MX2011000477A - Compuestos heterociclicos como pesticidas. - Google Patents
Compuestos heterociclicos como pesticidas.Info
- Publication number
- MX2011000477A MX2011000477A MX2011000477A MX2011000477A MX2011000477A MX 2011000477 A MX2011000477 A MX 2011000477A MX 2011000477 A MX2011000477 A MX 2011000477A MX 2011000477 A MX2011000477 A MX 2011000477A MX 2011000477 A MX2011000477 A MX 2011000477A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- haloalkyl
- alkoxy
- spp
- halogen
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 6
- 239000000575 pesticide Substances 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 22
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 16
- -1 nitro, amino Chemical group 0.000 claims description 542
- 229910052736 halogen Inorganic materials 0.000 claims description 237
- 125000000217 alkyl group Chemical group 0.000 claims description 208
- 150000001875 compounds Chemical class 0.000 claims description 206
- 125000004076 pyridyl group Chemical group 0.000 claims description 158
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 146
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 131
- 125000001188 haloalkyl group Chemical group 0.000 claims description 127
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 106
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 105
- 125000003545 alkoxy group Chemical group 0.000 claims description 102
- 125000000335 thiazolyl group Chemical group 0.000 claims description 101
- 125000002971 oxazolyl group Chemical group 0.000 claims description 99
- 239000000203 mixture Substances 0.000 claims description 97
- 125000002883 imidazolyl group Chemical group 0.000 claims description 95
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
- 239000001257 hydrogen Substances 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 73
- 125000004306 triazinyl group Chemical group 0.000 claims description 73
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 72
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 72
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 70
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 70
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 69
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 64
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 63
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 55
- 125000004414 alkyl thio group Chemical group 0.000 claims description 54
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 125000002541 furyl group Chemical group 0.000 claims description 50
- 125000001544 thienyl group Chemical group 0.000 claims description 49
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 45
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 45
- 239000001301 oxygen Substances 0.000 claims description 45
- 229910052760 oxygen Inorganic materials 0.000 claims description 45
- 229910052717 sulfur Chemical group 0.000 claims description 45
- 239000011593 sulfur Chemical group 0.000 claims description 45
- 125000001425 triazolyl group Chemical group 0.000 claims description 43
- 125000000532 dioxanyl group Chemical group 0.000 claims description 42
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 40
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 34
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 33
- 125000005968 oxazolinyl group Chemical group 0.000 claims description 33
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 32
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 32
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 31
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 31
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 31
- 125000000304 alkynyl group Chemical group 0.000 claims description 31
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 31
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 31
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 31
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 31
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 31
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 31
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 31
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 31
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 31
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 31
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 31
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 31
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 31
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 31
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 31
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 31
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims description 30
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 30
- 125000001041 indolyl group Chemical group 0.000 claims description 30
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 30
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 30
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 29
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 29
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 29
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 29
- 125000003282 alkyl amino group Chemical group 0.000 claims description 28
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 23
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 18
- 150000001204 N-oxides Chemical class 0.000 claims description 18
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 17
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 11
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 11
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 11
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 11
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 11
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 5
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 5
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 5
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 12
- 241000238631 Hexapoda Species 0.000 abstract description 9
- 241000238421 Arthropoda Species 0.000 abstract description 4
- 150000002367 halogens Chemical group 0.000 description 176
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- 241000196324 Embryophyta Species 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 50
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 49
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 238000001704 evaporation Methods 0.000 description 45
- 230000008020 evaporation Effects 0.000 description 45
- 235000019253 formic acid Nutrition 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 38
- 238000002360 preparation method Methods 0.000 description 34
- 150000003254 radicals Chemical class 0.000 description 34
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 239000003085 diluting agent Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 11
- 240000008042 Zea mays Species 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 235000005822 corn Nutrition 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
- 244000299507 Gossypium hirsutum Species 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- 239000002917 insecticide Substances 0.000 description 8
- 150000003217 pyrazoles Chemical class 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000000443 aerosol Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 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 6
- 244000068988 Glycine max Species 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 6
- 150000004867 thiadiazoles Chemical class 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 241000238876 Acari Species 0.000 description 5
- 241000239223 Arachnida Species 0.000 description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- 241000257303 Hymenoptera Species 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001409 amidines Chemical class 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000009261 transgenic effect Effects 0.000 description 5
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 4
- 241001674048 Phthiraptera Species 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 241001481703 Rhipicephalus <genus> Species 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
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- HYKQYVSNFPWGKQ-UHFFFAOYSA-N pyridine-2-carbothioamide Chemical compound NC(=S)C1=CC=CC=N1 HYKQYVSNFPWGKQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
-
- 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
- A01N43/74—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 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
-
- 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
- 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
- A01N43/88—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 three ring hetero atoms
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- 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
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08012898 | 2008-07-17 | ||
| PCT/EP2009/004832 WO2010006713A2 (de) | 2008-07-17 | 2009-07-04 | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2011000477A true MX2011000477A (es) | 2011-03-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2011000477A MX2011000477A (es) | 2008-07-17 | 2009-07-04 | Compuestos heterociclicos como pesticidas. |
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| Country | Link |
|---|---|
| US (2) | US8809547B2 (enExample) |
| EP (6) | EP2583557B1 (enExample) |
| JP (2) | JP5681105B2 (enExample) |
| KR (1) | KR20110030700A (enExample) |
| CN (2) | CN102159079B (enExample) |
| AR (1) | AR072572A1 (enExample) |
| AU (1) | AU2009270520A1 (enExample) |
| BR (2) | BR122018010510B1 (enExample) |
| CA (1) | CA2730844A1 (enExample) |
| CO (1) | CO6341525A2 (enExample) |
| ES (6) | ES2426953T3 (enExample) |
| MX (1) | MX2011000477A (enExample) |
| TW (1) | TW201022260A (enExample) |
| WO (1) | WO2010006713A2 (enExample) |
| ZA (1) | ZA201100371B (enExample) |
Families Citing this family (261)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102056916A (zh) * | 2008-06-13 | 2011-05-11 | 拜耳作物科学股份公司 | 作为杀虫剂的新的杂芳族酰胺和硫代酰胺 |
| ES2426953T3 (es) | 2008-07-17 | 2013-10-28 | Bayer Cropscience Ag | Compuestos heterocíclicos como pesticidas |
| UA107791C2 (en) | 2009-05-05 | 2015-02-25 | Dow Agrosciences Llc | Pesticidal compositions |
| BR112012006956A2 (pt) * | 2009-10-12 | 2015-09-15 | Bayer Cropscience Ag | 1- (pirida-3-il) -pirazóisol e 1- (pirimida-5-il) - pirazóisol como pesticidas |
| MX2012011784A (es) | 2010-04-16 | 2013-03-21 | Bayer Ip Gmbh | Nuevos compuestos heterociclicos como pesticidas. |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| EP2566865B1 (de) | 2010-05-05 | 2014-06-25 | Bayer Intellectual Property GmbH | Thiazolderivate als schädlingsbekämpfungsmittel |
| AU2011267053B2 (en) | 2010-06-18 | 2015-09-24 | Bayer Cropscience Aktiengesellschaft | Active substance combinations with insecticide and acaricide properties |
| AR083431A1 (es) | 2010-06-28 | 2013-02-27 | Bayer Cropscience Ag | Compuestos heterociclicos como pesticidas |
| JP2012017289A (ja) | 2010-07-08 | 2012-01-26 | Bayer Cropscience Ag | 殺虫性ピロリン誘導体 |
| WO2012004293A2 (de) | 2010-07-08 | 2012-01-12 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
| CN103188936B (zh) * | 2010-08-31 | 2016-04-20 | 陶氏益农公司 | 杀虫组合物 |
| JP2012062267A (ja) | 2010-09-15 | 2012-03-29 | Bayer Cropscience Ag | 殺虫性ピロリンｎ−オキサイド誘導体 |
| JP2012082186A (ja) | 2010-09-15 | 2012-04-26 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
| WO2012045680A2 (de) | 2010-10-04 | 2012-04-12 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
| JP2013541554A (ja) | 2010-10-21 | 2013-11-14 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | Ｎ−ベンジルヘテロ環式カルボキサミド類 |
| BR112013009823A2 (pt) * | 2010-10-22 | 2016-07-05 | Bayer Ip Gmbh | novos compostos heterocíclicos como pesticidas |
| WO2012059497A1 (en) | 2010-11-02 | 2012-05-10 | Bayer Cropscience Ag | N-hetarylmethyl pyrazolylcarboxamides |
| AP3821A (en) | 2010-11-03 | 2016-09-30 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| CN103313971B (zh) | 2010-11-15 | 2015-12-02 | 拜耳知识产权有限责任公司 | N-芳基吡唑（硫代）甲酰胺 |
| SG190295A1 (en) | 2010-11-29 | 2013-06-28 | Bayer Ip Gmbh | Alpha,beta-unsaturated imines |
| WO2012076704A2 (en) * | 2010-12-10 | 2012-06-14 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| CA2827304C (en) | 2011-02-17 | 2018-11-13 | Bayer Intellectual Property Gmbh | Use of sdhi fungicides on conventionally bred asr-tolerant, stem canker resistant and/or frog-eye leaf spot resistant soybean varieties |
| US9510594B2 (en) | 2011-02-17 | 2016-12-06 | Bayer Intellectual Property Gmbh | Use of SDHI fungicides on conventionally bred ASR-tolerant, stem canker resistant and/or frog-eye leaf spot resistant soybean varieties |
| US8946124B2 (en) | 2011-02-17 | 2015-02-03 | Bayer Intellectual Property Gmbh | Substituted 3-(biphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-ones for therapy and halogen-substituted spirocyclic ketoenols |
| AU2012222517B2 (en) | 2011-03-01 | 2016-09-22 | Bayer Intellectual Property Gmbh | 2-acyloxy-pyrrolin-4-ones |
| AR085509A1 (es) | 2011-03-09 | 2013-10-09 | Bayer Cropscience Ag | Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas |
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