NO166647B - ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE SUBSTITUTED DIPEPTIDES. - Google Patents
ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE SUBSTITUTED DIPEPTIDES. Download PDFInfo
- Publication number
- NO166647B NO166647B NO822023A NO822023A NO166647B NO 166647 B NO166647 B NO 166647B NO 822023 A NO822023 A NO 822023A NO 822023 A NO822023 A NO 822023A NO 166647 B NO166647 B NO 166647B
- Authority
- NO
- Norway
- Prior art keywords
- chloroacetamide
- methyl
- parts
- phytotoxic
- dimethyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 50
- 238000000034 method Methods 0.000 title description 8
- 108010016626 Dipeptides Proteins 0.000 title 1
- 230000000885 phytotoxic effect Effects 0.000 claims description 39
- 231100000208 phytotoxic Toxicity 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims 1
- -1 heptenyl Chemical group 0.000 description 97
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 66
- 239000002689 soil Substances 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
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- 239000000843 powder Substances 0.000 description 18
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- 239000000243 solution Substances 0.000 description 15
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- 150000001875 compounds Chemical class 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 238000010183 spectrum analysis Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 150000001298 alcohols Chemical class 0.000 description 5
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 5
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- 238000009835 boiling Methods 0.000 description 2
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- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 230000002089 crippling effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- DBKSIFHGBDIFFN-UHFFFAOYSA-N n,2-dimethylcyclohexan-1-imine Chemical compound CN=C1CCCCC1C DBKSIFHGBDIFFN-UHFFFAOYSA-N 0.000 description 1
- GSEJNBQMFWBHNW-UHFFFAOYSA-N n-(2-methylpropyl)cyclohexanimine Chemical compound CC(C)CN=C1CCCCC1 GSEJNBQMFWBHNW-UHFFFAOYSA-N 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
- NOBZIYQUVMLAAQ-UHFFFAOYSA-N n-ethylcyclohexanimine Chemical compound CCN=C1CCCCC1 NOBZIYQUVMLAAQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HICRSSQIWNQRPN-UHFFFAOYSA-N n-propan-2-ylcyclopentanimine Chemical compound CC(C)N=C1CCCC1 HICRSSQIWNQRPN-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SIJQHZADOOBQMG-UHFFFAOYSA-N n-propylcyclohexanimine Chemical compound CCCN=C1CCCCC1 SIJQHZADOOBQMG-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 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
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000004449 solid propellant Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000271 synthetic detergent 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
- 238000012360 testing method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Description
Fytotoksiske preparater som inneholder d-kloracetamider. Phytotoxic preparations containing d-chloroacetamides.
Nærværende oppfinnelse vedrører fytotoksiske preparater som. The present invention relates to phytotoxic preparations which.
består av eller inneholder nye N-(l-cykloalken-1-yl) - OUkloracetamider. consists of or contains new N-(1-cycloalken-1-yl)-OUchloroacetamides.
Uttrykket "fytotoksiske preparater" anvendes her <p>g i de etter-følgende krav på materialer som har en modifiserende virkning på plante - systemers vekst. Slike modifiserende virkninger omfatter alle avvikelser fra naturlig utvikling f. eks. drepning, hemning, avlivning, uttørring, re-gulering, forkrøbling, stimulering og lignende. På samme måte anvendes "fytotoksisk"og "fytotoksisitet" for å identifisere en vekstmodifiser ende virkning av forbindelsene og preparatene etter oppfinnelsen. The term "phytotoxic preparations" is used here <p>g in the subsequent requirements for materials which have a modifying effect on the growth of plant systems. Such modifying effects include all deviations from natural development, e.g. killing, inhibiting, killing, drying out, regulating, crippling, stimulating and the like. In the same way, "phytotoxic" and "phytotoxicity" are used to identify a growth modifying effect of the compounds and preparations according to the invention.
Uttrykket "plantesystem" anvendes her i betydningen "spirende frø, skytende stiklinger og etablert vegetasjon inkl. røtter og plantedeler over bakken". The term "plant system" is used here in the sense of "germinating seeds, shooting cuttings and established vegetation including roots and plant parts above ground".
' N-(1-cycloalken-1-yl) B--kloracetamidene som anvendes i preparatene etter nærværende oppfinnelse, representeres ved formelen The N-(1-cycloalken-1-yl) B-chloroacetamides used in the preparations according to the present invention are represented by the formula
hvor R betegner alkyl med 1-8 karbonatomer, alkoxyalkyl med 2-8 karbonatomer, alkenyl med 2-8 karbonatomer eller fenyl, og Y er valgt fra gruppen bestående av where R denotes alkyl with 1-8 carbon atoms, alkoxyalkyl with 2-8 carbon atoms, alkenyl with 2-8 carbon atoms or phenyl, and Y is selected from the group consisting of
hvor R<1> er alkyl med 1-4 karbonatomer, og n er en indeks fra 0 til 3. where R<1> is alkyl with 1-4 carbon atoms, and n is an index from 0 to 3.
N-(l-cycloalken-1 -yl) O-kloracetamidene som anvendes etter nærværende oppfinnelse, er umettet i ringen ved ringkarbonatomet over hvilket ringen er bundet til nitrogenatomet. Når cycloalkenylet er en 6-leddet ring, kan ringsystemet være konjugert, men må være umettet ved ringkarbonatomet over hvilket ringen er bundet til nitrogenatomet, d.v.s. The N-(1-cycloalken-1-yl) O-chloroacetamides used according to the present invention are unsaturated in the ring at the ring carbon atom above which the ring is bound to the nitrogen atom. When the cycloalkenyl is a 6-membered ring, the ring system may be conjugated but must be unsaturated at the ring carbon atom above which the ring is attached to the nitrogen atom, i.e.
i 1 eller 6 stilling. in 1 or 6 position.
Representative R radikaler i ct-kloracetamidene omfatter alkyl, f. eks. methyl, ethyl, n-propyl, isopropyl, n-butyl, sek-butyl, tert-butyl rette og forgrenede amyler, pentyler, hexyler, heptyler og octyler; alkenyl, f. eks. allyl, butenyl, pentenyl, hexenyl, heptenyl og oktenyl; alkoxyalkyl, f. eks. methoxymethyl, methoxyéthyl, methyxypropyl, methoxybutyl, met-hoxyheptyl, propoxypropyl, ethoxyethyl og butoxybutyl, <p>g fenyl. Representative R radicals in the ct-chloroacetamides include alkyl, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl straight and branched amyls, pentyls, hexyls, heptyls and octyls; alkenyl, e.g. allyl, butenyl, pentenyl, hexenyl, heptenyl and octenyl; alkoxyalkyl, e.g. methoxymethyl, methoxyethyl, methyxypropyl, methoxybutyl, methoxyheptyl, propoxypropyl, ethoxyethyl and butoxybutyl, <p>g phenyl.
Representative Y cykloalkenylradikaler for Ot -kloracetamidene omfatter f. eks . 1-cyklopentenyl, 3-methyl-1-cyklopentenyl, 5-methyl-l-cyklopentenyl, 3 , 4-dimethyl-1 -cyklopentenyl, 2, 5 -dimethyl-1 -cyklopentenyl, 5-methyl-5-cyklopentenyl, 3 ,4-dimethyl-5-cyklopentenyl, 5-(tert-butyl) -l-cyklopentenyl, 1-cyklohexenyl, 3-methyl-1-cyklohexenyl, 3 ,4-dimethyl -1 - cyklohexenyl, 6-methyl-1 - cyklohexenyl, 2, 4-dimethyl-1 -cyklohexenyl, 3-methyl-6-cyklohexenyl, 3 ,4-dimethyl-6-cyklohexenyl, 2, 6-dimethyl-1 - cyklohexenyl, 3,3-dimethyl-1 - cyklohexenyl, 6-(tert-butyl)-1 - cyklohexenyl, 1 , 3-cyklohexadienyl, 3-methyl-1, 3-cyklohexadienyl, 3 ,4-dimethyl-1, 3-cyklohexadienyl, 6-methyl-1, 3-cyklohexadienyl, 2, 4-dimethyl-l, 3-cyklo - 'hexadienyl, 3 -methyl-4, 6- cyklohexadienyl, 3 , 4-dimethyl-4, 6-cyklohexadienyl , 2, 6-dimethyl-4, 6-cyklohexadienyl, 5,5 -dimethyl-1 , 3 - cyklohexadienyl , 6 - (tert -butyl) -1, 3 - cyklohexadienyl, 3,5,5 -trimethyl-1, 3 -cyklohe - xadienyl, 1, 4-cyklohexadienyl, 3 -methyl-1, 4-cyklohexadienyl, 3,4-dimethyl-1 , 4-cyklohexadienyl, 6-methyl -1, 4-cyklohexadienyl, 2,4-dimethyl -1, 4-cyklohexadienyl, 2,6 -dimethyl-1, 4-cyklohexadienyl, 2,5 -dimethyl-1 , 4-cyklohexadienyl, 6 - (tert -butyl) -1 , 4-cyklohexadienyl, 3,6, 6-tri - methyl -1 , 4-cyklohexadienyl, 3 -methyl-3 , 6 - cyklohexadienyl, 6 -methyl-3 , 6 -cyklohexadienyl, 2, 6 -dimethyl-3 , 6 -cyklohexadienyl, 2,5,5 -trimethyl - 3 , 6 - cyklohexadienyl, 3,5,5 -trimethyl-3 , 6 - cyklohexadienyl, 2, 4-dimethyl - 3 , 6 - cyklohexadienyl, 6- (tert-butyl) -3 , 6 - cyklohexadienyl, 1, 5-cyklohexa- ,-- dienyl, 3 -methyl - 1 , 5 - cyklohexadienyl, 3 , 4-dimethyl -1 , 5 - cyklohexadienyl, 6-isopropyl-1, 5 - cyklohexadienyl, 6 -tert-butyl -1 , 5 - cyklohexadienyl, 2,6-dimethyl- 1, 5 - cyklohexadienyl, 3 - methyl-2 , 6 - cyklohexadienyl, 2, 5 , 5 -tri - methyl-2, 6- cyklohexadienyl, 3,5,5 -trimethyl-2, 6 - cyklohexadienyl, 6-(tert-butyl) - 2, 6-cyklohexadienyl, 6-methyl-2, 6-cyklohexadienyl, 1 -cykloheptenyl, 3-methyl-1 -cykloheptenyl, 3 , 4-dimethyl-1-cykloheptenyl, 7-methyl-1 -cykloheptenyl, 4, 5-dimethyl-l -cykloheptenyl, 2-methyl-l -cykloheptenyl, 6-methyl-1-cykloheptenyl, 7-methyl-7-cykloheptenyl, 7-(tert-butyl)-1-cykloheptenyl og 3 , 4-diisopropyl-l-cykloheptenyl. Representative Y cycloalkenyl radicals for the O -chloroacetamides include e.g. 1-cyclopentenyl, 3-methyl-1-cyclopentenyl, 5-methyl-1-cyclopentenyl, 3, 4-dimethyl-1-cyclopentenyl, 2, 5-dimethyl-1-cyclopentenyl, 5-methyl-5-cyclopentenyl, 3, 4-dimethyl-5-cyclopentenyl, 5-(tert-butyl)-l-cyclopentenyl, 1-cyclohexenyl, 3-methyl-1-cyclohexenyl, 3,4-dimethyl-1-cyclohexenyl, 6-methyl-1-cyclohexenyl, 2, 4-dimethyl-1 -cyclohexenyl, 3-methyl-6-cyclohexenyl, 3,4-dimethyl-6-cyclohexenyl, 2, 6-dimethyl-1 - cyclohexenyl, 3,3-dimethyl-1 - cyclohexenyl, 6- (tert-butyl)-1 - cyclohexenyl, 1, 3-cyclohexadienyl, 3-methyl-1, 3-cyclohexadienyl, 3, 4-dimethyl-1, 3-cyclohexadienyl, 6-methyl-1, 3-cyclohexadienyl, 2, 4-dimethyl-1, 3-cyclo - 'hexadienyl, 3 -methyl-4, 6- cyclohexadienyl, 3 , 4-dimethyl-4, 6-cyclohexadienyl , 2, 6-dimethyl-4, 6-cyclohexadienyl, 5,5 -dimethyl-1,3-cyclohexadienyl,6-(tert-butyl)-1,3-cyclohexadienyl,3,5,5-trimethyl-1,3-cyclohexadienyl,1,4-cyclohexadienyl,3-methyl-1 , 4-cyclohexadienyl, 3,4-dimethyl-1 , 4-cyclohexadienyl, 6-methyl -1, 4-cyclohexadienyl, 2,4-dimethyl -1, 4-cyclohexadienyl, 2,6-dimethyl-1, 4-cyclohexadienyl, 2,5-dimethyl-1, 4-cyclohexadienyl, 6-(tert-butyl) -1, 4-cyclohexadienyl, 3,6, 6-tri-methyl-1, 4-cyclohexadienyl, 3-methyl-3, 6-cyclohexadienyl, 6-methyl-3, 6-cyclohexadienyl, 2, 6-dimethyl-3 , 6 -cyclohexadienyl, 2,5,5 -trimethyl - 3 , 6 - cyclohexadienyl, 3,5,5 -trimethyl-3 , 6 - cyclohexadienyl, 2, 4-dimethyl - 3 , 6 - cyclohexadienyl, 6-(tert- butyl) -3, 6-cyclohexadienyl, 1, 5-cyclohexa- ,-- dienyl, 3 -methyl - 1 , 5 - cyclohexadienyl, 3 , 4-dimethyl -1 , 5 - cyclohexadienyl, 6-isopropyl-1 , 5 - cyclohexadienyl, 6 -tert-butyl -1 , 5 - cyclohexadienyl, 2 ,6-dimethyl- 1, 5 - cyclohexadienyl, 3 - methyl-2 , 6 - cyclohexadienyl, 2, 5 , 5 -tri - methyl-2, 6- cyclohexadienyl, 3,5,5 -trimethyl-2, 6 - cyclohexadienyl , 6-(tert-butyl)-2, 6-cyclohexadienyl, 6-methyl-2, 6-cyclohexadienyl, 1-cycloheptenyl, 3-methyl-1-cycloheptenyl, 3, 4-dimethyl-1-cycloheptenyl, 7-methyl -1-cycloheptenyl, 4, 5-dimethyl-1-cycloheptenyl, 2-methyl-1-cycloheptenyl, 6-methyl-1-cycloheptenyl, 7-methyl-7-cycloheptenyl, 7-(tert-butyl)-1-cycloheptenyl and 3,4-diisopropyl-1-cycloheptenyl.
Nærværende N-(l-cykloalken-1-yl) CC-kloracetamider fremstilles ved en fremgangsmåte som består i å omsette et klor acetyl-halogenid med et imin med formelen The present N-(1-cycloalken-1-yl) CC-chloroacetamides are prepared by a method which consists in reacting a chloro acetyl halide with an imine of the formula
hvor R er som foran definert og A er valgt fra gruppen where R is as defined above and A is selected from the group
hvor R' og n er som foran definert. where R' and n are as defined above.
Syntesen av de nærværende forbindelser kan angis som følger: The synthesis of the present compounds can be stated as follows:
hvor R er som foran definert og X er Cl, Br eller J. where R is as defined above and X is Cl, Br or J.
Omsetningen av kloracetylhalogenid med iminer kan utføres på forskjellig måte. Normalt er det ønsket for maksimalt utbytte at iminet er tilstede i minst en ekvimolar mengde til kloracetylhalogenidet og fortrinnsvis i overskudd av ekvimolar mengde. Reaksjonen utføres hensikts-messig ved romtemperatur, d.v.s. ca. 20 - 25°C. Imidlertid kan høyere eller lavere temperatur anvendes og temperaturen er ikke kritisk. F. eks. anvendes vanligvis temperaturer over ca. 4o°C når ingen syreakseptor anvendes. The reaction of chloroacetyl halide with imines can be carried out in different ways. Normally it is desired for maximum yield that the imine is present in at least an equimolar amount to the chloroacetyl halide and preferably in excess of the equimolar amount. The reaction is conveniently carried out at room temperature, i.e. about. 20 - 25°C. However, a higher or lower temperature can be used and the temperature is not critical. For example temperatures above approx. 4o°C when no acid acceptor is used.
Reaksjonen utføres fortrinnsvis i nærvær av en syreakseptor og The reaction is preferably carried out in the presence of an acid acceptor and
et inert organisk medium. Syreakseptor en er vanligvis tilstede i minst ek-vimolare mengder basert på mengden av hydrogenhalogenid som dannes ved reaksjonen. Egnede syreakseptorer, f. eks. alkalisk virkende eller basiske materialer med evnen til å binde syren som utvikles ved reaksjonen, er ter-tiære aminer slik som trimethylamin, triethylamin, pyridin, kvaternære ammoniumhydroxyder, N-ethylmorfolin o.l. , uorganiske baser slik som na-triumhydroxyd og kalsiumhydroxyd, natriumkarbonat o.l. Et overskudd av iminreaksjonskomponenter tjener også som en syreakseptor. an inert organic medium. Acid acceptor is usually present in at least equimolar amounts based on the amount of hydrogen halide formed in the reaction. Suitable acid acceptors, e.g. alkaline-acting or basic materials with the ability to bind the acid that develops in the reaction are tertiary amines such as trimethylamine, triethylamine, pyridine, quaternary ammonium hydroxides, N-ethylmorpholine and the like. , inorganic bases such as sodium hydroxide and calcium hydroxide, sodium carbonate etc. An excess of imine reaction components also serves as an acid acceptor.
Inerte organiske medier som kan anvendes ved utførelsen av oppfinnelsen omfatter f. eks. hydrokarboner slik som benzen, toluen, xylen, cyklohexan, methylcyklohexan, n-heptan, n-hexan o.l.; etere slik som iso-propyleter, n-butyleter, 1,4-dioxan, isobutyleter, diethyleter og lignende; alifatiske og cykloalifatiske ketoner slik som methylisopropylketon, methyl-isobutylketon, methylisoamylketon, diisopropylketon, cyklohexanon o. 1. ; og organiske halogenider slik som karbontetraklorid, n-butylklorid, ethylendi-klorid, tetraklorethylen o.1. Inert organic media that can be used in the execution of the invention include e.g. hydrocarbons such as benzene, toluene, xylene, cyclohexane, methylcyclohexane, n-heptane, n-hexane and the like; ethers such as isopropyl ether, n-butyl ether, 1,4-dioxane, isobutyl ether, diethyl ether and the like; aliphatic and cycloaliphatic ketones such as methylisopropylketone, methylisobutylketone, methylisoamylketone, diisopropylketone, cyclohexanone etc. 1.; and organic halides such as carbon tetrachloride, n-butyl chloride, ethylene dichloride, tetrachloroethylene, etc.
Fraskillelsen av det resulterende reaksjonsprodukt fra reaksjonsblandingen utføres lett. F. eks. skilles saltet slik som et tertiært aminhydro-kloridsalt som dannes under reaksjonen på grunn av nærvær av en tertiær aminforbindelse ved denne som en syreakseptor fra produktet som. inneholder reaksjonsblandingen ved enkle midler slik som filtrering, og oppløsnings-midlet fjernes fra det resulterende filtrat ved avdrivning eller destillasjon, fortrinnsvis vakumdestillasjon ved lav temperatur. Produktet kan renses på en hver av de vanlige kjente måter på området, f. eks . fraksjonert destillasjon ved redusert trykk, selektiv ekstraksjon, fraksjonert destillasjon under anvendelse av en bærergass eller en egnet kombinasjon av disse. Hvis ønsket kan produktet utsettes for filmdestillasjon, omkrystallisasjon eller en kombinasjon av begge for ytterligere rensning. The separation of the resulting reaction product from the reaction mixture is easily accomplished. For example the salt is separated as a tertiary amine hydrochloride salt which is formed during the reaction due to the presence of a tertiary amine compound at this as an acid acceptor from the product which. contains the reaction mixture by simple means such as filtration, and the solvent is removed from the resulting filtrate by stripping or distillation, preferably vacuum distillation at low temperature. The product can be cleaned in any of the usual ways known in the field, e.g. fractional distillation at reduced pressure, selective extraction, fractional distillation using a carrier gas or a suitable combination of these. If desired, the product can be subjected to film distillation, recrystallization or a combination of both for further purification.
N-(1-cykloalken-1-yl) a-kloracetamidene som anvendes i preparatene etter nærværende oppfinnelse, er flytende eller krystallinske faste materialer som er uoppløselige i vann, men noe oppløselig i mange organiske oppløsningsmidler slik som alkoholer, ketoner, benzen, toluen, xylen, hexan o.l. The N-(1-cycloalken-1-yl) α-chloroacetamides used in the preparations according to the present invention are liquid or crystalline solid materials which are insoluble in water, but somewhat soluble in many organic solvents such as alcohols, ketones, benzene, toluene , xylene, hexane etc.
Ifølge nærværende oppfinnelse er det blitt funnet at veksten av spirende frø, skytende stiklinger og etablert vegetasjon kan kontrolleres eller modifiseres ved å utsette frøene, stiklingene eller røttene eller plantedelen over jorden for etablert vegetasjon for virkningen av en effektiv mengde av et eller flere N-(l-cykloalken-1-yl) -kloracetamider som anvendes etter nærværende oppfinnelse. Disse forbindelser er effektive som generelle fytotoksiske midler inklusive post-emergens og pre-emergens-fytotoksiske midler, men deres mest fremtredende anvendelighet er som pre-emergens fytotoksiske midler. Dessuten karakteriseres disse forbindelser ved et spekt-rum for herbicid eller fytotoksisk aktivitet, d.v.s. de modifiserer veksten av en rekke forskjellige plantesystemer inklusive bred-bladede planter og gress-planter.. According to the present invention, it has been found that the growth of germinating seeds, shoot cuttings and established vegetation can be controlled or modified by exposing the seeds, cuttings or roots or aboveground plant part of established vegetation to the action of an effective amount of one or more N-( 1-cycloalken-1-yl)-chloroacetamides which are used according to the present invention. These compounds are effective as general phytotoxic agents including post-emergence and pre-emergence phytotoxic agents, but their most prominent utility is as pre-emergence phytotoxic agents. Moreover, these compounds are characterized by a spectrum of herbicidal or phytotoxic activity, i.e. they modify the growth of a number of different plant systems including broad-leaved plants and grass plants..
For korthetens og enkelhetens skyld vil uttrykket "aktiv komponent" i det følgende bli anvendt for å beskrive N-(l-cykloalken-1-yl) tt-kloracetamidene som anvendes i preparatene etter oppfinnelsen. For the sake of brevity and simplicity, the term "active component" will be used in the following to describe the N-(1-cycloalken-1-yl) tt-chloroacetamides used in the preparations according to the invention.
De fytotoksiske preparater etter nærværende oppfinnelse inneholder minst en aktiv komponent og et materiale som på området betegnes som et fytotoksisk hjelpemiddel i flytende eller fast form. Preparatene fremstilles ved å blande den aktive komponent med et hjelpemiddel inklusive fortynningsmidler, drøyemidler , bærere og kondisjoneringsmidler for å fremskaffe preparatet i form av finfordelte, partikkelformede faste stoffer, granulater, pel-lets, oppløsningsmidler og vandige dispersjoner eller emulsjoner. Således kan den aktive komponent anvendes ved et hjelpemiddel slik som et finfordelt fast stoff, en oppløsningsvæske av organisk opprinnelse, vann, et fuktningsmiddel, et dispergeringsmiddel, et emulgeringsmiddel eller enhver egnet kombinasjon av disse. The phytotoxic preparations according to the present invention contain at least one active component and a material which is referred to in the field as a phytotoxic aid in liquid or solid form. The preparations are made by mixing the active component with an aid including diluents, emollients, carriers and conditioners to produce the preparation in the form of finely divided, particulate solids, granules, pellets, solvents and aqueous dispersions or emulsions. Thus, the active component can be used with an aid such as a finely divided solid, a solvent of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent or any suitable combination of these.
Typiske finfordelte bærestoffer og drøyemidler for fytotoksiske preparater etter nærværende oppfinnelse omfatter f. eks. talkum, lere, pimpsten, silisiumoxyd, diatoméjord, valnøttmel, kritt, kvarts, fullerjord, svovel, pulverisert kork, pulverisert tre , tobakstøv, vulkanaske o. 1. Typiske flytende fortynningsmidler er kerosen, petroleumnafta, hexan, toluen, benzen, aceton, ethylen diklorid, xylen, alkoholer, dieseloljer, glycoler Typical finely divided carriers and retarding agents for phytotoxic preparations according to the present invention include e.g. talc, clay, pumice, silicon oxide, diatomaceous earth, walnut flour, chalk, quartz, fuller's earth, sulphur, powdered cork, powdered wood, tobacco dust, volcanic ash etc. 1. Typical liquid diluents are kerosene, petroleum naphtha, hexane, toluene, benzene, acetone, ethylene dichloride, xylene, alcohols, diesel oils, glycols
o.l. beer.
De fytotoksiske preparater etter oppfinnelsen, særlig væsker og fuktbare artikler inneholder vanligvis som et kondisjoneringsmiddel en eller flere overflateaktive midler i mengder tilstrekkelig til å gjøre et gitt preparat lett dispergerbart i vann eller olje. Med uttrykket "overflateaktivt middel" forståes at fuktningsmidler, dispergeringsmidler, suspenderingsmidler og emulgeringsmidler er inkludert herved. Uttrykket "fytotoksiske preparat" anvendes her og i de etterfølgende krav i den mening ikke bare å omfatte preparater i en egnet form for anvendelse, men også konsentrerte preparater som krever fortynning o.l. med en egnet mengde væske eller fast hjelpemiddel før anvendelsen. The phytotoxic preparations according to the invention, especially liquids and wettable articles, usually contain as a conditioning agent one or more surfactants in quantities sufficient to make a given preparation easily dispersible in water or oil. The term "surfactant" is understood to include wetting agents, dispersing agents, suspending agents and emulsifying agents. The term "phytotoxic preparation" is used here and in the following claims in the sense of not only including preparations in a suitable form for use, but also concentrated preparations that require dilution etc. with a suitable amount of liquid or solid aid before use.
De følgende eksempler vil illustrere fremstillingen av de aktive forbindelser og deres fytotoksiske virkning. I de følgende eksempler såvel som i beskrivelsen angis deler og prosent etter vekt med mindre annet er angitt. The following examples will illustrate the preparation of the active compounds and their phytotoxic action. In the following examples as well as in the description, parts and percentages are given by weight, unless otherwise stated.
Eksempel 1 Example 1
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(l-cyklohexan-1-yl) N-(isobutyl) « - kloracetamid. N-(1-cyclohexan-1-yl) N-(isobutyl) -chloroacetamide.
Til en oppløsning av 33,9 deler kloracetylklorid i ZOO deler benzen holdt ved en temperatur på ca. 5°C tilsettes langsomt under omrøring 45,9 deler N-cyklohexyliden N-isobutylamin. Etter omrøring ved ytterligere 30 minutter ved ca. 5°C tilsettes 30,3 deler triethylamin. Reaksjonsblandingen får varme seg opp til ca. 25°C og røres i en time. Reaksjonsblandingen filtreres derpå for å fjerne aminsaltene, og filtratet vaskes to ganger med vann. Benzenet fjernes ved fordampning og residuet destilleres fraksjonert for å gi en produktfraksjon som koker innen området 130 - 134°C ved et trykk på 3mm Hg. Produktet utgjør 36, 1 del av en oljeaktiv væske og strukturen bekreftes ved kjernemagnetisk reson-ans (NMR) spektralanalyse. To a solution of 33.9 parts of chloroacetyl chloride in ZOO parts of benzene held at a temperature of approx. 5°C, 45.9 parts of N-cyclohexylidene N-isobutylamine are added slowly while stirring. After stirring for a further 30 minutes at approx. 5°C, 30.3 parts of triethylamine are added. The reaction mixture is allowed to warm up to approx. 25°C and stirred for one hour. The reaction mixture is then filtered to remove the amine salts, and the filtrate is washed twice with water. The benzene is removed by evaporation and the residue is fractionally distilled to give a product fraction which boils within the range 130 - 134°C at a pressure of 3 mm Hg. The product comprises 36.1 parts of an oil-active liquid and the structure is confirmed by nuclear magnetic resonance (NMR) spectral analysis.
Beregnet for C12H2QNOCl: C. 63.0; H. 8.74; CI. 15.50 Funnet: C. 63.63; H. 8.85; Cl. 15.39 Calculated for C12H2QNOCl: C. 63.0; H. 8.74; CI. 15.50 Found: C. 63.63; H. 8.85; Cl. 15.39
Eksempel 2 Example 2
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(l-cyklohexan-1 -yl) N-(n-propyl) A-kloracetamid. N-(1-cyclohexan-1-yl) N-(n-propyl) A-chloroacetamide.
Til en oppløsning på 33,9 deler kloracetylklorid i 250 deler benzen, holdt ved en temperatur på ca. 5°C tilsettes langsomt under omrøring 41,7 deler N-cyklohexyliden N-(n-propyl)amin. Etter omrøring i ytterligere 30 minutter ved ca. 5°C tilsettes 30,3 deler triethylamin og r eaksjonsbland-ingen får varme seg opp til ca. 25°C. Reaksjonsblandingen røres om i 1 time ved 25°C, filtreres, vaskes to ganger med vann og benzenet fjernes ved fordampning. Residuet destilleres fraksjonert og gir en produktfraksjon som koker ved 125°C - 126°C ved et trykk på 3mm Hg. Denne fraksjon løses opp i hexan og omkrystalliseres og gir 37,8 deler av et fast produkt med smeltepunkt på 45 - 47°C. Strukturen bekreftes ved NMR spektralanalyse. To a solution of 33.9 parts of chloroacetyl chloride in 250 parts of benzene, kept at a temperature of about At 5°C, 41.7 parts of N-cyclohexylidene N-(n-propyl)amine are added slowly while stirring. After stirring for a further 30 minutes at approx. 5°C, 30.3 parts of triethylamine are added and the reaction mixture is allowed to warm up to approx. 25°C. The reaction mixture is stirred for 1 hour at 25°C, filtered, washed twice with water and the benzene is removed by evaporation. The residue is fractionally distilled and gives a product fraction which boils at 125°C - 126°C at a pressure of 3 mm Hg. This fraction is dissolved in hexane and recrystallized to give 37.8 parts of a solid product with a melting point of 45 - 47°C. The structure is confirmed by NMR spectral analysis.
Beregnet for CjjHjgNOCl: C, 61.40; H, 8.37; Cl, 16.50 Calculated for CjjHjgNOCl: C, 61.40; H, 8.37; Cl, 4.50 p.m
Funnet: C, 61.54; H, 8.50; Cl, 16.08 Found: C, 61.54; H, 8.50; Cl, 16.08
Eksempel 3 Example 3
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(l-cyklohexen-1-yl) N-(ethyl) d-kloracetamid. N-(1-cyclohexen-1-yl) N-(ethyl) d -chloroacetamide.
Til en oppløsning på 33,9 deler kloracetylklorid i 250 deler benzen, holdt ved en temperatur på ca. 5°C tilsettes langsomt under omrøring 37.5 deler N-cyklohexyliden-ethyl-amin. Etter omrøring i ytterligere 30 minutter ved ca. 5°C tilsettes 30,3 deler triethylamin, og reaksjons - blandingen får varme seg opp til ca. 25°C. Reaksjonsblandingen røres i 1 time ved 25°C, filtreres, vaskes to ganger med vann og benzenet fjernes ved fordampning. Residuet destilleres fraksjonert og gir produktfraksjonen som koker innen området 115 - 120°C ved et trykk på 2 mm Hg. Denne fraksjon løses opp i hexan og omkrystalliseres og gir 37,4 deler fast stoff med smeltepunkt på 27 - 28°C. Strukturen bekreftes ved NMR spektralanalyse. To a solution of 33.9 parts of chloroacetyl chloride in 250 parts of benzene, kept at a temperature of about At 5°C, 37.5 parts of N-cyclohexylidene-ethylamine are added slowly while stirring. After stirring for a further 30 minutes at approx. 5°C, 30.3 parts of triethylamine are added, and the reaction mixture is allowed to warm up to approx. 25°C. The reaction mixture is stirred for 1 hour at 25°C, filtered, washed twice with water and the benzene is removed by evaporation. The residue is fractionally distilled and gives the product fraction which boils within the range 115 - 120°C at a pressure of 2 mm Hg. This fraction is dissolved in hexane and recrystallized to give 37.4 parts of a solid with a melting point of 27 - 28°C. The structure is confirmed by NMR spectral analysis.
Beregnet for C1()Hl6NOCl: N, 6.98; Cl, 17.65; molv. 201 Calculated for C1()H16NOCl: N, 6.98; Cl, 17.65; mole. 201
Funnet: N, 7.30; Cl, 18.20; molv. 200 Found: N, 7.30; Cl, 18.20; mole. 200
Eksempel 4 Example 4
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(l-cyklohexen-1 -yl) N-(2-methoxyisopropyl) a-kloracetamid. N-(1-cyclohexen-1-yl)N-(2-methoxyisopropyl)α-chloroacetamide.
Til en oppløsning på 22.4 deler kloracetylklorid i 150 deler ben - zen, holdt ved en temperatur på ca. 5°C, tilsettes under omrøring 34 deler To a solution of 22.4 parts of chloroacetyl chloride in 150 parts of benzene, kept at a temperature of approx. 5°C, add 34 parts while stirring
N-cyklohexyliden N-(2-methoxyisopropyl)amin. Etter omrøring i ytterligere 30 minutter tilsettes 20.2 deler triethylamin, og reaksjonsblandingen får varme seg opp til ca. 25°C. Reaksjonsblandingen røres i en time ved 25°C , filtreres, vaskes to ganger med vann og benzenet fjernes ved fordampning. Residuet destilleres fraksjonert og gir produktfraksjonen som koker innen området 146 - 150 C ved et trykk på 2 mm Hg. Produktfraksjonen utgjør 24,1 deler av en oljeaktig væske og har den tilskrevne struktur. N-cyclohexylidene N-(2-methoxyisopropyl)amine. After stirring for a further 30 minutes, 20.2 parts of triethylamine are added, and the reaction mixture is allowed to warm up to approx. 25°C. The reaction mixture is stirred for one hour at 25°C, filtered, washed twice with water and the benzene is removed by evaporation. The residue is fractionally distilled and gives the product fraction which boils within the range 146 - 150 C at a pressure of 2 mm Hg. The product fraction comprises 24.1 parts of an oily liquid and has the attributed structure.
Beregnet for C12H19OzNCl: CI, 14.4; N, 5.7 Calculated for C12H19OzNCl: CI, 14.4; N, 5.7
Funnet: Cl , 14, 19; N, 5.94 Found: Cl , 14, 19; N, 5.94
Eksempel 5 Example 5
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(1 -cyklopenten-1 -yl) N-(isopropyl) <t-kloracetamid. N-(1-cyclopenten-1-yl)N-(isopropyl)<t-chloroacetamide.
Til en oppløsning på 22.6 deler kloracetylklorid i benzen noldt To a solution of 22.6 parts chloroacetyl chloride in benzene noldt
ved en temperatur på ca. 5°C tilsettes under omrøring 25 deler N-cyklo-pentyliden N-isopropylamin. Etter omrøring i ytterligere 30 minutter tilsettes 20 deler triethylamin.' Reaksjonsblandingen filtreres, vaskes med vann og filtratet tørkes over MgSO^. Residuet destilleres fraksjonert og gir produktfraksjonen som koker innen området 120 - 122°C ved et trykk på 2 mm Hg. Produktet utgjør 12.5 deler og den tilskrevne struktur be - kreftes ved NMR spektralanalyse. at a temperature of approx. 5°C, 25 parts of N-cyclopentylidene N-isopropylamine are added while stirring. After stirring for a further 30 minutes, 20 parts of triethylamine are added.' The reaction mixture is filtered, washed with water and the filtrate is dried over MgSO 4 . The residue is fractionally distilled and gives the product fraction which boils within the range 120 - 122°C at a pressure of 2 mm Hg. The product comprises 12.5 parts and the attributed structure is confirmed by NMR spectral analysis.
Beregnet for C1QHl6<N>OCl: Cl, 17.7; N, 6.95 Calculated for C1QHl6<N>OCl: Cl, 17.7; N, 6.95
Funnet: Cl, 19.20; N, 7.05 Found: Cl, 19.20; N, 7.05
Eksempel 6 Example 6
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(l -cyklohexen-1 -yl) N-(2-propen-l -yl) d-kloracetamid. N-(1-cyclohexen-1-yl)N-(2-propen-1-yl) d-chloroacetamide.
Til en oppløsning på 33.9 deler kloracetylklorid i 250 deler benzen, holdt ved en temperatur på ca. 5°C, tilsettes under omrøring 41 deler N-(cyklohexyliden) N-(2-propen.-1-yl)amin. Etter omrøring i ytterligere 30 minutter tilsettes 30.3 deler triethylamin og reaksjonsblandingen får varme seg opp til ca. 25°C. To a solution of 33.9 parts of chloroacetyl chloride in 250 parts of benzene, kept at a temperature of approx. 5°C, 41 parts of N-(cyclohexylidene)N-(2-propen.-1-yl)amine are added while stirring. After stirring for a further 30 minutes, 30.3 parts of triethylamine are added and the reaction mixture is allowed to warm up to approx. 25°C.
Reaksjonsblandingen røres om i en time ved 25°C, filtreres, vaskes to ganger med vann og benzenet fjernes ved fordampning. Residuet destilleres fraksjonert og gir produktfraksjonen som koker ved 136°C ved et trykk på 2 mm Hg. Produktet utgjør 37. 7 deler og den tilskrevne struktur bekreftes ved NMR spektralanalyse. The reaction mixture is stirred for one hour at 25°C, filtered, washed twice with water and the benzene is removed by evaporation. The residue is fractionally distilled and gives the product fraction which boils at 136°C at a pressure of 2 mm Hg. The product comprises 37.7 parts and the attributed structure is confirmed by NMR spectral analysis.
Beregnet for CnHl6NOCl: C, 62.0; H, 7.52; Cl, 16.65 Funnet C, 61.4; H. 7.29; Cl, 16.73 Calculated for CnHl6NOCl: C, 62.0; H, 7.52; Cl, 16.65 Found C, 61.4; H. 7.29; Cl, 16.73
Eksempel 7 Example 7
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(2-methyl-6-cyklohexen-l -yl) N-methyl <l-kloracetamid. N-(2-methyl-6-cyclohexen-1-yl) N-methyl <1-chloroacetamide.
Til en oppløsning på 5.6 deler kloracetylklorid i 250 deler benzen, holdt ved en temperatur på ca. 5°C, tilsettes langsomt under omrør-ing 7.2 deler N-(2-methylcyklohexyliden) N-methylamin. Etter omrøring i ytterligere 30 minutter ved'ca. 5°C tilsettes 6.9 deler triethylamin og reaksjonsblandingen oppvarmes under tilbakeløp i ca. 1 time. Reaksjonsblandingen kjøles, filtreres, vaskes med vann og benzenet fjernes ved fordampning. Residuet destilleres fraksjonert og gir produktfraksjonen som koker innen område 125°C - 130°C ved et trykk på 1 mm Hg. Denne fraksjon løses opp i hexan og omkrystalliseres og gir et fast produkt som har et smeltepunkt på 36 - 38°C. Den tilskrevne struktur bekreftes ved NMR spektralanalyse. To a solution of 5.6 parts of chloroacetyl chloride in 250 parts of benzene, kept at a temperature of approx. 5°C, add slowly while stirring 7.2 parts of N-(2-methylcyclohexylidene)N-methylamine. After stirring for a further 30 minutes at approx. 5°C, 6.9 parts of triethylamine are added and the reaction mixture is heated under reflux for approx. 1 hour. The reaction mixture is cooled, filtered, washed with water and the benzene is removed by evaporation. The residue is fractionally distilled and gives the product fraction which boils within the range 125°C - 130°C at a pressure of 1 mm Hg. This fraction is dissolved in hexane and recrystallized to give a solid product which has a melting point of 36 - 38°C. The attributed structure is confirmed by NMR spectral analysis.
Beregnet for Cl0Hl6NOCl: C, 59.50; H, 7.95; Cl, 17.70; N, 6.95 Funnet: C, 59.50; H, 7.89; CI, 17.84; N, 7.06 Calculated for Cl0H16NOCl: C, 59.50; H, 7.95; Cl, 17.70; N, 6.95 Found: C, 59.50; H, 7.89; CI, 17.84; N, 7.06
Eksempel 8 Example 8
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(4-methylcyklohexen-l -yl) N-isopropyl Ct-kloracetamid. N-(4-methylcyclohexen-1-yl)N-isopropyl Ct-chloroacetamide.
</> Til en oppløsning på 36.8 deler kloracetylkorid i 250 deler benzen tilsettes under omrøring 100 deler N-(4-methylcyklohexyliden) - isopropylamin. Reaksjonsblandingen får varme seg opp til ca. 50°C og røres om i 3 timer. Reaksjonsblandingen filtreres, vaskes med vann og benzenet fjernes ved fordampning. Residuet destilleres fraksjonert og gir produktfraksjonen, 36.6 deler, som har et kokepunkt på 150°C ved et trykk på 1.5 mm Hg. Den tilskrevne struktur av produktoljen er bekreftet ved NMR spektralanalyse. </> To a solution of 36.8 parts of chloroacetyl chloride in 250 parts of benzene, 100 parts of N-(4-methylcyclohexylidene)-isopropylamine are added while stirring. The reaction mixture is allowed to warm up to approx. 50°C and stirred for 3 hours. The reaction mixture is filtered, washed with water and the benzene is removed by evaporation. The residue is fractionally distilled and gives the product fraction, 36.6 parts, which has a boiling point of 150°C at a pressure of 1.5 mm Hg. The attributed structure of the product oil has been confirmed by NMR spectral analysis.
Beregnet for C12H21<N>OCl: N, 6.09; Cl, 15.4 Calculated for C12H21<N>OCl: N, 6.09; Cl, 15.4
Funnet: N, 6.07; Cl, 15.35 Found: N, 6.07; Cl, 15.35
Eksempel 9 Example 9
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(l, 3-cyklohexadien-1-yl) N-isopropyl Ot-kloracetamid. N-(1,3-cyclohexadien-1-yl)N-isopropyl O-chloroacetamide.
Til en oppløsning på 22.4 deler kloracetylklorid i 250 deler benzen, holdt ved en temperatur på ca. 5°C tilsettes langsomt under omrøring 27.6 deler N-(3-cyklohexen-1-yliden) N-isopropylamin. Etter omrøring i ytterligere 30 minutter ved ca. 5°C tilsettes 8.6 deler triethylamin og reaksjonsblandingen får varme seg opp til ca. 25°C. Reaksjonsblandingen filtreres, vaskes to ganger med vann og benzenet fjernes ved fordampning. Residuet destilleres fraksjonert og gir produktfraksjonen som koker innen området på 125 - 129°C ved et trykk på 1 mm Hg. Denne fraksjon løses opp i hexan og omkrystalliseres og gir det hvite faste stoff som har et smeltepunkt på 34-36°C. Den tilskrevne struktur bekreftes ved NMR spektralanalyse. To a solution of 22.4 parts of chloroacetyl chloride in 250 parts of benzene, kept at a temperature of approx. 5°C slowly add 27.6 parts of N-(3-cyclohexen-1-ylidene)N-isopropylamine with stirring. After stirring for a further 30 minutes at approx. 5°C, 8.6 parts of triethylamine are added and the reaction mixture is allowed to warm up to approx. 25°C. The reaction mixture is filtered, washed twice with water and the benzene is removed by evaporation. The residue is fractionally distilled and gives the product fraction which boils within the range of 125 - 129°C at a pressure of 1 mm Hg. This fraction is dissolved in hexane and recrystallized to give the white solid which has a melting point of 34-36°C. The attributed structure is confirmed by NMR spectral analysis.
Beregnet for CnH17NOCl: N, 6.56; Cl, 16.7 Calculated for CnH17NOCl: N, 6.56; Cl, 16.7
Funnet: N , 6. 63; C 1, 16. 52 Found: N , 6. 63; C 1, 16. 52
Dette eksempel beskriver fremstillingen av This example describes the production of
N-(3 , 5,5 -trimethyl -1 , 3 -cyklohexadien-1 -yl) N-(ethoxyethyl) Ot-kloracetamid. N-(3 , 5 , 5 - trimethyl - 2, 6 - cyklohexadien -1 -yl) N-ethoxyethyl «-klor acetamid, og N-(3,5,5-trimethyl-1,3-cyclohexadien-1-yl)N-(ethoxyethyl)O-chloroacetamide. N-(3,5,5-trimethyl-2,6-cyclohexadien-1-yl)N-ethoxyethyl «-chloroacetamide, and
N- (3 , 5 , 5 - trimethyl-3 , 6 - cyklohexadien -1 -yl) N-ethoxyethyl Ot-klor acetamid. N-(3,5,5-trimethyl-3,6-cyclohexadien-1-yl)N-ethoxyethyl Ot-chloroacetamide.
Til en oppløsning på 11.3 deler kloracetylklorid i 150 deler benzen, holdt ved en temperatur på ca. 5°C tilsettes langsomt under omrøring 20.9 deler N- (3 , 5 , 5-trimethyl-2-cyklohexen-1-yliden) N-ethoxyethylamin. Etter omrøring i ytterligere 30 minutter ved 5°C tilsettes 4,3 deler triethylamin og reaksjonsblandingen får varme seg opp til ca. 25°C. Reaksjonsblandingen filtreres, vaskes to ganger med vann og benzenet fjernes ved fordampning. NMR spektralanalyse viser at residuet inneholder de forbindelser som fremstilles i formlene a), b) og c) ovenfor. Residuet destilleres fraksjonert og gir fr aksj onsproduktet, 12. 7 deler, som har et kokepunkt på 135°C ved et trykk på 6 mm Hg. NMR spektralanalyse viser at produktet sammen- To a solution of 11.3 parts of chloroacetyl chloride in 150 parts of benzene, kept at a temperature of approx. 5°C, 20.9 parts of N-(3,5,5-trimethyl-2-cyclohexen-1-ylidene)N-ethoxyethylamine are added slowly while stirring. After stirring for a further 30 minutes at 5°C, 4.3 parts of triethylamine are added and the reaction mixture is allowed to warm up to approx. 25°C. The reaction mixture is filtered, washed twice with water and the benzene is removed by evaporation. NMR spectral analysis shows that the residue contains the compounds produced in the formulas a), b) and c) above. The residue is fractionally distilled and gives the fraction product, 12.7 parts, which has a boiling point of 135°C at a pressure of 6 mm Hg. NMR spectral analysis shows that the product together
settes hovedsakelig av forbindelsen etter formel a) ovenfor. is set mainly by the compound according to formula a) above.
Beregnet for C15H NO Cl: C, 63,20; H, 8,42; N, 4,90; Cl, 12,45 Funnet: C, 63,33', H, 8,35; N, 4,90; Cl, 12,42 Calculated for C15HNOCl: C, 63.20; H, 8.42; N, 4.90; Cl, 12.45 Found: C, 63.33', H, 8.35; N, 4.90; Cl, 12.42
Ved å følge fremgangsmåten av de foregående eksempler og ved anvendelse av kloracetylklorid og den hensatte iminforbindelse fremstilles de følgende N-(l-cykloalken-1 -yl) «-kloracetamider . By following the procedure of the preceding examples and by using chloroacetyl chloride and the prepared imine compound, the following N-(1-cycloalken-1-yl)-chloroacetamides are prepared.
Eksempel Example
11. N-(l-cyklohexen-1-yl) N-(isopropyl) Ot -kloracetamid 11. N-(1-cyclohexen-1-yl) N-(isopropyl) O -chloroacetamide
12. N-(l-cyklohexen-1-yl) N-(ethoxyethyl) cc -kloracetamid 12. N-(1-cyclohexen-1-yl) N-(ethoxyethyl) cc -chloroacetamide
13. N-(1-cyklohexen-1-yl) N-(methoxyethyl)&. -kloracetamid 13. N-(1-cyclohexen-1-yl)N-(methoxyethyl)&. -chloroacetamide
14. N-(l -cyklopenten-1 -yl) N - (ethoxyethyl) Ot -kloracetamid 14. N-(1-cyclopenten-1-yl)N-(ethoxyethyl)O-chloroacetamide
15. N-(3-methyl-1-cyklohexen-1-yl) N-(isopropyl) OC-kloracetamid 15. N-(3-methyl-1-cyclohexen-1-yl) N-(isopropyl) OC-chloroacetamide
16. N-(l-cyklohexen-1-yl) N-(methyl) R-kloracetamid 16. N-(1-cyclohexen-1-yl) N-(methyl) R -chloroacetamide
17. N -(l-cyklohexen- 1-yl) N-(heptyl) a-klo racetamid 17. N -(1-cyclohexen-1-yl) N -(heptyl) α-chloro racetamide
18. N-(l-cyklohexen-1 -yl) N-(methoxybutyl) a-kloracetamid 18. N-(1-cyclohexen-1-yl) N-(methoxybutyl) α-chloroacetamide
19. N-(l-cyklohexen-1-yl) N-(2-buten-l -yl) CC -kloracetamid 19. N-(1-cyclohexen-1-yl) N-(2-buten-1-yl) CC -chloroacetamide
20. N-(l-cyklopenten-1-yl) N-(n-butyl) CC-kloracetamid 20. N-(1-cyclopenten-1-yl) N-(n-butyl) CC -chloroacetamide
21. N-(l-cyklopenten-1 -yl) N - (2-propen-1 -yl) OC-kloracetamid 21. N-(1-cyclopenten-1-yl)N-(2-propen-1-yl)OC-chloroacetamide
22. N-(l-cyklohepten-1-yl) N - (isopropyl) a-kloracetamid 22. N-(1-cyclohepten-1-yl)N-(isopropyl)α-chloroacetamide
23. N-(l , 3-cyklohexadien-1-yl) N-(methyl) (x-kloracetamid 23. N-(1,3-cyclohexadien-1-yl)N-(methyl) (x-chloroacetamide
24. N-(3 -methyl-1 -cyklopenten- 1 -yl) N-(methyl) a-kloracetamid 24. N-(3-methyl-1-cyclopenten-1-yl) N-(methyl) α-chloroacetamide
25. N-(3 , 4-dimethyl-l-cyklopenten-1-yl) N-(methyl) CK-kloracetamid 25. N-(3,4-dimethyl-1-cyclopenten-1-yl)N-(methyl)CK-chloroacetamide
26. N- (3 , 4-dimethyl -5- cyklopenten -1 -yl) N- (isopropyl)ct-klor acetamid 27. N-/5-(tert-butyl)-! -cyklopenten-1 -yl/ N-(isopropyl)Ot-kloracetamid 26. N-(3,4-dimethyl-5-cyclopenten-1-yl)N-(isopropyl)ct-chloroacetamide 27. N-(5-(tert-butyl)-! -cyclopenten-1-yl/N-(isopropyl)O-chloroacetamide
28. N-(3-methyl-5-cyklopenten-1-yl) N-methyl «--kloracetamid 28. N-(3-methyl-5-cyclopenten-1-yl) N-methyl «--chloroacetamide
29. N-(3 , 4-dimethyl-l-cyklohexen-1 -yl) N-(isopropyl) a-kloracetamid 29. N-(3,4-dimethyl-1-cyclohexen-1-yl)N-(isopropyl)α-chloroacetamide
30. N-(5-methyl-1-cyklohexen-1-yl) N-(isopropyl) ot-kloracetamid 30. N-(5-methyl-1-cyclohexen-1-yl) N-(isopropyl) o -chloroacetamide
31. N-(3 , 4-dimethyl-6-cyklohexen-l -yl) N-(isopropyl) et-kloracetamid 32. N-(2 , 4-dimethyl-1 -cyklohexen-1 -yl) N-(isopropyl)ot-kloracetamid 33. N-(2, 4, 6-trimethyl -1 - cyklohexen-1 -yl) N-(isopropyl) «-kloracetamid 34. N-(2, 6-dimethyl-6-cyklohexen-l-yl) N-(isopropyl) ot -kloracetamid 35. N-/2, 6-di (tert-butyl)-1 -cyklohexen-1 -yl/N - (isopropyl) a-kloracetamid 31. N-(3,4-dimethyl-6-cyclohexen-1-yl)N-(isopropyl)eth-chloroacetamide 32.N-(2,4-dimethyl-1-cyclohexen-1-yl)N-(isopropyl )ot-chloroacetamide 33. N-(2, 4, 6-trimethyl -1 - cyclohexen-1 -yl) N-(isopropyl) «-chloroacetamide 34. N-(2, 6-dimethyl-6-cyclohexen-1- yl) N-(isopropyl) o -chloroacetamide 35. N-(2,6-di (tert-butyl)-1 -cyclohexen-1 -yl) N -(isopropyl) a -chloroacetamide
36. N-(3-methyl-6-cyklohexen-1-yl) N-methyl 0C-kloracetamid 36. N-(3-methyl-6-cyclohexen-1-yl) N-methyl OC-chloroacetamide
37. N-(6-methyl-1 , 3-cyklohexadien-1 -yl) N - (isopropyl) «-kloracetamid . '38. N-(5-methyl-4, 6-cyklohexadien-1 -yl) N-(isopropyl)oC-kloracetamid 39. N-(3-methyl-4, 6-cyklohexadien-1-yl) N-(isopropyl) a-kloracetamid 40. N-(3 , 5-dimethyl-1, 3-cyklohexadien-1 -yl) N-(isopropyl)«-kloracetamid 41. N-/2, 6-di(tert-butyl)-1 , 3-cyklohexadien-1 -yl/-N-methylOt-kloracetamid 42. N - (2-methyl -1, 3 - cyklohexadien -1 -yl) -N-methyl « -kloracetamid 43. N -(4-methyl - 1, 3 - cyklohexadien-1 -yl) -N-methyl Ol -kloracetamid 44. N-(3 , 5 - dimethyl - 1, 4-cyklohexadien - 1 -yl) -N-methyl 0( -kloracetamid 45. N- (2, 6-dimethyl-1, 4-cyklohexadien - 1 -yl) -N-methyl« -kloracetamid 46. N-(3 , 3 -dimethyl-1, 4-cyklohexadien - 1 -yl) -N-methyl Ot -kloracetamid 47. N-(6-tert-butyl-l, 4-cyklohexadien-1 -yl)-N-methyl Ot -kloracetamid 48. N -(4-isopropyl-1 ,4-cyklohexadien-1 -yl) -N- methyl ot -kloracetamid 49. N-(4-methyl-l ,4-cyklohexadien-l -yl)-N-isopropyl Ot -kloracetamid 37. N-(6-methyl-1,3-cyclohexadien-1-yl)N-(isopropyl)-chloroacetamide. '38. N-(5-methyl-4, 6-cyclohexadien-1-yl) N-(isopropyl)oC-chloroacetamide 39. N-(3-methyl-4, 6-cyclohexadien-1-yl) N-(isopropyl) a -chloroacetamide 40. N-(3,5-dimethyl-1,3-cyclohexadien-1-yl)N-(isopropyl)«-chloroacetamide 41.N-/2,6-di(tert-butyl)-1,3 -cyclohexadien-1 -yl/-N-methylOt-chloroacetamide 42. N - (2-methyl -1, 3 - cyclohexadien -1 -yl) -N-methyl « -chloroacetamide 43. N -(4-methyl - 1, 3 - cyclohexadien-1 -yl) -N-methyl O -chloroacetamide 44. N-(3 , 5 - dimethyl - 1, 4-cyclohexadien - 1 -yl) -N-methyl O( -chloroacetamide 45. N - (2 , 6-dimethyl-1, 4-cyclohexadien-1-yl)-N-methyl«-chloroacetamide 46. N-(3, 3-dimethyl-1, 4-cyclohexadien-1-yl)-N-methyl O -chloroacetamide 47. N-(6-tert-butyl-1,4-cyclohexadien-1-yl)-N-methyl O -chloroacetamide 48. N -(4-isopropyl-1,4-cyclohexadien-1-yl)-N- methyl ot -chloroacetamide 49. N-(4-methyl-1,4-cyclohexadien-1 -yl)-N-isopropyl ot -chloroacetamide
50. N -(3 -methyl-2 , 6 - cyklohexadien -1 -yl) -N -methyl 0* -kloracetamid 50. N -(3-methyl-2,6-cyclohexadien-1-yl)-N-methyl O*-chloroacetamide
51. N-(3 , 4-dimethyl-2, 6 - cyklohexadien -1 -yl)-N-methyl CS -kloracetamid 52. N-(4, 4-dimethyl -2, 6-cyklohexadien -1 -yl) -N-methylOt -kloracetamid 53 . N - (6 -tert-butyl-2, 6 - cyklohexadien -1 -yl) -N -methyl Ot -kloracetamid 54. N-(2, 6-dimethyl-2, 6-cyklohexadien-l -yl)-N-isopropylOt-kloracetamid 55. :'' N - (2, 4-dimethyl -2, 6-cyklohexadien-l -yl)-N-isopropylot -kloracetamid 56. N-(3-methyl-1 , 5-cyklohexadien-1-yl)-N-methyl OC -kloracetamid 57. N -(3 , 4-dimethyl-l, 4-cyklohexadien - 1 -yl) -N-methyl <X -kloracetamid 51. N-(3,4-dimethyl-2,6-cyclohexadien-1-yl)-N-methyl CS-chloroacetamide 52.N-(4,4-dimethyl-2,6-cyclohexadien-1-yl)- N-methylO -chloroacetamide 53 . N-(6-tert-butyl-2,6-cyclohexadien-1-yl)-N-methyl Ot-chloroacetamide 54. N-(2,6-dimethyl-2,6-cyclohexadien-1-yl)-N- isopropyl O-chloroacetamide 55. :'' N - (2, 4-dimethyl -2, 6-cyclohexadien-1 -yl)-N-isopropyl o -chloroacetamide 56. N-(3-methyl-1 , 5-cyclohexadien-1- yl)-N-methyl OC -chloroacetamide 57. N -(3,4-dimethyl-1,4-cyclohexadien-1-yl)-N-methyl<X-chloroacetamide
58. N- (5 -methyl -1, 5 - cyklohexadien -1 -yl) -N - methylOt -kloracetamid 58. N-(5-methyl-1,5-cyclohexadien-1-yl)-N-methylOt-chloroacetamide
59. N-(4-methyl-1 , 5-cyklohexadien-1 -yl) -N-methyl Ot -kloracetamid 59. N-(4-methyl-1,5-cyclohexadien-1-yl)-N-methyl O -chloroacetamide
60. N - (2, 6-dimethyl -1, 5 - cyklohexadien -1 -yl) -N-methyl Ot -kloracetamid 61. N -(2, 4, 4-trimethyl - 1, 5-cyklohexadien -1 -yl) -N-methylOf-kloracetamid 62. N-(6-tert-butyl - 1 , 5 -cyklohexadien -1 -yl) -N-methyl a -kloracetamid 60. N - (2, 6-dimethyl -1, 5 - cyclohexadien -1 -yl) -N-methyl O -chloroacetamide 61. N -(2, 4, 4-trimethyl - 1, 5-cyclohexadien -1 -yl ) -N-methylOf-chloroacetamide 62. N-(6-tert-butyl-1,5-cyclohexadien-1-yl)-N-methyl α-chloroacetamide
63. N-(3 -methyl-3 , 6-cyklohexadien-l-yl) -N -methyl Ot -kloracetamid 63. N-(3-methyl-3,6-cyclohexadien-1-yl)-N-methyl O-chloroacetamide
64. N-(2-methyl-3 , 6-cyklohexadien-l -yl) -N-methylOL -kloracetamid 64. N-(2-methyl-3,6-cyclohexadien-1-yl)-N-methylOL-chloroacetamide
65 . N - (2 , 5 - dimethyl-3 , 6-cyklohexadien - 1 -yl) -N-methyl 01 -kloracetamid 66. N-(6 -tert-butyl-3 , 6 -cyklohexadien-1 -yl) -N-isopropylOt-kloracetamid 67 . N-(3 , 6-dimethyl-3 , 6 - cyklohexadien - 1 -yl) -N-isopropylOt-klor acetamid 65 . N - (2 , 5 - dimethyl-3 , 6-cyclohexadien-1 -yl)-N-methyl 01 -chloroacetamide 66. N-(6 -tert-butyl-3 , 6 -cyclohexadien-1 -yl) -N- isopropylOt-chloroacetamide 67 . N-(3,6-dimethyl-3,6-cyclohexadien-1-yl)-N-isopropylO-chloroacetamide
68. N-(3-methyl-l-cyklohepten-1 -yl) N-(isopropyl)or -kloracetamid 68. N-(3-methyl-1-cyclohepten-1-yl) N-(isopropyl)or -chloroacetamide
69 . N-(3 , 4-dimethyl-l -cyklohepten- 1 -yl) N-(isopropyl) OL-kloracetamid 70. N-(7-tert-butyl-1 -cyklohepten- 1 -yl) N-(isopropyl) Ot -kloracetamid 71. N-(3 ,4-diisopropyl-1 - cyklohepten -1 - yl) N- (isopropyl)ot -kloracetamid 69 . N-(3,4-dimethyl-1-cyclohepten-1-yl)N-(isopropyl)OL-chloroacetamide 70. N-(7-tert-butyl-1-cyclohepten-1-yl)N-(isopropyl)Ot -chloroacetamide 71. N-(3,4-diisopropyl-1-cyclohepten-1-yl)N-(isopropyl)ot-chloroacetamide
72. N-(6-methyl-7-cyklohepten-l-yl) N-(isopropyl) ot -kloracetamid 72. N-(6-methyl-7-cyclohepten-1-yl) N-(isopropyl) o -chloroacetamide
73. N-(3 , 5-dimethyl-1-cyklohepten-1-yl) N-(isopropyl)ot-kloracetamid. 73. N-(3,5-dimethyl-1-cyclohepten-1-yl)N-(isopropyl)o-chloroacetamide.
Pre-emergens-fytotoksisiteten for N-(l-cykloalken-1-yl) Ot - klor acetamid er som er illustrerende for oppfinnelsen, vises ved følgende: The pre-emergence phytotoxicity for N-(1-cycloalken-1-yl) O - chloroacetamide, which is illustrative of the invention, is shown by the following:
Jord av god kvalitet anbringes i aluminiumpanner 25 x 14,5 x 7 Good quality soil is placed in aluminum pans 25 x 14.5 x 7
cm og pakkes sammen til en dybde på ca. 1 - 1, 25 cm fra toppen av pannen. Et bestemt antall av frø fra 19 forskjellige plantearter anbringes i toppen av jorden i forskjellige panner. De fytotoksiske preparater tilføres jorden på cm and packed together to a depth of approx. 1 - 1.25 cm from the top of the pan. A certain number of seeds from 19 different plant species are placed on top of the soil in different pans. The phytotoxic preparations are added to the soil
to metoder: two methods:
1) tilføring til overflaten av toppjordlaget, og 1) supply to the surface of the top soil layer, and
2) innblanding med eller innarbeidelse i toppjordlaget. 2) mixing with or incorporation into the top soil layer.
Ved overflatepåføringsmetoden dekkes frøene med et ca. 1 cm jordlag og jevnes ut. Det fytotoksiske preparat påføres ved påsprøytning av overflaten av topplaget av jorden før frøene vannes med en oppløsning som inneholder en tilstrekkelig mengde av aktive komponenter for å oppnå den ønskede mengde per arealenhet på jordoverflaten. With the surface application method, the seeds are covered with an approx. 1 cm layer of soil and leveled. The phytotoxic preparation is applied by spraying the surface of the top layer of the soil before the seeds are watered with a solution containing a sufficient amount of active components to achieve the desired amount per unit area on the soil surface.
Hvor innarbeidelse i jorden skjer, veies den nødvendige jordmeng-de for å fylle pannene og blandes med et fytotoksisk preparat som inneholder et kjent kvantum av aktiv komponent. Pannen fylles derpå med innblandingen og utjevnes. Vanningen utføres ved å la jorden i pannen absorbere fuktighet gjennom pannens perforerte bunn. Where incorporation into the soil takes place, the required amount of soil to fill the pans is weighed and mixed with a phytotoxic preparation containing a known quantity of active component. The pan is then filled with the mixture and levelled. Watering is carried out by allowing the soil in the pan to absorb moisture through the perforated bottom of the pan.
Pannene som inneholder frø anbringes i en fuktig sandbenk og hol-des i 14 dager under vanlige betingelser for sollys og vanning. Plantene ut-tas etter 14 dager og resultatene opptegnes. Den fytotoksiske pre-emergente aktivitets indeks baseres på gjennomsnittlig spiringsprosent for hver frøandel. Aktivitetsindeksen omdannes til en relativ numerisk skala for korthetens og enkelhetens skyld i eksemplene. Pre-emergens fytotoksisk aktivitetsindeksen som brukes i de følgende eksempler defineres som følger: The pans containing seeds are placed in a moist sand bench and kept for 14 days under normal conditions of sunlight and watering. The plants are removed after 14 days and the results are recorded. The phytotoxic pre-emergent activity index is based on the average germination percentage for each seed proportion. The activity index is converted to a relative numerical scale for the sake of brevity and simplicity in the examples. The pre-emergence phytotoxic activity index used in the following examples is defined as follows:
Pre-emergens fytotoksisk aktivitet for noen av N-(l-cykloalken-1-yl)-oc -kloracetamidene som anvendes i preparatene etter nærværende oppfinnelse, er opptegnet i tabell I for forskjellige tilføringsmengder av aktivitets kompo-nentene både til overflate og til innarbeidelse i jorden. Uttrykkene "SA" og "SI" i kolonnen for påføringsmetoden betyr overflatetilføring hhv. innarbeidelse i jorden. I tabell I er de forskjellige plantefrø betegnet med bokstaver som følger: Pre-emergence phytotoxic activity for some of the N-(1-cycloalken-1-yl)-oc-chloroacetamides used in the preparations according to the present invention are recorded in Table I for different addition amounts of the active components both to the surface and for incorporation in the earth. The terms "SA" and "SI" in the column for the application method mean surface application or incorporation into the soil. In Table I, the different plant seeds are designated by letters as follows:
A - vanlig gress A - ordinary grass
B - bredbladede vekster B - broad-leaved plants
C - Iponioea C - Iponioea
D - floghavre D - spelled oats
E - Bromus E - Bromine
F - raigress (Lolium perenne) F - rye grass (Lolium perenne)
G - reddik G - radish
H - sukkerroe H - sugar beet
I - bomull J - hvete I - cotton J - wheat
K - revehale K - fox tail
Li - hønsehirse (Echinochloa crus-galli) Li - chicken millet (Echinochloa crus-galli)
M - hirse (Digitaria M - millet (Digitaria
N - meldestokk (Chenopodium quinoa) N - Chenopodium quinoa (Chenopodium quinoa)
O - soyabønne O - soybean
P - vill bokhvete P - wild buckwheat
Q - tomat Q - tomato
R - Durra S - ris R - Sorghum S - rice
T - Chenopodium album T - Chenopodium album
U - Sebania exaltata U - Sebania exaltata
Tallene i tabell I viser den generelle fytotoksiske aktivitet såvel som den selektive fytotoksiske aktivitet for representative preparater ifølge oppfinnelsen. Det vil bemerkes at usedvanlig spesifikitet overfor gress oppnås ved ekstremt lave anvendelsesmengder slik som f. eks. ved 1125 g/da med N-(l -cyklohexen-1 -yl) -N-isopropyl-et-kloracetamid og N-(l -cyklohexen-1 - yl)-N-(n-propyl) oc -kloracetamid. The figures in Table I show the general phytotoxic activity as well as the selective phytotoxic activity for representative preparations according to the invention. It will be noted that exceptional specificity towards grass is achieved at extremely low application amounts, such as e.g. at 1125 g/da with N-(1-cyclohexen-1-yl)-N-isopropyl-et-chloroacetamide and N-(1-cyclohexen-1-yl)-N-(n-propyl)oc-chloroacetamide.
Det vil også bemerkes at N-(l-cykloalken-1-yl) Ot -kloracetamid fytotoksiske midler etter nærværende oppfinnelse ikke. er begrenset til å fjerne gress fra bredbladede planter da deres selektive virning er slik at visse arter av gress fjernes fra mais som også er en gressart. Av tabell-ene fremgår det også at N-(l-cyklohexen-1 -yl) -N-allyl-ot-kloracetamid har særlig sterk virkning. Preparater som inneholder denne forbindelse, er der-for foretrukket. It will also be noted that N-(1-cycloalken-1-yl) O -chloroacetamide phytotoxic agents according to the present invention do not. are limited to removing grasses from broadleaf plants as their selective weeding is such that certain species of grasses are removed from maize which is also a grass species. The tables also show that N-(1-cyclohexen-1-yl)-N-allyl-o-chloroacetamide has a particularly strong effect. Preparations containing this compound are therefore preferred.
Mangelen av fytotoksisk aktivitet for ot-klo r acetamid er som er lignende N-(l-cykloalken-1-yl) Ot-kloracetamidene som anvendes i preparatene etter nærværende oppfinnelse vises som følger: Pre-emergens drivhusprøver anvendes og frøplantningsmetoden og påføringen av Ot -kloracetamid utføres på samme måte som i foran nevnte pre-emergens eksemplene. Resultater og ytterligere detaljer vises i tabell II. Identifikasjonen av frøene, den fytotoksiske aktivitetsindeks og symbolene for påføringen er de samme som de som er anvendt foran. The lack of phytotoxic activity for ot-chloroacetamide is similar to the N-(l-cycloalken-1-yl) ot-chloroacetamides used in the preparations according to the present invention are shown as follows: Pre-emergence greenhouse samples are used and the seeding method and application of Ot -chloroacetamide is carried out in the same way as in the aforementioned pre-emergence examples. Results and further details are shown in Table II. The identification of the seeds, the phytotoxic activity index and the symbols for the application are the same as those used above.
Det er fra britisk patent 781. 702 kjent at forbindelsen N-cykloheksyl-N-allyl- * -kloracetamid har herbicid virkning. It is known from British patent 781, 702 that the compound N-cyclohexyl-N-allyl-*-chloroacetamide has a herbicidal effect.
Videre vises til tysk utlegnings skrift 1.108.978, som vedrører N-sub-stituerte Ot -haloacetamider med formelen: Reference is also made to German publication 1,108,978, which relates to N-substituted Ot-haloacetamides with the formula:
hvor R betegner hydrogen eller et hydrokarbonradikal med 1-4 karbonatomer, R' betegner et alifatisk hydrokarbonradikal, hydrogen, alkoksyalkyl, benzyl,fenyl, furfuryl eller cykloheksylradikal, og X betegner klor, brom eller jod. Imidlertid er radikalet Y, som særmerker foreliggende oppfinnelse, forskjellig fra de tilsvarende substituenter til nitrogenet i det tyske patent. Y betegner som foran definert et cykloalkenylradikal med 5-7 karbonatomer. At de i-følge oppfinnelsen anvendte forbindelser er fordelaktige overfor de tidligere kjente forbindelsene (2), (4) og (6) fremgår av følgende tabell Hb. Norsk patentansøkning nr. 166.647 where R denotes hydrogen or a hydrocarbon radical with 1-4 carbon atoms, R' denotes an aliphatic hydrocarbon radical, hydrogen, alkoxyalkyl, benzyl, phenyl, furfuryl or cyclohexyl radical, and X denotes chlorine, bromine or iodine. However, the radical Y, which distinguishes the present invention, is different from the corresponding substituents for the nitrogen in the German patent. Y denotes, as defined above, a cycloalkenyl radical with 5-7 carbon atoms. That the compounds used according to the invention are advantageous compared to the previously known compounds (2), (4) and (6) appears from the following table Hb. Norwegian patent application no. 166,647
Forbindelse 90: N-(l-cykloheksen-1-yl) -N-fenyl- «--kloracetamid (N-(l -cykloheksen-1 -yl) - <%-kloracetanilid), Compound 90: N-(1-cyclohexen-1-yl)-N-phenyl-"--chloroacetamide (N-(1-cyclohexen-1-yl)-<%-chloroacetanilide),
Post-emergent fytotoksisk aktivitet for forskjellige N-(l-cykloalken-1-yl) Ot-kloracetamider som anvendes i preparatene ifølge nærværende oppfinnelse, vises som følger. De aktive komponenter påføres i forstøvet form Post-emergent phytotoxic activity for various N-(1-cycloalken-1-yl)O-chloroacetamides used in the preparations according to the present invention is shown as follows. The active components are applied in atomized form
til 21 dagers gamle eksemplarer av de samme planter som anvendes ved forannevnte pre-emergens-prøver . Den fytotoksiske sprøytevæske er en aceton-vann-oppløsning som inneholder 0,5 % aktive komponenter. Oppløsningen på-føres plantene i forskjellige sett av panner med en mengde som er tilnærmet 1125 g aktive komponenter pr. da. De behandlede planter anbringes i drivhus og virkningen iakttas og opptegnes etter 14 dager. to 21-day-old specimens of the same plants used in the aforementioned pre-emergence tests. The phytotoxic spray liquid is an acetone-water solution containing 0.5% active components. The solution is applied to the plants in different sets of pans with an amount that is approximately 1125 g of active components per then. The treated plants are placed in a greenhouse and the effect is observed and recorded after 14 days.
Post-emergens fytotoksisk aktivitetsindeksen som anvendes i de følgende eksempler er basert på gjennomsnittlig prosentvis skade på hver planteart og defineres som følger: The post-emergence phytotoxic activity index used in the following examples is based on the average percentage damage to each plant species and is defined as follows:
Identifikasjonen av plantene som anvendes er den samme som i foran nevnte pre-emergens prøvene. Resultatene og ytterligere detaljer er gjengitt i tabell III. The identification of the plants used is the same as in the aforementioned pre-emergence samples. The results and further details are reproduced in Table III.
Som angitt foran består de fytotoksiske preparater etter oppfinnelsen av en aktiv komponent og et eller flere fytotoksiske hjelpemidler som kan \were As indicated above, the phytotoxic preparations according to the invention consist of an active component and one or more phytotoxic aids which can be
faste eller flytende drivmidler, bærere, kondisj one ring smidler o.l. Foretrukne fytotoksiske preparater som inneholder de aktive komponenter etter nærværende oppfinnelse er blitt utviklet slik at de aktive komponenter kan anvendes med stør-ste fordel for å modifisere veksten av plantesystemer i jorden. De foretrukne preparater består av fuktbare pulvere, vandige suspensjoner, dustepulvere, granulater, emulgerbare oljer og oppløsninger i oppløsningsmidler. Vanlig- solid or liquid propellants, carriers, conditioning agents, etc. Preferred phytotoxic preparations containing the active components according to the present invention have been developed so that the active components can be used with the greatest advantage to modify the growth of plant systems in the soil. The preferred preparations consist of wettable powders, aqueous suspensions, dusting powders, granules, emulsifiable oils and solutions in solvents. Usual-
vis kan disse foretrukne preparater alle inneholde et eller flere overflateaktive midler. however, these preferred preparations may all contain one or more surfactants.
Overflateaktive midler som kan brukes i de fytotoksiske preparater etter oppfinnelsen angis f. eks. i U.S. patent 2 426 417, 2 655 447, 2 412 510 Surface-active agents that can be used in the phytotoxic preparations according to the invention are indicated, e.g. in the U.S. patent 2 426 417, 2 655 447, 2 412 510
og 2 139 276. En uttømmende liste over slike midler er også angitt av J. W. McCutcheon i "Soap and Chemical Specialties", November 1947, side 8011 et seq. , betegnet "Synthetic Detergents"; "Detergents and Emulsifiers - Up to Date" (1960) av J.W. McCutcheon, Inc. , og Bulletin E-607 av Bureau of Ento-mology and Plant Quarantine fra U.S.D.A. Vanligvis er mindre enn 10 vektsdeler av flere aktive midler tilstede pr. 100 vektsdeler fytotoksiske preparater. and 2,139,276. An exhaustive list of such agents is also provided by J. W. McCutcheon in "Soap and Chemical Specialties", November 1947, pages 8011 et seq. , designated "Synthetic Detergents"; "Detergents and Emulsifiers - Up to Date" (1960) by J.W. McCutcheon, Inc., and Bulletin E-607 of the Bureau of Entomology and Plant Quarantine of the U.S.D.A. Usually less than 10 parts by weight of several active agents are present per 100 parts by weight of phytotoxic preparations.
Fuktbare pulvere er vann-dispergerbare preparater som inneholder en eller flere aktive komponenter, et inert fast drøyemiddel og et eller flere fukt-nings- og dispergeringsmidler. De inerte faste drøyemidler er vanligvis av mineralsk opprinnelse, slik som de naturlige lerer, diatoméjord og syntetiske mineraler avledet fra siliciumoxyd o.l. Eksempler på slike drøyemidler omfatter kaoliniter, attapulgitlere og syntetisk magnesiumsilikat. Wettable powders are water-dispersible preparations that contain one or more active components, an inert solid suspending agent and one or more wetting and dispersing agents. The inert solid suspending agents are usually of mineral origin, such as the natural clays, diatomaceous earth and synthetic minerals derived from silicon oxide and the like. Examples of such retarding agents include kaolinites, attapulgites and synthetic magnesium silicate.
Foretrukne fuktningsmidler er alkylbenzen og alkylnaftalensulfonater, sulfaterte fettalkoholer, aminer eller syreamider , langkjedede syreestere av natrium isothionat, estere av natrium sulfosuccinat, sulfaterte eller sulfonerte fettsyreester e , petroleumsulfonater, sulfonaterte vegetabilske oljer og diter-tiære acetyl glycoler. Foretrukne dispergeringsmidler er methylcellulose, polyvinylalkohol, natriumligninsulfonater , polymere alkylnaftalensulfonater, natriumnaftalensulfonat, polymethylen-bisnaftalensulfonat og natrium N-methyl-N-(langkjedede syre) taurater. Preferred wetting agents are alkylbenzene and alkylnaphthalenesulfonates, sulfated fatty alcohols, amines or acid amides, long-chain acid esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils and ditertiary acetyl glycols. Preferred dispersants are methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalenesulfonates, sodium naphthalenesulfonate, polymethylene bisnaphthalenesulfonate and sodium N-methyl-N-(long chain acid) taurates.
De fuktbare pulverformede preparater etter oppfinnelsen inneholder vanligvis 25 - 90 vektdeler aktive komponenter, 0,25 - 3,0 vektdeler fuktningsmidler, 0*25 - 7 vektdeler dispergeringsmiddel og 9,5 - 74,5 vektdeler inerte faste drøyemidler, og alle deler er vektdeler av det totale preparat. Hvor nød-vendig kan 0, 1 - 2,0 vektdeler av det faste inerte drøyemiddel erstattes av et korrosjonshemmende eller anti-skum-middel eller begge deler. The wettable powder preparations according to the invention usually contain 25 - 90 parts by weight of active components, 0.25 - 3.0 parts by weight of wetting agents, 0*25 - 7 parts by weight of dispersing agent and 9.5 - 74.5 parts by weight of inert solid suspending agents, and all parts are parts by weight of the total preparation. Where necessary, 0.1 - 2.0 parts by weight of the solid inert suspending agent can be replaced by a corrosion-inhibiting or anti-foaming agent or both.
Vandige suspensjoner fremstilles ved å blande sammen og male en Aqueous suspensions are prepared by mixing and grinding a
Vandig oppslemning av den vann-uoppløselig aktive komponent i nærvær av dispergeringsmidler for å oppnå en konsentrert oppslemning av meget finfordelte partikler. Den resulterende konsentrerte vandige suspensjon karakteriseres ved ekstremt liten partikkelstørrelse slik at når den er fortynnet og sprøytes ut, er dekningen meget ensartet. Aqueous slurry of the water-insoluble active component in the presence of dispersants to obtain a concentrated slurry of very finely divided particles. The resulting concentrated aqueous suspension is characterized by extremely small particle size so that when diluted and sprayed, the coverage is very uniform.
Dustepulvere er tette, finfordelte partikulære preparater som er bestemt for innføring i jorden i tørr form. Dustepulvere karakteriseres ved deres frittflytende og hurtige avsetningsegenskaper slik at de ikke er lett vind-bårede i områder hvor de ikke har noen verdi. Dustepulvere inneholder pri-mært en aktiv komponent og et tett, f rittflytende, finfordelt, partikkelformet drøyemiddel. Imidlertid deres virkning hjelpes noen ganger ved innarbeidelsen av et fuktningsmiddel slik som den forannevnte liste under fuktningspul-verpreparater, og letthet ved fremstillingen krever hyppig innarbeidelsen av et inert absorberende formalings hjelpemiddel. Egnede klasser av malhings-hj el - pemidler er de naturlige lerer, diatomeholdig jord og syntetiske mineraler avledet fra silisiumoxyd og silikat. Foretrukne malningshjelpemidler omfatter attapulgitlere, diatomejordholdig silisiumoxyd, syntetisk fint silisiumoxyd og syntetisk kalsium og magnesiumsilikater. Dusting powders are dense, finely divided particulate preparations intended for introduction into the soil in dry form. Dusting powders are characterized by their free-flowing and rapid deposition properties so that they are not easily wind-borne in areas where they have no value. Dusting powders primarily contain an active component and a dense, free-flowing, finely divided, particulate suspending agent. However, their action is sometimes aided by the incorporation of a wetting agent such as those listed above under wetting powder preparations, and ease of manufacture often requires the incorporation of an inert absorbent grinding aid. Suitable classes of malhing aids are the natural clays, diatomaceous earth and synthetic minerals derived from silicon oxide and silicate. Preferred grinding aids include attapulgites, diatomaceous earth silica, synthetic fine silica, and synthetic calcium and magnesium silicates.
De inerte finfordelte faste drøyemidler for dustepulverne kan være av enten vegetabilsk eller mineralsk opprinnelse. De faste drøyemidler er karakterisert ved å ha relativt lite overflateareal og liten væskeabsorbsjon. Egnede inerte faste drøyemidler for fytotoksiske dustepulvere omfatter glimmeraktig talkum, pyrofyllit, tette kaolinlerer, malt kalsiumfosfat og tobakkstøv. Pulverne inneholder vanligvis fra 0.5 - 95 deler aktive komponenter, 0-50 deler formalingshjelpemidler , 0 - 3 deler fuktningsmiddel og 5 - 99 , 5 deler tette faste drøyemidler, og alle deler er vektdeler og basert på den totale vekt av pulverne. The inert finely divided solid emulsifiers for the dusting powders can be of either vegetable or mineral origin. The solid suspending agents are characterized by having a relatively small surface area and low liquid absorption. Suitable inert solid propellants for phytotoxic dusting powders include mica-like talc, pyrophyllite, dense kaolin clays, ground calcium phosphate and tobacco dust. The powders usually contain from 0.5 - 95 parts active components, 0-50 parts grinding aids, 0 - 3 parts wetting agent and 5 - 99, 5 parts dense solid thickening agents, and all parts are parts by weight and based on the total weight of the powders.
De fuktbare pulvere som beskrevet foran, kan også brukes ved frem-stilling av dustepulvere. Mens slike fuktbare pulvere kan brukes direkte i støv-form, er det meget fordelaktig å fortynne dem ved blanding med et tett støvende fortynningsmiddel. På denne måte kan også dispergerende midler, korrosjons-hemmere og anti-skum-midler finnes som komponent av et dustepulver . The wettable powders as described above can also be used in the production of dusting powders. While such wettable powders can be used directly in dust form, it is very advantageous to dilute them by mixing with a dense dusting diluent. In this way, dispersing agents, corrosion inhibitors and anti-foam agents can also be found as components of a dusting powder.
Emulgerende oljer er vanligvis oppløsninger av aktiv komponent i med vann ikke blandbare oppløsningsmidler sammen med et overflateaktivt middel. Egnede oppløsningsmidler for den aktive komponent etter nærværende oppfinnelse omfatter hydrokarboner og med vann ikke' blandbare ethere , estere eller ketoner. Egnede overflateaktive midler er anioniske, kationiske og ikke-ion-iske slik som alkyl-aryl-polyethoxy-alkoholer, alkyl og alkyl-aryl-polyether - alkoholer, polyethylensorbitol eller sorbitan-fettsyre-estere , polyethylengly-kpl-fettsyreestere, fettalkoholamidkondensater , aminsalter fra fettalkoholsul-fater sammen med langkjedede alkoholer og olj eoppløselige petroleumsulfonater eller blandinger derav. De emulgerbare oljepreparater inneholder vanligvis fra 5-95 deler aktive komponenter, ca. 1 - 10 deler overflateaktivt middel og ca. 4-94 deler oppløsningsmiddel og alle deler er etter vekt og basert på den totale vekt av emulgeringsolje. Emulsifying oils are usually solutions of the active component in water-immiscible solvents together with a surface-active agent. Suitable solvents for the active component according to the present invention include hydrocarbons and water-immiscible ethers, esters or ketones. Suitable surfactants are anionic, cationic and non-ionic such as alkyl-aryl-polyethoxy alcohols, alkyl and alkyl-aryl polyether alcohols, polyethylene sorbitol or sorbitan fatty acid esters, polyethylene glycol fatty acid esters, fatty alcohol amide condensates, amine salts from fatty alcohol sulphates together with long-chain alcohols and oil-soluble petroleum sulphonates or mixtures thereof. The emulsifiable oil preparations usually contain from 5-95 parts of active components, approx. 1 - 10 parts surfactant and approx. 4-94 parts solvent and all parts are by weight and based on the total weight of emulsifying oil.
Granulater er fysikalsk stabile partikkelformete preparater som inneholder den aktive komponent heftende til eller fordelt over en basisk bærer av et inert, finfordelt partikkelformet drøyemiddel. For å hjelpe utvaskning av den aktive komponent fra det partikkelformete middel, kan et overflateaktivt middel slik som den angitt foran under fuktningspulvere være tilstede i preparatet. Naturlige lerer , pyrofyllitter og vermikulit er eksempler på anvendelige arter av partikkelformede miner aldrøyemidler . De foretrukne drøyemidler er porøse, absorbtive, forutformede partikler slik som forut - formet og skjermet, partikkelformet attapulgit eller varme-ekspandert, partikkelformet vermikulit, og de finfordelte lerer slik som kaolinlerer, hydra-tisert attapulgit eller bentonitiske lerer. Disse drøyemidler sprøytes på eller blandes med den aktive komponent for å danne de fytotoksiske granulater. Granules are physically stable particulate preparations that contain the active component attached to or distributed over a basic carrier of an inert, finely divided particulate emollient. To aid leaching of the active component from the particulate agent, a surface-active agent such as that indicated above under wetting powders may be present in the preparation. Natural clays, pyrophyllites and vermiculite are examples of usable species of particulate mine alders. The preferred suspending agents are porous, absorbent, preformed particles such as preformed and screened particulate attapulgite or heat-expanded particulate vermiculite, and the finely divided clays such as kaolin clays, hydrated attapulgite, or bentonite clays. These wetting agents are sprayed on or mixed with the active component to form the phytotoxic granules.
Mineralpartiklene som anvendes i de granulerte fytotoksiske preparater etter nærværende oppfinnelse har vanligvis en størrelse på 10 - lOOmesh, men fortrinnsvis slik at den større del av partiklene er fra 14 til 60 mesh med den optimale størrelse fra 20 til 40 mesh. Lere som har i det vesentlige alle partikler mellom 14 og 80 mesh og minst ca. 80 prosent mellom 20 og 40 mesh er særlig foretrukket for anvendelse i de granulære preparater. Uttrykket "mesh" som anvendes her betyr US-siktserie. The mineral particles used in the granulated phytotoxic preparations according to the present invention usually have a size of 10 - 100 mesh, but preferably such that the larger part of the particles is from 14 to 60 mesh with the optimal size from 20 to 40 mesh. Clay that has essentially all particles between 14 and 80 mesh and at least approx. 80 percent between 20 and 40 mesh is particularly preferred for use in the granular preparations. The term "mesh" as used herein means US sieve series.
De granulære fytotoksiske preparater etter oppfinnelsen inneholder vanligvis 5-30 vektdeler N-(l - cykloalken-1-yl) o: -kloracetamid pr. 100 vektdeler lere og 0-5 vektdeler partikkelformet lere. De foretrukne fytotoksiske granu-latpreparater inneholder 10-25 vektdeler aktive komponenter pr. 100 vektdeler lere. The granular phytotoxic preparations according to the invention usually contain 5-30 parts by weight of N-(1-cycloalken-1-yl)o:-chloroacetamide per 100 parts by weight of clay and 0-5 parts by weight of particulate clay. The preferred phytotoxic granulate preparations contain 10-25 parts by weight of active components per 100 parts by weight of clay.
De fytotoksiske preparater ifølge nærværende oppfinnelse kan også inneholde andre tilsetninger, f. eks. gjødningsmidler , andre fytotoksiske midler.o.l. som hjelpemiddel eller i kombinasjon med noen av de ovennevnte hjelpemidler. Fytotoksiske midler som er anvendelig i kombinasjon med foran beskrevne forbindelser omfatter f. eks. 2, 4-diklorphenoxy-eddiksyre , 2 , 4 , 5-triklorfenoxy - eddiksyre, 2-methyl-4-klorfenoxy-eddiksyre og saltene, esterne og amidene derav, triazinderivater , slik som 2, 4-bis(3-methoxypropylamino)-6-methyl-thio-S-triazin, 2-klor-4-ethylamino-6-isopropylamino-S-triazin, og 2-ethyl-amino-4-isopropylamino-6-methylmercapto-S-triazin, ureaderivater slik som 3 r (3 , 4-diklorphenyl) -1,1 -dimethyl -urea og 3 - (p -klorphenyl) -1,1 -dimethyl -urea, åcetanilider slik som N-isopropyl-Ot -kloracetanilid og N-ethyl- Ot-klor-2-methylacetanilid og 2-tert-butyl-2'-klor-6-methylacetanilid, og acetamider slik som N,N-diallyl-tt -kloracetamid, N-( <* -kloracetyl)hexamethylenimin, The phytotoxic preparations according to the present invention may also contain other additives, e.g. fertilizers, other phytotoxic agents, etc. as an aid or in combination with any of the above aids. Phytotoxic agents which can be used in combination with the compounds described above include, e.g. 2, 4-dichlorophenoxy-acetic acid, 2, 4, 5-trichlorophenoxy-acetic acid, 2-methyl-4-chlorophenoxy-acetic acid and their salts, esters and amides, triazine derivatives, such as 2, 4-bis(3-methoxypropylamino)- 6-methyl-thio-S-triazine, 2-chloro-4-ethylamino-6-isopropylamino-S-triazine, and 2-ethyl-amino-4-isopropylamino-6-methylmercapto-S-triazine, urea derivatives such as 3 r (3,4-dichlorophenyl)-1,1-dimethyl-urea and 3-(p-chlorophenyl)-1,1-dimethyl-urea, acetanilides such as N-isopropyl-O-chloroacetanilide and N-ethyl-O-chloro -2-methylacetanilide and 2-tert-butyl-2'-chloro-6-methylacetanilide, and acetamides such as N,N-diallyl-tt -chloroacetamide, N-( <* -chloroacetyl)hexamethyleneimine,
og N, N-diethyl-<*-bromacetamid, o.l. Gjødningsmidler som er anvendelige i kombinasjon med de aktive komponenter omfatter f. eks. ammoniumnitrat, urea og superfosfat. Andre anvendelige tilsetninger omfatter materialer i hvilke planteorganismer slår rot og vokser slik som kompost, gjødsel, humus, s and o.l. and N,N-diethyl-<*-bromoacetamide, etc. Fertilizers that can be used in combination with the active components include e.g. ammonium nitrate, urea and superphosphate. Other usable additives include materials in which plant organisms take root and grow, such as compost, fertiliser, humus, sand and the like.
Når der arbeides i overensstemmelse med nærværende oppfinnelse, fordeles effektive mengder N-(l-cykloalken-1 -yl) -kloracetamider i jorden eller plantevekstmidler og påføres til de deler av planten som er over jorden på en hver egnet måte. Tilføring til jorden eller det voksende medium kan utføres ved enkel blanding med mediet ved å påføre til overflaten av jorden og deretter arbeide ned i jorden til den ønskede dybde, eller ved anvendelse av en flytende bærer for å utføre penetrering og impregnering. Anvendelsen av væske og partikkelformede faste fytotoksiske preparater til overflaten av jorden eller til plantene over jorden kan utføres på egnet måte f. eks. ved dus-, tepulvere og håndspredere og forstøvningsanordninger. Preparatene kan på-føres fra fly som et pulver eller støv på grunn av deres effektivitet ved lave doseringer. Ved ytterligere metode kan fordelingen av en aktiv komponent i jorden utføres ved blanding med vannet som anvendes for å irrigere jorden. Med slike måter kan vannmengden varieres med porøsiteten og vannbehold-ningskapasiteten av jorden for å oppnå den ønskede dybde av fordelingen av de fytotoksiske midler. When working in accordance with the present invention, effective amounts of N-(1-cycloalken-1-yl)-chloroacetamides are distributed in the soil or plant growth agents and applied to the parts of the plant that are above ground in a suitable manner. Application to the soil or growing medium can be accomplished by simple mixing with the medium by applying to the surface of the soil and then working into the soil to the desired depth, or by using a liquid carrier to effect penetration and impregnation. The application of liquid and particulate solid phytotoxic preparations to the surface of the soil or to the plants above the soil can be carried out in a suitable manner, e.g. by shower, tea powders and hand spreaders and atomizing devices. The preparations can be applied from aircraft as a powder or dust due to their effectiveness at low dosages. In a further method, the distribution of an active component in the soil can be carried out by mixing with the water used to irrigate the soil. With such means, the amount of water can be varied with the porosity and water-holding capacity of the soil to achieve the desired depth of distribution of the phytotoxic agents.
Tilføringen av en effektiv eller fytotoksisk mengde av N-(l-cyklo-alken-l-yl) «,-kloracetamidene som anvendes i preparatene ifølge oppfinnelsen, til jorden eller vekstmediet eller plantesystemet er vesentlig og kritisk. Den eksakte mengde av aktiv komponent som skal anvendes, er anhengig av The supply of an effective or phytotoxic amount of the N-(1-cyclo-alken-1-yl)-,-chloroacetamides used in the preparations according to the invention to the soil or the growth medium or the plant system is essential and critical. The exact amount of active component to be used depends on
det ønskede respons i planten såvel som andre faktorer som planteartene og disses utvikling, den spesielle jord og dybden til hvilken de aktive komponenter fordeles i jorden, og mengden av regn såvel som det spesifikke N-(l-cyk-loalken -1-yl) OC-kloracetamid som anvendes. Ved behandling av løv for kontroll eller modifikasjon av plantevekst påføres de aktive komponenter i mengder av 100 - 6000 eller mer g pr. da. Ved anvendelse i jord for kontroll eller modifikasjon av veksten for spirende frø, skytende stiklinger og etablert vegetasjon tilføres de aktive komponenter i mengder av 1 - 3000 eller mere g pr.da. Ved slik anvendelse i jord er det ønskelig at de aktive komponenter fordeles på en dybde på minst 5 mm. Ved selektiv pre-emergens anvendelse tilføres de aktive komponenter vanligvis i mengder av 1 - 600 g pr. da. Det antas at en the desired response in the plant as well as other factors such as the plant species and their development, the particular soil and the depth to which the active components are distributed in the soil, and the amount of rain as well as the specific N-(l-cycloalkene-1-yl) OC-chloroacetamide used. When treating leaves for control or modification of plant growth, the active components are applied in quantities of 100 - 6000 or more g per then. When used in soil to control or modify the growth of germinating seeds, sprouting cuttings and established vegetation, the active components are added in quantities of 1 - 3000 or more g per day. For such application in soil, it is desirable that the active components are distributed to a depth of at least 5 mm. In case of selective pre-emergence application, the active components are usually added in amounts of 1 - 600 g per then. It is assumed that a
fagmann på området lett kan bestemme ut fra denne beskrivelse inklusive eksemplene påføringsmengden for en hver spesiell situasjon. a person skilled in the field can easily determine from this description including the examples the amount of application for each particular situation.
Uttrykkene "jord" og "vekstmedia" anvendes i nærværende beskrivelse i bredeste forstand og inkluderer all konvensjonell "jord" slik som definert i Webster's New International Dictionary, Second Edition, Unabridged (l96l). Således henviser uttrykkene til en hver substans eller media i hvilke vegetasjon slår rot og vokser, og omfatter således ikke bare jord, men også kompost, gjødsel, myrjord, humus, sand o.l. med evne til å understøtte plantevekst . The terms "soil" and "growth media" are used in the present description in the broadest sense and include all conventional "soil" as defined in Webster's New International Dictionary, Second Edition, Unabridged (l96l). Thus, the expressions refer to each substance or media in which vegetation takes root and grows, and thus includes not only soil, but also compost, fertiliser, bog soil, humus, sand etc. with the ability to support plant growth.
Claims (2)
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NO822023A NO166647C (en) | 1982-06-17 | 1982-06-17 | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE SUBSTITUTED DIPEPTIDES. |
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NO822023A NO166647C (en) | 1982-06-17 | 1982-06-17 | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE SUBSTITUTED DIPEPTIDES. |
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NO822023L NO822023L (en) | 1983-12-19 |
NO166647B true NO166647B (en) | 1991-05-13 |
NO166647C NO166647C (en) | 1991-08-21 |
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NO822023A NO166647C (en) | 1982-06-17 | 1982-06-17 | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE SUBSTITUTED DIPEPTIDES. |
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NO166647C (en) | 1991-08-21 |
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