IL29368A - Synergistic herbicidal compositions containing a 2-methylthio-1,3,5-triazine and a benzimidazole - Google Patents
Synergistic herbicidal compositions containing a 2-methylthio-1,3,5-triazine and a benzimidazoleInfo
- Publication number
- IL29368A IL29368A IL2936868A IL2936868A IL29368A IL 29368 A IL29368 A IL 29368A IL 2936868 A IL2936868 A IL 2936868A IL 2936868 A IL2936868 A IL 2936868A IL 29368 A IL29368 A IL 29368A
- Authority
- IL
- Israel
- Prior art keywords
- benzimidazole
- triazine
- substituted
- herbicidal composition
- trifluoromethyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 56
- 230000002363 herbicidal effect Effects 0.000 title claims description 29
- 230000002195 synergetic effect Effects 0.000 title claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims 5
- WOPHAXVWACNHPM-UHFFFAOYSA-N 2-(methylthio)-1,3,5-triazine Chemical compound CSC1=NC=NC=N1 WOPHAXVWACNHPM-UHFFFAOYSA-N 0.000 title 1
- 150000001556 benzimidazoles Chemical class 0.000 claims description 23
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 18
- 241000196324 Embryophyta Species 0.000 claims description 14
- -1 cyano, thiocyano, isothiocyano Chemical group 0.000 claims description 11
- VWPQFAPZLPFZDE-UHFFFAOYSA-N 6-iodo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(I)C=C2NC(C(F)(F)F)=NC2=C1 VWPQFAPZLPFZDE-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical group 0.000 claims description 8
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- KSROTSBULDYPKA-UHFFFAOYSA-N 4,5-dichloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound ClC1=CC=C2NC(C(F)(F)F)=NC2=C1Cl KSROTSBULDYPKA-UHFFFAOYSA-N 0.000 claims description 5
- 239000005574 MCPA Substances 0.000 claims description 5
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- QFJPFTPJLNGMHU-UHFFFAOYSA-N 4,5,6-trichloro-2-(1,1,2,2,2-pentafluoroethyl)-1H-benzimidazole Chemical compound ClC1=C(C(=CC=2N=C(NC21)C(C(F)(F)F)(F)F)Cl)Cl QFJPFTPJLNGMHU-UHFFFAOYSA-N 0.000 claims description 2
- FTDIVRFRWTWDKU-UHFFFAOYSA-N 4,5,7-trichloro-6-methyl-2-(trifluoromethyl)-1h-benzimidazole Chemical compound CC1=C(Cl)C(Cl)=C2N=C(C(F)(F)F)NC2=C1Cl FTDIVRFRWTWDKU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- PMISAFNVEGVLSS-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzimidazole-5-carbonitrile Chemical compound C1=C(C#N)C=C2NC(C(F)(F)F)=NC2=C1 PMISAFNVEGVLSS-UHFFFAOYSA-N 0.000 claims 1
- YVUODVQNPODCDR-UHFFFAOYSA-N 4,5,6,7-tetrachloro-1-methyl-2-(trifluoromethyl)benzimidazole Chemical compound CN1C(=NC2=C1C(=C(C(=C2Cl)Cl)Cl)Cl)C(F)(F)F YVUODVQNPODCDR-UHFFFAOYSA-N 0.000 claims 1
- BXCSXZJKEJQDKS-UHFFFAOYSA-N 4,5,6-trichloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound ClC1=C(Cl)C=C2NC(C(F)(F)F)=NC2=C1Cl BXCSXZJKEJQDKS-UHFFFAOYSA-N 0.000 claims 1
- JEOWEMPCQGMUDQ-UHFFFAOYSA-N 6-nitro-2-(1,1,2,2,2-pentafluoroethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC=C2N=C(C(F)(F)C(F)(F)F)NC2=C1 JEOWEMPCQGMUDQ-UHFFFAOYSA-N 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- 240000006694 Stellaria media Species 0.000 description 3
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- 244000144786 Chrysanthemum segetum Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241001289540 Fallopia convolvulus Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- 244000110797 Polygonum persicaria Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 241000407417 Veronica agrestis Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- LQTBGSYRMUUKKB-UHFFFAOYSA-N 3,3-dichloro-2-phenoxybutanoic acid Chemical compound ClC(C(C(=O)O)OC1=CC=CC=C1)(C)Cl LQTBGSYRMUUKKB-UHFFFAOYSA-N 0.000 description 1
- QLKDMIUEWFNEPV-UHFFFAOYSA-N 4,5,6,7-Tetrachloro-2-trifluoromethylbenzimidazole Chemical compound ClC1=C(Cl)C(Cl)=C2NC(C(F)(F)F)=NC2=C1Cl QLKDMIUEWFNEPV-UHFFFAOYSA-N 0.000 description 1
- KUMDVKHIEVZRRL-UHFFFAOYSA-N 4,5,6-trifluoro-2-methyl-1h-benzimidazole Chemical compound FC1=C(F)C(F)=C2NC(C)=NC2=C1 KUMDVKHIEVZRRL-UHFFFAOYSA-N 0.000 description 1
- WUDKQPQAAUQCLT-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1Cl WUDKQPQAAUQCLT-UHFFFAOYSA-N 0.000 description 1
- STOJWTVNHAJLBI-UHFFFAOYSA-N 6-chloro-4-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(Cl)=CC2=C1N=C(C(F)(F)F)N2 STOJWTVNHAJLBI-UHFFFAOYSA-N 0.000 description 1
- KMFHVMJKOGJJRE-UHFFFAOYSA-N 7-bromo-4,5,6-trichloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound ClC1=C(Cl)C(Br)=C2NC(C(F)(F)F)=NC2=C1Cl KMFHVMJKOGJJRE-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000007639 Anthemis cotula Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- 241000283014 Dama Species 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 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 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- NOKCSEDYJVNSDP-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCCCCCCC[Na] NOKCSEDYJVNSDP-UHFFFAOYSA-N 0.000 description 1
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 235000004442 Polygonum persicaria Nutrition 0.000 description 1
- NWQXYQUFNNDNES-UHFFFAOYSA-N S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)[Na] Chemical compound S(=O)(=O)(O)O.C(CCCCCCCCCCCCCCC)[Na] NWQXYQUFNNDNES-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 235000005545 Veronica americana Nutrition 0.000 description 1
- 240000005592 Veronica officinalis Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- JNSGIVNNHKGGRU-JYRVWZFOSA-N diethoxyphosphinothioyl (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOP(=S)(OCC)OC(=O)C(=N/OC)\C1=CSC(N)=N1 JNSGIVNNHKGGRU-JYRVWZFOSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
SynergistiG herbicidal compositions containing a 2«.methylthio-lf3 jS-triazine and a bensimidazole FISGKS PEST CONTROL LIMITED C:27812 The present invention relatee to novel compositions of matter particularly suitable for the selective control of weeds.
It has been found that the selective herbicidal compositions hereinafter described possesses exceptional activity for the selective control of certain¾«eds in certain crops'*" owing to the mutual synergistic effect of its two active ingredients indicated below.
Accordingly the present invention is for synergistic selective herbicidal compositions comprising a mixture of a triazine of the general 1 3 4 where R , R , R and R are hydrogen, alkyl or alkoxyalkyl groups, together with at least one substituted benzimidazole of the formula; where R** is hydrogen, a lower alkyl group or -COOR10 where ^ is optionally halogen-substituted lower alkyl, optionally alkyl-substitute a 6 7^ R8 9 aryl or cycloalkyl group; and R , R and R are the same or different and are each hydrogen, an optionally halogen-, hydroxy-or alkoxy-substituted alkyl, hydroxy, alkoxy, nitro, halogen, cyano, thiocyano, isothiocyanOj azido, carboxy, alkoxyearbonyl, carbamoyl, K-mono or Ν,Ν-disubstituted carbamo¾ amino mono- or disubstituted by alkyl, acyl or halogen-substituted acyi; mercapto, alkylthio, alkyl- - 3a - 29368/2 The substituted benzimidazoles identified above are active herbicides, and have been described for example in Israel Patent Specification ϊίο* 20714. " : Examples of these substituted benzimidazoles which may be mentioned include: 4,5, 6,7-tetrachloro-2-trifluoromethylbenzimidazole, 4.5.6-trichloro-2-trifluoromethylbenzimidazole, 4.5.7-trichloro-2-trifluoromethylbenzimidazole, 4.5-dichloro-2-trifluoromethylbenzimidazole, -iodo-2-trifluoromethylbenzimidazole, -cyano-2-trifluoromethylbenzimidazole, 4.6-dichloro-2-trifluoromethylbenzimidazole, . 4.7-dichloro-2-trifluoromethylbenzimidazole, 4-nitro-6-chloro-2-trifluoromethylbenzimidazole, 4-chloro-6-nitro-2-trif1uoromethylbenzimidazo1e, 4-chloro-2-trifluoromethylbenzimidazole, 4-bromo-5, 6,7-trichloro-2-trifluoromethylbenzimidazole, 4, 6, 7-trichloro-5-methyl-2-trifluoromethylbenzimidazole, 4 , 5, 6-trichloro-2-pentafluoroethylbenzimidazole, l-carboethoxy-4, 5,6-trichloro-2-trifluoromethylbenzimidazole and 4 , 5, 6, 7-tetrachloro-l-methyl-?2~trifluoromethylbenzimidazole.
According to a preferred embodiment of the invention, the substituted benzimidazole is 5-iodo-2-trifluoromethylbenzimidazole or 4,5-dichloro-2-trifluoromethylbenzimidazole. According to a further preferred embodiment, the present invention is for a mixture of 5-iodo-2-trifluoromethylbenzimidazole or 4, 5-dichloro-2-trifluoromethylbenzimidazole and 2-methyl-thio-4-isopropylamino-6-( amma-methoxypropyl )amino-l , 3 ,5-triazine.
It has bee found that the mixtures according to the present invention possess herbicidal activity considerabl in excess of the herbicidal . activity of the components of the mixture; the mixtures thus exhibit synergism.
The salts of the substituted benzimidazoles are water soluble, and 9i - 5 - benzimidazoles may be formulated in any of the usual ways for insoluble compounds, together with wetting agents, solvents, solid diluents etc.
The triazines have very low solubility in all liquids, and therefore require to be formulated as a suspension, for example as an aqueous suspension. In the erbicidal mixture, therefore, this. may comprise for example ah aqueous suspension of. both the benzi idazole and the triazine. Alternatively a physically stable formulation is a wettable powder formulation of a mixture of the finely ground triazine, an inert diluent and a solid salt, for example, the sodium salt, of the substituted benzimidazole.
The proportion of the triazine and the substituted benzimidazole in a composition may vary over a wide range, and comprises from about 1-50 parts of triazine admixed with from about 1-100 parts of the substituted benzimidazole. Suitably the composition contains.0.25 to 75 parts of the substituted benzimidazole to one part of the triazine, and according to a preferred embodiment the composition contains about 2 to 4 parts of the substituted benzimidazole to 1 part of the triazine.
The present invention is also for a process for the selective control of weeds in crops ; the rate of application may vary over a wide range according to the crop species, and generally is of the order of about 2 to 32 ounces per acre (140 g.-2.24 Kg. per hectare) of the active ingredients.
Thus it is preferred to use the composition such that there is applied to the crop from 0.25 to 8 ounces per acre (20 g. -560 g. per Hectare) of the triazine and from 2 to 16 ounces per acre (140g.-1.12 Kg, per hectare) of the substituted benzimidazole.
The compositions according to the present invention may also include one or more other selective herbicides,, and it has been found advantageous in some cases to include in the composition a substituted phenoxy- carboxylic carboxylic carboxyl generally comprises an alkyl and/or halogen substituted phenoxyallphatic/ acids, and their salts, for example alkali metal, amine, alkanolamine salts, and functional derivatives, for example esters and amides. These compounds may be of activity such that they are recognised as commercial herbicides, or may be of only slight herbicidal activity. Examples of carboxylic the substituted phenoxyaliphatic/acids which may be mentioned include 2,4-dichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxyacetic acid; 2,4,5-trichlorophenoxyacetic acid, gamma-2,4-i;dichlorophenoxy-butyric acid, gamma-2-methyl-4-chlorophenoxy-butyrip acid and alpha-2-methyl-4-chlorophenoxypropionic acid. These compounds are preferably used in the form of a salt. , . · carboxylic The amount of substituted phenoxyaliphatic/acid is suitably in the range 0.5 to 4 parts, and preferably 1-2 parts, per part of substituted benzimidazole in the mixture.
The compositions according to the present invention may include any of the usual components such as surface active agents, stickers, diluents and other additives used in the art. The composition might comprise liquids suitable for spraying or powders suitable for dusting. The extent of dilution for spraying does not appear to be critical.
The active ingredients may be dispersed or dissolved in the carrier for application in any suitable way.
Thus for example, the active ingredients may be dissolved in a water immiscible solvent, such as for example a high boiling hydrocarbon, suitably containing dissolved emulsifying agents so as to act as a self-emulsifiable oil on addition to water.
The active ingredients may also be admixed with a wetting agent with or without an inert diluent to form a wettable powder which is soluble or dispersible in water, or may be mixed with the inert diluent to form a solid or powdery product.
Inert diluents with which the aqtive ingredients may be incorporated include solid inert media comprising powdered or divided solid materials, for example, clays, sands, talc, mica, fertilizers and the like, such products either comprising dust or larger particle size materials.
The wetting agents used may comprise anionic compounds such as for example soaps, fatty sulphate esters such as dodecyl sodium sulphate, octadecyl sodium sulphate and cetyl sodium sulphate, fatty aromatic sulphonates such as alkyl-benzene sulphonates or butyl naphthalene sulphonate, more complex fatty sulphonates such as the amide condensation product of oleic acid and N-methyl taurine or the sodium sulphonate of dioctyl succinate.
The wetting agents may also comprise non-ionic wetting agents such as for example condensation products of fatty acids, fatty alcohols or fatty substituted phenols with ethylene oxide, or fatty esters and ethers of sugars or polyhydric alcohols, or the products obtained from the latter by condensation with ethylene oxide, or the products known as block copolymers of ethylene oxide and propylene oxide. The wetting agents may also comprise cationlc agents such as for example cetyl triraethylammonium bromide and the like.
The compositions according to the present invention are of particular value in the control of weeds in cereal crops, and particularly for post emergence treatment of the crop. Crops which may be protected in this way include wheat, barley, maize, oats, rice and sugar cane.
The extent of the control of the weed species using these mixtures is distinctly greater than what would be expected from the herbicldal activity of the individual components.
The following examples are given to illustrate the present invention; parts are by weight.
Example 1 A mixture of 2 parts of 5-iodo-2-trifluororaethylbenzimidazole (compound I) and 1 part of 2-methylthio-4-isopropylamino-6-(gamma- methoxypropyl)amino-l,3,5-triazine (compound II) as an aqueous suspension of a wettable powder was sprayed on to various young weed species at a rate equivalent to 9 ounces per acre (630 g. per hectare) of the 2 ingredients combined. At intervals of 4, 6 arid 8 days after spraying the degree of damage to the plants was assessed on a scale of 0 to 100 by comparison with unsprayed controls. For comparison, compound I at the rate of 12 ounces per acre (840 g. per hectare) and compound II at the rate of 6 ounces per acre (420 g. per hectare) were each sprayed alone.
The table below shows the amount of herbicidal effect on chickweed, mayweed, speedwell and cleavers caused by each composition at intervals of 4, 6 and.8 days after spraying.
Example 2 A mixture of 4 parts of 5-iodo-2-trifluoromethylbenzimidazole and 1 part of 2-methylthio-4-isopropylamino-6r(gamma-methoxypropyl )amino- 1,3,5-triazine, was prepared as an aqueous suspension of a wettable powder and -sprayed at the rate of 10 ounces per acre (700 g,/hectar e) on various oun weeds as described in.Exam le 1. The de ree of dama e to the weeds expressed as % weed control, was measured at 2, 4, 7 and 17 days after spraying and the results obtained are given below.
Example 3 The following compositions were prepared as aqueous suspensions of wettable powders :- A. 4, 5-dichloro-2-trifluoromethylbenzimidazole - 6 parts 2-methylthio-4-isopropylamino-6-(gamma- methoxypropy1)amino-l ,3, 5-triazine - 2 parts 2-methyl-4-chlorophenoxyacetic acid - 12 parts B„ 5-iodo-2-trifluoromethylbenzimidazole - 6 parts 2-methylthio-4-isopropylamino-6-(gamma- methoxypropyl)amino-l ,3, 5-triazine - 2 parts 2-methyl-4-chlorophenoxyacetic acid - 12 parts Solely by way of comparison the following single component compositions were also prepared: - C. 2-methyl-4-chlorophenoxyacetic acid D. 2-methylthio-4~isopropylamind-6-( gammamethoxypropyl)-amirio-l ,3,5- triazine.
These compositions were sprayed on fields of wheat and barley infested with various weed species when the crops were at the 2-3 leaf stage. The rate of application based on combined active ingredients was as follows:- A - 20 ounces per acre (140 g./hectare) B - 20 ounces per acre (140 g. ectare) C - 20 ounces per acre (140 g./hectare) D - 2 ounces per acre ( 14 g./hectare).
The degree of weed control expressed as a percentage of untreated controls was as follows:- Composition A B D Weed Species Black bindweed (P. convolvulus). 92 87 60 28 Redshank (P. persicaria) 100 97 30 7 Chickweed (S. media; 9S> 97 38 44 Knotgrass (f. avieni ^re 83 90 60 25 Field speedwell (V. agrestis) 87 80 35 10 Corn marigold (C. segetum) 79 52 36 30 In the preceding examples, the substituted benzimidazole and phenoxy- carboxylic aliphatic/acid were used in the form of the sodium salt; in accordance with usual practice weights are based on the acid equivalent.
The post-emergence treatment of weed infested crops according to the present invention is suitably applied when the crop is at the 2 to 5 leaf stage, and preferably at the 2 to 3 leaf stage.
Claims (22)
1. Synergistic herbicidal compositions comprising a mixture of a triazine of the formulas SCH, 1 2 3 4 where R , R , R and R are hydrogen, alkyl or alkoxyalkyl groups, together with at least one substituted benzimidazole of the formulas E6 ' where R^ is hydrogen, a lower alkyl group or -COOR where R is optionally halogen-substituted alkyl, optionally alkyl-substituted fi 7 ft Q aryl or cycloalkyl; and R , R , R and R are the same or different and are each hydrogen, an optionally halogen-, hydroxy- or alkoxy-substituted alkyl, hydroxy, alkoxy, nitro, halogen, cyano, thiocyano, isothiocyano, azido, carboxy, alkoxycarbonyl, carbamoyl, N-mono or NpN-disubstituted carbamoyl, amino mono- or disubstiuted by alkyl, acyl or halogen-substituted acyi mercapto, alkylthio, alkylsulphinyl, alkylsulphonyl, sulpho, alkoxysulphonyl, sulphamoyl or a saturated heterocyclic ring attached to the benzimidazole system through a nitrogen atom and X is trifluoromethyl, or pentafluoroethyl, or a salt or functional derivative of said benzimidazole, where such exist.
2. A herbicidal composition as claimed in claim 1 wherein the ratio of the triazine to the substituted benzimidazole is in the range 1-50 , parts of the. former to 1-100 parts of the latter.
3. A herbicidal composition as claimed in claim 2 wherein the ratio of the triazine to the substituted benzimidazole is approximately 1 part of the triazine to 2-4 parts of the substituted benzimidazole.
4. A herbicidal composition as claimed in any of the preceding claims wherein the triazine is 2-methylthlc~4-isopropylamino-6-( gamma-methoxypropyl) amino.- 1 ,3,5-triazine, 2,4-bis-isopropylamino-6-methylthio-s-triazine, 2-ethylamino-4-isopropylamino-6-methylthio-s-triazine, 2,4-bis(monoethylamin< 6~methyl-mercaptp—s-triazine or 2-isopropylamino-4-methylaraino-6-methyl-mercapto-s-triazine.
5. A herbicidal composition as claimed in any of the preceding claims " 1 2 wherein the triazine is one in which at least one of the groups R , R , . 3 4 R ,. and R is alkoxyalkyl „
6. A herbicidal composition as claimed in claim 5 wherein the triazine 1- 2 3 is one in which at least one of the groups R , R ,,R . and R is gamma-methoxyprop l .
7. A herbicidal composition as claimed in any. of the preceding claims wherein the triazine is 2-methylthio-4-isopropylamino-6-( gamma-methoxypropyl) amino-1β,5-triaziiie .
8. A herbicidal composition as claimed in any of the preceding claims wherein the substituted benzimidazole is 4,5,6;7-!-tetrachloro-2-trifluoro-. methylbenzimidazole, 4,5,6-trichlor-2-trifluoromethylbenzimidazole, 4,5,7-trichlorb-2-trifluoromethylbenzimidazole, 4 ,5-dichloro-2-trifluoro-methyl benzimidazole, 5-iodo-2-trifluoromethyl benzimidazole, 5-cyano-2-trifluoromethyl benzimidazole, 4,6-dichloro^2-trifluoromethylbenzimidazole, methyl benzimidazole, 4-chloro-6-nitro-2-trlfluoromethyl benzimidazole. 4-chloro-2-trifluororaethyl benzimidazole, 4-bromo-5,6,7-trlchloro-2-trifluoromethyl benzimidazole, 4, 6, 7-trichloro-5-methyl-2-trifluoromethyl benzimidazole, 4,5,6-trichloro-2-pentafluoroethyl benzimidazole, 5-nitro-2-pentafluoroethyl benzimidazole, morpholino trichloro-2-tri-fluoromethyl benzimidazol , l-carboethoxy- ,5,6-trichloro-2-trifluoromethyl benzimidazole or 4,5, 6, 7-tetrachloro-l-methyl-2-trifluoromethyl benzimidazole.
9. A herbicidal composition as claimed in any of the preceding claims wherein the substituted benzimidazole is 5-iodo-2-trifluoromethyl benzimidazole or 4,5-dichloro-2-trifliioromethyl benzimidazole.
10. A herbicidal composition as claimed in any of the preceding claims which comprises a mixture of 2-methylthlo-4-isopropylamino-6-( gamma methoxypropyl)amino-l,3,5-triazine and 5-iodo-2-trifluoromethyl benzimidazole or 4,5-dichloro-2-trifluoromethyl benzimidazole.
11. A herbicidal composition as claimed in claim 10 which comprises a mixture of 2-methylthio-4-isopropylamino-6-(gamma methoxypropyDamino-1,3,5-triazine and 5-iodo-2-trifluoromethyl benzimidazole in a ratio of approximately 1 part of the former 'to 2 - 4 parts of the latter.
12. A herbicidal composition as claimed in any of the preceding claims wherein the substituted benzimidazole is in the form of a salt.
13. A herbicidal composition as claimed in any; of the preceding claims which contains a surface active agent and/or a sticker and/or a diluent.
14. A herbicidal composition as claimed in any of the preceding claims which contains another selective herbicide.
15. A herbicidal composition as claimed in any of the preceding claims which also contains a substituted phenoxyaliphatic acid or a salt or functional derivative thereof. - 14 29368/2
16. A herbicidal composition as claimed in Claim 15 wherein the substituted phenoxyaliphatic carboxylic acid is 2-methyl-4-chlorophenoxyacetic acid or alpha-2-methyl-4-chloro-phenoxypropionic acid.
17. A herbicidal composition as claimed in Claim 15 or Claim 16 wherein the substituted phenoxyaliphatic carboxylic acid is present in amount comprisin 0.5 to 4 parts per part of substituted benzimidazole .
18. Herbicidal compositions as claimed in Claim 1 substantially as he-sslnbe ore described.
19. Herbicidal compositions as claimed in Claim 1 substantially as .hereinbefore described and illustrated in any of the preceding Examples.
20. A process for the preparation of herbicidal compositions as claimed in any of the preceding claims which comprises mixing together a triazine and a substituted benzimidazole as hereinbefore defined.
21. A process for the control of weeds in crops which comprises applying to the crop area or the soil a mixture of a triazine and a substituted benzimidazole as hereinbefore defined. '
22. A process for the control of weeds in crops as claimed in Claim 21 substantially as hereinbefore described. PC/rb
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB646667A GB1186165A (en) | 1967-02-10 | 1967-02-10 | Herbicidal Compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL29368A true IL29368A (en) | 1971-10-20 |
Family
ID=9814997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2936868A IL29368A (en) | 1967-02-10 | 1968-01-24 | Synergistic herbicidal compositions containing a 2-methylthio-1,3,5-triazine and a benzimidazole |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE710402A (en) |
| CH (1) | CH489191A (en) |
| DE (1) | DE1667976A1 (en) |
| FR (1) | FR1565485A (en) |
| GB (1) | GB1186165A (en) |
| IL (1) | IL29368A (en) |
| LU (1) | LU55407A1 (en) |
| NL (1) | NL6801652A (en) |
-
1967
- 1967-02-10 GB GB646667A patent/GB1186165A/en not_active Expired
-
1968
- 1968-01-24 IL IL2936868A patent/IL29368A/en unknown
- 1968-02-05 LU LU55407A patent/LU55407A1/xx unknown
- 1968-02-06 CH CH169168A patent/CH489191A/en not_active IP Right Cessation
- 1968-02-06 NL NL6801652A patent/NL6801652A/xx unknown
- 1968-02-06 BE BE710402D patent/BE710402A/xx unknown
- 1968-02-07 DE DE19681667976 patent/DE1667976A1/en active Pending
- 1968-02-09 FR FR1565485D patent/FR1565485A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1186165A (en) | 1970-04-02 |
| BE710402A (en) | 1968-08-06 |
| NL6801652A (en) | 1968-08-12 |
| LU55407A1 (en) | 1968-10-09 |
| DE1667976A1 (en) | 1971-07-29 |
| CH489191A (en) | 1970-04-30 |
| FR1565485A (en) | 1969-05-02 |
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