CH618845A5 - Plant growth regulators - Google Patents

Plant growth regulators Download PDF

Info

Publication number: CH618845A5
Authority: CH; Switzerland
Prior art keywords: keto; gluconate; isopropylidene; active ingredient; lower alkyl
Prior art date: 1973-03-26

Application number

CH233974A

Other languages

German (de)

English (en)

Inventor

William Szkrybalo

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

1974-02-20

Publication date

1980-08-29

1974-02-20 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1980-08-29 Publication of CH618845A5 publication Critical patent/CH618845A5/de

Links

239000005648 plant growth regulator Substances 0.000 title description 13
125000000217 alkyl group Chemical group 0.000 claims description 195
-1 nitro, hydroxy Chemical group 0.000 claims description 142
150000001875 compounds Chemical class 0.000 claims description 88
239000004480 active ingredient Substances 0.000 claims description 86
239000000203 mixture Substances 0.000 claims description 77
239000003795 chemical substances by application Substances 0.000 claims description 55
125000003342 alkenyl group Chemical group 0.000 claims description 32
125000000304 alkynyl group Chemical group 0.000 claims description 31
229950006191 gluconic acid Drugs 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical group 0.000 claims description 27
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 24
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 23
125000004432 carbon atom Chemical group C* 0.000 claims description 23
239000011734 sodium Chemical group 0.000 claims description 23
229910052708 sodium Inorganic materials 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 17
239000011591 potassium Chemical group 0.000 claims description 17
229910052700 potassium Inorganic materials 0.000 claims description 17
150000003863 ammonium salts Chemical group 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
238000000034 method Methods 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
239000000174 gluconic acid Substances 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
230000008635 plant growth Effects 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
230000001105 regulatory effect Effects 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
239000011575 calcium Substances 0.000 claims description 7
229910052791 calcium Inorganic materials 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
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 6
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
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical group [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000011777 magnesium Chemical group 0.000 claims description 5
229910052749 magnesium Inorganic materials 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
230000008569 process Effects 0.000 claims description 5
RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
125000005133 alkynyloxy group Chemical group 0.000 claims description 4
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
235000012208 gluconic acid Nutrition 0.000 claims description 4
239000008187 granular material Substances 0.000 claims description 4
125000005059 halophenyl group Chemical group 0.000 claims description 4
GLUUGHFHXGJENI-UHFFFAOYSA-O hydron piperazine Chemical group [H+].C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-O 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
239000012141 concentrate Substances 0.000 claims description 3
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
239000008262 pumice Substances 0.000 claims description 3
239000004575 stone Substances 0.000 claims description 3
OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 claims description 2
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 2
QALAKUHQOSUJEU-UHFFFAOYSA-N calcium;magnesium Chemical compound [Mg+2].[Ca+2] QALAKUHQOSUJEU-UHFFFAOYSA-N 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
241000196324 Embryophyta Species 0.000 description 80
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
230000000694 effects Effects 0.000 description 53
239000002253 acid Substances 0.000 description 49
239000000243 solution Substances 0.000 description 37
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
230000012010 growth Effects 0.000 description 32
235000013399 edible fruits Nutrition 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
244000025254 Cannabis sativa Species 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000004563 wettable powder Substances 0.000 description 14
239000007921 spray Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
238000003756 stirring Methods 0.000 description 12
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 10
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
238000009472 formulation Methods 0.000 description 10
238000012360 testing method Methods 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
230000002363 herbicidal effect Effects 0.000 description 8
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
239000002689 soil Substances 0.000 description 8
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 7
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 7
239000002585 base Substances 0.000 description 7
238000003306 harvesting Methods 0.000 description 7
230000001965 increasing effect Effects 0.000 description 7
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000000080 wetting agent Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
235000013339 cereals Nutrition 0.000 description 6
239000004009 herbicide Substances 0.000 description 6
239000003701 inert diluent Substances 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical group OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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239000000126 substance Substances 0.000 description 6
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244000070406 Malus silvestris Species 0.000 description 5
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150000001299 aldehydes Chemical class 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
231100000001 growth retardation Toxicity 0.000 description 5
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JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
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PSSHGMIAIUYOJF-XBWDGYHZSA-N [(3as,5ar,8ar,8bs)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methanol Chemical compound C1O[C@@]2(CO)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 PSSHGMIAIUYOJF-XBWDGYHZSA-N 0.000 description 4
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125000005037 alkyl phenyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
235000021016 apples Nutrition 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000021015 bananas Nutrition 0.000 description 1
HYJSGOXICXYZGS-UHFFFAOYSA-N benazolin Chemical compound C1=CC=C2SC(=O)N(CC(=O)O)C2=C1Cl HYJSGOXICXYZGS-UHFFFAOYSA-N 0.000 description 1
235000021028 berry Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-O bis(2-hydroxyethyl)azanium Chemical compound OCC[NH2+]CCO ZBCBWPMODOFKDW-UHFFFAOYSA-O 0.000 description 1
235000021029 blackberry Nutrition 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
PSGPXWYGJGGEEG-UHFFFAOYSA-N butyl 9-hydroxyfluorene-9-carboxylate Chemical compound C1=CC=C2C(C(=O)OCCCC)(O)C3=CC=CC=C3C2=C1 PSGPXWYGJGGEEG-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
229940077731 carbohydrate nutrients Drugs 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Chemical class 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 1
IVUXTESCPZUGJC-UHFFFAOYSA-N chloroxuron Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1OC1=CC=C(Cl)C=C1 IVUXTESCPZUGJC-UHFFFAOYSA-N 0.000 description 1
CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
235000016213 coffee Nutrition 0.000 description 1
235000013353 coffee beverage Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
229930186364 cyclamen Natural products 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000021588 free fatty acids Nutrition 0.000 description 1
230000005089 fruit drop Effects 0.000 description 1
235000013569 fruit product Nutrition 0.000 description 1
230000004345 fruit ripening Effects 0.000 description 1
230000005094 fruit set Effects 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
239000003292 glue Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
230000009422 growth inhibiting effect Effects 0.000 description 1
239000007954 growth retardant Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
235000021374 legumes Nutrition 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000035800 maturation Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000003607 modifier Substances 0.000 description 1
BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 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
231100001184 nonphytotoxic Toxicity 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 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
125000005981 pentynyl group Chemical group 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
229920000136 polysorbate Polymers 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
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000002244 precipitate Substances 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
235000015136 pumpkin Nutrition 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
238000010992 reflux Methods 0.000 description 1
235000009566 rice Nutrition 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
230000035945 sensitivity Effects 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
238000002791 soaking Methods 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
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
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010186 staining Methods 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
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 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
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
238000009827 uniform distribution Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000004383 yellowing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)

CH233974A 1973-03-26 1974-02-20 Plant growth regulators CH618845A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US34465773A	1973-03-26	1973-03-26

Publications (1)

Publication Number	Publication Date
CH618845A5 true CH618845A5 (en)	1980-08-29

Family

ID=23351436

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH233974A CH618845A5 (en)	1973-03-26	1974-02-20	Plant growth regulators

Country Status (22)

Country	Link
JP (1)	JPS49135973A (da)
AR (1)	AR217620A1 (da)
BE (1)	BE812762A (da)
BR (1)	BR7402334D0 (da)
CA (1)	CA1026328A (da)
CH (1)	CH618845A5 (da)
CU (1)	CU34040A (da)
DD (1)	DD111787A5 (da)
DE (1)	DE2414590A1 (da)
DK (1)	DK137481B (da)
ES (1)	ES424593A1 (da)
FR (1)	FR2284606A1 (da)
GB (1)	GB1464957A (da)
IE (1)	IE39096B1 (da)
IL (1)	IL44488A0 (da)
IN (1)	IN139466B (da)
IT (1)	IT1048279B (da)
LU (1)	LU69700A1 (da)
NL (1)	NL7403745A (da)
SE (1)	SE7404006L (da)
TR (1)	TR18146A (da)
ZA (1)	ZA74942B (da)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH47A (de) *		1888-12-31	Georg Winkler Friedrich	Sichtemaschine
ES135896A1 (es) *	1933-10-25	1934-12-16	Hoffmann La Roche	PROCEDIMIENTO PARA LA FABRICACIoN DEL áCIDO 2-CETO-1-GULoNICO
CH552549A (de) *	1970-05-13	1974-08-15	Hoffmann La Roche	Verfahren zur herstellung von saeuren von kohlenhydraten.
FR2199457B1 (da) *	1972-09-15	1975-10-17	Chimie Organique Biolog
CH578835A5 (da) *	1972-08-03	1976-08-31	Hoffmann La Roche

1974
- 1974-02-12 ZA ZA740942A patent/ZA74942B/xx unknown
- 1974-02-20 CH CH233974A patent/CH618845A5/de not_active IP Right Cessation
- 1974-03-12 TR TR18146A patent/TR18146A/xx unknown
- 1974-03-20 NL NL7403745A patent/NL7403745A/xx unknown
- 1974-03-22 DD DD177380A patent/DD111787A5/xx unknown
- 1974-03-22 FR FR7409886A patent/FR2284606A1/fr active Granted
- 1974-03-25 SE SE7404006A patent/SE7404006L/xx unknown
- 1974-03-25 IE IE638/74A patent/IE39096B1/xx unknown
- 1974-03-25 ES ES424593A patent/ES424593A1/es not_active Expired
- 1974-03-25 JP JP49032715A patent/JPS49135973A/ja active Pending
- 1974-03-25 CU CU7434040A patent/CU34040A/es unknown
- 1974-03-25 DK DK162174AA patent/DK137481B/da unknown
- 1974-03-25 IN IN652/CAL/74A patent/IN139466B/en unknown
- 1974-03-25 CA CA195,793A patent/CA1026328A/en not_active Expired
- 1974-03-25 BE BE142392A patent/BE812762A/xx unknown
- 1974-03-25 BR BR2334/74A patent/BR7402334D0/pt unknown
- 1974-03-25 IL IL44488A patent/IL44488A0/xx unknown
- 1974-03-25 GB GB1305074A patent/GB1464957A/en not_active Expired
- 1974-03-25 LU LU69700A patent/LU69700A1/xx unknown
- 1974-03-26 IT IT49716/74A patent/IT1048279B/it active
- 1974-03-26 DE DE2414590A patent/DE2414590A1/de not_active Ceased
1975
- 1975-10-06 AR AR260687A patent/AR217620A1/es active

Also Published As

Publication number	Publication date
DK137481B (da)	1978-03-13
FR2284606B1 (da)	1977-10-07
IE39096L (en)	1974-09-26
GB1464957A (en)	1977-02-16
IN139466B (da)	1976-06-19
SE7404006L (da)	1974-10-14
TR18146A (tr)	1976-10-11
ZA74942B (en)	1974-12-24
DK137481C (da)	1978-08-28
CA1026328A (en)	1978-02-14
IT1048279B (it)	1980-11-20
DD111787A5 (da)	1975-03-12
BR7402334D0 (pt)	1974-11-19
AU6709074A (en)	1975-09-25
IE39096B1 (en)	1978-08-02
LU69700A1 (da)	1976-02-04
AR217620A1 (es)	1980-04-15
NL7403745A (da)	1974-09-30
DE2414590A1 (de)	1974-10-17
IL44488A0 (en)	1974-06-30
ES424593A1 (es)	1976-12-01
JPS49135973A (da)	1974-12-27
CU34040A (da)	1975-09-09
BE812762A (fr)	1974-09-25
FR2284606A1 (fr)	1976-04-09

Publication	Publication Date	Title
EP0136615B1 (de)	1988-04-20	1-Methylamino-cyclopropan-1-carbonsäure-Derivate
DE69113131T2 (de)	1996-05-30	1-((0-Cyclopropylcarbonyl)phenyl)sulfamoyl)-3-(4,6-dimethoxy-2-pyrimidyl)harnstoff und Verfahren zu seiner Herstellung.
EP0243313B1 (de)	1990-05-16	Acyl-cyclohexandione und deren Oximäther mit herbizider und das Pflanzenwachstum regulierender Wirkung
DE2843722A1 (de)	1979-04-19	N- (2-chlor-4-pyridyl)-harnstoffe, verfahren zu deren herstellung sowie diese enthaltende pflanzenwachsregulatoren
EP0155911A1 (de)	1985-09-25	Purinderivate zur Regulierung des Pflanzenwachstums
US4337080A (en)	1982-06-29	Plant growth regulants
DE2615878C2 (de)	1985-09-19	Polycyclische stickstoffhaltige Verbindungen
EP0065712A2 (de)	1982-12-01	N-(1-Alkenyl)-chloressigsäureanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
US4104052A (en)	1978-08-01	Plant growth regulants
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
CH618845A5 (en)	1980-08-29	Plant growth regulators
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)
DE3900085A1 (de)	1989-07-20	Herstellung und biologische wirkung von aminoxyalkyl-phosphonig-, -phosphon-, und phosphinsaeurederivaten
DE3941160A1 (de)	1990-06-21	Lagerungsstabile salze von acyl-cyclohexandion-oximaethern mit herbizider und das pflanzenwachstum regulierender wirkung
US4067722A (en)	1978-01-10	Plant growth regulant compositions
EP0037019A1 (de)	1981-10-07	N-Allenyl-halogenacetanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Wachstumsregulatoren und Herbizide
EP0002757B1 (de)	1981-11-25	Phenoxy-phenylthio-milchsäurederivate, deren Herstellung, sie enthaltende herbizide und pflanzenwuchsregulierende Mittel sowie deren Verwendung
EP0287512A2 (de)	1988-10-19	Pflanzenwuchsregulatoren
EP0175652A2 (de)	1986-03-26	5-Acylaminopyrimidine
DE3219315A1 (de)	1983-11-24	Cyclohexan-1,3-dion-derivate
EP0154806A2 (de)	1985-09-18	Substituierte Oxirane
DE3121156A1 (de)	1982-12-09	Xylitderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wachstumsregulatorischer wirkung fuer pflanzen
DE3047924A1 (de)	1982-07-15	5-aryl-cyclohexan-1,3-dion-derivate, herbizide, die diese verbindungen enthalten, und verfahren zu ihrer herstellung
DE2317987A1 (de)	1973-10-31	Alpha-pyronderivate

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1982-10-29	PL	Patent ceased
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