CA1049282A - Synergistic compositions - Google Patents
Synergistic compositionsInfo
- Publication number
- CA1049282A CA1049282A CA225,044A CA225044A CA1049282A CA 1049282 A CA1049282 A CA 1049282A CA 225044 A CA225044 A CA 225044A CA 1049282 A CA1049282 A CA 1049282A
- Authority
- CA
- Canada
- Prior art keywords
- pyrazolium
- alkyl
- formula
- salt
- chloride
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 230000002195 synergetic effect Effects 0.000 title claims abstract description 10
- -1 aliphatic trimethylammonium salt Chemical class 0.000 claims abstract description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 22
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 235000007320 Avena fatua Nutrition 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 15
- 230000002363 herbicidal effect Effects 0.000 claims description 14
- 244000075850 Avena orientalis Species 0.000 claims description 13
- 235000005373 Uvularia sessilifolia Nutrition 0.000 claims description 13
- 150000001450 anions Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 10
- SGJNNTYIZXBZQH-UHFFFAOYSA-N 1,2-dimethyl-3,5-diphenyl-1,3-dihydropyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[NH+]1N(C)C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 SGJNNTYIZXBZQH-UHFFFAOYSA-N 0.000 claims description 9
- 241000209140 Triticum Species 0.000 claims description 9
- 235000021307 Triticum Nutrition 0.000 claims description 9
- 229940077388 benzenesulfonate Drugs 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 235000013339 cereals Nutrition 0.000 claims description 8
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 7
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 7
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000005082 stem growth Effects 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- HKXGOYJREGRGPC-UHFFFAOYSA-N 1,1-diphenylpyrazol-1-ium Chemical class N1=CC=C[N+]1(C=1C=CC=CC=1)C1=CC=CC=C1 HKXGOYJREGRGPC-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- 240000005979 Hordeum vulgare Species 0.000 claims description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 3
- 235000007238 Secale cereale Nutrition 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 3
- BARJCBPUNFDTCY-UHFFFAOYSA-N 1,2-dimethyl-3,5-diphenyl-1,3-dihydropyrazol-1-ium chloride Chemical compound [Cl-].C[NH+]1N(C(C=C1C1=CC=CC=C1)C1=CC=CC=C1)C BARJCBPUNFDTCY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims 2
- 241000209056 Secale Species 0.000 claims 1
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 229940000425 combination drug Drugs 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 8
- 239000004009 herbicide Substances 0.000 description 10
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 6
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 6
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 6
- 241000209764 Avena fatua Species 0.000 description 4
- 229920001213 Polysorbate 20 Polymers 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
- 244000237956 Amaranthus retroflexus Species 0.000 description 3
- 241000209761 Avena Species 0.000 description 3
- 235000004535 Avena sterilis Nutrition 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000011885 synergistic combination Substances 0.000 description 3
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 3
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- JARFAUHJHIUGCO-UHFFFAOYSA-N 1,2-dimethyl-3,5-diphenyl-3h-pyrazole Chemical compound CN1N(C)C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 JARFAUHJHIUGCO-UHFFFAOYSA-N 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- HRZXDBYSPQNHDA-UHFFFAOYSA-N 1-ethyl-2-methyl-3,5-diphenyl-1,3-dihydropyrazol-1-ium chloride Chemical compound [Cl-].C(C)[NH+]1N(C(C=C1C1=CC=CC=C1)C1=CC=CC=C1)C HRZXDBYSPQNHDA-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- WEAISLOOYZSMCM-UHFFFAOYSA-M 2-bromopropyl(trimethyl)azanium bromide Chemical compound [Br-].BrC(C[N+](C)(C)C)C WEAISLOOYZSMCM-UHFFFAOYSA-M 0.000 description 1
- PHHDQWZIARFHPV-UHFFFAOYSA-M 2-chloroethyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CCCl PHHDQWZIARFHPV-UHFFFAOYSA-M 0.000 description 1
- XVHOPCXTNOPRIP-UHFFFAOYSA-M 2-cyanoethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCC#N XVHOPCXTNOPRIP-UHFFFAOYSA-M 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- ZQKJDSWJSPZYNR-UHFFFAOYSA-M 4-bromobutyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCBr ZQKJDSWJSPZYNR-UHFFFAOYSA-M 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- MVHRMEFNTKSBAW-UHFFFAOYSA-N S(=O)(=O)(OC)[O-].C(C)(CC)N1[NH+](C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C Chemical compound S(=O)(=O)(OC)[O-].C(C)(CC)N1[NH+](C(=CC1C1=CC=CC=C1)C1=CC=CC=C1)C MVHRMEFNTKSBAW-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000005224 alkoxybenzenes Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical class CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- ODMCBOQBLGOAKC-UHFFFAOYSA-M methoxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].COC[N+](C)(C)C ODMCBOQBLGOAKC-UHFFFAOYSA-M 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- JKUAUCQIEHEDSL-UHFFFAOYSA-N trimethyl(2-sulfanylethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCS JKUAUCQIEHEDSL-UHFFFAOYSA-N 0.000 description 1
- FMMTUUIZTMQIFC-UHFFFAOYSA-M trimethyl(prop-2-enyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC=C FMMTUUIZTMQIFC-UHFFFAOYSA-M 0.000 description 1
- TZYULTYGSBAILI-UHFFFAOYSA-M trimethyl(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC=C TZYULTYGSBAILI-UHFFFAOYSA-M 0.000 description 1
- MJWZBZQBRJUWCP-UHFFFAOYSA-M trimethyl(thiiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CS1 MJWZBZQBRJUWCP-UHFFFAOYSA-M 0.000 description 1
- 239000004552 water soluble powder 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47353374A | 1974-05-28 | 1974-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049282A true CA1049282A (en) | 1979-02-27 |
Family
ID=23879926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA225,044A Expired CA1049282A (en) | 1974-05-28 | 1975-04-21 | Synergistic compositions |
Country Status (17)
| Country | Link |
|---|---|
| AR (1) | AR229922A1 (nl) |
| BE (1) | BE829528A (nl) |
| CA (1) | CA1049282A (nl) |
| CS (1) | CS181786B2 (nl) |
| DD (1) | DD119699A5 (nl) |
| DE (1) | DE2522471C2 (nl) |
| DK (1) | DK136751B (nl) |
| ES (1) | ES437989A1 (nl) |
| FI (1) | FI57042C (nl) |
| FR (1) | FR2272603B1 (nl) |
| GB (1) | GB1466634A (nl) |
| IE (1) | IE41071B1 (nl) |
| IT (1) | IT1057898B (nl) |
| NL (1) | NL7505964A (nl) |
| SE (1) | SE425940B (nl) |
| SU (1) | SU580798A3 (nl) |
| TR (1) | TR18239A (nl) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2260485C2 (de) * | 1971-12-17 | 1983-12-29 | American Cyanamid Co., Wayne, N.J. | 1,2-Dialkyl-3,5-diphenylpyrazoliumsalze und diese enthaltende herbizide Mittel |
-
1975
- 1975-04-21 AR AR258440A patent/AR229922A1/es active
- 1975-04-21 CA CA225,044A patent/CA1049282A/en not_active Expired
- 1975-04-28 GB GB1763375A patent/GB1466634A/en not_active Expired
- 1975-05-12 IT IT49532/75A patent/IT1057898B/it active
- 1975-05-13 TR TR18239A patent/TR18239A/xx unknown
- 1975-05-21 NL NL7505964A patent/NL7505964A/nl not_active Application Discontinuation
- 1975-05-21 DE DE2522471A patent/DE2522471C2/de not_active Expired
- 1975-05-22 CS CS7500003607A patent/CS181786B2/cs unknown
- 1975-05-26 IE IE1172/75A patent/IE41071B1/xx unknown
- 1975-05-27 DD DD186272A patent/DD119699A5/xx unknown
- 1975-05-27 BE BE156739A patent/BE829528A/xx not_active IP Right Cessation
- 1975-05-27 DK DK233475AA patent/DK136751B/da unknown
- 1975-05-28 SU SU7502137882A patent/SU580798A3/ru active
- 1975-05-28 SE SE7506105A patent/SE425940B/xx unknown
- 1975-05-28 FI FI751556A patent/FI57042C/fi not_active IP Right Cessation
- 1975-05-28 ES ES437989A patent/ES437989A1/es not_active Expired
- 1975-05-28 FR FR7516683A patent/FR2272603B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1057898B (it) | 1982-03-30 |
| FI751556A (nl) | 1975-11-29 |
| SE425940B (sv) | 1982-11-29 |
| FR2272603B1 (nl) | 1978-05-19 |
| FI57042C (fi) | 1980-06-10 |
| DK233475A (nl) | 1975-11-29 |
| GB1466634A (en) | 1977-03-09 |
| TR18239A (tr) | 1976-11-05 |
| DD119699A5 (nl) | 1976-05-12 |
| FI57042B (fi) | 1980-02-29 |
| FR2272603A1 (nl) | 1975-12-26 |
| SE7506105L (sv) | 1975-12-01 |
| ES437989A1 (es) | 1977-04-01 |
| CS181786B2 (en) | 1978-03-31 |
| DK136751C (nl) | 1978-05-29 |
| DK136751B (da) | 1977-11-21 |
| NL7505964A (nl) | 1975-12-02 |
| IE41071L (en) | 1975-11-28 |
| AU8054475A (en) | 1976-10-28 |
| BE829528A (fr) | 1975-11-27 |
| SU580798A3 (ru) | 1977-11-15 |
| IE41071B1 (en) | 1979-10-10 |
| DE2522471C2 (de) | 1984-12-20 |
| DE2522471A1 (de) | 1975-12-11 |
| AR229922A1 (es) | 1984-01-31 |
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