CA1280440C - Compositions a base de 4,6-dinitro-2-(trifluoromethyl) phenol, herbicides,acaricides et regulatrices pour la croissance des cultures; derives de cescompositions - Google Patents

Compositions a base de 4,6-dinitro-2-(trifluoromethyl) phenol, herbicides,acaricides et regulatrices pour la croissance des cultures; derives de cescompositions

Info

Publication number: CA1280440C
Authority: CA; Canada
Prior art keywords: trifluoromethyl; dinitro; phenol; phenyl; general formula
Prior art date: 1983-02-03
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 - Fee Related

Application number

CA000446607A

Other languages

English (en)

Inventor

Gyula Eifert

Peter Inczedy

Ferenc Bihari

Istvan Magyari

Jeno Meszaros

Erzsebet Schuszler

Rudolf Czovek

Egon Klumpp

Peter Bohus

Judit Timar

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.)

Budapesti Vegyimuevek Rt

Original Assignee

Budapesti Vegyimuevek Rt

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.)

1983-02-03

Filing date

1984-02-02

Publication date

1991-02-19

1984-02-02 Application filed by Budapesti Vegyimuevek Rt filed Critical Budapesti Vegyimuevek Rt

1984-02-02 Priority to CA000446607A priority Critical patent/CA1280440C/fr

1991-02-19 Application granted granted Critical

1991-02-19 Publication of CA1280440C publication Critical patent/CA1280440C/fr

2008-02-19 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 25
239000004480 active ingredient Substances 0.000 title claims abstract description 12
230000001105 regulatory effect Effects 0.000 title claims abstract description 9
GPGNBSPUWGESET-UHFFFAOYSA-N 2,4-dinitro-6-(trifluoromethyl)phenol Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F GPGNBSPUWGESET-UHFFFAOYSA-N 0.000 title claims description 13
230000002363 herbicidal effect Effects 0.000 title claims description 12
230000000895 acaricidal effect Effects 0.000 title claims description 9
229940027987 antiseptic and disinfectant phenol and derivative Drugs 0.000 title description 4
238000000034 method Methods 0.000 claims abstract description 12
150000001875 compounds Chemical class 0.000 claims description 19
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
241000196324 Embryophyta Species 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
150000001340 alkali metals Chemical class 0.000 claims description 9
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims 4
241000238631 Hexapoda Species 0.000 claims 2
238000002360 preparation method Methods 0.000 abstract description 9
239000004009 herbicide Substances 0.000 abstract description 5
240000008042 Zea mays Species 0.000 description 13
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 13
235000002017 Zea mays subsp mays Nutrition 0.000 description 13
235000005822 corn Nutrition 0.000 description 13
239000000243 solution Substances 0.000 description 13
238000012360 testing method Methods 0.000 description 10
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 8
239000004495 emulsifiable concentrate Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
-1 alkali metal salts Chemical class 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
238000005507 spraying Methods 0.000 description 5
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 4
240000006122 Chenopodium album Species 0.000 description 4
235000009344 Chenopodium album Nutrition 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
210000005069 ears Anatomy 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
230000002147 killing effect Effects 0.000 description 4
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 4
RLXKADBMLQPLDV-UHFFFAOYSA-N 2-chloro-1,5-dinitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C(C(F)(F)F)=C1 RLXKADBMLQPLDV-UHFFFAOYSA-N 0.000 description 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
229940031826 phenolate Drugs 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical class CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 2
OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 2
241000238876 Acari Species 0.000 description 2
235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
235000004135 Amaranthus viridis Nutrition 0.000 description 2
235000010960 Atriplex hastata Nutrition 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
235000008645 Chenopodium bonus henricus Nutrition 0.000 description 2
235000009332 Chenopodium rubrum Nutrition 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000006378 damage Effects 0.000 description 2
230000002950 deficient Effects 0.000 description 2
235000013601 eggs Nutrition 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
208000014674 injury Diseases 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
229920000847 nonoxynol Polymers 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
QZADIXWDDVQVKM-UHFFFAOYSA-N 1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC(C(F)(F)F)=C1 QZADIXWDDVQVKM-UHFFFAOYSA-N 0.000 description 1
BKIWBVMEQHQJFA-UHFFFAOYSA-N 2,4-dinitrophenol;n-methylmethanamine Chemical compound CNC.OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O BKIWBVMEQHQJFA-UHFFFAOYSA-N 0.000 description 1
FXZGYEWQIGIFMC-UHFFFAOYSA-N 2,6-dinitro-4-(trifluoromethyl)phenol Chemical compound OC1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O FXZGYEWQIGIFMC-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
241000239290 Araneae Species 0.000 description 1
235000006463 Brassica alba Nutrition 0.000 description 1
244000056139 Brassica cretica Species 0.000 description 1
244000140786 Brassica hirta Species 0.000 description 1
235000011371 Brassica hirta Nutrition 0.000 description 1
244000070406 Malus silvestris Species 0.000 description 1
PWNYGNTZMFUEFF-UHFFFAOYSA-N N(CCO)CCO.[N+](=O)([O-])C=1C(=C(C=CC1)O)[N+](=O)[O-] Chemical compound N(CCO)CCO.[N+](=O)([O-])C=1C(=C(C=CC1)O)[N+](=O)[O-] PWNYGNTZMFUEFF-UHFFFAOYSA-N 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
244000300264 Spinacia oleracea Species 0.000 description 1
235000009337 Spinacia oleracea Nutrition 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
150000005325 alkali earth metal hydroxides Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
235000021016 apples Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
230000034303 cell budding Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
QJQKPQISRLUNHD-UHFFFAOYSA-L disodium;2-methyl-4,6-dinitrophenol;methyl-dioxido-oxo-$l^{5}-arsane Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O.CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QJQKPQISRLUNHD-UHFFFAOYSA-L 0.000 description 1
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical class CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 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
239000008187 granular material Substances 0.000 description 1
230000012447 hatching Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000012546 transfer Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1

Landscapes

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

CA000446607A 1983-02-03 1984-02-02 Compositions a base de 4,6-dinitro-2-(trifluoromethyl) phenol, herbicides,acaricides et regulatrices pour la croissance des cultures; derives de cescompositions Expired - Fee Related CA1280440C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000446607A CA1280440C (fr)	1983-02-03	1984-02-02	Compositions a base de 4,6-dinitro-2-(trifluoromethyl) phenol, herbicides,acaricides et regulatrices pour la croissance des cultures; derives de cescompositions

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU362/83		1983-02-03
CA000446607A CA1280440C (fr)	1983-02-03	1984-02-02	Compositions a base de 4,6-dinitro-2-(trifluoromethyl) phenol, herbicides,acaricides et regulatrices pour la croissance des cultures; derives de cescompositions

Publications (1)

Publication Number	Publication Date
CA1280440C true CA1280440C (fr)	1991-02-19

Family

ID=4127088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000446607A Expired - Fee Related CA1280440C (fr)	1983-02-03	1984-02-02	Compositions a base de 4,6-dinitro-2-(trifluoromethyl) phenol, herbicides,acaricides et regulatrices pour la croissance des cultures; derives de cescompositions

Country Status (1)

Country	Link
CA (1)	CA1280440C (fr)

1984
- 1984-02-02 CA CA000446607A patent/CA1280440C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1993-08-21	MKLA	Lapsed

Publication	Publication Date	Title
CA1324316C (fr)	1993-11-16	Compositions licides contenant des acides carboxyliques
EP0014684A2 (fr)	1980-08-20	Dérivés substitués en position 2 d'acides phénoxy-5 phénylphosphoniques, procédé pour leur préparation et leur utilisation comme herbicides
EP0183384A1 (fr)	1986-06-04	Sel de dicamba à volatilité basse et herbicides
EP0062905B1 (fr)	1985-03-13	Phényléthers hétérocycliques, procédé de préparation et herbicides les contenant
US4117167A (en)	1978-09-26	Dinitroaniline derivatives
US3954998A (en)	1976-05-04	Substituted phenyl indandiones as miticides
US3784605A (en)	1974-01-08	2-(polysubstituted phenyl)-1,3-indandione compounds
CA1280440C (fr)	1991-02-19	Compositions a base de 4,6-dinitro-2-(trifluoromethyl) phenol, herbicides,acaricides et regulatrices pour la croissance des cultures; derives de cescompositions
US3427146A (en)	1969-02-11	Phenoxypyridazines as herbicides
US4596893A (en)	1986-06-24	2-trifluoromethyl-4,6-dinitro-phenol and derivatives thereof, process for the preparation thereof and herbicidal, acaricidal and crop regulation compositions containing same
US4531966A (en)	1985-07-30	Herbicide compositions
JP2994760B2 (ja)	1999-12-27	ヒドラジン誘導体
US4108632A (en)	1978-08-22	Use of phthalanilic acids to regulate the growth of corn plants
EP0046468A1 (fr)	1982-03-03	Dérivés de la quinoxaline et compositions herbicides
GB2135993A (en)	1984-09-12	Herbicidal and acaricidal dinitrophenol derivatives
CA1128539A (fr)	1982-07-27	Obtention et emploi comme pesticides d'ethers de furylmethyloximes
CA1077958A (fr)	1980-05-20	Carboxylates de phenoxyphenoxyalkylcyclopropane a action pesticide
US3445222A (en)	1969-05-20	Herbicidal compositions containing trisubstituted-phenyl n-methylcarbamates
US4348411A (en)	1982-09-07	Combating bacteria with halogenomethylsulphonylphenyl-phthalamic acids
JPS6249275B2 (fr)	1987-10-19
US5886207A (en)	1999-03-23	Optically active compound of flubrocythrinate, a process for preparing the same
AT325896B (de)	1975-11-10	Insektizide und akarizide zusammensetzungen
CA1093563A (fr)	1981-01-13	Carboxylates utilises comme pesticides
CA1213289A (fr)	1986-10-28	N-haloacetyl-2-alcoyl-6-acylanilines herbicides et derives
SU650478A3 (ru)	1979-02-28	Инсектицидное средство