WO2001090085A2 - Composes 6-methyl-4-trihalogenmethyltriazine - Google Patents

Composes 6-methyl-4-trihalogenmethyltriazine Download PDF

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Publication number
WO2001090085A2
WO2001090085A2 PCT/EP2001/005954 EP0105954W WO0190085A2 WO 2001090085 A2 WO2001090085 A2 WO 2001090085A2 EP 0105954 W EP0105954 W EP 0105954W WO 0190085 A2 WO0190085 A2 WO 0190085A2
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
phenyl
compounds
hydrogen
methyl
Prior art date
Application number
PCT/EP2001/005954
Other languages
German (de)
English (en)
Other versions
WO2001090085A3 (fr
Inventor
Steffen Kudis
Peter Plath
Ulf Misslitz
Markus Menges
Matthias Witschel
Helmut Walter
Cyrill Zagar
Original Assignee
Basf Aktiengesellschaft
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.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to AU76342/01A priority Critical patent/AU7634201A/en
Publication of WO2001090085A2 publication Critical patent/WO2001090085A2/fr
Publication of WO2001090085A3 publication Critical patent/WO2001090085A3/fr

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Classifications

    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom

Definitions

  • R 1 trichloromethyl, dichlorofluoromethyl or chlorodifluoromethyl
  • A is a single bond, linear or branched Ci-Co alkylene, in which one or two carbon atoms which are not adjacent to group X and group CR 3 R 4 can be replaced by oxygen;
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 6 -alkanoic acids, preferably Formate, acetate, propionate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • C 1 -C 6 -alkyl for: C 1 -C -alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1 , 1-Dimethylpropy1, 1, 2-Dimethylpropy1, 1-Methylpenty1, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl,
  • Ci-Cs-alkyl for: Ci-Cg-alkyl as mentioned above, and e.g. n-heptyl, 2-ethylhexyl and n-octyl;
  • C 2 -C 6 alkynyl for straight-chain or branched hydrocarbon groups having 2 to 6 carbon atoms and a triple bond in any position, e.g. B. ethynyl and C 3 -C 6 -alkynyl such as prop-1-in-l-yl, prop-2-in-l-yl, n-but-1-in-l-yl, n-but-l- in-3-yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in- 3-yl, n-pent-l-in-4-yl, n-pent-l-in-5-yl, n-pent-2-in-l-yl, n-pent-2-in-4- yl, n-pent-2-yn-5-yl, 3-methyl-but-l-yn-3-yl, 3-
  • _ 3 -C 6 -cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;
  • Thiocarbonyl ring member contains e.g. for cyclobutanon-2-yl, cyclobutanon-3-yl, cyclopentanon-2-yl, cyclopentanon-3-yl,
  • Cyclooctanthion-2-yl preferably for cyclopentanon-2-yl or cyclohexanon-2-yl
  • R 3 is hydrogen or -CC 4 alkyl, especially methyl
  • groups Ar which are suitable according to the invention are: 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-hydroxyphenyl, 2-, 3- or 4-trifluoromethylphenyl, 2-, 3- or 4-trif uormethoxyphenyl, 2-, 3- or 4-methylthiophenyl, 2-, 3- or 4-difluoromethoxyphenyl, 2-, 3- or 4-bromophenyl, 2-, 3- or 4-tolyl , 2-, 3- or 4-anisyl, 2-, 3- or 4-allyloxyphenyl, 2-, 3- or 4-propargyloxyphenyl, 2-, 3- or 4-nitrophenyl, 2-, 3- or 4-cyanophenyl , 3- or 4-isopropylphenyl, 3- or 4- (2, 2, 2-trifluoroethyl) phenyl, 3- or 4-ethynylphenyl, 3- or 4-ethenylphenyl, 3- or 4-acetylphenyl, 3-
  • compounds of general formula IA.f are particularly preferred (compounds of general formula IA in which R 2 is acetyl and R 4 is hydrogen, A is methylene, X is a single bond and R ° is hydrogen).
  • preferred compounds of the general formula IA.f are the compounds IA.f-1 to IA.f-657, in which the variables R 1 , R 3 , R a and R b in formula IA.f together in each case in one Row of Table 1 have the meanings given.
  • compounds of general formula iA.k are particularly preferred (compounds of general formula IA in which R 2 and R 4 are hydrogen, A is methylene, X is an oxygen atom and R c is hydrogen).
  • preferred compounds of the general formula IA.k are the compounds IA.k-1 bis IA.k-657, in which the variables R 1 , R 3 , R a and R b in formula IA.k together have the meanings given in one row of Table 1.
  • compounds of general formula IA.m are particularly preferred (compounds of general formula IA in which R 2 is acetyl and R 4 is hydrogen, A is methylene, X is an oxygen atom and R c is hydrogen).
  • Examples of preferred compounds of the general formula IA.m are the compounds IA.m-1 to IA.m-657, in which the variables R 1 , R 3 , R a and R b in the formula IA.m together are in each case one Row of Table 1 have the meanings given.
  • Particularly noteworthy is the reaction with acylating agents for introducing radicals R 5 C (0), the reaction with, for example, azidoformic acid esters R 5 OC (0) N 3 or carbonic anhydrides [R 5 OC (0)] 2 0 for introduction of residues R 5 OC (0) or with isocyanates R 5 NCO to introduce residues R 5 NHC (0).
  • CC1 3 can be prepared, for example, by reacting the N- (acetamidinyl) tichloroacetamidine IV with a carboxylic anhydride of the general formula [R 1 -C (0)] 2 0 under the reaction conditions given in GB 912,112.
  • Compound IV can be prepared, for example, in a known manner by basic condensation of acetamidine hydrochloride with trichloroacetonitrile (cf. GB 912.112 and Backer and Wanmaker, Rec. Trav. Chim. 70, 1951, p. 644).
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • VI 20 parts by weight of compound I are intimately mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condesate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
  • racem racemate
  • S S configuration on the C atom bearing R 3 .
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • compound no. IA.a-523 shows a very good herbicidal action against AMARE, ABUTH, BIDPI, GALAP and SETFA in the post-emergence with high selectivity at the same time spring wheat.
  • compound no. IA.a-82 shows a very good herbicidal action against AMARE, ABUTH, CHEAL, POLPE and SETFA in post-emergence.
  • compound no. 1A-9 shows a very good herbicidal action against AMARE, ABUTH, PHBU and SETFA in the post-emergence, with high selectivity in rice at the same time.
  • compound no. IA.a-515 shows a very good herbicidal action against AMARE, ABUTH, BIDPI, POLPE and SETFA in the post-emergence ,
  • compound no. IA.a-512 shows a very good herbicidal action against AMARE, ABUTH, BIDPI, POLPE and SETFA in post-emergence.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des composés 4-halogenalkyltriazine de formule générale I, dans laquelle les variables R?1, R2, R3, R4¿, A, X, et Ar ont les significations mentionnées dans la revendication 1, ainsi que l'utilisation de ces composés comme herbicides.
PCT/EP2001/005954 2000-05-26 2001-05-23 Composes 6-methyl-4-trihalogenmethyltriazine WO2001090085A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU76342/01A AU7634201A (en) 2000-05-26 2001-05-23 6-methyl-4-trihalomethyltriazine compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10026231 2000-05-26
DE10026231.7 2000-05-26

Publications (2)

Publication Number Publication Date
WO2001090085A2 true WO2001090085A2 (fr) 2001-11-29
WO2001090085A3 WO2001090085A3 (fr) 2002-08-01

Family

ID=7643723

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2001/005954 WO2001090085A2 (fr) 2000-05-26 2001-05-23 Composes 6-methyl-4-trihalogenmethyltriazine

Country Status (2)

Country Link
AU (1) AU7634201A (fr)
WO (1) WO2001090085A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7153822B2 (en) 2002-01-29 2006-12-26 Wyeth Compositions and methods for modulating connexin hemichannels
EP2327700A1 (fr) 2009-11-21 2011-06-01 Bayer CropScience AG Dérivés de triazine et leur utilisation pour combattre la croissance indésirable de plantes

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997020825A1 (fr) * 1995-12-07 1997-06-12 Tomono Agrica Co., Ltd. Derives de triazine et sels de ces derives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11246528A (ja) * 1997-12-05 1999-09-14 Tomono Agrica Co Ltd 含窒素芳香族化合物およびその塩

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997020825A1 (fr) * 1995-12-07 1997-06-12 Tomono Agrica Co., Ltd. Derives de triazine et sels de ces derives

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
KUBOYAMA, NOBUHIRO ET AL: "Photosynthetic electron transport inhibitory activity of 2-aralkylamino-4-methyl-6-trifluoromethyl- 1,3,5-triazine derivatives" J. PESTICIDE SCI. (1999), 24(2), 138-142, XP001041684 *
KUBOYAMA, NOBUHIRO ET AL: "Synthesis and herbicidal activity of 2-benzylamino-4-methyl-6- trifluoromethyl-1,3,5-triazine derivatives" J.PESTICIDE SCI. (1998), 23(3), 268-274, XP001041685 *
OKANO, NATSUKO ET AL: "Synthesis and structure-activity relationship of newer trichloromethyl-1,3,5-triazine nitrification inhibitors" J. PESTIC. SCI. (INT. ED.) (1993), 18(4), 361-8, XP002184346 *
PATENT ABSTRACTS OF JAPAN vol. 1999, no. 14, 22. Dezember 1999 (1999-12-22) & JP 11 246528 A (TOMONO AGRICA CO LTD), 14. September 1999 (1999-09-14) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7153822B2 (en) 2002-01-29 2006-12-26 Wyeth Compositions and methods for modulating connexin hemichannels
EP2327700A1 (fr) 2009-11-21 2011-06-01 Bayer CropScience AG Dérivés de triazine et leur utilisation pour combattre la croissance indésirable de plantes

Also Published As

Publication number Publication date
WO2001090085A3 (fr) 2002-08-01
AU7634201A (en) 2001-12-03

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