CH552596A - Verfahren zur herstellung neuer imidazolidin-3-carbonsaeure-derivate. - Google Patents

Verfahren zur herstellung neuer imidazolidin-3-carbonsaeure-derivate.

Info

Publication number: CH552596A
Authority: CH; Switzerland
Prior art keywords: imidazolidine; carboxylic acid; trioxo; alkyl; ester
Prior art date: 1971-03-26

Application number

CH451471A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

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.)

1971-03-26

Filing date

1971-03-26

Publication date

1974-08-15

1971-03-26 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1971-03-26 Priority to CH451471A priority Critical patent/CH552596A/de

1972-03-20 Priority to IL39042A priority patent/IL39042A/en

1972-03-21 Priority to CA137,606A priority patent/CA987328A/en

1972-03-22 Priority to IT22257/72A priority patent/IT953546B/it

1972-03-24 Priority to BR721757A priority patent/BR7201757D0/pt

1972-03-24 Priority to DE2214448A priority patent/DE2214448C3/de

1972-03-24 Priority to FR7210422A priority patent/FR2131604A5/fr

1972-03-24 Priority to DD161793A priority patent/DD102051A5/xx

1972-03-24 Priority to ZA722013A priority patent/ZA722013B/xx

1972-03-24 Priority to BG020053A priority patent/BG20590A3/xx

1972-03-24 Priority to US00237926A priority patent/US3818031A/en

1972-03-24 Priority to AR241128A priority patent/AR193249A1/es

1972-03-24 Priority to BE781182A priority patent/BE781182A/xx

1972-03-24 Priority to NL7204027A priority patent/NL7204027A/xx

1972-03-24 Priority to GB1408372A priority patent/GB1373556A/en

1972-03-25 Priority to TR18708A priority patent/TR18708A/tr

1972-03-25 Priority to ES401164A priority patent/ES401164A1/es

1972-03-25 Priority to JP3020872A priority patent/JPS565201B1/ja

1974-08-15 Publication of CH552596A publication Critical patent/CH552596A/de

Links

230000012010 growth Effects 0.000 title claims description 6
-1 tetrahydrofurfuryl Chemical group 0.000 claims abstract description 102
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
241000196324 Embryophyta Species 0.000 claims description 24
235000013399 edible fruits Nutrition 0.000 claims description 19
239000004480 active ingredient Substances 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
XOAYKINYVYDPDF-UHFFFAOYSA-N imidazolidine-1-carboxylic acid Chemical class OC(=O)N1CCNC1 XOAYKINYVYDPDF-UHFFFAOYSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
230000000694 effects Effects 0.000 claims description 9
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
230000015572 biosynthetic process Effects 0.000 claims description 7
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
125000003302 alkenyloxy group Chemical group 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
235000020971 citrus fruits Nutrition 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical class O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 claims description 5
244000099147 Ananas comosus Species 0.000 claims description 4
235000007119 Ananas comosus Nutrition 0.000 claims description 4
244000061456 Solanum tuberosum Species 0.000 claims description 4
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CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000004202 carbamide Substances 0.000 claims description 4
239000006185 dispersion Substances 0.000 claims description 4
MJJCZWPYKMGQHU-UHFFFAOYSA-N methylparabanic acid Chemical compound CN1C(=O)NC(=O)C1=O MJJCZWPYKMGQHU-UHFFFAOYSA-N 0.000 claims description 4
230000008635 plant growth Effects 0.000 claims description 4
235000012015 potatoes Nutrition 0.000 claims description 4
239000002689 soil Substances 0.000 claims description 4
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
230000001105 regulatory effect Effects 0.000 claims description 3
235000007516 Chrysanthemum Nutrition 0.000 claims description 2
240000005250 Chrysanthemum indicum Species 0.000 claims description 2
241000234653 Cyperus Species 0.000 claims description 2
240000006497 Dianthus caryophyllus Species 0.000 claims description 2
235000009355 Dianthus caryophyllus Nutrition 0.000 claims description 2
241000508725 Elymus repens Species 0.000 claims description 2
244000043261 Hevea brasiliensis Species 0.000 claims description 2
241000209510 Liliopsida Species 0.000 claims description 2
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241000208422 Rhododendron Species 0.000 claims description 2
235000004789 Rosa xanthina Nutrition 0.000 claims description 2
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240000002439 Sorghum halepense Species 0.000 claims description 2
238000005520 cutting process Methods 0.000 claims description 2
238000011161 development Methods 0.000 claims description 2
230000018109 developmental process Effects 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
239000004009 herbicide Substances 0.000 claims description 2
239000004816 latex Substances 0.000 claims description 2
229920000126 latex Polymers 0.000 claims description 2
235000021374 legumes Nutrition 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
238000005259 measurement Methods 0.000 claims description 2
239000000203 mixture Substances 0.000 claims description 2
230000001151 other effect Effects 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
239000000758 substrate Substances 0.000 claims description 2
238000012360 testing method Methods 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
125000001188 haloalkyl group Chemical group 0.000 abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000000460 chlorine Chemical group 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
VIGJKMRHILAFFC-UHFFFAOYSA-N 1-ethylimidazolidine-2,4,5-trione Chemical compound CCN1C(=O)NC(=O)C1=O VIGJKMRHILAFFC-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
230000004345 fruit ripening Effects 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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239000000155 melt Substances 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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239000000376 reactant Substances 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
SLTPVPJOGABILB-UHFFFAOYSA-N 2-methylpropyl 3-ethyl-2,4,5-trioxoimidazolidine-1-carboxylate Chemical compound C(C(C)C)OC(=O)N1C(N(C(C1=O)=O)CC)=O SLTPVPJOGABILB-UHFFFAOYSA-N 0.000 description 1
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
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125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
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125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH451471A 1971-03-26 1971-03-26 Verfahren zur herstellung neuer imidazolidin-3-carbonsaeure-derivate. CH552596A (de)

Priority Applications (18)

Application Number	Priority Date	Filing Date	Title
CH451471A CH552596A (de)	1971-03-26	1971-03-26	Verfahren zur herstellung neuer imidazolidin-3-carbonsaeure-derivate.
IL39042A IL39042A (en)	1971-03-26	1972-03-20	2,4,5-trioxoimidazolidine-1-carboxylic acid derivatives,their preparation and their use for the control of plant metabolism
CA137,606A CA987328A (en)	1971-03-26	1972-03-21	Heterocyclic compounds and their use for the control of plant metabolism
IT22257/72A IT953546B (it)	1971-03-26	1972-03-22	Composti eterociclici e loro impie go per regolare il metabolismo delle piante
BR721757A BR7201757D0 (pt)	1971-03-26	1972-03-24	Processo para obtencao de novos derivados de acido inidazolidino-triono-carboxilico bem como composicoes a base destes compostos e processo para regular o metabolismo de plantas
DE2214448A DE2214448C3 (de)	1971-03-26	1972-03-24	2,4,5-Trioxo-imidazolidin-3-carbonsäure und -thiocarbonsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Mittel zur Regulierung des Pflanzenstoffwechsels
FR7210422A FR2131604A5 (tr)	1971-03-26	1972-03-24
DD161793A DD102051A5 (tr)	1971-03-26	1972-03-24
ZA722013A ZA722013B (en)	1971-03-26	1972-03-24	New heterocyclic compounds and their use for the control of plant metabolism
BG020053A BG20590A3 (bg)	1971-03-26	1972-03-24	Средство за регулиране растежа на растенията
US00237926A US3818031A (en)	1971-03-26	1972-03-24	Imidazolidinetrionecarboxylic acid derivatives
AR241128A AR193249A1 (es)	1971-03-26	1972-03-24	Nuevos derivados del acido imidazolidintrioncarboxilico,procedimientos para su preparacion y composiciones que los incorporan
BE781182A BE781182A (fr)	1971-03-26	1972-03-24	Composes heterocycliques et leur application a la regulation dumetabolisme des plantes
NL7204027A NL7204027A (tr)	1971-03-26	1972-03-24
GB1408372A GB1373556A (en)	1971-03-26	1972-03-24	Heterocyclic compounds and their use for the control of plant metabolism
TR18708A TR18708A (tr)	1971-03-26	1972-03-25	Bitki bueyuemesinin ayarlanmasina mahsus terkipler
ES401164A ES401164A1 (es)	1971-03-26	1972-03-25	Procedimiento para la preparacion de nuevos derivados de acido imidazolintrion-3-carboxilico.
JP3020872A JPS565201B1 (tr)	1971-03-26	1972-03-25

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH451471A CH552596A (de)	1971-03-26	1971-03-26	Verfahren zur herstellung neuer imidazolidin-3-carbonsaeure-derivate.

Publications (1)

Publication Number	Publication Date
CH552596A true CH552596A (de)	1974-08-15

Family

ID=4277509

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH451471A CH552596A (de)	1971-03-26	1971-03-26	Verfahren zur herstellung neuer imidazolidin-3-carbonsaeure-derivate.

Country Status (4)

Country	Link
BR (1)	BR7201757D0 (tr)
CH (1)	CH552596A (tr)
TR (1)	TR18708A (tr)
ZA (1)	ZA722013B (tr)

1971
- 1971-03-26 CH CH451471A patent/CH552596A/de not_active IP Right Cessation
1972
- 1972-03-24 ZA ZA722013A patent/ZA722013B/xx unknown
- 1972-03-24 BR BR721757A patent/BR7201757D0/pt unknown
- 1972-03-25 TR TR18708A patent/TR18708A/tr unknown

Also Published As

Publication number	Publication date
TR18708A (tr)	1977-08-10
ZA722013B (en)	1972-12-27
BR7201757D0 (pt)	1973-05-03

Legal Events

Date	Code	Title	Description
1980-11-28	PL	Patent ceased

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.
DE2906507A1 (de)	1980-08-28	Mittel zur regulierung des pflanzenwachstums
DE2701091A1 (de)	1977-07-28	Fungizide zusammensetzungen und verbindungen
DE2406475C2 (de)	1983-04-28	5-Acetamido-2,4-dimethyltrifluormethansulfonanilid und dessen landwirtschaftlich geeignete Salze, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende Mittel
DE3415820A1 (de)	1984-10-31	1-carbalkoxyalkyl-3-aryloxy-4-(2'-carboxyphenyl)-azet-2-one, diese enthaltende pflanzenwachstumsregulierende mittel und verfahren zum regulieren des pflanzenwachstums
DE2261918A1 (de)	1973-06-28	Diphenylaether und verfahren zu ihrer herstellung und verwendung
CH644371A5 (de)	1984-07-31	In 2- und 4-stellung disubstituierte 5-thiazolcarbonsaeuren und deren funktionelle derivate.
DE2501797C2 (de)	1986-01-30	Methyl-2-nitro-5-(2',4'-dichlorphenoxy)thiobenzoat, Verfahren zu dessen Herstellung und seine Verwendung als Herbizid
DE3339644A1 (de)	1984-05-10	Neue substituierte heteroarylverbindungen, diese enthaltende fungizide mittel und verfahren zur bekaempfung von pilzen
DE2711230A1 (de)	1977-09-29	N-(4-benzyloxyphenyl)-n'-methyl-n'- methoxyharnstoff, verfahren zu seiner herstellung und seine verwendung als herbizid insbesondere in sojabohnenkulturen
EP0126249A1 (de)	1984-11-28	Chlorierte Phosphorylmethylcarbonyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung in Pflanzenschutzmitteln
DD145995A5 (de)	1981-01-21	Formulierungen fuer landwirtschaftliche zwecke
DE2214448C3 (de)	1982-03-25	2,4,5-Trioxo-imidazolidin-3-carbonsäure und -thiocarbonsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Mittel zur Regulierung des Pflanzenstoffwechsels
DE2239892A1 (de)	1973-03-01	Mittel zur bekaempfung von pflanzenpathogenen organismen
DE1670709A1 (de)	1970-12-03	Pestizide Mittel
CH528209A (de)	1972-09-30	Mittel zur Regulierung der Pflanzenentwicklung
CH563711A5 (en)	1975-07-15	Agents for regulating plant metabolism - contg. imidazolidine-2,4,5-trione-3-carboxylic acid derivs.
CH570381A5 (en)	1975-12-15	1-substd-2,4,5-trioxoimidazolidine-3-carboxylic and thiocarboxylic - esters - used in growth control in plants
EP0002455B1 (de)	1980-11-26	Acyloxyamide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenwachstumsregulatoren
DE2644486C2 (de)	1984-11-22	Substituierte Phenoxybenzoesäureanhydride, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbicide
DE2824517A1 (de)	1979-12-06	Mittel zur regulierung des pflanzenwachstums
DE2601376A1 (de)	1977-07-21	Phenoxycarbonsaeure-aryloxy(thio)carbonylaminomethylester, verfahren zu ihrer herstellung sowie ihre verwendung zur regulierung des pflanzenwachstums
DD144502A5 (de)	1980-10-22	Pflanzenwachstumsregulator
DD299298A5 (de)	1992-04-09	Neue oxazolidinone und -thione als pflanzenregulatoren