AU2019253885B2 - Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides - Google Patents
Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides Download PDFInfo
- Publication number
- AU2019253885B2 AU2019253885B2 AU2019253885A AU2019253885A AU2019253885B2 AU 2019253885 B2 AU2019253885 B2 AU 2019253885B2 AU 2019253885 A AU2019253885 A AU 2019253885A AU 2019253885 A AU2019253885 A AU 2019253885A AU 2019253885 B2 AU2019253885 B2 AU 2019253885B2
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- AU
- Australia
- Prior art keywords
- herbicidal
- alkyl
- compound
- arylalkyl
- herbicidal compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 50
- 150000001875 compounds Chemical class 0.000 title claims abstract description 46
- 125000003710 aryl alkyl group Chemical group 0.000 title claims abstract description 20
- -1 trialkylammonium hydroxides Chemical class 0.000 title claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 title description 4
- 125000005207 tetraalkylammonium group Chemical group 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 25
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 21
- 239000005627 Triclopyr Substances 0.000 claims description 13
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims description 13
- 239000002671 adjuvant Substances 0.000 claims description 8
- ROBSGBGTWRRYSK-SNVBAGLBSA-N (2r)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(C#N)C=C1F ROBSGBGTWRRYSK-SNVBAGLBSA-N 0.000 claims description 7
- 239000005504 Dicamba Substances 0.000 claims description 7
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 7
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000005561 Glufosinate Substances 0.000 claims description 5
- 239000005562 Glyphosate Substances 0.000 claims description 5
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 5
- 229940097068 glyphosate Drugs 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 claims description 3
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 claims description 3
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 claims description 3
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005468 Aminopyralid Substances 0.000 claims description 3
- 239000005498 Clodinafop Substances 0.000 claims description 3
- 239000005500 Clopyralid Substances 0.000 claims description 3
- 239000005558 Fluroxypyr Substances 0.000 claims description 3
- 239000005595 Picloram Substances 0.000 claims description 3
- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229940075419 choline hydroxide Drugs 0.000 claims description 3
- YUIKUTLBPMDDNQ-MRVPVSSYSA-N clodinafop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1F YUIKUTLBPMDDNQ-MRVPVSSYSA-N 0.000 claims description 3
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 3
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims description 3
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 claims description 3
- WNTGYJSOUMFZEP-SSDOTTSWSA-N (R)-mecoprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-SSDOTTSWSA-N 0.000 claims description 2
- ADDQHLREJDZPMT-AWEZNQCLSA-N (S)-metamifop Chemical compound O=C([C@@H](OC=1C=CC(OC=2OC3=CC(Cl)=CC=C3N=2)=CC=1)C)N(C)C1=CC=CC=C1F ADDQHLREJDZPMT-AWEZNQCLSA-N 0.000 claims description 2
- 239000002794 2,4-DB Substances 0.000 claims description 2
- YNTJKQDWYXUTLZ-UHFFFAOYSA-N 2-(3-chlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC(Cl)=C1 YNTJKQDWYXUTLZ-UHFFFAOYSA-N 0.000 claims description 2
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 2
- SVGBNTOHFITEDI-UHFFFAOYSA-N 2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1Cl SVGBNTOHFITEDI-UHFFFAOYSA-N 0.000 claims description 2
- BSFAVVHPEZCASB-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1 BSFAVVHPEZCASB-UHFFFAOYSA-N 0.000 claims description 2
- VAZKTDRSMMSAQB-UHFFFAOYSA-N 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 VAZKTDRSMMSAQB-UHFFFAOYSA-N 0.000 claims description 2
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 claims description 2
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 claims description 2
- DKHJWWRYTONYHB-UHFFFAOYSA-N CPP Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1 DKHJWWRYTONYHB-UHFFFAOYSA-N 0.000 claims description 2
- ZLSWBLPERHFHIS-UHFFFAOYSA-N Fenoprop Chemical compound OC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl ZLSWBLPERHFHIS-UHFFFAOYSA-N 0.000 claims description 2
- ANFHKXSOSRDDRQ-UHFFFAOYSA-N Isoxapyrifop Chemical compound C1CCON1C(=O)C(C)OC(C=C1)=CC=C1OC1=NC=C(Cl)C=C1Cl ANFHKXSOSRDDRQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005574 MCPA Substances 0.000 claims description 2
- 239000005575 MCPB Substances 0.000 claims description 2
- 101150039283 MCPB gene Proteins 0.000 claims description 2
- 239000005576 Mecoprop-P Substances 0.000 claims description 2
- 239000005600 Propaquizafop Substances 0.000 claims description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 2
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 38
- 150000003839 salts Chemical class 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 6
- 241000196324 Embryophyta Species 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000006378 damage Effects 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- 241000209140 Triticum Species 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 6
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 208000014674 injury Diseases 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 241000219094 Vitaceae Species 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
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- 238000009472 formulation Methods 0.000 description 4
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- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 240000001140 Mimosa pudica Species 0.000 description 3
- 235000016462 Mimosa pudica Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- WJLUBOLDZCQZEV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)C WJLUBOLDZCQZEV-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
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- 125000005208 trialkylammonium group Chemical group 0.000 description 3
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 2
- IUQJDHJVPLLKFL-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetate;dimethylazanium Chemical compound CNC.OC(=O)COC1=CC=C(Cl)C=C1Cl IUQJDHJVPLLKFL-UHFFFAOYSA-N 0.000 description 2
- ROKVVMOXSZIDEG-UHFFFAOYSA-N 2-(3,5,6-trichloropyridin-2-yl)oxyacetate;triethylazanium Chemical compound CCN(CC)CC.OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl ROKVVMOXSZIDEG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
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- 239000008187 granular material Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 241000894007 species Species 0.000 description 2
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- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 2
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 1
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- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 description 1
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- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 1
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- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 description 1
- ZMWGIGHRZQTQRE-UHFFFAOYSA-N 2-butoxyethyl 2-(2,4-dichlorophenoxy)acetate Chemical compound CCCCOCCOC(=O)COC1=CC=C(Cl)C=C1Cl ZMWGIGHRZQTQRE-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- BCIHMWNOJJYBSJ-UHFFFAOYSA-N 2-pyrimidin-2-yloxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=NC=CC=N1 BCIHMWNOJJYBSJ-UHFFFAOYSA-N 0.000 description 1
- SIYAHZSHQIPQLY-UHFFFAOYSA-N 4-(4-chlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1 SIYAHZSHQIPQLY-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (11)
Priority Applications (2)
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AU2019253885A AU2019253885B2 (en) | 2007-02-26 | 2019-10-25 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2021204118A AU2021204118A1 (en) | 2007-02-26 | 2021-06-18 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
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US60/903,417 | 2007-02-26 | ||
AU2013203406A AU2013203406B2 (en) | 2007-02-26 | 2013-04-10 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2015200368A AU2015200368B2 (en) | 2007-02-26 | 2015-01-27 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2016202508A AU2016202508C1 (en) | 2007-02-26 | 2016-04-20 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2017261483A AU2017261483C1 (en) | 2007-02-26 | 2017-11-14 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2019253885A AU2019253885B2 (en) | 2007-02-26 | 2019-10-25 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
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AU2017261483A Division AU2017261483C1 (en) | 2007-02-26 | 2017-11-14 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
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AU2021204118A Division AU2021204118A1 (en) | 2007-02-26 | 2021-06-18 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
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AU2016202508A Active AU2016202508C1 (en) | 2007-02-26 | 2016-04-20 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2017261483A Active AU2017261483C1 (en) | 2007-02-26 | 2017-11-14 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2019253885A Ceased AU2019253885B2 (en) | 2007-02-26 | 2019-10-25 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2021204118A Pending AU2021204118A1 (en) | 2007-02-26 | 2021-06-18 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
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AU2015200368A Active AU2015200368B2 (en) | 2007-02-26 | 2015-01-27 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2016202508A Active AU2016202508C1 (en) | 2007-02-26 | 2016-04-20 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
AU2017261483A Active AU2017261483C1 (en) | 2007-02-26 | 2017-11-14 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
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AU2021204118A Pending AU2021204118A1 (en) | 2007-02-26 | 2021-06-18 | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
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Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1056235A (en) * | 1964-05-26 | 1967-01-25 | May & Baker Ltd | Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them |
US3852340A (en) * | 1966-09-26 | 1974-12-03 | Akzona Inc | Plant hormone carboxylic acid salts of aliphatic polyamines |
JPS51106728A (en) * | 1975-03-12 | 1976-09-21 | Mitsubishi Gas Chemical Co | JOSOZAI |
US4534783A (en) * | 1984-01-03 | 1985-08-13 | Monsanto Co. | High concentration encapsulation of water soluble-materials |
EP0183384A1 (en) * | 1984-11-26 | 1986-06-04 | Sandoz Ltd. | Low-volatile salt of dicamba and herbicides |
EP0274369A1 (en) * | 1986-12-04 | 1988-07-13 | Monsanto Company | Glyphosate-ammonium sulfate herbicidal formulation |
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2015
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2016
- 2016-04-20 AU AU2016202508A patent/AU2016202508C1/en active Active
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2017
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AU2021204118A1 (en) | 2021-07-15 |
AU2016202508C1 (en) | 2018-11-29 |
AU2015200368A1 (en) | 2015-02-19 |
AU2017261483C1 (en) | 2024-04-18 |
AU2019253885A1 (en) | 2019-11-14 |
AU2015200368B2 (en) | 2016-04-21 |
AU2017261483B2 (en) | 2019-07-25 |
AU2016202508B2 (en) | 2017-08-31 |
AU2017261483A1 (en) | 2017-11-30 |
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