CN1100889A - 用于防止和控制有害植物生长和调节植物生长的组合物 - Google Patents
用于防止和控制有害植物生长和调节植物生长的组合物 Download PDFInfo
- Publication number
- CN1100889A CN1100889A CN93114184A CN93114184A CN1100889A CN 1100889 A CN1100889 A CN 1100889A CN 93114184 A CN93114184 A CN 93114184A CN 93114184 A CN93114184 A CN 93114184A CN 1100889 A CN1100889 A CN 1100889A
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- Prior art keywords
- inhibitor
- acid
- growth hormone
- compound
- weed killer
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- 230000008635 plant growth Effects 0.000 title claims abstract description 19
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- 229910052700 potassium Inorganic materials 0.000 claims description 2
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- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
- C07C281/14—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to a carbon atom of a six-membered aromatic ring
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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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
- A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
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Abstract
用某些除草的缩氨基脲及其盐作为除草剂和/
或调节植物生长物质的增效剂或促进剂。
Description
本发明是关于将生长素输送抑制剂用作除草剂的增效剂或促进剂,以及上述生长素输送抑制剂和除草剂的联合作用,含有至少一种与至少一种除草剂合用的生长素输送抑制剂的组合物和这些组合物在防止和控制有害植物的生长和在调节植物生长中的应用。
生长素输送抑制剂是这样一类化合物,其本身是除草剂且通过抑制在细胞中积累的和影响植物生长的生长素在转移膜中的运动而起作用,生长素输送抑制剂的实例如,抑草生,三碘苯甲酸(2,3,5-三碘苯甲酸)和地草死[3,3a一二氢-2-(对-甲氧苯基)-8H-吡唑并[5,1-a]异吲哚-8-酮](参见E.M.Beyer,Jr.Plant Physiol.,50,322(1972),E.M.Beyer,Jr.等人,PlantPhysiol.,57,839(1976)和如美国专利5,098,462和5,098,466和欧洲专利公开219451中所描述的缩氨基脲。本发明所用的特别优选的生长素输送抑制剂是式A的化合物
其中X和Y分别代表,氢、氟或氯,和
R为下列基团
其中Z为氢,氟或氯且M为氢,或盐形成部分,如,碱金属阳离子或未被取代或取代的铵离子。
如在美国专利5,098462和5,098466和欧洲专利公开219451中普遍地公开了式A化合物,以及它们的制备方法,它们作为除草剂和植物生长调节剂的用途,和含有它们的除草和调节植物生长的组合物,上述各个方面的内容,在本文中作为文献供参考。这些专利没有提到式A族的具体化合物或它的增效活性。
本文中术语除草剂,涉及防止或控制有害植物生长的化合物,根据在植物上除草作用的基本类型和方式,可将这类化合物分成亚类。例如根据G.F.Warren of Purdue University,Indiana,USA,除草剂可被分类为生长素输送抑制剂、生长调节除草剂、光合成抑制剂、色素抑制剂、生长抑制剂、氨基酸合成抑制剂、脂类生物合成抑制剂、细胞壁生物合成抑制剂、细胞膜快速破裂剂以及不属于上述类别中的“各种各样的”的除草剂。(生长调节除草剂包括,例如,生长素拮抗剂)。
根据本发明,现已令人惊奇地发现,通常其本身具有很高除草剂活性的生长素输送抑制剂,在与其它除草剂混合应用时,具有增效活性。文中本发明的除草剂可用作干燥剂和脱叶剂。
本文中的增效作用,指基于对生长素输送抑制剂和除草剂的活性分别观察,生长素输送抑制剂与除草剂的相互作用使得该活性比预期的活性要大。因此,混合使用产生明显优于单个除草活性物质的加合效果的除草活性。
增效作用本身以多种形式表现。因此,混合使用能采用单独使用生长素输送抑制剂和/或除草剂时不能完全有效的用量,或能够防治在以混合物中的相同单独剂量来使用每种活性成分时不能防治的多种类型的杂草。
而且,混合使用产生明显优于单独活性成分加合效果的除草活性。另外,本申请的生长素输送抑制剂能够增加除草效果,以致能使给定施用剂量的除草剂的防治或生长调节的最大水平得到增加,或另外,可以使最佳防治或生长调节的除草剂施用剂量降低。
混合使用可理解为同时,或立即连续施用(例如,在24小时内),桶混使用或以预先混合的固定组合物使用。
可采用生长素输送抑制剂增效的除草剂,特别是根据本发明式A化合物的非限定性的实例包括:
1.其它生长素输送抑制剂,例如,抑草生;
2.生长调节剂,包括a)苯甲酸类,例如,麦草畏;b)苯氧酸类i)乙酸型,例如,2,4-滴,2甲4氯,ⅱ)丙酸型,例如,2,4-滴丙酸,2甲4氯丙酸,ⅲ)丁酸型,例如,2,4-滴丁酸,2甲4氯丁酸;c)吡啶甲酸和有关化合物,例如,毒莠定,定草酯,氟草定,Clopyralid,
3.光合成抑制剂,包括a)S-三嗪类ⅰ)氯取代的,例如,莠去津,西玛津,氰草津,ⅱ)甲氧基取代的。例如,扑灭通,ⅲ)甲硫基取代的,例如,莠灭净;扑草净;b)其它三嗪类,例如,环嗪酮,嗪草酮;c)取代脲类,例如,敌草隆,优草隆,利谷隆,丁唑隆,塞唑隆,forchlorfenuron;d)尿嘧啶,例如,除草定,特草定,e)其它类,例如,噻草平,异苯敌草,灭草定,苯敌草,敌稗,杀草敏,达草止;
4.色素抑制剂,包括a)哒嗪酮类;例如,达草灭;b)异噁唑酮类,例如,广灭灵;c)美国专利4,695,673;4,921,526;5,006,150;5,089,046;EP-A338992;EP-A-394889和EP-A-506907中描述的三酮类和环二酮类(上述各自的内容在本文中作为文献供参考),包括例如2-(2-氯-4-甲基磺酰基苯甲氧基)-1,3环已二酮(Sulcotrione);2-(4-甲基磺酰基氧-2-硝基苯甲氧基)-4,4,6,6-四甲基-1,3-环已二酮;3-(4-甲基磺酰基氧-2-硝基苯甲氧基)-二环-[3,2,1]辛烷-2,4-二酮;3-(4-甲基磺酰基-2-硝基苯甲氧基)-二环-[3,2,1]辛烷-2,4-二酮;4-(4-氯-2-硝基苯甲氧基)-2,6,6-三甲基-2H-1,2-噁嗪-3,5(4H,6H)二酮;4-(4-甲硫基-2-硝基苯甲氧基)-2,6,6-三甲基-2H-1,2-噁嗪-3,5(4H,6H)-二酮;3-(4-甲硫基-2-硝基-苯甲氧基)-二环[3,2,1]辛烷-2,4-二酮;4-(2-硝基-4-三氟甲氧基苯甲氧基)-2,6,6-三甲基-2H-1,2-噁嗪-3,5(4H,6H)-二酮;d)其它类,例如杀草强,氟草酮;
5.生长抑制剂,包括a)有丝分裂中断剂ⅰ)二硝基苯胺类,例如氟乐灵,Prodiamine,氟草胺,丁氟消草,异乐灵,黄草消,胺硝草;ⅱ)其它类,例如,敌稗,dithiopyr,thiazapyr,拿草特;(b)形成籽苗的芽的抑制剂ⅰ)硫代氨基甲酸酯,例如,扑草灭,苏达灭,草灭特,草达灭,克草猛,杀草丹,野麦畏,灭草猛;c)仅为籽苗根的抑制剂,例如,地散磷,apropamide,环草隆;d)根和芽的抑制剂,包括氯乙酰胺类,例如,草不绿,乙基乙草胺,丙草胺,安塔,毒草安,和噻吩胺类如dimethenamid(2-氯-N-(1-甲基-2-乙氧基-乙基)-N-(2,4-二甲基-噻吩-3-基)乙酰胺,参见美国专利4,666,502),和其它类,如,恶庚草烷;
6.氨基酸合成抑制剂,包括a)草甘膦,草铵膦;b)磺酰脲类,例如甲磺隆,甲基甲磺隆,ethametsulfuron,nicosulfuron,醚苯磺隆,Primisulfuron,苄嘧磺隆,氯嘧磺隆,乙基氯嘧磺隆,氯磺隆,嘧磺隆,噻吩磺隆,tribenuron,trifluslfuron,clopyrasulfuron,和pyrazasulfuron;c)磺酰胺,例如,flumetsulam(DE498);d)啉唑啉酮类,例如,imazaquin,imazamethabenz,imazapyr,普杀特;
7.脂类生物合成抑制剂,包括a)环已二酮,例如,稀禾定,烯草酮;b)芳氧基苯氧类、例如,吡氟丁禾灵,禾草灵,吡氟禾草灵,喹禾灵;c)其它类,例如,恶唑禾草灵;
8.细胞壁生物合成抑制剂,例如,牧草腈,异恶胺;
9.细胞膜快速破裂剂,包括a)双吡啶鎓盐类,例如,对草快,敌草快,b)二苯醚类,例如,氟锁草醚,氟磺胺草醚,克阔乐,乙氧氟草醚;c)谷氨酸胺合成抑制剂,例如,草铵膦,d)其它类,例如,噁草酮;
10.各种各样的类,包括a)氨基甲酸酯,例如,黄草灵,b)腈类,例如,溴苯腈,碘苯腈;c)hydantocidin及衍生物,d)各种类,例如,多效唑,唑啶草,快杀稗,燕麦枯,菌多杀,调节膦,甲胂钠,甲胂一钠;
11.其它类
在EP-A-315889;EP-A-461,079和EP-A-549,524;和PCT申请W091/10653中描述的化合物(上述各自的内容在本文中作为文献供参考)包括例如
3-[(4,6-二甲氧基-2-嘧啶基)羟甲基]-N-甲基-2-吡啶羧酸胺;
4,7-二氯-3-(4,6-二甲氧-2-嘧啶基)-3-已酰基-氧-2苯并呋喃;
3-[(4,6-二甲氧-2-嘧啶基)羰基]-N,N-二甲基-2-吡啶羧酸胺;
3,6-二氯-2-[(4,6-二甲氧-2-嘧啶基)-羰基]苯甲酸;
6-氯-2-[(4,6-二甲氧-2-嘧啶基)硫]-苯甲酸(DPX-PE350或Pyrithiobac)和其盐。
应注意的是在某些情况下,一种生长素输送抑制剂可增强另一种生长素输送抑制剂的效果。生长素输送抑制剂效果的实质就是它所具有提高不同类别除草剂活性的能力,因此本发明还涉及防止或控制有害植物生长或调节植物生长的方法,该方法包括在需要防止或控制的地区混合使用除草或调节植物生长有效合计量的至少一种生长素输送抑制剂和至少一种其它除草剂,其中生长素输送抑制剂以增效剂量施用。
当然混合使用的剂量将随气候条件、季节、土壤生态和被防治的杂草等等而改变,然而,例如用0.00011至1.1kg/ha(0.0001至1.01b/A,优选0.0011至0.55kg/ha(0.0001至0.5lb/A),特别是0.011至0.11kg/ha(0.01至0.11b/A)剂量的生长素输送抑制与相应于单独使用需要的或明显低于单独使用需要的合用除草剂的剂量混合使用,能够获得很好的效果(下文所述的施用量是用最初测定值通过转换系数11b/A=1.1kg/ha换算为Lb/A来计算的)。
苗前或苗后使用的具体混合物的适用性和选择性,当然取决于合用除草剂的选择。
以上所提及的专利中描述了式A化合物的活性并且其它已知的生长素输送抑制剂的活性和适于混用的除草剂的活性已在文献中或其市售形式中进行了描述(还参见CROP PROTECTION CHEMICALS REFBRENCE,Chemical & Pharmaceutical Press / NY,NY)。
本发明还提供了含有至少一种生长素输送抑制剂和至少一种其它除草剂的除草或调节植物生长组合物,其中生长素输送抑制剂是以增效量存在的,特别优选的组合物含有式A化合物。
上述组合物含有与农用可接受的稀释剂相结合的活性物质,该组合物可以混有常规稀释剂的固体或液体的形式来使用,例如,可湿性粉剂形式或可乳化的浓缩物形式。
上述组合物可以常规方法生产,例如,通过将活性成分与稀释剂以及可有可无的其它配制组分(如表面活性剂和油)进行混合来生产。
本文中采用的术语稀释剂意为可被加入到活性组分中以提供更方便或更有利的施用形式,或获得可用或合乎需要强度活性的任何液体或固体的农用可接受的物质,稀释剂的实例为滑石、高岭土、硅藻土、二甲苯、非植物毒性油或水。
以喷雾形式施用的特定的制剂如水可分散的浓缩物、水可分散粒剂或可湿性粉剂,可含有如湿润剂或分散剂的表面活性剂,例如,甲醛与荼磺酸盐的缩合产物,烷芳基磺酸盐,木质素磺酸盐,脂肪烷基硫酸酯,乙氧基化的烷基酚或乙氧基化的脂肪醇。
通常,该制剂包括按重量计0.01至90%的活性成分和按重量计0至20%的农用可接受的表面活性剂,活性成分由至少一种生长素输送抑制剂和至少一种其它除草剂组成,浓缩形式的组合物通常含有按重量计大约2至90%,优选大约5至80%的活性物质。制剂的施用形式可以含有例如按重量计0.01至20%的活性物质。
当同时,或立即连续或桶混施用时,如果适合可使用市售形式的非生长素输送制剂合用的,且采用相当于或优选低于制造者推荐的剂量。按以上提及的EP-A-219451,美国专利5,098,462或多或5,098,466所描述的方法来制备生长激素输送抑制剂。
本发明的混合使用,还包括施用其它具有生物活性的化合物,例如,具有杀虫或杀真菌活性的化合物。
优选的施用方式包括通过将生长素输送抑制剂加入到含有其它除草剂合用物和适当的表面活性剂的桶中制备的桶混和对预混物的调整。
根据选择的混合使用合用物,可获得对大范围内的阔叶和禾本科杂草的苗前和苗后的活性。上述杂草的非限定性实例为
Setario sp-狗尾草
Brachiaria platyphylla-阔叶臂形草
Ipomoea sp-牵牛
Abutilon theophrasti-
麻
Hisbiscus trionum-野西瓜苗
Solanum sp-茄科,例如,银毛龙葵
Avena fatua-野燕麦
Sinapis alba-田白芥
Amaranthus sp-黎,刺苋
Xauthium strumarium-苍耳
Sorghum halepense-阿刺伯高梁
Echinochloa crus-galli-稗草
Cassia obtusifolia-钝叶决明
Digitaria sp-例如,马唐
Bromus tectorum-旱雀麦
Apera spica-venti-风草
Chenopodium album-藜
Sorghum bicolor-二色蜀黍
Portulaca oleracea-马齿苋
Sida spinsa-刺黄花稔
Campsis radiicans-美洲凌霄花
Rottboellia exaltata-罗氏草
Cynodon dactylon-狗牙根
Agropyron repens-匍匐冰草
Cyperus sp,-莎草
Panicum sp,例如,一稷
Lespedeza sp-胡枝子属
Trifolium sp-车轴草属
Hippuris vulgaris-问荆
Asclepias sp-马利筋属
Salvia sp-例如,鼠尾草
Salsola iberica-猪毛菜
Convolvulus arvensis-田旋花
Cirsium arvense-田蓟
Proboscidea louisianica-角胡麻
Senecio sp-欧洲千里光
Chorispora tennela-离子草
Alopecurus myosuroides-鼠尾看麦娘
Sisymbrium altissimum-田蒜芥
Caperionia palustris-texasweed
对作物的选择性通常依赖于选择的合用物。
例如式A化合物对玉米和小谷物作物显示极好的选择性。
预料到生长素输送抑制剂与多于一个的其它除草剂的混合物,例如,三元混合,也是可以的。
优选的生长素输送抑制剂是那些式A化合物,特别是那些其中M为氢或钠、钾、异丙基铵或2-(2-羟乙氧基)乙基铵离子(化合物A1)的化合物。
其它组的化合物包含其中Z代表氢(化合物A2);Z代表氟(化合物A3);Z代表氯(化合物A4)的式A化合物。
特别优选的个别生长素输送抑制剂是以游离酸或以盐形式,特别是以其钠盐形式的2-乙酰基烟酸4-(3,5-二氟苯基)缩氨基脲,以游离酸或以盐形式,特别是以钠盐形式的2-乙酰基烟酸4-(3-氟苯基)缩氨基脲,和以游离酸形式或以钠盐形式的2-乙酰基烟酸-4-(3-氯苯基)缩氨基脲。
优选除草混合合用物的类别为生长调节除草剂:如苯甲酸,苯氧乙酸,吡啶甲酸和有关的化合物,生长抑制剂如籽苗根和芽的抑制剂,细胞膜快速破裂剂如双吡啶鎓盐,氨基酸合成抑制剂如磺酸脲和磺酰胺。
优选混合使用的除草合用物的具体实例为麦草畏,赛苯隆,2.4-滴,dimethenamid,莠去津,氰草津,达草灭,氟草定,二甲戊乐灵,primisulfuron,nicosulfuron pendimethalin,chlorpyralid,对草快,呋草黄,flumetsulam(DE 49 &),且在一些情况下,可为草甘膦。
具体组合物的非限定性实例是那些含有例如,2-乙酰基烟酸4-(3,5-二氟苯基)缩氨基脲2-(2-羟乙氧基)乙基铵盐(a);或2-乙酰基烟酸4-(3-氟苯基)缩氨基脲钠盐(b);或2-乙酰基烟酸4-(3-氯苯基)缩氨基脲钠盐(c);2-乙酰基烟酸4-(3,5-二氟苯基)缩氨基脲(d);2-乙酰基烟酸4-(3,5-二氟苯基)缩氨基脲钠盐(e);各自与例如麦草畏(Z);dimethenamid(y);2,4-滴(x);或赛苯隆(w)的组合物。
如上所述,施用剂量依赖于各种因素,通常,当按以下给出的剂量使用混合使用的合用物时,可获得满意的结果;
化合物(a),(b),(c)或(d)0.0011至1.1kg/ha,优选0.011至0.55kg/ha,特别优选0.011至0.11kg/ha。
化合物(z)0.011至2.2kg/ha,优选0.05至0.55kg/ha,特别是0.11至0.55kg/ha。
化合物(y)0.11至4.4kg/ha,优选0.275至1.0kg/ha,特别是0.55至1.0kg/ha。
化合物(x)0.011至2.2kg/ha,优选0.11至1.1kg/ha,特别是0.275至0.825kg/ha。
化合物(w)0.011至1.1kg/ha,优选0.055至0.55kg/ha,特别是0.088至0.44kg/ha。
在调整的预混合物中个别成分的重量比将根据需要施用的剂量来变化,因此例如,在预混物中化合物(a)与化合物(z)的比例可在例如1:2000至100:1,优选1:50至5:1,特别是1:50至1:1(例如1:50至1:2.5)的范围内变化。
三元混合物的实例是化合物(e)与化合物(z)和nicosulfuron 或dimetheuamid。
而且例如化合物(d)或它的盐与化合物(z)的混合物可在其中加入对杂草具有活性的除草剂,如以上所列的5和7类。
其中z为氯或氟的式A化合物是新的,并且也形成本发明的一部分。因此本发明还涉及式XA化合物。
其中X,Y和M按式A定义,且Z’代表氯或氟。
本发明还涉及式XA化合物单独或与其它活性化合物组合用于防治杂草,含有单独的或与其它活性化合物组合的式XA化合物的除草组合物,以及式XA化合物的制备方法。
式XA的特定化合物是例如那些其中X为氟或氯,Y为氢或氟和Z为6-氟或6-氯(羧酸邻位)以盐或游离酸的形式存在的化合物。
其中Z’为6-氟或6-氯的式XA化合物是特别优选的。
式XA化合物及其作为除草组合物的制剂的使用可按本文中所述的方法或按美国专利5,098,462;5,098,466和EP-A-219451中描述的方法进行,文中这方面各自的内容作为文献供参考。
下述实施例将列示发明,但不构成对本发明的任何限制。
实施例1
田间试验
田间试验是在玉米田中的
麻和藜上进行的。在播种杂草出苗35天长到41至89cm高时施用。通过叶面喷布处理施用桶混制剂,上述化合物(a)按现在的样子桶混。上述化合物(z)以0.5kg/l.s.c市售商标BANVEL
的形式桶混。Aquagene是市售的表面活性剂,(Universal Coop Incorporated Minneapolis,MN)。所述值是由最初测定值根据转化系数:1公顷=2.47英亩;1公斤=2.2磅;1米=3.28英尺;和1加仑=3.78升换算为英亩,磅,英寸和加仑而计算的。
结果归纳如下。
剂量 防治百分率(%)
处理方式 kg/ha 茼麻 藜
Aquagene10 0 0
化合物(z) 0.275 18 30
化合物(a) 0.011 13 18
化合物(z)+ 0.275 27 40
Aquagene1
化合物(a)+ 0.011 13 18
Aquagene1
化合物(a)+ 0.011 57 90
化合物(z) 0.275
化合物(a)+ 0.011 65 93
化合物(z)+ 0.275
Aquagene1
(10.9 l/ha)
(a)加(z)的桶混组合物处理效果明显好于各种单独处理的效果。助剂在防治中产生某些增加作用,但与在防治中观察到的除草组合物明显增加的防治水平无关。(a)加(z)的组合物产生明显优于单独除草剂加合效果的反应,当以所述剂量单独使用时,该除草剂不显示满意的杂草防治效果。
对田间玉米没有影响。
实施例2
温室实验
温室实验是在
麻、藜、旋花和苍耳上进行的。在出苗后10天时处理并在处理后18天时进行评价。化合物(e)按ai技术,在等份丙酮和1/2%表面活性剂的水的混合物中配制。化合物(z)使用市售形式的在1/2%表面活性剂的水中的BANVEL
除草剂(=480g/1 a.i.等量)。在每个浓度重复3次的长形喷雾室中施用桶混物。
剂量 防治百分率(%)
化合物(e) 0.01 55 50 55 25
化合物(z)* 0.02 35 35 35 75
化合物(e)+ 0.01 98 100 98 100
化合物(z) 0.20
用Limpel公式表示增效结果,且用Duncan多次范围试验表示结果的统计意义。
*为市售的BANVEL
除草剂。
实施例3
2-乙酰基-6-氟苯甲酸4-(3,5-二氟苯基)缩氨基脲(表A化合物1)的制备
a)3-氟苯二甲酸酐的制备
将3-氟苯二甲酸15g与乙酸酐16.6g混合,并回流3小时,除去未反应的乙酸酐后,用甲苯重结晶剩余的白色固体。
b)2-乙酰基-6-氟苯甲酸的制备
将9g3-氟苯二甲酸酐和6.8g丙二酸在80ml三乙胺中混合,在油浴中加热到71-72℃,直到气体停止挥发。使反应混合物与50ml 10% HCl/H2O混合并用乙醚提取,蒸掉乙醚后,将所得黑色油状物在柱上,用1120%乙酸乙酯/已烷再用1130%乙酸乙酯/已烷进行色谱层析,最初得到3-氟同分异构体,接着得到所需的6-氟同分异构体,M.P.76-81.5℃。
c)标题化合物的制备
将3g 6-氟-2-乙酰基苯甲酸和3g 4-(3,5-二氟苯基)缩氨基脲在20ml甲醇中混合,并加热至澄清,然后在室温下将该溶液搅拌24hr。滤出白色固体物并在60℃下真空干燥,得到标题产物m.p.227℃(分解)。通过游离酸与25%甲醇钠/甲醇反应制备相应的钠盐。
可类似地制备下列式XA化合物。
表A
化合物号 X Y Z’ m.p
1 F F 6-F 酸227℃(分解),Na+盐
2 F H 6-F 酸174℃(分解)
3 Cl H 6-F 酸157℃(分解)
4 F F 6-Cl 酸174℃(分解)
5 F H 6-Cl 酸176℃(分解)
6 Cl H 6-Cl 酸204℃(分解)
Claims (14)
1、一种除草组合物,含有除草或调节植物生长有效合计量的至少一种生长素输送抑制剂和至少一种其它除草剂,其中生长素输送抑制剂以产生增效效果的量存在。
2、根据权利要求1的除草组合物,其中除草剂是生长素输送抑制剂,生长素调节除草剂,光合成抑制剂,色素抑制剂,生长抑制剂,氨基酸合成抑制剂,脂类生物合成抑制剂,细胞壁生物合成抑制剂或细胞膜快速破裂剂,较优选的是生长素调节除草剂,生长抑制剂,细胞膜快速破裂剂或氨基酸合成抑制剂。
3、根据权利要求1或2的除草组合物,其中除草剂是苯甲酸,苯氧乙酸,苯氧丙酸,苯氧丁酸,吡啶甲酸,氯一取代的S-三嗪,甲氧基取代的5-三嗪,甲硫基取代的S-三嗪,三嗪,取代脲,尿嘧啶,哒嗪酮,异鎓唑酮,二硝基苯胺,硫代氨基甲酸酯,氯乙酰胺,硫苯胺,磺酰脲,磺酰胺,咪唑啉酮,环已烷二酮,芳氧基苯氧化物,双吡啶鎓化物,二苯醚,氨基甲酸酯或腈,更优选的为苯甲酸,苯氧乙酸,吡啶甲酸或双吡啶鎓化物。
4、根据权利要求1的除草组合物,其中除草剂是麦草畏,赛苯隆,2,4一滴,dimethenamid,达草天,氟草定,chlorpyralid对草快,草甘膦,草铵膦,呋草黄,nicosulfuron,快杀稗或flumetsulam。
6、根据权利要求1至4任一的除草组合物其中生长素输送抑制剂为游离酸或盐形式的2-乙酰基烟酸4-(3,5-二氟苯基)缩氨基脲,2-乙酰基烟酸4(3-氟苯基)缩氨基脲或2-乙酰基烟酸-4-(3-氯苯基)缩氨基脲,优选地选自2-乙酰基烟酸4-(3,5-二氟苯基)缩氨基脲2-(2-羟乙氧基)乙基铵盐(a);或2-乙酰基烟酸4-(3-氟苯基)缩氨基脲钠盐(h);2-乙酰基烟酸4-(3-氯苯基)缩氨基脲钠盐(c);或2-乙酰基烟酸4-(3,5-二氟苯基)缩氨基脲(d)并且除草剂为麦草畏(z),dimethenamid(y);2,4-滴;或赛苯隆(w)。
7、根据权利要求1至4任一的除草组合物其中生长素输送抑制剂选自抑草生,三碘苯甲酸,和地草死。
8、根据权利要求1至7任一的除草组合物,其中生长素输送抑制剂与其它除草剂的重量比为1∶2000至100∶1;优选1∶50至5∶1,更优选1∶50至1∶1,且最优选1∶50至1∶2.5。
9、防止或控制有害植物生长或调节植物生长的方法,包括在需要防止或控制的地区混合使用除草或调节植物生长有效合计量的按权利要求1至8任一定义的至少一种生长素输送抑制剂和至少一种其它除草剂,其中生长素输送抑制剂以增效剂量施用。
10、根据权利要求9的方法,其中生长素输送抑制剂以0.0011至1.1kg/ha的剂量施用。
12、根据权利要求11的化合物,其中X为氟或氯,Y为氢或氟且Z’为6-氟或6-氯。
13、一种含有除草或调节植物生长有效量的权利要求11的化合物的除草或调节植物生长的组合物。
14、一种防止或控制有害植物生长或调节植物生长的方法,包括在需要防止或控制的地区施用除草或调节植物生长有效量的权利要求11的化合物。
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP93810647A EP0646315B1 (en) | 1992-11-05 | 1993-09-13 | Novel compositions containing an auxin transport inhibitor and another herbicide |
ZA936743A ZA936743B (en) | 1992-11-05 | 1993-09-13 | Auxin transport inhibitors as potentiators or enhancers of herbicides. |
SG1996001592A SG47443A1 (en) | 1992-11-05 | 1993-09-13 | Novel compositions |
AT93810647T ATE179865T1 (de) | 1993-09-13 | 1993-09-13 | Neue zusammensetzungen, die einen auxintransport- inhibitor und ein anderes herbizid enthalten |
HU9701067A HU221510B (en) | 1993-09-13 | 1993-09-14 | Synergetic herbicidal compositions containing semicarbazones and method for using thereof |
HU9302594A HU214006B (en) | 1992-11-05 | 1993-09-14 | Sinergetic herbicid compositions containing semicarbazones and method for using thereof |
CZ19931914A CZ286811B6 (cs) | 1992-11-05 | 1993-09-14 | Herbicidní prostředek |
CA002106277A CA2106277C (en) | 1992-11-05 | 1993-09-15 | Novel compositions containing an auxin transport inhibitor and another herbicide |
SK1002-93A SK284259B6 (sk) | 1992-11-05 | 1993-09-16 | Herbicídna kompozícia a spôsob ničenia alebo kontroly rastu nežiaducej vegetácie alebo regulácie rastu rastlín |
AU47483/93A AU670809B2 (en) | 1992-11-05 | 1993-09-20 | Herbicidal compositions and method involving auxin transport inhibitors |
HR93810647.3A HRP931225B1 (en) | 1992-11-05 | 1993-09-21 | Novel compositions applicable to herbicides |
IL10705393A IL107053A (en) | 1992-11-05 | 1993-09-21 | Synergistic herbicidal compositions comprising an auxin transport inhibitor and at least one other herbicide and certain such novel auxin inhibitors |
CN93114184A CN1100889A (zh) | 1992-11-05 | 1993-09-27 | 用于防止和控制有害植物生长和调节植物生长的组合物 |
BR9303987A BR9303987A (pt) | 1992-11-05 | 1993-09-30 | Composição herbicida, composto e processo para o combate ou controle do crescimento de plantas indesejáveis |
JP5247841A JPH07126118A (ja) | 1992-11-05 | 1993-10-04 | 新規組成物 |
TW82108476A TW304863B (zh) | 1992-11-05 | 1993-10-13 | |
RU93050547A RU2117429C1 (ru) | 1992-11-05 | 1993-11-05 | Гербицидная композиция |
RO94-01611A RO116153B1 (ro) | 1992-11-05 | 1994-10-04 | Compozitie erbicida sinergica si metoda pentru combaterea, controlul sau reglarea cresterii plantelor nedorite |
Applications Claiming Priority (16)
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US97205692A | 1992-11-05 | 1992-11-05 | |
EP93810647A EP0646315B1 (en) | 1992-11-05 | 1993-09-13 | Novel compositions containing an auxin transport inhibitor and another herbicide |
ZA936743A ZA936743B (en) | 1992-11-05 | 1993-09-13 | Auxin transport inhibitors as potentiators or enhancers of herbicides. |
SG1996001592A SG47443A1 (en) | 1992-11-05 | 1993-09-13 | Novel compositions |
HU9302594A HU214006B (en) | 1992-11-05 | 1993-09-14 | Sinergetic herbicid compositions containing semicarbazones and method for using thereof |
CZ19931914A CZ286811B6 (cs) | 1992-11-05 | 1993-09-14 | Herbicidní prostředek |
CA002106277A CA2106277C (en) | 1992-11-05 | 1993-09-15 | Novel compositions containing an auxin transport inhibitor and another herbicide |
SK1002-93A SK284259B6 (sk) | 1992-11-05 | 1993-09-16 | Herbicídna kompozícia a spôsob ničenia alebo kontroly rastu nežiaducej vegetácie alebo regulácie rastu rastlín |
AU47483/93A AU670809B2 (en) | 1992-11-05 | 1993-09-20 | Herbicidal compositions and method involving auxin transport inhibitors |
HR93810647.3A HRP931225B1 (en) | 1992-11-05 | 1993-09-21 | Novel compositions applicable to herbicides |
IL10705393A IL107053A (en) | 1992-11-05 | 1993-09-21 | Synergistic herbicidal compositions comprising an auxin transport inhibitor and at least one other herbicide and certain such novel auxin inhibitors |
CN93114184A CN1100889A (zh) | 1992-11-05 | 1993-09-27 | 用于防止和控制有害植物生长和调节植物生长的组合物 |
BR9303987A BR9303987A (pt) | 1992-11-05 | 1993-09-30 | Composição herbicida, composto e processo para o combate ou controle do crescimento de plantas indesejáveis |
JP5247841A JPH07126118A (ja) | 1992-11-05 | 1993-10-04 | 新規組成物 |
RU93050547A RU2117429C1 (ru) | 1992-11-05 | 1993-11-05 | Гербицидная композиция |
RO94-01611A RO116153B1 (ro) | 1992-11-05 | 1994-10-04 | Compozitie erbicida sinergica si metoda pentru combaterea, controlul sau reglarea cresterii plantelor nedorite |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1100889A true CN1100889A (zh) | 1995-04-05 |
Family
ID=34222767
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN93114184A Pending CN1100889A (zh) | 1992-11-05 | 1993-09-27 | 用于防止和控制有害植物生长和调节植物生长的组合物 |
Country Status (16)
Country | Link |
---|---|
EP (1) | EP0646315B1 (zh) |
JP (1) | JPH07126118A (zh) |
CN (1) | CN1100889A (zh) |
AU (1) | AU670809B2 (zh) |
BR (1) | BR9303987A (zh) |
CA (1) | CA2106277C (zh) |
CZ (1) | CZ286811B6 (zh) |
HR (1) | HRP931225B1 (zh) |
HU (1) | HU214006B (zh) |
IL (1) | IL107053A (zh) |
RO (1) | RO116153B1 (zh) |
RU (1) | RU2117429C1 (zh) |
SG (1) | SG47443A1 (zh) |
SK (1) | SK284259B6 (zh) |
TW (1) | TW304863B (zh) |
ZA (1) | ZA936743B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104823997A (zh) * | 2015-03-11 | 2015-08-12 | 潍坊中农联合化工有限公司 | 一种含氟吡草腙钠盐和2,4-二氯苯氧乙酸盐的除草组合物及其应用 |
CN106259427A (zh) * | 2016-08-17 | 2017-01-04 | 河北威远生化农药有限公司 | 一种增效草铵膦水剂 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE245899T1 (de) * | 1996-03-13 | 2003-08-15 | Syngenta Participations Ag | Herbizide kombinationen |
DE19710760A1 (de) * | 1997-03-14 | 1998-09-17 | Basf Ag | Fungizide Mischung |
DE19836673A1 (de) * | 1998-08-13 | 2000-02-17 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel für tolerante oder resistente Zuckerrübenkulturen |
ES2238425T3 (es) | 2000-01-25 | 2005-09-01 | Syngenta Participations Ag | Composicion herbicida. |
EP2114149A2 (en) * | 2007-01-29 | 2009-11-11 | Syngeta Participations AG | Herbicidal composition |
CN102300466B (zh) | 2009-02-02 | 2015-06-03 | 巴斯夫欧洲公司 | 包含抑草生的除草组合物 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3753680A (en) * | 1970-05-14 | 1973-08-21 | Stauffer Chemical Co | Arylidene semicarbazones and their utility as herbicides |
EP0219451B1 (en) * | 1985-08-20 | 1991-03-20 | Sandoz Ag | Semicarbazones and thiosemicarbazones |
EP0258182A1 (en) * | 1986-08-08 | 1988-03-02 | Sandoz Ag | Semicarbazones and thiosemicarbazones |
-
1993
- 1993-09-13 SG SG1996001592A patent/SG47443A1/en unknown
- 1993-09-13 EP EP93810647A patent/EP0646315B1/en not_active Expired - Lifetime
- 1993-09-13 ZA ZA936743A patent/ZA936743B/xx unknown
- 1993-09-14 CZ CZ19931914A patent/CZ286811B6/cs not_active IP Right Cessation
- 1993-09-14 HU HU9302594A patent/HU214006B/hu unknown
- 1993-09-15 CA CA002106277A patent/CA2106277C/en not_active Expired - Lifetime
- 1993-09-16 SK SK1002-93A patent/SK284259B6/sk not_active IP Right Cessation
- 1993-09-20 AU AU47483/93A patent/AU670809B2/en not_active Expired
- 1993-09-21 IL IL10705393A patent/IL107053A/en not_active IP Right Cessation
- 1993-09-21 HR HR93810647.3A patent/HRP931225B1/xx not_active IP Right Cessation
- 1993-09-27 CN CN93114184A patent/CN1100889A/zh active Pending
- 1993-09-30 BR BR9303987A patent/BR9303987A/pt not_active IP Right Cessation
- 1993-10-04 JP JP5247841A patent/JPH07126118A/ja active Pending
- 1993-10-13 TW TW82108476A patent/TW304863B/zh not_active IP Right Cessation
- 1993-11-05 RU RU93050547A patent/RU2117429C1/ru active
-
1994
- 1994-10-04 RO RO94-01611A patent/RO116153B1/ro unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104823997A (zh) * | 2015-03-11 | 2015-08-12 | 潍坊中农联合化工有限公司 | 一种含氟吡草腙钠盐和2,4-二氯苯氧乙酸盐的除草组合物及其应用 |
CN106259427A (zh) * | 2016-08-17 | 2017-01-04 | 河北威远生化农药有限公司 | 一种增效草铵膦水剂 |
CN106259427B (zh) * | 2016-08-17 | 2018-12-07 | 河北威远生物化工有限公司 | 一种增效草铵膦水剂 |
Also Published As
Publication number | Publication date |
---|---|
RO116153B1 (ro) | 2000-11-30 |
HRP931225A2 (en) | 1996-04-30 |
SG47443A1 (en) | 1998-04-17 |
BR9303987A (pt) | 1995-05-30 |
ZA936743B (en) | 1995-03-13 |
EP0646315B1 (en) | 1999-05-12 |
RU2117429C1 (ru) | 1998-08-20 |
HU9302594D0 (en) | 1993-11-29 |
CZ286811B6 (cs) | 2000-07-12 |
HUT68583A (en) | 1995-06-28 |
TW304863B (zh) | 1997-05-11 |
AU4748393A (en) | 1995-04-13 |
CA2106277A1 (en) | 1995-03-16 |
CA2106277C (en) | 2005-08-09 |
IL107053A0 (en) | 1993-12-28 |
SK284259B6 (sk) | 2004-12-01 |
HU214006B (en) | 1997-12-29 |
IL107053A (en) | 1998-10-30 |
AU670809B2 (en) | 1996-08-01 |
HRP931225B1 (en) | 1999-12-31 |
CZ191493A3 (en) | 1995-03-15 |
EP0646315A1 (en) | 1995-04-05 |
SK100293A3 (en) | 1995-04-12 |
JPH07126118A (ja) | 1995-05-16 |
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