DK149104B - Herbicidt virksomme 1,2,4-triazin-5-on-derivater, herbicidt middel og anvendelse af forbindelserne og midlet - Google Patents

Herbicidt virksomme 1,2,4-triazin-5-on-derivater, herbicidt middel og anvendelse af forbindelserne og midlet Download PDF

Info

Publication number: DK149104B
Authority: DK; Denmark
Prior art keywords: parts; compounds; agent; plants; active compound
Prior art date: 1977-07-20

Application number

DK319978AA

Other languages

Danish (da)

English (en)

Other versions

DK319978A (da

Inventor

Georg Pissiotas

Willy Meyer

Werner Schwarze

Herbert Klenk

Wolfgang Leuchtenberger

Original Assignee

Ciba Geigy Ag

Degussa

Priority date (The priority date 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 date listed.)

1977-07-20

Filing date

1978-07-17

Publication date

1986-01-27

1977-07-20 Priority claimed from DE19772732797 external-priority patent/DE2732797A1/de

1978-07-17 Application filed by Ciba Geigy Ag, Degussa filed Critical Ciba Geigy Ag

1979-01-21 Publication of DK319978A publication Critical patent/DK319978A/da

1986-01-27 Publication of DK149104B publication Critical patent/DK149104B/da

Links

150000001875 compounds Chemical class 0.000 title description 54
BFNNILAMSKQDRN-UHFFFAOYSA-N 2h-1,2,4-triazin-5-one Chemical class O=C1C=NNC=N1 BFNNILAMSKQDRN-UHFFFAOYSA-N 0.000 title description 6
241000196324 Embryophyta Species 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 16
238000002360 preparation method Methods 0.000 description 14
230000002363 herbicidal effect Effects 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000843 powder Substances 0.000 description 12
239000000243 solution Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000839 emulsion Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000000969 carrier Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000013078 crystal Substances 0.000 description 8
239000008187 granular material Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
-1 aryl glyoxylic acid Chemical compound 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
239000006072 paste Substances 0.000 description 7
229920000151 polyglycol Polymers 0.000 description 7
239000010695 polyglycol Substances 0.000 description 7
239000007921 spray Substances 0.000 description 7
235000010469 Glycine max Nutrition 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000004009 herbicide Substances 0.000 description 6
238000000034 method Methods 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 5
239000013543 active substance Substances 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
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 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
239000002904 solvent Substances 0.000 description 5
239000000725 suspension Substances 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
239000002689 soil Substances 0.000 description 4
239000007787 solid Substances 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
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 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229940126062 Compound A Drugs 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
238000000227 grinding Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
150000003918 triazines Chemical class 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
UJHMFTPWVRCYBJ-UHFFFAOYSA-N 2-(1-ethylcyclopropyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1(CC)CC1 UJHMFTPWVRCYBJ-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
244000061456 Solanum tuberosum Species 0.000 description 2
235000002595 Solanum tuberosum Nutrition 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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 2
230000035784 germination Effects 0.000 description 2
229940102396 methyl bromide Drugs 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 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
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 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
241000894007 species Species 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
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
DDCOGBPHOFARPW-UHFFFAOYSA-N 2-(1-methylcyclopropyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1(C)CC1 DDCOGBPHOFARPW-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
TZKRXCKERSCAQY-UHFFFAOYSA-N 4-amino-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical class NN1C(S)=NN=CC1=O TZKRXCKERSCAQY-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
FKDRVIBXTCXTTR-UHFFFAOYSA-N 4-amino-6-(1-methylcyclopropyl)-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound N=1N=C(S)N(N)C(=O)C=1C1(C)CC1 FKDRVIBXTCXTTR-UHFFFAOYSA-N 0.000 description 1
241000743339 Agrostis 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
244000025254 Cannabis sativa Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
244000192528 Chrysanthemum parthenium Species 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
241001354404 Cyanus Species 0.000 description 1
244000152970 Digitaria sanguinalis Species 0.000 description 1
235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
241000508725 Elymus repens Species 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
241000209510 Liliopsida Species 0.000 description 1
235000017945 Matricaria Nutrition 0.000 description 1
235000007232 Matricaria chamomilla Nutrition 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
244000088461 Panicum crus-galli Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
238000006434 Ritter amidation reaction Methods 0.000 description 1
241000209056 Secale Species 0.000 description 1
235000007238 Secale cereale Nutrition 0.000 description 1
244000062793 Sorghum vulgare Species 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
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001264 acyl cyanides Chemical class 0.000 description 1
150000001266 acyl halides Chemical class 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
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
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
125000004432 carbon atom Chemical group C* 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
UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 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
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution 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
238000009826 distribution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000003 effect on germination Effects 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
241001233957 eudicotyledons Species 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
239000003864 humus Substances 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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 1
230000007935 neutral effect Effects 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
238000010899 nucleation Methods 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
235000015927 pasta Nutrition 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
229920006395 saturated elastomer Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
BFGQTWYXWNCTSX-UHFFFAOYSA-N triazine-4,5-dione Chemical class O=C1C=NN=NC1=O BFGQTWYXWNCTSX-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 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)

DK319978AA 1977-07-20 1978-07-17 Herbicidt virksomme 1,2,4-triazin-5-on-derivater, herbicidt middel og anvendelse af forbindelserne og midlet DK149104B (da)

Applications Claiming Priority (2)

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
DE2732797		1977-07-20

Publications (2)

Publication Number	Publication Date
DK319978A DK319978A (da)	1979-01-21
DK149104B true DK149104B (da)	1986-01-27

Family

ID=6014415

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK319978AA DK149104B (da)	1977-07-20	1978-07-17	Herbicidt virksomme 1,2,4-triazin-5-on-derivater, herbicidt middel og anvendelse af forbindelserne og midlet

Country Status (27)

Country	Link
US (1)	US4402733A (cs)
AT (1)	AT362186B (cs)
AU (1)	AU520741B2 (cs)
BE (1)	BE869138A (cs)
BR (1)	BR7804647A (cs)
CA (1)	CA1079280A (cs)
CH (1)	CH638794A5 (cs)
CS (1)	CS199737B2 (cs)
DD (1)	DD139990A5 (cs)
DK (1)	DK149104B (cs)
EG (1)	EG13444A (cs)
ES (1)	ES471874A1 (cs)
FR (1)	FR2401145A1 (cs)
GB (1)	GB2002360B (cs)
GR (1)	GR65206B (cs)
HU (1)	HU182857B (cs)
IL (1)	IL55124A0 (cs)
IT (1)	IT1181588B (cs)
LU (1)	LU79992A1 (cs)
MX (1)	MX5454E (cs)
NL (1)	NL7807484A (cs)
NZ (1)	NZ187904A (cs)
PT (1)	PT68325A (cs)
SE (1)	SE444435B (cs)
SU (1)	SU810065A3 (cs)
TR (1)	TR19953A (cs)
ZA (1)	ZA784058B (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 ZA ZA00784058A patent/ZA784058B/xx unknown
- 1978-07-17 EG EG447/78A patent/EG13444A/xx active
- 1978-07-17 DK DK319978AA patent/DK149104B/da not_active Application Discontinuation
- 1978-07-17 AU AU38079/78A patent/AU520741B2/en not_active Expired
- 1978-07-18 LU LU79992A patent/LU79992A1/xx unknown
- 1978-07-18 IT IT50349/78A patent/IT1181588B/it active
- 1978-07-18 CS CS784784A patent/CS199737B2/cs unknown
- 1978-07-18 DD DD78206794A patent/DD139990A5/de unknown
- 1978-07-18 MX MX787267U patent/MX5454E/es unknown
- 1978-07-19 BE BE6046543A patent/BE869138A/xx not_active IP Right Cessation
- 1978-07-19 SE SE7807988A patent/SE444435B/sv unknown
- 1978-07-19 PT PT68325A patent/PT68325A/pt unknown
- 1978-07-19 ES ES471874A patent/ES471874A1/es not_active Expired
- 1978-07-19 BR BR7804647A patent/BR7804647A/pt unknown
- 1978-07-19 HU HU78CI1847A patent/HU182857B/hu 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
- 1978-07-19 CH CH778878A patent/CH638794A5/de not_active IP Right Cessation
- 1978-07-19 NZ NZ187904A patent/NZ187904A/xx unknown
- 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
DK319978A (da)	1979-01-21
MX5454E (es)	1983-08-10
NL7807484A (nl)	1979-01-23
GB2002360B (en)	1982-01-13
CS199737B2 (en)	1980-07-31
IL55124A0 (en)	1978-09-29
PT68325A (pt)	1978-08-01
SE7807988L (sv)	1979-01-21
EG13444A (en)	1982-03-31
FR2401145B1 (cs)	1983-07-08
BE869138A (fr)	1979-01-19
ATA524178A (de)	1980-09-15
BR7804647A (pt)	1979-03-20
CH638794A5 (de)	1983-10-14
AU520741B2 (en)	1982-02-25
IT1181588B (it)	1987-09-30
NZ187904A (en)	1981-03-16
CA1079280A (en)	1980-06-10
HU182857B (en)	1984-03-28
ES471874A1 (es)	1979-02-01
US4402733A (en)	1983-09-06
ZA784058B (en)	1979-07-25
AT362186B (de)	1981-04-27
DD139990A5 (de)	1980-02-06
TR19953A (tr)	1980-05-15
LU79992A1 (cs)	1978-12-12
GB2002360A (en)	1979-02-21
FR2401145A1 (fr)	1979-03-23
IT7850349A0 (it)	1978-07-18
SU810065A3 (ru)	1981-02-28
SE444435B (sv)	1986-04-14
AU3807978A (en)	1980-01-17
GR65206B (en)	1980-07-29

Legal Events

Date	Code	Title	Description
1986-08-11	PTS	Application withdrawn

Publication	Publication Date	Title
SK696184A3 (en)	1997-06-04	2-(2-subst.benzoyl)cyclohexane-1,3-diones, herbicidal agents on their base and their use
PL134968B1 (en)	1985-09-30	Herbicide and method of manufacture of novel derivatives of tetrahydrophtalimide
US4816064A (en)	1989-03-28	Triazine derivatives, herbicidal composition containing them, and method of controlling growth of undesired vegetation by using same
JPS595181A (ja)	1984-01-12	Ｎ−ヘテロシクロスルホニル−ｎ′−ピリミジニル尿素およびｎ−ヘテロシクロスルホニル−ｎ′−トリアジニル尿素、その製造方法および該化合物を含む植物の生長抑制剤
CZ205096A3 (en)	1996-10-16	Aryl- and heteroarylpyrimidines and herbicidal agents in which said compounds are comprised
EP0786937A2 (en)	1997-08-06	Herbicidal compositions
US4116674A (en)	1978-09-26	Process of severely damaging or killing unwanted plants with pyrimidine compounds
RU2040901C1 (ru)	1995-08-09	Сульфонилмочевины и способ борьбы с нежелательной растительностью
CS196383B2 (en)	1980-03-31	Herbicide and method of producing the active constituents
DK149104B (da)	1986-01-27	Herbicidt virksomme 1,2,4-triazin-5-on-derivater, herbicidt middel og anvendelse af forbindelserne og midlet
US3756803A (en)	1973-09-04	Herbicidal pyrido(1,2-delta)-s-triazinediones
US4648898A (en)	1987-03-10	Triazine derivatives and herbicides
SK106197A3 (en)	1997-12-10	Triazine derivatives
US4057417A (en)	1977-11-08	6-Sec.-butyl-1,2,4-triazin-5(4H)-one compounds and herbicidal compositions
US4220770A (en)	1980-09-02	Triazine compounds
CS228937B2 (en)	1984-05-14	Herbicide and method of preparing active substances thereof
RU2015970C1 (ru)	1994-07-15	Производные пиримидина, обладающие гербицидной активностью, способ борьбы с нежелательной растительностью
US4353736A (en)	1982-10-12	Method of selectively controlling weeds and herbicidal diphenyl ether oxime derivatives
US5536703A (en)	1996-07-16	Herbicidal substituted benzoyl bicycloalkanediones
CS242883B2 (en)	1986-05-15	Herbicide and method of its efficient component production
GB2103610A (en)	1983-02-23	Herbicidal compounds derived from N-sulphonyl-aryloxybenamides and the processes for their preparation and use
EP0147477B1 (en)	1987-11-04	Pyridyloxybenzanilide derivative and herbicide containing it
CS237322B2 (en)	1985-07-16	Herbicide agent and processing of active component
GB2133011A (en)	1984-07-18	Triazine derivative and an intermediate therefor useful as herbicides
US3843348A (en)	1974-10-22	Use of 6-(trifluoromethyl)hydrouracils as herbicides