CN108633902B - A kind of synergistic composition containing halosulfuronmethyl and its weeding application - Google Patents
A kind of synergistic composition containing halosulfuronmethyl and its weeding application Download PDFInfo
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- CN108633902B CN108633902B CN201810333459.1A CN201810333459A CN108633902B CN 108633902 B CN108633902 B CN 108633902B CN 201810333459 A CN201810333459 A CN 201810333459A CN 108633902 B CN108633902 B CN 108633902B
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- halosulfuronmethyl
- tertiary amines
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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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of synergistic composition containing halosulfuronmethyl and its weeding application, the group for also disclosing a kind of water dispersible granules is grouped as and preparation method thereof.Tertiary amines derived object formula (I) of the present invention and halosulfuronmethyl combined administration are measured to the activity of acalypha copperleaf using greenhouse pot culture method, and it is evaluated according to Colby method, the tertiary amines derived object formula (I) and halosulfuronmethyl are administered in combination E-E0 value and are all larger than 10% with synergistic function.Weed-control effect under the application dosage that tertiary amines derived object formula (I) and the total dosage of halosulfuronmethyl described in the test discovery of field synergistic function are 45g/ hectares is carried out to water dispersible granules and is higher than single medicine application, and rate of growth increases.
Description
Technical field
The present invention relates to agriculture plasm resource protection and prevention and control more particularly to a kind of synergistic combinations containing halosulfuronmethyl
Object and its weeding application.
Background technique
Halosulfuronmethyl category selective inner-adsorption conduction-type herbicide, by inhibiting the ALS enzyme of plant, (acetolactic acid is synthesized
Enzyme), the biosynthesis of branched-chain amino acid such as valine, isoleucine, leucine is prevented, the final synthesis for destroying protein is done
Herbicide is played the role of in the synthesis and cell division and growth for disturbing DNA, is mainly used for the grass family such as corn, rice, wheat, sugarcane and makees
Broadleaf weeds and sedge weed are prevented and kill off in object field, it is active it is high, dosage is few, the lasting period is long, broad weed-killing spectrum, to gramineous crop
The features such as safety and other herbicide miscibilties are strong, development and application has a extensive future.
Current pesticide just towards efficient, high-content, low toxicity, low-residual, without security risk, without environmental risk, without using
Risk direction development.With the speed-raising of increase and the pesticide reduction synergy action of eco-friendly pesticide demand, domestic market is to dosage form
The Pesticidal products demand environmentally protective, content is high is increasing.Therefore, the exploitation of new pesticide and the combination synergy of existing pesticide
Research and development and the research and development of novel agrochemical formulations become the chief motivation for accelerating pesticide market variation.
Summary of the invention
The purpose of the present invention is to provide a kind of composition, including tertiary amines derived object formula (I) and halosulfuronmethyl, the formulas
(I) structure is as follows
。
Further, the weight ratio of the tertiary amines derived object formula (I) and the halosulfuronmethyl is 1:6~6:1, preferably:
1:4~2:1.
It is used as and removes with the halosulfuronmethyl another object of the present invention is to provide a kind of tertiary amines derived object formula (I)
The application of careless agent.
Contain the tertiary amines derived object formula (I) and the halosulfuronmethyl another object of the present invention is to provide a kind of
Water dispersible granules.
Further, the water dispersible granules are made of following components in parts by weight:
(I) 5~20 part of tertiary amines derived object formula of the present invention
5~40 parts of halosulfuronmethyl
5~10 parts of fatty acid amide N methyl taurine sodium salt
5~10 parts of polycarboxylate
2~10 parts of starch derivatives
40~100 parts of kaolin.
Wherein, tertiary amines derived object formula (I) of the present invention and halosulfuronmethyl are active constituent, fatty acid amide N- methyl
Taurine sodium salt is wetting agent, and polycarboxylate is dispersing agent, and starch derivatives is disintegrating agent, and kaolin is solid carrier.Preparation
Method are as follows: according to above-mentioned formula, each component co-grinding after being soaked with water, is granulated, then done by Squeezinggranulator
The mixed material being in granular form that partial size is 200 microns~5000 microns is made in dry, screening.
The component ratio of the water dispersible granules prepared in some embodiments of the invention is only to verify tertiary amine of the present invention
Derivative formula (I) and halosulfuronmethyl joint have synergistic effect and use, and each component content is above-mentioned weight in water dispersible granules
The group of part is grouped as the arbitrary form of restriction.
Tertiary amines derived object formula (I) of the present invention is measured using greenhouse pot culture method and halosulfuronmethyl is administered in combination to iron
The activity of three-coloured amaranth, and evaluated according to Colby method, the tertiary amines derived object formula (I) and halosulfuronmethyl are administered in combination
E-E0 value, which is all larger than 10%, has synergistic function.
It is phonetic that the test discovery of field synergistic function the tertiary amines derived object formula (I) and chlorine pyrrole are carried out to water dispersible granules
Weed-control effect is higher than single medicine application under the application dosage that the grand total dosage of sulphur is 45g/ hectares, and rate of growth increases.
Specific embodiment
Embodiment 1: the synthesis of tertiary amines derived object formula (I)
The synthesis of 1.1 4- iodo -2- trifloro methyl phenols
2- trifloro methyl phenol (10 mmol) is dissolved in 20 ml methylene chloride, 2 ml DMF, stirring 10 are added thereto
Minute, N-iodosuccinimide (12 mmol) then is added thereto, system temperature rises to 80 DEG C or so, it reacts 2 hours,
System is down to room temperature, and filtering removes insoluble matter, and surplus solution washs twice with 2% diluted hydrochloric acid aqueous solution, and organic phase is with anhydrous
After sodium sulphate dries, filters, natural solvent flashing crystallization obtains 2.5g off-white color 4- iodo -2- trifloro methyl phenol crystal, produces
Rate 87%.1H-NMR (400 MHz, CDCl3) δ: 5.09(s, 1H), 6.48(d, 1H), 7.81(m, 2H). 13C-
NMR(75 MHz, CDCl3) δ: 84.79, 119.05, 124.47, 132.07, 141.65, 158.07. LC-MS
(ESI, pos, ion) m/z: 289 [M+H]。
The synthesis of 1.2 1- chlorine-4-iodine generation -2- trifluoromethylbenzenes
4- iodo -2- the trifloro methyl phenol (10 mmol) that 1.1 obtain is dissolved in 20 ml DMF, trichlorine is then added
Oxygen phosphorus (10.5 mmol), system is placed under microwave environment, is heated to 130 DEG C, is reacted 1 hour.After the reaction was completed, system drops
To room temperature, 30 ml water are added thereto, stir 10 minutes, add the extraction of 30 ml methylene chloride, organic phase anhydrous slufuric acid
Sodium dries, filters, and solvent is evaporated off in filtrate decompression, and residue uses petroleum ether as eluant, eluent, and flash column chromatography separation obtains 2.1
The solid powder of the faint yellow 1- chlorine-4-iodine generation -2- trifluoromethylbenzene of g, yield 69%.1H-NMR (400 MHz, CDCl3) δ:
7.09(d,1H), 7.92(m, 2H). 13C-NMR(75 MHz, CDCl3) δ: 84.79, 123.12, 130.38,
130.47, 131.79, 133.18, 140.45. LC-MS(ESI, pos, ion) m/z: 306 [M+H]。
The synthesis of bis- (pyridyl group -2- the methyl) -3- 5-trifluoromethylanilines of 1.3 4- chloro- N, N-
In the 1- chlorine-4-iodine generation -2- trifluoromethylbenzene (10 mmol) that reaction 1.2 obtains, is dissolved in 20 ml toluene, system
In sequentially add bis- (pyridyl group -2- methyl) amine (12mmol), acid chloride (0.5 mmol), 2,2 '-two (diphenylphosphoryl group) -1,
After ten minutes, 10 ml cesium carbonates (10 mmol) aqueous solution, heating is added in 1 '-dinaphthalene (12 mmol), 3 ml triethylamines, stirring
It is reacted 4 hours to 50 DEG C, after reaction, is added 20 ml water into system, stirred 20 minutes, liquid separation, organic phase is with anhydrous
Sodium sulphate is dry, concentration, and flash column chromatography separation obtains bis- (pyridyl group -2- the methyl) -3- trifluoros of 3.3 g yellow 4- chloro- N, N-
Methylaniline powder, yield 87.5%.1H-NMR (400 MHz, CDCl3) δ: 4.78(d, 4H), 6.71(dd, 1H),
7.04(d, 1H), 7.23-7.30(m, 4H), 7.52(d, 1H), 7.73(td, 2H), 8.50(dd, 2H). 13C-
NMR(75 MHz, CDCl3) δ: 54.51, 114.21, 116.12, 119.63, 120.06, 122.33, 123.12,
130.71, 130.72, 139.57, 148.71, 149.06, 156.3.LC-MS(ESI, pos, ion) m/z: 378
[M+H]。
The synthesis of bis- (pyridyl group -2- the methyl) -3- 5-trifluoromethylanilines of 1.4 4- (1- cyclohexylvinyl)-N, N-
Bis- (pyridyl group -2- the methyl) -3- 5-trifluoromethylanilines (10 mmol) of the 4- that 1.3 are obtained chloro- N, N- are dissolved in 30
In ml n,N-Dimethylformamide, system rouses 20 min of argon gas, then tetra-triphenylphosphine palladium is added in the air in emptying system,
60 DEG C are warming up to, continues to stir half an hour, 1- cyclohexyl-vinyl -1- boric acid (12 mmol) is added thereto, adds 10
Ml sodium carbonate (1g) aqueous solution is warming up to 90 DEG C, stirs 5 hours, and whole process holding is passed through argon gas, then cools down, and decompression is steamed
Except solvent, solid obtains 4.2 g 4- (1- cyclohexylvinyl)-N, N- bis- (pyridyl group -2- methyl)-quickly through chromatographic column
3- 5-trifluoromethylaniline off-white powder, yield 93%.1H-NMR (400 MHz, CDCl3) δ: 1.12-1.20(m, 3H),
1.60(m, 1H), 1.81(m, 2H), 2.30(m, 1H), 2.75(m, 2H), 4.16(m, 2H), 4.68-4.70(m,
3H), 4.92-4.94(m, 3H), 6.77(dd, 1H), 7.01-7.06(m, 2H), 7.24-7.31(m, 4H), 7.74
(td, 2H), 8.51(dd, 2H). 13C-NMR(75 MHz, CDCl3) δ: 25.15, 25.92, 31.77, 44.46,
54.51, 111.73, 114.35, 120.06, 122.33, 122.56, 123.9, 124.19, 125.78, 131.11,
139.57, 148.71, 149.06, 150.01, 156.3.LC-MS(ESI, pos, ion) m/z: 452 [M+H]。
Reference examples 1,2 and embodiment 2,3: water dispersible granules
Prescription proportion:
According to above-mentioned formula, each component co-grinding after being soaked with water, is granulated, then done by Squeezinggranulator
The mixed material being in granular form that partial size is 200 microns~5000 microns is made in dry, screening.
Embodiment 4~10:
Prescription proportion:
According to above-mentioned formula, each component co-grinding after being soaked with water, is granulated, then done by Squeezinggranulator
The mixed material being in granular form that partial size is 200 microns~5000 microns is made in dry, screening.
Test example 1: synergistic function is administered in combination
Tertiary amines derived object formula (I) of the present invention is measured using greenhouse pot culture method and halosulfuronmethyl is administered in combination to iron
The activity of three-coloured amaranth, tertiary amines derived object formula (I) of the present invention and halosulfuronmethyl are used respectively at 0.1% Tween-80 aqueous solution
Reason.It is built-in from topsoil of the farmland acquisition through air-drying with the plastic nutrition bowl of diameter 9cm, make soil in the method that bottom is supplied water
Earth keeps wet, the uniform weed seed of sowing full seed, after earthing 0.5cm, is placed within second day in PWT-510 type spray tower
Carry out that spraying (precision spraying area is 0.2m2, spraying liquid 10mL, the Tween-80 aqueous solution of control spray 0.1%).21 days after processing
Acalypha copperleaf aerial part fresh weight is weighed, fresh weight preventive effect is calculated, is evaluated by Colby method, result is 4 duplicate averages.
Colby method calculation formula are as follows: E0=X+Y-XY/100, wherein X is that preventing for single dose A is applied with the rate of application of p kg/ha
It imitates (%), Y is the preventive effect (%) that single dose B is applied with the rate of application of q kg/ha, and E0 is when the rate of application application with p+q kg/ha removes
Theoretical preventive effect (%) when careless agent A+B phase is mixed, E are the practical preventive effect (%) when herbicide A+B phase is mixed, are association as E-E0 > 10%
Same synergistic effect is acted on for reduction when E-E0 < -10%, is summation action when E-E0 is between ± 10%.Experimental result see the table below.
As seen from the above table, tertiary amines derived object formula (I) of the present invention and halosulfuronmethyl are measured using greenhouse pot culture method
The activity to acalypha copperleaf is administered in combination, and is evaluated according to Colby method, the tertiary amines derived object formula (I) and chlorine pyrrole are phonetic
The grand combined administration E-E0 value of sulphur, which is all larger than 10%, has synergistic function.
Test example 2: water dispersible granules field synergistic function.
Trial crops are sugarcane, and soil property is loam, and main weeds have herba digitariae, junglerice, the rhizome of nutgrass flatsedge, Pharbitis purpurea, green amaranth, match
The dominant weeds such as certain herbaceous plants with big flowers, beggar-ticks, fish yellow grass, Bermuda grass and Rottboellia exaltata L. F.Water dispersion prepared by reference examples 1,2 and embodiment 2,3
Granula is applied with 300g/ hectares, if blank group, totally 5 are handled, 4 repetitions of every processing, totally 20 processing cells, random district's groups
Arrangement, every plot area 30m2, cauline leaf spray is carried out in weed growth to 3-5 leaf phase.20 days after medicine, every cell takes at 4 points respectively,
Every 0.25m2, it investigates weeds type, quantity and simultaneously weighs, the calculating preventive effect compared with blank group weeds weight.When harvesting sugarcane, respectively
Cell individually harvests 30 plants of surveys and produces, and calculates rate of growth.Test result see the table below.
| Weed-control effect (%) | Rate of growth (%) | |
| Reference examples 1 | 26.1 | 21.0 |
| Reference examples 2 | 64.4 | 16.8 |
| Embodiment 2 | 93.7 | 52.3 |
| Embodiment 3 | 81.4 | 41.2 |
It is phonetic that the test discovery of field synergistic function the tertiary amines derived object formula (I) and chlorine pyrrole are carried out to water dispersible granules
Weed-control effect is higher than single medicine application under the application dosage that the grand total dosage of sulphur is 45g/ hectares, and rate of growth increases.
Claims (4)
1. a kind of composition, including tertiary amines derived object formula (I) and halosulfuronmethyl, formula (I) structure is as follows, the weight ratio of the tertiary amines derived object formula (I) and the halosulfuronmethyl is 1:6~6:1.
2. the weight ratio of composition as described in claim 1, the tertiary amines derived object formula (I) and the halosulfuronmethyl is 1:
4~2:1.
3. application of the composition as claimed in claim 1 or 2 as herbicide.
4. one kind contains the water dispersible granules of tertiary amines derived object formula (I) and the halosulfuronmethyl, by following weight parts
Group is grouped as:
(I) 5~20 part of tertiary amines derived object formula
5~40 parts of halosulfuronmethyl
5~10 parts of fatty acid amide N methyl taurine sodium salt
5~10 parts of polycarboxylate
2~10 parts of starch derivatives
40~100 parts of kaolin,
Formula (I) structure is as follows。
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| JP2009029787A (en) * | 2007-06-22 | 2009-02-12 | Ishihara Sangyo Kaisha Ltd | N-phenyl-methanamine derivative and pest control agent containing the same |
| TWI574622B (en) * | 2012-05-22 | 2017-03-21 | Ishihara Sangyo Kaisha | Herbicidal composition |
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