CA1056204A - Procede pour faciliter le detachement des fruits - Google Patents

Procede pour faciliter le detachement des fruits

Info

Publication number: CA1056204A
Authority: CA; Canada
Prior art keywords: alkyl; hydrogen; phenylalkyl; alkylcarbamoyl; alkoxycarbonyl
Prior art date: 1972-07-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA177,507A

Other languages

English (en)

Other versions

CA177507S (en

Inventor

Merrill Wilcox

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

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

1972-07-27

Filing date

1973-07-27

Publication date

1979-06-12

1973-07-27 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1979-06-12 Application granted granted Critical

1979-06-12 Publication of CA1056204A publication Critical patent/CA1056204A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 22
230000008569 process Effects 0.000 title claims abstract description 19
230000028245 fruit abscission Effects 0.000 title claims abstract description 11
-1 C2-C5 alken-yl Chemical group 0.000 claims abstract description 38
239000001257 hydrogen Substances 0.000 claims abstract description 29
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
150000003839 salts Chemical class 0.000 claims abstract description 26
150000001875 compounds Chemical class 0.000 claims abstract description 23
235000013399 edible fruits Nutrition 0.000 claims abstract description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 19
150000002431 hydrogen Chemical group 0.000 claims abstract description 18
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 18
125000004691 alkyl thio carbonyl group Chemical group 0.000 claims abstract description 17
125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 17
125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 15
125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims abstract description 13
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 13
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 9
231100001184 nonphytotoxic Toxicity 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical group 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract 2
LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical compound O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 claims description 20
239000013543 active substance Substances 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 12
241000196324 Embryophyta Species 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
238000003306 harvesting Methods 0.000 claims description 8
235000020971 citrus fruits Nutrition 0.000 claims description 6
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
KTQVJAPIQPIIPF-IOBHVTPZSA-N (1Z,2Z)-N,N'-dihydroxyethanediimidoyl dichloride Chemical compound O\N=C(/Cl)\C(\Cl)=N\O KTQVJAPIQPIIPF-IOBHVTPZSA-N 0.000 claims description 2
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
241000207199 Citrus Species 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052748 manganese Inorganic materials 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
150000001340 alkali metals Chemical class 0.000 claims 1
JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 claims 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
230000006578 abscission Effects 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
238000009835 boiling Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
230000009471 action Effects 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
150000002923 oximes Chemical class 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000002689 soil Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000011161 development Methods 0.000 description 3
230000018109 developmental process Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000012360 testing method Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
241000257303 Hymenoptera Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical group C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
FYFYCAVDUPOEOO-HNQUOIGGSA-N (ne)-n-(2-nitroethylidene)hydroxylamine Chemical compound O\N=C\C[N+]([O-])=O FYFYCAVDUPOEOO-HNQUOIGGSA-N 0.000 description 1
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
244000099147 Ananas comosus Species 0.000 description 1
235000007119 Ananas comosus Nutrition 0.000 description 1
241000167854 Bourreria succulenta Species 0.000 description 1
101100275770 Caenorhabditis elegans cri-3 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
235000005976 Citrus sinensis Nutrition 0.000 description 1
240000002319 Citrus sinensis Species 0.000 description 1
240000000560 Citrus x paradisi Species 0.000 description 1
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
101000760663 Hololena curta Mu-agatoxin-Hc1a Proteins 0.000 description 1
101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
244000141359 Malus pumila Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
241000207836 Olea <angiosperm> Species 0.000 description 1
101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
240000006365 Vitis vinifera Species 0.000 description 1
235000014787 Vitis vinifera Nutrition 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
159000000013 aluminium salts Chemical class 0.000 description 1
229910000329 aluminium sulfate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000021016 apples Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
235000021028 berry Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000007767 bonding agent Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000019693 cherries Nutrition 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000004660 morphological change Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
JMASXNZVWWFJRF-UHFFFAOYSA-N n-(2-chloroethylidene)hydroxylamine Chemical compound ON=CCCl JMASXNZVWWFJRF-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
125000003544 oxime group Chemical group 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
230000037390 scarring Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

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

CA177,507A 1972-07-27 1973-07-27 Procede pour faciliter le detachement des fruits Expired CA1056204A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US27565772A	1972-07-27	1972-07-27

Publications (1)

Publication Number	Publication Date
CA1056204A true CA1056204A (fr)	1979-06-12

Family

ID=23053304

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA177,507A Expired CA1056204A (fr)	1972-07-27	1973-07-27	Procede pour faciliter le detachement des fruits
CA220,722A Expired CA1014555A (en)	1972-07-27	1975-02-25	Process for the promotion and facilitation of fruit abscission

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA220,722A Expired CA1014555A (en)	1972-07-27	1975-02-25	Process for the promotion and facilitation of fruit abscission

Country Status (2)

Country	Link
CA (2)	CA1056204A (fr)
TR (1)	TR17881A (fr)

1973
- 1973-07-27 CA CA177,507A patent/CA1056204A/fr not_active Expired
- 1973-07-27 TR TR17881A patent/TR17881A/xx unknown
1975
- 1975-02-25 CA CA220,722A patent/CA1014555A/en not_active Expired

Also Published As

Publication number	Publication date
TR17881A (tr)	1976-09-01
CA1014555A (en)	1977-07-26

Publication	Publication Date	Title
US4052194A (en)	1977-10-04	Oxime abscission agents
US4479900A (en)	1984-10-30	1-Carbalkoxyalkyl-3-aryloxy-4-(2'-carboxyphenyl)-azetidin-2-ones
JPS6254103B2 (fr)	1987-11-13
UA45941C2 (uk)	2002-05-15	Композиція для дефоліації рослин та спосіб дефоліації рослин
JPWO1998055460A1 (ja)	2000-12-19	４−キノリノール誘導体及びこれを有効成分として含有する農園芸用殺菌剤
WO2011153865A1 (fr)	2011-12-15	3-ortho-méthylphényl-2-oxo-1-oxaspiro[4,4]non-3-èn-4-ol comportant une activité biologique, ses dérivés et son procédé de préparation
US4070481A (en)	1978-01-24	Substituted 2-higher alkyl-3-hydroxy-1,4-naphthoquinone carboxylic acid esters and their use as miticides
US4045459A (en)	1977-08-30	Agent for the regulation of plant growth
IL42831A (en)	1977-04-29	Process and compositions containing certain oxime derivatives and novel glyoximes for the facilitation of the abscission and ripening of fruit
US4013444A (en)	1977-03-22	Inhibiting grass growth with 5-acetamido-2,4-dimethyltrifluoromethanesulfonanilide
CA1056204A (fr)	1979-06-12	Procede pour faciliter le detachement des fruits
CA1132583A (fr)	1982-09-28	Imides de l'acide cyclobutanedicarboxylique, procedes pour les fabriquer, et leur utilisation comme fongicides
US4102668A (en)	1978-07-25	β-Halogenoethyl-silanes as plant growth regulators
CN117402170A (zh)	2024-01-16	一种喹啉类化合物及其制备方法和应用
EP0093384B1 (fr)	1986-06-11	Dérivés de thiophène et composition fongicide les contenant
CA1053247A (fr)	1979-04-24	Agents de germination
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