IL43536A - Tetrahydro-1,3,5-triazine-2,6-diones their production and their use as herbicides - Google Patents
Tetrahydro-1,3,5-triazine-2,6-diones their production and their use as herbicidesInfo
- Publication number
- IL43536A IL43536A IL7343536A IL4353673A IL43536A IL 43536 A IL43536 A IL 43536A IL 7343536 A IL7343536 A IL 7343536A IL 4353673 A IL4353673 A IL 4353673A IL 43536 A IL43536 A IL 43536A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- process according
- triazine
- acid
- tetrahydro
- Prior art date
Links
- YTFXKURWTLWPKK-UHFFFAOYSA-N 1,3,5-triazinane-2,4-dione Chemical class O=C1NCNC(=O)N1 YTFXKURWTLWPKK-UHFFFAOYSA-N 0.000 title claims abstract 3
- 239000004009 herbicide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 229910052736 halogen Chemical group 0.000 claims abstract description 14
- 150000002367 halogens Chemical group 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 90
- 238000000034 method Methods 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 32
- -1 hydroxylamino Chemical group 0.000 claims description 22
- 241000196324 Embryophyta Species 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 239000011230 binding agent Substances 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 6
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- BKCXNNIZYGZXTB-UHFFFAOYSA-N isocyanoformyl chloride Chemical compound ClC(=O)[N+]#[C-] BKCXNNIZYGZXTB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- DFZLOSJVNQSHSO-UHFFFAOYSA-N n-carbonochloridoylcarbamoyl chloride Chemical compound ClC(=O)NC(Cl)=O DFZLOSJVNQSHSO-UHFFFAOYSA-N 0.000 claims description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UDUMWDDMSHXGGQ-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-methylazanium;iodide Chemical compound I.CSC(N)=NC UDUMWDDMSHXGGQ-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- 101100310622 Mus musculus Soga1 gene Proteins 0.000 description 3
- 241001310793 Podium Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- HRDFVQLHRAQAKQ-UHFFFAOYSA-N methyl n'-ethylcarbamimidothioate Chemical compound CCNC(=N)SC HRDFVQLHRAQAKQ-UHFFFAOYSA-N 0.000 description 3
- VJTOMRZQGQNLTP-UHFFFAOYSA-N n-carbonochloridoyl-n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)N(C(Cl)=O)C(Cl)=O VJTOMRZQGQNLTP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XIXMILKULCLASF-UHFFFAOYSA-N 1-methyl-6-methylsulfanyl-3-propan-2-yl-1,3,5-triazinane-2,4-dione Chemical compound CSC1NC(=O)N(C(C)C)C(=O)N1C XIXMILKULCLASF-UHFFFAOYSA-N 0.000 description 2
- GEWRKGDRYZIFNP-UHFFFAOYSA-N 1h-1,3,5-triazine-2,4-dione Chemical compound OC1=NC=NC(O)=N1 GEWRKGDRYZIFNP-UHFFFAOYSA-N 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 240000005702 Galium aparine Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241000209082 Lolium Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- CNGFQZPAQMNBPP-UHFFFAOYSA-N [c-methylsulfanyl-n-(propan-2-ylideneamino)carbonimidoyl]azanium;iodide Chemical compound I.CS\C(N)=N/N=C(C)C CNGFQZPAQMNBPP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- ZSERAKDDJUCIBK-UHFFFAOYSA-N n-carbonochloridoyl-n-phenylcarbamoyl chloride Chemical compound ClC(=O)N(C(Cl)=O)C1=CC=CC=C1 ZSERAKDDJUCIBK-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VWXLCWNPSOUPPE-UHFFFAOYSA-N (1-amino-2-methylpropylidene)azanium;chloride Chemical compound Cl.CC(C)C(N)=N VWXLCWNPSOUPPE-UHFFFAOYSA-N 0.000 description 1
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 1
- CZWPBJXVNBIDMC-UHFFFAOYSA-N 1-amino-3-(3,4-dichlorophenyl)-6-methylsulfanyl-1,3,5-triazinane-2,4-dione Chemical compound O=C1N(N)C(SC)NC(=O)N1C1=CC=C(Cl)C(Cl)=C1 CZWPBJXVNBIDMC-UHFFFAOYSA-N 0.000 description 1
- CIHUHBUKIKNJLK-UHFFFAOYSA-N 1-amino-3-cyclohexyl-6-methylsulfanyl-1,3,5-triazinane-2,4-dione Chemical compound O=C1N(N)C(SC)NC(=O)N1C1CCCCC1 CIHUHBUKIKNJLK-UHFFFAOYSA-N 0.000 description 1
- JUEFDVSMEHYRSK-UHFFFAOYSA-N 1-benzyl-3-ethylurea Chemical compound CCNC(=O)NCC1=CC=CC=C1 JUEFDVSMEHYRSK-UHFFFAOYSA-N 0.000 description 1
- QNMWSLMZPATZTD-UHFFFAOYSA-N 1-benzyl-3-methylurea Chemical compound CNC(=O)NCC1=CC=CC=C1 QNMWSLMZPATZTD-UHFFFAOYSA-N 0.000 description 1
- BBUVNFZPAAVCSX-UHFFFAOYSA-N 1-cyclohexyl-3-ethylurea Chemical compound CCNC(=O)NC1CCCCC1 BBUVNFZPAAVCSX-UHFFFAOYSA-N 0.000 description 1
- YKLDLMXTBHWMPV-UHFFFAOYSA-N 1-cyclohexyl-3-methylurea Chemical compound CNC(=O)NC1CCCCC1 YKLDLMXTBHWMPV-UHFFFAOYSA-N 0.000 description 1
- SAWZLGZLJDMTPD-UHFFFAOYSA-N 1-ethyl-3-propan-2-ylurea Chemical compound CCNC(=O)NC(C)C SAWZLGZLJDMTPD-UHFFFAOYSA-N 0.000 description 1
- SQBHGDSDVWCPHN-UHFFFAOYSA-N 1-methyl-3-phenylurea Chemical compound CNC(=O)NC1=CC=CC=C1 SQBHGDSDVWCPHN-UHFFFAOYSA-N 0.000 description 1
- YLFYUSNPIHLTBP-UHFFFAOYSA-N 1-methyl-3-propan-2-ylurea Chemical compound CNC(=O)NC(C)C YLFYUSNPIHLTBP-UHFFFAOYSA-N 0.000 description 1
- BWOCAYWNSPWKBO-UHFFFAOYSA-N 3-(ethylamino)-1,3,5-triazinane-2,4-dione Chemical compound C(C)NN1C(NCNC1=O)=O BWOCAYWNSPWKBO-UHFFFAOYSA-N 0.000 description 1
- SJPRWVGEDDRASQ-UHFFFAOYSA-N 3-benzyl-6-methylsulfanyl-1-(propan-2-ylideneamino)-1,3,5-triazinane-2,4-dione Chemical compound O=C1N(N=C(C)C)C(SC)NC(=O)N1CC1=CC=CC=C1 SJPRWVGEDDRASQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BICLGOYLQCSGFL-UHFFFAOYSA-N 6-(hydroxyamino)-1-methyl-3-propan-2-yl-1,3,5-triazinane-2,4-dione Chemical compound CC(C)N1C(=O)NC(NO)N(C)C1=O BICLGOYLQCSGFL-UHFFFAOYSA-N 0.000 description 1
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 241000208175 Daucus Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000551547 Dione <red algae> Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000007351 Eleusine Nutrition 0.000 description 1
- 241000209215 Eleusine Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 244000214240 Galinsoga parviflora Species 0.000 description 1
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum 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
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000209048 Poa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000209051 Saccharum Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 240000001261 Urtica urens Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- OVEBGEVIVUYCEI-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-cyclohexylazanium;iodide Chemical compound I.CSC(N)=NC1CCCCC1 OVEBGEVIVUYCEI-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 235000015115 caffè latte Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
- ANPPAZLOAHBWAU-UHFFFAOYSA-N ethyl N'-(butan-2-ylideneamino)carbamimidothioate hydroiodide Chemical compound I.CCSC(=N)NN=C(C)CC ANPPAZLOAHBWAU-UHFFFAOYSA-N 0.000 description 1
- KNTDDRFBTCHDMF-UHFFFAOYSA-N ethyl n'-butylcarbamimidothioate Chemical compound CCCCNC(=N)SCC KNTDDRFBTCHDMF-UHFFFAOYSA-N 0.000 description 1
- MDGDHIMLZYCSAG-UHFFFAOYSA-N ethyl n'-phenylcarbamimidothioate;hydroiodide Chemical compound I.CCSC(N)=NC1=CC=CC=C1 MDGDHIMLZYCSAG-UHFFFAOYSA-N 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- KRZGKJJPEOUIBI-UHFFFAOYSA-N hydron;thiourea;iodide Chemical compound I.NC(S)=N KRZGKJJPEOUIBI-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- KOUKMIYVWNIWSJ-UHFFFAOYSA-N methyl N'-(ethylideneamino)carbamimidothioate hydroiodide Chemical compound I.CSC(=N)NN=CC KOUKMIYVWNIWSJ-UHFFFAOYSA-N 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- KGGGDOUUGUNODJ-UHFFFAOYSA-N methyl n'-ethylcarbamimidothioate;hydroiodide Chemical compound I.CCNC(=N)SC KGGGDOUUGUNODJ-UHFFFAOYSA-N 0.000 description 1
- NROPRCUPBJFONT-UHFFFAOYSA-N methyl n'-phenylcarbamimidothioate Chemical compound CSC(N)=NC1=CC=CC=C1 NROPRCUPBJFONT-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- JMUUPPALQRUKTR-UHFFFAOYSA-N n-carbonochloridoyl-n-(4-chlorophenyl)carbamoyl chloride Chemical compound ClC(=O)N(C(Cl)=O)C1=CC=C(Cl)C=C1 JMUUPPALQRUKTR-UHFFFAOYSA-N 0.000 description 1
- YJFBQAVICWDKHD-UHFFFAOYSA-N n-carbonochloridoyl-n-cyclohexylcarbamoyl chloride Chemical compound ClC(=O)N(C(Cl)=O)C1CCCCC1 YJFBQAVICWDKHD-UHFFFAOYSA-N 0.000 description 1
- ZCLVKRFCNWGTIS-UHFFFAOYSA-N n-carbonochloridoyl-n-methylcarbamoyl chloride Chemical compound ClC(=O)N(C)C(Cl)=O ZCLVKRFCNWGTIS-UHFFFAOYSA-N 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- DFWRZHZPJJAJMX-UHFFFAOYSA-N propanimidamide;hydrochloride Chemical compound Cl.CCC(N)=N DFWRZHZPJJAJMX-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/38—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2254200A DE2254200C2 (de) | 1972-11-06 | 1972-11-06 | Tetrahydro-1,3,5-triazin-2,6-dione, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43536A0 IL43536A0 (en) | 1974-03-14 |
| IL43536A true IL43536A (en) | 1977-05-31 |
Family
ID=5860916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL7343536A IL43536A (en) | 1972-11-06 | 1973-11-01 | Tetrahydro-1,3,5-triazine-2,6-diones their production and their use as herbicides |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US4056527A (sk) |
| JP (1) | JPS6034953A (sk) |
| AR (1) | AR213259A1 (sk) |
| AT (1) | AT328790B (sk) |
| AU (1) | AU497238B2 (sk) |
| BE (1) | BE806964A (sk) |
| BG (1) | BG20539A3 (sk) |
| BR (1) | BR7308613D0 (sk) |
| CH (2) | CH596767A5 (sk) |
| CS (1) | CS187386B2 (sk) |
| DD (1) | DD112344A5 (sk) |
| DE (1) | DE2254200C2 (sk) |
| DK (1) | DK136067C (sk) |
| EG (1) | EG11056A (sk) |
| ES (2) | ES420258A1 (sk) |
| FI (1) | FI56683C (sk) |
| FR (1) | FR2205517B1 (sk) |
| GB (1) | GB1397888A (sk) |
| HU (1) | HU169963B (sk) |
| IE (1) | IE38471B1 (sk) |
| IL (1) | IL43536A (sk) |
| IT (1) | IT1046112B (sk) |
| KE (1) | KE2585A (sk) |
| LU (1) | LU68742A1 (sk) |
| MY (1) | MY7600036A (sk) |
| NL (1) | NL177111C (sk) |
| NO (1) | NO140061C (sk) |
| PH (1) | PH11488A (sk) |
| PL (1) | PL91285B1 (sk) |
| RO (1) | RO72337A (sk) |
| SE (1) | SE404800B (sk) |
| SU (1) | SU762759A3 (sk) |
| TR (1) | TR17724A (sk) |
| YU (1) | YU283473A (sk) |
| ZA (1) | ZA738488B (sk) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3983116A (en) * | 1973-04-05 | 1976-09-28 | E. I. Du Pont De Nemours And Company | Herbicidal triazines |
| US4035365A (en) | 1973-11-01 | 1977-07-12 | Imperial Chemical Industries Limited | Triazinediones |
| GB1543037A (en) | 1975-02-05 | 1979-03-28 | Ici Ltd | Selective herbicidal triazine-diones |
| US4068081A (en) | 1974-02-15 | 1978-01-10 | Imperial Chemical Industries Limited | Δ-Triazine-2,6-dione |
| US3907795A (en) * | 1974-05-24 | 1975-09-23 | Du Pont | 3-(Tetrahydro-2-pyranyl)-1,3,5-triazinediones and their use as herbicides |
| US4174445A (en) * | 1976-10-23 | 1979-11-13 | Bayer Aktiengesellschaft | Preparation of arthropodicidally active substituted triazine-2,4-diones |
| DE3006263A1 (de) | 1980-02-20 | 1981-08-27 | Bayer Ag, 5090 Leverkusen | Verfahren und herstellung von 1-amino-1,3,5-triazin-2,4(1h, 3h)-dionen |
| US4348331A (en) * | 1980-09-19 | 1982-09-07 | Bayer Aktiengesellschaft | Process for the preparation of N-substituted imido-dicarboxylic acid diaryl esters |
| AU7715981A (en) * | 1980-11-21 | 1982-05-27 | Bayer Aktiengesellschaft | Synergistic herbicidal mixtures |
| DE3106724A1 (de) * | 1981-02-24 | 1982-09-09 | Bayer Ag, 5090 Leverkusen | "verfahren zur herstellung von 1-amino-1,3,5-triazin-2,4 (1h, 3h)-dionen" |
| DE3238007A1 (de) * | 1982-10-13 | 1984-04-19 | Bayer Ag, 5090 Leverkusen | Herbizide mittel auf basis von triazinon- und triazindion-derivaten |
| DE3409065A1 (de) * | 1984-03-13 | 1985-09-26 | Bayer Ag, 5090 Leverkusen | 3-cyclopropylmethyl-1,3,5-triazin-2,4-dione |
| DE3412946A1 (de) * | 1984-04-06 | 1985-10-17 | Bayer Ag, 5090 Leverkusen | 3-(2,2-tetramethylen-propyl)-1,3,5-triazin-2,4-dione |
| JP2635869B2 (ja) * | 1991-11-20 | 1997-07-30 | 株式会社東芝 | 熱交換器 |
| CA2128232A1 (en) * | 1992-01-15 | 1993-07-22 | Kofi Sam Amuti | Herbicides for citrus, oil palm, rubber and other plantation crops |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3835133A (en) * | 1971-03-15 | 1974-09-10 | Sandoz Ltd | Hexahydro-1,3,5-triazine-2,4-diones |
| BE788872A (fr) * | 1971-09-16 | 1973-03-15 | Du Pont | Nouvelles 1,3, 5-triazinediones, leur preparation et compositions herbicides les contenant |
| IL42103A (en) * | 1972-05-24 | 1976-05-31 | Du Pont | 6-amino-s-triazine-2,4-(1h,3h)-diones and corresponding 4-thio compounds,their preparation and their use as herbicides |
| IL42095A0 (en) * | 1972-05-24 | 1973-07-30 | Du Pont | Novel 1,3,5-triazinediones,their preparation and their use as herbicides |
| US3873540A (en) * | 1973-01-22 | 1975-03-25 | Du Pont | 1,3,5-triazinediones |
| US3855219A (en) * | 1972-07-03 | 1974-12-17 | Du Pont | 1,3,5-triazinediones |
| US3983116A (en) * | 1973-04-05 | 1976-09-28 | E. I. Du Pont De Nemours And Company | Herbicidal triazines |
| US3933815A (en) * | 1974-06-24 | 1976-01-20 | E. I. Du Pont De Nemours And Company | Trifluoromethyl triazines |
-
1972
- 1972-11-06 DE DE2254200A patent/DE2254200C2/de not_active Expired
-
1973
- 1973-10-18 US US05/407,693 patent/US4056527A/en not_active Expired - Lifetime
- 1973-10-24 PH PH15153A patent/PH11488A/en unknown
- 1973-10-31 YU YU02834/73A patent/YU283473A/xx unknown
- 1973-11-01 CS CS737524A patent/CS187386B2/cs unknown
- 1973-11-01 IL IL7343536A patent/IL43536A/en unknown
- 1973-11-02 IT IT30895/73A patent/IT1046112B/it active
- 1973-11-02 DD DD174431A patent/DD112344A5/xx unknown
- 1973-11-02 BG BG024913A patent/BG20539A3/xx unknown
- 1973-11-02 FI FI3392/73A patent/FI56683C/fi active
- 1973-11-02 SU SU731969697A patent/SU762759A3/ru active
- 1973-11-03 RO RO197376523A patent/RO72337A/ro unknown
- 1973-11-05 ZA ZA738488A patent/ZA738488B/xx unknown
- 1973-11-05 AU AU62167/73A patent/AU497238B2/en not_active Expired
- 1973-11-05 AR AR250846A patent/AR213259A1/es active
- 1973-11-05 CH CH880277A patent/CH596767A5/xx not_active IP Right Cessation
- 1973-11-05 LU LU68742A patent/LU68742A1/xx unknown
- 1973-11-05 BR BR8613/73A patent/BR7308613D0/pt unknown
- 1973-11-05 EG EG417/73A patent/EG11056A/xx active
- 1973-11-05 PL PL1973166334A patent/PL91285B1/pl unknown
- 1973-11-05 NO NO734255A patent/NO140061C/no unknown
- 1973-11-05 CH CH1552373A patent/CH596765A5/xx not_active IP Right Cessation
- 1973-11-05 GB GB5123173A patent/GB1397888A/en not_active Expired
- 1973-11-05 IE IE1985/73A patent/IE38471B1/xx unknown
- 1973-11-05 DK DK597873A patent/DK136067C/da not_active IP Right Cessation
- 1973-11-05 TR TR17724A patent/TR17724A/xx unknown
- 1973-11-05 NL NLAANVRAGE7315118,A patent/NL177111C/xx active Search and Examination
- 1973-11-06 AT AT932973A patent/AT328790B/de not_active IP Right Cessation
- 1973-11-06 BE BE137446A patent/BE806964A/xx not_active IP Right Cessation
- 1973-11-06 HU HUBA2990A patent/HU169963B/hu unknown
- 1973-11-06 FR FR7339335A patent/FR2205517B1/fr not_active Expired
- 1973-11-07 ES ES420258A patent/ES420258A1/es not_active Expired
- 1973-12-11 SE SE7315000A patent/SE404800B/xx unknown
-
1975
- 1975-12-02 KE KE2585*UA patent/KE2585A/xx unknown
-
1976
- 1976-04-15 ES ES447080A patent/ES447080A1/es not_active Expired
- 1976-12-31 MY MY197636A patent/MY7600036A/xx unknown
-
1984
- 1984-05-10 JP JP59091989A patent/JPS6034953A/ja active Granted
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3759939A (en) | Certain 1-(1,3,4-thiadiazol-2-yl)-imidazolidinone-(2) compounds | |
| IL43536A (en) | Tetrahydro-1,3,5-triazine-2,6-diones their production and their use as herbicides | |
| US3920653A (en) | 1-Aminouracil compounds and herbicidal compositions | |
| IL44710A (en) | 1-phenyl-2-azolyl-formamidines their preparation and their use as herbicides | |
| US3758492A (en) | 1-(1,3,4-thiadiazol-2-yl)-imidazolidinone-(2) compounds | |
| IL30585A (en) | Compounds 1,2,4- Thiodiazolyl urea, their preparation and use for weed control | |
| US3415827A (en) | Pesticidal triazinyl azides | |
| JP2849390B2 (ja) | 新規２−（置換イミノ）−１，３，４−ジヒドロチアジアゾール類 | |
| US4057417A (en) | 6-Sec.-butyl-1,2,4-triazin-5(4H)-one compounds and herbicidal compositions | |
| IL26698A (en) | Amidothionophosphoric acid ester | |
| US3981714A (en) | Cyclic N-thiadiazolyl-(2)-carboxylic acid compounds and herbicidal compositions | |
| CA1166250A (en) | Substituted tetrahydropyrimidinone derivatives, process for their preparation and their use as herbicides | |
| IE50227B1 (en) | 5-amino-4-cyano-1-(2,4,6-trichlorophenyl)pyrazole,process for its preparation,herbicidal compositions containing it and their use | |
| IL32523A (en) | N-acyl-2-amino-1,3,4-thiazoles,their preparation and their use as herbicides | |
| US4128412A (en) | Herbicidal composition and method using N-(2-ethylsulfonyl-1,3,4-thiadiazol-5-yl)-N-methyl-N'-methyl urea | |
| US3954785A (en) | Acylated urea compounds and herbicidal compositions | |
| US3940391A (en) | 3,4-Dihydro-1,2,4-triazine compounds | |
| US4195181A (en) | 1,3,4-Thiadiazole compounds and herbicidal compositions | |
| EP0129830B1 (en) | N-alkylaminopyrazole derivatives, process for preparing the same, and herbicides containing the same | |
| US3758481A (en) | Ridine m-(2,4-dichloro - 5-(haloalkoxy)-phenylcarbomoyl)-pyrrolidine or pipe | |
| US3984468A (en) | Herbicidal N-trifluoromethylmercaptophenyl ureas | |
| IL32577A (en) | Herbicidal agents containing imidazolidinone derivatives | |
| US4017529A (en) | Herbicidal allophanimidates | |
| US4000173A (en) | 3-aryl-2-halothiopropionic acid s-esters | |
| US3962304A (en) | Alkoxy-substituted benzyl dithiocarbamic acid esters |