CN113115788A - Compound weeding composition and preparation method thereof - Google Patents

Compound weeding composition and preparation method thereof Download PDF

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Publication number
CN113115788A
CN113115788A CN202110345914.1A CN202110345914A CN113115788A CN 113115788 A CN113115788 A CN 113115788A CN 202110345914 A CN202110345914 A CN 202110345914A CN 113115788 A CN113115788 A CN 113115788A
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glufosinate
ammonium
diuron
compound
prepared
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丁元
郭晓刚
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Anhui Xitian Biotechnology Co ltd
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Anhui Xitian Biotechnology Co ltd
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N57/00Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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 the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06Preparation of nitro compounds
    • C07C201/12Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00Preparation of derivatives of isocyanic acid
    • C07C263/10Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1809Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
    • C07C273/1818Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
    • C07C273/1827X being H
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids R2P(=O)(OH); Thiophosphinic acids, i.e. R2P(=X)(XH) (X = S, Se)
    • C07F9/301Acyclic saturated acids which can have further substituents on alkyl

Abstract

The invention provides a compound weeding composition, which is prepared by mixing glufosinate-ammonium and diuron, wherein the glufosinate-ammonium content is 1-60 parts by weight, and the diuron content is 1-40 parts by weight. After glutamine synthetase in glufosinate-ammonium is inhibited, synthesis of glutamine is inhibited, nitrogen metabolism in plants is disordered, synthesis of substances such as proteins and nucleotides is reduced, photosynthesis is inhibited, chlorophyll synthesis is reduced, the content of ammonium ions in cells is increased, cell membranes are damaged, chloroplasts are disintegrated, photosynthesis starts to be inhibited within 2-6 hours of the weeds to be treated, growth stops within 1 day, symptoms such as greenness and necrosis appear within 2-3 days, the whole plants die within 1-2 weeks, and diluted diuron can invade into soil rhizomes, so that a long-acting weed removal inhibiting effect is guaranteed.

Description

Compound weeding composition and preparation method thereof
Technical Field
The invention relates to the technical field of compound herbicides, in particular to a compound herbicide composition and a preparation method thereof.
Background
Herbicides, also known as herbicides, are chemical agents that kill weeds or unwanted plants without affecting the normal growth of crops. Can be used for preventing and controlling farmland weeds or killing weeds or shrubs in non-agricultural lands. They can be classified into selective herbicides and biocidal herbicides according to their action characteristics. By selective herbicide is meant a herbicide that selectively kills certain species of plants, but not others, at a range of dosages and concentrations, the effect of which is influenced by the herbicide, the plant and the environmental conditions. They are divided by action into biocidal and selective herbicides, the selective herbicides being effective in most cases, in particular derivatives of nitrophenol, chlorophenol, carbamic acid. The development of the herbicide in the world is gradually steady, the herbicide mainly develops high-efficiency, low-toxicity, broad-spectrum and low-dosage varieties, the disposable treatment agent with little environmental pollution gradually becomes the mainstream, and the common varieties are organic compounds and can be widely used for preventing and controlling harmful plants such as weeds, miscellaneous irrigation, miscellaneous trees and the like in farmlands, orchards, flower nursery gardens, grasslands, uncultivated areas, railway lines, riverways, reservoirs, warehouses and the like.
However, the existing glufosinate-ammonium adopts a contact weeding method, weeds can be quickly killed in a short time, but the fundamental influence on the weeds is avoided, the effective time of the traditional glufosinate-ammonium reagent can only be maintained about half a month, and the weeds still need to be killed in a later period according to the period, so that the treatment period is long, and the consumption of manpower and material resources is also brought; therefore, the existing requirements are not met, and a compound herbicide composition of glufosinate-diuron and a preparation method thereof are provided.
Disclosure of Invention
The invention aims to overcome the defects in the prior art, provides a compound weeding composition and a preparation method thereof, and aims to solve the problems that the existing glufosinate in the background technology adopts a contact weeding method, weeds can be quickly killed in a short time, but the fundamental influence on the weeds is avoided, the effective time of the traditional glufosinate reagent can only be maintained for about half a month, and the weeds are required to be killed according to the period in the later period, so that the treatment period is long, and the consumption of manpower and material resources is caused.
In order to solve the technical problems, the invention adopts the technical scheme that: the compound weeding composition is prepared by mixing 1-60 parts of glufosinate-ammonium and 1-60 parts of diuron by weight.
The compound weeding composition is prepared by mixing 5-20 parts of glufosinate-ammonium and 20-50 parts of diuron by weight.
Further, the compound herbicide also comprises an auxiliary agent, wherein the content of the auxiliary agent is 45-60 parts, and the auxiliary agent is one or more of a wetting agent, a dispersing agent, an emulsifying agent, an antifreezing agent, a defoaming agent, a thickening agent, a mildew preventive, a solvent, a disintegrating agent and a filler.
Furthermore, the formulation of the compound herbicide composition comprises four kinds of wettable powder, water dispersible granules, water suspending agents and oil suspending agents.
A preparation method of a compound weeding composition comprises the following steps:
the method comprises the following steps: glutamic acid is taken as a raw material, and then lactone is formed by dehydration, and then the lactone is subjected to ring opening by hydrogen chloride to regenerate an intermediate (S) -2-methoxycarbonylamino-4-chloro-methyl butyrate;
step two: reacting the intermediate produced in the step with diethyl methylphosphite to obtain a glufosinate-ammonium derivative, and finally processing to obtain L-glufosinate-ammonium;
step three: mixing and stirring the prepared L-glufosinate-ammonium and diatomite, firstly performing adsorption operation after uniformly stirring, and then adding a dispersant of ammonium polyacrylate salt, liquid paraffin, a suspending agent and other auxiliaries into the raw materials;
step four: after the mixing is finished, putting the prepared product into a jet mill, and impacting the material by high-speed airflow or hot steam generated by compressed air by utilizing the autogenous grinding function of the material to ensure that the materials have strong collision and friction effects with each other so as to form powdery particles;
step five: after the preparation of the product in the fourth step is finished, mixing a certain amount of melt-dehydrated p-chloronitrobenzene with a proper amount of catalyst anhydrous ferric chloride, heating to 105 ℃ for introducing chlorine, reacting at 110 ℃ for 8-9h to obtain 3, 4-dichloronitrobenzene;
step six: reducing the 3, 4-dichloronitrobenzene prepared in the step to generate 3, 4-dichloroaniline, and then preparing 3, 4-dichloroisocyanic acid phenyl toluene liquid;
step seven: cooling 3, 4-dichloro phenyl isocyanate toluene to below 20 ℃, dropwise adding 30-40% dimethylamine aqueous solution, then centrifugally filtering, recovering the solvent, washing a filter cake to be neutral, and drying at 90-100 ℃ to prepare diuron;
step eight: mixing the diuron particles prepared in the fourth step and the glufosinate-ammonium powder prepared in the seventh step according to a proportion, and adding other additives to obtain the compound weeding composition.
Further, in the sixth step, introducing phosgene to the toluene solution at 0 ℃ for saturation, then dropwise adding 3, 4-dichloroaniline, controlling the temperature to be 0-10 ℃ for about 15min, then continuously introducing phosgene, slowly increasing the reaction temperature to 40 ℃, increasing the phosgene flow, then heating to 65-75 ℃, reacting for 1-2h, clearing the materials, stopping introducing phosgene, rapidly heating to 90-100 ℃, introducing nitrogen or dry air, and removing excessive phosgene and hydrochloric acid gas to prepare the 3, 4-dichloroisocyanate toluene solution.
Further, in the seventh step, the ratio of ester to amine is 1:1.05, the reaction temperature is automatically raised to 34 ℃, the reaction temperature is controlled not to exceed 50 ℃, the final pH is 9-10, and the reaction is carried out for 2.5 hours at 15 ℃.
Compared with the prior art, the invention has the beneficial effects that:
1. the diuron particles and the glufosinate powder are matched according to the ratio of 1:2, finally, two kinds of products are independently packaged in a single batch according to the ratio, after glutamine synthetase in glufosinate is inhibited, synthesis of glutamine is inhibited, nitrogen metabolism in plants is disordered, synthesis of substances such as protein and nucleotide is reduced, photosynthesis is inhibited, chlorophyll synthesis is reduced, the content of ammonium ions in cells is increased, cell membranes are damaged, chloroplast is disintegrated, photosynthesis starts to be inhibited within 2-6 hours of medicinal weeds, growth is stopped within 1 day, symptoms such as green loss and necrosis appear within 2-3 days, the whole plant withers within 1-2 weeks, and diluted diuron can invade into soil rhizomes, so that the long-acting weed removal inhibition effect is guaranteed.
2. The compound weeding composition is prepared by mixing glufosinate-ammonium and diuron, wherein a glufosinate-ammonium reagent is wettable powder, the adhesiveness of the wettable powder is strong, the medicine can be better adsorbed on the surfaces of stems and leaves in the spraying process, the diuron reagent is a water dispersible granule, and the water dispersible granule does not use an organic solvent, so that the environmental pollution can be reduced, no dust flies during spraying, the compound weeding composition is safe for operators, the environmental pollution is reduced, meanwhile, the content of effective components in the interior is high in the manufacturing process, few additives are added, and the relative density of the product is high.
Detailed Description
It is easily understood that according to the technical solution of the present invention, a person skilled in the art can propose various alternative structures and implementation ways without changing the spirit of the present invention. Therefore, the following detailed description is merely illustrative of the technical solutions of the present invention, and should not be construed as being all of the present invention or limiting or restricting the technical solutions of the present invention.
A compound weeding composition is prepared by mixing 5-20 parts of glufosinate-ammonium and 20-50 parts of diuron by weight. The compound herbicide also comprises an auxiliary agent, wherein the content of the auxiliary agent is 45-60 parts, and the auxiliary agent is one or more of a wetting agent, a dispersing agent, an emulsifying agent, an antifreezing agent, a defoaming agent, a thickening agent, a mildew preventive, a solvent, a disintegrating agent and a filler. The formulation of the compound weeding composition comprises four kinds of wettable powder, water dispersible granules, water suspending agent and oil suspending agent.
Diuron is a systemic herbicide and has certain contact killing performance. After being absorbed into human plants by roots and leaves of the plants, the plants inhibit photosynthesis of the plants, so that the leaves turn yellow and die finally. Diuron can be selectively used for weeding through potential difference and time difference under the condition of low dosage, and can be used as a biocidal herbicide under the condition of high dosage.
When the glufosinate-ammonium is sprayed on plants, the glufosinate-ammonium can be quickly absorbed into the plants through stems and leaves and is conducted on xylem by plant transpiration, but the glufosinate-ammonium can be quickly decomposed and loses efficacy by microorganisms in soil after contacting the soil, so that the glufosinate-ammonium is rarely or hardly absorbed by roots, and the glufosinate-ammonium has low toxicity to other organisms except the plants and is high in safety.
A preparation method of a compound weeding composition comprises the following steps:
the method comprises the following steps: glutamic acid is taken as a raw material, and then lactone is formed by dehydration, and then the lactone is subjected to ring opening by hydrogen chloride to regenerate an intermediate (S) -2-methoxycarbonylamino-4-chloro-methyl butyrate;
step two: reacting the intermediate produced in the step with diethyl methylphosphite to obtain glufosinate-ammonium derivatives, and finally processing the glufosinate-ammonium derivatives to obtain L-glufosinate-ammonium which has chirality, wherein L-glufosinate-ammonium has a weeding effect and D-type racemes are usually produced, and the D-glufosinate-ammonium has almost no activity;
step three: mixing and stirring the prepared L-glufosinate-ammonium and diatomite, firstly performing adsorption operation after uniformly stirring, and then adding a dispersant of ammonium polyacrylate salt, liquid paraffin, a suspending agent and other auxiliaries into the raw materials;
step four: after the mixing is finished, putting the prepared product into a jet mill, and impacting the material by high-speed airflow or hot steam generated by compressed air by utilizing the autogenous grinding function of the material to ensure that the materials generate strong collision and friction effects with each other so as to form powdery particles, wherein the diameter of the medicine particles is required to be less than 44 microns, and the average particle size is 25 microns;
step five: after the preparation of the product in the fourth step is finished, mixing a certain amount of melt-dehydrated p-chloronitrobenzene with a proper amount of catalyst anhydrous ferric chloride, heating to the temperature of 100-;
step six: reducing the 3, 4-dichloronitrobenzene prepared in the step to generate 3, 4-dichloroaniline, and then preparing 3, 4-dichloroisocyanic acid phenyl toluene liquid;
step seven: cooling 3, 4-dichloro phenyl isocyanate toluene to below 20 ℃, dropwise adding 30-40% dimethylamine aqueous solution, then centrifugally filtering, recovering the solvent, washing a filter cake to be neutral, and drying at 90-100 ℃ to prepare diuron;
step eight: mixing the diuron particles prepared in the fourth step and the glufosinate-ammonium powder prepared in the seventh step according to a proportion, and adding other additives to obtain the compound weeding composition.
The following embodiments are specifically described below.
Example 1
40% glufosinate-ammonium and diuron compounded weeding dispersible oil suspending agent
20% of glufosinate-ammonium, 20% of diuron, 12% of castor oil polyoxyethylene ether, 3% of calcium dodecylbenzene sulfonate, 5% of alkylphenol polyoxyethylene polyoxypropylene ether and the balance of vegetable oil to 100%.
Example 2
55% glufosinate-ammonium and diuron compound weeding wettable powder
5% of glufosinate-ammonium, 50% of diuron, 7% of sodium dodecyl sulfate, 6% of sodium lignosulfonate, 2% of polyvinyl alcohol, 2% of white carbon black and kaolin, and the balance is up to 100%.
Example 3
45% glufosinate-ammonium and diuron compound weeding suspending agent
5% of glufosinate-ammonium, 40% of diuron, 6% of phenethyl phenol polyoxypropylene ether, 2.5% of alkyl naphthalene sulfonate, 1% of silicone, 2.5% of sodium benzoate, 1.5% of ethylene glycol, 1% of Arabic gum and the balance of water to 100%.
Example 4
40% glufosinate-ammonium and diuron compound weeding water dispersible granule
20% of glufosinate-ammonium, 20% of diuron, 8% of carboxylate dispersant, 4% of sodium dodecyl sulfate and the balance of high clay to 100%.
The field efficacy embodiment: field control effect of glufosinate-diuron compound weeding composition
The corn field in the countryside has a plurality of weed species, the broad-leaved weeds and the gramineous weeds are mixed, the broad-leaved weeds and the gramineous weeds mainly comprise amaranthus retroflexus, Convolvulus arvensis, green bristlegrass, digitaria sanguinea, lii and the like, and a large amount of wheat green (wheat self-growing wheat seedlings) is also contained. The severe occurrence of weeds poses a significant hazard to local corn production. The test agents and the amounts are shown in table 2, and are repeated in 4 treatment cells, each cell having an area of 20 square meters. The weed condition of each plot was investigated before the application, once every 7 days, for 2 applications. Weed growth was investigated 7 days after the last application and control effects were calculated. The experimental results are shown below:
TABLE 2 field control Effect of glufosinate-diuron compounded herbicidal compositions
Treatment of Dosage (g/hm) of active ingredient2) Prevention effect/%)
Example 1 65 94.3
Example 2 65 92.6
Example 3 65 93.9
20% glufosinate-ammonium wettable powder 54 74.2
35% diuron suspension 68 77.6
As can be seen from Table 2, when glufosinate-ammonium and diuron are compounded and used, the control effect on field weeds is obviously improved, and compared with a single agent, the herbicide composition has an obvious synergistic effect.
The technical scope of the present invention is not limited to the above description, and those skilled in the art can make various changes and modifications to the above-described embodiments without departing from the technical spirit of the present invention, and such changes and modifications should fall within the protective scope of the present invention.

Claims (7)

1. The compound weeding composition is characterized by being prepared by mixing 1-60 parts of glufosinate-ammonium and 1-60 parts of diuron by weight.
2. The compound herbicidal composition as claimed in claim 1, wherein the compound herbicidal composition is prepared by mixing 5 to 20 parts by weight of glufosinate-ammonium and 20 to 50 parts by weight of diuron.
3. The compound herbicide composition as claimed in claim 2, further comprising an auxiliary agent in an amount of 45-60 parts, wherein the auxiliary agent is one or more of a wetting agent, a dispersing agent, an emulsifier, an antifreeze agent, a defoamer, a thickener, a mildewproof agent, a solvent, a disintegrant, and a filler.
4. The compound herbicidal composition according to claim 3, wherein the formulation of the compound herbicidal composition comprises four kinds of wettable powder, water dispersible granules, water suspension concentrate and dispersible oil suspension concentrate.
5. A method for preparing a compound herbicidal composition as claimed in any one of claims 1 to 4, characterized by comprising the steps of:
the method comprises the following steps: glutamic acid is taken as a raw material, and then lactone is formed by dehydration, and then the lactone is subjected to ring opening by hydrogen chloride to regenerate an intermediate (S) -2-methoxycarbonylamino-4-chloro-methyl butyrate;
step two: reacting the intermediate produced in the step with diethyl methylphosphite to obtain a glufosinate-ammonium derivative, and finally processing to obtain L-glufosinate-ammonium;
step three: mixing and stirring the prepared L-glufosinate-ammonium and diatomite, firstly performing adsorption operation after uniformly stirring, and then adding a dispersant of ammonium polyacrylate salt, liquid paraffin, a suspending agent and other auxiliaries into the raw materials;
step four: after the mixing is finished, putting the prepared product into a jet mill, and impacting the material by high-speed airflow or hot steam generated by compressed air by utilizing the autogenous grinding function of the material to ensure that the materials generate strong collision and friction effects with each other so as to form powdery glufosinate-ammonium particles;
step five: after the preparation of the product in the fourth step is finished, mixing a certain amount of melt-dehydrated p-chloronitrobenzene with a proper amount of catalyst anhydrous ferric chloride, heating to the temperature of 100-;
step six: reducing the 3, 4-dichloronitrobenzene prepared in the step to generate 3, 4-dichloroaniline, and then preparing 3, 4-dichloroisocyanic acid phenyl toluene liquid;
step seven: cooling 3, 4-dichloro phenyl isocyanate toluene to below 20 ℃, dropwise adding 30-40% dimethylamine aqueous solution, then centrifugally filtering, recovering the solvent, washing a filter cake to be neutral, and drying at 90-100 ℃ to prepare diuron;
step eight: mixing the diuron particles prepared in the fourth step and the glufosinate-ammonium powder prepared in the seventh step according to a proportion, and adding other additives to obtain the compound weeding composition.
6. The preparation method of the compound herbicide composition of glufosinate-diuron according to claim 5, which is characterized by comprising the following steps: and in the sixth step, introducing phosgene to the toluene solution at 0 ℃ for saturation, then dropwise adding 3, 4-dichloroaniline, controlling the temperature to be 0-10 ℃ for about 15min, then continuously introducing phosgene, slowly increasing the reaction temperature to 40 ℃, increasing the phosgene flow, then heating to 65-75 ℃, reacting for 1-2h, clearing the materials, stopping introducing phosgene, rapidly heating to 90-100 ℃, introducing nitrogen or dry air, and removing excess phosgene and hydrochloric acid gas to obtain the 3, 4-dichloroisocyanic acid phenyl ester toluene solution.
7. The preparation method of the compound herbicide composition of glufosinate-diuron according to claim 5, which is characterized by comprising the following steps: in the seventh step, the ratio of ester to amine is 1:1.05, the reaction temperature is automatically raised to 34 ℃, meanwhile, the reaction temperature is controlled not to exceed 50 ℃, the pH is 9-10 at the end point of dripping, and the reaction is carried out for 2.5 hours at 15 ℃.
CN202110345914.1A 2021-03-31 2021-03-31 Compound weeding composition and preparation method thereof Pending CN113115788A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5429101A (en) * 2000-07-12 2002-01-17 Aventis Cropscience Gmbh Defoliant
WO2019030092A1 (en) * 2017-08-09 2019-02-14 Basf Se Herbicidal mixtures comprising l-glufosinate or its salt and at least one photosynthesis inhibitor

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5429101A (en) * 2000-07-12 2002-01-17 Aventis Cropscience Gmbh Defoliant
WO2019030092A1 (en) * 2017-08-09 2019-02-14 Basf Se Herbicidal mixtures comprising l-glufosinate or its salt and at least one photosynthesis inhibitor

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
无: "敌草隆", 《HTTPS://WWW.CHEMSRC.COM/CAS/330-54-1_ 23804 4.HTML》 *
毛明珍等: "草铵膦的合成研究进展", 《农药》 *

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Application publication date: 20210716