CN107250127B - 除草化合物 - Google Patents
除草化合物 Download PDFInfo
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- CN107250127B CN107250127B CN201680009376.6A CN201680009376A CN107250127B CN 107250127 B CN107250127 B CN 107250127B CN 201680009376 A CN201680009376 A CN 201680009376A CN 107250127 B CN107250127 B CN 107250127B
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- 239000011593 sulfur Chemical group 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
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- ZRGSCNJDNKWIDN-UHFFFAOYSA-N tert-butyl N-methyl-N-(2-methyl-5-pyridin-3-ylpyrazol-3-yl)carbamate Chemical compound CN(C(OC(C)(C)C)=O)C=1N(N=C(C=1)C=1C=NC=CC=1)C ZRGSCNJDNKWIDN-UHFFFAOYSA-N 0.000 description 1
- RBNIYENBVMHGCZ-UHFFFAOYSA-N tert-butyl N-methyl-N-(3-methyl-1-pyrimidin-5-ylpyrazol-4-yl)carbamate Chemical compound CN(C(OC(C)(C)C)=O)C=1C(=NN(C=1)C=1C=NC=NC=1)C RBNIYENBVMHGCZ-UHFFFAOYSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
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- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
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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
- A01N43/74—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
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- A—HUMAN NECESSITIES
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- 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
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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
- A01N43/80—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 1,2
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- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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- A—HUMAN NECESSITIES
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- 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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- A—HUMAN NECESSITIES
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Abstract
本发明涉及除草活性的吡啶并‑/嘧啶并‑吡唑衍生物,连同涉及用于制备此类衍生物的方法和中间体。本发明进一步延伸到包括此类衍生物的除草组合物,连同延伸到此类化合物和组合物在有用植物的作物中控制不希望的植物生长中的用途,特别是在控制杂草中的用途。
Description
本发明涉及除草活性的吡啶并-/嘧啶并-吡唑衍生物,连同涉及用于制备此类衍生物的方法和中间体。本发明进一步延伸到包括此类衍生物的除草组合物,连同延伸到此类化合物和组合物在有用植物的作物中控制不希望的植物生长中的用途,特别是在控制杂草中的用途。
除草嘧啶并-咪唑是从WO 2005/047281已知的。在WO 2013/162715、WO 2013/162716、WO 2013/062981和WO 2012/061290 中描述了用作杀螨/杀昆虫/杀软体动物/杀线虫剂或用于在控制无脊椎动物害虫中的吡啶并-/嘧啶并-吡唑衍生物。
本发明是基于以下发现:如在本文所定义的具有化学式(I)的吡啶并-吡唑和嘧啶并-吡唑衍生物展示了出人意料地良好的除草活性。
因此,在本发明的第一个方面,提供了具有化学式(I)的化合物,
或其盐或N-氧化物作为除草剂的用途,其中Q是选自
X1是N或CR1;
R1是氢、卤素、氰基、C1-C6烷基、C3-C6环烷基、C2-C6烯基、 C2-C6炔基、C1-C6烷氧基、C(O)OR6或S(O)n(C1-C6烷基)、甲酰基、羟基、-C(O)NR6R7、NR6R7、苄氧基、C1-C6卤代烷氧基或C1-C6卤代烷基;
R2是氢、卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C(O)OR6、或S(O)n(C1-C6烷基)、C1-C6烷氧基、C1-C6卤代烷氧基;
n是0、1、或2;
R3是氢、氰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C2-C6烯氧基、C3-C10环烷基、NR6R7;
R4是O、S、或N(C1-C6烷基);
X2是O、S、或NR8;
R5是氢,C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C10环烷基, C3-C10环烯基,C1-C6卤代烷基,C2-C6卤代烯基,C1-C6烷氧基,C1-C6卤代烷氧基,C2-C6烯氧基,C2-C6炔氧基,C3-C10环烷氧基,C3-C10环烯氧基,C2-C6卤代烯氧基,C6-C10芳基或被从1至3个独立地选自卤素、硝基、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基的基团取代的C6-C10芳基;C3-C10杂环基或被从1至3个独立地选自卤素、硝基、氰基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、和C1-C3卤代烷氧基的基团取代的C3-C10杂环基;或NR6R7;
或R3和R5连同X2以及它们所连接的原子一起形成饱和或部分不饱和5-9元环系统,该5-9元环系统任选地包括1至3个独立地选自S、 O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代;
或R3和R8连同它们所连接的原子一起形成饱和或部分不饱和5-9 元环系统,该5-9元环系统任选地包括1至3个独立地选自S、O和N 的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代;
R6和R7各自独立地是氢、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、或C2-C6炔基,
或R6和R7连同它们所连接的氮原子一起形成饱和或部分不饱和 3-6元环,该3-6元环任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代;
R8是氢、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基或C2-C6炔基;C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯氧基、C2-C6炔氧基、 C3-C10环烷基氧基、C3-C10环烯氧基、C2-C6卤代烯氧基;
或R7和R8连同它们所连接的碳原子一起形成饱和或部分不饱和3-9元环,该3-9元环任选地包括1至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代,
R9是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、 C2-C6炔基、C1-C6卤代烷氧基、C1-C6烷氧基、或C3-C6环烷基;
R10是氢、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基硫基、-C(O)OR6、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、或C2-C6炔基。
具有化学式(I)的化合物可以作为不同的几何异构体或以不同的互变异构的形式存在。本发明涵盖了所有的此类异构体和互变异构体,以及它们的处于所有比例的混合物,连同同位素形式(例如氘化的化合物)的用途。
可能的情况是具有化学式(I)的化合物包含一个或多个不对称中心并且因此可以产生光学异构体和非对映异构体。尽管没有相对于立体化学示出,本发明包括所有此类光学异构体和非对映异构体连同外消旋的和拆分的对映异构体纯的R和S立体异构体以及这些R和S 立体异构体的其他混合物及其农用化学上可接受的盐的用途。
每个烷基部分单独或者作为较大基团(如烷氧基、烷硫基、烷氧基羰基、烷基羰基、烷氨基羰基或二烷氨基羰基等)的一部分可以是直链或支链的。典型地,该烷基是例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、新戊基、或正己基。烷基基团通常是C1-C6烷基基团(除了在已经更狭窄地定义时),但优选地是C1-C4烷基或C1-C3烷基基团,并且更优选地是C1-C2烷基基团 (例如甲基)。
烯基和炔基部分可以处于直链或支链的形式,并且这些烯基部分适当时可以是具有(E)-或(Z)-构型。烯基和炔基部分可以含有一个或多个任何组合的双和/或三键,但优选地含有仅一个双键(对于烯基来说) 或仅一个三键(对于炔基来说)。
烯基或炔基部分典型地是C2-C4烯基或C2-C4炔基,更具体地是乙烯基(ethenyl)(乙烯基(vinyl))、丙-2-烯基(烯丙基)、乙炔基、丙-2-炔基(炔丙基)、或丙-1-炔基。
优选地,术语环烷基是指环丙基、环丁基、环戊基或环己基。
在本说明书的背景下,术语“芳基”优选地意指苯基。如在此所用,术语“杂芳基”意指包含至少一个环杂原子并且由单环组成的芳香族环系统。优选地,单环将包含独立地选自氮、氧以及硫的1、2 或3个杂原子。典型地,“杂芳基”是呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、 1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、或1,3,5- 三嗪基。
杂环基基团以及杂环(单独的或作为更大基团(例如杂环基-烷基 -)的部分)是包含至少一个杂原子的环系统并且可以是处于单环或双环形式。优选地,杂环基基团将包含多达两个杂原子,这些杂原子将优选地选自氮、氧以及硫。杂环基团的实例包括氧杂环丁烷基、硫杂环丁烷基、氮杂环丁烷基以及7-氧杂-双环[2.2.1]庚-2-基。包含单个氧原子作为杂原子的杂环基基团是最优选的。杂环基基团优选地是3元至8元环,更优选地3元至6元环。
卤素(或卤代)涵盖了氟、氯、溴或碘。该卤素对应地应用于其他定义背景下的卤素,如卤代烷基或卤代苯基。
具有从1至6个碳原子链长的卤代烷基基团是,例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、 2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基、2,2,2-三氯乙基、七氟正丙基以及全氟正己基。
烷氧基基团优选地具有从1至6个碳原子的链长。烷氧基是,例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基或戊氧基或己氧基异构体,优选地是甲氧基和乙氧基。还应当领会的是,两个烷氧基取代基可以存在于相同碳原子上。
卤代烷氧基是,例如氟甲氧基、二氟甲氧基、三氟甲氧基、2,2,2- 三氟乙氧基、1,1,2,2-四氟乙氧基、2-氟乙氧基、2-氯乙氧基、2,2-二氟乙氧基或2,2,2-三氯乙氧基,优选地二氟甲氧基、2-氯乙氧基或三氟甲氧基。
C1-C6烷基-S-(烷基硫基)是,例如甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基,优选地是甲硫基或乙硫基。
C1-C6烷基-S(O)-(烷基亚磺酰基)是,例如甲基亚磺酰基、乙基亚磺酰基、正丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基或叔丁基亚磺酰基,优选地是甲基亚磺酰基或乙基亚磺酰基。
C1-C6烷基-S(O)2-(烷基磺酰基)是,例如甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基或叔丁基磺酰基,优选地是甲基磺酰基或乙基磺酰基。
具有化学式(I)的化合物可以与胺类(例如,氨水、二甲胺和三乙胺)、碱金属和碱土金属碱类或季铵碱类形成,和/或用作农学上可接受的盐。在用作成盐物的碱金属和碱土金属氢氧化物、氧化物、醇化物以及碳酸氢盐和碳酸盐之中,要强调的是锂、钠、钾、镁和钙的氢氧化物、醇化物、氧化物以及碳酸盐,但尤其是钠、镁和钙的那些。还可以使用对应的三甲基锍盐。
当具有化学式(I)的化合物含有碱部分时,该具有化学式(I)的化合物还可以与各种有机和/或无机酸(例如乙酸、丙酸、乳酸、柠檬酸、酒石酸、琥珀酸、富马酸、马来酸、丙二酸、扁桃酸、苹果酸、邻苯二甲酸、盐酸、氢溴酸、磷酸、硝酸、硫酸、甲磺酸、萘磺酸、苯磺酸、甲苯磺酸、樟脑磺酸以及类似地已知可接受的酸)形成(和/ 或用作)农学上可接受的盐。
具有化学式(I)的化合物还可以是/用作成盐过程中形成的水合物形式。
X1、X2、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10以及n的优选值是如以下列出的,并且根据本发明的具有化学式(I)的化合物可以包括所述值的任何组合。熟练的技术人员将理解,用于任何指定组的实施例的值可以与用于任何其他组的实施例的值组合,其中这些组合不相互排斥。
优选地,R1是氢、卤素、甲酰基、氰基、C1-C6烷氧基、C1-C6烷基磺酰基、C1-C6烷基硫基、C1-C6卤代烷氧基、-C(O)NR6R7、NR6R7、或C1-C6卤代烷基。更优选地,R1是氢、氟、氯、氰基、三氟甲基、甲氧基、二氟甲氧基、甲酰基、甲烷磺酰基、甲酰胺、甲硫醇或氨基。
优选地,R2是卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、 C2-C6烯基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基硫基、 -C(O)OR6、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、或C2-C6炔基。更优选地,R2是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、-C(=O)OR6、或C2-C6炔基。甚至更优选地,R2是甲基、三氟甲基、氯、溴、碘、氟、乙烯基、乙炔基、甲氧基羰基、-CO2H、或环丙基;
如上所述,R3是C1-C6烷基、C2-C6烯基、C2-C6炔基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C2-C6烯氧基、C3-C10环烷基、或NR6R7。优选地,R3是氢、或C1-C3烷基。更优选地,R3是氢或甲基。
优选地,R4是O。
优选地,X2是O、或NR8。
优选地,R5是C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C10环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯氧基、C2-C6炔氧基、C3-C10环烷氧基、C3-C10环烯氧基、 C2-C6卤代烯氧基、C6-C20芳基、C3-C20杂环基、或NR6R7。更优选地, R5是甲基、乙基、异丙基、叔丁基或叔丁氧基。
优选地,R8是氢、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、或C2-C6炔基。
优选地R9是氢、氯、氟、溴、甲基或三氟甲基。更优选地,R9是氢、氯、氟、或溴。甚至更优选地,R9是氢、或氯。
优选地,R10是C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基硫基、-C(O)OR6、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、或C2-C6炔基。更优选地, R10是C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、-C(O)OR6、或C2-C6炔基。甚至更优选地R10是甲基、三氟甲基或二氟甲基。
在实施例中(其中R3和R5,连同X2以及它们所连接的原子一起形成饱和或部分不饱和5-9元环系统,该5-9元环系统任选地包括1 至3个独立地选自S、O和N的杂原子并且任选地被1至3个独立地选自卤素或C1-C6烷基的基团取代),优选的是形成以下基团T(即 T1或T2):
其中X2和R4是如本文所定义的,并且A表示与吡啶并/嘧啶并- 吡唑部分的附接点。优选地,在基团T1和T2中,R4是O并且X2是 O或NR8。甚至更优选地,R4是O并且X2是O或NR8,并且R8是甲基。
下表1提供了用于根据本发明所述的用途的具有化学式(I)的除草化合物的具体实例。
表1具有化学式(I)的化合物
具有化学式(I)的化合物可以使用有机化学领域中技术人员已知的技术,根据以下方案进行制备,其中取代基X1、X2、R1、R2、 R3、R4、R5、R6、R7、R8、R9、R10和n具有(除非另有明确说明) 上文所描述的定义。下文描述了用于生产具有化学式(I)的化合物的通用方法。除非在本文中另外说明,否则该合成方法源自WO 2013/162715、WO 2013/162716、WO 2013/062981和WO 2012/061290。用于制备本发明的化合物的起始材料可以购买自通常的商品供应商或者可以由已知的方法制备。起始材料以及中间体可以在使用前,通过现有技术的方法说明(例如层析、结晶、蒸馏和过滤)进行纯化。
方案1
如上述方案1所示,在合适的碱(如氢化钠)和合适的溶剂(如 DMSO)存在下,用二硫化碳和碘甲烷处理经适当取代的具有化学式 (II)的杂环甲基酮可以得到具有化学式(III)的化合物。可以在碱(如三乙胺)存在下,在溶剂(如乙醇)中,用合适的具有化学式(XXXII) 的胺处理具有化学式(III)的化合物,以提供具有化学式(IV)的化合物和/或它们的立体异构体。
可以通过如WO 2013/162716中所述,在极性质子溶剂(如乙醇) 中,用适当经取代的具有化学式(XXX)的肼进行处理,将具有化学式(IV)的化合物进一步转化成具有化学式(V)的氨基吡唑。可以在非质子溶剂(例如二氯甲烷)中或在使用过量的碱(例如吡啶)作为溶剂来得到具有化学式(Ib)的化合物的条件下,在合适的碱(例如吡啶)存在下,通过与合适的具有化学式(XXXI)的试剂(其中LG 是合适的离去基团(例如,该试剂(XXXI)是二碳酸二叔丁酯))反应,对得到的具有化学式(V)的氨基吡唑进行进一步加工。
作为替代方案,当R9=H时,可以在合适的溶剂(如乙腈)中,用合适的试剂(如N-氯代琥珀酰亚胺)对具有化学式(V)的化合物进行卤化,得到具有化学式(VI)的化合物,其进而可以在非质子溶剂(例如二氯甲烷)中或在使用过量的碱(例如吡啶)作为溶剂来得到(Ib)的条件下,在合适的碱(例如吡啶)存在下,通过与合适的具有化学式(XXXI)的试剂(例如,二碳酸二叔丁酯)反应进行进一步加工。
如下面方案2中所示,具有化学式(Ib)的化合物可以经由起始于β-二酮酸酯(例如2,4-二氧代-4-(3-吡啶基)丁酸乙酯)的序列进行制备,其中该二酮酸酯可以通过在合适的碱(例如氢化钠)存在下,在合适的溶剂(例如THF)中,将适当取代的具有化学式(II)的杂芳基酮与草酸二酯(例如草酸二乙酯)缩合来制备。
具有化学式(VII)的β-二酮酸酯可以与适当取代的具有化学式 (XXX)的肼在极性质子溶剂(如乙醇)中反应,以给出具有化学式 (VIII)的吡嗪酯。在典型条件(例如氢氧化钠,水和1,4-二噁烷)下进行碱性皂化,然后根据需要分离,得到具有化学式(IX)的酸,该酸可以与合适的试剂(如二苯基磷酰叠氮化物(DPPA))反应形成酰基叠氮化物,该酰基叠氮化物经历原位库尔修斯反应,以产生异氰酸酯,然后用合适的具有化学式(XXXIII)的醇(X2=O)淬灭该异氰酸酯,得到具有化学式(Ic)的氨基甲酸酯。然后可以在温和条件下(使用例如在极性非质子溶剂如N,N-二甲基甲酰胺中氢化钠)用合适的具有化学式(XXXIV)的烷基化剂进一步烷基化这些氨基甲酸酯,其中LG是合适的离去基团(这样的烷基化试剂的实例是甲基碘),得到具有化学式(Ib)的化合物。
方案2
如上面方案3所示,制备具有化学式(Ib)的化合物的另一种方法是通过具有化学式(X)的化合物(其可以通过各种已知方法制备,包括但不限于,由Ridge等人在J.Med.Chem.1979,22,1385-1389[药物化学杂志1979,22,1385-1389]中描述的那些)。具有化学式(X)的化合物可以与合适的具有化学式(XXX)的肼缩合,得到具有化学式 (XI)的区域异构的氨基吡唑。
在非质子溶剂(例如二氯甲烷)中或在使用过量的碱(例如吡啶) 作为溶剂的条件下在合适的碱(例如吡啶)存在下,可以将所得到的具有化学式(XI)的氨基吡唑通过与具有化学式(XXXI)的合适试剂(如二碳酸二叔丁基酯)反应来进行进一步加工,来提供具有化学式(Ic)的化合物(分离形成的产品混合物之后)即,本发明所述化合物的实例,其中R3=H)。在典型的极性非质子溶剂(如N,N-二甲基甲酰胺)中,用合适的碱(例如氢化钠)去质子化后,用合适的具有化学式(XXXIV)的亲电子试剂(如甲基碘)进行烷基化,产生具有化学式(Ib)的化合物。
方案3
如方案4所示,在合适的碱存在下和在合适的溶剂中,通过用具有化学式(XLI)的化合物(其中LG是合适的离去基团,例如Cl, Br,I或OT)进行烷基化,可以可替代地由具有化学式(XIa)的氨基吡唑(具有化学式XI的化合物,其中R10=H)制备具有化学式(XI) 的氨基吡唑(其中R10≠H)。合适的溶剂/碱组合包括Cs2CO3/DMF (参见例如M.K.Ameriks等人,生物有机与药物化学快报(2009),613 [Bioorg.Med.Chem,Lett.(2009),613])和KOH/丙酮(参见例如G. Guillaumet等人,Bioorg.Med.Chem.Lett.(2006),1078[生物有机与药物化学快报(2006),1078])。
方案4
如方案5所示,如在WO 2013/062981中所传授的,可以在极性质子溶剂(如乙醇)中,使用氢气、合适的催化剂(例如氧化铝上的 5%Pd)和酸溶液(例如50%HBr),在氢化条件下,将具有化学式 (XII)的化合物的硝基官能度还原成胺,得到具有化学式(XIII)的化合物(其可作为盐(例如HBr盐)被分离)。
在溶剂(如水/THF)和合适的碱(如碳酸氢钠)的混合物存在下,可以使用合适的具有化学式(XXXI)的试剂(如二碳酸二叔丁酯)将具有化学式(XIII)的化合物转化成具有化学式(XIIV)的化合物。
如在WO 2013/062981中所传授的,在具有合适碱(如磷酸钾) 的极性非质子溶剂(如乙腈)中,在催化量的氯化铜(II)与配体(如 N,N'-二甲基乙烷-1,2-二胺)的存在下,可以通过与具有化学式(XV) 的化合物反应,将具有化学式(XIIV)的化合物进一步转化成具有化学式(Id)的化合物,得到具有化学式(Id)的化合物,该所得化合物为本发明所述化合物,其中R3=H。在极性非质子溶剂(如N,N-二甲基甲酰胺)中,用具有化学式(XXXIV)的合适的烷基化剂(如甲基碘)和合适的碱进一步烷基化产生具有化学式(Ia)的化合物。
方案5
如在方案6中所示,当R4=O,X2=O以及R5=t-Bu时,在温和的酸性条件下(例如,用在醚中的HCl),可以将所得到的N-Boc 基团去除,以提供胺盐,例如HCl盐。具有化学式(I)的化合物的酸性裂解(例如用溶剂如四氢呋喃中的HCl)得到具有化学式(XVI)的化合物作为其盐,例如作为其HCl盐。然后可以在碱(例如吡啶)存在下,通过与合适的具有化学式(XXXV)的氯甲酸酯(如氯甲酸乙酯)反应,将具有化学式(XVI)的化合物进一步转化为例如具有化学式(If)的化合物。
方案6
作为替代方案,然后可以通过与碳酰氯或具有化学式(XXXVII) 的适合的碳酰氯等效物(如CDI或4-硝基苯基氯甲酸酯)反应,进一步转化具有化学式(XVI)的化合物,以给出具有化学式(Ie)的化合物。然后与具有化学式(XXXIII)的醇、胺或硫醇进一步反应,得到具有化学式(Ig)的化合物。
作为另外的替代方案,可以通过与合适的具有化学式(XXXVI) 的异氰酸酯(例如叔丁基-异腈)反应,将具有化学式(XVI)的化合物转化为例如具有化学式(Ih)的化合物。当X2=N,可以在碱(例如碳酸钾)存在下,用合适的具有化学式(XXXVIII)的亲电子试剂 (例如甲基碘)进一步烷基化具有化学式(Ih)的化合物,以给出具有化学式(Ii)的化合物。
方案7
如方案7所示,如在WO 2013/186089中所传授的,可以在溶剂如(1,4-二噁烷)中,通过用具有化学式(XXXIX)的双功能试剂(例如 1-氯-2-异硫氰酸基乙烷或1-溴-4-异氰酸基合丁烷)处理,将具有化学式(XVI)的化合物转化为具有化学式(Ik)的化合物。
方案8
如方案8所示,在醚溶剂(如1,4-二噁烷)中,将具有化学式(Ip) 的化合物用具有化学式(XX)的双官能试剂(例如氯甲酸氯乙酯)以及碱(例如氢化钠)进行酰化,得到具有化学式(XXI)的化合物。可以在溶剂(如二氯甲烷)中,用酸性试剂(如TFA),在温和条件下裂解N-Boc基团,以得到具有化学式(Ip)的化合物。
经由在极性非质子溶剂(例如N,N-二甲基甲酰胺)中用合适的碱 (例如氢化钠)去质子化,通过环化对具有化学式(Ip)的化合物进一步官能化,以得到具有化学式(Iq)的化合物。
如本文所描述的具有化学式(I)的化合物可以自身被用作除草剂,但是通常使用配制佐剂(例如载体、溶剂和表面活性剂(SFA)) 将它们配制成除草组合物。因此,本发明进一步提供了包括如本文所描述的除草化合物和农业上可接受的配制佐剂的除草组合物。该组合物可以处于浓缩物的形式,在使用前稀释这些浓缩物,尽管也可以制成即用型组合物。通常用水进行最终稀释,但是可以替代水或除了水之外使用例如液体肥料、微量营养素、生物有机体、油或溶剂。
这些除草组合物总体上包含按重量计从0.1%到99%、尤其是按重量计从0.1%到95%的具有化学式(I)的化合物以及按重量计从 1%到99.9%的配制佐剂,该配制佐剂优选地包括按重量计从0%到 25%的表面活性物质。
这些组合物可以选自多种配制品类型,这些配制品类型中的很多从《关于植物保护产物的FAO标准的发展和使用的手册》(Manual on Development and Use of FAOSpecifications for Plant Protection Products),第5版,1999年中得知。这些包括可尘化粉剂(DP)、可溶性粉剂(SP)、水溶性颗粒剂(SG)、水可分散性颗粒剂(WG)、可湿性粉剂(WP)、颗粒剂(GR)(缓释或快释的)、可溶的浓缩物(SL)、油易混合的液体(OL)、超低体积液体(UL)、可乳化的浓缩物(EC)、可分散性浓缩物(DC)、乳液(水包油(EW)和油包水(EO)两者)、微乳液(ME)、悬浮液浓缩物(SC)、气溶胶、胶囊悬浮液(CS)以及种子处理配制品。在任何情况下,所选择的配制品类型将取决于所设想的具体目的以及具有化学式(I)的化合物的物理、化学和生物特性。
可尘化粉剂(DP)可以通过将具有化学式(I)的化合物与一种或多种固体稀释剂(例如,天然粘土、高岭土、叶蜡石、膨润土、氧化铝、蒙脱石、硅藻土(kieselguhr)、白垩土、硅藻土(diatomaceous earths)、磷酸钙、碳酸钙和碳酸镁、硫、石灰、面粉、滑石和其他有机和无机的固体载体)混合并将该混合物机械地碾磨成细粉末来制备。
可溶性粉剂(SP)可以通过将具有化学式(I)的化合物与一种或多种水-溶性无机盐(如碳酸氢钠、碳酸钠或硫酸镁)或一种或多种水溶性有机固体(如多糖)以及任选地一种或多种湿润剂、一种或多种分散剂或所述试剂的混合物进行混合来制备以改进水分散性/水溶性。然后将该混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水溶性颗粒剂(SG)。
可湿性粉剂(WP)可以通过将具有化学式(I)的化合物与一种或多种固体稀释剂或载体、一种或多种湿润剂以及优选地,一种或多种分散剂,以及优选地,一种或多种的悬浮剂混合来制备以促进在液体中的分散。然后将该混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水可分散性颗粒剂(WG)。
可以这样形成颗粒剂(GR):通过将具有化学式(I)的化合物与一种或多种粉状固体稀释剂或载体的混合物造粒来形成,或者通过将具有化学式(I)的化合物(或其在适宜试剂中的溶液)吸收进多孔颗粒材料(例如浮石、凹凸棒石粘土、漂白土、硅藻土(kieselguhr)、硅藻土(diatomaceous earths)或玉米芯粉),或通过将具有化学式(I) 的化合物(或其在适宜试剂中的溶液)吸附到硬芯材料(例如沙、硅酸盐、矿物碳酸盐、硫酸盐或磷酸盐)上并且如果必要的话,进行干燥来由预成型的空白颗粒形成。通常用于帮助吸收或吸附的试剂包括溶剂(如脂肪族和芳香族石油溶剂、醇、醚、酮以及酯)和粘着剂(如聚乙酸乙烯酯、聚乙烯醇、糊精、糖以及植物油)。一种或多种其他添加剂还可以包括在颗粒(例如乳化剂、湿润剂或分散剂)。
可分散的浓缩物(DC)可以通过将具有化学式(I)的化合物溶于水或有机溶剂(如酮、醇或乙二醇醚)中来制备。这些溶液可以包含表面活性剂(例如以改进水稀释或防止喷雾罐中的结晶)。
可乳化的浓缩物(EC)或水包油乳液(EW)可以通过将具有化学式(I)的化合物溶于有机溶剂(任选地包含一种或多种湿润剂、一种或多种乳化剂或者所述试剂的混合物)中来制备。在EC中使用的适合的有机溶剂包括芳香族烃类(如烷基苯或烷基萘,例如 SOLVESSO100、SOLVESSO 150和SOLVESSO 200;SOLVESSO 是注册商标)、酮类(如环己酮或甲基环己酮)和醇类(如苯甲醇、糠醇或丁醇)、N-烷基吡咯烷酮类(如N-甲基吡咯烷酮或N-辛基吡咯烷酮)、脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲基酰胺)和氯化烃类。EC产品可以在添加到水中时自发地乳化,从而产生具有足够稳定性的乳液,以允许通过适当设备进行喷洒施用。
EW的制备涉及获得作为液体(如果它在室温下不是液体,则它可以在典型地低于70℃的合理温度下熔化)或处于溶液中(通过将它溶于适当的溶剂中)的具有化学式(I)的化合物,然后在高剪切下将所得液体或溶液乳化进包含一种或多种SFA的水中,以产生乳液。在EW中使用的适合的溶剂包括植物油、氯化烃(如氯苯)、芳香族溶剂(如烷基苯或烷基萘)以及其他在水中具有低溶解度的适当的有机溶剂。
微乳液(ME)可以通过将水与一种或多种溶剂和一种或多种SFA 的掺合物混合来制备,以自发地产生热力学稳定的各向同性的液体配制品。具有化学式(I)的化合物一开始就存在于水中或溶剂/SFA掺合物中。在ME中使用的适合的溶剂包括此前描述的在EC或EW中使用的那些。ME可以是水包油系统或油包水系统(存在哪种系统可以通过电导率测量来确定)并且可以适合用于在相同配制品中混合水溶性的和油溶性的杀有害生物剂。ME适合于稀释到水中,同时保持为微乳液或者形成常规的水包油乳液。
悬浮浓缩物(SC)可以包括具有化学式(I)的化合物的精细分散的不溶固体颗粒的水性或非水性悬浮液。SC可以任选地使用一种或多种分散剂通过在适合的介质中球磨或珠磨具有化学式(I)的固体化合物来制备,以产生该化合物的精细颗粒悬浮液。在该组合物中可以包括一种或多种湿润剂,并且可以包括悬浮剂以降低颗粒的沉降速率。可替代地,可以干磨具有化学式(I)的化合物并且将其添加到包含此前描述的试剂的水中,以产生希望的最终产物。
气溶胶配制品包含具有化学式(I)的化合物和适合的推进剂(例如,正丁烷)。还可将具有化学式(I)的化合物溶于或分散于适合的介质(例如水或可与水混溶的液体,如正丙醇)中以提供在不加压的手动喷雾泵中使用的组合物。
胶囊悬浮液(CS)可以通过以与制备EW配制品类似的方式来制备,除了附加的聚合步骤之外,这样使得获得油滴的水分散体,其中每个油滴都被聚合物外壳包裹并且含具有化学式(I)的化合物以及其可任选的载体或稀释剂。该聚合物壳可以通过界面缩聚反应或通过凝聚程序来制备。这些组合物可以提供具有化学式(I)的化合物的受控释放并且它们可以用于种子处理。具有化学式(I)的化合物也可以被配制在可生物降解的聚合物基质中,以提供该化合物的缓慢的控制释放。
该组合物可以包括一种或多种添加剂以改进该组合物的生物性能,例如通过改进表面上的湿润性、保留或分布;处理过的表面上的防雨性;或具有化学式(I)的化合物的吸收或迁移性。这样的添加剂包括表面活性剂(SFA)、基于油的喷雾添加剂,例如某些矿物油或天然植物油(例如大豆和油菜籽油),以及这些与其他生物增强佐剂 (可帮助或修饰具有化学式(I)的化合物的作用的成分)的掺合物。
湿润剂、分散剂和乳化剂可以是阳离子类型、阴离子类型、两性类型或非-离子类型的SFA。
适合的阳离子类型的SFA包括季铵化合物(例如鲸蜡三甲基溴化铵)、咪唑啉以及胺盐。
适合的阴离子型SFA包括脂肪酸的碱金属盐、脂肪族硫酸单酯的盐(例如月桂硫酸钠)、磺化的芳香族化合物的盐(例如十二烷基苯磺酸钠、十二烷基苯磺酸钙、丁基萘磺酸盐以及二-异丙基-萘磺酸钠和三-异丙基-萘磺酸钠的混合物)、醚硫酸盐、醇醚硫酸盐(例如月桂醇聚醚-3-硫酸钠)、醚羧酸盐(例如月桂醇聚醚-3-羧酸钠)、磷酸酯类(来自一种或多种脂肪醇与磷酸(主要是单酯)或与五氧化二磷 (主要是二酯)之间反应的产物,例如月桂醇与四磷酸之间的反应;另外这些产物可以被乙氧基化)、硫代琥珀酰胺酸盐、石蜡或烯烃磺酸盐、牛磺酸盐以及木质磺酸盐。
适合的两性型的SFA包括甜菜碱、丙酸盐和甘氨酸盐。
适合的非-离子型SFA包括环氧烷类(如环氧乙烷、环氧丙烷、环氧丁烷或其混合物)与脂肪醇类(如油醇或鲸蜡醇)或与烷基酚类 (如辛基酚、壬基酚或辛基甲酚)的缩合产物;衍生自长链脂肪酸或己糖醇酐的偏酯;所述偏酯与环氧乙烷的缩合产物;嵌段聚合物(包含环氧乙烷和环氧丙烷);烷醇酰胺;单酯(例如脂肪酸聚乙二醇酯);氧化胺(例如月桂基二甲基氧化胺);以及卵磷脂。
适合的悬浮剂包括亲水性胶体(诸如多糖、聚乙烯吡咯烷酮或羧甲基纤维素钠)和膨胀性粘土(诸如膨润土或凹凸棒石)。
如本文所描述的除草组合物可以进一步包括至少一种另外的杀有害生物剂。例如,具有化学式(I)的化合物还可以与其他除草剂或植物生长调节剂组合使用。在优选的实施例中,该另外的杀有害生物剂是除草剂和/或除草剂安全剂。这类混合物的实例(其中‘I’代表具有化学式(I)的化合物)是:I+乙酰草胺、I+氟锁草醚、I+氟锁草醚钠、I+苯草醚、I+丙烯醛、I+甲草胺、I+阿洛昔芬、I+莠灭净、I+氨唑草酮、I+酰嘧磺隆、I+氯氨吡啶酸、I+杀草强、I +莎稗磷、I+黄草灵、I+莠去津、I+唑啶草酮、I+四唑嘧磺隆、 I+BCPC、I+氟丁酰草胺、I+草除灵、I+苯卡巴腙、I+氟草胺、 I+呋草磺、I+苄嘧磺隆、I+苄嘧磺隆甲酯、I+地散磷、I+灭草松、I+双苯嘧草酮、I+苯并双环酮、I+吡草酮、I+氟吡草酮、 I+治草醚、I+双丙氨膦、I+双草醚、I+双草醚钠、I+硼砂、I +丁溴啶、I+溴丁酰草胺、I+溴草腈、I+丁草胺、I+丁胺磷、I +地乐胺、I+丁苯草酮、I+丁酸盐、I+卡可基酸、I+氯酸钙、I +唑草胺、I+长杀草、I+唑草酮、I+唑酮草酯、I+氯芴素、I+ 氯芴素甲酯、I+杀草敏、I+氯嘧磺隆、I+氯嘧磺隆乙酯、I+氯乙酸、I+绿麦隆、I+氯普芬、I+氯磺隆、I+敌草索、I+敌草索二甲酯、I+吲哚酮草酯、I+环庚草醚、I+醚磺隆、I+咯草隆、 I+烯草酮、I+炔草酯、I+炔草酯炔丙酯、I+广灭灵、I+稗草胺、 I+二氯吡啶酸、I+氯酯磺草胺、I+氯酯磺草胺甲酯、I+氰草津、 I+环草敌、I+环丙嘧磺隆、I+噻草酮、I+氰氟草酯、I+氰氟草酯-丁基、I+2,4-D、I+杀草隆、I+茅草枯、I+棉隆、I+2,4-DB、 I+甜菜安、I+麦草畏、I+敌草腈、I+2,4-滴丙酸、I+精2,4-滴丙酸、I+禾草灵、I+禾草灵甲酯、I+双氯磺草胺、I+野燕枯、I +野燕枯甲基磺酸盐、I+吡氟酰草胺、I+氟吡草腙、I+噁唑隆、 I+哌草丹、I+二甲草胺、I+异戊净、I+二甲吩草胺、I+精二甲吩草胺、I+噻节因、I+二甲胂酸、I+敌乐胺、I+特乐酚、I+ 草乃敌、I+异丙净、I+敌草快、I+敌草快二溴化物、I+氟硫草定、I+敌草隆、I+草多索、I+EPTC、I+禾草畏、I+丁氟消草、 I+胺苯磺隆、I+胺苯磺隆甲酯、I+乙烯利、I+甜菜呋、I+氟乳醚、I+乙氧嘧磺隆、I+乙氧苯草胺、I+精噁唑禾草灵、I+精噁唑禾草灵-乙酯、I+四唑酰草胺、I+硫酸亚铁、I+麦草氟M、I +啶嘧磺隆、I+双氟磺草胺、I+吡氟禾草灵、I+吡氟禾草灵丁酯、 I+精吡氟禾草灵、I+精吡氟禾草灵-丁酯、I+异丙吡草酯、I+氟酮磺隆、I+氟酮磺隆-钠、I+氟吡磺隆、I+氟消草、I+氟噻草胺、 I+氟哒嗪草酯、I+氟哒嗪草酯乙酯、I+氟节胺、I+唑嘧磺草胺、 I+氟烯草酸、I+氟烯草酸戊酯、I+丙炔氟草胺、I+氟炔草胺(flumipropin)、I+伏草隆、I+乙羧氟草醚、I+乙羧氟草醚乙酯、 I+氟虫腙(fluoxaprop)、I+氟胺草唑、I+氟替丙酸(flupropacil)、 I+四氟丙酸、I+氟啶嘧磺隆、I+氟啶嘧磺隆-甲基-钠、I+抑草丁、I+氟啶草酮、I+氟咯草酮、I+使它隆、I+呋草酮、I+嗪草酸、I+嗪草酸甲酯、I+氟磺胺草醚、I+甲酰胺磺隆、I+蔓草磷、I+草铵膦、I+草铵膦铵、I+草甘膦、I+氟氯吡啶酯、I+氯吡嘧磺隆、I+氯吡嘧磺隆甲酯、I+吡氟氯禾灵、I+精吡氟氯禾灵、 I+环嗪酮、I+咪草酯、I+咪草酯甲酯、I+甲氧咪草烟、I+甲咪唑烟酸、I+灭草烟、I+咪唑喹啉酸、I+咪草烟、I+咪唑磺隆、 I+茚草酮、I+三嗪茚草胺、I+碘甲烷、I+碘磺隆、I+I+碘甲磺隆钠、I+碘苯腈、I+异丙隆、I+异噁隆、I+异噁酰草胺、I+ 异噁氯草酮、I+异噁唑草酮、I+异噁草醚、I+卡灵草、I+克阔乐、I+环草定、I+利谷隆、I+2甲4氯丙酸、I+精2甲4氯丙酸、 I+苯噻酰草胺、I+氟磺酰草胺、I+甲基二磺隆、I+甲基二磺隆甲酯、I+硝磺草酮、I+威百亩、I+噁唑酰草胺、I+苯嗪草酮、I +吡草胺、I+甲基苯噻隆、I+灭草唑、I+甲基胂酸、I+甲基杀草隆、I+异硫氰酸甲酯、I+异丙甲草胺、I+S-异丙甲草胺、I+磺草唑胺、I+甲氧隆、I+赛克嗪、I+甲磺隆、I+甲磺隆甲酯、I+ 草达灭、I+绿谷隆、I+萘丙胺、I+敌草胺、I+抑草生、I+草不隆、I+烟嘧磺隆、I+正甲基草甘膦、I+壬酸、I+达草灭、I+ 油酸(脂肪酸)、I+坪草丹、I+嘧苯胺磺隆、I+氨磺灵、I+丙炔噁草酮、I+噁草酮、I+环氧嘧磺隆、I+噁嗪草酮、I+乙氧氟草醚、I+百草枯、I+百草枯二氯化物、I+克草猛、I+二甲戊乐灵、I+五氟磺草胺、I+五氯苯酚、I+甲氯酰草胺、I+环戊噁草酮、I+烯草胺、I+甜菜宁、I+毒莠定、I+氟吡酰草胺(picolinafen)、 I+唑啉草酯、I+哌草磷、I+丙草胺、I+氟嘧磺隆、I+氟嘧磺隆甲酯、I+氨氟乐灵、I+环苯草酮、I+调环酸钙、I+扑灭通、I +扑草净、I+扑草胺、I+敌稗、I+喔草酯、I+扑灭津、I+苯胺灵、I+异丙草胺、I+丙苯磺隆、I+丙苯磺隆钠、I+拿草特、I +苄草丹、I+氟磺隆、I+双唑草腈、I+吡草醚、I+吡草醚乙酯、 I+磺酰草吡唑(pyrasulfotole)、I+吡唑特、I+吡嘧磺隆、I+吡嘧磺隆乙酯、I+苄草唑(pyrazoxyfen)、I+嘧啶肟草醚、I+稗草畏、I+氯苯咕醇(pyridafol)、I+哒草特、I+环酯草醚、I+嘧草醚、I+嘧草醚甲酯、I+吡丙醚、I+嘧硫草醚、I+嘧硫草醚钠、 I+罗克杀草砜、I+甲氧磺草胺、I+快杀稗、I+喹草酸、I+灭藻醌、I+喹禾灵、I+精喹禾灵、I+砜嘧磺隆、I+苯嘧磺草胺、I +稀禾定、I+环草隆、I+西玛津、I+西草净、I+氯酸钠、I+磺草酮、I+甲磺草胺、I+嘧磺隆、I+嘧磺隆甲酯、I+草硫膦 (sulfosate)、I+磺酰磺隆、I+硫酸、I+丁噻隆、I+特呋三酮、 I+环磺酮、I+吡喃草酮、I+特草定、I+甲氧去草净、I+特丁津、I+去草净、I+甲氧噻草胺、I+噻草啶、I+噻吩磺隆、I+噻酮磺隆(thiencarbazone)、I+噻吩磺隆甲酯、I+禾草丹、I+苯吡唑草酮、I+肟草酮、I+野麦畏、I+醚苯磺隆、I+三嗪氟草胺、 I+苯磺隆、I+苯磺隆甲酯、I+绿草定、I+草达津、I+三氟啶磺隆、I+三氟啶磺隆钠、I+氟乐灵、I+氟胺磺隆、I+氟胺磺隆甲酯、I+三羟基三嗪、I+抗倒酯乙酯、I+三氟甲磺隆以及I+[3-[2- 氯-4-氟-5-(1-甲基-6-三氟甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-3-基)苯氧基]-2-吡啶基氧基]乙酸乙酯(CAS RN 353292-31-6)。本发明的具有化学式(I)的化合物和/或组合物还可以与在WO 06/024820和/或 WO 07/096576中披露的除草化合物组合。
具有化学式(I)的化合物的混合配伍物还可以处于酯或盐的形式,如例如在杀有害生物剂手册(The Pesticide Manual),第十六版,英国作物保护委员会(British CropProtection Council),2012中所提到。
具有化学式(I)的化合物还可以在与其他农用化学品(例如杀真菌剂、杀线虫剂或杀昆虫剂)的混合物中使用,这些农用化学品的实例在杀有害生物剂手册(见上文)中给出)。
具有化学式(I)的化合物与混合配伍物的混合比优选地是从1: 100至1000:1。
这些混合物可以有利地用于以上提到的这些配制品中(在这种情况下“活性成分”涉及具有化学式I的化合物与混合配伍物的对应混合物)。
如本文所描述的具有化学式(I)的化合物还可以与一种或多种安全剂组合使用。同样地,如本文所描述的具有化学式(I)的化合物与一种或多种另外的除草剂的混合物还可以与一种或多种安全剂组合使用。这些安全剂可以是AD 67(MON 4660)、解草嗪、解毒喹、环丙磺酰胺(CAS RN 221667-31-8)、二氯丙烯胺、解草唑乙酯、解草啶、氟草肟、解草噁唑和对应的R异构体、双苯噁唑酸乙酯、吡唑解草酸二乙酯、解草腈、N-异丙基-4-(2-甲氧基-苯甲酰基氨磺酰基)- 苯甲酰胺(CAS RN 221668-34-4)。其他可能性包括例如在EP 0365484中披露的安全剂化合物,例如N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。特别优选的是具有化学式I的化合物与环丙磺酰胺、双苯噁唑酸-乙基、解毒喹和/或N-(2-甲氧基苯甲酰基)-4-[(甲基- 氨基羰基)氨基]苯磺酰胺的混合物。
该具有化学式(I)的化合物的这些安全剂还可以处于酯或盐的形式,如例如在杀有害生物剂手册(The Pesticide Manual)(见上文) 中所提到。提及解毒喹还适用于锂、钠、钾、钙、镁、铝、铁、铵、季铵、锍或其鏻盐(如在WO 02/34048中披露的),并且对解草唑乙酯(fenchlorazole-ethyl)的提及还适用于解草唑(fenchlorazole),等等。
优选地,具有化学式(I)的化合物与安全剂的混合比是从100:1 至1:10,尤其是从20:1至1:1。
这些混合物可有利地用于以上提到的这些配制品中(在这种情况下“活性成分”涉及具有化学式(I)的化合物与安全剂的对应混合物)。
如上所述,包括此类化合物的具有化学式(I)的化合物和/或组合物可以用于控制不想要的植物生长的方法中,和特别是用于在有用植物的作物中控制不想要的植物生长中。因此,本发明进一步提供了选择性地控制场所中的杂草的方法,该场所包括作物植物和杂草,其中该方法包括向该场所施用杂草控制量的如本文所描述的具有化学式 (I)的化合物、或组合物。‘控制’意指杀死、减少或延迟生长或防止或减少发芽。通常有待控制的植物是不想要的植物(杂草)。‘场所’意指其中植物正生长或将生长的区域。
具有化学式(I)的化合物的施用率可以在宽范围之内变化并且取决于土壤的性质、施用方法(出苗前或出苗后;拌种;施用至种子垄沟;免耕施用等)、作物植物、有待控制的杂草、主要气候条件、以及受施用方法支配的其他因素、施用时间以及目标作物。根据本发明的具有化学式I的化合物通常以从10g/ha至2000g/ha,尤其是从 50g/ha到1000g/ha的比率施用。
通常通过喷洒该组合物进行施用,典型地是通过用于大面积的装在拖拉机上的喷洒机,但是还可以使用其他方法如撒粉(针对粉末)、滴加或浸湿。
可以使用根据本发明的组合物的有用植物,包括作物如谷物,例如大麦和小麦、棉花、油菜籽油菜、向日葵、玉米、稻、大豆、甜菜、甘蔗以及草皮。
作物植物还可以包括树,如果树、棕榈树、椰子树或其他坚果。还包括藤本植物(如葡萄)、灌木果树、果实植物和蔬菜。
作物应被理解为还包括通过常规的育种方法或通过基因工程已经赋予对除草剂或多种类别的除草剂(例如ALS-抑制剂、GS-抑制剂、 EPSPS-抑制剂、PPO-抑制剂、ACC酶-抑制剂以及HPPD-抑制剂) 的耐受性的那些作物。通过常规的育种方法已经赋予其对咪唑啉酮(例如,甲氧咪草烟)的耐受性的作物的实例是夏季油菜(卡罗拉(canola))。通过基因工程方法而赋予对除草剂的耐受性的作物的实例包括例如草甘膦和草丁膦抗性的玉米品种,这些玉米品种在和商标名下是可商购的。在具体优选方面,该作物植物已经如在例如WO 2010/029311中所传授的被工程化,以过表达尿黑酸茄呢基转移酶。
农作物还应理解为通过基因工程方法已经赋予其对有害昆虫有抗性的那些农作物,例如Bt玉米(对欧洲玉米螟有抗性)、Bt棉花(对棉铃象鼻虫有抗性)以及还有Bt马铃薯(对科罗拉多甲虫有抗性) Bt玉米的实例是的Bt 176玉米杂交体(先正达种子公司(Syngenta Seeds))。Bt毒素是由苏芸金芽孢杆菌土壤细菌天然形成的蛋白质。毒素或能够合成此类毒素的转基因植物的实例描述于 EP-A-451 878、EP-A-374 753、WO 93/07278、WO95/34656、WO 03/052073以及EP-A-427 529中。包括一个或多个编码杀昆虫剂抗性和表达一种或多种毒素的基因的转基因植物的实例是(玉米)、Yield(玉米)、(棉花)、 (棉花)、(马铃薯)、以及其植物作物或种子材料均可以是抗除草剂的并且同时是抗昆虫摄食的 (“叠加的”转基因结果)。例如,种子可以在具有表达杀虫的Cry3 蛋白的能力的同时是耐草甘膦的。
作物还应被理解为包括通过常规的育种或基因工程的方法获得并且包含所谓的输出性状(例如改进的储存稳定性、更高的营养价值以及改进的香味)的那些。
其他有用的植物包括例如在高尔夫球场、草地、公园以及路旁的或者商业上种植用于草地的草皮草,以及观赏植物,如花卉或者灌木。
可以使用这些组合物来控制不想要的植物(统称为‘杂草’)。待控制的杂草包括单子叶(例如禾本科)的物种(例如剪股颖属 (Agrostis)、看麦娘属(Alopecurus)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、莎草属(Cyperus)、马唐属(Digitaria)、稗属(Echinochloa)、穇属(Eleusine)、黑麦草属(Lolium)、雨久花属(Monochoria)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、藨草属(Scirpus)、狗尾草属(Setaria)以及高粱属(Sorghum));和双子叶的物种(例如苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、藜属(Chenopodium)、菊属(Chrysanthemum)、白酒草属(Conyza)、拉拉藤属(Galium)、番薯属(Ipomoea)、地肤属(Kochia)、旱金莲属(Nasturtium)、蓼属(Polygonum)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、繁缕属(Stellaria)、婆婆纳属(Veronica)、堇菜属(Viola)以及苍耳属(Xanthium))。杂草还可以包括可被认为是作物植物但是在作物区外生长的植物(‘逃逸者(escapes)’),或从先前栽培的不同作物留下的种子生长的植物 (‘志愿者(volunteers)’)。此类志愿者或逃逸者可以是对某些其他除草剂耐受的。
优选地,待控制和/或生长抑制的杂草包括单子叶杂草、更优选地禾本科单子叶杂草、特别的来自以下属的那些:剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、莎草属(Cyperus)(莎草科(sedge)的属)、马唐属(Digitaria)、稗属(Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、飘拂草属(Fimbristylis)(莎草科的属)、灯心草属(Juncus)(灯心草科(rush)的属)、千金子属(Leptochloa)、黑麦草属(Lolium)、鸭舌草属(Monochoria)、露籽草属(Ottochloa)、黍属(Panicum)、狼尾草属(Pennisetum)、虉草属(Phalaris)、早熟禾属(Poa)、筒轴草属(Rottboellia)、慈菇属(Sagittarta)、藨草属(Scirpus) (莎草科的属)、狗尾草属(Setaria)和/或高粱属(Sorghum),和 /或自生自长的玉米(自生自长的玉蜀黍)杂草;具体地:大穗看麦娘 (Alopecurus myosuroides)(ALOMY,英文名“黑草”)、阿披拉草(Apera spica-venti)、野燕麦(Avena fatua)(AVEFA,英文名“野生燕麦”)、长颖燕麦(Avena ludoviciana)、不实燕麦(Avena sterilis)、燕麦(Avenasativa)(英文名“燕麦(oats)”(自生植物))、伏生臂形草(Brachiaria decumbens)、车前臂形草(Brachiaria plantaginea)、宽叶臂形草(Brachiaria platyphylla)(BRAPP)、旱雀麦(Bromus tectorum)、水平尾马唐(Digitaria horizontalis)、两耳马唐(Digitariainsularis)、马唐(Digitaria sanguinalis)(DIGSA)、稗草(Echinochloa crus-galli)(英文名“常见稗草”,ECHCG)、水田稗(Echinochloa oryzoides)、光头稗(Echinochloa colona或 colonum)、牛筋草(Eleusine indica)、野黍(Eriochloa villosa)(英文名“乌利千草杯”)、千金子(Leptochloa chinensis)、亚马逊千金子(Leptochloa panicoides)、多年生黑麦草(Lolium perenne) (LOLPE,英文名“多年生的黑麦草”)、多花黑麦草(Loliummultiflorum)(LOLMU,英文名“意大利黑麦草”)、欧黑麦草(Lolium persicum)(英文名“波斯黑麦草”)、硬直黑麦草(Lolium rigidum)、洋野黍(Panicum dichotomiflorum)(PANDI)、黍稷(Panicum miliaceum)(英文名“野生黍稷”)、小子虉草(Phalaris minor)、奇异虉草(Phalaris paradoxa)、早熟禾(Poa annua)(POAAN,英文名“一年生早熟禾”)、滨海藨草(Scirpus maritimus)、萤蔺 (Scirpus juncoides)、翠绿狗尾草(Setaria viridis)(SETVI,英文名“绿狗尾草”)、大狗尾草(Setaria faberi)(SETFA,英文名“大狗尾草(giantfoxtail)”)、狗尾草(Setaria glauca)、金狗尾草(Setaria lutescens)(英文名“金黄狗尾草”)、两色蜀黍(Sorghum bicolor)、和/或假高粱(Sorghum halapense)(英文名“约翰逊草”)、和/或高粱(Sorghum vulgare);和/或自生自长的玉米(自生自长的玉蜀黍) 杂草。
在一个实施例中,待控制的禾草科单子叶杂草包括来自以下各属的杂草:剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属 (Bromus)、蒺藜草属(Cenchrus)、马唐属(Digitaria)、稗属(Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、千金子属(Leptochloa)、黑麦草属(Lolium)、露籽草属(Ottochloa)、黍属(Panicum)、狼尾草属(Pennisetum)、虉草属(Phalaris)、早熟禾属(Poa)、筒轴草属(Rottboellia)、狗尾草属(Setaria)和 /或高粱属(Sorghum)、和/或自生自长的玉米(自生自长的玉蜀黍) 杂草;特别地:来自以下各属的杂草:剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、马唐属(Digitaria)、稗属(Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、千金子属(Leptochloa)、黑麦草属(Lolium)、黍属(Panicum)、虉草属(Phalaris)、早熟禾属(Poa)、筒轴草属(Rottboellia)、狗尾草属(Setaria)、和/或高粱属(Sorghum)、和/或自生自长的玉米(自生自长的玉蜀黍)杂草。
在另外的实施例中,禾草科单子叶杂草是“暖季型”(温暖气候型)禾本科杂草;在这种情况下,它们优选地包括(例如是):来自以下各属的杂草:臂形草属(Brachiaria)、蒺藜草属(Cenchrus)、马唐属(Digitaria)、稗属(Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、千金子属(Leptochloa)、露籽草属(Ottochloa)、黍属(Panicum)、狼尾草属(Pennisetum)、虉草属(Phalaris)、筒轴草属(Rottboellia)、狗尾草属(Setaria)和/或高粱属(Sorghum)、和/或自生自长的玉米(自生自长的玉蜀黍)杂草。更优选地,例如待控制和/或生长抑制的禾草科单子叶杂草是“暖季型”(温暖气候)禾草科杂草,其包括(例如是)来自以下各属的杂草:臂形草属 (Brachiaria)、蒺藜草属(Cenchrus)、马唐属(Digitaria)、稗属 (Echinochloa)、椮属(Eleusine)、野黍属(Eriochloa)、黍属(Panicum)、狗尾草属(Setaria)和/或高粱属(Sorghum)、和/或自生自长的玉米(自生自长的玉蜀黍)杂草。
在另一个具体实施例中,禾本科单子叶杂草是“冷季”(凉爽气候)禾本科杂草;在该情况下它们典型地包括来自以下各属的杂草:剪股颖属、看麦娘属、阿披拉草属、燕麦属、雀麦属、黑麦草属和/ 或早熟禾属。
现在通过举例更详细地说明本发明的不同方面和实施例。应当理解的是,在不偏离本发明范围的情况下,可以对细节做出修改。
制备实例
贯穿以下实例,在Varian Unity Inova仪器上或者在Bruker AVANCE-II仪器上在400Mhz或500MHz下记录1H NMR光谱。
使用了以下缩写:s=单峰;bs=宽单峰;d=二重峰;bd=宽二重峰;dd=双二重峰;t=三重峰;q=四重峰;m=多重峰;THF =四氢呋喃;EtOAc=乙酸乙酯;EtOH=乙醇;DMSO=二甲基亚砜;DPPA=叠氮磷酸二苯酯;DMF=N,N-二甲基甲酰胺;dppf=1,1′- 双(联苯膦基)二茂铁;Pd(OAc)2=乙酸钯(II);Et3N=三乙胺;MeOH =甲醇。
使用Accelrys Draw 4.0中的‘Text from structure’功能生成化学名称。
实例P1 化合物A2,叔-丁基N-[2-甲基-5-(3-吡啶基)吡唑-3-基] 氨基甲酸酯的制备
1.1步骤1:2,4-二氧代-4-(3-吡啶基)丁酸乙酯的制备
将NaH(60%w/w,9.91g,248.0mmol)添加到装有无水THF (170mL)的烧瓶中。添加草酸二乙酯(24.13g,165.1mmol),并用无水THF(15mL)洗涤。将该混合物加热至回流,然后在回流下伴随搅拌缓慢添加1-(3-吡啶基)乙酮(10.0g,82.55mmol)在THF(15 mL)中的溶液。15分钟后,将该混合物冷却至室温,并在搅拌和冷却下缓慢添加到在水(375mL)中的2MHCl(130mL)的混合物中。将所得混合物用固体NaHCO3处理直到轻微碱性,然后用EtOAc萃取三次。将合并的有机物用盐水洗涤一次,干燥(MgSO4)并真空浓缩,得到深棕色胶状物,令其静置固化。
通过洗涤和用己烷倾析除去矿物油。将固体溶于温热乙醇(350 mL)中并用脱色木炭处理。5分钟后,将该溶液通过硅藻土热过滤。将滤液真空浓缩,得到粗的2,4-二氧代-4-(3-吡啶基)丁酸乙酯(15.0g),其不经进一步纯化即可使用。
1H NMR(400MHz,CDCl3)δ=9.21(1H,d),8.83(1H,dd),8.29 (1H,m),7.46-7.52(1H,m),7.08(1H,s),4.39-4.46(2H,q),1.40-1.46 (3H,t)。
1.2步骤2:2-甲基-5-(3-吡啶基)吡唑-3-甲酸乙酯的制备
向填充溶解于EtOH(120mL)中的2,4-二氧代-4-(3-吡啶基)丁酸乙酯(10.0g,45.2mmol)的烧瓶中添加甲基肼(2.4mL,46.0mmol)。将混合物加热至回流,持续2.5小时,然后静置过夜。
真空除去溶剂,并使用EtOAc/己烷梯度,将粗材料经由硅胶快速柱色谱法纯化,以得到乙基2-甲基-5-(3-吡啶基)吡唑-3-甲酸酯(2.52 g)。
1H NMR(400MHz,CDCl3)δ=9.02(1H,m),8.56(1H,dd),8.11 (1H,m),7.34(1H,dd),7.17(1H,s),4.39(2H,q),4.25(3H,s),1.42(3H, t)
1.3步骤3:2-甲基-5-(3-吡啶基)吡唑-3-甲酸乙基酯的制备
向冷却于冰浴中、装有溶解于1,4-二噁烷(17mL)中的2-甲基 -5-(3-吡啶基)吡唑-3-甲酸乙基酯(2.52g,10.9mmol)的烧瓶中滴加在水(3.3mL)中的NaOH(1.09g,27.3mmol)。将所得的双相溶液在环境温度下搅拌2小时,然后分批添加水直至均匀(13.2mL)。
将反应混合物在环境温度下再搅拌2小时,此后将溶剂真空浓缩至约50%体积,并用水(20mL)稀释。将反应混合物用2M HCl(13.5 mL)酸化,并将固体沉淀物在泵上过滤,用水洗涤并空气干燥过夜,以得到呈灰白色固体的2-甲基-5-(3-吡啶基)吡唑-3-甲酸(1.70g)。
1H NMR(400MHz,d6-DMSO)δ=9.06(1H,m),8.53(1H,dd), 8.20(1H,d),7.45(1H,m),7.43(1H,s),4.15(3H,s)。
1.4步骤4:N-[2-甲基-5-(3-吡啶基)吡唑-3-基]氨基甲酸叔丁基酯的制备
伴随搅拌,向装有悬浮于叔丁醇(37mL)和甲苯(37mL)中的 2-甲基-5-(3-吡啶基)吡唑-3-甲酸(1.70g,8.34mmol)的烧瓶中滴加三乙胺(1.18mL,8.38mmol)和DPPA(2.30g,8.40mmol),并然后将所得混合物逐渐加热至回流。回流4.5小时后,使反应混合物冷却,并真空除去溶剂。使用EtOAc/己烷梯度,将残余物经由硅胶快速柱色谱法纯化,以得到呈无色胶状的N-[2-甲基-5-(3-吡啶基)吡唑-3- 基]氨基甲酸叔丁基酯(0.75g)。
1H NMR(400MHz,CDCl3)δ=8.98(1H,bs),8.53(1H,bs),8.05 (1H,m),7.30(1H,m),6.63(1H,bs),6.53(1H,bs),3.81(3H,s),1.53 (9H,s)。
实例P2 化合物A1,N-甲基-N-[2-甲基-5-(3-吡啶基)吡唑-3-基] 氨基甲酸叔丁基酯的制备
将N-[2-甲基-5-(3-吡啶基)吡唑-3-基]氨基甲酸叔丁基酯(245mg, 0.893mmol)溶于无水DMF(2.5mL)中,在冰浴中冷却,然后以单一部分添加NaH(60%w/w,42.9mg,1.07mmol)。5分钟后,允许混合物温热至环境温度5分钟(溶液变成棕色)。重新应用冰浴,并滴加无水DMF(0.7mL)中的MeI(133.1mg,0.938mmol)溶液。 30分钟后,将反应升温至环境温度并再搅拌1小时。
用含有2M Hcl(89μL)的水(13mL)淬灭反应。将该混合物用EtOAc萃取3次,并且将合并的有机物用盐水洗涤2次,并且然后干燥(MgSO4)。真空浓缩溶剂并使用EtOAc/己烷梯度,将残余物经由硅胶快速柱色谱法纯化,以得到呈琥珀色胶状的N-甲基-N-[2-甲基 -5-(3-吡啶基)吡唑-3-基]氨基甲酸叔丁基酯(125.0mg)。
1H NMR(400MHz,CDCl3)δ=8.97(1H,d),8.51-8.56(1H,m) 8.07(1H,d),7.28-7.35(1H,m),6.40(1H,s),3.75(3H,s),3.22(3H,s), 1.45(9H,s)。
实例P3 化合物A3,N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯的制备
3.1步骤1:3-甲基-1-嘧啶-5-基-吡唑-4-甲酸乙酯的制备
向装有溶解于1,4-二噁烷(5mL)中的5-溴嘧啶(248mg,1.56 mmol)的烧瓶中添加K2CO3(359mg,2.59mmol)、CuI(124mg, 0.065mmol)、反式-N,N'-二甲基环己烷-1,2-二胺(28.5mg,0.195 mmol)和3-甲基-1H-吡唑-4-甲酸乙酯(200mg,1.30mmol)。这得到蓝色悬浮液,将其加热至110℃并搅拌过夜。
一夜之间,该反应已经变成了深灰色。冷却后,将反应混合物倒入EtOAc和水中。将其用EtOAc萃取两次。将合并的有机物用盐水洗涤并干燥(MgSO4),将合并的有机物真空浓缩,得到棕色固体,将该棕色固体经由硅胶快速柱色谱法使用EtOAc/己烷梯度纯化,以得到呈白色固体的3-甲基-1-嘧啶-5-基-吡唑-4-甲酸乙酯(255mg)。
1H NMR(400MHz,CDCl3)δ=9.18(1H,s),9.14(2H,s),8.42(1H, s),4.35(2H,q),2.58(3H,s),1.39(3H,t)。
3.2步骤2:3-甲基-1-嘧啶-5-基-吡唑-4-甲酸的制备
向装有在1,4-二噁烷(3.4mL)中的3-甲基-1-嘧啶-5-基-吡唑-4- 甲酸乙酯(180mg,0.775mmol)的烧瓶中添加溶解于水(1.7mL) 中的NaOH(68.2mg 1.71mmol),以形成淡黄色溶液,将所得溶液在55℃搅拌过夜。
将反应混合物真空浓缩以除去有机物,并将水层用1M HCl酸化至pH 3,得到白色固体。在泵上滤出沉淀物并用水洗涤两次,然后用 EtOAc洗涤并空气干燥,得到呈白色固体的3-甲基-1-嘧啶-5-基-吡唑 -4-甲酸(84mg)。
1H NMR(400MHz,d6-DMSO)δ=9.35(2H,s),9.15(1H,s),9.10 (1H,s),2.42(3H,s)。
3.3步骤3:N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯,化合物A3的制备
向装有3-甲基-1-嘧啶-5-基-吡唑-4-甲酸(0.206g,1.01mmol)和叔丁醇(7mL)的烧瓶中通过注射器滴加三乙胺(0.141mL,1.0 mmol)。向其中通过注射器滴加DPPA(0.219mL,1.01mmol),并将混合物加热至回流过夜。
过夜形成白色沉淀,并且冷却后,将其在泵中过滤出,并真空浓缩滤液,留下黄色残余物。将其在水和EtOAc之间分配。用另外3部分EtOAc萃取水层。将合并的有机物用盐水洗涤,干燥(MgSO4),并蒸发至干,得到膏状固体(297mg)。将该粗产物通过硅胶快速柱层析法用EtOAc/异己烷梯度洗脱进行纯化,以给出呈白色固体(64 mg)的N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯。
1H NMR(400MHz,CDCl3)δ=9.08(3H,s),8.28(1H,s),6.17(1H, s),2.31(3H,s),1.54(9H,s)。
实例P4 N-甲基-N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯,化合物A5的制备
在氮气下,向装有溶解于DMF(1mL)中并于冰浴中冷却的N-(3- 甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯(68.0mg,0.25mmol) 的烧瓶中以单一部分添加NaH(60%w/w 11.0mg,0.27mmol),得到亮黄色溶液。将混合物在冰浴中搅拌10分钟,然后温热至环境温度持续40分钟。重新应用冰浴,并通过注射器滴加MeI(16μL,0.26 mmol)。将反应在环境温度下搅拌2小时,并用水淬灭和用Et2O萃取两次。将合并的有机物用盐水洗涤,干燥(MgSO4),并真空浓缩,得到呈白色固体的N-甲基-N-(3-甲基-1-嘧啶-5-基-吡唑-4-基)氨基甲酸叔丁基酯(51mg)。
1H NMR(400MHz,CDCl3)δ=9.10(1H,s),9.06(2H,s),7.85(1H, s),3.21(3H,s),2.28(3H,s),1.57(9H,s)。
实例P5 异丙基N-[2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-基]氨基甲酸酯,化合物A58的制备
步骤一:嘧啶-5-甲酸甲酯的合成
将一氧化碳气体引入在MeOH(120mL)中的5-溴嘧啶(15.9g, 0.1mol)、dppf(2.22g,4mmol)、Pd(OAc)2(448mg,2mmol) 和Et3N(20.2g,0.2mol)的混合物中并将内压增加至30巴。将反应混合物在95℃下搅拌约4小时,然后冷却至室温并过滤。减压浓缩滤液,并将残余物通过硅胶柱色谱纯化(洗脱剂:石油醚/乙酸乙酯= 5:1),得到呈白色固体的嘧啶-5-甲酸甲酯(9.6g,70%收率)。
1H NMR(400MHz,CDCl3)δ=9.36(1H,s),9.27(2H,s),3.98(3H, s)。
步骤二:3-嘧啶-5-基-1H-吡唑-5-胺的合成
将嘧啶-5-甲酸甲酯(5.3g,38mmol)添加到在乙腈(1.57g,38 mmol)和THF(50mL)中的NaH(2.4g,60mmol)的悬浮液中,并将混合物在回流下加热过夜。滤出沉淀,并用二乙醚洗涤,得到呈黄色固体的3-氧代-3-嘧啶-5-基-丙腈钠盐,其不经进一步纯化直接用于下一步骤。
将在EtOH(100mL)中的3-氧代-3-嘧啶-5-基-丙腈钠盐(5g)、肼盐酸盐(3.0g,44mmol)、乙酸(1.7g,30mmol)和盐酸(0.2mL, 1M)的混合物在回流下加热3小时。然后将反应混合物冷却至室温并真空浓缩。将残余物通过硅胶柱色谱纯化,得到呈黄色固体的5-嘧啶-5-基-1H-吡唑-3-胺(1.5g)。
1H NMR(400MHz,DMSO-d6)δ=11.84(1H,bs),9.03(3H,s), 5.85(1H,s),5.09(2H,bs)。
步骤三:2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-胺的合成
在高压釜中,将CHClF2(26.66g,310mmol)引入在二噁烷(30 mL)和水(20mL)中的5-嘧啶-5-基-1H-吡唑-3-胺(5g,31mmol) 和KOH(8.68g,155mmol)的混合物中。将反应混合物在100℃加热,并将内压增加至15巴。搅拌4h后,将反应混合物冷却至室温,用水(50mL)稀释并用EtOAc萃取3次。将合并的萃取液用无水硫酸钠干燥,真空浓缩并通过硅胶快速色谱纯化(洗脱剂石油醚/乙酸乙酯3:1),得到呈黄色固体的1-(二氟甲基)-5-嘧啶-5-基-吡唑-3-胺(260 mg)和想要的2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-胺(260mg)。
1H NMR(400MHz,DMSO-d6)δ=9.17(1H,s),9.14(2H,s),7.65 (1H,t),6.19(2H,s),5.97(1H,s)。
步骤四:N-[2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-基]氨基甲酸异丙基酯,化合物A58的合成
向装有2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-胺(100mg,0.47mmol) 的小瓶中添加二氯甲烷(7mL)与吡啶(94mg,1.184mmol)并将该混合物搅拌5分钟。滴加氯甲酸异丙酯(1M,在甲苯中)(0.59mmol, 0.59mL),并将混合物搅拌过夜。将样品真空浓缩并预先吸附到硅胶上,然后使用EtOAc/己烷梯度通过快速柱色谱纯化,得到呈稠胶状物的所希望的产物(82mg)。
1H NMR(400MHz,CDCl3)δ=9.22(1H,s),9.16(2H,s),7.28(1H, t),7.20(1H,bs),6.92(1H,bs),5.05(1H,m),1.30(6H,d)。
实例P6 N-[2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-基]-N-甲基-氨基甲酸异丙基酯,化合物A59的制备
向装有异丙基N-[2-(二氟甲基)-5-嘧啶-5-基-吡唑-3-基]氨基甲酸酯(82mg,0.276mmol)的烧瓶中添加DMF(5mL)并搅拌至均匀。将混合物冷却至0℃(冰浴),并以单一部分添加氢化钠(65%w/w,在矿物油中)(12mg,0.29mmol)。5分钟后,将混合物从冰浴中取出并在环境温度下再搅拌5分钟。然后将烧瓶重新冷却至0℃(冰浴),并滴加碘甲烷(42mg,0.295mmol,0.0180mL)。10分钟后,允许混合物温热至环境温度并再搅拌30分钟。将混合物用2M HCl (500μL)淬灭并真空浓缩。然后将所得残余物溶解在CH2Cl2中并预先吸附到硅胶上,然后使用EtOAc/己烷梯度在硅胶上通过快速柱色谱纯化。此步骤得到呈白色固体的所需化合物(44mg)。
1H NMR(400MHz,CDCl3)δ=9.22(1H,s),9.12(2H,s),7.14(1H, t),6.60(1H,s),4.98(1H,m),3.27(3H,s),1.22(6H,bd)。
实例P7 N-[3-氯-1-(3-吡啶基)吡唑-4-基]-N-甲基-氨基甲酸叔丁基酯,化合物A60的制备
N-[3-氯-1-(3-吡啶基)吡唑-4-基]氨基甲酸叔丁基酯是根据US 8901153中的程序制备的。
经约5分钟,向装有在DMF(6mL)中并在冰浴中冷却的N-[3- 氯-1-(3-吡啶基)吡唑-4-基]氨基甲酸叔丁基酯(200mg,0.69mmol) 的烧瓶中滴加氢化钠(60%w/w,在油中)(30mg,0.75mmol)。在这段时间反应混合物变成深黄色,并且可观察到细小的沉淀。然后将混合物温热至室温并搅拌5分钟。重新应用冰浴,并滴加碘甲烷(212 mg,1.49mmol,92μL)。将混合物在冰浴中搅拌2小时,然后温热至环境温度,并用盐水(5mL)稀释。将反应用EtOAc(3×10mL) 萃取,并将合并的有机物真空浓缩,并且然后装载到SiO2柱上,然后通过硅胶快速柱色谱(用EtOAc/己烷梯度洗脱)纯化,得到呈无色油状物的所需化合物(102mg)。
1H NMR(400MHz,CDCl3)δ=8.92(1H,d),8.57(1H,d),8.07 (1H,m),7.90(1H,bs),7.42(1H,m),3.22(3H,s),1.39(9H,s)。
使用上述实例P1至P7中关于化合物A1、A2、A3、A5、A58、 A59和A60的方法,以类似的方式制备本发明的其他实例。下表2总结了这些化合物的物理数据。
表2:通过上述方法制备的化合物
生物学实例
B1出苗前除草活性
将多种测试物种的种子播种在盆中的标准土壤中。普通小麦 (TRZAW)、水稻(ORYSA)、野燕麦(AVEFA)、大穗看麦娘 (Alopecurus myosuroides)(ALOMY)、稗草(ECHCG)、黑麦草(LOLPE)。在温室(在24℃/16℃白天/夜晚下;14小时光照; 65%湿度)中在受控条件下培养一天之后(出苗前),用水性喷雾溶液喷洒这些植物,该水性喷雾溶液源自工业级活性成分在丙酮/水(50: 50)溶液中的配制品,该溶液含有0.5%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。然后使测试植物在受控制的条件(在24℃/16℃日/夜下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。13天之后,对测试进行评估(5=对植物完全性的损害;0=对植物没有损害)。结果示于下面的表3中。
表3通过出苗前施用具有化学式(I)的化合物对杂草物种的控制
B1a出苗前除草活性
将多种测试物种的种子播种在盆中的标准土壤中。反枝苋 (AMARE)、大狗尾草(SETFA)、玉米(ZEAMX)、茼麻(Abutilon threophrasti)(ABUTH)、稗草(ECHCG)、黑麦草(LOLPE)。在温室(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)中在受控条件下培养一天之后(出苗前),用水性喷雾溶液喷洒这些植物,该水性喷雾溶液源自工业级活性成分在丙酮/水(50:50)溶液中的配制品,该溶液含有0.5%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯, CAS RN 9005-64-5)。然后使测试植物在受控制的条件(在24℃/16℃日/夜下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。13天之后,对测试进行评估(5=对植物完全性的损害;0=对植物没有损害)。结果示于下面的表4中
表4通过出苗前施用具有化学式(I)的化合物对杂草物种的控制
B2出苗后除草活性
将多种测试物种的种子播种在盆中的标准土壤中。普通小麦 (TRZAW)、水稻(ORYSA)、野燕麦(AVEFA)、大穗看麦娘 (Alopecurus myosuroides)(ALOMY)、稗草(ECHCG)、黑麦草(LOLPE)。在温室(在24℃/16℃白天/夜晚下;14小时光照; 65%湿度)中在受控条件下栽培(出苗前)八天后,用水性喷雾溶液喷洒这些植物,该水性喷雾溶液源自工业级活性成分在丙酮/水(50: 50)溶液中的配制品,该溶液含有0.5%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。然后使测试植物在受控制的条件(在24℃/16℃日/夜下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。13天之后,对测试进行评估(5=对植物完全性的损害;0=对植物没有损害)。结果在下表5中示出。
表5通过出苗后施用具有化学式(I)的化合物对杂草物种的控制
B2a出苗后除草活性
将多种测试物种的种子播种在盆中的标准土壤中。反枝苋 (AMARE)、大狗尾草(SETFA)、玉米(ZEAMX)、茼麻(ABUTH)、稗草(ECHCG)、黑麦草(LOLPE)。在温室(在24℃/16℃白天/ 夜晚下;14小时光照;65%湿度)中在受控条件下栽培(出苗前)八天后,用水性喷雾溶液喷洒这些植物,该水性喷雾溶液源自工业级活性成分在丙酮/水(50:50)溶液中的配制品,该溶液含有0.5%吐温 20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。然后使测试植物在受控制的条件(在24℃/16℃日/夜下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。13天之后,对测试进行评估(5=对植物完全性的损害;0=对植物没有损害)。结果在下表6中示出。
表6通过出苗后施用具有化学式(I)的化合物对杂草物种的控制
Claims (4)
3.一种控制不想要的植物生长的方法,该方法包括将如在权利要求1或权利要求2中定义的具有化学式(I)的化合物施用至不想要的植物或施用至其所在场所。
4.一种在包括作物植物和杂草的场所选择性地控制杂草的方法,其中该方法包括:向该场所施用杂草控制量的如在权利要求1或权利要求2中定义的具有化学式(I)的化合物。
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RU2571076C2 (ru) | 2010-11-03 | 2015-12-20 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидная композиция |
US9282739B2 (en) * | 2012-04-27 | 2016-03-15 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
JP2014111559A (ja) | 2012-07-04 | 2014-06-19 | Nissan Chem Ind Ltd | ピラゾール誘導体および有害生物防除剤 |
-
2015
- 2015-02-10 GB GBGB1502164.5A patent/GB201502164D0/en not_active Ceased
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2016
- 2016-02-03 CN CN201680009376.6A patent/CN107250127B/zh not_active Expired - Fee Related
- 2016-02-03 EP EP16702570.9A patent/EP3255989B1/en active Active
- 2016-02-03 ES ES16702570T patent/ES2836423T3/es active Active
- 2016-02-03 WO PCT/EP2016/052232 patent/WO2016128266A1/en active Application Filing
- 2016-02-03 US US15/549,707 patent/US10905123B2/en active Active
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103619171A (zh) * | 2010-11-03 | 2014-03-05 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
CN104010505A (zh) * | 2011-10-26 | 2014-08-27 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
WO2013162715A2 (en) * | 2012-04-27 | 2013-10-31 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
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ES2836423T3 (es) | 2021-06-25 |
WO2016128266A1 (en) | 2016-08-18 |
US20180027815A1 (en) | 2018-02-01 |
EP3255989B1 (en) | 2020-09-16 |
US10905123B2 (en) | 2021-02-02 |
CN107250127A (zh) | 2017-10-13 |
BR112017017193A2 (pt) | 2018-06-26 |
GB201502164D0 (en) | 2015-03-25 |
EP3255989A1 (en) | 2017-12-20 |
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