NO750122L - - Google Patents

Info

Publication number: NO750122L
Authority: NO; Norway
Prior art keywords: keto; compound; compounds according; isopropylidene; lower alkyl
Prior art date: 1973-03-26

Application number

NO750122A

Other languages

English (en)

Norwegian (no)

Inventor

W Czkrybalo

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-03-26

Filing date

1975-01-16

Publication date

1974-09-27

1974-09-27 Publication of NO750122L publication Critical patent/NO750122L/no

1975-01-16 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1975-01-16 Priority to NO750122A priority Critical patent/NO750122L/no

Links

150000001875 compounds Chemical class 0.000 claims description 312
125000000217 alkyl group Chemical group 0.000 claims description 184
-1 nitro, hydroxy Chemical group 0.000 claims description 52
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical group 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 27
125000003342 alkenyl group Chemical group 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 25
125000000304 alkynyl group Chemical group 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
230000008635 plant growth Effects 0.000 claims description 12
230000001105 regulatory effect Effects 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
150000003863 ammonium salts Chemical group 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
150000001721 carbon Chemical group 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 5
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical group [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
239000011734 sodium Chemical group 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
239000011575 calcium Substances 0.000 claims description 4
229910052791 calcium Inorganic materials 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000005059 halophenyl group Chemical group 0.000 claims description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical group [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
GLUUGHFHXGJENI-UHFFFAOYSA-O hydron piperazine Chemical compound [H+].C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-O 0.000 claims description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
239000011591 potassium Chemical group 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-O bis(2-hydroxyethyl)azanium Chemical compound OCC[NH2+]CCO ZBCBWPMODOFKDW-UHFFFAOYSA-O 0.000 claims description 2
QALAKUHQOSUJEU-UHFFFAOYSA-N calcium;magnesium Chemical compound [Mg+2].[Ca+2] QALAKUHQOSUJEU-UHFFFAOYSA-N 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 3
239000011777 magnesium Substances 0.000 claims 3
229910052749 magnesium Inorganic materials 0.000 claims 3
VBUYCZFBVCCYFD-JJYYJPOSSA-M 2-dehydro-D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C([O-])=O VBUYCZFBVCCYFD-JJYYJPOSSA-M 0.000 claims 1
241000790917 Dioxys <bee> Species 0.000 claims 1
125000005110 aryl thio group Chemical group 0.000 claims 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
241000196324 Embryophyta Species 0.000 description 51
230000000694 effects Effects 0.000 description 32
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
230000012010 growth Effects 0.000 description 26
239000003795 chemical substances by application Substances 0.000 description 25
239000000243 solution Substances 0.000 description 23
239000013543 active substance Substances 0.000 description 22
239000002253 acid Substances 0.000 description 21
235000013399 edible fruits Nutrition 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
230000005089 fruit drop Effects 0.000 description 11
244000025254 Cannabis sativa Species 0.000 description 10
239000007921 spray Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 8
230000002363 herbicidal effect Effects 0.000 description 8
239000005648 plant growth regulator Substances 0.000 description 8
239000002585 base Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000000843 powder Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000004009 herbicide Substances 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
238000000034 method Methods 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical group OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
240000003768 Solanum lycopersicum Species 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
241000894007 species Species 0.000 description 4
230000004936 stimulating effect Effects 0.000 description 4
230000000638 stimulation Effects 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
238000005292 vacuum distillation Methods 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
235000007516 Chrysanthemum Nutrition 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
206010011224 Cough Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
244000299507 Gossypium hirsutum Species 0.000 description 3
208000012766 Growth delay Diseases 0.000 description 3
239000004166 Lanolin Substances 0.000 description 3
244000070406 Malus silvestris Species 0.000 description 3
235000002637 Nicotiana tabacum Nutrition 0.000 description 3
244000061176 Nicotiana tabacum Species 0.000 description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000004927 clay Substances 0.000 description 3
230000003111 delayed effect Effects 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229960002737 fructose Drugs 0.000 description 3
229950006191 gluconic acid Drugs 0.000 description 3
238000003306 harvesting Methods 0.000 description 3
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
229940039717 lanolin Drugs 0.000 description 3
235000019388 lanolin Nutrition 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 3
229960003868 paraldehyde Drugs 0.000 description 3
239000000047 product Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
238000005507 spraying Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000006188 syrup Substances 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
244000105624 Arachis hypogaea Species 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
240000005250 Chrysanthemum indicum Species 0.000 description 2
240000000560 Citrus x paradisi Species 0.000 description 2
244000241257 Cucumis melo Species 0.000 description 2
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
240000002395 Euphorbia pulcherrima Species 0.000 description 2
229930091371 Fructose Natural products 0.000 description 2
239000005715 Fructose Substances 0.000 description 2
235000004341 Gossypium herbaceum Nutrition 0.000 description 2
240000002024 Gossypium herbaceum Species 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
235000011430 Malus pumila Nutrition 0.000 description 2
235000015103 Malus silvestris Nutrition 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
241000207836 Olea <angiosperm> Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
240000007377 Petunia x hybrida Species 0.000 description 2
240000001987 Pyrus communis Species 0.000 description 2
235000014443 Pyrus communis Nutrition 0.000 description 2
241000208422 Rhododendron Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
244000269722 Thea sinensis Species 0.000 description 2
244000078534 Vaccinium myrtillus Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
230000009471 action Effects 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000012208 gluconic acid Nutrition 0.000 description 2
239000003630 growth substance Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
239000007788 liquid Substances 0.000 description 2
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
230000035800 maturation Effects 0.000 description 2
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
235000014571 nuts Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
235000020232 peanut Nutrition 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
230000000979 retarding effect Effects 0.000 description 2
230000005070 ripening Effects 0.000 description 2
238000012360 testing method Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 2
SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
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150000002825 nitriles Chemical class 0.000 description 1
XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000003415 peat Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
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239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000001120 potassium sulphate Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
238000013138 pruning Methods 0.000 description 1
235000021013 raspberries Nutrition 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
230000007958 sleep Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
235000021012 strawberries Nutrition 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
244000045561 useful plants Species 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO750122A 1973-03-26 1975-01-16 NO750122L (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO750122A NO750122L (fr)	1973-03-26	1975-01-16

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US34465773A	1973-03-26	1973-03-26
NO741060		1974-03-25
NO750122A NO750122L (fr)	1973-03-26	1975-01-16

Publications (1)

Publication Number	Publication Date
NO750122L true NO750122L (fr)	1974-09-27

Family

ID=27352705

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO750122A NO750122L (fr)	1973-03-26	1975-01-16

Country Status (1)

Country	Link
NO (1)	NO750122L (fr)

1975
- 1975-01-16 NO NO750122A patent/NO750122L/no unknown

Publication	Publication Date	Title
US4799950A (en)	1989-01-24	Plant growth regulating composition
US4594092A (en)	1986-06-10	Substituted nitro and cyanoguanidines and their use of increasing crop yields
US4337080A (en)	1982-06-29	Plant growth regulants
SE449817B (sv)	1987-05-25	Medel med gametocid verkan innehallande som aktiv komponent minst ett nitroaryl-alkyl-sulfon-derivat samt anvendning derav
US4104052A (en)	1978-08-01	Plant growth regulants
EP0113070B1 (fr)	1988-01-13	L'utilisation de nitro- et cyanoguanidines substitués pour augmenter les récoltes
EP0065712B1 (fr)	1987-07-22	Anilides N-(1-alkényl) d'acide chloracétiques, procédé pour leur préparation, et leur utilisation comme herbicides et régulateurs de la croissance de plantes
US4007206A (en)	1977-02-08	2,3:4,6-Di-O(substituted)-2-keto-L-gulonic acid, salts and esters
US3981860A (en)	1976-09-21	2,3:4,5-Di-O-substituted gluconates
KR100338856B1 (ko)	2002-11-08	신규한피리미딘유도체,제초제및식물성장조절제
EP0206028B1 (fr)	1989-09-20	Augmentation de la croissance des plantes
NO750122L (fr)	1974-09-27
JPH03133948A (ja)	1991-06-07	シクロヘキセノン化合物およびその除草剤または植物成長調節剤としての利用法
US4067722A (en)	1978-01-10	Plant growth regulant compositions
US4944788A (en)	1990-07-31	Substituted nitro and cyanoguanidines and their use for increasing crop yields
ACKERSON et al.	1985	Selection of rice herbicide from several sulfonylurea compounds.
JPH02178203A (ja)	1990-07-11	作物の増収剤および増収方法
EP0270701B1 (fr)	1992-03-11	Avancement de la croissance des plantes
AU604911B2 (en)	1991-01-03	Herbicidal thiocarboxylic acid derivatives
DE2339239C3 (de)	1980-08-21	26.02.73 V.St.vAmerika 335607 02.04.73 V.StvAmerika 347035 Mittel zur Regulation des Pflanzenwachstums F. Hoff mann-La Roche & Co AG, Basel (Schweiz)
EP0145663B1 (fr)	1989-06-21	1-Di- ou triazolyl-2,3-diphényl-propan-2,3-dioles comme herbicides et régulateurs de croissance de plantes
FI60713C (fi)	1982-03-10	Saosom tillvaextregulatorer foer vaexter anvaendbara salter och estrar av 2,3:4,6-di-0-isopropyliden-2-ketogulonsyra
EP0037019A1 (fr)	1981-10-07	N-allényl-halogène acétanilides, procédé pour leur préparation et leur utilisation comme régulateurs de croissance et herbicides
EP0175652A2 (fr)	1986-03-26	5-Acylaminopyrimidines
JPS63275504A (ja)	1988-11-14	植物生長調節剤