CN1033050A - 嘧啶衍生物及其制备方法和其除草剂组合物及除草方法 - Google Patents
嘧啶衍生物及其制备方法和其除草剂组合物及除草方法 Download PDFInfo
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- CN1033050A CN1033050A CN88107663A CN88107663A CN1033050A CN 1033050 A CN1033050 A CN 1033050A CN 88107663 A CN88107663 A CN 88107663A CN 88107663 A CN88107663 A CN 88107663A CN 1033050 A CN1033050 A CN 1033050A
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- Prior art keywords
- salt
- alkyl group
- pyrimidine derivatives
- low alkyl
- molecular formula
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- 238000000034 method Methods 0.000 title claims description 21
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- 238000002360 preparation method Methods 0.000 title claims description 13
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- 235000015320 potassium carbonate Nutrition 0.000 description 1
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical class [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
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- 238000009331 sowing Methods 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
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- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
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- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
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- General Health & Medical Sciences (AREA)
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- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catching Or Destruction (AREA)
Abstract
具有分子式为(I)为嘧啶衍生物,
其中X为卤原子,低级烷基或苯氧基(所述的苯
氧基可以被卤原子,低级烷基或低级烷氧基取代),R
为卤原子,低级烷基,烷氧基烷基,苄氧基烷基,烷氧
苯羰基烷基,氰烷基或
基团(其中R1为
氢原子或低级烷基,R2为低级烷基或,可被硝基取代
的苯基),或者其盐。
Description
本发明涉及新颖嘧啶衍生物或其盐,它们的生产方法,以其为组份的除草组合物和使用这些物质的除草方法。
最近,已研制开发了一大批除草剂并已用于实践,除草剂为节约农业作业的能源和提高生产的效率作出了贡献。另外,已知各种2-苯氧基嘧啶衍生物作为除草剂是有效的[(1)日本待审公开专利174059/1987,(2)日本待审公开专利55729/1979和(3)农业生物化学30卷第9号896页(1966)]。
然而,在上述参考文献(1)中公开的化合物,尽管它们显示出高效除草效应,但对农作物有个安全性问题。另外,在上述参考文献(2)和(3)中公开的化合物的不足在于其对一年生草类的除草活性是不够的,对多年生草类也没有显示出显著的除草活性。
本发明者对嘧啶衍生物进行了广泛的研究以研制开发一种具有更优异除草活性的化合物,结果发现本发明的在苯基硫嘧啶衍生物的嘧啶和苯环上的特定位置引入取代物的化合物对多年生草类及一年生草类显示出优异的除草效果,同时,它们对农作物,特别是对于棉花,具有高度安全性。本发明的完成是基于这些发现。
本发明提供的嘧啶衍生物具有一般式:
其中X为诸如氯、溴、磺或氟的卤素原子,低级烷基,特别是C1-C4烷基,或苯氧基(其中所述的苯氧基可以被诸如氯、溴、磺或氟的卤原子,低级烷基,特别是C1-C4烷氧基取代,或低级烷氧基,特别是C1-C4烷氧基取代),R为卤原子,低级烷基,特别是C1-C6烷基,烷氧基烷基,特别是C1-C4烷氧基C1-C4烷基,苄氧基烷基,特别是苄氧基C1-C4烷基,烷氧羰基烷基,特别是C1-C4烷氧羰基C1-C4烷基,氰基烷基或 基团(其中R1为氢原子或低级烷基,特别是C1-C4烷基,R2为低级烷基,特别是C1-C4烷基或可以被硝基取代的苯基),或者为其盐。
本发明还提供了包含除草有效量的分子式为Ⅰ的嘧啶衍生物或其盐的除草剂组合物,和农用辅剂。
另外,本发明提供了除草的方法,该方法包括把具有除草作用的有效量的分子式Ⅰ的嘧啶衍生物或其盐施加到要治理的场所。
现以较好的具体例子来详细说明本发明。
在分子式Ⅰ中,X较好地是在6-位取代,特别是X为在6-位的氯原子,甲基或氟原子。
R较好的是氢原子,低级烷基,烷氧基烷基或苄氧基烷基。最好的是氢原子。
在分子式Ⅰ的化合物中,较好的是下列一般式Ⅰ-1和Ⅰ-2。
其中R如权项1中所定义的,X为卤素原子或低级烷基;
基中R如权项1中所定义的,Y为氢原子,卤素原子,低级烷基或低级烷氧基。
现将本发明化合物的具体例子列于表1。表中所给的化合物的编号与说明书械拿枋鏊承蛳喽杂Α?
在本发明的化合物中,苯甲酸衍生物(其中的R为氢原子)或其盐显示出特别优异的除草效果。
盐,可以是碱金属盐,碱土金属盐,过渡金属盐或有机铵盐。
编号为1,2,11,12,17,18,21的化合物及其盐对作物,特别是棉花,在具有优异除草活性和无明显植物毒性方面是特别上乘的。
本发明的化合物可以下列方法制备,
式中,Y1为卤素原子,烷基磺酰基,或者为取代的或未取代的苄磺酰基,X和R如前所定义的。
本发明的一般式为Ⅰ的化合物可以通过将分子式Ⅱ的化合物与分子式Ⅲ的化合物在碱存在下,较好地是于溶剂中,在室温至溶剂沸点的温度区间内反应1至24小时而得。当反应在无溶剂情况下进行,反应可在120至160℃的温度范围内用碱金属碳酸盐作为碱进行,比如无水碳酸钾。
该反应中所用的溶剂包括,举例来说有,诸如苯、甲苯或二甲苯的烃溶剂,诸如二氯甲烷或氯仿的卤代烃,诸如甲醇、乙醇、异丙醇的醇类溶剂,诸如乙醚、异丙醚、四氢呋喃、1,4-二噁烷的醚类溶剂,诸如丙酮或甲乙酮的酮类溶剂,诸如乙酸甲酯或乙酸乙酯的酯类溶剂,诸如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺或二甲基亚砜的非质子传递的非极性溶剂以及乙腈和水。
碱,可以是诸如钠或钾的碱金属,碱金属氢化物或碱土金属氢化物,比如,氢化钠、氢化钾或氢化钙;诸如碳酸钠、碳酸钾、碳酸氢钠或碳酸氢钾的碳酸盐;以及诸如氢氧化钠或氢氧化钾的金属氢氧化物。
另外,本发明的化合物还可按下述方法制得,
式中,R和X如前所定义的。
分子式Ⅰ的化合物可以通过将由分子式Ⅳ的化合物转化过来的分子式Ⅴ的重氮盐与分子式Ⅵ的化合物在碱溶液中于低温,特别是在-20℃至10℃的温度范围内反应而得。
如重氮盐,氢硼酸盐、氢碘酸盐、四氟硼酸盐或硫酸盐可以加至盐酸中。另外,碱溶液可以通过将诸如氢氧化钠,氢氧化钾,氢氧化钡或氢氧化钙等强碱加入溶剂中配制而成。
分子式Ⅰ的2-[(4,6-二甲氧基嘧啶-2-基)硫代]苯甲酸衍生物可按上述方法制得,可以与碳酸氢钠,氢氧化钠,氢氧化钾,氢化钠或类似物反应转化成其相应的碱金属盐。然后,可以使氯化钙与碱金属盐反应,或碳酸钙或氢化钙与相应的苯甲酸反应以得到碱土金属盐。还有,将氯化铁或类似物与碱金属盐反应使其转化成过渡金属盐,比如铁盐。
进一步,还可以将苯甲酸通过让它与诸如一级胺,二级胺,三级胺,二乙醇胺,三乙醇胺,烷氧基烷基胺,环己胺或吗啉的脂族胺,或者与诸如苯胺或萘胺的芳族胺反应而转化成有机铵盐。
下面结合实施例进一步详细描述本发明,然而,应该明白本发明不只限于这些特别的例子。
实施例1
2-[(4,6-二甲氧基嘧啶-2-基)硫代]-6-甲基苯甲酸(编号2的化合物)的制备
将50克2=氨基=6=甲基苯甲酸盐酸盐用浓盐酸和2.3克亚硝酸钠转化成重氮盐。然后,于0至5℃,将该重氮盐逐滴滴入预先准备好的二硫化钠溶液中(用8.7克硫化钠,1.1克硫,1.5克氢氧化钠和15毫升水配成),滴加完成后,混合液于室温搅拌2小时以完全反应。将反应溶液倒入大量水中,往其中加入浓盐酸。然后,用乙酸乙酯抽提混合物,将碳酸氢钠水溶液加到乙酸乙酯层中,碳酸氢钠可溶成份就被抽提出来。将5.8克焦硫酸钠加至水溶液中,再将混合物回流30分钟以完全反应。往反应溶液中加入浓盐酸,然后用乙酸乙酯抽提混合物,干燥抽提液,接着减压蒸出溶剂,得到3.6克(产率65%)的2-巯基-6-甲基苯甲酸。
随后,将3.6克2-巯基-6-甲基苯甲酸,4.7克4,6-二甲氧基-2-甲基磺酰嘧啶和3.5克无水碳酸钾溶于20毫升二甲基甲酰胺中,然后,于110至120℃搅拌混合物1小时,将反应溶液倾入大量水中,往其中加入浓盐酸。接着,用氯仿抽提混合物,氯仿层用水洗涤后再干燥,然后减压蒸去溶剂。粗晶体用己烷/乙酸乙酯作展开剂的柱上色谱层析法提纯,再从乙酸乙酯中重结晶得到0.8克2-[(4,6-二甲氧基嘧啶-2-基]硫代-6-甲基苯甲酸,为白色粉状,熔点为131-132℃。
实施例2
2-氯-6-[(4,6-二甲氧基嘧啶-2-基)硫代]苯甲酸(编号为1的化合物)的制备
将5.0克2-氨基-6-氯代苯甲酸盐酸盐用2.3克亚硝酸钠和浓盐酸转化成重氮盐。然后,该重氮盐于0℃逐滴加入含有4.8克4,6-二甲氧基-2-巯基嘧啶,2.4克氢氧化钠和40毫升水的溶液中,在滴加完成后,在室温下搅拌该混合物液2小时以完全反应。将浓盐酸加入反应液中的,然后,用乙酸乙酯抽提混合液,干燥抽提液,再减压蒸去溶剂。所得残留物经色谱层析法提纯得到1.8克2-氯-6-[(4,6-二甲氧基嘧啶-2-基)硫代]苯甲酸,为赭色粉状,熔点为148-151℃。
实施例3
2-氯-6-[(4,6-二甲氧基嘧啶-2-基)硫代]苯甲酸三乙醇铵(编号为25的化合物)的制备
将1.57克2-氯-6-[(4,6-二甲氧基嘧啶-2-基)硫代苯甲酸和0.72克三乙醇胺溶于20毫升的四氢呋喃中,于室温下搅拌该溶液30分钟。将溶剂从溶液中蒸出,将异丙醚加到残留物中使之固化。过滤分离出固体,然后干燥,得到2.0克2-氯-6-[(4,6-二甲氧基嘧啶-2-基)硫代]苯甲酸三乙醇铵,为白色固体,熔点为94-101℃。
本发明的除草组合物包括其有除草有效量,比如,0.5%至95%重量份,较好的为1至80%重量份的本发明化合物和农用助剂。本发明的除草剂可以单独使用,或配成不同的制剂,比如,可湿性粉剂,颗粒剂,乳油或配以载体、表面活性剂、分散剂或通常用于农业化学品制剂的助剂的粉剂。
用于制剂中的载体,可以是诸如Jeeklite,滑石,膨润土,粘土,高岭土,硅藻土,白碳黑,蛭石,熟石灰,硅砂,硫酸铵或尿素等的固体载体;诸如异丙醇,二甲苯,环己烷或甲基萘等的液体载体。这里所述的表面活性剂和分散剂可以是醇磺酸酯,烷基芳基磺酸酯,木质素磺酸盐,聚氧乙烯乙二醇醚,聚氧乙烯烷基芳基醚或聚氧乙烯山梨醇单烷基酯。助剂可以是羧甲基纤维素,聚乙二醇或阿拉伯树胶。在实际使用中,该除草剂在使用前可以稀释至合适的浓度,或可以直接使用。
本发明除草剂可以与其他除草剂结合使用。
本发明除草剂通过在莠草发芽之前或之后对水稻田里的莠草进行地面灌溉施药或通过叶面施药。另外,本发明除草剂施加于旱地或非农作物地时,可在莠草发芽之前或之后进行地面施药或者叶面施药。
对于地面施药,本发明除草剂的施加剂量为每10公亩1克至1公斤活性成分。对于叶面施药,将其稀释至1至10,000ppm的浓度以每10公亩1克至1公斤活性成分的剂量施加。
现给出本发明除草剂组合物的制剂实例,但应该明白,本发明不只限制在这些特定的实例中。在这些实例中“%”表示重量百分比。
制剂实例1(可湿性粉剂)
将10%编号为1的化合物,0.5% Emulgen 810(商标,Kao公司),0.5% Demol N(商标,Kao公司),20% Kunilite 201(商标,Kunimine Kogyo公司)和69% Jeeklite CA(商标,Jeeklite有限公司)均匀地混合并磨成粉状,得到可湿性粉剂。
制剂实例2(乳油)
将30%编号为1的化合物,20%环己烷,11%聚氧乙烯烷基芳基醚,4%烷基苯磺酸钙和35%甲基萘均匀溶解,得到乳油。
制剂实例3(颗粒剂)
将5%编号为1的化合物,2%月桂醇-磺酸酯钠盐,5%木质素磺酸钠,2%羧甲基纤维素和86%粘土均匀混合并磨成粉状,取100重量份该混合物加入20重量份水,捏和该混合物,用造粒机挤出成14至32目的颗粒,再干燥得到粒料。
制剂实例4(粉剂)
将2%编号为2的化合物,5%硅藻土和93%粘土均匀混合并磨成粉状,得到粉剂。
本发明的化合物和除草剂组合物能有效地控制长在水稻田里的诸如稗(Echinochloa crus-galli),莎草(Cyperus difformis),雨久花(Monchoria vaginalis)等一年生草;以及诸如泽泻属花条痕状(Alisma canaliculatum)的灯心草(Scirpus hotarui),晚花的莎草(Cyperus serotinus),矮慈姑(Sagittaria pygmaea)和荸齐(Eleocharis Kurogwai)等的多年生草。另外,还可有效地控制长在旱田的诸如稗(Echinochloa crus-galli),马唐草(Digitaria sanguinalis),蟋蟀草(Eleusine indica),绿狐尾草(Setaria viridis),水狐尾草(Alopecurus aequalis),一年生早熟禾草(Poa annua),野燕麦(Avena fatua),意大利黑麦草(Lolium multiform),蓼属植物(polygonum Capathifolium),细苋(Amaranthus viridis),藜(Chenopodium album),绒毛叶(Abutilon theophrasti),多刺黄花稔(Sida spinosa),决明(Cassia tora),繁缕(Stellaria media),牵牛花(lpomoea spp),普通苍耳(Xanthium strumarium)谷莎草(Cyperus iria),宽叶臂形草(Brachiaria platphylla),罗氏草(Rotloboellia exaltata),柔毛雀麦(Bromus tectorum),野荞麦(Polygonum convolvulus),野十字花(Brassica arvensis)和裙边鬼针草(Bidens frondosa)等的一年生草;以及诸如紫螺莎草(Cyperus rotundus),约翰逊草(Sorghum halepense),百慕大草(Cynodon dactylon)和匍匐冰草(Agropyron repens)等的多年生草。在另一方面,对农作物,特别是棉花,其安全性是高的。
当本发明的除草剂用作棉花除草剂时,具有以下特点;另外,当其用作除棉花外的农作物的除草剂时,同样有各种优点。
(1)本发明的除草剂在草发芽前的地面施药和草发芽后的叶面施药的每种施药方法中,对于棉花是高度安全的。相应地,本发明除草剂可用作草发芽前的地面施药和草发芽后的叶面施药的棉花除草剂。
(2)本发明的除草剂对诸如普通苍耳和牵牛花之类的令人感到棘手的莠草具有除草作用,而且在草发芽前至发芽后的长时期内是有效的。
(3)本发明的除草剂在泥土中具有适当地可分解性,对邻近农作物无明显促进作用。
现以试验实例描述本发明除草剂的除草活性。试验实例1(旱地里草发芽前的地面施药法)
在一罐泥土中(表面面积600cm2),播下棉花(Go),稗(Ec),约翰逊草(So),蓼属植物(Po),细苋(Am),藜(Ch),牵牛花(Ip)和普通苍耳(Xa)的籽;种下紫螺莎草(Cr)的块茎;再盖上一层0.5至1cm厚的泥土。播种后一天,将预定量的按制剂实例1中的方法制成的可湿性粉剂用水稀释并以每10公亩100升的比例施加到泥土表面。在施药后的第20天进行测量,以表2中的定义为标准评价所得结果,并将指数列于表3和表4。
对比化合物1如下定义(同样适用于其他表中):
对比化合物1:2-[(4,6-二甲氧基嘧啶-2-基)氧代]苯甲酸(在日本待审公开专利174059/1987中公开的)
试验实例2(旱地里草发芽后叶面施药法)
在一罐泥中(表面面积为600cm2)播下棉花(Go),稗(Ec),约翰逊草(So),蓼属植物(Po),细苋(Am),藜(Ch),牵牛花(Ip)和普通苍耳(Xa)的籽,种下紫螺莎草(Cr)的块茎;再盖上一层0.5至1cm厚的泥土。将该罐在20至25℃的温室中培养2周,然后,将预定量的按制剂实例1中的方法配制的可湿性粉剂用水稀释,以每公亩100升的比例施加于叶片上。施药后的第14天进行测量,以表2中的定义为标准评价所得结果,并将指数列于表5和表6。
试验实例3(旱地里的叶面施药法)
在一罐泥土中(表面面积为100cm2),播下稗(Ec),马唐草(Di),蓼属植物(Po),细苋(Am)藜(Ch),和谷莎草(Ci)的籽,再盖以一层0.5至1cm厚的泥土。将罐在20至25℃的温室中培养2周,然后将预定量的按制剂实例1中的方法配制的可湿性粉剂用水稀释,以每10公亩100升的比例施加于叶片上。用除草剂处理后的第14天进行测量,以表2中的定义为标准评价所得结果,并将指数列于表7和表8。
对比化合物2,3和4如下定义(同样适用于表中)
对比化合物2:乙基-3-[(5-氯代嘧啶-2-基)氧代]苯甲酸酯(日本待审公开专利55729/1979中公开的),
对比化合物3:乙基-5[(5-氯代嘧啶-2-基)氧代]-2-硝基苯甲酸酯(日本待审公开专利55729/1979中公开的)
对比化合物4:2-(2-甲苯氧基-4,6-二甲基嘧啶)农业和生物化学,30卷,第9号,896页中公开的)
试验实例4(旱地里地面施药法)
在一罐泥土中(表面面积为100cm2),播下稗(Ec),马唐草(Di),蓼属植物(Po),细苋(Am),藜(Ch),和谷莎草(Ci)的籽,并盖上一层0,5至1cm厚的泥土。播种一天后,将预定量的按制剂实例1中的方法配制的可湿性粉剂用水稀释,并以每10公亩100升的比例施加于嗤恋谋砻妫ɑ钚宰榉莸募亮课?00g/10a)。施药后的第20天进行测量,以表2中的定义为标准评价所得结果,并将指数列于表9和表10。
试验实例5(水稻田里控制莠草的试验)
在一罐水稻田泥土中,播下稗(Ec),莎草(Cd),雨久花(Mo)和灯心草(Sc)籽,加水至3cm深。播种2天后,将预定量的按制剂实例1中的方法配制的可湿性粉剂用水稀释,并以每10公亩100克活性组份的剂量滴加至水表面。施药后的第21天进行测量,以表2中的定义为标准评价所得结果,并将指数列于表11和表12。
Claims (12)
2、如权项1所述的嘧啶衍生物,其特征在于:其中X是在6-位取代。
3、如权项1所述的嘧啶衍生物,其特征在于:其中的R为氢原子,低级烷基,烷氧基烷基或苄氧基烷基。
4、如权项1所述的嘧啶衍生物或其盐,其特征在于:有分子式(Ⅰ-1),
其中R如权项1中所定义的,X为卤素原子或低级烷基。
5、如权项1所述的嘧啶衍生物,其特征在于:其中的盐是碱金属盐,碱土金属盐,过滤金属盐或有机铵盐。
6、如权项1所的所述的嘧啶衍生物或其盐,其特征在于:具有分子式(Ⅰ-2)
其中的R如权项1中所定义,Y为氢原子,卤素原子,低级烷基或低级烷氧基。
7、如权项1所述的嘧啶衍生物,其特征在于:其中的R为氢原子。
8、如权项1所述的嘧啶衍生物,其特征在于:该嘧啶衍生物为2-氯-6-[(4,6-二甲氧基嘧啶-2-基)硫代]苯甲酸或其盐。
9、如权项1所述的嘧啶衍生物,其特征在于:其中的X为6-位的氯原子,甲基或氟原子。
10、除草剂组合物,其特征在于:该组合物含有如权项1所述的分子式为Ⅰ的具有除草有效量的嘧啶衍生物或其盐以及农业助剂。
11、杀死莠草的方法,其特征在于:该方法包括将有除草有效量的如权项1所述的分子式为Ⅰ的嘧啶衍生物或其盐施加于要治理的场所。
12、制备具有分子式Ⅰ的嘧啶衍生物或其盐的方法,
式中X为卤素原子,低级烷基或苯氧基(其中所述的苯氧基可以被卤素原子,低级烷基或低级烷氧基取代),R为氢原子,低级烷基,烷氧基烷基,苄氧基烷基,烷氧基羰基烷基,氰烷基或 基(其中R1为氢原子或低级烷基,R2为低级烷基或可以被硝基取代苯基,该方法包括将具有分子式Ⅱ的化合物
式中X和R如前定义,与具有分子式Ⅲ的化合物反应
式中Y1为卤素原子,烷基磺酰基,取代的或未取代的苄磺酰基;以得到具有分子式Ⅰ的化合物或者将具有分子式Ⅳ的化合物
式中X和R如前定义,转化成具有一般式Ⅴ的重氮盐,再将重氮盐与具有一般式Ⅵ的化合物反应,式中X和R如前定义,得到一般式Ⅰ的化合物;
还可以任意选择地,将具有分子式Ⅰ的化合物与碱反应,得到具有分子式Ⅰ的化合物的盐。
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CN 92102226 CN1028171C (zh) | 1987-11-04 | 1992-03-26 | 嘧啶衍生物及其盐的制备方法 |
CN 92102225 CN1033132C (zh) | 1987-11-04 | 1992-03-26 | 杀死莠草的方法 |
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CN 92102226 Division CN1028171C (zh) | 1987-11-04 | 1992-03-26 | 嘧啶衍生物及其盐的制备方法 |
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CN1033050A true CN1033050A (zh) | 1989-05-24 |
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US (2) | US4923501A (zh) |
EP (1) | EP0315889B1 (zh) |
KR (1) | KR960012178B1 (zh) |
CN (1) | CN1025981C (zh) |
AU (1) | AU611219B2 (zh) |
BR (1) | BR8805749A (zh) |
DE (1) | DE3855427T2 (zh) |
GR (1) | GR3021341T3 (zh) |
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1988
- 1988-10-28 US US07/264,015 patent/US4923501A/en not_active Expired - Lifetime
- 1988-11-02 EP EP88118254A patent/EP0315889B1/en not_active Expired - Lifetime
- 1988-11-02 DE DE3855427T patent/DE3855427T2/de not_active Expired - Lifetime
- 1988-11-03 RU SU884356788A patent/RU2024227C1/ru active
- 1988-11-03 UA UA4356788A patent/UA21892A/uk unknown
- 1988-11-03 TR TR00785/88A patent/TR28607A/xx unknown
- 1988-11-04 AU AU24717/88A patent/AU611219B2/en not_active Expired
- 1988-11-04 BR BR888805749A patent/BR8805749A/pt not_active IP Right Cessation
- 1988-11-04 CN CN88107663A patent/CN1025981C/zh not_active Expired - Lifetime
- 1988-11-04 KR KR1019880014516A patent/KR960012178B1/ko not_active IP Right Cessation
-
1989
- 1989-10-02 US US07/415,871 patent/US4932999A/en not_active Expired - Lifetime
-
1992
- 1992-06-30 RU SU925011920A patent/RU2049781C1/ru active
-
1996
- 1996-10-15 GR GR960402714T patent/GR3021341T3/el unknown
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100381427C (zh) * | 2005-09-02 | 2008-04-16 | 浙江化工科技集团有限公司 | 苄胺类化合物、制备方法及其用途 |
CN102037970A (zh) * | 2011-01-25 | 2011-05-04 | 青岛瀚生生物科技股份有限公司 | 一种含有嘧草硫醚的农药剂型 |
CN103039454A (zh) * | 2013-01-22 | 2013-04-17 | 南京高正农用化工有限公司 | 一种嘧草硫醚与百草枯除草组合物及其应用 |
CN103039454B (zh) * | 2013-01-22 | 2014-12-03 | 南京高正农用化工有限公司 | 一种嘧草硫醚与百草枯除草组合物及其应用 |
CN103333121A (zh) * | 2013-07-22 | 2013-10-02 | 金坛市信德农业科技有限公司 | 具有除草活性的氟嘧肟草醚类化合物及其制备方法 |
CN103333121B (zh) * | 2013-07-22 | 2015-11-18 | 金坛市信德农业科技有限公司 | 具有除草活性的氟嘧肟草醚类化合物及其制备方法 |
CN105272924A (zh) * | 2013-07-22 | 2016-01-27 | 金坛市信德农业科技有限公司 | 具有除草活性的氟嘧啶草醚类化合物及其制备方法 |
CN105272924B (zh) * | 2013-07-22 | 2016-08-17 | 金坛市信德农业科技有限公司 | 具有除草活性的氟嘧啶草醚类化合物及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
EP0315889A2 (en) | 1989-05-17 |
RU2024227C1 (ru) | 1994-12-15 |
BR8805749A (pt) | 1989-07-18 |
AU2471788A (en) | 1989-05-04 |
TR28607A (tr) | 1996-11-15 |
US4923501A (en) | 1990-05-08 |
AU611219B2 (en) | 1991-06-06 |
EP0315889A3 (en) | 1990-07-25 |
US4932999A (en) | 1990-06-12 |
DE3855427D1 (de) | 1996-08-22 |
GR3021341T3 (en) | 1997-01-31 |
RU2049781C1 (ru) | 1995-12-10 |
KR890008112A (ko) | 1989-07-08 |
EP0315889B1 (en) | 1996-07-17 |
DE3855427T2 (de) | 1996-12-05 |
CN1025981C (zh) | 1994-09-28 |
UA21892A (uk) | 1998-04-30 |
KR960012178B1 (ko) | 1996-09-16 |
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