WO2004084631A1 - Verwendung von hydroxyaromaten als safener - Google Patents
Verwendung von hydroxyaromaten als safener Download PDFInfo
- Publication number
- WO2004084631A1 WO2004084631A1 PCT/EP2004/002797 EP2004002797W WO2004084631A1 WO 2004084631 A1 WO2004084631 A1 WO 2004084631A1 EP 2004002797 W EP2004002797 W EP 2004002797W WO 2004084631 A1 WO2004084631 A1 WO 2004084631A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbonyl
- alkyl
- radical
- formula
- alkoxy
- Prior art date
Links
- -1 aromatic hydroxy compounds Chemical class 0.000 title claims description 187
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 95
- 239000001257 hydrogen Substances 0.000 claims abstract description 95
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 239000000575 pesticide Substances 0.000 claims abstract description 38
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 35
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 35
- 125000002252 acyl group Chemical group 0.000 claims abstract description 12
- 230000000885 phytotoxic effect Effects 0.000 claims abstract description 12
- 239000003905 agrochemical Substances 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 239000000411 inducer Substances 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 134
- 125000000217 alkyl group Chemical group 0.000 claims description 133
- 125000003545 alkoxy group Chemical group 0.000 claims description 116
- 125000003282 alkyl amino group Chemical group 0.000 claims description 108
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 75
- 229910052736 halogen Inorganic materials 0.000 claims description 69
- 150000002367 halogens Chemical class 0.000 claims description 69
- 239000004009 herbicide Substances 0.000 claims description 56
- 125000001589 carboacyl group Chemical group 0.000 claims description 49
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 41
- 125000004414 alkyl thio group Chemical group 0.000 claims description 39
- 125000001188 haloalkyl group Chemical group 0.000 claims description 38
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 36
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 29
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 244000038559 crop plants Species 0.000 claims description 19
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 19
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 11
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 10
- 239000002917 insecticide Substances 0.000 claims description 10
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 9
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
- 239000000417 fungicide Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 5
- 239000005645 nematicide Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- 239000000642 acaricide Substances 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 230000007613 environmental effect Effects 0.000 claims description 4
- 231100000208 phytotoxic Toxicity 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 244000052769 pathogen Species 0.000 claims description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 239000004476 plant protection product Substances 0.000 claims 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 229910003827 NRaRb Inorganic materials 0.000 abstract 1
- 244000045561 useful plants Species 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 120
- 230000002363 herbicidal effect Effects 0.000 description 31
- 241000196324 Embryophyta Species 0.000 description 29
- 239000002253 acid Substances 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 11
- 240000008042 Zea mays Species 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000002689 soil Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000004043 oxo group Chemical group O=* 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000005560 Foramsulfuron Substances 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 239000005571 Isoxaflutole Substances 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 6
- 230000002349 favourable effect Effects 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 6
- 229940088649 isoxaflutole Drugs 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 239000005562 Glyphosate Substances 0.000 description 5
- 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 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229940100389 Sulfonylurea Drugs 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 235000007244 Zea mays Nutrition 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 4
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- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 4
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- 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 4
- 239000000243 solution Substances 0.000 description 4
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 4
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
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- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical compound 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 4
- XBYZOHTXPQOOJM-UHFFFAOYSA-N 1,2-oxazol-3-yl(phenyl)methanone Chemical class C=1C=CC=CC=1C(=O)C=1C=CON=1 XBYZOHTXPQOOJM-UHFFFAOYSA-N 0.000 description 3
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 3
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 description 3
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 3
- ZOGDSYNXUXQGHF-UHFFFAOYSA-N 5-(3-butanoyl-2,4,6-trimethylphenyl)-2-[(Z)-N-ethoxy-C-ethylcarbonimidoyl]-3-hydroxycyclohex-2-en-1-one Chemical compound C(C)ON=C(CC)/C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)C(CCC)=O)C)=O ZOGDSYNXUXQGHF-UHFFFAOYSA-N 0.000 description 3
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 3
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- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 3
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
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- DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 description 1
- GAIFAPDHLCPUMF-IWIPYMOSSA-N methyl 2-[(e)-[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxyacetate Chemical compound C1=C([N+]([O-])=O)C(C(=N\OCC(=O)OC)/COC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 GAIFAPDHLCPUMF-IWIPYMOSSA-N 0.000 description 1
- YGHJGQYNECSZDY-UHFFFAOYSA-N methyl 2-[4-(6-chloroquinoxalin-2-yl)oxyphenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 YGHJGQYNECSZDY-UHFFFAOYSA-N 0.000 description 1
- YWDFLVXKSADHHE-UHFFFAOYSA-N methyl 2-[4-(6-fluoroquinoxalin-2-yl)oxyphenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CN=C(C=C(F)C=C2)C2=N1 YWDFLVXKSADHHE-UHFFFAOYSA-N 0.000 description 1
- MDXGYOOITGBCBW-UHFFFAOYSA-N methyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 MDXGYOOITGBCBW-UHFFFAOYSA-N 0.000 description 1
- LYPWWQLKWQNQKV-UHFFFAOYSA-N methyl 2-[5-ethyl-2-[[4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(CC)=CC=C1COC1=CC=C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)C=C1 LYPWWQLKWQNQKV-UHFFFAOYSA-N 0.000 description 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
- ZVQSMXOVGFSOBT-UHFFFAOYSA-N methyl 3-(4,6-dimethoxypyrimidin-2-yl)oxypyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=C1OC1=NC(OC)=CC(OC)=N1 ZVQSMXOVGFSOBT-UHFFFAOYSA-N 0.000 description 1
- OESAUMRCEWQSAA-UHFFFAOYSA-N methyl 3-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylamino]thiophene-2-carboxylate Chemical compound S1C=CC(NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC OESAUMRCEWQSAA-UHFFFAOYSA-N 0.000 description 1
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 description 1
- DDDGRPLHUZOASC-UHFFFAOYSA-N methyl 5-[carbamoyl-(4,6-dimethylpyrimidin-2-yl)sulfamoyl]-1-pyridin-2-ylpyrazole-4-carboxylate Chemical compound COC(=O)C=1C=NN(C=2N=CC=CC=2)C=1S(=O)(=O)N(C(N)=O)C1=NC(C)=CC(C)=N1 DDDGRPLHUZOASC-UHFFFAOYSA-N 0.000 description 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
- MYURAHUSYDVWQA-UHFFFAOYSA-N methyl n'-(4-chlorophenyl)-n,n-dimethylcarbamimidate Chemical compound COC(N(C)C)=NC1=CC=C(Cl)C=C1 MYURAHUSYDVWQA-UHFFFAOYSA-N 0.000 description 1
- 229960002939 metizoline Drugs 0.000 description 1
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- LCGPAEGODAEUGN-UHFFFAOYSA-N n,n-diethyl-3-(2-ethyl-6-methylphenyl)sulfonyl-1,2,4-triazole-1-carboxamide Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC=CC=2C)CC)=N1 LCGPAEGODAEUGN-UHFFFAOYSA-N 0.000 description 1
- XESCSVABNVAQQS-UHFFFAOYSA-N n-(3-chloro-4-propan-2-ylphenyl)-2-methylpentanamide Chemical compound CCCC(C)C(=O)NC1=CC=C(C(C)C)C(Cl)=C1 XESCSVABNVAQQS-UHFFFAOYSA-N 0.000 description 1
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 description 1
- QTGVGIVRLSGTJJ-UHFFFAOYSA-N n-(acetamidomethyl)-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(CNC(C)=O)C(=O)CCl QTGVGIVRLSGTJJ-UHFFFAOYSA-N 0.000 description 1
- KGMBZDZHRAFLBY-UHFFFAOYSA-N n-(butoxymethyl)-n-(2-tert-butyl-6-methylphenyl)-2-chloroacetamide Chemical compound CCCCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(C)(C)C KGMBZDZHRAFLBY-UHFFFAOYSA-N 0.000 description 1
- LKVOXDJKFRBRQV-UHFFFAOYSA-N n-(dimethyl-$l^{4}-sulfanylidene)-4-(dipropylamino)-3,5-dinitrobenzenesulfonamide Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(=O)(=O)N=S(C)C)C=C1[N+]([O-])=O LKVOXDJKFRBRQV-UHFFFAOYSA-N 0.000 description 1
- IDFXUDGCYIGBDC-UHFFFAOYSA-N n-[4-ethylsulfanyl-2-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound CCSC1=CC=C(NS(C)(=O)=O)C(C(F)(F)F)=C1 IDFXUDGCYIGBDC-UHFFFAOYSA-N 0.000 description 1
- KDOKZLSGPVBDLS-UHFFFAOYSA-N n-[5-(1-chloro-2-methylpropan-2-yl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide Chemical compound S1C(C(C)(CCl)C)=NN=C1NC(=O)C1CC1 KDOKZLSGPVBDLS-UHFFFAOYSA-N 0.000 description 1
- DGPBHERUGBOSFZ-UHFFFAOYSA-N n-but-3-yn-2-yl-2-chloro-n-phenylacetamide Chemical compound C#CC(C)N(C(=O)CCl)C1=CC=CC=C1 DGPBHERUGBOSFZ-UHFFFAOYSA-N 0.000 description 1
- NMBXMBCZBXUXAM-UHFFFAOYSA-N n-butyl-1-dibutoxyphosphorylcyclohexan-1-amine Chemical compound CCCCOP(=O)(OCCCC)C1(NCCCC)CCCCC1 NMBXMBCZBXUXAM-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- BUCOQPHDYUOJSI-UHFFFAOYSA-N prohexadione Chemical compound CCC(=O)C1C(=O)CC(C(O)=O)CC1=O BUCOQPHDYUOJSI-UHFFFAOYSA-N 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
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- 238000001694 spray drying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
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- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
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- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 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
- 230000009261 transgenic effect Effects 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- VLCQZHSMCYCDJL-UHFFFAOYSA-N tribenuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 VLCQZHSMCYCDJL-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/55—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
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- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
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- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/90—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl and carboxyl groups
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- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
Definitions
- the present invention relates to the field of safeners or resistance inductors for protecting crop plants or useful plants from damage caused by the use of agrochemicals such as xenobiocides or biocides, for example herbicides, insecticides, acaricides, nematicides or fungicides, infection by pathogens such as fungi, bacteria, viruses or also occur due to harmful environmental factors such as drought or drought. More particularly, the invention relates to the novel use of certain hydroxyaromatic compounds as safeners and new compounds from this group.
- agrochemicals such as xenobiocides or biocides
- pathogens such as fungi, bacteria, viruses or also occur due to harmful environmental factors such as drought or drought.
- the invention relates to the novel use of certain hydroxyaromatic compounds as safeners and new compounds from this group.
- US-A-4,808,208 describes the use of phenols such as mono- or dihydroxy-acetophenone or hydroxycinnamic acids and some derivatives thereof Carboxylic acids as safeners for soybean crops against the phytotoxic effects of the herbicide glyphosate (phosphonomethylglycine and its salts).
- These phenols include known herbicides such as the hydroxybenzonitriles bromoxynil and loxynil and also analogs in which the nitrile group has been replaced by a carboxy, carbalkoxy or alkyl group.
- WO-A-92/11761 describes herbicide-biocide-antidote combinations, where the biocide can mean an insecticide, fungicide or nematicide and the antidotes are selected from the group of structurally different amides, generally including aromatic amides, in order to avoid " negative synergism "in the interaction of herbicide and biocide.
- the invention therefore relates to the use of aenes of the formula (I) or their salts,
- R 1 carboxy or a derivative of the carboxyl group, preferably a radical of the formula
- X is a divalent radical of the formula O, S or NR a or N-NR yes a nRb D , where R a and R b are as defined below,
- Y is a group of the formula O, S, NR c or NR c -NR d R e , where R c , R d and R e are as defined below,
- R is hydrogen or a hydrocarbon radical which is unsubstituted or substituted, or a heterocyclic radical which is unsubstituted or substituted, or acyl, and
- Hydrocarbon radical which is unsubstituted or substituted means each of the radicals B 1 , B 2 , B 3 , in each case independently of one another, is an acyl radical and each of the radicals C 1 , C 2 , C 3 , in each case independently of one another, is a heterocyclic radical, which is unsubstituted or substituted means, Z, Z ', Z ", in each case independently of one another, a group of the formula O, S (O) x or
- Hydrocarbon residue which is unsubstituted or substituted, or one
- Formula (I) also includes all stereoisomers of the compounds whose specific stereochemical configuration is not explicitly expressed by the formula, and their mixtures.
- Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not specified separately in the general formulas (I).
- the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods or else by stereoselective reactions in combination with the use of stereochemically pure starting materials are produced.
- the compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, such as, for example, HCl, HBr, H 2 SO or HNO 3 , but also oxalic acid or sulfonic acids, to a basic group, such as, for example, amino or alkylamino.
- a suitable substituents which are present in deprotonated form such as, for example, sulfonic acids or carboxylic acids, can form internal salts with groups which can in turn be protonated, such as amino groups.
- Salts can also be formed in that, in the case of suitable substituents, such as, for example, sulfonic acids or carboxylic acids, the hydrogen is replaced by a cation which is suitable for agriculture.
- salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts.
- metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts.
- a hydrocarbon radical is an aliphatic, cycloaliphatic or aromatic monocyclic or, in the case of an optionally substituted hydrocarbon radical, also a bicyclic or polycyclic organic radical based on the elements carbon and hydrogen, for example comprising the radicals alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl , Naphthyl, indanyl, indenyl, etc .; The same applies to the hydrocarbonoxy radicals.
- the hydrocarbon and hydrocarbonoxy radicals in the above definitions preferably have 1 to 20 C atoms, more preferably 1 to 16 C atoms, in particular 1 to 12 C atoms.
- hydrocarbon radicals and the more specific radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio as well as the corresponding unsaturated and / or substituted radicals can each be straight-chain or branched in the carbon skeleton.
- (-C-C) alkyl means a shorthand notation for open-chain alkyl having one to 4 carbon atoms, ie includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
- General alkyl radicals with a larger specified range of carbon atoms e.g. B.
- "(-C-C 6 ) alkyl” also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
- the lower carbon skeletons for example those having 1 to 6 carbon atoms or unsaturated groups having 2 to 6 carbon atoms, are preferred for the hydrocarbon radicals, such as alkyl, alkenyl and alkynyl radicals, even in composite radicals.
- Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl;
- Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals;
- Alkenyl means, for example, vinyl, allyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl, preferably allyl, 1-methylprop-2-en-1-
- (C 2 -C 6 ) -alkynyl means, for example, ethynyl, propargyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl or 2-hexynyl, preferably propargyl, but-2- in-1-yl, but-3-in-1-yl or 1-methyl-but-3-in-1-yl.
- Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
- substituents also having a double bond on the cycloalkyl radical, e.g. B. an alkylidene group such as methylidene are included.
- multi-cyclic aliphatic systems are also included, such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, Bicyclo [2.1.0] pentan-2-yl, BicyclIo [2.1.0] pentan-5-yl, adamantan-1-yl and adamantan-2-yl.
- Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl.
- substituted cycloalkenyl the explanations for substituted cycloalkyl apply accordingly.
- Halogen means, for example, fluorine, chlorine, bromine or iodine.
- Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF2O, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
- Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
- a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; unless otherwise defined, it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S; it is preferably an aliphatic heterocyclyl radical with 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms.
- the heterocyclic residue can e.g. be a heteroaromatic residue or ring (heteroaryl), e.g. a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms.
- heteroaromatic ring with a heteroatom from the group N, O and S for example pyridyl, pyrrolyl, thienyl or furyl; furthermore it is preferably a corresponding heteroaromatic ring with 2 or 3 heteroatoms, e.g. B. pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl and triazolyl.
- It is furthermore preferably a partially or completely hydrogenated heterocyclic radical having a hetero atom from the group N, O and S, for example oxiranyl, oxetanyl, oxolanyl ( tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl or piperidyl.
- a substituted heterocyclic radical having 2 heteroatoms from the group N, O and S, for example piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl.
- Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and additionally oxo.
- the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example in the case of N and S.
- Substituted radicals such as a substituted alkyl, alkenyl, alkynyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents for example one or more, preferably 1, 2 or 3 radicals from the group halogen, alkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and Alkylsulfinyl, alkylsulfonyl and, in the case of cyclic radicals, also alkyl, haloalkyl, alkylthioalkyl, alkoxyalkyl, optionally substituted mono- and dial
- cyclic systems are also included with those substituents which are bonded to the ring with a double bond, for. B. are substituted with an alkylidene group such as methylidene or ethylidene or an oxo group, imino group or substituted imino group.
- first substituent level can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
- second substituent level can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
- substituents mentioned by way of example can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
- second substituent level can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
- substituents mentioned by way of example can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined
- Preferred substituents for the substituent levels are, for example
- radicals with carbon atoms those with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
- Substituents from the group halogen for example fluorine and chlorine, (C 1 -C 4 ) alkyl, preferably methyl or ethyl, (CrC) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) alkoxy, preferably methoxy or ethoxy, are generally preferred, (C ⁇ -C 4 ) haloalkoxy, nitro and Cyano.
- the substituents methyl, methoxy, fluorine and chlorine are particularly preferred.
- Substituted amino such as mono- or disubstituted amino means a radical from the group of substituted amino radicals which are, for example, N-substituted by one or two identical or different radicals from the group alkyl, alkoxy, acyl and aryl; preferably mono- and dialkylamino, mono- and diarylamino, acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred;
- Aryl is preferably phenyl or substituted phenyl; the definition given below applies to acyl, preferably (-C-C 4 ) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
- Optionally substituted phenyl is preferably phenyl which is unsubstituted or one or more times, preferably up to three times, by identical or different radicals from the group halogen, (CrC) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl , (C- ⁇ -C) haloalkoxy and nitro is substituted, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and trichlorophenyl , 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
- Acyl means a residue of an organic acid which is formally formed by removing a hydroxyl group on the acid function, the organic residue in the acid also being able to be linked to the acid function via a hetero atom.
- Examples of acyl are the residue -CO-R of a carboxylic acid HO-CO-R and residues of acids derived therefrom such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the residue of carbonic acid monoesters, N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamic acids , Phosphonic acids, phosphinic acids.
- Acyl means, for example, formyl, alkylcarbonyl such as [(-CC 4 ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of organic Acids.
- alkylcarbonyl such as [(-CC 4 ) alkyl] carbonyl
- phenylcarbonyl alkyloxycarbonyl
- phenyloxycarbonyl benzyloxycarbonyl
- alkylsulfonyl alkylsulfinyl
- N-alkyl-1-iminoalkyl N-alkyl-1-iminoalkyl and other residues of organic Acids.
- radicals in the alkyl or phenyl part can be further substituted, for example in the alkyl part by one or more radicals from the group halogen, alkoxy, phenyl and phenoxy;
- substituents in the phenyl part are the substituents mentioned generally above for substituted phenyl.
- Acyl preferably means an acyl radical in the narrower sense, i.e. H. an organic acid residue in which the acid group is directly connected to the carbon atom of an organic residue, for example formyl, alkylcarbonyl such as acetyl or [(CrC) alkyl] carbonyl, phenylcarbonyl, alkylsulfonyl, alkylsulfinyl and other residues of organic acid
- R 1 denotes a nitrile group (-CN).
- R c , R d and R e are as defined below, and / or R is hydrogen, (C 8 -C 8 ) alkyl, (C 2 -C 18 ) alkenyl, (C 2 -C 18 ) alkynyl,
- Hetero ring atoms and a total of 5 or 6 ring atoms, which is bonded to the group C ( X) with an N hetero ring atom and which can also contain hetero atoms from the group N, O and S in addition to the N atom in the yl position as hetero ring atoms and the unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (dG 4 ) alkyl, (dC 4 ) alkoxy, (d- d) haloalkyl, (C ⁇ -C 4 ) haloalkoxy, (dC 4 ) alkylthio and oxo is substituted, where each of the radicals R a , R b , R c , R d and R e in the radicals X and Y is each independently and independently of the radical R as defined for R or a radical of the formula - OR *, where R * is independent of R as defined for R, and / or R 2
- C 4 ) alkyl (C 2 -C) alkenyl, (C 2 -C 4 ) alkynyl or (C 3 -C 6 ) cycloalkyl, each of the latter 4 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy , Amino, cyano, nitro, thiocyanato, (-C-C 4 ) alkoxy, (dC 4 ) haloalkoxy, (C ⁇ -C) alkylthio, (C ⁇ -C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyI, (CC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, mono (CrC 4 ) alkylamino, di (C ⁇ -C 4 ) alkylamino, (C ⁇ -C 4 ) alkanoyl, (dC
- X is a divalent radical of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below,
- Y is a group of the formula O, S, NR C or NR c -NR d R e , where R c , R d and R e are as defined below,
- R is hydrogen, (C 1 -C 2 ) alkyl, (C 2 -C 2 ) alkenyl, (C 2 -C 2 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkenyl, (C 3 -C 6 ) Cycloalkyl- (dC 4 ) alkyl, phenyl, phenyl- (C ⁇ -C) alkyl, heterocyclyl or heterocyclyl- (C ⁇ -C 4 ) alkyl, each of the latter 10 residues unsubstituted or by one or more residues from the Halogen, hydroxy group, (-C-C 4 ) alkoxy, (C ⁇ -C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (d- C 4 ) alkylthio, (CC 4 ) Al
- X is preferably a divalent radical of the formula O, S or NR a or N-NR a R b
- Y is a group of the formula O, S, NR C or NR c -NR d R e , preferably O or
- R is hydrogen, (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl,
- Heterocyclyl- (dC 4 ) alkyl where each of the latter 9 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (Cr C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, mono (dC 4 ) alkylamino, di (CrC 4 ) alkylamino, (C ⁇ -C 4 ) alkanoyl, (C ⁇ -C 4 ) haloalkanoyl, [(C ⁇ -C 4 ) alkoxy ] carbonyl and in the case of cyclic radicals also (-CC) alkyl and (-CC) haloalkyl is substituted, or (CrC 4 ) alkanoyl, (C ⁇ -C 4 ) haloalkan
- R 1 is a radical of the formula -CO-OR, wherein
- R is hydrogen, (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (C ⁇ -C 4 ) alkyl, phenyl, phenyl- (-C-C 4 ) alkyl, heterocyclyl or heterocyclyl- (dC 4 ) alkyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (C ⁇ -C 4 ) Alkoxy, (d- C 4 ) haloalkoxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, mono (dC 4 ) alkylamino, di (dC 4 ) alkylamino
- R is hydrogen, (dC 6 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, or (C 3 -C 6 ) cycloalkyl- (dC 4 ) alkyl, each of the latter 5 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (d-
- R 1 is very particularly a radical of the formula
- R (Ci-dJAlkyl means that is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (dC) alkoxy and (-C-C 4 ) alkylthio, and
- M + is a cation suitable for agriculture, preferably a cation equivalent of an alkali metal or alkaline earth metal, in particular a sodium ion or potassium ion, or also an optionally substituted ammonium ion, preferably NH 4 + or ammonium ions of organic amines or quaternary (quaternary) ammonium ions.
- R 1 carboxyl and salts thereof, methoxycarbonyl, ethoxycarbonyl, n-
- R 1 preferably also denotes a radical of the formula
- R and R a are as defined above, preferably
- Heterocyclyl- (-C-C 4 ) alkyl each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (CrC 4 ) alkoxy, (d- C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (C 1 -C) alkylsulfonyl,
- R a is hydrogen or, independently of one another, as defined above, or preferably the radical R is
- R 1 methoxy-acetiminocarbonyl, ethoxy-acetiminocarbonyl, n-propoxy-acetiminocarbonyl, isopropoxy-acetiminocarbonyl, (2-hydroxy-ethoxy) - acetiminocarbonyl, acetoxy-iminocarbonyl, acetoxy-methyliminocarbonyl, acetoxy-ethyliminocarbonyl, acetoxy-acetiminocarbonyl.
- R 1 preferably also denotes a radical of the formula -CO-NR c R, in which R and R c are as defined above, preferably R is hydrogen, (CC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (dC 4 ) alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, heterocyclyl or Heterocyclyl- (dC 4 ) alkyl, each of the latter 9 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (Cr C 4 ) haloalkoxy, (C 1 -C 4 ) alkyIthio, (-C-C 4 ) alkylsulfinyl,
- R c is hydrogen or, independently of one another, as defined above or preferably the radical R is
- R c is hydrogen, (dC 4 ) alkyl, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (dC 4 ) alkoxy and (C ⁇ -C 4 ) alkylthio, or
- R 1 aminocarbonyl, N-methylaminocarbonyl, N-ethylaminocarbonyl, N- (n-propyl) aminocarbonyl, N-isopropylaminocarbonyl, N-butylaminocarbonyl, N- (2-hydroxyethyl) aminocarbonyl, N-cycopropylaminocarbonyl, N-acetylaminocarbonyl , N-propionylaminocarbonyl, N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N-ethyl-N-methyl- aminocarbonyl, N-acetyl-N-methylaminocarbonyl.
- R 2 and R 6 each independently of the other, hydrogen, halogen, (C ⁇ -d) alkyl, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, (dC 4 ) alkoxy, (CC 4 ) haloalkoxy, (dd ) AIkyithio, (dC 4 ) alkylsulfinyl, (dG 4 ) alkylsulfonyI, (C ⁇ -C 4 ) haloalkylsulfinyl, (C ⁇ -C 4 ) haloalkylsulfonyl, mono (C ⁇ -C) aIkyIamino, di (C ⁇ -C 4 ) alkyIamino, (C ⁇ -C 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(CC) alkoxy] carbonyl, [(C ⁇ -C 4 ) haloalkoxy] carbonyl
- R 2 and R 6 are hydrogen, halogen, (-C-C) alkyl, (dC 4 ) hydroxyalkyl or (dC 4 ) haloalkyl.
- R 3 (a) in the case n 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 1 or B 1 or
- each of the radicals A 1 , A 2 , A 3 is hydrogen, (d- C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl or (C 3 -C 6 ) cycloalkyl, each of the latter 4 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, (CrC) alkoxy, (Cr C 4 ) haloalkoxy, (dC 4 ) alkylthio, (CC
- R 1 to R 5 have the meaning given and the radicals R 3 , R 4 and R 5 which are bonded to the oxygen atoms shown are each hydrogen or an acyl radical according to B 1 , B 2 or B 3 , preferably at least one of the oxygen bound radicals mean hydrogen.
- the compounds of formula (I) can be prepared by derivatizing the hydroxybenzoates and their carboxyl derivatives as base compounds by conventional methods, e.g. B. acylated or etherified.
- the invention also relates to the method for protecting crops or useful plants from phytotoxic effects of agrochemicals, such as pesticides, or from environmental factors which cause damage to plants, characterized in that compounds of the formula (I) or their salts are used as safeners or Applies resistance inductors, preferably an effective amount of the compounds of formula (I) or their salts applied to the plants, parts of the plants or seeds or seeds thereof.
- the safeners are suitable, together with active ingredients (pesticides) for the selective control of harmful organisms in a number of plant crops, for example in economically important crops such as cereals (wheat, barley, triticale, rye, rice, corn, millet), sugar beet, sugar cane, rape , Cotton and soy.
- cereals wheat, barley, triticale, rye, rice, corn, millet
- sugar beet sugar cane
- rape cotton and soy.
- Cotton Of particular interest is the use in monocot crops such as cereals (wheat, barley, rye, triticale, sorghum), including maize and rice, and monocot vegetable crops, but also in dicot crops such as soybean, rapeseed, cotton, wine, vegetables, Fruit plants and ornamental plants.
- Partially tolerant mutant cultures or partially tolerant transgenic cultures of interest are also of interest here, e.g. B.
- corn crops is resistant to glufosinate or glyphosate, or soybean cultures which is resistant to herbicidal imidazolinones.
- the particular advantage of the new safeners is their effective action in crops that are normally not tolerant of the pesticides mentioned.
- the compounds of the formula (I) according to the invention can be applied together with the pesticides at the same time or in any order with the active compounds and are then able to reduce or completely eliminate harmful side effects of these active compounds in crop plants, without the effectiveness of these active compounds against undesired ones Harm harmful organisms or significantly reduce them. Damage caused by the use of several pesticides, e.g. by several herbicides or by herbicides in combination with insecticides or fungicides, can be significantly reduced or completely eliminated. This allows the area of application of conventional pesticides to be expanded considerably.
- these agents are applied after appropriate dilution either directly to the area under cultivation, to the already germinated harmful and / or useful plants or to the already emerged harmful and / or useful plants.
- these agents can be used in the so-called tank mix process - i.e.
- the advantageous effects of the compounds (I) according to the invention are observed if they are used together with the pesticides in the pre-emergence or in the post-emergence, for example with simultaneous application as a tank mix or as a co-formulation or with a separate application in parallel or in succession (split Application). It is also possible to repeat the application several times. Sometimes it can make sense to combine a pre-emergence application with a post-emergence application. Usually, the application is a post-emergence application to the crop or crop with simultaneous or later application of the pesticide.
- the use of the compounds (I) according to the invention in seed dressing, the (immersion) treatment of seedlings or the treatment of other propagation material (for example potato tubers) is also suitable.
- the agents according to the invention can contain one or more pesticides.
- suitable pesticides are herbicides, insecticides, fungicides, acaricides and nematicides which, if used alone, would result in phytotoxic damage to the crop plants or in which damage would be likely.
- Corresponding pesticidal active substances from the groups of herbicides, insecticides, acaricides, nematicides and fungicides, in particular herbicides, are of particular interest.
- the weight ratio of safener to pesticide can be varied within wide limits and is generally in the range from 1: 100 to 100: 1, preferably 1:20 to 20: 1, in particular 1:10 to 10: 1.
- the optimal weight ratio of safener to pesticide depends both on the safener used and the particular pesticide as well as on the type of crop or crop to be protected.
- the required amount of safener can be used depending on the pesticide and type the crop to be protected can be varied within wide limits and is generally in the range from 0.001 to 10 kg, preferably 0.005 to 5 kg, in particular 0.1 to 1 kg of safener per hectare.
- seed dressing for example 0.005 to 20 g of safener per kilogram of seed, preferably 0.01 to 10 g of safener per kilogram of seed, in particular 0.05 to 5 g of safener per kg of seed, are used.
- the suitable concentration is generally in the range from 1 to 10000 ppm, preferably 100 to 1000 ppm, based on the weight.
- the quantities and weight ratios required for successful treatment can be determined by simple preliminary tests.
- the safeners can be formulated in the customary manner separately or together with the pesticides.
- the subject is therefore also the crop or crop protection agents.
- Insecticides that can cause plant damage alone or together with herbicides include the following:
- Organophosphates e.g. Terbufos (Counter ® ), Fonofos (Dyfonate ® ), Phorate
- Pyrethroid insecticides such as tefluthrin (Force ® ), deltamethrin (Decis ® ) and
- Herbicides the phytotoxic side effects on crop plants of which can be reduced by means of compounds of the formula I, can be of very different structural classes and have very different mechanisms of action. Preference is given to commercially available herbicides, as described, for example, in the manual “The Pesticide Manual", 13th Edition 2003, The British Crop Protection Council and the e-Pesticide Manual Version 3 (2003) or also in the names are also referred to in the "Comp ⁇ ndium of Pesticide Common Names" (available on the Internet) and the literature cited there.
- active substances whose phytotoxic effect on crops and crop plants can be reduced by the compounds (I) according to the invention are: acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie [[[[1 - [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidenes] amino] oxy] acetic acid and its methyl ester; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid, amitrol; AMS, ie ammonium sulfamate; anilof
- Herbicides whose phytotoxic side effects on crop plants can be reduced by means of compounds of the formula I are e.g. Herbicides from the group of carbamates, thiocarbamates, haloacetanilides, substituted phenoxy, naphthoxy and phenoxyphenoxycarboxylic acid derivatives as well as heteroaryloxyphenoxyalkanecarboxylic acid derivatives, such as quinolyloxy, quinoxalyloxy, pyridyloxy, benzoxazolyloxycarboxy and benzoxyalkoxy benzoxy , benzoylcyclohexanediones, benzoylisoxazoles, benzoylpyrazoles, imidazolinones, pyrimidinyloxy-pyridine carboxylic acid derivatives, pyrimidyloxy benzoic acid derivatives, sulfonylureas, sulphonylaminocarbonyltriazolinones, triazolo-pyrim
- Phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts Phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts, cyclohexanedione oximes, benzoylcyclohexanediones, benzoylisoxazoles, sulfonylureas, sulfonylaminocarbonyltriazolinones, imidazolinones and mixtures of the active ingredients mentioned with one another and / or with active ingredients which are used, for example, to expand the spectrum of active ingredients, are used to broaden the spectrum of active ingredients. Bentazone, Cyanazine, Atrazine, Bromoxynil, Dicamba and other leaf herbicides.
- Suitable herbicides which can be combined with the safeners according to the invention are, for example: A) Herbicides of the phenoxyphenoxy and
- Phenoxyphenoxy and benzyloxyphenoxy carboxylic acid derivatives e.g. 2- (4-
- TriazinylaminocarbonyI- [benzene, pyridine, pyrazole, thiophene and (alkylsulfonyl) alkylamino] sulfamides. Preferred as a substituent on the pyrimidine ring or
- Triazine rings are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or dimethylamino, where all substituents can be combined independently of one another.
- Substituents in the benzene, pyridine, pyrazole, thiophene or (alkylsulfonyl) alkylamino part are alkyl, alkoxy, halogen, nitro, alkoxycarbonyl, aminocarbonyl,
- Alkylaminocarbonyl dialkylaminocarbonyl, alkoxyaminocarbonyl, haloalkoxy
- Haloalkyl alkylcarbonyl, alkoxyalkyl, (alkanesulfonyl) alkylamino.
- alkanesulfonyl alkylamino.
- alkoxyphenoxysulfonylureas e.g. B.
- Acetochlor alachlor, butachlor, dimethachlor, dimethenamid, metazachlor, metolachlor, S-metolachlor, pethoxamide, pretilachlor, propachlor, propisochlor and thenylchlor;
- thiocarbamates e.g. S-ethyl-N, N-dipropylthiocarbamate (EPTC), S-ethyl-N, N-diisobutylthiocarbamate (butylates),
- Imazamethabenz-methyl imazapic, imazamox, imazapyr, imazaquin and imazethapyr;
- M phosphinic acids and derivatives, e.g. B.
- N glycine derivatives, e.g. B.
- S- (N-aryl-N-alkyl-carbamoylmethyl) dithiophosphonic acid esters such as S- [N- (4-
- R pyridinecarboxylic acids, e.g. B. Clopyralid, Fluroxypyr, Picloram and Triciopyr;
- T) pyridinecarboxamides e.g. B. Diflufenican and Picolinafen;
- V Plant growth regulators, e.g. B. Forchlorfenuron and thidiazuron.
- herbicides of groups A to V are known, for example, from the publications mentioned above and from "The Pesticide Manual", The British Crop Protection Council, 13th Edition, 2003, or the e-Pesticide Manual, Version 3.0, British Crop Protection Council 2003 ,
- Emulsifiable concentrates which are obtained by dissolving the active ingredients in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
- emulsifiers are, for example, alkylarylsulfonic acid calcium salts, fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters and polyoxyethylene sorbitan fatty acid esters;
- Dusts which are obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, diatomaceous earth or flours can be obtained.
- suspension concentrates based on water or oil which can be prepared, for example, by wet grinding using bead mills; water soluble powder; water soluble concentrates;
- Granules such as water-soluble granules, water-dispersible granules and granules for spreading and soil application;
- Wettable powders which, in addition to the active substance, also contain diluents or inert substances and surfactants;
- the crop protection agents can optionally include customary adhesives, wetting agents, dispersants, penetrants, emulsifiers, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH or the like Contain viscosity-influencing agents.
- the crop protection agents generally contain 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the general formula I or a combination of safener and pesticide. They also contain 1 to 99.9, in particular 4 to 99.5% by weight of one or more solid or liquid additives and 0 to 25, in particular 0.1 to 25% by weight of a surfactant.
- the active substance concentration in emulsifiable concentrates is the concentration of safener and / or pesticide, usually 1 to 90, in particular 5 to 80 wt .-%. Dusts usually contain 1 to 30, preferably 5 to 20% by weight of active ingredient.
- the active substance concentration in wettable powders is generally 10 to 90% by weight.
- the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
- the formulations present in commercial form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable Concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, granules and sprayable solutions are usually no longer diluted with other inert substances before use.
- the application rate of the safener varies with the external conditions, such as temperature, humidity, the type of herbicide used and others.
- n-butyl n-Bu n-butyl
- Seeds of various crops and weeds were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam.
- the herbicides and the safeners in the form of liquid (e.g. emulsion concentrates) or dry (e.g. water-dispersible powders) formulations were diluted to the required concentrations with deionized water and applied to the soil surface using a spray sled using a water application rate of 300 liters per hectare.
- the safeners were used as 20 percent water-dispersible powders, the herbicide isoxaflutole as an aqueous suspension concentrate (see Table 1.1.1).
- the pots were placed in a greenhouse under favorable growing conditions.
- Herbicide H1 Isoxaflutole
- Verb. 1272 3,5-Dimethoxy-4-hydroxybenzoic acid (see Tab. 1)
- Verb. 1050 3,5-Dihydroxybenzoic acid (see Tab. 1)
- Seeds of various crops and weeds were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam.
- the pots were placed in a greenhouse under favorable growth conditions over a period of about two to three weeks so that the plants reached a growth stage of 2 to 4 leaves.
- the herbicides in the form of liquid (e.g. emulsion concentrates) or dry (e.g.
- water-dispersible powder formulations were mixed with a standard additive (based on rapeseed oil methyl ester), diluted to the required concentrations with deionized water and sprayed on using a water application rate of 300 liters per hectare the green parts of the plant and applied to the uncovered part of the soil surface.
- a standard additive based on rapeseed oil methyl ester
- the safeners and the herbicide foramsulfuron were each used as 20 percent water-dispersible powder (for results see Table 1.2.1).
- the pots were placed in a greenhouse under favorable growing conditions.
- Herbicide H2 Foramsulfuron
- Verb. 1272 3,5-Dimethoxy-4-hydroxybenzoic acid (see Tab. 1)
- Verb. 1050 3,5-Dihydroxybenzoic acid (see Tab. 1)
- the number of crop seeds required for each safener application rate was calculated. Sufficient seeds were weighed into screw-top glass bottles. The glass bottles had almost twice the volume of the weighed seeds. The safeners were formulated as 20 percent water dispersible powders. These formulations were weighed out so that the required application rates (g ai / kg seed) were achieved. The samples were added to the seeds in the glass containers, then enough water was added to form a suitable dressing liquid. The glass bottles were sealed and then placed in an overhead shaker (which rotated the bottles at medium speed for up to an hour) so that the seeds were evenly coated with the dressing liquid. The bottles were opened and the seed could be used in pre-emergence or post-emergence experiments as described below.
- the seeds treated with safener and untreated seeds as controls were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam.
- the herbicides in the form of liquid (e.g. emulsion concentrates) or dry (e.g. water-dispersible powders) formulations were diluted to the required concentrations with deionized water and applied to the soil surface using a spraying carriage using a water application rate of 300 liters per hectare.
- the herbicide isoxaflutole was used as an aqueous suspension concentrate.
- Verb. 1050 3,5-Dihydroxybenzoic acid (see Tab. 1)
- ZEAMA Zea mays (maize), variety 'Lorenzo' GLXMA Glycine max (soybean), variety 'Lambert' B2.3) Post-emergence application of herbicides after seed dressing with safener
- the seeds treated with safener and untreated seeds were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam.
- the pots were placed in a greenhouse under favorable growth conditions over a period of about two to three weeks so that the plants reached a growth stage of 2 to 4 leaves.
- the herbicides in the form of liquid (e.g. emulsion concentrates) or dry (e.g.
- water-dispersible powder formulations were mixed with a standard additive (based on rapeseed oil methyl ester), diluted to the required concentrations with deionized water and with a spraying carriage using a water application rate of 300 liters per hectare applied to the green parts of the plant and to the uncovered part of the soil surface.
- a standard additive based on rapeseed oil methyl ester
- the herbicide foramsulfuron was used as a 20 percent water-dispersible powder (for results see Table 2.3.1).
- the pots were placed in a greenhouse under favorable growing conditions.
- Herbicide H2 Foramsulfuron
- Verb. 1272 3,5-Dimethoxy-4-hydroxybenzoic acid (see Tab. 1)
- Verb. 1050 3,5-Dihydroxybenzoic acid (see Tab. 1)
Abstract
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002520228A CA2520228A1 (en) | 2003-03-26 | 2004-03-18 | Use of aromatic compounds as safeners |
AU2004224813A AU2004224813B2 (en) | 2003-03-26 | 2004-03-18 | Use of aromatic hydroxy compounds as safeners |
EA200501466A EA014910B1 (ru) | 2003-03-26 | 2004-03-18 | Применение гидроксиароматических соединений в качестве защитных веществ для культурных и полезных растений, способ защиты полезных и культурных растений от фитотоксических побочных воздействий агрохимикатов и средство защиты растений на их основе |
BRPI0408943-0A BRPI0408943A (pt) | 2003-03-26 | 2004-03-18 | aplicação de compostos hidroxiaromáticos como antìdotos |
JP2006504717A JP2006521311A (ja) | 2003-03-26 | 2004-03-18 | 芳香族ヒドロキシ化合物の薬害軽減剤としての使用 |
MXPA05010296A MXPA05010296A (es) | 2003-03-26 | 2004-03-18 | Utilizacion de compuestos hidroxilicos aromaticos como antidotos. |
YUP-2005/0691A RS20050691A (en) | 2003-03-26 | 2004-03-18 | Use of aromatic hydroxy compounds as safeners |
CN2004800079696A CN1764374B (zh) | 2003-03-26 | 2004-03-18 | 芳族羟基化合物用作安全剂的用途 |
EP04721478A EP1610611A1 (de) | 2003-03-26 | 2004-03-18 | Verwendung von hydroxyaromaten als safener |
HR20050844A HRP20050844A2 (en) | 2003-03-26 | 2005-09-23 | Use of aromatic hydroxy compunds as safeners |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10313480.8 | 2003-03-26 | ||
DE10313480 | 2003-03-26 |
Publications (1)
Publication Number | Publication Date |
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WO2004084631A1 true WO2004084631A1 (de) | 2004-10-07 |
Family
ID=33038768
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/002797 WO2004084631A1 (de) | 2003-03-26 | 2004-03-18 | Verwendung von hydroxyaromaten als safener |
Country Status (17)
Country | Link |
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US (1) | US20040224844A1 (de) |
EP (1) | EP1610611A1 (de) |
JP (1) | JP2006521311A (de) |
KR (1) | KR20060002857A (de) |
CN (1) | CN1764374B (de) |
AR (1) | AR043770A1 (de) |
AU (1) | AU2004224813B2 (de) |
BR (1) | BRPI0408943A (de) |
CA (1) | CA2520228A1 (de) |
EA (1) | EA014910B1 (de) |
HR (1) | HRP20050844A2 (de) |
MX (1) | MXPA05010296A (de) |
RS (1) | RS20050691A (de) |
TW (1) | TW200505334A (de) |
UA (1) | UA90844C2 (de) |
WO (1) | WO2004084631A1 (de) |
ZA (1) | ZA200506657B (de) |
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ZA200506657B (en) | 2007-01-31 |
AR043770A1 (es) | 2005-08-10 |
CN1764374B (zh) | 2010-09-22 |
BRPI0408943A (pt) | 2006-04-04 |
AU2004224813A1 (en) | 2004-10-07 |
KR20060002857A (ko) | 2006-01-09 |
JP2006521311A (ja) | 2006-09-21 |
UA90844C2 (ru) | 2010-06-10 |
EA014910B1 (ru) | 2011-02-28 |
EA200501466A1 (ru) | 2006-04-28 |
TW200505334A (en) | 2005-02-16 |
HRP20050844A2 (en) | 2006-11-30 |
US20040224844A1 (en) | 2004-11-11 |
CA2520228A1 (en) | 2004-10-07 |
EP1610611A1 (de) | 2006-01-04 |
CN1764374A (zh) | 2006-04-26 |
RS20050691A (en) | 2008-04-04 |
AU2004224813B2 (en) | 2010-11-25 |
MXPA05010296A (es) | 2005-11-17 |
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