CN1527812A - 具有除草活性的新的取代的苯胺衍生物 - Google Patents

具有除草活性的新的取代的苯胺衍生物 Download PDF

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CN1527812A
CN1527812A CNA028140923A CN02814092A CN1527812A CN 1527812 A CN1527812 A CN 1527812A CN A028140923 A CNA028140923 A CN A028140923A CN 02814092 A CN02814092 A CN 02814092A CN 1527812 A CN1527812 A CN 1527812A
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P·拉波尔塔
F·贝塔瑞尼
G·梅泽
D·波尔托索
L·福尔纳里
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Abstract

通式(I)化合物，其中：R代表氢原子、C1－C8烷基或卤代烷基、C2－C8烷氧基烷基或卤代烷氧基烷基、C2－C8链烯基或卤代链烯基、C2－C8炔基或卤代炔基，可任选被卤素原子和/或C1－C4烷基或卤代烷基取代的C3－C8环烷基或C4－C9环烷基烷基，C1－C8烷氧基或卤代烷氧基，NRaRb基团；Ra和Rb相同或不同，并代表氢原子；C1－C8烷基；苯基或苄基，所述苯基或苄基可任选被下列基团取代：卤素原子、CN、NO2、C1－C4烷基、卤代烷基、烷氧基、卤代烷氧基；或者Ra与Rb一起代表可任选被氧原子间断的C2－C8亚烷基链；Rn代表氢原子或C1－C4烷基或卤代烷基；R1代表氢原子、卤素原子、C1－C4烷基或卤代烷基、C1－C4烷氧基或卤代烷氧基、C1－C4烷硫基或卤代烷硫基、氰基、硝基；R2代表C1－C4烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基或卤代烷硫基，或卤素原子；X和X1相同或不同，并代表氢原子或卤素原子；A代表氧原子、－CR3R4O－基团、－OCR3R4－基团，其中R3和R4相同或不同，并代表氢原子或C1－C4烷基、卤代烷基。

Description

具有除草活性的新的取代的苯胺衍生物
本发明涉及新的取代的苯胺衍生物。
更具体来说，本发明涉及具有除草活性的新的邻位取代的苯胺衍生物，其制备方法及其作为控制农作物中的杂草的除草剂的应用。
德国专利申请2,855,699中描述了具有除草活性的间位取代的苯胺衍生物。然而，这些化合物作为除草剂显得不令人满意，因为它们需要高的施用剂量。
专利申请WO 98/03500中描述了相对于胺基在“邻位”被不同取代的苯氧基、苯氧基甲基或苯基甲氧基取代的杂环基-或苯基-甲酰苯胺。该专利申请的化合物在本质上具有杀真菌剂和杀虫剂的活性。
本申请人现在已经发现，一系列新的苯胺衍生物具有令人惊奇的高除草活性，同时对于一种或多种土地耕种作物具有低的植物毒害作用，所述苯胺衍生物在“邻位”—相对于胺基—被苯氧基甲基、苯基甲氧基或苯氧基取代，而所述苯氧基甲基、苯基甲氧基或苯氧基取代基又被特定基团取代。
因此，本发明的目的涉及新的通式(I)化合物：
其中：
-R代表氢原子、C1-C8烷基或卤代烷基、C2-C8烷氧基烷基或卤代烷氧基烷基、C2-C8链烯基或卤代链烯基、C2-C8炔基或卤代炔基，可任选被卤素原子和/或C1-C4烷基或卤代烷基取代的C3-C8环烷基或C4-C9环烷基烷基，C1-C8烷氧基或卤代烷氧基，NRaRb基团；
-Ra和Rb相同或不同，并代表氢原子；C1-C8烷基；苯基或苄基，所述苯基或苄基可任选被下列基团取代：卤素原子、CN、NO2、C1-C4烷基、卤代烷基、烷氧基、卤代烷氧基；或者Ra与Rb一起代表可任选被氧原子间断的C2-C8亚烷基链；
-Rn代表氢原子或C1-C4烷基或卤代烷基；
-R1代表氢原子、卤素原子、C1-C4烷基或卤代烷基、C1-C4烷氧基或卤代烷氧基、C1-C4烷硫基或卤代烷硫基、氰基、硝基；
-R2代表C1-C4烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基或卤代烷硫基，或卤素原子；
-X和X1相同或不同，并代表氢原子或卤素原子；
-A代表氧原子、-CR3R4O-基团、-OCR3R4-基团，其中R3和R4相同或不同，并代表氢原子或C1-C4烷基、卤代烷基。
在其活性方面特别值得关注的通式(I)化合物的具体实例列在表1中详细说明：
                           表1
X    X1   R2     A         R1     Rn      R
H    H     CF3    CH2O     CH3    H        环丙基
H    H     CF3    OCH2     CH3    H        环丙基
H    H     CF3    O         CH3    H        环丙基
H    H     CF3    CH2O     CH3    H        异丙基
H    H     CF3    OCH2     CH3    H        异丙基
H    H     CF3    O         CH3    H        异丙基
H    H     CF3    CH2O     CH3    H        正丙基
H    H     CF3    OCH2     CH3    H        正丙基
H    H     CF3    O         CH3    H        正丙基
H    H     CF3    CH2O     CH3    H        乙基
H    H     CF3    OCH2     CH3    H        乙基
H    H     CF3    O         CH3    H        乙基
H    H     CF3    CH2O     CH3    H        甲基
H    H     CF3    OCH2     CH3    H        甲基
H    H     CF3    O         CH3    H        甲基
H    H     CF3    CH2O     CH3    H        ClCH2
H    H     CF3    OCH2     CH3    H        ClCH2
H    H     CF3    O         CH3    H        ClCH2
H    H     CF3    CH2O     CH3    H        H
H    H     CF3    OCH2     CH3    H        H
H    H     CF3    O         CH3    H        H
F    H     CF3    OCH2     CH3    H        环丙基
F    H     CF3    O         CH3    H        环丙基
H    H     OCF2H  CH2O     CH3    H        环丙基
H    H     OCF2H  OCH2     CH3    H        环丙基
H    H     OCF2H  O         CH3    H        环丙基
H    H     OCF2H  CH2O     CH3    H        异丙基
H    H     OCF2H  OCH2     CH3    H        异丙基
H    H     OCF2H  O         CH3    H        异丙基
H    H     CF3    CH2O     CH3    H        1-甲基环丙基
H    H     CF3    OCH2     CH3    H        1-甲基环丙基
H    H     CF3    O         CH3    H        1-甲基环丙基
H    H     CF3    CH2O     CH3    H        环丁基
H    H     CF3    OCH2     CH3    H        环丁基
H    H     CF3    O         CH3    H        环丁基
                          表1(续)
X    X1  R2     A          R1     Rn       R
H    H    CF3    CH2O      CH3    H        环戊基
H    H    CF3    OCH2      CH3    H        环戊基
H    H    CF3    O          CH3    H        环戊基
H    H    CF3    CH2O      CH3    H        异丁基
H    H    CF3    OCH2      CH3    H        异丁基
H    H    CF3    O          CH3    H        异丁基
H    H    CF3    CH2O      CH3    H        CH3OCH2
H    H    CF3    OCH2      CH3    H        CH3OCH2
H    H    CF3    O          CH3    H        CH3OCH2
H    H    CF3    CH2O      CH3    H        (CH3)2N
H    H    CF3    OCH2      CH3    H        (CH3)2N
H    H    CF3    O          CH3    H        (CH3)2N
H    H    CF3    CH2O      CH3    H        1-吡咯烷基
H    H    CF3    OCH2      CH3    H        1-吡咯烷基
H    H    CF3    O          CH3    H        1-吡咯烷基
H    H    CF3    CH2O      CH3    H        1-吗啉基
H    H    CF3    OCH2      CH3    H        1-吗啉基
H    H    CF3    O          CH3    H        1-吗啉基
H    H    CF3    CH2O      H       H        环丙基
H    H    CF3    OCH2      H       H        环丙基
H    H    CF3    O          H       H        环丙基
H    H    CF3    CH2O      F       H        环丙基
H    H    CF3    OCH2      F       H        环丙基
H    H    CF3    O          F       H        环丙基
H    H    CF3    OCH2      Cl      H        环丙基
H    H    CF3    CH2O      CH3    H        CH3O
H    H    CF3    OCH2      CH3    H        CH3O
H    H    CF3    O          CH3    H        CH3O
H    H    CF3    CH2O      CH3    H        CH3CH2O
H    H    CF3    OCH2      CH3    H        CH3CH2O
H    H    CF3    O          CH3    H        CH3CH2O
H    F    CF3    CH2O      CH3    H        环丙基
H    F    CF3    OCH2      CH3    H        环丙基
H    F    CF3    O          CH3    H        环丙基
本发明的另一个目的涉及制备通式(I)化合物的方法。
通式(I)化合物可依据反应方案1，通过将通式(II)胺衍生物与通式(III)化合物反应来制得。
反应方案1
在所述式中，R、Rn、R1、R2、X、X1和A具有上述含义，Z代表卤素原子、烷氧基、羟基。
进行上述方法的反应条件可根据式(III)化合物的性质而变。
例如，当Z代表卤素原子时，该反应优选在惰性溶剂存在下，以及在有机或无机碱存在下，于-20℃至反应混合物沸点温度进行。
可用于上述反应的溶剂的实例包括水、脂族或脂环族烃(石油醚、己烷、环己烷等)、氯代烃(二氯甲烷、氯仿、四氯化碳、二氯甲烷等)、芳族烃(苯、甲苯、二甲苯、氯苯等)、醚(乙醚、二异丙基醚、二甲氧基乙烷、二氧杂环己烷、四氢呋喃等)、酯(乙酸乙酯等)、酮(丙酮、甲基乙基酮、甲基丙基酮、甲基异丁基酮等)、腈(乙腈、苄腈等)、非质子偶极溶剂(二甲基甲酰胺、二甲基乙酰胺、六甲基磷酸三酰胺、二甲亚砜、环丁砜、N-吡咯烷酮等)。
可用于该反应的无机碱是例如氢氧化物、碳酸钠、钠和钾的碳酸盐和碳酸氢盐。
可用于该反应的有机碱是例如三乙胺、吡啶、4-N，N-二甲基氨基吡啶、N，N-二甲基苯胺、N-甲基哌啶、二甲基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)、二氮杂二环十一碳烯(DBU)。
或者，其中A代表-CR3R4O-基团的通式(I)化合物可这样制得：依据反应方案2，将通式(IV)衍生物与通式(V)苯酚缩合，以生成通式(Ia)醚，
反应方案2
在该反应方案所示的通式中，R、Rn、R1、R2、R3、R4、X和X1具有如上所定义的含义，Z1代表卤素原子，优选氯或溴，或RzSO3所示基团，其中Rz代表C1-C4烷基或任选被C1-C4烷基取代的苯基。
该醚化反应优选在一种或多种惰性有机溶剂存在下，以及在碱，优选无机碱存在下于-10℃至反应混合物沸点温度进行。
可用于该反应的有机溶剂是例如芳族烃(苯、甲苯、二甲苯、氯苯等)、醚(乙醚、二异丙基醚、二甲氧基乙烷、二氧杂环己烷、四氢呋喃等)、醇和二醇(甲醇、乙醇、甲基纤溶剂、乙二醇等)、酮(丙酮、甲基乙基酮、甲基丙基酮、甲基异丁基酮等)、腈(乙腈、苄腈等)、非质子偶极溶剂(二甲基甲酰胺、二甲基乙酰胺、六甲基磷酸三酰胺、二甲亚砜、环丁砜、N-吡咯烷酮等)。
可用于该反应的无机碱是例如氢化钠、氢化钾、氢氧化钠、氢氧化钾、碳酸钠和碳酸钾。
该反应可依据Dehmlow和Dehmlow在“Phase Transfer Catalysis”(1983)，Verlag Chemie中描述的方法，在作为溶剂的使用水以及与其不可混溶的有机溶剂的二相系统中，在相转移催化剂存在下有利地进行。
类似地，其中A代表-OCR3R4-基团的通式(I)化合物还可这样制得：依据反应方案3，将通式(VI)苯酚与通式(VII)衍生物反应，以生成通式(Ib)醚，
反应方案3
在该反应方案所示的通式中，R、Rn、R1、R2、R3、R4、X和X1具有如上所定义的含义，Z2代表卤素原子，优选氯或溴，或RzSO3所示基团，其中Rz代表C1-C4烷基或任选被C1-C4烷基取代的苯基。
操作过程以及可用于反应方案3所示醚化反应的溶剂与碱的类型与在描述反应方案2的反应时所提及的那些完全类似。
当自身是未知的时，通式(II)、(III)、(IV)、(V)、(VI)和(VII)中间体可依据有机化学领域已知的方法容易地制得。
如上所述，通式(I)化合物具有高除草活性，这使得它们可适用于耕种的田地以保护有用的农作物不被杂草影响。
特别是，本发明化合物在许多单子叶和双子叶杂草的芽前和苗后控制都有效。同时，在芽前和/或苗后处理期间，对于有用的农作物，本发明化合物表现出相容性或者没有毒害作用。
可用通式(I)化合物有效地控制的杂草的实例是：苘麻(Abutilontheofrasti)、泽泻(Alisma plantago)、苋属(Amaranthus spp.)、Amni maius、荠(Capsella bursa pastoris)、藜(Chenopodium.Album)、Convolvulus sepium、猪殃殃(Galium aparine)、Geraniumdissectum、番薯属(Ipomea spp.)、母菊属(Matricaria spp.)、虞美人(Papaver rhoeas)、Phaseolus aureus、春蓼(Polygonumpersicaria)、马齿苋(Portulaca oleracea)、Sida spinosa、野欧白芥(Sinapis arvensis)、龙葵(Solanum nigrum)、繁缕(Stellariamedia)、婆婆纳属(Veronica spp.)、堇菜属(Viola spp.)、苍耳属(Xanthium spp.)、大穗看麦娘(Alopecurus myosuroides)、野燕麦(Avena fatua)、莎草属(Cyperus spp.)、马唐(Digitariasanguinalis)、稗属(Echinocloa spp.)、Heleocaris avicularis、异蕊花属(Heteranthera spp.)、黍属(Panicum spp.)、早熟禾属(Poaspp.)、莞草属(Scirpus spp.)、蜀黍属(Sorghum spp.)等。
在以施用于耕种田地的剂量使用时，上述化合物对于任何耕种作物例如稻( Oryza  sativa)、小麦( Triticum  sp.)、大麦( Hordeum vulgare)、玉米( Zea  mays)、大豆( Glycine  max)都不表现出任何毒害作用。
本发明的另一个目的涉及控制栽种区域中的杂草的方法，包括施用通式(I)化合物。
为了获得所需效果而施用的化合物的量可根据多种因素而变，例如所用的化合物、欲保护的农作物、欲消灭的杂草、侵害程度、气候条件、土地特性、施用方法等。
每公顷1g-1000g的化合物剂量一般能提供足够的控制。
在用于农业中时，使用含有一种或多种还可能作为异构体混合物的通式(I)化合物作为活性组分的具有除草活性的组合物经常是有利的。
组合物可以以干粉剂、可湿性粉剂、乳油、微乳剂、糊剂、粒剂、溶液、悬浮液等形式使用；组合物类型的选择取决于具体应用。
本发明组合物可依据已知方法制得，例如通过任选在表面活性剂存在下用溶剂和/或固体稀释介质将活性组分稀释或溶解来制得。
高岭土、矾土、二氧化硅、滑石、膨润土、白垩、石英、白云石、绿坡缕石、蒙脱石、硅藻土、纤维素、淀粉等可用作固体惰性稀释剂或载体。
水或有机溶剂例如芳族烃(二甲苯、烷基苯的混合物等)、脂族烃(己烷、环己烷等)、卤代芳族烃(氯苯等)、醇(甲醇、丙醇、丁醇、辛醇等)、酯(乙酸异丁酯等)、酮(丙酮、环己酮、苯乙酮、异佛尔酮、乙基戊基酮等)或植物油或矿物油或它们的混合物等可用作液体惰性稀释剂。
还可以使用非离子型润湿剂和乳化剂(聚乙氧基化烷基苯酚、聚乙氧基化脂肪醇等)、阴离子型润湿剂和乳化剂(烷基苯磺酸盐、烷基磺酸盐等)、阳离子型润湿剂和乳化剂(烷基铵的季铵盐等)。
还可以加入分散剂(例如木质素及其盐、纤维素衍生物、藻酸盐等)、稳定剂(例如抗氧化剂、紫外线吸收剂等)。
为了拓宽上述组合物的作用范围，可加入其它组分例如其它除草剂、杀真菌剂、杀虫剂、沙螨剂、肥料等。
可加入到含有一种或多种通式(I)化合物的组合物中的其它除草剂的实例如下：乙草胺、三氟羧草醚、苯草醚、AKH-7088、甲草胺、禾草灭、莠灭净、amicarbazone、酰嘧磺隆、杀草强、莎稗磷、磺草灵、莠去津、唑啶炔草、四唑嘧磺隆、叠氮津、BAY MKH 6561、beflubutamid、草除灵、乙丁氟灵、呋草黄、苄嘧磺隆、地散磷、灭草松、benzfendizone、benzobicyclon、吡草酮、苯噻隆、甲羧除草醚、双丙氨酰膦、双草醚、除草定、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、butafenacil、抑草磷、丁烯草胺、仲丁灵、丁氧环酮、丁草敌、cafenstrole、双酰草胺、氟酮唑草、甲氧除草醚、草灭畏、氯溴隆、氯炔灵、氯甲丹、氯草敏、氯嘧磺隆、草枯醚、绿麦隆、枯草隆、氯苯胺灵、氯磺隆、敌草索、氯硫酰草胺、cinidon ethyl、环庚草醚、醚磺隆、烯草酮、炔草酯、异噁草松、氯甲酰草胺、二氯吡啶酸、唑嘧磺胺盐、cumyluron(JC-940)、氰草津、环草敌、环丙嘧磺隆、噻草酮、氰氟草酯、2，4-D、2，4-DB、香草隆、茅草枯、甜菜安、敌草净、麦草畏、敌草腈、2，4-滴丙酸、精2，4-滴丙酸、氯甲草、唑嘧磺胺、乙酰甲草胺、枯莠隆、野燕枯、吡氟酰草胺、二氟吡隆、唑隆、哌草丹、二甲草胺、异戊净、二甲吩草胺、氨氟灵、地乐酚、地乐酯、特乐酚、双苯酰草胺、异丙净、敌草快、氟硫草定、1-敌草隆、草止津、茵多酸、EPTC、戊草丹、乙丁烯氟灵、胺苯黄隆、磺噻隆、乙嗪草酮(SMY1500)、乙氧呋草黄、ethoxyfen-ethyl(HC-252)、乙氧嘧黄隆、乙苯酰草(HW 52)、噁唑禾草灵、精噁唑禾草灵、fentrazamide、非草隆、氟燕灵、麦草伏M、啶嘧磺隆、florasulam、吡氟禾草灵、精吡氟禾草灵、fluazolate(JV 485)、flucarbazone-sodium、氯乙氟灵、flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropin、氟草隆、乙羧氟草醚、氟除草醚、氟胺草唑、四氟丙酸、氟啶黄隆、芴丁酯、氟啶草酮、flurochloridone、氯氟吡氧乙酸、呋草酮、达草氟、氟磺胺草醚、foramsulfuron、杀木膦、氟氧草醚、草铵膦、草甘膦、氯吡嘧磺隆、吡氟氯禾灵、精吡氟氯禾灵、环嗪酮、咪草酸、咪草啶酸、imazapic、咪唑烟酸、咪唑喹啉酸、咪唑乙烟酸、唑吡嘧磺隆、indanofan、iodosulfuron、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草胺、isoxachlortole、异噁氟草、异噁草醚、KPP-421、乳氟禾草灵、环草定、利谷隆、LS830556、2甲4氯、2甲4氯乙硫酯、2甲4氯丁酸、2甲4氯丙酸、精2甲4氯丙酸、苯噻酰草胺、mesotrione、苯嗪草酮、吡唑草胺、甲基苯噻隆、灭草唑、盖草津、甲基杀草隆、吡喃隆、溴谷隆、异丙甲草胺、S-异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲磺隆、禾草敌、庚酰草胺、绿谷隆、萘丙胺、敌草胺、萘草胺、NC-330、草不隆、烟嘧磺隆、氟氯草胺、氟草敏、坪草丹、氨磺乐灵、炔丙噁唑草、噁草酮、环丙氧黄隆、氯噁嗪草、乙氧氟草醚、百草枯、克草敌、二甲戊灵、甲氯酰草胺、戊噁唑草、pethoxamid、甜草宁、氨氯吡啶酸、picolinafen、哌草磷、丙草胺、氟嘧磺隆、氨氟乐灵、profluazol、甘扑津、扑灭通、扑草净、毒草胺、敌稗、噁草酸、扑灭津、苯胺灵、异丙草胺、炔苯酰草胺、苄草丹、氟磺隆、pyraclonil、氟唑草酯、吡唑特、吡嘧磺隆、苄草唑、嘧苯草肟、稗草丹、pyridafol、哒草特、pyriftalid、肟啶草、嘧草硫醚、二氯喹啉酸、氯甲喹啉酸、喹禾灵、精喹禾灵、砜嘧磺隆、稀禾定、环草隆、西玛津、西草净、磺草酮、甲磺草胺、甲嘧磺隆、乙黄黄隆、2，3，6-TBA、TCA-钠、牧草胺、丁噻隆、tepraloxydim、特草定、甲氧去草净、特丁津、特丁净、噻吩草胺、噻氟隆、噻唑烟酸、噻二唑胺、噻吩磺隆、禾草丹、仲草丹、嘧草胺、三甲苯草酮、野麦畏、醚苯磺隆、triaziflam、苯磺隆、三氯吡氧乙酸、草达津、trifloxysulfuron、氟乐灵、氟胺磺隆、tritosulfuron、UBI-C4874、灭草敌。
活性物质在上述组合物中的浓度可在宽的范围内变化，这取决于所述活性化合物、它们的预定应用、环境条件和所用的制剂类型。
活性物质的浓度一般优选为1-90％。
下面提供本发明的某些示例性非限制性实例。
实施例1
制备N-[4-甲基-2-(3-三氟甲基苯基)-甲氧基苯基]环丙烷甲酰胺(C-1)
将N-(2-羟基-4-甲基苯基)环丙烷甲酰胺(1g；5.2mmol)在N，N-二甲基甲酰胺(DMF；13ml)中的溶液置于保持在氮气氛下的100ml烧瓶内。加入碳酸钾(1g；7.2mmol)，将该混合物在室温搅拌，并加入3-三氟甲基苄基氯(1.1g；5.6mmol)在DMF(2ml)中的溶液。在搅拌下将该混合物于60℃加热3小时。冷却后，将其倒入水(150ml)中，用乙酸乙酯(3×50ml)萃取，将有机相用水(2×50ml)洗涤，用硫酸钠干燥，过滤并浓缩。将粗产物(1.6g)从己烷/乙酸乙酯8∶2混合物中结晶。获得了1.3g固体结晶，熔点为153-155℃。
实施例2
制备N-[4-甲基-2-(3-三氟甲基苯氧基)-甲基苯基]环丙烷甲酰胺(C-2)
在0℃、搅拌下，在保持在氮气氛下的100ml烧瓶内，将环丙烷甲酰氯(0.54g；5.16mmol)在二氯甲烷(5ml)中的溶液滴加到4-甲基-2-三氟甲基-苯氧基甲基)苯胺(1.4g；5mmol)和三乙胺(0.55g；5.44mmol)在二氯甲烷(15ml)内的混合物中。在搅拌下将该混合物加热回流3小时。冷却后，将该混合物倒入水(150ml)中，用二氯甲烷(3×50ml)萃取，将有机相用水(2×50ml)洗涤，用硫酸钠干燥，过滤并浓缩。获得了1.5g所需产物(1H-NMR，元素分析)。
实施例3
按照类似于上文实施例1和2中描述的方法，制得了如下表2所示的通式(I)化合物(C)。
Figure A0281409200171
                                      表2
C       X      X1    R2     A        R1     Rn     R            M.P.(℃)
1       H      H      CF3    CH2O    CH3    H      环丙基        153-155
2       H      H      CF3    OCH2    CH3    H      环丙基
3       H      H      CF3    O        CH3    H      环丙基
4       H      H      CF3    CH2O    CH3    H      异丙基
5       H      H      CF3    OCH2    CH3    H      异丙基
6       H      H      CF3    O        CH3    H      异丙基
7       H      H      CF3    CH2O    CH3    H      正丙基
8       H      H      CF3    OCH2    CH3    H      正丙基
9       H      H      CF3    O        CH3    H      正丙基
10      H      H      CF3    CH2O    CH3    H      乙基
11      H      H      CF3    OCH2    CH3    H      乙基
12      H      H      CF3    O        CH3    H      乙基
13      H      H      CF3    CH2O    CH3    H      甲基
14      H      H      CF3    OCH2    CH3    H      甲基
15      H      H      CF3    O        CH3    H      甲基
16      H      H      CF3    CH2O    CH3    H      ClCH2
17      H      H      CF3    OCH2    CH3    H      ClCH2
18      H      H      CF3    O        CH3    H      ClCH2
19      H      H      CF3    CH2O    CH3    H      H
20      H      H      CF3    OCH2    CH3    H      H
21      H      H      CF3    O        CH3    H      H
22      F      H      CF3    OCH2    CH3    H      环丙基
23      F      H      CF3    O        CH3    H      环丙基
24      H      H      OCF2H  CH2O    CH3    H      环丙基
25      H      H      OCF2H  OCH2    CH3    H      环丙基
26      H      H      OCF2H  O        CH3    H      环丙基
27      H      H      OCF2H  CH2O    CH3    H      异丙基
28      H      H      OCF2H  OCH2    CH3    H      异丙基
29      H      H      OCF2H  O        CH3    H      异丙基
30      H      H      CF3    CH2O    CH3    H      1-甲基环丙基
31      H      H      CF3    OCH2    CH3    H      1-甲基环丙基
32      H      H      CF3    O        CH3    H      1-甲基环丙基
33      H      H      CF3    CH2O    CH3    H      环丁基
34      H      H      CF3    OCH2    CH3    H      环丁基
                                     表2(续)
C      X      X1   R2     A        R1     Rn     R            M.P.(℃)
35     H      H     CF3    O        CH3    H      环丁基
36     H      H     CF3    CH2O    CH3    H      环戊基
37     H      H     CF3    OCH2    CH3    H      环戊基
38     H      H     CF3    O        CH3    H      环戊基
39     H      H     CF3    CH2O    CH3    H      异丁基
40     H      H     CF3    OCH2    CH3    H      异丁基
41     H      H     CF3    O        CH3    H      异丁基
42     H      H     CF3    CH2O    CH3    H      CH3OCH2
43     H      H     CF3    OCH2    CH3    H      CH3OCH2
44     H      H     CF3    O        CH3    H      CH3OCH2
45     H      H     CF3    CH2O    CH3    H      (CH3)2N
46     H      H     CF3    OCH2    CH3    H      (CH3)2N
47     H      H     CF3    O        CH3    H      (CH3)2N
48     H      H     CF3    CH2O    CH3    H      1-吡咯烷基
49     H      H     CF3    OCH2    CH3    H      1-吡咯烷基
50     H      H     CF3    O        CH3    H      1-吡咯烷基
51     H      H     CF3    CH2O    CH3    H      1-吗啉基
52     H      H     CF3    OCH2    CH3    H      1-吗啉基
53     H      H     CF3    O        CH3    H      1-吗啉基
54     H      H     CF3    CH2O    H       H      环丙基
55     H      H     CF3    OCH2    H       H      环丙基
56     H      H     CF3    O        H       H      环丙基
57     H      H     CF3    CH2O    F       H      环丙基
58     H      H     CF3    OCH2    F       H      环丙基
59     H      H     CF3    O        F       H      环丙基
60     H      H     CF3    OCH2    Cl      H      环丙基
61     H      H     CF3    CH2O    CH3    H      CH3O
62     H      H     CF3    OCH2    CH3    H      CH3O
63     H      H     CF3    O        CH3    H      CH3O
64     H      H     CF3    CH2O    CH3    H      CH3CH2O
65     H      H     CF3    OCH2    CH3    H      CH3CH2O
66     H      H     CF3    O        CH3    H      CH3CH2O
67     H      F     CF3    CH2O    CH3    H      环丙基
68     H      F     CF3    OCH2    CH3    H      环丙基
实施例4
测定芽前除草活性和植物毒害作用
依据下述方法评价本发明化合物的芽前除草活性。
将进行测试的植物品种(杂草或农作物)栽种在直径超过10cm，高为10cm，并含有沙壤土的花瓶中。每种植物使用10只花瓶。
对于每种杂草和农作物，将花瓶进一步分成两组，每组包括5只花瓶。
栽培24小时后，用轻的淋浴润湿花瓶。润湿1小时后，用含有10％v丙酮、所需浓度的测试化合物和0.5％吐温20的水-丙酮分散液处理第一组花瓶。
第二组花瓶仅用含有10％体积的丙酮和0.5％吐温20的水-丙酮溶液处理，并用作对照(空白)。
处理后，给所有花瓶浇水，并保持在如下的控制环境条件下：
-温度：24℃
-相对湿度：60％
-光照期：16小时
-光强度：10,000lux
处理后28天，基于下列取值等级来评价除草活性，其中这些值是指相对于未处理的植物(空白)，所测定的处理的植物的损害百分比：
-  0＝0-9％损害
-  1＝10-29％损害
-  2＝30-49％损害
-  3＝50-69％损害
-  4＝70-89％损害
-  5＝90％损害-植物死亡
表3列出了用下列植物品种以500g/ha的剂量评价的化合物C-1、C-2和C-3的所得结果：
反枝苋(AR)、荠(CP)、藜(CA)、猪殃殃(GA)、母菊(Matricariachamomilla)(MC)、虞美人(PR)、马齿苋(PO)、繁缕(SM)、大穗看麦娘(AM)、洋野黍(Panicum dicothomiflorum)(PD)、玉米(M)、小麦(F)。
表3：500g/ha的剂量的芽前除草活性
  植物   → AR  CP  CA  GA  MC  PR  PO  SM  AM  PD  M  F↓化合物
C-1         5   5   5   5   5   5   5   5   5   5   0  0C-2         5   5   5   5   5   5   5   5   5   5   0  0C-3         5   5   5   5   5   5   5   5   5   5   0  0

Claims (11)

1.通式(I)化合物：
其中：
-R代表氢原子、C1-C8烷基或卤代烷基、C2-C8烷氧基烷基或卤代烷氧基烷基、C2-C8链烯基或卤代链烯基、C2-C8炔基或卤代炔基，可任选被卤素原子和/或C1-C4烷基或卤代烷基取代的C3-C8环烷基或C4-C9环烷基烷基，C1-C8烷氧基或卤代烷氧基，NRaRb基团；
-Ra和Rb相同或不同，并代表氢原子；C1-C8烷基；苯基或苄基，所述苯基或苄基可任选被下列基团取代：卤素原子、CN、NO2、C1-C4烷基、卤代烷基、烷氧基、卤代烷氧基；或者Ra与Rb一起代表可任选被氧原子间断的C2-C8亚烷基链；
-Rn代表氢原子或C1-C4烷基或卤代烷基；
-R1代表氢原子、卤素原子、C1-C4烷基或卤代烷基、C1-C4烷氧基或卤代烷氧基、C1-C4烷硫基或卤代烷硫基、氰基、硝基；
-R2代表C1-C4烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基或卤代烷硫基，或卤素原子；
-X和X1相同或不同，并代表氢原子或卤素原子；
-A代表氧原子、-CR3R4O-基团、-OCR3R4-基团，其中R3和R4相同或不同，并代表氢原子或C1-C4烷基、卤代烷基。
2.制备通式(I)化合物的方法，包括依据反应方案1将通式(II)胺衍生物与通式(III)化合物反应：
反应方案1
Figure A028140920003C1
其中R、Rn、R1、R2、X、X1和A具有上述含义，Z代表卤素原子、烷氧基、羟基。
3.权利要求2的方法，其中Z代表卤素原子，并且该反应在惰性溶剂中，在有机或无机碱存在下，于-20℃至反应混合物沸点温度进行。
4.制备其中A代表-CR3R4O-基团的通式(I)化合物的方法，包括依据反应方案2，将通式(IV)衍生物与通式(V)苯酚缩合，以生成通式(Ia)醚，
反应方案2
Figure A028140920003C2
Figure A028140920004C1
其中R、Rn、R1、R2、R3、R4、X和X1具有如上所定义的含义，Z1代表卤素原子或RzSO3基团，其中Rz代表C1-C4烷基或任选被C1-C4烷基取代的苯基，
并且该反应在一种或多种惰性有机溶剂和碱存在下，于-10℃至反应混合物沸点温度进行。
5.制备其中A代表-OCR3R4-基团的通式(I)化合物的方法，包括依据反应方案3，将通式(VI)苯酚与通式(VII)衍生物反应，以生成通式
(Ib)醚，
反应方案3
Figure A028140920004C2
其中R、Rn、R1、R2、R3、R4、X和X1具有如上所定义的含义，Z1代表卤素原子或RzSO3基团，其中Rz代表C1-C4烷基或任选被C1-C4烷基取代的苯基，
并且该反应在一种或多种惰性有机溶剂和碱存在下，于-10℃至反应混合物沸点温度进行。
6.权利要求1的化合物作为除草剂的应用。
7.除草组合物，包含固体载体、液体稀释剂、表面活性剂或其它专门的添加剂以及至少一种权利要求1的化合物。
8.上一权利要求的组合物，其中所述化合物的浓度为1-90％。
9.权利要求8的组合物，其中所述组合物还包含其它除草剂。
10.控制栽种区域中的杂草的方法，包括将权利要求1的化合物或权利要求7的组合物施用到所述区域。
11.权利要求10的方法，其中活性化合物以每公顷1g-1000g的剂量施用。
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