CA1069537A - Benzophenones substitues - Google Patents

Benzophenones substitues

Info

Publication number: CA1069537A
Authority: CA; Canada
Prior art keywords: compound; lower alkyl; alkyl group; general formula; group
Prior art date: 1971-08-24
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

CA272,797A

Other languages

English (en)

Inventor

Akira Kurozumi

Osamu Yamada

Hiroshi Yamamoto

Kensaku Ito

Fumio Futatsuya

Shuichi Ishida

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.)

Nippon Kayaku Co Ltd

Original Assignee

Nippon Kayaku Co 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.)

1971-08-24

Filing date

1977-02-28

Publication date

1980-01-08

1971-08-24 Priority claimed from JP46064658A external-priority patent/JPS515446B2/ja

1977-02-28 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1977-02-28 Priority to CA272,797A priority Critical patent/CA1069537A/fr

1980-01-08 Application granted granted Critical

1980-01-08 Publication of CA1069537A publication Critical patent/CA1069537A/fr

Status Expired legal-status Critical Current

Links

239000012965 benzophenone Substances 0.000 title 1
150000008366 benzophenones Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 73
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
230000008635 plant growth Effects 0.000 claims abstract description 15
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 9
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 8
230000001105 regulatory effect Effects 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 claims description 7
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
230000005764 inhibitory process Effects 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 5
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
230000012010 growth Effects 0.000 claims description 3
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims description 2
239000011592 zinc chloride Substances 0.000 claims description 2
235000005074 zinc chloride Nutrition 0.000 claims description 2
241000195493 Cryptophyta Species 0.000 claims 1
230000009074 negative regulation of seed germination Effects 0.000 claims 1
238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 4
230000005494 condensation Effects 0.000 abstract 1
238000009833 condensation Methods 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 30
239000000203 mixture Substances 0.000 description 24
230000002363 herbicidal effect Effects 0.000 description 16
240000007594 Oryza sativa Species 0.000 description 14
239000002689 soil Substances 0.000 description 13
238000011282 treatment Methods 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
235000007164 Oryza sativa Nutrition 0.000 description 12
235000009566 rice Nutrition 0.000 description 12
208000027418 Wounds and injury Diseases 0.000 description 9
230000006378 damage Effects 0.000 description 9
208000014674 injury Diseases 0.000 description 9
239000004480 active ingredient Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
244000058871 Echinochloa crus-galli Species 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000003621 irrigation water Substances 0.000 description 6
239000012876 carrier material Substances 0.000 description 5
238000011835 investigation Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 5
-1 2,3',5'-trimethyl-4-methoxybenzophenone Chemical compound 0.000 description 4
230000035784 germination Effects 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 4
241000634867 Eleocharis uniglumis Species 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
235000021186 dishes Nutrition 0.000 description 3
239000003337 fertilizer Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
238000002054 transplantation Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
240000008575 Ammannia baccifera Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000722895 Callitriche Species 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
235000002848 Cyperus flabelliformis Nutrition 0.000 description 2
240000001505 Cyperus odoratus Species 0.000 description 2
235000001248 Dentaria laciniata Nutrition 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
240000007038 Lindernia dubia Species 0.000 description 2
235000003990 Monochoria hastata Nutrition 0.000 description 2
240000000178 Monochoria vaginalis Species 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 2
SZXCCXFNQHQRGF-UHFFFAOYSA-N di(propan-2-yloxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)OP(S)(=S)OC(C)C SZXCCXFNQHQRGF-UHFFFAOYSA-N 0.000 description 2
239000000428 dust Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
208000037974 severe injury Diseases 0.000 description 2
230000009528 severe injury Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
PXCFVJKIUZFOBB-UHFFFAOYSA-N (3,4-dimethylphenyl)-(4-methoxy-3-methylphenyl)methanone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=C(C)C(C)=C1 PXCFVJKIUZFOBB-UHFFFAOYSA-N 0.000 description 1
USLLBSBMCWXMDV-UHFFFAOYSA-N (3,5-dimethylphenyl)-(4-methoxy-3-methylphenyl)methanone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC(C)=CC(C)=C1 USLLBSBMCWXMDV-UHFFFAOYSA-N 0.000 description 1
YPQPOBMMKCTTSS-UHFFFAOYSA-N (3-chloro-4-methoxyphenyl)-(4-methylphenyl)methanone Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)C1=CC=C(C)C=C1 YPQPOBMMKCTTSS-UHFFFAOYSA-N 0.000 description 1
YXHWDTFELQGMHC-UHFFFAOYSA-N (4-butylphenyl)-(4-methoxy-3-methylphenyl)methanone Chemical compound C1=CC(CCCC)=CC=C1C(=O)C1=CC=C(OC)C(C)=C1 YXHWDTFELQGMHC-UHFFFAOYSA-N 0.000 description 1
WZGSCYGKCLQNIY-UHFFFAOYSA-N (4-ethoxy-2-methylphenyl)-(3-methylphenyl)methanone Chemical compound CC1=CC(OCC)=CC=C1C(=O)C1=CC=CC(C)=C1 WZGSCYGKCLQNIY-UHFFFAOYSA-N 0.000 description 1
VFZTVBCRUWBKJP-UHFFFAOYSA-N (4-ethoxy-3-methylphenyl)-(3-methylphenyl)methanone Chemical compound C1=C(C)C(OCC)=CC=C1C(=O)C1=CC=CC(C)=C1 VFZTVBCRUWBKJP-UHFFFAOYSA-N 0.000 description 1
BTLBJCJZLLBALM-UHFFFAOYSA-N (4-ethylphenyl)-(4-methoxy-3-methylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)C1=CC=C(OC)C(C)=C1 BTLBJCJZLLBALM-UHFFFAOYSA-N 0.000 description 1
GVJONPIVJYQGFK-UHFFFAOYSA-N (4-methoxy-2-methylphenyl)-(3-methylphenyl)methanone Chemical compound CC1=CC(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 GVJONPIVJYQGFK-UHFFFAOYSA-N 0.000 description 1
DYOYUSFOYASYEL-UHFFFAOYSA-N (4-methoxy-2-methylphenyl)-(4-methylphenyl)methanone Chemical compound CC1=CC(OC)=CC=C1C(=O)C1=CC=C(C)C=C1 DYOYUSFOYASYEL-UHFFFAOYSA-N 0.000 description 1
OJUHYBHGOJCPDF-UHFFFAOYSA-N (4-methoxy-3-methylphenyl)-(2-methylphenyl)methanone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC=C1C OJUHYBHGOJCPDF-UHFFFAOYSA-N 0.000 description 1
NHNDQYASMVHSNF-UHFFFAOYSA-N (4-methoxy-3-methylphenyl)-(3-propylphenyl)methanone Chemical compound CCCC1=CC=CC(C(=O)C=2C=C(C)C(OC)=CC=2)=C1 NHNDQYASMVHSNF-UHFFFAOYSA-N 0.000 description 1
ADJSCMQXCLCSEH-UHFFFAOYSA-N (4-methoxy-3-methylphenyl)-(4-methylphenyl)methanone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=C(C)C=C1 ADJSCMQXCLCSEH-UHFFFAOYSA-N 0.000 description 1
UPMCXBZHLHKJKO-UHFFFAOYSA-N (4-methoxy-3-propan-2-ylphenyl)-(3-methylphenyl)methanone Chemical compound C1=C(C(C)C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 UPMCXBZHLHKJKO-UHFFFAOYSA-N 0.000 description 1
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical class C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
YHOYYHYBFSYOSQ-UHFFFAOYSA-N 3-methylbenzoyl chloride Chemical compound CC1=CC=CC(C(Cl)=O)=C1 YHOYYHYBFSYOSQ-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
244000055702 Amaranthus viridis Species 0.000 description 1
235000004135 Amaranthus viridis Nutrition 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000011293 Brassica napus Nutrition 0.000 description 1
235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
208000018380 Chemical injury Diseases 0.000 description 1
235000009344 Chenopodium album Nutrition 0.000 description 1
235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
235000009332 Chenopodium rubrum Nutrition 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
235000017896 Digitaria Nutrition 0.000 description 1
241001303487 Digitaria <clam> Species 0.000 description 1
235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
240000003176 Digitaria ciliaris Species 0.000 description 1
235000017898 Digitaria ciliaris Nutrition 0.000 description 1
235000005476 Digitaria cruciata Nutrition 0.000 description 1
235000006830 Digitaria didactyla Nutrition 0.000 description 1
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
241000144035 Eleocharis baldwinii Species 0.000 description 1
235000014716 Eleusine indica Nutrition 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241001523358 Glyceria Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
241000241602 Gossypianthus Species 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
MOMWFXLCFJOAFX-UHFFFAOYSA-N OOOOOOOO Chemical compound OOOOOOOO MOMWFXLCFJOAFX-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000005791 algae growth Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
238000009313 farming Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
244000037666 field crops Species 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
208000006278 hypochromic anemia Diseases 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000005286 illumination Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
235000003267 mannagrass Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
BOIGFJNPJFOCRH-UHFFFAOYSA-N n,n-diethyl-1,3,5-triazin-2-amine Chemical compound CCN(CC)C1=NC=NC=N1 BOIGFJNPJFOCRH-UHFFFAOYSA-N 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000007226 seed germination Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
229940082004 sodium laurate Drugs 0.000 description 1
JXIRGOVTQVCGKR-UHFFFAOYSA-M sodium;dinaphthalen-1-ylmethanesulfonate Chemical compound [Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)S(=O)(=O)[O-])=CC=CC2=C1 JXIRGOVTQVCGKR-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000020681 well water Nutrition 0.000 description 1
239000002349 well water Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA272,797A 1971-08-24 1977-02-28 Benzophenones substitues Expired CA1069537A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA272,797A CA1069537A (fr)	1971-08-24	1977-02-28	Benzophenones substitues

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP46064658A JPS515446B2 (fr)	1971-08-24	1971-08-24
CA150,094A CA1025688A (fr)	1971-08-24	1972-08-24	Regulateurs de croissance vegetale
CA272,797A CA1069537A (fr)	1971-08-24	1977-02-28	Benzophenones substitues

Publications (1)

Publication Number	Publication Date
CA1069537A true CA1069537A (fr)	1980-01-08

Family

ID=27162235

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA272,797A Expired CA1069537A (fr)	1971-08-24	1977-02-28	Benzophenones substitues

Country Status (1)

Country	Link
CA (1)	CA1069537A (fr)

1977
- 1977-02-28 CA CA272,797A patent/CA1069537A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-01-08	MKEX	Expiry

Publication	Publication Date	Title
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US4338122A (en)	1982-07-06	Biocidal 2-aryl-1,3-cyclopentanedione compounds and alkali metal and ammonium salts thereof
CA1059125A (fr)	1979-07-24	Herbicide de type n-haloacetyl-1,2-dihydro-4h-3,1-benzoxazine
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GB2189483A (en)	1987-10-28	Chlorodiflouromethoxyphenyl derivatives and their use as miticides
US3873304A (en)	1975-03-25	Plant growth regulants
US3983176A (en)	1976-09-28	Benzophenones as plant growth regulants
US3644422A (en)	1972-02-22	2-(substituted phenoxymethyl) dioxolanes
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US3932458A (en)	1976-01-13	Antimicrobial and plant-active 4,5-dihalopyrrole-2-carbonitriles
GB2101600A (en)	1983-01-19	2,4-Hexadienoic acid derivatives useful as weed-killers and phytogrowth regulators
US3985539A (en)	1976-10-12	4,5-Dihalopyrrole-2-carbonitrile-containing terrestrial and aquatic hebicidal composition
US3385689A (en)	1968-05-28	Method of controlling undesirable plant growth
EP0238997B1 (fr)	1990-06-20	Fongicide pour l'agriculture et l'horticulture
US3655761A (en)	1972-04-11	Certain oxime esters
US4364768A (en)	1982-12-21	3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones and their use as plant growth regulants
KR860002167B1 (ko)	1986-12-22	3-니트로벤젠술폰 아닐리드 유도체의 제조방법
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