DE2263805A1 - Verfahren zum aendern des bluehens und/oder der geschlechtlichen vermehrung von pflanzen - Google Patents
Verfahren zum aendern des bluehens und/oder der geschlechtlichen vermehrung von pflanzenInfo
- Publication number
- DE2263805A1 DE2263805A1 DE2263805A DE2263805A DE2263805A1 DE 2263805 A1 DE2263805 A1 DE 2263805A1 DE 2263805 A DE2263805 A DE 2263805A DE 2263805 A DE2263805 A DE 2263805A DE 2263805 A1 DE2263805 A1 DE 2263805A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- carbon atoms
- triazine
- dione
- methoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 34
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 title description 11
- -1 alkyl radical Chemical class 0.000 claims description 113
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- GEWRKGDRYZIFNP-UHFFFAOYSA-N 1h-1,3,5-triazine-2,4-dione Chemical compound OC1=NC=NC(O)=N1 GEWRKGDRYZIFNP-UHFFFAOYSA-N 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 9
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 8
- 240000008042 Zea mays Species 0.000 claims description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 7
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 208000006278 hypochromic anemia Diseases 0.000 claims description 5
- 235000009973 maize Nutrition 0.000 claims description 5
- 230000017074 necrotic cell death Effects 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- YILOZLHPVUQWQF-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-methoxy-1h-1,3,5-triazine-2,4-dione Chemical group O=C1NC(OC)=NC(=O)N1C1=CC=C(Cl)C=C1 YILOZLHPVUQWQF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000009399 inbreeding Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 3
- OBJPNFKDMUZZGU-UHFFFAOYSA-N 6-methoxy-3-(4-methylphenyl)-1h-1,3,5-triazine-2,4-dione Chemical compound O=C1NC(OC)=NC(=O)N1C1=CC=C(C)C=C1 OBJPNFKDMUZZGU-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- QRHLEENUCKIKLP-UHFFFAOYSA-N 3-(2-chlorophenyl)-6-methoxy-1h-1,3,5-triazine-2,4-dione Chemical compound O=C1NC(OC)=NC(=O)N1C1=CC=CC=C1Cl QRHLEENUCKIKLP-UHFFFAOYSA-N 0.000 claims description 2
- 230000010165 autogamy Effects 0.000 claims description 2
- FQSPZUVKFIKBQM-UHFFFAOYSA-N 1-methoxy-1,3,5-triazine-2,4-dione Chemical compound CON1C(NC(N=C1)=O)=O FQSPZUVKFIKBQM-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229910001422 barium ion Inorganic materials 0.000 claims 2
- 229910001424 calcium ion Inorganic materials 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229910001416 lithium ion Inorganic materials 0.000 claims 2
- 229910001425 magnesium ion Inorganic materials 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 229910001414 potassium ion Inorganic materials 0.000 claims 2
- 229910001415 sodium ion Inorganic materials 0.000 claims 2
- MKDREKCWGSOBTF-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-methoxy-1h-1,3,5-triazine-2,4-dione Chemical group O=C1NC(OC)=NC(=O)N1C1=CC=C(F)C=C1 MKDREKCWGSOBTF-UHFFFAOYSA-N 0.000 claims 1
- SNULTPQANPFFQH-UHFFFAOYSA-N 6-methoxy-1h-1,3,5-triazine-2,4-dione Chemical compound COC1=NC(=O)NC(=O)N1 SNULTPQANPFFQH-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZTHJQNRRSGRVOM-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1C(NC(N=C1OC)=O)=O Chemical compound ClC1=CC=C(C=C1)N1C(NC(N=C1OC)=O)=O ZTHJQNRRSGRVOM-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 241000196324 Embryophyta Species 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000012948 isocyanate Substances 0.000 description 19
- 150000002513 isocyanates Chemical class 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 235000013399 edible fruits Nutrition 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 7
- 230000005094 fruit set Effects 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002540 isothiocyanates Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000008117 seed development Effects 0.000 description 5
- VZOPVKZLLGMDDG-UHFFFAOYSA-N 1-oxido-4-phenylpyridin-1-ium Chemical compound C1=C[N+]([O-])=CC=C1C1=CC=CC=C1 VZOPVKZLLGMDDG-UHFFFAOYSA-N 0.000 description 4
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229940069428 antacid Drugs 0.000 description 4
- 239000003159 antacid agent Substances 0.000 description 4
- 230000001458 anti-acid effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 210000005069 ears Anatomy 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 4
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000014639 sexual reproduction Effects 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
- VZNCSZQPNIEEMN-UHFFFAOYSA-N 1-fluoro-2-isocyanatobenzene Chemical compound FC1=CC=CC=C1N=C=O VZNCSZQPNIEEMN-UHFFFAOYSA-N 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- DEZNOFAJXWNMHJ-UHFFFAOYSA-N methyl (ne)-n-[amino(methoxy)methylidene]carbamate Chemical compound COC(N)=NC(=O)OC DEZNOFAJXWNMHJ-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 2
- DUUSMHZSZWMNCB-UHFFFAOYSA-N 2-isocyanatobutane Chemical compound CCC(C)N=C=O DUUSMHZSZWMNCB-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- NHOUNTPDGFGWGU-UHFFFAOYSA-N 3-methyl-6-methylsulfanyl-1h-1,3,5-triazine-2,4-dione Chemical compound CSC1=NC(=O)N(C)C(=O)N1 NHOUNTPDGFGWGU-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- FTZJLXIATZSKIL-UHFFFAOYSA-N 4-chloro-1-isocyanato-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1N=C=O FTZJLXIATZSKIL-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- VNTDZDJWMPDWKA-UHFFFAOYSA-N 6-ethoxy-3-propan-2-yl-1h-1,3,5-triazine-2,4-dione Chemical compound CCOC1=NC(=O)N(C(C)C)C(=O)N1 VNTDZDJWMPDWKA-UHFFFAOYSA-N 0.000 description 2
- 244000003416 Asparagus officinalis Species 0.000 description 2
- 235000005340 Asparagus officinalis Nutrition 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 235000016623 Fragaria vesca Nutrition 0.000 description 2
- 240000009088 Fragaria x ananassa Species 0.000 description 2
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 230000005200 bud stage Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000004459 forage Substances 0.000 description 2
- ZTLKDDKOSDHKJG-UHFFFAOYSA-N formic acid;isothiocyanic acid Chemical compound N=C=S.OC=O ZTLKDDKOSDHKJG-UHFFFAOYSA-N 0.000 description 2
- 230000005078 fruit development Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 2
- DUDXQIXWPJMPRQ-UHFFFAOYSA-N isocyanatomethylcyclohexane Chemical compound O=C=NCC1CCCCC1 DUDXQIXWPJMPRQ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- MMBDAJMDNVQFDV-UHFFFAOYSA-N methyl n-[amino(methylsulfanyl)methylidene]carbamate Chemical compound COC(=O)N=C(N)SC MMBDAJMDNVQFDV-UHFFFAOYSA-N 0.000 description 2
- 239000012053 oil suspension Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 2
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- VFIZBHJTOHUOEK-UHFFFAOYSA-N s-ethylisothiourea Chemical compound CCSC(N)=N VFIZBHJTOHUOEK-UHFFFAOYSA-N 0.000 description 2
- YPSUCTSXOROPBS-UHFFFAOYSA-N s-methyl chloromethanethioate Chemical compound CSC(Cl)=O YPSUCTSXOROPBS-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RDUIJJYNVCVETK-UHFFFAOYSA-N 1,2,4-trichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=C(N=C=O)C=C1Cl RDUIJJYNVCVETK-UHFFFAOYSA-N 0.000 description 1
- XBXSUYKXSAPAGL-UHFFFAOYSA-N 1,4-dichloro-2-isocyanato-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(N=C=O)C=C1Cl XBXSUYKXSAPAGL-UHFFFAOYSA-N 0.000 description 1
- TZGKNLNAPLNEFB-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-methoxy-2h-1,3,5-triazine Chemical compound C1=NC(OC)=NCN1C1=CC=C(Cl)C=C1 TZGKNLNAPLNEFB-UHFFFAOYSA-N 0.000 description 1
- KNUFXVUMTBAHOS-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-methylsulfanyl-2H-1,3,5-triazine Chemical compound ClC1=CC=C(C=C1)N1CN=C(N=C1)SC KNUFXVUMTBAHOS-UHFFFAOYSA-N 0.000 description 1
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- ZVFNUQWYLXXSJM-UHFFFAOYSA-N 1-ethyl-2-isocyanatobenzene Chemical compound CCC1=CC=CC=C1N=C=O ZVFNUQWYLXXSJM-UHFFFAOYSA-N 0.000 description 1
- OSZNGHFIWUGOCS-UHFFFAOYSA-N 1-ethylsulfanyl-1,3,5-triazine-2,4-dione Chemical compound C(C)SN1C(NC(N=C1)=O)=O OSZNGHFIWUGOCS-UHFFFAOYSA-N 0.000 description 1
- DSVGFKBFFICWLZ-UHFFFAOYSA-N 1-fluoro-4-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C=C1 DSVGFKBFFICWLZ-UHFFFAOYSA-N 0.000 description 1
- KVMKUTIUJGYHBA-UHFFFAOYSA-N 1-iodo-4-isocyanatobenzene Chemical compound IC1=CC=C(N=C=O)C=C1 KVMKUTIUJGYHBA-UHFFFAOYSA-N 0.000 description 1
- JRVZITODZAQRQM-UHFFFAOYSA-N 1-isocyanato-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=C=O JRVZITODZAQRQM-UHFFFAOYSA-N 0.000 description 1
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 1
- QNKQBDZVEKZFBN-UHFFFAOYSA-N 1-isocyanato-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(N=C=O)C=C1 QNKQBDZVEKZFBN-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- OLBJNSPBWLCTOT-UHFFFAOYSA-N 2,4-dichloro-1-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C(Cl)=C1 OLBJNSPBWLCTOT-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- CUPHDOKPZZCASO-UHFFFAOYSA-N 2-bromo-1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C(Br)=C1 CUPHDOKPZZCASO-UHFFFAOYSA-N 0.000 description 1
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
- FQKMESZJXXOIOR-UHFFFAOYSA-N 2-isocyanatoethylcyclopropane Chemical compound O=C=NCCC1CC1 FQKMESZJXXOIOR-UHFFFAOYSA-N 0.000 description 1
- VOTZJLLPYYCZRY-UHFFFAOYSA-N 2-methoxy-4-nitrophenyl isocyanate Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N=C=O VOTZJLLPYYCZRY-UHFFFAOYSA-N 0.000 description 1
- RIFDGUOJYIBEAB-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6-ethoxy-1h-1,3,5-triazine-2,4-dione Chemical compound O=C1NC(OCC)=NC(=O)N1C1=CC=C(Cl)C=C1Cl RIFDGUOJYIBEAB-UHFFFAOYSA-N 0.000 description 1
- VHIRFPKDMVNOEJ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6-methoxy-1h-1,3,5-triazine-2,4-dione Chemical compound O=C1NC(OC)=NC(=O)N1C1=CC=C(Cl)C=C1Cl VHIRFPKDMVNOEJ-UHFFFAOYSA-N 0.000 description 1
- VQMSJDFOMBPAFN-UHFFFAOYSA-N 3-(2-fluorophenyl)-6-methylsulfanyl-1h-1,3,5-triazine-2,4-dione Chemical compound O=C1NC(SC)=NC(=O)N1C1=CC=CC=C1F VQMSJDFOMBPAFN-UHFFFAOYSA-N 0.000 description 1
- INCWWIJWEOKKED-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-6-methoxy-1h-1,3,5-triazine-2,4-dione Chemical compound O=C1NC(OC)=NC(=O)N1C1=CC=C(F)C(F)=C1 INCWWIJWEOKKED-UHFFFAOYSA-N 0.000 description 1
- CZXBEYVRYBKXFG-UHFFFAOYSA-N 3-(4-bromophenyl)-6-methoxy-1h-1,3,5-triazine-2,4-dione Chemical compound O=C1NC(OC)=NC(=O)N1C1=CC=C(Br)C=C1 CZXBEYVRYBKXFG-UHFFFAOYSA-N 0.000 description 1
- BNIIRTCQLRNZHG-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-6-methoxy-1h-1,3,5-triazine-2,4-dione Chemical compound O=C1NC(OC)=NC(=O)N1C1=CC=C(Cl)C=C1C BNIIRTCQLRNZHG-UHFFFAOYSA-N 0.000 description 1
- SHPPDIBKHYVIKL-UHFFFAOYSA-N 3-isocyanatoprop-1-yne Chemical compound O=C=NCC#C SHPPDIBKHYVIKL-UHFFFAOYSA-N 0.000 description 1
- FWRITIJOCHMKJX-UHFFFAOYSA-N 3-tert-butyl-6-methylsulfanyl-1h-1,3,5-triazine-2,4-dione Chemical compound CSC1=NC(=O)N(C(C)(C)C)C(=O)N1 FWRITIJOCHMKJX-UHFFFAOYSA-N 0.000 description 1
- TVSXDZNUTPLDKY-UHFFFAOYSA-N 4-isocyanatobenzonitrile Chemical compound O=C=NC1=CC=C(C#N)C=C1 TVSXDZNUTPLDKY-UHFFFAOYSA-N 0.000 description 1
- BMUNHUMVENRHMM-UHFFFAOYSA-N 6-methoxy-3-(2-methylphenyl)-1h-1,3,5-triazine-2,4-dione Chemical compound O=C1NC(OC)=NC(=O)N1C1=CC=CC=C1C BMUNHUMVENRHMM-UHFFFAOYSA-N 0.000 description 1
- JVZWEKUDXYFSIY-UHFFFAOYSA-N 6-methylsulfanyl-3-propan-2-yl-1h-1,3,5-triazine-2,4-dione Chemical compound CSC1=NC(=O)N(C(C)C)C(=O)N1 JVZWEKUDXYFSIY-UHFFFAOYSA-N 0.000 description 1
- CWJZFKZMWCMPNW-UHFFFAOYSA-N 6-methylsulfanyl-3-propan-2-yl-1h-1,3,5-triazine-2,4-dione;sodium Chemical compound [Na].CSC1=NC(=O)N(C(C)C)C(=O)N1 CWJZFKZMWCMPNW-UHFFFAOYSA-N 0.000 description 1
- 206010001557 Albinism Diseases 0.000 description 1
- 240000007185 Albizia julibrissin Species 0.000 description 1
- 235000011468 Albizia julibrissin Nutrition 0.000 description 1
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 1
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- HQYSSRNHFWTIIU-UHFFFAOYSA-N C1(CC1)SC(N)=N Chemical compound C1(CC1)SC(N)=N HQYSSRNHFWTIIU-UHFFFAOYSA-N 0.000 description 1
- UQJCRIFQAIQYQG-UHFFFAOYSA-N COC(C=C1)=CC=C1N(C(NC(OC)=N1)=O)C1=O Chemical compound COC(C=C1)=CC=C1N(C(NC(OC)=N1)=O)C1=O UQJCRIFQAIQYQG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 241000551547 Dione <red algae> Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 235000017367 Guainella Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- QDONANKXGYICRB-UHFFFAOYSA-N O=C1NC(SC)=NC(=O)N1C1=CC=CC=C1Cl Chemical compound O=C1NC(SC)=NC(=O)N1C1=CC=CC=C1Cl QDONANKXGYICRB-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 108700003853 RON Proteins 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ICMGLRUYEQNHPF-UHFFFAOYSA-N Uraprene Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N(C(=O)N(C)C(=O)C=2)C)CC1 ICMGLRUYEQNHPF-UHFFFAOYSA-N 0.000 description 1
- RKZXQQPEDGMHBJ-LIGJGSPWSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentakis[[(z)-octadec-9-enoyl]oxy]hexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC RKZXQQPEDGMHBJ-LIGJGSPWSA-N 0.000 description 1
- NRQDOLSQDLZUIR-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC1F)N1C(NC(=NC1=O)OC)=O Chemical compound [N+](=O)([O-])C=1C=C(C=CC1F)N1C(NC(=NC1=O)OC)=O NRQDOLSQDLZUIR-UHFFFAOYSA-N 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 244000193174 agave Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- FDYQDWOZZOUKNF-UHFFFAOYSA-N azane 3-(4-chlorophenyl)-6-methoxy-1H-1,3,5-triazine-2,4-dione Chemical compound N.O=C1NC(OC)=NC(=O)N1C1=CC=C(Cl)C=C1 FDYQDWOZZOUKNF-UHFFFAOYSA-N 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 235000006263 bur ragweed Nutrition 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 235000003488 common ragweed Nutrition 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- MCVXJUWPGZMOBO-UHFFFAOYSA-N cyclohexyl carbamimidothioate Chemical compound NC(=N)SC1CCCCC1 MCVXJUWPGZMOBO-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910000462 iron(III) oxide hydroxide Inorganic materials 0.000 description 1
- QYKPRMWZTPVYJC-UHFFFAOYSA-N isocyanatocyclooctane Chemical compound O=C=NC1CCCCCCC1 QYKPRMWZTPVYJC-UHFFFAOYSA-N 0.000 description 1
- DBBRJAWSDTYYBM-UHFFFAOYSA-N isocyanatocyclopropane Chemical compound O=C=NC1CC1 DBBRJAWSDTYYBM-UHFFFAOYSA-N 0.000 description 1
- XIRJLSRMAMZTGY-UHFFFAOYSA-N isocyanic acid;isothiocyanic acid Chemical compound N=C=O.N=C=S XIRJLSRMAMZTGY-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- MDFRYRPNRLLJHT-UHFFFAOYSA-N methyl carbamimidate;sulfuric acid Chemical compound COC(N)=N.OS(O)(=O)=O MDFRYRPNRLLJHT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- KUAYFRMVCMNNGZ-UHFFFAOYSA-N methyl n'-(propan-2-ylcarbamoyl)carbamimidate Chemical compound CO\C(N)=N/C(=O)NC(C)C KUAYFRMVCMNNGZ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GRSBAMVBFWRBBH-UHFFFAOYSA-N o-ethyl chloromethanethioate Chemical compound CCOC(Cl)=S GRSBAMVBFWRBBH-UHFFFAOYSA-N 0.000 description 1
- YDICNEUIDBDVBZ-UHFFFAOYSA-N o-methyl n-[amino(methylsulfanyl)methylidene]carbamothioate Chemical compound COC(=S)N=C(N)SC YDICNEUIDBDVBZ-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000008119 pollen development Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- CPRHDNAFELKMOF-UHFFFAOYSA-N prop-2-ynyl carbamimidothioate Chemical compound NC(=N)SCC#C CPRHDNAFELKMOF-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004546 suspension concentrate 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
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G7/00—Botany in general
-
- G—PHYSICS
- G07—CHECKING-DEVICES
- G07F—COIN-FREED OR LIKE APPARATUS
- G07F17/00—Coin-freed apparatus for hiring articles; Coin-freed facilities or services
- G07F17/32—Coin-freed apparatus for hiring articles; Coin-freed facilities or services for games, toys, sports, or amusements
- G07F17/34—Coin-freed apparatus for hiring articles; Coin-freed facilities or services for games, toys, sports, or amusements depending on the stopping of moving members in a mechanical slot machine, e.g. "fruit" machines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Biodiversity & Conservation Biology (AREA)
- Botany (AREA)
- Ecology (AREA)
- Forests & Forestry (AREA)
- Environmental Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US301852A US3898073A (en) | 1972-10-30 | 1972-10-30 | Method for altering plant flowering and sexual reproduction |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2263805A1 true DE2263805A1 (de) | 1974-05-09 |
Family
ID=23165177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2263805A Pending DE2263805A1 (de) | 1972-10-30 | 1972-12-28 | Verfahren zum aendern des bluehens und/oder der geschlechtlichen vermehrung von pflanzen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3898073A (enExample) |
| DE (1) | DE2263805A1 (enExample) |
| FR (1) | FR2204340B1 (enExample) |
| IT (1) | IT984890B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4366317A (en) * | 1981-06-22 | 1982-12-28 | Philip Morris Incorporated | Process for synthesis of N-(hydrocarbyl)substituted-p-menthane-3-carboxamide |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2321989A (en) * | 1942-01-15 | 1943-06-15 | Du Pont | Triazone ring compound |
| US3040044A (en) * | 1958-06-19 | 1962-06-19 | Diamond Alkali Co | Trihalo-2, 4-dioxohexahydro-1, 3, 5-triazines and method of preparing same |
| US3462257A (en) * | 1965-09-13 | 1969-08-19 | Scott & Sons Co O M | Turf management with azauracils plus fertilizer |
-
1972
- 1972-10-30 US US301852A patent/US3898073A/en not_active Expired - Lifetime
- 1972-12-28 DE DE2263805A patent/DE2263805A1/de active Pending
- 1972-12-28 FR FR7246561A patent/FR2204340B1/fr not_active Expired
- 1972-12-29 IT IT33850/72A patent/IT984890B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| US3898073A (en) | 1975-08-05 |
| FR2204340B1 (enExample) | 1976-06-04 |
| FR2204340A1 (enExample) | 1974-05-24 |
| IT984890B (it) | 1974-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2715786C2 (enExample) | ||
| EP0342569B1 (de) | Heterocyclische 2-Alkoxyphenoxysulfonylharnstoffe und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren | |
| EP0121082A1 (de) | Guanidin-Derivate | |
| EP0131258A2 (de) | Neue N-Alkoxy- N-Alkylsulfonylaminosulfonylharnstoffe, und neue (Pyrimido) Triazino-thiatriazinoxide als Vorprodukte | |
| DE2648008B2 (de) | Acetanilide | |
| DE2604989A1 (de) | 1,5-alkylen-3-aryl-hydantoin-derivate, verfahren zu ihrer herstellung und mittel mit herbizider und/oder fungizider wirkung | |
| DE3604042A1 (de) | Imidazolidin(thi)on-derivate, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz | |
| EP0071958B1 (de) | Heterocyclisch substituierte Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft | |
| DE2809035A1 (de) | N'- eckige klammer auf 4-(phenethyloxy)-phenyl eckige klammer zu -n-methyl- n-methoxyharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur unkrautbekaempfung | |
| EP0128116B1 (de) | Anellierte N-Phenylsulfonyl-N'-pyrimidinyl- und -triazinylharnstoffe | |
| DE3123018A1 (de) | Substituierte cyclohexan-1,3-dion-derivate, verfahren zu deren herstellung und herbicide mittel | |
| EP0353641B1 (de) | Heterozyklisch substituierte Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren | |
| DD202378A5 (de) | Herbizide und wachstumsregulierende mittel | |
| EP0165572A2 (de) | Neue herbizid wirksame Sulfonylharnstoffe | |
| EP0336354A1 (de) | Heterocyclisch substituierte Alkyl- und Alkenylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren | |
| EP0291851A2 (de) | Herbizide Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Beeinflussung des Pflanzenwachstums | |
| EP0342568A1 (de) | Heterocyclisch substituierte Phenoxysulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren | |
| DE2428070C2 (de) | Butyramide und Butyrate, ihre Herstellung und diese enthaltende aphizide Mittel | |
| DE2263805A1 (de) | Verfahren zum aendern des bluehens und/oder der geschlechtlichen vermehrung von pflanzen | |
| EP0319689B1 (de) | Heterocyclisch substituierte N-Sultam-sulfonamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren | |
| EP0337946A1 (de) | Harnstoffe | |
| DE3880987T2 (de) | Mittel zur erzeugung einer maennlichen sterilitaet in pflanzen. | |
| EP0409114A1 (de) | Heterocyclisch substituierte Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren | |
| EP0142629A1 (de) | Neue Pyrazolyl- und Isoxazolylsulfonylharnstoffe | |
| EP0464838B1 (de) | Substituierte Sulfonylalkylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |