CN101607940A - A kind of fluorine Anthranilamide compound of Arthropodicidal - Google Patents
A kind of fluorine Anthranilamide compound of Arthropodicidal Download PDFInfo
- Publication number
- CN101607940A CN101607940A CNA2009101593501A CN200910159350A CN101607940A CN 101607940 A CN101607940 A CN 101607940A CN A2009101593501 A CNA2009101593501 A CN A2009101593501A CN 200910159350 A CN200910159350 A CN 200910159350A CN 101607940 A CN101607940 A CN 101607940A
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- CN
- China
- Prior art keywords
- compound
- alkyl group
- formula
- agriculture
- fluorine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 fluorine Anthranilamide compound Chemical class 0.000 title claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- PXBFMLJZNCDSMP-UHFFFAOYSA-N ortho-aminobenzoylamine Natural products NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 230000000749 insecticidal effect Effects 0.000 claims 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000000642 acaricide Substances 0.000 claims 1
- 229940124277 aminobutyric acid Drugs 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 229960000074 biopharmaceutical Drugs 0.000 claims 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 1
- 229940041033 macrolides Drugs 0.000 claims 1
- 230000001069 nematicidal effect Effects 0.000 claims 1
- 239000005645 nematicide Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention provides a kind of fluorine Anthranilamide compound that contains, with and the N-oxide compound and be applicable to the agricultural and non-agricultural salt, general structure I, wherein R
1, R
2, R
3, R
4a, R
4b, and R
5Be defined as in the description.
Description
Technical Field
The present invention relates to an arthropodicidal fluoroanthranilamide compound.
Background
The american dupont company, 2005, disclosed an arthropodicidal anthranilamide (CN02815924.1), formula i,
R1is CH3Or F, Cl or Br;
R2is F, Cl, Br, I or CF3；
R3Is CF3Cl, Br or OCH2CF3；
R4aIs C1-C4An alkyl group;
R4bis H or CH3；
R5Is Cl, Br;
or a salt suitable for use in agriculture.
The invention is based on the patent and aims at R3And/or R5Structural modifications are made in order to develop a more effective arthropodicidal novel compound.
Disclosure of Invention
The compounds of the present invention, including the N-oxides, as well as salts suitable for use in agriculture, non-agriculture, agricultural compositions comprising the compounds and their arthropodicidal effect in agriculture and non-agriculture.
The structural general formula I:
wherein,
R1is CH3Or element;
R2is element or CF3；
R3Is F, or when R5When is F, R3Is CF3F, Cl, Br, I, or OCH2CF3；
R4aIs C1-C4An alkyl group;
R4bis H or CH3；
R5Is F, or when R3When is F, R5Is F, Cl, Br, I;
or salts suitable for use in agriculture and non-agriculture.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to be limiting. All parts and percentages in the examples are by weight.
Example preparation of a typical compound IIa:
substrate 4(4.5g, 20mmol) and methanesulfonyl chloride (3g, 26mmol) were dissolved in anhydrous tetrahydrofuran, cooled to-5 ℃, a tetrahydrofuran (20ml) solution of substrate 5(3.97g, 20mmol) was added dropwise, pyridine (2.6g, 31.2mmol) was added dropwise, the reaction was kept at temperature for 30 minutes, then warmed to room temperature for 6 hours, post-treatment, water was slowly added with stirring, filtration, the solid was washed with tetrahydrofuran, vacuum-dried to give 7.2g of a yellow solid, yield 88.9%, HPLC purity 97%.1H NMR(400Hz，d6-DMSO)δppm：2.42(s，3H，CH3)，2.89(s，3H，CH3)，6.68(s，1H，pyrazole-H)，7.75(s，1H，Ar-H)，7.19-7.41(m，6H，Ar-H)，7.89(bs，1H，NH)，8.27(s，1H，NH)
Example two preparation of typical compound IIIa:
substrate 6(5.72g, 20mmol) and methanesulfonyl chloride (3g, 26mmol) were dissolved in anhydrous tetrahydrofuran, cooled to-5 ℃, a tetrahydrofuran (20ml) solution of substrate 5(3.97g, 20mmol) was added dropwise, pyridine (2.6g, 31.2mmol) was added dropwise, the reaction was kept at temperature for 30 minutes, then warmed to room temperature for 6 hours, post-treatment, water was slowly added with stirring, filtration, the solid was washed with tetrahydrofuran, and vacuum-dried to give a yellow solid 8.6g, yield 92%, HPLC purity 96.8%.1H NMR(400Hz，d6-DMSO)δppm：2.40(s，3H，CH3)，2.83(s，3H，CH3)，6.11(s，1H，pyrazole-H)，7.68(s，1H，Ar-H)，7.11-7.32(m，6H，Ar-H)，7.89(bs，1H，NH)，8.09(s，1H，NH)
Example three preparation of typical compound IVa:
dissolving a substrate 7(4.83g, 20mmol) and methylsulfonyl chloride (3g, 26mmol) in anhydrous tetrahydrofuran, cooling to-5 ℃, adding a tetrahydrofuran (20ml) solution of the substrate 5(3.97g, 20mmol) dropwise, adding pyridine (2.6g, 31.2mmol) dropwise, keeping the temperature for reaction for 30 minutes, raising the temperature to room temperature for reaction for 6 hours, carrying out aftertreatment, slowly adding water while stirring, filtering, washing the solid with tetrahydrofuran, and drying in vacuum to obtain a yellow solid 8.0g, the yield is 95%, and the HPLC purity is 97%;1H NMR(400Hz，d6-DMSO)δppm：2.46(s，3H，CH3)，2.93(s，3H，CH3)，6.39(s，1H，pyrazole-H)，7.79(s，1H，Ar-H)，7.01-7.22(m，6H，Ar-H)，7.81(bs，1H，NH)，8.29(s，1H，NH)。
Claims (8)
- A fluorine-containing anthranilamide compound, or an N-oxide, having the general structural formula I:wherein,R1is CH3.Or element;R2is element or CF3；R3Is F, or when R5When is F, R3Is CF3F, Cl, Br, I, or OCH2CF3；R4aIs C1-C4An alkyl group;R4bis H or CH3；R5Is F, or when R3When is F, R5Is F, Cl, Br, I;or salts suitable for use in agriculture and non-agriculture.
- 2. The compound of claim 1, wherein R4aIs C1-C4Alkyl and R4bIs H; or R4aIs CH3And R4bIs CH3。
- 3. A compound of the formula (II),
R1is CH3.Or element;R2is element or CF3；R4aIs C1-C4An alkyl group;R4bis H or CH3。 - 4. A compound of the formula (III),
R1is CH3.Or element;R2is element or CF3；R3Is CF3Cl, Br, I, or OCH2CF3；R4aIs C1-C4An alkyl group;R4bis H or CH3。 - 5. A compound of the formula IV,
R1is CH3.Or element;R2is element or CF3；R5Is Cl, Br, I;R4ais C1-C4An alkyl group;R4bis H or CH3。 - 6. The compounds as claimed in claims 1, 4 and 5, characterized in that they can be used as compositions for controlling invertebrate pests, in combination with one or more surfactants, solid diluents or liquid diluents.
- 7. The compounds as claimed in claims 1, 4 and 5, characterized in that they can be used as compositions for controlling invertebrate pests, in combination with one or more other biologically active compounds or agents, including pyrethroids, carbamates, nicotinoids, sodium neurona-channel blockers, insecticidal macrolides, aminobutyric acid antagonists, insecticidal ureas.
- 8. The composition of claim 7, wherein the one or more additional biologically active compounds or combination of agents is selected from the group consisting of insecticides, nematocides, miticides, and biologicals.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2009101593501A CN101607940A (en) | 2009-07-13 | 2009-07-13 | A kind of fluorine Anthranilamide compound of Arthropodicidal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2009101593501A CN101607940A (en) | 2009-07-13 | 2009-07-13 | A kind of fluorine Anthranilamide compound of Arthropodicidal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101607940A true CN101607940A (en) | 2009-12-23 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2009101593501A Pending CN101607940A (en) | 2009-07-13 | 2009-07-13 | A kind of fluorine Anthranilamide compound of Arthropodicidal |
Country Status (1)
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| CN (1) | CN101607940A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013096497A1 (en) | 2011-12-19 | 2013-06-27 | E. I. Du Pont De Nemours And Company | Nanoparticles compositions containing polymers and anthranilic acid diamide insecticides for propagule coating |
| US8563470B2 (en) | 2010-12-13 | 2013-10-22 | E I Du Pont De Nemours And Company | Anthranilic diamide and cyclodextrin compositions for propagule coating |
| US8563469B2 (en) | 2010-12-13 | 2013-10-22 | E I Du Pont De Nemours And Company | Acrylate/methacrylate-based random copolymer/anthranilic diamide compositions for propagule coating |
| US8569268B2 (en) | 2010-12-13 | 2013-10-29 | E I Du Pont De Nemours And Company | Acrylate/methacrylate-based diblock copolymer/anthranilic diamide compositions for propagule coating |
| US8575065B2 (en) | 2010-12-13 | 2013-11-05 | E I Du Pont De Nemours And Company | Acrylate/methacrylate-based star copolymer/anthranilic diamide compositions for propagle coating |
| US8652998B2 (en) | 2010-12-13 | 2014-02-18 | E I Du Pont De Nemours And Company | Branched copolymer/anthranilic diamide compositions for propagule coating |
| US8709976B2 (en) | 2010-12-13 | 2014-04-29 | E I Du Pont De Nemours And Company | Anthranilic diamide compositions for propagle coating |
| WO2014168601A1 (en) | 2011-12-19 | 2014-10-16 | E. I. Du Pont De Nemours And Company | Acrylate/methacrylate-based triblock copolymer / anthranilic diamide compositions for propagule coating |
| WO2015076779A1 (en) | 2013-11-19 | 2015-05-28 | Halliburton Energy Services, Inc | Measuring critical shear stress for mud filtercake removal |
| US9149039B2 (en) | 2011-12-19 | 2015-10-06 | E I Du Pont De Nemours And Company | Anthranilic diamide/polymer propagule-coating compositions |
| CN114621144A (en) * | 2022-03-23 | 2022-06-14 | 南开大学 | Cyano-substituted phenyl pyrazole amide derivative and preparation method and application thereof |
-
2009
- 2009-07-13 CN CNA2009101593501A patent/CN101607940A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8563470B2 (en) | 2010-12-13 | 2013-10-22 | E I Du Pont De Nemours And Company | Anthranilic diamide and cyclodextrin compositions for propagule coating |
| US8563469B2 (en) | 2010-12-13 | 2013-10-22 | E I Du Pont De Nemours And Company | Acrylate/methacrylate-based random copolymer/anthranilic diamide compositions for propagule coating |
| US8569268B2 (en) | 2010-12-13 | 2013-10-29 | E I Du Pont De Nemours And Company | Acrylate/methacrylate-based diblock copolymer/anthranilic diamide compositions for propagule coating |
| US8575065B2 (en) | 2010-12-13 | 2013-11-05 | E I Du Pont De Nemours And Company | Acrylate/methacrylate-based star copolymer/anthranilic diamide compositions for propagle coating |
| US8652998B2 (en) | 2010-12-13 | 2014-02-18 | E I Du Pont De Nemours And Company | Branched copolymer/anthranilic diamide compositions for propagule coating |
| US8709976B2 (en) | 2010-12-13 | 2014-04-29 | E I Du Pont De Nemours And Company | Anthranilic diamide compositions for propagle coating |
| WO2013096497A1 (en) | 2011-12-19 | 2013-06-27 | E. I. Du Pont De Nemours And Company | Nanoparticles compositions containing polymers and anthranilic acid diamide insecticides for propagule coating |
| WO2014168601A1 (en) | 2011-12-19 | 2014-10-16 | E. I. Du Pont De Nemours And Company | Acrylate/methacrylate-based triblock copolymer / anthranilic diamide compositions for propagule coating |
| US9149039B2 (en) | 2011-12-19 | 2015-10-06 | E I Du Pont De Nemours And Company | Anthranilic diamide/polymer propagule-coating compositions |
| US9204644B2 (en) | 2011-12-19 | 2015-12-08 | E I Du Pont De Nemours And Company | Nanoparticles compositions containing polymers and anthranilic acid diamide insecticides for propagule coating |
| WO2015076779A1 (en) | 2013-11-19 | 2015-05-28 | Halliburton Energy Services, Inc | Measuring critical shear stress for mud filtercake removal |
| CN114621144A (en) * | 2022-03-23 | 2022-06-14 | 南开大学 | Cyano-substituted phenyl pyrazole amide derivative and preparation method and application thereof |
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Legal Events
| Date | Code | Title | Description |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
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Application publication date: 20091223 |