JPS5814402B2 - ジヨソウザイ - Google Patents

ジヨソウザイ

Info

Publication number: JPS5814402B2
Authority: JP; Japan
Prior art keywords: chloro; trifluoromethylphenoxy; ester; phenoxy; soil
Prior art date: 1975-09-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP11598275A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5241229A (en

Inventor

横道勲

高橋量平

坂下信行

重原格

西山隆三

藤川敢市

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.)

Ishihara Mining & Chemical Co

Original Assignee

Ishihara Mining & Chemical Co

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.)

1975-09-27

Filing date

1975-09-27

Publication date

1983-03-18

1975-09-27 Application filed by Ishihara Mining & Chemical Co filed Critical Ishihara Mining & Chemical Co

1975-09-27 Priority to JP11598275A priority Critical patent/JPS5814402B2/ja

1976-09-09 Priority to NZ181994A priority patent/NZ181994A/xx

1976-09-10 Priority to US05/722,327 priority patent/US4070177A/en

1976-09-16 Priority to GB38458/76A priority patent/GB1497520A/en

1976-09-20 Priority to AU17909/76A priority patent/AU501045B2/en

1976-09-24 Priority to IT2760776A priority patent/IT1070841B/it

1976-09-27 Priority to FR7628996A priority patent/FR2325638A1/fr

1976-09-27 Priority to DE2643438A priority patent/DE2643438C2/de

1976-09-27 Priority to CA262,067A priority patent/CA1101435A/en

1977-03-30 Publication of JPS5241229A publication Critical patent/JPS5241229A/ja

1977-09-29 Priority to US05/837,815 priority patent/US4203758A/en

1983-03-18 Publication of JPS5814402B2 publication Critical patent/JPS5814402B2/ja

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 claims description 15
230000002363 herbicidal effect Effects 0.000 claims description 13
239000004009 herbicide Substances 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 6
-1 alkaline earth metal salt Chemical class 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000005907 alkyl ester group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
241000196324 Embryophyta Species 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
239000002689 soil Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
239000000047 product Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000000034 method Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
244000058871 Echinochloa crus-galli Species 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
241000209504 Poaceae Species 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
230000009036 growth inhibition Effects 0.000 description 3
ZHRWGXGLANKCJJ-UHFFFAOYSA-N methyl 2-[2-bromo-5-[2-chloro-4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C1=C(Br)C(OC(C)C(=O)OC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 ZHRWGXGLANKCJJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
244000088415 Raphanus sativus Species 0.000 description 2
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
239000003513 alkali Substances 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
XZRJRQZCBIXCIE-UHFFFAOYSA-N methyl 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-cyanophenoxy]propanoate Chemical compound C1=C(C#N)C(OC(C)C(=O)OC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 XZRJRQZCBIXCIE-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000002420 orchard Substances 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
SMTUQFOSYBWARH-UHFFFAOYSA-N 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-cyanophenoxy]acetic acid Chemical compound C1=C(C#N)C(OCC(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 SMTUQFOSYBWARH-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
IKTVFFPUVYZPHG-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-hydroxybenzonitrile Chemical compound C1=C(C#N)C(O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IKTVFFPUVYZPHG-UHFFFAOYSA-N 0.000 description 1
241000254060 Aquatica lateralis Species 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
235000001602 Digitaria X umfolozi Nutrition 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
240000003173 Drymaria cordata Species 0.000 description 1
244000025670 Eleusine indica Species 0.000 description 1
235000014716 Eleusine indica Nutrition 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
240000000249 Morus alba Species 0.000 description 1
235000008708 Morus alba Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241001076438 Oxya japonica Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000009422 growth inhibiting effect Effects 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000002147 killing effect Effects 0.000 description 1
KXXFZIVJIBOARD-UHFFFAOYSA-N methyl 2-[2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)OC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 KXXFZIVJIBOARD-UHFFFAOYSA-N 0.000 description 1
ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
BZCKRPHEZOHHBK-UHFFFAOYSA-N methyl 2-phenoxyacetate Chemical compound COC(=O)COC1=CC=CC=C1 BZCKRPHEZOHHBK-UHFFFAOYSA-N 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
DDZWFIDYJFRMQK-UHFFFAOYSA-M sodium;2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-cyanophenoxy]propanoate Chemical compound [Na+].C1=C(C#N)C(OC(C)C([O-])=O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 DDZWFIDYJFRMQK-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000009333 weeding Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

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

JP11598275A 1975-09-27 1975-09-27 ジヨソウザイ Expired JPS5814402B2 (ja)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
JP11598275A JPS5814402B2 (ja)	1975-09-27	1975-09-27	ジヨソウザイ
NZ181994A NZ181994A (en)	1975-09-27	1976-09-09	(2-chloro-4-trifluorom-ethylphenoxy)-phenoxy acids,esters,ethers,amides and nitriles and herbicidal compositions
US05/722,327 US4070177A (en)	1975-09-27	1976-09-10	Herbicidal phenoxy-phenoxy alkane carboxylic acid derivatives
GB38458/76A GB1497520A (en)	1975-09-27	1976-09-16	Substituted 3-phenoxy phenoxy alkane carboxylic acids nitriles esters and amides and herbicidal compositions thereo
AU17909/76A AU501045B2 (en)	1975-09-27	1976-09-20	Phenoxyphenoxyalkanr carboxlic acid derivatives
IT2760776A IT1070841B (it)	1975-09-27	1976-09-24	Erbicida contenente derivati dell acido fenossi fenossi-alcano carbossilico
FR7628996A FR2325638A1 (fr)	1975-09-27	1976-09-27	Herbicides a base d'acide phenoxy phenoxy alcane carboxylique
DE2643438A DE2643438C2 (de)	1975-09-27	1976-09-27	Phenoxy-phenoxyalkancarbonsäurederivate und diese enthaltende herbicide Mittel
CA262,067A CA1101435A (en)	1975-09-27	1976-09-27	Herbicide
US05/837,815 US4203758A (en)	1975-09-27	1977-09-29	Herbicidal phenoxy-phenoxyalkane thio esters

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP11598275A JPS5814402B2 (ja)	1975-09-27	1975-09-27	ジヨソウザイ

Publications (2)

Publication Number	Publication Date
JPS5241229A JPS5241229A (en)	1977-03-30
JPS5814402B2 true JPS5814402B2 (ja)	1983-03-18

Family

ID=14675935

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP11598275A Expired JPS5814402B2 (ja)	1975-09-27	1975-09-27	ジヨソウザイ

Country Status (2)

Country	Link
JP (1)	JPS5814402B2 (it)
IT (1)	IT1070841B (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5828262B2 (ja) *	1976-03-17	1983-06-15	石原産業株式会社	フエノキシフエノキシアルカンカルボン酸誘導体及びそれらを含有する除草剤
CH626318A5 (it) *	1977-03-08	1981-11-13	Ciba Geigy Ag
DE2961372D1 (en) *	1978-01-20	1982-01-28	Ciba Geigy Ag	Phenoxy-phenoxy-alkylcarboxylic acid derivatives with herbicidal activity, their preparation, compositions containing them and their use

1975
- 1975-09-27 JP JP11598275A patent/JPS5814402B2/ja not_active Expired
1976
- 1976-09-24 IT IT2760776A patent/IT1070841B/it active

Also Published As

Publication number	Publication date
JPS5241229A (en)	1977-03-30
IT1070841B (it)	1985-04-02

Publication	Publication Date	Title
US4134751A (en)	1979-01-16	Herbicidal compound, herbicidal composition containing the same and method of use thereof
US4070177A (en)	1978-01-24	Herbicidal phenoxy-phenoxy alkane carboxylic acid derivatives
JPS5840947B2 (ja)	1983-09-08	トリフルオロメチルピリドキシフェノキシプロピオン酸誘導体
JPS6341905B2 (it)	1988-08-19
JPS5828262B2 (ja)	1983-06-15	フエノキシフエノキシアルカンカルボン酸誘導体及びそれらを含有する除草剤
CA1090348A (en)	1980-11-25	.alpha. METHYL MALONIC ACID DERIVATIVES
JPS5814402B2 (ja)	1983-03-18	ジヨソウザイ
KR880002603B1 (ko)	1988-12-04	페녹시알킬아마이드 유도체의 제조방법
JPS63122672A (ja)	1988-05-26	ピラゾ−ル誘導体および選択性除草剤
JPS5934705B2 (ja)	1984-08-24	フエノキシフエノキシアルカンニトリル誘導体及びそれらを含有する除草剤
JPH0248550B2 (it)	1990-10-25
CA1093577A (en)	1981-01-13	Phenoxy-phenoxy propionic acids and derivatives thereof
JPS6025401B2 (ja)	1985-06-18	除草剤
JPS6136485B2 (it)	1986-08-19
JPH04275201A (ja)	1992-09-30	除草剤組成物
CA1089873A (en)	1980-11-18	Phenoxy-phenoxy valeric acids and derivatives thereof
KR800000902B1 (ko)	1980-09-10	α-[4-(4-트리플루오로메틸 페녹시) 페녹시] 프로피온산계 화합물의 제조방법
JPS62148493A (ja)	1987-07-02	新規ホスホン酸誘導体および除草剤
JPS585163B2 (ja)	1983-01-29	サツソウザイ
JPS6263573A (ja)	1987-03-20	トリフルオロメチルピリドキシフエノキシプロピオン酸またはその誘導体
JPS61178904A (ja)	1986-08-11	除草剤
JPH0517910B2 (it)	1993-03-10
JPS5817441B2 (ja)	1983-04-07	ジヨソウザイ
JPS6134417B2 (it)	1986-08-07
JPS5890570A (ja)	1983-05-30	オキサジアゾリン誘導体及び除草剤