CN110922326A - Dicamba tetramethylguanidine salt and preparation method and application thereof - Google Patents
Dicamba tetramethylguanidine salt and preparation method and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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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
- A01N47/40—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 the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
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Abstract
The invention discloses dicamba tetramethylguanidine salt and a preparation method and application thereof, the dicamba tetramethylguanidine salt is obtained by reacting dicamba and tetramethylguanidine, and has the advantages of both dicamba and tetramethylguanidine, on one hand, the synthesis of nucleic acid and protein in a plant body is promoted, so that cells are excessively divided and elongated, and tissues are malformed due to excessive growth, thereby hindering material transportation, causing weed death and having quick response; on the other hand, the compound has the advantages of high molecular weight, high safety and difficult volatilization, so that the compound is safe and environment-friendly in the processes of processing, storage, transportation, construction and the like, can effectively kill various broadleaf weeds in a wheat field when being applied in the field, improves the attachment rate of the liquid medicine on the leaf surfaces of the weeds, promotes the weeding activity and delays the generation of weed resistance.
Description
Technical Field
The invention relates to the technical field of herbicides, in particular to dicamba tetramethylguanidine salt and a preparation method and application thereof.
Background
Wheat is the second major food crop in China, accounts for 20% -27% of the total area of the food crops in China over the years, and the planting range almost extends to all agricultural areas. The wheat field weed control area in China accounts for 30% of the planting area, wherein the serious weed accounts for about 10%, and the wheat field weed control is an important measure for guaranteeing the wheat production. The wheat field has a lot of weeds, and the weeds grow rapidly, the growth amount is large, the weeds compete for water, fertilizer and space with wheat, wheat seedlings are greatly damaged by the weeds, plants are short and yellow in thin stems and leaves, the growth of the wheat in the middle and later stages is poor, and the yield is influenced. The common weeds have the characteristics of early maturity, irregular and staged seedling emergence, are not beneficial to control, and many weeds have amazing reproductive capacity and even can die and grow repeatedly, for example, Amaranthus retroflexus can restore the growth after being manually pulled out and dried in the field for 3 days. In order to reduce economic loss caused by weeds and reduce labor intensity, and meanwhile, the chemical weeding method is gradually accepted by people because of convenient weeding, quick response and long control time.
The existing herbicide for removing weeds in wheat fields is a compound herbicide generally, has large using amount, is easy to generate resistance for crops, is limited by the types, regions, climatic conditions and operation modes of the herbicide, is not easy to be processed into different formulations, and cannot effectively prevent weeds in wheat fields; therefore, the herbicide can be quickly absorbed in weeds, can effectively prevent and kill off the weeds in the wheat field, does not influence the growth of wheat, does not poison the succeeding crops, and has high safety, and the research and the development of the herbicide for the wheat field are urgently needed.
Disclosure of Invention
In order to solve the problems, the invention aims to provide dicamba tetramethylguanidine salt and a preparation method and application thereof.
In order to achieve the purpose, the invention is realized by the following technical scheme:
dicamba tetramethylguanidine salt with structural formula
The invention also comprises a preparation method of the dicamba tetramethylguanidine salt, which comprises the following steps: dissolving dicamba in toluene, stirring and heating to reflux, dripping tetramethylguanidine into the toluene, continuing refluxing for 3-4 hours after dripping is finished, stirring and cooling to 20-30 ℃, performing suction filtration, and drying a filter cake to obtain dicamba tetramethylguanidine salt; wherein the molar volume ratio of dicamba to tetramethylguanidine to toluene is 1 mol: 0.9-1.3 mol: 1-1.5L.
The invention also discloses a herbicide preparation containing the dicamba tetramethylguanidine salt, which is prepared by taking the dicamba tetramethylguanidine salt as an effective component, wherein the total mass percentage of the dicamba tetramethylguanidine salt in the herbicide preparation is 0.1-95%.
Preferably, the herbicide preparation is in the form of aqueous solution, soluble liquid, suspending agent, missible oil, aqueous emulsion, oil suspending agent, microemulsion, suspoemulsion, microcapsule suspending agent, seed coating agent, film-spreading oil agent, ultra-low volume spray, wettable powder, soluble powder, dry suspending agent, emulsifiable granules, emulsifiable powder, granules, water dispersible granules, effervescent tablets, smoke agent or macroparticles.
Preferably, the herbicide preparation is an aqueous agent or a soluble liquid agent, and the total mass percentage of the dicamba tetramethylguanidine salt in the herbicide preparation is 1-80%.
Preferably, the herbicide preparation is missible oil or oil suspending agent, and the total mass percentage of the dicamba tetramethylguanidine salt in the herbicide preparation is 1-40%.
Preferably, the water agent comprises, by mass, 60-70 parts of dicamba tetramethylguanidine salt, 1-3 parts of polyoxyethylene sorbitan monooleate, 0.5-1.5 parts of isooctylphenol polyoxyethylene ether, 1.5-2.5 parts of fatty alcohol polyoxyethylene ether and 25-35 parts of water.
Preferably, the solvent is a soluble liquid agent consisting of 35-45 parts by mass of dicamba tetramethylguanidine salt, 1-3 parts by mass of alkylphenol formaldehyde resin polyoxyethylene ether, 1-3 parts by mass of dodecylbenzene sulfonic acid isopropylamine salt, 0.5-1.5 parts by mass of polycarboxylate and 50-60 parts by mass of N-methylpyrrolidone.
Preferably, the oil suspension agent comprises, by mass, 25-35 parts of dicamba tetramethylguanidine salt, 6-10 parts of fatty amine polyoxyethylene ether, 3-5 parts of polyoxyethylene polyoxypropylene block copolymer, 1-3 parts of heptamethyltrisiloxane polyoxyethylene ether, 1-3 parts of organobentonite, 0.5-1.5 parts of white carbon black and 50-55 parts of methyl oleate.
Preferably, the composition comprises, by mass, 15-20 parts of dicamba tetramethylguanidine salt, 5-10 parts of fatty amine polyoxyethylene ether, 1-5 parts of polyoxyethylene alkyl alcohol acylamino amine, 2-6 parts of sodium dodecyl sulfate and 65-70 parts of cyclohexanone.
Compared with the prior art, the invention has the following advantages:
the dicamba tetramethylguanidine salt is obtained by reacting dicamba and tetramethylguanidine, has the advantages of dicamba and tetramethylguanidine, and on one hand, by promoting the synthesis of nucleic acid and protein in plants, cells excessively divide and elongate, tissues are malformed due to excessive growth, thereby obstructing the transportation of substances, causing the death of weeds and having quick response; on the other hand, the compound has the advantages of high molecular weight, high safety and difficult volatilization, so that the compound is safe and environment-friendly in the processes of processing, storage, transportation, construction and the like, can effectively kill various broadleaf weeds in a wheat field when being applied in the field, improves the attachment rate of the liquid medicine on the leaf surfaces of the weeds, promotes the weeding activity and delays the generation of weed resistance.
The herbicide preparation prepared by adopting the dicamba tetramethylguanidine salt as the effective component has the advantages that the effective component has high boiling point, is not easy to volatilize in actual field application, has larger molecular weight, improves the specific gravity of the applied liquid drop, ensures that the liquid drop is not easy to deviate from a target area, reduces the drifting risk, is easier to be absorbed by plants, has quick response, can reduce the drug resistance of weeds, and prolongs the service life of the herbicide; the dicamba tetramethylguanidine salt is easy to disperse in the herbicide preparation, is easy to be absorbed by an inert carrier, has high stability and is not easy to decompose, and can play a good role in dispersion and emulsification after a small amount of surfactant is added, so that the obtained herbicide preparation is easier to be absorbed by crops and takes effect quickly; the herbicide preparation can effectively prevent and kill off broadleaf weeds in wheat fields, but does not affect the growth of wheat, does not produce toxicity to succeeding crops, and has high safety.
Detailed Description
The synthesis mechanism of the dicamba tetramethylguanidine salt is as follows:
the ingredients that may be included in the herbicide formulation include, but are not limited to, the following: polyoxyethylene sorbitan monooleate, isooctylphenol polyoxyethylene ether, fatty alcohol polyoxyethylene ether, tristyryl polyoxyethylene ether, distyryl cumylphenol polyoxyethylene ether, phenethylnaphthol polyoxyethylene ether, fatty amine polyoxyethylene ether, polyoxyethylene alkyl alcohol amine, fatty acid polyoxyethylene ester, castor oil ethylene oxide adduct, abietic acid ethylene oxide adduct, xylitol anhydride monostearate, polyoxyethylene xylitol anhydride monostearate, sucrose fatty acid ester, triglycerol monostearate, alkylphenol formaldehyde resin polyoxyethylene ether, aryl phenol polyoxyethylene ether formaldehyde condensate, polyoxyethylene polyoxypropylene block copolymer, alkylpolyglucoside, calcium dodecylbenzene sulfonate, dodecylbenzene sulfonate isopropylamine salt, dodecylbenzene sulfonate triethanolamine salt, fatty acid ester sulfonate, alkylnaphthalene sulfonate, alkyl naphthalene sulfonate, and the like, Sodium lauryl sulfate, castor oil butyl sulfate triethanolamine salt, alkyl phosphate triethanolamine salt, alkyl benzene sulfonate, alkyl (aryl) naphthalene sulfonate formaldehyde condensate, N-methyl fatty acyl taurate salt, lignosulfonate salt, alkylphenol polyoxyethylene ether formaldehyde condensate sulfate, fatty alcohol polyoxyethylene ether sulfate, alkyl phosphate, fatty alcohol polyoxyethylene ether phosphate, alkyl (aryl) phenol polyoxyethylene ether phosphate, polycarboxylate, azone, sulfonated castor oil, heptamethyltrisiloxane polyoxyethylene ether, 2-butyloctylbenzene sulfonate sodium salt, fatty amide N-methyl taurate sodium salt, rapeseed oleic acid ethanolamide polyoxyethylene ether, octanol citric acid monoester disodium salt, carboxymethyl starch sodium, hydroxypropyl starch, hydroxypropyl cellulose, sodium carboxymethyl cellulose, sodium lauryl sulfate, alkyl benzene sulfonate, alkyl (aryl) naphthalene sulfonate formaldehyde condensate, N-methyl fatty acyl taurate, lignosulfonate, alkylphenol polyoxyethylene ether formaldehyde condensate sulfate, Polyvinylpyrrolidone, ammonium sulfate, sodium sulfate, potassium dihydrogen carbonate, dipotassium hydrogen carbonate, potassium chloride, urea, sodium gluconate, white carbon black, magnesium aluminum silicate, xanthan gum, organic bentonite, propylene glycol, glycerol, sodium benzoate, karson, light calcium carbonate, kaolin, diatomite, attapulgite, wheat starch, soluble starch, talcum powder, ethanol, methanol, N-butanol, N-dimethylformamide, N-methylpyrrolidone, N-dimethyl sulfoxide, solvent oil, cyclohexanone, methyl oleate, turpentine oil, epoxidized soybean oil, wheat oil, rapeseed oil, methyl caprylate and N, N-dimethyldecanamide.
The invention is further described with reference to specific examples.
Example 1
Dicamba tetramethylguanidine salt with structural formula
The preparation method of the dicamba tetramethylguanidine salt comprises the following steps: dissolving 221g of dicamba in 1L of toluene, stirring and heating to reflux, dripping 104g of tetramethylguanidine into the dicamba, controlling the dripping speed during dripping to prevent flushing caused by violent reaction, continuously refluxing for 3 hours after dripping is finished, stirring and cooling to 20 ℃, performing suction filtration, and drying a filter cake to obtain the dicamba tetramethylguanidine salt.
Example 2
The preparation method of the dicamba tetramethylguanidine salt comprises the following steps: dissolving 221g of dicamba in 1.5L of toluene, stirring and heating to reflux, dropwise adding 419.5g of tetramethylguanidine into the dicamba, controlling the dropwise adding speed during dropwise adding to prevent flushing caused by severe reaction, continuously refluxing for 4 hours after dropwise adding is finished, stirring and cooling to 30 ℃, performing suction filtration, and drying a filter cake to obtain the dicamba tetramethylguanidine salt.
Example 3
The preparation method of the dicamba tetramethylguanidine salt comprises the following steps: dissolving 221g of dicamba in 1.2L of toluene, stirring and heating to reflux, dropwise adding tetramethylguanidine into the dicamba, controlling the dropwise adding speed during dropwise adding to prevent flushing caused by violent reaction, continuously refluxing for 3.5 hours after dropwise adding is finished, stirring and cooling to 25 ℃, performing suction filtration, and drying a filter cake to obtain the dicamba tetramethylguanidine salt.
The nuclear magnetic hydrogen spectrum data and the nuclear magnetic carbon spectrum data of the dicamba tetramethylguanidine salt obtained in the examples 1 to 3 are as follows:
1HNMR(CDCl3，400MHZ)：δ：3.16(s,12H,-CH3)，3.96(s,3H,-OCH3)，7.29(d,1H,Ar-H)， 7.76(d,1H,Ar-H)，9.56(s,2H,-NH2)。
13CNMR(CDCl3，100MHZ)：δ：38.7(-CH3)，62.6(-OCH3)，125.1(-Ar-C)，125.2(-Ar-C)，126.3(-Ar-C)，134.7(-Ar-C)，138.0(-Ar-C)，158.8(-Ar-C)，159.0(-C＝N)，178.1(-C＝O)。
example 4
A herbicide containing dicamba tetramethylguanidine salt is a seed coating agent prepared from 0.1% of dicamba tetramethylguanidine salt and 99.9% of organic bentonite in percentage by weight.
Example 5
A herbicide preparation containing dicamba tetramethylguanidine salt is an emulsifiable powder prepared from 80% of dicamba tetramethylguanidine salt, 2% of fatty alcohol-polyoxyethylene ether phosphate, 1% of isooctylphenol polyoxyethylene ether and 2% of sodium carboxymethylcellulose.
Example 6
A herbicide containing dicamba tetramethylguanidine salt is an emulsifiable concentrate prepared from 10% of dicamba tetramethylguanidine salt, 2% of rapeseed oleic acid ethanolamide polyoxyethylene ether, 1% of triglycerol monostearate, 2% of alkylphenol formaldehyde resin polyoxyethylene ether and 85% of n-butyl alcohol in percentage by weight.
Example 7
A herbicide preparation containing dicamba tetramethylguanidine salt is an aqueous agent prepared from 80% of dicamba tetramethylguanidine salt, 2% of polyoxyethylene sorbitan monooleate, 1% of isooctylphenol polyoxyethylene ether, 2% of fatty alcohol polyoxyethylene ether and 15% of water in percentage by weight.
Example 8
A herbicide preparation containing dicamba tetramethylguanidine salt is an aqueous agent prepared from 1% of dicamba tetramethylguanidine salt, 2% of polyoxyethylene sorbitan monooleate, 1% of isooctylphenol polyoxyethylene ether, 2% of fatty alcohol polyoxyethylene ether and 94% of water in percentage by weight.
Example 9
A herbicide preparation containing dicamba tetramethylguanidine salt is an aqueous agent consisting of 60 parts by weight of dicamba tetramethylguanidine salt, 1 part by weight of polyoxyethylene sorbitan monooleate, 0.5 part by weight of isooctylphenol polyoxyethylene ether, 1.5 parts by weight of fatty alcohol polyoxyethylene ether and 25 parts by weight of water.
Example 10
A herbicide preparation containing dicamba tetramethylguanidine salt is an aqueous agent consisting of 70 parts by weight of dicamba tetramethylguanidine salt, 3 parts by weight of polyoxyethylene sorbitan monooleate, 1.5 parts by weight of isooctylphenol polyoxyethylene ether, 2.5 parts by weight of fatty alcohol polyoxyethylene ether and 35 parts by weight of water.
Example 11
A herbicide preparation containing dicamba tetramethylguanidine salt is an aqueous agent consisting of 65 parts by weight of dicamba tetramethylguanidine salt, 2 parts by weight of polyoxyethylene sorbitan monooleate, 1 part by weight of isooctylphenol polyoxyethylene ether, 2 parts by weight of fatty alcohol polyoxyethylene ether and 30 parts by weight of water.
Example 12
A herbicide preparation containing dicamba tetramethylguanidine salt is a soluble liquid agent which consists of 35 parts of dicamba tetramethylguanidine salt, 1 part of alkylphenol formaldehyde resin polyoxyethylene ether, 1 part of dodecylbenzene sulfonic acid isopropylamine salt, 0.5 part of polycarboxylate and 50 parts of N-methyl pyrrolidone in parts by weight.
Example 13
A herbicide preparation containing dicamba tetramethylguanidine salt is a soluble liquid agent which consists of 45 parts of dicamba tetramethylguanidine salt, 3 parts of alkylphenol formaldehyde resin polyoxyethylene ether, 3 parts of dodecylbenzene sulfonic acid isopropylamine salt, 1.5 parts of polycarboxylate and 60 parts of N-methylpyrrolidone in parts by weight.
Example 14
A herbicide preparation containing dicamba tetramethylguanidine salt is a soluble liquid agent which consists of 40 parts of dicamba tetramethylguanidine salt, 2 parts of alkylphenol formaldehyde resin polyoxyethylene ether, 2 parts of dodecylbenzene sulfonic acid isopropylamine salt, 1 part of polycarboxylate and 55 parts of N-methylpyrrolidone in parts by weight.
Example 15
A herbicide preparation containing dicamba tetramethylguanidine salt comprises, by weight, 25 parts of dicamba tetramethylguanidine salt, 6 parts of fatty amine polyoxyethylene ether, 3 parts of polyoxyethylene polyoxypropylene block copolymer, 1 part of heptamethyltrisiloxane polyoxyethylene ether, 1 part of organobentonite, 0.5 part of white carbon black and 50 parts of methyl oleate.
Example 16
A herbicide preparation containing dicamba tetramethylguanidine salt comprises, by weight, 35 parts of dicamba tetramethylguanidine salt, 10 parts of fatty amine polyoxyethylene ether, 5 parts of polyoxyethylene polyoxypropylene block copolymer, 3 parts of heptamethyltrisiloxane polyoxyethylene ether, 3 parts of organic bentonite, 1.5 parts of white carbon black and 55 parts of methyl oleate.
Example 17
A herbicide preparation containing dicamba tetramethylguanidine salt comprises, by weight, 30 parts of dicamba tetramethylguanidine salt, 8 parts of fatty amine polyoxyethylene ether, 4 parts of polyoxyethylene polyoxypropylene block copolymer, 2 parts of heptamethyltrisiloxane polyoxyethylene ether, 2 parts of organic bentonite, 1 part of white carbon black and 52 parts of methyl oleate.
Example 18
A herbicide preparation containing dicamba tetramethylguanidine salt is an emulsifiable concentrate which comprises, by weight, 15 parts of dicamba tetramethylguanidine salt, 5 parts of fatty amine polyoxyethylene ether, 1 part of polyoxyethylene alkyl alcohol acylamine, 2 parts of sodium dodecyl sulfate and 65 parts of cyclohexanone.
Example 19
A herbicide preparation containing dicamba tetramethylguanidine salt is an emulsifiable concentrate which comprises, by weight, 20 parts of dicamba tetramethylguanidine salt, 10 parts of fatty amine polyoxyethylene ether, 5 parts of polyoxyethylene alkyl alcohol amine, 6 parts of sodium dodecyl sulfate and 70 parts of cyclohexanone.
Example 20
A herbicide preparation containing dicamba tetramethylguanidine salt is an emulsifiable concentrate which comprises 18 parts by weight of dicamba tetramethylguanidine salt, 6 parts by weight of fatty amine polyoxyethylene ether, 3 parts by weight of polyoxyethylene alkyl alcohol acylamine, 5 parts by weight of sodium dodecyl sulfate and 68 parts by weight of cyclohexanone.
1 indoor Activity measurement test
1.1 Using the herbicide formulations of examples 6, 11, 14, 17 and 20, the co-toxicity coefficient was determined for the common weed Amaranthus retroflexus in wheat fields.
Test method
Respectively sowing quantitative amaranthus retroflexus seeds in disposable paper cups of 9cm, sowing 10-15 seeds in each cup, culturing in an illumination incubator, performing spray treatment on a crawler-type crop spray when the amaranthus retroflexus is in a 3-6 leaf stage, continuously culturing in a greenhouse after treatment, periodically observing the weed control effect of each treatment, weighing the fresh weight of each treated weed after 30 days, and measuring the results as shown in table 1.1.
TABLE 1.1 indoor Activity measurement results
As can be seen from the data in Table 1.1, the control effect of the dicamba tetramethylguanidine salt on the Amaranthus retroflexus is smaller than that of the ED50 of the existing product 48% dicamba AS (dimethylamine salt), and the control effect is better.
1.2 the herbicide formulation of example 14 and 48% dicamba AS (dimethylamine salt) were tested for their co-toxicity coefficient against the common wheat weeds Capsella bursa-pastoris, Trigonella viridis, Descurainia sophia, Cirsium setosum and Lepidium meyenii.
Test method
Respectively sowing quantitative seeds of capsella bursa-pastoris, maigre, descurainia sophia, herba cepbalanoplosis segeti and Lepidium meyenii in disposable paper cups with the length of 9cm, sowing 10-15 seeds in each cup, culturing in an illumination incubator, performing spray treatment on a crawler-type crop spray when various weeds are in a 3-6 leaf period, continuously culturing in a greenhouse after treatment, periodically observing the weed control effect of each treatment, weighing the fresh weight of each treated weed after 30 days, and determining the result as shown in table 1.2.
TABLE 1.2 results of the tests on the determination of various weeds
As can be seen from the measurement results in Table 1.2, the ED of the tetramethylguanidine salt of dicamba of the present invention is comparable to that of the existing dicamba AS (dimethylamine salt)50Smaller (g/mu), more excellent herbicidal activity and smaller application amount.
2. Test of field drug effect
Reagent to be tested: 5 herbicide formulations of examples 6, 11, 14, 17 and 20;
control agents: 48% dicamba AS (dimethylamine salt);
test work: wheat;
the wheat seedlings are 3-5 leaves, the growth vigor is good, the plants are robust, and other plant diseases and insect pests do not exist.
Control target: predominant weeds in wheat fields such as shepherd's purse, Ma Jia Gong, seeding wild wormwood, field thistle, striga asiatica, redroot amaranth, Chenopodium quinoa, wild oat and the like.
The test method comprises the following steps: various medicaments are accurately weighed according to the area of a test cell, and are uniformly sprayed by a knapsack sprayer after being diluted by water, and a special fan-shaped spray head for herbicides is selected as the spray head. During spraying, the pesticide liquid is required to be uniformly sprayed into a test cell, the phenomena of missed spraying and excessive spraying are avoided, the weed death condition is observed 20 days and 40 days after the pesticide liquid is sprayed after the test, the weeding activities of various pesticides are compared, in addition, the production condition of crops is observed within 1-15 days after the pesticide liquid is sprayed, whether the pesticide liquid has the pesticide damage to the crops is examined, and the field pesticide effect test results of 20 days and 40 days after the pesticide liquid is sprayed are respectively shown in tables 2 and 3.
TABLE 2 field test results of efficacy (post-dose 20d)
TABLE 3 field efficacy test results (post-drug 40d)
The dosage of the dicamba tetramethylguanidine salt in the invention is only g a.i./mu, the dosage is less, the total control effect after 20 days of application reaches more than 90%, the total control effect of the optimal embodiment reaches 99%, the total control effect after 40 days of application reaches more than 95%, and the total control effect of the optimal embodiment reaches 100%, and the data in the tables 2 and 3 show that the dicamba tetramethylguanidine salt has obvious control effect on broad-leaved weeds in wheat fields, has obvious synergism compared with the existing herbicides, and has long duration.
TABLE 4 investigation results of safety of the agents on crops
Safety investigation is carried out on the wheat in each test cell, and the wheat in each treatment cell is found to grow well without any drug spot, which indicates that the herbicide preparation of the invention is safe to the wheat.
3. Stability test
The herbicide formulations of examples 6, 11, 14, 17 and 20 were subjected to stability tests, specifically including thermal storage stability, expressed as the rate of decomposition, and low temperature stability, expressed as the volume of educt at the bottom of the centrifuge tube, and the results are shown in table 5.
Table 5 stability test results
As can be seen from the data in table 5, the herbicide formulations of the present invention have good heat storage stability and low temperature stability.
Claims (10)
1. The dicamba tetramethylguanidine salt is characterized by having a structural formula
2. The method of producing dicamba tetramethylguanidine salt according to claim 1, comprising the steps of: dissolving dicamba in toluene, stirring and heating to reflux, dripping tetramethylguanidine into the toluene, continuing refluxing for 3-4 hours after dripping is finished, stirring and cooling to 20-30 ℃, performing suction filtration, and drying a filter cake to obtain dicamba tetramethylguanidine salt; wherein the molar volume ratio of dicamba to tetramethylguanidine to toluene is 1 mol: 0.9-1.3 mol: 1-1.5L.
3. A herbicide preparation containing dicamba tetramethylguanidine salt is characterized in that the herbicide preparation is prepared by taking the dicamba tetramethylguanidine salt as an effective component, wherein the total mass percentage of the dicamba tetramethylguanidine salt in the herbicide preparation is 0.1-95%.
4. The herbicide formulation containing dicamba tetramethylguanidine salt as claimed in claim 3, wherein the herbicide formulation is in the form of aqueous solution, soluble liquid, suspension, emulsifiable concentrate, aqueous emulsion, oil suspension, microemulsion, suspoemulsion, microcapsule suspension, seed coating agent, film-spreading oil agent, ultra-low volume spray, wettable powder, soluble powder, dry suspension, emulsifiable granules, emulsifiable powder, granules, water dispersible granules, effervescent tablets, smoking agent or macrogranules.
5. The herbicide preparation containing dicamba tetramethylguanidine salt according to claim 3, wherein the herbicide preparation is water-soluble or liquid-soluble, and the total mass percentage of dicamba tetramethylguanidine salt in the herbicide preparation is 1-80%.
6. The herbicide preparation containing dicamba tetramethylguanidine salt according to claim 3, wherein the herbicide preparation is in the form of emulsifiable concentrate or oil suspension, and the total mass percentage of dicamba tetramethylguanidine salt in the herbicide preparation is 1-40%.
7. The herbicide formulation containing dicamba tetramethylguanidine salt according to claim 5, wherein the herbicide formulation is an aqueous agent comprising, by mass, 60 to 70 parts of dicamba tetramethylguanidine salt, 1 to 3 parts of polyoxyethylene sorbitan monooleate, 0.5 to 1.5 parts of isooctylphenol polyoxyethylene ether, 1.5 to 2.5 parts of fatty alcohol polyoxyethylene ether, and 25 to 35 parts of water.
8. A herbicide formulation containing dicamba tetramethylguanidine salt according to claim 5, characterized by a soluble liquid agent comprising, by mass, 35 to 45 parts of dicamba tetramethylguanidine salt, 1 to 3 parts of alkylphenol formaldehyde resin polyoxyethylene ether, 1 to 3 parts of dodecylbenzene sulfonic acid isopropylamine salt, 0.5 to 1.5 parts of polycarboxylate, and 50 to 60 parts of N-methylpyrrolidone.
9. A herbicide formulation containing dicamba tetramethylguanidine salt according to claim 6, characterized in that the oil suspension agent comprises 25 to 35 parts by mass of dicamba tetramethylguanidine salt, 6 to 10 parts by mass of fatty amine polyoxyethylene ether, 3 to 5 parts by mass of polyoxyethylene polyoxypropylene block copolymer, 1 to 3 parts by mass of heptamethyltrisiloxane polyoxyethylene ether, 1 to 3 parts by mass of organobentonite, 0.5 to 1.5 parts by mass of white carbon black and 50 to 55 parts by mass of methyl oleate.
10. The herbicide formulation containing dicamba tetramethylguanidine salt according to claim 6, characterized by comprising 15 to 20 parts by mass of dicamba tetramethylguanidine salt, 5 to 10 parts by mass of fatty amine polyoxyethylene ether, 1 to 5 parts by mass of polyoxyethylene alkyl alcohol amide, 2 to 6 parts by mass of sodium lauryl sulfate and 65 to 70 parts by mass of cyclohexanone.
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| US20120172220A1 (en) * | 2009-06-30 | 2012-07-05 | Flamel Technologies S.A. | N-phosphonomethylglycine guanidine derivative salts |
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