CN1038508C - 杂芳氧乙酰胺 - Google Patents
杂芳氧乙酰胺 Download PDFInfo
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- CN1038508C CN1038508C CN93116584A CN93116584A CN1038508C CN 1038508 C CN1038508 C CN 1038508C CN 93116584 A CN93116584 A CN 93116584A CN 93116584 A CN93116584 A CN 93116584A CN 1038508 C CN1038508 C CN 1038508C
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
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- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
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- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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Abstract
本发明涉及下面式(Ⅰ)所示的新型杂芳氧乙酰胺及其制备方法和作为除草剂的用途。式(Ⅰ)中,R代表氢或在所有情况下代表选择取代的烷基、链烯基或链炔基,A代表二价亚烷基,Ar代表选择取代的芳基,X1、X2和X3在所有情况下各自独立地代表氢原子或基团C-R1,Z代表氧或硫,其中R1代表氢、卤素、氰基、在所有情况下代表选择取代的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、或选择取代的芳基,但是基团X1、X2和X3中至少有一个代表基团C-R1。
Description
本发明涉及新型杂芳氧乙酰胺、其制备工艺及其作为除草剂的用途。
已经知道某些杂芳氧乙酰胺,例如化合物2-(6-氯-2-苯并噁唑基氧)-N-异丙基-N-苄氧基-乙酰胺具有除草性能(参见,例如,国际申请PC T WO 9106544;美国专利4,408,055)。
但是,这些以前已知的化合物对于难以对付的杂草的除草活性以及各种重要作物对这些化合物的耐受性在各种应用领域中都不完全令人满意。
R代表氢或在所有情况下代表选择取代的烷基、链烯基或链炔基,
A代表二价亚烷基,
Ar代表选择取代的芳基,
X1、X2和X3在所有情况下各自独立地代表氢原子或基团C-R1,
Z代表氧或硫,其中
R1代表氢、卤素、氰基、在所有情况下代表选择取代的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、或选择取代的芳基,但是基团X1、X2和X3中至少有一个代表基团C-R1。
适当时,式(I)的化合物可以以几何异构体和/或旋光异构体或各种组成的异构体混合物存在,这取决于取代基的性质。本发明对纯异构体及异构体混合物提出权利要求。
此外,已经发现通式(I)的新型杂芳氧乙酰胺可由式(II)所示的取代的杂环化合物与式(III)所示的羟基乙酰胺反应制得,如果有必要的话,反应可在稀释剂、反应辅助剂和催化剂存在下进行,上述式(I)、式(II)和式(III)中:
R代表氢或在所有情况下代表选择取代的烷基、链烯基或链炔基,
A代表二价亚烷基,
Ar代表选择取代的芳基,
X1、X2和X3在所有情况下各自独立地代表氢原子或基团C-R1,
Z代表氧或硫,其中
R1代表氢、卤素、氰基、在所有情况下代表选择取代的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、或选择取代的芳基,但是基团X1、X2和X3中至少有一个代表基团C-R1。
E代表吸电子离去基团。
最后,已经发现通式(I)的新型杂芳氧乙酰胺具有除草性能。
令人惊奇的是,与先有技术中已知的杂芳氧乙酰胺,例如,化合物2-(6-氯-2-苯并噁唑基氧)-N-异丙基-N-苄氧基-乙酰胺或化合物2-(2-苯并噻唑基氧)-N-甲基-N-苯基-乙酰胺(从化学结构上和其作用观点上看都是相似的)相比,按照本发明的通式(I)的杂芳氧乙酰胺对难以控制的杂草具有相当更好的除草活性,而且各种重要作物对这些化合物具有同样好的耐受性。
式(I)给出了按照本发明的杂芳氧乙酰胺的一般定义。较好的式(I)化合物是其中各基团具有如下定义的那些化合物:
R代表氢、具有1-8个碳原子并由相同或不同取代基任选一元取代或多元取代的直链或支化烷基,适宜的取代基有:
卤素、氰基、具有1-6个碳原子的直链或支化的烷氧基础、具有1-6个碳原子的直链或支化的烷硫基或苯基;
此外还代表具有2-8个碳原子并由相同或不同卤素取代基任选一元取代或多元取代的直链或支化的链烯基,还进一步代表具有2-8个碳原子并由相同或不同卤素取代基任选一元取代或多元取代的直链或支化的链炔基,
A代表具有1-6个碳原子的直链或支化的二价亚烷基,
Ar代表具有6-10个碳原子并由相同或不同取代基一元取代或多元取代的芳基,适宜的取代基有:
卤素、氰基、硝基、在所有情况下为具有1-6个碳原子的直链或支化的烷基、烷氧基或烷硫基,或在所有情况下为直链或支化的卤烷基、卤代烷氧基、或卤代烷硫基,这些基团中每个都具有1-6个碳原子和1-13个相同或不同的卤原子,
X1、X2和X3各自独立地代表氮原子或基团C-R1,
Z代表氧或硫,其中
R1代表氢、卤素、氰基,在所有情况下代表具有1-6个碳原子的直链或支化烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,在所有情况下代表直链或支化的卤烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,这些基团中每个都具有1-6个碳原子和1-13个相同或不同的卤原子,或者代表下式所示的基团:其中R2代表氢或卤素,
R3在所有情况下代表具有1-6个碳原子的直链或支化的烷基,具有1-6个碳原子和1-13个相同或不同的卤原子的卤烷基,在各个烷基部分含有1-6个碳原子的烷氧烷基或在各个烷基部分含有1-6个碳原子的烷硫烷基,或具有6-10个碳原子并由相同或不同取代基选择性地一元取代或多元取代的芳基,适宜的取代基有:
卤素、氰基、硝基,在所有情况下为具有1-6个碳原子的直链或支化的烷基、烷氧基、或烷硫基,或在所有情况下为具有1-6个碳原子和1-13个相同或不同卤原子的直链或支化的卤烷基、卤代烷氧基或卤代烷硫基,
Z1代表氧、硫、亚磺酰基或磺酰基,但基团X1、X2或X3中至少有一个代表基团C-R1。
特别好的式(I)化合物是其中各基团具有如下定义的那些化合物:
R代表氢、具有1-6个碳原子并被任选一元取代的直链或支化烷基,适宜的取代基有:
氰基、具有1-4个碳原子的直链或支化的烷氧基,具有1-4个碳原子的直链或支化的烷硫基或苯基;
或R代表具有1-4个碳原子和1-9个相同或不同卤原子的直链或支化卤烷基,
此外R还代表具有2-6个碳原子并由相同或不同卤素取代基任选一元至三元取代的直链或支化的链烯基,
R还可代表具有2-6个碳原子并由相同或不同卤素取代基任选一元至三元取代的直链或支化的炔基,
A代表具有1-4个碳原子的直链或支化的二价亚烷基,
Ar代表由相同或不同取代基一元至三元取代的苯基,适宜的取代基有:
卤素、氰基、硝基,在所有情况下为具有1-4个碳原子的直链或支化的烷基、烷氧基或烷硫基,或在所有情况下为具有1-4个碳原子和1-9个相同或不同卤原子的直链或支化的卤烷基、卤代烷氧基、或卤代烷硫基,
X1、X2和X3在所有情况下各自独立地代表氮原子或基团C-R1,
Z代表氧或硫,其中
R1代表氢、卤素、氰基,在所有情况下代表具有1-4个碳原子的直链或支化烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,在所有情况下代表直链或支化的卤烷基、卤代烷基氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,这些基团中每个都具有1-4个碳原子和1-9个相同或不同的卤原子,或者代表下式所示的基团:其中R2代表氢或卤素,
R3在所有情况下代表具有1-4个碳原子的直链或支化的烷基,具有1-4个碳原子和1-9个相同或不同卤原子的卤烷基,在各个烷基部分含有1-4个碳原子的烷氧烷基或在各个烷基部分含有1-4个碳原子的烷硫烷基,或者代表由相同或不同取代基任选一元至三元取代的苯基,适宜的取代基有:
卤素、氰基、硝基,在所有情况下为具有1-4个碳原子的直链或支化的烷基、烷氧基或烷硫基,或在所有情况下为具有1-4个碳原子和1-9个相同或不同卤原子的直链或支化的卤烷基、卤代烷氧基或卤代烷硫基,
Z1代表氧、硫、亚磺酰基或磺酰基,但基团X1、X2或X3中至少有一个代表基团C-R1。
更特别好的式(I)化合物是其中各基团具有如下定义的那些化合物:
R代表氢、具有1-4个碳原子并被任选一元取代的直链或支化的烷基,适宜的取代基有:
氰基、具有1-3个碳原子的直链或支化的烷氧基,具有1-3个碳原子的直链或支化的烷硫基或苯基;
或R代表具有1-3个碳原子和1-7个相同或不同卤原子(特别是氟、氯和/或溴)的直链或支化卤烷基,
此外R还代表具有2-4个碳原子并由相同或不同卤素取代基,尤其氟、氯和/或溴,任选一元或二元取代的直链或支化的链烯基,
R还可代表具有2-4个碳原子并由相同或不同卤素取代基,尤其氟、氯和/或溴,任选一元或二元取代的直链或支化的链炔基,
A代表具有1-3个碳原子的直链或支化的二价亚烷基,
Ar代表由相同或不同取代基一元或二元取代的苯基,适宜的取代基有:
氟、氯、溴、氰基、硝基、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、甲氧基、乙氧基、正-或异-丙氧基,正-、异-、仲-或叔-丁氧基、甲硫基、乙硫基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基或二氟甲硫基,
X1、X2和X3在所有情况下各自独立地代表氮原子或基团C-R1,
Z代表氧或硫,其中
R1代表氢、卤素、尤其氟、氯和/或溴,氰基,在所有情况下代表具有1-3个碳原子的直链或支化的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,在各种情况下代表直链或支化的卤烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,这些基团中每个都具有1-3个碳原子和1-7个相同或不同的卤原子,尤其氟、氯和/或溴,或者代表下式所示的基团:其中R2代表氢或氟或氯,
R3在所有情况下代表具有1-3个碳原子的直链或支化的烷基,具有1-3个碳原子和1-7个相同或不同卤原子,尤其氟、氯和/或溴原子的卤烷基,在各个烷基部分含有1-3个碳原子的烷氧烷基或在各个烷基部分含有1-3个碳原子的烷硫烷基,或者代表由相同或不同取代基任选一元或二元取代的苯基,适宜的取代基有:
氟、氯、溴、氰基、硝基、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、甲氧基、乙氧基、正-或异-丙氧基,正-、异-、仲-或叔-丁氧基,甲硫基、乙硫基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基或二氟甲硫基,
Z1代表氧、硫、亚磺酰基或磺酰基,但其中基团X1、X2或X3中至少有一个代表基团C-R1。
除了在制备实例中提到的化合物之外,可以特别提到的式(I)的杂芳氧乙酰胺如下:
式(II)给出了作为实施本发明工艺的起始化合物所需的取代杂环的一般定义。在式(II)中,X1、X2、X3和Z较好代表在叙述本发明式(I)的物质时作为这些取代基较好的例子所提到的那些基团。
E代表普通的离去基团,较好是卤素,尤其氯、溴或碘,或者在所有情况下代表任选取代的烷基磺酰氧基或芳基磺酰氧基,例如,尤其甲磺酰氧基、三氟甲磺酰氧基或对甲苯磺酰氧基。
式(II)的取代杂环是已知的,或者可用类似已知工艺制得(如参照EP348,737)。
式(III)给出了作为实施本发明工艺的离析物进一步所需的羟基乙酰胺的一般定义。在式(III)中,R、A和Ar较好代表在叙述本发明式(I)的物质时作为这些取代基较好的例子所提到的那些基团。
式(III)的羟基乙酰胺是已知的,或者可用类似已知工艺制得(如参照国际申请PCT WO 9106544)。
适用于实施本发明工艺的稀释剂是惰性有机溶剂。这些溶剂尤其包括:脂族、脂环族或芳族任选卤化的烃类,例如,汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚类,如二乙基醚、二异丙基醚、二噁烷、四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;酮类,如丙酮、丁槽或甲基异丁基酮;腈类,如乙腈、丙腈或苯甲腈;胺类,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;酯类,如乙酸甲酯或乙酸乙酯;亚砜,如二甲基亚砜;醇类,如甲醇、乙醇、正丙醇或异丙醇,其与水的混合物,纯水或含水盐溶液。
本工艺优选使用的盐是碱金属或碱土金属的氯化物或硫酸盐,例如氯化钠、氯化钾或氯化钙。氯化钠水溶液是特别好的。
本发明工艺较好是在适当的反应辅助剂存在下进行。适用的反应辅助剂是所有常用的无机碱或有机碱。例如包括碱土金属的氢氧化物或碱金属的氢氧化物,如氢氧化钠、氢氧化钙、氢氧化钾或者氢氧化铵,碱金属碳酸盐,如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵、碱金属乙酸盐或碱土金属乙酸盐,如乙酸钠、乙酸钾、乙酸钙或乙酸铵以及叔胺化合物,如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、吡啶、哌啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮二环辛烷(DABCO)、二氮二环壬烯(DBN)或二氮二环十一烯(DBU)。
如果合适的话,本发明的工艺也可在两相体系中,如在水/甲苯或水/二氯甲烷中进行,如合适,可在适当相转移催化剂存在下进行。可以提及的这类催化剂的例子有;碘化四丁胺、溴化三丁基甲基磷、氯化三甲基C13/C15烷基铵、溴化三甲基C13/C15烷基铵、二苄基二甲基铵硫酸甲酯盐、氯化二甲基C12/C14烷基苄基铵、溴化二甲基C12/C14烷基苄基铵、氢氧化四丁基铵、氯化三乙基苄基铵、氯化甲基三辛基铵、氯化三甲基苄基铵、15-冠(醚)-5、18-冠(醚)-6或三-[2-(2-甲氧基乙氧基)-乙基]-胺。
进行本发明的工艺时,反应温度可以在相当大的范围内变化。通常,本工艺在-50-110℃的温度范围进行,较好在-20-80℃之间进行。
为实施本发明的工艺,对每摩尔式(II)的取代杂环通常使用0.5-5.0摩尔,较好0.8-1.5摩尔式(III)的羟基乙酰胺,0.5-5.0摩尔,较好0.8-1.5摩尔的碱作为反应辅助剂,且如合适的话,使用0.001-2.0摩尔,较好0.001-1.0摩尔的相转移催化剂。
反应完成之后用已方法(在此请参照,例如EP 348,737或国际申请PCT WO 9106544或制备实例)将反应产物进行后处理并分离。
用通用方法,如柱色谱法或重结晶精制式(I)的最终产物。
这些化合物可用熔点表征,或者,在这些化合物不能结晶的情况下,可用折射指数或质谱数据(1H NMR)表征。
按照本发明的活性化合物可以用作脱叶剂、干燥剂、阔叶植物毁灭剂,尤其可用作除草剂。所谓杂草,在最广阔的意义上,要理解成一切生长在不希望其出现的位置上的植物。按照本发明的物质是否起到灭生性除草剂或选择性除草剂的作用,基本上取决于用量。
按照本发明的活性化合物的使用可涉及诸如下列植物:
以下各属双子叶杂草:芸苔属,独行菜属,猪殃殃属,繁缕属,母菊属,春黄菊属,牛膝菊属,藜属,荨麻属,千里光属,苋属,马齿苋属,齿苋属,苍耳属,旋花属,番薯属,蓼属,田菁属,豚草属,蓟属,飞廉属,苦苣菜属,茄属,焊菜属,水松叶属,母草属,野芝麻属,婆婆纳属,麻属,刺酸模属,曼陀罗属,堇菜属,鼬瓣花属,罂粟属,矢车菊属,三叶草属,毛莨属和蒲公英属。
以下各属双子叶栽培作物:棉属,大豆属,菾菜属,胡罗卜属,菜豆属,豌豆属,茄属,亚麻属,番薯属,巢菜属,烟草属,番茄属,花生属,蒪菜属,莴苣属,黄瓜属和南瓜属。
以下各属单子叶杂草:稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,羊茅属,蟋蟀草属,臂形草属,黑麦草属,雀麦属,燕麦属,莎草属,蜀黍属,冰草属,狗牙根属,雨久花属,飘拂草属,慈姑属,荸荠属,蔗草属,雀稗属,鸭嘴草属,尖瓣花属,龙爪茅属,翦股颖属,看麦娘属和野豚鼠草属(Apera)。
以下各属单子叶栽培作物:稻属,玉蜀黍属,小麦属,大麦属,燕麦属,黑麦属,蜀黍属,黍属,甘蔗属,凤梨属,天门冬属和葱属。
然而,按照本发明的活性化合物的用途绝不仅限于以上各属,而且也以同样的方式扩展到其它植物。
因浓度而异,这类化合物适合于诸如工业场地和铁路线上以及有或无树林的道路和广场上的灭生性除草。同样,这类化合物也可用于多年生栽培植物如造林、装饰性园林、果树园、葡萄园、桔园、坚果园、香蕉园、咖啡园、茶园、橡胶园、油棕园、可可园、软果园和酒花田除草,草坪、草地和牧场除草,以及一年生栽培植物的选择性除草。
在这方面,按照本发明的活性化合物可特别成切地用来防冶双子叶栽培作物,例如大豆中的单子叶杂草。
这些活性化合物可以转变成习用配方,例如溶液、乳液、可湿性粉剂、悬浮液、粉剂、尘剂、膏剂、可溶性粉剂、颗粒剂、悬浮液-乳液浓制剂、浸渍了活性化合物的天然材料和合成材料、及包入聚合物材料中的甚微细胶囊。
这些配方是用已知方法生产的,例如将活性化合物与增充剂即液体溶剂、加压下的液化气体和/或固体载体混合,任选地使用表面活性剂即乳化剂和/或分散剂和/或泡沫形成剂。
在使用水作为增充剂的情况下,有机溶剂等也可以用作为助溶剂。作为液体溶剂,适用的主要有:芳烃,如二甲苯、甲苯或烷基萘;氯代芳烃或氯代脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷或链烷烃,例如石油馏分、矿物油和植物油;醇类如丁醇或二醇,及其醚类和酯类;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。
作为固体载体,适用的有:例如铵盐和研磨的天然无机物,如高岭土、粘土、滑石、白垩、石英、美国活性白土、蒙脱土或硅藻土,及研磨的合成无机物,如高分散的二氧化硅、氧化铝和硅酸盐;作为颗粒剂的固体载体,适用的有;例如粉碎并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,和有机材料如锯末、椰子壳、玉米芯和烟草杆的颗粒;作为乳化剂和/或泡沫形成剂,适用的有:例如非离子型和阴离子型乳化剂,如聚氧乙烯脂肪酸酯、聚氧化乙烯脂肪醇醚,例如烷芳基聚二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;作为分散剂,适用的有:例如木质素亚硫酸盐废液和甲基纤维素。
在这些配方中可以使用粘合剂如羧甲基纤维素及粉末、颗粒或胶乳等形成的天然与合成聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷酯和卵磷脂,和合成磷脂。进一步可能的添加剂是矿物油和植物油。
也可以使用着色剂,如无机颜料,诸如氧化铁、氧化钛和普鲁士蓝,和有机染料,诸如茜素染料、偶氮染料和金属酞菁染料,及痕量营养物,如铁、锰、硼、铜、钴、钼和锌的盐类。
这些配方一般含有0.1%~95%(重量)活性化合物,较好是0.5%~90%。
为了控制杂草,按照本发明的活性化合物(原药或其配方形式)也可与已知的除草剂(成品配方或可能的罐混物)形成混合物再使用。
用于这类混合物的适合除草剂是已知的除草剂,例如酰替苯胺类,如二氟酚(diflufenican)和敌稗;芳基羧酸类,如二氯吡啶甲酸、麦草畏和毒莠定;芳氧基链烷酸类,如2,4-D(2,4-滴)、2,4-DB(2,4-滴丁酸)、2,4-DP(2,4-滴丙酸)、氟氧吡啶(fluroxypyr)、MCPA(2甲4氯)、M CPP(2甲4氯丙酸)和木草畏(triclopyr);芳氧基-苯氧基链烷酸酯,如禾草灵(diclofop-methyl),乙基酚丙酸(fenoxaprop-ethyl),禾草枯(fulazifop-buryl),甲基海酚丙(haloxyfop-methyl)和2-[4-[(6-氯-2-喹喔啉基)氧]苯氧基]丙酸乙酯(quizalofop-ethyl),azinone类,例如5-氨基-4-氯-2-苯基哒嗪-3(2H)-酮(Chloridazon)和哒草灭;氨基甲酸酯类,例如氯苯胺灵、异苯敌、苯敌草和苯胺灵,氯乙酰替苯胺类,例如草不绿、灭草胺、去草胺、甲吡唑安(metazachlor),甲代隆、氯苯胺和毒草胺;二硝基苯胺类,例如黄草消、芽草平和氟乐灵;二苯醚类,例如氟草灭,治草醚,氟糖酚(fluoroglycofen),虎威,halosafen,乳酚(lactofen)和氟草胺;脲类,例如绿麦隆,敌草隆,伏草隆,异丙隆,利谷隆和噻唑隆;羟胺类,例如枯杀达,乙氧定(c lethodim)环氧定(cycloxydim),禾莠净和烷氧定(tralkoxydim);咪唑啉酮类,例如咪唑乙畏(imazethapyr),咪唑甲苯(imazamethabenz),咪唑吡啶(imazapyr)和咪唑喹啉(imazaquin);腈类,例如溴苯腈,敌草腈和碘苯腈;氧乙酰胺类,例如mefenacet;磺酰脲类,例如amidosulfuron,甲基苯磺隆(bensulfuron-methyl),乙基氯默隆(chlorimuron-ethyl),阔草脲,cinosulfuron,甲基甲磺隆(metoulfuron-methyl),nicosulfuron,primisulfuron,乙基吡唑杀隆(pyrazosulfuron-ethyl),甲基西酚杀隆(thifensulfuron-methyl),三硫隆(triasulfuron)和甲三苯隆(tribenuron-methyl);硫代氨基甲酸酯类,例如苏达灭,草灭特,燕麦敌,扑草灭,esprocarb,草达灭,扑硫威(prosulphocarb),杀草丹和野麦畏;三嗪类,例如阿特拉津,草净津,西玛津,西草净,去草净和特丁津(terbuthylazin e);三嗪酮类,例如敌草灵(hexazinone),灭它通(metamitron)和赛克津;及其它除草剂,例如氨基三唑,benfuresate,噻草平,辛甲灵(cinmethylin),氯马腙(clomazone),氯吡啶(clopyralid),燕麦清(difenzoquat),dithiopyr,草定完,卤吡咯酮(fluorochloridone),glufosinate,草甘膦,异噁苯(isoxaben),草利达(pyridate),quinchlorac,quinmerac,sulphosate和2-(3,5-二氯(苯基)-2-(2,2,2-三氯乙基)环氧乙烷(tridiphane)。
与其它已知活性化合物如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养剂及土壤结构改良剂的混合物也可以使用。
这些活性化合物可以原药形式、其配方形式、或通过进一步稀释而从其制备的使用形式例如可直接使用的溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂加以使用。它们是以浇水、喷雾、雾化或喷洒等习用方式使用的。
按照本发明的活性化合物既可以在植物发芽前也可在植物发芽后施用。
它们也可以在播种前混入土壤中。
活性化合物的用量可以在一个很大的范围内变化。这基本上取决于预期效果的性质。一般地说,用量是每公顷土壤表面为0.01-10千克活性化合物,较好是0.05~5千克/公顷。
下面实例可以说明本发明活性化合物的制备方法和用途。
制备实例:
7.1克(0.025摩尔)N-异丙基-N-苄氧基-羟基乙酰胺、5.8克(0.025摩尔)2-甲磺酰基-5-三氟甲基-1,3,4-噻二唑、3.7克(0.027摩尔)碳酸钾和0.5克溴化四丁铵在50毫升丙酮中的悬浮液于0℃-5℃搅拌12小时。为进行后处理,将水加入到反应混合物中,混合物用甲基·叔丁基醚萃取,有机相用水洗涤并在硫酸钠上干燥,最后在真空中除去溶剂。得到9.0克(理论产量的96%)2-[(5-三氟甲基-1,3,4-噻二唑-2-基)-氧]-N-异丙基-N-苄氧基-乙酰胺油状物,其折射率为nD 20=1.4945。
用类似方法制得了下面通式(I)的杂芳氧乙酰胺:
应用实例:
实例A
芽前试验/温室
溶剂:5重量份丙酮
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的适当制剂,可将1重量份该活性化合物与上述规定量的溶剂混合,加入上述规定量的乳化剂,用水将浓液稀释至所要求的浓度。
将试验植物的种子种于正常的土壤中,24小时后用活性化合物的制剂浇灌。较好是使每单位面积的水量保持恒定。制剂中活性化合物的浓度并不重要,只有每单位面积所施用的活性化合物的量才是决定性的。三周后,与未处理的对照植物的生长情况相比,定出对植物的损害程度,以损害%表示。
该数据表示:
%=没有影响(象未处理的对照植物)
100%=全部推毁。
本试验表明,与先有技术相比,本发明的化合物,例如制备实例1,2和4的化合物,具有明显优异的活性且在作物中有类似的良好的选择性。
Claims (4)
1.通式(I)的杂芳氧乙酰胺式中:
R代表氢、具有1-4个碳原子并任选被一元取代的直链或支化的烷基,适宜的取代基有:
氰基、具有1-3个碳原子的直链或支化的烷氧基,具有1-3个碳原子的直链或支化的烷硫基或苯基,
或R代表具有1-3个碳原子和1-7个相同或不同卤原子的直链或支化卤烷基,
此外R还代表具有2-4个碳原子并任选被相同或不同卤素取代基一元或二元取代的直链或支化的链烯基,以及
R还代表具有2-4个碳原子并任选被相同或不同卤素取代基一元或二元取代的直链或支化的链炔基,
A代表具有1-3个碳原子的直链或支化的二价亚烷基,
Ar代表由相同或不同取代基一元或二元取代的苯基,适宜的取代基有:
氟、氯、溴、氰基、硝基、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、甲氧基、乙氧基、正-或异-丙氧基,正-、异-、仲-或叔-丁氧基,甲硫基、乙硫基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基或二氟甲硫基,
X1、X2和X3在所有情况下各自独立地代表氮原子或基团C-R1,
Z代表氧或硫,其中
R1代表氢,卤素,氰基,在各种情况下具有1-3个碳原子的直链或支化的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,在各种情况下直链或支化的卤烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,这些基团中每个都具有1-3个碳原子和1-7个相同或不同的卤原子,或者代表下式所示的基团:其中R2代表氢、氟或氯,
R3代表在每种情况下具有1-3个碳原子的直链或支化的烷基,具有1-3个碳原子和1-7个相同或不同卤原子的卤烷基,在各个烷基部分含有1-3个碳原子的烷氧烷基或在各个烷基部分含有1-3个碳原子的烷硫烷基,或者代表任选被相同或不同取代基一元或二元取代的苯基,适宜的取代基有:
氟、氯、溴、氰基、硝基、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、甲氧基、乙氧基、正-或异-丙氧基,正-、异-、仲-或叔-丁氧基,甲硫基、乙硫基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基或二氟甲硫基,
Z1代表氧、硫、亚磺酰基或磺酰基,但其中基团X1、X2或X3中至少有一个代表基团C-R1。
2.通式(I)杂芳氧乙酰胺的制备方法:式中:
R代表氢、具有1-4个碳原子并任选被一元取代的直链或支化的烷基,适宜的取代基有:
氰基、具有1-3个碳原子的直链或支化的烷氧基,具有1-3个碳原子的直链或支化的烷硫基或苯基,
或R代表具有1-3个碳原子和1-7个相同或不同卤原子的直链或支化卤烷基,
此外R还代表具有2-4个碳原子并任选被相同或不同卤素取代基一元或二元取代的直链或支化的链烯基,以及
R还代表具有2-4个碳原子并任选被相同或不同卤素取代基一元或二元取代的直链或支化的链炔基,
A代表具有1-3个碳原子的直链或支化的二价亚烷基,
Ar代表由相同或不同取代基一元或二元取代的苯基,适宜的取代基有:
氟、氯、溴、氰基、硝基、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、甲氧基、乙氧基、正-或异-丙氧基,正-、异-、仲-或叔-丁氧基,甲硫基、乙硫基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基或二氟甲硫基,
X1、X2和X3在所有情况下各自独立地代表氮原子或基团C-R1,
Z代表氧或硫,其中
R1代表氢,卤素,氰基,在各种情况下具有1-3个碳原子的直链或支化的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,在各种情况下直链或支化的卤烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,这些基团中每个都具有1-3个碳原子和1-7个相同或不同的卤原子,或者代表下式所示的基团:其中R2代表氢、氟或氯,
R3代表在每种情况下具有1-3个碳原子的直链或支化的烷基,具有1-3个碳原子和1-7个相同或不同卤原子的卤烷基,在各个烷基部分含有1-3个碳原子的烷氧烷基或在各个烷基部分含有1-3个碳原子的烷硫烷基,或者代表任选被相同或不同取代基一元或二元取代的苯基,适宜的取代基有:
氟、氯、溴、氰基、硝基、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、甲氧基、乙氧基、正-或异-丙氧基,正-、异-、仲-或叔-丁氧基,甲硫基、乙硫基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基或二氟甲硫基,
Z1代表氧、硫、亚磺酰基或磺酰基,但其中基团X1、X2或X3中至少有一个代表基团C-R1,
该方法的特征在于,使式(II)的取代杂环与式(II)的羟基乙酰胺反应,如果有必要的话,反应可在稀释剂、反应辅助剂和催化剂存在下进行,式中,X1、X2、X3、Z、R、A和Ar的定义如上所述,E代表吸电子离去基团。
3.除草剂,其特征在于,它们含有至少一种权利要求1的通式(I)的杂芳氧乙酰胺。
4.权利要求1的通式(I)的杂芳氧乙酰胺用于抵抗不希望植物的用途。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE4229193A DE4229193A1 (de) | 1992-09-02 | 1992-09-02 | Heteroaryloxyacetamide |
DEP4229193.3 | 1993-09-02 |
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Publication Number | Publication Date |
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CN1085900A CN1085900A (zh) | 1994-04-27 |
CN1038508C true CN1038508C (zh) | 1998-05-27 |
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Application Number | Title | Priority Date | Filing Date |
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CN93116584A Expired - Fee Related CN1038508C (zh) | 1992-09-02 | 1993-09-02 | 杂芳氧乙酰胺 |
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EP (1) | EP0585756A3 (zh) |
JP (1) | JPH06263747A (zh) |
KR (1) | KR940007013A (zh) |
CN (1) | CN1038508C (zh) |
DE (1) | DE4229193A1 (zh) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0029171A1 (de) * | 1979-11-17 | 1981-05-27 | Bayer Ag | Azolyloxy-carbonsäure-N-oxy-amide, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Verwendung, sie enthaltende herbizide Mittel und deren Herstellung |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH03204867A (ja) * | 1989-10-31 | 1991-09-06 | Hokko Chem Ind Co Ltd | アラルキルオキシアミン誘導体および除草剤 |
-
1992
- 1992-09-02 DE DE4229193A patent/DE4229193A1/de not_active Withdrawn
-
1993
- 1993-08-20 EP EP19930113340 patent/EP0585756A3/de not_active Withdrawn
- 1993-08-27 JP JP5234283A patent/JPH06263747A/ja active Pending
- 1993-09-02 CN CN93116584A patent/CN1038508C/zh not_active Expired - Fee Related
- 1993-09-30 KR KR1019930017062A patent/KR940007013A/ko not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0029171A1 (de) * | 1979-11-17 | 1981-05-27 | Bayer Ag | Azolyloxy-carbonsäure-N-oxy-amide, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Verwendung, sie enthaltende herbizide Mittel und deren Herstellung |
Also Published As
Publication number | Publication date |
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EP0585756A3 (en) | 1994-05-18 |
KR940007013A (ko) | 1994-04-26 |
DE4229193A1 (de) | 1994-03-03 |
JPH06263747A (ja) | 1994-09-20 |
CN1085900A (zh) | 1994-04-27 |
EP0585756A2 (de) | 1994-03-09 |
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