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WO1992008719A1 - PYRIDO[2,3-d]PYRIMIDIN-2,4(1H,3H)-DIONES - Google Patents

PYRIDO[2,3-d]PYRIMIDIN-2,4(1H,3H)-DIONES Download PDF

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Publication number
WO1992008719A1
WO1992008719A1 PCT/EP1991/002055 EP9102055W WO9208719A1 WO 1992008719 A1 WO1992008719 A1 WO 1992008719A1 EP 9102055 W EP9102055 W EP 9102055W WO 9208719 A1 WO9208719 A1 WO 9208719A1
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Prior art keywords
alkyl
alkylthio
group
alkoxy
thiocarbonyl
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German (de)
English (en)
Inventor
Helmut Hagen
Peter Raatz
Helmut Walter
Andreas Landes
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BASF SE
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BASF SE
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Priority to KR1019930701368A priority Critical patent/KR930702293A/ko
Priority to CA002095433A priority patent/CA2095433A1/fr
Priority to JP3517111A priority patent/JPH06502152A/ja
Publication of WO1992008719A1 publication Critical patent/WO1992008719A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to pyrido [2,3-d] pyrimidine-2,4 (1H, 3H) -diones of the general formulas 1a and 1b
  • R 1 , R 2 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or
  • R 3 is hydrogen, C 1 -C 4 alkyl, amino, hydroxy, mercapto,
  • R 4 are hydrogen, C 4 alkyl, C ⁇ -C 4 alkoxycarbonyl, C 1 -C 4 - (alkylthio) carbonyl, C ⁇ -C4-alkoxy (thiocarbonyl), C 1 -C 4 - (alkylthio) thiocarbonyl , Cyano or aminocarbonyl; or
  • R 3 u. R 4 together C 3 -C 6 alkylene, C 3 -C 6 alkenylene or
  • R 5 is hydrogen, C 1 -C 4 alkyl, cyano, a group C (O) R 7 or a group C (S) R 7 ;
  • R 6 is C 1 -C 4 alkyl, C 6 aryl (C 2 -C 4 ) alkenyl, C 6 -, C 10 - or
  • C 14 aryl where the aryl groups can carry one to three of the groups mentioned for R 11 , a group CH 2 R 8 , C 1 -C 4 alkoxycarbonyl, C 1 -C 4 - (alkylthio) carbonyl,
  • R 8 halogen, hydroxy, mercapto, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 - (alkylthio) carbonyl, C 1 -C 4 alkoxy (thiocarbonyl), C 1 -C 4 - (alkylthio) thiocarbonyl or a group
  • R 9 is C 1 -C 5 alkyl, C 1 -C 4 haloalkyl, a group NR 1 R 2 or a group OR 1 ;
  • R 10 is C 1 -C 4 alkyl, C 6 - or C 10 aryl, which can carry one to three of the groups mentioned for R 11 ;
  • R 11 is halogen, hydroxy, mercapto, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkyl, nitro or amino;
  • R 1 and R 2 are not simultaneously H, methyl or ethyl, b) R 3 and R 4 are not simultaneously H, c) R 5 and R 6 are not simultaneously H, d) if R 1 Methyl, R 2 is i-butyl and R 3 is amino, R 4 is not H, e) if R 1 is methyl, R 2 H and R 5 are phenyl, R 6 is not
  • Hydroxy is f) if R 1 is methyl, R 2 H and R6 are amino, R 5 is not carboxy or ethoxycarbonyl, g) if R 1 is H, R 2 is methyl and R 5 is H, R 6 is not hydroxy, h) if R 1 H, R 2 are methyl and R 4 are ethoxycarbonyl, R 6 is not methyl or amino, i) if R 5 is cyano, R 6 is hydroxy and R 1 is n-butyl, R 2 is not H, j) if R 5 is cyano, R 6 is hydroxy and R 1 is n-propyl, R 2
  • the invention relates to processes for the preparation of the compounds Ia and Ib and herbicidal compositions which contain 2- (4-heteroaryloxy) - or 2- (4-aryloxy) -phenoxyacetic acid or propionic acid derivatives and / or cyclohexenone derivatives as herbicides
  • Contain active substances and compounds la and Ib as antidotes Contain active substances and compounds la and Ib as antidotes, and methods for the selective control of undesirable plant growth with these herbicidal compositions.
  • R a is a phenyl group, a pyridyl group, a benzoxazyl group, a benzothiazyl group or a benzpyrazinyl group, where these aromatic ring systems can carry up to two of the following radicals: halogen, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 ⁇ haloalkoxy,
  • R b is hydrogen, a C 1 -C 4 alkyl group or the equivalent
  • a plant-compatible cation and R c are hydrogen or a methyl group, are from the literature, for example from DE-A-2223894, DE-A-2433067, DE-A-25 76 251, DE-A-30 04770, BE-A-868875 and BE-A-858618 (see also Table A).
  • R d is a C 1 -C 6 alkyl group
  • A is a C 4 -alkylene or C 4 -alkenylene chain, these chains being able to carry one to three C 1 -C 3 -alkyl groups and / or halogen atoms or a 3- to 6-membered group optionally substituted by C 1 -C 3 -alkyl Alkylene chain which contains an oxygen or sulfur atom not directly adjacent to the oxime ether part as a ring member;
  • Halogen C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkyloxy, carboxyl, C 1 -C 4 - Alkoxycarbonyl and / or benzyloxycarbonyl; n is 0 to 3 or 1 to 5 if B is halogen;
  • R e is a C 1 -C 4 alkoxy-C 1 -C 6 alkyl or C 1 -C 4 alkylthio-C 1 - C 6 alkyl group; a C 3 -C 7 cycloalkyl group or a C 5 -C 7 cycloalkenyl group, where these groups can carry one to three of the following substituents: C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, hydroxy and / or
  • Halogen a 5-membered saturated heterocycle which contains one or two oxygen and / or sulfur atoms as heteroatoms and which can carry up to three of the following groups:
  • -C 4 alkyl a phenyl group or a pyridyl group, where these groups can carry one to three of the following substituents: halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy and / or -NR f R g , wherein
  • R f is hydrogen, a C 1 -C 4 alkyl group, a C 3 -C 6 alkenyl group or a C 3 -C 6 alkynyl group and R 9 is hydrogen, a C 1 -C 4 alkyl group, a C 3 -C 6 alkenyl group, a C 3 -C 6 alkynyl group, a C 1 -C 6 acyl group or a benzoyl radical, the aromatic ring being one to three of the following substituents: nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio and / or C 1 -C 4 haloalkyl.
  • the object of the invention was to provide compounds which at least reduce the disadvantages which exist when using the abovementioned herbicides of the formulas XI and XII to such an extent that the crop yield of the crop plants is no longer or not significantly reduced. Accordingly, the compounds la and Ib defined at the outset were found.
  • alkali metal salts in particular the potassium or sodium salt, alkaline earth metal salts, in particular the calcium, magnesium or barium salt, manganese, copper, zinc or iron salts and ammonium, phosphonium, sulfonium or sulfoxonium salts, for example, are preferred Ammonium salts, tetraalkylammonium salts, benzyltriarylammonium salts, trialkylsulfonium salts or trialkylsulfoxonium salts.
  • R 1 , R 2 are hydrogen; C 1 -C 4 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, especially methyl and ethyl; C 1 -C 4 haloalkyl, especially C 1 -C 2 haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,
  • C 3 -C 7 cycloalkyl such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, especially cyclopropyl;
  • R 3 is hydrogen, hydroxy, mercapto, amino; C 1 -C 4 alkyl as mentioned for R 1 , especially methyl and
  • Ethyl, C 1 -C 4 alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;
  • C 6 - or C 10 -aryl such as phenyl, naphthyl, which can carry one to three of the groups mentioned for R 11 , preferably nitro, fluorine and chlorine;
  • R 4 is hydrogen; C 1 -C 4 alkyl as mentioned for R 1 , preferably methyl and ethyl; C 1 -C 4 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl, 1-methylethoxycarbonyl,
  • butyloxycarbonyl 1-methylpropyloxycarbonyl, 2-methylpropyloxycarbonyl, 1,1-dimethylethoxycarbonyl;
  • C 3 -C 6 - (alkylthio) carbonyl such as (methylthio) carbonyl, (ethylthio) carbonyl, (propylthio) carbonyl, (1-methylethylthio) carbonyl, (butylthio) carbonyl, (1-methylpropylthio) carbonyl, (2-methylpropylthio) carbonyl, (1,1-dimethylethylthio) carbonyl;
  • C 1 -C 4 alkoxy (thiocarbonyl) such as methoxy (thiocarbonyl), ethoxy (thiocarbonyl), propyloxy (thiocarbonyl), 1-methylethoxy (thiocarbonyl), butyloxy (thiocarbonyl), 1-methylpropyloxy (thiocarbonyl), 2-methylprop
  • But-2-en-1,4-ylene; 1,2-phenylene; R 5 is hydrogen, C 1 -C 4 -alkyl as mentioned for R 1 , preferably methyl and ethyl; the groups C (O) R 7 and C (S) R 7 , in which R 7 preferably denotes amino, methoxy, ethoxy, hydroxy, methyl, ethyl, phenyl, methoxycarbonyl, ethoxycarbonyl;
  • R 6 C 1 -C 4 alkyl as mentioned for R 1 , preferably methyl and
  • C 6 - or C 10 -aryl such as phenyl, naphthyl, which can carry one to three of the groups mentioned for R 11 , preferably chlorine, nitro and methyl; the group CH 2 R 8 , where R 8 preferably represents chlorine, methoxycarbonyl and hydroxycarbonyl; C 1 -C 4 alkoxycarbonyl as mentioned for R 4 ; C 1 -C 4 - (alkylthio) carbonyl as mentioned for R 4 ; C 1 -C 4 alkoxy (thiocarbonyl) as mentioned for R 4 ; C 1 -C 4 - (alkylthio) thiocarbonyl as mentioned for R 4 ;
  • C 1 -C 4 alkoxy such as methoxy, ethoxy, propyloxy, 1-methylethoxy, butyloxy, 1-methyl-propyloxy, 2-methylpropyloxy and 1,1-dimethylethoxy, particularly preferably 1-methylethoxy
  • C 1 -C 4 alkylthio as mentioned for R 3
  • C 1 -C 4 alkylamino such as methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino
  • the group NHCXR9 where X is preferably oxygen, in particular methylcarbonylamino and ethylcarbonylamino
  • NHSO 2 R 10 in particular 4-tolylsulfonamino
  • R 6 together C 3 -C 6 alkylene such as tri- and tetramethylene, C 3 -C 5 alkenylene such as prop-1-en-1,3-ylene, but-1-en-1,4-ylene and but- 2-en-1,4-ylene or 1,2-phenylene, with C 1 -C 4 alkyl such as methyl and ethyl, C 1 -C 4 haloalkyl such as trifluoromethyl and C 3 -C 7 cycloalkyl such as cyclo propyl, cyclopentyl and cyclohexyl can be mono- or disubstituted and can also contain carbonyl or thiocarbonyl groups, particularly preferred are prop-1,3-diyl-carbonyl, 2, 2-dimethyl
  • Di- (C 1 -C 4 alkyl) amino such as N, N-dimethylamino, N, N-diethylamino, N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino , N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1,1-dimethylethyl) amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino,
  • R 9 C 1 -C 4 alkyl as mentioned for R 1 , particularly preferably methyl and ethyl; C 1 -C 4 haloalkyl as mentioned for R 1 ; the group NR 1 R 2 , preferably amino, dimethylamino; the group OR 1 , preferably hydroxy, methoxy, ethoxy; R 10 C 1 -C 4 alkyl as mentioned for R 1 ; C 6 - or C 10 -aryl such as phenyl, naphthyl, which can carry one to three of the groups mentioned for R 11 , in particular 2-methylphenyl, 3-methylphenyl, 4-methylphenyl;
  • R 11 halogen, especially fluorine and chlorine; Hydroxy;
  • the compounds I according to the invention are accessible in various ways.
  • Substituted pyridopyrimidines are obtained e.g. by condensation of 4-aminopyrimidines with ethoxymethylene-malonic acid derivatives or by reaction of 4-amino-5-formylpyrimidines with ⁇ -diketones (E. Lunt and CG. Newton in
  • the reaction mixture is subsequently heated to a temperature in the range from 20 to 150, preferably from 70 to 110 ° C., and is left there for 3 to 12, in particular 5 to 7, hours before it is cooled to room temperature.
  • Solid products are generally obtained which precipitate as solids during cooling and can be separated off by customary methods.
  • the molar ratio of compound II to alkenal III is generally chosen in the range from 0.7: 1 to 1.2: 1.
  • the pyrimidine derivatives II are generally known and easily accessible (see D.J. Brown in Comprehensive Heterocycl. Chem., Vol. 3, Pergamon Press, Oxford, pp. 106-142).
  • Another method of preparing the pyridopyrimidine derivatives Ia is to react the compound II with a ⁇ -alkoxyacrylic acid derivative IV using a method known per se, which is described in J. Heterocyclic Chem. 22 (1985), 1469, the intermediate V is generally isolated and then reacted further to the compound la at elevated temperature.
  • those ⁇ -alkoxyacrylic acid derivatives IV are used in which R 12 is C 2 -C 5 -alkoxycarbonyl, C 2 -C 5 -alkoxythiocarbonyl or cyano and Rl3 for a C2-Cs-alkyl group such as ethyl, n-propyl, 1- Methylethyl, n-butyl, 1,1-dimethylpropyl or n-pentyl.
  • the compounds IV are generally known and easily accessible.
  • the starting compounds Ib can be obtained, for example, in a known manner by reacting a compound II with a ⁇ -aminoalkyl ketone VI (see Arch. Pharm., 311 (1978), 406).
  • the R5 ' is preferably hydrogen and C 1 -C 4 alkyl, in particular methyl and ethyl
  • R 14 is C 1 -C 4 alkyl, preferably methyl and ethyl.
  • Another method of preparing the compounds Ib consists in reacting a pyrimidine derivative VIIa or VIIIb in a manner known per se (see J. Heterocycl. Chem. 22 (1985) 345) with a malonic acid derivative Villa, VHIb or VIIIc.
  • R 5 denotes cyano, the group C (O) R 7 or the group C (S) R 7 , R 15 C 1 -C 4 alkyl such as methyl, ethyl, n-propyl, i-propyl, n-butyl , i-butyl, sec.-butyl, tert.-butyl, especially ethyl;
  • R 6 ' C 1 -C 4 alkyl, as mentioned under R 15 , in particular methyl;
  • C 6 -, C 10 - or C 14 -aryl such as phenyl and naphthyl, especially phenyl; wherein the aryl groups can carry one to three of the groups mentioned for R 11 or the group CH 2 R 8 .
  • the compounds Ib can be prepared by preparing a compound Ib in which R 6 is hydroxy in a manner known per se (see P. Gurtyus, P. Sohär and H. Wamhoff, Liebigs Ann. Chem. (1984 ), 1653) with the compound IX, R 16 -Nu.
  • R 16 stands for C 1 -C 4 alkyl as mentioned under R 1 , preferably i-propyl and n-butyl, and Nu means a nucleofugic leaving group such as a halogen, preferably iodine.
  • An additional method of preparing the compounds Ib is to prepare a compound Ib in which R 6 is amino in a manner known per se with a compound Xa, R9 (cx) Nu, or Xb, R 10 -SO 2 -Nu to implement.
  • Specific examples of herbicidal (heteroaryloxy) or aryloxyphenoxyacetic acid derivatives of the formula XI are listed in Table A below.
  • Specific examples of herbicidal cyclohexenones of the formula XII are listed in Tables B to R below (see German applications DE-A 4014985 and
  • Herbicidal agents and antidote compounds can be applied together or separately after emergence onto the leaves and shoots of the crop plants and the unwanted grasses.
  • the antidote agent is preferably applied simultaneously with the herbicidal active ingredient.
  • Herbicidal active ingredient and antidote can be formulated here as a spraying agent in suspendable, emulsifiable or soluble form together or separately.
  • treating the crop seeds with the antidote before sowing is also important.
  • the herbicidal active ingredient is then applied alone in the customary manner.
  • herbicidal (heteroaryloxy) or aryloxyphenoxyacetic acid derivatives XI different amounts of an antidote compound are required if the herbicide is used in different crops.
  • the proportions are variable in a wide range. They are also dependent on the structure of the (heteroaryloxy) or aryloxyphenoxyacetic acid derivatives and the particular target culture.
  • Suitable proportions of antidote compound: herbicidal active ingredient are between 0.01: 1 to 10: 1; preferably between 0.1: 1 to
  • herbicidal active ingredient are between 0.01: 1 to 10: 1, preferably 0.25: 1 to 4: 1 parts by weight both when applied together and when applied separately.
  • the new herbicidal compositions can comprise further herbicidal or growth-regulating active compounds of other chemical structure, the antagonistic effect being retained .
  • the herbicidal active ingredients or the antidote are, for example, in the form of directly sprayable solutions, powders, suspensions, also high-strength aqueous, oily or other suspensions, or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents or granules applied by spraying, atomizing, dusting, scattering or pouring.
  • strongly polar solvents such as e.g. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders), oil dispersions by adding water.
  • herbicidal active ingredient and / or antidote as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of herbicidal active ingredient and / or antidote, wetting agents, adhesives, dispersants or emulsifiers and, if appropriate, solvents or oil, which are suitable for dilution with water are suitable for dilution with water.
  • Polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin sulfite liquors and methyl cellulose are considered.
  • Powders, materials for spreading and dusts can be prepared by mixing or grinding the herbicidal active ingredient and / or antidote together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin,
  • Attaclay limestone, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as flour, tree bark, wood and nutshell flour,
  • the formulations contain between 0.01 and 95% by weight of herbicidal active ingredient and antidote, preferably between 0.5 and 90% by weight.
  • the application rates of herbicidal active ingredient are 0.2 to 5 kg / ha of active substance (a.S.).
  • reaction mixture was then heated to 95 ° C. over 30 minutes and held at this temperature for 6 hours.
  • the mixture was then cooled to room temperature and the product was separated off by filtration. After drying, 15.6 g (67%) of yellow crystalline product remained (active ingredient example 1.006).
  • test plants For the post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 20 cm and only then treated.
  • the herbicidal compositions were suspended or emulsified in water as distribution agents and sprayed by means of finely distributing nozzles.
  • herbicidal active ingredients were each in the form of commercially formulated products (100 g / l emulsion concentrate)
  • test vessels were set up in the greenhouse, with 18 to 30 ° C being preferred for heat-loving species and 10 to 25 ° C for those from temperate climates.
  • the agents were suspended in water as carriers and distributing agents and applied to the plants dripping wet using a mobile spray booth which had finely distributing nozzles.
  • the trial period lasted 3 to 5 weeks. During this time, the plants were cared for and their response to each treatment was monitored.
  • the damage caused by the chemical agents was assessed on a scale from 0 to 100% compared to the untreated control plants. 0 means no damage and 100 means complete destruction of the plants.
  • the antidotic example compounds significantly improve the tolerance of the herbicides B.15 and E.34 for crops belonging to the family of the Gramineae (grasses).
  • Table 6 The antidotic example compounds significantly improve the tolerance of the herbicides B.15 and E.34 for crops belonging to the family of the Gramineae (grasses).
  • Antidote herbicide Antidote crop undesirable plant no.Mize Setaria viridis - 0.125 75 100

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Abstract

Des pyrido[2,3-d]pyrimidin-2,4(1H,3H)-diones ont la formule (Ia) et (Ib), dans lesquelles R1, R2 désignent H, alkyle, cycloalkyle substitués ou non; R3 désigne H, alkyle substitué ou non; R4 désigne H, alkyle, alcoxycarbonyle, (alkylthio)carbonyle, alcoxy(thiocarbonyle), (alkylthio)thiocarbonyle, cyano ou aminocarbonyle; ou R3 et R4 désignent ensemble alcylène, alcénylène ou 1,2-phénylène; R5 désigne H, alkyle, cyano, C(O)R?7, C(S)R7; R6¿ désigne alkyle, aralcényle, aryle ou hétaryle éventuellement substitués, CH¿2R?8, alcoxycarbonyle, (alkylthio)carbonyle, alcoxy(thiocarbonyle), (alkylthio)thiocarbonyle, OH, SH, alcoxyle, alkylthio, NH¿2?, alkylamino, NHCXR?9¿, NHSO¿2?R?10; R5 et R6¿ désignent ensemble alcylène, alcénylène ou 1,2-phénylène éventuellement substitués pouvant également contenir des groupes carbonyles ou thiocarbonyles; R7 désigne H, alkyle, OH, SH, alcoxyle, alkylthio, alcoxycarbonyle, (alkylthio)carbonyle, alcoxy(thiocarbonyle), (alkylthio)thiocarbonyle, NH¿2?, alkylamino, dialkylamino, aryle ou arylamino éventuellement substitués; R?8¿ désigne halogène, OH, SH, alcoxyle, alkylthio, alcoxycarbonyle, (alkylthio)carbonyle, alcoxy(thiocarbonyle), (alkylthio)thiocarbonyle ou la formule (a); R9 désigne alkyle, alkyle halogène, NR?1R2 ou OR1; R10¿ désigne alkyle, aryle substitué ou non, R11 désigne halogène, OH, SH, alcoxyle, alkylthio, alkyle, nitro ou amino; X désigne oxygène ou soufre. L'invention concerne ces composés, ainsi que leurs sels utilisables en agriculture, qui contiennent un substituant azotique ou hydroxyle, et des herbicides qui contiennent des dérivés d'acide propionique ou phénoxyacétique 2-[4-(hétéro)-aryloxyle] et/ou des dérivés de cyclohexenone en tant que substances herbicides actives et des pyrido[2,3-d]pyrimidin-2,4(1H, 3H)-diones, ainsi que, dans le cas où des groupes terminaux acides ou des atomes basiques d'azote sont présents, les sels de (Ia) ou de (Ib) en tant qu'antidotes.
PCT/EP1991/002055 1990-11-08 1991-10-30 PYRIDO[2,3-d]PYRIMIDIN-2,4(1H,3H)-DIONES Ceased WO1992008719A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1019930701368A KR930702293A (ko) 1990-11-08 1991-10-30 치환 피리도[2,3-d]피리미딘-2,4(1H,3H)-디온
CA002095433A CA2095433A1 (fr) 1990-11-08 1991-10-30 Derives de substitution de pyrido[2,3-d]pyrimidine-2,4(1h,3h)-diones
JP3517111A JPH06502152A (ja) 1990-11-08 1991-10-30 置換ピリド〔２，３−ｄ〕−ピリミジン−２，４（１Ｈ，３Ｈ）−ジオン

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4035479A DE4035479A1 (de) 1990-11-08 1990-11-08 Substituierte pyrido (2,3-d)pyrimidin-2,4(1h,3h)-dione
DEP4035479.2 1990-11-08

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WO1992008719A1 true WO1992008719A1 (fr) 1992-05-29

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PCT/EP1991/002055 Ceased WO1992008719A1 (fr) 1990-11-08 1991-10-30 PYRIDO[2,3-d]PYRIMIDIN-2,4(1H,3H)-DIONES

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EP0537463A3 (en) * 1991-09-18 1993-05-26 Basf Aktiengesellschaft Substituted pyrido(2,3-d)pyrimidines as antidotes
EP0696590A1 (fr) * 1994-06-17 1996-02-14 Nippon Zoki Pharmaceutical Co., Ltd. Dérivés de pyrido 2,3-d pyrimidine, leurs préparation et leurs utilisation comme agents anti-asthmatiques
US5502177A (en) * 1993-09-17 1996-03-26 Gilead Sciences, Inc. Pyrimidine derivatives for labeled binding partners
US6242452B1 (en) 1998-10-15 2001-06-05 Nippon Zoki Pharmaceutical Co., Ltd. 7-aminopyrido[2,3-D]pyrimidine derivatives
US6440978B2 (en) 2000-04-13 2002-08-27 Nippon Zoki Pharmaceutical Co., Ltd. Therapeutic agent for dermatitis
US6787554B2 (en) 2001-11-26 2004-09-07 Warner-Lambert Llc Triazolo[4,3-a]pyrido[2,3-d]pyrimidin-5-one derivatives
CN101597277B (zh) * 2008-06-04 2011-08-03 山东新时代药业有限公司 S-泮托拉唑及盐的制备方法
WO2015186061A1 (fr) 2014-06-03 2015-12-10 Novartis Ag Dérivés de pyridopyrimidinedione
WO2015186063A1 (fr) 2014-06-03 2015-12-10 Novartis Ag Dérivés de naphthyridinédione
US9327039B2 (en) 2004-12-16 2016-05-03 Resolution Chemicals Limited Particle size reduction apparatus, and use thereof
CN108727367A (zh) * 2017-04-18 2018-11-02 山东先达农化股份有限公司 含吡啶并嘧啶二酮的苯并噁嗪酮类化合物及其制备方法和应用和除草剂组合物
US20210122750A1 (en) * 2019-10-25 2021-04-29 Saint Louis University Gpr183 antagonists for the treatment of pain
CN114621244A (zh) * 2020-12-14 2022-06-14 成都百裕制药股份有限公司 吡啶衍生物及其在医药上的应用

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US7378423B2 (en) 2004-06-11 2008-05-27 Japan Tobacco Inc. Pyrimidine compound and medical use thereof
US11958857B1 (en) 2023-11-13 2024-04-16 King Faisal University 5-(1H-indol-3-yl)-1,3-substitutedpyrimido[4,5-d]pyrimidine-2,4,7(1H,3H,8H)-trione as anticancer agents
US11976076B1 (en) 2023-11-14 2024-05-07 King Faisal University Substituted 7,8-dihydropyrimido[4,5-d]pyrimidines as anti-tubercular agents

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Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5597776A (en) * 1991-09-18 1997-01-28 Basf Aktiengesellschaft Substituted pyrido[2, 3-dipyrimidines as antidotes for herbicidal cyclohexenones
EP0537463A3 (en) * 1991-09-18 1993-05-26 Basf Aktiengesellschaft Substituted pyrido(2,3-d)pyrimidines as antidotes
US6005096A (en) * 1993-09-17 1999-12-21 Gilead Sciences, Inc. Pyrimidine derivatives
US6967079B2 (en) 1993-09-17 2005-11-22 Isis Pharmaceuticals, Inc. Pyrimidine derivatives for labeled binding partners
US5502177A (en) * 1993-09-17 1996-03-26 Gilead Sciences, Inc. Pyrimidine derivatives for labeled binding partners
US5763588A (en) * 1993-09-17 1998-06-09 Gilead Sciences, Inc. Pyrimidine derivatives for labeled binding partners
US6617437B1 (en) 1993-09-17 2003-09-09 Isis Pharmaceuticals, Inc. Pyrimidine derivatives for labeled binding partners
US5776942A (en) * 1994-06-17 1998-07-07 Nippon Zoki Pharmaceutical Co., Ltd. Bronchodilating pyrido 2,3-d!pyrimidine derivatives
AU694958B2 (en) * 1994-06-17 1998-08-06 Nippon Zoki Pharmaceutical Co., Ltd. A remedy for bronchial asthma
EP0696590A1 (fr) * 1994-06-17 1996-02-14 Nippon Zoki Pharmaceutical Co., Ltd. Dérivés de pyrido 2,3-d pyrimidine, leurs préparation et leurs utilisation comme agents anti-asthmatiques
US6242452B1 (en) 1998-10-15 2001-06-05 Nippon Zoki Pharmaceutical Co., Ltd. 7-aminopyrido[2,3-D]pyrimidine derivatives
US6440978B2 (en) 2000-04-13 2002-08-27 Nippon Zoki Pharmaceutical Co., Ltd. Therapeutic agent for dermatitis
US6787554B2 (en) 2001-11-26 2004-09-07 Warner-Lambert Llc Triazolo[4,3-a]pyrido[2,3-d]pyrimidin-5-one derivatives
US9327039B2 (en) 2004-12-16 2016-05-03 Resolution Chemicals Limited Particle size reduction apparatus, and use thereof
CN101597277B (zh) * 2008-06-04 2011-08-03 山东新时代药业有限公司 S-泮托拉唑及盐的制备方法
WO2015186061A1 (fr) 2014-06-03 2015-12-10 Novartis Ag Dérivés de pyridopyrimidinedione
WO2015186063A1 (fr) 2014-06-03 2015-12-10 Novartis Ag Dérivés de naphthyridinédione
CN108727367A (zh) * 2017-04-18 2018-11-02 山东先达农化股份有限公司 含吡啶并嘧啶二酮的苯并噁嗪酮类化合物及其制备方法和应用和除草剂组合物
CN108727367B (zh) * 2017-04-18 2021-01-05 山东先达农化股份有限公司 含吡啶并嘧啶二酮的苯并噁嗪酮类化合物及其制备方法和应用和除草剂组合物
US20210122750A1 (en) * 2019-10-25 2021-04-29 Saint Louis University Gpr183 antagonists for the treatment of pain
US11919895B2 (en) * 2019-10-25 2024-03-05 Saint Louis University GPR183 antagonists for the treatment of pain
CN114621244A (zh) * 2020-12-14 2022-06-14 成都百裕制药股份有限公司 吡啶衍生物及其在医药上的应用
CN114621244B (zh) * 2020-12-14 2023-08-18 成都百裕制药股份有限公司 吡啶衍生物及其在医药上的应用

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EP0556225A1 (fr) 1993-08-25
JPH06502152A (ja) 1994-03-10
CA2095433A1 (fr) 1992-05-09
KR930702293A (ko) 1993-09-08
HUT64760A (en) 1994-02-28
DE4035479A1 (de) 1992-05-14

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