CN109320506A - A kind of difluorophenyl furodiazole insecticidal/acaricidal agent - Google Patents
A kind of difluorophenyl furodiazole insecticidal/acaricidal agent Download PDFInfo
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- CN109320506A CN109320506A CN201811323531.9A CN201811323531A CN109320506A CN 109320506 A CN109320506 A CN 109320506A CN 201811323531 A CN201811323531 A CN 201811323531A CN 109320506 A CN109320506 A CN 109320506A
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- Prior art keywords
- compound
- difluorophenyl
- insecticidal
- furodiazole
- ethyl
- Prior art date
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- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 18
- -1 difluorophenyl furodiazole Chemical compound 0.000 title claims abstract description 12
- 230000000749 insecticidal effect Effects 0.000 title claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 11
- 239000000642 acaricide Substances 0.000 claims abstract description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 5
- 239000002917 insecticide Substances 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 abstract description 5
- 241000238631 Hexapoda Species 0.000 abstract description 2
- 230000002147 killing effect Effects 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000500437 Plutella xylostella Species 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- IHNSIFFSNUQGQN-UHFFFAOYSA-N tioxazafen Chemical compound C1=CSC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 IHNSIFFSNUQGQN-UHFFFAOYSA-N 0.000 description 7
- 102000002322 Egg Proteins Human genes 0.000 description 6
- 108010000912 Egg Proteins Proteins 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 210000004681 ovum Anatomy 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052956 cinnabar Inorganic materials 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/82—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 three ring hetero atoms
Abstract
The present invention provides a kind of difluorophenyl furodiazole compounds, and structure is as shown in general formula I:In formula: R1Selected from methyl or ethyl；R2Selected from methyl, ethyl or tert-butyl；R3Selected from H or Cl.Generalformulaⅰcompound has inhibitory or killing effect to pest, harmful mite, can be used as insecticide, acaricide for agricultural insect pest, the prevention and treatment of mite evil.
Description
Technical field is related to a kind of difluorophenyl furodiazole and kills the invention belongs to the field of insecticidal/acaricidal agent in pesticide
Worm acaricide and its for agricultural or forestry pest harmful mite prevention and treatment.
The background technique growth that agriculturally pest harmful mite harms the crops, leads to the underproduction and quality decline.At present to pest
The prevention and treatment of harmful mite relies primarily on chemical pesticide, frequently uses insecticidal/acaricidal agent due to a large amount of, pest harmful mite produces it sternly
A series of problems, such as drug resistance of weight, causes dosage increasing, and preventive effect is lower and lower, and the lasting period shortens, agriculture residual raising.Newly
Different role mechanism insecticidal/acaricidal agent exploitation and application, be solve Pest-resistant effective means.CN
104054719A discloses structureBiologically active compound (KC), which is
Two replace furodiazole compound, and completely new chemical structure assigns its new mechanism of action and outstanding properties of product, for big
The prevention and treatment of the crops nematode such as beans, cotton, corn has the characteristics that low dosage, long holding effect and low nuisanceless, has been used as novel defence line
Kind commercialization (commercial disignation Tioxazafen) is formulated in worm agent.Although the compounds of this invention (I) has in structure to it similar
Place, but in the prior art type I compound as described in the present invention and its be used as agricultural insecticidal acaricide it is not disclosed.
The purpose of the present invention is to provide a kind of structure novel, simple synthetic methods, safe and efficient desinsection for summary of the invention
Acaricide, it can be used for the prevention and treatment of agricultural or forestry pest harmful mite.
Technical scheme is as follows:
A kind of difluorophenyl furodiazole compound, structure is as shown in general formula I:
In formula: R1Selected from methyl or ethyl；R2Selected from methyl, ethyl or tert-butyl；R3Choosing
From H or Cl.
Generalformulaⅰcompound of the present invention can be prepared by the following method: II compound of formula is with III compound of formula with three in toluene
Ethamine is acid binding agent, and type I compound is made in reflux cyclization.The embodiment of the present invention is shown in specific preparation.Table 1 lists I chemical combination of general formula
The structure and physical property of object.
1 generalformulaⅰcompound structure of table and physical property
| Compound | R1 | R2 | R3 | Appearance | Fusing point (DEG C) |
| Ⅰa | CH3 | CH2CH3 | Cl | White solid | 95.8-97.3 |
| Ⅰb | CH2CH3 | CH3 | H | White solid | 153.6-155.2 |
| Ⅰc | CH3 | C(CH3)3 | H | Faint yellow solid | 104.1-106.2 |
| Ⅰd | CH2CH3 | C(CH3)3 | H | Faint yellow solid | 50.2-52.1 |
The advantages and positive effects of the present invention:
The compounds of this invention (general formula I) has structure novel, preparation method are easy, worm mite is simultaneous to control as insecticidal/acaricidal agent
Advantage.Compared with commodity Tioxazafen compound (KC), the compounds of this invention has aphid diamondback moth and mite ovum good
Effect is killed in suppression.The compounds of this invention (general formula I) has different structure and Insecticiding-miticiding from existing commercial insecticidal/acaricidal agent
Mechanism, and the compounds of this invention is heterocyclic nitrogen compound, is had to beneficial organism hypotoxicity, degradable, Environmental compatibility
Good feature has especially suitable for the improvement of resistanc pest harmful mite generally existing at present as initiative pesticide new variety
Exploitation and application prospect well.
The compounds of this invention is pest control or mite evil, can be used alone, can also make with other active substance combinations
With to improve the comprehensive performance of product.
The invention also includes using generalformulaⅰcompound as the insecticide acaricide composition of active component, wherein active component is in group
The weight percentage for closing object is 1~99%.The insecticide acaricide composition further includes acceptable carrier in agricultural or forestry.
It should be clear that various variations or change can be carried out within the scope of the restriction of claim of the invention.
Specific embodiment
Following synthesis example, raw test result can be used to further illustrate the present invention, but be not intended to limit the present invention.
Synthesize example
The preparation of example 1, chemical compounds I a:
(1) III a (R of intermediate1For-CH3, R2For-CH2CH3, R3For the synthesis of-Cl):
In 250mL reaction flask plus 0.03mol (2.04g) sodium ethoxide, 100mL ethyl alcohol are solvent, and ice-water bath reacts, successively
2- butanone (A) 0.03mol (2.16g), diethy-aceto oxalate (B) 0.03mol (4.38g), TLC tracking reaction is added dropwise, 2h has reacted
Entirely, revolving removing ethyl alcohol, water on the rocks, hydrochloric acid tune pH to 3 or so, methylene chloride extraction, liquid separation, organic phase are dry with anhydrous sodium sulfate
Dry, revolving removes methylene chloride, obtains brown liquid compound C 4.64g, yield 90%.
Compound C is added to methylene chloride (100mL) to do in the 250mL reaction flask of solvent, 80% hydrazine hydrate is added dropwise
0.03mol (1.2g), room temperature reaction, TLC track fully reacting, and methylene chloride extracts, liquid separation, and organic phase is dry with anhydrous sodium sulfate
Dry, revolving removes methylene chloride, obtains oily liquids compound D 4.38g, yield 87%.
Compound D is added to methylene chloride (100mL) to do in the 250mL reaction flask of solvent, dimethyl suflfate is added dropwise
0.03mol (3.78g), 80 DEG C of reactions, TLC track fully reacting, and revolving removes methylene chloride, obtains oily liquids compound E.It will
Compound E is added to ethyl acetate and does in the reaction flask of solvent, be added dropwise 0.03mol (4.02g) sulfonic acid chloride, back flow reaction, TLC with
Track fully reacting, ethyl acetate extraction, liquid separation, organic phase is dry with anhydrous sodium sulfate, and revolving removes ethyl acetate, obtains oily liquid
Body compound F.It is dissolved with ethyl alcohol, 15% potassium hydroxide aqueous solution hydrolysis, then with salt acid for adjusting pH to there is solid precipitation.It takes out
Filter, obtains solid chemical compound G, dry 3.69g, yield 80%.
Toluene makees solvent, compound G and 0.03mol (3.57g) thionyl chloride is added in reaction flask, 80 DEG C of reaction 3h,
TLC tracks fully reacting, and revolving removes toluene, obtains compound III a 5.11g, yield 99%.
(2) synthesis of intermediate II:
0.11mol (7.65g) hydroxylamine hydrochloride is added in 250mL reaction flask, 50g ethyl acetate makees solvent, then adds respectively
80 DEG C of reaction 4h, TLC tracking are heated in 0.11mol triethylamine (11.11g) and 0.1mol (13.9g) 2,6- difluorobenzonilyile, stirring
Fully reacting, it is cooling, it filters, filtrate revolving removes EA, and it is cooling, obtain II 14.62g of compound as white solid, yield 85%.
(3) synthesis of chemical compounds I a:
Take 0.02mol (2.78g) intermediate II in 250mL reaction flask, 40g toluene makees solvent, adds 0.02mol (2.2g)
Triethylamine, is added dropwise compound III a 0.02mol (4.14g) obtained, and stirring room temperature reaction 3h, TLC track intermediate II reaction
Completely, reflux is reheated, the reaction was continued, and 6h is complete to being dehydrated.Add water, liquid separation, toluene is mutually dry with anhydrous sodium sulfate, and revolving is removed
Remove toluene, cooling I a 5.32g of compound as white solid, yield 82%.
The preparation of example 2, chemical compounds I b:
(1) III b (R of intermediate1For-CH2CH3, R2For-CH3, R3For the synthesis of-H):
The synthesis of 1 intermediate of synthetic method reference example, III a.
(2) synthesis of chemical compounds I b:
Take 0.02mol (2.78g) intermediate II in 250mL reaction flask, 40g toluene makees solvent, adds 0.02mol (2.2g)
Triethylamine is added dropwise intermediate III b (1- ethyl -3- methyl -4-H- pyrazole acyl chloride) 0.02mol (3.45g) obtained, stirs room temperature
3h is reacted, TLC tracks intermediate II fully reacting, is heated to reflux, and the reaction was continued, and 6h is complete to being dehydrated.Add water, liquid separation, toluene phase
Dry with anhydrous sodium sulfate, revolving removes toluene, cooling I b 4.81g of compound as white solid, yield 83%.
The preparation of example 3, chemical compounds I c:
(1) III c (R of intermediate1For-CH3, R2For-CMe3, R3For the synthesis of-H)
The synthesis of 1 intermediate of synthetic method reference example, III a.
(2) preparation of chemical compounds I c
Take 0.02mol (2.78g) intermediate II in 250mL reaction flask, 40g toluene makees solvent, adds 0.02mol (2.2g)
Intermediate III c (1- methyl -3- tert-butyl -4-H- pyrazole acyl chloride) 0.02mol (4.01g) obtained, teeter chamber is added dropwise in triethylamine
Temperature reaction 3h, TLC tracking fully reacting, is heated to reflux, the reaction was continued, and 6h is complete to being dehydrated.Add water, liquid separation, toluene is mutually used anhydrous
Sodium sulphate is dry, and revolving removes toluene, cooling faint yellow solid chemical compounds I c 5.4g, yield 85%.
The preparation of example 4, chemical compounds I d:
(1) III d (R of intermediate1For-CH2CH3, R2For-CMe3, R3For the synthesis of-H)
The synthesis of 1 intermediate of synthetic method reference example, III a.
(2) preparation of chemical compounds I d:
Take 0.02mol (2.78g) intermediate II in 250mL reaction flask, 40g toluene makees solvent, adds 0.02mol (2.2g)
Intermediate III d (1- ethyl -3- tert-butyl -4-H- pyrazole acyl chloride) 0.02mol (4.29g) obtained, teeter chamber is added dropwise in triethylamine
Temperature reaction 3h, TLC tracking fully reacting, is heated to reflux, the reaction was continued, and 6h is complete to being dehydrated.Add water, liquid separation, toluene is mutually used anhydrous
Sodium sulphate is dry, and revolving removes toluene, cooling faint yellow solid chemical compounds I d 5.78g, yield 87%.
Compound nuclear magnetic data in general formula I of the present invention is as follows:
Chemical compounds I a:1H NMR(500MHz,DMSO-d6)δ7.83–7.74(m,1H),7.41(t,2H),4.19(s,3H),
2.65(q,2H),1.23(t,3H)。
Chemical compounds I b:1H NMR(500MHz,DMSO-d6)δ7.66–7.57(m,1H),7.26(t,2H),7.18(s,1H),
4.45(q,2H),2.23(s,3H),1.32(t,3H)。
Chemical compounds I c:1H NMR(500MHz,DMSO-d6)δ7.79–7.69(m,1H),7.37(t,2H),7.09(s,1H),
4.16(s,3H),1.28(s,9H)。
Chemical compounds I d:1H NMR(500MHz,DMSO-d6)δ7.78–7.69(m,1H),7.36(t,2H),7.09(s,1H),
4.57(q,2H),1.36(t,3H),1.28(s,9H)。
Biological activity test
Example 5, insecticidal activity assay
(1) diamondback moth activity determination method is killed
Kill diamondback moth activity test method: the compounds of this invention is to diamondback moth determination of activity using international resistance action committee member
The leaf dipping method that meeting (IRAC) proposes.With prepared medical fluid to be measured, cabbage leaves are impregnated with straight peen ophthalmology tweezers, time 3-5 second,
Extraction raffinate is got rid of, 1 tablet once, totally 3, each sample, is successively placed on processing paper by sample flag sequence.After medical fluid is dry, it is put into
Have in the straight type pipe of markd 10cm long, accesses 3 age diamondback moth larvae 30, cover nozzle with gauze.Test process is set
In in standard process chamber, 48h inspection result touches polypide to pull out needle, and motionless person is death.Calculating the death rate, (3 weights are done in test
It is multiple, be averaged).
2 generalformulaⅰcompound of table kills diamondback moth active testing result
According to test result it is found that I a of the compounds of this invention, I b are significantly better than the killing effect of diamondback moth
Tioxazafen (KC), chemical compounds I c, I d and Tioxazafen (KC) are suitable.
(2) acaricidal ovum activity measuring method
Acaricidal ovum activity is measured using infusion process and the method for statistical correction Mortality of insect.Detailed process is: will be for examination
Medicament is diluted to required concentration by effective component respectively, is aseptically respectively drawn in 50mL medical fluid injection culture dish, then divide
Jin Ru there be the blade of cinnabar mite ovum (group that mite ovum is normally raised by indoor standardized method), to add 50mL aqua sterilisa
Plate does blank control.Culture dish is placed in 24 ± 1 DEG C of constant incubators.The investigation statistics death rate after 48h.
The acaricidal activity test result of 3 generalformulaⅰcompound of table
According to test result it is found that I a of the compounds of this invention, I b kill effect and are better than to the suppression of Tetranychus cinnabarinus mite ovum
Tioxazafen (KC), chemical compounds I c, I d and Tioxazafen (KC) are suitable.
Claims (3)
1. a kind of difluorophenyl furodiazole compound, structure is as shown in general formula I:
In formula: R1Selected from methyl or ethyl；R2Selected from methyl, ethyl or tert-butyl；R3Selected from H
Or Cl.
2. a kind of purposes of difluorophenyl furodiazole compound according to claim 1, it is characterised in that general formula I chemical combination
Object is used as agricultural or forestry insecticidal/acaricidal agent, has control efficiency to agricultural pests harmful mite.
3. a kind of insecticide acaricide composition is active component and agricultural or forestry containing generalformulaⅰcompound described in claim 1
Upper acceptable carrier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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