MXPA97005448A - Herbic composition - Google Patents
Herbic compositionInfo
- Publication number
- MXPA97005448A MXPA97005448A MXPA/A/1997/005448A MX9705448A MXPA97005448A MX PA97005448 A MXPA97005448 A MX PA97005448A MX 9705448 A MX9705448 A MX 9705448A MX PA97005448 A MXPA97005448 A MX PA97005448A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- alkyl
- formula
- halogen
- substituted
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 83
- HBPDKDSFLXWOAE-UHFFFAOYSA-N Tebuthiuron Chemical compound CNC(=O)N(C)C1=NN=C(C(C)(C)C)S1 HBPDKDSFLXWOAE-UHFFFAOYSA-N 0.000 title 1
- 230000002363 herbicidal Effects 0.000 claims abstract description 87
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 239000004009 herbicide Substances 0.000 claims abstract description 74
- 239000000126 substance Substances 0.000 claims abstract description 35
- 125000004432 carbon atoms Chemical group C* 0.000 description 498
- 125000000217 alkyl group Chemical group 0.000 description 200
- 229910052736 halogen Inorganic materials 0.000 description 116
- 150000002367 halogens Chemical group 0.000 description 116
- 125000003545 alkoxy group Chemical group 0.000 description 89
- 229910052799 carbon Inorganic materials 0.000 description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 75
- 229910052739 hydrogen Inorganic materials 0.000 description 74
- 239000001257 hydrogen Substances 0.000 description 72
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 59
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 59
- 230000001012 protector Effects 0.000 description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 52
- 125000003342 alkenyl group Chemical group 0.000 description 49
- -1 RgCO- or R90N = CRg- Chemical group 0.000 description 42
- 125000004093 cyano group Chemical group *C#N 0.000 description 42
- 125000000753 cycloalkyl group Chemical group 0.000 description 42
- 125000001188 haloalkyl group Chemical group 0.000 description 39
- 125000004438 haloalkoxy group Chemical group 0.000 description 34
- 125000000304 alkynyl group Chemical group 0.000 description 23
- 125000004001 thioalkyl group Chemical group 0.000 description 22
- 244000045561 useful plants Species 0.000 description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 13
- 101710005824 Chc Proteins 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 125000003302 alkenyloxy group Chemical group 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 125000004043 oxo group Chemical group O=* 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 125000005133 alkynyloxy group Chemical group 0.000 description 7
- 125000004429 atoms Chemical group 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 235000008216 herbs Nutrition 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 6
- 235000008504 concentrate Nutrition 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 235000005824 corn Nutrition 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000000885 phytotoxic Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000000262 haloalkenyl group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 230000001681 protective Effects 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 229910052701 rubidium Inorganic materials 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- 235000021307 wheat Nutrition 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N Diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000002605 anti-dotal Effects 0.000 description 4
- 239000000729 antidote Substances 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 239000000460 chlorine Chemical group 0.000 description 4
- 239000007931 coated granule Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000000466 oxiranyl group Chemical group 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 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
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 230000002633 protecting Effects 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- 229920001451 Polypropylene glycol Polymers 0.000 description 3
- 235000007238 Secale cereale Nutrition 0.000 description 3
- 240000002057 Secale cereale Species 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 229910052801 chlorine Chemical group 0.000 description 3
- 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 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229910052705 radium Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N Isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N Nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Natural products CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 125000004310 dioxan-2-yl group Chemical group [H]C1([H])OC([H])([H])C([H])(*)OC1([H])[H] 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005347 halocycloalkyl group Chemical group 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N n-methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229910052904 quartz Inorganic materials 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N 1,2-Diaminopropane Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-Amino-2-propanol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- MHVSMFDBVMPRGT-UHFFFAOYSA-N 1-methoxyethanamine Chemical compound COC(C)N MHVSMFDBVMPRGT-UHFFFAOYSA-N 0.000 description 1
- KBLAMUYRMZPYLS-UHFFFAOYSA-M 2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-M 0.000 description 1
- QZEDXQFZACVDJE-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 QZEDXQFZACVDJE-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N 2-(methylamino)ethanesulfonic acid Chemical class CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-Ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- JYCQQPHGFMYQCF-UHFFFAOYSA-N 2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCO)C=C1 JYCQQPHGFMYQCF-UHFFFAOYSA-N 0.000 description 1
- BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-N,N-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N 3-aminopropanol Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- SPVVMXMTSODFPU-UHFFFAOYSA-N 3-methyl-N-(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCNCCC(C)C SPVVMXMTSODFPU-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical class NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- KWXICGTUELOLSQ-UHFFFAOYSA-N 4-Dodecylbenzenesulfonic Acid Chemical class CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-N 0.000 description 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N Azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N Bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N Dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N Dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N Dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N Ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 240000003598 Fraxinus ornus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N Hexylamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- 229940102253 ISOPROPANOLAMINE Drugs 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N Isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N N,N-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- DJUWKQYCYKRJNI-UHFFFAOYSA-N N-ethoxyaniline Chemical class CCONC1=CC=CC=C1 DJUWKQYCYKRJNI-UHFFFAOYSA-N 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N N-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N N-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N N-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N N-methoxyaniline Chemical class CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- XJINZNWPEQMMBV-UHFFFAOYSA-N N-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N N-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N N-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N N-octyloctan-1-amine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N N-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N Pentadecylamine Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N Pentylamine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 229940067631 Phospholipids Drugs 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N Quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- 229960000391 Sorbitan trioleate Drugs 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N Tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N Triethyl phosphate Chemical class CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N Triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N Trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-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
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- PRXRUNOAOLTIEF-XDTJCZEISA-N [2-[(2R,3S,4R)-4-hydroxy-3-[(Z)-octadec-9-enoyl]oxyoxolan-2-yl]-2-[(Z)-octadec-9-enoyl]oxyethyl] (Z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@@H](O)[C@@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-XDTJCZEISA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000003972 agrochemical formulation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000003042 antagnostic Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 125000006515 benzyloxy alkyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000001488 breeding Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 150000003940 butylamines Chemical class 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 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
- 239000004202 carbamide Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 101700043453 chch-3 Proteins 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000254 damaging Effects 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N decan-1-amine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- TUKQLEWOUPCTOS-UHFFFAOYSA-N dimagnesium;dioxido(oxo)silane;hydroxy-oxido-oxosilane;hydrate Chemical compound O.[Mg+2].[Mg+2].O[Si]([O-])=O.O[Si]([O-])=O.[O-][Si]([O-])=O TUKQLEWOUPCTOS-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 150000005452 ethyl sulfates Chemical class 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N ethylene glycol monomethyl ether Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005291 haloalkenyloxy group Chemical group 0.000 description 1
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N heptan-1-amine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N hexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 229940113083 morpholine Drugs 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical class CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- AXIPBRXJGSXLHF-UHFFFAOYSA-N piperidine;pyrrolidine Chemical compound C1CCNC1.C1CCNCC1 AXIPBRXJGSXLHF-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- VQOIVBPFDDLTSX-UHFFFAOYSA-M sodium;3-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC(S([O-])(=O)=O)=C1 VQOIVBPFDDLTSX-UHFFFAOYSA-M 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N stearylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229960001663 sulfanilamide Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 230000002522 swelling Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Abstract
The present invention relates to: A selective herbicidal composition, which comprises, in addition to customary inert forming aids, an active substance comprising a mixture of: a) a herbicidally effective amount of a herbicide of the formula I: b) an antagonistically effective herbicide amount of a compound of the formula IIa: a compound of the formula IIb1: a compound of the formula IIb2: a compound of the formula IIc: a compound of the formula IIe: a compound of the formula IIf: or a compound of the formula IIg: wherein the substituents are as defined in the claim
Description
HERBICIDE COMPOSITION
The present invention relates to a selective herbicidal composition for controlling grasses and broad-leaved herbs in crops of useful plants, in particular in corn and cereal crops such as rye, barley, oats and in particular, wheat, which composition comprises a herbicide and a protector (counteracting agent, antidote), and - which safeguards useful plants, but herbs against the phytotoxic effect of the herbicide, and the use of this composition for the control of herbs in crops of useful plants. When herbicides are used it is possible, depending, for example, on the concentration and mode of application of the herbicide, on the crop plant, or on the nature of the soil and climatic conditions, such as the period of exposure to the herbicide. light, temperature, and amounts of precipitation, that the crop plants are damaged too much to a considerable degree. In order to counteract this and similar problems, a variety of substances have already been proposed as protectants, which are capable of antagonizing the harmful effect of the herbicide on the crop plant, that is, of protecting the crop plant from this effect , while virtually does not cause harm to the herbicidal effect on the herbs that are to be controlled. In this context, it has been discovered that the proposed protectants often have a very specific action both with respect to the crop plants and with respect to the herbicide, and in some cases, in addition, depending on the mode of application; in other words, often a particular protector is suitable only for a specific crop plant and for a specific class of herbicidal substance, or a specific herbicide. It has now been discovered that the protectors known from Patent Numbers EP-A-402, 366; WO 91/7874 and WO 94/987, are suitable for protecting crop plants against the phytotoxic effect of a certain class of N-acyl sulfonamide herbicides. These herbicides are known, for example, from Patent Numbers EP-A-592, 680; EP-A-51, 551; EP-A-353, 640; WO 94/5644, WO 92/16511; EP-A-44, 286; and 92/1677. Accordingly, according to the invention, a selective herbicidal composition is proposed which comprises, in addition to customary inert formulation aids such as vehicles, solvents, and wetting agents, an active substance comprising a mixture of: a) an amount herbicidally effective of a herbicide of the formula I:
2_SO2-N-CO- "CR.R,) I, -NT"? V? (I), R, wherein: Z is alkyl of 1 to 10 carbon atoms, alkyl of 1 to 10 carbon atoms substituted by halogen, cycloalkyl of 3 to 8 carbon atoms, R70-, R7S (0) n- , R7R8N-, R8CO-, R9ON = CR8-, (CH3) 3Si-, -CN or oxiranyl, alkenyl of 2 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms substituted by halogen, phenyl, phenyl substituted by halogen alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, cycloalkyl of 3 to 8 carbon atoms, R70-, R7S (0) n-, R7R8N-, (CH3) 3Si-, CN, RgCO-, or R9ON = CR8-, alkynyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms substituted by halogen, alkyl of 1 to 10 carbon atoms, phenyl, phenyl substituted by halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms , alkoxy from 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, R0-, R7S (0) n-, R7R8N-, (CH3) 3Si-, -CN, oxo, = NOR7, R8CO-, or R ^ N ^ Rg-, cycloalkenyl of 3 to 8 carbon atoms, cycloalkenyl of 3 to 8 carbon atoms substituted by halogen, alkyl of 1 to 10 carbon atoms, phenyl, substituted phenyl by halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 1 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl R70-, R7S (0) n-, R7R8N-, (CH3) 3Si-, -CN , OXO, = NOR7, RgCO-, or R9ON = CR8-, -NR5R6, R10CON (R6) - or R10SO2N (R6) -, wherein: R7 is hydrogen, alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, phenyl, or phenyl substituted by halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms-carbonyl, n is 0, 1, or 2, R8 is as defined for R7, or is alkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 8 carbon atoms, or alkynyloxy of 3 to 8 carbon atoms, R9 is alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 8 carbon atoms, or alkynyl of 2 to 8 carbon atoms,
R10 is alkyl of 1 to 10 carbon atoms, alkyl of
1 to 10 carbon atoms substituted by halogen, R70-R7S (0) n-, -NR7R8 or -CN, alkenyl of 2 to 8 carbon atoms, alkenyl of
2 to 8 carbon atoms substituted by halogen, R0-, R7S (0) n-, NR7R8 or -CN, phenyl, or phenyl substituted by halogen, alkyl of
1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, wherein R7, n , and R8 are as defined, R5 is alkyl of 1 to 10 carbon atoms,
1 to 10 carbon atoms substituted by halogen, cycloalkyl of 3 to 8 carbon atoms, R70-, R7S (0) n, R7RgN- R8C0-, R90N = CR8-, (CH3) 3Si-, -CN or oxiranyl, alkenyl from 2 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms substituted by halogen, phenyl, phenyl substituted by halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, cycloalkyl of 3 to 8 carbon atoms, R70-, R7S (0) n-, R7R8N-, (CH3) 3Si -, -CN, RgCO- or R90N = CRg-, alkynyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms substituted by halogen, alkyl of 1 to 10 carbon atoms carbon, phenyl, phenyl substituted by halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, R70-, R7S (0) n-, R7R8N-, (CH3) 3Si-, -CN, oxo, = NOR7, RgCO-, or R90N = CRg-, cycloalkenyl from 3 to 8 carbon atoms, cycloalkenyl of 3 to 8 carbon atoms substituted by halogen, alkyl of 1 to 10 carbon atoms, phenyl, phenyl substituted by halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, C 1 -C 6 alkoxy, haloalkoxy of 1 to 6 carbon atoms or C 1 -C 6 alkoxy-carbonyl, R70-, R7S (0) n-, R7R8N-, (CH3) 3Si-, -CN, oxo, = NOR7, RgCO-, or
R9ON = CRg-, or is R70- where R7 is as defined, and R6 is as defined for R5, or is hydrogen, or together with R5 forms an alkylene radical of 4 to 7 carbon atoms, or Z is a radical of the formula:
(0) f (26) (25)
wherein: R50 is hydrogen, halogen, -N02, -CN, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen, -CN, -OCH3 or -SCH3, alkenyl of 2 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms substituted by halogen or OCH3, alkynyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms substituted by halogen, -0CH3 or -Si (CH3) 3, cycloalkyl from 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms substituted by -F, -Cl, or -CH3, C (O) R100, -OCH2CH2OR100, -OH, -C (R100) (OR110) (OR120 ), -CO2R130, -C (O) NR140R150, -N3, -SO2NR140R150, -SO3R160, -OSO2R170, phenyl, phenyl substituted by halogen, -CH3 or -OCH3, -OR? 80, -S (O) bR180 or - - (CH2) SG, where bys, independently of one another, are 0 6 1, RgO is hydrogen, halogen, -CN, -N02, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen, -CO2R130, -SO2NR140Rj50, -NR140R150, alkoxy of 1 2 carbon atoms, -ORj ^, -SÍO ^ Rj ^, haloalkoxy of 1 or 2 carbon atoms, thioalkyl of 1 or 2 carbon atoms, halotioalkyl of 1 or 2 carbon atoms, -CN, -OH or -SH , -CO2R130, -SONR10R150"^ 140 * 150 '-S (°) bR190 or - ° R190' R70, independently in each presentation, is hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, phenyl, phenyl substituted by halogen, -S (O) bR190 or -ORj, 90 /
-S (O) bR190, -OR190 or halogen, R8Q is hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4, halogen, -CO2R130, -SO2NR140R? 50, -OSO2R170, --S (O) bR180, -CN or -N02, and R () Q is hydrogen, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen or phenyl, alkenyl of 2 to 4 carbon atoms, phenyl, or phenyl substituted by halogen, alkyl of 1 to 4 carbon atoms, -N02 / -CN, or alkoxy of 1 to 4 carbon atoms, wherein R100 is hydrogen, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen or -OCH3, cycloalkyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms substituted by halogen or -CH3, alkenyl of 2 to 4 carbon atoms or alkynyl of 2 to 4 carbon atoms, R110 and R120, independently of each other, are 1 to 4 carbon atoms, or R110 and R120 are together -CH2CH2-, CH2OCH2- or -CH2C (CH3) 2CH2-, R130 is hydrogen, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen, -CN, -CO2R100, -NR140R1S0, -OR100 or Si (CH3) 3, alkynyl of 3 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms arbono substituted by -CH 3 or -Si (CH 3) 3, cycloalkyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms-alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or - If (CH3) 3, R140 is hydrogen or alkyl of 1 to 4 carbon atoms,
R150 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or alkenyl of 2 to 4 carbon atoms, or R140 and R150 are together - (CH2) 2 (CH2) a- (CH2 ) 2- or - (CH2) 2- 0 (CH2) 2-, where a is 0 or 1, R160 is alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 4 carbon atoms, R | 70 is alkyl from 1 to 4 carbon atoms OR -NR ^ R ^ Q, wherein R ^ 40 and R150 are as defined, RJ8Q is alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 2 to 4 carbon atoms-alkyl, alkenyl of 2 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms, phenyl, or phenyl substituted by halogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms carbon, or haloalkyl of 1 to 3 carbon atoms, R [90 is alkyl of 1 to 4 carbon atoms, or alkyl of
1 to 4 carbon atoms substituted by -F, -Cl, or -ORj60, q is 0 or 1, G is a radical of the formula:
wherein R260 is hydrogen or alkyl of 1 to 3 carbon atoms, and R270 is hydrogen, alkyl of 1 to 3 carbon atoms, or alkenyl of 2 to 4 carbon atoms, R2 is hydrogen, alkyl of 1 to 10 carbon atoms, carbon, alkyl of 1 to 10 carbon atoms substituted by alkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, alkenyl of 3 to 8 carbon atoms or benzyl, X and Y, independently one of the another, are = N-, = CH-or = CR-, where either X or Y should be = N-, and where R is halogen, alkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 atoms of carbon substituted by halogen, alkoxy of 1 to 6 carbon atoms or haloalkoxy of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms or haloalkoxy of 1 to 6 carbon atoms, R3 and R4 »independently of each other , are hydrogen, halogen, alkyl of 1 to 10 carbon atoms, R70- R7S (0) n,
R7R8N-, haloalkyl of 1 to 10 carbon atoms, haloalkoxy of 1 to 10 carbon atoms, alkoxy of 6 carbon atoms-alkyl of 1 to 6 carbon atoms or thiophenyl, wherein R7, n, and R8 are as are defined, or R3 or R4, together with R, form a radical -0CH2CH2 (CH2) m- or - (CH2) mCH2CH20-, where m is 0 or 1, Ra is hydrogen, alkyl of 1 to 8 carbon atoms , alkyl of 1 to 8 carbon atoms substituted by hydroxy, alkoxy of 1 to 8 carbon atoms, phenoxy, thioalkyl of 1 to 8 carbon atoms, thiophenyl, (CH 3) 3 Si-, cycloalkyl of 3 to 8 carbon atoms, phenyl, or dialkyl of 1 to 8 carbon atoms-amino, alkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms substituted by halogen, or Ra is alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms substituted by alkyl of 1 to 3 carbon atoms, or Ra is cycloalkenyl of 3 to 6 carbon atoms, phenyl, substituted phenyl or by alkyl of 1 to 8 carbon atoms, halogen, nitro, -CN, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, phenoxy, -NR7R8 or
RgCO-, wherein R7 and R are as defined, or Ra is hydroxyl, halogen, tetrahydrothienyl, tetrahydrofuryl, furyl, pyridyl, or thienyl, Rb is hydrogen, alkyl of 1 to 8 carbon atoms, or
phenyl, or Ra and Rb, together with the carbon atoms with which they are
united, they form a radical of the formula -CO-, and m is 0 or 1; and also salts and stereoisomers of the compounds of the formula I,
and b) an antagonistically effective amount of herbicide of a compound of the formula lia:
wherein: RQIQ is hydrogen, alkyl of 1 to 8 carbon atoms, or alkyl of 1 to 8 carbon atoms which is substituted by alkoxy of 1 to 6 carbon atoms or alkenyloxy of 3 to 6 carbon atoms, and X2 is hydrogen or chlorine, of a compound of the formula Ilbj:
wherein: E is nitrogen or methine, Rjj is -CC13 or phenyl unsubstituted or substituted by p. halogen, R] 2 and R | 3, independently of one another, are hydrogen or halogen, and R] 4 is alkyl of 1 to 4 carbon atoms, of a compound of formula IIb2:
wherein: R12 and R13 are as defined above, and R66 'R67-R68 < independently of one another, they are alkyl of 1 to 4 carbon atoms, of a compound of the formula lie:
where: A2 is a group:
R 25 and R 26"independently of each other, are hydrogen, alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms,
alkyl of 1 to 4 carbon atoms which is substituted by alkoxy
from 1 to 4 carbon atoms or Rj or R2 together form an alkylene bridge of 4 to 6 carbon atoms which may be interrupted by oxygen, sulfur, SO, S02, NH, or -N (alkyl of 1 to 4 carbon atoms) carbon) -, R27 is hydrogen, or alkyl of 1 to 4 carbon atoms, - Raa is hydrogen, halogen, cyano, trifluoromethyl, nitro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, thioalkyl from 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon atoms-sulfonyl, -COORj, -C0NRkR, n, -C0Rn, -S02NRkR, n, or -0S02- alkyl of 1 to 4 carbon atoms; R is hydrogen, halogen, cyano, nitro, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon-sulfonyl atoms, -COORj, -CONRkRm, -COR ,,, -S02NRkR, n, -0S02-alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms substituted by alkoxy of 1 to 4 carbon atoms or halogen, alkenyloxy of 3 to 6 carbon atoms, or alkenyloxy of 3 to 6 carbon atoms substituted by halogen, or alkynyloxy of 3 to 6 carbon atoms, or Ra and Rb together form an alkylene bridge of 3 to 4 carbon atoms, which may be substituted by halogen or alkyl of 1 to 4 carbon atoms, or form an alkenylene bridge of 3 to 4 carbon atoms which may be substituted by halogen or alkyl of 1 to 4 carbon atoms, or form a 4-carbon-carbon alkydienylene bridge which may be its substituted by halogen or alkyl of 1 to 4 carbon atoms, - Rb and Rb independently of each other, are hydrogen, halogen, alkyl of 1 to 4 carbon atoms, trifluoromethyl, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, or -COORJ; Rc is hydrogen, halogen, nitro, alkyl of 1 to 4 carbon atoms or methoxy; Hydrogen, halogen, nitro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon-sulfonyl atoms, -COORj OR CONRkRm; Re is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, -COORj, trifluoromethyl or methoxy, or Rd and Re together form an alkylene bridge of 3 to 4 carbon atoms; Rf is hydrogen, halogen, or alkyl of 1 to 4 carbon atoms;
R? and Ry, independently of one another, are hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, -COOR2g, trifluoromethyl, nitro, or cyano; R;, Rfc, and Rm, independently of one another, are hydrogen or alkyl of 1 to 4 carbon atoms; or Rk ^ m together form an alkylene bridge of 4 to 6 carbon atoms, which may be interrupted by oxygen, NH, or -N (alkyl of 1 to 4 carbon atoms) -; Rn is alkyl of 1 to 4 carbon atoms, phenyl, or phenyl which is substituted by halogen, alkyl of 1 to 4 carbon atoms, methoxy, nitro, or trifluoromethyl; R28 is hydrogen, alkyl of 1 to 10 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, dialkyl of the 4 carbon-aminoalkyl atoms of 1 to 4 carbon atoms, haloalkyl of 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, haloalkenyl of 2 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, halocycloalkyl of 3 to 7 carbon atoms, alkyl of 1 to 8 carbon atoms, carbonyl, allylcarbonyl, cycloalkyl of 3 to 7 carbon atoms, benzoyl which is unsubstituted or which is substituted on the phenyl ring by up to three identical or different substituents consisting of halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms? or furoyl, thienyl; or alkyl of 1 to 4 carbon atoms substituted by phenyl, halophenyl, alkyl of 1 to 4 carbon atoms-phenyl, alkoxy of 1 to 4 carbon atoms-phenyl, haloalkyl of
1 to 4 carbon atoms - phenyl, haloalkoxy of 1 to 4 carbon atoms - phenyl, alkoxy of 1 to 6 carbon atoms - carbonyl, alkoxy of 1 to 4 carbon atoms - alkoxy of 1 to 8 carbon atoms - carbonyl, alkenyloxy of 3 to 8 carbon atoms-carbonyl, alkynyloxy of 3 to 8 carbon atoms-carbonyl, thioalkyl of 1 to 8 carbon atoms-carbonyl, thioalkenyl of
3 to 8 carbon atoms - carbonyl, thioalkynyl of 3 to 8 carbon atoms - carbonyl, carbamoyl, monoalkyl of 1 to 4 carbon atoms - aminocarbonyl, dialkyl of 1 to 4 carbon atoms - aminocarbonyl; or phenylaminocarbonyl which is unsubstituted or which is substituted on the phenyl by up to three identical or different substituents consisting of halogen, alkyl of 1 to
4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms, or by a single substituent of cyano or nitro, or dioxolan-2-yl which is unsubstituted or is substituted by one or two alkyl radicals of 1 to 4 carbon atoms, or dioxan-2-yl which is unsubstituted or is substituted by one or two alkyl radicals of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms which is substituted by cyano, nitro, carboxyl, or thioalkyl of 1 to 8 carbon atoms-alkoxy of 1 to 8 carbon atoms-carbonyl, of a compound of the formula lie:
K 3 or \ N N € - CHC1 (He) R /
wherein: R3 and R3, independently of one another, are alkyl
from 1 to 6 carbon atoms or alkenyl of 2 to 6 carbon atoms; or R33 and R34 are together
R35 and R36, independently of one another, are hydroge¬
or, or alkyl of 1 to 6 carbon atoms; or R3 and R34 are together
? • R37 and R38 'independently of one another, are alkyl of 1 to 4 carbon atoms, or R37 and R38 are together - (CH2) 5 ~; R39 is hydrogen, alkyl of 1 to 4 carbon atoms,
or R 3 and R34 are j untos
R40 'R41' R42 'R43' R44 'R45' R46 'R47' R48 'R49' R050 'R51' R52, R53, R54, and R55, independently of one another, are hydrogen or alkyl of 1 to 4 carbon atoms, - of a compound of the formula Ilf:
wherein: R63 is hydrogen or chloro, and R64 is cyano or trifluoromethyl, or a compound of the formula Ilg:
wherein R65 is hydrogen or methyl,
The invention also relates to a process for the selective control of herbs in crops of useful plants, which comprises treating the useful plants, their seeds or seedbeds, or their cultivation area, of one. simultaneously or separately, with a herbicidally effective amount of a herbicide of the formula I, and an antagonistically effective herbicide amount of a protector of one of the formulas Ia to Ilg. Among the plants which can be protected by the protectants of the formulas Ia and Ilg against the damaging effect of the aforementioned herbicides, corn and cereals such as rye, barley, oats, and in particular wheat are particularly suitable. The term crops should also be understood to refer to those that have been made tolerant to herbicides or to classes of herbicides by conventional methods of breeding or genetic manipulation.
The herbs to be controlled can be both monocotyledonous and dicotyledonous herbs. The areas that are considered as growing areas are the land areas in which the crop plants are already growing, or the land areas sown with the seeds of these crop plants, and also the areas intended to be cultivated with these plants. culture. The alkyl groups mentioned in the definitions of the substituents of the compounds of the formulas I and lia to Ilg can be straight or branched chain, and are, for example, methyl, ethyl, normal propyl, isopropyl, normal butyl, secondary butyl , isobutyl, tertiary butyl, and also pentyl, hexyl, heptyl, octyl, nonyl, decyl, and the branched isomers thereof. These alkyl groups can carry other substituents, for example halogen, especially fluorine, chlorine, or bromine, alkoxy, thioalkyl, cycloalkyl, phenyl, amino, acyl (for example, R8CO-) or oxo (0 =). Suitable alkoxy, thioalkyl, haloalkyl, and haloalkoxy groups are derived from the aforementioned alkyl groups. Examples of the unsaturated substituent groups are ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, and their isomers, which differ in the different position of the bond or bonds unsaturated in the molecule, the isomers that include branching points, and the cis and trans isomers in the case of alkenes. For example, propenyl substituted by chlorine can exist in both forms:
Accordingly, the substituted compounds of the formula I also constitute isomers which can be obtained and / or used in the pure form or as a mixture. Examples of the alkenyloxy, alkynyloxy, haloalkenyl, and haloalkenyloxy groups can be derived from the aforementioned alkyl groups. Cycloalkyl groups comprise, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. The corresponding cycloalkenes can be mono- or poly-unsaturated. The term "substituted" refers, where possible in the corresponding group, not only to a monosubstitution, but also to a polysubstitution. In the same way, the invention encompasses agriculturally compatible salts that can form the compounds of formula I, for example, with amines, alkali metal and alkaline earth metal bases, or quaternary ammonium bases. Among the alkali metal and alkaline earth metal hydroxides, as salt formers, particular emphasis should be given to the hydroxides of lithium, sodium, potassium, magnesium, or calcium, but especially those of sodium or potassium. Examples of amines suitable for forming ammonium salts are not only ammonia but also amines alquíli-cas 1 -C 18 primary alkyl, secondary, and tertiary hydroxyalkyl amines of 1 to 4 carbon atoms, and amines alcoxialquílicas of 2 to 4 carbon atoms, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, metilnonilamina, methylpent-tadecilamina, methyloctadecylamine, ethylbutylamine, etilheptilami-na, etiloctilamina, hexilheptilamina, hexiloctila ina, dimethylether-, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine , diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N, N-diethanolamine, N-ethylpropanolamine ina, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2, 3-dimetilbutenil-2-amine, dibutenil-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine, and ethoxyethylamine; heterocyclic amines such as, for example, pyridine, quinoline, isoquinoline, morpholine, piperidine; pyrrolidine, indoline, quinuclidine and azepine, - primary arylamines such as, for example, anilines, methoxyanilines, ethoxyanilines, o-, m-, and p - toluidines, phenylenediamines, bencidi-nas, naphthylamines, I-, m-, and p-chloroanilines; but especially triethylamine, isopropylamine, and diisopropylamine. Preferred compositions according to the present invention comprise as herbicide a compound of formula I wherein R3 and R4 are methoxy. Another group of preferred compositions comprises as a herbicide a compound of the formula I wherein R3 and R4 are methoxy, and Z is alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 8 carbon atoms, or haloalkenyl of 2 to 8 atoms of carbon. Among these compounds, a particular preference is given to those which comprise as a herbicide, a compound of the formula I wherein Z is -CH 2 -CH (CH 3) 2, -CH 2 C (CH 3) = CH 2 or -CH 2 -CH = CHC 1. Particular importance is given to those compositions comprising as herbicide, a compound of the formula I wherein Z is -CH2-CH (CH3) 2, -CH2C (CH3) = CH2 or -CH2-CH = CHC1 and m is
0. Preferred compositions comprise as a protector, a compound of the formula lia, Ilbj, Hb2, or líe.
Among these, particular preference is given to those with protectors of the formulas Ilbj and llb2, and also to those with the protectants of the formula lia. A particular value is given to the compositions comprising as herbicide, a compound of the formula I wherein Z is -CH2-CH (CH3) 2, -CH2-C (CH3) = CH2 or -CH2-CH = CHC1 and m is 0, and as a protector a compound of the formula lia, in particular of the formula lia »,:
The preferred compounds of the formula I are listed in the following Tables.
Table 1; Composed of the formula la:
Compound No. ()] -CH2-CH = CHC1 (Z) () 2 -CH2-CH = CHC1 (E) () 3 -CH2-CC1 = CH:. { 4-CH2-CC1 = CHC] () 5 -CH2-C (CH3) = CHC] () 6 -CH2-CBr = CH2 () 7 -CH2-CC1 = CHCH3 .OS -CH -, - CH = CHBr. 09-CH2-CHC1-CH2C1 O.10 -CH, 1
.11 -CH2-C (CH3) 3
.1-CH2-CH2CN 14 -CH2-CH = CC1CH3 15 -CH2-CH = C (CH3) 2 16 -CH2-CH2-C (CH) 3 = CH2 17 -CH2-CH = CCI2 18 -CH = CH- CH: CH3 1 19 NH2 j 2 () -CCHH22 - CH = CHC1
Compounds Nos. 1.01 to 1.21 and their preparation are described in European Patent Number EP-A-592, 680. Compounds 1.03 to 1.21 are mixtures of isomers (Z) and (E).
Table 2: Compounds of the formula Ib:
Compound No. R-,
•
2) 2
The compounds Nos. 2.01 to 2.10 and their preparation are described in European Patent No. EP-A-514, 551, those of Numbers 2.11 to 2.13 in International Patent No. WO 92/1677, those of No. 14 in the International Patent No. WO 94/5644 and those of Number 15 in International Patent No. WO 92/16511.
Table 3a; Compounds of the formula le:
Compound No, - - -CEA-,
3. 01 -CO: CH3 H -OCH3 -OCH3
3. 02 -CO2CH3 H -CO- -OCH3 -OCH3
3. 03 -CG \ CH3 H -CH2- -OCH3 -OCH3
3. 04 -NO; H -CH2- -OCH3 -OCH3
305 -. 305 -NO: H -OCH3 -OCH3
3. 06 -CF, H -CO- -OCH3 -OCH3
307 -. 307 -CF, H -CO- -CH3 -CH3
3 OS -CO: CH? H -OCH3 -CH3
3. 09 -CO2CH3 H -CO- -OCH3 -CH3
3. 10 -CF3 H -CO- -OCH3 -CH3
3. 11 -Br H -CO- -OCH3 -OCH3
3. 12 -OC2Hs H -CO- -OCH3 -OCH3
3. 13 -N02 6-F -co- -OCH3 -OCH3
3. 1; -OCH3 H -co- -OCH3 -OCH3
3. 15 -CO: CH3 5-C1 -OCH3 -OCH3
3. 16 -li H -OCH3 -OCH3
Compounds Nos. 3.01 to 3.16 and their preparation are described in European Patent No. EP-A-353, 40.
Table 3b: Compound of the formula Id:
Compound No -eSaSb- 3.17 S02N (CH3) 2 -OCH
Compound No. 3.17 and its preparation are described in European Patent No. EP-A-444, 286. The protectants which are particularly suitable for use in the compositions according to the invention, are listed in the following Tables.
Table 4: Compounds of the formula lia:
Compound No. X. ^ 010- Table 5: Compounds of formula IIb (
Compound No. R 14- ^ 11- 5 = 12- * 13- E
. 01 CH, Phenyl 2-C1 H CH
02 CH, Phenyl 2-C1 4-C1 CH
03 CH, Feni! 2-F H CH
04 CH, - Chlorophenyl 2-F H CH
. 05 C2H5 CC13 2-C1 4-C1 N
. 06 CH, Phenyl 2-C1 4-CF3 N
. 07 CH, Phenyl 2-C1 4-CF3 N
. 08 CH, 2- Fluorophenyl 2-C1 H CH
7abla 6: Compound of formula IIb2:
Compound No.% S- ^ 67- Ó6- 42- - ^ 13-
6. 01 CH3 CH3 CH3 2-C1 4-C1 0.02 CH3 C2H CH3 2-C1 4-C1 6.03 CH3 C H C2H5 2-C1 4-C1
Table 7; Composed of the formula lie
O CH, II _C_NHS02- / • NH-C - N (He) R 26
Compound No. 26-
Table 8: Compounds of the formula lie
R 33 O ~ N- C - CHCI, (He) R 34
Compound No. 33- ^ 34- - 33 ± £ 34-
Table 9; Composite of the formula Ilf
Compound No. R63 ^ 64- 9.01 H C 9.02 Cl CF
Table 10 Compound of the formula Ilg
Compound No, ^ 65- 10.01 H 10.02 CH,
The protectants listed in Tables 4 to 10 and their preparation are known, for example, from Patent Numbers EP-A-492, 366, WO 91/7874 and WO 94/987.
Depending on the intended use, a protector of the formulas in Ilg can be used to pre-treat the seeds of the crop plant (seed coatings or nurseries), or it can be placed in the soil before or after sowing . However, it can also be applied, by itself or together with the herbicide, immediately after the emergence of the plants. The treatment of the plants or the seeds with the protector, therefore, can in principle take place independently of the point in time of the application of the herbicide. However, the treatment of the plant can also be carried out by the simultaneous application of herbicide and protector (for example, as a tank mixture). The concentration of application of the protector to the herbicide to be applied, depends largely on the application method. In a field treatment performed either using a tank mixture comprising a combination of protector and herbicide, or by separate application of protector and herbicide, the ratio of the herbicide to the protector is generally from 1: 100 to 1: 1, preferably from 1:50 to 1: 5. In general, in the treatment of the field, apply from 0.001 to 5.0 kilograms of protector / hectare, preferably from 0.001 to 0.5 kilograms of protector / hectare. The application concentrations of the herbicide are generally between 0.001 and 2 kilograms / hectare, but preferably between 0.005 and 1 kilograms / hectare. The compositions according to the invention are suitable for all application methods which are customary in agriculture, for example application before emergence, application after emergence, and seed coating. In general, in the seed coating, 0.001 to 10 kilograms of protector / kilogram of seeds are applied, preferably 0.05 to 2 grams of protector / kilogram of seeds. If the protector is applied in liquid form shortly before sowing, accompanied by the swelling of the seeds, then it is convenient to use protective solutions comprising the active substance in a concentration of 10,000 ppm, preferably 100 to 1,000 ppm . For the application, the protectors of the formula II, or the combinations of these protectants with the herbicides of the formula I, are conveniently processed together with the auxiliaries that are customary in the formulation technique, to give particular formulations, for example concentrates in emulsion, brush-applicable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dry powders, granules or microcapsules. The formulations are produced in a known manner, for example by intimate mixing and / or milling of the active substances with liquid or solid formulation aids such as, for example, solvents or solid carriers. In addition, it is possible, in addition, to use surface activity compounds (surfactants) to produce the formulations.
Suitable solvents may be aromatic hydrocarbons, preferably fractions of 8 to 12 carbon atoms, for example mixtures of substituted xylene or naphthalenes, phthalates such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols, and ethers and esters thereof, such as ethanol, diethylene glycol, 2-methoxyethanol or 2-ethoxyethanol, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide. , or dimethyl formamide, and unmodified or epoxidized vegetable oils, such as coconut oil or epoxidized soybean oil; or water. As solid carriers, for example for dry powders and dispersible powders, in general use is made of ground natural minerals, such as calcite, talc, kaolin, montmorilo-nite, or attapulgite. In order to improve the physical properties of the formulation, it is also possible to add highly dispersed silica or highly dispersed absorbent polymers. Suitable adsorbent granulate carriers are porous types, for example pumice, broken septum, sepiolite or bentonite, while suitable non-sorbent carrier materials are, for example, calcite or sand. In addition, it is possible to use a large number of previously granulated materials of an inorganic or organic nature, such as, in particular, dolomite or waste from crushed plants. Suitable surface active compounds, depending on the protector and, if appropriate, the herbicide, are also nonionic, cationic, and / or anionic surfactants having good emulsifying, dispersing, and wetting properties. References to surfactants also include mixtures of surfactants. Suitable anionic surfactants can be both water-soluble soaps, and synthetic, water-soluble surface-active compounds. The soaps that may be mentioned are the alkali metal, alkaline earth metal, or substituted or unsubstituted ammonium salts of higher fatty acids (10 to 22 carbon atoms), for example the sodium or potassium salts of oleic or stearic acid, or mixtures of natural fatty acids which can be obtained, for example, from coconut oil or tallow oil. Other salts that may be mentioned are the methyl taurine salts of fatty acid. However, so-called synthetic surfactants, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives, or alkylarylsulfonate are more frequently used. Fatty sulphonates or fatty sulfates are generally present as alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts, and have an alkyl radical of 8 to 22 carbon atoms, the alkyl moiety also including alkyl. acyl radicals, the examples being the ocalcal sodium salt of lignin sulphonic acid, of dodecylsulfuric ester, or of a mixture of fatty alcohol sulphate prepared from natural fatty acids. Also included here are the sulfuric ester and sulfonic acid salts with fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid radical having from 8 to 22 carbon atoms. Examples of the alkylaryl sulfonates are the sodium, calcium, or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or a condensation product of naphthalenesulfonic acid formaldehyde. Suitable phosphates are also suitable, for example the phosphoric ether salts of adduct of p-nonylphenol- (4-14), ethylene oxide, or phospholipids. Suitable nonionic surfactants are primarily derived from polyglycol ether of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids, and alkylphenols, which may contain from 3 to 30 glycol ether groups, and from 8 to 20 carbon atoms in the hydrocarbon radical (aliphatic), and from 6 to 18 carbon atoms in the alkyl radical of the alkylphenols. Other suitable nonionic surfactants are the water-soluble adducts, which contain from 20 to 250 ethylene glycol ether groups, and from 10 to 100 groups of propylene glycol ether, polyethylene oxide and polypropylene glycol, glycol of ethylene diamine polypropylene and alkyl polypropylene glycol having from 1 to 10 carbon atoms in the alkyl chain. The aforementioned compounds typically contain from 1 to 5 ethylene glycol units per unit of propylene glycol. Examples of nonionic surfactants that may be mentioned are nonylphenol polyethoxyethanols, polyglycolic ethers of castor oil, adducts of polypropylene or polyethylene oxide, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Also suitable are polyoxyethylene sorbitan fatty acid esters, such as polyoxyethylene sorbitan trioleate. Cationic surfactants are primarily quaternary ammonium salts having, as the N substituent, at least one alkyl radical having from 8 to 22 carbon atoms, and as other substituents, unmodified or halogenated lower alkyl, benzyl, or hydroxyalkyl radicals lower. The salts are preferably in the form of halides, methyl sulfates, or ethyl sulfates, for example stearyltrimethyl ammonium chloride or ammonium benzyldi (2-chloroethyl) ethyl bromide. Surfactants customary in the art of the formulation, which may also be used in the compositions according to the invention, are described, inter alia, in "Me Cutcheon's Detergents and Emulsifiers Annual," MC Publishing Corp., Ridge Ood, New Jersey , 1981, Stache, H., "Tensid-Taschenbuch" [Handbook of Surfactants], Cari Hanser Verlag, Munich / Vienna, 1981, and M. and J. Ash, "Encyclopedia of Surfactants", Volumes I-III, Chemical Publishing Co., New York, 1980-81. Agrochemical formulations generally contain from 0.1 to 99 percent by weight, in particular from 0.1 to 95 percent by weight of protector or a protective / herbicidal active mixture, from 1 to 99.9 percent by weight, in particular from 5 to 95 percent by weight. to 99.8 weight percent of a solid or liquid formulation aid, and from 0 to 25 weight percent, in particular from 0.1 to 25 weight percent of a surfactant. Although the preferred commercial product usually comprises concentrated compositions, the end user generally employs diluted compositions. The compositions may also comprise other additives, such as stabilizers, defoamers, viscosity regulators, binders, adhesives and fertilizers or other active substances. For the use of formulas protectors
Ilg, or of the compositions comprising them to protect the crop plants against the harmful effects of the herbicides of the formula I, a variety of methods and techniques are suitable, the examples being the following: i) Seed coating a) The seeds are coated by agitating them, in a container, together with an active substance of the formulas lia to Ilg, formulated as a wettable powder, until the active ingredient is uniformly distributed on the surface of the seeds (dry seed coating). In this case, about 1 to 500 grams of active substance of the formulas lia a Ilg [from 4 grams to 2 kilograms of wettable powder) per 100 kilograms of seeds are used. b) The seeds are coated with an emulsion concentrate of the active substance of the formulas lia to Ilg according to method a) (wet seed coating). c) The seeds are coated by immersing them in a liquor containing 100 to 1000 ppm of active substance of the formulas lia to Ilg for 1 to 72 hours, and then, if desired, drying the seeds (soaking of seeds). The coating of the seeds and the treatment of the nursery that has begun to germinate, of course, is the preferred method of application, since the treatment with the active substance is directed entirely towards the target crop. As a rule, 1 to 1000 grams of antidote are used, preferably 5 to 150 grams of antidote per 100 kilograms of seeds, it being possible to deviate from these limit concentrations upwards or downwards (repeat the coating), depending on the method, which also makes possible the addition of other active substances or micronutrients.
ii) Application as a tank mix A liquid preparation of an antidote and herbicide mixture is used (mutual quantitative ratio between 10: 1 and
1: 100), with the application concentration of the herbicide
0. 005 to 5.0 kilograms per hectare. These mixtures in tanks are applied before or after sowing.
iii) Application in the furrow of the seeds The protector is introduced into the open furrow of the seeds, which contains the seeds, as an emulsion concentrate, a wettable powder, or in the form of granules.
After the seed furrow has been covered, the herbicide is applied before emergence in a customary manner.
iv) Controlled release of the active substance The active substance of the formulas lia to Ilg is applied in solution to mineral granule vehi or polymerised granules (urea / formaldehyde), which are then dried. If desired, a coating (coated granules) can be applied, which makes it possible to release the active substance in regulated quantities for a defined period.
The following examples illustrate the invention in greater detail without limiting it.
"IfPl?.? < ** formulation for mixtures of herbicides of the formula I and protectors of the formulas Ha to Ils (%» percent in Weight)
Fl. Concentrates in emulsion a) b) c) d) Mixture of active substance 5% 10% 25% 50% Dodecylbenzenesulfonate calcium 6% 8% 6% 8%
Polyglycol ether of castor oil (36 moles of ethylene oxide) 4% 4% 4%
Polyglycol ether of octylphenol (7 to 8 moles of ethylene oxide) 4% 2% Cyclohexanone 10% 20% Mixture of aromatic hydrocarbons of 9 to 12 carbon atoms 85% 78% 55% 16%
From these concentrates, by dilution with water, it is possible to produce emulsions of any desired concentration.
F2 Solutions a) b) c) d)
Mixture of active substance 5% 10% 50% 90% l-methoxy-3- (3-methoxypropoxy) -propane 20% 20% Polyethylene glycol, molecular weight: 400 20% 10% N-methyl-2-pyrrolidone 30% 10% Aromatic hydrocarbon mixture of 9 to 13 carbon atoms 75% 60% The solutions are suitable for use in the formula of very fine drops.
F3 Wettable powders a) b) O d)
Mixture of active substance 5% 25% 50% 80% Sodium ligninsulfonate 4% - 3% - Sodium lauryl sulfate 2% 3% _ 4% Sodium diisobutyl naphthalenesulfonate 6% 5% 6%
Octyl-phenol polyglycol ether (7 to 8 moles of ethylene oxide) - 1% 2% Highly dispersed silica 1% 3% 5% 10% Kaolin 88% 62% 35% The active substance is completely mixed with the additives, and The mixture is completely milled in a suitable mill. Wettable powders are obtained that can be diluted with water to give suspensions of any concentration
F 4. Coated granules a) b) c) Mixture of active substance 0. 1% 5% 15% Highly dispersed silica 0. 9% 2% 2% Inorganic vehicle material (0.1-1 mm), such as, for example, CaCo3 or Si02 99.0% 93% 83% The active substance is dissolved in methylene chloride, the solution is sprayed on the vehicle , and subsequently the solvent is evaporated in vacuo.
F5 Coated granules a) b) c) Mixture of active substance 0.1% 5% 15% Polyethylene glycol molecular weight: 200 1.0% 2% 3% Highly dispersed silica 0.9% 1% 2% Inorganic vehicle material (0.1-1 mm. ) such as, for example, CaCO3 or Si02 98.0% 92% 80% The finely ground active substance is uniformly applied in a mixer to the carrier material, which has been moistened with polyethylene glycol. Dust-free coated granules are obtained in this manner.
F6 Extruded granules a) b) c) d)
Mixture of active substance 0.1% 3% 5% 15% Sodium ligninsulfonate 1.5% 2% 3% 4% Carboxymethyl cellulose 1.4% 2% 2% 2% Kaolin 97.0% 93% 90% 79% The active substance is mixed with the additives , and the mixture is milled and moistened with water. This mixture is extruded and subsequently dried in a stream of air.
F7 Dry powders a) b) O Mixture of active substance 0.1% 1% 5%
Talcum 39.9% 49% 35%
Kaolin 60.0% 50% 60% Ready-to-use dry powders are obtained by mixing the active substance with the vehicles, and grinding the mixture in a suitable mill.
F8 Concentrates in suspension a) b) c) d) Mixture of active substance 3% 10% 25% 50% Ethylene glycol 5% 5% 5% 5% Nonylphenol polyglycol ether (15 moles of ethylene oxide) - 1 % 2% - 3% sodium ligninsulfonate 3% 4% 5% 1% carboxymethyl cellulose 1% 1% 1% 37% formaldehyde aqueous solution 0.2% 0.2% 0.2% 0.2%
Emulsion in silicone oil 0.8% 0.8% 0.8% 0.8% Water 87% 79% 62% 38%
The finely ground active substance is intimately mixed with the additives. In this way, a suspension concentrate is obtained, from which, by dilution with water, suspensions of any desired concentration can be produced.
The ability of the protectants of the formulas Ia to Ilg to protect the crop plants against the phytotoxic effect of the herbicides of the formula I is illustrated in the following examples.
Biological Examples Example Bl; Applications of mixtures of a herbicide of the formula I with a protector of the formulas lia to Ilg to cereals after emergence. Under greenhouse conditions, wheat is grown in plastic pots until the 2.5-leaf stage. In this step, both the herbicides of the formula I alone, as well as the mixture of the herbicides with a protector of the formulas I to Ilg, are applied to the test plants. The application takes place in the form of an aqueous suspension of the test substances (Formulation Example F7) with 500 liters of water / hectare. The application concentrations for the herbicide and the protector can be seen in Tables Bl, B2, B3, and B4. 28 days after the application, the test is evaluated using a percentage scale. The 100 percent denotes that the test plant died, while the 0 percent indicates that there was no phytotoxic effect. The results obtained (see Table Bl below) show that, with the protectors of the formulas lia to Ilg, the damage caused to the wheat by the herbicide of the formula I can be reduced in a substantial manner.
Table Bl; Herbicidal action of compounds of formula I without protector Herbicide 125 g / ha 60 g / ha 30 g / ha 15 g / ha 8 g / ha 4 gte No. 1.01 90% 75% 65% 90% 75% 65% 90 % 75% 65% 90% 75% 65% 90% 75% 65% 90% 75% 65% NO. 1.21 55% 30% 20% 10% Table B2; Herbicidal action of the compounds of the formula I with protective
Herbicide No. 1.01 125 g / ha 60 g / ha 30 g / ha Protector No. 125 s / h at 60 s / h at 30 g / ha 4.04 35% 30% 10% 5.01 50% 35% 25% 4.01 40% 30% 20% 5.08 45% 15% 15% 5.05 70% 40% 30% 4.02 40% 20% 10% 6.02 55% 35% 15%
Table B3; Herbicidal action of the compounds of the formula I with protective
Herbicide No. 1.21 60 g / ha 30 g / ha 15 g / ha 8 g / ha 4 g / ha Protector No. 30 g / ha 30 g / ha 30 g / ha 30 g / ha 30 g / ha 4.01 20% 10% 5% 0% 0% Table B4; Herbicide of the compounds of the formula I with protector; Herbicide No. 1.01 60 g / ha 30 g / ha 15 g / ha 8 g / ha 4 g / ha Protector 4.01 35% 30% 10% 5% 0%
g ampio B2; Applications of mixtures of a herbicide of the formula I with a protector of the formulas lia to Ilg to corn after emergence. Under greenhouse conditions, maize is grown in plastic pots until the 2.5-leaf stage. In this step, both the herbicides of the formula I alone, as well as the mixture of the herbicides with a protector of the formulas Ia to Ilg, are applied to the test plants. The application takes place in the form of an aqueous suspension of the test substances (Formulation Examples F7) with 500 liters of water / hectare. The application concentrations for the herbicide and the protector can be seen from Table B5. 19 days after the application, the test is evaluated using a percentage scale. 100 percent denotes «that the test plant died, while 0 percent denotes that there was no phytotoxic effect. The results obtained show that, with the protectors of the formulas lia to Ilg, the damage caused to corn by the herbicide of the formula can be substantially reduced.
I.
Table B5; Herbicidal action of the compounds of the formula I and "" »mixture thereof with the protectants of the formula II in corn Herbicide No. 1.01 8 g / ha 4 g / ha Protector 125 g / ha 125 g / ha No ^ sin protector 70% 45% 8,007 45% 25% 7,003 60% 30% 8,005 60% 20% 7,004 50% 35%
B-) ampio B3; Mixture applications of a herbicide of the formula I with a protector of the formulas to Ilg to rice after emergence Under greenhouse conditions, the test plants are sown or planted in plastic troughs in conventional soil. Then water is introduced to the surface of the earth. After 3 days, the water level is raised by 2 centimeters, and the herbicide is applied as an aqueous suspension (Example F7) by itself, and in a tank mix with the protectors. The application concentrations for the herbicide can be seen in Table B6. The application concentration for the protector is 125 grams / hectare. Then the cultivation of the test plants in the greenhouse is continued under optimal conditions. 13 days after the application, the test is evaluated using a scale of percentages. The 100 percent denotes that the test plant died, while the 0 percent indicates that there was no phytotoxic effect. The results obtained show that, with the protectors of the formulas Ia to Ilg, the damage caused to rice by the herbicide of the formula I can be substantially reduced:
Table B6; Herbicidal action of the compounds of the formula I and a »m fT. i? At * 103 same with the protectors of formula II in rice Herbicide "Rice" Yamabiko "" Rice "S-201" type of water
No. 1.01 8 g / ha 4 g / ha 8 g / ha 4 g / ha
Protector No. without protector 75% 65% 70 60 7.001 35% 30% 20 0 NOVELTY OF THE INVENTION
Having described the above invention, it is considered as a novelty, and therefore, the content of the following is claimed as property:
CLAIMS
1. A selective herbicidal composition, which comprises, in addition to customary inert formulation aids, an active substance comprising a mixture of: a) a herbicidally effective amount of a herbicide of the formula I:
R, z_S02-N-CO- (CRaRb) m-t- '^ (I), R2 Y.
wherein: Z is alkyl of 1 to 10 carbon atoms, alkyl of 1 to 10 carbon atoms substituted by halogen, cycloalkyl of 3 to 8 carbon atoms, R70-, R7S (0) n-, R7RgN-, RgCO-, R9ON = CR8-, (CH3) 3Si-, -CN or oxiranyl, alkenyl of 2 to 8 carbon atoms , alkenyl of 2 to 8 carbon atoms substituted by halogen, phenyl, phenyl substituted by halogen, alkyl of 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, cycloalkyl of 3 to 8 carbon atoms, R70-, R7S (0) n-, R7RgN-, (CH3) 3Si-, CN, RgCO-, or R9ON = CR8-, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms substituted by halogen, alkyl of 1 to 10 carbon atoms, phenyl, phenyl substituted by halogen , alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, R70- , R7S ( 0) n-, R7R8N-, (CH3) 3Si-, -CN, oxo, = NOR7, R8CO-, or R9ON = CR8-, cycloalkenyl of 3 to 8 carbon atoms, cycloalkenyl of 3 to 8 carbon atoms substituted by halogen, alkyl of 1 to 10 carbon atoms, phenyl, phenyl substituted by halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl R70-, R7S (0) n-, R7R8N-, (CH3) 3Si-, -CN, oxo, = NOR7, R8CO-, or R9ON = CR8-, -NR5R6, R10CON (R6) - or R10SO2N (R6) -, wherein: R7 is hydrogen, alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, phenyl, or phenyl substituted by halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon-carbonyl atoms, n is 0, 1, or 2, R8 is as defined by R7, or is C1-6 alkoxy, C3-8 alkenyloxy, or C3-8 alkynyloxy, R9 is alkyl of 1 to 10 carbon atoms, alkenyl of
2 to 8 carbon atoms, or alkenyl of 2 to 8 carbon atoms, R10 is alkyl of 1 to 10 carbon atoms, alkyl of 1 to 10 carbon atoms substituted by halogen, R70- R7S (0) E-, - NR7R8 or -CN, alkenyl of 2 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms substituted by halogen, R70-, R7S (0) n-, NR7R or -CN, phenyl, or phenyl substituted by halogen, alkyl of the 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, wherein R7, n , and R8 are as defined, R5 is alkyl of 1 to 10 carbon atoms, alkyl of 1 to 10 carbon atoms substituted by halogen, cycloalkyl of 3 to 8 carbon atoms, R70-, R7S (0) n, R7R8N - R8CO-, R9ON = CR8-, (CH3) 3Si-, -CN or oxiranyl, alkenyl of 2 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms substituted by halogen, phenyl, phenyl substituted by halogen, alkyl of 1 a 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, cycloalkyl of 3 to 8 carbon atoms carbon, R70-, R7S (0) n-, R7R8N-, (CH3) 3Si-, -CN, R8CO- or R9ON = CR8-, alkynyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms substituted by halogen, alkyl of 1 to 10 carbon atoms, phenyl, phenyl substituted by halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, R70-, R7S (0) n-, R7R8N-, (CH3) 3Si-, -CN, oxo, = N0R7, RgC0-, or R9ON = CR8-, cycloalkenyl of 3 to 8 carbon atoms, cycloalkenyl of 3 to 8 carbon atoms substituted by halogen, alkyl of 1 to 10 carbon atoms, phenyl, phenyl substituted by halogen, alkyl of 1 to 6 ato carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, R70-, R7S (0) n -, R7R8N-, (CH3) 3Si-, -CN, oxo, = NOR7, R8CO-, or R9ON = CR8-, or R70- wherein R7 is as defined, and Rg is as defined for R5, or is hydrogen, or together with R5 forms an alkylene radical of 4 to 7 carbon atoms, or Z is a radical of the formula: (25)
wherein: R50 is hydrogen, halogen, -N02, -CN, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen, -CN, -OCH3 or -SCH, alkenyl of 2 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms substituted by halogen or OCH3, alkynyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms substituted by halogen, -0CH3 or -Si (CH3) 3, cycloalkyl from 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms substituted by -F, -Cl, or -CH3,
C (O) R100, -OCH2CH2OR100, -OH, -C (R100) (OR110) (ORI20), "CO2R130, C (O) NR140R150, -N3, -SO2NR, 40R150, -SO3RJ60, -OSO2R170, phenyl, phenyl substituted by halogen, -CH3 or -OCH3, -O-R180, -S (O) hR180 or - (CH2) SG, where b and s, independently of each other, are 0 or
1, R60 is hydrogen, halogen, -CN, -N02, alkyl of 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen, -CO2R130, -SO2NR140R150, -NR140R150, alkoxy of 1 or 2 carbon atoms carbon, -OR190 # -S (O) bR190, haloalkoxy of 1 or 2 carbon atoms, thioalkyl of 1 or 2 carbon atoms, halotioalkyl of 1 or 2 carbon atoms, -CN, -OH or -SH, -CO2R130 , -SO2NR140R150 -NR14oRi5o * -S (O) bR190 or -OR190, R70 / independently in each presentation, is hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 atoms carbon, phenyl, phenyl substituted by halogen, -S (O) bR190 or -OR190, S (O) bR190, -OR190 or halogen, Rβ0 is hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4, Halogen, -CO2R130, -SO2NR140R150, -OSO2R170, -S (O) bR180, -CN or -N02, and R90 is hydrogen, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen or phenyl, alkenyl of 2 to 4 carbon atoms, phenyl, or phenyl substituted by halogen, alkyl of 1 to 4 carbon atoms, -N02, -CN, or alkoxy of 1 to 4 carbon atoms, wherein R100 is hydrogen, alkyl of 1 to. 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen or -OCH 3, cycloalkyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms substituted by halogen or -CH 3, alkenyl of 2 to 4 atoms carbon or alkynyl of 2 to 4 carbon atoms, R110 and R120 'independently of each other, are alkyl of 1 to 4 carbon atoms, or R110 and R120 are together -CH2CH2-, -CH2OCH2- or -CH2C (CH3) 2CH2- "Rl30 is hydrogen, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halogen, -CN, -CO2R100, -NRi ^ lSO" "OR100 ° Si (CH3) 3, alkynyl of 3 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms substituted by -CH 3 or -Si (CH 3) 3, cycloalkyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms-alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or -Si (CH3) 3, Rj40 is hydrogen or alkyl of 1 to 4 carbon atoms,
RJ5Q is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or alkenyl of 2 to 4 carbon atoms, or R140 and R150 are together - (CH2) 2 (CH2) a- (CH2 ) 2- or - (CH2) 20- (CH2) 2-, where a is 0 or 1, RjgO is alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 4 carbon atoms, Rj70 is alkyl of 1 to 4 carbon atoms OR -NR140R150, where R ^ and RJ5Q are as defined, R180 is alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 2 to 4 carbon atoms-alkyl, alkenyl of 2 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms, phenyl, or phenyl substituted by halogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, or haloalkyl of 1 to 3 carbon atoms, R190 is alkyl of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms substituted by -F, -Cl, or -ORjg0 which is 0 or 1, G is a radical of the formula:
wherein R260 is hydrogen or alkyl of 1 to 3 carbon atoms, and R270 is hydrogen, alkyl of 1 to 3 carbon atoms, or alkenyl of 2 to 4 carbon atoms, R2 is hydrogen, alkyl of 10 carbon atoms , alkyl of 1 to 10 carbon atoms substituted by alkoxy of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms-carbonyl, alkenyl of 3 to 8 carbon atoms or benzyl, X and Y, independently of each other , are = N-, = CH-or = CR-, where either X or Y should be = N-, and where R is halogen, alkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms carbon substituted by halogen, alkoxy of 1 to 6 carbon atoms or haloalkoxy of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms or haloalkoxy of 1 to 6 carbon atoms, R3 and R4, independently of each other, they are hydrogen, halogen, alkyl of 1 to 10 carbon atoms, R70- R7S (0) n,
R7R8N-, haloalkyl of 1 to 10 carbon atoms, haloalkoxy of 1 to 10 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms or thiophenyl, wherein R7, n, and R8 are as defined, or R3 or R4, together with R, form a radical -OCH2CH2 (CH2) m- or - (CH2) mCH2CH20-, where m is 0 or 1, Ra is hydrogen, alkyl of 1 to 8 atoms carbon, alkyl of 1 to 8 carbon atoms substituted by hydroxy, alkoxy of 1 to 8 carbon atoms, phenoxy, thioalkyl of 1 to 8 carbon atoms, thiophenyl, (CH 3) Si-, cycloalkyl of 3 to 8 carbon atoms carbon, phenyl, or dialkyl of 1 to 8 carbon atoms-amino, alkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms substituted by halogen, or Ra is alkynyl of 2 to 6 carbon atoms, cycloalkyl from 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms substituted by alkyl of 1 to 3 carbon atoms, or Ra is cycloalkenyl of 3 to 6 carbon atoms, phenyl, substituted phenyl by alkyl of 1 to 8 carbon atoms, halogen, nitro, -CN, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, phenoxy, -NR7Rg or R8CO-, wherein R7 and R8 are as defined, or Ra is hydroxyl, halogen, tetrahydrothienyl, tetrahydrofuryl, furyl, pyridyl, or thienyl,, R |, is hydrogen, alkyl of 1 to 8 carbon atoms, or phenyl, or Ra Rb 'together with the carbon with which they are attached, form a radical of the formula -CO-, and m is 0 or 1; and also salts and stereoisomers of the compounds of the formula I, and b) an antagonistically effective amount of herbicide of a compound of the formula lia:
wherein: RQIQ is hydrogen, alkyl of 1 to 8 carbon atoms, or alkyl of 1 to 8 carbon atoms which is substituted by alkoxy of 1 to 6 carbon atoms or alkenyloxy of 3 to 6 carbon atoms, and X2 is hydrogen chloride, of a compound of the formula Ilbj:
wherein: E is nitrogen or methine, R 11 is -CC13 or phenyl unsubstituted or substituted by halogen, R | 2 and R13, independently of each other, are hydrogen or halogen, and R | is alkyl of 1 to 4 carbon atoms, of a compound of formula IIb:
wherein: R12 and Ri3 are as defined above, and R66 »R67» and R68 'independently of each other, are alkyl of 1 to 4 carbon atoms, of a compound of the formula loe:
where: A2 is a group:
R25 and R26 'independently of one another, are hydrogen, alkyl of 1 to £ carbon atoms, cycloalkyl "- 2 to 8 carbon atoms, alkenyl of 3 to 6 carbon atoms,
, alkynyl of 3 to 6 carbon atoms,, or
alkyl of 1 to 4 carbon atoms which is substituted by alkoxy
from 1 to 4 carbon atoms or; or
Rj or R2 together form an alkylene bridge of 4 to 6 carbon atoms which may be interrupted by oxygen, sulfur, SO, S02, NH, or -N (alkyl of 1 to 4 carbon atoms) -, R27 is hydrogen, or alkyl of 1 to 4 carbon atoms, -
Raa is hydrogen, halogen, cyano, trifluoromethyl, nitro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon atoms-sulfonyl, -COORj, -CONRkRm, -CORn, -S02NRkRm, or -0S02-alkyl of 1 to 4 carbon atoms, -Rg is hydrogen, halogen, cyano, nitro, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon atoms-sulfonyl, -COORj, -C0NRkRm, -CORn, -S02NRkRm, -OS02-alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms substituted by alkoxy of 1 to 4 carbon atoms or halogen, alkenyloxy of 3 to 6 carbon atoms, or alkenyloxy of 3 to 6 carbon atoms substituted by halogen, or alkynyloxy of 3 to 6 carbon atoms, or Ra and Rb together form a alkylene bridge of 3 to 4 carbon atoms, which may be substituted by halogen or alkyl of 1 to 4 carbon atoms, or form an alkenylene bridge of 3 to 4 carbon atoms which may be substituted by halogen or alkyl of 1 to 4 carbon atoms; to 4 carbon atoms, or they form a C 4 -aldienylene bridge which may be substituted by halogen or alkyl of 1 to 4 carbon atoms; Rbb and Rh "independently of each other, are hydrogen, halogen, alkyl of 1 to 4 carbon atoms, trifluoromethyl, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, or -COORJ; Rc is hydrogen, halogen, nitro, alkyl of 1 to 4 carbon atoms or methoxy; Hydrogen, halogen, nitro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon-sulfonyl atoms, -COORj Ó CONRkR, n; Re is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, -COORj, trifluoromethyl or methoxy, or R¿ and Re together form an alkylene bridge of 3 to 4 carbon atoms, - Rf is hydrogen, halogen, or alkyl from 1 to 4 carbon atoms, - Rx and Ry, independently of one another, are hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, -COOR8, trifluoromethyl, nitro, or cyano, -Rji Rk, and Rm, independently of each other, are hydrogen or alkyl of 1 to 4 carbon atoms, - or Rk and Rm together form an alkylene bridge of 4 to 6 atoms of carbon, which may be interrupted by oxygen, NH, or -N (alkyl of 1 to 4 carbon atoms) -, - Rjj is alkyl of 1 to 4 carbon atoms, phenyl, or phenyl which is substituted by halogen, alkyl of 1 to 4 carbon atoms, methoxy, nitro, or trifluoromethyl;
R28 is hydrogen, alkyl of 1 to 10 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, dialkyl from 1 to 4 carbon atoms-aminoalkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, haloalkenyl of 2 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, halocycloalkyl of 3 to 7 carbon atoms, alkyl of 1 to 8 carbon atoms, carbonyl, allylcarbonyl, cycloalkyl of 3 to 7 carbon atoms, benzoyl which is unsubstituted or substituted on the phenyl ring by up to three identical substituents
0 different consisting of halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms, - or furoyl, thienyl; or alkyl of 1 to 4 carbon atoms substituted by phenyl, halophenyl, alkyl of 1 to 4 carbon atoms-phenyl, alkoxy of 1 to 4 carbon atoms-phenyl, haloalkyl of
1 to 4 carbon atoms-phenyl, haloalkoxy of 1 to 4 carbon atoms-phenyl, alkoxy of 1 to 6 carbon atoms-carbonyl, alkoxy of 1 to 4 carbon atoms-alkoxy of 1 to 8 carbon atoms-carbonyl , alkenyloxy of 3 to 8 carbon atoms-carbonyl, alkynyloxy of 3 to 8 carbon atoms-carbonyl, thioalkyl of 1 to 8 carbon atoms-carbonyl, thioalkenyl of 3 to 8 carbon atoms-carbonyl, thioalkynyl of 3 to 8 carbon-carbonyl, carbamoyl, monoalkyl of 1 to 4 carbon atoms-aminocarbonyl, dialkyl of 1 to 4 carbon atoms-aminocarbonyl, or phenylaminocarbonyl atoms which is unsubstituted or substituted on phenyl by up to three identical or different substituents consisting of halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms, or by a single substituent of cyano or nitro , or dioxolan-2-yl which is unsubstituted or which is is substituted by one or two alkyl radicals of 1 to 4 carbon atoms, or dioxan-2-yl which is unsubstituted or which is substituted by one or two alkyl radicals of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms which is substituted by cyano, nitro, carboxyl, or thioalkyl of 1 to 8 carbon atoms-alkoxy of 1 to 8 carbon atoms-carbonyl, of a compound of the formula le:
«33 o \ II / - (He)« 34 '
wherein: R33 and R34, independently of one another, are alkyl of 1 to 6 carbon atoms or alkenyl of 2 to 6 carbon atoms; or R33 and R34 are together
R35 and R36, independently of one another, are hydrogen, or alkyl of 1 to 6 carbon atoms, - or R33 and R3 are together
R37 and R38, independently of one another, are alkyl of 1 to 4 carbon atoms, or R37 and R38 are together - (CH2) 5 -, - R39 is hydrogen, alkyl of 1 to 4 carbon atoms,
or R33 and R3 are j untos
R40- R41 '^ 42' R43 'R44' R45 'R46' R47 'R48' R49 '^ 50' R51 'R52, R53, R54, and R55, independently of each other, are hydrogen or alkyl of 1 to 4 carbon atoms carbon, - of a compound of the formula Ilf:
wherein: R3 is hydrogen or chloro, and Rg4 is cyano or trifluoromethyl, or a compound of the formula Ilg:
wherein: R65 is hydrogen or methyl. 2. A composition according to claim 1, which comprises as a herbicide a compound of the formula
1 wherein R3 and R are methoxy. 3. A composition according to the claim
1, which comprises as herbicide a compound of the formula I wherein R3 and R are methoxy, and Z is alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 8 carbon atoms, or haloalkenyl of
2 to 8 carbon atoms.
4. A composition according to claim 3, which comprises as a herbicide, a compound of the formula I wherein Z is -CH 2 -CH (CH 3) 2, -CH 2 C (CH 3) = CH 2 or -CH 2 -CH = CHC 1. 5. A composition according to the claim
1, which comprises as a herbicide, a compound of the formula I wherein Z is -CH2-CH (CH3) 2, -CH2C (CH3) = CH2 or -CH2-CH = CHC1 and m is
0. 6 A composition according to claim 1, which comprises as a protector a compound of the formulas
Ha, Hbj, Hb2, or He. 7. A composition according to claim 6, which comprises as protector a compound of the formulas Hbj or Hb2. 8. A composition according to the claim
6, which comprises as protector a compound of the formula Ha. 9. A composition according to claim 1, which comprises as a herbicide, a compound of the formula I wherein Z is -CH2-CH (CH3) 2, -CH2-C (CH3) = CH2 or -CH2-CH = CHC1 Y m is 0, and as protective a compound of formula Ha. 10. A composition according to claim 9, which comprises as a protector a compound of the formula Ha ?: OCH2C02-CH (CH3) -C5H1, -n
11. A process for the selective control of broadleaf grasses and grasses in crops of useful plants, which comprises treating the useful plants, their seeds or seedbeds, or their growing area, in a simultaneous or separate manner, with a herbicidally amount effective of a herbicide of the formula I, and an antagonistically effective herbicide amount of a protector of the formulas Ha to Hg. 12. A process according to claim 11, wherein crops of useful plants or cultivation areas for crops of useful plants are treated, with 0.001 to 2 kilograms / hectare of a herbicide of the formula I, and with an amount from 0.001 to 0.5 kilograms / hectare of a protector of the formulas Ha to Hg. 13. A process according to claim 11, wherein the crops of useful pLantas are those of corn or cereals, especially rye, barley, oats, or wheat.
Claims (1)
- SUMMARY OF THE INVENTION A selective herbicidal composition, which comprises, in addition to customary inert forming aids, an active substance comprising a mixture of: a) a herbicidally effective amount of a herbicide of the formula I: b) an antagonistically effective herbicide amount of a compound of the formula Ha: a compound of the formula Hbj a compound of the formula IIb2: a compound of the formula He: a compound of the formula He: R, or \ p NC-CHCU (He) R a compound of formula IIf or a compound of the formula Hg: wherein the substituents are as defined in claim 1. * * * * *
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH145/95 | 1995-01-19 | ||
CH14595 | 1995-01-19 | ||
PCT/EP1996/000032 WO1996022022A1 (en) | 1995-01-19 | 1996-01-05 | Herbicidal composition |
Publications (2)
Publication Number | Publication Date |
---|---|
MX9705448A MX9705448A (en) | 1997-10-31 |
MXPA97005448A true MXPA97005448A (en) | 1998-07-03 |
Family
ID=
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