IE83260B1 - Synergistic herbicidal agents - Google Patents
Synergistic herbicidal agentsInfo
- Publication number
- IE83260B1 IE83260B1 IE1998/0064A IE980064A IE83260B1 IE 83260 B1 IE83260 B1 IE 83260B1 IE 1998/0064 A IE1998/0064 A IE 1998/0064A IE 980064 A IE980064 A IE 980064A IE 83260 B1 IE83260 B1 IE 83260B1
- Authority
- IE
- Ireland
- Prior art keywords
- salts
- composition
- methyl
- compound
- weight
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 23
- 230000002195 synergetic Effects 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 58
- 239000000126 substance Substances 0.000 claims description 53
- 241000196324 Embryophyta Species 0.000 claims description 28
- 230000002363 herbicidal Effects 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000011780 sodium chloride Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- -1 sulfonylureas (I) Chemical class 0.000 claims description 11
- 239000004562 water dispersible granule Substances 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 8
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 230000001276 controlling effect Effects 0.000 claims description 6
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 6
- 240000000218 Cannabis sativa Species 0.000 claims description 5
- 239000005507 Diflufenican Substances 0.000 claims description 5
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 claims description 5
- 239000000839 emulsion Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- IWEDIXLBFLAXBO-UHFFFAOYSA-N Dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 238000010410 dusting Methods 0.000 claims description 4
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 3
- MZHCENGPTKEIGP-UHFFFAOYSA-N Dichlorprop Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 claims description 3
- LLWADFLAOKUBDR-UHFFFAOYSA-N MCPB Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000005575 MCPB Substances 0.000 claims description 3
- WNTGYJSOUMFZEP-UHFFFAOYSA-N Mecoprop Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 3
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 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 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- VJYIFXVZLXQVHO-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims description 2
- 239000002794 2,4-DB Substances 0.000 claims description 2
- LOQQVLXUKHKNIA-UHFFFAOYSA-N 3-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]thiophene-2-carboxylic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 claims description 2
- NUFNQYOELLVIPL-UHFFFAOYSA-N Acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005496 Chlorsulfuron Substances 0.000 claims description 2
- 239000005504 Dicamba Substances 0.000 claims description 2
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 2
- YQVMVCCFZCMYQB-UHFFFAOYSA-N Flamprop Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 YQVMVCCFZCMYQB-UHFFFAOYSA-N 0.000 claims description 2
- BGZZWXTVIYUUEY-UHFFFAOYSA-N Fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 claims description 2
- KFEFNHNXZQYTEW-UHFFFAOYSA-N Imazamethabenz Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC(C)=CC=C1C(O)=O KFEFNHNXZQYTEW-UHFFFAOYSA-N 0.000 claims description 2
- CONWAEURSVPLRM-UHFFFAOYSA-N Lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 claims description 2
- 239000005574 MCPA Substances 0.000 claims description 2
- 239000005586 Nicosulfuron Substances 0.000 claims description 2
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 2
- 239000005624 Tralkoxydim Substances 0.000 claims description 2
- DQFPEYARZIQXRM-LTGZKZEYSA-N Tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 claims description 2
- 239000005626 Tribenuron Substances 0.000 claims description 2
- 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 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 101700021309 mcpB Proteins 0.000 claims description 2
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(N-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003094 microcapsule Substances 0.000 claims description 2
- 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 claims description 2
- JBDHZKLJNAIJNC-LLVKDONJSA-N prop-2-ynyl (2R)-2-[4-(5-chloro-3-fluoropyridin-2-yl)oxyphenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 claims description 2
- 239000011814 protection agent Substances 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 239000005506 Diclofop Substances 0.000 claims 1
- OOLBCHYXZDXLDS-UHFFFAOYSA-N Diclofop Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 claims 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N Diclofop methyl Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 claims 1
- 239000005590 Oxyfluorfen Substances 0.000 claims 1
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- 235000013339 cereals Nutrition 0.000 description 10
- 239000000306 component Substances 0.000 description 7
- 239000000575 pesticide Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 5
- 240000007842 Glycine max Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 241001148683 Zostera marina Species 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000003666 Amidosulfuron Substances 0.000 description 4
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- NEVDMPLXCGERDI-UHFFFAOYSA-N (4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(N)=O)=N1 NEVDMPLXCGERDI-UHFFFAOYSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 229960005069 Calcium Drugs 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 241000234646 Cyperaceae Species 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 241001233957 eudicotyledons Species 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000000749 insecticidal Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 1
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- WNTGYJSOUMFZEP-SSDOTTSWSA-N (R)-mecoprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-SSDOTTSWSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-D Substances 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-Dichlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- LBCZOTMMGHGTPH-UHFFFAOYSA-N 2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCO)C=C1 LBCZOTMMGHGTPH-UHFFFAOYSA-N 0.000 description 1
- QRYZQUDTXKBYAB-UHFFFAOYSA-N 2-[carbamoyl-(4,6-dimethoxypyrimidin-2-yl)sulfamoyl]-N,N-dimethylpyridine-3-carboxamide Chemical compound COC1=CC(OC)=NC(N(C(N)=O)S(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 QRYZQUDTXKBYAB-UHFFFAOYSA-N 0.000 description 1
- KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical compound NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-M 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-M 0.000 description 1
- 239000005484 Bifenox Substances 0.000 description 1
- 229960003563 Calcium Carbonate Drugs 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 description 1
- 235000019754 Grower Diet Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005576 Mecoprop-P Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N Nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- UCPWLHPWJKHSKR-UHFFFAOYSA-N OC=1C(CC(CC=1)C1=C(C=C(C=C1C)C)C)=O Chemical compound OC=1C(CC(CC=1)C1=C(C=C(C=C1C)C)C)=O UCPWLHPWJKHSKR-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- GPGLBXMQFQQXDV-UHFFFAOYSA-N Primisulfuron Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 GPGLBXMQFQQXDV-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M Sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 240000001016 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N Triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- HWKQNAWCHQMZHK-UHFFFAOYSA-N Trolnitrate Chemical compound [O-][N+](=O)OCCN(CCO[N+]([O-])=O)CCO[N+]([O-])=O HWKQNAWCHQMZHK-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000000274 adsorptive Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2R)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 230000000855 fungicidal Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000001338 necrotic Effects 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N o-Nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N p-acetaminophenol Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000002335 preservative Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 229910052904 quartz Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000002829 reduced Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
SYNERGISTIC HERBICIDAL AGENTS
HOECHST SCHERING AGREVO GMBH
-
The invention is in the field of the crop protection
agents which can be employed against nmnocotyledon and
dicotyledon weeds, in particular in the combinations of
herbicides.
The action of an individual herbicide used in acceptable
application rates is frequently insufficient for con-
trolling the spectrum of nwnocotyledon and dicotyledon
weeds which exists in agricultural practise. To allow
the grower to control the weed spectrum in cereals,
maize and other crops with one or a few application(s)
of herbicidal active substances, it is sometimes nmre
suitable to use combinations of a variety of active
substances. Synergistic combinations of amidosulfuron
(with fenoxaprop-ethyl, ioxynil and isoproturon) are
already part of the prior art (EP—A-298,901, EP-A-
l,677 and EP-A-401,678).
Further combinations of herbicides have now been found
whose action, surprisingly, exceeds the extent which
would have been expected taking into account the
individual action of the components. The combinations of
herbicides, according to the invention, therefore allow
a surprisingly’ great reduction in. application. rate of
each of the components.
therefore relates to herbicidal ‘com-
The invention
positions which comprise
A) a compound of the formula I or salts thereof
in combination with
B) diflufenican
in a synergistically active amount.
The compound of the formula (I) is known as
amidosulfuron and disclosed in EP—A-0,131,258 (US-A-
4,718,937).
Amidosulfuron is a. herbicidally’ active substance from
the group comprising the sulfonylureas and is generally
rice and
120 g of a.i./ha,
controlling a broad spectrum of annual and perennial
applied pre- and. post-emergence in cereals,
maize at application rates of 5 —
broad-leaf weeds and Cyperaceae (g of a.i./ha = gram per
hectare based on active ingredient). For use, the active
substance is generally formulated as a WP (water-soluble
powder) or WDG (water—dispersible granules) and employed
in the customary manner in the form of a dilution with
water.
N-(2,4—difluorophenyl)—2-[3-(tri-
is employed
Diflufenican, i.e.
fluoromethyl)phenoxy]pyridinecarboxamide,
pre- and post—emergence for controlling weeds in cereals
500 g of a.i./ha. It
is marketed mostly in the form of readymixes together
and other crops at a rate of 50 —
with other herbicidally active substances (cf. "The
Pesticide Manual", British Crop Protection Council, 9“
Edition 1991, and references cited therein.
In a further use form according to the invention, the
and B)
applied in combination with one or npre compounds from
the the growth-
regulator—type, nitrodiphenyl
herbicidal agents frown A) may additionally be
consisting of herbicides of
dicamba
group
and its salts,
ethers, sulfonylureas which differ from those of the
formula (1), and their salts and selective grass
herbicides.
Particularly ,suitable growth-regulator-type herbicides
are the following:
-
a) MCPB i.e. 4-(4—chloro-2—methylphenoxy)-
butanoic acid or salts thereof (for
example the sodium salt);
b) mecoprop i.e. 2-(4-chloro-2—methylphenoxy)-
propionic acid or salts thereof; in the
forn1 of a racemic mixture or as the
(R)—isomer (mecoprop-P);
‘ c) 2,4-D i.e. 2-(2,4—dichlorophenoxy)acetic acid
or salts thereof or esters thereof;
d) 2,4-DB i.e. 4-(2,4-dichlorophenoxy)butanoic
acid or salts thereof;
e) dichlorprop i.e. 2-(2,4-dichlorophenoxy)propionic
acid or salts thereof or esters there-
of,
f) MCPA i.e. 2-(4-chloro—2—methylphenoxy)acetic
acid or salts thereof.
The abovementioned compounds a) to f) represent standard
herbicides which are used post—emergence in a large
number of for controlling
broad-leaf weeds and Cyperaceae.
agriculturally used crops
Application rates of
100 - 3000 g of a.i./ha as individual active substances
cover in each case a specific sector of the weed flora.
The various compounds are used in the forms of the salts
"The Pesticide Manual",
th Edition 1991 and
and/or esters (references: cf.
British Crop Protection Council,
references cited therein).
Dicamba, i.e. 3,6—dichloro-2—methoxybenzoic acid (or the
salts thereof and esters thereof),
herbicidal active substance which is applied analogously
to the growth~regulator herbicides. The active substance
is also a widely used
is mainly used post—emergence (for example, inter alia,
in the forum of the
(cf. "The Pesticide
in cereals and maize), likewise
salts thereof and/or esters thereof
Manual", already mentioned above).
Particularly suitable nitrodiphenyl ethers are the
following:
'
a)
i.e. methyl
application rate 50 —
Bifenox, 5—(2,4-dichlorophenoxy)—
1000 g of
a.i./ha when used as single active substance pre-
—nitrobenzoate;
and post-emergence, for example in cereals, rice
and maize.
Fluorglycofen, i.e. carboxymethyl 5-[2-chloro-
-(trifluoromethyl)phenoxy]nitrobenzoate;
application as single active substance for example
only 5 - 50 g of a.i./ha pre- and post-emergence in
cereals and soya.
i.e.
Acifluorfen, 5-[2—chloro—4-(trifluoromethy1)-
phenoxy]nitrobenzoic acid or salts thereof;
application as single active substance for example
at a rate of 100 — 500 g of a.i./ha pre- and post-
emergence in soya and cereals.
i.e. 5-[2-chloro(trifluoromethyl)—
application as
dxyfluorfen,
phenoxy]ethoxynitrobenzene;
single active substance for example at a rate of
100 - 1000_g of a.i./ha pre- and post-emergence in
soya or on areas not under cultivation.
Lactofen, i.e. 1-(ethoxycarbonyl)ethy1 5-[2-chloro-
4-(trifluoromethyl)phenoxy]nitrobenzoate;
application as single active substance for example
at a rate of 50 - 500 g of a.i./ha pre- and post-
emergence in soya and cereals.
i.e. N—methylsulfonyl—5-[2-chloro~4-
(trifluoromethyl)phenoxy]nitrobenzamide;
Fomesafen,
application as single active substance for example
at a rate of 50 - 1000 g of a.i./ha pre- and post-
emergence in soya or cereals.
All of the ni;rophenyl ethers mentioned are described in
“The Pesticide Manual"
(already mentioned above).
<
_ 5 -
Particularly suitable sulfonylureas are the following:
sulfonylureas which are employed mainly in cereals,
in some cases in potatoes and in grassland for
post—emergence control of broad-leaf and grass
weeds (for example at a rate of 5 - 80 g of
agi./ha), for example
aa) triasulfuron, i.e. 1-[2-(2-chloroethoxy)-
phenylsulfonyl]—3-(4-methoxy—6—methy1-
1,3,5—triazinyl)—urea;
ab) chlorsulfuron, i.e. l—(2—chlorophenyl—
sulfonyl)(4—methoxy-6—methyl-1,3,5—triazin—
2-yl)-urea;
i.e.
ac) tribenuron or tribenuron-methyl, 1-[g-
(carboxy— or methoxycarbonyl)phenylsulfonyl]—
3-methyl(4-methoxy—6-methyl-1,3,5-triazin—
2-yl)-urea;
ad) thifensulfuron or thifensulfuron-methyl, i.e.
1-[2—(carboxy- or methoxycarbonyl)—thiophen
yl-su1fonyl](4—methoxy—6—methyl—1,3,5-
triazin—2-yl)-urea and
sulfonylureas which are employed. mainly in. maize
and perennial crops for post—emergence control of
grass and broad-leaf weeds (5 — 80 g of a.i./ha),
for example
ba) nicosulfuron, i.e. 1-[3-(dimethylamino-
carbonyl)—pyridin—2-yl—sulfonyl](4,6-
dimethoxypyrimidin—2—yl)-urea;
bb) primisulfuron or primisulfuron—methyl, i.e. 1-
[2-(carboxy- or methylcarbonyl)—pheny1—
su1fonyl][4,6-bis(difluoromethoxy)-
pyrimidinyl]-urea;
bc) DPX-E 9636,
-yl—sulfonyl]-3—(4,6-dimethoxypyrimid—2—yl)-
PCT Patent Application PCT/EP 90/023
(WO 91/10660) , those of the
formula A1 or salts thereof
preferably
i,
/ ‘ 3*
‘S _o_ o , ..=(
\ _5,-KH"|'L-8—<\ 1: (Al)
N O }z_( —
II
in which
E is CH or N, preferably CH,
R‘ is iodine or NR9R1°,
R5 is H, halogen, cyano, C1—C3—alkyl, C1—Cg—
alkoxy, C1-C3—haloalkyl, C1—C3—haloalkoxy,
C1-C3-alkylthio, (C1-C3—alkoxy) -C1-C3-alkyl,
(C1-C3-alkoxy)-carbonyl, mono- or di-(C1-C3'-
alkyl) -amino, C1-C3-alkyl-sulfinyl or
-sulfonyl, SO;-N'R°Rb or CO-NR“Rb, in
particular H,
R‘ and R”, independently of one another are H,
C1-C3-alkyl, C1-—C3—alkenyl, C1-C3-alkynyl, or
together are — (CH2) 4- , - (CH2) 5- or
-(C'H2)2'0“(C'H2)2'.
R‘ is H or CH3,
R7 is halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-
haloalkyl, preferably CF3, C1—C;—haloalkoxy,
preferably OCHF2 or OCHZCF3,
R8 is C1—C2—alkyl, C1-C2—haloalkoxy, preferably
OCHF2 or C1-C2-alkoxy, and
R9 is C1-C4-alkyl and R” is C1-C4-alkylsulfonyl,
The herbicides mentioned above under aa)
described in
above) .
or R9 and R”
formula ‘(CH2)3SO2" or -(CH-2)4SO;-.
together are a chain of the
to ba) are
"The Pesticide Manual" (already mentioned
-
_ 7 _
Primisulfuron and primisulfuron—methyl are known from
Brighton Crop Protection Conference - Weeds - 1987,
p. 41 - 48.
DPX-E 9636 is known from Brighton Crop Protection
Conference - Weeds - 1989, p. 33 et seq..
Suitable grass herbicides are mainly the following
herbicides for the selective post-emergence control of
harmful plants (grass weeds and broad-leaf weeds) in
dichlorophenoxy)phenoxy]propionic acid or its
methyl ester;
2-[1-(ethoxyimino)-propyl]
b) tralkoxydim, . i.e.
hydroxy-5—mesitylcyclohexen-l—one;
c) difenzoquat, i.e. 1,2-dimethyl-3,S-diphenyl-
pyrazolium salts;
d) imazamethabenz, i.e. a mixture of 6-(4—isopropyl
methyl-5—oxoimidazolin-2—yl)methyl—benzoic
acid and —4—methyl-benzoic acid or their methyl
esters;
e) flamprop or flamprop-methyl, i.e. N-benzoyl-N-(3-
chlorofluorophenyl)—alanine, or its methyl
ester; ‘
fluoropyridin—2-yloxy)-phenoxy]—propionate.
The last—mentioned compounds a) to e) are likewise des-
cribed in "The Pesticide Manual" (see above).
CGA—184927 is known from EP—A-191,736 and Brighton Crop
Protection Conference - Weeds — 1989.
Surprisingly, it has emerged that, when amidosulfuron
and the active compound B are used jointly, super-
additive (= synergistic) effects were observed. The
_ 3 _
activity in the combinations exceeded the activity of
These
effects allow the rate of application to be reduced, a
the individual products employed when used alone.
larger spectrum of broad-leaf and grass weeds to be
controlled, more rapid action, an extended long-term
action, complete control of the harmful plants with only
one or few applications, and an extended interval during
which the
combination. These properties are required in practical
active compounds may be applied in
weed control in order to keep agricultural crops free
from undesired competing plants and thus to guarantee,
and/or to increase, the yields in terms of quality and
quantity. These novel combinations markedly exceed the
prior art with a view to the above—described properties.
The choice of the ratio by weight and the applications
rates are a function of, for example, the other com-
ponent in the mixture, the development stage of the
broad-leaf weeds or grass weeds, the weed spectrum,
environmental factors and climatic conditions.
The ratios by weight A:B of the combined herbicides can
therefore vary within wide
1:200 to 20:1.
limits and are generally
The following ratios by weight are preferably used:
In the case of combinations of the compounds of the
formula (I) or salts thereof V
1:200 to 5:1,
1:50 to 2:1;
— with diflufenican: preferably
The application rates of the herbicide A in the active
substance combinations
100 g of a.i./ha (a.i. =
The application rates of compound B in the mixtures are
are preferably between 5 and
relative to active ingredient).
generally from 5 to 1000 g of a.i./ha, preferably
- with diflufenican 20 to 1000 g of a.i./ha,
The substance combinations according to the
invention can exist as mixed formulations of the two
active
components which are then applied in the customary
the fornx of a dilution. with water, or are
manner in
A prepared in the form of so—called tank mixes by jointly
diluting the separately formulated components with
water .
The A type and B type compounds or their combinations
can be formulated in many ways, depending on the
prevailing biological and/or chemicophysical parameters.
The following are possible exemplary formulations:
wettable powders (WP), emulsifiable concentrates (EC),
aqueous solutions (SL), emulsions (EW) such as oil—in-
water and water—in-oil emulsions, sprayable solutions or
emulsions, oil- or water-based dispersions, suspo—
emulsions, dusting jpowders (DP), seed-dressing agents,
granules for soil application or for broadcasting, or
water-dispersible granules (WG), ULV formulations,
microcapsules or waxes.
The individual formulation types are known in principle
and are described, for example, in: Winnacker-Kfichler,
"Chemische Technologie Volume 7,
[Chemical Technology]",
C. Hauser Verlag Munich, 4th Ed. 1986; van Valkenburg,
"Pesticides Formulations", Marcel Dekker N.Y., I973;
K. Martens, "Spray Drying Handbook", 3rd Ed. 1979,
G. Goodwin Ltd. London.
The formulation auxiliaries required such as inert
materials, surfactants, solvents and other additives are
equally known and are described, for example, in:
"Handbook of Insecticide Dust Diluents
Carriers", 2nd Ed., Darland Caldwell N.J.;
H.v. Olphen, "Introduction. to Clay’ Colloid. Chemistry";
2nd Ed., J. Wiley & N.Y.
Guide", 2nd Ed., N.Y.
"Detergents and Emulsifiers Annual",
Watkins, and
Books,
Marsden, "Solvents
1950;
MC Publ. Corp.,
Sons,
Interscience, McCutcheon's,
-
_ 10 _
Ridegewood N.J.; Sisley and Wood, "Encyclopedia of
Surface Active Egents", Chem. Publ. Co. N.Y. 1964;
Schonfeldt, Athylenoxidaddukte
[Surface—active Ethylene Oxide Adducts]", Wiss. Verlags-
Stuttgart 1976,
"Chemische Technologie_[Chemical Technology]", Volume 7,
C. Hauser Verlag Munich, 4th Ed. 1986.
Inc.,
"Grenzfléchenaktive
gesellschaft, Winnacker—Kfichler,
Based on these formulations, it is also possible to
prepare combinations with other pesticidally active
substances such as other herbicides, fungicides or
insecticides, as well as safeners, fertilizers and/or
growth regulators, for example in the form of a finished
formulation or a tank mix.
Wettable powders are preparations which can be dispersed
uniformly in water and which comprise, beside the active
substance, ionic or non-ionic surfactants (wetting
agents, dispersants), for example polyoxethylated alkyl-
phenols, polyethoxylated fatty alcohols or fatty amines,
fatty alcohol polyglycol ether sulfates, alkane-
sulfonates or Valkylbenzenesulfonates, sodium lignin-
sulfonate, sodium 2,2‘-dinaphthylmethane—6,6'—
disulfonate, sodium dibutylnaphthalenesulfonate or else
sodium oleoylmethyltaurinate, besides a diluent or inert
substance.
Emulsifiable concentrates are prepared by dissolving the
active substance in an organic solvent, for example
cyclohexanone, dimethylformamide, xylene, or
with the
addition of one or more ionic or non—ionic surfactants
butanol,
else higher-boiling aromatics or hydrocarbons,
(emulsifiers). The following are examples of emulsifiers
which can be used: calcium alkylarylsulfonates such as
calcium dodecylbenzenesulfonate, or non—ionic
emulsifiers such as fatty acid polyglycol esters,
alkylaryl polyglycol ethers, fatty alcohol polyglycol
ethers, propylene oxide/ethylene oxide condensation
products, alkyl polyethers, sorbitan fatty acid esters,
V
_ 11 -
polyoxyethylene sorbitan fatty acid esters or
polyoxethylene sorbitol esters.
Dusting powders are obtained by grinding, the active
substance with finely divided solid substances, for
example talc, natural clays such as kaolin, bentonite
and pyrophyllite, or diatomaceous earth.
Granules can be prepared either by spraying the active
substance onto adsorptive, granulated inert material or
by applying active substance concentrates to the surface
of carrier substances such as sand, kaolinites or granu-
lated inert material with the aid of adhesives, for
example polyvinyl alcohol, sodium polyacrylate or else
mineral oils. Suitable active substances can also be
granulated in the fashion customary for the preparation
of fertilizer granules, if desired in the form of a
Water—dispersible granules are
spray-drying,
disk granulation,
mixture with fertilizers.
generally prepared by methods such as
fluidized-bed granulation, mixing with
high—speed mixers and extrusion without solid inert
material.
As a rule, the agrochemical preparations comprise 0.1 to
99 percent by weight, in particular 2 to 95 % by weight,
of active substances of types A + B. The concentrations
of the .active substances A + B can differ in- the
formulations.
For example, the active substance concentration in
wettable powders is approximately 10 to 95 % by weight,
the remainder to 100 % by weight is composed of
customary formulation components. In the case of
emulsifiable concentrates, the active substance
concentration can be approximately 1 to 85 % by weight,
preferably 5 to 80 % by weight. Formulations in the form
of dusts comprise approximately’ 1 to 25 % by’ weight,
substance,
usually 5 to 20 % by weight, of active
sprayable solutions approximately 0.2 to 25 % by weight,
‘
preferably 2 to 20 % by weight, of active substance. In
the
active substance content depends partly on whether the
solid which
fillers The
content in the case of the water-dispersible granules is
the case of granules such as dispersible granules,
active compound is liquid or and on
granulation auxiliaries and are used.
generally between 10 and 90 % by weight.
substance formulations mentioned
the
emulsifiers,
the active
comprise
Besides,
optionally adhesives, wetting agents,
dispersants, penetrants, preservatives,
antifreeze agents and solvents, fillers, colorants and
carriers, defoamers, evaporation inhibitors, pH regu-
lators and viscosity regulators which are customary in
each case.
For‘ use, the formulations which exist in. commercially
available form are optionally diluted in the customary
manner, for example using water in the case of wettable
powders, emulsifiable concentrates, dispersions and
water-dispersible granules. Preparations in the form of
dusts, granules_for soil application or for broadcasting
as well as sprayable solutions are customarily not
diluted further with
application.
other inert substances before
The active substances can be applied to the plants,
parts of the plants, seeds of the plants or the area
under cultivation.
The active substances are preferably applied jointly in
the form of tank mixes, the optimally formulated con-
centrated formulations of the single active substances
being mixed concomitantly with water in the tank, and
the spray mixture obtained is applied.
The examples which follow are intended to illustrate the
invention:
‘
A.
a)
-13..
Formulation examples
A dusting agent is obtained by mixing 10 parts by
weight of an active substance combination according
to the invention and 90 parts by weight of talc as
inert substance and. comminuting the mixture in. a
hammer mill.
A wettable powder which is readily dispersible in
water is obtained by mixing 25 parts by weight of
active substances A + B, 64 parts by weight of
kaolin—containing quartz as inert substance,
parts by weight of potassium ligninsulfonate and
1 part by weight of sodium oleoylmethyltaurate as
and dispersing agent, .
wetting and grinding the
mixture in a pinned disk mill.
A dispersion concentrate which is readily disper-
sible in water is obtained by mixing 20 parts by
weight of active substances A + B with 6 parts by
weight of alkylphenol polyglycol ether (°Triton
X 207) ,
glycol
parts by’ weight of isotridecanol poly-
(8 E0)
paraffinic mineral oil
255 to 277°C),
a ball mill to a fineness of below 5 microns.
ether and 71 parts by weight of
(boiling range, for example,
approx. and grinding the mixture in
An enmlsifiable concentrate is obtained .from
parts by weight of cyclohexanone _as
solvent and 10 parts by weight of oxethylated nony-
lphenol as emulsifier.
Water—dispersible granules are obtained by mixing
75 parts by weight of active substances A + B,
parts by weight of calcium ligninsulfonate,
parts by weight of sodium lauryl sulfate,
3 parts by weight of polyvinyl alcohol and
7 parts,by weight of kaolin,
‘
_ 14 _
grinding the mixture on a pinned disk mill and
granulating the powder in a fluidized bed by spray-
ing on water as granulation liquid.
f) Alternatively, water-dispersible granules are
obtained by homogenizing and precomminuting
parts by weight of active substances A + B,
parts by weight of sodium 2,2‘-dinaphthyl—
methane~6,6'-disulfonate,
2 parts by weight of sodium oleoylmethyltaurate,
1 part by weight of polyvinyl alcohol,
17 parts by weight of calcium carbonate and
50 parts by weight of water
colloid mill,
mixture on a bead null,
on a subsequently grinding the
and atomizing and drying
the resulting suspension in a spray tower by means
of a single-substance nozzle.
B. Biological examples
broad—leaf
grass weeds had grown under natural field conditions
Various economically important weeds and
(field trials). The herbicide mixtures were applied in
the 2-
harmful plants by’ means of plot spray equipment.
to 5-leaf stage of the crop plants and the
The
water application rate was 300 - 400 liters of water per
hectare.
Within 4 weeks after the application, the herbicidal
activity of the treated plots was assessed by comparison
The
plant
with untreated control plots by visual scoring.
herbicidal the"
growth and chlorotic and necrotic effects up to the
total the
qualitatively and quantitatively
action as regards influencing
destruction of weeds was assessed
and indicated as
percentage action (0 — 100 %).
Examples show that only high dosage rates of the single
active substances allow good control of individual
substances allow good effects to be achieved on all test
individual
the
control level required is achieved by markedly lower
weed species. The additive action of the
components was markedly exceeded (synergism), i.e.
application rates. These effects broaden the spectrum of
action.
The crop tolerance, assessed in the form of damage, is
not adversely affected, i.e. the combinations can be
judged as fully selective.
Claims (1)
- Patent claims A herbicidal composition which comprises A) a compound of the formula I or salts thereof OCH . 3 R — OCH, in combination with B) diflufenican, in a synergistically active amount. which compounds A composition as claimed in claim 1, additionally comprises one or more selected from the group consisting of growth- regulator—type herbicides, and also dicamba and salts thereof, nitrodiphenyl ethers, sulfonylureas (I), and salts thereof, and selective grass herbicides. which differ from the urea of the formula A composition as claimed in claim 2, wherein.the growth—regulator-type herbicides are selected from 2,44D, also the group consisting of MCPB, 2,4-DB, MCPA, and nitrodiphenyl ethers from the group consisting of mecoprop, dichlorprop and lactofen and fomesafen, acifluorfen, oxyfluorfen, and also sulfonylureas from the group consisting of triasulfuorn, chlorsulfuron, tribenuron, tribenuron-methyl, thifensulfuron, thifensulfuron- methyl, nicosulfuron, pirimisulfuron, pirimisul- furon—methyl, DPX—E 9636 and pyridylsulfonylureas, and also grass herbicides from the group consisting of diclofop, diclofop—methyl, tralkoxydim, difenzoquat, imazamethabenz, flamprop, flamprop-methyl and CGA-184927. A composition as claimed in one of the preceding claims, which comprises the compound (I) or salts thereof and the compound B in a ratio by weight of 1:200 to 20:1. A composition as claimed in one of the preceding claims, which comprises, besides the active substances of type A or B, customary formulation auxiliaries. A process for the preparation of a synergistically active composition as claimed in one or more of claims 1 to 5, which comprises formulating the compound of the formula (I) or salts thereof with the B type compound analogously to a customary crop protection agent formulation selected from the group consisting of wettable powders, emulsifiable concentrates, aqueous solutions, emulsions, sprayable solutions (tank mix), oil— or water-based dispersions, suspoemulsions, dusting powders, seed-dressing agents, granules for soil application or for broadcasting, water-dispersible granules, ULV formulations, microcapsules and waxe S . A method of controlling undesired plants, which comprises applying a herbicidally effective amount of a combination. of active substances A -+ B as defined in one or more of claims 1 to 5, to these plants or to the area under cultivation. The method as claimed in claim 7, wherein the application rates of the compounds of the formula (I) or salts thereof are from 5 to 100 g/ha and the application rates of the compound B are from 5 to 1000 g/ha. The method as claimed in claim 7 or 8, wherein the active substances of types A and B are applied in a ratio by weight of 1:200 to 20:1. The use of a synergistically active composition as defined controlling undesired plant growth. in one or more of claims 1 to 5 for The use as claimed in claim 10, —wherein harmful plants in crops of useful plants are controlled selectively. A composition as claimed in claim 1, substantially as hereinbefore described and exemplified. F. R. KELLY & CO., AGENTS FOR THE APPLICANTS.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEGERMANY12/07/1991P4123111.2 | |||
DE4123111 | 1991-07-12 |
Publications (3)
Publication Number | Publication Date |
---|---|
IE980064A1 IE980064A1 (en) | 2000-02-23 |
IE19980064A1 IE19980064A1 (en) | 2003-03-05 |
IE83260B1 true IE83260B1 (en) | 2004-01-28 |
Family
ID=
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU650552B2 (en) | Synergistic herbicidal compositions | |
AU646560B2 (en) | Herbicidal compositions with increased crop safety | |
CN105165869B (en) | Synergistic herbicide compositions | |
US5599769A (en) | Synergistic herbicidal compositions comprising glyphosate or glufosinate in combination with a sulfonylurea herbicide | |
US5696051A (en) | Synergistic herbicide combinations | |
CA2096115C (en) | Synergistic herbicidal compositions | |
CN104273147B (en) | Synergistic herbicide compositions | |
IE83260B1 (en) | Synergistic herbicidal agents | |
IE83804B1 (en) | Synergistic herbicidal compositions | |
IE19980064A1 (en) | Synergistic herbicidal agents | |
CN104273150B (en) | Synergistic herbicide compositions | |
CN104273149B (en) | Synergistic herbicide compositions | |
CN104273148A (en) | Synergistic herbicide composition | |
CN104273151A (en) | Synergistic herbicide composition |