺和吡螨胺的杀螨组合物 |
CN114605386A (zh) * | 2022-04-11 | 2022-06-10 | 青岛科技大学 | 一种含氟嘧啶硫醚芳香酯类杀虫杀螨剂 |
CN114605386B (zh) * | 2022-04-11 | 2023-12-12 | 青岛科技大学 | 一种含氟嘧啶硫醚芳香酯类杀虫杀螨剂 |
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