AU638261B2 - Substituted alpha-pyrimidinyloxy(thio)-and alpha-triazinyloxy(thio)carboxylic acid derivatives, processes for their preparation and their use as herbicides, fungicides and plant growth regulators - Google Patents
Substituted alpha-pyrimidinyloxy(thio)-and alpha-triazinyloxy(thio)carboxylic acid derivatives, processes for their preparation and their use as herbicides, fungicides and plant growth regulators Download PDFInfo
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- AU638261B2 AU638261B2 AU59096/90A AU5909690A AU638261B2 AU 638261 B2 AU638261 B2 AU 638261B2 AU 59096/90 A AU59096/90 A AU 59096/90A AU 5909690 A AU5909690 A AU 5909690A AU 638261 B2 AU638261 B2 AU 638261B2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
-
- 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
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
-
- 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
- C07D251/38—Sulfur 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
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
638 261 COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION NAME ADDRESS OF APPLICANT: Re eo rC ai
S-
.o Schering Aktiengesellschaft 170-178 Mullerstrasse 1000 Berlin Federal Republic of Germany NAME(S) OF INVENTOR(S): Christoph HARDE Erhard NORDHOFF Anita KRUGER Gabriele KRUGER Gerhard TARARA Peter WEGNER Nikolaus HEINRICH Clemens KOTTER Gerhard JOHANN Richard REES ADDRESS FOR SERVICE: DAVIES COLLISON Patent Attorneys 1 Little Collins Street, Melbourne, 3000.
COMPLETE SPECIFICATION FOR THE INVENTION ENTITLED: Substituted a-pyrimidinyloxy(thio)- and o-triazinyloxy(thio)carboxylic acid derivatives, processes for their preparation and their use as herbicides, fungicides and plant growth regulators The following statement is a full description of this invention, including the best method of performing it known to me/us:- I I
LL
-2- Description This invention relates to new substituted a-pyrimdinyloxycarboxylic acid derivatives, processes for their preparation and their use as herbicides, fungicides and plant growth regulators.
It is known that pyrimidine derivatives possess herbicidal activity (EP 223 406, 249 708, 287 072, 287 079 and 347 811). However, the herbicidal activity of these known compounds is often insufficient or selectivity problems are seen in important crops.
The object of the present invention is to make new compounds that do not have these disadvantages and have improved biological properties over the known compounds.
15 It has now been found that substituted a-pyrimidinyloxycarboxylic acid derivatives of general formula I ci (I3 -H--O0 :0 in which A is a C 1
-C
6 -alkyl, a C 3
-C
6 -cycloalkyl or an (a-methyl)benzyl group each of which is substituted in the 1-position by fluorine, and
R
1 is hydrogen, a C 1
-C
4 -alkyl or benzyl group, show interesting herbicidal, fungicidal and plant growth regulant activity.
According to the present invention there is also provided a process for the preparation of compounds of general formula I characterised in that: A) compounds of general formula II 7 930406,p:\oper\dab,59096.spe,2 -3- CH 0 cx o in which R 2 is a halogen atom, an alkylsulfonyl group or a phenylsulfonyl group are reacted with compounds of general formula III
(III)
Ho COOR o in which A and R1 have the meanings given under general formula I, in a suitable 15 solvent in the presence of a suitable base, or B) compounds of general formula IV CH H S 20 COOR (IV)
N
CH 0 S S in which A and R 1 have the meanings given under general formula I are treated with an alkali metal base or an alkaline earth metal base, in a suitable polar solvent, to give compounds of general formula V CH 0 \o coo M
(V)
CHo N ^2 930215,p:\opcrkd2b.590963PC.3 -4in which A has the meaning given under general formula I and M 1 is an alkali metal atom or an equivalent of an alkaline earth metal atom, and then with a suitable acid in a suitable solvent to give compounds of general formula VI CH 0 10 CHso 0o0V in which A has the meaning given under general formula I, or C) compounds of general formula VIII v (VIII) S are reacted with a compound of general formula IX a suitable base, or D) a compound of general formula X 930406,p:\oper\dab,59096.spe.4 CH 0
S(X)
CH 0 in which R 1 has the meaning given under general formula I is reacted with a compound of general formula XI
A-R
2
(XI)
.i 10 in which A has the meaning given under general formula I and R 2 is a halogen S'I. atom, an alkylsulfonyl group or a phenylsulfonyl group in a suitable solvent in the presence of a suitable base.
*see
*G
The expression "halogen" means fluorine, chlorine, bromine and iodine. By the term S 15 alkali metal is meant lithium, sodium or potassium and by the term alkaline earth metal is meant calcium, strontium or barium.
The individual process variants are preferably carried out in the presence of a diluent. For this, a solvent which is inert to the reactants is used.
Suitable solvents include water, aliphatic, alicyclic and aromatic oO *o 930406p:\oper\dab,59096.spe,S I I 6 hydrocarbons, that can be optionally chlorinated, such as for example hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride and trichloroethane, ethers, such as for example diisopropyl ether, dibutyl ether, propylene oxide, dioxane and tetrahydrofuran; ketones, such as for example acetone, methyl ethyl ketone, methyl isopropyl ketone, nitriles, such as for example acetonitrile and propionitrile, alcohols, such as for example methanol, ethanol, isopropanol, butanol and ethylene glycol, esters, such as for example ethyl acetate and amyl acetate, amides, such as for example dimethylformamide and dimethylacetamide, sulphones and sulphoxides, such as for example dimethyl sulphoxide, and bases, such as for example pyridine.
The presence of a catalyst can be an advantage. Suitable catalysts 15 include potassium iodide and onium compounds. such as quaternary ammonium, phosphonium and arsonium compounds as well as sulphonium compounds. Also suitable are polyglycol ethers, especially cyclic ethers, such as 18-crown-6, and tertiary amines, such as for example tributylamine. Preferred compounds are quaternary ammonium compounds, 20 such as for example benzyltriethylammonium chloride and tetrabutylamrimonium bromide.
The reactions, can be carried out under atmospheric pressure but if desired higher or lower pressures can be used.
The process variant A) is preferably carried out in an aromatic hydrocarbon, such as benzene, toluene or xylene, a halogenated hydrocarbon, such as methylene chloride or chloroform, an alcohol, such as methanol, ethanol or isopropanol, an ether, such as for example diethyl ether, diisopropyl ether, tetrahydrofuran or dioxane, a ketone, such as for example acetone or methyl ethyl ketone, an ester, such as methyl acetate or ethyl acetate, or a polar aprotic solvent, such as dimethylformamide, dimethylacetamide or dimethyl sulphoxide, or another solvent, such as acetonitrile or water.
7 Bases that can be used include an alkali metal, such as sodium or potassium, an alkali metal or alkaline earth metal hydride, such as sodium hydride, potassium hydride or calcium hydride, a carbonate, such as sodium carbonate or potassium carbonate, or a metal hydroxide, such as sodium hydroxide or potassium hydroxide.
The reaction is suitably carried out between room temperature and the boiling point of the particular solvent or solvent mixture. The reaction time lies between 1 and 24 hours.
SThe reaction can also be carried out in the absence of a solvent, at a 10 temperature between 120 and 160 C, by using as alkali metal carbonate, such as anhydrous potassium carbonate.
The preparation of the a-hydroxy or a-mercapto carboxylic acid 6 derivatives used in this process variant can be carried out using the following literature processes: J. Org. Chem. 33, 2565 (1968); J.
Amer. Chem. Soc. 95, 7146 (1973); J. Chem. Soc. 1957, 3262; J. Org.
Chem. 33, 1831 (1968); Can. J. Chem. 60, (1982) 2707 and Bull. Soc. Chim. Fr. 1969, 2721.
eees alcohol, such as ethanol, propanol or isopropanol, a ketone h as acetone or methyl ethyl ketone, water or a mixture of aer and a polar solvent.
Bases that can be used include carb es, such as sodium carbonate, potassium carbonate or calci -rbonate, and metal hydroxides, such as sodium hydroxide or asium hydroxide.
The temperat of the reaction falls within room temperature and the boili oint of the particular solvent or solvent mixture. The E-a4 sa--t-ima: ;rnn hf'.twerf Ovnl rI ipr, :hr A catalytic reduction (hydrogenation) can also be used.
Suitable solvents for process variant (iii) include hyd carbons, such as benzene, toluene or xylene, halogenated hydrocar s, such as methylene chloride or chloroform, alcohols, such methanol, ethanol or isopropanol, ethers, such as for example die yl ether, diisopropyl ether, tetrahydrofuran or 1,4-dioxane, keto such as acetone or methyl ethyl ketone, esters, such as meth acetate or ethyl acetate, or nitriles, such as acetonitrile.
Bases that can be used include a alkali metal, such as sodium or potassium, an alkali metal or kaline earth metal hydride, such as sodium hydride, potassium ride or calcium hydride, a carbonate, such as sodium carbonat potassium carbonate or calcium carbonate, or a metal hydroxide, s as sodium hydroxide or potassium hydroxide.
Organic ammonium bes that can be used include for example, ammonia an alkylamine imary amine), a dialkylamine (secondary amine) or a trialkylami (tertiary amine).
The te erature of the reaction falls within room temperature and the boi ng point of the particular solvent or solvent mixture. The .@00.
*of* 00 4! of* s 0 0000 0090 00 0* 0 LU P 4- d An F RW.L.- A q P IR A A M P.14 pq RnL_-L Y- *00 Suitable solvents for process variant B) include hydrocarbons, such as benzene, toluene or xylene, halogenated hydrocarbons, such as methylene chloride or chloroform, ethers, such as for example diethyl ether, diisopropyl ether, tetrahydrofuran or 1,4-dioxane, ketones, 25 such as acetone or methyl ethyl ketone, esters, such as methyl acetate or ethyl acetate, or polar aprotic solvents, such as dimethylformamide, dimethylacetamide or dimethyl sulphoxide, and other solvents,.such as acetonitrile or water.
Bases that can be used include an alkali metal, such as sodium or potassium, an alkali metal or alkaline earth metal hydride, such as 9 sodium hydride, potassium hydride or calcium hydride, a carbonate, such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or potassium hydrogen carbonate, or a metal hydroxide, such as sodium hydroxide or potassium hydroxide.
The temperature of the reaction falls within room temperature and the boiling point of the particular solvent or solvent mixture. The reaction time lies between 5 minutes and 24 hours.
The process variant C) is preferably carried out in an aprotic solvent, such as benzene, toluene, xylene, tetrahydrofuran, diethyl ether, hexane, dimethylformamide, dimethylacetamide or dimethyl sulphoxide. For deprotinating the compound of general formula X, a base, such as sodium hydride, potassium tert-butylate or lithium diisopropylamide can be used.
0*eO The temperature of the reaction lies between -78°C and the boiling point of the particular solvent or solvent mixture. The reaction time lies between 0.5 and 24 hours.
Compounds of general formula X are described in the literature or can be prepared by methods analogous to those described in the literature.
(Khim.-Farm. Zh. 16 931-4 [1982]; Ukr. Khim. Zh. (Russ. Ed) 49 i 20 1205-8 [1983]; Fizol. Akt. Veshchestva 18. 75-9 [1986]; and USSR Patent 791746).
The compounds of the invention prepared by these processes can be isolated from the reaction mixtures in conventional manner, for example by distillation of the solvent at normal or reduced pressure, by precipitation with water or by extraction.
A higher level of purity can be achieved as a rule by column chromatography as well as by fractional distillation or crystallisation.
*v The compounds of the invention are, as a rule, colourless and odourless liquids or crystals that are soluble in water, slightly soluble in aliphatic hydrocarbons such as petroleum ether, hexane, pentane and cyclohexane and highly soluble in halogenated hydrocarbons, such as chloroform, methylene chloride and carbon tetrachloride, aromatic hydrocarbons, such as benzene, toluene and xylene, ethers, such as diethyl ether, tetrahydrofuran and dioxane, nitriles, such as acetonitrile, alcohols, such as methanol and ethanol, amides, such as dimethylformamide, and sulphoxides, such as dimethyl sulphoxide.
SThe compounds of the invention show a good herbicidal activity in broad leaved weeds and grasses. A selective use in various crops is possible, for example in such as rape, beets, soya beans, cotton, e* rice, barley, wheat and other cereals. Individual active substances 15 are particularly suitable as selective herbicides in beet, cotton, soya and cereals. However the compounds can be used for control of weeds in permanent crops, such as for example forestry, ornamental trees, fruit, vine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plantations and for the selective 20 control of weeds in annual crops.
The compounds of the invention can used for example against the following plant species: Dicotyledonous weeds of the species Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Brassica, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Lamium, Veronica, Abutilon, Datura, Viola, Galeopsis, Papaver, Centaurea and Chrysanthemum.
Monocotyledonous weeds of the species Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron, Sagittaria, Monocharia, Fimbristylis, 11 Eleocharis, Ischaemum and Apera.
The rates of use vary depending on the manner of pre- and postemergent use between 0.001 and 5 kg/ha.
The compounds of the invention can also be used as defoliants, desiccants and as total herbicides. They also influence plant growth and can thus be used to influence plant growth of crops. Some compounds also show fungicidal activity.
The compounds of the invention can be used either alone or in admixture with one another or with other active agents. Optionally, 10 other plant-protective agents or pesticides can be added, depending on the purpose for the treatment. When it is desired to broaden the spectrum of activity, other herbicides can also be added. Herbicidally active mixing partners suitable in this connection include for example, the active agents listed in Weed Abstracts, vol. 38, No.3 (1989) under the heading "Lists of common names and abbreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts".
An improvement in the intensity and speed of action can be obtained, for example, by addition of suitable adjuvants, such as organic 20 solvents, wetting agents and oils. Such additives may allow a decrease in the dose.
The designated active ingredients or their mixtures can suitably be used, for example, as powders, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers and/or diluents and, optionally, binding, wetting, emulsifying and/or dispersing adjuvants.
Suitable liquid carriers are, for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulphoxide, dimethylformamide and other 12 mineral-oil fractions and plant oils.
Suitable sol.'d carriers include mineral earths, e.g. bentonite, silica gel, talc, kaolin, attapulgite, limestone, silicic acid and plant products, e.g. flours.
As surface-active agents there can be used for example calcium lignosulphonate, polyoxyethylenealkylphenyl ethers, naphthalenesulphoni acids and their salts, phenolsulphonic acids and their salts, formaldehyde condensates, fatty alcohol sulphates, as well as substituted benzenesulphonic acids and their salts.
se 10 The percentage of the active ingredient(s) in the various preparations can vary within wide limits. For example, the compositions can contain about 10 to 90 percent by weight active ingredients, and about 90 to 10 percent by weight liquid or solid carriers, as well as, optionally up to 20 percent by weight of surfactant.
The agents can be applied in customary fashion, for example with water as the carrier in spray mixture volumes of approximately 100 to 1,000 0**4 1/ha. The agents can be applied using low-volume or ultra-low-volume techniques or in the form of so-called microgranules.
The preparation of these formul .ons can be carried out in known manner, for example by milling or mixing processes. Optionally, individual components can be mixed just before use for example by the piC so-called commonly used tank-mixing method.
a 4 Formulations can be prepered, for example, from the following ingredients, Wettable Powder percent b percent b percent b percent b weight active ingredient weight kaolin weight silicic acid weight of a mixture of calcium lignosulphonate and the sodium salt of N-methyl-N-oleyltaurine a *u a u *300 0O 00: a *0 a 2) 40 25 10 percent percent percent percent by weight active ingredient by weight bentonite by weight colloidal silicic acid by weight of a mixture of calcium lignosulphonate and alkylphenyl polyglycol ether B) Paste 5 15 b000 0606 a ad 0 a S percent by percent by percent by percent by percent by percent by weight active ingredient weight sodium aluminium silicate weight cetyl polyglycol ether with 8 mol of ethylene oxide weight spindle oil weight polyethylene glycol weight water C) Emulsifiable Concentrate percent by weight active ingredient percent by weigh-: cyclohexanone percent by weight xylene percent by weight of a mixture of calcium dodecylbenzenesulphonat' and nonylphenolpolyoxyethylene.
-14- The following Examples illustrate the preparation of compounds of the invention.
Example 1 Methyl 2-(4,6-dimethoxy-2-pyrimidinyloxy)-3-fluoro-3-methylbutanoate 4 g (26.6 mmol) Methyl 3-fluoro-2-hydroxy-3-methylbutanoate and 5.81 g (26.6 mmol) 4,6-dimethoxy-2-methylsulphonylpyrimidine were dissolved in 75 ml dimethylformamide at 20"C and treated with 1.84 g (13.3 mmol) potassium carbonate. The suspension was stirred for 5 hours at 20 0 C i and heated for one hour at 60 0 C. The reaction mixture was then poured into 150 ml ice-water and extracted with three lots of 75 ml ethyl acetate. The combined ethyl acetate phase was washed with water, dried over magnesium sulphate, filtered and evaporated. The solid residue was purified by silica gel column chromatography using hexane/ethyl acetate as eluent.
Yield: 2.9 g 37.7% of theory mp: 73-74°C
F.
s ee o**
.J
2-(4,6-Dimethoxy-2-pyrimidinylbxy)-3-fluoro-3-methylbutanoic acid 2 g (6.9 mmol) Methyl 2-(4,6-dimethoxy-2-pyrimidinyloxy)-3-fluoro-3methylbutanoate was dissolved in a mixture of 20 ml water and 10 ml methanol and treated with 387 mg (6.9 mmol) potassium hydroxide. After i. stirring for 4 hours at 50'C, the mixture was added to 50 ml water and S extracted with 50 ml ethyl acetate. The aqueous phase was acidified with hydrochloric acid until it was pH 2 and extracted with three lots of 100 ml ethyl acetate. The combined ethyl acetate phase was washed with water, dried over magnesium sulphate, filtered and evaporated.
JB AYield: 1.0 g 54.5% of theory mp: 107-108'C 930215,p:\oper\dab,59096.spe,14 15 following compounds of the invention of general formula In a similar manner, the I were -prepared: Example No.
3 4 7 8 9 CF(0H 3 2
CF(CH
3 Phenyl 1 -Flu orocyclohexyl OF(0H 3 Phenyl 1 -Fluorocyclopentyl 1-Flu orocyclohexyl cyc lopentyl
CH
2
OH
3
OH
2
CHS
OH
3
H
OH
3
H-
H
OCH
3
OCH
3
OCH
3
OCH
3
OCH
3 00H 3
OCH
3 00H 3 00H 3
OCH
3 00H 3
OCH
3 00H 3
OCH
3 x Y o OH 0 OH O OH o OH o OH o OH 0 OH Physical constant mp.: 73 -740C mp.: 10600 mp.: 99-10000 mp.: 135-13600 mp.: 89.9000 mp.: 140-14100C mp.: 138-1400C 0* S S. 0OS*
S.
S S @0
S
e.g.
S.
C.
S.
*5 06 S .0 I.
0SS S *4 50 0* 0 0 0 0000 O Cs 3 5 0* 00 00 S 45 *Ih 0 E~ S
S
O 50
S
.5 0
S.
0 4.0095
S
q3021Sp: oper~dab,59096Spe1S 16 The following examples illustrate the possibilities for use of the compounds of the invention.
Example A ln a greenhouse, the noted plant species were treated pre-emergently with. the, noted compounds of the invention, at a rate of 1 .0 kg active ingredient/ha. The compounds of the invention were sprayed evenly over the soil as emulsions or suspensions in 500 litres water/ha. Three weeks after the treatment, the compounds of the invention showed excellent activity against the weeds.
In the following table,: 0 =,no damage 1 1 24% damage 2 25 74% damage 3 75 89% dama,3e 4 90 100% damage :AVEFA Avena fatua CYPES Cyperus esculentus ABUTH Abutilon theophrasti ~*IPOSS £p~moea purpurea **MATCH Matricaria chamomilla POLSS =Pol.ygonum sp.
SOLSS Solanum sp.
:VERPE Veronica persica a.VIOSS Viola sp 930215.p: operkdab,59096.spe,16 17 A S C A I MP S V V V E Y B P A 0 0 F I E T P U 0 T L L R 0 Compoundof the F V E T S C S S P S Invention A I S H S H S 8 E S Example 1 3 4 4 3 3 3 Example 2 3 4 4 3 3 4 Untreated 0 0 0 0 0 0 0 0 0 0 Example B tn a greenhouse, the noted plant species were treated p'ost-emergently with the noted compounds of the invention, at a rate of 0.1 kg active ingredient/ha. The compounds of the invention were sprayed evenly over the plants as emulsions in 500 litres water/ha. Two weeks after the treatment, the compounds of the invention showed a high crop selectivity in cotton with excellent activity against the weeds. The comparison material did not show similar high efficacy.
In the following table: *0 no damage *1 =1 24Z damarta too* 2 25 74% damage 3 =75 9'9% damage to 04 90 100% damage GOSHI' Gossypium hirsutum *ALOMY =Alopecurus myosuroides to PANSS Panicum maximum ABTJTH =Abutilon theophrasti to: IPOSS Ipomea purpurea POLSS =Polygonum sp.
SOLSS =Solanim sp.
VERPE Veronica persica VIOSS =Viola sp 930216, p: \oper\dab,59G96.spe, 17 18 G A 0 L 0 H M I Y P A I P S A B P0 0 N U 0 L L S T S S S S H S S S V V E I R 0 P S E S Compound of the Invention Example 1 Untreated 13 34 33 3 00 00 00 0 3 3 0 0 Comnarison (EP 0 347 811) Compound No. 243 01 11 01 21 0 0 9 0 *O 0 0 0 a 930216,p: Wperdab5996.spc, 18 19 Example C In a greenhouse, the noted plant species were treated post-emergently with the noted compounds of the invention, at a rate of 0.1 kg active ingredient/ha. The compounds of the invention were sprayed evenly over the plants as emulsions in 500 litres water/ha. Two weeks after the treatmerit, the compounds of the invention showed a high crop selectivity in cotton with excellent activity against the weeds. The comparison material did not show similar high efficacy.
In the following table: 0 =no damage 1 =1 24% damage 2 =25 74% damage 3 =75 89% damage 4 90 100% damage.
GOSHI =Gossypium hirsutum AGRRE Elymus repens BROTE =Bromus te--torum SETVI S~taria viridis PANSS Panicum maximum SORHA =Sorghum halepense ABUTH Abutilon theophrasti :::GALAP =Galium aparine IPOSS Ipomea. purpurea *MATCH Matricar lA chamomilla PQLSS Polygonrunm sp.
*SEBEX =Sesbani e:galtata .:VERPE Veronica Petsica T Ilu930215,p:Aope~A~b,59096.sMc19 20 A B G R R 0 E T E E S P E A T N V S I S S A 0 B R U H T A H I M P A 0 T S C S H P S 0OE L B S E S X Compound of th(: Invention Example 1 Untreated Comparison (EP 0 347 811) Compound No. 4 1 333 3 333 33 44 3 0 00 00 0 00 00 000 01 02 22 02 00 12 2 ft...
ft...
ft ft ft. ft ft ft...
ft.
ft ft.
ft. ft ft. ft.
ft ft ft ft ft ft ft ft...
ft ft ft ft ft.
ft...
ft ft ft ft ft ft ft ft., 930216,p:\oper~dab,59096.spe,2J
Claims (1)
- 21- THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS: 1. Substituted a-pyrimidinyloxycarboxylic acid derivatives of general formula CH' H CH 0 6* 6 6 6 6*66 6e@@ 6 60 6 0 0000 SO 0@ S. 0* @6 S *i S OOS S OS SO 5 S 060@ 0@ 00 6 *055: S 10 in which A is a C 1 -C 6 -alkyl, a C 3 -C 6 -cycloalkyl or an (a-methyl)benzyl group each of which is substituted in the 1-position by fluorine, and R 1 is hydrogen, a C 1 -C 4 -alkyl or bernyl group. 15 2. Process for the preparation of compounds of general formula I, ace Irding to claim 1, characterised in that A) compounds of general formula II CH 0 in which R 2 is a halogen atom, an alkylsulfonyl group or a phenylsulfonyl group are reacted with compounds of general formula III HO C(III) H COOR1 ee 930406,p:\oper\dab,59096.spe,21 -22 in which A and R 1 have the meanings given under general formula I, in a suitable solvent in the presence of a suitable base, or B) compounds of general formula IV CH 0 0- COOR (IV) H CH 0O 3 in which A and R 1 have the meaning give in claim 1. are treated with an alkali metal base or an alkaline earth metal base, in a suitable polar solvent, to give compounds of general formula V SCo0 (V) 20 CHo in which A has the meaning give in claim 1 and M 1 is an alkali metal atom or an equivalent of an alkaline earth metal atom, and then with a suitable acid in a suitable solvent to give compounds of general formula VI CH 0 0 COO H (VI) c: C 30 c 3 930215,p:\oper\dab,59096sp9,22 23 in which A has the meaning given in claim 1, or C) compounds of general formula VIII 0 H (VIII) CH 0 are reacted with a compound of general formula IX So (IX) Z COOR in which A and R 1 have the meanings give in claim 1 and Z is a halogen atom or an alkylsulfonyloxy group, in the presence of a suitable solvent and a suitable base, or D) a compound of general formula X HCH CH o in which R 1 has the meaning give in claim 1 is reacted with a compound of general 0 formula XI s base .2 00• A-R 2 (XI) *000' 3Q in which A has the meaning give in claim 1 and R 2 is a halogen atom, an alkylsulfonyl group or a phenylsulfonyl group in a suitable solvent in the presence of a suitable base. 930215,p:\oper\db,59096pe,23 24 3. A herbicidal composition which comprises a compound of general formula I according to claim 1, in admixture with agriculturally acceptable carriers or diluents. 4. A method of conmbating weeds which comprises applying to the weeds or their locus a compound of generai formula I according to claim 1. Compounds of formula processes for their preparation or herbicidal compositions or methods invol'Iving them, substantially as hereinbefore described wi.th reference to the Examples. DATED this 16th day of February, 1993 Schering Aktiengesellschaft By Its Patent Attorneys DAVIES COLLISON CAVE Ges Go 04 to S 930215,p;\opcrdab,59096.spz,24
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3924259A DE3924259A1 (en) | 1989-07-19 | 1989-07-19 | SUBSTITUTED (ALPHA) -PYRIMIDINYLOXY (THIO) AND (ALPHA) -TRIAZINYLOXY (THIO) CARBONIC ACID DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF AND THEIR USE AS AGENTS WITH HERBICIDES, FUNGALIZING AGENTS AND PLANTING AGENTS |
| DE3924259 | 1989-07-19 | ||
| DE19904009481 DE4009481A1 (en) | 1990-03-22 | 1990-03-22 | New pyrimidinyl:oxy(thio)-and tri:azinyl:oxy(thio)-alkanoic acid deriv |
| DE4009481 | 1990-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5909690A AU5909690A (en) | 1991-01-24 |
| AU638261B2 true AU638261B2 (en) | 1993-06-24 |
Family
ID=25883266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU59096/90A Ceased AU638261B2 (en) | 1989-07-19 | 1990-07-18 | Substituted alpha-pyrimidinyloxy(thio)-and alpha-triazinyloxy(thio)carboxylic acid derivatives, processes for their preparation and their use as herbicides, fungicides and plant growth regulators |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0409368B1 (en) |
| JP (1) | JPH03135963A (en) |
| KR (1) | KR910002807A (en) |
| CN (1) | CN1048852A (en) |
| AR (1) | AR246960A1 (en) |
| AT (1) | ATE82271T1 (en) |
| AU (1) | AU638261B2 (en) |
| BR (1) | BR9003337A (en) |
| CA (1) | CA2021486A1 (en) |
| DE (1) | DE59000454D1 (en) |
| DK (1) | DK0409368T3 (en) |
| ES (1) | ES2053089T3 (en) |
| FI (1) | FI903486A7 (en) |
| GR (1) | GR3006945T3 (en) |
| HU (1) | HU208962B (en) |
| IE (1) | IE902544A1 (en) |
| IL (1) | IL94999A (en) |
| PH (1) | PH27080A (en) |
| PT (1) | PT94745A (en) |
| TR (1) | TR26400A (en) |
| YU (1) | YU131690A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU652961B2 (en) * | 1990-10-19 | 1994-09-15 | Ube Industries, Ltd. | 3-alkoxyalkanoic acid derivative, process for preparing the same and herbicide using the same |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0517215B1 (en) * | 1991-06-07 | 1998-09-02 | Ube Industries, Ltd. | Pyrimidine or triazine derivative, process for preparing the same and herbicide using the same |
| TW211581B (en) * | 1991-11-07 | 1993-08-21 | Hoechst Ag | |
| DE4142570A1 (en) * | 1991-12-21 | 1993-06-24 | Basf Ag | GLYCOLALDEHYDE AND MILK ACID DERIVATIVES, THEIR PREPARATION AND USE |
| DE4201875A1 (en) * | 1992-01-24 | 1993-07-29 | Basf Ag | THIOCARBONSAEUREDERIVATE, PROCESSES AND INTERMEDIATE PRODUCTS FOR THEIR MANUFACTURE |
| EP0562510A1 (en) * | 1992-03-27 | 1993-09-29 | Hoechst Aktiengesellschaft | Optically active pyrimidinyl- or triazinyl-oxy-(or -thio)-carbonic acid derivatives, processes for their production and their use as herbicides or plant growth regulators |
| EP0565951A1 (en) * | 1992-04-13 | 1993-10-20 | Nihon Bayer Agrochem K.K. | Herbicidally active pyrimidinylthioalkane derivatives |
| CA2110500A1 (en) * | 1992-06-17 | 1993-12-23 | Christoph Luthy | Pyrimidinyl- and tetrazinyl compounds with herbicidal activity |
| JP2985992B2 (en) * | 1992-07-21 | 1999-12-06 | 宇部興産株式会社 | 3-Alkoxy-N-cycloalkylsulfonylalkanoic acid amide derivative, production method thereof and herbicide |
| JPH06145153A (en) * | 1992-09-18 | 1994-05-24 | Nippon Bayeragrochem Kk | Herbicidal hydrazones |
| EP0593998A1 (en) * | 1992-10-23 | 1994-04-27 | Nihon Bayer Agrochem K.K. | Pyrimidinylthioalkane herbicides |
| JPH06293743A (en) * | 1993-02-15 | 1994-10-21 | Nippon Bayeragrochem Kk | Herbicidal pyrimidinyloxy/triaziinyloxyalkanol derivative |
| DE4313411A1 (en) * | 1993-04-23 | 1994-10-27 | Basf Ag | 3-Halogen-3-hetarylcarboxylic acid derivatives, processes and intermediates for their preparation |
| DE4313413A1 (en) * | 1993-04-23 | 1994-10-27 | Basf Ag | 3- (Het) aryloxy (thio) carboxylic acid derivatives, processes and intermediates for their preparation |
| DE4313412A1 (en) * | 1993-04-23 | 1994-10-27 | Basf Ag | 3- (Het) aryl-carboxylic acid derivatives, processes and intermediates for their preparation |
| DE4329911A1 (en) * | 1993-09-04 | 1995-03-09 | Basf Ag | Substituted lactic acid derivatives with an N-organic radical in the beta position |
| DE19533023B4 (en) | 1994-10-14 | 2007-05-16 | Basf Ag | New carboxylic acid derivatives, their preparation and use |
| WO2011053090A2 (en) * | 2009-11-02 | 2011-05-05 | 서울대학교 산학협력단 | Novel 2, 4-pyrimidine derivatives and use thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4968340A (en) * | 1988-06-20 | 1990-11-06 | Kumiai Chemical Industry Co., Ltd. | Alkanoic acid derivatives and herbicidal compositions |
| AU5618890A (en) * | 1989-06-02 | 1990-12-06 | Shell Internationale Research Maatschappij B.V. | 2-(substituted methoxy)-triazine/pyrimidine compounds, processes for their preparation and their use as herbicides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0223406B1 (en) * | 1985-10-15 | 1990-08-29 | Kumiai Chemical Industry Co., Ltd. | Pyrimidine derivatives and herbicidal uses thereof |
-
1990
- 1990-07-06 IL IL9499990A patent/IL94999A/en not_active IP Right Cessation
- 1990-07-09 YU YU131690A patent/YU131690A/en unknown
- 1990-07-10 FI FI903486A patent/FI903486A7/en not_active Application Discontinuation
- 1990-07-12 BR BR909003337A patent/BR9003337A/en not_active Application Discontinuation
- 1990-07-12 IE IE254490A patent/IE902544A1/en unknown
- 1990-07-18 AU AU59096/90A patent/AU638261B2/en not_active Ceased
- 1990-07-18 PT PT94745A patent/PT94745A/en not_active Application Discontinuation
- 1990-07-18 HU HU904537A patent/HU208962B/en not_active IP Right Cessation
- 1990-07-18 CA CA002021486A patent/CA2021486A1/en not_active Abandoned
- 1990-07-18 CN CN90104763A patent/CN1048852A/en active Pending
- 1990-07-18 KR KR1019900010880A patent/KR910002807A/en not_active Withdrawn
- 1990-07-19 TR TR90/0636A patent/TR26400A/en unknown
- 1990-07-19 JP JP2189609A patent/JPH03135963A/en active Pending
- 1990-07-19 PH PH40863A patent/PH27080A/en unknown
- 1990-07-19 ES ES90250184T patent/ES2053089T3/en not_active Expired - Lifetime
- 1990-07-19 AT AT90250184T patent/ATE82271T1/en not_active IP Right Cessation
- 1990-07-19 EP EP90250184A patent/EP0409368B1/en not_active Expired - Lifetime
- 1990-07-19 DE DE9090250184T patent/DE59000454D1/en not_active Expired - Lifetime
- 1990-07-19 DK DK90250184.0T patent/DK0409368T3/en active
- 1990-07-19 AR AR90317404A patent/AR246960A1/en active
-
1993
- 1993-01-29 GR GR920402669T patent/GR3006945T3/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4968340A (en) * | 1988-06-20 | 1990-11-06 | Kumiai Chemical Industry Co., Ltd. | Alkanoic acid derivatives and herbicidal compositions |
| AU5618890A (en) * | 1989-06-02 | 1990-12-06 | Shell Internationale Research Maatschappij B.V. | 2-(substituted methoxy)-triazine/pyrimidine compounds, processes for their preparation and their use as herbicides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU652961B2 (en) * | 1990-10-19 | 1994-09-15 | Ube Industries, Ltd. | 3-alkoxyalkanoic acid derivative, process for preparing the same and herbicide using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1048852A (en) | 1991-01-30 |
| HU208962B (en) | 1994-02-28 |
| EP0409368B1 (en) | 1992-11-11 |
| TR26400A (en) | 1995-03-15 |
| IL94999A0 (en) | 1991-06-10 |
| DK0409368T3 (en) | 1993-02-22 |
| ATE82271T1 (en) | 1992-11-15 |
| FI903486A0 (en) | 1990-07-10 |
| AR246960A1 (en) | 1994-10-31 |
| DE59000454D1 (en) | 1992-12-17 |
| EP0409368A2 (en) | 1991-01-23 |
| EP0409368A3 (en) | 1991-07-24 |
| GR3006945T3 (en) | 1993-06-30 |
| ES2053089T3 (en) | 1994-07-16 |
| IL94999A (en) | 1994-10-07 |
| HUT54353A (en) | 1991-02-28 |
| FI903486A7 (en) | 1991-01-20 |
| KR910002807A (en) | 1991-02-26 |
| PT94745A (en) | 1991-03-20 |
| AU5909690A (en) | 1991-01-24 |
| IE902544A1 (en) | 1991-02-27 |
| CA2021486A1 (en) | 1991-01-20 |
| BR9003337A (en) | 1991-08-27 |
| HU904537D0 (en) | 1990-12-28 |
| JPH03135963A (en) | 1991-06-10 |
| PH27080A (en) | 1993-02-01 |
| YU131690A (en) | 1993-10-20 |
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