AU2005226870B2 - Herbicide-safener combination - Google Patents
Herbicide-safener combination Download PDFInfo
- Publication number
- AU2005226870B2 AU2005226870B2 AU2005226870A AU2005226870A AU2005226870B2 AU 2005226870 B2 AU2005226870 B2 AU 2005226870B2 AU 2005226870 A AU2005226870 A AU 2005226870A AU 2005226870 A AU2005226870 A AU 2005226870A AU 2005226870 B2 AU2005226870 B2 AU 2005226870B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- halogen
- hydrogen
- alkoxy
- ill
- 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.)
- Ceased
Links
- -1 akynyl Chemical group 0.000 claims description 121
- 150000001875 compounds Chemical class 0.000 claims description 104
- 239000001257 hydrogen Substances 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 229910052736 halogen Inorganic materials 0.000 claims description 74
- 150000002367 halogens Chemical class 0.000 claims description 73
- 239000004009 herbicide Substances 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 244000038559 crop plants Species 0.000 claims description 25
- 230000002363 herbicidal effect Effects 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 230000009261 transgenic effect Effects 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 12
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 11
- YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims description 11
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 8
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 8
- UKSLKNUCVPZQCQ-UHFFFAOYSA-N Fluxofenim Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)=NOCC1OCCO1 UKSLKNUCVPZQCQ-UHFFFAOYSA-N 0.000 claims description 8
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- XXWNKVBJDWSYBN-UHFFFAOYSA-N diethoxy-phenoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=CC=CC=C1 XXWNKVBJDWSYBN-UHFFFAOYSA-N 0.000 claims description 7
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 7
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 0.000 claims description 7
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 235000013311 vegetables Nutrition 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 238000009395 breeding Methods 0.000 claims 1
- 230000001488 breeding effect Effects 0.000 claims 1
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 146
- 150000003254 radicals Chemical class 0.000 description 77
- 241000196324 Embryophyta Species 0.000 description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 69
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 50
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 46
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 33
- 239000000460 chlorine Chemical group 0.000 description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 20
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 17
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 11
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
- 230000001276 controlling effect Effects 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 235000010469 Glycine max Nutrition 0.000 description 10
- 244000068988 Glycine max Species 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 235000013339 cereals Nutrition 0.000 description 9
- 235000005822 corn Nutrition 0.000 description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 7
- 244000075850 Avena orientalis Species 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 235000007319 Avena orientalis Nutrition 0.000 description 6
- 240000002791 Brassica napus Species 0.000 description 6
- 235000006008 Brassica napus var napus Nutrition 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 244000062793 Sorghum vulgare Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 6
- 125000006413 ring segment Chemical group 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 5
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 244000299507 Gossypium hirsutum Species 0.000 description 5
- 235000007238 Secale cereale Nutrition 0.000 description 5
- 244000082988 Secale cereale Species 0.000 description 5
- 235000021536 Sugar beet Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000019713 millet Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- WMMQJAQJAPXWDO-UHFFFAOYSA-N (4-chlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=C(Cl)C=C1 WMMQJAQJAPXWDO-UHFFFAOYSA-N 0.000 description 4
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 4
- 239000002794 2,4-DB Substances 0.000 description 4
- OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 description 4
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 4
- 239000005562 Glyphosate Substances 0.000 description 4
- 101150081923 IL4 gene Proteins 0.000 description 4
- 239000005586 Nicosulfuron Substances 0.000 description 4
- 239000005616 Rimsulfuron Substances 0.000 description 4
- 240000000111 Saccharum officinarum Species 0.000 description 4
- 235000007201 Saccharum officinarum Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011814 protection agent Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 3
- MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 description 3
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 3
- 239000005504 Dicamba Substances 0.000 description 3
- 239000005561 Glufosinate Substances 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 235000003222 Helianthus annuus Nutrition 0.000 description 3
- 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 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 239000005574 MCPA Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000219843 Pisum Species 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 240000003461 Setaria viridis Species 0.000 description 3
- 235000002248 Setaria viridis Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000000729 antidote Substances 0.000 description 3
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 3
- 229940097068 glyphosate Drugs 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 125000000262 haloalkenyl group Chemical group 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- 125000002950 monocyclic group Chemical group 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SJWOCKTZFQIKHZ-UHFFFAOYSA-N (1-ethoxy-1-oxopropan-2-yl) 3,6-dichloro-2-methoxybenzoate Chemical compound CCOC(=O)C(C)OC(=O)C1=C(Cl)C=CC(Cl)=C1OC SJWOCKTZFQIKHZ-UHFFFAOYSA-N 0.000 description 2
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 2
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 description 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- PYKLUAIDKVVEOS-RAXLEYEMSA-N (e)-n-(cyanomethoxy)benzenecarboximidoyl cyanide Chemical compound N#CCO\N=C(\C#N)C1=CC=CC=C1 PYKLUAIDKVVEOS-RAXLEYEMSA-N 0.000 description 2
- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 description 2
- DYPQUENOGZXOGE-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)C1=CC=C(Cl)C=C1 DYPQUENOGZXOGE-UHFFFAOYSA-N 0.000 description 2
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 2
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- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004015140.7 | 2004-03-27 | ||
| DE102004015140 | 2004-03-27 | ||
| DE102004031345.8 | 2004-06-30 | ||
| DE102004031345 | 2004-06-30 | ||
| PCT/EP2005/002672 WO2005092103A1 (de) | 2004-03-27 | 2005-03-12 | Herbizid-safener-kombination |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2005226870A1 AU2005226870A1 (en) | 2005-10-06 |
| AU2005226870B2 true AU2005226870B2 (en) | 2010-06-10 |
Family
ID=34962868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005226870A Ceased AU2005226870B2 (en) | 2004-03-27 | 2005-03-12 | Herbicide-safener combination |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7563749B2 (https=) |
| EP (1) | EP1732391B1 (https=) |
| JP (1) | JP2007530473A (https=) |
| KR (1) | KR20060131926A (https=) |
| AR (1) | AR050143A1 (https=) |
| AT (1) | ATE442044T1 (https=) |
| AU (1) | AU2005226870B2 (https=) |
| BR (1) | BRPI0509289A (https=) |
| CA (1) | CA2560908A1 (https=) |
| CR (1) | CR8557A (https=) |
| DE (1) | DE502005008105D1 (https=) |
| EA (1) | EA011892B1 (https=) |
| ES (1) | ES2329592T3 (https=) |
| IL (1) | IL178033A0 (https=) |
| PL (1) | PL1732391T3 (https=) |
| PT (1) | PT1732391E (https=) |
| UA (1) | UA84201C2 (https=) |
| WO (1) | WO2005092103A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA011812B1 (ru) * | 2004-03-27 | 2009-06-30 | Байер Кропсайенс Аг | Комбинация гербицидов |
| EP1728430A1 (de) * | 2005-06-04 | 2006-12-06 | Bayer CropScience GmbH | Herbizide Mittel |
| US7951995B2 (en) | 2006-06-28 | 2011-05-31 | Pioneer Hi-Bred International, Inc. | Soybean event 3560.4.3.5 and compositions and methods for the identification and detection thereof |
| BR122017006111B8 (pt) | 2006-10-31 | 2022-12-06 | Du Pont | Métodos para controlar ervas daninhas |
| EP2145537A1 (en) * | 2008-07-09 | 2010-01-20 | Bayer CropScience AG | Plant growth regulator |
| AU2010209649B2 (en) * | 2009-02-02 | 2015-01-22 | Basf Se | Herbicidal compositions comprising naptalam |
| EP2255637A1 (en) * | 2009-05-02 | 2010-12-01 | Bayer CropScience AG | Method for weed control in lawn or turf |
| BR112012029397B1 (pt) * | 2010-05-17 | 2018-08-28 | Nufarm Australia Ltd | processo para a preparação de sais de amina sólidos de herbicidas à base de ácido carboxílico aromático substituído |
| CN103237894A (zh) | 2010-08-13 | 2013-08-07 | 先锋国际良种公司 | 包含具有羟基苯丙酮酸双加氧酶(hppd)活性的序列的组合物和方法 |
| WO2012071039A1 (en) | 2010-11-24 | 2012-05-31 | Pioner Hi-Bred International, Inc. | Brassica gat event dp-061061-7 and compositions and methods for the identification and/or detection thereof |
| WO2012071040A1 (en) | 2010-11-24 | 2012-05-31 | Pioneer Hi-Bred International, Inc. | Brassica gat event dp-073496-4 and compositions and methods for the identification and/or detection thereof |
| TWI667347B (zh) | 2010-12-15 | 2019-08-01 | 瑞士商先正達合夥公司 | 大豆品種ｓｙｈｔ０ｈ２及偵測其之組合物及方法 |
| US9247735B2 (en) * | 2011-01-19 | 2016-02-02 | Rotam Agrochem International Company Limited | Crop plant-compatible herbicidal compositions containing herbicides and safeners |
| CA2848622A1 (en) * | 2011-09-16 | 2013-03-21 | Bayer Intellectual Property Gmbh | Use of 5-phenyl- or 5-benzyl-2-isoxazoline-3-carboxylates for improving plant yield |
| WO2013188291A2 (en) | 2012-06-15 | 2013-12-19 | E. I. Du Pont De Nemours And Company | Methods and compositions involving als variants with native substrate preference |
| CA2894213A1 (en) | 2012-12-21 | 2014-06-26 | Pioneer Hi-Bred International, Inc. | Compositions and methods for auxin-analog conjugation |
| WO2014159306A1 (en) | 2013-03-13 | 2014-10-02 | Pioneer Hi-Bred International, Inc. | Glyphosate application for weed control in brassica |
| BR112015023286A2 (pt) | 2013-03-14 | 2018-03-06 | Arzeda Corp | polipeptídeo recombinante com atividade da dicamba descarboxilase, construto de polinucleotídeo, célula, método de produção de uma célula hospedeira compreendendo um polinucleotídeo heterólogo que codifica um polipeptídeo tendo atividade da dicamba descarboxilase, método para descarboxilar dicamba, um derivado de dicamba ou um metabolito de dicamba, método para a detecção de um polipeptideo e método para a detecção da presença de um polinucleotideo que codifica um polipeptideo tendo atividade da dicamba descarboxilase |
| AU2014236154A1 (en) | 2013-03-14 | 2015-09-17 | Pioneer Hi-Bred International, Inc. | Compositions having dicamba decarboxylase activity and methods of use |
| US10329578B2 (en) | 2013-10-18 | 2019-06-25 | Pioneer Hi-Bred International, Inc. | Glyphosate-N-acetyltransferase (GLYAT) sequences and methods of use |
| WO2018029104A1 (de) | 2016-08-11 | 2018-02-15 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazolinylderivate, verfahren zu deren herstellung und ihre verwendung als herbizide und/oder pflanzenwachstumsregulatoren |
| GB2555462B (en) * | 2016-10-31 | 2021-07-07 | Rotam Agrochem Int Co Ltd | Herbicidal composition comprising mesotrione |
| WO2025015330A2 (en) * | 2023-07-13 | 2025-01-16 | The Board Of Trustees Of The University Of Arkansas | Enhancing tolerance of rice to bleaching herbicides with a fenclorim seed treatment |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4323122A1 (de) * | 1993-07-10 | 1995-01-12 | Hoechst Schering Agrevo Gmbh | Mischungen aus Herbiziden und Antidots |
| US5476936A (en) * | 1993-09-27 | 1995-12-19 | Bayer Aktiengesellschaft | N-azinyl-N'-(het)arylsulphonyl-ureas |
| EP1008297A2 (de) * | 1990-12-21 | 2000-06-14 | Aventis CropScience GmbH | Mischungen aus Herbiziden und Antidots |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4137070A (en) | 1971-04-16 | 1979-01-30 | Stauffer Chemical Company | Herbicide compositions |
| US4021224A (en) | 1971-12-09 | 1977-05-03 | Stauffer Chemical Company | Herbicide compositions |
| US4021229A (en) | 1972-09-05 | 1977-05-03 | Stauffer Chemical Company | Sulfonamide herbicide antidote compositions and method of use |
| MA19709A1 (fr) | 1982-02-17 | 1983-10-01 | Ciba Geigy Ag | Application de derives de quinoleine a la protection des plantes cultivees . |
| ATE103902T1 (de) | 1982-05-07 | 1994-04-15 | Ciba Geigy Ag | Verwendung von chinolinderivaten zum schuetzen von kulturpflanzen. |
| MX159669A (es) | 1983-12-12 | 1989-08-02 | Ciba Geigy Ag | Procedimiento para la preparacion de derivados de acilamida |
| US4601745A (en) | 1983-12-12 | 1986-07-22 | Ciba-Geigy Corporation | Composition for the protection of cultivated plants against the phytotoxic action of herbicides |
| DE3525205A1 (de) | 1984-09-11 | 1986-03-20 | Hoechst Ag, 6230 Frankfurt | Pflanzenschuetzende mittel auf basis von 1,2,4-triazolderivaten sowie neue derivate des 1,2,4-triazols |
| EP0191736B1 (de) | 1985-02-14 | 1991-07-17 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| DE3633840A1 (de) | 1986-10-04 | 1988-04-14 | Hoechst Ag | Phenylpyrazolcarbonsaeurederivate, ihre herstellung und verwendung als pflanzenwachstumsregulatoren und safener |
| DE3808896A1 (de) | 1988-03-17 | 1989-09-28 | Hoechst Ag | Pflanzenschuetzende mittel auf basis von pyrazolcarbonsaeurederivaten |
| DE3817192A1 (de) | 1988-05-20 | 1989-11-30 | Hoechst Ag | 1,2,4-triazolderivate enthaltende pflanzenschuetzende mittel sowie neue derivate des 1,2,4-triazols |
| US5215570A (en) | 1988-10-20 | 1993-06-01 | Ciba-Geigy Corporation | Sulfamoylphenylureas |
| ES2054088T3 (es) | 1988-10-20 | 1994-08-01 | Ciba Geigy Ag | Sulfamoilfenilureas. |
| DE3939010A1 (de) | 1989-11-25 | 1991-05-29 | Hoechst Ag | Isoxazoline, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschuetzende mittel |
| DE3939503A1 (de) | 1989-11-30 | 1991-06-06 | Hoechst Ag | Neue pyrazoline zum schutz von kulturpflanzen gegenueber herbiziden |
| US5700758A (en) | 1989-11-30 | 1997-12-23 | Hoechst Aktiengesellschaft | Pyrazolines for protecting crop plants against herbicides |
| EP0492366B1 (de) | 1990-12-21 | 1997-03-26 | Hoechst Schering AgrEvo GmbH | Neue 5-Chlorchinolin-8-oxyalkancarbonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Antidots von Herbiziden |
| TW259690B (https=) | 1992-08-01 | 1995-10-11 | Hoechst Ag | |
| DE4331448A1 (de) | 1993-09-16 | 1995-03-23 | Hoechst Schering Agrevo Gmbh | Substituierte Isoxazoline, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung als Safener |
| DE19621522A1 (de) | 1996-05-29 | 1997-12-04 | Hoechst Schering Agrevo Gmbh | Neue N-Acylsulfonamide, neue Mischungen aus Herbiziden und Antidots und deren Verwendung |
| DE19742951A1 (de) | 1997-09-29 | 1999-04-15 | Hoechst Schering Agrevo Gmbh | Acylsulfamoylbenzoesäureamide, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung |
| AR031027A1 (es) | 2000-10-23 | 2003-09-03 | Syngenta Participations Ag | Composiciones agroquimicas |
| BR0206859A (pt) * | 2001-01-31 | 2004-01-13 | Bayer Cropscience Gmbh | Método para proteger colheitas empregando carboxilatos de isoxazolina |
-
2005
- 2005-03-12 BR BRPI0509289-2A patent/BRPI0509289A/pt not_active IP Right Cessation
- 2005-03-12 UA UAA200611344A patent/UA84201C2/ru unknown
- 2005-03-12 WO PCT/EP2005/002672 patent/WO2005092103A1/de not_active Ceased
- 2005-03-12 EA EA200601704A patent/EA011892B1/ru not_active IP Right Cessation
- 2005-03-12 JP JP2007504300A patent/JP2007530473A/ja active Pending
- 2005-03-12 PT PT05716020T patent/PT1732391E/pt unknown
- 2005-03-12 ES ES05716020T patent/ES2329592T3/es not_active Expired - Lifetime
- 2005-03-12 DE DE502005008105T patent/DE502005008105D1/de not_active Expired - Lifetime
- 2005-03-12 KR KR1020067020021A patent/KR20060131926A/ko not_active Ceased
- 2005-03-12 EP EP05716020A patent/EP1732391B1/de not_active Expired - Lifetime
- 2005-03-12 CA CA002560908A patent/CA2560908A1/en not_active Abandoned
- 2005-03-12 AU AU2005226870A patent/AU2005226870B2/en not_active Ceased
- 2005-03-12 AT AT05716020T patent/ATE442044T1/de active
- 2005-03-12 PL PL05716020T patent/PL1732391T3/pl unknown
- 2005-03-23 AR ARP050101172A patent/AR050143A1/es not_active Application Discontinuation
- 2005-03-25 US US11/090,985 patent/US7563749B2/en not_active Expired - Fee Related
-
2006
- 2006-08-11 CR CR8557A patent/CR8557A/es not_active Application Discontinuation
- 2006-09-12 IL IL178033A patent/IL178033A0/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1008297A2 (de) * | 1990-12-21 | 2000-06-14 | Aventis CropScience GmbH | Mischungen aus Herbiziden und Antidots |
| DE4323122A1 (de) * | 1993-07-10 | 1995-01-12 | Hoechst Schering Agrevo Gmbh | Mischungen aus Herbiziden und Antidots |
| US5476936A (en) * | 1993-09-27 | 1995-12-19 | Bayer Aktiengesellschaft | N-azinyl-N'-(het)arylsulphonyl-ureas |
Also Published As
| Publication number | Publication date |
|---|---|
| PL1732391T3 (pl) | 2010-02-26 |
| AU2005226870A1 (en) | 2005-10-06 |
| IL178033A0 (en) | 2006-12-31 |
| EP1732391A1 (de) | 2006-12-20 |
| UA84201C2 (en) | 2008-09-25 |
| US7563749B2 (en) | 2009-07-21 |
| CR8557A (es) | 2008-02-28 |
| DE502005008105D1 (de) | 2009-10-22 |
| EA011892B1 (ru) | 2009-06-30 |
| PT1732391E (pt) | 2009-11-18 |
| KR20060131926A (ko) | 2006-12-20 |
| BRPI0509289A (pt) | 2007-09-18 |
| ES2329592T3 (es) | 2009-11-27 |
| EP1732391B1 (de) | 2009-09-09 |
| EA200601704A1 (ru) | 2007-02-27 |
| US20050233904A1 (en) | 2005-10-20 |
| WO2005092103A1 (de) | 2005-10-06 |
| AR050143A1 (es) | 2006-10-04 |
| CA2560908A1 (en) | 2005-10-06 |
| JP2007530473A (ja) | 2007-11-01 |
| ATE442044T1 (de) | 2009-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: BAYER CROPSCIENCE AG Free format text: FORMER APPLICANT(S): BAYER CROPSCIENCE GMBH |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |