WO2000034257A1 - 2-imino-thiazolines substituees et leur utilisation comme herbicides - Google Patents

2-imino-thiazolines substituees et leur utilisation comme herbicides Download PDF

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Publication number
WO2000034257A1
WO2000034257A1 PCT/EP1999/009281 EP9909281W WO0034257A1 WO 2000034257 A1 WO2000034257 A1 WO 2000034257A1 EP 9909281 W EP9909281 W EP 9909281W WO 0034257 A1 WO0034257 A1 WO 0034257A1
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WO
WIPO (PCT)
Prior art keywords
cyano
substituted
chlorine
fluorine
methyl
Prior art date
Application number
PCT/EP1999/009281
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German (de)
English (en)
Inventor
Klaus-Helmut Müller
Mark Wilhelm Drewes
Dieter Feucht
Rolf Pontzen
Ingo Wetcholowsky
Original Assignee
Bayer 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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU15578/00A priority Critical patent/AU1557800A/en
Publication of WO2000034257A1 publication Critical patent/WO2000034257A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the invention relates to new substituted 2-imino-thiazolines, processes for their preparation and their use as herbicides.
  • A represents a single bond or optionally substituted alkanediyl (alkylene),
  • R 1 represents nitro, cyano, thiocarbamoyl, nitroalkyl, cyanoalkyl, thiocarbamoylalkyl or formylalkyl,
  • R 2 represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl or alkoxycarbonyl,
  • R 3 represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each optionally substituted alkyl or alkoxycarbonyl
  • R 4 represents hydrogen, cyano, halogen or alkoxy, or optionally substituted cycloalkyl, aryl or heterocyclyl
  • hydrocarbon chains such as alkyl or alkanediyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.
  • A preferably represents a single bond or, optionally, by
  • R 1 preferably represents nitro, cyano, thiocarbamoyl or nitroalkyl, cyanoalkyl, thiocarbamoylalkyl or formylalkyl, each having up to 6 carbon atoms.
  • R 2 preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C r C 4 alkoxy, each having up to 4 carbon atoms.
  • R 3 preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted by cyano, halogen, or C j ⁇ -C alkyl alkoxy or alkoxycarbonyl each having up to 4
  • R 4 preferably represents hydrogen, cyano, halogen, alkoxy having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C 4 -alkyl, optionally by nitro, cyano, Halogen, C, -C 4 alkyl, C, -C 4 haloalkyl,
  • R 1 particularly preferably represents nitro, cyano, thiocarbamoyl, nitromethyl, nitroethyl, nitropropyl, cyanomethyl, cyanoethyl or cyanopropyl.
  • R 2 particularly preferably represents hydrogen, cyano, carboxy, carbamoyl,
  • R 3 particularly preferably represents hydrogen, cyano, carboxy, carbamoyl,
  • R 4 particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, in each case optionally by cyano,
  • R 1 very particularly preferably represents nitro or cyano (in particular cyano).
  • R 2 very particularly preferably represents chlorine, bromine, methyl or ethyl.
  • R 3 very particularly preferably represents hydrogen or methyl.
  • R 4 very particularly preferably represents optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfmyl, ethylsulfinyl, trifluoromethylsulfmyl,
  • R 1 represents nitro or cyano (especially cyano),
  • R 2 represents chlorine, bromine, methyl or ethyl
  • R 3 represents hydrogen or methyl
  • R 4 represents hydrogen, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • the new substituted 2-imino-thiazolines of the general formula (I) have interesting biological properties. They are particularly characterized by strong herbicidal - and to a certain extent also by insecticidal - effectiveness.
  • R 2 , R 3 and R 4 have the meaning given above,
  • R 1 has the meaning given above and
  • X represents halogen or the grouping -O-CO-alkyl
  • Compounds can be prepared by reacting compounds of the formula (II) with customary nitrating agents, such as, for example, nitric acid - optionally in a mixture with sulfuric acid or acetic acid - by customary methods.
  • customary nitrating agents such as, for example, nitric acid - optionally in a mixture with sulfuric acid or acetic acid - by customary methods.
  • the compounds of the general formula (I) can also be synthesized as shown schematically below:
  • Formula (II) provides a general definition of the 2-imino-thiazolines to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • A, R 2 , R 3 and R 4 preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the invention Formula (I) has been given as preferred, particularly preferred or very particularly preferred for A, R 2 , R 3 and R 4 .
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US-A-5459277, EP-A-545431).
  • Formula (III) provides a general definition of the alkylating or acylating agents to be used as starting materials in the process according to the invention.
  • R 1 preferably has the meaning which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for R 1 ;
  • X preferably represents fluorine, chlorine, bromine, iodine or the grouping -O-CO- (C, -C 4 - alkyl), in particular chlorine, bromine, iodine or -O-CO-CH 3 .
  • the starting materials of the general formula (III) are known synthetic chemicals.
  • reaction aids for the process according to the invention.
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium,
  • DBU 1,8-diazabicyclo [5,4,0] -undec-7-ene
  • Phase transfer catalysts are also suitable as further reaction aids for the process according to the invention.
  • Examples of such catalysts are:
  • Tetrabutylammonium bromide Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl-trimethylammonium chloride, hexadecyl-trimethylammonium-bromide, benzylchloride, benzyl methylammonium hydroxide, benzyl triethylammonium hydroxide, benzyl tributyl ammonium chloride, benzyl tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl hexadecylphosphonium bromide, butyl triphenyl Tetraphenylphosphonium bromide.
  • the process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using diluents.
  • suitable diluents for carrying out the process according to the invention are, above all, inert organic solvents.
  • aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propio nitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide;
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours.
  • the work-up is carried out using customary methods (cf. the manufacturing examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow in places grow where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Brassica, lactuca, cucumis, cucurbita Brassica, lactuca, cucumis, cucurbita.
  • Scirpus Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris.
  • the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.
  • the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth.
  • the active compounds according to the invention for combating weeds in permanent crops for example forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm,
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and decotyledon crops, both in the pre-emergence and in the post-emergence process.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as Chlorobenzene
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating agents are possible: e.g.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin,
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, spraying or scattering.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amount of active compound is applied in 1000 liters of water per hectare.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Example B the compounds according to Preparation Examples 1 and 8, with good tolerance to crop plants, such as, for example, cotton and barley, show a strong action against weeds.
  • Example B the compounds according to Preparation Examples 1 and 8, with good tolerance to crop plants, such as, for example, cotton and barley, show a strong action against weeds.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compounds according to Preparation Examples 1 and 8 show good tolerance to crop plants, such as e.g. Wheat, effective against weeds.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouvelles 2-imino-thiazolines substituées de la formule générale (I) dans laquelle A désigne une liaison double ou alcanediyle (alkylène) éventuellement substitué; R1 désigne nitro, cyano, thiocarbamoyle, nitroalkyle, cyanoalkyle, thiocarbamoylalkyle ou formylalkyle; R2 désigne hydrogène, cyano, carboxy, carbamoyle, thiocarbamoyle, halogène, ou dans chaque cas, alkyle ou alcoxycarbonyle éventuellement substitué; R3 désigne hydrogène, cyano, carboxy, carbamoyle, thiocarbamoyle, halogène, ou dans chaque cas, alkyle ou alcoxycarbonyle éventuellement substitué, et R4 désigne hydrogène, cyano, halogène ou alcoxy, ou dans chaque cas, cycloalkyle, aryle ou hétérocyclyle éventuellement substitué, y compris les isomères E et Z possibles de ces composés. L'invention concerne par ailleurs des procédés permettant de préparer lesdits composés et leur utilisation comme herbicides.
PCT/EP1999/009281 1998-12-10 1999-11-30 2-imino-thiazolines substituees et leur utilisation comme herbicides WO2000034257A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU15578/00A AU1557800A (en) 1998-12-10 1999-11-30 Substituted 2-imino-thiazolines and their use as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1998156966 DE19856966A1 (de) 1998-12-10 1998-12-10 Substituierte 2-Imino-thiazoline
DE19856966.1 1998-12-10

Publications (1)

Publication Number Publication Date
WO2000034257A1 true WO2000034257A1 (fr) 2000-06-15

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PCT/EP1999/009281 WO2000034257A1 (fr) 1998-12-10 1999-11-30 2-imino-thiazolines substituees et leur utilisation comme herbicides

Country Status (3)

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AU (1) AU1557800A (fr)
DE (1) DE19856966A1 (fr)
WO (1) WO2000034257A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002010155A1 (fr) * 2000-07-29 2002-02-07 Bayer Cropscience Ag Arylcetones substituees et leur utilisation en tant qu'herbicides
WO2017005673A1 (fr) * 2015-07-06 2017-01-12 Bayer Cropscience Aktiengesellschaft Hétérocycles contenant de l'azote utiles en tant que pesticides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0259738A2 (fr) * 1986-09-10 1988-03-16 Nihon Tokushu Noyaku Seizo K.K. Composés hétérocycliques
EP0446802A1 (fr) * 1990-03-12 1991-09-18 Sumitomo Chemical Company, Limited Iminothiazolines, leur production, leur utilisation comme herbicide et les intermédiaires nécessaires à leur production
WO1998000408A1 (fr) * 1996-07-02 1998-01-08 Novartis Ag Derives heterocycliques n-phenylimino et leur utilisation comme herbicides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0259738A2 (fr) * 1986-09-10 1988-03-16 Nihon Tokushu Noyaku Seizo K.K. Composés hétérocycliques
EP0446802A1 (fr) * 1990-03-12 1991-09-18 Sumitomo Chemical Company, Limited Iminothiazolines, leur production, leur utilisation comme herbicide et les intermédiaires nécessaires à leur production
WO1998000408A1 (fr) * 1996-07-02 1998-01-08 Novartis Ag Derives heterocycliques n-phenylimino et leur utilisation comme herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PAOLINI J P ET AL, JOURNAL OF MEDICINAL CHEMISTRY., vol. 14, no. 10, 1971, pages 988 - 990, XP002131798, ISSN: 0022-2623 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002010155A1 (fr) * 2000-07-29 2002-02-07 Bayer Cropscience Ag Arylcetones substituees et leur utilisation en tant qu'herbicides
WO2017005673A1 (fr) * 2015-07-06 2017-01-12 Bayer Cropscience Aktiengesellschaft Hétérocycles contenant de l'azote utiles en tant que pesticides
CN107848975A (zh) * 2015-07-06 2018-03-27 拜耳作物科学股份公司 作为杀虫剂的含氮杂环
US10239859B2 (en) 2015-07-06 2019-03-26 Bayer Cropscience Aktiengesellschaft Nitrogen-containing heterocycles as pesticides
AU2016289413B2 (en) * 2015-07-06 2020-03-26 Bayer Cropscience Aktiengesellschaft Nitrogenous heterocycles as a pesticide

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Publication number Publication date
DE19856966A1 (de) 2000-06-15
AU1557800A (en) 2000-06-26

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