CN1466578A - 吡唑基联苯羧酰胺类化合物及其防治有害微生物的用途 - Google Patents
吡唑基联苯羧酰胺类化合物及其防治有害微生物的用途 Download PDFInfo
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- CN1466578A CN1466578A CNA018161596A CN01816159A CN1466578A CN 1466578 A CN1466578 A CN 1466578A CN A018161596 A CNA018161596 A CN A018161596A CN 01816159 A CN01816159 A CN 01816159A CN 1466578 A CN1466578 A CN 1466578A
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- FAENXWZZEZJZRI-UHFFFAOYSA-N 2-phenyl-n-(1h-pyrazol-5-yl)benzamide Chemical class C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)NC=1C=CNN=1 FAENXWZZEZJZRI-UHFFFAOYSA-N 0.000 title claims abstract description 19
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Abstract
本发明涉及新的式(I)的吡唑基联苯羧酰胺类化合物,其中R1,R2,X,m,Y和n各自如说明书中所定义。本发明还涉及制备所述物质的其它方法和使用其防治有害微生物的用途,以及新的中间体产物及其制备方法。
Description
本发明涉及新的吡唑基联苯羧酰胺类化合物,其多种制备方法及其防治有害微生物的用途。
已知多种N-羧酰苯胺类化合物具有杀真菌活性(参见:WO 93/11117,EP-A 0545 099,EP-A 0 589 301,WO 99/09013,DE 198 40 322)。所以,可使用N-(2-环己基)-1,3-二甲基-5-氟吡唑-4-羧酰苯胺,N-(2-苯基)-1,3-二甲基-吡唑-4-羧酰苯胺和N-[2-(2-氟苯基)]-1,3-二甲基-吡唑-4-羧酰苯胺防治真菌。上述物质的活性是好的;可是,在一些情况下它们不适合在低剂量使用。
因此本发明提供了新的式(I)的吡唑基联苯羧酰胺类化合物:其中
R1代表氢、C1-C6-烷基、C1-C6-卤代烷基、苯甲基或吡啶甲基,
R2代表氢或C1-C6-烷基,
X代表卤素、硝基、氰基、羟基、羧基、C1-C8-烷基、带有1-5个卤素原子的C1-C6-卤代烷基、C1-C8-烷氧基、带有1-5个卤素原子的C1-C6-卤代烷氧基、C1-C8-烷硫基、带有1-5个卤素原子的C1-C6-卤代烷硫基、C2-C8-链烯氧基、C2-C8-链炔氧基、C3-C8-环烷基、C1-C8-烷氧基羰基或代表-C(R2)=N-OR1,
m代表0-3的整数,其中m代表2或3时,X代表相同或不同的基团,
Y代表卤素、硝基、氰基、羟基、羧基、C1-C8-烷基、带有1-5个卤素原子的C1-C6-卤代烷基、C1-C8-烷氧基、带有1-5个卤素原子的C1-C6-卤代烷氧基、C1-C8-烷硫基、带有1-5个卤素原子的C1-C6-卤代烷硫基、C2-C8-链烯氧基、C2-C8-链炔氧基、C3-C8-环烷基、C1-C8-烷氧基羰基或代表C1-C6-烷氧亚胺基(Alkoximino)-C1-C6-烷基和
n代表0-4的整数,其中n代表2、3或4时,Y代表相同或不同的基团。
而且,现已发现式(I)的吡唑基联苯羧酰胺类化合物的制备是通过:
a)式(II)的羧酸衍生物与式(III)的苯胺衍生物反应其中
R1,R2,X,m,Y和n各自具有上述定义,
如果需要反应在催化剂存在下,如果需要反应在酸结合剂和如果需要反应在稀释剂存在下进行,
或
(b)式(IV)的羧酰胺衍生物与式(V)的硼酸衍生物反应其中X和m各自具有上述定义,其中
R1,R2,Y和n各自为上述定义和
G1和G2各自代表氢或一起代表四甲基亚乙基,
如果需要反应在催化剂存在下,如果需要反应在酸结合剂存在下和如果需要反应在稀释剂存在下进行,
或
R1,R2,Y和n各自具有上述定义
如果需要反应在催化剂存在下,如果需要反应在酸结合剂存在下和如果需要反应在稀释剂存在下进行,
或
d)式(VIII)的联苯基酰基衍生物与式(IX)的烷氧基胺反应其中
R2,X,m,Y和n各自具有上述定义和,
R1-O-NH2×HCl (IX)其中R1具有上述定义,
如果需要反应在酸结合剂和如果需要反应在稀释剂存在下进行,
或
e)式(I-a)的羟胺衍生物与式(X)的化合物反应其中
R2,X,m,Y和n各自具有上述定义,
R3-E (X)其中R3代表C1-C6-烷基和
E代表氯、溴、碘、甲磺酰基或对甲苯磺酰基,
或R3和E一起代表硫酸(二-C1-C6-烷基)酯,
如果需要反应在酸结合剂存在下和如果需要反应在稀释剂存在下进行,
或
f)式(IV)的羧酰胺衍生物与式(VII)的苯基肟衍生物反应
其中X和m各自具有上述定义其中
R1,R2,Y和n各自具有上述定义
反应在钯或铂催化剂存在下和在4,4,4’,4’5,5,5’,5’-八甲基-2,2’-双-1,3,2-二氧硼戊环(dioxaborolan)存在下,如果需要反应在酸结合剂存在下和如果需要反应在稀释剂存在下进行。
最后,已经发现新的式(I)的吡唑基联苯羧酰胺类化合物具有非常好的杀微生物活性并在作物保护和材料保护中用于防治有害微生物。
令人惊奇的是,根据本发明的式(I)吡唑基联苯羧酰胺类化合物比现有技术中结构非常接近并具有相同作用目的的活性化合物有较好的杀真菌活性。
式(I)提供了根据本发明吡唑基联苯羧酰胺类化合物的一般性定义。
R1优选代表氢、C1-C4-烷基、具有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷基、苯甲基或吡啶甲基。
R2优选代表氢或C1-C4-烷基。
X优选代表氟、氯、溴、硝基、氰基、羟基、羧基、C1-C6-烷基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷基、C1-C6-烷氧基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷氧基、C1-C6-烷硫基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷硫基、C2-C6-链烯氧基、C2-C6-链炔氧基、C3-C7-环烷基、C1-C4-烷氧基羰基或代表-C(R2)=N-OR1。
m优选代表0-3的整数,其中如果m代表2或3时,X代表相同或不同的基团。
Y优选代表氟、氯、溴、硝基、氰基、羟基、羧基、C1-C6-烷基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷基、C1-C6-烷氧基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷氧基、C1-C6-烷硫基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷硫基、C2-C6-链烯氧基、C2-C6-链炔氧基、C3-C7-环烷基、C1-C4-烷氧基羰基或代表C1-C4-烷氧亚胺基-C1-C4-烷基。
n优选代表0-3的整数,其中n代表2或3时,Y代表相同或不同的基团。
R1特别优选代表氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-氯乙基、苯甲基、2-吡啶基甲基、3-吡啶基甲基或4-吡啶基甲基。
R2特别优选代表氢、甲基、乙基、正丙基、异丙基或正丁基。
X特别优选代表氟、氯、溴、硝基、氰基、羟基、羧基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氯甲基、三氟甲基、二氟甲基、二氟氯甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、三氟甲硫基、二氟氯甲硫基、烯丙氧基、炔丙氧基、环丙基、环戊基、环己基、环庚基、甲氧羰基、乙氧羰基或代表-C(R2)=N-OR1。
m特别优选代表0-2的整数,其中如果m代表2时,X代表相同或不同的基团。
Y特别优选代表氟、氯、溴、硝基、氰基、羟基、羧基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氯甲基、三氟甲基、二氟甲基、二氟氯甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、三氟甲硫基、二氟氯甲硫基、烯丙氧基、炔丙氧基、环丙基、环戊基、环己基、环庚基、甲氧羰基、乙氧羰基或甲氧亚胺甲基。
n特别优选代表0-2的整数,其中n代表2时,Y代表相同或不同的基团。
给出的特别优选的式(I-b)化合物中R1,R2,X,m,Y和n各自为上述给出的优选的或特别优选的定义。
给出的特别优选的式(I-c)化合物中R1,R2,X,m,Y和n各自为上述给出的优选的或特别优选的定义。
进一步给出了优选的式(I-d)化合物其中R1,R2,X,m,Y和n各自为上述给出的定义。
给出的特别优选的式(I-d)化合物中R1,R2,X,m,Y和n各自为上述给出的优选的或特别优选的定义。
优选或特别优选的化合物是带有上述优选或特别优选取代基的化合物。
如烷基或链烯基的饱和或不饱和烃基可以各自是直链或支链的,也可能包括在具有杂原子的化合物中,如在烷氧基中。
可选择取代基可以是单-或多取代的,其中在多取代情况下的取代基可以是相同或不同的。具有相同的参数的多数基团,例如m个基团X在m>1时可以是相同或不同的。
卤素取代的基团,例如卤代烷基是单-或多卤代的。在多卤代时,卤原子可以是相同或不同的。在此,卤素代表氟、氯、溴和碘,特别是氟、氯和溴。
可是,上述一般的或优选基团定义或实例也可以根据需要彼此组合,即,包括各自范围和优选范围之间的任意组合。适用于终产物的定义,相应的也适合前体和中间体。
上述定义可以根据需要以任意的方式彼此组合。而且,可以不使用单独的定义。
使用2’-溴-1,3-二甲基-5-氟吡唑-4-羧酰苯胺和(4-甲氧亚氨基甲基)-苯基硼酸作为原料和催化剂,根据本发明的方法(b)的过程可用下式例示。
使用2’-(4-肟基乙基)-苯基-1,3-二甲基-5-氟吡唑-4-羧酰苯胺和溴甲烷作为原料,根据本发明的方法(e)的过程可用下式例示。
使用2’-溴-1,3-二甲基-5-氟吡唑-4-羰酰苯胺和1-溴-4-甲氧亚氨基甲基-苯作为原料和催化剂和4,4,4’,4’5,5,5’,5’-八甲基-2,2’-双-1,3,2-二氧硼戊环,根据本发明的方法(f)的过程可用下式例示。
方法和中间体的例示说明
式(II)提供了进行本发明方法(a)作为原料所需的羧酸衍生物的一般定义。在上式中,G优选代表氯、溴、羟基、甲氧基或乙氧基,特别优选氯、羟基或甲氧基。
式(II)的羧酸衍生物是已知的或可通过已知方法制备的(参见:WO 93/11 117,EP-A 0 545 099,EP-A 0 589 301和EP-A 0 589 313)。
式(III)提供了进行本发明方法(a)作为反应成分所需苯胺衍生物的一般定义。在上式中,R1,R2,X,m,Y和n各自的优选定义为在对本发明式(I)化合物的说明中对于这些基团或参数已经提及的优选或特别优选的含义。
式(III)的苯胺衍生物是新的。其中的一些可以通过已知方法制备(参见:EP-A 0 545 099和EP-A 0 589 301)。
式(III)的苯胺衍生物还可通过下述方法制备:
Hal代表卤素,其中R1,R2,Y,n,G1和G2各自具有上述定义,
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下,和如果需要在催化剂存在下进行,
或者
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下,和如果需要在催化剂存在下进行。
式(XI)提供了进行本发明方法(g)作为反应成分所需的2-卤代苯胺衍生物的一般定义。在上式中,X和m各自的优选定义为在对本发明式(I)化合物的说明中对于这些基团或参数已经提及的优选或特别优选的含义。Hal优选代表氟、氯或溴,特别是氯或溴。
式(XI)的2-卤代苯胺衍生物可市售得到或可以通过相应的硝基化合物采用还原反应制备。
式(XII)提供了进行本发明方法(h)作为反应成分所需的苯胺硼酸的一般定义。在上式中,X和m各自的优选定义为在对本发明式(I)化合物的说明中对于这些基团或参数已经提及的优选或特别优选的含义。G1和G2各自优选代表氢或一起代表四甲基亚乙基。
式(XII)的苯胺硼酸可市售得到。
式(IV)提供了进行本发明方法(b)和(f)作为原料所需的羧酰胺衍生物的一般定义。在上式中,X和m各自的优选定义为在对本发明式(I)化合物的说明中对这些基团已经提及的优选或特别优选的含义。
式(IV)的羧酰胺衍生物是已知的或可以通过已知方法制备(参见:W0 91/01311,EP-A 0 371 950)。
式(V)提供了进行本发明方法(b)和方法(g)作为反应成分所需的硼酸衍生物的一般定义。在上式中,R1,R2,Y和n各自的优选定义为在对本发明式(I)化合物的说明中对这些基团或参数已经提及的优选或特别优选的含义。
式(V)的硼酸衍生物是新的并可用下述方法制备:
i)式(XIII)的苯基硼酸与式(IX)的烷氧基胺反应,其中R2,Y,n,G1和G2各自具有上述定义
R1-O-NH2×HCl (IX)其中
R1具有上述定义,
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下,和如果需要在催化剂存在下进行。
式(XIII)提供了进行本发明方法(h)作为反应成分所需的苯基硼酸的一般定义。在上式中,R2,Y和n各自的优选定义为在对本发明式(I)化合物的说明中对于这些基团或参数已经提及的优选或特别优选的含义。G1和G2各自优选代表氢或一起为四甲基亚乙基。
式(XIII)的苯基硼酸可市售获得。
式(VI)提供了进行本发明方法(c)作为反应成分所需的羧酰胺-硼酸衍生物的一般定义。在上式中,X和m各自的优选定义为在对本发明式(I)化合物的说明中对于这些基团已经提及的优选或特别优选的含义。G1和G2各自优选代表氢或一起为四甲基亚乙基。
式(VI)的羧酰胺-硼酸衍生物是新的,它们可以通过下述方法制备,
X,m,G1和G2各自具有上述定义,
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下,和如果需要在催化剂存在下进行。
式(VII)提供了进行本发明方法(c),(f)和(h)作为反应成分所需的苯基肟衍生物的一般定义。在上式中,R1,R2,Y和n各自的优选定义为在对本发明式(I)化合物的说明中对于这些基团已经提及的优选或特别优选的含义。
式(VII)的苯基肟衍生物是已知的或可通过已知方法制备(参见:Synth.Commun.
2000,
30,665-669,Synth.Commun.
1999,
29,1697-1701)。
式(VIII)提供了进行本发明方法(d)作为原料所需的联苯基酰基衍生物的一般定义。在上式中R2,X,m,Y和n各自的定义为在对本发明式(I)化合物的说明中对于这些基团已经提及的优选或特别优选的含义。
式(VIII)的联苯基酰基衍生物是新的。它们可通过下述方法制备:
R2,X,m,Y和n各自具有上述定义,
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下进行。
式(XIV)提供了进行本发明方法(k)作为反应成分所需的2-苯甲醛-苯胺-衍生物的一般定义。在上式中,R2,X,m,Y和n各自的优选定义为在对本发明式(I)化合物的说明中对于这些基团已经提及的优选或特别优选的含义。
式(XIV)的2-苯甲醛-苯胺-衍生物是新的。它们可通过下述方法制备:
X和m各自具有上述定义和
Hal代表卤素,其中
R2,Y,n,G1和G2各自具有上述定义,
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下进行。
式(IX)提供了进行本发明方法(d)和方法(i)作为反应成分所需的烷氧基胺的一般定义。在上式中R1的优选定义为在对本发明式(I)化合物的说明中对于这些基团已经提及的优选或特别优选的含义。在本说明书中优选提及的是使用其盐酸盐。可是,在根据本发明的方法中还可以使用游离的烷氧基胺。
式(IX)的烷氧基胺可市售获得。
式(I-a)提供了进行本发明方法(e)作为原料所需的羟胺衍生物的一般定义。在上式中R2,X,m,Y和n各自的优选定义为在对本发明式(I)化合物的说明中对于这些基团已经提及的优选或特别优选的含义。
根据本发明的式(I-a)的羟胺衍生物是新的。它们可通过本发明上述方法(a)、(b)、(c)、(d)或(f)中的任一种方法制备。
式(X)提供了进行本发明方法(e)作为反应成分所需化合物的一般定义。在上式中R3优选代表C1-C4-烷基,特别优选甲基、乙基、正丙基、异丙基或正丁基。E优选代表氯、溴、碘、甲磺酰基或对甲苯磺酰基。E特别优选代表氯或溴。
式(X)化合物可市售获得。
进行本发明方法(a)、(b)、(c)、(d)、(e)和(f)的适合的酸结合剂是用于上述反应中的各种常规无机和有机碱。优选使用碱土金属或碱金属氢氧化物,如氢氧化钠、氢氧化钙、氧化钾、或氢氧化铵,碱金属碳酸盐,如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠,碱金属或碱土金属乙酸盐,如乙酸钠、乙酸钾、乙酸钙,以及叔胺,如三甲基胺、三乙基胺、三丁基胺、N,N-二甲基苯胺,吡啶,N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。可是,也可以在不加酸结合剂时进行反应或使用过量的胺成分,以便将胺同时作为酸结合剂。
进行本发明方法(a)、(b)、(c)、(d)、(e)和(f)的适合稀释剂是各种常规惰性有机溶剂。优选使用可任选卤代的脂族、脂环或芳香烃,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;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,如乙醚、二异丙基醚、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;腈,如乙腈、丙腈、正-或异-丁腈或苯甲腈;酰胺如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-N-甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯如乙酸甲酯或乙酸乙酯;亚砜,如二甲基亚砜,或砜,如环丁砜。
进行本发明方法(a)、(b)、(c)、(d)、(e)和(f)时,反应温度在各种情况下可在相当宽的范围内变化。通常,反应在0℃至140℃的温度下进行,优选在10℃至120℃。
本发明方法(a)、(b)、(c)、(d)、(e)和(f)通常可在大气压力下进行。可是,在一些情况下也可在加压或减压下操作。
当进行本发明方法(a)时,对每摩尔式(II)的酰卤通常使用1摩尔或过量的式(III)苯胺衍生物和1-3摩尔的酸结合剂。可是,还可使用其它比例的反应成分。通过常规方法进行后处理。通常,反应混合物与水混合并分离有机相,干燥后,减压浓缩。如果需要可采用常规方法,如色谱分离或重结晶,从所得的残余物中分离可能存在的任何不纯物。
当进行本发明方法(b)时,对每摩尔式(IV)的羧酰胺通常使用1摩尔或过量的式(V)硼酸胺衍生物和1-5摩尔的酸结合剂。可是,还可使用其它比例的反应成分。通过常规方法进行后处理。通常,反应混合物与水混合并分离沉淀并干燥。如果需要可采用常规方法,如色谱分离或重结晶,从所得的残余物中分离可能存在的任何不纯物。
当进行本发明方法(c)时,对每摩尔式(VI)的羧酰胺-硼酸衍生物通常使用1摩尔或过量的式(VII)苯基肟衍生物和1-10摩尔的酸结合剂以及0.5-5mol%的催化剂。可是,还可使用其它比例的反应成分。通过常规方法进行后处理。通常,反应混合物与水混合并分离沉淀并干燥。如果需要可采用常规方法,如色谱分离或重结晶,从所得的残余物中分离可能存在的任何不纯物。
当进行本发明方法(d)时,对每摩尔式(VIII)的联苯基酰基衍生物通常使用1摩尔或过量的式(IX)烷氧基胺和1-5摩尔的酸结合剂。可是,还可使用其它比例的反应成分。通过常规方法进行后处理。通常,反应混合物与水混合并分离沉淀,用水和二异丙基醚冲洗然后干燥。如果需要可采用常规方法,如色谱分离或重结晶,从所得的残余物中分离可能存在的任何不纯物。
当进行本发明方法(e)时,对每摩尔式(I-a)的羟胺衍生物通常使用1摩尔或过量的式(X)试剂和1-5摩尔的酸结合剂。可是,还可使用其它比例的反应成分。通过常规方法进行后处理。通常,反应混合物与水混合并分离沉淀并干燥。如果需要可采用常规方法,如色谱分离或重结晶,从所得的残余物中分离可能存在的任何不纯物。
当进行本发明方法(f)时,对每摩尔式(IV)的羧酰胺衍生物通常使用1摩尔或过量的式(VII)苯基肟衍生物和1-5摩尔的酸结合剂和1-5摩尔的催化剂。可是,还可使用其它比例的反应成分。通过常规方法进行后处理。通常,反应混合物与水混合并分离沉淀并干燥。如果需要可采用常规方法,如色谱分离或重结晶,从所得的残余物中分离可能存在的任何不纯物。
根据本发明的物质具有强的杀微生物活性,并可在作物保护和材料保护中用来防治有害微生物,如真菌和细菌。
可使用本活性化合物在作物保护中用作杀真菌剂,以防治根肿病菌纲、卵菌纲、弧菌纲、结合菌纲、子囊菌纲、担子菌纲和半知菌纲。
可使用本活性化合物在作物保护中用作杀细菌剂,以防治假单胞菌科、根瘤菌科、肠杆菌科、棒状杆菌科和链霉菌科。
在上述类名中提及的一些致病真菌和细菌病害非限定地是例如:
黄单胞菌属:例如野油菜黄单胞菌水稻致病变种;
假单孢菌属:例如丁香假单胞菌属;lachrymans;
欧氏植病杆菌属:如梨火疫病欧氏杆菌;
腐霉属,例如:终极腐霉;
疫病属,例如:蔓延疫霉;
假霜霉属,例如:律草假霜霉或古巴假霜霉;
单轴霉属,例如:葡萄生单轴霉;
盘梗霉属,例如:莴苣盘梗霉;
霜霉属,例如:豌豆霜霉或芸苔霜霉;
白粉菌属,例如:禾白粉菌;
球壳霉属,例如:苍耳单丝壳菌;
柄球霉属,例如:苹果白粉病柄球菌;
黑星菌属,例如:苹果黑星菌;
核腔菌属,例如:圆核腔菌或麦类核腔菌(分生孢子型:眼斑点病,同物异名:长蠕孢属);
旋孢霉属,例如:禾旋孢霉(分生孢子型:眼斑点病,同物异名:长蠕孢属);
单孢锈菌属,例如:菜豆单孢锈霉;
柄锈菌属,例如:隐匿柄锈菌;
核盘菌属,例如:油菜核盘菌;
腥黑粉菌属,例如:小麦网腥黑粉菌;
黑粉菌属,例如裸黑粉菌或燕麦黑粉菌;
薄膜革菌属,例如:佐佐木氏薄膜革菌;
梨孢霉属,例如:稻瘟病;
镰刀霉属,例如:禾杆镰孢;
葡萄孢属,例如:灰葡萄孢;
壳针孢霉属,例如:颍枯壳针孢;
小球腔菌属,例如:小麦小球腔菌;
尾孢霉属,例如:小豆尾孢;
链格孢属,例如:甘蓝黑斑病链革孢;
假尾孢霉属,例如:Pseudocercosporella herpotrichoides。
事实上在处理上述植物的地上部分、植物的繁殖体和种子、以及土壤时,植物对防治植物病害所需浓度下的本活性化合物有好的植物耐受性。
可使用本发明活性化合物特别有效地防治园艺和果树和蔬菜上生长的病害,例如:防治黑星菌属、葡萄孢属、核盘菌属、丝核菌属、钩丝壳霉属、单丝壳菌属、柄球菌属、链格孢属和毛盘孢属的病害。对水稻病害如梨孢属和薄膜革菌属也有好的防治效果。
本发明活性化合物还适合增加作物产量。另外,它们显示出低毒性和好的植物耐受性。
根据本发明的活性化合物可以处理所有植物和植物部分。本文中对植物可理解为所有植物和植物群落如有用和有害的野生植物或作物(包括天然存在的作物)。被种植的作物是可通过常规的栽培和最佳的方法,或通过生物技术和基因工程方法或上述方法的组合获得的作物,作物包括转基因植物和包括根据栽培者权利被保护或不被保护的植物的变种。应理解的是植物部分的定义为所有地上和地下部分和植物组织,如茎枝、叶、花和根,例如可被述及的为叶、针叶、茎、茎干、花、子实体、果实和种子以及根、块茎和根茎。植物部分还包括收获的植物和植蔬和生成的繁殖材料,例如插枝、块茎、根茎、切枝和种子。
在材料保护中,本发明的物质可用来保护工业材料防治有害微生物的侵染和损害。
在本文中工业材料应理解的定义为已制备的用于工业的无机材料。例如,可以被本发明活性化合物保护而防止微生物带来的变化或损害的工业材料的例子可以是可能被微生物侵染或损坏的粘着剂、胶料、纸和纸板、纺织品、皮革、木材、油漆和塑料品、冷却润滑剂和其它材料。一部分生产设备也被包括在上述被保护的材料范围内,例如可能被微生物增殖损害的冷却水管。在本发明范围内提及的工业材料优选为粘着剂、胶料、纸和纸板、皮革、木材、油漆、冷却润滑剂和传热液,特别优选木材。
可述及的工业材料能够降解或改变的微生物例如为:细菌、真菌、酵母、藻和粘液微生物。本发明活性化合物优选用来防治真菌、特别是霉菌、木材脱色和木材损坏真菌(担子菌类),并可防治粘液微生物和藻。
可述及的微生物例如为下述种类:
链格孢属,例如纤细链格孢,
曲霉属,例如黑色曲霉,
毛壳霉属,例如球毛壳霉,
粉孢革菌属,例如单纯粉孢革菌,
香菇属,例如Lentinus tigrinus,
青霉菌属,例如灰绿青霉,
多孔菌属,例如变色多孔菌,
短柄霉属,如出芽短柄霉,
Sclerophoma,例如Sclerophoma pityophila,
木霉属,例如绿色木霉,
艾希氏杆菌属,例如大肠杆菌,
假单孢菌属,例如铜绿假单孢菌,
葡萄球菌属,金黄色葡萄球菌。
根据其特定的物理和/或化学性质,本活性化合物可被转化成为常规的制剂,如液剂,乳剂,悬浮剂,粉剂,泡沫剂,糊剂,颗粒剂,气雾剂,在聚合物中的微细胶囊和种子包衣组合物,以及超低容量冷弥雾剂和热弥雾剂。
这些制剂是以已知方法生产的,例如,通过将活性成分与填充剂,即液体溶剂,加压液化气体,和/或固体载体混合而生产,制剂中任选可使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。一般来讲,适当的液体溶剂主要有:芳香烃类,如二甲苯,甲苯或烷基萘,氯代芳烃类或氯代脂肪烃类,如氯苯,二氯乙烷或二氯甲烷,脂肪烃类,如环己烷或烷属烃,例如石油馏份,醇类,如丁醇或乙二醇及其醚和酯类,酮类,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。液化气体填充剂或载体的定义为在常温和常压下是气体的加压液体,例如气雾推进剂,如卤代烃类以及丁烷,丙烷,氮气和二氧化碳。适合的固体载体有:例如,天然矿物粉末,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅,氧化铝和硅酸盐。适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石,大理石,浮石,海泡石和白云石,以及无机和有机粉末的合成颗粒,和有机材料的颗粒如锯末,坚果壳,玉米穗茎和烟草茎。适当的乳化剂和/或成泡剂有:例如非离子和阴离子乳化剂,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,芳基磺酸盐以及蛋白水解产物。适合的分散剂有:例如木质素亚硫酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素、天然及合成的粉末、颗粒或胶乳状聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
可能使用的着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和痕量营养物如盐,例如,铁、锰、硼、铜、钴、钼和锌盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5%-90%的活性化合物。
根据本发明的活性化合物可以单独或以其制剂形式使用,也可以与其它已知活性化合物的混合物的形式存在,其它活性化合物如杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂,以拓宽,例如活性谱或防止抗性的发展。在许多情况下,可以获得增效作用,即混合物的活性大于单独成分的活性。
适合的混合成分的实例如下述化合物:
杀真菌剂:
aldimorph、氨丙膦酸、氨丙膦酸钾盐、andoprim、敌菌灵、氧环唑、腈嘧菌酯
苯霜灵、麦锈灵、苯菌灵、苄烯酸、苄烯酸异丁酯、双丙氨膦、乐杀螨、联苯、联苯三唑醇、灭瘟素、糠菌唑、乙嘧酚磺酸酯、丁硫啶,
石硫合剂、capsimycin、敌菌丹、克菌丹、多菌灵、萎锈灵、carvon、灭螨猛、灭瘟唑、苯咪唑菌、地茂散、氯化苦、百菌清、乙菌利、clozylacon、硫杂灵、霜脲氰、环丙唑醇、嘧菌环胺、酯菌胺,
咪菌威、双氯酚、苄氯三唑醇、diclofluanid、哒菌酮、氯硝胺、乙霉威、苯醚甲环唑、二甲嘧酚、烯酰吗啉、烯唑醇、烯唑醇-M、敌螨普、二苯胺、吡菌硫、灭菌磷、二氰蒽醌、十二环吗啉、多果定、敌菌酮,
敌瘟磷、氧唑菌、乙环唑、乙嘧酚、土菌灵,
噁唑酮菌、咪菌腈、氯苯嘧啶醇、腈苯唑、呋菌胺、种衣酯、拌种咯、苯锈啶、丁苯吗啉、醋酸三苯基锡、羟基三苯锡、福美铁、嘧菌腙、氟啶胺、氟联苯菌、氟氯菌核利、氟喹唑、呋嘧醇、氟硅唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、三乙膦酸铝、三乙膦酸钠、四氯苯酞、麦穗宁、呋霜灵、呋吡唑灵、灭菌胺、呋菌唑、呋醚唑、拌种胺,
双胍盐,
六氯苯、己唑醇、噁霉灵,
抑霉唑、亚胺唑、双胍辛、双八胍盐、双胍辛醋酸盐、iodocarb、种菌唑、异稻瘟净(IBP)、异菌脲、irumamycin、稻瘟灵、氯苯咪菌酮,
春雷霉素、亚胺菌、含铜制剂如:氢氧化铜、环烷酸铜、王铜、硫酸铜、氧化铜、喹啉酮和波尔多液,
代森锰铜、代森锰锌、代森锰、meferimzone、嘧菌胺、灭锈胺、甲霜灵、叶菌唑、磺菌威、呋菌胺、代森联、苯吡咯菌、噻菌胺、米多霉素、腈菌唑、甲菌利,
福美镍、异丙消、氟苯嘧啶醇,
呋酰胺、噁霜灵、oxamocarb、喹菌酮、氧化萎锈灵、oxyfenthiin,
多效唑、稻瘟酯、戊菌唑、戊菌隆、氯瘟磷、多马霉素、哌丙灵、多抗霉素、polyoxorim、烯丙苯噻唑、咪鲜胺、腐霉利、霜霉威、propanosine-sodium、丙环唑、丙森锌、吡菌磷、啶斑肟、嘧霉胺、咯喹酮、氯吡呋醚,
唑喹菌酮、五氯硝基苯(PCNB)、喹氧灵,
硫磺粉和硫制剂,
戊唑醇、叶枯酞、四氯硝基苯、四环唑、四氟醚唑、噻菌灵、噻菌腈、溴氟唑菌、甲基硫菌灵、福美双、硫氰苯甲酰胺、甲基立枯磷、甲苯氟磺胺、三唑酮、三唑醇、叶锈特、咪唑嗪、水杨菌胺、三环唑、十三吗啉、氟菌唑、嗪胺灵、灭菌唑,
烯效唑,
有效霉素、乙烯菌核利、烯霜苄唑,
氰菌胺、代森锌、福美锌以及
咪草酸,
OK-8705,
OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-β-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-α-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基}-氨基甲酸-1-异丙基酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮-O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-甲酰苯胺,
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
2,6-二氯-5-(甲硫基)-4-嘧啶基-硫氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)-磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡萄糖基)-a-D-吡喃葡萄糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴甲基)-戊二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异硫氰酸根合甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈,
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲胺,
8-羟基喹啉硫酸盐,
9H-呫吨-9-羧酸-2-[(苯基氨基)-羰基]-酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)-氧基]-2,5-噻吩二羧酸酯,
顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙基酯,
碳酸氢钾,
甲基四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-氨基丙酸甲酯,
N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-氨基丙酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯-4,5-二-(2-丙炔氧基)-苯基]-N’-甲氧基-甲基亚氨酸酰胺,
N-甲酰基-N-羟基-DL-氨基丙酸钠盐,
[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸O,O-二乙酯,
苯基丙基硫代氨基磷酸O-甲基-S-苯基酯,
1,2,3-苯并噻二唑-7-硫代羧酸S-甲酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃]-3’-酮,
杀细菌剂:
溴硝丙二醇、双氯酚、三氯甲基吡啶、福美镍、春雷霉素、辛噻酮、呋喃羧酸、土霉素、烯丙苯噻唑、链霉素、叶枯酞、硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
阿维菌素、乙酰甲胺磷、啶虫脒、氟丙菊酯、棉铃威、涕灭威、砜灭威、顺式氯氰菊酯、甲体氯氰菊酯、双甲脒、齐墩螨素、AZ 60541、艾扎丁、甲基吡噁磷、谷硫磷A、谷硫磷M、三唑锡,
日本甲虫芽孢杆菌、球形芽孢杆菌、枯草芽孢杆菌、苏云金杆菌、baculoviruses、蚕白僵菌、纤细白僵菌、噁虫威、丙硫克百威、杀虫磺、苯螨特、高效氟氯氰菊酯、联苯肼酯、联苯菊酯、bioethanomethrin、生物氯菊酯、仲丁威、溴硫磷A、合杀威、噻嗪酮、特嘧硫磷、丁酮威、butylpyridaben,
硫线磷、甲萘威、克百威、三硫磷、丁硫克百威、杀螟丹、chloethocarb、氯氧磷、氟唑虫清、毒虫畏、氟啶脲、氯甲磷、毒死蜱、甲基毒死蜱、chlovaphorthrin、顺式苄呋菊酯、顺式氯菊酯、clocythrin、除线威、四螨嗪、杀螟腈、cycloprene、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺,
溴氰菊酯、甲基内吸磷、内吸磷硫赶式异构体、甲基内吸磷硫赶式异构体、丁醚脲、二嗪磷、敌敌畏、除虫脲、乐果、甲基毒虫畏、苯虫醚、乙拌磷、碘酰丁二辛、苯氧炔螨,
elfusilanate、emamectin、右旋烯炔菊酯、硫丹、虫霉属、S-氰戊聚酯、乙硫苯威、乙硫磷、灭线磷、醚菊酯、特苯噁唑、乙嘧硫磷、苯线磷、喹螨醚、苯丁锡、杀螟硫磷、苯硫威、fenoxacrim、苯氧威、甲氰菊酯、fenpyrad、fenpyrithrin、唑螨酯、氰戊菊酯、氟虫腈、氟啶胺、啶蜱脲、溴氟菊酯、氟环脲、氟氰戊菊酯、氟虫脲、flutenzine、氟胺氰菊酯、地虫硫磷、丁苯硫磷、噻唑磷、fubfenprox、呋线威,
颗粒体病毒,
特丁苯酰肼、六六六、庚烯磷、氟铃脲、噻螨酮、烯虫乙酯、吡虫啉、氯唑磷、异柳磷、噁唑磷、齐墩螨素,
核多角体病毒,
高效氯氟氰菊酯、氟丙氧脲,
马拉硫磷、灭蚜磷、四聚乙醛、甲胺磷、Metharhiziumanisopliae、Metharhizium flavoviride、杀扑磷、甲硫威、灭多威、甲氧苯酰肼、速灭威、噁虫酮、速灭磷、米尔螨素、久效磷,
二溴磷、烯啶虫胺、硝虫噻嗪、双苯氟脲,
氧乐果、杀线威、亚砜磷,
玫烟色拟青霉、对硫磷A、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶磷、嘧啶磷A、丙溴磷、猛杀威、残杀威、丙硫磷、发硫磷、吡蚜酮、吡唑硫磷、反灭虫菊、除虫菊素、哒螨灵、pyridathion、嘧胺苯醚、蚊蝇醚,
喹硫磷,
ribavirin
杀抗松、硫线磷、氟硅菊酯、艾克敌105、sulfotep、硫丙磷
氟胺氰菊酯、虫酰肼、吡螨胺、嘧丙磷、氟苯脲、七氟菊酯、双硫磷、灭虫畏、特丁硫磷、杀虫畏、辛体氯氰菊酯、thiamethoxam、噻丙腈、thiatriphos、硫环杀、硫双威、久效威、敌贝特、溴氯氰菊酯、四溴菊酯、苯螨噻、唑蚜威、三唑磷、triazuron、氯咪唑、敌百虫、杀铃脲、混杀威、
蚜灭多、氟吡唑虫、麦柯特尔
YI 5302
己体氯氰菊酯、zolaprofos
(1R-顺)-[5-(苯基甲基)-3-呋喃基]-甲基-3-[(二氢-2-氧代-3(2H)-亚呋喃基)-甲基]-2,2-二甲基环丙烷羧酸酯,
(3-苯氧基苯基)-甲基-2,2,3,3-四甲基环丙烷羧酸酯,
1-[(2-氯-5-噻唑基)甲基]四氢-3,5-二甲基-N-硝基-1,3,5-三嗪-2(1H)-亚胺,
2-(2-氯-6-氟苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-噁唑,
2-(乙酰氧基)-3-十二烷基-1,4-萘二酮,
2-氯-N-[[[4-(1-苯基乙氧基)-苯基]-氨基]-羰基]-苯甲酰胺,
2-氯-N-[[[4-(2,2-二氯-1,1-二氟乙氧基)-苯基]-氨基]-羰基]-苯甲酰胺,
3-甲基苯基-丙基氨基甲酸酯,
4-[4-(4-乙氧基苯基)-4-甲基戊基]-1-氟-2-苯氧基-苯,
4-氯-2-(1,1-二甲基乙基)-5-[[2-(2,6-二甲基-4-苯氧基苯氧基)乙基]硫代]-3(2H)-哒嗪酮,
4-氯-2-(2-氯-2-甲基丙基)-5-[(6-碘-3-吡啶基)甲氧基]-3(2H)-哒嗪酮,
4-氯-5-[(6-氯-3-吡啶基)甲氧基]-2-(3,4-二氯苯基)-3(2H)-哒嗪酮,
苏云金芽孢杆菌EG-2348株系,
[2-苯甲酰基-1-(1,1-二甲基乙基)]-苯甲酰肼,
2,2-二甲基-3-(2,4-二氯苯基)-2-氧代-1-氧杂螺[4,5]癸-3-烯-4-基丁酸酯,
[3-[(6-氯-3-吡啶基)甲基]-2-亚噻唑烷基]-氨基腈,
二氢-2-(硝基亚甲基)-2H-1,3-噻嗪-3(4H)-甲醛,
[2-[[1,6-二氢-6-氧代-1-(苯基甲基)-4-哒嗪基]氧基]乙基]-氨基甲酸乙酯
N-(3,4,4-三氟-1-氧代-3-丁烯基)-甘氨酸,
N-(4-氯苯基)-3-[4-(二氟甲氧基)苯基]-4,5-二氢-4-苯基-1H-吡唑-1-甲酰胺,
N-[(2-氯-5-噻唑基)甲基]-N’-甲基-N”-硝基-胍,
N-甲基-N’-(1-甲基-2-丙烯基)-1,2-肼硫代二甲酰胺,
N-甲基-N’-2-丙烯基-1,2-肼硫代二甲酰胺,
[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸O,O-二乙酯
也可能是与其它已知活性化合物,如除草剂,或与肥料和植物生长调节剂的混合物。
而且,本发明式(I)化合物还具有非常好的抗霉菌活性。它们具有非常宽的抗霉菌活性谱,特别是抗嗜皮菌和酵母菌、霉菌和双相真菌(diphasic fungi)。
例如假丝酵母属,如红色假丝酵母、团假丝酵母,表皮癣菌属,如絮状表皮癣属,曲霉属,如黑色曲霉和烟曲霉,发癣菌属,如须发癣菌,小孢子菌属如犬小孢子菌和头癣小孢子菌。
上述列出的真菌不会限制覆盖的霉菌谱,仅仅是例示说明。
本活性化合物可以其本身或其制剂形式,或从中进一步稀释制备的应用形式使用,如现用溶液,悬浮液,可湿性粉剂,糊剂,可溶粉剂,粉剂和颗粒剂。可以常规方式使用活性化合物,例如泼浇,喷雾,弥雾,撒播,喷粉,成泡,分散等。还可通过超低容量的方法,或注射活性化合物的制剂或活性化合物本身至土壤的方法使用活性化合物。还可以处理植物的种子。
当使用本发明活性化合物作为杀真菌剂时,根据使用的方式,使用量可在相当宽的范围内变化。在处理植物体部分时,活性化合物的使用量通常为0.1至10,000g/ha,优选10至1000g/ha。在种子包衣时,通常对每公斤种子需要0.001至50g,优选每公斤种子0.01至10g的活性化合物。在处理土壤时,活性化合物的使用量通常在0.1至10,000g/ha,优选1至5000g/ha。
用于保护工业材料的组合物包含的活性化合物的量一般为1至95%,优选10至75%。
本发明活性化合物的使用浓度根据要防治的微生物的发生和性质和被组合物保护的材料而确定。最佳的使用量可根据系列试验测定。通常,基于被保护的材料,使用的浓度为0.001至5%重量,优选0.05至1.0%重量。
如果需要,在材料保护中使用的本发明活性化合物或由其制备的制剂、浓缩物或完全常用制剂的活性和活性谱可通过加入其它的杀微生物活性化合物、杀真菌剂、杀细菌剂、除草剂、杀虫剂或其它活性化合物扩大活性谱或获得特定的效果,例如增加对昆虫的保护来提高。与根据本发明的化合物相比,上述混合物具有较宽的活性谱。
本发明活性化合物的制备和应用如下述实施例中所述。
制备实施例
方法(a)
在室温下,将1.3g(0.0057mol)的2’-氨基-1,1’-联苯基-4-甲醛-O-甲基肟的20ml甲苯溶液,与0.57g(0.0057mol)的三甲基胺混合。在室温下,伴随搅拌将1.0g(0.0057mol)的5-氟-1,3-二甲基-1H-吡唑-4-甲酰氯的5ml甲苯溶液滴加到上述混合物中。加完后,将反应混合物加热到50℃并在此温度下搅拌2个小时。为进行后处理,将反应混合物冷却至室温,再与25ml的甲苯混合并用水冲洗。分离有机相,用硫酸钠干燥,过滤并在减压下浓缩。所留剩余物用二异丙基醚重结晶。以此方法,得到1.45g(理论值的6 9.4%)的5-氟-N-{4’-[(甲氧基亚氨基)甲基]-1,1’-联苯-2-基}-1,3-二甲基-1H-吡唑-4-甲酰胺,为无色结晶,熔点114-116℃。
方法(b)
在室温下,将0.35g(0.001mol)的N-(2-溴-4,6-二氟苯基)-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺,0.06g(0.00005mol)的四-(三苯基膦)钯,0.32g(0.0018mol)的4-[(甲氧亚氨基)甲基]苯基硼酸和10ml的1,2-二甲氧基乙烷的混合物与0.5g(0.0047mol)的碳酸钠的3ml水溶液混合。然后将反应混合物加热至回流温度并保持在此温度下15小时。为进行后处理,将反应混合物在200ml的水中搅拌。吸滤过滤掉所得沉淀并干燥。所留剩余物在硅胶上色谱分离,用环己烷∶乙酸乙酯=1∶1作为流动相。浓缩洗脱液,得到0.20g(理论值的48%)的N-{3,5-二氟-4’-[(甲氧基亚氨基)甲基]-1,1’-联苯-2-基}-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺,为固体,熔点164-167℃。
方法(c)
在室温下,将1.28g(12mmol)的碳酸钠溶于6ml的水中,加入0.71g(2mmol)的5-氟-1,3-二甲基-N-[2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯基]-1H-吡唑-4-甲酰胺、1.39g(6mmol)的4-溴-2-氟苯甲醛-O-甲基肟、0.03g(0.05mmol)的PdCl2(dppf)和40ml的二甲基亚砜的混合物中。将反应混合物在80℃下搅拌15小时。
为进行后处理,将反应混合物在400ml的水中搅拌,吸滤滤出所得沉淀并干燥。然后将粗产物在硅胶柱色谱纯化,用环己烷∶乙酸乙酯=1∶1作为流动相。浓缩得到0.11g(理论值的14%)的5-氟-N-{3’-氟-4’-[(甲氧基亚氨基)甲基]-1,1’-联苯-2-基}-1,3-二甲基-1H-吡唑-4-甲酰胺,为结晶,熔点158-161℃。
实施例4
方法(d)
将1.0g(0.0028mol)的N-(4’-乙酰基-1,1’-联苯-2-基)-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺,0.30g(0.0036mol)的O-甲基羟胺盐酸盐,0.30g(0.0036mol)的乙酸钠和6ml甲醇的混合物,在室温下搅拌12小时。为进行后处理,将反应混合物在水中搅拌,吸滤过滤出所得沉淀,用水然后用少量二异丙基醚冲洗并干燥。得到0.91g(理论值的85.4%)的5-氟-N-[4’-(N-甲氧基乙烷亚氨基(imidoyl))-1,1’-联苯-2-基]-1,3-二甲基-1H-吡唑-4-甲酰胺,熔点153℃。
1H-NMR谱(DMSO/TMS):δ=3.60ppm。
方法(g)
在室温下,将2.9g(0.017mol)的2-溴苯胺,0.68g的四-(三苯基膦)钯,5.5g(0.031mol)的4-[(甲氧基亚氨基)甲基]苯基硼酸和40ml的1,2-二甲氧基乙烷的混合物与8.2g(0.077mol)碳酸钠的35ml水溶液混合。然后将反应混合物加热至回流温度并沸腾12小时。为进行后处理,将反应混合物冷却至室温并用乙醚提取。分离有机相并与水混合。再次分离有机相,用硫酸钠充分干燥,最后在减压下浓缩。所留剩余物在硅胶上色谱分离,用环己烷∶乙酸乙酯=3∶1作为流动相。浓缩洗脱液,得到3.8g(以2-溴苯胺为基础的理论值的98.8%)的2’-氨-1,1’-联苯基-4-甲醛-O-甲基肟,为油状物。
1H-NMR谱(DMSO/TMS):δ=3.90(3H)ppm。
方法(i)
将5.0g(0.033mol)的4-甲酰基苯基硼酸、3.4g(0.041mol)的O-甲基羟胺盐酸盐、3.4g(0.041mol)乙酸钠、40ml甲醇和10ml水的混合物在室温下搅拌12小时。为进行后处理,将反应混合物在水中搅拌,吸滤过滤出所得沉淀,用水冲洗并在50℃下减压干燥。得到5.56g(理论值的93.1%)的4-[(甲氧基亚氨基)甲基]苯基硼酸,为无色结晶,熔点199-200℃。
方法(j)
在室温下将0.55g(4mmol)的碳酸钾和0.30g(0.0017mol)的5-氟-1,3-二甲基-1H-吡唑-4-甲酰氯加入到0.39g(1.5mmol)的2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯胺盐酸盐和20ml乙腈的混合物中。将反应混合物在室温下搅拌20小时。
为进行后处理,将反应混合物在150ml水中搅拌并用乙酸乙酯提取,提取物用硫酸钠干燥。在减压下浓缩有机相,且固体剩余物在二异丙基醚中搅拌。得到0.25g(理论值的46%)的5-氟-1,3-二甲基-N-[2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯基]-1H-吡唑-4-甲酰胺,为结晶形式,熔点100-103℃。
在上表和制备实施例中的logP值的测定是根据HPLC(高效液相色谱)的欧洲经济共同体规程79/831附件V.A8(EEC Directive79/831Annex V.A8)在反相柱(C18)上进行的。温度:43℃。
在酸性范围的测定是在pH2.3,使用的流动相为0.1%磷酸水溶液和乙腈下进行;线性梯度为10%乙腈至90%乙腈。(在表中标记为a))。
在中性范围的测定是在pH7.5,使用的流动相为0.01M磷酸缓冲水溶液和乙腈下进行;线性梯度为10%乙腈至90%乙腈。(在表中标记为b))。
进行校准是使用已知logP值的无支链的烷-2-酮(具有3-16个碳原子)(logP值是通过使用线性内插法在两个连续的链烷酮之间的保留值测定的)进行的。
λ最大值是通过使用200nm-400nmUV谱在色谱图中的最大信号测定的。
应用实施例
实施例A
柄球菌试验(苹果)/保护作用
溶剂:24.5重量份丙酮
24.5重量份二甲基乙酰胺
乳化剂:1.0重量份烷基芳基聚乙二醇醚
为了制备活性化合物适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,并将浓缩物用水稀释到所需浓度。
为了试验保护活性,用设定使用量的活性化合物的制剂向幼小植株喷雾。喷雾层干燥后,用苹果白粉病柄球菌Podosphaeraleucotricha致病真菌的孢子水悬浮液对植物接种。然后将植物放置在大约23℃和相对大气湿度大约70%的温室中。
在接种10天后进行评价。0%表示防治率与对照相同,100%防治率表示未观察到侵染。
在本试验中例如下述制备实施例的本发明化合物存在比现有技术好的活性。
实施例B
单丝壳菌试验(黄瓜)/保护作用
溶剂:24.5重量份丙酮
24.5重量份二甲基乙酰胺
乳化剂:1.0重量份烷基芳基聚乙二醇醚
为了制备活性化合物适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,并用水将浓缩物稀释到所需浓度。
为了试验保护活性,用设定使用量的活性化合物的制剂向小苗喷雾。喷雾层干燥后,用苍耳单丝壳菌Sphaerotheca fuliginea的孢子水悬浮液对植物接种。然后将植物放置在大约23℃和相对大气湿度大约70%的温室中。
在接种10天后进行评价。0%表示防治率与对照相同,100%防治率表示未观察到侵染。
在本试验中例如下述制备实施例的本发明化合物存在比现有技术好的活性。
实施例C
黑星菌试验(苹果)/保护作用
溶剂:24.5重量份丙酮
24.5重量份二甲基乙酰胺
乳化剂:1.0重量份烷基芳基聚乙二醇醚
为了制备活性化合物适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,并用水将浓缩物稀释到所需浓度。
为了试验保护活性,用设定使用量的活性化合物的制剂向幼小植株喷雾。喷雾层干燥后,用苹果黑星病Venturia inaequalis致病真菌的分生孢子水悬浮液对植物接种,然后将植物放置在大约20℃和相对大气湿度为100%的接种室中1天。
然后将植物放置在大约21℃和相对大气湿度大约90%的温室中。
在接种12天后进行评价。0%表示防治率与对照相同,100%防治率表示未观察到侵染。
在本试验中例如下述制备实施例的本发明化合物存在比现有技术好的活性。
实施例D
柄锈菌试验(小麦)/保护作用
溶剂:25重量份N,N-二甲基乙酰胺
乳化剂:0.6重量份烷基芳基聚乙二醇醚
为了制备活性化合物适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,并用水将浓缩物稀释到所需浓度。
为了试验保护活性,用设定使用量的活性化合物的制剂向幼小植株喷雾。喷雾层干燥后,用隐匿柄锈菌Puccinia recondita的分生孢子悬浮液对植物接种,然后将植物放置在20℃和相对大气湿度100%的接种室中48小时。
然后将植物放置在温度大约20℃和相对大气湿度80%的温室中,以发展锈菌疱状突起。
在接种10天后进行评价。0%表示防治率与对照相同,100%防治率表示未观察到侵染。
在本试验中例如下述制备实施例的本发明化合物存在比现有技术好的活性。
实施例E
链革孢属试验(番茄)/保护作用
溶剂:49重量份N,N-二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了制备活性化合物适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,并用水将浓缩物稀释到所需浓度。
为了试验保护活性,用设定使用量的活性化合物的制剂向番茄幼苗喷雾。处理后1天,用马铃薯早疫病链格孢Alternaria solani的孢子悬浮液对植物接种,然后将植物保留在相对大气湿度100%和20℃下24小时。然后将植物保持在相对大气湿度96%和20℃温度下。
在接种7天后进行评价。0%表示防治率与对照相同,100%防治率表示未观察到侵染。
在本试验中例如下述制备实施例的本发明化合物存在比现有技术好的活性。
表E:链革孢属试验(番茄)/保护作用
实施例F
担子菌纲大菌落的抑制试验
从密粘褶菌Gloeophyllum trabeum,单纯粉孢革菌Coniophoraputeana,卧孔菌Poria placenta,香菇Lentinus tigrinus,杂色革盖菌Coriolus versicolor的菌落中移出菌丝体部分,并在26℃接种在包括麦芽提取物蛋白胨的琼脂培养基上。将包括活性化合物的培养基对菌丝生长的抑制与没有加入活性化合物的培养基上的径向生长比较,并用抑制百分率评价。
在此试验中,例如下述制备实施例的本发明化合物具有好的活性:
Claims (21)
1.式(I)的吡唑基联苯羧酰胺类化合物:其中
R1代表氢、C1-C6-烷基、C1-C6-卤代烷基、苯甲基或吡啶甲基,
R2代表氢或C1-C6-烷基,
X代表卤素、硝基、氰基、羟基、羧基、C1-C8-烷基、带有1-5个卤素原子的C1-C6-卤代烷基、C1-C8-烷氧基、带有1-5个卤素原子的C1-C6-卤代烷氧基、C1-C8-烷硫基、带有1-5个卤素原子的C1-C6-卤代烷硫基、C2-C8-链烯氧基、C2-C8-链炔氧基、C3-C8-环烷基、C1-C8-烷氧基羰基或代表-C(R2)=N-OR1,
m代表0-3的整数,其中m代表2或3时,X代表相同或不同的基团,
Y代表卤素、硝基、氰基、羟基、羧基、C1-C8-烷基、带有1-5个卤素原子的C1-C6-卤代烷基、C1-C8-烷氧基、带有1-5个卤素原子的C1-C6-卤代烷氧基、C1-C8-烷硫基、带有1-5个卤素原子的C1-C6-卤代烷硫基、C2-C8-链烯氧基、C2-C8-链炔氧基、C3-C8-环烷基、C1-C8-烷氧基羰基或代表C1-C6-烷氧亚胺基-C1-C6-烷基和
n代表0-4的整数,其中n代表2、3或4时,Y代表相同或不同的基团。
2.根据权利要求1的式(I)吡唑基联苯羧酰胺类化合物,其中
R1代表氢、C1-C4-烷基、具有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷基、苯甲基或吡啶甲基,
R2代表氢或C1-C4-烷基,
X代表氟、氯、溴、硝基、氰基、羟基、羧基、C1-C6-烷基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷基、C1-C6-烷氧基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷氧基、C1-C6-烷硫基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷硫基、C2-C6-链烯氧基、C2-C6-链炔氧基、C3-C7-环烷基、C1-C4-烷氧基羰基或代表-C(R2)=N-OR1,
m代表0-3的整数,其中如果m代表2或3时,X代表相同或不同的基团,
Y代表氟、氯、溴、硝基、氰基、羟基、羧基、C1-C6-烷基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷基、C1-C6-烷氧基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷氧基、C1-C6-烷硫基、带有1-5个氟原子、氯原子和/或溴原子的C1-C2-卤代烷硫基、C2-C6-链烯氧基、C2-C6-链炔氧基、C3-C7-环烷基、C1-C4-烷氧基羰基或代表C1-C4-烷氧亚胺基-C1-C4-烷基,
n代表0-3的整数,其中n代表2或3时,Y代表相同或不同的基团。
3.根据权利要求1的式(I)吡唑基联苯羧酰胺类化合物,其中
R1代表氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-氯乙基、苯甲基、2-吡啶基甲基、3-吡啶基甲基或4-吡啶基甲基,
R2代表氢、甲基、乙基、正丙基、异丙基或正丁基,
X代表氟、氯、溴、硝基、氰基、羟基、羧基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氯甲基、三氟甲基、二氟甲基、二氟氯甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、三氟甲硫基、二氟氯甲硫基、烯丙氧基、炔丙氧基、环丙基、环戊基、环己基、环庚基、甲氧羰基、乙氧羰基或代表-C(R2)=N-OR1,
m代表0-2的整数,其中如果m代表2时,X代表相同或不同的基团,
Y代表氟、氯、溴、硝基、氰基、羟基、羧基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氯甲基、三氟甲基、二氟甲基、二氟氯甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、三氟甲硫基、二氟氯甲硫基、烯丙氧基、炔丙氧基、环丙基、环戊基、环己基、环庚基、甲氧羰基、乙氧羰基或甲氧亚胺基甲基,
n代表0-2的整数,其中n代表2时,Y代表相同或不同的基团。
4.根据权利要求1的式(I)的吡唑基联苯羧酰胺类化合物的制备方法,其特征在于
a)式(II)的羧酸衍生物与式(III)的苯胺衍生物反应其中
R1,R2,X,m,Y和n各自为权利要求1中所给出的定义,
如果需要反应在催化剂存在下,如果需要反应在酸结合剂和如果需要反应在稀释剂存在下进行,
或
(b)式(IV)的羧酰胺衍生物与式(V)的硼酸衍生物反应其中X和m各自如权利要求1中所定义,其中
R1,R2,Y和n各自为权利要求1中所定义和
G1和G2各自代表氢或一起代表四甲基亚乙基,
如果需要反应在催化剂存在下,如果需要反应在酸结合剂和如果需要反应在稀释剂存在下进行,
或
(c)式(VI)的羧酰胺-硼酸衍生物与式(VII)的苯基肟衍生物反应其中X和m各自如权利要求1中所定义和
G1和G2各自代表氢或一起代表四甲基亚乙基,其中
R1,R2,Y和n各自如权利要求1中所定义,
如果需要反应在催化剂存在下,如果需要反应在酸结合剂和如果需要反应在稀释剂存在下进行,
或
d)式(VIII)的联苯基酰基衍生物与式(IX)的烷氧基胺反应其中
R2,X,m,Y和n各自如权利要求1中所定义,
R1-O-NH2×HCl (IX)其中R1如权利要求1中所定义,
如果需要反应在酸结合剂和如果需要反应在稀释剂存在下进行,
或
R2,X,m,Y和n各自为权利要求1中所定义,
R3-E (X)其中R3代表C1-C6-烷基和
E代表氯、溴、碘、甲磺酰基或对甲苯磺酰基,
或R3和E一起代表硫酸(二-C1-C6-烷基)酯,
如果需要反应在酸结合剂和如果需要反应在稀释剂存在下进行,
或
R1,R2,Y和n各自如权利要求1中所定义
反应在钯或铂催化剂存在下和在4,4,4’,4’5,5,5’,5’-八甲基-2,2’-双-1,3,2-二氧硼戊环存在下,如果需要反应在酸结合剂和如果需要反应在稀释剂存在下进行。
7.式(I-d)的吡唑基联苯羧酰胺类化合物其中R1,R2,X,m,Y和n各自如权利要求1中所定义。
9.根据权利要求8的式(III)的苯胺衍生物的制备方法,其特征在于:
Hal代表卤素,其中
R1,R2,Y,n各自如权利要求1中所定义和
G1和G2各自为氢或一起代表四甲基亚乙基,
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下,和如果需要在催化剂存在下进行,
或
G1和G2各自为氢或一起代表四甲基亚乙基,其中
R1,R2,Y和n各自和权利要求1中所定义
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下,和如果需要在催化剂存在下进行。
13.根据权利要求12的式(VI)的羧酰胺-硼酸衍生物的制备方法,其特征在于,
j)式(II)的羧酸衍生物与式(XII)的苯胺硼酸反应其中G如权利要求1中所定义其中
X和m各自如权利要求1中所定义和
G1和G2各自为氢或一起代表四甲基亚乙基,
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下,和如果需要在催化剂存在下进行。
15.根据权利要求14的式(VIII)的联苯基酰基衍生物的制备方法,其特征在于
k)式(II)的羧酸衍生物与式(XIV)的2-苯甲醛-苯胺-衍生物反应其中G如权利要求1中所定义,其中
R2,X,m,Y和n各自如权利要求1中所定义,
如果需要反应在酸结合剂存在下,和如果需要在惰性有机稀释剂存在下进行。
16.式(XIV)的2-苯甲醛-苯胺-衍生物,其中R2,X,m,Y和n各自如权利要求1中所定义。
18.防治有害微生物的组合物,其特征在于,组合物包含至少一种根据权利要求1的式(I)的吡唑基联苯羧酰胺,以及填充剂和/或表面活性剂。
19.使用根据权利要求1的式(I)的吡唑基联苯羧酰胺类化合物用于防治有害微生物的用途。
20.防治有害微生物的方法,其特征在于,将根据权利要求1的式(I)的吡唑基联苯羧酰胺类化合物使用到微生物和/或其生长地。
21.防治有害微生物组合物的制备方法,其特征在于,根据权利要求1的式(I)的吡唑基联苯羧酰胺类化合物和填充剂和/或表面活性剂混合。
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US4863947A (en) * | 1985-01-11 | 1989-09-05 | Rohm And Haas | N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamides and methods of their production |
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