WO2020119415A1 - 一种除草组合物及其应用 - Google Patents

一种除草组合物及其应用 Download PDF

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WO2020119415A1
WO2020119415A1 PCT/CN2019/119984 CN2019119984W WO2020119415A1 WO 2020119415 A1 WO2020119415 A1 WO 2020119415A1 CN 2019119984 W CN2019119984 W CN 2019119984W WO 2020119415 A1 WO2020119415 A1 WO 2020119415A1
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component
methyl
herbicidal composition
weeds
butyl
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PCT/CN2019/119984
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English (en)
French (fr)
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崔东亮
马宏娟
杨吉春
关爱莹
刘长令
罗艳梅
卢政茂
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沈阳中化农药化工研发有限公司
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Application filed by 沈阳中化农药化工研发有限公司 filed Critical 沈阳中化农药化工研发有限公司
Priority to US17/413,933 priority Critical patent/US20220087263A1/en
Priority to BR112021011353A priority patent/BR112021011353A8/pt
Priority to EP19897244.0A priority patent/EP3900537A4/en
Publication of WO2020119415A1 publication Critical patent/WO2020119415A1/zh

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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
    • A01N43/72—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
    • A01N43/80—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 1,2
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides

Definitions

  • the invention belongs to the field of agricultural herbicides, and relates to a herbicidal composition and its application.
  • Patent WO2016095768 reported isoxazoline-containing uracil compounds as shown in general formula I:
  • the compound of general formula I has very good herbicidal activity, and can effectively control barnyard grass, barnyard grass, sedge grass, sedge grass, crabgrass, hellebore, velvetleaf, zinnia, amaranthus retroflexus, purslane, Weeds of different leaf stages, such as Xanthium sibiricum, Solanum nigrum, Cassia, wild watermelon seedlings, and wild soybean, can obtain good herbicidal effects at low doses.
  • Diquat is a biocide herbicide that can be quickly absorbed by green plant tissues, and it has a very strong destructive effect on the lipid synthesis of plants and the double-layer membrane of chloroplasts, which stops the photosynthesis and the plants lose their water. Withered and died, it loses its activity soon after contact with the soil. Widely used for rapid weeding in fields, orchards, non-cultivated land, before harvesting, etc. However, the herbicide has poor conductivity, and can only damage the weed application site, and cannot kill the root system of the weed.
  • the object of the present invention is to provide a herbicidal composition and its application.
  • a herbicidal composition the active component of the herbicidal composition consists of component A and component B, component A is a compound having the following structural formula I; component B is diquat; two active components A and The weight ratio of component B is 1:40-40:1.
  • R 1 is selected from methyl
  • R 2 and R 3 may be the same or different, and are respectively selected from hydrogen, fluorine or chlorine;
  • R 4 is selected from CO 2 R 6 ;
  • R 5 is selected from hydrogen, methyl, ethyl, tert-butyl or trifluoromethyl
  • R 6 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, allyl, propargyl, methoxyethyl , Ethoxyethyl, 2-tetrahydrofuran methylene or 3-tetrahydrofuran methylene.
  • the weight ratio between component A and component B in the composition is 1:20 to 20:1;
  • R 1 is selected from methyl
  • R 2 is selected from fluorine
  • R 3 is selected from chlorine
  • R 4 is selected from CO 2 R 6 ;
  • R 5 is selected from methyl
  • R 6 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, allyl, propargyl, methoxyethyl , Ethoxyethyl, 2-tetrahydrofuran methylene or 3-tetrahydrofuran methylene;
  • the component B is diquat.
  • the weight ratio between component A and component B in the composition is 1:10 to 10:1;
  • R 1 is selected from methyl
  • R 2 is selected from fluorine
  • R 3 is selected from chlorine
  • R 4 is selected from CO 2 C 2 H 5 , CO 2 C 3 H 7 or CO 2 C 4 H 9
  • R 5 is selected from methyl
  • the component B is diquat.
  • the weeds are grass weeds, broad-leaved weeds, sedge weeds, algae, ferns, and woody shrubs.
  • a herbicide the effective herbicidal ingredient is the herbicidal composition, and the weight percentage of the herbicidal composition is 0.1-95%.
  • Halogen refers to fluorine, chlorine, bromine or iodine.
  • Alkyl linear or branched alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl.
  • Haloalkyl straight-chain or branched-chain alkyl groups. The hydrogen atoms on these alkyl groups may be partially or fully substituted with halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, di Fluoromethyl, trifluoromethyl, etc.
  • the herbicidal composition of the present invention is applied to places where undesired vegetation is present or expected to exist, that is, it can be selectively or non-selectively used where places where undesired vegetation is present or expected to be present.
  • it can be applied to stems and leaves of undesirable vegetation, or post-emergence treatment of burnt waste and crops that are tolerant and non-tolerant crops before planting or after planting or after planting.
  • the herbicide is applied to non-cultivated land, orchard, rubber plantation, idle cultivated land, rubber plantation, eucalyptus forest, cedar forest, forest, fire protection road, lawn, railway, highway, airport and warehouse.
  • the tolerant and non-tolerant crops are selected from rice, corn, legume crops, rape, vegetables, cotton, sugar beet, small grain cereals, soybeans, peanuts, sugar cane, sunflowers, cultivated crops, woody plants.
  • the orchard includes apple orchard, peach orchard, vineyard, pear orchard, tea orchard, mulberry orchard.
  • the undesirable vegetation includes gramineous weeds, broad-leaved weeds, sedge weeds, algae, ferns, and woody shrubs.
  • the herbicidal composition of the present invention mixes two active components to expand the herbicidal spectrum, reduce the amount and frequency of use, prevent the development of resistant weeds and control resistant weeds.
  • the herbicidal composition of the present invention utilizes the complementarity of different action mechanisms, and has the characteristics of contact and systemic absorption, which increases the adaptability to unfavorable environments such as drought and low temperature in the field, speeds up the reaction speed, and weeds more thoroughly;
  • the herbicidal composition of the present invention extends the period of application, and can further inhibit and control the weeds of grasses with larger leaf ages; at the same time, it can protect certain glyphosate-tolerant weeds such as small sphaeranthus and bermudagrass , Goosegrass, etc. have a high control effect;
  • the herbicide stem and leaf spray treatment of the present invention can be used to prevent most weeds in non-cultivated land, orchards, idle cultivated land, rubber plantations, eucalyptus forests, forests, fire lanes, lawns, railways, highways, airports and warehouses.
  • the synergistic effect of the herbicidal composition of the present invention on gramineous weeds and broad-leaved weeds can be further illustrated by the following examples, but the present invention is by no means limited thereto, wherein the active components of the herbicidal composition of the present invention are groups Divided into A and component B, said component A is a compound represented by formula I, component B is diquat. The percentages in all proportions are weight percentages, and the active component is calculated in terms of effective content.
  • Example 1 The bioassay of indoor combined action of weeds was carried out on the compound A and B of the present invention.
  • the compound A is compound A-3, A-4 and A-5 in Table 1 of the compound of general formula I example.
  • the weed cultivation method is as follows: the quantitative weed seeds velvetleaf and barnyard grass are sown in a paper cup with a nutrient soil of 7 cm in diameter respectively, and then cultivated in a greenhouse after sowing, covering the soil, suppressing and spraying water. Gramineae weeds grow to 5-7 leaf stage, broad-leaved weeds 6-8 leaf stage, stem and leaf spray treatment, the experiment is set up 3 times.
  • the treatment solution was naturally dried and placed in the greenhouse according to conventional methods. According to the suppression or death of the weeds, a visual control effect survey was conducted 30 days after the treatment (see Table 2 to Table 7).
  • composition method The samples of the tested pharmaceuticals are all original drugs, first dissolved in a mixed solvent of acetone:dimethylformyl (1:2, V/V), and then formulated into a certain concentration with 1 ⁇ Tween 80 water Mother liquid, and then prepare different doses of treatment liquid according to the test protocol.
  • the invention uses the Gowing method to evaluate the combined effect of the proposed composition.
  • test results showed that components A-3, A-4 and A-5 were mixed with component B respectively, showing a significant increase in grass weeds barnyard grass and velvetleaf Effect.

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  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

一种除草剂组合物及其应用方法，组合物为A、B两种活性成分，其中组分A选自通式（I）所示的化合物。组分B选自敌草快。本除草剂组合物特别适用于防除对有机磷类除草剂特别是草甘膦具有耐性或抗性的杂草。

Description

一种除草组合物及其应用 技术领域
本发明属于农用除草剂领域，涉及一种除草组合物及其应用。
背景技术
专利WO2016095768报道了如通式I所示的含异恶唑啉脲嘧啶类化合物：
Figure PCTCN2019119984-appb-000001
通式I化合物具有很好的除草活性，可以有效地控制稗草、稗草、异型莎草、水莎草、马唐、荩草、苘麻、百日草、反枝苋、马齿苋、苍耳、龙葵、决明、野西瓜苗、野大豆等不同叶期的杂草，在低剂量下就可以获得很好的除草效果。
敌草快为触杀灭生性除草剂，药剂可迅速被绿色植物组织吸收，对植物的脂类合成和叶绿体的双层膜具有极强的破坏力，使光合作用终止，植物徐苏失水、枯萎死亡，与土壤接触后很快失去活性。广泛用于大田、果园、非耕地、收割前等快速除草。但该除草剂传导性较差，只能使杂草着药部位受害，不能杀死杂草的根系。
发明内容
本发明的目的在于提供一种除草组合物及其应用。
为实现上述目的，本发明的技术方案如下：
一种除草组合物，除草组合物活性组分由组分A和组分B组成，组分A为具有如下结构式I所示的化合物；组分B为敌草快；两种活性组分A和组分B的重量比为1:40～40:1。
Figure PCTCN2019119984-appb-000002
式I中：
R 1选自甲基；
R 2、R 3可相同或不同，分别选自氢、氟或氯；
R 4选自CO 2R 6；
R 5选自氢、甲基、乙基、叔丁基或三氟甲基；
R 6选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、2-四氢呋喃亚甲基或3-四氢呋喃亚甲基。
优选，所述组合物中组分A和组分B两组分之间的重量比为1:20～20:1；
所述组分A，式I中：
R 1选自甲基；
R 2选自氟
R 3选自氯；
R 4选自CO 2R 6；
R 5选自甲基；
R 6选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、2-四氢呋喃亚甲基或3-四氢呋喃亚甲基；
所述组分B为敌草快。
更优选，所述组合物中组分A和组分B两组分之间的重量比为1:10～10:1；
所述组分A，式I中：
R 1选自甲基；
R 2选自氟
R 3选自氯；
R 4选自CO 2C 2H 5、CO 2C 3H 7或CO 2C 4H 9
R 5选自甲基；
所述组分B为敌草快。
一种除草组合物的应用，所述组合物在防除杂草中的应用。
所述杂草为禾本科杂草、阔叶杂草、莎草科杂草、藻类、蕨类和木本灌木。
一种除草剂，除草有效成分为所述的除草组合物，除草组合物的重量百分含量为0.1～95％。
上面给出的通式I化合物的定义中，汇集所用术语一般定义如下：
卤素：指氟、氯、溴或碘。烷基：直链或支链烷基，例如甲基、乙基、丙基、异丙基、正丁基或叔丁基。卤代烷基：直链或支链烷基，在这些烷基上的氢原子可部分或全部被卤原子所取代，例如，氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基等。
通式I的部分化合物可以用表1中列出的具体化合物来说明，但本发明并不仅限于这些化合物；且通式化合物可按照WO2016095768中记载制备获得，表中的化合物R 1＝CH 3，其他基团如表1所示。
Figure PCTCN2019119984-appb-000003
表1
Figure PCTCN2019119984-appb-000004
Figure PCTCN2019119984-appb-000005
Figure PCTCN2019119984-appb-000006
本发明除草组合物施用于存在或预期存在的不希望植被的场所，即可以选择性或非选择性地用于存在或预期存在的不希望植被的场所。具体是可以施用于不希望植被的茎叶，或作物种植前或播种后出苗前的烧荒及耐受作物及非耐受作物的苗后处理。
所述的除草剂施用于非耕地、果园、橡胶园、闲置耕地、橡胶园、桉树林、杉树林、森林、防火道、草坪、铁路、公路、机场及仓库场所。
所述耐受和非耐受作物选自水稻、玉米、豆类作物、油菜、蔬菜、棉花、甜菜、小粒谷物、大豆、花生、甘蔗、向日葵、栽培作物、木本植物。所述的果园包括苹果园、桃园、葡萄园、梨园、茶园、桑园、柑橘园。所述不希望的植被包括禾本科杂草、阔叶杂草、莎草科杂草、藻类、蕨类和木本灌木。
本发明所具优点：
1、本发明除草组合物中两种活性成分之间具有非常明显的增效作用，进而降低了各活性成分的用量；
2、本发明的除草组合物将两种活性组分混用扩大杀草谱、降低使用量和使用频率、防止抗性杂草抗性产生和防除抗性杂草。
3、本发明除草组合物利用不同作用机制的互补，兼具触杀和内吸的特性，增加了对田间干旱、低温等不良环境的适应性，加快了反应速度，除草更彻底；
4、本发明除草组合物扩大了施药适期，进一步可对较大叶龄禾本科杂草，持续抑制和防除作用增强；同时，对某些草甘膦耐性杂草如小飞蓬、狗牙根、牛筋草等具有很高的防除效果；
5、本发明除草剂茎叶喷雾处理，可用于防除非耕地、果园、闲置耕地、橡胶园、桉树林、森林、防火道、草坪、铁路、公路、机场及仓库等场所的大多数杂草。
具体实施方式
本发明除草组合物对禾本科杂草和阔叶杂草的协同增效作用可通过下列实施例作进一步说明，但本发明绝非仅限于此，其中，本发明除草组合物活性组分为组分A和组分B，所述组分A为式Ⅰ所示的化合物，组分B为敌草快。所有配比中的百分比均为重量百分比，活性组分以有效含量计算。
生物活性测定实施例
实施例1对本发明组分A与组分B复配进行了对杂草的室内联合作用生物测定，组分A以通式I化合物表1中A-3、A-4、A-5化合物为例。
通过室内盆栽试验，明确组合物对杂草的联合作用。
杂草培养方法为：将定量的杂草种子苘麻和稗草分别播于直径为7cm的装有营养土的纸杯中，播后覆土、镇压、淋水后在温室培养。禾本科杂草长至5～7叶期、阔叶杂草6～8叶期，茎叶喷雾处理，试验设3次重复。处理待药液自然风干，放于温室内按常规方法管理，根据杂草受抑制或死亡的情况，于处理后30天，进行目测防效调查(参见表2-表7)。
药剂配制方法：供试药剂药剂样品均为原药，先用丙酮：二甲基甲酰(1：2，V/V)的混合溶剂溶解，再用1‰吐温80水配制成一定浓度的母液，然后按照试验方案配制不同剂量的处理液。
本发明采用Gowing法对提出的组合物的联合作用进行评价。
Figure PCTCN2019119984-appb-000007
式中：
X—除草剂组分A用量为P时的杂草防效；
Y—除草剂组分B用量为Q时的杂草防效；
E 0—除草剂组分A用量为P时的理论防效+除草剂组分B用量为Q时的理论防效；
E—除草剂组分A与除草剂组分B按上述比例混用后的实测防效。
当E-E 0>10％时，为增效作用；当E-E 0<-10％时，为拮抗作用；当E-E 0值介于±10％时，为加成作用。
表2组分A-3与B混用对稗草和苘麻的联合作用
Figure PCTCN2019119984-appb-000008
Figure PCTCN2019119984-appb-000009
表3组分A-4与B混用对稗草和苘麻的联合作用
Figure PCTCN2019119984-appb-000010
表4组分A-5与B混用对稗草和苘麻的联合作用
Figure PCTCN2019119984-appb-000011
试验结果(表2，表3，表4)表明，组分A-3、A-4和A-5分别与组分B混用，对禾本科杂草稗草和苘麻均表现出明显的增效作用。

Claims (6)

  1. 一种除草组合物，其特征在于：除草组合物活性组分由组分A和组分B组成，组分A为具有如下结构式I所示的化合物；组分B为敌草快；两种活性组分A和组分B的重量比为1:40～40:1。
    Figure PCTCN2019119984-appb-100001
    式I中：
    R 1选自甲基；
    R 2、R 3可相同或不同，分别选自氢、氟或氯；
    R 4选自CO 2R 6；
    R 5选自氢、甲基、乙基、叔丁基或三氟甲基；
    R 6选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、2-四氢呋喃亚甲基或3-四氢呋喃亚甲基。
  2. 根据权利要求1所述的除草组合物，其特征在于：所述组合物中组分A和组分B两组分之间的重量比为1:20～20:1；
    所述组分A，式I中：
    R 1选自甲基；
    R 2选自氟
    R 3选自氯；
    R 4选自CO 2R 6；
    R 5选自甲基；
    R 6选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、2-四氢呋喃亚甲基或3-四氢呋喃亚甲基；
    所述组分B为敌草快。
  3. 根据权利要求2所述的除草组合物，其特征在于：所述组合物中组分A和组分B两组分之间的重量比为1:10～10:1；
    所述组分A，式I中：
    R 1选自甲基；
    R 2选自氟
    R 3选自氯；
    R 4选自CO 2C 2H 5、CO 2C 3H 7或CO 2C 4H 9
    R 5选自甲基；
    所述组分B为敌草快。
  4. 一种权利要求1所述的除草组合物的应用，其特征在于：所述组合物在防除杂草中的应用。
  5. 根据权利要求4所述的除草组合物的应用，其特征在于：所述杂草为禾本科杂草、阔叶杂草、莎草科杂草、藻类、蕨类和木本灌木。
  6. 一种除草剂，其特征在于：除草有效成分为权利要求1所述的除草组合物，除草组合物的重量百分含量为0.1～95％。
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