CN110357860A - A kind of quinazoline diones class compound and its application and a kind of pesticide herbicide - Google Patents

A kind of quinazoline diones class compound and its application and a kind of pesticide herbicide Download PDF

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Publication number
CN110357860A
CN110357860A CN201910272386.4A CN201910272386A CN110357860A CN 110357860 A CN110357860 A CN 110357860A CN 201910272386 A CN201910272386 A CN 201910272386A CN 110357860 A CN110357860 A CN 110357860A
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compound
quinazoline diones
class compound
formula
weeds
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CN110357860B (en
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杨光富
何波
王现全
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Liaoning Xianda Agricultural Science Co.,Ltd.
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Shandong Cynda Chemical Co Ltd
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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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/72—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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Abstract

The present invention relates to pesticide herbicide fields, disclose a kind of quinazoline diones class compound and its application and a kind of pesticide herbicide, quinazoline diones class compound of the invention has structure shown in formula (I), and R is H or is group shown in formula (I-1).Quinazoline diones class compound provided by the invention has excellent activity of weeding and excellent crop safety.

Description

A kind of quinazoline diones class compound and its application and a kind of pesticide herbicide
Technical field
The present invention relates to pesticide herbicide fields, and in particular to a kind of quinazoline diones class compound and the quinazoline two The application of ketone compounds and a kind of pesticide herbicide containing the quinazoline diones class compound.
Background technique
P-hydroxybenzene pyruvic acid (HPP) dioxygenase (4-HPPD) is confirmed to be herbicide action target in the last century 90's Mark.
4-HPPD is widely present in aerobe body, is primarily involved in the metabolism of tyrosine in organism.In plant Interior, the metabolite p-hydroxybenzene pyruvic acid (HPP) of tyrosine generates alcapton under the action of 4-HPPD, and alcapton further turns It is melted into plastoquinone and tocopherol.Plastoquinone and tocopherol are the important as precursors of photosynthesis of plant.Therefore, by inhibiting plant The synthesis of endoplast quinone and tocopherol hinders the normal photosynthesis of plant, cause plant occur alphosis and it is dead.With The features such as HPPD is that the herbicide of target has efficiently, low toxicity, environmentally friendly and good to succession crop safety.Therefore, 4- HPPD herbicide is a kind of very with the herbicide of researching value and development prospect.
2015, CN104557739A filtered out the HPPD class inhibitor molecules containing quinazoline diones segment for the first time, The structure of representative substances is as follows, which is mainly used for preventing and treating the weeds in sorghum field etc.:
Then, WO2017/140612A1 further discloses a series of HPPD class inhibitor molecules on this basis, so And the biological activity test result of particular compound is not provided in the prior art.
Rice is very important cereal crops, and the prevention and treatment of paddy field weed to raising rice yield and solves world's grain Food crises problem has very important effect.At this stage, the malignant weed barnyard grass of paddy field, resistance barnyard grass, semen euphorbiae etc. are tight The normal growth of ghost image Xiangshui County rice, especially resistance barnyard grass develop very fast, and the difficulty of prevention and cure of the following antagonism barnyard grass is got over Come bigger.
Therefore it provides there is good preventive effect and the novel HPPD class of high safety to press down the weeds in paddy field etc. Preparation is of great significance.
Summary of the invention
The object of the present invention is to provide have excellent preventive effect and right to the weeds in the crop plantings such as paddy field ground Crops have the novel HPPD class inhibitor of high safety.
To achieve the goals above, the first aspect of the present invention provides a kind of quinazoline diones class compound, the compound With structure shown in formula (I):
Wherein, in formula (I), R is H or is group shown in formula (I-1).
When the R is H, quinazoline diones class compound of the invention is structure shown in following compound 1:
Compound 1:
When the R be formula (I-1) shown in group when, quinazoline diones class compound of the invention is following compound Structure shown in 2:
Compound 2:
It was found by the inventors of the present invention that the knot that compound 1 provided by the invention and compound 2 provide compared with the existing technology The close compound of structure, and the sample for reference hereinafter provided relative to this paper obviously have better activity of weeding, Particularly, compound 1 and compound 2 provided by the invention also obviously have higher crop safety.Further, of the invention Inventor also found that the compound of the present invention 1 is very excellent to the crop safety of corn and wheat also, of the invention Compound 2 has higher safety to field crops (such as rice) relative to compound 1.
There is no particular limitation at the method for quinazoline diones class compound shown in formula (I) for pairing of the present invention, this field The synthetic method in compound structure combination chemical field that technical staff provides according to the present invention can obtain suitable preparation The method of quinazoline diones class compound shown in formula (I), this is no longer going to repeat them by the present invention.
The second aspect of the present invention provides quinazoline diones class compound answering in controlling weeds described in first aspect With.
Preferably, the weeds include barnyard grass, semen euphorbiae, herba setariae viridis, herba digitariae, Triticum tauschii, herba bromi japonici, wild avena sativa, amur foxtail, Alopecurus, rye grass, rice packet grass, Cassia grass, morning glory, Siberian cocklebur, nutgrass flatsedge, common vetch, Amaranthus retroflexus, false acid pulp, Eclipta prostrata, horse Bitterroot, thorn amaranth, beggar-ticks, Paspalum distichum, rice Leersia Sw, triquetrousc murdannia herb, angustifolia arrowhead herb, rhizoma alismatis, Monochoria korsakowii, dayflower, Monochoria vaginalis, firefly At least one of Lin, difformed galingale herb etc..
The third aspect of the present invention provides quinazoline diones class compound described in first aspect and is selected from grass family in prevention and treatment Application at least one of weeds, broadleaf weeds and sedge weed weeds.
Preferably, in the present invention, the broadleaf weeds include three-coloured amaranth, Chenopodium album, piemarker, rice packet grass, Cassia grass, lead a cow, Siberian cocklebur, Amaranthus retroflexus, false acid pulp, Eclipta prostrata, purslane, thorn amaranth, triquetrousc murdannia herb, angustifolia arrowhead herb, rhizoma alismatis, Monochoria korsakowii, dayflower, Monochoria vaginalis and At least one of nutgrass flatsedge.The nutgrass flatsedge includes firefly Lin, difformed galingale herb etc..
Preferably, in the present invention, the gramineae weed includes barnyard grass, semen euphorbiae, herba setariae viridis, herba digitariae, Triticum tauschii, sparrow Wheat, wild avena sativa, amur foxtail, Alopecurus, rye grass, nutgrass flatsedge, common vetch, beggar-ticks, Paspalum distichum, in rice Leersia Sw extremely Few one kind.
The fourth aspect of the present invention provides quinazoline diones class compound described in first aspect as pesticide herbicide Using.
The fifth aspect of the present invention provides a kind of pesticide herbicide, which is made of active constituent and auxiliary material, The active constituent includes at least one of quinazoline diones class compound described in aforementioned first aspect.
Preferably, in the pesticide herbicide, the content of the active constituent is 1~99.9999 weight %.
Under preferable case, the dosage form of the pesticide herbicide be selected from missible oil, suspending agent, wettable powder, pulvis, granula, At least one of aqua, poison bait, mother liquor and female powder.
The suspending agents such as may include dry suspending agent, dispersible oil-suspending agent and aqueous emulsion.
Auxiliary material in the pesticide herbicide of the invention include but is not limited to surfactant, protecting colloid, adhesive, Thickener, thixotropic agent, bleeding agent, chelating agent, dyestuff, colorant and polymer etc., such as can also be serve as carrier other Conven-tional adjuvants.
Carrier herein indicates one or more organic matters, inorganic matter, natural products or the substance of synthesis.They are helped In the application of active constituent, which is usually inert and must be agriculturally acceptable, especially can be processed What plant was received.Carrier can be solid, such as: clay, silica, resin, wax, is consolidated natural or synthetic silicate Body fertilizer etc.；Either liquid, such as: water, alcohols, ketone, petroleum distillate, aromatic hydrocarbons or wax hydrocarbon, chlorohydrocarbon, liquefied gas etc..
The ingredient of surfactant of the present invention includes emulsifier, dispersing agent or wetting agent, they can be ionic Or it is non-ionic.The example that can be mentioned that is: polyacrylate, lignosulfonates, phenolsulfonic acid or naphthalene sulfonate, epoxy Ethane and aliphatic alcohol or with aliphatic acid or with aliphatic amine and substituted phenol (especially alkylphenol or aryl phenol) Polymer, sulfonic acid succinate, taurine derivatives and alcohol phosphate or the ethylating phenol phosphate ester of polyhydroxy, alkyl Sulphonic acid ester salt, alkylaryl sulfonates, alkyl sulfate, lauryl ether sulfate, aliphatic alcohol sulfate and sulphation ten Six-ten seven-octadecanols and sulphated fatty alcohol glycol ether, in addition there are the condensations of naphthalene or naphthalene sulfonic acids and phenol and formaldehyde Object, polyoxethylene octylphenyl methyl phenyl ethers anisole, ethoxylation iso-octyl ether, octyl phenol or nonyl phenol, alkyl phenyl polyglycol ether, three fourths Base phenyl polyglycol ether, three hard ester group phenyl polyglycol ethers, alkyl aryl polyether alcohol, pure and mild fatty alcohol/ethylene oxide contracting Close object, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylation polyoxypropylene, laruyl alcohol polyglycol ether acetal, sorb Alcohol ester, lignin sulfite waste liquor and protein, albuminate, polysaccharide, Hydrophobic Modified Starch, polyvinyl alcohol, polycarboxylic acids Salt, polyoxyalkylated object, polyvinylamine, polyvinylpyrrolidone and copolymer.
The present invention is not particularly limited the method for preparing the pesticide herbicide, and those skilled in the art can use Conventional preparation method is prepared to form corresponding reagent in pesticide field.
Pesticide herbicide of the present invention includes but is not limited to be used for crops for example, by spraying method.
Quinazoline diones class compound provided by the invention and pesticide herbicide containing the quinazoline diones class compound All advantages with HPPD class herbicide, and have it is environmental-friendly, succession crop safety, dosage are low, quick-acting is good, herbicide Compose the advantages that wide, highly-safe.
Particularly, quinazoline diones class compound provided by the invention is at least one of corn, wheat and rice table Excellent crop safety is revealed.
Quinazoline diones class compound provided by the invention has very gramineae weed, broadleaf weeds and sedge weed High activity of weeding, it is especially significant to the preventive effect of weeds in rice, corn and wheat planting ground, such as to the standing grain in paddy field Undergraduate course weeds (barnyard grass, semen euphorbiae, Paspalum distichum, herba setariae viridis, herba digitariae, rice Leersia Sw etc.)；Broadleaf weeds (triquetrousc murdannia herb, angustifolia arrowhead herb, Rhizoma alismatis, Monochoria korsakowii, dayflower, Monochoria vaginalis etc.)；Nutgrass flatsedge (firefly Lin, difformed galingale herb etc.) etc..
Specific embodiment
The endpoint of disclosed range and any value are not limited to the accurate range or value herein, these ranges or Value should be understood as comprising the value close to these ranges or value.For numberical range, between the endpoint value of each range, respectively It can be combined with each other between the endpoint value of a range and individual point value, and individually between point value and obtain one or more New numberical range, these numberical ranges should be considered as specific open herein.
The present invention selects following substance as sample for reference:
Compound D1:Compound D2:Compound D3:Compound D4:Compound D5:Compound D6:Compound D7:Compound D8:Compound D9:Compound D10:Compound D11:Compound D12:Compound D13:Compound D14:Compound D15:Compound D16:Compound D17:Compound D18:Compound D19:Compound D20:Compound D21:Compound D22:Compound D23:Compound D24:Compound D25:Compound D26:Compound D27:Compound D28:Compound D29:Compound D30:Compound D31:Compound D32:Compound D33:Compound D34:Compound D35:Compound D36:Compound D37:Compound D38:Compound D39:Compound D40:Compound D41:Compound D42:Compound D43:Compound D44:Compound D45:
The method of preparation the compound of the present invention 1, compound 2 and aforementioned sample for reference is for example referred to The synthetic method mentioned in CN104557739A is only the difference according to substituent group, feed change type.
According to a kind of preferred embodiment, the preparation method of compound 1 and compound 2 presented below is made below Raw material involved in standby example is that analysis is pure:
Preparation example 1: compound 1 is synthesized using following synthetic route
The preparation of compound 2a: 2- methyl -6- aminobenzoic acid (as compound 1a) (100mmol) is dissolved in acetic acid In (1200ml), the lower ICl acetic acid solution that 1mol/L is added dropwise is stirred, is added dropwise and continues to be stirred to react 2h.Meeting in reaction process A large amount of solids are precipitated, TLC tracks reaction process, after completion of the reaction.Decompression, which filters, removes filtrate, obtained solid acetic acid 500mL It washes twice, up to pale solid, yield 93% after drying.
The preparation of compound 3a: under nitrogen protection, compound 2a (20mmol), pyridine 30ml are added to two neck of 100mL In bottle.After stirring is completely dissolved to solid, chlorophenyl isocyanate (25mmol) between being slowly added into reaction system.It will reaction Liquid is heated to 100 DEG C and reacts 24 hours.After completion of the reaction, it is slowly added to after reaction solution is cooled to room temperature in ice water and stirs 30 points Clock, obtained solid is filtered, is washed, ether is washed, up to compound 3a, yield 92% after drying.
The preparation of compound 4a: by compound 3a (12mmol), DMF (36mL) and K2CO3(14mmol) is added to reaction flask In.After being stirred to react 30min, dimethyl suflfate (24mmol) is slowly added dropwise, rear room temperature is added dropwise and is stirred to react overnight.TLC Reaction process is tracked, after completion of the reaction, reaction solution is poured slowly into 200mL ice water.And it is vigorously stirred 30min, obtained solid is taken out Filter, washing, ether washing, up to compound 4a, yield 87% after drying.
The preparation of compound 5a: by 4a (12mmol), CuCN (24mmol) is added in reaction flask, is added under nitrogen protection 60mL dry DMF, system is heated to flow back and react about 12h.TLC tracks reaction process, is evaporated under reduced pressure after completion of the reaction DMF is removed, 60mL acetone is added after cooling into reaction flask and is vigorously stirred 30min, is filtered to remove insoluble in reaction flask Solid.White solid is obtained after filtrate concentration, thick yield is 85%；
The preparation of compound 6a: crude product 5a (10mmol) is dissolved in acetic acid (29mL), water (124mL), trifluoromethanesulfonic acid In (7.3mL), the 98mL concentrated sulfuric acid is slowly added dropwise under stirring.After being added dropwise, it is warming up to reflux and reacts 12h, TLC tracking reaction Process.System is cooled to room temperature after completion of the reaction, and is poured into 200mL ice water and is vigorously stirred 30min.Obtained solid is taken out Up to compound 5a, thick yield 88% after filter, washing and drying.
The preparation of compound 7a: by compound 6a (116.3mmol), it is anti-that the DCM steamed again (581.5ml) is added to 1000mL It answers in bottle, oxalyl chloride (174.5mmol) is slowly added dropwise under ice-water bath；After being added dropwise, continue to stir 15min.It is slowly added dropwise 10 DMF is dripped into reaction system, after being added dropwise to, is continued to be stirred to react 2h under ice-water bath and is completely dissolved to solid.End of reaction Removed under reduced pressure solvent afterwards.Prepared acyl chlorides is dissolved in spare in the dry DCM of 200mL.
By 1,3- dimethyl -5- pyrazolone (174.5mmol) under ice-water bath, DCM (350mL) is added in reaction flask.It is slow Slow be added dropwise continues to continue stirring 15 minutes at such a temperature after triethylamine (348.9mmol) is added dropwise.Rapidly by above-mentioned acyl chlorides Dichloromethane solution be added drop-wise in the reaction system, time for adding control in 5min or so.After being added dropwise, the reaction was continued 15min.TLC tracks reaction process to raw material and disappears.After completion of the reaction, solid is precipitated in reaction system, it is molten to filter obtained solid It is placed in methylene chloride at 0 DEG C and stands 12 hours.It filtering and removes filter residue, remaining liq is evaporated under reduced pressure to obtain white solid, Yield is 92%.
The preparation of compound 1: by compound 7a (45.7mmol), dry acetonitrile 685.5mL is added in reaction flask.According to It is secondary that triethylamine (91.4mmol) is added into reaction solution, acetone cyanohydrin (1.5ml).Above-mentioned reaction system is heated to 80 under stirring DEG C, react about 30h.TLC tracks reaction process to raw material and disappears.After completion of the reaction, vacuum distillation removes solvent, and obtained solid is molten Methylene chloride organic phase is washed in methylene chloride, and with 1M HCl solution.Organic phase is collected in liquid separation, after organic phase dries precipitation Solid recrystallizing methanol.Yield is 94%.
Preparation example 2: the preparation method of compound 2
Compound 1 (91.3mmol) is dissolved in THF (457ml), sequentially adds triethylamine (182.7mmol), N, N- diethyl Base formyl chloride (182.7mmol) and DMAP (27.4mmol).It is warming up to reflux 5 hours, to which after the reaction was completed, cooling restores to room Wen Hou stands 2 hours at 0 DEG C, filters and removes solid, and obtained solid is produced with Diethyl ether recrystallization up to thick after filtrate decompression distillation Object, crude product methylene chloride dissolve and methylene chloride organic phase are washed with water twice, and vacuum distillation removes solvent, obtained solid Diethyl ether recrystallization, yield 91% are used again.
The preparation method of compound in above-mentioned sample for reference is referring to aforementioned preparation example 1 and preparation example 2.
The characterize data of above-mentioned sample for reference and the compound of the present invention is listed in Table 1 below respectively:
Table 1: compound structure characterize data
Greenhouse biological activity test is carried out using aforementioned sample for reference and the compound of the present invention.
Test case 1: the general sieve experiment in greenhouse
A certain amount of raw medicine is weighed with assay balance, is made into 1 weight with the DMF dissolution containing 1 weight % Tween-80 emulsifier The mother liquor of % is measured, the liquid storage for being then diluted to various concentration with distilled water is spare.
For trying weeds: referring to table 2.It is spraying using cauline leaf after seedling: to take internal diameter 7cm dixie cup, fill composite earth (vegetable garden soil: nursery Matrix, 1:2, v/v) at 3/4, directly sowing weeds grass seeds, earthing 0.2cm are spare to the 4-5 leaf phase to length.Sample for reference with And the compound of the present invention is according to 10g.a.i/mu；Mesotrione is administered according to 10g.a.i/mu dosage in auto spraying tower Afterwards, hot-house culture is moved into after Target crops blade face to be tested medical fluid dries, and (temperature remains 25-28 DEG C, and humidity remains 70%), investigation result after 30 days, the results are shown in Table 2.
Investigation method: target victim symptom and growth inhibition situation are estimated after test process 30 days, and claims aerial part fresh Weight calculates fresh weight inhibition rate (%), indicates preventive effect (%) with fresh weight inhibition rate.
Fresh weight inhibition rate (%)=(control fresh weight-processing fresh weight)/control fresh weight × 100
Activity of weeding evaluation (drug resistance, slight inhibitions, slight albefaction, mild malformation, severe deformities, complete albefaction, completely extremely The symptoms such as die):
G grades-with control, drug resistance, preventive effect is less than 10%；
F grades-growth slightly influences, slight to inhibit, poor activity, and preventive effect is 10% to less than 20%；
E grades-growth has an impact, slight albefaction, poor activity, and preventive effect is 20% to less than 50%；
D grades-growth has an impact, mild malformation, and activity is medium, and preventive effect is 50% to less than 70%；
C grades-more sensitive, severe deformities, preferably, preventive effect is 70% to less than 90% to activity；
B grades-extremely sensitive, complete albefaction, activity is good, and into sieve, preventive effect is 90% to less than 100%；
A grades-completely dead, active good, preventive effect 100%.
Table 2: greenhouse is general to screen out careless activity experiment result
Above-mentioned activity of weeding test result shows that the compound of the present invention 1 and compound 2 prevent weeds with excellent Effect.Moreover, the compound of the present invention is especially to the control efficiency of herba setariae viridis better than commercialization medicament mesotrione.
Compare compound D1- compound D11, relative to the compound of the present invention, compound D1- compound D11 is to test The control efficiency of weeds is below the compound of the present invention, and each compound is more obvious to the preventive effect difference of different weeds. Especially compound D8 and compound D11 is to test weeds substantially without control efficiency.
Further, the modification of substituent group is carried out to the pyrazole ring segment in the structure of the compound of the present invention, introduces first When base, ethyl, propyl, cyclopropyl, the activity of weeding of synthesized compound D12 to compound D15 are substantially better than corresponding original Drug compound D36 to compound D39.This N being found especially that from side illustration the present inventor, N- diethyl formyl substrate Section has apparent facilitation to the activity of weeding for improving HPPD class inhibitor.
In order to further verify N, N- diethyl formoxyl segment is to the facilitation of bioactivity, by N, N- diethyl first Acyl moieties carry out cyclisation processing, are chosen at five yuan or hexa-atomic for being widely present and having preferable bioactivity in pesticide and medicine Ring synthesizes compound D16 to compound D19, however, the activity of weeding of the series compound is lost substantially.On this basis, it protects Formoxyl is stayed to introduce the alkyl of other substitutions, such as alkoxy, three-membered ring, four-membered ring, five-membered ring and hexatomic ring.General sieve experiment In, it is optimal with the activity of weeding of furan nucleus and the derivative of thiphene ring, it is close with the activity of weeding of the compound of the present invention.
By comparative analysis, (compound D21, compound D22, compound D23, chemical combination when introducing three-membered ring or four-membered ring Object D24), activity of weeding generally reduces, and when the alkyl for introducing other substitutions, such as when alkoxy, activity of weeding is relative to raw medicine Molecule increases, suitable with the compound of the present invention to the control efficiency of gramineae weed, but imitates to the prevention and treatment of broadleaf weeds Fruit is less than the compound of the present invention.
Comprehensive analysis, N, N- diethyl formoxyl segment have the activity of weeding for improving HPPD class inhibitor of the invention Important role.
Test case 2: greenhouse primary dcreening operation experiment
A certain amount of raw medicine is weighed with assay balance, is made into 1 weight with the DMF dissolution containing 1 weight % Tween-80 emulsifier The mother liquor of % is measured, the liquid storage for being then diluted to various concentration with distilled water is spare.
Using pot-culture method: for examination target referring to table 3, table 4a, table 4b.Internal diameter 6cm flowerpot is taken, dress composite earth (vegetable garden soil: is educated Seedling matrix, 1:2, v/v) at 3/4, directly sowing is for trying target seed (bud rate >=85%), earthing 0.2cm, target to be tested Length is spare to or so the 3 leaf phases.Each compound according to 2,4,8g.a.i/mu dosage after the application of auto spraying tower, target to be tested Blade face medical fluid moves into hot-house culture after drying, investigation result after 30 days, is as a result listed in table 3, table 4a, in table 4b.
Investigation method is identical with test case 1.
Table 3: representation compound activity of weeding primary dcreening operation experimental result
Table 4a: representation compound is to Security of rice primary dcreening operation experimental result
Table 4b: safety primary dcreening operation experimental result of the representation compound to corn and wheat
Primary dcreening operation experimental result is analyzed, and compares general sieve experimental result, it can be seen that D30 pairs of compound of compound D25- The ideal and preventive effect difference with the compound of the present invention of the preventive effect of the weeds of general sieve is less obvious.
Further primary dcreening operation experimental result discovery, with the reduction of dosage, compound D25- compound D30 is to dog tail Grass and the preventive effect of barnyard grass generally reduce, and the compound of the present invention 1 and compound 2 with the reduction of dosage to herba setariae viridis and Barnyard grass still is able to reach ideal control efficiency.
Crop safety test result shows that compound D25- compound D30 has the crop (long-grained nonglutinous rice, japonica rice) of test Apparent phytotoxicity phenomenon can not further be developed as green, safety and selective herbicide.
Show compound D25- compound D30 to the crop of test the crop safety test result of corn and wheat There is apparent phytotoxicity phenomenon, can not further be developed as green, safety and selective herbicide.
And the compound of the present invention at least one of rice, corn and wheat show excellent crop safety and It is very prominent to paddy field main weeds control efficiency, it can be used as molecule drug candidate and carry out industrialization development.
Test case 3: the further activity of test compound 2
A certain amount of raw medicine is weighed with assay balance, is made into 1 weight with the DMF dissolution containing 1 weight % Tween-80 emulsifier The mother liquor of % is measured, the liquid storage for being then diluted to various concentration with distilled water is spare.
Using pot-culture method: for examination target referring to table 5 and table 6.Internal diameter 6cm flowerpot is taken, composite earth (vegetable garden soil: nursery base is filled Matter, 1:2, v/v) at 3/4, directly sowing test weed seed (bud rate >=85%), earthing 0.2cm is long to 3 leaf phases to weeds Left and right is spare.Each compound after the application of auto spraying tower, dries in the air according to 2.5,5.0 and 10g a.i./mu dosage to blade face medical fluid Hot-house culture is moved into after dry, as a result investigation result after 30 days is listed in table 5- table 6.
Investigation method is identical with test case 1.
Table 5: the secondary experimental result of the activity of weeding of compound 2
Dosage/g.a.i/mu Herba setariae viridis Three-coloured amaranth Chenopodiaceae Semen euphorbiae Piemarker
2.5 B A A A A
5.0 A A A A A
10.0 A A A A A
Table 6: the activity of weeding of 2 antagonism barnyard grass of compound
Test case 4: the further safety of test the compound of the present invention
A certain amount of raw medicine is weighed with assay balance, is made into 1 weight with the DMF dissolution containing 1 weight % Tween-80 emulsifier The mother liquor of % is measured, the liquid storage for being then diluted to various concentration with distilled water is spare.
Using pot-culture method: for examination target referring to table 7.Take internal diameter 6cm flowerpot, dress composite earth (vegetable garden soil: seedling medium, 1: 2, v/v) at 3/4, directly sowing above-mentioned test crop seed (bud rate >=85%), earthing 0.2cm, to long to 3 leaf phases or so It is spare.Each compound according to 2.5,5.0 and 10g a.i./mu dosage auto spraying tower application after, after after blade face, medical fluid dries Hot-house culture is moved into, investigation result after 30 days, the results are shown in Table 7.
Investigation method is identical with test case 1.
Table 7: safety of the compound 2 to Different Crop
Further crop safety test shows that compound 2 shows excellent crop safety to rice.Meanwhile Compound 2 has excellent preventive effect to the main weeds of paddy field, is especially to the control efficiency of semen euphorbiae and resistance barnyard grass It is very outstanding, it can be effectively solved the difficult problem of paddy field resistance barnyard grass prevention and treatment.
From the structural analysis of compound, N is introduced on the basis of compound 1, N- diethyl formoxyl segment synthesizes chemical combination Object 2, the introducing of the segment are not only able to maintain the bioactivity of original molecule, and the crop-selective for also adding original molecule is (right Rice shows the safety of height).Absolutely prove that the segment has extraordinary biological function.
Test case 5: the further safety of test compound
A certain amount of raw medicine is weighed with assay balance (0.0001g), is dissolved with the DMF containing 1 weight % Tween-80 emulsifier It is made into the mother liquor of 1 weight %, the liquid storage for being then diluted to various concentration with distilled water is spare.
Using pot-culture method: for examination target referring to table 8.Take internal diameter 6cm flowerpot, dress composite earth (vegetable garden soil: seedling medium, 1: 2, v/v) above-mentioned for trying target seed (bud rate >=85%) to directly sowing at 3/4, earthing 0.2cm, to long to a 1-2 leaf phase left side It is right spare.Each compound after the application of auto spraying tower, is dried according to 2.5,5.0 and 10g a.i./mu dosage to blade face medical fluid After move into hot-house culture, investigation result after 30 days, the results are shown in Table 8.
Investigation method is identical with test case 1.
The results are shown in Table 8.
Table 8: safety of the compound 2 to different cultivars rice
Analyze above-mentioned test result discovery, control efficiency of the compound of the present invention 2 to barnyard grass, herba setariae viridis, semen euphorbiae etc. Significantly, while to rice excellent safety is shown.The further crop safety in later period assesses discovery, and compound 2 is not to Rice with kind shows excellent crop safety, has extraordinary application prospect.
Test case 6: field trial
Crop test: for tried 6 kinds of rice (four Ye Yixin), peaceful round-grained rice 48, imperial round-grained rice 29, Y two excellent, Huang Huazhan, it is excellent No. 2 glutinous, Glutinous excellent No. 6.
Weeds test: referring to table 9- table 10
Test method: with 20m2For a cell, each processing is repeated 3 times, and 12 days cauline leafs are located by spraying after direct sowing of rice Reason, water on 48h after application are retained 5-7 days.
20 days after processing, treatment region and control zone are observed, with ocular estimate, according to investigation method identical with test case 1 Count the preventive effect of weeds and the safety of crop.
Test place: Sanya, Hainan
As a result it is listed in table 9- table 10.
Table 9: the field weeding activity experiment result of compound 2
Table 10: the field experiment result of compound 2
The above results show that under 5g.a.i/ mus of usage amounts, albefaction is obvious after compound 2 makes barnyard grass 4 days, and to thousand Gold special efficacy.
Under comparable conditions, for for trying 6 kinds of rice (four Ye Yixin): peaceful round-grained rice 48, imperial round-grained rice 29, Y two be excellent, Huang Huazhan, Glutinous excellent No. 2, it is excellent No. 6 glutinous, when using the compound of the present invention 2, rice will not generate albinism, without phytotoxicity.
To sum up, compound provided by the invention to the weeds in the crop plantings such as paddy field ground have good preventive effect with And there is excellent safety to crop.
The preferred embodiment of the present invention has been described above in detail, and still, the present invention is not limited thereto.In skill of the invention In art conception range, can with various simple variants of the technical solution of the present invention are made, including each technical characteristic with it is any its Its suitable method is combined, and it should also be regarded as the disclosure of the present invention for these simple variants and combination, is belonged to Protection scope of the present invention.

Claims (9)

1. a kind of quinazoline diones class compound, which has structure shown in formula (I):
Wherein, in formula (I), R is H or is group shown in formula (I-1).
2. compound according to claim 1, wherein in formula (I), R H.
3. compound according to claim 1, wherein in formula (I), R is group shown in formula (I-1).
4. application of the quinazoline diones class compound in controlling weeds described in any one of claim 1-3.
5. quinazoline diones class compound described in any one of claim 1-3 is selected from gramineae weed, broad-leaved in prevention and treatment Application at least one of weeds and sedge weed weeds.
6. application of the quinazoline diones class compound as pesticide herbicide described in any one of claim 1-3.
7. a kind of pesticide herbicide, which is made of active constituent and auxiliary material, and the active constituent includes that right is wanted Seek at least one of quinazoline diones class compound described in any one of 1-3.
8. pesticide herbicide according to claim 7, wherein the content of the active constituent is 1~99.9999 weight Measure %.
9. pesticide herbicide according to claim 7 or 8, wherein the dosage form of the pesticide herbicide is selected from missible oil, suspends At least one of agent, wettable powder, pulvis, granula, aqua, poison bait, mother liquor and female powder.
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