ES2319972T3 - Iminobenzoxazinas, iminobenzotiazinas e iminoquinazolinas para controlar plagas de invertebrados. - Google Patents
Iminobenzoxazinas, iminobenzotiazinas e iminoquinazolinas para controlar plagas de invertebrados. Download PDFInfo
- Publication number
- ES2319972T3 ES2319972T3 ES02780457T ES02780457T ES2319972T3 ES 2319972 T3 ES2319972 T3 ES 2319972T3 ES 02780457 T ES02780457 T ES 02780457T ES 02780457 T ES02780457 T ES 02780457T ES 2319972 T3 ES2319972 T3 ES 2319972T3
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- Spain
- Prior art keywords
- chloro
- alkyl
- halogen
- ring
- independently
- 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.)
- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 claims abstract description 264
- 238000000034 method Methods 0.000 claims abstract description 121
- -1 C 1-C 4 alkylthio Chemical group 0.000 claims abstract description 113
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 108
- 150000002367 halogens Chemical group 0.000 claims abstract description 108
- 125000001424 substituent group Chemical group 0.000 claims abstract description 81
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 64
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 53
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 52
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 43
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 36
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 19
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims abstract description 19
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 13
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 150000001204 N-oxides Chemical class 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 108
- 239000000203 mixture Substances 0.000 claims description 90
- 229910052801 chlorine Inorganic materials 0.000 claims description 59
- 229910052794 bromium Inorganic materials 0.000 claims description 56
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 39
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 29
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 17
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 14
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- FJCWUDNZLHEOHG-UHFFFAOYSA-N 7,9-dichloro-5-[2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-3-yl]-2,3-dihydroimidazo[1,2-c]quinazoline Chemical compound N1=C(C(F)(F)F)C=C(C=2N3CCN=C3C3=CC(Cl)=CC(Cl)=C3N=2)N1C1=NC=CC=C1Cl FJCWUDNZLHEOHG-UHFFFAOYSA-N 0.000 claims description 6
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 6
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 6
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 5
- LGHATAABPWJILK-UHFFFAOYSA-N 2-[2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-3-yl]-8-methyl-n-propan-2-yl-3,1-benzoxazin-4-imine Chemical compound N=1C2=C(C)C=CC=C2C(=NC(C)C)OC=1C1=CC(C(F)(F)F)=NN1C1=NC=CC=C1Cl LGHATAABPWJILK-UHFFFAOYSA-N 0.000 claims description 5
- 101150065749 Churc1 gene Proteins 0.000 claims description 5
- 102100038239 Protein Churchill Human genes 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- PBMPZEQGCZRCOJ-UHFFFAOYSA-N 2-[5-bromo-2-(3-chloropyridin-2-yl)pyrazol-3-yl]-8-methyl-n-propan-2-yl-3,1-benzoxazin-4-imine Chemical compound N=1C2=C(C)C=CC=C2C(=NC(C)C)OC=1C1=CC(Br)=NN1C1=NC=CC=C1Cl PBMPZEQGCZRCOJ-UHFFFAOYSA-N 0.000 claims description 4
- BJUPQUWZTOPDNZ-UHFFFAOYSA-N 2-[5-bromo-2-(3-chloropyridin-2-yl)pyrazol-3-yl]-n-tert-butyl-8-methyl-3,1-benzoxazin-4-imine Chemical compound CC1=CC=CC(C(O2)=NC(C)(C)C)=C1N=C2C1=CC(Br)=NN1C1=NC=CC=C1Cl BJUPQUWZTOPDNZ-UHFFFAOYSA-N 0.000 claims description 4
- CRYCGVUSMMFXPQ-UHFFFAOYSA-N 6-chloro-2-[2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-3-yl]-n,8-dimethyl-3,1-benzoxazin-4-imine Chemical compound N=1C2=C(C)C=C(Cl)C=C2C(=NC)OC=1C1=CC(C(F)(F)F)=NN1C1=NC=CC=C1Cl CRYCGVUSMMFXPQ-UHFFFAOYSA-N 0.000 claims description 4
- DEFDNYDOZUXEMX-UHFFFAOYSA-N 6-chloro-2-[2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-3-yl]-n-ethyl-8-methyl-3,1-benzoxazin-4-imine Chemical compound N=1C2=C(C)C=C(Cl)C=C2C(=NCC)OC=1C1=CC(C(F)(F)F)=NN1C1=NC=CC=C1Cl DEFDNYDOZUXEMX-UHFFFAOYSA-N 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- BKMVAXAIDVJQEJ-UHFFFAOYSA-N n-tert-butyl-2-[2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazol-3-yl]-8-methyl-3,1-benzoxazin-4-imine Chemical compound CC1=CC=CC(C(O2)=NC(C)(C)C)=C1N=C2C1=CC(C(F)(F)F)=NN1C1=NC=CC=C1Cl BKMVAXAIDVJQEJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 6
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 abstract description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 abstract 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 3
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- 238000006243 chemical reaction Methods 0.000 description 70
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- 239000002253 acid Substances 0.000 description 45
- 239000000460 chlorine Substances 0.000 description 44
- 239000002904 solvent Substances 0.000 description 42
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 41
- 238000003786 synthesis reaction Methods 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 33
- 238000012360 testing method Methods 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000002585 base Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 241000196324 Embryophyta Species 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 230000009418 agronomic effect Effects 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 18
- 238000009472 formulation Methods 0.000 description 17
- 150000007513 acids Chemical class 0.000 description 16
- 150000003217 pyrazoles Chemical class 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 241000238631 Hexapoda Species 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 241001124076 Aphididae Species 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- 230000003647 oxidation Effects 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 240000001307 Myosotis scorpioides Species 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- 241000209149 Zea Species 0.000 description 12
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 235000005822 corn Nutrition 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- 241000238876 Acari Species 0.000 description 11
- 241000255925 Diptera Species 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 241000244206 Nematoda Species 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 230000006378 damage Effects 0.000 description 10
- 230000014509 gene expression Effects 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 241000219146 Gossypium Species 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
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- 239000004480 active ingredient Substances 0.000 description 8
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 241000254173 Coleoptera Species 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
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- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 6
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- 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 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000002168 alkylating agent Substances 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
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- 238000000605 extraction Methods 0.000 description 6
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- 230000026030 halogenation Effects 0.000 description 6
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- 230000007062 hydrolysis Effects 0.000 description 6
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- 150000004679 hydroxides Chemical class 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- CWXOAQXKPAENDI-UHFFFAOYSA-N sodium methylsulfinylmethylide Chemical group [Na+].CS([CH2-])=O CWXOAQXKPAENDI-UHFFFAOYSA-N 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 210000003454 tympanic membrane Anatomy 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- A01N43/86—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 1,3
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
-
- 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
- C07D413/10—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 linked by a carbon chain containing aromatic 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32939201P | 2001-10-15 | 2001-10-15 | |
| US329392P | 2001-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2319972T3 true ES2319972T3 (es) | 2009-05-18 |
Family
ID=23285170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02780457T Expired - Lifetime ES2319972T3 (es) | 2001-10-15 | 2002-10-15 | Iminobenzoxazinas, iminobenzotiazinas e iminoquinazolinas para controlar plagas de invertebrados. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7148217B2 (enExample) |
| EP (1) | EP1435785B1 (enExample) |
| JP (1) | JP4317752B2 (enExample) |
| KR (1) | KR100840083B1 (enExample) |
| CN (1) | CN100503604C (enExample) |
| AU (1) | AU2002343512B2 (enExample) |
| BR (1) | BR0213646A (enExample) |
| DE (1) | DE60230651D1 (enExample) |
| ES (1) | ES2319972T3 (enExample) |
| MX (1) | MXPA04003445A (enExample) |
| RU (1) | RU2298007C2 (enExample) |
| WO (1) | WO2003032731A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR036872A1 (es) * | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
| MY142967A (en) | 2001-08-13 | 2011-01-31 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
| TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| KR101011837B1 (ko) * | 2002-01-22 | 2011-01-31 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 무척추 해충 방제를 위한 퀴나졸린(디)온 |
| BR0311707A (pt) * | 2002-06-13 | 2005-03-15 | Du Pont | Composto, composição e método de controle de pelo menos uma praga invertebrada |
| AU2003295491B2 (en) * | 2002-11-15 | 2009-10-08 | E.I. Du Pont De Nemours And Company | Novel anthranilamide insecticides |
| CL2004000234A1 (es) * | 2003-02-12 | 2005-04-15 | Biogen Idec Inc | Compuestos derivados 3-(piridin-2-il)-4-heteroaril-pirazol sustituidos, antagonistas de aik5 y/o aik4; composicion farmaceutica y uso del compuesto en el tratamiento de desordenes fibroticos como esclerodermia, lupus nefritico, cicatrizacion de herid |
| WO2006023783A1 (en) * | 2004-08-17 | 2006-03-02 | E.I. Dupont De Nemours And Company | Novel anthranilamides useful for controlling invertebrate pests |
| JP5215669B2 (ja) * | 2004-11-18 | 2013-06-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アントラニルアミド殺虫剤 |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| MX2008002236A (es) * | 2005-08-24 | 2008-03-27 | Du Pont | Antranilamidas para controlar plagas de invertebrados. |
| EP2008521A1 (en) * | 2007-06-28 | 2008-12-31 | Syngeta Participations AG | Methods of controlling insects |
| US8110608B2 (en) | 2008-06-05 | 2012-02-07 | Ecolab Usa Inc. | Solid form sodium lauryl sulfate (SLS) pesticide composition |
| US20090318393A1 (en) * | 2008-06-23 | 2009-12-24 | Shalaby Shalaby W | Film-forming liquid formulations for controlled release of pesticides |
| PH12012502031A1 (en) * | 2010-04-27 | 2017-06-07 | Sumitomo Chemical Co | Pesticidal composition and its use |
| PL2563131T3 (pl) | 2010-04-27 | 2017-09-29 | Sumitomo Chemical Company, Limited | Kompozycja szkodnikobójcza i jej zastosowanie |
| JP5712504B2 (ja) | 2010-04-27 | 2015-05-07 | 住友化学株式会社 | 有害生物防除組成物およびその用途 |
| JP5724211B2 (ja) | 2010-04-28 | 2015-05-27 | 住友化学株式会社 | 植物病害防除組成物およびその用途 |
| WO2011135834A1 (en) * | 2010-04-28 | 2011-11-03 | Sumitomo Chemical Company, Limited | Pesticidal composition and its use |
| RU2569962C2 (ru) | 2010-04-28 | 2015-12-10 | Сумитомо Кемикал Компани, Лимитед | Композиция для борьбы с заболеваниями растений и ее применение |
| JP5789918B2 (ja) * | 2010-04-28 | 2015-10-07 | 住友化学株式会社 | 植物病害防除組成物およびその用途 |
| BR112013001477A2 (pt) * | 2010-07-20 | 2016-05-31 | Bayer Ip Gmbh | isca de gel para o controle de insetos rastejantes prejudiciais |
| US8968757B2 (en) | 2010-10-12 | 2015-03-03 | Ecolab Usa Inc. | Highly wettable, water dispersible, granules including two pesticides |
| JP6457942B2 (ja) * | 2012-10-05 | 2019-01-23 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ｇｄｆ−８阻害剤 |
| BR112018077223A2 (pt) * | 2016-07-27 | 2019-04-09 | Basf Se | compostos de pirimidina, uso de compostos de pirimidina, composições herbicidas, método para controlar vegetação indesejada e uso das composições herbicidas |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146718A (en) * | 1978-04-10 | 1979-03-27 | Bristol-Myers Company | Alkyl 5,6-dichloro-3,4-dihydro-2(1h)-iminoquinazoline-3-acetate hydrohalides |
| DE2934543A1 (de) * | 1979-08-27 | 1981-04-02 | Basf Ag, 6700 Ludwigshafen | Substituierte n-benzoylanthranilsaeurederivate und deren anydroverbindungen, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| NO179282C (no) * | 1991-01-18 | 1996-09-11 | Rhone Poulenc Agrochimie | Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter |
| NL9202078A (nl) | 1992-11-30 | 1994-06-16 | Rijkslandbouwhogeschool | Nieuwe N-acyl-antranilzuurverbindingen en toepassing van N-acyl-antranilzuurverbindingen bij de bestrijding van insecten. |
| US5602126A (en) * | 1993-11-22 | 1997-02-11 | E. I. Du Pont De Nemours And Company | Arthropodicidal anilides |
| WO1995018116A1 (en) * | 1993-12-29 | 1995-07-06 | E.I. Du Pont De Nemours And Company | Arthropodicidal oxadiazine-, thiadiazine- or triazine-carboxanilides |
| DE4428380A1 (de) | 1994-08-11 | 1996-02-15 | Bayer Ag | 4-Trifluormethylbenzamide |
| WO1996038419A1 (en) | 1995-05-31 | 1996-12-05 | Nissan Chemical Industries, Ltd. | 5-pyrazolecarboxamide derivatives and plant disease control agent |
| TW515786B (en) | 1997-11-25 | 2003-01-01 | Nihon Nohyaku Co Ltd | Phthalic acid diamide derivatives, agricultural and horticultural insecticides, and a method for application of the insecticides |
| DE19840322A1 (de) | 1998-09-04 | 2000-03-09 | Bayer Ag | Pyrazol-carboxanilide |
| GT199900185A (es) * | 1998-11-06 | 2001-04-18 | Novedosa pirimidin-4-enamina como fungicida. | |
| PL351432A1 (en) * | 1999-04-15 | 2003-04-22 | Devgen Nv | Compound screening method |
| AR030154A1 (es) | 1999-07-05 | 2003-08-13 | Nihon Nohyaku Co Ltd | Derivado de ftalamida, derivado de amina heterociclico util como intermediario para la produccion del mismo, insecticida agrohorticola y metodo para utilizar dicho insecticida |
| WO2001032628A1 (en) | 1999-11-03 | 2001-05-10 | Bristol-Myers Squibb Pharma Company | Cyano compounds as factor xa inhibitors |
| MY138097A (en) | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
-
2002
- 2002-10-15 DE DE60230651T patent/DE60230651D1/de not_active Expired - Lifetime
- 2002-10-15 MX MXPA04003445A patent/MXPA04003445A/es not_active Application Discontinuation
- 2002-10-15 BR BR0213646-5A patent/BR0213646A/pt not_active Application Discontinuation
- 2002-10-15 JP JP2003535546A patent/JP4317752B2/ja not_active Expired - Fee Related
- 2002-10-15 AU AU2002343512A patent/AU2002343512B2/en not_active Ceased
- 2002-10-15 CN CNB028203585A patent/CN100503604C/zh not_active Expired - Fee Related
- 2002-10-15 EP EP02780457A patent/EP1435785B1/en not_active Expired - Lifetime
- 2002-10-15 WO PCT/US2002/032845 patent/WO2003032731A1/en not_active Ceased
- 2002-10-15 ES ES02780457T patent/ES2319972T3/es not_active Expired - Lifetime
- 2002-10-15 US US10/488,233 patent/US7148217B2/en not_active Expired - Fee Related
- 2002-10-15 KR KR1020047005481A patent/KR100840083B1/ko not_active Expired - Fee Related
- 2002-10-15 RU RU2004114856/04A patent/RU2298007C2/ru not_active IP Right Cessation
-
2006
- 2006-07-21 US US11/490,898 patent/US7326704B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| RU2004114856A (ru) | 2005-09-10 |
| CN1568144A (zh) | 2005-01-19 |
| US20040214828A1 (en) | 2004-10-28 |
| US20060258649A1 (en) | 2006-11-16 |
| EP1435785A1 (en) | 2004-07-14 |
| BR0213646A (pt) | 2004-08-24 |
| RU2298007C2 (ru) | 2007-04-27 |
| US7326704B2 (en) | 2008-02-05 |
| EP1435785B1 (en) | 2008-12-31 |
| KR100840083B1 (ko) | 2008-06-19 |
| DE60230651D1 (de) | 2009-02-12 |
| JP4317752B2 (ja) | 2009-08-19 |
| MXPA04003445A (es) | 2004-07-08 |
| JP2005506341A (ja) | 2005-03-03 |
| WO2003032731A1 (en) | 2003-04-24 |
| US7148217B2 (en) | 2006-12-12 |
| AU2002343512B2 (en) | 2007-12-06 |
| KR20050037476A (ko) | 2005-04-22 |
| CN100503604C (zh) | 2009-06-24 |
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