CA1063126A - 2-halobenzylethers - Google Patents

2-halobenzylethers

Info

Publication number: CA1063126A
Authority: CA; Canada
Prior art keywords: group; methyl; ethyl; formula; carbon atoms
Prior art date: 1974-09-23
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

CA233,345A

Other languages

English (en)

Other versions

CA233345S (en

Inventor

Peter Kirby

Eirlys R. Barker-Isaac

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.)

Shell Canada Ltd

Original Assignee

Shell Canada Ltd

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.)

1974-09-23

Filing date

1975-08-12

Publication date

1979-09-25

1975-08-12 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1979-09-25 Application granted granted Critical

1979-09-25 Publication of CA1063126A publication Critical patent/CA1063126A/fr

Status Expired legal-status Critical Current

Links

-1 polymethylene group Polymers 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
RKTMLPDIXLJDMA-UHFFFAOYSA-N 1-fluoro-2-[(2-fluorophenyl)methoxymethyl]benzene Chemical class FC1=CC=CC=C1COCC1=CC=CC=C1F RKTMLPDIXLJDMA-UHFFFAOYSA-N 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
241000196324 Embryophyta Species 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000005059 halophenyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
150000002009 diols Chemical class 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
238000002844 melting Methods 0.000 claims 2
230000008018 melting Effects 0.000 claims 2
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
125000005118 N-alkylcarbamoyl group Chemical group 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
239000000203 mixture Substances 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000002689 soil Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
238000009472 formulation Methods 0.000 description 5
230000002363 herbicidal effect Effects 0.000 description 5
231100000167 toxic agent Toxicity 0.000 description 5
239000003440 toxic substance Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000000654 additive Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
238000005507 spraying Methods 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
240000006240 Linum usitatissimum Species 0.000 description 2
235000004431 Linum usitatissimum Nutrition 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
241000219843 Pisum Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
239000011149 active material Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 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
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000007865 diluting Methods 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
235000004426 flaxseed Nutrition 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
150000004760 silicates Chemical class 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
235000019354 vermiculite Nutrition 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
241000743985 Alopecurus Species 0.000 description 1
241001621841 Alopecurus myosuroides Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
235000006463 Brassica alba Nutrition 0.000 description 1
244000056139 Brassica cretica Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
244000140786 Brassica hirta Species 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
244000192528 Chrysanthemum parthenium Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
235000017945 Matricaria Nutrition 0.000 description 1
235000007232 Matricaria chamomilla Nutrition 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
235000011096 Papaver Nutrition 0.000 description 1
240000001090 Papaver somniferum Species 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
235000007244 Zea mays Nutrition 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005036 alkoxyphenyl group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000007798 antifreeze agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
239000010426 asphalt Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000001175 calcium sulphate Substances 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000002361 compost Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
229940117360 ethyl pyruvate Drugs 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
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 1
150000002334 glycols Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 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
239000008268 mayonnaise Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000012184 mineral wax Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000003415 peat Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA233,345A 1974-09-23 1975-08-12 2-halobenzylethers Expired CA1063126A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB4131074A GB1521685A (en)	1974-09-23	1974-09-23	2-halobenzyl ethers

Publications (1)

Publication Number	Publication Date
CA1063126A true CA1063126A (fr)	1979-09-25

Family

ID=10419110

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA233,345A Expired CA1063126A (fr)	1974-09-23	1975-08-12	2-halobenzylethers

Country Status (12)

Country	Link
JP (1)	JPS5156449A (fr)
BE (1)	BE833582A (fr)
BR (1)	BR7506091A (fr)
CA (1)	CA1063126A (fr)
DD (1)	DD121595A5 (fr)
DE (1)	DE2542212A1 (fr)
ES (1)	ES441149A1 (fr)
FR (1)	FR2285387A1 (fr)
GB (1)	GB1521685A (fr)
IT (1)	IT1042758B (fr)
NL (1)	NL7511145A (fr)
SU (1)	SU587839A3 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0046488A3 (fr) *	1980-07-28	1982-06-02	Hüls Troisdorf Aktiengesellschaft	Trioxa-2,5,7 bicyclo(2.2.2)octanones-6 et trioxa-3,6,8 bicyclo(3.2.1)octanones-4 substituées, dérivés d'acides dioxanne-1,3 carboxyliques et dioxolanne-1,3 carboxyliques-2, ainsi que leur préparation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE756427A (fr) *	1969-09-23	1971-03-22	Shell Int Research
GB1469530A (en) *	1973-07-03	1977-04-06	Shell Int Research	1,3-dioxolane-2-carboxamide derivatives and their use as herbicidal agents

1974
- 1974-09-23 GB GB4131074A patent/GB1521685A/en not_active Expired
1975
- 1975-08-12 CA CA233,345A patent/CA1063126A/fr not_active Expired
- 1975-09-19 BE BE1006890A patent/BE833582A/xx unknown
- 1975-09-22 BR BR7506091A patent/BR7506091A/pt unknown
- 1975-09-22 NL NL7511145A patent/NL7511145A/xx not_active Application Discontinuation
- 1975-09-22 FR FR7528950A patent/FR2285387A1/fr active Granted
- 1975-09-22 IT IT2750875A patent/IT1042758B/it active
- 1975-09-22 JP JP11379475A patent/JPS5156449A/ja active Pending
- 1975-09-22 SU SU752172109A patent/SU587839A3/ru active
- 1975-09-22 DD DD18848375A patent/DD121595A5/xx unknown
- 1975-09-22 DE DE19752542212 patent/DE2542212A1/de not_active Withdrawn
- 1975-09-22 ES ES441149A patent/ES441149A1/es not_active Expired

Also Published As

Publication number	Publication date
AU8505875A (en)	1977-03-31
BE833582A (nl)	1976-03-19
GB1521685A (en)	1978-08-16
DD121595A5 (fr)	1976-08-12
SU587839A3 (ru)	1978-01-05
BR7506091A (pt)	1976-08-03
JPS5156449A (en)	1976-05-18
IT1042758B (it)	1980-01-30
ES441149A1 (es)	1977-07-01
DE2542212A1 (de)	1976-04-08
NL7511145A (nl)	1976-03-25
FR2285387A1 (fr)	1976-04-16
FR2285387B1 (fr)	1979-01-05

Publication	Publication Date	Title
PL140539B1 (en)	1987-05-30	Plant growth controlling herbicide and method of obtaining novel derivatives of cyclohexanodionocarboxylic acid
DK145891B (da)	1983-04-05	N-substituerede halogen-2-pyrrolidinoner til anvendelse i herbicider samt fremgangsmaade til fremstilling deraf
US4116669A (en)	1978-09-26	Herbicidal tetrahydrofuran derivatives
CS223978B2 (en)	1983-11-25	Herbicide means
IL35165A (en)	1974-10-22	2-alkyl-glycerol derivatives,their preparation and herbicidal compositions containing them
EP0310186B1 (fr)	1992-07-15	Dérivés oximino éther
RU2015970C1 (ru)	1994-07-15	Производные пиримидина, обладающие гербицидной активностью, способ борьбы с нежелательной растительностью
KR920005411B1 (ko)	1992-07-03	치환된 테트라졸의 제법
AU606890B2 (en)	1991-02-21	Diphenyl ether herbicides
GB2050168A (en)	1981-01-07	Ethynyl compounds as herbicides
AU625390B2 (en)	1992-07-09	Diphenyl ether herbicides
EP0182407B1 (fr)	1990-05-16	Acides et esters alpha-aminooxy-C4-alcanoiques
US4400198A (en)	1983-08-23	Herbicidal tetrahydrofuran derivatives
US4249933A (en)	1981-02-10	Herbicidal agents containing a thiolcarbamate
CA1088089A (fr)	1980-10-21	Esters d'oxime de phenylalanine
EP0184256B1 (fr)	1989-10-18	Diphényléthers herbicides
US3986860A (en)	1976-10-19	Cyclic acetals of alpha-oxocarboxylic acid derivatives
EP0002842A1 (fr)	1979-07-11	Dérivés de l'acide thiopropionique, compositions herbicides et/ou régulatrices de la croissance des plantes les contenant et méthodes pour contrôler la croissance des plantes indésirables
CA1062260A (fr)	1979-09-11	Derives n'n-disubstitues de l'analine
US5508251A (en)	1996-04-16	Herbicidal methods and compositions comprising epoxy compounds
US3993698A (en)	1976-11-23	Herbicidal 2-alkyl glycerol derivatives
GB1602046A (en)	1981-11-04	Herbicidal a-fluorophenylacetic acid derivatives and their use
US4042369A (en)	1977-08-16	Compositions and methods of combatting weeds in crops with 2,6-dihalobenzyl ether
GB2035309A (en)	1980-06-18	Diphenyl esters and herbicidal compositions containing them
EP0261710B1 (fr)	1990-05-23	Herbicides de phénylurée