CS199737B2 - Herbicide - Google Patents
Herbicide Download PDFInfo
- Publication number
- CS199737B2 CS199737B2 CS784784A CS478478A CS199737B2 CS 199737 B2 CS199737 B2 CS 199737B2 CS 784784 A CS784784 A CS 784784A CS 478478 A CS478478 A CS 478478A CS 199737 B2 CS199737 B2 CS 199737B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- parts
- active ingredient
- plants
- acid
- water
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 10
- 239000004009 herbicide Substances 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 239000004480 active ingredient Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 15
- BFNNILAMSKQDRN-UHFFFAOYSA-N 2h-1,2,4-triazin-5-one Chemical class O=C1C=NNC=N1 BFNNILAMSKQDRN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000006072 paste Substances 0.000 description 8
- 229920000151 polyglycol Polymers 0.000 description 8
- 239000010695 polyglycol Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- -1 carboxylic acid nitrile Chemical class 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000010410 dusting Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- GATGYGMXVVUIDP-UHFFFAOYSA-N 1-ethylcyclopropane-1-carbonyl cyanide Chemical compound N#CC(=O)C1(CC)CC1 GATGYGMXVVUIDP-UHFFFAOYSA-N 0.000 description 3
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical class O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 2
- UDUFDKGYJXWAOL-UHFFFAOYSA-N 4-amino-6-(1-ethylcyclopropyl)-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound N=1NC(=S)N(N)C(=O)C=1C1(CC)CC1 UDUFDKGYJXWAOL-UHFFFAOYSA-N 0.000 description 2
- WKGYMUDKPAOIIP-UHFFFAOYSA-N 4-amino-6-(1-methylcyclopropyl)-3-methylsulfanyl-1,2,4-triazin-5-one Chemical compound O=C1N(N)C(SC)=NN=C1C1(C)CC1 WKGYMUDKPAOIIP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 240000005702 Galium aparine Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- 239000012022 methylating agents Substances 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WWXJUZNBLMMFCG-UHFFFAOYSA-N n-tert-butyl-2-(1-ethylcyclopropyl)-2-oxoacetamide Chemical compound CC(C)(C)NC(=O)C(=O)C1(CC)CC1 WWXJUZNBLMMFCG-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PDQQMDHQCMDAET-UHFFFAOYSA-N 1-ethylcyclopropane-1-carbonyl chloride Chemical compound CCC1(C(Cl)=O)CC1 PDQQMDHQCMDAET-UHFFFAOYSA-N 0.000 description 1
- FGGFZGZVRCCRRL-UHFFFAOYSA-N 1-methylcyclopropane-1-carbonyl cyanide Chemical compound N#CC(=O)C1(C)CC1 FGGFZGZVRCCRRL-UHFFFAOYSA-N 0.000 description 1
- UJHMFTPWVRCYBJ-UHFFFAOYSA-N 2-(1-ethylcyclopropyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1(CC)CC1 UJHMFTPWVRCYBJ-UHFFFAOYSA-N 0.000 description 1
- HFBHPHBIBAUDNE-UHFFFAOYSA-N 2h-1,2,4-triazin-3-one Chemical class O=C1N=CC=NN1 HFBHPHBIBAUDNE-UHFFFAOYSA-N 0.000 description 1
- SYTQFBVTZCYXOV-UHFFFAOYSA-N 3,5,5-trimethylcyclohex-2-en-1-one Chemical compound CC1=CC(=O)CC(C)(C)C1.CC1=CC(=O)CC(C)(C)C1 SYTQFBVTZCYXOV-UHFFFAOYSA-N 0.000 description 1
- FSVMLCNADDOSKY-UHFFFAOYSA-N 4-amino-6-(1-ethylcyclopropyl)-3-methylsulfanyl-1,2,4-triazin-5-one Chemical compound N=1N=C(SC)N(N)C(=O)C=1C1(CC)CC1 FSVMLCNADDOSKY-UHFFFAOYSA-N 0.000 description 1
- 241001184547 Agrostis capillaris Species 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 241001666377 Apera Species 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 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
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 244000082988 Secale cereale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001264 acyl cyanides Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- SXQXMCWCWVCFPC-UHFFFAOYSA-N aluminum;potassium;dioxido(oxo)silane Chemical compound [Al+3].[K+].[O-][Si]([O-])=O.[O-][Si]([O-])=O SXQXMCWCWVCFPC-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000019993 champagne Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772732797 DE2732797A1 (de) | 1977-07-20 | 1977-07-20 | Herbizid wirksames 1.2.4-triazin- 5-on-derivat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199737B2 true CS199737B2 (en) | 1980-07-31 |
Family
ID=6014415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS784784A CS199737B2 (en) | 1977-07-20 | 1978-07-18 | Herbicide |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4402733A (es) |
| AT (1) | AT362186B (es) |
| AU (1) | AU520741B2 (es) |
| BE (1) | BE869138A (es) |
| BR (1) | BR7804647A (es) |
| CA (1) | CA1079280A (es) |
| CH (1) | CH638794A5 (es) |
| CS (1) | CS199737B2 (es) |
| DD (1) | DD139990A5 (es) |
| DK (1) | DK149104B (es) |
| EG (1) | EG13444A (es) |
| ES (1) | ES471874A1 (es) |
| FR (1) | FR2401145A1 (es) |
| GB (1) | GB2002360B (es) |
| GR (1) | GR65206B (es) |
| HU (1) | HU182857B (es) |
| IL (1) | IL55124A0 (es) |
| IT (1) | IT1181588B (es) |
| LU (1) | LU79992A1 (es) |
| MX (1) | MX5454E (es) |
| NL (1) | NL7807484A (es) |
| NZ (1) | NZ187904A (es) |
| PT (1) | PT68325A (es) |
| SE (1) | SE444435B (es) |
| SU (1) | SU810065A3 (es) |
| TR (1) | TR19953A (es) |
| ZA (1) | ZA784058B (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2733181B2 (de) * | 1977-07-22 | 1979-08-30 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von N-substituierten a -Ketocarbonsäureamiden |
| DE2733180C3 (de) * | 1977-07-22 | 1983-04-14 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von 4-Amino-3-methylmercapto-1,2,4-triazin- 5-on-Derivaten |
| DE3026093C2 (de) * | 1980-07-10 | 1983-02-10 | Degussa Ag, 6000 Frankfurt | 1-Methyl-2-chlorcyclopropancarbonsäure und deren verzweigte und unverzweigte C↓1↓ bis C↓6↓-Alkylester, sowie Verfahren zu deren Herstellung |
| US6852857B2 (en) * | 2002-05-16 | 2005-02-08 | Bayer Materialscience Llc | Method of preparing substituted 4-amino-3-alkylthio-1,2,4-triazine-5-ones |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966715A (en) * | 1966-04-16 | 1976-06-29 | Bayer Aktiengesellschaft | Herbicidal agents |
| CH492399A (de) * | 1968-03-20 | 1970-06-30 | Agripat Sa | Herbizides Mittel |
| DE2107757C3 (de) * | 1971-02-18 | 1980-02-28 | Bayer Ag, 5090 Leverkusen | 4-Amino-1,2,4-triazin-5-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| BE786840A (fr) * | 1971-07-29 | 1973-01-29 | Bayer Ag | Procede de preparation de 1,2,4-triazine -5-ones |
| US3914224A (en) * | 1973-11-12 | 1975-10-21 | Du Pont | 1,3,5-S-Triazines |
-
1978
- 1978-06-26 GR GR56598A patent/GR65206B/el unknown
- 1978-07-11 NL NL7807484A patent/NL7807484A/xx not_active Application Discontinuation
- 1978-07-12 IL IL55124A patent/IL55124A0/xx unknown
- 1978-07-14 SU SU782636093A patent/SU810065A3/ru active
- 1978-07-17 DK DK319978AA patent/DK149104B/da not_active Application Discontinuation
- 1978-07-17 ZA ZA00784058A patent/ZA784058B/xx unknown
- 1978-07-17 AU AU38079/78A patent/AU520741B2/en not_active Expired
- 1978-07-17 EG EG447/78A patent/EG13444A/xx active
- 1978-07-18 DD DD78206794A patent/DD139990A5/de unknown
- 1978-07-18 CS CS784784A patent/CS199737B2/cs unknown
- 1978-07-18 LU LU79992A patent/LU79992A1/xx unknown
- 1978-07-18 MX MX787267U patent/MX5454E/es unknown
- 1978-07-18 IT IT50349/78A patent/IT1181588B/it active
- 1978-07-19 NZ NZ187904A patent/NZ187904A/xx unknown
- 1978-07-19 ES ES471874A patent/ES471874A1/es not_active Expired
- 1978-07-19 CH CH778878A patent/CH638794A5/de not_active IP Right Cessation
- 1978-07-19 BE BE6046543A patent/BE869138A/xx not_active IP Right Cessation
- 1978-07-19 PT PT68325A patent/PT68325A/pt unknown
- 1978-07-19 HU HU78CI1847A patent/HU182857B/hu unknown
- 1978-07-19 BR BR7804647A patent/BR7804647A/pt unknown
- 1978-07-19 SE SE7807988A patent/SE444435B/sv unknown
- 1978-07-19 CA CA307,680A patent/CA1079280A/en not_active Expired
- 1978-07-19 AT AT524178A patent/AT362186B/de not_active IP Right Cessation
- 1978-07-20 GB GB7830564A patent/GB2002360B/en not_active Expired
- 1978-07-20 FR FR7821516A patent/FR2401145A1/fr active Granted
- 1978-11-14 TR TR19953A patent/TR19953A/xx unknown
-
1981
- 1981-04-20 US US06/255,517 patent/US4402733A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EG13444A (en) | 1982-03-31 |
| AT362186B (de) | 1981-04-27 |
| DK149104B (da) | 1986-01-27 |
| ES471874A1 (es) | 1979-02-01 |
| AU3807978A (en) | 1980-01-17 |
| CA1079280A (en) | 1980-06-10 |
| SE7807988L (sv) | 1979-01-21 |
| PT68325A (pt) | 1978-08-01 |
| ATA524178A (de) | 1980-09-15 |
| DD139990A5 (de) | 1980-02-06 |
| DK319978A (da) | 1979-01-21 |
| ZA784058B (en) | 1979-07-25 |
| LU79992A1 (es) | 1978-12-12 |
| HU182857B (en) | 1984-03-28 |
| TR19953A (tr) | 1980-05-15 |
| AU520741B2 (en) | 1982-02-25 |
| MX5454E (es) | 1983-08-10 |
| NL7807484A (nl) | 1979-01-23 |
| IT7850349A0 (it) | 1978-07-18 |
| GR65206B (en) | 1980-07-29 |
| GB2002360B (en) | 1982-01-13 |
| BR7804647A (pt) | 1979-03-20 |
| US4402733A (en) | 1983-09-06 |
| CH638794A5 (de) | 1983-10-14 |
| GB2002360A (en) | 1979-02-21 |
| FR2401145A1 (fr) | 1979-03-23 |
| SU810065A3 (ru) | 1981-02-28 |
| BE869138A (fr) | 1979-01-19 |
| IT1181588B (it) | 1987-09-30 |
| NZ187904A (en) | 1981-03-16 |
| FR2401145B1 (es) | 1983-07-08 |
| IL55124A0 (en) | 1978-09-29 |
| SE444435B (sv) | 1986-04-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0336494B1 (en) | Triazine herbicides | |
| JP3041315B2 (ja) | 殺菌性化合物、その製造方法及びそれを含有する殺菌剤組成物 | |
| US4816064A (en) | Triazine derivatives, herbicidal composition containing them, and method of controlling growth of undesired vegetation by using same | |
| CZ659089A3 (en) | Derivatives of propenic acid, process of their preparation, fungicidal, insecticidal and acaricidal agents in which the derivatives are comprised and their use | |
| CZ110696A3 (en) | Dihydropyridazinones a pyridazinones, their use as fungicides and insecticides | |
| CZ205096A3 (en) | Aryl- and heteroarylpyrimidines and herbicidal agents in which said compounds are comprised | |
| US4116674A (en) | Process of severely damaging or killing unwanted plants with pyrimidine compounds | |
| HU182516B (en) | Herbicide compositions containing 2- or 4-amino-5-/alkyl-thio/-pyrimidines and process for preparing the active substance | |
| US6251829B1 (en) | Herbicidal benzoyloxy carboxylates and carboxamides | |
| CS199737B2 (en) | Herbicide | |
| US4225336A (en) | Phenoxyalkyloxazolines, as selective herbicides in cereals | |
| US4648898A (en) | Triazine derivatives and herbicides | |
| US3965139A (en) | 2-Chloro-N-(cyanomethyl)acetanilides | |
| US4353736A (en) | Method of selectively controlling weeds and herbicidal diphenyl ether oxime derivatives | |
| US4220770A (en) | Triazine compounds | |
| DE2726016A1 (de) | Herbizid wirksames 1,2,4-triazin- 5-on-derivat | |
| DE2856750A1 (de) | Herbizid wirksame 1.2.4-triazin-5-on- derivate | |
| US4816065A (en) | Herbicides | |
| EP0275131B1 (en) | Herbicidal oxoindanes and tetrahydronaphthalenes | |
| DD207846A5 (de) | Herbizide mittel | |
| US5089044A (en) | Substituted pyrimidinyloxy(thio)- and triazinyloxy (thio)acrylic acid derivatives, processes for their preparation and their use as herbicides, fungicides and plant growth regulators | |
| AU661159B2 (en) | N-acyldihydroquinoline derivatives, a method for producing the same and their use as herbicides | |
| CA1087615A (en) | Cyclopropyl derivatives of 1,2,4-triazine-5-one | |
| EP0581184B1 (en) | 3-Alkoxy-N-cycloalkylsulfonylalkanoic amide derivative, process for preparing the same and herbicide using the same | |
| US3669970A (en) | 3,5,6-substituted-6-(trifluoromethyl)-hydrouracils |