CA2314121A1

CA2314121A1 - Derive de l'acide salicylique et son utilisation en tant qu'intermediaire pour la preparation de derive salicylaldehyde

Derive de l'acide salicylique et son utilisation en tant qu'intermediaire pour la preparation de derive salicylaldehyde Download PDF

Info

Publication number: CA2314121A1
Authority: CA; Canada
Prior art keywords: alkyl; carry; halogen atoms; haloalkyl; radicals
Prior art date: 1989-06-14
Legal status : Abandoned

Application number

CA002314121A

Other languages

English (en)

Inventor

Uwe Josef Vogelbacher

Karl Eicken

Joachim Rheinheimer

Norbert Goetz

Albrecht Harreus

Gerhard Paul

Karl-Otto Westphalen

Bruno Wuerzer

Current Assignee

BASF SE

Original Assignee

Individual

Priority date

1989-06-14

Filing date

1990-06-13

Publication date

1990-12-14

1989-06-14 Priority claimed from DE3919435A external-priority patent/DE3919435A1/de

1990-06-13 Application filed by Individual filed Critical Individual

1990-12-14 Publication of CA2314121A1 publication Critical patent/CA2314121A1/fr

Status Abandoned legal-status Critical Current

Links

150000003872 salicylic acid derivatives Chemical class 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title abstract description 13
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 title abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
239000011593 sulfur Substances 0.000 claims abstract description 7
125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
125000005493 quinolyl group Chemical group 0.000 claims abstract description 5
125000001544 thienyl group Chemical group 0.000 claims abstract description 5
-1 C1-C4-alkylthio Chemical group 0.000 claims description 183
125000005843 halogen group Chemical group 0.000 claims description 44
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
150000002367 halogens Chemical group 0.000 claims description 13
229910052783 alkali metal Inorganic materials 0.000 claims description 11
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 8
150000001340 alkali metals Chemical class 0.000 claims description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
150000001342 alkaline earth metals Chemical class 0.000 claims description 4
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical compound [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 description 43
239000000203 mixture Substances 0.000 description 33
241000196324 Embryophyta Species 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000000243 solution Substances 0.000 description 29
150000003254 radicals Chemical class 0.000 description 28
239000004480 active ingredient Substances 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
238000000034 method Methods 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 12
239000003630 growth substance Substances 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 11
235000017168 chlorine Nutrition 0.000 description 11
229940060038 chlorine Drugs 0.000 description 11
230000012010 growth Effects 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
238000003756 stirring Methods 0.000 description 11
238000011282 treatment Methods 0.000 description 11
150000003839 salts Chemical class 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
244000038559 crop plants Species 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
239000011737 fluorine Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
239000012043 crude product Substances 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
150000002431 hydrogen Chemical group 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
239000002689 soil Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
230000002363 herbicidal effect Effects 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
235000013399 edible fruits Nutrition 0.000 description 6
239000007789 gas Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
ITDVJJVNAASTRS-UHFFFAOYSA-N 4,6-dimethoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CC(OC)=NC(S(C)(=O)=O)=N1 ITDVJJVNAASTRS-UHFFFAOYSA-N 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
125000004414 alkyl thio group Chemical group 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
229960001760 dimethyl sulfoxide Drugs 0.000 description 5
239000004009 herbicide Substances 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000000843 powder Substances 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
244000299507 Gossypium hirsutum Species 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
240000008042 Zea mays Species 0.000 description 4
235000002017 Zea mays subsp mays Nutrition 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
239000004359 castor oil Substances 0.000 description 4
229960001777 castor oil Drugs 0.000 description 4
235000019438 castor oil Nutrition 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
125000001072 heteroaryl group Chemical group 0.000 description 4
239000005457 ice water Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
230000008569 process Effects 0.000 description 4
229940083608 sodium hydroxide Drugs 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
229910052720 vanadium Inorganic materials 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010582 Pisum sativum Nutrition 0.000 description 3
240000004713 Pisum sativum Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000011575 calcium Substances 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000008504 concentrate Nutrition 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
230000009746 freeze damage Effects 0.000 description 3
238000007429 general method Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000004438 haloalkoxy group Chemical group 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
150000002440 hydroxy compounds Chemical class 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
150000002790 naphthalenes Chemical class 0.000 description 3
239000006072 paste Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
230000008635 plant growth Effects 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
241000894007 species Species 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003463 sulfur Chemical class 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
125000004743 1-methylethoxycarbonyl group Chemical group CC(C)OC(=O)* 0.000 description 2
YFQUUTHSRAMYCN-UHFFFAOYSA-N 2-(4,6-dimethoxypyrimidin-2-yl)oxy-6-(1,2,4-triazol-1-yl)benzoic acid Chemical compound COC1=CC(OC)=NC(OC=2C(=C(C=CC=2)N2N=CN=C2)C(O)=O)=N1 YFQUUTHSRAMYCN-UHFFFAOYSA-N 0.000 description 2
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
YPMSIWYNTPSPMV-UHFFFAOYSA-N 2-fluoro-6-methoxybenzonitrile Chemical compound COC1=CC=CC(F)=C1C#N YPMSIWYNTPSPMV-UHFFFAOYSA-N 0.000 description 2
PFAKRVWIAMBGIR-UHFFFAOYSA-N 2-methoxy-6-(1,2,4-triazol-1-yl)benzamide Chemical class COC1=CC=CC(N2N=CN=C2)=C1C(N)=O PFAKRVWIAMBGIR-UHFFFAOYSA-N 0.000 description 2
PPANHTQOMIEQJW-UHFFFAOYSA-N 2-methoxy-6-(1,2,4-triazol-1-yl)benzoic acid Chemical class COC1=CC=CC(N2N=CN=C2)=C1C(O)=O PPANHTQOMIEQJW-UHFFFAOYSA-N 0.000 description 2
BGGKKMWCAVQJBU-UHFFFAOYSA-N 2-methoxy-6-pyrazol-1-ylbenzoic acid Chemical class COC1=CC=CC(N2N=CC=C2)=C1C(O)=O BGGKKMWCAVQJBU-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 description 2
125000006050 3-methyl-2-pentenyl group Chemical group 0.000 description 2
241000218642 Abies Species 0.000 description 2
244000291564 Allium cepa Species 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
235000003840 Amygdalus nana Nutrition 0.000 description 2
244000105624 Arachis hypogaea Species 0.000 description 2
235000021537 Beetroot Nutrition 0.000 description 2
241000335053 Beta vulgaris Species 0.000 description 2
235000011297 Brassica napobrassica Nutrition 0.000 description 2
240000002791 Brassica napus Species 0.000 description 2
235000011293 Brassica napus Nutrition 0.000 description 2
240000000385 Brassica napus var. napus Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
235000003222 Helianthus annuus Nutrition 0.000 description 2
244000043261 Hevea brasiliensis Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
240000004658 Medicago sativa Species 0.000 description 2
235000004357 Mentha x piperita Nutrition 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
240000007817 Olea europaea Species 0.000 description 2
235000007195 Pennisetum typhoides Nutrition 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
235000011432 Prunus Nutrition 0.000 description 2
241000220299 Prunus Species 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
241001506137 Rapa Species 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
240000006394 Sorghum bicolor Species 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
244000299461 Theobroma cacao Species 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000001464 adherent effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000000969 carrier Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229940117916 cinnamic aldehyde Drugs 0.000 description 2
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
235000020971 citrus fruits Nutrition 0.000 description 2
239000007859 condensation product Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000006378 damage Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
244000013123 dwarf bean Species 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
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235000013526 red clover Nutrition 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
210000000614 rib Anatomy 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
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230000007017 scission Effects 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([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
238000004904 shortening Methods 0.000 description 1
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235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000021012 strawberries Nutrition 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
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239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
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150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
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125000000335 thiazolyl group Chemical group 0.000 description 1
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125000001425 triazolyl group Chemical group 0.000 description 1
LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
230000008511 vegetative development Effects 0.000 description 1
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239000011701 zinc Substances 0.000 description 1
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