JPS6239148B2 - - Google Patents

Info

Publication number: JPS6239148B2
Authority: JP; Japan
Prior art keywords: phenoxy; hydroxy; trifluoromethylphenoxy; formula; pentanoate
Prior art date: 1979-12-28
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

JP17157179A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5695148A (en

Inventor

Katsumi Nanjo

Shinzo Someya

Takayoshi Katsurayama

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.)

Kanesho KK

Original Assignee

Kanesho KK

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.)

1979-12-28

Filing date

1979-12-28

Publication date

1987-08-21

1979-12-28 Application filed by Kanesho KK filed Critical Kanesho KK

1979-12-28 Priority to JP17157179A priority Critical patent/JPS5695148A/ja

1981-08-01 Publication of JPS5695148A publication Critical patent/JPS5695148A/ja

1987-08-21 Publication of JPS6239148B2 publication Critical patent/JPS6239148B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 46
-1 [4′-(4′′-trifluoromethylphenoxy)phenoxy]-pentanoate Chemical compound 0.000 claims description 35
230000002363 herbicidal effect Effects 0.000 claims description 22
239000004009 herbicide Substances 0.000 claims description 21
GDNQEDDYBXSHKE-UHFFFAOYSA-N 3-hydroxy-4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pentanoic acid Chemical compound C1=CC(OC(C)C(O)CC(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 GDNQEDDYBXSHKE-UHFFFAOYSA-N 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
229910052783 alkali metal Inorganic materials 0.000 claims description 7
150000001340 alkali metals Chemical class 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
150000001342 alkaline earth metals Chemical class 0.000 claims description 5
CSJOULZYIVQPFN-UHFFFAOYSA-N ethyl 3-hydroxy-4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pentanoate Chemical compound C1=CC(OC(C)C(O)CC(=O)OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 CSJOULZYIVQPFN-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
125000005210 alkyl ammonium group Chemical group 0.000 claims description 4
159000000000 sodium salts Chemical class 0.000 claims description 4
229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
239000012279 sodium borohydride Substances 0.000 claims description 3
229910000497 Amalgam Inorganic materials 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 2
239000007868 Raney catalyst Substances 0.000 claims description 2
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
229910003446 platinum oxide Inorganic materials 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims 2
125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
WLGUJYJYKYELCZ-UHFFFAOYSA-N 4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pentanoic acid Chemical compound C1=CC(OC(CCC(O)=O)C)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 WLGUJYJYKYELCZ-UHFFFAOYSA-N 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
241000196324 Embryophyta Species 0.000 description 19
150000003839 salts Chemical class 0.000 description 18
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 11
239000002689 soil Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
239000004927 clay Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000009333 weeding Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
235000016068 Berberis vulgaris Nutrition 0.000 description 3
241000335053 Beta vulgaris Species 0.000 description 3
235000001602 Digitaria X umfolozi Nutrition 0.000 description 3
235000017898 Digitaria ciliaris Nutrition 0.000 description 3
235000005476 Digitaria cruciata Nutrition 0.000 description 3
235000006830 Digitaria didactyla Nutrition 0.000 description 3
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 3
235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
244000058871 Echinochloa crus-galli Species 0.000 description 3
244000025670 Eleusine indica Species 0.000 description 3
235000014716 Eleusine indica Nutrition 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
230000000694 effects Effects 0.000 description 3
HSVWOVVJHMSOBT-UHFFFAOYSA-N methyl 3-hydroxy-4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pentanoate Chemical compound C1=CC(OC(C)C(O)CC(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 HSVWOVVJHMSOBT-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
ZTVIKZXZYLEVOL-DGKWVBSXSA-N 2-hydroxy-2-phenylacetic acid [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester Chemical group C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C(O)C1=CC=CC=C1 ZTVIKZXZYLEVOL-DGKWVBSXSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
244000055702 Amaranthus viridis Species 0.000 description 2
235000004135 Amaranthus viridis Nutrition 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
235000009344 Chenopodium album Nutrition 0.000 description 2
235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
235000009332 Chenopodium rubrum Nutrition 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
240000008415 Lactuca sativa Species 0.000 description 2
235000003228 Lactuca sativa Nutrition 0.000 description 2
229920001732 Lignosulfonate Polymers 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000209504 Poaceae Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000005215 alkyl ethers Chemical class 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000011835 investigation Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 description 1
MVHWKYHDYCGNQN-UHFFFAOYSA-N 1,5-dichloro-3-fluoro-2-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(F)C=C(Cl)C=C1Cl MVHWKYHDYCGNQN-UHFFFAOYSA-N 0.000 description 1
NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 description 1
UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
RQAPBIOXXSQHEU-UHFFFAOYSA-N 2,3-dichloro-6-methylbenzoic acid Chemical compound CC1=CC=C(Cl)C(Cl)=C1C(O)=O RQAPBIOXXSQHEU-UHFFFAOYSA-N 0.000 description 1
239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
KGKGSIUWJCAFPX-UHFFFAOYSA-N 2,6-dichlorothiobenzamide Chemical compound NC(=S)C1=C(Cl)C=CC=C1Cl KGKGSIUWJCAFPX-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
PYSWMLOJSZEZCM-UHFFFAOYSA-N 3,6-dichloro-2-methylbenzoic acid Chemical compound CC1=C(Cl)C=CC(Cl)=C1C(O)=O PYSWMLOJSZEZCM-UHFFFAOYSA-N 0.000 description 1
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 1
ILOZECIQNMSVCK-UHFFFAOYSA-N 4-methyl-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=CC=C(C)C=C1 ILOZECIQNMSVCK-UHFFFAOYSA-N 0.000 description 1
DFNAFDHFFUVITM-UHFFFAOYSA-N 4-methylsulfonyl-2,6-dinitro-n-propylaniline Chemical compound CCCNC1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O DFNAFDHFFUVITM-UHFFFAOYSA-N 0.000 description 1
GGYVZXWCUIEFEK-UHFFFAOYSA-N 6-butan-2-yl-4,6-dinitrocyclohexa-2,4-dien-1-ol Chemical compound CCC(C)C1([N+]([O-])=O)C=C([N+]([O-])=O)C=CC1O GGYVZXWCUIEFEK-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
235000007320 Avena fatua Nutrition 0.000 description 1
NJHLTTCFUKEVCV-UHFFFAOYSA-N C.[In] Chemical compound C.[In] NJHLTTCFUKEVCV-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
DXXVCXKMSWHGTF-UHFFFAOYSA-N Chlomethoxyfen Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 DXXVCXKMSWHGTF-UHFFFAOYSA-N 0.000 description 1
VCBRBUKGTWLJOB-UHFFFAOYSA-N Chloranocryl Chemical compound CC(=C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VCBRBUKGTWLJOB-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000234646 Cyperaceae Species 0.000 description 1
QAHFOPIILNICLA-UHFFFAOYSA-N Diphenamid Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 QAHFOPIILNICLA-UHFFFAOYSA-N 0.000 description 1
HHMCAJWVGYGUEF-UHFFFAOYSA-N Fluorodifen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O HHMCAJWVGYGUEF-UHFFFAOYSA-N 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
SUFWRMCGIVJFOS-UHFFFAOYSA-N IC=1C=C(C#N)C=C(C1O)I.BrC=1C=C(C#N)C=C(C1O)Br.C1(=CC=CC=C1)C(C#N)C1=CC=CC=C1.ClC1=C(C#N)C(=CC=C1)Cl Chemical compound IC=1C=C(C#N)C=C(C1O)I.BrC=1C=C(C#N)C=C(C1O)Br.C1(=CC=CC=C1)C(C#N)C1=CC=CC=C1.ClC1=C(C#N)C(=CC=C1)Cl SUFWRMCGIVJFOS-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
239000005574 MCPA Substances 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
244000184734 Pyrus japonica Species 0.000 description 1
244000088415 Raphanus sativus Species 0.000 description 1
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
241001092459 Rubus Species 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
241000005601 Trisetum Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
XQNAUQUKWRBODG-UHFFFAOYSA-N chlornitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C=C1Cl XQNAUQUKWRBODG-UHFFFAOYSA-N 0.000 description 1
238000011109 contamination Methods 0.000 description 1
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 1
IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
229940116901 diethyldithiocarbamate Drugs 0.000 description 1
BJIKOZOULYUROB-UHFFFAOYSA-N dimethoxymethanethione Chemical group COC(=S)OC BJIKOZOULYUROB-UHFFFAOYSA-N 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
WHISHDWWUNQJFB-UHFFFAOYSA-N ethyl 3-oxo-4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pentanoate Chemical compound C1=CC(OC(C)C(=O)CC(=O)OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 WHISHDWWUNQJFB-UHFFFAOYSA-N 0.000 description 1
GRCZGXVEUFISNI-UHFFFAOYSA-N ethyl 4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pentanoate Chemical compound C1=CC(OC(C)CCC(=O)OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 GRCZGXVEUFISNI-UHFFFAOYSA-N 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
239000002917 insecticide Substances 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
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
IEPVFABAADVNMN-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2,2-dimethylpentanamide Chemical compound CCCC(C)(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 IEPVFABAADVNMN-UHFFFAOYSA-N 0.000 description 1
PJFGPJQBWSEWKX-UHFFFAOYSA-N n-[(2,4-dichlorophenoxy)-methoxyphosphinothioyl]propan-2-amine Chemical compound CC(C)NP(=S)(OC)OC1=CC=C(Cl)C=C1Cl PJFGPJQBWSEWKX-UHFFFAOYSA-N 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000003375 plant hormone Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000009331 sowing Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000011272 standard treatment Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Landscapes

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

JP17157179A 1979-12-28 1979-12-28 Novel herbicide and its preparation Granted JPS5695148A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP17157179A JPS5695148A (en)	1979-12-28	1979-12-28	Novel herbicide and its preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP17157179A JPS5695148A (en)	1979-12-28	1979-12-28	Novel herbicide and its preparation

Publications (2)

Publication Number	Publication Date
JPS5695148A JPS5695148A (en)	1981-08-01
JPS6239148B2 true JPS6239148B2 (de)	1987-08-21

Family

ID=15925607

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP17157179A Granted JPS5695148A (en)	1979-12-28	1979-12-28	Novel herbicide and its preparation

Country Status (1)

Country	Link
JP (1)	JPS5695148A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4540804A (en) *	1984-10-12	1985-09-10	Stauffer Chemical Company	Herbicide intermediates

1979
- 1979-12-28 JP JP17157179A patent/JPS5695148A/ja active Granted

Also Published As

Publication number	Publication date
JPS5695148A (en)	1981-08-01

Publication	Publication Date	Title
US4439229A (en)	1984-03-27	Substituted phthalimides herbicides
KR840001718B1 (ko)	1984-10-17	니트로디페닐 에테르류의 제조방법
US4070178A (en)	1978-01-24	Herbicidal diphenyl ethers
US4093446A (en)	1978-06-06	Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
US4063929A (en)	1977-12-20	Herbicidal 4-trifluoromethyl-4'nitrodiphenyl ethers
US4039588A (en)	1977-08-02	Herbicidal 4-nitro-diphenyl ethers
US4209318A (en)	1980-06-24	Herbicidal esters of 4-trifluoromethyl-3-carboxamido-4-nitro diphenyl ethers
US4076741A (en)	1978-02-28	Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
CA1140563A (en)	1983-02-01	Herbicidal esters of 4-trifluormethyl-3'- carboxy-4'-nitro diphenyl ethers
US4059435A (en)	1977-11-22	Herbicidal 4-trifluoromethyl-3-cyanoalkoxy-4-nitro diphenyl ethers
GB1560416A (en)	1980-02-06	Trifluoromethylphenyl derivatives
US4163661A (en)	1979-08-07	Phenoxyphenoxy crotonic acid derivatives and herbicidal composition
US3954875A (en)	1976-05-04	Benzophenone herbicides
US3551484A (en)	1970-12-29	3,5-disubstituted benzamides
US4877897A (en)	1989-10-31	4-Trifluoromethyl-4'-nitrodiphenyl ethers
US3489784A (en)	1970-01-13	(chlorinated alpha,alpha,alpha - trifluoro-m-tolyl)acetonitriles,acetamides and acetic acids
US3640699A (en)	1972-02-08	3 5-disubstituted benzamides
US5290756A (en)	1994-03-01	4-trifluoromethyl-4'-nitrodiphenyl ethers
JPS6239148B2 (de)	1987-08-21
USRE31455E (en)	1983-12-06	Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
US4335249A (en)	1982-06-15	Herbicidal diphenyl ethers, sulfides, sulfoxides and sulfones
JPS6225136B2 (de)	1987-06-01
US4894479A (en)	1990-01-16	Herbicidal diphenyl ethers
US4306900A (en)	1981-12-22	Herbicidal nitrodiphenyl ethers
US4386954A (en)	1983-06-07	Herbicidal diphenyl ethers