• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    heteroaryl-n-aryl carbamate molecules, and pesticidal composition. the present invention relates to new heteroaryl-n-aryl carbamates and their use in pest control, such as insecticides and acaricides. this invention also includes the preparation of the pesticidal compositions containing the compounds and methods of controlling insects using the compounds.
    公开号:BR112012002677A2
    申请号:R112012002677-1
    申请日:2010-08-05
    公开日:2021-03-09
    发明作者:William LAMBERT；Gary Crouse；Thomas Sparks；Denise Cudworth
    申请人:Dow Agrosciences Llc；
    IPC主号:
    专利说明:

    Invention Patent Descriptive Report for "MOLECULES OF HETEROARYL-N-ARYL CARBAMATES, AND PERFORMED COMPOSITION".
    FIELD OF THE INVENTION 5 This claim claims the benefit of the United States Provisional Order Serial Number 61 / 232,142 filed on August 7,
    2009. The invention described in this document is related to the field of pesticides and their use in pest control.
    BACKGROUND OF THE INVENTION Pests cause millions of human deaths throughout the world each year. In addition, there are more than ten thousand species of pests that cause losses in agriculture. These agricultural losses amount to billions of US dollars each year. Termites do damage to various structures such as houses. These termite damage losses amount to billions of US dollars each year. As a final note, many stored food pests eat and adulterate stored food. These losses of stored food amount to billions of US dollars each year, but more importantly, they deprive people of the necessary food. There is an acute need for new pesticides. Insects are developing resistance to pesticides in current use. Hundreds of insect species are resistant to one or more pesticides. The development of resistance to some of the older pesticides, such as DDT, carbamates, and organophosphates, is well known. However, even resistance to some of the newer pesticides has developed. Therefore, there is a need for new pesticides and particularly for pesticides that have new modes of action. SUBSTITUTES (NON-EXHAUSTIVE LIST) The examples produced for the substituents are (with the exception of halo) not exhaustive and should not be construed as limiting the invention described in this document. "alkenyl" means an acyclic substituent, unsaturated (hair prior to concentration. The desired 4- (1H- [1,2,4] triazol-3-yl) -benzonitrile was obtained in 98% purity by trituration with Et2O followed by filtration (12.17 g, 0.072 mol, 48%) Step 2. 4- [1- (4-Trifluoromethoxyphenyl) -1H- [1,2,4] triazol-3-yl] - 5 benzonitrile. 70 mg, 0.41 mmol), 1-iodo-4-trifluoromethoxybenzene (142 mg, 0.493 mmol), Cs2CO3 (535 mg, 1.644 mmol), CuI (3 mg, 0.012 mmol), 8-hydroxyquinoline (2 mg, 0.012 mmol), and DMF / H2O (2 mL; 10: 1 solution) were combined in a 10 mL EMC microwave reaction vessel equipped with a magnetic stir bar and subjected to 10 microwave irradiation at 150 ° C for 30 min The contents were then filtered and concentrated to dryness, providing the intermediate 1,3-diphenyl triazole (18 mg, 13%) Example 16: Preparation of 4- [1- (4-pentafluoroethylsulfanylphenyl) - 1H- [1,2,4] triazol-3-yl] -benzonitrile. N
    N C2F5S N 15 CN Step 1. 1-Bromo-4-pentafluoroethylsulfanylbenzene. The title compound was prepared using perfluoroalkylation conditions originally described by Popov et al., J. Fluorine Chem. 1982, 21, 365. In a solution of 4-bromobenzenethiol (500 mg, 2.64 mmol, 1.00 eq) and 20 triethylbenzyl ammonium chloride (60 mg, 0.26 mmol, 0.10 eq) in 10 mL 1: 1 Et2O / NaOH (25% aq) at 0 ° C 1,1,1,2,2-pentafluor-2-iodoethane gas was bubbled for 30 min (> 5 eq). During this time, a UV lamp was directed to the reaction vessel, while the temperature was kept below 10 ° C by intermittent use of an ice bath. The contents were then warmed to room temperature, extracted in Et2O (300 ml), dried (MgSO4) and concentrated under reduced pressure. A portion of this crude material was used in subsequent reactions without further purification (200 mg of residue: 120 mg of product, 0.39 mmol, 1.2 eq). Step 2. 4- [1- (4-Pentafluoroethylsulfanylphenyl) -1H- [1,2,4] triazol-3-yl] -benzonitrile. Coupling with 4- (1H- [1,2,4] triazol-3-yl) -benzonitrile as described above produced 4- [1- (4-pentafluoroethylsulfanylphenyl) -1H- [1,2,4] triazole-3 -il] -benzonitrile (70 mg, 46%). Example 17: Preparation of 4- [1- (4-pentafluoroethyloxy-phenyl) -1H- [1,2,4] triazol-3-yl] -benzaldehyde. N N
    N CHO C2F5O 5 Step 1. A solution of 3-p-tolyl-1H- [1,2,4] triazole (4.85 g, 30.5 mmol), 4-bromophenyl pentafluoroethyl ether (10.0 g, 34 , 4 mmols), Cs2CO3 (25 g, 77 mmols), CuI (1.25 g, 6.5 mmols) and 8-hydroxyquinoline (0.35 g, 2.4 mmols) in 9: 1 DMF / H2O (50 ml) was stirred vigorously and heated to 10 130 ° C (internal temperature) for 20 h. The solution was then cooled, poured into water and acidified with 2N HCl at pH 2. Ether (250 ml) was then added, and the solution was stirred and filtered before separating layers. The organic layer was dried and concentrated, and the resulting pasty solid was heated with hexanes (100 ml). The hot hexane layer 15 was decanted from the insoluble residue, the resulting solution cooled to 0 ° C, and the precipitated solid was filtered and air dried to provide 1- (4-pentafluoroethyloxy-phenyl) -3-p-tolyl -1H- [1,2,4] triazole (7.0 g, 61% based on the starting triazole) as an off-white solid: melting point 130-132 ° C; ESIMS m / z 370.8 (M + H). 20 Step 2. The product from Step 1 (7.0 g, 18.7 mmols) was dissolved in acetonitrile (200 ml) and stirred at room temperature, at the same time as ceric ammonium nitrate (32 g, 58 mmols) in water (60 ml) was added in portions over 10 min. The solution was then heated to reflux for 4 h, cooled and diluted with water (200 ml). The solution was extracted with ether (2 x 200 ml), and the combined organic layer was dried and concentrated to produce an orange oil. This material was dissolved in dioxane (40 ml) and treated with a solution of KOH (5 g, 90 mmols) in water (20 ml). The solution was heated to reflux for 2 h, then cooled and diluted with water (100 ml). The precipitated aldehyde was collected by filtration. Recrystallization from MeOH / H2O produced the pure aldehyde as a white solid (2.2 g, 30%): melting point 137-144 ºC 1H NMR (300
    MHz, CDCl3) 10.1 (s, 1H), 8.65 (s, 1H), 8.40 (d, J = 8.4 Hz, 2H), 8.0 (d, J = 8.4 Hz , 2H), 7.85 (d, J = 9 Hz, 2H), 7.45 (d, J = 9 Hz, 2H); ESIMS m / z 384.2 (M + H). Example 18: Preparation of 4- [1- (4-pentafluoroethyloxy-phenyl) -1H-5 [1,2,4] triazol-3-yl] -benzoic acid. N AT THE
    N C2F5O OH A solution of 4- [1- (4-pentafluoroethyloxy-phenyl) -1H- [1,2,4] triazol-3-yl] -benzaldehyde (1.7 g, 4.4 mmol), bromate sodium (2.1 g, 13.9 mmols) and sodium bisulfate (0.53 g, 4.5 mmols) in acetonitrile (50 ml) was heated under reflux for 5 h during the time that a voluminous precipitate formed up. The solution was then cooled and poured into water (100 mL), filtered and dried to provide the acid (1.67 g) as a white solid: melting point 225 ° C; 1H NMR (300 MHz, CDCl3) 10.1 (s, 1H), 8.63 (s, 1H), 8.35 (d, J = 8.4 Hz, 2H), 8.5 (d, J = 8.4 Hz, 2H), 7.85 (d, J = 9 Hz, 2H), 7.43 15 (d, J = 9 Hz, 2H); ESIMS m / z 399.2 (M + H +). Example 19: Preparation of 4- [1- (4-pentafluoroethyloxy-phenyl) -1H- [1,2,4] triazol-3-yl] -benzoylazide. N AT THE
    N C2F5O N3 A solution of 4- [1- (4-pentafluoroethyloxy-phenyl) -1H- 20 [1,2,4] triazol-3-yl] -benzoic acid (1.67 g, 4.2 mmol), diphenylphosphoryl azide (1.26 g, 4.58 mmols) and triethylamine (0.5 g, 5 mmols) in dry t-BuOH (10 mL) was heated to 75 ° C for 90 min, resulting in the dissolution of the particulate acid - the subsequent and subsequent precipitation of the azide. The cooled solution was then poured onto ice (10 g), and the resulting mixture was filtered and dried to provide the azide (0.80 g) as a white solid: melting point 112-115 ° C dec; 1H NMR (300 MHz, CDCl3) 8.62 (s, 1H), 8.33 (d, J = 8.4 Hz, 2H), 8.16 (d, J = 8.4 Hz, 2H), 7 , 85 (d, J = 9 Hz, 2H), 7.42 (d, J = 9 Hz, 2H); ESIMS m / z 425 (M + H). Example 20: Preparation of 4- [1- (4-butylphenyl) -1H- [1,2,4] triazol-3-yl] -30 benzonitrile. N N N
    CN A solution of 4-n-butylphenylhydrazine (1.0 g, 5 mmol) and 4-cyanobenzaldehyde (0.8 g, 6.0 mmol) in i-PrOH (15 mL) was heated in a steam bath for 2 h, and then it was cooled and diluted with water (55 ml). The resulting orange solid was filtered and air-dried to produce the hydrazone (1.30 g) as a yellow solid, melting point 107 ° C. A solution of this hydrazone (1.1 g, 4.0 mmols) and NCS (0.67 g, 5 mmols) in i-PrOH (20 mL) was stirred under nitrogen at room temperature for 2 h, for the time where the original solid dissolved and a new solid formed. The resulting orange solution was then treated with tetrazole (0.45 g, 6.4 mmols) and triethylamine (960 L, 7.0 mmols). The orange-brown solution was heated to reflux for 2 h. The solution was then cooled, diluted with water (25 mL), extracted with EtOAc, dried, concentrated and purified by chromatography (Biotage, 4: 1 hexane: EtOAc) to produce the triazole (0.42 g , 35%) as an off-white solid: melting point 124 ° C; 1H NMR (300 MHz, CDCl3) 8.58 (s, 1H), 8.33 (d, J = 8 Hz, 2H), 7.78 (d, J = 8 Hz, 2H), 7.64 (d , J = 8.2 Hz, 2H), 7.33 (d, J = 8.2 Hz, 2H), 2.70 (t, J = 7.8 Hz, 2H), 1.63 (m, 2H ), 1.38 (m, 2H), 0.95 (t, J = 7.5 Hz, 3H); E- SIMS m / z 303.1. Example 21: Preparation of 4- [1- (4-pentafluoroethyl-phenyl) -1H- [1,2,4] triazol-3-yl] -benzaldehyde. N N N
    CHO C2F5 Step 1. 1- (4-Pentafluoroethyl-phenyl) -3-p-tolyl-1H- [1,2,4] triazole. Pentafluoroethyl iodide (521 mg, 2.12 mmols) was condensed in a 25 ml bottle containing 1-bromo-4-iodobenzene (300 mg, 1.06 mmol), copper powder (0) (135 mg, 2.12 mmols), and DMSO (5 ml). The frasconette was then sealed and subjected to microwave irradiation at 150 ° C for 60 min. GC-MS confirmed the consumption of the starting material, which also produces the intermediates 1-bromo-4-pentafluoroethylbenzene and 1-iodo-4-30 pentafluoroethylbenzene. The mixture (1.06 mmol) was transferred to a flask
    权利要求:
    Claims (4)
    [1]
    1. Molecule, characterized by the fact that it has the following formula: 5 in which: (a) Ar 1 is a substituted phenyl, in which said substituted phenyl has one or more substituents independently selected from C 1 -C 6 haloalkyl and C1-C 6 haloalkoxy; (b) Het is a triazolyl; (c) Ar2 is a phenyl; (d) x1 is o or s; (e) X2 is o or S; (f) R4 is H or a C 1 -C 6 alkyl; (g) n = O, 1, or 2; (h) Rx and Ry are independently selected from H, C1- Cs alkyl, C1-Cs haloalkyl, C3-C 6 cycloalkyl, C3-Cs halocycloalkyl, C3-Cs cycloalkoxy, C3-C 6 halocycloalkoxy, C1-Cs alkoxy , C1-C 6 haloalkoxy, C2-Cs alkenyl, C2-Cs alkynyl, S (= O) n (C 1-Cs alkyl}, S (= O) n (C1-Cs haloalkyl), OS02 (C1- C 6 alkyl), OS02 (C1-C 6 haloalkyl), C (= O} H, C (= O) (C1-C 6 alkyl), C (= O) O (C1-C 6 alkyl}, C (= O) (C1-Cs haloalkyl}, C (= O) O (C1-Cs haloalkyl), C (= O) (C3-C 6 cycloalkyl), C {= O) O (C 3- Cs cycloalkyl), C (= O) (C2-Cs alkenyl), C (= O) O (C2-Cs alkenyl), (C1-C 6 alkyl) O (C1-Cs alkyl), (C1-Cs alkyl) S (C1-Cs alkyl), C (= O) (C1-Cs alkyl) C (= O) O (C1-C 6 alkyl), phenyl, and phenoxy; and (i) R 1, R2, and R3 are independently selected from H, CN, C1-Cs alkyl, C1-Cs haloalkyl, C3-C 6 cycloalkyl, C2-C 6 alkenyl, C2-Cs alkynyl, C (= O) (C1-C 6 alkyl), phenyl and Het-1.
    [2]
    2. Molecule according to claim 1, characterized by the fact that it is selected from compounds 1 to 136.
    [3]
    3. Molecule, characterized in that it is an acid addition salt, a salt derivative, a solvate or a pesticidably acceptable ester derivative of a molecule as defined in claim 1 or 2.
    [4]
    4. Composition, characterized by the fact that it comprises a molecule, as defined in claim 1 or 2, and at least one other compound showing insecticidal, herbicidal, acaricidal, nematicidal or fungicidal activity.
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    CN111970925A|2018-03-23|2020-11-20|孟山都技术有限公司|Aqueous nematicidal compositions comprising dispersants to inhibit crystal growth|
    TW202118760A|2019-07-17|2021-05-16|美商陶氏農業科學公司|Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto|
    CN111990009B|2020-09-11|2021-10-29|中国科学院成都生物研究所|Method for promoting germination of Cotinus coggygria seeds in Sichuan|
    法律状态:
    2021-03-16| B15I| Others concerning applications: loss of priority|Free format text: PERDA DA PRIORIDADE US 61/232,142 DE 07/08/2009 REIVINDICADA NO PCT/US2010/044538 DEVIDO A NAO APRESENTACAO DO CONTEUDO DO DOCUMENTO DE PRIORIDADE JUNTO AO REQUERIMENTO DE ENTRADA NA FASE NACIONAL E O MESMO TAMBEM NAO ESTAR DISPONIVEL NA BIBLIOTECA DIGITAL DA OMPI, CONFORME AS DISPOSICOES PREVISTAS NA LEI 9.279 DE 14/05/1996 (LPI) ART. 164O E NO ART. 26 DA RESOLUCAO INPI-PR 77/2013. |
    2021-03-23| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|
    2021-06-29| B06U| Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]|
    2021-10-13| B11B| Dismissal acc. art. 36, par 1 of ipl - no reply within 90 days to fullfil the necessary requirements|
    2021-12-14| B350| Update of information on the portal [chapter 15.35 patent gazette]|
    优先权:
    申请号 | 申请日 | 专利标题
    US23214209P| true| 2009-08-07|2009-08-07|
    PCT/US2010/044538|WO2011017513A1|2009-08-07|2010-08-05|Pesticidal compositions|
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