CN105367548A - Cyan dihalogenation pyrazol amide series compound and preparation method and application thereof - Google Patents
Cyan dihalogenation pyrazol amide series compound and preparation method and application thereof Download PDFInfo
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- CN105367548A CN105367548A CN201510689355.0A CN201510689355A CN105367548A CN 105367548 A CN105367548 A CN 105367548A CN 201510689355 A CN201510689355 A CN 201510689355A CN 105367548 A CN105367548 A CN 105367548A
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- 0 BCN*(CC(NCC=C)=CC)C(C[C@]1Cl)C1C(Cl)=* Chemical compound BCN*(CC(NCC=C)=CC)C(C[C@]1Cl)C1C(Cl)=* 0.000 description 5
- JRPQUOVJMJGZGX-NTSWFWBYSA-N CC(C)(C[C@@H]1Cl)[C@@H]1NC Chemical compound CC(C)(C[C@@H]1Cl)[C@@H]1NC JRPQUOVJMJGZGX-NTSWFWBYSA-N 0.000 description 1
- JSSYXJOQIJTIQB-AATRIKPKSA-N CCC/C(/Cl)=C(/C)\N Chemical compound CCC/C(/Cl)=C(/C)\N JSSYXJOQIJTIQB-AATRIKPKSA-N 0.000 description 1
Classifications
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- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Abstract
The invention discloses a cyan dihalogenation pyrazol amide series compound and a preparation method and application thereof. The general chemical molecular formula of the compound is C<17>H<7>N<6>O<2>Cl<2>BrR1R2, wherein R1 represents methyl, Cl or Br; R2 represents H, methyl, isopropyl, ethyl, allyl, butyl or isobutyl. The preparation method of the compound comprises the steps of treating triethylamine or pyridine as an acid binding agent, making substitued 2-amino-5-cyan-N-benzamide react with 1-(3chloropyridine)-2-group)-3-bromine-4-chlorine-1H-pyrazol-5-formyl chloride in acetonitrile at the temperature of 0-40 DEG C for two hours, and obtaining the compound; or treating acetonitrile or methylbenzene as solvent, conducting backflow for 3-4 hours, and obtaining the compound. The compound is used for pest control in sanitation, agriculture or forestry and is high in insecticidal activity and systemic property and wide in insecticidal spectrum.
Description
Technical field
The present invention relates to field of pesticides, specifically a kind of cyano group dihalo pyrazol acid amide compounds and its preparation method and application.
Background technology
E.I.Du Pont Company reported the novel cyanogen insect amide (CY, cyantraniliprole) with systemic activity in 2000, for novel ryanodine receptor suppresses insecticides.This product has systemic activity, extensively can prevent and treat lepidopteran, Hemiptera and coleopteran pest.The structural formula of compound cyanogen insect amide (CY, cyantraniliprole) is:
In patent CN103232431 " a kind of dihalo pyrazol acid amide compounds and application thereof ", disclose a kind of dihalo pyrazol acid amide compounds (KC), structural formula is:
In structural formula KC, R1 is methyl, Cl or Br; R2 is Cl or Br, R3 is H, methyl, sec.-propyl, ethyl or allyl group.
Cl or Br of the R2 position of KC is become cyano group by the present invention, although the compounds of this invention structurally with cyanogen worm benzamide (CY, cyantraniliprole) and in the structure of dihalo pyrazole amide (KC) similarity is had, but the cyano group dihalo pyrazole amide formula I that replaces containing cyano group of the present invention and application performance have no open, and have the insecticidal activity stronger compared with CY and KC and interior absorption containing the cyano group dihalo pyrazole amide formula I that cyano group replaces.
Summary of the invention
The object of the present invention is to provide a kind of novel structure, synthetic method simple and cyano group dihalo pyrazol acid amide compounds of highly effective and safe and preparation method thereof, also disclose the pest control that this compound is applied to agricultural, forestry, to solve the problem proposed in above-mentioned background technology.
For achieving the above object, the invention provides following technical scheme:
A kind of cyano group dihalo pyrazol acid amide compounds, its chemical structure of general formula is:
In formula, R1 is methyl, Cl or Br; R2 is H, methyl, sec.-propyl, ethyl, allyl group, butyl or isobutyl-.
As the further scheme of the present invention: in its chemical structure of general formula, R1 is preferably methyl or Cl, R2 are preferably methyl, ethyl or sec.-propyl.
A preparation method for cyano group dihalo pyrazol acid amide compounds, preparation process is:
Formula II compound and formula III compound using triethylamine or pyridine as acid binding agent, react 2h and prepare formula I in acetonitrile at 0 ~ 40 DEG C of temperature; Or formula II compound and formula III compound with acetonitrile or toluene for solvent, backflow 3 ~ 4h prepares formula I.The structure of compound of Formula I and physical properties in table 1,
The structure of table 1 partial Formula I and physical properties
| Compound | R1 | R2 | Outward appearance, fusing point (DEG C) |
| 1 | CH3 | CH3 | White solid, 216 ~ 230 |
| 2 | CH3 | CH2CH3 | White solid, 230 ~ 245 |
| 3 | CH3 | CH(CH3)2 | White solid, 240 ~ 250 |
| 4 | Cl | CH3 | White solid, 215 ~ 225 |
| 5 | Cl | CH2CH3 | White solid, 225 ~ 235 |
An application for cyano group dihalo pyrazol acid amide compounds, this compound is used for the pest control of health, agricultural or forestry.
Compared with prior art, the invention has the beneficial effects as follows:
Cl or Br of the R2 position of KC is become cyano group by the present invention, and due to specific polarity and the wetting ability of cyano group, this compound cyano group dihalo pyrazole amide I has strong systemic activity, and insecticidal spectrum comparatively KC is wider.
Cyano group is linked into 4-position phenyl ring by the present invention first, prepare cyano group dihalo pyrazol acid amide compounds wide compared with the insecticidal spectrum of dihalo pyrazol acid amide compounds KC, not only there is splendid insecticidal activity to lepidoptera pest, and to insects such as aphid, plant hopper, thrips, there is very high insecticidal activity.
The compounds of this invention, when pest control, can be used alone and also can use to improve insecticidal effect with other active substance combination.Compound of the present invention can make the insect-killing composition of active ingredient, and wherein active ingredient part by weight is in the composition 1 ~ 99%, this insect-killing composition is agricultural, forestry and hygienic insecticide field accept carrier.
Embodiment
Below in conjunction with the embodiment of the present invention, be clearly and completely described the technical scheme in the embodiment of the present invention, obviously, described embodiment is only the present invention's part embodiment, instead of whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art, not making the every other embodiment obtained under creative work prerequisite, belong to the scope of protection of the invention.
The compound of following embodiment is in table 1
The preparation of embodiment 1 compound 1,
(1) synthesis of 1-(3-chloropyridine-2-base) the chloro-1H-pyrazole-5-ethyl formate of the bromo-4-of-3-
33.25g (0.1mol) 1-(3-chloropyridine-2-base)-3-bromo-4 is added in 250ml reaction flask, 5-dihydro-1-H pyrazole-5-ethyl formate and 100ml acetonitrile, 27g (0.2mol) SULPHURYL CHLORIDE is added under stirring, backflow 4h, thin-layer chromatography TLC detects raw material and disappears, distilling off solvent, obtains yellow oily liquid 30g, productive rate 82%.
Wherein, bromo-4, the 5-dihydro-1H pyrazole-5-ethyl formate reference (Wang Yanjun of 1-(3-chloropyridine-2-base)-3-, magnify forever, Wu Xiaoming, the synthesis [J] of Rynaxypyr. agricultural chemicals, 2010, (03): 170-174) method preparation.
(2) synthesis of 1-(3 chloropyridine-2-base) the chloro-1H-pyrazoles of the bromo-4-of-3--5-formic acid
36.6g (0.1mol) 1-(3-chloropyridine-2-base) the chloro-1H-pyrazole-5-ethyl formate of the bromo-4-of-3-and 50ml methyl alcohol is added respectively in 250ml reaction flask, add the NaOH solution 40ml of 20% under stirring, at 50-60 DEG C, react 2h, distill out methyl alcohol, cooling, instillation HCl, adjustment pH is 2-3, separates out white solid, suction filtration, vacuum-drying, obtains white solid 33g, yield 90%.
(3) synthesis of 1-(3 chloropyridine-2-base) the chloro-1H-pyrazoles of the bromo-4-of-3--5-formyl chloride
33.8g (0.1mol) 1-(3-chloropyridine-2-base) the chloro-1H-pyrazoles of the bromo-4-of-3--5-formic acid and 60ml tetrahydrofuran (THF) is added in 250ml reaction flask, instillation 19.05g (0.15mol) oxalyl chloride, stirring at room temperature 10h, distilling off solvent, obtain salmon liquid 34g, yield 95%.
(4) synthesis of the iodo-3-tolyl acid of 2-amino-5-
2-amino-3-tolyl acid 5g (0.033mol) is in 100ml reaction flask, add 30mlDMF, add NIS iodination reagent (7.8g, 0.035mol) under stirring at room temperature, temperature is elevated to 80 DEG C of reaction 2h, TLC monitoring has been reacted, cool to 30 DEG C, reaction solution is poured in frozen water, stir 20min, filtration obtains 8.9g gray solid, productive rate 97%.
(5) synthesis of 2-amino-5-cyano-3 tolyl acid
2-amino-5-iodo-3-tolyl acid 4.27g (0.015mol) CuCN1.87g (0.021mol) is in 100ml reaction flask, add 50mlDMF, temperature is elevated to 145 DEG C of reactions, keeps this temperature 5h, TLC detection reaction to complete, the most of solvent of decompression removing, add 50ml water and 5ml quadrol, cross and filter insolubles, filtrate adjusts pH to slightly acidic, filtration obtains 2.54g beige solid, productive rate 94%.
(6) 6-cyano group-8-methyl isophthalic acid H-benzo [the d] [synthesis of 1,3] oxazine-2,4-diketone
2-amino-5-cyano-3 tolyl acid 8.8g (0.05mol), tetrahydrofuran (THF) 30ml, be stirred to after solid dissolves completely and add solid phosgene 4.5g (0.015mol), stirring at room temperature 2h, reaction solution has a large amount of red brown solid to separate out, saturated aqueous sodium carbonate stir about 30min is added after sloughing solvent, filter washing and obtain red brown solid 6.7g, productive rate 66%.
(7) 2-amino-5-cyano-N, 3-dimethyl benzamide synthesis
Get 6-cyano group-8-methyl isophthalic acid H-benzo [d] [1,3] oxazines-2,4-diketone 2.0g (0.01mol), acetonitrile 20ml, triethylamine 2g (0.02mol) are in being furnished with in the 50ml single port bottle stirring magneton, stir lower dropping 25% aqueous methylamine solution 2.5g (0.02mol), after stirring at room temperature 2h to reaction clarification, steam solvent, reaction is extracted with ethyl acetate 3 times, merge organic phase and use saturated common salt water washing, anhydrous sodium sulfate drying, except desolventizing obtains yellow solid 1.12g, yield 58%.
1HNMR(400MHz，DMSO，TMS)d：8.28(s，1H，NH)，7.78(s，1H，Ph-6-H)，7.28(s，1H，Ph-4-H)，7.28(s，2H，NH2)，2.76(d，3H，NHCH3)，2.11(s，3H，Ph-CH3)。
(8) synthesis of compound 1
1.98g (0.01mol) 2-amino-5-cyano-N is added in 100ml reaction flask, 3-dimethyl benzamide, 10ml acetonitrile, the mixing solutions of instillation 3.92g (0.011mol) 1-(3 chloropyridine-2-base) the chloro-1H-pyrazoles of the bromo-4-of-3--5-formyl chloride and 5ml acetonitrile, backflow 3h, suction filtration, acetonitrile wash 10ml tri-times, vacuum-drying, obtains white powder 4.8g, yield 83%.
1HNMR(400MHz，DMSO，TMS)d：10.0(s，1H，Ph-NH)，8.54-8.55(dd，1H，pyridin-6-H)，8.25(m，1H,Pyridin-4-H)，8.0(t，1H，Pyridin-5H)，7.7-7.8(s，1H，Ph-3-H)7.6-7.7(s，1H，Ph-5-H)，6.4(d，1H，NH)，2.7(d，3H，CH3)，2.2(s，3H，Ph-CH3)。
The synthesis of embodiment 2 compound 2
(1) 2-amino-5-cyano-N-ethyl-3-methyl benzamide synthesis
Get 6-cyano group-8-methyl isophthalic acid H-benzo [d] [1,3] oxazines-2,4-diketone 2.0g (0.01mol), acetonitrile 20ml, triethylamine 2g (0.02mol) are in being furnished with in the 50ml single port bottle stirring magneton, stir lower dropping ethylamine solution 4g (0.02mol), after stirring at room temperature 2h to reaction clarification, steam solvent, reaction is extracted with ethyl acetate 3 times, merge organic phase and use saturated common salt water washing, anhydrous sodium sulfate drying, except desolventizing obtains yellow solid 1.5g, yield 62%.
(2) synthesis of compound 2
2.13g (0.01mol) 2-amino-5-cyano-N-ethyl-3-methyl benzamide is added in 100ml reaction flask, 10ml acetonitrile, the mixing solutions of instillation 3.92g (0.011mol) 1-(3 chloropyridine-2-base) the chloro-1H-pyrazoles of the bromo-4-of-3--5-formyl chloride and 5ml acetonitrile, backflow 3h, suction filtration, acetonitrile wash 10ml tri-times, vacuum-drying, obtain white powder 5.2g, yield 84%.
1HNMR(400MHz，DMSO，TMS)d：10.0(s，1H，Ph-NH)，8.54-8.55(dd，1H，pyridin-6-H)，8.25(m，1H,Pyridin-4-H)，8.0(t，1H，Pyridin-5H)，7.7-7.8(s，1H，Ph-3-H)7.6-7.7(s，1H，Ph-5-H)，6.4(d，1H，NH)，2.7(m，2H，CH2)，2.2(s，3H，Ph-CH3)，1.,4-1.5(t,3H,CH3)。
The synthesis of embodiment 3 compound 4
(1) synthesis of the iodo-3-chloro-benzoic acid of 2-amino-5-
2-amino-3-chloro-benzoic acid 5.2g (0.033mol) is in 100ml reaction flask, add 30mlDMF, add NIS iodination reagent (7.8g, 0.035mol) under stirring at room temperature, temperature is elevated to 80 DEG C of reaction 2h, TLC monitoring has been reacted, cool to 30 DEG C, reaction solution is poured in frozen water, stir 20min, filtration obtains 8.9g gray solid, productive rate 95%.
(2) synthesis of 2-amino-5-cyano-3 chloro-benzoic acid
2-amino-5-iodo-3-chloro-benzoic acid 4.37g (0.015mol) CuCN1.87g (0.021mol) is in 100ml reaction flask, add 50mlDMF, temperature is elevated to 145 DEG C of reactions, keeps this temperature 5h, TLC detection reaction to complete, the most of solvent of decompression removing, add 50ml water and 5ml quadrol, cross and filter insolubles, filtrate adjusts pH to slightly acidic, filtration obtains 2.64g beige solid, productive rate 94%.
(3) the chloro-1H-benzo [d] of the 6-cyano group-8-[synthesis of 1,3] oxazine-2,4-diketone
2-amino-5-cyano-3 chloro-benzoic acid 9.0g (0.05mol), tetrahydrofuran (THF) 30ml, be stirred to after solid dissolves completely and add solid phosgene 4.5g (0.015mol), stirring at room temperature 2h, reaction solution has a large amount of red brown solid to separate out, saturated aqueous sodium carbonate stir about 30min is added after sloughing solvent, filter washing and obtain red brown solid 6.9g, productive rate 65%.
(4) 2-amino-5-cyano-N-methyl-3-chlorobenzamide synthesis
Get the chloro-1H-benzo [d] [1 of 6-cyano group-8-, 3] oxazines-2,4-diketone 2.2g (0.01mol), acetonitrile 20ml, triethylamine 2g (0.02mol) are in being furnished with in the 50ml single port bottle stirring magneton, stir lower dropping 25% aqueous methylamine solution 2.5g (0.02mol), after stirring at room temperature 2h to reaction clarification, steam solvent, reaction is extracted with ethyl acetate 3 times, merge organic phase and use saturated common salt water washing, anhydrous sodium sulfate drying, except desolventizing obtains yellow solid 1.22g, yield 59%.
1HNMR(400MHz，DMSO，TMS)d：8.35(s，1H，NH)，7.84(s，1H，Ph-6-H)，7.38(s，1H，Ph-4-H)，7.35(s，2H，NH2)，2.78(d，3H，NHCH3)。
(5) synthesis of compound 4
The chloro-benzamide of 2.12g (0.01mol) 2-amino-5-cyano-N methyl-3-is added in 100ml reaction flask, 10ml acetonitrile, the mixing solutions of instillation 3.92g (0.011mol) 1-(3 chloropyridine-2-base) the chloro-1H-pyrazoles of the bromo-4-of-3--5-formyl chloride and 5ml acetonitrile, backflow 3h, suction filtration, acetonitrile wash 10ml tri-times, vacuum-drying, obtain white powder 4.7g, yield 81%.
1HNMR(400MHz，DMSO，TMS)d：10.4(s，1H，Ph-NH)，8.54-8.55(dd，1H，pyridin-6-H)，8.25(m，1H,Pyridin-4-H)，8.0(t，1H，Pyridin-5H)，7.8-7.9(s，1H，Ph-3-H)7.7-7.8(s，1H，Ph-5-H)，6.8(d，1H，NH)，2.8(d，3H，NHCH3)。
The synthesis of embodiment 4 compound 5
(1) 2-amino-5-cyano-N-ethyl-3-chlorobenzamide synthesis
Get the chloro-1H-benzo [d] [1 of 6-cyano group-8-, 3] oxazines-2,4-diketone 2.2g (0.01mol), acetonitrile 20ml, triethylamine 2g (0.02mol) are in being furnished with in the 50ml single port bottle stirring magneton, stir lower dropping ethylamine solution 5g (0.02mol), after stirring at room temperature 2h to reaction clarification, steam solvent, reaction is extracted with ethyl acetate 3 times, merge organic phase and use saturated common salt water washing, anhydrous sodium sulfate drying, except desolventizing obtains yellow solid 1.39g, yield 60%.
1HNMR(400MHz，DMSO，TMS)d：8.38(s，1H，NH)，7.84(s，1H，Ph-6-H)，7.38(s，1H，Ph-4-H)，7.32(s，2H，NH2)，2.73(m，2H，NHCH2)，1.56(t，3H，CH2CH3)。
(2) synthesis of compound 5
The chloro-benzamide of 2.22g (0.01mol) 2-amino-5-cyano-N ethyl-3-is added in 100ml reaction flask, 10ml acetonitrile, the mixing solutions of instillation 3.92g (0.011mol) 1-(3 chloropyridine-2-base) the chloro-1H-pyrazoles of the bromo-4-of-3--5-formyl chloride and 5ml acetonitrile, backflow 3h, suction filtration, acetonitrile wash 10ml tri-times, vacuum-drying, obtain white powder 4.9g, yield 81%.
1HNMR(400MHz，DMSO，TMS)d：10.4(s，1H，Ph-NH)，8.54-8.55(dd，1H，pyridin-6-H)，8.25(m，1H,Pyridin-4-H)，8.0(t，1H，Pyridin-5H)，7.8-7.9(s，1H，Ph-3-H)7.7-7.8(s，1H，Ph-5-H)，6.7(d，1H，NH)，2.7(m，2H，NHCH2)，1.4-1.5(t，3H，CH2CH3)。
Also can prepare compound 3 according to the method described above, the qualification of its nucleus magnetic resonance is as follows:
1HNMR(400MHz，DMSO，TMS)d：10.0(s，1H，Ph-NH)，8.54-8.55(dd，1H，pyridin-6-H)，8.25(m，1H,Pyridin-4-H)，8.0(t，1H，Pyridin-5H)，7.7-7.8(s，1H，Ph-3-H)7.6-7.7(s，1H，Ph-5-H)，6.4(d，1H，NH)，3.9(m，1H，CH(CH3)2)，2.2(s，3H，Ph-CH3)，1.1-1.2(d,6H,CH(CH3)2)。
Embodiment 5 biological activity determination
Test example: the mixed solvent getting 2.5ml acetone/methanol (volume ratio 1:1) joins in the weighing bottle filling 3mg compound (purity is in 100%), stirring makes it fully dissolve, add the standing water that 2.5ml contains 0.2% tween 80, after stirring, obtain the new compound solution 5ml of 600mg/L.
Blank: process with acetone/methanol/water (volume ratio 1:1:2, the tween 80 containing 0.1%).
Compound insecticidal activity adopts sterilant microscreen standard operation spray method, and observe taking food and death condition after insect larvae process day by day, divide rank according to 0-100,100 expressions are all killed, or prevention effect is 100%.
Mainly toxicity mensuration is done, in table 2 to bollworm and aphid
Table 2 biologically active data table
It is suitable to bollworm preventive effect that compound 1 disclosed by the invention compares KC dihalo pyrazol acid amide compounds, slightly high.But compound 1 pair of aphid has and well prevents and treats activity, this is not available for KC dihalo pyrazole amide.Because aphid is piercing mouth parts insect, interior absorption compound is only had just to have high reactivity to it, so compound 1 has interior absorption.
For in test compound, concentration to have at 0.2ppm the preventive effect being greater than 90% compound to bollworm has compound 2, compound 3, compound 4, compound 5.
For in test compound, concentration to have at 1ppm the preventive effect being greater than 90% compound to aphid has compound 2, compound 3, compound 4, compound 5.
To those skilled in the art, obviously the invention is not restricted to the details of above-mentioned one exemplary embodiment, and when not deviating from spirit of the present invention or essential characteristic, the present invention can be realized in other specific forms.Therefore, no matter from which point, all should embodiment be regarded as exemplary, and be nonrestrictive, scope of the present invention is limited by claims instead of above-mentioned explanation, and all changes be therefore intended in the implication of the equivalency by dropping on claim and scope are included in the present invention.
Claims (4)
1. a cyano group dihalo pyrazol acid amide compounds, is characterized in that, its chemical structure of general formula is:
In formula, R1 is methyl, Cl or Br; R2 is H, methyl, sec.-propyl, ethyl, allyl group, butyl or isobutyl-.
2. cyano group dihalo pyrazol acid amide compounds according to claim 1, is characterized in that, the R1 in its chemical structure of general formula is preferably methyl or Cl, R2 are preferably methyl, ethyl or sec.-propyl.
3. a preparation method for cyano group dihalo pyrazol acid amide compounds as claimed in claim 1 or 2, it is characterized in that, preparation process is:
Formula II compound and formula III compound using triethylamine or pyridine as acid binding agent, react 2h and prepare formula I in acetonitrile at 0 ~ 40 DEG C of temperature; Or formula II compound and formula III compound with acetonitrile or toluene for solvent, backflow 3 ~ 4h prepares formula I.
4. an application for cyano group dihalo pyrazol acid amide compounds as claimed in claim 1 or 2, is characterized in that, this compound is used for the pest control of health, agricultural or forestry.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110066270A (en) * | 2018-01-24 | 2019-07-30 | 湖南化工研究院有限公司 | Multiamide class compound and the preparation method and application thereof |
| CN110845472A (en) * | 2018-08-21 | 2020-02-28 | 沈阳中化农药化工研发有限公司 | Preparation method of pyrazole amide compound |
| WO2024038436A1 (en) | 2022-08-16 | 2024-02-22 | Adama Makhteshim Ltd. | Process for preparing cyantraniliprole via amino-cyano-benzene derivative |
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| CN103232431A (en) * | 2013-01-25 | 2013-08-07 | 青岛科技大学 | Dihalogenated pyrazole amide compound and its use |
| WO2015144683A1 (en) * | 2014-03-27 | 2015-10-01 | Bayer Cropscience Ag | Insecticidal and nematocidal active ingredient combinations |
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| CN110066270A (en) * | 2018-01-24 | 2019-07-30 | 湖南化工研究院有限公司 | Multiamide class compound and the preparation method and application thereof |
| CN110066270B (en) * | 2018-01-24 | 2021-02-26 | 湖南化工研究院有限公司 | Polyamide compound and preparation method and application thereof |
| CN110845472A (en) * | 2018-08-21 | 2020-02-28 | 沈阳中化农药化工研发有限公司 | Preparation method of pyrazole amide compound |
| CN110845472B (en) * | 2018-08-21 | 2022-08-26 | 沈阳中化农药化工研发有限公司 | Preparation method of pyrazole amide compound |
| WO2024038436A1 (en) | 2022-08-16 | 2024-02-22 | Adama Makhteshim Ltd. | Process for preparing cyantraniliprole via amino-cyano-benzene derivative |
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