CN1331560A - 基于吗啉或哌啶衍生物和肟醚衍生物的杀菌混剂 - Google Patents
基于吗啉或哌啶衍生物和肟醚衍生物的杀菌混剂 Download PDFInfo
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- CN1331560A CN1331560A CN99814749A CN99814749A CN1331560A CN 1331560 A CN1331560 A CN 1331560A CN 99814749 A CN99814749 A CN 99814749A CN 99814749 A CN99814749 A CN 99814749A CN 1331560 A CN1331560 A CN 1331560A
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- alkyl
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- halogen
- methyl
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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- A—HUMAN NECESSITIES
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- 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
- A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
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Abstract
本发明涉及一种杀菌混剂,包括增效有效量的下列活性组份:a)选自化合物(Ⅰa)、(Ⅰb)、(Ⅰc)和(Ⅰd)的吗啉或哌啶衍生物(Ⅰ)和式Ⅱ化合物,取代基X1至X5和R1至R4具有如下含义:X1代表C1－C4－卤代烷基,C1－C4－卤代烷氧基或卤素;X1至X5彼此独立地代表氢、卤素、C1－C4－烷基、C1－C4－卤代烷基、C1－C4－烷氧基或C1－C4－卤代烷氧基;R1代表C1－C4－烷基、C2－C6－链烯基、C2－C6－链炔基、C1－C4－烷基－C3－C7－环烷基、C1－C4－烷基－C3－C7－环烯基,以及这些基团可以带有选自如下的取代基:卤素、氰基和C1－C4－烷氧基;R2代表苯基或含有至少一个选自N、O和S的杂原子的5－或6－元饱和或不饱和杂环基,所述环状基团可以具有一个至三个选自下列的取代基:卤素、C1－C4－烷基、C1－C4－烷氧基、C1－C4－卤代烷基、C1－C4－卤代烷氧基、C1－C4－烷氧基－C2－C4－链烯基、C1－C4－烷氧基－C2－C4－链炔基;R3和R4彼此独立地代表C1－C4－烷基、C1－C4－烷氧基、C1－C4－烷硫基、N－C1－C4－烷基胺基、C1－C4－卤代烷基或C1－C4－卤代烷氧基。
Description
本发明涉及防治有害真菌的杀菌混剂和使用该混剂防治有害真菌的方法。
WO97/40673提出的杀菌混剂，其中除了来自肟醚和/或氨基甲酸酯的其他杀菌剂活性化合物之外，还包括式Ia、Ib和/或Ic的活性化合物。
[n＝10，11，12(60-70％)或13]
其他包括式Ia-Ic活性化合物的杀菌混剂公开在EP-A 797386、WO97/06681、EP-B 425857、EP-B 524496、EP-A 690792、WO 94/22308和EP-B 645087中。
1996年布赖顿作物保护会议(Brighton Crop ProtectionConference)“有害动物和病害”，第47-52页公开了式Id活性化合物：
DE 19722223中描述了式II化合物和来自strobilurins的活性化合物的混剂。
本发明的目的是提供其他特别有效的防治有害真菌、尤其是防治某些病症病害的混剂。
我们业已发现，使用一种混剂可以令人惊讶地达到该目的，该混剂作为活性化合物，包括增效有效量的本文开始定义的式I吗啉或哌啶衍生物，以及作为另外的杀菌活性组份的至少一种式II杀菌活性化合物
式中取代基X1至X5和R1至R4定义如下：
X1是C1-C4-卤代烷基、C1-C4-卤代烷氧基或卤素
X2至X5彼此独立地是氢、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基；
R1是C1-C4-烷基、C2-C6-链烯基、C2-C6-链炔基、C1-C4-烷基-C3-C7-环烷基，其中这些基团可以带有选自卤素、氰基和C1-C4-烷氧基的取代基，
R2是苯基或含有至少一个选自N、O和S的杂原子的5-或6-元环饱和或不饱和杂环基，其中所述杂环基可以具有一个至三个选自以下的取代基：卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-烷氧基-C2-C4-链烯基、C1-C4-烷氧基-C2-C4-链炔基，
R3和R4彼此独立地是氢、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、N-C1-C4-烷基胺基、C1-C4-卤代烷基或C1-C4-卤代烷氧基。
本发明混剂具有增效作用，因此它们特别适合用于防治有害真菌，尤其是白粉病真菌。
在本发明的上下文中，卤素是氟、氯、溴和碘，特别是氟、氯和溴。术语“烷基”包括直链和支链烷基。这些基团优选是直链或支链C1-C12-烷基，尤其是C1-C6-烷基。烷基例如是甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、[(原文中)脱漏]1，1-二甲基乙基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1，2-二甲基丙基、1，1-二甲基丙基、2，2-二甲基丙基、1-乙基丙基、正己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1，2-二甲基丁基、1，3-二甲基丁基、2，3-二甲基丁基、1，1-二甲基丁基、2，2-二甲基丁基、3，3-二甲基丁基、1，1，2-三甲基丙基、1，2，2-三甲基丙基、1-乙基丁基、2-乙基丁基、1-乙基-2-甲基丙基、正庚基、1-甲基己基、1-乙基戊基、2-乙基戊基、1-丙基丁基、辛基、癸基、十二烷基。
卤代烷基是被一个或多个卤原子、特别是氟和氯部分或完全卤代的上述定义的烷基。优选有1至3个卤原子存在，并且特别优选二氟甲烷[原文如此]和三氟甲基。
链烯基包括直链和支链C2-C6-链烯基。链烯基的例子是2-丙烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1，1-二甲基-2-丙烯基、1，2-二甲基-2-丙烯基、1-乙基-2-丙烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1，1-二甲基-2-丁烯基、1，1-二甲基-3-丁烯基、1，1-二甲基-3-丁烯基、1，2-二甲基-2-丁烯基、1，2-二甲基-3-丁烯基、1，3-二甲基-2-丁烯基、1，3-二甲基-3-丁烯基、2，2-二甲基-3-丁烯基、2，3-二甲基-2-丁烯基、2，3-二甲基-3-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1，1，2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基和1-乙基-2-甲基-2-丙烯基，特别是2-丙烯基、2-丁烯基、3-甲基-2-丁烯基和3-甲基-2-戊烯基。
链烯基可以被一个或多个卤原子、特别是氟和氯部分或完全卤代。优选具有1至3个卤原子。
链炔基包括直链和支链C3-C6-链炔基。链炔基的例子是2-丙炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-甲基-2-丁炔基、1，1-二甲基-2-丙炔基、1-乙基-2-丙炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-4-戊炔基、4-甲基-2-戊炔基、1，2-二甲基-2-丁炔基、1，1-二甲基-3-丁炔基、1，2-二甲基-3-丁炔基、2，2-二甲基-3-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基。
C1-C4-亚烷基-C3-C7-环烷基是通过C1-C4-亚烷基相连的C3-C7-环烷基，如环丙基、环丁基、环戊基或环己基。
合适的取代基R2是除苯基(未取代或取代)之外，特别是噻吩基、吡唑基、吡咯基、咪唑基、噻唑基、呋喃基、哒嗪基和嘧啶基。环系上优选取代基是卤素(特别是F和Cl)、C1-C4-烷氧基(特别是甲氧基)和C1-C4-烷基(特别是甲基、乙基)。环上取代基的数目可以是1至3个，特别是1或2个。特别优选苯基或取代的苯基、噻吩基、噻吩基-C1-C4-烷基、吡唑基和吡唑-C1-C4-烷基。
取代基R3和R4是C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、N-C1-C4-烷基胺基、C1-C4-卤代烷基或C1-C4-卤代烷氧基。优选取代基R3和R4是氢、F、Cl、甲基、乙基、甲氧基、甲硫基和N-甲基胺基。R3和R4也可以一起形成基团＝O。
吗啉或哌啶衍生物I(Ia：通用名称为丁苯吗啉，US-A4,202,894；Ib：通用名称为苯锈啶，US-A4,202,894；Ic：通用名称为十三吗啉，DE-A1164 152)，它们的制备和它们对有害真菌的作用是已知的，并且是商业上可购得的产品。
式II化合物和它们的制备方法描述在WO-A96/19442和较早期的申请DE1 97 41098.7和1 97 41099.5中。
在式II化合物中，优选如下定义的这些化合物，即，其中X1是C1-C4-卤代烷基，特别是三氟甲基，C1-C4-卤代烷氧基，特别是二氟甲氧基或三氟甲氧基或卤素，特别是氯以及X2和X3是氢原子或卤素，特别是氢原子。X4和X5优选是氢、卤素(特别是Cl或F)、C1-C4-烷氧基(特别是甲氧基或乙氧基)、C1-C4-卤代烷基(特别是三氟甲基)或C1-C4-卤代烷氧基(特别是三氟甲氧基)。
优选取代基R1是C1-C4-烷基(甲基、乙基、正丙基和异丙基和叔丁基)、C1-C4-亚烷基-C3-C7-环烷基、C1-C4-链烯基(特别是乙烯基、丙烯基和丁烯基，其中可以被取代，特别是被卤素(优选Cl)取代)、丙炔基、氰基甲基和甲氧基甲基。在C1-C4-亚烷基-C3-C7-环烷基取代基中，亚甲基取代的化合物，特别是亚甲基环丙基、亚甲基环戊基、亚甲基环己基和亚甲基环己烯基是特别优选的。在这些取代基的环上可以被取代，优选被卤素取代。
合适的取代基R2是除苯基(未取代或取代)之外，特别是噻吩基、吡唑基、吡咯基、咪唑基、噻唑基、呋喃基、哒嗪基和嘧啶基。在这些环系上优选的取代基是卤素(特别是F和Cl)、C1-C4-烷氧基(特别是甲氧基)和C1-C4-烷基(特别是甲基、乙基)。环上取代基的数目可以是1至3个，特别是1或2个。特别优选苯基或取代苯基。
优选的式II化合物示于在上文中已提到的WO96/019442的表中。在这些化合物中，又特别优选下表1中所列的化合物(R3和R4均为氢)。
表1
| No. | X1 | X2 | X3 | X4 | X5 | R1 | R2 |
| II.1 | CF3 | H | H | H | H | 乙基 | Ph-4-OMe |
| II.2 | CF3 | H | H | H | H | 甲基 | Ph-4-OMe |
| II.3 | CF3 | H | H | H | H | -CH2-cPr | 2-噻吩基 |
| II.4 | CF3 | H | H | H | H | -CH2-cPr | 3-噻吩基 |
| II.5 | CF3 | H | H | H | H | -CH2-cPr | Ph-2，4-F2 |
| II.6 | CF3 | H | H | H | H | -CH2-cPr | Ph-2-F |
| II.7 | CF3 | H | H | H | H | -CH2-cPr | Ph-2-F-4-OMe |
| II.8 | CF3 | H | H | H | H | -CH2-cPr | Ph-3-Me |
| II.9 | CF3 | H | H | H | H | -CH2-cPr | Ph-3-Me-4-OMe |
| II.10 | CF3 | H | H | H | H | -CH2-cPr | Ph-4-F |
| II.11 | CF3 | H | H | H | H | -CH2-cPr | Ph-4-Me |
| II.12 | CF3 | H | H | H | H | -CH2-cPr | Ph-4-OMe |
| II.13 | CF3 | H | H | H | H | -CH2-cPr | Ph |
| II.14 | CF3 | H | H | H | H | -CH2-CH＝CH2 | Ph |
| II.15 | CF3 | H | H | H | H | -CH2-CH＝CH2 | Ph-4-OMe |
| II.16 | CF3 | H | H | H | H | -CH2-CH＝CCl2 | Ph-4-OMe |
| II.17 | CF3 | H | H | H | F | -CH2-CH3 | Ph-4-OMe |
| II.18 | CF3 | H | H | H | F | -CH2CH3 | Ph |
| II.19 | CF3 | H | H | H | F | -CH3 | Ph-4-OMe |
| II.20 | CF3 | H | H | H | F | -CH2-cPr | Ph |
| II.21 | CF3 | H | H | H | F | -CH2-cPr | Ph-2-F |
| II.22 | CF3 | H | H | H | F | -CH2-cPr | Ph-2，4-F2 |
| II.23 | CF3 | H | H | H | F | -CH2-cPr | Ph-2-F-3-Me |
| II.24 | CF3 | H | H | H | F | -CH2-cPr | Ph-2-F-4-OMe |
| II.25 | CF3 | H | H | H | F | -CH2-cPr | Ph-3，5-Me2 |
| II.26 | CF3 | H | H | H | F | -CH2-cPr | 3-甲基吡唑-1-基 |
| II.27 | CF3 | H | H | H | F | -CH2-cPr | 3-甲基-2-噻吩基 |
| II.28 | CF3 | H | H | H | F | -CH2-cPr | 2-噻吩基 |
| II.29 | CF3 | H | H | H | F | -CH2-cPr | 3-噻吩基 |
| II.30 | CF3 | H | H | H | F | -CH2-CHF2 | Ph-4-OMe |
| II.31 | CF3 | H | H | H | F | -CH2-OCH3 | Ph-4-OMe |
| II.32 | CF3 | H | H | H | F | -CH2-OCH3 | Ph |
| No. | X1 | X2 | X3 | X4 | X5 | R1 | R2 |
| II.33 | CF3 | H | H | H | F | -CH2CN | Ph-4-Ome |
| II.34 | CF3 | H | H | H | F | -CH2CN | Ph |
| II.35 | CF3 | H | H | H | F | -CH2-C≡CH | Ph |
| II.36 | CF3 | H | H | H | F | -CH2-C≡CH | Ph-4-OMe |
| II.37 | CF3 | H | H | H | F | -CH2-C≡CH | ph-2-F |
| II.38 | CF3 | H | H | H | F | -CH2-C≡CH | Ph-4-Me |
| II.39 | CF3 | H | H | H | F | -CH2-C≡CH | 2-噻吩基 |
| II.40 | CF3 | H | H | H | F | -CH2-C≡CH | Ph-2-F-4-OMe |
| II.41 | CF3 | H | H | H | F | 异丙基 | Ph |
| II.42 | CF3 | H | H | H | F | 正丁基 | Ph |
| II.43 | CF3 | H | H | H | F | 正丙基 | Ph |
| II.44 | CF3 | H | H | H | F | 叔丁基 | Ph |
| II.45 | CF3 | H | H | H | Cl | -CH3 | |
| II.46 | CF3 | H | H | H | Cl | -CH2CN | Ph-4-OMe |
| II.47 | CF3 | H | H | H | Cl | -CH2-OMe | Ph-4-OMe |
| II.48 | CF3 | H | H | H | Cl | -CH2-cPr | Ph |
| II.49 | CF3 | H | H | H | Cl | -CH2-cPr | 3-甲基吡唑-1-基 |
| II.50 | CF3 | H | H | H | Cl | -CH2-cPr | 2-噻吩基 |
| II.51 | CF3 | H | H | H | Cl | -CH2-cPr | Ph-2，4-F2 |
| II.52 | CF3 | H | H | H | Cl | -CH2-C≡CH | Ph-4-OMe |
| II.53 | CF3 | H | H | H | CF3 | -CH3 | Ph-4-OMe |
| II.54 | CF3 | H | H | H | CF3 | -CH2CH2Cl | Ph-4-OMe |
| II.55 | CF3 | H | H | H | CF3 | -CH2-cPr | 2-噻吩基 |
| II.56 | CF3 | H | H | H | CF3 | -CH2-cPr | Ph-2-F-5-Me |
| II.57 | CF3 | H | H | H | CF3 | -CH2-cPr | Ph-4-OMe |
| II.58 | CF3 | H | H | H | CF3 | -CH2-cPr | Ph |
| II.59 | CF3 | H | H | H | OCH3 | -CH2CH3 | Ph-4-OMe |
| II.60 | CF3 | H | H | H | OCH3 | -CH2-cPr | Ph-4-OMe |
| II.61 | CF3 | H | H | H | OCH3 | -CH2-cPr | Ph |
| II.62 | CF3 | H | H | Cl | F | -CH2-CH2Cl | Ph |
| II.63 | CF3 | H | H | Cl | F | -CH2-CH＝CH2 | Ph-4-OMe |
| II.64 | CF3 | H | H | Cl | F | -CH2-cPr | 2-噻吩基 |
| II.65 | CF3 | H | H | Cl | F | -CH2-cPr | Ph-2-F |
| II.66 | CF3 | H | H | Cl | F | -CH2-cPr | Ph |
| II.67 | CF3 | H | H | Cl | F | -CH2-cPr | Ph-2-F-5-Me |
| II.68 | CF3 | H | H | Cl | Cl | -CH2-CH＝CH2 | Ph-4-OMe |
| II.69 | CF3 | H | H | Cl | Cl | -CH2CH2Cl | Ph |
| II.70 | CF3 | H | H | Cl | Cl | -CH2CH3 | Ph-2-F-5-Me |
| No. | X1 | X2 | X3 | X4 | X5 | R1 | R2 |
| II.71 | CF3 | H | H | Cl | Cl | -CH2-cPr | Ph-3，5-Me2 |
| II.72 | CF3 | H | H | SCH3 | F | -CH2-cPr | Ph-4-OMe |
| II.73 | CF3 | H | H | OCH3 | F | -CH2-cPr | Ph-4-OMe |
| II.74 | CF3 | H | F | H | H | -CH2-cPr | Ph |
| II.75 | CF3 | H | F | H | H | -CH2-CH3 | Ph-4-OMe |
| II.76 | CF3 | H | H | F | F | -CH2CH3 | Ph |
| II.77 | CF3 | H | H | F | F | -CH2-CH2Cl | Ph-2-F-5-Me |
| II.78 | CF3 | H | H | F | F | -CH2-OCH3 | Ph-4-OMe |
| II.79 | CF3 | H | H | F | F | -CH2-cPr | Ph |
| II.80 | CF3 | H | H | F | F | -CH2-cPr | 3-甲基吡唑-1-基 |
| II.81 | CF3 | H | H | F | F | -CH2-cPr | 3-甲基-2-噻吩基 |
| II.82 | CF3 | H | H | F | F | -CH2-cPr | Ph-2-F-3-Me |
| II.83 | CF3 | H | H | F | F | -CH2-cPr | Ph-2-F-4-OMe |
| II.84 | CF3 | H | H | F | F | -CH2-cPr | Ph-2-F-5-Me |
| II.85 | CF3 | H | H | F | F | -CH2-cPr | Ph-4-OMe |
| II.86 | CF3 | H | H | F | F | -CH2-cPr | Ph-4F |
| II.87 | CF3 | H | H | F | F | i-propyl | Ph-4-OMe |
| II.88 | CF3 | H | H | F | F | n-butyl | Ph-4-OMe |
| II.89 | CF3 | H | H | F | F | -CH2-C≡CH | Ph-4-OMe |
| II.90 | CF3 | H | H | CF3 | F | -CH3 | Ph-4-OMe |
| II.91 | CF3 | H | H | CF3 | F | -CH2-CH＝CH2 | Ph |
| II.92 | CF3 | H | H | CF3 | F | -CH2-cPr | Ph |
| II.93 | CF3 | H | H | Cl | C1 | -CH2-cHxe-3 | Ph |
| II.94 | CF3 | H | H | F | H | -CH2-cPr | Ph-4-F |
| II.95 | CF3 | H | H | Cl | Cl | -CH2-cHex | Ph |
| II.96 | CF3 | H | H | H | F | -CH2-SCH3 | Ph |
| II.97 | CF3 | H | H | H | F | -CH2-SOCH3 | Ph |
| II.98 | CF3 | H | H | H | F | -CH2-SO2CH3 | Ph |
| II.99 | CF3 | H | H | H | F | -CH2-NHMe | Ph |
| II.100 | CF3 | H | H | H | F | CH2-CONH2 | Ph |
| II.101 | CF3 | H | H | H | F | CH2CON(CH3)2 | Ph |
在上述表中，cPr是环丙基，cHxe-n是在n-位上不饱和的环己烯基，c-Hex是环己基和Ph是苯基。
特别优选这样的式II化合物，即，其中R1是基团CH2-cPr和R2是未取代或取代的苯基。在这些化合物中，又优选X4和X5[原文如此]各为卤素，优选F的那些化合物。
其他优选式II化合物示于下面表2和表3中。
表2：式II′化合物式中取代基定义如下：
| No. | X1 | R′ | m.p.(℃) |
| II.102 | H | 4-CH3-C6H4-CH2 | 86-88 |
| II.103 | H | 4-F-C6H4-CH2 | 79-81 |
| II.104 | H | 4-Cl-C6H4-CH2 | 105-107 |
| II.105 | H | 4-CH3O-C6H4-CH2 | 73-76 |
| II.106 | H | 4-CF3-C6H4-CH2 | |
| II.107 | 5-F | 4-CH3-C6H4-CH2 | 87-90 |
| II.108 | 5-F | 4-F-C6H4-CH2 | 71-74 |
| II.109 | 5-F | 4-Cl-C6H4-CH2 | 85-87 |
| II.110 | 5-F | 4-CH3O-C6H4-CH2 | 90-92 |
| II.111 | 5-F | 4-CF3-C6H4-CH2 | |
| II.112 | H | 2-噻吩基甲基 | 87-89 |
| II.113 | H | 3-噻吩基甲基 | |
| II.114 | 5-F | 2-噻吩基甲基 | 90-93 |
| II.115 | 5-F | 3-噻吩基甲基 | |
| II.116 | 5-F | 3-CH3-C6H4-CH2 | 72-75 |
| II.117 | 5-F | 2-F-C6H4-CH2 | 73-76 |
| II.118 | 5-F | 4-CH2FO-C6H4-CH2 | 油状物 |
表3：式II″化合物
| No. | OX1 | X2 | R1 | R″ | m.p.℃ |
| II.119 | CHF2 | H | C2H5 | C6H5-CH2 | |
| II.120 | CHF2 | H | C2H5 | 4-CH3O-C6H4-CH2 | |
| II.121 | CHF2 | H | CH2-CH＝CH2 | C6H5-CH2 | |
| II.122 | CHF2 | H | CH2-C≡CH | C6H5-CH2 | |
| II.123 | CHF2 | H | CH2-C≡CH | 4-CH3O-C6H4-CH2 | |
| II.124 | CHF2 | H | cPr | C6H5-CH2 | |
| II.125 | CF3 | H | cPr | C6H5-CH2 | |
| II.126 | CHF2 | H | cPr | 4-F-C6H4-CH2 | 75-77 |
| II.127 | CHF2 | H | cPr | 4-Cl-C6H4-CH2 | 81-83 |
| II.128 | CHF2 | H | cPr | 4-CH3O-C6H4-CH2 | 57-59 |
| II.129 | CHF2 | H | cPr | 4-CF3-C6H4-CH2 | |
| II.130 | CHF2 | H | cPr | 2-噻吩基甲基 | 油状物 |
| II.131 | CHF2 | H | cPr | 3-噻吩基甲基 | 油状物 |
| II.132 | CHF2 | H | cPr | 吡唑基-1-甲基 | |
| II.133 | CHF2 | H | cPr | 4-CH3-C6H4-CH2 | |
| II.134 | CHF2 | 5-F | CH2-CH＝CH2 | C6H5-CH2 | |
| II.135 | CHF2 | 5-F | CH2-CH＝CH2 | 4-CH3-C6H4-CH2 | |
| II.136 | CHF2 | 5-F | CH2-C≡CH | C6H5-CH2 | |
| II.137 | CHF2 | 5-F | CH2-C≡CH | 4-CH3O-C6H4-CH2 | |
| II.138 | CHF2 | 5-F | cPr | C6H5-CH2 | 62-65 |
| II.139 | CHF2 | 5-F | cPr | 4-F-C6H4-CH2 | 64-67 |
| II.140 | CHF2 | 5-F | cPr | 4-Cl-C6H4-CH2 | 72-75 |
| II.141 | CHF2 | 5-F | cPr | 4-CH3-C6H4-CH2 | 74-76 |
| II.142 | CHF2 | 5-F | cPr | 4-CH3O-C6H4-CH2 | 79-81 |
| II.143 | CHF2 | 5-F | cPr | 4-CF3-C6H4-CH2 | |
| II.144 | CF3 | 5-F | cPr | C6H5-CH2 | |
| II.145 | CHF2 | 4-F | cPr | C6H5-CH2 | |
| II.146 | CHF2 | 4-F | cPr | 4-CH3O-C6H4-CH2 | |
| II.147 | CHF2 | H | cPr | 4-CH3-C6H4-CH2 | 69-71 |
这些化合物的物理数据和它们的制备方法在已经提到的WO96/19442、DE197441098.7和DE19741099.5中给出。
化合物I和II的比例可以在较宽的范围内变化；优选所用活性化合物的比例按重量计为20∶1至1∶20，特别是10∶1至1∶10。
当加工混剂时，优选使用纯品有效成分I和II，混剂中可以混入另外的防治有害真菌或其他有害生物，如昆虫、螨类或线虫的有效成分，或者也可以混入其他的除草或生长调节的有效成分或肥料。
化合物I和II的混剂、或化合物I和II可以同时、结合地或分别地施用，对植物病原真菌、特别是来自子囊菌纲、担子菌纲、藻菌纲和半知菌纲的种类均显示出突出的广谱活性。它们中的一些品种具有内吸作用，因此可以作为叶面和土壤处理的杀菌剂使用。
它们对于各种作物及种子上的大量的真菌病害具有特别重要的意义，这些作物如棉花、蔬菜类(如黄瓜、菜豆、番茄、马铃薯和葫芦科植物)、大麦、禾草、燕麦、香蕉、咖啡、玉米、果树类、稻、黑麦、大豆、葡萄藤、小麦、观赏植物、甘蔗。
它们特别适合用于防治下列植物病源真菌病害：禾谷类白粉病(白粉菌)，葫芦科植物白粉病，苹果白粉病，葡萄白粉病，禾谷类锈病，棉花、稻和草坪上的丝核菌属(菌核病)，禾谷类和甘蔗的黑粉菌属(黑穗病)，苹果黑星病，禾谷类网斑病(Helminthosporium)，小麦颖枯病，草莓、蔬菜、观赏植物和葡萄的灰葡萄孢(灰霉病)，落花生尾孢(褐斑病)，小麦和大麦的眼斑病(Pseudocercosporella herpotrichoides)，稻瘟病，马铃薯和番茄的致病疫霉菌(晚疫病)，葡萄霜霉病，啤酒花和黄瓜的假霜霉属(霜霉病)，蔬菜和果树的链格孢属，香蕉球腔菌属和各种植物的镰孢属和轮枝孢属。
另外，它们可以用于材料保护(如木材保护)，如防治由拟青霉菌引起的木材腐烂。
化合物I和II可以同时，即，一起或分开使用，或在分开使用的情况下，依次施用，一般都对防治效果没有任何影响。
取决于所需要的效果，特别是用于农作物区，本发明混剂的使用量为0.01至10kg/ha，优选0.1至5kg/ha，特别是0.2至3.0kg/ha。
化合物I施用量为0.01至25 kg/ha，优选0.01至10kg/ha，特别是0.05至5.0kg/ha。
相应地，在化合物II的情况下，其施用量为0.01至2kg/ha，优选0.02至2kg/ha，特别是0.02至1.0kg/ha。
用作种子处理时，每千克种子的该混剂施用量通常为0.001至250g，优选0.01至100g，特别是0.01至50g。
如果防治植物病原有害真菌，对种子、植株或播前或播后的土壤、或者芽前或苗后的土壤通过喷雾或喷粉分开使用或结合使用化合物I和II或化合物I和II的混剂都是有效的。
本发明的杀菌增效混剂或化合物I和II可加工成例如可直接喷雾溶液、粉剂和悬浮剂或高浓度水剂、油剂或其他悬浮剂、分散制剂、乳剂、油分散制剂、膏剂、粉尘剂、撒施剂或颗粒剂的剂型形式，通过喷雾、弥雾、喷粉、撒施或泼浇使用。使用的形式取决于预定的目的，在任何情况下，它们应该保证本发明的混剂得到尽可能良好均匀的分布。
剂型加工以已知的方法进行，如通过用溶剂和/或载体分散活性化合物，如果需要使用乳化剂或分散剂，如果以水作为稀释剂，也可以使用其他的有机溶剂作为助溶剂。适合该目的的辅助剂主要是：溶剂如芳烃类(如二甲苯)、氯代芳烃类(如氯苯)、链烷烃类(如矿物油馏份)、醇类(如甲醇、丁醇)、酮类(如环己酮)、胺类(如乙醇胺、二甲基甲酰胺)和水；载体如研磨的天然矿物(如高岭土、粘土、滑石、白垩)和研磨的合成矿物(如微细粉碎的硅石、硅酸盐)；乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐类和芳基磺酸盐类)和分散剂如木素亚硫酸盐废液或甲基纤维素。
合适的表面活性剂是芳烃磺酸类，如木素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸，以及脂肪酸类、烷基和烷基芳基磺酸类、烷基硫酸类、月桂基醚硫酸类和脂肪醇硫酸类的碱金属盐、碱土金属盐和铵盐，和磺化的十六醇、十七醇和十八醇的盐，以及脂肪醇乙二醇醚类的盐，磺化的萘及其衍生物与甲醛的缩合物，萘或萘磺酸与苯酚和甲醛的缩合物，聚氧乙烯辛基苯酚醚，乙氧基化的异辛基苯酚、辛基苯酚或壬基苯酚，烷基苯酚或三丁基苯基聚乙二醇醚，烷基芳基聚醚醇，异十三醇、脂肪醇/环氧乙烷缩合物，乙氧基化蓖麻油，聚氧乙烯烷基醚或聚氧丙烯烷基醚，月桂醇聚乙二醇醚乙酸酯，山梨醇酯类，木素亚硫酸盐废液或甲基纤维素。
用于撒施和喷粉的粉剂[(原文中)脱漏]撒施剂可以通过化合物I或II或化合物I和II的混合物与固体载体混合或一起研磨制备。
颗粒剂(如包衣颗粒、浸渍颗粒或均质颗粒)通常用一种或多种活性化合物与固体载体相结合来制备。
填料或固体载体是，例如矿物土，如硅石类、硅胶类、硅酸盐类、滑石、高岭土、石灰石、石灰、白垩、胶块粘土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁，合成矿物材料和化学肥料如硫酸铵、磷酸铵、硝酸铵、尿素和植物源产品如谷物粉、树皮粉、木屑和坚果壳粉、纤维素粉或其他的固体载体。
制剂中化合物I或II之一或化合物I和II的混合物含量按重量计通常为0.1至95％，优选0.5至90％。所用活性化合物纯度为90％至100％，优选95％至100％(依据核磁共振波谱或高效液相色谱[原文如此])。
化合物I或II、混合物，或相应制剂通过以下方法使用，即以杀菌有效量的混合物，或分开施用的情况下，以杀菌有效量的化合物I和II处理有害真菌、它们的侵染场所或植物、种子、土壤、场所、材料或空间以防止它们受真菌侵染。
可在有害真菌侵染之前或侵染之后进行施用。
含有活性化合物的制剂例子是：
I.含有90重量份活性化合物和10重量份N-甲基吡咯烷酮；该溶液剂适合以微细雾滴的形式使用；
II.一种混合物，含有20重量份活性化合物、80重量份二甲苯、10重量份8至10摩尔环氧乙烷与1摩尔N-单乙醇油酰胺的加成物、5重量份十二烷基苯磺酸钙、5重量份40摩尔环氧乙烷与1摩尔蓖麻油的加成物；通过在水中良好分散得到一种分散液。
III.一种水分散制剂，有20重量份活性化合物、40重量份环己酮、30重量份异丁醇、20重量份40摩尔环氧乙烷与1摩尔蓖麻油的加成物；
IV.一种水分散制剂，含有20重量份活性化合物、25重量份环己醇、65重量份沸点为210至280℃的矿物油馏份和10重量份40摩尔环氧乙烷与1摩尔蓖麻油的加成物；
V.一种混合物，含有80重量份活性化合物、3重量份二异丁基萘-1-磺酸钠、10重量份来自亚硫酸纸浆废液的木素磺酸钠和7重量份粉状硅胶，混合物在锤磨机中研磨；通过混合物在水中良好分散得到一种喷雾混合液；
VI.一种紧密混合物，含有3重量份活性化合物和97重量份微细粉碎的高岭土；该粉剂含3％重量活性化合物；
VII.一种紧密的混合物，含有30重量份活性化合物、92重量份粉状硅胶和8重量份喷在硅胶表面上的石蜡油；该制剂使活性化合物具有良好的粘着性能；
VIII.一种稳定的水分散制剂，含有40重量份活性化合物、10重量份苯酚磺酸/尿素/甲醛缩合物的钠盐、2重量份硅胶和48重量份水；该分散制剂可进一步稀释；
IX.一种稳定的油分散制剂，含有20重量份活性化合物、2重量份十二烷基苯磺酸钙、8重量份脂肪醇聚乙二醇醚、20重量份苯酚磺酸/尿素/甲醛缩合物的钠盐和88重量份石蜡矿物油。
应用实施例
本发明混剂的增效活性可通过下述试验证明：
在含有按重量计63％环己酮和27％乳化剂的混合物中，活性化合物分别或一起加工成10％乳油，用水稀释至所需要的浓度。
效果评价通过检测受侵染叶片面积的百分率进行。这些百分率转换成防治效果。防治效果(W)通过下面Abbot公式计算：
W＝(1－α/β)·100
α对应于处理植株的真菌侵染百分率％，和
β对应于未处理(对照)植株的真菌侵染百分率％
防效为0表示处理植株的侵染水平相当于未处理对照植株；防效为100表示处理植株没有被侵染。
活性化合物混剂的期望防效采用Colby公式计算[R.S.Colby，《杂草》(Weeds)，15，20-22(1967)]，并与观测防效比较。
Colby公式：E＝x＋y－x·y/100
E：表示当以浓度a和b使用活性化合物A和B混剂时，相对于未处理对照的期望防效％
x：表示当以浓度a使用活性化合物A时，相对于未处理对照的防治效果％
y：表示当以浓度b使用活性化合物B时，相对于未处理对照的防治效果％
应用实施例1—防治小麦白粉病的活性
品种为“Kanzler”的盆栽小麦的幼苗叶片用含有10％活性化合物、63％环己酮和27％乳化剂的储备溶液配成的活性化合物水乳液喷雾，直到雾滴滴下为止，喷雾后24h液膜干涸，用小麦白粉病菌(禾谷类白粉菌小麦型(Erysiphe graminis forma specialis tritici))孢子撒粉接种。然后把供试植株置于温度20—24℃和相对湿度60—90％的人工气候箱中培养7天。叶片受侵染的发展程度用目测法确定。
受侵染叶片面积百分数的目测法观察值转换成以百分率表示的相对于未处理对照的防效。防效为0表示和未处理植株同样的侵染程度，防效为100表示侵染程度为0％。活性化合物组合应用的期望防效采用Colby公式(Colby，S.R.“除草剂组合应用增效和拮抗反应的计算”，《杂草》(Weeds)，15(1967)，20-22页)计算，并与观测防效比较。
所用的组份II是表2中的化合物II.79和II.138。
试验结果列于下面表1和表2中：
表1：
| 实施例 | 活性化合物 | 浓度(ppm) | 相对于未处理对照的防效％ |
| 1C | 无 | (67％侵染) | 0 |
| 2C | 化合物II.79 | 10.25 | 5555 |
| 3C | 化合物II.138 | 0.6 | 65 |
| 4C | 化合物I.a(通用名称：丁苯吗啉) | 0.25 | 55 |
| 5C | 化合物I.b(通用名称：苯锈啶) | 0.25 | 55 |
| 6C | 化合物I.c(通用名称：十三吗啉) | 10.25 | 00 |
表2：
| 实施例 | 本发明混剂(浓度ppm) | 观测防效 | 计算防效* |
| 7 | 0.25ppm Ia＋0.25ppm II.79 | 96 | 80 |
| 8 | 1ppm Ic＋1ppm II.79 | 85 | 55 |
| 9 | 0.25ppm Ic＋0.25ppm II.79 | 90 | 55 |
| 10 | 0.25ppm Ib＋0.25ppm II.79 | 93 | 80 |
| 11 | 0.25ppm Ia＋0.06ppm II.138 | 100 | 84 |
| 12 | 0.25ppm Ic＋0.06ppm II.138 | 96 | 65 |
| 13 | 0.25ppm Ib＋0.06ppm II.138 | 25 | 84 |
*采用Colby公式计算
试验结果表明所有混合比例的观测防效均高于采用Colby公式预先计算的防效。
Claims (3)
1.一种杀菌混剂，作为活性组份包括增效有效量的以下组分：
a)选自化合物Ia、Ib、Ic和Id的吗啉或哌啶衍生物II
[n＝10，11，12(60-70％)或13]和b)式II化合物
式中取代基X1至X5和R1至R4定义如下：
X1是C1-C4-卤代烷基、C1-C4-卤代烷氧基或卤素；
X2至X5彼此独立地是氢、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基，
R1是C1-C4-烷基、C2-C6-链烯基、C2-C6-链炔基、C1-C4-烷基-C3-C7-环烷基，其中这些基团可以带有选自卤素、氰基和C1-C4-烷氧基的取代基，
R2是苯基或含有至少一个选自N、O和S的杂原子的5-或6-元饱和或不饱和杂环基，其中所述环状基团可以具有一至三个选自如下的取代基：卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-烷氧基-C2-C4-链烯基、C1-C4-烷氧基-C2-C4-链炔基，
R3和R4彼此独立地是氢、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、N-C1-C4-烷基胺基、C1-C4-卤代烷基或C1-C4-卤代烷氧基。
2.前述权利要求任一项所述的杀菌混剂，该杀菌混剂分成两部分，其中一部分包括在固体或液体载体中的一种或多种化合物I，以及另一部分包括在固体或液体载体中的一种或多种式II化合物。
3.一种防治有害真菌的方法，包括将权利要求1或2任一项的杀菌混剂处理真菌、它们的侵染场所或材料、植物、种子、土壤、场所或空间，以保护它们免受真菌侵染，其中化合物I和一种或多种式II化合物可以同时施用，也就是一起或分开施用，或依次施用。
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| CN102919241B (zh) * | 2010-12-08 | 2014-08-13 | 陕西美邦农药有限公司 | 一种含十三吗啉的杀菌组合物 |
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|---|---|---|---|---|
| DE3735555A1 (de) | 1987-03-07 | 1988-09-15 | Bayer Ag | Aminomethylheterocyclen |
| KR100242358B1 (ko) * | 1994-12-19 | 2000-02-01 | 쓰끼하시 다미까따 | 벤즈아미드 옥심 유도체, 그의 제법 및 농원예용 살균제 |
| JPH11511145A (ja) | 1995-08-17 | 1999-09-28 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌剤混合物 |
| US6156796A (en) * | 1996-06-04 | 2000-12-05 | Nippon Soda Co., Ltd. | Agricultural/horticultural fungicidal compositions |
-
1998
- 1998-12-19 DE DE19858911A patent/DE19858911A1/de not_active Withdrawn
-
1999
- 1999-11-12 UA UA2001075131A patent/UA72237C2/uk unknown
- 1999-11-30 TW TW088120875A patent/TW585741B/zh not_active IP Right Cessation
- 1999-12-11 HU HU0104754A patent/HUP0104754A3/hu unknown
- 1999-12-11 CN CNB998147494A patent/CN1158922C/zh not_active Expired - Fee Related
- 1999-12-11 CA CA002654713A patent/CA2654713A1/en not_active Abandoned
- 1999-12-11 CZ CZ20012196A patent/CZ294893B6/cs not_active IP Right Cessation
- 1999-12-11 AT AT99967931T patent/ATE238657T1/de not_active IP Right Cessation
- 1999-12-11 PL PL348414A patent/PL198430B1/pl unknown
- 1999-12-11 PT PT99967931T patent/PT1139749E/pt unknown
- 1999-12-11 DK DK99967931T patent/DK1139749T3/da active
- 1999-12-11 JP JP2000589040A patent/JP2002532522A/ja not_active Withdrawn
- 1999-12-11 AU AU24311/00A patent/AU771670B2/en not_active Ceased
- 1999-12-11 BR BR9916383-7A patent/BR9916383A/pt not_active Application Discontinuation
- 1999-12-11 KR KR1020017007637A patent/KR100692505B1/ko not_active IP Right Cessation
- 1999-12-11 DE DE59905363T patent/DE59905363D1/de not_active Expired - Lifetime
- 1999-12-11 ES ES99967931T patent/ES2198986T3/es not_active Expired - Lifetime
- 1999-12-11 US US09/868,515 patent/US7026315B1/en not_active Expired - Fee Related
- 1999-12-11 CA CA002356114A patent/CA2356114C/en not_active Expired - Fee Related
- 1999-12-11 EP EP99967931A patent/EP1139749B1/de not_active Expired - Lifetime
- 1999-12-11 WO PCT/EP1999/009803 patent/WO2000036917A1/de active IP Right Grant
- 1999-12-11 IL IL14344799A patent/IL143447A0/xx not_active IP Right Cessation
- 1999-12-11 SK SK869-2001A patent/SK8692001A3/sk unknown
- 1999-12-16 CO CO99078799A patent/CO5221026A1/es not_active Application Discontinuation
- 1999-12-17 AR ARP990106535A patent/AR021903A1/es active IP Right Grant
-
2001
- 2001-07-18 ZA ZA200105911A patent/ZA200105911B/xx unknown
-
2006
- 2006-01-17 US US11/332,221 patent/US20060154924A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103980290A (zh) * | 2013-12-06 | 2014-08-13 | 华东理工大学 | 具有杀虫活性的吗啉并环类化合物、及其制备和用途 |
| CN103980290B (zh) * | 2013-12-06 | 2016-08-17 | 华东理工大学 | 具有杀虫活性的吗啉并环类化合物、及其制备和用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2654713A1 (en) | 2000-06-29 |
| DK1139749T3 (da) | 2003-08-18 |
| TW585741B (en) | 2004-05-01 |
| CZ294893B6 (cs) | 2005-04-13 |
| ES2198986T3 (es) | 2004-02-01 |
| AU2431100A (en) | 2000-07-12 |
| KR20010104690A (ko) | 2001-11-26 |
| US7026315B1 (en) | 2006-04-11 |
| PL348414A1 (en) | 2002-05-20 |
| CO5221026A1 (es) | 2002-11-28 |
| CN1158922C (zh) | 2004-07-28 |
| DE59905363D1 (de) | 2003-06-05 |
| PT1139749E (pt) | 2003-09-30 |
| SK8692001A3 (en) | 2002-01-07 |
| HUP0104754A2 (hu) | 2002-05-29 |
| BR9916383A (pt) | 2001-09-11 |
| ZA200105911B (en) | 2002-07-18 |
| DE19858911A1 (de) | 2000-06-21 |
| WO2000036917A1 (de) | 2000-06-29 |
| US20060154924A1 (en) | 2006-07-13 |
| UA72237C2 (en) | 2005-02-15 |
| IL143447A0 (en) | 2002-04-21 |
| EP1139749A1 (de) | 2001-10-10 |
| EP1139749B1 (de) | 2003-05-02 |
| KR100692505B1 (ko) | 2007-03-09 |
| CZ20012196A3 (cs) | 2001-12-12 |
| CA2356114A1 (en) | 2000-06-29 |
| JP2002532522A (ja) | 2002-10-02 |
| PL198430B1 (pl) | 2008-06-30 |
| HUP0104754A3 (en) | 2002-12-28 |
| ATE238657T1 (de) | 2003-05-15 |
| CA2356114C (en) | 2009-05-05 |
| AR021903A1 (es) | 2002-09-04 |
| AU771670B2 (en) | 2004-04-01 |
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