DD231714A5 - PLANT PROTECTION AGENTS AND METHODS OF CONCENTRATING SCHAEDLINGEN AND UNKRAEUTERN - Google Patents
PLANT PROTECTION AGENTS AND METHODS OF CONCENTRATING SCHAEDLINGEN AND UNKRAEUTERN Download PDFInfo
- Publication number
- DD231714A5 DD231714A5 DD84266211A DD26621184A DD231714A5 DD 231714 A5 DD231714 A5 DD 231714A5 DD 84266211 A DD84266211 A DD 84266211A DD 26621184 A DD26621184 A DD 26621184A DD 231714 A5 DD231714 A5 DD 231714A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- group
- plant protection
- alkyl
- dinitrophenol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 239000011814 protection agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 241000196324 Embryophyta Species 0.000 claims abstract description 10
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000004476 plant protection product Substances 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 13
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 240000008042 Zea mays Species 0.000 description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 10
- 239000000243 solution Substances 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
- 230000000694 effects Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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 description 4
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical group CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 4
- 240000001592 Amaranthus caudatus Species 0.000 description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- -1 alkali metal salts Chemical class 0.000 description 3
- 235000012735 amaranth Nutrition 0.000 description 3
- 239000004178 amaranth Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 2
- 241000219312 Chenopodium Species 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 2
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 2
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 2
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 2
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 244000300264 Spinacia oleracea Species 0.000 description 2
- 235000009337 Spinacia oleracea Nutrition 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
- 238000002835 absorbance Methods 0.000 description 2
- 210000003763 chloroplast Anatomy 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000839 emulsion Substances 0.000 description 2
- 244000230030 foxtail bristlegrass Species 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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
- 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 1
- VRQKCPBODHTCFI-UHFFFAOYSA-N 2-nitro-4,6-bis(trifluoromethyl)phenol Chemical class OC1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1C(F)(F)F VRQKCPBODHTCFI-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
- 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
- 235000011371 Brassica hirta Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241001057636 Dracaena deremensis Species 0.000 description 1
- 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 1
- 206010061217 Infestation Diseases 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000218206 Ranunculus Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 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
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- JSWPEXGHOFWWKT-UHFFFAOYSA-N cyclohexanone;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound O=C1CCCCC1.CC1=CC(=O)CC(C)(C)C1 JSWPEXGHOFWWKT-UHFFFAOYSA-N 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
- 238000007865 diluting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Die Erfindung betrifft neue Pflanzenschutzmittel, die als Wirkstoff Verbindungen der allgemeinen Formel (I) enthalten, worin X fuer Wasserstoff, ein Alkalimetall oder ein Erdalkalimetall, fuer eine Alkyl- oder Alkenylcarbonylgruppe mit 1-10 Kohlenstoffatomen, fuer eine gegebenenfalls durch Halogen substituierte Phenylcarbonylgruppe oder eine Gruppe der allgemeinen Formel H HNR1R2R3steht, in der R1, R2 und R3 unabhaengig voneinander Wasserstoff, eine Alkyl-, eine Alkoxyalkyl-, eine Alkenyl-, eine Hydroxyalkyl-, eine Cycloalkyl- oder eine gegebenenfalls substitutierte Phenylgruppe bedeuten. Die Erfindung betrifft ferner ein Verfahren zum Bekaempfen von Schaedlingen und Unkraeutern. Formel IThe invention relates to novel crop protection compositions containing as active ingredient compounds of general formula (I) wherein X is hydrogen, an alkali metal or an alkaline earth metal, an alkyl or alkenylcarbonyl group having 1-10 carbon atoms, an optionally halogen-substituted phenylcarbonyl or a Group of the general formula H HNR1R2R3 stands in which R1, R2 and R3 are independently hydrogen, an alkyl, an alkoxyalkyl, an alkenyl, a hydroxyalkyl, a cycloalkyl or an optionally substituted phenyl group. The invention further relates to a method for controlling pests and weeds. Formula I
Description
Die Erfindung betrifft ein Pflanzenschutzmittel und ein Verfahren zum Bekämpfen von Schädlingen und Unkräutern. Charakteristik der bekannten technischen LösungenThe invention relates to a plant protection product and a method for controlling pests and weeds. Characteristic of the known technical solutions
Es ist bekannt, daß das 2-Methyl-4,6-dinitrophenol (Dinitro-ortho-kresol; DNOC) und seine Alkalisalze eine herbizide und akarizide Wirkung aufweisen. Zusammensetzungen mit dieser Substanz als Wirkstoff sind z. B. Novenda und Kresonit. Ebenfalls ein bekanntes Herbizid ist das 2-sec.-Butyl-4,6-dinitrophenol (DNBP), eine dem Dinitro-ortho-kresol verwandte Verbindung, die in kleineren Dosen auch als Biostimulator in Maiskulturen verwendet werden kann (Ohlrogge, A. J.: The Development of DNBP [Dinoseb] as a Biostimulant for Com in Plant Growth Regulators; Editor: Stutte CA. 79-87 pp. Advances in chemistry series; 159. American Chemical Society, Washington, 1977).It is known that the 2-methyl-4,6-dinitrophenol (dinitro-ortho-cresol, DNOC) and its alkali metal salts have a herbicidal and acaricidal activity. Compositions containing this substance as an active ingredient are, for. B. Novenda and cresonite. Another well-known herbicide is 2-sec-butyl-4,6-dinitrophenol (DNBP), a dinitro-ortho-cresol-related compound that can also be used as a biostimulator in maize crops in smaller doses (Ohlrogge, AJ: The Development of DNBP [Dinoseb] as a Biostimulant for Com in Plant Growth Regulator; Editor: Stutte CA 79-87 pp Advances in chemistry series; 159 American Chemical Society, Washington, 1977).
In der GB-PS 1378994 ist die Herstellung von 2,4-bis(Trifluormethyl)-6-nitrophenols und seiner Derivate beschrieben. Die Herstellung des2,6-Dinitro-4-trifluormethylphenols und seiner Derivate ist in der US-PS 3813446 beschrieben. Diese bekannten Verfahren werden in organischen Lösungsmitteln, gegebenenfalls in Gegenwart eines Phasentransfer-Katalysators ausgeführt. Dabei laufen auch unerwünschte Nebenreaktionen ab, zum Beispiel die Bildung von Ätherderivaten in methanolischem Medium, oder die Hydrolyse der Trifluormethylgruppe zur Carboxylgruppe.In GB-PS 1378994 the preparation of 2,4-bis (trifluoromethyl) -6-nitrophenols and its derivatives is described. The preparation of 2,6-dinitro-4-trifluoromethylphenol and its derivatives is described in U.S. Patent 3,813,446. These known processes are carried out in organic solvents, if appropriate in the presence of a phase transfer catalyst. In this case also run off unwanted side reactions, for example, the formation of ether derivatives in methanolic medium, or the hydrolysis of the trifluoromethyl group to the carboxyl group.
Ziel der Erfindung ,Aim of the invention
Mit der Erfindung sollen neue pestizide Mittel mit herbizider, akarizider und wachstumsregulierender Wirkung bereitgestellt werden.The invention is intended to provide novel pesticidal compositions having herbicidal, acaricidal and growth-regulating effects.
Erfindungsgemäß enthalten die neue Mittel neben üblichen Hilfs- und Trägerstoffen als Wirkstoff eine Verbindung der allgemeinen Formel (I), worinAccording to the invention, the novel agents contain, in addition to customary auxiliaries and excipients, as active ingredient a compound of the general formula (I) in which
X für Wasserstoff, ein Alkalimetall oder ein Erdalkalimetall, für eine Alkyl- oder Alkenylcarbonylgruppe mit 1 bis 10 Kohlenstoffatomen, für eine gegebenenfalls durch Halogen substituierte Phenylcarbonyigruppe oder eine Gruppe der allgemeinen FormelX is hydrogen, an alkali metal or an alkaline earth metal, an alkyl or alkenylcarbonyl group having 1 to 10 carbon atoms, an optionally substituted by halogen phenylcarbonyyl or a group of the general formula
HNR1R2R3 HNR 1 R 2 R 3
steht,stands,
in der R1, R2 und R3 unabhängig voneinander Wasserstoff, eine Alkyl-, eine Alkoxyalkyl-, eine Alkenyl-, eine Hydroxyalkyl-, eine Cycloalkyl, oder eine gegebenenfalls substituierte Phenylgruppe bedeuten.in which R 1 , R 2 and R 3 independently of one another represent hydrogen, an alkyl, an alkoxyalkyl, an alkenyl, a hydroxyalkyl, a cycloalkyl or an optionally substituted phenyl group.
Diese Verbindungen können hergestellt werden, indem man im ersten Schritt aus 2-Chlor-3,5-dinitro-benzotrifluorid durch Umsetzen mit einem Alkali- oder Erdalkalihydroxyd das entsprechende Alkali- oder Erdaikaliphenolat herstellt. Die Reaktion wird ohne Katalysator in wäßrigem Medium bei 20-1000C, vorzugsweise bei 60-80°C, und einer Laugenkonzentration von 5-20Gew.-%, vorzugsweise 10-15Gew.-%, ausgeführt. Das bei der Hydrolyse erhaltene Phenolat kann mittels einer Säure in an sich bekannte Weise in das Phenolderivat übergeführt werden. Gewünschtenfalls kann aus dem erhaltenen Phenol (X = H) durch Umsetzen mit einer entsprechenden Base eine andere Verbindung der allgemeinen Formel (I) hergestellt werden. Die Verbindungen der allgemeinen Formel (I) werden aus dem Reaktionsgemisch isoliert und können dann zu Pflanzenschutzmitteln weiterverarbeitet werden. Zu diesem Zweck werden die im Pflanzenschutz allgemein üblichen Träger-, Streck- und Hilfsmittel verwendet. Die Form der Zusammensetzung wird entsprechend dem Anwendungszweck gewählt. Je nach der Anwendungsweise und dem Typ des Mittels enthalten die Zusammensetzungen vorzugsweise 0,1-80 Gew.-% Wirkstoff. Die Formulierungen werden in Pflanzenkulturen zur Vernichtung von Schädlingen beziehungsweise zur Regulierung des pflanzlichen Wachstums eingesetzt.These compounds can be prepared by preparing the corresponding alkali or Erdaikaliphenolat in the first step from 2-chloro-3,5-dinitro-benzotrifluoride by reacting with an alkali or alkaline earth metal hydroxide. The reaction is conducted without a catalyst in an aqueous medium at 20-100 0 C, preferably at 60-80 ° C, and a sud concentration of 5-20Gew .-%, preferably 10-15Gew .-% executed. The phenolate obtained in the hydrolysis can be converted into the phenol derivative by means of an acid in a manner known per se. If desired, another compound of general formula (I) can be prepared from the resulting phenol (X = H) by reaction with a corresponding base. The compounds of the general formula (I) are isolated from the reaction mixture and can then be further processed into crop protection agents. For this purpose, the carrier, extenders and auxiliaries which are generally customary in crop protection are used. The shape of the composition is selected according to the purpose of use. Depending on the mode of application and the type of agent, the compositions preferably contain 0.1-80% by weight of active ingredient. The formulations are used in crops for the destruction of pests or for the regulation of plant growth.
Die Erfindung wird an Hand der folgenden Beispiele näher erläutert, ist jedoch nicht auf diese Beispiele beschränkt.The invention will be explained in more detail with reference to the following examples, but is not limited to these examples.
60gew.-%iges Emulsionskonzentrat (EC60)60% by weight emulsion concentrate (EC60)
433g 2-Trifluormethyl-4,6-dinitrophenol (97%ig) werden bei 400C in einem Gemisch aus 200g Isophoron und 25g Xylol gelöst.433g 2-trifluoromethyl-4,6-dinitrophenol (97%) are dissolved at 40 0 C in a mixture of 200 g of isophorone, and 25 g of xylene.
Die Lösung wird auf Raumtemperatur gekühlt und durch ein GAF-Fiiter der Porenweite 0,1 μπι filtriert. Dem Filtrat werden als Emulgator 36g Tensiofix B7425 und 6g Tensiofix LS unter Rühren zugesetzt.The solution is cooled to room temperature and filtered through a GAF filter of pore size 0.1 μπι . 36 g of Tensiofix B7425 and 6 g of Tensiofix LS are added to the filtrate as an emulsifier with stirring.
•60gew.-%iges Emulsionskonzentrat (EC60)60% strength by weight emulsion concentrate (EC60)
Man arbeitet nach der im Beispiel 1 beschriebenen Weise, verwendet jedoch statt Isophoron Cyclohexanon und statt Xylol das Lösungsmittel Aromatol. Als Emulgatoren werden die in der folgenden Tabelle genannten Produkte eingesetzt.The procedure described in Example 1, but using instead of isophorone cyclohexanone and instead of xylene, the solvent aromatol. The emulsifiers used are the products mentioned in the following table.
Emulgator ing: A B CEmulsifier: A B C
TensiofixAS -18 — 10TensiofixAS -18 - 10
TensiofixLS 24 — —TensiofixLS 24 - -
Emuisogen EL - — 12 25Emuisogen EL - - 12 25
SapogenatT180 — 10 —SapogenatT180 - 10 -
SapogenatT500 — 20 7Sapogenate T500 - 20 7
20gew.-%iges wasserlösliches Konzentrat (WSC20)20% by weight water-soluble concentrate (WSC20)
Zu 300g einer 30%igen wäßrigen Lösung von 2-Trifluormethyl-4,6-dinitro-natriumphenolat werden als Emulgator 50g Äthylenglycol und 4g Tensiofix CG-21 gegeben. Die Lösung wird unter Rühren mit entsalzenem Wasser auf 450g aufgefülltTo 300 g of a 30% strength aqueous solution of 2-trifluoromethyl-4,6-dinitro-sodium phenolate, 50 g of ethylene glycol and 4 g of Tensiofix CG-21 are added as emulsifier. The solution is made up to 450g with desalted water while stirring
20gew.-%ige ölige Paste20 wt .-% oily paste
620g 2-Trifluormethyl-4,6-dinitrophenol werden in 500g Cyclohexanon gelöst und zu der Lösung 120g kosmetisches Vaselineöl gegeben. Mit Hilfe eines Ultra-turrax-Mischers wird die erhaltene Lösung mit einer 10%igen Lösung des Emulgators Tensiofix PO-132 emulgiert, wobei die Temperatur auf 300C gehalten wird. Das Gemisch wird auf 150C abgekühlt. Innerhalb einer Stunde wird unter langsamen Rühren die 0,2%ige Lösung von Kelsan S in Äthylenglycol in einer Menge von 50g in dem Gemisch verteilt.620 g of 2-trifluoromethyl-4,6-dinitrophenol are dissolved in 500 g of cyclohexanone and added to the solution 120 g of cosmetic Vaseline oil. With the aid of an Ultra-turrax mixer, the resulting solution is emulsified with a 10% solution of the emulsifier Tensiofix PO-132, wherein the temperature is maintained at 30 0 C. The mixture is cooled to 15 0 C. Within one hour, the 0.2% solution of Kelsan S in ethylene glycol in an amount of 50 g is distributed in the mixture with slow stirring.
Wirkungsuntersuchungeneffect studies
Untersuchung der herbiziden Wirkung im GewächshausExamination of the herbicidal effect in the greenhouse
In Anzuchtgefäße wurden die Samen von weißem Senf, krummem Amaranth, weißem Gänsefuß (Melde), italienischem Fennich, Winterweizen und Mais ausgesät. Nach dem Auflaufen wurden die Pflanzen im 2—4 blättrigen Stadium mit 0,2%iger Spritzbrühe (hergestellt durch Verdünnen von aus den Versuchsverbindungen hergestellten 10%igen EC- und WSC-Präparaten) besprüht, wobei jede Verbindung in den Aufwandsmengen von 2,5 5 und 10 kg/ha getestet wurde. Am 14. Tag nach der Behandlung wurde die Schädigung der Pflanzen in Prozent ermittelt. Die Ergebnisse sind in der Tabelle 1 zusammengestellt.The seeds of white mustard, curly amaranth, white goosefoot (reporting), Italian fennich, winter wheat and corn were sown in seed pots. After emergence, the plants were sprayed in the 2-4 leaved stage with 0.2% spray liquor (prepared by diluting 10% EC and WSC preparations prepared from the test compounds), each compound being applied in the amounts of 2.5 5 and 10 kg / ha was tested. On the 14th day after the treatment, the damage to the plants was determined in percent. The results are summarized in Table 1.
Bestimmung der Hemmung der Hill-ReaktionDetermination of inhibition of the Hill reaction
Mittels der Methode von Arnon u. a. wurden aus Spinat Chloroplasten isoliert. Zu einem Gramm von den Adern gereinigter Spinatblätter wurden 6 ml 0,35 molare Kochsalzlösung und 0,6 ml 0,2 molarer TRIS-Puffer gegeben. Das Ganze wurde gemahlen, durch mehrere Schichten Gaze filtriert und dann bei einer Drehzahl von 2000 5 Minuten lang zentrifugiert. Der Clorop9lasten-Niederschlag wurde in 0,035 molarer Kochsalzlösung suspendiert, im Potter-Rohr homogenisiert und die erhaltene Chloroplast-Suspension bei 0°C bis zur Verwendung gelagert.By means of the method of Arnon u. a. were isolated from spinach chloroplasts. To one gram of the strains of purified spinach leaves was added 6 ml of 0.35 molar saline and 0.6 ml of 0.2M TRIS buffer. The whole was ground, filtered through several layers of gauze and then centrifuged at a speed of 2000 for 5 minutes. The cloroparene precipitate was suspended in 0.035 molar saline, homogenized in the Potter tube, and the resulting chloroplast suspension stored at 0 ° C until use.
Aus der Chlöroplast-Suspension und K3Fe(CN)6, K2HPO4, TRIS. HCI-Puffer und MgCI2 wird ein Gemisch bereitet. Zu diesem werden im Konzentrationsbereich von 10~10 bis 10~3 Mol hergestellte Lösungen der Verbindungen der allgemeinen Formel (I) (als Inhibitoren) beziehungsweise als Standardsubstanzen entsprechende Lösungen von N-(3,4-Dichlorphenyl)-N',N-dimethylcarbamid (DCMU) und Dinitro-ortho-kresol (DNOC) gegeben. Die erhaltenen Gemische werden 20 Minuten lang einer Beleuchtungsstärke von 5000 lux ausgesetzt. Dann wird die Reaktion durch Zugabe von 25%iger Trichloressigsäure (TCA) abgebrochen. Der Niederschlag wird durch Zentrifugieren entfernt, und die Extinktion der Lösung wird bei 420 nm mit einem Photometer des Typs Spektromom 204 gemessen. Die Meßreihe wird mit im Dunkeln gehaltenen Proben wiederholt. Die Hemmung der Hill-Reaktion wurde auf Grund des Unterschiedes der Extinktion der im Licht und der im Dunkeln gehaltenen Proben ermittelt und mittels einer Eichkurve in ^g/ml Maliumferrocyanid umgerechnet. (Die Prozentwerte der HemmungFrom the Chlöroplast suspension and K 3 Fe (CN) 6 , K 2 HPO 4 , TRIS. HCI buffer and MgCl 2 , a mixture is prepared. To this are in the concentration range from 10 -10 to 10 -3 mol prepared solutions of the compounds of general formula (I) (as inhibitors) or as standard substances corresponding solutions of N- (3,4-dichlorophenyl) -N ', N-dimethylcarbamid (DCMU) and dinitro-ortho-cresol (DNOC). The resulting mixtures are exposed for 20 minutes to an illuminance of 5000 lux. Then the reaction is stopped by the addition of 25% trichloroacetic acid (TCA). The precipitate is removed by centrifugation and the absorbance of the solution is measured at 420 nm with a Spectrophotometer 204 spectrophotometer. The series of measurements is repeated with samples kept in the dark. The inhibition of the Hill reaction was determined by the difference in absorbance of light and dark samples and converted to μg / ml of malium ferrocyanide by a calibration curve. (The percentages of inhibition
wurden als Funktion der Konzentration dargestellt, und aus der Kurve wurden die zu einer 50%igen Hemmung gehörenden Konzentrationen abgelesen (I50).)were plotted as a function of concentration, and from the curve the concentrations corresponding to a 50% inhibition were read ( I50 ).)
Die Ergebnisse sind in der Tabelle 2 dargestellt.The results are shown in Table 2.
Verbindungconnection
l50(Mikromol/dm3)l 50 (micromoles / dm 3 )
2-TrifIuormethyl-4,6-dinitrophenol2-TrifIuormethyl-4,6-dinitrophenol
2-Trifluormethyl-4,6-dinitrophenol-diäthanolamin 2-Trifluormethyl-4,6-dinitrophenol-dimethylamin 2-Trifluormethyl-4,6-dinitrophenol-NH4 2-trifluoromethyl-4,6-dinitrophenol-diethanolamine 2-trifluoromethyl-4,6-dinitrophenol-dimethylamine 2-trifluoromethyl-4,6-dinitrophenol-NH 4
2-Trifluormethyl-4,6-dinitrophenol-Na2-trifluoromethyl-4,6-dinitrophenol-Na
2-Trifluormethyl-4,6-dinitrophenol-K2-trifluoromethyl-4,6-dinitrophenol-K
Vergleichssubstanzen:Comparison substances:
Dinitro-ortho-kresol-NaDinitro-ortho-cresol-Na
N-(3,4-Dichlorphenyl)-N',N'-N- (3,4-dichlorophenyl) -N ', N'-
dimethylcarbamiddimethylcarbamid
0,21 0,57 0,52 0,25 0,20 0,310.21 0.57 0.52 0.25 0.20 0.31
0,86 0,0710.86 0.071
Aus diesen Angaben ist ersichtlich, daß 2-Trifluormethyl-4,6-dinitropheno! und seine Salze ähnlich wie das N-(3,4-DichlorphenyO-N'.N'-dimethylcarbamid Inhibitoren des zweiten photochemischen Systems sind und ihre Wirksamkeit etwa zwischen der des N-(3,4-Dichlorphenyl)-N',N'-dimethylcarbamids und des Dinitro-ortho-kresols liegt. Von den als Wirkstoff eingesetzten Verbindungen zeigen in diesem Test die Aminsalze eine geringere Wirksamkeit als die Alkali- und Ammoniumsalze.From these data it can be seen that 2-trifluoromethyl-4,6-dinitropheno! and its salts are similar to the N- (3,4-dichlorophenyl-N'.N'-dimethylcarbamide) inhibitors of the second photochemical system and their effectiveness is approximately between that of N- (3,4-dichlorophenyl) -N ', N' Of the compounds used as the active ingredient in this test, the amine salts show less activity than the alkali and ammonium salts.
Untersuchung der herbziden Wirksamkeit an Mais (Freiland) Die Untersuchungen wurden mit dem gemäß Beispiel 3 formulierten 2-Trifluormethyl-4,6-dinitrophenol-Na WSC20 beziehungsweise dem gemäß Beispiel 1 formulierten 2-Trifluormethyl-4,6-dinitrophenol EC60 vorgenommen. Am 25726.April wurden in braunen Waldboden, der 1,8% organische Substanzen enthielt, Maiskörner der Sorte Pioneer 3950 mit einer Keimzahl von73000/ha 8-10cm tief ausgesät. Am 30. Mai wurde mit einer Parzellensprühvorrichtung (Sprühkopf Tee-Jet 11002,1,5atm Druck) und einer Wasseraufwandmenge von 300 Liter/ha gespritzt. Zu diesem Zeitpunkt hatten die meisten Maispfianzen 3-4 Blätter, die meisten Unkräuter 2-4 Blätter. Jede Zusammensetzung wurde in vier Parallelversuchen getestet. Zum Zeitpunkt der Behandlung war die Fläche zu 87,5% mit Unkraut bedeckt. Davon waren 58% Amaranth, 27% Gänsefuß und der Rest Hahnenfuß. Die Wirkung wurde am 15. Juni ausgewertet. Dabei wurden die herbizide Wirkung auf die Unkräuter und die am Mais wahrgenommene phytotoxische Wirkung mit Hilfe der EWRC-Skala bestimmt.Examination of the herbicidal activity on maize (field) The investigations were carried out using the 2-trifluoromethyl-4,6-dinitrophenol-Na WSC20 formulated according to Example 3 or the 2-trifluoromethyl-4,6-dinitrophenol EC60 formulated according to Example 1. On 25726.April, corn kernels of the variety Pioneer 3950 were seeded in brown forest soil containing 1.8% organic substances with a germ count of 73000 / ha 8-10cm deep. On May 30, sprayed with a Parzellensprühvorrichtung (spray head tea jet 11002,1,5atm pressure) and a water application rate of 300 liters / ha. At this time, most corn plants had 3-4 leaves, most weeds had 2-4 leaves. Each composition was tested in four parallel experiments. At the time of treatment, the area was 87.5% covered with weeds. Of these, 58% were amaranth, 27% goosefoot and the remainder ranunculus. The effect was evaluated on 15 June. The herbicidal activity on the weeds and the phytotoxic effect on the maize were determined using the EWRC scale.
Tabelle 3 zeigt die Bewertungsskala, in Tabelle 4 sind die Ergebnisse zusammengefaßt. Jeder Wert ist der Mittelwert von 4 Parallelversuchen.Table 3 shows the rating scale, in Table 4 the results are summarized. Each value is the mean of 4 parallel experiments.
EWRC — WertskalaEEA - Value Scale
Wachstums- und Ertragsförderung bei Mais Am 20. April wurde Mais der Sorte MVSC 3780 mit einer Keimzahl von 55000/ha ausgesät. Zu Beginn der Blütezeit, am 22. Juli, wurde von einem Hubschrauber aus mit 2-Trifluormethyl-4,6-dinitrophenol-Na (20WSC) gesprüht. Die Aufwandmenge betrug 0,25 Liter/ha (= 0,05kg/ha). Jeder der beiden Parallelversuche wurde auf einer 4 Hektar großen Parzelle durchgeführt. ProGrowth and earnings support for corn On April 20, maize of the variety MVSC 3780 with a germ count of 55,000 / ha was sown. At the beginning of flowering on July 22, a helicopter was sprayed with 2-trifluoromethyl-4,6-dinitrophenol-Na (20WSC). The application rate was 0.25 liters / ha (= 0.05 kg / ha). Each of the two parallel experiments was carried out on a 4-hectare plot. Per
Hektar wurden 50 Liter Wasser verwendet. Der Mais wurde am 3. November geerntet. Die Ergebnisse sind in der folgenden Tabelle 5 zusammengestellt.Hectares were used 50 liters of water. The corn was harvested on 3 November. The results are summarized in the following Table 5.
Die Versuche erwiesen, daß das 2-Trifluormethyl-4,6-dinitrophenol-Na seine ertragssteigernde Wirkung über größere Körner und eine bessere Besetzung des Kolbens mit Körnern ausübt.The experiments have shown that the 2-trifluoromethyl-4,6-dinitrophenol-Na exerts its yield-increasing effect on larger grains and a better occupation of the piston with grains.
Seispiel 9 Untersuchung der akariziden Wirksamkeit Die Versuche wurden an in Abständen von 7,5m χ 4,5m gepflanzten Apfelbäumen (Golden delicious) vorgenommen. Am 16. März, vor dem Austreiben der Sprossen wurde von einem Haftlinger-Sprühauto aus mit einer Hochdrucksprühpistole (20 bar) gesprüht, 48 Stunden nach der Behandlung wurden von jeder Parzelle, gleich, ob behandelt oder unbehandelt, 5x10 Fruchttriebe gesammelt (auf jeder Parzelle wuchsen 5 Bäume) und diese im Laboratorium so lange beobachtet, bis im Falle der unbehandelten Kontrolle aller Webermilben ausgeschlüpft waren (12.Tag). Die Mortalität wurde aus der Anzahl der ausgeschlüpften Milben in Prozent der Kontrolle berechnet. Die Ergebnisse sind in der Tabelle 6 angegeben.Example 9 Investigation of the acaricidal activity The experiments were carried out on apple trees (Golden delicious) planted at intervals of 7.5 m χ 4.5 m. On March 16, prior to sprouting the sprouts, sprayed from a Haftlinger sprayer with a high pressure spray gun (20 bar), 48 hours after the treatment, 5x10 fruit shoots were collected from each plot, whether treated or untreated (on each plot 5 trees grew) and these in the laboratory observed so long, in the case of the untreated control all Webermilben had hatched out (12.Tag). The mortality was calculated from the number of hatched mites as a percentage of the control. The results are shown in Table 6.
Die Verbindungen der allgemeinen Formel (I) übertreffen, wie die Tabelle zeigt, die Wirkung der Referenzsubstanz Dinitro-orthokresol (Paste Novenda 25).The compounds of the general formula (I) exceed, as the table shows, the effect of the reference substance dinitro-orthocresol (Paste Novenda 25).
O-XO-X
O2MO 2 M
(I(I
/VO:/ VO:
Claims (3)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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HU83362A HU190439B (en) | 1983-02-03 | 1983-02-03 | Herbicidal, akaricidal and plant growth regulating compsitions comprising 2-/trifluoromethyl/-4,6-dinitrophenol or its salts as active substance and process for preparing the active substances |
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DD84259849A DD215535A5 (en) | 1983-02-03 | 1984-02-03 | PROCESS FOR PRODUCING NEW DINITROPHENOLES |
DD84266211A DD231714A5 (en) | 1983-02-03 | 1984-08-13 | PLANT PROTECTION AGENTS AND METHODS OF CONCENTRATING SCHAEDLINGEN AND UNKRAEUTERN |
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JPS55139341A (en) * | 1979-04-18 | 1980-10-31 | Kumiai Chem Ind Co Ltd | Dinitrophenol derivative, its preparation, and agricultural and horticultural germicidal and herbicidal agent, containing it as effective component |
DE3315798A1 (en) * | 1983-04-30 | 1984-10-31 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING 6-CHLORINE-2,4-DINITROPHENOL |
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ATA33384A (en) | 1987-04-15 |
ES529614A0 (en) | 1985-08-01 |
GB2135993B (en) | 1987-05-07 |
HU190439B (en) | 1986-09-29 |
CS80184A2 (en) | 1987-11-12 |
IT1173208B (en) | 1987-06-18 |
JPS6041639A (en) | 1985-03-05 |
DE3403437A1 (en) | 1984-08-09 |
PL246022A1 (en) | 1985-01-30 |
PL137335B1 (en) | 1986-05-31 |
FR2540489B1 (en) | 1987-08-21 |
AU579090B2 (en) | 1988-11-17 |
AT384422B (en) | 1987-11-10 |
GB2135993A (en) | 1984-09-12 |
DK47384D0 (en) | 1984-02-02 |
DK47384A (en) | 1984-08-04 |
CH658243A5 (en) | 1986-10-31 |
HUT33948A (en) | 1985-01-28 |
CS257773B2 (en) | 1988-06-15 |
FR2540489A1 (en) | 1984-08-10 |
IT8419428A0 (en) | 1984-02-02 |
RO88543A (en) | 1986-02-28 |
GR81696B (en) | 1984-12-12 |
GB8402445D0 (en) | 1984-03-07 |
ES8506581A1 (en) | 1985-08-01 |
GB8402952D0 (en) | 1984-03-07 |
YU19584A (en) | 1988-04-30 |
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