JP4686457B2 - グリホサートの高強度、低粘度除草製剤 - Google Patents
グリホサートの高強度、低粘度除草製剤 Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims description 142
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims description 56
- 239000005562 Glyphosate Substances 0.000 title claims description 54
- 229940097068 glyphosate Drugs 0.000 title claims description 54
- 230000002363 herbicidal effect Effects 0.000 title claims description 43
- 238000009472 formulation Methods 0.000 title description 104
- 239000004094 surface-active agent Substances 0.000 claims description 51
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 40
- -1 alkyl ether amine Chemical class 0.000 claims description 23
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 23
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000012141 concentrate Substances 0.000 claims description 9
- 239000002280 amphoteric surfactant Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
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- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 229920001282 polysaccharide Polymers 0.000 claims description 4
- 239000005017 polysaccharide Substances 0.000 claims description 4
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000007942 carboxylates Chemical group 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003760 tallow Substances 0.000 claims 1
- 150000004656 dimethylamines Chemical class 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- VDCHTAFVUAPYGO-UHFFFAOYSA-N n-methylmethanamine;2-(phosphonomethylamino)acetic acid Chemical compound CNC.OC(=O)CNCP(O)(O)=O VDCHTAFVUAPYGO-UHFFFAOYSA-N 0.000 description 12
- 239000004009 herbicide Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 150000003973 alkyl amines Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- LIOPHZNMBKHGAV-UHFFFAOYSA-M potassium;2-(phosphonomethylamino)acetate Chemical compound [K+].OC(=O)CNCP(O)([O-])=O LIOPHZNMBKHGAV-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000012266 salt solution Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 238000007046 ethoxylation reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000002169 ethanolamines Chemical class 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 206010015946 Eye irritation Diseases 0.000 description 2
- 239000005627 Triclopyr Substances 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 231100000013 eye irritation Toxicity 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 238000011272 standard treatment Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- 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 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
(a)化学式
(b)化学式
(i)R4は、場合により1又はそれ以上のエーテル結合に割り込まれた、ベンジルまたはC8−C24、好ましくはC12−C18直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、R5、R6およびR7は、独立してC1−C4アルキル基、好ましくはメチル基であり、
(ii)R4およびR5は独立して、場合により1又はそれ以上のエーテル結合に割り込まれたC8−C24、好ましくはC12−C18直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、R6およびR7は独立してC1−C4アルキル基、好ましくはメチル基であり、
(iii)R4は、場合により1又はそれ以上のエーテル結合に割り込まれたC8−C24、好ましくはC12−C18、直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、R5は、2〜22個の、好ましくは2〜15個のC2−C4アルキレンオキシド単位、好ましくはエチレンオキシド単位を有するポリオキシアルキレン鎖であり、R6およびR7は独立して、C1−C4アルキル基、好ましくはメチル基であり、あるいは
(iv)R4は、場合により1又はそれ以上のエーテル結合に割り込まれたC8−C24、好ましくはC12−C18直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、R5およびR6は、2〜22個の、好ましくは2〜15個のC2−C4アルキレンオキシド単位、好ましくはエチレンオキシド単位を有するポリオキシアルキレン鎖であり、R7はC1−C4アルキル基、好ましくはメチル基である、
を含む)を有する、第4級アンモニウム界面活性剤、
(c)化学式
(v)R8は、C8−C24、好ましくはC12−C18直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、R9およびR10は独立して、C1−C4アルキル基、好ましくはメチル基または水素原子であり、nは1〜5の整数である、または
(vi)R8は、[R11−CONH−(CH2)x−]ラジカル(式中、R11はC8−C24、好ましくはC12−C18、直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、xは1〜5の整数である)であり、R9およびR10は独立して、C1−C4アルキル基、好ましくはメチル基または水素原子であり、nは1〜5の整数である、
を含む)を有する、両性界面活性剤、
(d)化学式
(e)化学式
(f)一般化学式
を有するアルキルポリグリコシド、
(g)化学式
を有するアルキルポリグリコシドのアニオン性エステル誘導体(欧州特許第EP 0258 814 B1号を参照)、あるいは
(h)その混合物。
グリホサートDMA塩濃縮物は、グリホサートテクニカルウェットケーキ 408gと、水 61gによる40% ジメチルアミン水溶液 283gと反応させることによって調製した。濃縮物は62%のグリホサートDMA塩を含有していた。溶液は1.259g/mlの密度を有する。
グリホサートDMA塩製剤を、温室試験において一連の5種類の双子葉および3種類の単子葉雑草に対する効力について評価した。製剤は100、200、400、600および800gae/haにて、標準処理としてのRoundup Ultra(商標)除草剤、Roundup UltraMAX(商標)およびRoundup WeatherMAX(商標)除草剤(すべてMonsanto)と共に使用した。噴霧体積は187リットル/ヘクタール(l/ha)であった。雑草は使用時には3葉期であった。各処理は、3回反復した。評価は、使用14日後に、防除%の目視評価によって行った。
グリホサート塩溶液は、グリホサートDMA塩濃縮物およびグリホサートK塩濃縮物を、480g/l グリホサート酸当量をそれぞれ含有する溶液を調製するために必要な量の水で希釈することによって調製した。
5つの広葉種(IPOHE、CHEAL、EPHHL、ABUTHおよびCASOB)に、表6に示す混合物と同様に個々の製剤を噴霧した。
除草剤の相互作用をColbyの式によって解析した。予測される混合物反応に関するこの式は、
y1+2=y1+y2−(y1y2)/100
であり、式中、y1+2は予測される混合物反応であり、y1およびy2は個々の除草剤の防除パーセント値である。
グリホサートMMA塩濃縮物は、グリホサートテクニカルウェットケーキ 505gを、水 121gによる41% メチルアミン水溶液 238gと反応させることによって調製した。濃縮物は62% グリホサートMMA塩を含有していた。溶液は1.302g/mlの密度を有する。
グリホサートMMA塩製剤を、温室試験において一連の5種類の双子葉および3種類の単子葉雑草に対する効力について評価した。製剤は100、200、400、600および800gae/haにて、標準処理としてのRoundup WeatherMAX除草剤(Monsanto)と共に使用した。噴霧体積は140リットル/ヘクタール(l/ha)である。雑草は使用時には3葉期であった。各処理は3回反復した。評価は、使用14日後に、防除%の目視評価によって行った。
表9は、400gae/haの使用率での個々の雑草種についての防除パーセントを示す。
Claims (7)
- (a)水と、(b)組成物1リットル当たり350グラム酸当量を超える量の、水溶液中の主にモノメチルアミンまたはジメチルアミン塩の形のグリホサートと、(c)組成物1リットル当たり20〜200グラムの全量の、少なくとも1つの界面活性剤とから本質的に成り、140センチポイズ未満の粘度を有する、高濃度除草濃縮組成物であって、
前記界面活性剤が、
(a)化学式
(b)化学式
(i)R 4 は、場合により1又はそれ以上のエーテル結合に割り込まれた、ベンジルまたはC 8 −C 24 直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、R 5 、R 6 およびR 7 は、独立してC 1 −C 4 アルキル基であり、
(ii)R 4 およびR 5 は独立して、場合により1又はそれ以上のエーテル結合に割り込まれたC 8 −C 24 直鎖または分岐鎖, 飽和または不飽和ヒドロカルビル基であり、R 6 およびR 7 は独立してC 1 −C 4 アルキル基であり、
(iii)R 4 は、場合により1又はそれ以上のエーテル結合に割り込まれたC 8 −C 24 直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、R 5 は、2〜22個のC 2 −C 4 アルキレンオキシド単位を有するポリオキシアルキレン鎖であり、R 6 およびR 7 は独立して、C 1 −C 4 アルキル基であり、あるいは
(iv)R 4 は、場合により1又はそれ以上のエーテル結合に割り込まれたC 8 −C 24 直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、R 5 およびR 6 は、2〜22個のC 2 −C 4 アルキレンオキシド単位を有するポリオキシアルキレン鎖であり、R 7 はC 1 −C 4 アルキル基である、
を含む)を有する、第4級アンモニウム界面活性剤、
(c)化学式
(v)R 8 は、C 8 −C 24 直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、R 9 およびR 10 は独立して、C 1 −C 4 アルキル基または水素原子であり、nは1〜5の整数である、または
(vi)R 8 は、[R 11 −CONH−(CH 2 ) x −]ラジカル(式中、R 11 はC 8 −C 24 直鎖または分岐鎖、飽和または不飽和ヒドロカルビル基であり、xは1〜5の整数である)であり、R 9 およびR 10 は独立して、C 1 −C 4 アルキル基または水素原子であり、nは1〜5の整数である、
を含む)を有する、両性界面活性剤、
(d)化学式
(e)化学式
(f)一般化学式
を有するアルキルポリグリコシド、
(g)化学式
を有するアルキルポリグリコシドのアニオン性エステル誘導体、あるいは
(h)その混合物、
である、高濃度除草濃縮組成物。 - 組成物1リットル当たり440グラム超グリホサート酸当量を含有する、請求項1に記載の組成物。
- 100センチポイズ未満の粘度を有する、請求項1に記載の組成物。
- 界面活性剤が、獣脂アミンエトキシラートのブレンドおよび式
- 粘度が100センチポイズ未満であり、組成物1リットル当たり480グラム超グリホサート酸当量を含有する、請求項4に記載の組成物。
- 請求項1に記載の水希釈組成物を草木に使用することを含む、望ましくない草木を防除する方法。
- 前記(h)その混合物が、前記(a)のアルキルエーテルアミン界面活性剤と前記(c)の両性界面活性剤との混合物である、請求項1に記載の高濃度除草濃縮組成物。
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US49355403P | 2003-08-04 | 2003-08-04 | |
US60/493,554 | 2003-08-04 | ||
PCT/US2004/003472 WO2005016002A1 (en) | 2003-08-04 | 2004-02-06 | High-strength, low viscosity herbicidal formulations of glyphosate |
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JP4686457B2 true JP4686457B2 (ja) | 2011-05-25 |
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ES2413083T3 (es) * | 2009-04-22 | 2013-07-15 | Dow Agrosciences Llc | Composiciones herbicidas, de mucha fuerza, de sales de glifosato y 2,4 D |
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IT1395428B1 (it) * | 2009-07-01 | 2012-09-14 | Lamberti Spa | Concentrato acquoso di erbicida |
WO2011008281A1 (en) * | 2009-07-14 | 2011-01-20 | Rhodia Operations | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
DE102009041003A1 (de) * | 2009-09-10 | 2011-03-24 | Clariant International Limited | Pestizidzubereitungen |
US20110175026A1 (en) * | 2010-01-15 | 2011-07-21 | Lamberti Spa | Process for wetting a water repellant soil |
EP3066926A3 (en) * | 2010-04-20 | 2016-11-02 | Dow AgroSciences LLC | Aqueous herbicidal concentrates of auxinic carboxylic acids with reduced eye irritancy |
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WO2012061106A1 (en) | 2010-10-25 | 2012-05-10 | Stehpan Company | Glyphosate formulations based on compositions derived from natural oil metathesis |
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CY1118428T1 (el) | 2017-06-28 |
AU2004264781B2 (en) | 2010-02-18 |
CA2531340C (en) | 2011-08-09 |
EP1651048B1 (en) | 2016-08-17 |
RU2336700C2 (ru) | 2008-10-27 |
MXPA06001389A (es) | 2006-05-15 |
WO2005016002A1 (en) | 2005-02-24 |
PL221513B1 (pl) | 2016-04-29 |
ZA200600081B (en) | 2007-03-28 |
PT1651048T (pt) | 2016-09-26 |
ES2593006T3 (es) | 2016-12-05 |
PL378935A1 (pl) | 2006-06-12 |
US20050032649A1 (en) | 2005-02-10 |
BRPI0413266A (pt) | 2006-10-10 |
BRPI0413266B8 (pt) | 2022-06-28 |
JP2007501226A (ja) | 2007-01-25 |
AU2004264781A1 (en) | 2005-02-24 |
HUE030940T2 (en) | 2017-06-28 |
CA2531340A1 (en) | 2005-02-24 |
BRPI0413266B1 (pt) | 2015-07-21 |
AR043383A1 (es) | 2005-07-27 |
CN1826055B (zh) | 2010-05-26 |
EP1651048A1 (en) | 2006-05-03 |
CN1826055A (zh) | 2006-08-30 |
RU2006106709A (ru) | 2006-07-27 |
UA80911C2 (en) | 2007-11-12 |
CO5650202A2 (es) | 2006-06-30 |
US7316990B2 (en) | 2008-01-08 |
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