CN1894219A - 旋光甲酰胺及其用于防治不想要的微生物的应用 - Google Patents
旋光甲酰胺及其用于防治不想要的微生物的应用 Download PDFInfo
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- CN1894219A CN1894219A CN 200480037963 CN200480037963A CN1894219A CN 1894219 A CN1894219 A CN 1894219A CN 200480037963 CN200480037963 CN 200480037963 CN 200480037963 A CN200480037963 A CN 200480037963A CN 1894219 A CN1894219 A CN 1894219A
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- methyl
- trifluoromethyl
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Abstract
以下结构式(I)的新的旋光甲酰胺,其多种制备方法以及其用于防治不想要的微生物的应用,以及新的中间体及其制备。其中,R、M和A具有说明书中所述的含义。
Description
本发明涉及新的旋光甲酰胺,其多种制备方法以及其用于防治不想要的微生物的应用。
已知多种甲酰胺具有杀真菌性能(参见,例如WO 03/010149、WO02/059086、WO 02/38542、WO 00/09482、DE-A 102 29 595、EP-A 0 591699、EP-A 0 589 301以及EP-A 0 545 099)。例如,已知于WO 03/010149的5-氟-1,3-二甲基-N-[2-(1,3,3-三甲基丁基)苯基]-1H-吡唑-4-甲酰胺的外消旋物,以及已知于DE-A 102 29 595的N-[2-(1,3-二甲基丁基)苯基]-2-碘苯甲酰胺。这些化合物的活性良好,但在以低浓度施用时,在很多情况下还不能满足需要。
由于对现代杀虫剂的多种要求,例如对于那些影响药效、作用时间、作用谱、施用范围、毒性、与其他活性化合物的结合情况、与制剂赋形剂的结合情况或合成的各种要求,以及由于可能出现的抗性,因此永远不能认为这类化合物的开发已经结束。因此,持续存在对某些方面至少部分优于已知化合物的新化合物的高需求。
现已发现以下结构式(I)的旋光甲酰胺,
其中,
R代表氢、氟、氯、甲基、乙基或三氟甲基,
M代表
其中,带有*标记的键与酰胺连接,带有#标记的键与烷基支链连接,
R1代表氢、氟、氯、甲基或三氟甲基,
A代表以下结构式(A1)的基团
R2代表甲基、三氟甲基或二氟甲基,
R3代表氢、氟或氯,
或者,
A代表以下结构式(A2)的基团
R4代表三氟甲基、氯、溴或碘,
或者,
A代表以下结构式(A3)的基团
R5代表甲基、三氟甲基或二氟甲基。
结构式(I)的化合物具有S构型[结构式(I)中标有S的C原子]。还发现结构式(I)的旋光甲酰胺通过以下方式得到:
a)在任选存在催化剂时,在任选存在缩合剂时,在任选存在酸结合剂时,以及在任选存在稀释剂时,
以下结构式(II)的羧酸衍生物
其中,
A具有上述含义,并且
X1代表卤素或羟基,
与以下结构式(III)的胺反应,
其中,R和M具有上述含义,
或者,
b)以下结构式(I-rac)的外消旋化合物
其中,R、M和A具有上述含义,
在存在呈液相的洗脱剂或洗脱剂混合物时,在手性硅胶固定相上进行色谱分离,
或者,在形成盐的条件下与旋光酸分级结晶,并且,随后释出纯对映体的或富含对映体的结构式(I)的化合物,
或者,
c)以下结构式(IV)的化合物
其中,R、M和A具有上述含义,
或者,以下结构式(V)的化合物
其中,R、M和A具有上述含义,
或者,以上两种化合物的混合物,在存在旋光催化剂或存在具有旋光配位体的催化剂时进行氢化。
还发现结构式(I)的新的旋光甲酰胺具有非常良好的杀微生物性能,并且适于在植物保护及材料保护中防治不想要的微生物。
与已知的甲酰胺比较,结构式(I)的新的旋光甲酰胺的特征在于更好的活性以及更低的施用量,并因此具有对环境较低的不利影响以及降低的毒性。
本发明的旋光甲酰胺由结构式(I)总体定义。以下给出之前以及此后定义的结构式的优选基团的定义。这些定义同样适用于结构式(I)的最终产物以及所有中间体。
R优
选代表氢、甲基或乙基。
R
更优选代表氢或甲基。
M
优选代表M-1。
M还
优选代表M-2。
M还
优选代表M-3。
M
优选代表M-4。
M
更优选代表M-1,其中R1代表氢。
M还
更优选代表M-2,其中R1代表氢。
R1 优选代表氢。
R1还
优选代表氟,其中氟
更优选在苯胺基团的4、5或6位,
尤其优选在4或6位,
极优选在4位[参见以上结构式(I)]。
A
优选代表A1基团。
A
更优选代表含义为5-氟-1,3-二甲基-1H-吡唑-4-基、3-三氟甲基-1-甲基-1H-吡唑-4-基或3-二氟甲基-1-甲基-1H-吡唑-4-基的A1。
A尤其优选代表含义为5-氟-1,3-二甲基-1H-吡唑-4-基的A1。
A还
优选代表A2基团。
A
更优选代表含义为2-三氟甲基苯基或2-碘苯基的A2。
A还
优选代表A3基团。
A
更优选代表含义为1,4-二甲基-吡唑-3-基、1-甲基-4-三氟甲基-吡唑-3-基或1-甲基-4-二氟甲基-吡唑-3-基的A3。
A尤其优选代表含义为1-甲基-4-三氟甲基-吡唑-3-基的A3。
R2 优选代表甲基或三氟甲基。
R3 优选代表氢或氟。
R4 优选代表三氟甲基或碘。
R5 优选代表三氟甲基。
然而,上述基团在总体或优选范围内的定义或说明还可在各自范围或优选范围之间自行相互结合。这适用于最终产物以及前体和中间体。
给出的定义还可根据需要相互结合。而且,单独的定义可能省略。
优选、更优选以及尤其优选的化合物为各自具有优选、更优选或尤其优选的取代基的结构式(I)的化合物。
方法及中间产物的说明
方法(a)
如1-甲基-4-(三氟甲基)-1H-吡唑-3-羰基氯以及{2-[(1S)-1,3,3-三甲基丁基]-苯基}胺作为起始原料,则本发明的方法(a)可由以下反应式表示:
实施本发明的方法(a)而需要作为起始原料的羧酸衍生物由结构式(II)总体定义。该结构式(II)中,A优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的A的含义。X1优选代表氯、溴或羟基,更优选代表氯。
结构式(II)的羧酸衍生物是已知的(参见WO 93/11117、EP-A 0 545099、EP-A 0 589 301以及EP-A 0 589 313)。
此外,实施本发明的方法(a)而需要作为起始原料的胺由结构式(III)总体定义。该结构式(III)中,R和M优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的这些基团的含义。
结构式(III)的胺是新的。
结构式(III-a)的胺
其中,
R具有上述含义,
M1代表M-1,
可由,例如以下方式制备:
d)在第一步中,任选存在催化剂时,任选存在碱时并且任选存在稀释剂时,以下结构式(VI)的苯胺衍生物,
其中,R1具有上述含义,
与以下结构式(VII)的烯烃反应
其中,R具有上述含义,
由此得到以下结构式(VIII)的链烯基苯胺在第二步中,任选在存在稀释剂以及任选存在催化剂时氢化,
其中,R和R1具有上述含义,
由此得到的以下结构式(III-a-rac)的外消旋苯胺衍生物在第三步中在存在呈液相的洗脱剂或洗脱剂混合物时,在一种手性硅胶固定相上进行色谱分离,
其中,R和R1具有上述含义。
结构式(VIII)化合物的氢化还可任选在存在旋光催化剂或存在催化剂和旋光配位体时进行,从而得到结构式(III-a)的旋光化合物。
结构式(III-a-rac)的化合物还可在形成盐的条件下在存在旋光酸的条件下分级结晶,并且,随后得到以对映体组成的纯的或富含结构式(III-a)的化合物。通常,所有的旋光酸都适于非对映异构体盐的形成。
实例有:(1S)-(+)-2-莰酮-10-磺酸、(1R)-(-)-2-莰酮-10-磺酸、S,S-(-)-酒石酸、R,R-(+)-酒石酸、R-乳酸、S-乳酸或旋光氨基酸,优选天然的旋光的氨基酸。
实施本发明的方法(d)而需要作为起始原料的苯胺衍生物由结构式(VI)总体定义。该结构式(VI)中,R1优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的这些基团的含义。
结构式(VI)的苯胺衍生物是已知的。
实施本发明的方法(d)而需要作为起始原料的烯烃由结构式(VII)总体定义。该结构式(VII)中,R优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的该基团的含义。
结构式(VII)的烯烃是已知的,或者可通过已知方法得到。
实施本发明的方法(d)而作为中间体出现的链烯基苯胺由结构式(VIII)总体定义。该结构式(VIII)中,R和R1优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的这些基团的含义。
结构式(VIII)链烯基苯胺是已知的,并且/或者,可通过已知方法得到。
以下结构式(III-b)的胺
其中,
R具有上述含义,
M2代表M-2、M-3或M-4,
可通过,例如以下方式获得
e)结构式(III-b-rac)的外消旋胺
其中,R和M2具有上述含义,
在存在呈液相的洗脱剂或洗脱剂混合物时,在手性硅胶固定相上进行色谱分离。
结构式(III-b-rac)的外消旋胺是已知的,并且/或者,可通过已知方法得到(参见,例如WO 02/38542、EP-A 1 036 793以及EP-A 0 737 682)。
方法(b)
实施本发明的方法(b)而需作为起始原料的外消旋化合物由结构式(I-rac)总体定义。该结构式中,R、M和A优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的这些基团的含义。
用于实施方法(b)的结构式(I-rac)的外消旋化合物是已知的,并且可通过已知方法制备(参见,例如WO 03/010149、WO 02/38542以及DE-A 102 29 595)。结构式(I-rac)的外消旋化合物可通过,例如,结构式(II)的羧酸衍生物与结构式(III-a-rac)或(III-b-rac)的外消旋化合物以类似于本发明的方法(a)的反应得到。
在实施本发明的方法(b)中,使用制备色谱法,优选使用高效液相色谱法(HPLC)。在此,使用手性硅胶固定相。已证实Chiracel OD特别适于将结构式(I-rac)的化合物分离成两种对映体。该分离材料是市售的。其他固定相也可用作色谱材料。
如将结构式(I-rac)的化合物通过分级结晶分离为单独的旋光化合物,则所有旋光酸都适于非对映异构体盐的形成。所述旋光酸的实例有:(1S)-(+)-2-莰酮-10-磺酸、(1R)-(-)-2-莰酮-10-磺酸、S,S-(-)-酒石酸、R,R-(+)-酒石酸、R-乳酸、S-乳酸或旋光氨基酸,优选天然的旋光的氨基酸。
方法(c)
如N-[2-(1,3-二甲基丁-1-烯-1-基)苯基]-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、氢以及旋光催化剂用作起始原料,则本发明的方法(c)可由以下反应式表示:
实施本发明的方法(c)而需作为起始原料的化合物由结构式(IV)和(V)总体定义。这些结构式中,R、M和A优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的这些基团的含义。
结构式(IV)和(V)的化合物(或这些化合物的混合物)通过以下方式获得:
f)在任选存在催化剂时,在任选存在缩合剂时,在任选存在酸结合剂时以及在任选存在稀释剂时,
以下结构式(II)的羧酸衍生物
其中,
A具有上述含义,并且
X1代表卤素或羟基,
或者与以下结构式(VIII)的链烯基苯胺反应,
其中,R和R1具有上述含义,
或者与以下结构式(IX)的链烯基苯胺反应,
其中,R和R1具有上述含义。
或者,
g)在存在催化剂时,在任选存在碱时以及在任选存在稀释剂时,结构式(X)的甲酰胺
其中,M和A具有上述含义,并且,
Y代表溴或碘,
或者与以下结构式(VII)的烯烃反应,
其中R具有上述含义,
或者与以下结构式(XI)的烯烃反应,
其中R具有上述含义。
实施本发明的方法(f)而需作为起始原料的结构式(II)的羧酸衍生物已在方法(a)的有关介绍中说明。
实施本发明的方法(f)而也需作为起始原料的结构式(VIII)的羧酸衍生物已在方法(d)的有关介绍中说明。
实施本发明的方法(f)而需作为起始原料的链烯基苯胺由结构式(IX)总体定义。该结构式(IX)中,R和R1优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的这些基团的含义。
结构式(IX)的链烯基苯胺是已知的,并且/或者,可通过已知方法得到。
实施本发明的方法(g)而需作为起始原料的甲酰胺由结构式(X)总体定义。该结构式(X)中,M和A优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的这些基团的含义。
结构式(X)的甲酰胺是已知的,并且/或者,可通过已知方法得到(参见WO 03/010149)。
实施本发明的方法(g)而也需作为起始原料的结构式(VII)的烯烃已在方法(d)的有关介绍中说明。
实施本发明的方法(g)而需作为起始原料的烯烃由结构式(XI)总体定义。该结构式(XI)中,R优选、更优选或尤其优选具有在本发明的结构式(I)化合物的有关说明中已定义的优选、更优选以及尤其优选的这些基团的含义。
结构式(XI)的烯烃是已知的,并且/或者,可通过已知方法得到。
反应条件
所有惰性有机溶剂都适合作为用于实施本发明的方法(a)和(f)的稀释剂。所述稀释剂优选包括:脂族、脂环族或芳香族烃,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;卤代烃,例如氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,例如二乙醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;或酰胺,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰胺。
本发明的方法(a)和(f)任选在存在合适的酸受体时实施。所有常规的无机或有机碱都是合适的。所述碱优选包括碱土金属或碱金属的氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨基钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,以及叔胺,例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环十一碳烯(DBU)。
本发明的方法(a)和(f)任选在存在合适的缩合剂时实施。通常用于这类酰胺化反应的所有缩合剂都可使用,例如酰卤形式剂,例如,碳酰氯、三溴化磷、三氯化磷、五氯化磷、磷酰氯或亚硫酰氯;酸酐形式剂,例如氯甲酸乙酯、氯甲酸甲酯、氯甲酸异丙酯、氯甲酸异丁酯或甲磺酰氯;碳化二亚胺,例如N,N’-二环己基碳化二亚胺(DDC)或者其他常用缩合剂,例如五氧化磷、多磷酸、N,N’-羰基二咪唑、2-乙氧基-N-乙氧基羰基-1,2-二氢醌(EEDQ)、三苯膦/四氯化碳,或溴三吡唑烷酮基磷鎓六氟磷酸盐(bromotripyrrolidinophosphonium hexaflurophosphate)。
本发明的方法(a)和(f)任选在存在催化剂时实施。所述催化剂例如4-二甲基氨基吡啶、1-羟基苯并三唑或二甲基甲酰胺。
实施本发明的方法(a)和(f)时,反应温度可各自在宽范围内变化。通常采用的温度在0℃至150℃之间,优选在0℃至80℃之间。
用于实施方法(a)的结构式(I)化合物的制备中,对于每摩结构式(II)的羧酸衍生物,通常使用0.2至5mol,优选0.5至2mol的结构式(III)的苯胺衍生物。
用于实施方法(f)的结构式(IV)和(V)化合物的制备中,对于每摩结构式(II)的羧酸衍生物,通常使用0.2至5mol,优选0.5至2mol的结构式(VIII)或(IX)的链烯基苯胺衍生物。
所有常规惰性有机溶剂、其混合物、或其与水的混合物都适合用作实施本发明的方法(b)的洗脱剂。优选合适的洗脱剂有任选卤代的脂族、脂环族或芳香族烃,例如石油醚、己烷、庚烷、环己烷、二氯甲烷、氯仿;醇,例如甲醇、乙醇、丙醇;腈,例如乙腈;酯,例如乙酸甲酯或乙酸乙酯。更优选使用脂族烃,例如己烷或庚烷,以及醇,例如甲醇或丙醇,尤其优选正庚醇以及异丙醇或它们的混合物。
实施本发明的方法(b)时,反应温度可各自在宽范围内变化。通常采用的温度在10℃至60℃之间,优选在10℃至40℃之间,更优选室温。
实施本发明的方法(b)时,通常使用约1%的外消旋化合物(I-rac)溶液用于色谱分离。然而,还可使用其他浓度。以常规方法进行后处理。通常的步骤如下,高度浓缩洗脱剂,滤掉固体,并以正庚烷洗涤后干燥。残留物通过色谱法与仍可能存在的杂质分开。正庚烷或环己烷和乙酸乙酯的混合物用作洗脱剂,其组成必须根据各待纯化的化合物调整。
所有惰性有机溶剂都适于作为实施本发明的方法(d)的第一步以及本发明的方法(g)的稀释剂。所述惰性有机溶剂优选包括腈,例如乙腈、丙腈、正或异丁腈或苄腈;或者酰胺,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰胺。
本发明的方法(d)的第一步已及本发明的方法(g)任选在存在合适的酸受体时进行。所有常规的无机或有机碱都是合适的。所述碱优选包括碱土金属或碱金属的氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨基钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,以及叔胺,例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环十一碳烯(DBU)。
本发明的方法(d)的第一步已及本发明的方法(g)在存在一种或多种催化剂时实施。特别合适的催化剂为钯盐或其络合物。优选包括氯化钯、乙酸钯、二氯化四(三苯膦)钯或二氯化双(三苯膦)钯。当分别向反应添加钯盐以及络合配位体时,钯络合物也可在反应混合物中生成。合适的配位体优选为有机磷化合物。例如三苯膦、三-邻-甲苯基膦、2,2’-双(二苯膦基)-1,1’-联萘、二环己膦联苯、1,4-双-(二苯膦基)丁烷、双二苯膦基二茂铁、二(叔丁基膦基)联苯、二(环己膦基)联苯、2-二环己膦基-2’-N,N-二甲基氨基联苯、三环己膦、三-叔丁基膦。也可略掉配位体。
本发明的方法(d)的第一步已及本发明的方法(g)在任选进一步存在另一种金属盐时实施,所述金属盐例如铜盐,如碘化铜(I)。
实施本发明的方法(d)的第一步已及本发明的方法(g)时,反应温度可在宽范围内变化。通常采用的温度在20℃至180℃之间,优选在50℃至150℃之间。
用于实施方法(d)的第一步的结构式(VIII)链烯基苯胺的制备中,对于每摩结构式(VI)的苯胺,通常使用1至5mol,优选1至3mol的结构式(VII)的烯烃。
用于实施方法(g)的结构式(IV)和(V)化合物的制备中,对于每摩结构式(X)的甲酰胺,通常使用1至5mol,优选1至3mol的结构式(VII)或(XI)的烯烃。
所有惰性有机溶剂都适于作为实施本发明的方法(c)以及本发明的方法(d)的第二步(氢化)的稀释剂。所述惰性有机溶剂优选包括脂族或脂环族烃,例如石油醚、己烷、庚烷、环己烷、甲基环己烷或萘烷;醚,例如二甲醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷或1,2-二乙氧基乙烷;醇,例如甲醇、乙醇、正或异丙醇、正、异、仲或叔丁醇、乙二醇、1,2-丙二醇、乙氧基乙醇、甲氧基乙醇、二甘醇一甲基醚、二甘醇一乙基醚,以及其与水或纯水的混合物。
本发明的方法(d)的第二步(氢化)在存在催化剂时实施。所有通常用于氢化的催化剂都是合适的。所述催化剂例如任选在载体上的阮内镍、钯、钌或铂,所述载体例如活性炭。
实施本发明的方法(c)以及方法(d)中的手性氢化在存在旋光配位体时实施。所述旋光配位体的实例有(R,R)-Me-DuPhos/RuCl2 的结合或(S,S)-Me-DuPhos/RuCl2 的结合(根据需要的对映体)。
本发明的方法(d)的第二步的氢化还可在存在三乙基硅烷的条件下——而不是在氢气并结合催化剂时——实施。
实施本发明的方法(c)以及本发明的方法(d)的第二步时,反应温度可在宽范围内变化。通常采用的温度在0℃至150℃之间,优选在20℃至100℃之间。
本发明的方法(d)以及本发明的方法(d)的第二步在氢气压0.5至200bar之间,优选2至50bar之间,更优选3至10bar之间实施。
在各种情况下,所有常规惰性有机溶剂、其混合物或者可能的其与水的混合物都适于作为实施本发明的方法(d)的第三步以及本发明的方法(e)的洗脱剂。优选合适的所述惰性有机溶剂有任选被取代的脂族、脂环族或芳族烃,例如石油醚、己烷、庚烷、环己烷、二氯甲烷、氯仿;醇,例如甲醇、乙醇、丙醇;腈,例如乙腈;酯,例如乙酸甲酯或乙酸乙酯。更优选脂族烃,例如己烷或庚烷,以及醇,例如甲醇或丙醇,尤其优选正庚烷以及异丙醇或其混合物。
实施本发明的方法(d)的第三步以及本发明的方法(e)时,反应温度各自可在宽范围内变化。通常使用的温度在10℃至60℃之间,优选在10℃至40℃之间,特别优选为室温。
实施本发明的方法(d)的第三步以及方法(e)时,通常分别使用约1%的外消旋化合物(III-a-rac)和(III-b-rac)溶液用于色谱分离。然而,也可使用其他浓度。以常规方法进行后处理。通常高度浓缩洗脱剂,滤掉固体,并在以正庚烷洗涤后干燥。残留物用色谱法与仍然可能存在的杂质分开。正庚烷或环己烷和乙酸乙酯的混合物用作洗脱剂,其组成必须根据各待纯化的化合物调整。
除非另有说明,本发明的所有方法都在常压下实施。然而,还可在升高的或降低的压力下实施,通常为0.1至10bar。
本发明的物质具有高杀微生物活性,可在作物保护和材料保护中用于防治不想要的微生物,例如真菌和细菌。
杀真菌剂可用于在农作物保护中防治根肿菌(Plasmodiophoromycete)、卵菌(Oomycete)、壶菌(Chytridiomycete)、接合菌(Zygomycete)、子囊菌(Ascomycete)、担子菌(Basidiomycete)及半知菌(Deuteromycete)。
杀细菌剂可用于在农作物保护中防治假单孢菌(Pseudomonadaceae)、根瘤菌(Rhizobiaceae)、Enterobateriaceae、Corynebacteriaceae以及链霉菌(Streptomycetaceae)。
以示例而非限制的方式列举一些归入以上所列菌类的引起真菌及细菌疾病的病原体:
黄单胞(Xanthomonas)菌种,例如野油菜黄单胞菌水稻致病变种(Xanthomonas campestris pv.oryzae);
假单胞(Pseudomonas)菌种,例如丁香假单胞菌黄瓜致病变种(Pseudomonas syringae pv.lachrymans);
欧文氏(Erwinia)菌种,例如解淀粉欧文氏菌(Erwinia amylovora);
腐霉(Pythium)菌种,例如终极腐霉(Pythium ultimum);
疫霉(Phytophthora)菌种,例如致病疫霉(Phytophthorainfestans);
假霜霉(Pseudoperonospora)菌种,例如草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);
轴霜霉(Plasmopara)菌种,例如葡萄生轴霜霉(Plasmoparaviticola);
盘霜霉(Bremia)菌种,例如莴苣盘霜霉(Bremia lactucae);
霜霉(Peronospora)菌种,例如豌豆霜霉(Peronospora pisi)或十字花科霜霉(P.brassicae);
白粉菌(Erysiphe)菌种,例如禾谷白粉菌(Erysiphe graminis);
单囊壳属(Sphaerotheca)菌种,例如凤仙花单囊壳(Sphaerothecafuliginea);
叉丝单囊壳属(Podosphaera)菌种,例如白叉丝单囊壳(Podosphaeraleucotricha);
黑星菌属(Venturia)菌种,例如苹果黑星病菌(Venturiainaequalis);
核腔菌属(Pyrenophora)菌种,例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(P.graminea)(分生孢子形式:Drechslera,syn:Helminthosporium);
旋孢腔菌属(Cochliobolus)菌种,例如禾旋孢腔菌(Cochliobolussativus)(分生孢子形式:Drechslera,syn:Helminthosporium);
单胞锈菌属(Uromyces)菌种,例如疣顶单胞锈菌(Uromycesappendiculatus);
柄锈菌(Puccinia)菌种,例如隐匿柄锈菌(Puccinia recondita);
核盘菌属(Sclerotinia)菌种,例如核盘菌(Sclerotiniasclerotiorum);
腥黑粉菌属(Tilletia)菌种,例如小麦网腥黑粉菌(Tilletiacaries);
黑粉菌(Ustilago)菌种,例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);
薄膜革菌属(Pellicularia)菌种,例如佐佐木薄膜革菌(Pellicularia sasakii);
梨孢(Pyricularia)菌种,例如稻梨孢(Pyricularia oryzae);
镰孢属(Fusarium)菌种,例如黄色镰孢(Fusarium culmorum);
葡萄孢属(Botrytis)菌种,例如灰葡萄孢(Botrytis cinerea);
壳针孢属(Septoria)菌种,例如颖枯壳针孢(Septoria nodorum);
小球腔菌属(Leptosphaeria)菌种,例如Leptosphaeria nodorum;
尾孢属(Cercospora)菌种,例如变灰尾孢(Cercospora canescens);
链格孢属(Alternaria)菌种,例如芸薹链格孢(Alternariabrassicae);
假小尾孢属(Pseudocercosporella)菌种,例如小麦基腐病菌(Pseudocercosporella herpotrichoides)。
丝核菌属(Rhizoctonia),例如立枯丝核菌(Rhizoctonia solani)。
本发明的活性化合物还在植物中显示出强的强化作用(fortifyingaction)。因此,它们适于活化植物内部的防御性能以抵抗不想要的微生物的侵袭。
在本发明中,植物强化(抗性诱发)化合物应被理解为这样的物质,它们能够激发植物的防御系统,从而,当经处理的植物之后被不想要的微生物接种时,所述植物表现出对上述微生物显著的抵抗性。
在本发明中,不想要的微生物应被理解为植物致病真菌、细菌以及病毒。因此,本发明的化合物可用于在处理后的某段时间内保护植物抵抗所述病原体的侵袭。所获得的保护作用的时间通常为自以活性化合物处理植物起1至10天,优选1至7天。
本发明的活性化合物在防治植物病害所需浓度具有的良好的植物耐受性,这就使得可对植物的地上部分、离体繁殖株、种子以及土壤进行处理。
本发明的活性化合物能够以特别好的效果防治谷类疾病,例如防治柄锈菌属种(Puccinia),以及葡萄栽培、水果和蔬菜栽培中出现的疾病,例如防治葡萄孢属种(Botrytis)、黑星菌属种(Venturia)和链格孢属种(Alternaria)。
本发明的活性化合物还适于提高农作物的产量。此外,它们还表现出低毒性以及良好的植物耐受性。
如果合适,本发明的活性化合物还可以在某些浓度和施用率下用作除草剂,以调节植物生长,并防治动物害虫。如果合适,它们还可用作合成其它活性化合物的中间体或前体。
所有的植物及植物部位(part)均可依据本发明来处理。本发明中植物的含义应理解为所有的植物及植物种群,例如需要的及不需要的野生植物或农作物植物(包括自然存在的农作物植物)。农作物植物可以是通过常规植物育种及优选法,或通过生物技术及基因工程,或通过所述方法的结合而获得的植物,包括转基因植物,也包括受或不受植物种苗权保护的植物品种。植物部位的含义应理解为植物所有的地上和地下部位以及植物器官,例如芽、叶、花及根,可提及的实例为叶、针叶(needle)、茎、干、花、子实体、果实、种子、根、块茎及根茎。植物部位还包括采收物和无性及有性繁殖物,例如插条、块茎、根茎、侧枝及种子。
本发明的使用活性化合物对植物及植物部位进行的处理,依据常规处理方法直接进行或使活性化合物作用于其环境、生境或贮存区域,所述常规处理方法包括例如浸泡、喷雾、蒸发、弥雾(misting)、撒播、涂抹(coating),在繁殖物、特别是种子的情况下,也可涂布一层或多层。
在材料的保护中,本发明的化合物可用于保护工业材料免受不想要的微生物的侵染及破坏。
本发明中的工业材料的含义应理解为已制成准备用于工业的非活体材料。例如,拟由本发明的活性化合物保护以免受微生物改变或破坏的工业材料可为粘合剂、胶料、纸张及板材、织物、皮革、木材、漆及塑料制品、冷却润滑剂(cooling lubricant)及其它可受微生物侵染或破坏的材料。可被微生物繁殖损害的生产工厂部件,例如冷却水回路,亦在可保护材料的范围内。在本发明范围内可提及的工业材料优选为粘合剂、胶料、纸张及板材、皮革、木材、漆、冷却润滑剂及传热液体,尤其优选木材。
可提及的可使工业材料发生劣化或改变的微生物为,例如细菌、真菌、酵母菌、藻类及粘液生物(slime organism)。本发明的活性化合物优选作用于真菌,特别是霉菌、木材退色真菌及木腐真菌(担子菌),以及粘液生物及藻类。
可列举以下各属的微生物作为实例:
链格孢属(Alternaria),例如链格孢(Alternaria tenuis),
曲霉属(Aspergillus),例如黑曲霉(Aspergillus nigar),
毛壳菌(Chaetomium),例如球毛壳菌(Chaetomium globosum),
粉革菌属(Coniophora),例如Coniophora puetana,
香菇属(Lentinus),例如虎皮香菇菌(Lentinus tigrinus),
青霉属(Penicillium),例如灰绿青霉(Penicillium glaucum),
多孔菌(Polyporus),例如杂色多孔菌(Polyporus versicolor),
短梗霉属(Aureobasidium),例如出芽短梗霉(Aureobasidiumpullulans),
核茎点属(Sclerophoma),例如Sclerophoma pityophila,
木霉属(Trichoderma),例如绿色木霉(Trichoderma viride),
埃希氏菌属(Escherichia),例如大肠埃希氏菌(Escherichia coli),
假单胞菌属(Pseudomonas),例如铜绿假单胞菌(Pseudomonasaeruginosa),
葡萄球菌属(Staphylococcus),例如金黄色葡萄球菌(Staphylococcusa ureus)。
依据其具体的物理和/或化学特性,本发明的活性化合物可转化为常规制剂,例如溶液、乳剂、悬浮剂、粉剂、泡沫、膏剂、颗粒剂、气雾剂、聚合物与种子包衣(coating)组合物中的微胶囊剂以及ULV冷却与加温弥雾(fogging)制剂。
所述制剂以已知方式制备,例如将活性化合物与填充剂(extender)混合,即与液体溶剂、加压液化气和/或固体载体混合,同时可任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。如果使用的填充剂为水,还可使用例如有机溶剂作为辅助溶剂。适合的液体溶剂主要有:芳香族化合物,例如二甲苯、甲苯或烷基萘;氯化芳香族化合物或氯化脂肪烃,例如氯苯、氯乙烯或二氯甲烷;脂肪烃,例如环己烷或石蜡,如石油馏分;醇,例如丁醇或乙二醇及其醚及酯;酮,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺或二甲基亚砜;或水。液化气填充剂或载体的含义应理解为在标准温度及大气压下为气态的液体,例如气溶胶喷雾剂,例如卤代烃,或丁烷、丙烷、氮气及二氧化碳。适合的固体载体为:例如粉碎的天然矿物,例如高岭土、粘土、滑石粉、白垩、石英、凹凸棒石、蒙脱石或硅藻土;以及粉碎的合成矿物,例如细分散二氧化硅、氧化铝及硅酸盐。适用于颗粒剂的固体载体为:例如粉碎并分级的天然岩石,例如方解石、浮石、大理石、海泡石及白云石;或合成的无机及有机粉颗粒,以及有机物颗粒,例如锯木屑、椰壳、玉米穗轴及烟草茎。适合的乳化剂和/或发泡剂为:例如非离子及阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,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,或蛋白质水解产物。适合的分散剂为:例如木素亚硫酸盐废液及甲基纤维素。
制剂中可使用增粘剂,例如羧甲基纤维素,以及粉末、颗粒或胶乳形式的天然及合成聚合物,例如阿拉伯树胶、聚乙烯醇及聚乙酸乙烯酯,或天然磷脂,例如脑磷脂及卵磷脂,以及合成磷脂。其它添加剂可为矿物油及植物油。
可使用着色剂,例如无机颜料,例如氧化铁、氧化钛及普鲁士蓝,以及有机染料,例如茜素染料、偶氮染料及金属酞菁染料,以及微量营养物,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐及锌盐。
制剂一般包括0.1至95重量百分比的活性化合物,优选0.5至90重量百分比。
本发明的活性化合物可以其本身或其制剂的形式使用,还可以与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀昆虫剂混合使用,以拓宽例如其作用谱或防止抗性的产生。在很多情况下,获得了协同效应,即混合物的活性大于单独组分的活性。
合适的混合组分有例如以下化合物:
杀真菌剂:
2-苯基苯酚、8-羟基喹啉硫酸盐、acibenzolar-S-methyl、aldimorph、amidoflumet、氨丙膦酸(ampropylfos)、氨丙膦酸钾、andoprim、敌菌灵(anilazine)、戊环唑(azaconazole)、腈嘧菌酯(azoxystrobin)、苯霜灵(benalaxyl)、麦锈灵(benodanil)、苯菌灵(benomyl)、异丙基-benthiavalicarb、苄烯酸(benzamacril)、异丁基苄烯酸、双丙氨膦(bilanafos)、乐杀螨(binapacryl)、联苯、双苯三唑醇(bitertanol)、灭瘟素(blasticidin-S)、糠菌唑(bromuconazole)、磺嘧菌灵(bupirimate)、粉并定(buthiobate)、丁胺、多硫化钙、卡巴西霉素(capsimycin)、敌菌丹(captafol)、克菌丹(captan)、多菌灵(carbendazim)、萎锈灵(carboxin)、氯环丙酰胺(carpropamid)、香芹酮(carvone)、灭螨猛(chinomethionat)、灭瘟唑(chlobenthiazone)、苯咪唑菌(chlorfenazole)、地茂散(chloroneb)、百菌清(chlorothalonil)、乙菌利(chlozolinate)、clozylacon、氰霜唑(cyazofamid)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、环唑醇(cyproconazole)、嘧菌环胺(cyprodinil)、酯菌胺(cyprofuram)、Dagger G、双乙氧咪唑威(debacarb)、抑菌灵(dichlofluanid)、二氯萘醌(dichlone)、双氯酚(dichlorophen)、diclocymet、哒菌清(diclomezine)、氯硝胺(dicloran)、乙霉威(diethofencarb)、噁醚唑(difenoconazole)、氟嘧菌胺(diflumetorim)、甲菌定(dimethirimol)、烯酰吗啉(dimethomorph)、dimoxystrobin、烯唑醇(diniconazole)、烯唑醇-M(diniconazole-M)、敌螨普(dinocap)、二苯胺(diphenylamine)、双吡硫翁(dipyrithione)、灭菌磷(ditalimfos)、二氰蒽醌(dithianon)、dodine、敌菌酮(drazoxolon)、克瘟散(edifenphos)、氧唑菌(epoxiconazole)、韩乐宁(ethaboxam)、乙菌定(ethirimol)、氯唑灵(etridiazole)、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、菌拿灵(fenapanil)、异嘧菌醇(fenarimol)、腈苯唑(fenbuconazole)、甲呋酌苯胺(fenfuram)、环酰菌胺(fenhexamid)、种衣酯(fenitropan)、稻瘟酰胺(fenoxanil)、拌种咯(fenpiclonil)、苯锈啶(fenpropidin)、丁苯吗啉(fenpropimorph)、福美铁(ferbam)、氟啶胺(fluazinam)、flubenzimine、氟噁菌(fludioxonil)、氟联苯菌(flumetover)、氟吗啉(flumorph)、氟氯菌核利(fluoromide)、氟嘧菌酯(fluoxastrobin)、喹唑菌酮(fluquinconazole)、呋嘧醇(flurprimidol)、氟硅唑(flusilazole)、磺菌胺(flusulfamide)、氟酰胺(flutolanil)、粉唑醇(flutriafol)、灭菌丹(folpet)、藻菌磷(fosetyl-A1)、藻菌磷钠(fosetyl-sodium)、麦穗宁(fuberidazole)、呋氨丙灵(fufalaxyl)、呋吡唑灵(furametpyr)、灭菌胺(furcarbanil)、拌种胺(furmecyclox)、双胍盐(guazatine)、六氯苯(hexachlorobenzene)、己唑醇(hexaconazole)、土菌消(hymexazole)、烯菌灵(imazalil)、酰胺唑(imibenconazole)、双胍辛胺乙酸盐(iminoctadine triacetate)、克热净(烷苯磺酸盐)(iminoctadine tris(albesil))、iodocarb、环戊唑醇(ipconazole)、异稻瘟净(iprobenfos)、异丙定(iprodione)、缬霉威(iprovalicarb)、人间霉素(irumamycin)、稻瘟灵(isoprothiolane)、氯苯咪菌酮(isovaledione)、春雷霉素(kasugamycin)、亚胺菌(kresoxim-methyl)、代森锰锌(mancozeb)、代森锰(maneb)、meferimzone、嘧菌胺(mepanipyrim)、丙氧灭锈胺(mepronil)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)、环戊唑菌(metconazole)、磺菌威(methasulfocarb)、甲呋菌胺(methfuroxam)、代森联(metiram)、叉氨苯酰胺(metominostrobin)、噻菌胺(metsulfovax)、米多霉素(mildiomycin)、腈菌唑(myclobutanil)、甲菌利(myclozolin)、多马霉素(natamycin)、nicobifen、异丙消(nitrothal-isopropyl)、noviflumuron、氟苯嘧啶醇(nuarimol)、甲呋酰胺(ofurace)、orysastrobin、噁霜灵(oxadixyl)、喹菌酮(oxolinic acid)、oxpoconazole、氧化萎锈灵(oxycarboxin)、oxyfenthiin、多效唑(paclobutrazol)、稻瘟酯(pefurazoate)、戊菌唑(penconazole)、戊菌隆(pencycuron)、双氯苯磷(phosdiphen)、四氯苯酞(phthalide)、啶氧菌酯(picoxystrobin)、粉病灵(piperalin)、多抗霉素(polyoxins)、polyoxorim、噻菌灵(probenazole)、丙氯灵(prochloraz)、杀菌利(procymidone)、百维灵(propamocarb)、propanosine-sodium、丙环唑(propiconazole)、丙森锌(propineb)、proquinazid、prothioconazole、吡唑醚菌酯(pyraclostrobin)、定菌磷(pyrazophos)、啶斑肟(pyrifenox)、二甲嘧菌胺(pyrimethanil)、咯喹酮(pyroquilon)、氯吡呋醚(pyroxyfur)、pyrrolenitrine、唑喹菌酮(quinconazole)、喹氧灵(quinoxyfen)、五氯硝基苯(quintozene)、硅氟唑(simeconazole)、螺噁茂胺(spiroxamine)、硫、戊唑醇(tebuconazole)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、tetcyclacis、氟醚唑(tetraconazole)、涕必灵(thiabendazole)、噻菌腈(thicyofen)、溴氟唑菌(thifluzamide)、甲基托布津(thiophanate-methyl)、福美双(thiram)、tioxymid、甲基立枯磷(tolclofos-methyl)、对甲抑菌灵(tolylfluanid)、三唑酮(triadimefon)、唑菌醇(triadimenol)、丁三唑(triazbutil)、唑菌嗪(triazoxide)、tricyclamide、三环唑(tricyclazole)、克啉菌(tridemorph)、肟菌酯(trifloxystrobin)、氟菌唑(triflumizole)、嗪氨灵(triforine)、戊叉唑菌(triticonazole)、烯效唑(uniconazole)、有效霉素A(validamycin A)、烯菌酮(vinclozolin)、代森锌(zineb)、福美锌(ziram)、苯酰菌胺(zoxamide)、(2S)-N-[2-[4-[[3-(4-氯苯基)-2-丙炔基]氧]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲基磺酰基)氨基]丁酰胺、1-(1-萘基)-1H-吡咯-2,5-二酮、2,3,5,6-四氯-4-(甲基磺酰基)吡啶、2-氨基-4-甲基-N-苯基-5-噻唑甲酰胺、2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺、3,4,5-三氯-2,6-吡啶二腈、actinovate、顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、1-(2,3-二氢-2,2-二甲基-1H-茚-l-基)-1H-咪唑-5-羧酸甲酯、碳酸氢钾、N-(6-甲氧基-3-吡啶基)环丙烷甲酰胺、N-丁基-8-(1,1-二甲基乙基)-1-氧杂螺[4.5]癸烷-3-胺、四硫代碳酸钠;以及铜盐及其制剂,例如波尔多液、氢氧化铜、环烷酸铜、氯氧化铜(copperoxychloride)、硫酸铜、硫杂灵(cufraneb)、氧化铜、代森锰铜(mancopper)、喹啉铜(oxine-copper)。
杀细菌剂:
溴硝丙二醇(bronopol)、双氯酚、三氯甲基吡啶(nitrapyrin)、二甲基二硫代氨基甲酸镍(nickel dimethyldithiocarbamate)、春雷霉素、异噻菌酮(octhilinone)、羧酸呋喃(furancarboxylic acid)、土霉素(oxytetracyclin)、噻菌灵、链霉素(streptomycin)、叶枯酞、硫酸铜和其他铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
1.乙酰胆碱酯酶(AChE)抑制剂
1.1氨基甲酸酯类(例如,棉铃威(alanycarb)、涕灭威(aldicarb)、砜灭威(aldoxycarb)、除害威(allyxycarb)、灭害威(aminocarb)、甲基吡恶磷(azamethiphos)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、必克虱(bufencarb)、畜虫威(butacarb)、丁叉威(butocarboxim)、氧丁叉威(butoxycarboxim)、西维因(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、除线威(choethocarb)、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、敌蝇威(dimetilan)、苯虫威(ethiofencarb)、丁苯威(fenobucarb)、苯硫威(fenothiocarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、威百亩(metam-sodium)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、猛杀威(promecarb)、残杀威(propoxur)、硫双灭多威(thiodicarb)、特氨叉威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、XMC、灭杀威(xylylcarb))
1.2有机磷酸酯类(例如,高灭磷(acephate)、唑啶磷(azamethiphos)、谷硫磷(azinphos-methyl)、乙基谷硫磷(azinphos-ethyl)、乙基溴硫磷(bromophos-ethyl)、溴苯烯磷(bromfenvinfod(-methyl))、特嘧硫磷(butathiofos)、硫线磷(cadusafos)、三硫磷(carbophenothion)、壤虫氯磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲磷(chlormephos)、甲基毒死蜱(chlorpyrifos-methyl)、乙基毒死蜱、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、毒虫畏(chlorfenvinphos)、甲基一○五九(demeton-S-methyl)、磺吸磷(demeton-S-methylsulfone)、氯亚磷(dialifos)、二嗪农(diazinon)、除线磷(dichlofenthion)、敌敌畏(dichlorvos)/DDVP、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、蔬果磷(dioxabenzofos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、灭克磷(ethoprophos)、氧嘧啶磷(etrimfos)、氨磺磷(famphur)、克线磷(fenamiphos)、杀螟松(fenitrothion)、丰索磷(fensulfothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazofos)、地虫磷(fonofos)、安果(formothion)、丁苯硫磷(fosmethilan)、噻唑酮磷(fosthiazate)、庚虫磷(heptenophos)、碘硫磷(iodofenphos)、异稻瘟净(iprobenfos)、氟唑磷(isazofos)、丙胺磷(isofenphos)、O-水杨酸异丙酯、异噁唑啉(isoxathion)、马拉松(malathion)、灭蚜磷(mecarbam)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧化乐果(omethoate)、砜吸磷(oxydemeton-methyl)、甲基一六○五(parathion methyl)、一六○五(-乙基)、稻丰散(phenthoate)、三九一一(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、乙丙磷威(phosphocarb)、腈肟磷(phoxim)、虫螨磷(pirimiphos methyl)、乙基虫螨磷(pirimiphos ethyl)、丙溴磷(profenofos)、丙虫磷(propaphos)、烯虫磷(propetamphos)、丙硫磷(prothiofos)、发果(prothoate)、吡唑硫磷(pyraclofos)、打杀磷(pyridaphenthion)、pyridathion、喹噁磷(quinalphos)、硫线磷(sebufos)、硫特普(sulfotep)、乙丙硫磷(sulprofos)、嘧丙磷(tebupirimphos)、双硫磷(temephos)、特丁磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭多(vamidothion))
2.钠通道抑扬调节剂/电压依赖性钠通道阻断剂
2.1合成除虫菊酯类(例如,氟酯菊酯(acrinathrin)、丙烯除虫菊(d-顺-反,d-反)(allethrin(d-cis-trans,d-trans))、β-氟氯氰菊酯(beta-cyfluthrin)、氟氯菊酯(bifenthrin)、反丙烯除虫菊(bioallethrin)、反丙烯除虫菊-S-环戊基异构体、bioethanomethrin、生物氯菊酯(biopermethrin)、右旋反灭虫菊酯(bioresmethrin)、chlovaporthrin、顺-氯氰菊酯、顺-灭虫菊(cis-resmethrin)、顺-氯菊酯(cis-permethrin)、功夫菊酯(clocythrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、氯氟氰菊酯(cyhalothrin)、氯氰菊酯(α-、β-、θ-、ζ-)(cypermethrin(alpha-,beta-,theta-,zeta-))、苯醚氯菊酯(cyphenothrin)、DDT、溴氰菊酯(deltamethrin)、烯炔菊酯(1R异构体)(empenthrin(1R isomer))、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、五氟苯菊酯(fenfluthrin)、甲氰菊酯(fenpropathrin)、吡氯氰菊酯(fenpyrithrin)、灭杀菊酯(fenvalerate)、溴氟菊酯(flubrocythrinate)、氟氰戊菊酯(flucythrinate)、氟丙苄醚(flufenprox)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(fluvalinate)、fubfenprox、γ-氯氟氰菊酯(gamma-cyhalothrin)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、λ-氯氟氰菊酯(lambda-cyhalothrin)、甲氧苄氟菊酯(metofluthrin)、氯菊酯(顺-、反-)、苯醚菊酯(1R反式异构体)(phenothrin(1R trans isomer)、炔酮菊酯(prallethrin)、丙氟菊酯(profluthrin)、protrifenbute、反灭虫菊(pyresmethrin)、灭虫菊、RU-15525、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、环戊烯丙菊酯(terallethrin)、胺菊酯(1R反式异构体)(tetramethrin(1Rtrans-isomer))、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、ZXI 8901、除虫菊素(pyrethrin)(除虫菊(pyrethrum)))
2.2噁二嗪类(oxadiazine)(例如噁二唑虫(indoxacarb))
3.乙酰胆碱受体激动剂/拮抗剂
3.1氯烟碱基类(chloronicotinyls)/新类烟碱(neonicotinoids)(例如,吡虫清(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉、硝胺烯啶(nitenpyram)、硝虫噻嗪(nithiazine)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam))
3.2烟碱(nicotine)、杀虫磺(bensultap)、巴丹(cartap)
4.乙酰胆碱受体抑扬调节剂
4.1 spinosyn类(例如艾克敌105(spinosad))
5.GABA受控氯通道拮抗剂
5.1环戊二烯有机氯类(例如,毒杀芬(camphechlor)、氯丹(chlordane)、硫丹(endosulfan)、林丹(gamma-HCH)、HCH、七氯(heptachlor)、林丹(lindane)、甲氧滴滴涕(methoxychlor))
5.2 fiprole类(例如,乙酞虫睛(acetoprole)、乙虫清(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole))
6.氯通道激活剂类
6.1 Mectin类(例如,阿维菌素(abamectin,avermectin)、埃玛菌素(emamectin)、埃玛菌素苯甲酸盐(emamectin-benzoate)、伊维菌素(ivermectin)、弥拜菌素(milbemectin)、米尔倍霉素(milbemycin))
7.保幼激素mimetic类(例如,噁茂醚(diofenolan)、epofenonane、双氧威(fenoxycarb)、蒙五一二(hydroprene)、蒙七七七(kinoprene)、蒙五一五(methoprene)、蚊蝇醚(pyriproxifen)、烯虫硫酯(triprene))
8.蜕皮激素激动剂/干扰剂类(disruptor)
8.1二酰基肼类(例如,环虫酰肼(chromafenozide)、特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide))
9.甲壳质生物合成抑制剂
9.1苯甲酰脲类(例如,双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟啶蜱脲(fluazuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氟幼脲(penfluron)、伏虫磷(teflubenzuron)、杀虫隆(triflumuron))
9.2噻嗪酮(buprofezin)
9.3灭蝇胺(cyromazine)
10.氧化性磷酸化抑制剂,ATP干扰剂类
10.1杀螨硫隆(diafenthiuron)
10.2有机锡类(例如唑环锡(azocyclotin)、三环锡(cyhexatin)、杀螨锡(fenbutatin-oxide))
11.通过打断H-质子梯度而起作用的氧化性磷酸化去偶剂(decoupler)类
11.1吡咯类(例如氟唑虫清(chlorfenapyr))
11.2二硝基酚类(例如乐杀螨(binapacryl)、敌螨通(dinobuton)、敌螨普(dinocap)、DNOC)
12.侧链-I(Side-I)电子转移抑制剂类
12.1 METI类(例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧胺苯醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad))
12.2灭蚁腙(hydramethylnon)
12.3开乐散(dicofol)
13.侧链-II电子转移抑制剂类
13.1鱼藤酮(rotenone)
14.侧链-III电子转移抑制剂类
14.1灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)
15.昆虫肠道膜微生物干扰剂类
苏云金杆菌(Bacillus thuringiensis)菌株
16.脂肪合成抑制剂类
16.1季酮酸类(例如,螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen))
16.2特特拉姆酸类(tetramic acids)(例如,3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1-氮杂螺[4.5]十二-3-烯-4-基碳酸乙酯(alias:碳酸的3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1-氮杂螺[4.5]十二-3-烯-4-基乙基酯,CAS Reg.No.:382608-10-8)以及碳酸的顺-3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1-氮杂螺[4.5]十二-3-烯-4-基乙基酯(CAS Reg.No.:203313-25-1))
17.甲酰胺类(例如氟啶虫酰胺(flonicamid))
18.octopaminergic激动剂类(例如虫螨脒(amitraz))
19.镁激励ATP酶抑制剂类(例如克螨特(propargite))
20.邻苯二酰胺类(例如N2-[1,1-二甲基-2-(甲基磺酰基)乙基]-3-碘-N1-[2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]-1,2-苯二氨甲酰(CAS Reg.No.:272451-65-7)、flubendiamide)
21.沙蚕毒素类似物(例如硫赐安(thiocyclam hydrogenoxalate)、杀虫双(thiosultap-sodium))
22.生物类,激素类或信息素类(例如,艾扎丁(azadirachtin)、杆菌属种、僵菌属种、十二碳二烯醇(codlemone)、绿僵菌属种(Metarrhizium spec.)、拟青霉属种(Paecilomyces spec.)、敌贝特(thuringiensin)、轮枝菌属种(Verticillium spec.))
23.具有未知或未确定作用机理的活性化合物类
23.1熏蒸剂类(例如,磷化铝、一溴甲烷、硫酰氟)
23.2选择性拒食剂类(例如,冰晶石、氟啶虫酰胺(flonicamid)、拒嗪酮(pymetrozine))
23.3螨生长抑制剂类(例如,四螨嗪(clofentezine)、特苯噁唑(etoxazole)、噻螨酮(hexythiazox))
23.4 amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、噻嗪酮(buprofezin)、灭螨锰、杀虫脒(chlordimeform)、乙酯杀螨醇(chlorobenzilate)、氯化苦(chloropicrin)、clothiazoben、cycloprene、地昔尼尔(dicyclanil)、fenoxacrim、氟硝二苯胺(fentrifanil)、噻唑螨(flubenzimine)、flufenerim、氟替阿嗪(flutenzin)、诱虫十六酯(gossyplure)、灭蚁腙(hydramethylnone)、japonilure、恶虫酮(metoxadiazone)、石油、胡椒基丁醚(piperonyl butoxide)、油酸钾、啶虫丙醚(pyridalyl)、氟虫胺(sulfluramid)、三氯杀螨砜(tetradifon)、杀螨好(tetrasul)、苯赛螨(thiarathene)、verbutin,
以及化合物3-甲基苯基丙基氨基甲酸酯(Tsumacide Z)、化合物3-(5-氯-3-吡啶基)-8-(2,2,2-三氟乙基)-8-氮杂二环[3.2.1]辛烷-3-腈(CAS注册号185982-80-3)以及相应的3-内异构体(CAS注册号185984-60-5)(参见WO 96/37494、WO 98/25923),以及含有杀昆虫性能的活性植物提取物、线虫、真菌或病毒的制剂。
与其它已知化合物一例如除草剂一的混合物,或与肥料以及生长调节剂、安全剂和/或化学信息素的混合物也是可以的。
此外,本发明的式(I)化合物还具有非常好的抗真菌活性。这些化合物具有非常宽的抗真菌作用谱,特别是针对皮肤癣菌(dermatophyte)和酵母菌、霉菌和双相真菌(diphasic fungi)(例如针对念珠菌属(Candida)菌种、例如白色念珠菌(Candida albicans)、光滑念珠菌(Candidaglabrata)),以及絮状表面癣菌(Epidermophyton floccosum),曲霉(Aspergillus)菌种、例如黑曲霉(Aspergillus niger)和烟曲霉(Aspergillus fumigatus),毛癣菌属(Trichophyton)菌种,例如须癣毛癣菌(Trichophyton mentagrophytes),小孢霉属(Microsporon)菌种例如犬小孢霉(Microsporon canis)和Microsporon audouinii。所列真菌仅为说明目的,而并非限制可涵盖的真菌谱。
本发明的活性化合物可以其本身、其制剂形式或由其制备的使用形式使用,例如即用的溶液剂、悬浮剂、可湿性粉剂、膏剂、可溶性粉剂、粉末剂和颗粒剂。施用以常规方式进行,例如浇灌、喷雾、雾化、撒播(broadcasting)、喷粉、发泡、抛撒等。还可通过超低容量法(ultra-lowvolume process)施用活性化合物,或者将活性化合物制剂或活性化合物本身注射至土壤内。还可处理植物种子。
本发明的活性化合物用作杀真菌剂时,施用率可依据施用类型在较宽的范围内变化。对于植物部位的处理,活性化合物施用率一般为0.1至10000g/ha,优选10至1000g/ha。对于拌种,活性化合物施用率一般为0.001至50g每公斤种子,优选0.01至10g每公斤种子。对于土壤处理,活性化合物施用率一般为0.1至10000g/ha,优选1至5000g/ha。
如上所述,可依据本发明处理所有的植物及其部位。在一个优选实施方案中,处理了野生植物种和植物栽培种,或由常规生物育种方法—例如杂交或原生质体融合—获得的植物种和植物栽培种,以及所述植物种和栽培种的部位。在另一优选实施方案中,处理了由基因工程、如果合适还可与常规方法相结合而获得的转基因植物和植物栽培种(遗传修饰的生物(genetically modified organism))及其部位。术语“部位”或“植物的部位”或“植物部位”解释如上。
特别优选依据本发明进行处理的植物为各自市售或使用的植物栽培种。植物栽培种的含义理解为由常规育种、诱变或重组DNA技术育种的具有新特性(“特征”)的植物。它们可以是栽培种、品种(variety)、生物型(biotype)和基因型形式。
依据植物种或植物栽培种、其种植地点和生长条件(土壤、气候、植物生长期、营养),本发明的处理也可产生超加和性(superadditive)(“协同”)效应。由此,例如,对于可按本发明使用的物质和组合物,可降低其施用率和/或加宽其作用谱和/或提高其活性,以及改善植物生长、提高高温或低温耐受性、提高干旱或水或土壤含盐量耐受性、提高开花品质、使采收更简易、加速成熟、提高产量、改善采收产品的质量和/或提高其营养价值、改善采收产品的贮存稳定性和/或其加工性能,这些可超过实际预期的效果。
优选由本发明处理的转基因植物或植物栽培种(即通过遗传工程获得)包括在重组修饰中接受了遗传物质的所有植物,所述遗传物质将特别有利的有用特性(“特征”)赋予所述植物。所述特性的实例有改善植物生长、提高高温或低温耐受性、提高干旱或水或土壤含盐量耐受性、提高开花品质、使采收更简易、加速成熟、提高产量、改善采收产品的质量和/或提高其营养价值、改善采收产品的贮存稳定性和/或其加工性能。需特别提及的所述特性的其他实例为改善植物对动物和微生物害虫的抵抗力,例如对昆虫、螨虫、植物致病真菌、细菌和/或病毒的抵抗力,以及提高植物对某些除草活性化合物的耐受性。可列举的转基因植物的实例为重要的作物植物,例如谷物(小麦、稻)、玉米、大豆、马铃薯、棉花、烟草、油菜和果树(苹果、梨、柑橘类水果以及葡萄),特别强调的为玉米、大豆、马铃薯、棉花、烟草和油菜。特别强调的特征为通过在植物体内形成毒素,特别是由苏云金杆菌的遗传物质(例如基因Cry I A(a)、Cry I A(b)、Cry I A(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c Cry2Ab、Cry3Bb和CryI F及其结合)在植物体内形成的毒素,来提高植物对昆虫、蛛形纲动物、线虫和蜗牛(slugs and snails)的抵抗力(以下简称为“Bt植物”)。特别强调的其他特征为通过系统获得性抗性(SAR)、系统素、植物抗毒素、引发物和抗性基因以及相应的表达蛋白质和毒素来提高植物对真菌、细菌和病毒的抵抗力。尤其强调的特性为提高植物对某些除草活性化合物的耐受性,例如咪唑啉酮类、磺酰脲类、草甘磷(glyphosate)或phosphinotricin(例如“PAT”基因)。赋予所需要特征的基因也可各自在转基因植物体内相互结合。可列举的“Bt植物”的实例有市售的商标名称为YIELD GARD(例如玉米、棉花、大豆)、Knock0ut(例如玉米)、StarLink(例如玉米)、Bollgard(棉花)、Nucotn(棉花)和NewLeaf(马铃薯)的玉米品种、棉花品种、大豆品种和马铃薯品种。可列举的具有除草剂耐受性的植物的实例有市售的商标名称为Roundup Ready(具有草甘磷耐受性,例如玉米、棉花、大豆)、Liberty Link(具有phosphinotricin耐受性,例如油菜)、IMI(具有咪唑啉酮耐受性)和STS(具有磺酰脲耐受性,例如玉米)的玉米品种、棉花品种和大豆品种。可列举的具有除草剂抗性的植物(以常规的除草剂耐受性方式育种的植物)还包括名称为Clearfield的市售品种(例如玉米)。当然,以上叙述也适用于具有所述的或待开发的基因特征的植物栽培种,所述植物栽培种将在未来进行开发和/或上市。
特别有利地,所列出的植物可依据本发明用本发明的通式(I)化合物或活性化合物混合物进行处理。上述活性化合物或混合物的优选范围也适用于所述植物的处理。特别强调的为用本发明特别提及的化合物或混合物对植物进行处理。
本发明活性化合物的制备方法和应用由以下实施例阐述。
制备实施例
实施例1
将(+/-)-N-[2-(1,3-二甲基丁基)苯基]-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺(200mg)溶于25ml正庚烷/异丙醇9∶1(v/v=体积/体积)。然后,溶液在硅胶相Chiralcel OD[制造商:Daicel(日本);柱尺寸:500mm×40mm(I.D.);粒径:20μm;流速:40ml/min]上通过高效色谱法(HPLC)以正庚烷/异丙醇9∶1(v/v)的洗脱剂进行色谱分离。为了分离全部量,每30分钟将5ml份量(各对应于40mg的外消旋物)加入到柱。以波长210nm的UV探测器进行化合物探测。分析检测对映体纯度后,合并分别洗脱分离得到的物质,并在真空中尽可能地浓缩,滤掉残留物,并且以正庚烷洗涤后干燥。由此分离得到的粗产品在硅胶上纯化(洗脱剂:正庚烷/乙酸乙酯1∶9→1∶4,各自为v/v)。
得到87mg的N-{2-[(1S)-1,3-二甲基丁基]苯基}-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺(熔点52-54℃,旋光度(rotation)[α]D=+6.7,c=0.87;甲醇,20℃,ee值=99%)。
在以下条件下通过分析HPLC确定结构式(I)甲酰胺的对映体纯度:
分离相:Chiralcel OD(Daicel Japan);5μm
柱:250mm×4.6mm(I.D.)
洗脱剂:正庚烷/2-丙醇10∶1
流速:0.5ml/min
UV探测:210nm
以类似于实施例1的方法,并依照总体步骤说明的具体内容,得到下表列出的结构式(I)的化合物。
表1
上表及制备实施例中给出的logP值根据EEC手册79/831附件V.A8(EEC-Directive 79/831 Annex V.A8)通过HPLC(高效液相色谱法)反向柱(C18)上确定。温度:43℃。
确定是在酸性范围内在pH2.3以0.1%的含水磷酸和乙腈为流动相进行;线性梯度从10%的乙腈至90%的乙腈。
采用logP值已知的无支链的烷-2-酮(带有3至16个碳原子)进行校正(用保留时间通过两种连续烷酮之间的线性内插法来确定logP值)。
λ最大值(lambda max value)在采用200nm至400nm的UV光谱的色谱信号最大值中确定。
应用实施例
实施例A
叉丝单囊壳属测试(苹果)/保护
溶剂: 24.5重量份的丙酮
24.5重量份的二甲基乙酰胺
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物的制剂,将1重量份的活性化合物与上述用量的溶剂及乳化剂混合,并将浓液以水稀释至所需浓度。
为了测试保护活性,以所述施用率将活性化合物制剂喷洒至幼小植物上。喷洒层干燥后,将苹果斑点病病原体白叉丝单囊壳(Podosphaeraleucotricha)的含水孢子悬液接种于该植物上。然后将该植物置于温度为约23℃、大气相对湿度约70%的温室中。
接种后10天进行评估。0%表示相当于于对照样的药效,100%表示未观察到侵染。
表A
叉丝单囊壳属测试(苹果)/保护
实施例B
单囊壳属(Sphaerotheca)测试(黄瓜)/保护
溶剂: 24.5重量份的丙酮
24.5重量份的二甲基乙酰胺
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物的制剂,将1重量份的活性化合物与上述用量的溶剂及乳化剂混合,并将浓液以水稀释至所需浓度。
为了测试保护活性,以所述施用率将活性化合物制剂喷洒至幼小黄瓜植株上。喷洒层干燥后,以凤仙花单囊壳(Sphaerotheca fuliginea)的含水孢子悬液接种于该植物上。然后将该植物置于温度约23℃、大气相对湿度约70%的温室中。
接种后7天进行评估。0%表示相当于对照样的药效,100%表示未观察到侵染。
表B
单囊壳属测试(黄瓜)/保护
表B
单囊壳属测试(黄瓜)/保护
表B
单囊壳属测试(黄瓜)/保护
实施例C
黑星菌属测试(苹果)/保护
溶剂: 24.5重量份的丙酮
24.5重量份的二甲基乙酰胺
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物的制剂,将1重量份的活性化合物与上述用量的溶剂及乳化剂混合,并将浓液以水稀释至所需浓度。
为了测试保护活性,以所述施用率将活性化合物制剂喷洒至幼小植物上。喷洒层干燥后,将苹果霉菌病原体苹果黑星病菌(Venturiainaequalis)的含水分生孢子悬液接种于该植物上,然后在约20℃、大气相对湿度约100%的培养室继续放置一天。
然后将该植物放置到约21℃、大气相对湿度约90%的温室中。
接种后10天进行评估。0%表示相当于对照样的药效,100%表示未观察到侵染。
表C
黑星菌属测试(苹果)/保护
表C
黑星菌属测试(苹果)/保护
表C
黑星菌属测试(苹果)/保护
实施例D
葡萄孢属(Botrytis)测试(豆)/保护
溶剂: 24.5重量份的丙酮
24.5重量份的二甲基乙酰胺
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物的制剂,将1重量份的活性化合物与上述用量的溶剂及乳化剂混合,并将浓液以水稀释至所需浓度。
为了测试保护活性,以所述施用率将活性化合物制剂喷洒至幼小植物上。喷洒层干燥后,在每片叶子上放置移植有灰葡萄孢(Botrytiscinerea)的两小片琼脂。将接种后的植物置于约20℃、大气相对湿度100%的暗室中。
接种后2天,评估叶子上侵染区域的尺寸。0%表示相当于对照样的药效,100%表示未观察到侵染。
表D
葡萄孢属(Botrytis)测试(豆)/保护
表D
葡萄孢属(Botrytis)测试(豆)/保护
表D
葡萄孢属(Botrytis)测试(豆)/保护
实施例E
链格孢属(蕃茄)/保护
溶剂: 24.5重量份的丙酮
24.5重量份的二甲基乙酰胺
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物的制剂,将1重量份的活性化合物与上述用量的溶剂及乳化剂混合,并将浓液以水稀释至所需浓度。
为了测试保护活性,以所述施用率将活性化合物制剂喷洒至幼小植物上。喷洒层干燥后,将早疫病病菌(Alternaria solani)的含水孢子悬液接种于该植物上。然后将该植物在约20℃、大气相对湿度约100%的培养室继续放置一天。
接种后3天进行评估。0%表示相当于对照样的药效,100%表示未观察到侵染。
表E
链格孢属(蕃茄)/保护
Claims (8)
2.权利要求1的结构式(I)的旋光甲酰胺,其中
R代表氢、甲基或乙基,
M代表M-1或M-2,
R1代表氢、氟、氯、甲基或三氟甲基,
R2代表甲基或三氟甲基,
R3代表氢或氟,
R4代表三氟甲基或碘,
R5代表三氟甲基。
3.制备权利要求1的结构式(I)的旋光甲酰胺的方法,其特征在于,
a)在任选存在催化剂时,在任选存在缩合剂时,在任选存在酸结合剂时,以及在任选存在稀释剂时,
以下结构式(II)的羧酸衍生物
其中,
A具有权利要求1所述的含义,并且
X1代表卤素或羟基,
与以下结构式(III)的胺反应,
其中,R和M具有权利要求1所述的含义,或者,
b)以下结构式(I-rac)的外消旋化合物
其中,R、M和A具有权利要求1所述的含义,
在存在呈液相的洗脱剂或洗脱剂混合物时,在手性硅胶固定相上进行色谱分离,
或者,在形成盐的条件下与旋光酸分级结晶,并且,随后释出纯对映体的或富含对映体的结构式(I)的化合物,或者,
c)以下结构式(IV)的化合物
其中,R、M和A具有权利要求1所述的含义,
或者,以下结构式(V)的化合物
其中,R、M和A具有权利要求1所述的含义,
或者以上两种化合物的混合物,在存在旋光催化剂或存在具有旋光配位体的催化剂时,进行氢化。
4.用于防治不想要的微生物的制剂,其特征在于,所述制剂至少含有一种权利要求1的结构式(I)的旋光甲酰胺以及填充剂和/或表面活性剂。
5.权利要求1的结构式(I)的旋光甲酰胺的应用,用于防治不想要的微生物。
6.防治不想要的微生物的方法,其特征在于,将权利要求1的旋光甲酰胺施用到微生物和/或其生境。
7.制备用于防治不想要的微生物的制剂的方法,其特征在于将权利要求1的结构式(I)的旋光甲酰胺与填充剂和/或表面活性剂混合。
8.以下结构式的胺
其中,R和M具有权利要求1所述的含义。
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CN104628646A (zh) * | 2015-02-16 | 2015-05-20 | 中国科学院上海有机化学研究所 | N-吡唑基甲酰苯胺类化合物、中间体、组合物、制备方法及应用 |
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CN103329905B (zh) * | 2013-07-24 | 2014-08-27 | 安徽省农业科学院植物保护与农产品质量安全研究所 | 一种含氟唑菌苯胺和井冈霉素的杀菌组合物 |
CN104628646A (zh) * | 2015-02-16 | 2015-05-20 | 中国科学院上海有机化学研究所 | N-吡唑基甲酰苯胺类化合物、中间体、组合物、制备方法及应用 |
CN104628646B (zh) * | 2015-02-16 | 2017-11-07 | 中国科学院上海有机化学研究所 | N‑吡唑基甲酰苯胺类化合物、中间体、组合物、制备方法及应用 |
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