NO146563B - HERBICIDE PREPARATIONS CONTAINING A QUARTERLY BIPYRIDYLIUM SALT AND A TRIAZOLO-PYRIMIDINE - Google Patents
HERBICIDE PREPARATIONS CONTAINING A QUARTERLY BIPYRIDYLIUM SALT AND A TRIAZOLO-PYRIMIDINE Download PDFInfo
- Publication number
- NO146563B NO146563B NO770586A NO770586A NO146563B NO 146563 B NO146563 B NO 146563B NO 770586 A NO770586 A NO 770586A NO 770586 A NO770586 A NO 770586A NO 146563 B NO146563 B NO 146563B
- Authority
- NO
- Norway
- Prior art keywords
- triazolo
- pyrimidine
- preparation
- bipyridylium
- herbicidal
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 59
- 230000002363 herbicidal effect Effects 0.000 title claims description 31
- 150000003839 salts Chemical class 0.000 title claims description 21
- 239000004009 herbicide Substances 0.000 title claims description 12
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title description 15
- 150000001768 cations Chemical class 0.000 claims description 14
- -1 alkyl radical Chemical class 0.000 claims description 12
- UQDVRVNMIJAGRK-UHFFFAOYSA-N 2-amino-6-methyl-4-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-one Chemical group C1=C(C)C(=O)N(CCC)C2=NC(N)=NN21 UQDVRVNMIJAGRK-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 231100000206 health hazard Toxicity 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 description 16
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 239000000575 pesticide Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 206010047700 Vomiting Diseases 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000008673 vomiting Effects 0.000 description 5
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001983 poloxamer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 229940035044 sorbitan monolaurate Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- WXJYKXOIFICRPR-UHFFFAOYSA-L 1-methyl-4-(1-methylpyridin-1-ium-4-yl)pyridin-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.COS([O-])(=O)=O.C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 WXJYKXOIFICRPR-UHFFFAOYSA-L 0.000 description 1
- LOOHCHSAHWOXSE-UHFFFAOYSA-N 2-amino-4,6-dipropyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-one Chemical compound CCCN1C(=O)C(CCC)=CN2N=C(N)N=C21 LOOHCHSAHWOXSE-UHFFFAOYSA-N 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- TUKFDCPBHWPGCF-UHFFFAOYSA-N 6-methyl-4-propyl-2-(propylamino)-[1,2,4]triazolo[1,5-a]pyrimidin-5-one Chemical compound CCCN1C(=O)C(C)=CN2N=C(NCCC)N=C21 TUKFDCPBHWPGCF-UHFFFAOYSA-N 0.000 description 1
- 208000032484 Accidental exposure to product Diseases 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005630 Diquat Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PSYBGEADHLUXCS-UHFFFAOYSA-N Isocil Chemical compound CC(C)N1C(=O)NC(C)=C(Br)C1=O PSYBGEADHLUXCS-UHFFFAOYSA-N 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- WGVWLKXZBUVUAM-UHFFFAOYSA-N Pentanochlor Chemical compound CCCC(C)C(=O)NC1=CC=C(C)C(Cl)=C1 WGVWLKXZBUVUAM-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- XJCLWVXTCRQIDI-UHFFFAOYSA-N Sulfallate Chemical compound CCN(CC)C(=S)SCC(Cl)=C XJCLWVXTCRQIDI-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- PXWUKZGIHQRDHL-UHFFFAOYSA-N atraton Chemical compound CCNC1=NC(NC(C)C)=NC(OC)=N1 PXWUKZGIHQRDHL-UHFFFAOYSA-N 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- MXZACTZQSGYANA-UHFFFAOYSA-N chembl545463 Chemical compound Cl.C1=CC(OC)=CC=C1C(N=C1)=CN2C1=NC(C)=C2O MXZACTZQSGYANA-UHFFFAOYSA-N 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- PPJXIHLNYDVTDI-UHFFFAOYSA-N dicloralurea Chemical compound ClC(Cl)(Cl)C(O)NC(=O)NC(O)C(Cl)(Cl)Cl PPJXIHLNYDVTDI-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940059082 douche Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- JVCVWQYGXOSMDW-UHFFFAOYSA-L ethyl 2-[4-[1-(2-ethoxy-2-oxoethyl)pyridin-1-ium-4-yl]pyridin-1-ium-1-yl]acetate;dibromide Chemical compound [Br-].[Br-].C1=C[N+](CC(=O)OCC)=CC=C1C1=CC=[N+](CC(=O)OCC)C=C1 JVCVWQYGXOSMDW-UHFFFAOYSA-L 0.000 description 1
- UDXNHDHJDIMFFU-UHFFFAOYSA-N ethyl n-(6-methyl-5-oxo-4-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)carbamate Chemical compound C1=C(C)C(=O)N(CCC)C2=NC(NC(=O)OCC)=NN21 UDXNHDHJDIMFFU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- VFGNPYWQUOSOSR-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)acetamide Chemical compound CC(=O)NC1=C(C)C=CC=C1Cl VFGNPYWQUOSOSR-UHFFFAOYSA-N 0.000 description 1
- JHCUDKMENCRKFQ-UHFFFAOYSA-N n-(2-chlorophenyl)-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=CC=C1Cl JHCUDKMENCRKFQ-UHFFFAOYSA-N 0.000 description 1
- SCYGGCAQZFJGRF-UHFFFAOYSA-N n-(3,4-dichlorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(Cl)C(Cl)=C1 SCYGGCAQZFJGRF-UHFFFAOYSA-N 0.000 description 1
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical class C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Animal Behavior & Ethology (AREA)
- Otolaryngology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Denne oppfinnelse angår herbicide preparater inneholdende This invention relates to herbicidal preparations containing
et herbicid kvartært bipyridylium-salt som aktiv bestanddel. a herbicidal quaternary bipyridylium salt as active ingredient.
Gjennom årene er en rekke forskjellige pesticider utviklet Over the years, a number of different pesticides have been developed
for jordbruksformål for bekjempelse av sopp, skadeinsekter og ugress. Selv om disse stoffer nødvendigvis er giftige for visse former for liv, vil de når de anvendes med forsiktighet og i overensstemmelse med offisielle forskrifter,' ikke representere noen fare for menneske-liv. Til tross for forsøk på å oppmuntre de som kommer i kontakt med pesticider til å ta i bruk sikre håndteringsmetoder, forekommer imidlertid tilfeller med misbruk av pesticider. En særlig usikker praksis når det gjelder flytende pesticider, er at en liten mengde av det konsentrerte pesticid overføres til en husholdningsbeholder som f.eks. kan være en flaske for drikkevarer, for senere anvendelse hjemme. Risikoen som er knyttet til denne praksis, er selvsagt at et barn eller en uforsiktig voksen som kommer over flasken, kan svelge innholdet med muligens alvorlige følger. for agricultural purposes to combat fungi, harmful insects and weeds. Although these substances are necessarily toxic to certain forms of life, when used with care and in accordance with official regulations, they will not represent any danger to human life. However, despite efforts to encourage those who come into contact with pesticides to adopt safe handling methods, cases of pesticide misuse do occur. A particularly unsafe practice when it comes to liquid pesticides is that a small amount of the concentrated pesticide is transferred to a household container such as can be a bottle for beverages, for later use at home. The risk associated with this practice is, of course, that a child or a careless adult who comes across the bottle may swallow the contents with potentially serious consequences.
Vi har nu funnet det mulig å redusere sannsynligheten for alvorlige følger av slik utilsiktet svelging ved å fremkalle brekning. Dette kan i noen tilfeller resultere i hurtig fjernelse av det pesticide preparat fra maven og fordøyelseskanalen før dødelige mengder av pesticidet kan assimileres av kroppen. We have now found it possible to reduce the likelihood of serious consequences from such accidental ingestion by inducing vomiting. In some cases, this can result in the rapid removal of the pesticide preparation from the stomach and digestive tract before lethal amounts of the pesticide can be assimilated by the body.
Vi har funnet at tilsetning av et kjent triazolo[1,5-a]-pyrimidin-derivat med formel (I) som angitt nedenfor, til et herbicid kvartært bipyridyliumsalt i et herbicid preparat gir et preparat som hvis det svelges, har en tendens til å fremkalle brekning og derved utdrivning av preparatet. We have found that the addition of a known triazolo[1,5-a]-pyrimidine derivative of formula (I) as set forth below to a herbicidal quaternary bipyridylium salt in a herbicidal preparation produces a preparation which, if swallowed, tends to to induce vomiting and thereby expulsion of the preparation.
I henhold til oppfinnelsen tilveiebringes således et herbicid preparat med redusert helsefare, inneholdende et salt av et herbicid kvartært bipyridyliumkation og et s-triazolo[1,5-a]-pyrimidinderivat med formelen: According to the invention, a herbicidal preparation with a reduced health risk is thus provided, containing a salt of a herbicidal quaternary bipyridylium cation and an s-triazolo[1,5-a]-pyrimidine derivative with the formula:
hvor R er hydrogen, et C..-alkylradikal eller et COOEt-radikal, 2 3 where R is hydrogen, a C..-alkyl radical or a COOEt radical, 2 3
R er et C^^-alkylradikal eller et allylradikal, og R er et C^_^-alkylradikal, og,addisjonssalter derav. s-triazolo[1,5-a]-pyrimidinring-strukturen er nummerert som vist nedenfor: R is a C^^-alkyl radical or an allyl radical, and R is a C^^^-alkyl radical, and addition salts thereof. The s-triazolo[1,5-a]-pyrimidine ring structure is numbered as shown below:
Spesielle derivater av 5-okso-4,5-dihydro-s-triazolo-[1/5-a]pyrimidin for anvendelse i henhold til oppfinnelsen, er: 6-metyl-4-n-propyl-2-n-propylaitu.no-, Special derivatives of 5-oxo-4,5-dihydro-s-triazolo-[1/5-a]pyrimidine for use according to the invention are: 6-methyl-4-n-propyl-2-n-propylaitu. no-,
2-amino-6-metyl-4-allyl-, 2-amino-6-methyl-4-allyl-,
2-amino-4,6-di-n-propyl-, og 2-amino-4,6-di-n-propyl-, and
2-etoksykarbonylamino-6-mety1-4-n-propyl-derivatene. The 2-ethoxycarbonylamino-6-methyl-4-n-propyl derivs.
Et særlig egnet triazolo-pyrimidin for anvendelse i preparatene ifølge oppfinnelsen er 2-amino-6-metyl-5-okso-4-n-propy1-4,5-dihydro-s-triazolo[1,5-a]pyrimidin (II). A particularly suitable triazolo-pyrimidine for use in the preparations according to the invention is 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine (II ).
De herbicide kvartære bipyridyliumsalter for anvendelse i preparatene ifølge oppfinnelsen, er de som har de følgende formler: eller The herbicidal quaternary bipyridylium salts for use in the preparations according to the invention are those which have the following formulas: or
hvor R og R"*", som er like eller forskjellige, betyr alkyl-radikaler med fra 1 til 4 karbonatomer som eventuelt er substituert where R and R"*", which are the same or different, mean alkyl radicals with from 1 to 4 carbon atoms which are optionally substituted
med hydroksyl, halogen, karboksyl, alkoksy, alkylkarbonyl, alkoksykarbonyl, karbamoyl eller N-substituert karbamoyl; with hydroxyl, halogen, carboxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, carbamoyl or N-substituted carbamoyl;
[X]n betyr et anion, og n er et helt tall fra 1 til 4. [X]n means an anion, and n is an integer from 1 to 4.
Særlig foretrukne herbicide kvartære bipyridyliumsalter Particularly preferred herbicidal quaternary bipyridylium salts
er de nedenfor angitte: 1,l'-dimetyl-4,4<1->bipyridylium-di(metylsulfat) (paraquat-dimetosulfat) are those listed below: 1,1'-dimethyl-4,4<1->bipyridylium-di(methylsulfate) (paraquat-dimethosulfate)
l,l'-etylen-2,2,-bipyridylium-dibromid (diquat-dibromid) 1,1'-ethylene-2,2,-bipyridylium dibromide (diquat dibromide)
1,1'-dimetyl-4,4'-bipyridylium-diklorid (paraquat-diklorid) 1,1'-dimethyl-4,4'-bipyridylium dichloride (paraquat dichloride)
1,1'-di-2-hydroksyetyl-4,4'-bipyridylium-diklorid 1-(2-hydroksyetyl-l'-metyl)-4,4'-bipyridylium-diklorid 1,1'-di-karbamoylmetyl-4,4'-bipyridylium-diklorid 1,1'-bis-N,N-dimetylkarbamoylmetyl-4,4'-bipyridyliumdiklorid 1,1'-dimetyl-4,4<1->bipyridylium-sulfat (paraquat-sulfat) 1,1'-di-2-hydroxyethyl-4,4'-bipyridylium dichloride 1-(2-hydroxyethyl-1'-methyl)-4,4'-bipyridylium dichloride 1,1'-di-carbamoylmethyl-4 ,4'-bipyridylium dichloride 1,1'-bis-N,N-dimethylcarbamoylmethyl-4,4'-bipyridylium dichloride 1,1'-dimethyl-4,4<1->bipyridylium sulfate (paraquat sulfate)
1,1'-bis-N,N-dietylkarbamoylmetyl-4,4'-bipyridylium-diklorid 1,1'-diacetonyl-4,4'-bipyridylium-diklorid 1,1'-bis-N,N-diethylcarbamoylmethyl-4,4'-bipyridylium dichloride 1,1'-diacetonyl-4,4'-bipyridylium dichloride
1,1'-dietoksykarbonylmetyl-4,4'-bipyridylium-dibromid 1,1'-diethoxycarbonylmethyl-4,4'-bipyridylium dibromide
Navnene i parentes efter noen av forbindelsene i den ovenstående liste er de godtatte trivialnavn for disse forbindelser. Således er "paraquat" trivialnavnet for 1,1'-dimetyl-4,4'-bipyridylium-kationet. Paraquat er et særlig foretrukket bipyridylium-kation for anvendelse i preparatene ifølge oppfinnelsen. Et særlig foretrukket anion [X]<n>~ er klorid-anionet av praktiske og økonomiske grunner, men et hvilket som helst anion som fører til et passende vannoppløselig salt, kan eventuelt anvendes. Den herbicide virkning skyldes utelukkende kationet, og konsentrasjonen av et herbicid bipyridyliumsalt-preparat angis av denne grunn ofte som kationet alene. Den mengde herbicid kvartært bipyridyliumsalt som er tilstede i preparatene ifølge oppfinnelsen, er vanligvis fra 1,0 til 99,9 vekt%. The names in parentheses after some of the compounds in the above list are the accepted trivial names for these compounds. Thus "paraquat" is the trivial name for the 1,1'-dimethyl-4,4'-bipyridylium cation. Paraquat is a particularly preferred bipyridylium cation for use in the preparations according to the invention. A particularly preferred anion [X]<n>~ is the chloride anion for practical and economic reasons, but any anion leading to a suitable water-soluble salt may optionally be used. The herbicidal effect is due exclusively to the cation, and the concentration of a herbicidal bipyridylium salt preparation is therefore often stated as the cation alone. The amount of herbicidal quaternary bipyridylium salt present in the preparations according to the invention is usually from 1.0 to 99.9% by weight.
Preparatene ifølge oppfinnelsen kan inneholde et bære-middel eller fortynningsmiddel, og kan være faste stoffer, f.eks. granuler, eller væsker, f.eks. vandige oppløsninger. The preparations according to the invention may contain a carrier or diluent, and may be solid substances, e.g. granules, or liquids, e.g. aqueous solutions.
I henhold til en .foretrukket utførelsesform for oppfinnelsen tilveiebringes et konsentrert herbicid preparat inneholdende en vandig oppløsning av et salt av et herbicid kvartært-bipyridyliumkation og et triazolo-pyrimidin som definert ovenfor. Fortrinnsvis er det herbicide kvartære bipyridylium-kation paraquat. According to a preferred embodiment of the invention, a concentrated herbicide preparation is provided containing an aqueous solution of a salt of a quaternary bipyridylium cation herbicide and a triazolo-pyrimidine as defined above. Preferably, the herbicidal quaternary bipyridylium cation is paraquat.
Mengden av herbicid kvartært bipyridylium-kation som The amount of herbicide quaternary bipyridylium cation which
er til stede i den vandige oppløsning, er fortrinnsvis fra 50 til 400 g pr. liter. is present in the aqueous solution, is preferably from 50 to 400 g per litres.
Fortrinnsvis inneholder preparatet også et overflateaktivt middel. Preferably, the preparation also contains a surfactant.
Overflateaktive midler kan være av kationisk, ikke-ionisk eller anionisk karakter. Generelt foretrekkes kationiske og ikke-ioniske overflateaktive midler fremfor anioniske overflateaktive midler for anvendelse i preparatene ifølge oppfinnelsen, eftersom sistnevnte kan reagere på uønsket måte med det kvartære bipyridyliumsalt i preparatene. Eksempler på ikke-ioniske overflateaktive midler for anvendelse i preparatene ifølge oppfinnelsen, omfatter kondensasjonsprodukter av etylenoksyd med alkylfenoler så som oktylfenol, nonylfenol og oktylkresol. Andre ikke-ioniske midler er partialestrene avledet fra lang-kjedete fettsyrer og heksitol-anhydrider, f.eks. sorbitan-monolaurat; kondensasjonsprodukter av nevnte partialestere med etylenoksyd; og lecitiner. Eksempler på kationiske overflateaktive midler omfatter kvartære salter og kondensater av etylenoksyd med aminer, f.eks. stoffene som selges under varemerkene "Ethomeen", "Ethoduomeen", "Duoquad" og "Arquad". Surfactants can be cationic, non-ionic or anionic in nature. In general, cationic and non-ionic surfactants are preferred over anionic surfactants for use in the preparations according to the invention, since the latter may react in an undesirable manner with the quaternary bipyridylium salt in the preparations. Examples of non-ionic surfactants for use in the preparations according to the invention include condensation products of ethylene oxide with alkylphenols such as octylphenol, nonylphenol and octylcresol. Other nonionic agents are the partial esters derived from long-chain fatty acids and hexitol anhydrides, e.g. sorbitan monolaurate; condensation products of said partial esters with ethylene oxide; and lecithins. Examples of cationic surfactants include quaternary salts and condensates of ethylene oxide with amines, e.g. the drugs sold under the trade names "Ethomeen", "Ethoduomeen", "Duoquad" and "Arquad".
Særlig foretrukne overflateaktive midler er de kombinasjoner av overflateaktive midler som er beskrevet i britisk patent 998.264 for anvendelse i preparater inneholdende herbicide kvartære bipyridyliumsalter. Particularly preferred surfactants are the combinations of surfactants described in British patent 998,264 for use in preparations containing herbicidal quaternary bipyridylium salts.
Fremstillingen av triazolo-pyrimidinene (I) er beskrevet The preparation of the triazolo-pyrimidines (I) is described
i britisk patent 1.234.635, som det skal henvises til. in British Patent 1,234,635, to which reference should be made.
De brekningsfremkallende egenskaper hos preparatet be-stemmes særlig av den mengde triazolo-pyrimidin som det inneholder. Ved bestemmelse av de mest passende mengder av triazolo-pyrimidin for anvendelse i et preparat, må man ta hensyn til effektiviteten av triazolo-pyrimidinet i forhold til giftigheten av herbicidet. Den mengde triazolo-pyrimidin som innføres, er fortrinnsvis slik at en hvilken som helst mengde av preparatet som inneholder en mulig dødelig dose av herbicidet, vil inneholde tilstrekkelig av triazolo-pyrimidinet til å fremkalle brekning. Selvsagt kan hverken dødelige doser eller brekningsfremkallende doser måles direkte hos mennesker, og de kan bare beregnes på grunnlag av dyreforsøk. The vomiting-inducing properties of the preparation are determined in particular by the amount of triazolo-pyrimidine it contains. In determining the most appropriate amounts of triazolo-pyrimidine for use in a preparation, consideration must be given to the effectiveness of the triazolo-pyrimidine in relation to the toxicity of the herbicide. The amount of triazolo-pyrimidine introduced is preferably such that any amount of the preparation containing a potentially lethal dose of the herbicide will contain sufficient of the triazolo-pyrimidine to induce vomiting. Of course, neither lethal doses nor vomiting-inducing doses can be measured directly in humans, and they can only be calculated on the basis of animal experiments.
Preparater i henhold til oppfinnelsen inneholder fortrinnsvis fra 0,1 til 5 vektdeler av triazolo-pyrimidinet (f.eks. triazolo-pyrimidinet II) pr. 100 deler herbicid kvartært bipyridylium-kation (f.eks. paraquat). Hensiktsmessig er mengden av triazolo-pyrimidinet (f.eks. triazolopyrimidinet II) som anvendes, 0,25 til 2,0 deler pr. 100 deler herbicid kvartært bipyridylium-kation (f.eks. paraquat). Preparations according to the invention preferably contain from 0.1 to 5 parts by weight of the triazolo-pyrimidine (e.g. the triazolo-pyrimidine II) per 100 parts herbicide quaternary bipyridylium cation (eg paraquat). Suitably, the amount of the triazolo-pyrimidine (eg, the triazolopyrimidine II) used is 0.25 to 2.0 parts per 100 parts herbicide quaternary bipyridylium cation (eg paraquat).
Konsentrerte vandige preparater ifølge oppfinnelsen er korroderende. De må håndteres med forsiktighet for å unngå spruting i øynene eller på huden, og de må ikke få komme i kontakt med korroderbare metaller før fortynning. Concentrated aqueous preparations according to the invention are corrosive. They must be handled with care to avoid splashing in the eyes or on the skin, and they must not be allowed to come into contact with corrodible metals before dilution.
Preparatene i henhold til oppfinnelsen kan også inneholde farvede farvestoff- eller pigment-forbindelser for å gi dem en karakteristisk og adskillende farve. Eksempler på slike forbindelser er "Monastral Blue BNV Paste" og "Lissamine Turquoise VN 150". The preparations according to the invention can also contain colored dye or pigment compounds to give them a characteristic and distinguishing colour. Examples of such compounds are "Monastral Blue BNV Paste" and "Lissamine Turquoise VN 150".
Preparatene i henhold til oppfinnelsen kan også inneholde et stinkende middel. Eksempler på slike stinkende midler er: alkylpyridiner som beskrevet i britisk patent 1.406.881; n-valeriansyre; og tetrahydrotiofen. The preparations according to the invention can also contain a smelly agent. Examples of such malodorous agents are: alkylpyridines as described in British Patent 1,406,881; n-valeric acid; and tetrahydrothiophene.
Eventuelt kan triazolo-pyrimidinene (I) innføres i tiksotropiske preparater av herbicide kvartære salter. Særlig kan triazolo-pyrimidinene (I) innføres i preparatene inneholdende herbicide kvartære bipyridyliumsalter beskrevet i vårt britiske patent 1.395.502. Disse preparater omfatter en vandig oppløsning av et herbicid kvartært bipyridyliumsalt inneholdende et geldannende middel, f.eks. findelt kiselsyre, eller en kombinasjon av xantan-gummien som selges under varemerket "Kelzan" med natriummetaborat. Xantan-gummi er et komplekst polysakkarid. Optionally, the triazolo-pyrimidines (I) can be introduced into thixotropic preparations of herbicidal quaternary salts. In particular, the triazolo-pyrimidines (I) can be introduced into the preparations containing herbicidal quaternary bipyridylium salts described in our British patent 1,395,502. These preparations comprise an aqueous solution of a herbicidal quaternary bipyridylium salt containing a gelling agent, e.g. finely divided silicic acid, or a combination of the xanthan gum sold under the trade name "Kelzan" with sodium metaborate. Xanthan gum is a complex polysaccharide.
Preparatene i henhold til oppfinnelsen kan også inneholde et annet herbicid enn et herbicid kvartært bipyridyliumsalt som definert ovenfor. Eksempler på slike herbicider er: Amider (f.eks. N,N-diallylkloracetamid, 3,4-diklorpropionanilid, N- (3-klor-4-metylfenyl)-2-metylpentamid). The preparations according to the invention may also contain a herbicide other than a quaternary bipyridylium salt herbicide as defined above. Examples of such herbicides are: Amides (e.g. N,N-diallylchloroacetamide, 3,4-dichloropropionanilide, N-(3-chloro-4-methylphenyl)-2-methylpentamide).
Karbamater (f.eks. isopropyl-N-fenylkarbamat, isopropyl-N-(3-klorfenyl)-karbamat, 4-klor-2-but-2-ynyl-N-(3-klorfenyl)-karbamat, 2-klorallyl-N,N-dietyl-ditiokarbamat). Urinstoffer/anilider (f.eks. N,N'-di-(2,2,2-triklor-l-hydroksy-etyl)urinstoff, 3,4-dikloracetanilid, o-klorisobutyranilid, a-brom-3,4-dikloracetanilid, 3,4-diklorformanilid, 2-acetamido-3-klortoluen). Carbamates (eg isopropyl-N-phenylcarbamate, isopropyl-N-(3-chlorophenyl)-carbamate, 4-chloro-2-but-2-ynyl-N-(3-chlorophenyl)-carbamate, 2-chloroallyl- N,N-diethyl dithiocarbamate). Ureas/anilides (e.g. N,N'-di-(2,2,2-trichloro-1-hydroxy-ethyl)urea, 3,4-dichloroacetanilide, o-chloroisobutyranilide, α-bromo-3,4- dichloroacetanilide, 3,4-dichloroformanilide, 2-acetamido-3-chlorotoluene).
Diaziner (f.eks. 3,4,5,6-tetrahydro-3,5-dimetyl-2-tio-2H-l,3,5-tiadiazin, 5-brom-3-isopropyl-6-metyluracil, 5-amino-4-klor-2-fenyl-3-pyridazon, 1,2,3,6-tetrahydro-3,6-dioksopyridazin). Diazines (e.g. 3,4,5,6-tetrahydro-3,5-dimethyl-2-thio-2H-1,3,5-thiadiazine, 5-bromo-3-isopropyl-6-methyluracil, 5- amino-4-chloro-2-phenyl-3-pyridazone, 1,2,3,6-tetrahydro-3,6-dioxopyridazine).
Triaziner (f.eks. 2-klor-4,6-bisetylamino-1,3,5-triazin, 2-klor-4-etylamino-6-isopropylamino-l,3,5-triazin, 2-klor-4,6-bisisopropylamino-l,3,5-triazin, 4-etylamino-6-isopropylamino-2-metoksy-l,3,5-triazin, 4,6-bisisopropylamino-2-metoksy-l,3,5-triazin). Triazines (e.g. 2-chloro-4,6-bisethylamino-1,3,5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine, 2-chloro-4, 6-bisisopropylamino-1,3,5-triazine, 4-ethylamino-6-isopropylamino-2-methoxy-1,3,5-triazine, 4,6-bisisopropylamino-2-methoxy-1,3,5-triazine) .
Innføring av triazolo-pyrimidinet (I) i preparatene Introduction of the triazolo-pyrimidine (I) into the preparations
i henhold til oppfinnelsen har ingen skadelig innvirkning på preparatenes herbicide aktivitet. De følgende eksempler skal tjene til å illustrere oppfinnelsen ytterligere. according to the invention has no harmful effect on the herbicidal activity of the preparations. The following examples shall serve to further illustrate the invention.
Eksempel 1 Example 1
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-amino-6-metyl-5-okso-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidin (II) i vandig oppløsning. This example illustrates a preparation according to the invention which contains 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine (II) in aqueous solution.
Paraquat konsentrat er en oppløsning av paraquat-diklorid inneholdende 25 til 30 vekt% 1,l<1->dimetyl-4,4'-bipyridylium-kation. Den anvendte mengde ble valgt for å gi et preparat inneholdende 20 % vekt/volum paraquat kation. Preparatet ble fremstilt ved å røre bestanddelene sammen. Paraquat concentrate is a solution of paraquat dichloride containing 25 to 30% by weight of 1,1<1->dimethyl-4,4'-bipyridylium cation. The amount used was chosen to give a preparation containing 20% w/v paraquat cation. The preparation was prepared by mixing the ingredients together.
Eksempel 2 Example 2
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder triazolo-pyrimidinet (II) i vandig oppløsning. Preparatet inneholder de følgende bestanddeler. This example illustrates a preparation according to the invention which contains the triazolo-pyrimidine (II) in aqueous solution. The preparation contains the following ingredients.
"Lissapol" NX er et varemerke for et overflateaktivt middel inneholdende et kondensat av fra 7 til 8 moldeler etylenoksyd med 1 moldel p-nonylfenol. "Lissapol" NX is a trademark for a surfactant containing a condensate of from 7 to 8 moles of ethylene oxide with 1 mole of p-nonylphenol.
DS 4392 er et kodenummer for et overflateaktivt middel inneholdende en blanding av aminer avledet fra soyabønne-fettsyrer kondensert med omtrentlig 15 moldeler etylenoksyd. DS 4392 is a code number for a surfactant containing a mixture of amines derived from soybean fatty acids condensed with approximately 15 mole parts of ethylene oxide.
"Silcolapse" er et varemerke for et skumningsdempende middel inneholdende et silikonderivat. "Silcolapse" is a trademark for an antifoam agent containing a silicone derivative.
Preparatet beskrevet ovenfor ble fremstilt ved å røre bestanddelene sammen. The preparation described above was prepared by mixing the ingredients together.
Eksempel 3 Example 3
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder et geldannende middel i tillegg til triazolo-pyrimidinet (II). Preparatet inneholder de følgende bestanddeler This example illustrates a preparation according to the invention which contains a gel-forming agent in addition to the triazolo-pyrimidine (II). The preparation contains the following ingredients
Det ovenfor beskrevne preparat ble fremstilt ved å røre bestanddelene sammen og var tilstrekkelig flytende efter frem-stilling til at det kunne helles i beholdere. Ved henstand i 15 til 20 minutter dannet preparatet en gel og kunne ikke helles med mindre det ble kraftig ristet. The preparation described above was prepared by stirring the ingredients together and was sufficiently liquid after preparation that it could be poured into containers. On standing for 15 to 20 minutes, the preparation formed a gel and could not be poured unless vigorously shaken.
Eksempel 4 Example 4
Dette eksempel illustrerer et tørt, frittstrømmende granulært preparat som er både stabilt ved lagring og lett kan omdannes til en vandig oppløsning for anvendelse som en dusj. This example illustrates a dry, free-flowing granular formulation that is both stable on storage and readily reconstitution to an aqueous solution for use as a douche.
En oppløsning ble fremstilt med følgende sammensetning, hvor de angitte prosentmengder er efter vekt. A solution was prepared with the following composition, where the indicated percentages are by weight.
310 g av den ovenfor beskrevne oppløsning ble derefter satt i en tynn strøm til 690 g tørret magnesiumsulfat som befant seg i beholderen i en "HOBART" CE. 100 deigblander. Efter at det resulterende produkt var tørt, ble det ført gjennom en granuleringsmaskin og til slutt omrørt i en sikt med 30 masker pr. 2,5 lineær cm for å fjerne støv. De resulterende granuler hadde en størrelse på minst 0,9 mm og hadde en opp-løsningshastighet på 150 sekunder. 310 g of the above described solution was then added in a thin stream to 690 g of dried magnesium sulfate contained in the container of a "HOBART" CE. 100 dough mixers. After the resulting product was dry, it was passed through a granulating machine and finally agitated in a 30 mesh per sieve. 2.5 linear cm to remove dust. The resulting granules had a size of at least 0.9 mm and had a dissolution rate of 150 seconds.
Eksempel 5 Example 5
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-amino-6-metyl-5-okso-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidin (II) og et stinkende middel i vandig oppløsning. This example illustrates a preparation according to the invention which contains 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine (II) and a smelly agent in aqueous solution.
Det ovenfor beskrevne preparat ble fremstilt ved å røre bestanddelene sammen. The preparation described above was prepared by stirring the ingredients together.
Eksempel 6 Example 6
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-amino-6-metyl-5-okso-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidin (II) i en fortykket, farvet, vandig oppløsning. This example illustrates a preparation according to the invention which contains 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine (II) in a thickened, colored, aqueous solution.
"Synperonic" og "Nansa" er varemerker. "Synperonic" 2 "Synperonic" and "Nansa" are trademarks. "Synperonic" 2
er et kondensasjonsprodukt av en blanding av 67% C, 3 Q( 3 33% C^-alifatiske alkoholer med to ekvivalenter etylenoksyd. "Synperonic" 16 er et kondensasjonsprodukt av en blanding av 67% C, 3 °<? 33% C^-alifatiske alkoholer med 16 ekvivalenter etylenoksyd. "Nansa" 1106 er natriumdodecyl- (hovedsakelig C, 2 lineær kjede)-benzensulfonat. Monastral BNVS pasta er en dispersjon inneholdende 15% vekt/volum kobberftalocyanin-pigment i vann. Pyridin-base er en blanding bestående hovedsakelig av alkylpyridiner. is a condensation product of a mixture of 67% C, 3 Q( 3 33% C^-aliphatic alcohols with two equivalents of ethylene oxide. "Synperonic" 16 is a condensation product of a mixture of 67% C, 3 °<? 33% C^ -aliphatic alcohols with 16 equivalents of ethylene oxide. "Nansa" 1106 is sodium dodecyl-(mainly C, 2 linear chain)-benzenesulfonate. Monastral BNVS paste is a dispersion containing 15% w/v copper phthalocyanine pigment in water. Pyridine base is a mixture consisting mainly of alkylpyridines.
Eksempel 7 Example 7
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-amino-6-metyl-5-okso-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidin (II) i vandig oppløsning. This example illustrates a preparation according to the invention which contains 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine (II) in aqueous solution.
Diquat-ion er 1,1'-etylen-2,2'-bipyridylium-kation. Diquat ion is 1,1'-ethylene-2,2'-bipyridylium cation.
Det ovenfor beskrevne preparat ble fremstilt ved å røre bestanddelene sammen og hadde en pH på 6,5 i 0,3. The preparation described above was prepared by stirring the ingredients together and had a pH of 6.5 in 0.3.
Eksempel 8 Example 8
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-amino-6-metyl-5-okso-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidin (II) i vandig oppløsning. This example illustrates a preparation according to the invention which contains 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine (II) in aqueous solution.
Morfamquat-ion er 1,1'-bis(3,5-dimetylmorfolino-karbonylmetyl)-4,4'-bipyridylium-ion. Det ovenfor beskrevne preparat ble fremstilt ved å røre bestanddelene sammen. Morphamquat ion is 1,1'-bis(3,5-dimethylmorpholinocarbonylmethyl)-4,4'-bipyridylium ion. The preparation described above was prepared by stirring the ingredients together.
Eksempel 9 Example 9
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-amino-6-metyl-5-okso-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidin (II) i vandig oppløsning. Det ovenfor beskrevne preparat ble fremstilt ved å røre bestanddelene sammen. This example illustrates a preparation according to the invention which contains 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine (II) in aqueous solution. The preparation described above was prepared by stirring the ingredients together.
"Tween" er et varemerke. "Tween" 20 er et kondensasjonsprodukt av 1 mol sorbitan-monolaurat med 20 mol etylenoksyd. "Tween" is a trademark. "Tween" 20 is a condensation product of 1 mol of sorbitan monolaurate with 20 mol of ethylene oxide.
Eksempel 10 Example 10
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-n-propylamino-6-metyl-5-okso-4-n-propyl-4,5-dihydro-s-triazolo[l,5-a]pyrimidin i vandig opp-løsning. This example illustrates a preparation according to the invention containing 2-n-propylamino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine in aqueous solution.
Eksempel 11 Example 11
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-amino-5-okso-4,6-di-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidin i vandig oppløsning. This example illustrates a preparation according to the invention which contains 2-amino-5-oxo-4,6-di-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine in aqueous solution.
Eksempel 12 Example 12
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-etoksykarbonylamino-6-metyl-5-okso-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidin i vandig oppløsning. This example illustrates a preparation according to the invention which contains 2-ethoxycarbonylamino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine in aqueous solution.
Eksempel 13 Example 13
Dette eksempel illustrerer et preparat i henhold til oppfinnelsen som inneholder 2-amino-6-metyl-5-okso-4-allyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidin i vandig oppløsning. This example illustrates a preparation according to the invention which contains 2-amino-6-methyl-5-oxo-4-allyl-4,5-dihydro-s-triazolo[1,5-a]pyrimidine in aqueous solution.
Claims (2)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15584/76A GB1507407A (en) | 1976-04-15 | 1976-04-15 | Herbicidal compositions |
| GB3458976 | 1976-08-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO770586L NO770586L (en) | 1977-10-18 |
| NO146563B true NO146563B (en) | 1982-07-19 |
| NO146563C NO146563C (en) | 1982-10-27 |
Family
ID=26251408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO770586A NO146563C (en) | 1976-04-15 | 1977-02-22 | HERBICIDE PREPARATIONS CONTAINING A QUARTERLY BIPYRIDYLIUM SALT AND A TRIAZOLO-PYRIMIDINE |
Country Status (39)
| Country | Link |
|---|---|
| JP (1) | JPS52128222A (en) |
| AR (1) | AR217825A1 (en) |
| BE (1) | BE852862A (en) |
| BG (1) | BG27712A3 (en) |
| BR (1) | BR7702375A (en) |
| CA (1) | CA1096191A (en) |
| CH (1) | CH628208A5 (en) |
| CU (1) | CU34684A (en) |
| CY (1) | CY1025A (en) |
| DD (1) | DD129965A5 (en) |
| DE (1) | DE2709307C2 (en) |
| DK (1) | DK145811C (en) |
| DO (1) | DOP1977002588A (en) |
| EG (1) | EG12605A (en) |
| ES (1) | ES457860A1 (en) |
| FI (1) | FI58711C (en) |
| FR (1) | FR2347883A1 (en) |
| GB (1) | GB1507407A (en) |
| GR (1) | GR61602B (en) |
| HK (1) | HK70179A (en) |
| HU (1) | HU179721B (en) |
| IE (1) | IE44883B1 (en) |
| IL (1) | IL51570A (en) |
| IT (1) | IT1077294B (en) |
| KE (1) | KE2994A (en) |
| LU (1) | LU77128A1 (en) |
| MY (1) | MY8000150A (en) |
| NL (1) | NL172115C (en) |
| NO (1) | NO146563C (en) |
| NZ (1) | NZ183410A (en) |
| OA (1) | OA05635A (en) |
| PH (1) | PH13711A (en) |
| PL (1) | PL101203B1 (en) |
| PT (1) | PT66431B (en) |
| RO (1) | RO71904A (en) |
| SE (1) | SE444631B (en) |
| TR (1) | TR19211A (en) |
| YU (1) | YU44402B (en) |
| ZM (1) | ZM2977A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE46306B1 (en) * | 1977-02-11 | 1983-05-04 | Ici Ltd | Safeguarded toxic chemical compositions containing an emetic |
| FR2588723B1 (en) * | 1985-11-12 | 1990-04-13 | Sds Biotech Kk | SOLID ANTI-SWALLOWING HERBICIDE COMPOSITION CONTAINING PARAQUAT AND A THICKENING AGENT |
| GB9015134D0 (en) * | 1990-07-10 | 1990-08-29 | Ici Plc | Herbicidal compositions |
| KR100329374B1 (en) * | 1999-09-22 | 2002-03-22 | 우종일 | Water dispersable granule comprising paraquat dichloride and its manufacturing method |
| CN108218766A (en) * | 2017-12-11 | 2018-06-29 | 东南大学 | A kind of preparation method of the compound containing paraquat or diquat |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH348003A (en) * | 1958-04-21 | 1960-07-31 | Complements Alimentaires S A R | Process for manufacturing toxic rat poison baits |
| IE33549B1 (en) * | 1968-09-13 | 1974-08-07 | Ici Ltd | S-triazolo (1,5-a) pyrimidine derivatives |
| AT292698B (en) * | 1969-09-12 | 1971-09-10 | Ici Ltd | Process for the preparation of new s-triazolo [1,5-a] pyrimidines |
| GB1406881A (en) * | 1972-04-13 | 1975-09-17 | Ici Ltd | Herbicidal compositions |
| GB1450531A (en) * | 1972-10-27 | 1976-09-22 | Ici Ltd | Herbicidal compositions |
-
1976
- 1976-04-15 GB GB15584/76A patent/GB1507407A/en not_active Expired
-
1977
- 1977-01-31 IT IT19802/77A patent/IT1077294B/en active
- 1977-02-16 CY CY1025A patent/CY1025A/en unknown
- 1977-02-18 IE IE357/77A patent/IE44883B1/en not_active IP Right Cessation
- 1977-02-22 NO NO770586A patent/NO146563C/en unknown
- 1977-02-22 NZ NZ183410A patent/NZ183410A/en unknown
- 1977-03-01 IL IL51570A patent/IL51570A/en unknown
- 1977-03-01 PH PH19512A patent/PH13711A/en unknown
- 1977-03-03 DE DE2709307A patent/DE2709307C2/en not_active Expired
- 1977-03-04 DK DK96777A patent/DK145811C/en not_active IP Right Cessation
- 1977-03-14 GR GR52988A patent/GR61602B/en unknown
- 1977-03-15 NL NLAANVRAGE7702758,A patent/NL172115C/en not_active IP Right Cessation
- 1977-03-17 RO RO7789689A patent/RO71904A/en unknown
- 1977-03-18 AR AR266919A patent/AR217825A1/en active
- 1977-03-19 EG EG163/77A patent/EG12605A/en active
- 1977-03-22 CU CU7734684A patent/CU34684A/en unknown
- 1977-03-23 PL PL1977196854A patent/PL101203B1/en unknown
- 1977-03-24 BE BE176106A patent/BE852862A/en not_active IP Right Cessation
- 1977-03-28 FR FR7709213A patent/FR2347883A1/en active Granted
- 1977-03-30 ZM ZM7729A patent/ZM2977A1/en unknown
- 1977-04-06 BG BG7735933A patent/BG27712A3/en unknown
- 1977-04-11 DO DO1977002588A patent/DOP1977002588A/en unknown
- 1977-04-11 TR TR19211A patent/TR19211A/en unknown
- 1977-04-13 PT PT66431A patent/PT66431B/en unknown
- 1977-04-13 JP JP4157577A patent/JPS52128222A/en active Granted
- 1977-04-13 YU YU977/77A patent/YU44402B/en unknown
- 1977-04-13 SE SE7704238A patent/SE444631B/en not_active IP Right Cessation
- 1977-04-13 LU LU77128A patent/LU77128A1/xx unknown
- 1977-04-13 FI FI771161A patent/FI58711C/en not_active IP Right Cessation
- 1977-04-13 DD DD7700198379A patent/DD129965A5/en unknown
- 1977-04-14 OA OA56141A patent/OA05635A/en unknown
- 1977-04-14 BR BR7702375A patent/BR7702375A/en unknown
- 1977-04-14 HU HU77IE775A patent/HU179721B/en unknown
- 1977-04-15 CH CH471677A patent/CH628208A5/en not_active IP Right Cessation
- 1977-04-15 CA CA276,251A patent/CA1096191A/en not_active Expired
- 1977-04-15 ES ES457860A patent/ES457860A1/en not_active Expired
-
1979
- 1979-09-27 KE KE2994A patent/KE2994A/en unknown
- 1979-10-04 HK HK701/79A patent/HK70179A/en unknown
-
1980
- 1980-12-31 MY MY1980150A patent/MY8000150A/en unknown
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