CN112513033A - 除草活性的双环苯甲酰基吡唑 - Google Patents
除草活性的双环苯甲酰基吡唑 Download PDFInfo
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- CN112513033A CN112513033A CN201980049886.XA CN201980049886A CN112513033A CN 112513033 A CN112513033 A CN 112513033A CN 201980049886 A CN201980049886 A CN 201980049886A CN 112513033 A CN112513033 A CN 112513033A
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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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
- C07D417/02—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 two hetero rings
- C07D417/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Abstract
本发明涉及作为除草剂的通式(I)的双环苯甲酰基吡唑。在式(I)中,A、X1和X2代表(CH2)n、O或S(O)n。R、Ra、Rb、Rp1、Rp2和Rp3代表基团如氢、卤素、烷基、烷氧基和环烷基。
Description
本发明涉及除草剂的技术领域,特别是用于选择性防治有用植物作物中的杂草和禾本科杂草(weed grass)的除草剂的技术领域。
具体地,本发明涉及取代的双环苯甲酰基吡唑、其制备方法及其作为除草剂的用途。
WO 97/08164 A1和JPH10130267尤其记载了在苯甲酰基的2,3-位或3,4-位稠合的取代的苯甲酰基吡唑。这些已知化合物的除草活性、特别是在低施用率下的除草活性和/或它们与作物植物的相容性仍然需要改进。
由于所述原因,仍然需要有效的除草剂和/或植物生长调节剂,以选择性地用于作物植物中或用在非作物土地上,其中这些活性成分优选在施用中应具有其他有利的特性,例如提高的与作物植物的相容性。
因此,本发明的一个目的是提供具有除草活性的化合物,其即使在相对低的施用率下也对经济上重要的有害植物非常有效,并且可选择性地用于作物植物中,优选对有害植物具有良好的活性,并且同时优选与作物植物具有良好的相容性。优选地,这些除草化合物应当对广谱的禾本科杂草特别有效且高效,并且优选还对大量的杂草具有良好的活性。
出乎意料地,现已发现下文式(I)的化合物及其盐对广谱的经济上重要的单子叶和双子叶一年生有害植物具有优异的除草活性。
因此,本发明提供通式(I)的化合物及其农业化学上可接受的盐,
其中符号和下标(indices)具有以下含义:
A代表(CH2)n,
X1、X2彼此独立地各自代表O或S(O)n,
R代表卤代-(C1-C6)-烷基,
Ra、Rb彼此独立地各自代表氢、氟、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基、(C1-C6)-烷硫基、氰基,或
Ra和Rb连同它们所连接的碳原子一起形成羰基或硫代羰基,
Rp1代表氢、(C1-C4)-烷基羰基氧基-(C1-C4)-烷基、(C1-C4)-烷氧基羰基氧基-(C1-C4)-烷基、(C1-C6)-烷基磺酰基、(C1-C4)-烷氧基-(C1-C6)-烷基磺酰基,或在每种情况下被n个选自卤素、(C1-C4)-烷基和(C1-C4)-烷氧基的相同或不同的基团取代的苯基磺酰基、硫代苯基-2-磺酰基、苯甲酰基、苯甲酰基-(C1-C6)-烷基或苄基,
Rp2代表(C1-C4)-烷基,
Rp3代表氢、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C8)-环烷基、(C1-C4)-烷基-(C3-C8)-环烷基或(C3-C6)-卤代环烷基,
n代表0、1或2。
式(I)的化合物能够形成盐。可以通过碱作用于那些带有酸性氢原子的式(I)的化合物而形成盐。合适的碱为例如有机胺,如三烷基胺、吗啉、哌啶或吡啶;以及铵、碱金属或碱土金属的氢氧化物、碳酸盐和碳酸氢盐,特别是氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠和碳酸氢钾。这些盐为其中酸性氢被农业上合适的阳离子替代的化合物,例如金属盐,特别是碱金属盐或碱土金属盐,特别是钠盐和钾盐;或铵盐、与有机胺的盐或季铵盐,例如具有式[NRR′R″R″′]+的阳离子的盐,其中R至R″′各自彼此独立地代表有机基团,特别是烷基、芳基、芳烷基或烷基芳基。还合适的为烷基锍盐和烷基氧化锍盐,如(C1-C4)-三烷基锍盐和(C1-C4)-三烷基氧化锍盐。
式(I)的化合物可通过将合适的无机酸或有机酸添加到碱性基团上而形成盐,所述无机酸或有机酸为例如无机酸(如HCl、HBr、H2SO4、H3PO4或HNO3),或有机酸,例如羧酸(如甲酸、乙酸、丙酸、草酸、乳酸或水杨酸)或磺酸(如对甲苯磺酸);所述碱性基团为例如氨基、烷基氨基、二烷基氨基、哌啶子基(piperidino)、吗啉代(morpholino)或吡啶并(pyridino)。在这种情况下,这些盐包含酸的共轭碱作为阴离子。
以去质子化形式存在的合适的取代基(例如磺酸或羧酸)可以与本身可被质子化的基团(如氨基)形成内盐。
烷基是指在每种情况下具有指定的碳原子数的饱和的直链或支链烃基基团,例如C1-C6-烷基,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。
卤素取代的烷基是指以下直链或支链烷基:其中这些基团中的一些或全部的氢原子可被卤素原子替代,例如C1-C2-卤代烷基,如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、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、五氟乙基和1,1,1-三氟丙-2-基。
环烷基是指具有优选3-8个环碳原子的碳环饱和环体系,例如环丙基、环丁基、环戊基或环己基。在任选取代的环烷基的情况下,包括具有取代基的环体系,还包括在环烷基上具有双键的取代基,例如亚烷基,如亚甲基。
在任选取代的环烷基的情况下,还包括多环脂族体系,例如双环[1.1.0]丁-1-基、双环[1.1.0]丁-2-基、双环[2.1.0]戊-1-基、双环[2.1.0]戊-2-基、双环[2.1.0]戊-5-基、双环[2.2.1]庚-2-基(降冰片基)、金刚烷-1-基和金刚烷-2-基。
在取代的环烷基的情况下,还包括螺环脂族体系,例如螺[2.2]戊-1-基、螺[2.3]己-1-基和螺[2.3]己-4-基、3-螺[2.3]己-5-基。
烷氧基是指在每种情况下具有指定的碳原子数的饱和直链或支链烷氧基,例如C1-C6-烷氧基,如甲氧基、乙氧基、丙氧基、1-甲基乙氧基、丁氧基、1-甲基丙氧基、2-甲基丙氧基、1,1-二甲基乙氧基、戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、2,2-二甲基丙氧基、1-乙基丙氧基、己氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、1-甲基戊氧基、2-甲基戊氧基、3-甲基戊氧基、4-甲基戊氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,2-二甲基丁氧基、2,3-二甲基丁氧基、3,3-二甲基丁氧基、1-乙基丁氧基、2-乙基丁氧基、1,1,2-三甲基丙氧基、1,2,2-三甲基丙氧基、1-乙基-1-甲基丙氧基和1-乙基-2-甲基丙氧基。卤素取代的烷氧基是指下列在每种情况下具有指定的碳原子数的直链或支链烷氧基:其中这些基团中的一些或全部的氢原子可被如上所述的卤素原子替代,例如C1-C2-卤代烷氧基,如氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、1-氯乙氧基、1-溴乙氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-1,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、五氟乙氧基和1,1,1-三氟丙-2-氧基。
术语“卤素”是指氟、氯、溴或碘。如果该术语用于基团,则“卤素”是指氟、氯、溴或碘原子。
根据取代基的性质以及其连接方式,式(I)的化合物可以立体异构体的形式存在。例如,如果存在一个或多个不对称取代的碳原子和/或亚砜基,则可能出现对映异构体和非对映异构体。通过常规的分离方法,例如通过色谱分离方法,可从在制备过程中获得的混合物中获得立体异构体。同样可以通过使用光学活性原料和/或助剂进行立体选择性反应来选择性地制备立体异构体。
本发明还涉及为式(I)所涵盖但没有具体定义的所有立体异构体及其混合物。然而,为了简单起见,下文将总是提及式(I)的化合物,尽管这应理解为不仅是指纯的化合物,而且如果合适,还指具有不同量的异构化合物的混合物。
如果一个基团被基团多取代,则这意味着该基团被一个或多个相同或不同的选自上述那些的基团取代。
在下文中描述的所有式中,除非另有不同定义,取代基和符号具有与式(I)中所述相同的含义。化学式中的箭头表示其与分子的其余部分连接的点。
以下是对各取代基各自的优选、特别优选和非常特别优选的定义的说明。下文中未说明的通式(I)的其他取代基具有上文给出的定义。
优选通式(I)的化合物,其中符号和下标具有以下含义:
A代表(CH2)n,
X1、X2彼此独立地各自代表O或S(O)n,
R代表卤代-(C1-C3)-烷基,
Ra、Rb彼此独立地各自代表氢、氟、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基,或
Ra和Rb连同它们所连接的碳原子一起形成羰基或硫代羰基,
Rp1代表氢,
Rp2代表(C1-C4)-烷基,
Rp3代表氢、(C1-C4)-烷基、(C1-C4)-卤代烷基或环丙基,
n代表0、1或2。
特别优选通式(I)的化合物,其中符号和下标具有以下含义:
A代表(CH2)n,
X1、X2彼此独立地各自代表O或S(O)n,
R代表三氟甲基、二氟甲基或五氟乙基,
Ra、Rb彼此独立地各自代表氢、氟、甲基、乙基、三氟甲基、二氟甲基、甲氧基、乙氧基,或
Ra和Rb连同它们所连接的碳原子一起形成羰基或硫代羰基,
Rp1代表氢,
Rp2代表(C1-C4)-烷基,
Rp3代表氢、(C1-C4)-烷基、(C1-C4)-卤代烷基或环丙基,
n代表0、1或2。
在本发明的上下文中,取代基A、X1、X2、R、Ra、Rb、R1、R2、Rp1、Rp2、Rp3或下标n的各个优选和特别优选的含义可以根据需要彼此组合。这意味着本发明涵盖通式(I)的化合物,其中,例如,取代基X1具有优选的含义,而取代基A、X2、R、Ra、Rb、R1、R2、Rp1、Rp2、Rp3和下标n具有一般的定义,或者取代基R具有优选的含义,取代基Ra具有特别优选的含义,而其余的取代基具有一般含义。
下表1中列出的本发明的式(I)的化合物是非常特别优选的。
使用的缩写具有以下含义:
Me=甲基 Et=乙基 cPr=环丙基
表1:通式(I)的化合物,其中Rp1、Ra和Rb代表氢,A代表(CH2)n,并且其他取代基和下标具有以下所述含义。
本发明的式(I)的化合物可类似于WO 2009/018925 A1中详述的方法通过在脱水剂例如羰基二咪唑的存在下使式(II)的苯甲酸衍生物与吡唑反应,并随后在氰化物源如丙酮氰醇的存在下进行重排来制备。
所需的式(II’)的化合物可例如使用方案1至7中描述的合成路线来制备。
其中符号和下标具有以下含义:
L代表卤素或R3O,
R3代表氢或(C1-C6)-烷基,
A代表(CH2)n,
X1、X2彼此独立地各自代表O或S(O)n,
R代表卤代-(C1-C6)-烷基,
Ra、Rb彼此独立地各自代表氢、氟、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基、(C1-C6)-烷硫基、氰基,或
Ra和Rb连同它们所连接的碳原子一起形成羰基或硫代羰基,
n代表0、1或2。
在以下方案1至3所示的式中,如果A代表(CH2)n,其中n=0,则取代基L、Ra、Rb和R具有针对式(II’)的化合物给出的含义。
Y代表卤素。
方案1
其中X1代表氧且X2代表硫的式(II')的化合物还可如下制备:例如,根据方案1中给出的反应顺序——从取代的3-硫代烷基水杨酸衍生物开始——通过硫氧化、Pummerer重排和环化进行。在这里Y代表卤素。取代的3-硫代烷基水杨酸衍生物原则上是已知的和/或可通过US 2015/322003中给出的方法来制备。
方案2
其中X1代表氧且X2代表硫的式(II’)的化合物还可如下制备:例如,根据方案2中给出的反应顺序——从方案1中的Pummerer重排产物开始——通过水解得到硫醇(IV)并随后进行环化。Y代表可水解基团,如卤化物或酰氧基。
方案3
其中X1和X2代表硫的式(II’)的化合物可如下制备:例如,根据方案3中给出的反应顺序——从取代的3-硫代烷基-2-卤代苯甲酸衍生物开始——通过硫氧化、Pummerer重排和通过用硫化物进行双取代的环化来进行。在这里Y代表卤素。取代的3-硫代烷基苯甲酸衍生物原则上是已知的和/或可例如通过US2011/45980或US2008/305956中给出的方法来制备。
在以下方案4和5所示的式中,如果A代表(CH2)n,其中n=1,则取代基L、Ra、Rb和R具有针对式(II’)的化合物给出的含义。LG代表离去基团,如卤化物或磺酸盐。
方案4
其中X1代表氧且X2代表硫的式(II’)的化合物可例如根据方案4中给出的反应顺序,从尤其可根据方案2制备的硫醇(IV)开始合成。
方案5
其中X1和X2代表硫的式(II’)的化合物可如下制备:例如,根据方案5中给出的反应顺序——从例如取代的2,3-二卤代苯甲酸衍生物开始——通过用乙烷-1,2-二硫醇进行的双取代来进行环化。2,3-取代的苯甲酸衍生物原则上是已知的。
在以下方案6和7所示的式中,如果A代表(CH2)n,其中n=2,则取代基L、Ra、Rb和R具有针对式(II’)的化合物给出的含义。LG代表离去基团,例如卤化物或磺酸盐。
方案6
其中X1代表氧且X2代表硫的式(II’)的化合物可例如根据方案6中给出的反应顺序,从尤其可根据方案2制备的硫醇(IV)开始合成。
方案7
其中X1和X2代表硫的式(II’)的化合物可如下制备:例如根据方案7中给出的反应顺序——从例如取代的2,3-二卤代苯甲酸衍生物开始——通过用丙烷-1,3-二硫醇进行的双取代来进行环化。2,3-取代的苯甲酸衍生物原则上是已知的。
可通过上述反应合成的式(I)的化合物和/或其盐的集合还可以平行的方式制备,在这种情况下,其可以手动、半自动或全自动的方式完成。例如,可使反应、产物和/或中间体的后处理或纯化自动进行。总之,这应当理解为意指例如D.Tiebes在CombinatorialChemistry–Synthesis,Analysis,Screening(编辑:Günther Jung),Wiley,1999,第1至34页中记载的过程。
本发明式(I)的化合物(和/或其盐)——在下文中统称为“本发明的化合物”——对广谱的经济上重要的单子叶和双子叶一年生有害植物具有优异的除草功效。
因此,本发明还提供一种防治不想要的植物或调节植物生长(优选在植物作物中)的方法,其中将一种或多种本发明的化合物施用于植物(例如有害植物,如单子叶或双子叶杂草或不想要的作物植物)、种子(例如谷粒、种子或营养繁殖体如块茎或带芽的嫩枝部位)或植物生长的区域(例如栽培区域)。本发明的化合物可例如在播种前(如果合适,还通过掺入土壤中)、出苗前或出苗后施用。可通过本发明的化合物防治的单子叶和双子叶杂草植物群的一些代表的具体实例如下,尽管列举并不意图限于特定的属种。
以下属的单子叶有害植物:山羊草属(Aegilops)、冰草属(Agropyron)、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)、鸭跖草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、藨草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
以下属的双子叶杂草:苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、单花葵属(Anoda)、春黄菊属(Anthemis)、蔷薇属(Aphanes)、蒿属(Artemisia)、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针草属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、拉拉藤属(Galium)、木槿属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、粟米草属(Mullugo)、勿忘我属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、苦苣菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、车轴草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)、苍耳属(Xanthium)。
当将本发明的化合物在萌芽前施用至土壤表面时,杂草幼苗的出苗被完全阻止,或者杂草生长直至其达到子叶期,但之后停止生长。
如果将活性化合物在出苗后施用至植物的绿色部位,则在处理后生长停止,并且有害植物停留在施用时的生长阶段,或其在一定时间后彻底死亡,从而以此方式非常早地并以持久的方式消除对作物植物有害的杂草竞争。
本发明的化合物可在有用植物作物中具有选择性,并且还可用作非选择性除草剂。
活性化合物凭借其除草和植物生长调节特性还可用于防治已知的或尚未开发的遗传修饰植物作物中的有害植物。通常,转基因植物的特征在于特别有利的性能,例如对农用工业中使用的某些活性化合物(特别是某些除草剂)的抗性;对植物病害或植物病害的病原体(例如某些昆虫或微生物如真菌、细菌或病毒)的抗性。其他具体特征涉及例如采收物的数量、品质、贮存性、组成和具体成分。例如,存在已知的具有增加的淀粉含量或改变的淀粉品质的转基因植物,或采收物中具有不同脂肪酸组成的那些转基因植物。其他特定性能在于对非生物胁迫因素例如热、冷、干旱、盐度和紫外线辐射的耐受性或抗性。
优选在经济上重要的有用植物和观赏植物的转基因作物中使用本发明式(I)的化合物或其盐。式(I)的化合物可在对除草剂的植物毒性作用具有抗性或通过基因工程使其具有抗性的有用植物作物中用作除草剂。
产生与现有植物相比具有改进特性的新植物的常规方法包括例如传统培育方法和产生突变体。或者,具有改变特性的新植物可借助重组方法产生(参见,例如EP 0221044、EP 0131624)。例如,已记载了以下几种情形:以改性植物中合成的淀粉为目的的作物植物遗传修饰体(例如WO 92/011376 A、WO 92/014827 A、WO 91/019806A);通过“基因叠加”对草铵膦类(参见,例如EP 0242236 A、EP0242246 A)或草甘膦类(WO 92/000377 A)或磺酰脲类(EP 0257993A、US 5,013,659)的某些除草剂或这些除草剂的结合物或混合物具有抗性的转基因作物植物,如转基因作物植物,例如具有商品名或名称OptimumTM GATTM(耐受草甘膦ALS)的玉米或大豆,
-能够产生使植物对特定害虫具有抗性的苏云金芽孢杆菌(Bacillusthuringiensis)毒素(Bt毒素)的转基因作物植物,例如棉花(EP 0142924 A、EP 0193259A),
-具有改变的脂肪酸组成的转基因作物植物(WO 91/013972 A),
-具有新的成分或次级代谢产物(例如新的植物抗毒素,其使得抗病性增加)的遗传修饰作物植物(EP 0309862 A、EP 0464461A),
-具有降低的光呼吸作用的遗传修饰植物,其具有更高的产量和更高的胁迫耐受性(EP 0305398 A),
-产生药学上或诊断上重要的蛋白质的转基因作物植物(“分子药耕(molecularpharming)”),
-以更高的产量或更好的品质为特征的转基因作物植物,
-以例如上述新特性的组合为特征的转基因作物植物(“基因叠加”)。
许多可用于产生具有改进性能的新的转基因植物的分子生物学技术原则上是已知的;参见,例如I.Potrykus和G.Spangenberg(编辑),Gene Transfer to Plants,Springer Lab Manual(1995),Springer Verlag Berlin,Heidelberg或Christou,"Trendsin Plant Science"1(1996)423-431。
对于这样的遗传操作,可将能够突变或通过重组DNA序列进行序列改变的核酸分子引入到质粒中。借助于标准方法,例如可进行碱基交换、移除部分序列或添加天然或合成序列。为了将DNA片段彼此连接,可将衔接子(adapter)或接头(linker)置于片段上,参见,例如Sambrook等人,1989,Molecular Cloning,A Laboratory Manual,第二版,ColdSpring Harbor Laboratory Press,Cold Spring Harbor,NY;或Winnacker"Gene undKlone"[Genes and Clones],VCH Weinheim,第二版,1996。
例如,具有降低的基因产物活性的植物细胞的产生可通过表达至少一种相应的反义RNA、用于实现共抑制作用的正义RNA或通过表达至少一种适当构建的特异性切割上述基因产物的转录物的核酶来实现。为此,首先可使用包含基因产物的完整编码序列(包括可存在的任何侧翼序列)的DNA分子,以及仅包含部分编码序列的DNA分子,在这种情况下,这些部分编码序列必须足够长以在细胞中具有反义作用。还可使用与基因产物的编码序列具有高度同源性但与其不完全相同的DNA序列。
当在植物中表达核酸分子时,所合成的蛋白质可位于植物细胞的任意所需区室中。然而,为实现在特定区室内的定位,例如可将编码区与确保定位于特定区室中的DNA序列连接。这类序列是本领域技术人员已知的(参见,例如Braun等人,EMBO J.11(1992),3219-3227;Wolter等人,Proc.Natl.Acad.Sci.USA 85(1988),846-850;Sonnewald等人,Plant J.1(1991),95-106)。核酸分子还可在植物细胞的细胞器中表达。
可通过已知技术使转基因植物细胞再生,以产生完整植株。原则上,转基因植物可为任何所需植物种类的植物,即不仅可为单子叶植物,还可为双子叶植物。因此,可获得其特性通过超表达、阻抑(suppression)或抑制同源(=天然)基因或基因序列或表达异源(=外源)基因或基因序列而改变的转基因植物。
本发明的化合物(I)可优选用于对以下物质具有抗性的转基因作物中:生长调节剂(例如2,4-D、麦草畏(dicamba)),或抑制必需植物酶(例如乙酰乳酸合酶(ALS)、EPSP合酶、谷氨酰胺合酶(GS)或羟基苯丙酮酸双加氧酶(HPPD))的除草剂,或选自磺酰脲类、草甘膦类、草铵膦类或苯甲酰基异噁唑类和类似活性化合物的除草剂,或这些活性化合物的任意所需的结合物。
本发明的化合物可特别优选用于对草甘膦类和草铵膦类、草甘膦类和磺酰脲类或咪唑啉酮类的结合物具有抗性的转基因作物植物中。最优选地,本发明的化合物可用于转基因作物植物,例如具有商品名或名称OptimumTM GATTM的玉米或大豆(耐受草甘膦ALS)。
当将本发明的活性化合物用于转基因作物中时,不仅产生在其他作物中观察到的对有害植物的效果,还经常产生对在特定转基因作物中的施用具有特异性的效果,例如改变的或特别是拓宽的可防治的杂草谱、改变的可用于施用的施用率、优选与转基因作物对其具有抗性的除草剂的良好的相容性,以及影响转基因作物植物的生长和产量。
因此,本发明还涉及本发明的式(I)的化合物作为除草剂用于防治转基因作物植物中的有害植物的用途。
本发明的化合物可以常规制剂中的可湿性粉剂、可乳化浓缩剂、可喷雾溶液剂、撒粉产品或颗粒剂的形式施用。因此,本发明还提供包含本发明的化合物的除草组合物和植物生长调节组合物。
根据所需的生物学和/或物理化学参数,可以多种方式配制本发明的化合物。可能的制剂包括,例如:可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩剂、可乳化浓缩剂(EC)、乳剂(EW)如水包油乳剂和油包水乳剂、可喷雾溶液剂、悬浮浓缩剂(SC)、基于油或水的分散剂、油混溶性溶液剂、胶囊悬浮剂(CS)、撒粉产品(DP)、拌种剂、用于撒播和土壤施用的颗粒剂、微颗粒形式的颗粒剂(GR)、喷雾颗粒剂、吸收和吸附颗粒剂、水分散性颗粒剂(WG)、水溶性颗粒剂(SG)、ULV制剂、微胶囊剂和蜡剂。这些单独的制剂类型原则上是已知的,并且记载于例如以下文献中:Winnacker-Küchler,"Chemische Technologie[ChemicalTechnology]",第7卷,C.Hanser Verlag Munich,第四版,1986,Wade van Valkenburg,"Pesticide Formulations",Marcel Dekker,N.Y.,1973,K.Martens,"Spray Drying"Handbook,第三版,1979,G.Goodwin Ltd.London。
所需的制剂助剂,如惰性物质、表面活性剂、溶剂和其他添加剂同样是已知的,并且记载于例如以下文献中:Watkins,"Handbook of Insecticide Dust Diluents andCarriers",第二版,Darland Books,Caldwell N.J.;H.v.Olphen,"Introduction to ClayColloid Chemistry",第二版,J.Wiley&Sons,N.Y.;C.Marsden,"Solvents Guide",第二版,Interscience,N.Y.1963;McCutcheon,"Detergents and Emulsifiers Annual",MCPubl.Corp.,Ridgewood N.J.;Sisley和Wood,"Encyclopedia of Surface ActiveAgents",Chem.Publ.Co.Inc.,N.Y.1964;" -addukte"[Interface-active Ethylene Oxide Adducts],Wiss.Verlagsgesell.,Stuttgart 1976;Winnacker-Küchler,"Chemische Technologie",第7卷,C.Hanser Verlag Munich,第四版,1986。
基于这些制剂,还可制备与其他活性化合物(例如杀昆虫剂、杀螨剂、除草剂、杀真菌剂)以及与安全剂、肥料和/或生长调节剂的结合物,例如以成品制剂的形式或作为桶混物(tank mix)。
可与本发明的化合物以混合制剂形式或以桶混物形式结合使用的活性化合物为,例如已知的基于抑制以下物质的活性化合物:例如乙酰乳酸合酶、乙酰辅酶A羧化酶、纤维素合酶、烯醇式丙酮酰莽草酸-3-磷酸合酶(enolpyruvylshikimate-3-phosphatesynthase)、谷氨酰胺合酶、对羟基苯丙酮酸双加氧酶、八氢番茄红素脱氢酶(phytoenedesaturase)、光合系统I、光合系统II或原卟啉原氧化酶(protoporphyrinogen oxidase),例如Weed Research 26(1986)441-445或"The Pesticide Manual",第16版,The BritishCrop Protection Council and the Royal Soc.of Chemistry,2006以及其中所引用的文献中所记载。可与本发明的化合物结合的已知的除草剂或植物生长调节剂为例如以下活性化合物,其中所述活性化合物以其根据国际标准化组织(ISO)的“通用名称”命名,或以化学名称或代码编号命名。即使未明确提及,它们也总是包括所有的施用形式,例如酸、盐、酯以及所有的异构体形式,例如立体异构体和光学异构体。
这种除草混配物的实例为:
乙草胺(acetochlor)、三氟羧草醚(acifluorfen)、三氟羧草醚钠(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、二丙烯草胺(allidochlor)、禾草灭(alloxydim)、禾草灭钠(alloxydim-sodium)、莠灭净(ametryn)、氨唑草酮(amicarbazone)、乙酰胺(amidochlor)、酰嘧磺隆(amidosulfuron)、4-氨基-3-氯-6-(4-氯-2-氟-3-甲基苯基)-5-氟吡啶-2-羧酸、环丙嘧啶酸(aminocyclopyrachlor)、环丙嘧啶酸钾(aminocyclopyrachlor-potassium)、环丙嘧啶酸甲酯(aminocyclopyrachlor-methyl)、氯氨吡啶酸(aminopyralid)、杀草强(amitrole)、氨基磺酸铵(ammoniumsulfamate)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、氟丁酰草胺(beflubutamid)、草除灵(benazolin)、草除灵乙酯(benazolin-ethyl)、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron)、苄嘧磺隆(bensulfuron-methyl)、地散磷(bensulide)、灭草松(bentazone)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟吡草酮(bicyclopyron)、甲羧除草醚(bifenox)、双丙氨膦(bilanafos)、双丙氨膦钠(bilanafos-sodium)、双草醚(bispyribac)、双草醚钠(bispyribac-sodium)、除草定(bromacil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、丁酰溴苯腈(bromoxynil-butyrate)、溴苯腈钾(bromoxynil-potassium)、庚酰溴苯腈(bromoxynil-heptanoate)和辛酰溴苯腈(bromoxynil-octanoate)、羟草酮(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁苯草酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、双酰草胺(carbetamide)、唑酮草酯(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、草灭畏(chloramben)、氯溴隆(chlorbromuron)、伐草克(chlorfenac)、伐草克钠(chlorfenac-sodium)、燕麦酯(chlorfenprop)、氯芴素(chlorflurenol)、氯芴素(chlorflurenol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、氯酞酰亚胺(chlorophthalim)、绿麦隆(chlorotoluron)、敌草索(chlorthal-dimethyl)、氯磺隆(chlorsulfuron)、吲哚酮草酯(cinidon)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、氯酰草膦(clacyfos)、烯草酮(clethodim)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、异噁草松(clomazone)、氯甲酰草胺(clomeprop)、二氯吡啶酸(clopyralid)、氯酯磺草胺(cloransulam)、氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氨基氰(cyanamide)、氰草津(cyanazine)、环草敌(cycloate)、cyclopyranil、cyclopyrimorate、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop)、氰氟草酯(cyhalofop-butyl)、环草津(cyprazine)、2,4-D、2,4-D-丁氧基乙酯(2,4-D-butotyl)、2,4-D-丁酯(2,4-D-butyl)、2,4-D-二甲基铵(2,4-D-dimethylammonium)、2,4-D-二乙醇胺(2,4-D-diolamin)、2,4-D-乙酯(2,4-D-ethyl)、2,4-D-2-乙基己酯(2,4-D-2-ethylhexyl)、2,4-D-异丁酯、2,4-D-异辛酯、2,4-D-异丙基铵、2,4-D-钾、2,4-D-三异丙醇铵和2,4-D-三乙醇胺、2,4-DB、2,4-DB-丁酯、2,4-DB-二甲基铵、2,4-DB-异辛酯、2,4-DB-钾和2,4-DB-钠、杀草隆(daimuron(dymron))、茅草枯(dalapon)、棉隆(dazomet)、正癸醇、甜菜安(desmedipham)、detosyl-pyrazolate(DTP)、麦草畏、敌草腈(dichlobenil)、2-(2,4-二氯苄基)-4,4-二甲基-1,2-噁唑烷-3-酮、2-(2,5-二氯苄基)-4,4-二甲基-1,2-噁唑烷-3-酮、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、禾草灵(diclofop)、禾草灵(diclofop-methyl)、精禾草灵(diclofop-P-methyl)、双氯磺草胺(diclosulam)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、二氟吡隆钠(diflufenzopyr-sodium)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、精二甲吩草胺(dimethenamid-P)、dimetrasulfuron、氨氟灵(dinitramine)、特乐酚(dinoterb)、双苯酰草胺(diphenamid)、敌草快(diquat)、二溴敌草快(diquat dibromide)、氟硫草定(dithiopyr)、敌草隆(diuron)、DNOC、茵多酸(endothal)、EPTC、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron)、胺苯磺隆(ethametsulfuron-methyl)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、氟乳醚(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-9600、F-5231(即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4,5-二氢-5-氧代-1H-四唑-1-基]苯基]乙磺酰胺)、F-7967(即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵乙酯(fenoxaprop-ethyl)、精噁唑禾草灵乙酯(fenoxaprop-P-ethyl)、fenoxasulfone、fenquinotrione、四唑酰草胺(fentrazamide)、麦草伏(flamprop)、高效麦草氟异丙酯(flamprop-M-isopropyl)、高效麦草氟甲酯(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、氟酮磺隆(flucarbazone)、氟酮磺隆(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet)、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac)、氟烯草酸(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、氟草隆(fluometuron)、抑草丁(flurenol)、芴醇丁酯(flurenol-butyl)、芴醇二甲铵(flurenol-dimethylammonium)和芴醇甲酯(flurenol-methyl)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚(fluoroglycofen-ethyl)、四氟丙酸(flupropanate)、氟啶嘧磺隆(flupyrsulfuron)、氟啶嘧磺隆钠(flupyrsulfuron-methyl-sodium)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、氯氟吡氧乙酸异辛酯(fluroxypyr-meptyl)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、氟磺胺草醚钠(fomesafen-sodium)、甲酰氨磺隆(foramsulfuron)、杀木膦(fosamine)、草铵膦、草铵膦铵、精草铵膦钠(glufosinate-P-sodium)、精草铵膦铵、精草铵膦钠、草甘膦、草甘膦铵、草甘膦异丙基铵、草甘膦二铵、草甘膦二甲基铵、草甘膦钾、草甘膦钠和草硫膦(glyphosate-trimesium)、H-9201(即O-(2,4-二甲基-6-硝基苯基)O-乙基异丙基硫代磷酰胺酯(O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropylphosphoramidothioate))、氟氯吡啶酯(halauxifen)、氟氯吡啶酯(halauxifen-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆(halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氟吡禾灵乙氧基乙酯、精氟吡禾灵乙氧基乙酯、氟吡甲禾灵(haloxyfop-methyl)、精氟吡甲禾灵(haloxyfop-P-methyl)、环嗪酮(hexazinone)、HW-02(即(2,4-二氯苯氧基)乙酸1-(二甲氧基磷酰基)乙酯)、咪草酯(imazamethabenz)、咪草酯(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、甲氧咪草烟铵、甲咪唑烟酸(imazapic)、甲咪唑烟酸铵、咪唑烟酸(imazapyr)、咪唑烟酸异丙基铵、咪唑喹啉酸(imazaquin)、咪唑喹啉酸铵、咪唑乙烟酸(imazethapyr)、咪唑乙烟酸亚铵(imazethapyr-immonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、三嗪茚草胺(indaziflam)、碘甲磺隆(iodosulfuron)、碘甲磺隆钠(iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、辛酰碘苯腈(ioxynil-octanoate)、碘苯腈钾和碘苯腈钠、三唑酰草胺(ipfencarbazone)、异丙隆(isoproturon)、异噁隆(isouron)、异噁酰草胺(isoxaben)、异噁唑草酮(isoxaflutole)、特胺灵(karbutilate)、KUH-043(即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺酰基)-5,5-二甲基-4,5-二氢-1,2-噁唑)、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、MCPA、MCPA-丁氧基乙酯、MCPA-二甲基铵、MCPA-2-乙基己酯、MCPA-异丙基铵、MCPA-钾和MCPA-钠、MCPB、MCPB-甲酯、MCPB-乙酯和MCPB-钠、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸钠和2-甲-4-氯丙酸丁氧基乙酯、精2-甲-4-氯丙酸(mecoprop-P)、精2-甲-4-氯丙酸丁氧基乙酯、精2-甲-4-氯丙酸二甲基铵、精2-甲-4-氯丙酸-2-乙基己酯和精2-甲-4-氯丙酸钾、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、甲基二磺隆(mesosulfuron)、甲基二磺隆(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、嗪吡嘧磺隆(metazosulfuron)、甲基苯噻隆、甲硫嘧磺隆(methiopyrsulfuron)、methiozolin、异硫氰酸甲酯(methyl isothiocyanate)、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、精异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、禾草敌(molinate)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron ester)、MT-5950(即N-[3-氯-4-(1-甲基乙基)-苯基]-2-甲基戊酰胺)、NGGC-011、敌草胺(napropamide)、NC-310(即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、壬酸(nonanoicacid(pelargonic acid))、氟草敏(norflurazon)、油酸(脂肪酸)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔噁草酮(oxadiargyl)、噁草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefon)、乙氧氟草醚(oxyfluorfen)、百草枯(paraquat)、二氯百草枯(paraquat dichloride)、克草猛(pebulate)、二甲戊灵(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚(pentachlorphenol)、环戊噁草酮(pentoxazone)、烯草胺(pethoxamid)、矿物油(petroleum oils)、甜菜宁(phenmedipham)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、氟嘧磺隆(primisulfuron-methyl)、氨氟乐灵(prodiamine)、环苯草酮(profoxydim)、扑灭通(prometon)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)、噁草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆钠(propoxycarbazone-sodium)、丙嗪嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、双唑草腈(pyraclonil)、吡草醚(pyraflufen)、吡草醚(pyraflufen-ethyl)、磺酰草吡唑(pyrasulfotole)、吡唑特(pyrazolynate(pyrazolate))、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、pyribambenz、异丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、达草止(pyridafol)、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧草醚(pyriminobac-methyl)、pyrimisulfan、嘧草硫醚(pyrithiobac)、嘧草硫醚(pyrithiobac-sodium)、砜吡草唑(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(quizalofop)、喹禾灵乙酯(quizalofop-ethyl)、精喹禾灵(quizalofop-P)、精喹禾灵乙酯(quizalofop-P-ethyl)、精喹禾糠酯(quizalofop-P-tefuryl)、砜嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、SL-261、磺草酮(sulcotrione)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆(sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、SYN-523、SYP-249(即1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸酯)、SYP-300(即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)-3,4-二氢-2H-1,4-苯并噁嗪-6-基]-3-丙基-2-硫代咪唑烷-4,5-二酮)、2,3,6-TBA、TCA(三氟乙酸)、TCA-钠、丁噻隆(tebuthiuron)、呋喃磺草酮(tefuryltrione)、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、特丁通(terbumeton)、特丁津(terbuthylazine)、去草净(terbutryn)、噻吩草胺(thenylchlor)、噻唑烟酸(thiazopyr)、噻酮磺隆(thiencarbazone)、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆(thifensulfuron-methyl)、禾草丹(thiobencarb)、tiafenacil、tolpyralate、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、氟酮磺草胺(triafamone)、野麦畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、苯磺隆(tribenuron-methyl)、三氯吡氧乙酸(triclopyr)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆钠(trifloxysulfuron-sodium)、trifludimoxazin、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)、三氟甲磺隆(tritosulfuron)、硫酸脲、灭草敌(vernolate)、XDE-848、ZJ-0862(即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苄基}苯胺),以及以下化合物:
作为可能的混配物的植物生长调节剂的实例为:
活化酯(acibenzolar)、阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、5-氨基乙酰丙酸、嘧啶醇(ancymidol)、6-苄基氨基嘌呤、芸苔素内酯(brassinolide)、邻苯二酚(catechol)、矮壮素(chlormequat chloride)、调果酸(cloprop)、环丙酸酰胺(cyclanilide)、3-(环丙-1-烯基)丙酸、丁酰肼(daminozide)、棉隆、正癸醇、调呋酸(dikegulac)、调呋酸钠(dikegulac-sodium)、茵多酸(endothal)、茵多酸二钾(endothal-dipotassium)、茵多酸二钠(endothal-disodium)和单(N,N-二甲基烷基铵)、乙烯利(ethephon)、氟节胺(flumetralin)、抑草丁、芴醇丁酯、呋嘧醇(flurprimidol)、氯吡脲(forchlorfenuron)、赤霉酸(gibberellic acid)、抗倒胺(inabenfide)、吲哚-3-乙酸(IAA)、4-吲哚-3-基丁酸、稻瘟灵(isoprothiolane)、烯丙苯噻唑(probenazole)、茉莉酸(jasmonic acid)、茉莉酸甲酯、马来酰肼、助壮素(mepiquat chloride)、1-甲基环丙烯、2-(1-萘基)乙酰胺、1-萘基乙酸、2-萘氧基乙酸、硝基酚盐混合物(nitrophenoxidemixture)、4-氧代-4[(2-苯乙基)氨基]丁酸、多效唑(paclobutrazole)、N-苯基邻氨甲酰苯甲酸、调环酸(prohexadione)、调环酸钙(prohexadione-calcium)、茉莉酮(prohydrojasmone)、水杨酸、独角金内酯(strigolactone)、四氯硝基苯(tecnazene)、噻苯隆(thidiazuron)、三十烷醇(triacontanol)、抗倒酯(trinexapac)、抗倒酯(trinexapac-ethyl)、tsitodef、烯效唑(uniconazole)、精烯效唑(uniconazole-P)。
可与本发明的式(I)的化合物结合使用以及任选地与其他活性化合物(如上文所列的杀昆虫剂、杀螨剂、除草剂、杀真菌剂)结合使用的安全剂优选选自:
S1)式(S1)的化合物,
其中符号和下标定义如下:
nA代表0至5、优选0至3的自然数;
RA 1代表卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、硝基或(C1-C4)-卤代烷基;
WA代表未取代或取代的二价杂环基团,其选自具有1至3个选自N和O的环杂原子的部分不饱和的或芳族的五元杂环,其中所述环中存在至少一个氮原子和至多一个氧原子,优选选自(WA 1)至(WA 4)的基团,
mA代表0或1;
RA 2代表ORA 3、SRA 3或NRA 3RA 4或具有至少一个氮原子和最高达3个杂原子(优选选自O和S)的饱和或不饱和的3元至7元杂环,所述杂环通过氮原子与(S1)中的羰基连接,并且为未取代的或被选自以下的基团取代:(C1-C4)-烷基、(C1-C4)-烷氧基或任选取代的苯基,优选式ORA 3、NHRA 4或N(CH3)2的基团,尤其是式ORA 3的基团;
RA 3代表氢或优选具有总共1至18个碳原子的未取代的或取代的脂族烃基;
RA 4代表氢、(C1-C6)-烷基、(C1-C6)-烷氧基或取代的或未取代的苯基;
RA 5代表H、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C1-C4)-烷氧基-(C1-C8)-烷基、氰基或COORA 9,其中RA 9代表氢、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C6)-羟基烷基、(C3-C12)-环烷基或三-(C1-C4)-烷基甲硅烷基;
RA 6、RA 7、RA 8是相同或不同的,并且代表氢、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C3-C12)-环烷基或取代的或未取代的苯基;
优选:
a)二氯苯基吡唑啉-3-羧酸类的化合物(S1a),优选化合物如1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-甲酸、1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-甲酸乙酯(S1-1)(“吡唑解草酯(mefenpyr-diethyl)”),以及相关化合物,如WO-A-91/07874中所记载;
b)二氯苯基吡唑羧酸的衍生物(S1b),优选化合物如1-(2,4-二氯苯基)-5-甲基吡唑-3-甲酸乙酯(S1-2)、1-(2,4-二氯苯基)-5-异丙基吡唑-3-甲酸乙酯(S1-3)、1-(2,4-二氯苯基)-5-(1,1-二甲基乙基)吡唑-3-甲酸乙酯(S1-4)以及相关化合物,如EP-A-333 131和EP-A-269 806中所记载;
c)1,5-二苯基吡唑-3-羧酸的衍生物(S1c),优选化合物如1-(2,4-二氯苯基)-5-苯基吡唑-3-甲酸乙酯(S1-5)、1-(2-氯苯基)-5-苯基吡唑-3-甲酸甲酯(S1-6)以及相关化合物,例如EP-A-268554中所记载;
d)三唑羧酸类的化合物(S1d),优选化合物如解草唑(-乙酯),即1-(2,4-二氯苯基)-5-三氯甲基-(1H)-1,2,4-三唑-3-甲酸乙酯(S1-7),以及相关化合物,如EP-A-174 562和EP-A-346 620中所记载;
e)5-苄基-2-异噁唑啉-3-羧酸或5-苯基-2-异噁唑啉-3-羧酸或5,5-二苯基-2-异噁唑啉-3-羧酸类的化合物(S1e),优选化合物如5-(2,4-二氯苄基)-2-异噁唑啉-3-甲酸乙酯(S1-8)或5-苯基-2-异噁唑啉-3-甲酸乙酯(S1-9)以及相关化合物,如WO-A-91/08202中所记载,或5,5-二苯基-2-异噁唑啉-3-甲酸(S1-10)或5,5-二苯基-2-异噁唑啉-3-甲酸乙酯(S1-11)(“双苯噁唑酸(isoxadifen-ethyl)”)或5,5-二苯基-2-异噁唑啉-3-甲酸正丙酯(S1-12)或5-(4-氟苯基)-5-苯基-2-异噁唑啉-3-甲酸乙酯(S1-13),如专利申请WO-A-95/07897中所记载。
S2)式(S2)的喹啉衍生物,
其中符号和下标定义如下:
RB 1代表卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、硝基或(C1-C4)-卤代烷基;
nB代表0至5、优选0至3的自然数;
RB 2代表ORB 3、SRB 3或NRB 3RB 4或具有至少一个氮原子和最高达3个杂原子(优选选自O和S)的饱和或不饱和的3元至7元杂环,所述杂环通过氮原子与(S2)中的羰基连接,并且为未取代的或被选自以下的基团取代:(C1-C4)-烷基、(C1-C4)-烷氧基或任选取代的苯基,优选式ORB 3、NHRB 4或N(CH3)2的基团,尤其是式ORB 3的基团;
RB 3代表氢或优选具有总共1至18个碳原子的未取代的或取代的脂族烃基;
RB 4代表氢、(C1-C6)-烷基、(C1-C6)-烷氧基或取代的或未取代的苯基;
TB代表(C1或C2)-烷二基链,其为未取代的或被一个或两个(C1-C4)-烷基取代或被[(C1-C3)-烷氧基]羰基取代;
优选:
a)8-喹啉氧基乙酸类的化合物(S2a),优选
(5-氯-8-喹啉氧基)乙酸1-甲基己酯(“解毒喹(cloquintocet-mexyl)”)(S2-1),
(5-氯-8-喹啉氧基)乙酸(1,3-二甲基丁-1-基)酯(S2-2),
(5-氯-8-喹啉氧基)乙酸4-烯丙氧基丁酯(S2-3),
(5-氯-8-喹啉氧基)乙酸1-烯丙氧基丙-2-基酯(S2-4),
(5-氯-8-喹啉氧基)乙酸乙酯(S2-5),
(5-氯-8-喹啉氧基)乙酸甲酯(S2-6),
(5-氯-8-喹啉氧基)乙酸烯丙酯(S2-7),
(5-氯-8-喹啉氧基)乙酸2-(2-亚丙基亚氨氧基)-1-乙酯(S2-8)、
(5-氯-8-喹啉氧基)乙酸2-氧代丙-1-基酯(S2-9)以及相关化合物,如EP-A-86750、EP-A-94 349和EP-A-191 736或EP-A-0492 366中所记载,以及(5-氯-8-喹啉氧基)乙酸(S2-10)、其水合物和盐,例如其锂盐、钠盐、钾盐、钙盐、镁盐、铝盐、铁盐、铵盐、季铵盐、锍盐或鏻盐,如WO-A-2002/34048中所记载;
b)(5-氯-8-喹啉氧基)丙二酸类的化合物(S2b),优选化合物如(5-氯-8-喹啉氧基)丙二酸二乙酯、(5-氯-8-喹啉氧基)丙二酸二烯丙酯、(5-氯-8-喹啉氧基)丙二酸甲基乙酯以及相关化合物,如EP-A-0 582 198中所记载。
S3)式(S3)的化合物
其中符号和下标定义如下:
RC 1代表(C1-C4)-烷基、(C1-C4)-卤代烷基、(C2-C4)-烯基、(C2-C4)-卤代烯基、(C3-C7)-环烷基,优选二氯甲基;
RC 2、RC 3是相同或不同的,并且代表氢、(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C1-C4)-卤代烷基、(C2-C4)-卤代烯基、(C1-C4)-烷基氨基甲酰基-(C1-C4)-烷基、(C2-C4)-烯基氨基甲酰基-(C1-C4)-烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、二氧杂环戊基-(C1-C4)-烷基、噻唑基、呋喃基、呋喃基烷基、噻吩基、哌啶基、取代的或未取代的苯基,或RC 2和RC 3一起形成取代的或未取代的杂环,优选噁唑烷、噻唑烷、哌啶、吗啉、六氢嘧啶或苯并噁嗪环;
优选:
二氯乙酰胺类的活性化合物,其通常用作苗前安全剂(作用于土壤的安全剂),例如
“二氯丙烯胺(dichlormid)”(N,N-二烯丙基-2,2-二氯乙酰胺)(S3-1),
购自Stauffer的“R-29148”(3-二氯乙酰基-2,2,5-三甲基-1,3-噁唑烷)(S3-2),
购自Stauffer的“R-28725”(3-二氯乙酰基-2,2-二甲基-1,3-噁唑烷)(S3-3),
“解草嗪(benoxacor)”(4-二氯乙酰基-3,4-二氢-3-甲基-2H-1,4-苯并噁嗪)(S3-4),
购自PPG Industries的“PPG-1292”(N-烯丙基-N-[(1,3-二氧杂环戊-2-基)甲基]二氯乙酰胺)(S3-5),
购自Sagro-Chem的“DKA-24”(N-烯丙基-N-[(烯丙基氨基羰基)甲基]二氯乙酰胺)(S3-6),
购自Nitrokemia或Monsanto的“AD-67”或“MON 4660”(3-二氯乙酰基-1-氧杂-3-氮杂螺[4.5]癸烷)(S3-7),
购自TRI-Chemical RT的“TI-35”(1-二氯乙酰基氮杂环庚烷)(S3-8),
购自BASF的“diclonon”(dicyclonon)或“BAS145138”或“LAB145138”((RS)-1-二氯乙酰基-3,3,8a-三甲基全氢吡咯并[1,2-a]嘧啶-6-酮)(S3-9),
“呋喃解草唑(furilazole)”或“MON 13900”((RS)-3-二氯乙酰基-5-(2-呋喃基)-2,2-二甲基噁唑烷)(S3-10);以及其(R)异构体(S3-11)。
S4)式(S4)的N-酰基磺酰胺及其盐,
其中符号和下标定义如下:
AD代表SO2-NRD 3-CO或CO-NRD 3-SO2;
XD代表CH或N;
RD 1代表CO-NRD 5RD 6或NHCO-RD 7;
RD 2代表卤素、(C1-C4)-卤代烷基、(C1-C4)-卤代烷氧基、硝基、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基或(C1-C4)-烷基羰基;
RD 3代表氢、(C1-C4)-烷基、(C2-C4)-烯基或(C2-C4)-炔基;
RD 4代表卤素、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-卤代烷氧基、(C3-C6)-环烷基、苯基、(C1-C4)-烷氧基、氰基、(C1-C4)-烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基或(C1-C4)-烷基羰基;
RD 5代表氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C5-C6)-环烯基、苯基或含有vD个选自氮、氧和硫的杂原子的3元至6元杂环基,其中最后提及的七个基团被vD个选自以下的取代基取代:卤素、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C2)-烷基亚磺酰基、(C1-C2)-烷基磺酰基、(C3-C6)-环烷基、(C1-C4)-烷氧基羰基、(C1-C4)-烷基羰基和苯基,并且在环状基团的情况下,还选自(C1-C4)-烷基和(C1-C4)-卤代烷基;
RD 6代表氢、(C1-C6)-烷基、(C2-C6)-烯基或(C2-C6)-炔基,其中最后提及的三个基团被vD个选自以下的基团取代:卤素、羟基、(C1-C4)-烷基、(C1-C4)-烷氧基和(C1-C4)-烷硫基,或
RD 5和RD 6与带有它们的氮原子一起形成吡咯烷基或哌啶基;
RD 7代表氢、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、(C1-C6)-烷基、(C3-C6)-环烷基,其中最后提及的二个基团被vD个选自以下的取代基取代:卤素、(C1-C4)-烷氧基、(C1-C6)-卤代烷氧基和(C1-C4)-烷硫基,并且在环状基团的情况下,还选自(C1-C4)-烷基和(C1-C4)-卤代烷基;
nD代表0、1或2;
mD代表1或2;
vD代表0、1、2或3;
在这些基团中,优选例如以下式(S4a)的N-酰基磺酰胺类的化合物,其例如由WO-A-97/45016已知,
其中
RD 7代表(C1-C6)-烷基、(C3-C6)-环烷基,其中最后提及的2个基团被vD个选自以下的取代基取代:卤素、(C1-C4)-烷氧基、(C1-C6)-卤代烷氧基和(C1-C4)-烷硫基,并且在环状基团的情况下,还选自(C1-C4)-烷基和(C1-C4)-卤代烷基;
RD 4代表卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3;
mD代表1或2;
vD代表0、1、2或3;
以及
例如以下式(S4b)的酰基氨磺酰基苯甲酰胺,其例如由WO-A-99/16744已知,
例如那些化合物,其中
RD 5=环丙基且(RD 4)=2-OMe(“环丙磺酰胺(cyprosulfamide)”,S4-1),
RD 5=环丙基且(RD 4)=5-Cl-2-OMe(S4-2),
RD 5=乙基且(RD 4)=2-OMe(S4-3),
RD 5=异丙基且(RD 4)=5-Cl-2-OMe(S4-4),和
RD 5=异丙基且(RD 4)=2-OMe(S4-5)
以及
式(S4c)的N-酰基氨磺酰基苯基脲类的化合物,其例如由EP-A-365484已知,
其中
RD 8和RD 9彼此独立地代表氢、(C1-C8)-烷基、(C3-C8)-环烷基、(C3-C6)-烯基、(C3-C6)-炔基,
RD 4代表卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3,
mD代表1或2;
例如
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3-甲基脲,
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3,3-二甲基脲,
1-[4-(N-4,5-二甲基苯甲酰基氨磺酰基)苯基]-3-甲基脲,
以及
式(S4d)的N-苯基磺酰基对苯二甲酰胺,其例如由CN 101838227已知,
例如那些化合物,其中
RD 4代表卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3;
mD代表1或2;
RD 5代表氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C5-C6)-环烯基。
S5)羟基芳族化合物和芳族-脂族羧酸衍生物类的活性化合物(S5),例如
3,4,5-三乙酰氧基苯甲酸乙酯、3,5-二甲氧基-4-羟基苯甲酸、3,5-二羟基苯甲酸、4-羟基水杨酸、4-氟水杨酸、2-羟基肉桂酸、2,4-二氯肉桂酸,如WO-A-2004/084631、WO-A-2005/015994、WO-A-2005/016001中所记载。
S6)1,2-二氢喹喔啉-2-酮类的活性化合物(S6),例如
1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮、1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-硫酮、1-(2-氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮盐酸盐、1-(2-甲基磺酰基氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮,如WO-A-2005/112630中所记载。
S7)式(S7)的化合物,如WO-A-1998/38856中所记载,
其中符号和下标定义如下:
RE 1、RE 2彼此独立地代表卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷基、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、硝基;
AE代表COORE 3或COSRE 4;
RE 3、RE 4彼此独立地代表氢、(C1-C4)-烷基、(C2-C6)-烯基、(C2-C4)-炔基、氰基烷基、(C1-C4)-卤代烷基、苯基、硝基苯基、苄基、卤代苄基、吡啶基烷基和烷基铵,
nE 1代表0或1,
nE 2、nE 3彼此独立地代表0、1或2,
优选:
二苯基甲氧基乙酸,
二苯基甲氧基乙酸乙酯,
二苯基甲氧基乙酸甲酯(CAS登记号41858-19-9)(S7-1)。
S8)式(S8)的化合物或其盐,如WO-A-98/27049中所记载,
其中
XF代表CH或N,
nF在XF=N的情况下为0至4的整数,以及
在XF=CH的情况下为0至5的整数,
RF 1代表卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、硝基、(C1-C4)-烷硫基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基、任选取代的苯基、任选取代的苯氧基,
RF 2代表氢或(C1-C4)-烷基,
RF 3代表氢、(C1-C8)-烷基、(C2-C4)-烯基、(C2-C4)-炔基或芳基,其中上述含碳基团各自为未取代的或被一个或多个、优选最高达三个相同或不同的选自卤素和烷氧基的基团取代,
优选以下化合物或其盐,其中
XF代表CH,
nF代表0至2的整数,
RF 1代表卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基,
RF 2代表氢或(C1-C4)-烷基,
RF 3代表氢、(C1-C8)-烷基、(C2-C4)-烯基、(C2-C4)-炔基或芳基,其中上述含碳基团各自为未取代的或被一个或多个、优选最高达三个相同或不同的选自卤素和烷氧基的基团取代。
S9)3-(5-四唑基羰基)-2-喹诺酮类的活性化合物(S9),例如
1,2-二氢-4-羟基-1-乙基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号219479-18-2)、1,2-二氢-4-羟基-1-甲基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号95855-00-8),如WO-A-1999/000020中所记载。
S10)式(S10a)或(S10b)的化合物
如WO-A-2007/023719和WO-A-2007/023764中所记载,
其中
RG 1代表卤素、(C1-C4)-烷基、甲氧基、硝基、氰基、CF3、OCF3,
YG、ZG彼此独立地代表O或S,
nG代表0至4的整数,
RG 2代表(C1-C16)-烷基、(C2-C6)-烯基、(C3-C6)-环烷基、芳基、苄基、卤代苄基,
RG 3代表氢或(C1-C6)-烷基。
S11)氧基亚氨基化合物类的活性化合物(S11),其已知为拌种剂,例如
“解草腈(oxabetrinil)”((Z)-1,3-二氧杂环戊-2-基甲氧基亚氨基(苯基)乙腈)(S11-1),其已知为抗异丙甲草胺损害的粟/高粱用拌种安全剂,
“氟草肟(fluxofenim)”(1-(4-氯苯基)-2,2,2-三氟-1-乙酮O-(1,3-二氧杂环戊-2-基甲基)肟)(S11-2),其已知为抗异丙甲草胺损害的粟/高粱用拌种安全剂,以及
“解草胺腈(cyometrinil)”或“CGA-43089”((Z)-氰基甲氧基亚氨基(苯基)乙腈)(S11-3),其已知为抗异丙甲草胺损害的粟/高粱用拌种安全剂。
S12)异硫代苯并二氢吡喃酮类(isothiochromanones)的活性化合物(S12),例如[(3-氧代-1H-2-苯并噻喃-4(3H)-亚基)甲氧基]乙酸甲酯(CAS登记号205121-04-6)(S12-1)以及来自WO-A-1998/13361的相关化合物。
S13)组(S13)的一种或多种化合物:
“萘二甲酸酐”(1,8-萘二甲酸酐)(S13-1),其已知为抗硫代氨基甲酸酯除草剂损害的玉米用拌种安全剂,
“解草啶(fenclorim)”(4,6-二氯-2-苯基嘧啶)(S13-2),其已知为在播种的稻中用于丙草胺的安全剂,
“解草胺(flurazole)”(2-氯-4-三氟甲基-1,3-噻唑-5-甲酸苄酯)(S13-3),其已知为抗甲草胺和异丙甲草胺损害的粟/高粱用拌种安全剂,
购自American Cyanamid的“CL 304415”(CAS登记号31541-57-8)(4-羧基-3,4-二氢-2H-1-苯并吡喃-4-乙酸)(S13-4),其已知为抗咪唑啉酮损害的玉米用安全剂,
购自Nitrokemia的“MG 191”(CAS登记号96420-72-3)(2-二氯甲基-2-甲基-1,3-二氧戊环)(S13-5),其已知为玉米用安全剂,
购自Nitrokemia的“MG 838”(CAS登记号133993-74-5)(1-氧杂-4-氮杂螺[4.5]癸烷-4-二硫代甲酸2-丙烯酯)(S13-6),
“乙拌磷(disulfoton)”(S-2-乙硫基乙基二硫代磷酸O,O-二乙酯)(S13-7),
“增效磷(dietholate)”(O-苯基O,O-二乙基硫代磷酸酯)(S13-8),
“mephenate”(甲基氨基甲酸4-氯苯酯)(S13-9)。
S14)除了对有害植物具有除草作用外,还对作物植物如稻具有安全剂作用的活性化合物,例如
“哌草丹”或“MY-93”(1-苯基乙基哌啶-1-硫代甲酸S-1-甲酯),其已知为抗除草剂禾草敌损害的稻用安全剂,
“杀草隆”或“SK 23”(1-(1-甲基-1-苯基乙基)-3-对甲苯基脲),其已知为抗唑吡嘧磺隆除草剂损害的稻用安全剂,
“苄草隆”=“JC-940”(3-(2-氯苯基甲基)-1-(1-甲基-1-苯基乙基)脲,参见JP-A-60087254),其已知为抗一些除草剂损害的稻用安全剂,
“苯草酮(methoxyphenone)”或“NK 049”(3,3'-二甲基-4-甲氧基二苯甲酮),其已知为抗一些除草剂损害的稻用安全剂,
购自Kumiai的“CSB”(1-溴-4-(氯甲基磺酰基)苯)(CAS登记号54091-06-4),其已知为稻中抗一些除草剂损害的安全剂。
S15)式(S15)的化合物或其互变异构体
如WO-A-2008/131861和WO-A-2008/131860中所记载,其中
RH 1代表(C1-C6)-卤代烷基,和
RH 2代表氢或卤素,和
RH 3、RH 4彼此独立地代表氢、(C1-C16)-烷基、(C2-C16)-烯基或(C2-C16)-炔基,
其中最后提及的3个基团各自为未取代的或被一个或多个选自以下的基团取代:卤素、羟基、氰基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷基氨基、二[(C1-C4)-烷基]氨基、[(C1-C4)-烷氧基]羰基、[(C1-C4)-卤代烷氧基]羰基、未取代的或取代的(C3-C6)-环烷基、未取代的或取代的苯基和未取代的或取代的杂环基,
或(C3-C6)-环烷基、(C4-C6)-环烯基、在环的一侧上稠合成4至6元饱和或不饱和碳环的(C3-C6)-环烷基,或在环的一侧上稠合成4至6元饱和或不饱和碳环的(C4-C6)-环烯基,
其中最后提及的4个基团各自为未取代的或被一个或多个选自以下的基团取代:卤素、羟基、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷基氨基、二[(C1-C4)-烷基]氨基、[(C1-C4)-烷氧基]羰基、[(C1-C4)-卤代烷氧基]羰基、未取代的或取代的(C3-C6)-环烷基、未取代的或取代的苯基和未取代的或取代的杂环基,
或
RH 3代表(C1-C4)-烷氧基、(C2-C4)-烯氧基、(C2-C6)-炔氧基或(C2-C4)-卤代烷氧基,且
RH 4代表氢或(C1-C4)-烷基,或
RH 3和RH 4与直接连接的氮原子一起代表四元至八元杂环,所述杂环除了氮原子外还可含有其他环杂原子,优选最高达两个选自N、O和S的其他环杂原子,并且所述杂环为未取代的或被一个或多个选自以下的基团取代:卤素、氰基、硝基、(C1-C4)-烷基、
(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基和(C1-C4)-烷硫基。
S16)主要用作除草剂,但还对作物植物具有安全剂作用的活性化合物,例如
(2,4-二氯苯氧基)乙酸(2,4-D),
(4-氯苯氧基)乙酸,
(R,S)-2-(4-氯-邻甲苯氧基)丙酸(mecoprop),
4-(2,4-二氯苯氧基)丁酸(2,4-DB),
(4-氯-邻甲苯氧基)乙酸(MCPA),
4-(4-氯-邻甲苯氧基)丁酸,
4-(4-氯苯氧基)丁酸,
3,6-二氯-2-甲氧基苯甲酸(麦草畏),
3,6-二氯-2-甲氧基苯甲酸1-(乙氧基羰基)乙酯(lactidichlor-ethyl)。
特别优选的安全剂为吡唑解草酯、环丙磺酰胺、双苯噁唑酸、解毒喹和二氯丙烯胺。
可湿性粉剂为可在水中均匀分散的制剂,其除了活性化合物之外,以及除了稀释剂或惰性物质之外,还包含离子型和/或非离子型表面活性剂(润湿剂、分散剂),例如聚乙氧基化烷基酚、聚乙氧基化脂肪醇、聚乙氧基化脂肪胺、脂肪醇聚乙二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木质素磺酸钠、2,2'-二萘基甲烷-6,6'-二磺酸钠、二丁基萘磺酸钠或油酰基甲基牛磺酸钠。为了制备可湿性粉剂,将除草活性化合物例如在常规设备如锤磨机、鼓风磨机和空气喷射磨机中细磨,并同时或随后与制剂助剂混合。
可乳化浓缩剂通过将活性化合物溶于有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或相对高沸点的芳族化合物或烃类)或有机溶剂的混合物中,并添加一种或多种离子型和/或非离子型表面活性剂(乳化剂)而制备。可使用的乳化剂的实例为:烷基芳基磺酸钙,如十二烷基苯磺酸钙;或非离子型乳化剂,如脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷-环氧乙烷缩合产物、烷基聚醚、脱水山梨糖醇酯(例如脱水山梨糖醇脂肪酸酯)或聚氧乙烯脱水山梨糖醇酯(例如聚氧乙烯脱水山梨糖醇脂肪酸酯)。
撒粉产品通过将活性化合物与细分散的固体一起研磨而获得,所述细分散的固体为例如滑石、天然粘土(如高岭土、膨润土和叶蜡石)或硅藻土。
悬浮浓缩剂可以是水基或油基的。其可借助市售珠磨机,并任选地添加例如已在上文针对其他制剂类型所列出的表面活性剂,通过例如湿式研磨法制备。
乳剂,例如水包油乳剂(EW),可使用含水有机溶剂和任选地已在上文例如针对其他制剂类型所列出的表面活性剂,借助例如搅拌器、胶体磨机和/或静态混合器来制备。
颗粒剂可通过将活性化合物喷洒于吸附性颗粒状惰性物质上制备或通过借助胶粘剂(例如聚乙烯醇、聚丙烯酸钠或矿物油)将活性化合物浓缩物施用于载体物质(如砂、高岭石或颗粒状惰性物质)的表面来制备。还可将合适的活性化合物以常用于制备肥料颗粒剂的方式——如果需要与肥料混合——进行造粒。
水分散性颗粒剂通常通过常规方法如喷雾干燥法、流化床造粒法、盘式造粒法、用高速混合器混合且在没有固体惰性物质的情况下挤出来制备。
关于盘式颗粒、流化床颗粒、挤出机颗粒和喷雾颗粒的制备,参见例如"Spray-Drying Handbook"第三版,1979,G.Goodwin Ltd.,London,J.E.Browning,"Agglomeration",Chemical and Engineering1967,第147页及后文;"Perry's ChemicalEngineer's Handbook",第五版,McGraw-Hill,New York 1973,第8-57页中的方法。
关于作物保护组合物制剂的其他详细信息,参见例如G.C.Klingman,"WeedControl as a Science",John Wiley and Sons,Inc.,New York,1961,第81-96页和J.D.Freyer,S.A.Evans,"Weed Control Handbook",第五版,Blackwell ScientificPublications,Oxford,1968,第101-103页。
农业化学制剂通常含有0.1至99重量%、特别是0.1至95重量%的本发明的化合物。在可湿性粉剂中,活性化合物的浓度为例如约10至90重量%,补足至100重量%的余量由常规制剂成分组成。在可乳化浓缩剂中,活性化合物的浓度可为约1重量%至90重量%且优选5重量%至80重量%。粉剂形式的制剂包含1重量%至30重量%的活性化合物,优选地通常5重量%至20重量%的活性化合物;可喷雾溶液剂含有约0.05重量%至80重量%、优选2重量%至50重量%的活性化合物。在水分散性颗粒剂的情况下,活性化合物的含量部分取决于活性化合物是液体还是固体形式,以及使用何种造粒助剂、填料等。在水分散性颗粒剂中,活性化合物的含量为例如1重量%至95重量%,优选为10重量%至80重量%。
此外,所提及的活性化合物制剂任选地包含各自常规的粘着剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、抗冻剂和溶剂、填料、载体和染料、消泡剂、蒸发抑制剂和影响pH和粘度的试剂。
基于这些制剂,还可制备与其他农药活性物质(例如杀昆虫剂、杀螨剂、除草剂、杀真菌剂)以及与安全剂、肥料和/或生长调节剂的结合物,例如以成品制剂的形式或作为桶混物。
为了施用,如果合适,将市售形式的制剂以常规方式稀释,例如在可湿性粉剂、可乳化浓缩剂、分散剂和水分散性颗粒剂的情况下,用水稀释。粉剂型制剂、用于土壤施用的颗粒剂或用于撒播的颗粒剂和可喷雾溶液剂在施用前通常不用其他惰性物质进一步稀释。
式(I)的化合物所需的施用率根据外界条件(尤其包括温度、湿度和所用除草剂的类型)而变化。施用率可在宽范围内变化,例如0.001至1.0kg/ha或更多的活性物质,但其优选为0.005至750g/ha。
载体为天然或合成的有机或无机物质,将其与活性化合物混合或结合以更好地施用,特别是施用至植物或植物部位或种子。载体——其可为固体或液体——通常是惰性的且应适用于农业中。有用的固体或液体载体包括:例如铵盐和天然岩粉,如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土;和合成的岩粉,如细分散的二氧化硅、氧化铝和天然或合成的硅酸盐、树脂、蜡、固体肥料;水;醇,尤其是丁醇;有机溶剂、矿物油和植物油,以及它们的衍生物。同样可使用这样的载体的混合物。用于颗粒剂的有用的固体载体包括:例如粉碎并分级的天然岩石(如方解石、大理石、浮石、海泡石、白云石)、无机粉末和有机粉末的合成颗粒以及有机材料(如锯屑、椰壳、玉米穗轴和烟草秆)的颗粒。
合适的液化的气态增量剂或载体为在标准温度和大气压下为气态的液体,例如气溶胶推进剂(aerosol propellant),如卤代烃,或丁烷、丙烷、氮气和二氧化碳。
在制剂中,可以使用增粘剂,如羧甲基纤维素;粉末、颗粒或胶乳形式的天然和合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯;或天然磷脂(如脑磷脂和卵磷脂)和合成磷脂。其他添加剂可为矿物油和植物油。
当所用的增量剂为水时,还可使用例如有机溶剂作为助溶剂。有用的液体溶剂主要为:芳族化合物,如二甲苯、甲苯或烷基萘;氯代芳族化合物或氯代脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷或石蜡,例如矿物油馏分、矿物油和植物油;醇,如丁醇或乙二醇及其醚和酯;酮,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基甲酰胺和二甲基亚砜;以及水。
本发明的组合物可另外包含其他组分,例如表面活性剂。有用的表面活性剂为具有离子或非离子性质的乳化剂和/或发泡剂、分散剂或润湿剂,或这些表面活性剂的混合物。其实例为聚丙烯酸的盐;木质素磺酸的盐;酚磺酸或萘磺酸的盐;环氧乙烷与脂肪醇或与脂肪酸或与脂肪胺的缩聚物;取代的酚(优选烷基酚或芳基酚);磺基琥珀酸酯的盐;牛磺酸衍生物(优选牛磺酸烷基酯);聚乙氧基化醇或酚的磷酸酯;多元醇的脂肪酸酯;以及含有硫酸根、磺酸根和磷酸根的化合物的衍生物,例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐、蛋白质水解产物、木质素亚硫酸盐废液(lignosulfite wasteliquors)和甲基纤维素。如果活性化合物之一和/或惰性载体之一不溶于水并且施用在水中进行时,则需要存在表面活性剂。表面活性剂的比例为本发明的组合物的5至40重量%。可以使用染料,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝;和有机染料,如茜素染料、偶氮染料和金属酞菁染料;以及微量营养物,如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
如果合适,还可存在其他另外的组分,例如保护胶体、粘合剂(binder)、胶粘剂(adhesive)、增稠剂、触变物质、渗透剂、稳定剂、螯合剂、络合剂。通常,活性化合物可与通常用于制剂目的的任何固体或液体添加剂结合。通常,本发明的组合物和制剂含有0.05至99重量%、0.01至98重量%、优选0.1至95重量%且更优选0.5至90重量%、最优选10至70重量%的活性化合物。本发明的活性化合物或组合物可以其本身的形式使用,或根据其各自的物理和/或化学性质,以其制剂的形式或由其制备的使用形式使用,如气溶胶、胶囊悬浮剂、冷雾浓缩剂、暖雾浓缩剂、封装的颗粒剂、细颗粒剂、用于处理种子的可流动浓缩剂、即用型溶液剂、可撒播粉剂、可乳化浓缩剂、水包油乳剂、油包水乳剂、大颗粒剂、微颗粒剂、油分散性粉剂、油混溶性可流动浓缩剂、油混溶性液剂、泡沫剂、糊剂、农药种衣剂(pesticidecoated seed)、悬浮浓缩剂、悬乳浓缩剂、可溶性浓缩剂、悬浮剂、可湿性粉剂、可溶性粉剂、粉剂和颗粒剂、水溶性颗粒剂或片剂、用于处理种子的水溶性粉剂、可湿性粉剂、用活性化合物浸渍的天然产物和合成物质,以及聚合物质和种子包衣材料中的微胶囊剂,以及ULV冷雾和暖雾制剂。
所提及的制剂可以本身已知的方式制备,例如通过将活性化合物与至少一种以下常规物质混合来制备:增量剂、溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、润湿剂、防水剂、任选地干燥剂和UV稳定剂,以及任选地染料和颜料、消泡剂、防腐剂、二次增稠剂、增粘剂、赤霉素以及其他加工助剂。
本发明的组合物不仅包括可即用的并且可用合适的设备施用到植物或种子上的制剂,还包括在使用前必须用水稀释的市售浓缩物。
本发明的活性化合物可以其本身形式存在,或以其(市售标准)制剂或由这些制剂与其他(已知)活性化合物的混合物制备的使用形式存在,所述其他(已知)活性化合物为例如杀昆虫剂、引诱剂、止繁殖剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂、除草剂、肥料、安全剂或化学信息素。
根据本发明,使用活性化合物或组合物对植物和植物部位的处理通过使用常规处理方法直接进行或通过作用于其环境、生境或贮藏空间进行,所述常规处理方法为例如浸渍、喷洒、雾化(atomizing)、灌溉、蒸发、撒粉、弥雾(fogging)、撒播、发泡、涂抹、铺展(spreading-on)、浇水(浸透)、滴灌,并且在繁殖材料的情况下,特别是在种子的情况下,还以用于干种子处理的粉剂、用于种子处理的溶液剂、用于浆料处理的水溶性粉剂的形式,通过结壳、通过涂覆一层或多层包衣等进行。还可通过超低容量法施用活性化合物,或将活性化合物制剂或活性化合物本身注射到土壤中。
还如下文所述,使用本发明的活性化合物或组合物处理转基因种子也是特别重要的。这涉及含有至少一种异源基因的植物的种子,所述异源基因能够表达具有杀虫特性的多肽或蛋白。转基因种子中的异源基因可源自以下微生物属种:例如,芽孢杆菌属(Bacillus)、根瘤菌属(Rhizobium)、假单孢菌属(Pseudomonas)、沙雷氏菌属(Serratia)、木霉属(Trichoderma)、棒状杆菌属(Clavibacter)、球囊霉属(Glomus)或粘帚霉属(Gliocladium)。这种异源基因优选源自芽孢杆菌属,在这种情况下,基因产物有效地对抗欧洲玉米螟和/或西方玉米根虫。异源基因更优选源自苏云金芽孢杆菌。
在本发明的上下文中,将本发明的组合物单独或以合适的制剂形式施用于种子。优选地,在种子足够稳定的状态下处理种子以在处理过程中不发生损害。通常,可在采收和播种之间的任何时间处理种子。通常使用已与植物分离并且已去除穗轴、壳、茎、表皮、绒毛或果肉的种子。例如,可使用已采收、清洁并干燥至小于15重量%的含水量的种子。或者,还可使用例如在干燥后已用水处理然后再干燥的种子。
通常,在处理种子时,必须确保选择施用于种子的本发明的组合物和/或其他添加剂的量,以使种子的发芽不受损害,并且由其长出的植物不受损害。特别是在可在一定施用率下表现出植物毒性作用的活性化合物的情况下,必须确保这一点。
本发明的组合物可直接施用,即不含任何其他组分且无需进行稀释。通常,优选以合适的制剂形式将组合物施用于种子。用于种子处理的合适的制剂和方法是本领域技术人员已知的,并且记载于例如以下文献中:US 4,272,417 A、US 4,245,432 A、US 4,808,430、US5,876,739、US 2003/0176428 A1、WO 2002/080675 A1、WO2002/028186 A2。
可将本发明的活性化合物转变成常规的拌种制剂,例如溶液剂、乳剂、悬浮剂、粉剂、泡沫剂、浆剂或其他种子包衣组合物,以及ULV制剂。
这些制剂以已知方式通过将活性化合物与常规添加剂混合而制备,所述常规添加剂为例如常规的增量剂和溶剂或稀释剂、染料、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、胶粘剂、赤霉素以及水。
可存在于可根据本发明使用的拌种制剂中的染料为通常用于此目的的所有染料。可使用微溶于水的颜料或溶于水的染料。实例包括已知的名称为罗丹明B、C.I.颜料红112和C.I.溶剂红1的染料。
可存在于可根据本发明使用的拌种制剂中的有用的润湿剂为促进润湿并通常用于配制农业化学活性化合物的所有物质。可优选使用萘磺酸烷基酯,如萘磺酸二异丙酯或萘磺酸二异丁酯。
可存在于可根据本发明使用的拌种制剂中的合适的分散剂和/或乳化剂为通常用于配制农业化学活性化合物的所有非离子、阴离子和阳离子分散剂。优选使用非离子或阴离子分散剂,或非离子或阴离子分散剂的混合物。合适的非离子分散剂尤其包括环氧乙烷/环氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基酚聚乙二醇醚,及其磷酸化或硫酸化衍生物。合适的阴离子分散剂尤其为木质素磺酸盐、聚丙烯酸盐和芳基磺酸盐-甲醛缩合物。
可存在于可根据本发明使用的拌种制剂中的消泡剂为通常用于配制农业化学活性化合物的所有抑制泡沫的物质。可优选使用硅酮消泡剂和硬脂酸镁。
可存在于可根据本发明使用的拌种制剂中的防腐剂为可在农业化学组合物中用于此类目的的所有物质。实例包括双氯酚和苄醇半缩甲醛。
可存在于可根据本发明使用的拌种制剂中的二次增稠剂为可在农业化学组合物中用于此类目的的所有物质。优选的实例包括纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土和细分散的二氧化硅。
可存在于可根据本发明使用的拌种制剂中的有用的粘着剂为可用于拌种产品中的所有常规的粘合剂。优选的实例包括聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和甲基纤维素(tylose)。
可根据本发明使用的拌种制剂可直接或预先用水稀释后用于处理宽范围的不同的种子,包括转基因植物的种子。在这种情况下,在与通过表达形成的物质的相互作用中还可发生另外的协同效应。
为了用可根据本发明使用的拌种制剂或通过添加水由其制备的制剂处理种子,有用的设备为所有可常规用于拌种的混合单元。具体而言,拌种过程为:将种子放置到混合器内,加入特定所需量的拌种制剂(以其本身的形式或在预先用水稀释后),并将它们混合直至制剂均匀地分布于种子上。如果合适,随后进行干燥操作。
鉴于良好的植物相容性、有利的恒温动物毒性和良好的环境相容性,本发明的活性化合物适合用于保护植物和植物器官、用于提高采收产量和用于改善采收作物的品质。它们可优选用作作物保护剂。它们对通常敏感和具有抗性的物种以及对所有或特定的发育阶段具有活性。
可根据本发明处理的植物包括以下主要作物植物:玉米、大豆、棉花、油菜(Brassica oil seeds)如甘蓝型油菜(Brassica napus)(例如加拿大油菜(Canola))、芜菁(Brassica rapa)、芥菜型油菜(B.juncea)(例如(野生)芥菜(mustard))和埃塞俄比亚芥(Brassica carinata)、稻、小麦、甜菜、甘蔗、燕麦、黑麦、大麦、粟和高粱、黑小麦、亚麻、藤本植物(grapes)以及各种植物分类群的各种水果和蔬菜,所述植物分类群为例如蔷薇科属种(Rosaceae sp.)(例如仁果如苹果和梨,以及核果如杏、樱桃、扁桃和桃,以及浆果如草莓)、Ribesioidae属种、胡桃科属种(Juglandaceae sp.)、桦木科属种(Betulaceae sp.)、漆树科属种(Anacardiaceae sp.)、山毛榉科属种(Fagaceae sp.)、桑科属种(Moraceaesp.)、木犀科属种(Oleaceae sp.)、猕猴桃科属种(Actinidaceae sp.)、樟科属种(Lauraceae sp.)、芭蕉科属种(Musaceae sp.)(例如香蕉树和大蕉(plantation))、茜草科属种(Rubiaceae sp.)(例如咖啡)、山茶科属种(Theaceae sp.)、梧桐科属种(Sterculiceae sp.)、芸香科属种(Rutaceae sp.)(例如柠檬、橙和葡萄柚)、茄科属种(Solanaceae sp.)(例如番茄、马铃薯、胡椒、茄子)、百合科属种(Liliaceae sp.)、菊科属种(Compositae sp.)(例如莴苣、朝鲜蓟(artichoke)和菊苣(chicory)——包括根菊苣(root chicory)、苣荬菜(endive)或普通菊苣(common chicory))、伞形科属种(Umbelliferae sp.)(例如胡萝卜、欧芹(parsley)、芹菜(celery)和块根芹)、葫芦科属种(Cucurbitaceae sp.)(例如黄瓜——包括嫩黄瓜(gherkin)、南瓜、西瓜、葫芦(calabash)和甜瓜(melon))、葱科属种(Alliaceae sp.)(例如韭葱和洋葱)、十字花科属种(Cruciferae sp.)(例如白球甘蓝(white cabbage)、红球甘蓝(red cabbage)、西兰花(broccoli)、花椰菜(cauliflower)、抱子甘蓝(Brussels sprout)、小白菜(pak choi)、球茎甘蓝(kohlrabi)、萝卜、山葵(horseradish)、水芹(cress)和大白菜)、豆科属种(Leguminosae sp.)(例如花生、豌豆和菜豆——例如红花菜豆(runner bean)和蚕豆(broad bean))、藜科属种(Chenopodiaceae sp.)(例如瑞士甜菜、饲用甜菜、菠菜、甜菜根)、锦葵科(Malvaceae)(例如秋葵(okra))、天门冬科(Asparagaceae)(例如芦笋(asparagus));园艺和森林中的有用植物和观赏植物;以及在每种情况下这些植物的遗传修饰型。
如上所述,可根据本发明处理所有的植物及其部位。在一个优选的实施方案中,处理野生植物物种和植物栽培种,或处理通过常规生物育种技术如杂交或原生质体融合而获得的那些植物及其部位。在另一个优选的实施方案中,处理通过基因工程方法——如果合适,与常规方法结合——获得的转基因植物和植物栽培种(遗传修饰生物体)及其部位。术语“部位”或“植物的部位”或“植物部位”已在上文中解释。根据本发明,特别优选处理各市售的常规植物栽培种的植物或在使用的那些植物。植物栽培种应理解为意指通过常规育种、通过突变或通过重组DNA技术生长出的具有新特性(“性状”)的植物。它们可以是栽培种、变种、生物型和基因型。
本发明的处理方法可用于处理遗传修饰生物体(GMO),例如植物(如作物植物和树木)或种子。遗传修饰植物(或转基因植物)是其中异源基因已被稳定地整合到基因组中的植物。表述“异源基因”主要意指在植物或植物细胞外提供或组装的基因,并且当其被引入到细胞核基因组、叶绿体基因组或线粒体基因组中时,特别地通过表达目的蛋白质或多肽,或通过下调或使存在于植物内的一种或多种其他基因沉默(例如使用反义技术、共抑制技术或RNA干扰(RNAi)技术或微RNA(miRNA)技术)而赋予转化植物新的或改进的农学性状或其他性状。已被整合到基因组中的异源基因也称为转基因。已被整合到植物基因组中的转基因称为转化株系(transformation event)或转基因株系(transgenic event)。
取决于植物物种或植物栽培种、其所在地和生长条件(土壤、气候、生长期、营养),本发明的处理还可产生超加和(“协同”)效应。例如,可出现以下超过实际预期的效果:可根据本发明使用的活性成分和组合物的施用率降低和/或活性谱拓宽和/或功效提高、更好的植物生长、增加的对高温或低温的耐受性、提高的对干旱或对水或土壤盐渍度的耐受性、提高的开花性能、更容易的采收、加速成熟、更高的采收产量、更大的果实、更大的植株高度、更绿的叶子颜色、更早的开花、采收产品的更高的品质和/或更高的营养价值、果实内更高的糖浓度、采收产品更好的储存稳定性和/或可加工性。
在某些施用率下,本发明的活性成分结合物还可对植物具有强化作用。因此,它们适用于调动植物的防御系统来抵抗不想要的微生物的侵袭。这可能是本发明的结合物例如抵抗真菌的活性增强的原因之一。在本发明的上下文中,植物强化(诱导抗性)物质应理解为意指能够以这样的方式刺激植物防御系统的那些物质或物质的结合物,即在随后接种不想要的微生物时,所处理的植物对这些微生物表现出高度的抗性。在本文中,不想要的微生物应理解为意指植物病原性真菌、细菌和病毒。因此,本发明的物质可用于保护植物在处理后的一定时间内免受上述病原体的侵袭。在用活性成分处理植物后,得到保护的时间通常持续1至10天、优选1至7天。
优选根据本发明处理的植物和植物栽培种包括所有具有赋予这些植物特别有利的、有用的性状的遗传物质的植物(通过育种手段和/或生物技术手段获得)。
同样优选根据本发明处理的植物和植物品种对一种或多种生物胁迫因素具有抗性,即所述植物对动物和微生物害虫,例如对线虫、昆虫、螨、植物病原性真菌、细菌、病毒和/或类病毒具有更好的防御。
抗线虫植物或抗昆虫植物的实例记载于例如以下文献中:美国专利申请11/765,491、11/765,494、10/926,819、10/782,020、12/032,479、10/783,417、10/782,096、11/657,964、12/192,904、11/396,808、12/166,253、12/166,239、12/166,124、12/166,209、11/762,886、12/364,335、11/763,947、12/252,453、12/209,354、12/491,396、12/497,221、12/644,632、12/646,004、12/701,058、12/718,059、12/721,595、12/638,591,以及WO 11/002992、WO 11/014749、WO11/103247、WO 11/103248、WO 12/135436、WO 12/135501、WO2013134523、WO 2013134535、WO 2014036238、WO 2014126986A1、WO 2014138339、WO 2014003769、WO2015021367、WO2015021354、WO 2015077525、WO 2015038262、WO 2015041769、WO2015088937A。
植物对其他类型病原体的抗性的实例记载于例如WO13/050410、WO 2013127988、WO 2013135726、WO 2015036378、WO 2015036469、WO 2015177206中。
还可根据本发明处理的植物和植物栽培种为对一种或多种非生物胁迫因素具有抗性的那些植物。非生物胁迫条件可包括,例如干旱、低温暴露、热暴露、渗透胁迫、水涝、增加的土壤盐渍度、增加的矿物暴露、臭氧暴露、强光暴露、有限的氮营养素利用率、有限的磷营养素利用率或避荫。
还可根据本发明处理的植物和植物品种为特征在于提高的产量特征的那些植物。所述植物中提高的产量可归因于例如改善的植物生理机能、生长和发育,例如水利用效率、保水效率、改善的氮利用、增强的碳同化、改善的光合作用、增加的发芽效率和加速的成熟。此外,产量还可受到改善的植物结构(在胁迫和非胁迫条件下)的影响,其包括但不限于提早开花、杂交制种的开花控制、幼苗活力、植物大小、节间数和节间距、根系生长、种子大小、果实大小、荚果大小、荚果数或穗数、每个荚果或穗的种子数、种子质量、提高的种子饱满度、减少的种子散布、减少的荚开裂和抗倒伏性。其他产量性状包括种子组成,例如碳水化合物含量、蛋白质含量、油含量和油组成、营养价值、抗营养化合物的减少、改善的加工性能和更好的储存稳定性。
可根据本发明处理的植物为已经表达出杂种优势或杂交效果的特征的杂交植物,所述杂种优势或杂交效果通常引起更高的产量、活力、更好的健康和对生物和非生物胁迫因素的抗性。这样的植物通常通过使一种自交雄性不育亲系(杂交母本)与另一种自交雄性能育亲系(杂交父本)杂交而产生。杂交种子通常采收自雄性不育植物并出售给种植者。雄性不育植物有时(例如在玉米的情况下)可通过去雄(flag removal),即机械去除雄性生殖器官(或雄花)产生;然而,雄性不育性更通常是基于植物基因组中的遗传定子;特别是如果待从杂交植物上采收的所需种子材料为种子时,则通常确保杂交植物中的雄性能育性得以恢复。这可通过确保杂交父本具有合适的能育性恢复基因来实现,所述能育性恢复基因能够使包含负责雄性不育性的遗传定子的杂交植物中的雄性能育性恢复。雄性不育性的遗传定子可位于细胞质中。例如,记载了芸苔属种(Brassica species)的细胞质雄性不育性(CMS)的实例(WO 92/05251、WO 95/09910、WO 98/27806、WO 05/002324、WO 06/021972和US6,229,072)。然而,雄性不育性的遗传定子还可位于细胞核基因组中。雄性不育植物还可通过植物生物技术方法(如基因工程)获得。WO 89/10396中记载了一种特别有用的获得雄性不育植物的方法,其中,例如,核糖核酸酶(如芽孢杆菌RNA酶)在雄蕊中的绒毡层细胞中选择性表达。然后可通过在绒毡层细胞中表达核糖核酸酶抑制剂(如芽胞杆菌RNA酶抑制剂)来恢复能育性(例如WO 91/02069)。含有雄性不育性基因和能育性恢复基因的其他植物,以及用于杂交制种的体系记载于例如WO2014170387和WO 2014195152中。
可根据本发明处理的植物或植物栽培种(通过植物生物技术方法如基因工程获得)还包括除草剂耐受性植物,即对一种或多种给定的除草剂具有耐受性的植物。此类植物可通过遗传转化获得,或通过选择含有赋予这种除草剂耐受性的突变的植物而获得。
除草剂抗性植物为例如草甘膦耐受性植物,即对除草剂草甘膦或其盐具有耐受性的植物。可通过多种方式使植物对草甘膦具有耐受性。因此,例如,可通过用编码5-烯醇式丙酮酰莽草酸-3-磷酸合酶(EPSPS)的基因对植物进行转化来获得草甘膦耐受性植物。此类EPSPS基因的实例为鼠伤寒沙门氏菌(Salmonella typhimurium)细菌的AroA基因(突变体CT7)(Science 1983,221,370-371)、土壤杆菌属种(Agrobacterium sp.)细菌的CP4基因(Curr.Topics Plant Physiol.1992,7,139-145)、编码矮牵牛EPSPS的基因(Science1986,233,478-481)、编码番茄EPSPS的基因(J.Biol.Chem.1988,263,4280-4289)或编码属EPSPS的基因(WO 01/66704)。所述EPSPS基因还可以是突变的EPSPS,例如EP 0837944、WO00/66746、WO00/66747或WO 02/26995、WO 2011/000498中所记载。草甘膦耐受性植物还可通过表达编码草甘膦氧化还原酶的基因来获得,如US5,776,760和US 5,463,175中所记载。草甘膦耐受性植物还可通过表达编码草甘膦乙酰基转移酶的基因来获得,例如WO 02/036782、WO03/092360、WO 05/012515和WO 07/024782中所记载。草甘膦耐受性植物还可通过选择含有上述基因的天然产生的突变体的植物来获得,例如WO 01/024615或WO 03/013226中所记载。表达赋予草甘膦耐受性的EPSPS基因的植物记载于例如以下美国专利申请中:11/517,991、10/739,610、12/139,408、12/352,532、11/312,866、11/315,678、12/421,292、11/400,598、11/651,752、11/681,285、11/605,824、12/468,205、11/760,570、11/762,526、11/769,327、11/769,255、11/943801或12/362,774。含有赋予草甘膦耐受性的其他基因(例如脱羧酶基因)的植物记载于例如以下美国专利申请中:11/588,811、11/185,342、12/364,724、11/185,560或12/423,926。
其他除草剂抗性植物为例如对抑制谷氨酰胺合酶的除草剂(如双丙氨膦(bialaphos)、草丁膦(phosphinothricin)或草铵膦)具有耐受性的植物。此类植物可通过表达解除除草剂毒性的酶或通过使用对抑制作用具有抗性的谷氨酰胺合酶的突变体来获得,记载于例如美国专利申请11/760,602中。此类有效的解毒酶的一个实例为编码草丁膦乙酰基转移酶的酶(如链霉菌属种(Streptomyces species)的bar或pat蛋白)。表达外源性草丁膦乙酰基转移酶的植物记载于例如以下美国专利中:5,561,236、5,648,477、5,646,024、5,273,894、5,637,489、5,276,268、5,739,082、5,908,810和7,112,665。
其他除草剂耐受性植物还有对抑制羟基苯丙酮酸双加氧酶(HPPD)的除草剂具有耐受性的植物。HPPD是催化将对羟基苯丙酮酸(HPP)转化成尿黑酸的反应的酶。根据WO 96/38567、WO99/24585、WO 99/24586、WO 09/144079、WO 02/046387或US6,768,044、WO 11/076877、WO 11/076882、WO 11/076885、WO11/076889、WO 11/076892、WO 13/026740、WO 13/092552、WO13/092551、WO 12/092555、WO 2014043435、WO 2015138394、WO2015135881,可使用编码天然产生的抗性HPPD酶的基因,或编码突变的或嵌合的HPPD酶的基因来转化对HPPD抑制剂具有耐受性的植物。
对HPPD抑制剂的耐受性还可通过用编码尽管天然HPPD酶被HPPD抑制剂抑制却仍能形成尿黑酸的酶的基因使植物转化而获得。此类植物和基因记载于WO 99/34008和WO02/36787中。除使用编码HPPD耐受性酶的基因之外,还可通过使用编码具有预苯酸盐脱氢酶活性(PDH活性)的酶的基因使植物转化来改善植物对HPPD抑制剂的耐受性,如WO 04/024928中所记载。此外,可通过向植物的基因组中添加编码用于代谢或降解HPPD抑制剂的酶(如WO07/103567和WO 08/150473中所示的CYP450酶)的基因来使植物对HPPD抑制剂除草剂更具耐受性。
其他除草剂抗性植物还有对乙酰乳酸合酶(ALS)抑制剂具有耐受性的植物。已知的ALS抑制剂包括例如磺酰脲、咪唑啉酮、三唑并嘧啶、嘧啶基氧基(硫代)苯甲酸酯和/或磺酰基氨基羰基三唑啉酮除草剂。已知ALS酶(也称作乙酰羟酸合酶,AHAS)中的不同突变赋予对不同除草剂和除草剂组的耐受性,例如Tranel和Wright(Weed Science 2002,50,700-712)以及美国专利5,605,011、5,378,824、5,141,870和5,013,659中所记载。磺酰脲耐受性植物和咪唑啉酮耐受性植物的生产记载于美国专利5,605,011、5,013,659、5,141,870、5,767,361、5,731,180、5,304,732、4,761,373、5,331,107、5,928,937和5,378,824以及WO96/33270中。其他咪唑啉酮耐受性植物还记载于例如WO 04/040012、WO 04/106529、WO 05/020673、WO05/093093、WO 06/007373、WO 06/015376、WO 06/024351和WO06/060634中。其他磺酰脲耐受性植物和咪唑啉酮耐受性植物还记载于例如WO 07/024782、WO 11/076345、WO12/058223、WO12/150335、WO 2013127766、WO 2014090760、WO 2015004242、WO2015024957、WO 2015082413和美国专利申请61/288958中。
其他对咪唑啉酮和/或磺酰脲具有耐受性的植物可通过诱变、通过在除草剂的存在下在细胞培养物中选择或通过诱变育种而获得,例如,对于大豆,如US 5,084,082中所记载;对于稻,如WO 97/41218中所记载;对于甜菜,如US 5,773,702和WO 99/057965中所记载;对于莴苣,如US 5,198,599中所记载;或对于向日葵,如WO 01/065922中所记载。
对2,4-D或麦草畏具有耐受性的植物记载于例如US6153401中。
还可根据本发明处理的植物或植物品种(通过植物生物技术方法如基因工程获得)为昆虫抗性转基因植物,即对某些目标昆虫的侵袭具有抗性的植物。此类植物可通过遗传转化或通过选择含有赋予这种昆虫抗性的突变的植物而获得。
在本发明的上下文中,术语“昆虫抗性转基因植物”包括含有至少一种转基因的任何植物,所述转基因包含编码以下物质的编码序列:
1)苏云金芽孢杆菌的杀虫晶体蛋白或其杀虫部分,例如在苏云金芽孢杆菌毒素命名法中由Crickmore等人(Microbiology and Molecular Biology Reviews 1998,62,807-813)所编纂、由Crickmore等人(2005)更新(在线:http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/)的杀虫晶体蛋白,或其杀虫部分,例如Cry蛋白类Cry1Ab、Cry1Ac、Cry1B、Cry1C、Cry1D、Cry1F、Cry2Ab、Cry3Aa或Cry3Bb的蛋白或其杀虫部分(例如EP-A 1999141和WO07/107302),或由合成基因编码的那些蛋白,例如WO2013134523、WO2013134535和美国专利申请12/249,016中所记载;或
2)苏云金芽孢杆菌的晶体蛋白或其部分,其在除苏云金芽孢杆菌以外的另一晶体蛋白或其部分的存在下具有杀虫性,例如由Cry34和Cry35晶体蛋白组成的二元毒素(Nat.Biotechnol.2001,19,668-72;Applied Environm.Microbiol.2006,71,1765-1774)或由Cry1A或Cry1F蛋白和Cry2Aa或Cry2Ab或Cry2Ae蛋白组成的二元毒素(美国专利申请12/214,022和EP-A 2 300 618);或
3)杂合杀虫蛋白,其包含苏云金芽孢杆菌的不同杀虫晶体蛋白的部分,如上述1)的蛋白的杂合体或上述2)的蛋白的杂合体,例如由玉米株系MON89034产生的Cry1A.105蛋白(WO07/027777);或
4)上述1)至3)中任一项的蛋白,其中一些、特别是1至10个氨基酸被另一种氨基酸替代,以获得对目标昆虫物种更高的杀虫活性,和/或扩大受影响的目标昆虫物种的范围,和/或由于在克隆或转化过程中引入到编码DNA中的变化,如玉米株系MON863或MON88017中的Cry3Bb1蛋白,或玉米株系MIR 604中的Cry3A蛋白;或
5)苏云金芽孢杆菌或蜡状芽孢杆菌(Bacillus cereus)的杀虫分泌蛋白或其杀虫部分,例如http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html中所列的营养期杀虫蛋白(VIP),例如VIP3Aa蛋白类的蛋白;或
6)苏云金芽孢杆菌或蜡状芽胞杆菌的分泌蛋白,其在苏云金芽孢杆菌或蜡状芽胞杆菌的另一种分泌蛋白的存在下具有杀虫性,如由VIP1A和VIP2A蛋白组成的二元毒素(WO94/21795);或
7)杂合杀虫蛋白,其包含苏云金芽孢杆菌或蜡状芽孢杆菌的不同分泌蛋白的部分,如上述1)中蛋白的杂合体或上述2)中蛋白的杂合体;或
8)上述5)至7)中任一项的蛋白,其中一些、特别是1至10个氨基酸被另一种氨基酸替代,以获得对目标昆虫物种更高的杀虫活性,和/或扩大受影响的目标昆虫物种的范围,和/或由于在克隆或转化过程中引入到编码DNA中的变化(同时仍编码杀虫蛋白),如棉花株系COT 102中的VIP3Aa蛋白;或
9)苏云金芽孢杆菌或蜡状芽胞杆菌的分泌蛋白,其在苏云金芽孢杆菌的晶体蛋白的存在下具有杀虫性,如由VIP3和Cry1A或Cry1F组成的二元毒素(美国专利申请61/126083和61/195019),或由VIP3蛋白和Cry2Aa或Cry2Ab或Cry2Ae蛋白组成的二元毒素(美国专利申请12/214,022和EP-A 2 300618);或
10)上述9)的蛋白,其中一些、特别是1至10个氨基酸被另一种氨基酸替代,以获得对目标昆虫物种更高的杀虫活性,和/或扩大受影响的目标昆虫物种的范围,和/或由于在克隆或转化过程中引入到编码DNA中的变化(同时仍编码杀虫蛋白)。
当然,本文中所使用的昆虫抗性转基因植物还包括含有编码上述1-10类中任一项的蛋白的基因的组合的任何植物。在一个实施方案中,昆虫抗性植物含有多于一种编码上述1-10类中任一项的蛋白的转基因,以便在使用靶向不同目标昆虫物种的不同蛋白时扩大受影响的目标昆虫物种的范围,或在使用对相同目标昆虫物种具有杀虫性但具有不同作用模式(如与昆虫中不同的受体结合位点结合)的不同蛋白时延迟昆虫对植物的抗性的发展。
在本发明的上下文中,“昆虫抗性转基因植物”还包括含有至少一种包含在表达时产生双链RNA的序列的转基因的任何植物,所述双链RNA在被植物害虫昆虫食用时会抑制该害虫昆虫的生长,例如WO 07/080126、WO 06/129204、WO 07/074405、WO 07/080127和WO07/035650中所记载。
还可根据本发明处理的植物或植物栽培种(通过植物生物技术方法如基因工程获得)对非生物胁迫因素具有耐受性。此类植物可通过遗传转化或通过选择含有赋予这种胁迫抗性的突变的植物而获得。特别有用的胁迫耐受性植物包括以下植物:
1)含有能够降低植物细胞或植物中的聚(二磷酸腺苷-核糖)聚合酶(PARP)基因的表达和/或活性的转基因的植物,如WO00/04173、WO 06/045633、EP-A 1 807 519或EP-A 2018 431中所记载。
2)含有能够降低植物或植物细胞中的PARG编码基因的表达和/或活性的增强胁迫耐受性的转基因的植物,例如WO04/090140中所记载。
3)含有编码烟酰胺腺嘌呤二核苷酸补救生物合成路径的植物功能酶的增强胁迫耐受性的转基因的植物,所述植物功能酶包括烟酰胺酶、烟酰酸磷酸核糖基转移酶、烟酸单核苷酸腺苷酰转移酶、烟酰胺腺嘌呤二核苷酸合酶或烟酰胺磷酸核糖基转移酶,例如EP-A1 794 306、WO 06/133827、WO 07/107326、EP-A 1 999 263或WO 07/107326中所记载。
还可根据本发明处理的植物或植物栽培种(通过植物生物技术方法如基因工程获得)显示出改变的采收产品的数量、品质和/或储存稳定性,和/或改变的采收产品的特定组分的特性,所述植物或植物栽培种为例如:
1)合成改性淀粉的转基因植物,与野生型植物细胞或植物中的合成淀粉相比,该改性淀粉就其物理化学特性而言,特别是直链淀粉的含量或直链淀粉/支链淀粉的比例、支化度、平均链长、侧链分布、粘性行为、胶凝强度、淀粉颗粒大小和/或淀粉颗粒形貌发生改变,从而使该改性淀粉更适合于特定的应用。合成改性淀粉的这些转基因植物公开于例如以下文献中:EP-A 0 571 427、WO 95/04826、EP-A 0 719 338、WO96/15248、WO 96/19581、WO 96/27674、WO 97/11188、WO97/26362、WO 97/32985、WO 97/42328、WO 97/44472、WO97/45545、WO 98/27212、WO 98/40503、WO 99/58688、WO99/58690、WO 99/58654、WO 00/08184、WO 00/08185、WO00/08175、WO 00/28052、WO 00/77229、WO 01/12782、WO01/12826、WO 02/101059、WO 03/071860、WO 04/056999、WO 05/030942、WO 05/030941、WO 05/095632、WO05/095617、WO 05/095619、WO 2005/095618、WO 05/123927、WO 06/018319、WO 06/103107、WO06/108702、WO07/009823、WO 00/22140、WO 06/063862、WO 06/072603、WO 02/034923、WO08/017518、WO 08/080630、WO08/080631、WO 08/090008、WO 01/14569、WO 02/79410、WO03/33540、WO 04/078983、WO 01/19975、WO 95/26407、WO 96/34968、WO 98/20145、WO 99/12950、WO 99/66050、WO 99/53072、US 6,734,341、WO 00/11192、WO 98/22604、WO 98/32326、WO 01/98509、WO 01/98509、WO 05/002359、US 5,824,790、US 6,013,861、WO 94/04693、WO 94/09144、WO 94/11520、WO 95/35026、WO 97/20936、WO 10/012796、WO 10/003701、WO13/053729、WO13/053730。
2)合成非淀粉碳水化合物聚合物的转基因植物,或与未经遗传修饰的野生型植物相比,合成具有改变的特性的非淀粉碳水化合物聚合物的转基因植物(例如WO2015044209)。实例为产生多聚果糖(尤其是菊糖和果聚糖型)的植物,如EP-A0 663 956、WO96/01904、WO 96/21023、WO 98/39460和WO 99/24593中所记载;产生α-1,4-葡聚糖的植物,如WO95/31553、US 2002031826、US 6,284,479、US 5,712,107、WO97/47806、WO 97/47807、WO 97/47808和WO 00/14249中所记载;产生α-1,6-支化α-1,4-葡聚糖的植物,如WO 00/73422中所记载;和产生交替聚糖(alternan)的植物,如WO00/47727、WO 00/73422、US 5,908,975和EP-A 0 728 213中所记载。
3)产生透明质酸的转基因植物,例如WO 06/032538、WO07/039314、WO 07/039315、WO 07/039316、JP-A 2006-304779和WO 05/012529中所记载。
4)特征为例如“高可溶性固含量”、“温和”(低刺激性,LP)和/或“长期储存性”(LS)的转基因植物或杂交植物,例如鳞茎类,如美国专利申请12/020,360中所记载。
5)表明产量增加的转基因植物,例如WO 11/095528、WO2014161908、WO2015032428或WO 2015117265中所公开。
6)提供具有改进特性的果实或蔬菜的植物,包括转基因植物,如WO 2013156204、WO 2013120781、WO 2014090968、WO2014049002、WO 2014079896、WO 2014118150、WO2015040098A1中所记载。
还可根据本发明处理的植物或植物栽培种(其可通过植物生物技术方法如基因工程获得)为具有改变的纤维特性的植物,如棉花植物。此类植物可通过遗传转化或通过选择含有赋予这种改变的纤维特性的突变的植物而获得,所述植物包括:
a)含有改变形式的纤维素合酶基因的植物,如棉花植物,如WO 98/00549中所记载;
b)含有改变形式的rsw2或rsw3同源核酸的植物,如棉花植物,如WO 04/053219中所记载;
c)具有增加的蔗糖磷酸合酶的表达的植物,如棉花植物,如WO01/17333中所记载;
d)具有增加的蔗糖合酶的表达的植物,如棉花植物,如WO02/45485中所记载;
e)其中例如通过下调纤维选择性β-1,3-葡聚糖酶而改变在纤维细胞基部胞间连丝门控的时机的植物,如棉花植物,如WO05/017157或WO 09/143995中所记载;
f)具有改变的反应性的纤维——例如通过表达N-乙酰葡糖胺转移酶基因(包括nodC)和几丁质合酶基因——的植物,如棉花植物,如WO 06/136351、WO 2011/089021、WO2011/089021、WO 2012/074868和WO 2015140191中所记载。
还可根据本发明处理的植物或植物栽培种(其可通过植物生物技术方法如基因工程获得)为具有改变的油分布特性的植物,如油菜或相关的芸苔属植物。此类植物可通过遗传转化或通过选择含有赋予这种改变的油特性的突变的植物而获得,所述植物包括:
a)产生具有高油酸含量的油的植物,如油菜植物,例如US5,969,169、US 5,840,946、US 6,323,392、US 6,063,947或WO2014006158、WO 2014006159、WO 2014006162中所记载;
b)产生具有低亚麻酸含量的油的植物,如油菜植物,如US6,270,828、US 6,169,190或US 5,965,755、WO 2011/060946中所记载;
c)产生具有低饱和脂肪酸含量的油的植物,如油菜植物,例如US 5,434,283或美国专利申请12/668303或WO 2014006158、WO 2014006159中所记载。
还可根据本发明处理的植物或植物栽培种(其可通过植物生物技术方法如基因工程获得)为具有改变的落粒(seed shattering)特性的植物,如油菜或相关的芸苔属植物。此类植物可通过遗传转化或通过选择含有赋予这种改变的落粒特性的突变的植物而获得;这些植物包括具有延迟的或减少的落粒的油菜植物,如美国专利申请61/135,230、WO 09/068313和WO 10/006732中所记载。
还可根据本发明处理的植物或植物栽培种(其可通过植物生物技术方法如基因工程获得)为具有改变的翻译后蛋白质修饰模式的植物,如烟草植物,例如WO 10/121818和WO10/145846中所记载。
可根据本发明处理的转基因有用植物优选为包含转化株系或转化株系的组合的植物,并且其列于例如不同国家或地区的登记机构的数据库中,其包括:株系531/PV-GHBK04(棉花,昆虫防治,记载于WO 2002/040677中);株系1143-14A(棉花,昆虫防治,未保藏,记载于WO 06/128569中);株系1143-51B(棉花,昆虫防治,未保藏,记载于WO 06/128570中);株系1445(棉花,除草剂耐受性,未保藏,记载于US-A 2002-120964或WO 02/034946中);株系17053(稻,除草剂耐受性,保藏为PTA-9843,记载于WO 10/117737中);株系17314(稻,除草剂耐受性,保藏为PTA-9844,记载于WO10/117735中);株系281-24-236(棉花,昆虫防治-除草剂耐受性,保藏为PTA-6233,记载于WO 05/103266或US-A 2005-216969中);株系3006-210-23(棉花,昆虫防治-除草剂耐受性,保藏为PTA-6233,记载于US-A 2007-143876或WO 05/103266中);株系3272(玉米,品质性状,保藏为PTA-9972,记载于WO 06098952或US-A2006-230473中);株系40416(玉米,昆虫防治-除草剂耐受性,保藏为ATCC PTA-11508,记载于WO 11/075593中);株系43A47(玉米,昆虫防治-除草剂耐受性,保藏为ATCC PTA-11509,记载于WO11/075595中);株系5307(玉米,昆虫防治,保藏为ATCC PTA-9561,记载于WO 10/077816中);株系ASR-368(翦股颖(bent grass),除草剂耐受性,保藏为ATCC PTA-4816,记载于US-A 2006-162007或WO 04/053062中);株系B16(玉米,除草剂耐受性,未保藏,记载于US-A 2003-126634中);株系BPS-CV127-9(大豆,除草剂耐受性,保藏为NCIMB编号41603,记载于WO 10/080829中);株系BLR1(油菜植株,雄性不育性再栽培,保藏为NCIMB41193,记载于WO 2005/074671中);株系CE43-67B(棉花,昆虫防治,保藏为DSM ACC2724,记载于US-A 2009-217423或WO 06/128573中);株系CE44-69D(棉花,昆虫防治,未保藏,记载于US-A2010-0024077中);株系CE44-69D(棉花,昆虫防治,未保藏,记载于WO 06/128571中);株系CE46-02A(棉花,昆虫防治,未保藏,记载于WO 06/128572中);株系COT102(棉花,昆虫防治,未保藏,记载于US-A 2006-130175或WO 04/039986中);株系COT202(棉花,昆虫防治,未保藏,记载于US-A 2007-067868或WO 05/054479中);株系COT203(棉花,昆虫防治,未保藏,记载于WO 05/054480中);株系DAS21606-3/1606(大豆,除草剂耐受性,保藏为PTA-11028,记载于WO 012/033794中);株系DAS40278(玉米,除草剂耐受性,保藏为ATCC PTA-10244,记载于WO11/022469中);株系DAS-44406-6/pDAB8264.44.06.1(大豆,除草剂耐受性,保藏为PTA-11336,记载于WO 2012/075426中);株系DAS-14536-7/pDAB8291.45.36.2(大豆,除草剂耐受性,保藏为PTA-11335,记载于WO 2012/075429中);株系DAS-59122-7(玉米,昆虫防治-除草剂耐受性,保藏为ATCC PTA 11384,记载于US-A2006-070139中);株系DAS-59132(玉米,昆虫防治-除草剂耐受性,未保藏,记载于WO 09/100188中);株系DAS68416(大豆,除草剂耐受性,保藏为ATCC PTA-10442,记载于WO 11/066384或WO11/066360中);株系DP-098140-6(玉米,除草剂耐受性,保藏为ATCC PTA-8296,记载于US-A2009-137395或WO 08/112019中);株系DP-305423-1(大豆,品质性状,未保藏,记载于US-A2008-312082或WO 08/054747中);株系DP-32138-1(玉米,杂交体系,保藏为ATCC PTA-9158,记载于US-A 2009-0210970或WO 09/103049中);株系DP-356043-5(大豆,除草剂耐受性,保藏为ATCC PTA-8287,记载于US-A 2010-0184079或WO 08/002872中);株系EE-1(茄子,昆虫防治,未保藏,记载于WO 07/091277中);株系FI117(玉米,除草剂耐受性,保藏为ATCC 209031,记载于US-A 2006-059581或WO 98/044140中);株系FG72(大豆,除草剂耐受性,保藏为PTA-11041,记载于WO 2011/063413中);株系GA21(玉米,除草剂耐受性,保藏为ATCC 209033,记载于US-A 2005-086719或WO98/044140中);株系GG25(玉米,除草剂耐受性,保藏为ATCC209032,记载于US-A 2005-188434或WO 98/044140中);株系GHB119(棉花,昆虫防治-除草剂耐受性,保藏为ATCC PTA-8398,记载于WO 08/151780中);株系GHB614(棉花,除草剂耐受性,保藏为ATCC PTA-6878,记载于US-A 2010-050282或WO 07/017186中);株系GJ11(玉米,除草剂耐受性,保藏为ATCC 209030,记载于US-A 2005-188434或WO 98/044140中);株系GM RZ13(甜菜,病毒抗性,保藏为NCIMB-41601,记载于WO 10/076212中);株系H7-1(甜菜,除草剂耐受性,保藏为NCIMB 41158或NCIMB41159,记载于US-A 2004-172669或WO 04/074492中);株系JOPLIN1(小麦,真菌抗性,未保藏,记载于US-A 2008-064032中);株系LL27(大豆,除草剂耐受性,保藏为NCIMB41658,记载于WO 06/108674或US-A 2008-320616中);株系LL55(大豆,除草剂耐受性,保藏为NCIMB 41660,记载于WO 06/108675或US-A2008-196127中);株系LLcotton25(棉花,除草剂耐受性,保藏为ATCC PTA-3343,记载于WO 03/013224或US-A 2003-097687中);株系LLRICE06(稻,除草剂耐受性,保藏为ATCC-23352,记载于US 6,468,747或WO 00/026345中);株系LLRice62(稻,除草剂耐受性,保藏为ATCC-203352,记载于WO 00/026345中);株系LLRICE601(稻,除草剂耐受性,保藏为ATCC PTA-2600,记载于US-A 2008-2289060或WO 00/026356中);株系LY038(玉米,品质性状,保藏为ATCC PTA-5623,记载于US-A 2007-028322或WO05/061720中);株系MIR162(玉米,昆虫防治,保藏为PTA-8166,记载于US-A 2009-300784或WO 07/142840中);株系MIR604(玉米,昆虫防治,未保藏,记载于US-A 2008-167456或WO 05/103301中);株系MON15985(棉花,昆虫防治,保藏为ATCC PTA-2516,记载于US-A 2004-250317或WO 02/100163中);株系MON810(玉米,昆虫防治,未保藏,记载于US-A 2002-102582中);株系MON863(玉米,昆虫防治,保藏为ATCC PTA-2605,记载于WO 04/011601或US-A 2006-095986中);株系MON87427(玉米,授粉防治,保藏为ATCC PTA-7899,记载于WO 11/062904中);株系MON87460(玉米,胁迫耐受性,保藏为ATCC PTA-8910,记载于WO 09/111263或US-A 2011-0138504中);株系MON87701(大豆,昆虫防治,保藏为ATCC PTA-8194,记载于US-A 2009-130071或WO 09/064652中);株系MON87705(大豆,品质性状-除草剂耐受性,保藏为ATCC PTA-9241,记载于US-A 2010-0080887或WO 10/037016中);株系MON87708(大豆,除草剂耐受性,保藏为ATCCPTA-9670,记载于WO 11/034704中);株系MON87712(大豆,产量,保藏为ATCC PTA-10296,记载于WO 12/051199中);株系MON87754(大豆,品质性状,保藏为ATCC PTA-9385,记载于WO10/024976中);株系MON87769(大豆,品质性状,保藏为ATCC PTA-8911,记载于US-A 2011-0067141或WO 09/102873中);株系MON88017(玉米,昆虫防治-除草剂耐受性,保藏为ATCCPTA-5582,记载于US-A2008-028482或WO 05/059103中);株系MON88913(棉花,除草剂耐受性,保藏为ATCC PTA-4854,记载于WO 04/072235或US-A2006-059590中);株系MON88302(油菜植株,除草剂耐受性,保藏为PTA-10955,记载于WO 2011/153186中);株系MON88701(棉花,除草剂耐受性,保藏为PTA-11754,记载于WO 2012/134808中);株系MON89034(玉米,昆虫防治,保藏为ATCC PTA-7455,记载于WO 07/140256或US-A 2008-260932中);株系MON89788(大豆,除草剂耐受性,保藏为ATCC PTA-6708,记载于US-A 2006-282915或WO 06/130436中);株系MS11(油菜,授粉防治-除草剂耐受性,保藏为ATCC PTA-850或PTA-2485,记载于WO 01/031042中);株系MS8(油菜,授粉防治-除草剂耐受性,保藏为ATCC PTA-730,记载于WO 01/041558或US-A 2003-188347中);株系NK603(玉米,除草剂耐受性,保藏为ATCCPTA-2478,记载于US-A2007-292854中);株系PE-7(稻,昆虫防治,未保藏,记载于WO08/114282中);株系RF3(油菜,授粉防治-除草剂耐受性,保藏为ATCC PTA-730,记载于WO 01/041558或US-A 2003-188347中);株系RT73(油菜,除草剂耐受性,未保藏,记载于WO 02/036831或US-A 2008-070260中);株系SYHT0H2/SYN-00H2-5(大豆,除草剂耐受性,保藏为PTA-11226,记载于WO 2012/082548中);株系T227-1(甜菜,除草剂耐受性,未保藏,记载于WO 02/44407或US-A 2009-265817中);株系T25(玉米,除草剂耐受性,未保藏,记载于US-A2001-29014或WO 01/051654中);株系T304-40(棉花,昆虫防治-除草剂耐受性,保藏为ATCCPTA-8171,记载于US-A2010-077501或WO 08/122406中);株系T342-142(棉花,昆虫防治,未保藏,记载于WO 06/128568中);株系TC1507(玉米,昆虫防治-除草剂耐受性,未保藏,记载于US-A 2005-039226或WO04/099447中);株系VIP1034(玉米,昆虫防治-除草剂耐受性,保藏为ATCC PTA-3925,记载于WO 03/052073中);株系32316(玉米,昆虫防治-除草剂耐受性,保藏为PTA-11507,记载于WO11/084632中);株系4114(玉米,昆虫防治-除草剂耐受性,保藏为PTA-11506,记载于WO 11/084621中);株系EE-GM3/FG72(大豆,除草剂耐受性,ATCC登录号PTA-11041,WO 2011/063413A2);株系DAS-68416-4(大豆,除草剂耐受性,ATCC登录号PTA-10442,WO2 011/066360A1);株系DAS-68416-4(大豆,除草剂耐受性,ATCC登录号PTA-10442,WO 2011/066384A1);株系DP-040416-8(玉米,昆虫防治,ATCC登录号PTA-11508,WO2011/075593A1);株系DP-043A47-3(玉米,昆虫防治,ATCC登录号PTA-11509,WO 2011/075595A1);株系DP-004114-3(玉米,昆虫防治,ATCC登录号PTA-11506,WO 2011/084621A1);株系DP-032316-8(玉米,昆虫防治,ATCC登录号PTA-11507,WO 2011/084632A1);株系MON-88302-9(油菜植株,除草剂耐受性,ATCC登录号PTA-10955,WO 2011/153186A1);株系DAS-21606-3(大豆,除草剂耐受性,ATCC登录号PTA-11028,WO 2012/033794A2);株系MON-87712-4(大豆植株,品质性状,ATCC登录号PTA-10296,WO2012/051199A2);株系DAS-44406-6(大豆,堆叠的除草剂耐受性,ATCC登录号PTA-11336,WO2012/075426A1);株系DAS-14536-7(大豆,堆叠的除草剂耐受性,ATCC登录号PTA-11335,WO2012/075429A1);株系SYN-000H2-5(大豆,堆叠的除草剂耐受性,ATCC登录号PTA-11226,WO 2012/082548A2);株系DP-061061-7(油菜植株,除草剂耐受性,未保藏,WO2012071039A1);株系DP-073496-4(油菜植株,除草剂耐受性,未保藏,US2012131692);株系8264.44.06.1(大豆,堆叠的除草剂耐受性,ATCC登录号PTA-11336,WO 2012075426A2);株系8291.45.36.2(大豆,堆叠的除草剂耐受性,ATCC登录号PTA-11335,WO 2012075429A2);株系SYHT0H2(大豆,ATCC登录号PTA-11226,WO2012/082548A2);株系MON88701(棉花,ATCC登录号PTA-11754,WO 2012/134808A1);株系KK179-2(紫花苜蓿,ATCC登录号PTA-11833,WO2013003558A1);株系pDAB8264.42.32.1(大豆,堆叠的除草剂耐受性,ATCC登录号PTA-11993,WO2013010094A1);株系MZDT09Y(玉米,ATCC登录号PTA-13025,WO 2013012775A1);株系KK179-2(紫花苜蓿,ATCC登录号PTA-11833,WO2013003558A1);株系pDAB8264.42.32.1(大豆,堆叠的除草剂耐受性,ATCC登录号PTA-1 1993,WO2013010094A1);株系MZDT09Y(玉米,ATCC登录号PTA-13025,WO2013012775A1);株系VCO-01981-5(玉米,除草剂耐受性,NCIMB登录号41842,WO2013014241A1);株系DAS-81419-2X DAS-68416-4(大豆,堆叠的昆虫抗性和除草剂耐受性,ATCC登录号PTA-10442,WO2013016516A1);株系DAS-81419-2(大豆,堆叠的昆虫抗性和除草剂耐受性,ATCC登录号PTA-12006,WO2013016527A1);株系HCEM485(玉米,除草剂耐受性,ATCC登录号PTA-12014,WO2013025400A1);株系pDAB4468.18.07.1(棉花,除草剂耐受性,ATCC登录号PTA-12456,WO2013112525A2);株系pDAB4468.19.10.3(棉花,除草剂耐受性,ATCC登录号PTA-12457,WO2013112527A1)。
随后的实施例详细说明了本发明。
A.化学实施例
实施例1-44:7-(5-羟基-1-乙基-吡唑-3-羰基)-4-(三氟甲基)-1,3-苯并氧硫杂环戊烷的合成
将97mg(0.6mmol)羰基二咪唑加入到125mg(0.5mmol)4-(三氟甲基)-1,3-苯并氧硫杂环戊烷-7-甲酸和73mg(0.65mmol)5-羟基-1-乙基吡唑于10mL乙腈中的溶液中。在室温下搅拌4天后,加入101mg(1mmol)三乙胺、20mg(0.2mmol)丙酮氰醇和一刮勺尖(Spatelspitze)的KCN。5天后,将溶剂浓缩,将残余物溶于二氯甲烷中,并用10%浓度的硫酸洗涤。将有机相干燥,浓缩,并将所得残余物通过RP-HPLC纯化。产量114mg(65%)。
中间体1-44A:2-羟基-3-甲基亚磺酰基-4-(三氟甲基)苯甲酸乙酯的合成
将20mg硫酸和2.4mL(27mmol)过氧化氢(35%浓度)加入到6.45g(22.5mmol)2-羟基-3-甲硫基-4-(三氟甲基)苯甲酸乙酯于15mL乙腈中的溶液中,然后将混合物在60℃下加热20小时。在加入亚硫酸氢钠溶液后,将混合物浓缩,抽滤出残余物,并用水和少量乙酸乙酯洗涤。将有机相用饱和氯化钠溶液洗涤,干燥并浓缩,所得粗产物不经纯化即可进一步反应。产量6.64g。(NMR,DMSO-d6:11.80(brs,1H),8.05(d,1H),7.45(d,1H),4.39(q,2H),3.15(s,3H),1.34(t,3H))
中间体1-44B:2-羟基-3-氯甲基硫基-4-(三氟甲基)苯甲酸乙酯的合成
在用水冷却的情况下,将6mL亚硫酰氯滴加到5.6g(18.2mmol)2-羟基-3-甲基亚磺酰基-4-(三氟甲基)苯甲酸乙酯中(放出气体!),然后继续搅拌15分钟。将混合物浓缩并使其不经纯化即可进一步反应。(NMR,DMSO-d6:11.68(brs,1H),8.07(dd,1H),7.45(d,1H),5.32(s,2H),4.45(q,2H),1.38(t,3H))
中间体1-44C:4-(三氟甲基)-1,3-苯并氧硫杂环戊烷-7-甲酸的合成
在冰浴冷却的情况下,将溶解于5mL乙腈中的5g(18.2mmol)2-羟基-3-氯甲基硫基-4-(三氟甲基)苯甲酸乙酯加入到170g 20%浓度的氢氧化钠水溶液中。将混合物静置过夜,然后用浓盐酸酸化至pH 1,抽滤出沉淀物,并用水洗涤。随后将其溶于5%浓度的氢氧化钠水溶液中,通过抽滤除去未溶解的副产物,并通过用浓盐酸酸化沉淀,干燥后,得到3.9g产物。(NMR,DMSO-d6:δ=13.37(br s,1H);7.63(d,1H);7.31(d,1H);5.99(s,2H))
所公开的实施例的NMR数据以常规形式(δ值、氢原子数、多重分裂峰)列出,或以所谓的NMR峰列表形式列出。在NMR峰列表方法中,所选择的实施例的NMR数据以NMR峰列表的形式记录,其中对于每个信号峰,首先列出以ppm计的δ值,然后列出信号强度(通过空格隔开)。不同信号峰的δ值/信号强度数对通过分号彼此间隔列出。
因此,一个实施例的峰列表采取以下形式:
δ1(强度1);δ2(强度2);……;δi(强度i);……;δn(强度n)
尖峰信号的强度与NMR谱的打印实例中以cm计的信号高度相关,并显示了信号强度的真实比例。在宽峰信号的情况下,可以显示几个峰或信号的中间部分及其与谱图中的最强信号相比的相对强度。
1H NMR谱图的化学位移的校准使用四甲基硅烷和/或溶剂的化学位移完成,特别是在DMSO中测量的谱图的情况下。因此,四甲基硅烷峰可以但不是必须出现在NMR峰列表中。
1H NMR峰列表与常规1H NMR打印件相似,因此通常包含在常规NMR说明中列出的所有峰。
此外,如同常规的1H NMR打印件,它们可以显示溶剂信号、目标化合物的立体异构体(其同样由本发明提供)的信号和/或杂质的峰的信号。
在溶剂和/或水的δ范围内的化合物信号的报告中,1H NMR峰的列表显示了标准溶剂峰,例如在DMSO-D6中的DMSO的峰和水的峰,其通常平均具有高的强度。
此类立体异构体和/或杂质可以是特定的制备方法所特有的。因此,通过参考“副产物指纹(by-product fingerprints)”,它们的峰可帮助识别对制备方法的再现性。
专业人员在通过已知方法(MestreC、ACD模拟,以及使用经验评估的预期值)计算目标化合物的峰时,可视需要任选地使用另外的强度滤波器来分离目标化合物的峰。这种分离类似于常规1H NMR说明中相关峰的拾取。
可在研究公开数据库(Research Disclosure Database)第564025号中找到1HNMR峰列表的其他详细信息。
分析数据
B.制剂实施例
1.撒粉产品
撒粉产品通过以下方式获得:将10重量份式(I)的化合物与90重量份作为惰性物质的滑石混合,并将混合物在锤磨机中粉碎。
2.可分散粉剂
易分散于水中的可湿性粉剂通过以下方式获得:将25重量份式(I)的化合物、64重量份作为惰性物质的含高岭土的石英、10重量份木质素磺酸钾和1重量份作为润湿剂和分散剂的油酰基甲基牛磺酸钠混合,并将混合物在销盘式磨机中研磨。
3.分散浓缩剂
易分散于水中的分散浓缩剂通过以下方式获得:将20重量份式(I)的化合物、6重量份烷基酚聚乙二醇醚(X 207)、3重量份异十三烷醇聚乙二醇醚(8EO)和71重量份石蜡基矿物油(沸程为例如约255℃至大于277℃)混合,并将混合物在摩擦式球磨机中研磨至低于5微米的细度。
4.可乳化浓缩剂
可乳化浓缩剂由以下物质获得:15重量份式(I)的化合物、75重量份作为溶剂的环己酮和10重量份作为乳化剂的乙氧基化壬基酚。
5.水分散性颗粒剂
水分散性颗粒剂通过以下方式获得:混合
75重量份式(I)的化合物,
10重量份木质素磺酸钙,
5重量份十二烷基硫酸钠,
3重量份聚乙烯醇,和
7重量份高岭土,
将混合物在销盘式磨机中研磨,并在流化床中通过喷淋施用水作为造粒液体而使粉末粒化。
水分散性颗粒剂还通过以下方式获得:在胶体磨机中均质化和预粉碎
25重量份式(I)的化合物,
5重量份2,2'-二萘基甲烷-6,6'-二磺酸钠,
2重量份油酰基甲基牛磺酸钠,
1重量份聚乙烯醇,
17重量份碳酸钙,和
50重量份水,
然后将混合物在珠磨机中研磨,并在喷雾塔中借助单相喷嘴使由此获得的悬浮液雾化和干燥。
C.生物实施例
试验说明
在下表中,使用以下缩写:
不希望的植物/杂草:
ABUTH:苘麻(Abutilon theophrasti)
AMARE:反枝苋(Amaranthus retroflexus)
CYPES:油莎草(Cyperus esculentus)
ECHCG:稗草(Echinochloa crus-galli)
SETVI:狗尾草(Setaria viridis)
STEME:繁缕(Stellaria media)
VERPE:阿拉伯婆婆纳(Veronica persica)
VIOTR:三色堇(Viola tricolor)
1.苗前除草作用和作物植物相容性
将单子叶和双子叶杂草植物和作物植物的种子置于塑料盆或有机种植盆中,并用土壤覆盖。然后,将配制成可湿性粉剂(WP)或可乳化浓缩剂(EC)形式的本发明化合物以水性悬浮液或乳液的形式施用至覆盖土壤的表面上,添加0.5%添加剂,在600L/ha(换算值)的水施用率下。在处理后,将盆置于温室中并保持在试验植物的良好的生长条件下。在约3周后,与未处理的对照组比较,目测评估制剂的效果,以百分比计。下表显示了本发明的许多化合物对重要的有害植物的除草活性。例如,100%活性=植物已经死亡,0%活性=类似对照植物。
表1:对CYPES的苗前作用
表2:对ECHCG的苗前作用
表3:对SETVI的苗前作用
表4:对ABUTH的苗前作用
表5:对AMARE的苗前作用
表6:对STEME的苗前作用
表7:对VIOTR的苗前作用
表8:对VERPE的苗前作用
2.苗后除草作用和作物植物相容性
将单子叶和双子叶杂草以及作物植物的种子置于塑料盆或有机种植盆的砂壤土中,用土壤覆盖,并在生长条件受控的温室中培育。在播种后2至3周,在一叶期对试验植物进行处理。然后,将配制成可湿性粉剂(WP)或可乳化浓缩剂(EC)形式的本发明化合物以水性悬浮液或乳液的形式喷洒至植物的绿色部位上,添加0.5%添加剂,在600L/ha(换算值)的水施用率下。在试验植物已在温室中在最佳生长条件下保持约3周后,与未处理的对照组比较,目测评估制剂的活性。下表显示了本发明的许多化合物对重要的有害植物的除草活性。例如,100%活性=植物已经死亡,0%活性=类似对照植物。
表9:对ECHCG的苗后作用
表10:对SETVI的苗后作用
表11:对ABUTH的苗后作用
表12:对AMARE的苗后作用
表13:对STEME的苗后作用
表14:对VIOTR的苗后作用
表15:对VERPE的苗后作用
Claims (9)
1.通式(I)的化合物及其农业化学上可接受的盐,
其中符号和下标具有以下含义:
A代表(CH2)n,
X1、X2彼此独立地各自代表O或S(O)n,
R代表卤代-(C1-C6)-烷基,
Ra、Rb彼此独立地各自代表氢、氟、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基、(C1-C6)-烷硫基、氰基,或
Ra和Rb连同它们所连接的碳原子一起形成羰基或硫代羰基,
Rp1代表氢、(C1-C4)-烷基羰基氧基-(C1-C4)-烷基、(C1-C4)-烷氧基羰基氧基-(C1-C4)-烷基、(C1-C6)-烷基磺酰基、(C1-C4)-烷氧基-(C1-C6)-烷基磺酰基,或在每种情况下被n个选自卤素、(C1-C4)-烷基和(C1-C4)-烷氧基的相同或不同的基团取代的苯基磺酰基、硫代苯基-2-磺酰基、苯甲酰基、苯甲酰基-(C1-C6)-烷基或苄基,
Rp2代表(C1-C4)-烷基,
Rp3代表氢、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C8)-环烷基、(C1-C4)-烷基-(C3-C8)-环烷基或(C3-C6)-卤代环烷基,
n代表0、1或2。
2.如权利要求1中所要求保护的化合物,其中
A代表(CH2)n,
X1、X2彼此独立地各自代表O或S(O)n,
R代表卤代-(C1-C3)-烷基,
Ra、Rb彼此独立地各自代表氢、氟、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基,或
Ra和Rb连同它们所连接的碳原子一起形成羰基或硫代羰基,
Rp1代表氢,
Rp2代表(C1-C4)-烷基,
Rp3代表氢、(C1-C4)-烷基、(C1-C4)-卤代烷基或环丙基,
n代表0、1或2。
3.如权利要求1或2中所要求保护的化合物,其中
A代表(CH2)n,
X1、X2彼此独立地各自代表O或S(O)n,
R代表三氟甲基、二氟甲基或五氟乙基,
Ra、Rb彼此独立地各自代表氢、氟、甲基、乙基、三氟甲基、二氟甲基、甲氧基、乙氧基,或
Ra和Rb连同它们所连接的碳原子一起形成羰基或硫代羰基,
Rp1代表氢,
Rp2代表(C1-C4)-烷基,
Rp3代表氢、(C1-C4)-烷基、(C1-C4)-卤代烷基或环丙基,
n代表0、1或2。
4.一种除草组合物,其特征在于除草有效量的至少一种如权利要求1至3中任一项所要求保护的式(I)的化合物。
5.如权利要求4中所要求保护的除草组合物,将其与制剂助剂混合。
6.一种防治不想要的植物的方法,其特征在于,将有效量的至少一种如权利要求1至3中任一项所要求保护的式(I)的化合物或如权利要求4或5所要求保护的除草组合物施用至植物或不想要的植物的位置。
7.如权利要求1至3中任一项所要求保护的式(I)的化合物或如权利要求4或5所要求保护的除草组合物用于防治不想要的植物的用途。
8.如权利要求7中所要求保护的用途,其特征在于,将式(I)的化合物用于防治有用植物作物中的不想要的植物。
9.如权利要求8中所要求保护的用途,其特征在于,有用植物为转基因有用植物。
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-
2019
- 2019-05-29 WO PCT/EP2019/064008 patent/WO2019233863A1/de unknown
- 2019-05-29 JP JP2020567481A patent/JP2021525774A/ja active Pending
- 2019-05-29 EP EP19728922.6A patent/EP3802521A1/de not_active Withdrawn
- 2019-05-29 CN CN201980049886.XA patent/CN112513033A/zh active Pending
- 2019-05-29 BR BR112020024615-8A patent/BR112020024615A2/pt not_active IP Right Cessation
- 2019-05-29 US US15/734,496 patent/US20210323950A1/en active Pending
- 2019-06-04 AR ARP190101501A patent/AR114912A1/es unknown
Also Published As
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EP3802521A1 (de) | 2021-04-14 |
US20210323950A1 (en) | 2021-10-21 |
BR112020024615A2 (pt) | 2021-03-02 |
JP2021525774A (ja) | 2021-09-27 |
AR114912A1 (es) | 2020-10-28 |
WO2019233863A1 (de) | 2019-12-12 |
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