WO1994025467A1 - Derives de la thiadiazabicyclononane, leurs procede et intermediaires de preparation et leur utilisation comme herbicides - Google Patents

Derives de la thiadiazabicyclononane, leurs procede et intermediaires de preparation et leur utilisation comme herbicides Download PDF

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Publication number
WO1994025467A1
WO1994025467A1 PCT/EP1994/001234 EP9401234W WO9425467A1 WO 1994025467 A1 WO1994025467 A1 WO 1994025467A1 EP 9401234 W EP9401234 W EP 9401234W WO 9425467 A1 WO9425467 A1 WO 9425467A1
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WO
WIPO (PCT)
Prior art keywords
formula
compounds
compound
active ingredient
chlorine
Prior art date
Application number
PCT/EP1994/001234
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English (en)
Inventor
Georg Pissiotas
Hans Moser
Hans-Georg Brunner
Original Assignee
Ciba-Geigy Ag
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 Ciba-Geigy Ag filed Critical Ciba-Geigy Ag
Priority to AU66799/94A priority Critical patent/AU6679994A/en
Priority to EP94914415A priority patent/EP0696286A1/fr
Publication of WO1994025467A1 publication Critical patent/WO1994025467A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/08—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members

Definitions

  • the present invention relates to novel, herbicidal phenyliminothiadiazabicyclononanone derivatives, a process for their preparation, compositions which contain these compounds, and their use for combating weeds, especially in crops of useful plants, in particular cereals, rice, maize and soya, or for inhibiting plant growth.
  • Herbicidal phenyliminothiadiazabicyclononanone derivatives are disclosed e.g. in
  • the present invention therefore relates to the compounds of the formula I
  • M is hydrogen, an alkali metal or alkaline earth metal cation or an ammonium cation
  • A is C 2 -C 6 alkylene
  • R 1 is chlorine or bromine
  • R 2 is hydrogen or fluorine.
  • suitable alkylene groups can be straight-chain or branched alkylene groups, for example ethylene, n-propylene, isopropylene, n-butylene, isobutylene, sec-butylene, tert-butylene, n-pentylene and n-hexylene radicals, and the branched isomers thereof.
  • alkali metal and alkaline earth metal cations those of lithium, sodium, potassium, magnesium or calcium are especially to be emphasized, but in particular those of sodium or potassium.
  • Suitable ammonium cations are derived e.g. from primary, secondary and tertiary aliphatic and aromatic amines, such as methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine,
  • primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadec
  • n-pentenyl-2-amine 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, diethanolamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine; heterocyclic amines, e.g.
  • pyridine quinoline, isoquinoline, morpholine, thiomorpholine, N-methylmorpholine, N-methylthiomorpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, e.g. anilines, methoxyanilines,
  • ethoxyanilines o, m or p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- or p-chloroanilines.
  • ammonium cations are derived from quaternary ammonium bases and are, in general, the cations of haloammonium salts, e.g. the tetramethylammonium cation, the trimethylbenzylammonium cation, the triethylbenzylammonium cation, the
  • the compounds of the formula I have the effect that the compounds can occur either as optically active individual isomers or in the form of racemic mixtures.
  • the active compounds of the formula I are to be understood as meaning both the pure optical antipodes and the racemates.
  • particularly preferred compounds are those in which R 1 is chlorine and R 2 is fluorine.
  • particularly preferred compounds of the formula la are those in which A is C 2 -C 4 alkylene, R 1 is chlorine and R 2 is fluorine.
  • EP-A-0 312 064 and EP-A-0468 924 comprises converting a compound of the formula II using thiophosgene under customary conditions to the isothiocyanate of the formula III
  • the isothiocyanate of the formula III is obtained in a manner known per se by reacting the corresponding amine of the formula II with thiophosgene. Processes of this type are described, for example, in EP-A-0 304 920, pages 53 and 55; EP-A-0 312 064, page 11, last section and page 12, lines 12-18; and EP-A-0468 924, page 21, lines 29-47, page 22, Example H2, and page 27, Example H17.
  • the compound of the formula IV is obtained in a manner known per se by reacting the isothiocyanate of the formula III with hexahydropyridazine of the formula V. Reactions of this type are described, for example, in EP-A-0 312 064, page 11, last section, page 12, lines 19-24; EP-A-0468 924, page 16, last section and page 17, first section, page 19, lines 42-46 and page 22, Example H3.
  • cyclization of the hexahydropyridazinylthiocarbonylamino derivative of the formula IV can expediently be carried out using phosgene, diphosgene (trichloromethyl chloroformate) or triphosgene (bis(trichloromethyl) carbonate) in an inert solvent at low temperatures, preferably 0 to 50°C, particularly preferably at 0 to 15°C. Cyclizations of this type are described, for example, in EP-A-0312 064, page 11, lines 1-40 and
  • hexahydropyridazine of the formula V is known or can be prepared analogously to processes known from the literature, for example Bull. Soc. Chim. France 1957, 704; EP-A-0 304 920, pages 9-11 (Schemes 2-4); and EP-A-0468 924, page 19, last section, page 20, first section and page 28, Example H18.
  • the final product of the formula I can be isolated in the customary manner by carefully concentrating and/or evaporating the solvent in vacuo and purified by recrystallizing or triturating the solid residue in solvents in which it does not readily dissolve, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
  • Suitable application methods for use, according to the invention, of the compounds of the formula I or compositions comprising these are all those customary in agriculture, e.g. pre-emergence application, post-emergence application and seed dressing, and also various methods and techniques, for example the controlled release of active ingredient.
  • the active ingredient in solution is absorbed on mineral granular supports or polymerized granules (urea/formaldehyde) and dried.
  • a coating can additionally be applied (coated granules), which enables the active ingredient to be delivered in metered form over a certain period.
  • the compounds of the formula I can be employed in unchanged form, i.e. as they are obtained in the synthesis, but they are preferably processed in the customary manner using the auxiliaries conventional in formulation technology, e.g. to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusting agents, granules or microcapsules.
  • the application processes such as spraying, atomizing, dusting, wetting, scattering or watering are chosen accordingly, like the nature of the compositions, the desired targets and the given conditions.
  • compositions i.e. the compositions, preparations or combinations comprising the active ingredient of the formula I or at least one active ingredient of the formula I and, if desired, one or more solid or liquid additives
  • additives e.g. solvents or solid carriers.
  • surface-active compounds surfactants
  • surfactants can also be used in the production of the formulations.
  • Possible solvents are: aromatic hydrocarbons, in particular the fractions C 8 to C 12 , such as mixtures of alkylbenzenes, e.g. xylene mixtures or alkylated naphthalenes; aliphatic and cycloaliphatic hydrocarbons such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols, such as ethanol, propanol or butanol; glycols and their ethers and esters, such as propylene glycol or dipropylene glycol ethers, ketones such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water; vegetable oils and their esters, such as rapeseed, castor or soya bean oil; and if desired also silicone oils.
  • aromatic hydrocarbons in particular the fractions C 8 to C 12 , such as mixtures of alkyl
  • Solid carriers used are as a rule ground natural minerals, such as calcites, talc, kaolin, montmorillonite or attapulgite.
  • highly disperse silicic acid or highly disperse absorbent polymers can also be added.
  • Possible granulated, absorptive granular supports are porous types, e.g. pumice, brick dust, sepiolite or bentonite, and possible non-sorptive support materials are e.g. calcite or sand.
  • a multiplicity of pregranulated materials of inorganic or organic nature such as, in particular, dolomite or comminuted plant remains can be used.
  • suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants are also understood as meaning surfactant mixtures.
  • Suitable anionic surfactants can be either so-called water-soluble soaps or water-soluble synthetic surface-active compounds.
  • Soaps which may be mentioned are the alkali metal, alkaline earth metal or unsubstituted or substituted ammonium salts of higher fatty acids (C 10 -C 22 ), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained e.g. from coconut or tallow oil.
  • the fatty acid methyl tauride salts may also be mentioned.
  • so-called synthetic surfactants are used, in particular fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
  • the fatty alcohol sulfonates or sulfates as a rule are present as alkali metal, alkaline earth metal or unsubstituted or substituted ammonium salts and contain an alkyl radical having 8 to 22 C atoms, alkyl also including the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate or of a fatty alcohol sulfate mixture prepared from natural fatty acids. Included here are also the salts of sulfuric acid esters and sulfonic acids of fatty alcohol-ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid radical having 8-22 C atoms.
  • Alkylarylsulfonates are e.g. the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic acid-formaldehyde condensation product.
  • phosphates e.g. salts of the phosphoric acid ester of a
  • p-nonylphenol-(4-14)-ethylene oxide adduct or phospholipids are also suitable.
  • Non-ionic surfactants are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic)
  • hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols are hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
  • non-ionic surfactants are the water-soluble polyethylene oxide adducts of polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol having 1 to 10 carbon atoms in the alkyl chain and containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups.
  • the said compounds customarily contain 1 to 5 ethylene glycol units per propylene glycol unit.
  • non-ionic surfactants examples include nonylphenol
  • polyethoxyethanols castor oil polyglcyol ethers, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and
  • Fatty acid esters of polyoxyethylenesorbitan such as polyoxyethylenesorbitan trioleate are also suitable.
  • the cationic surfactants are primarily quaternary ammonium salts which, as
  • N substituents contain at least one alkyl radical having 8 to 22 C atoms and, as further substituents, contain lower, free or halogenated alkyl or benzyl radicals or lower hydroxyalkyl radicals.
  • the salts are preferably present as halides, methylsulfates or ethyl-sulfates, e.g. the stearyltrimethylammonium chloride or the
  • the herbicidal preparations as a rule contain 0.1 to 99 %, in particular 0.1 to 95 %, of active ingredient of the formula I, 1 to 99 % of a solid or liquid formulation auxiliary and 0 to 25 %, in particular 0.1 to 25 %, of a surfactant.
  • compositions can also contain further additives such as stabilizers, e.g. from free or epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, adhesives and fertilizers or other active ingredients for achieving specific effects.
  • stabilizers e.g. from free or epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, adhesives and fertilizers or other active ingredients for achieving specific effects.
  • Emulsifiable concentrates are:
  • Active ingredient 1 to 90 %, preferably 5 to 50 %
  • Surface-active agent 5 to 30 %, preferably 10 to 20 %
  • Solvent 15 to 94 %, preferably 70 to 85 %
  • Active ingredient 0.1 to 50 %, preferably 0.1 to 1 %
  • Solid carrier 99.9 to 90 %, preferably 99.9 to 99 %
  • AAccttiivvee ingredient 5 to 75 %, preferably 10 to 50 %
  • Surface-active agent 1 to 40 %, preferably 2 to 30 %
  • Active ingredient 0.5 to 90 %, preferably 1 to 80 %
  • Surface-active agent 0.5 to 20 %, preferably 1 to 15 %
  • Solid carrier 5 to 95 %, preferably 15 to 90 %
  • Active ingredient 0.1 to 30 %, preferably 0.1 to 15 %
  • Solid carrier 99.5 to 70 %, preferably 97 to 85 %
  • the active ingredients of the formula I are as a rule successfully employed at application rates of 0.001 to 2 kg/ha, in particular 0.005 to 1 kg/ha.
  • the dosage necessary for the desired effect can be determined by tests. It is dependent on the type of action, the development stage of the crop plant and of the weed and on the application (site, time, process) and, limited by these parameters, can vary within wide ranges.
  • the compounds of the formula I are distinguished by selective herbicidal properties which give them an excellent capacity for use in crops of useful plants, in particular in cereals, rice, maize and soya.
  • Crops are also understood as meaning those which have been made tolerant to herbicides or herbicide classes by conventional cultural or recombinant DNA methods.
  • a suspension of 39.0 g of 2-[1-(5-amino-2-chloro-4-fluorophenylthio)] butyric acid in 100 ml of ethylene chloride is added in portions with stirring at room temperature to a mixture of 29.6 g of calcium carbonate, 14.8 ml of thiophosgene in 200 ml of ethylene chloride and 200 ml of water.
  • the reaction mixture is treated with 200 ml of water and 400 ml of ethyl acetate and rendered acidic using 2 N hydrochloric acid.
  • the organic phase is separated off and dried over sodium sulfate.
  • Aromatic hydrocarbon mixture 85% 78% 55% 16%
  • Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
  • the solutions are suitable for application in the form of very small drops.
  • the active ingredient is well mixed with the additives and well ground in a suitable mill. Wettable powders are obtained which can be diluted with water to give suspensions of any desired concentration.
  • Active ingredient as in Tables 1-3 0.1 % 5 % 15 % Highly disperse silicic acid 0.9 % 2 % 2 % Inorg. carrier 99.0 % 93 % 83 % ( ⁇ 0.1- 1 mm)
  • the finely ground active ingredient is uniformly applied in a mixer to the carrier material moistened with polyethylene glycol. Dust-free coated granules are obtained in this manner.
  • the active ingredient is mixed with the additives, and the mixture is ground and moistened with water. This mixture is extruded and then dried in a stream of air.
  • Ready-to-apply dusting agents are obtained by mixing the active ingredient with the carriers and grinding in a suitable mill.
  • the finely ground active ingredient is intimately mixed with the additives.
  • a suspension concentrate is thus obtained from which suspensions of any desired concentration can be prepared by diluting with water.
  • Monocotyledonous and dicotyledonous test plants are raised in a greenhouse in plastic pots containing standard soil and sprayed at the 4- to 6-leaf stage with an aqueous suspension of the test substances of the formula I, prepared from a 25 % wettable powder (Example F3, b)), corresponding to a dosage of 2 kg of AITha (500 1 of water/ha).
  • Test plants Sinapis, Solanum, Ipomoea, Stellaria.

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

Abstract

L'invention concerne les composés de la formule (I). Dans cette formule M représente un hydrogène, un cation de métal alcalin ou alcalino-terreux ou un cation ammonium, A représente un alkylène C2-C6, R1 représente le chlore ou le brome et R2 représente hydrogène ou fluor. L'invention concerne également la préparation de ces composés et leur utilisation en tant qu'herbicides.
PCT/EP1994/001234 1993-05-03 1994-04-21 Derives de la thiadiazabicyclononane, leurs procede et intermediaires de preparation et leur utilisation comme herbicides WO1994025467A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU66799/94A AU6679994A (en) 1993-05-03 1994-04-21 Thiadiazabicyclononane derivatives, process and intermediates for their preparation and their use as herbicides
EP94914415A EP0696286A1 (fr) 1993-05-03 1994-04-21 Derives de la thiadiazabicyclononane, leurs procede et intermediaires de preparation et leur utilisation comme herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH134693 1993-05-03
CH1346/93-3 1993-05-03

Publications (1)

Publication Number Publication Date
WO1994025467A1 true WO1994025467A1 (fr) 1994-11-10

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PCT/EP1994/001234 WO1994025467A1 (fr) 1993-05-03 1994-04-21 Derives de la thiadiazabicyclononane, leurs procede et intermediaires de preparation et leur utilisation comme herbicides

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EP (1) EP0696286A1 (fr)
AU (1) AU6679994A (fr)
WO (1) WO1994025467A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273417A1 (fr) * 1986-12-24 1988-07-06 Kumiai Chemical Industry Co., Ltd. Dérivés de thiadiazabicyclononane et compositions herbicides
JPH02188588A (ja) * 1989-01-14 1990-07-24 Nissan Chem Ind Ltd 縮合ヘテロ環誘導体、その製法及び除草剤
EP0457714A1 (fr) * 1990-03-22 1991-11-21 Ciba-Geigy Ag Dérivés de thiadiazabicyclononane, leur procédé de préparation, intermédiaires et leur application comme herbicides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0273417A1 (fr) * 1986-12-24 1988-07-06 Kumiai Chemical Industry Co., Ltd. Dérivés de thiadiazabicyclononane et compositions herbicides
JPH02188588A (ja) * 1989-01-14 1990-07-24 Nissan Chem Ind Ltd 縮合ヘテロ環誘導体、その製法及び除草剤
EP0457714A1 (fr) * 1990-03-22 1991-11-21 Ciba-Geigy Ag Dérivés de thiadiazabicyclononane, leur procédé de préparation, intermédiaires et leur application comme herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 114, no. 3, 21 January 1991, Columbus, Ohio, US; abstract no. 23974g, J. SATO ET AL: "Preparation of condensed heterocycles as herbicides" page 710; *

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Publication number Publication date
AU6679994A (en) 1994-11-21
EP0696286A1 (fr) 1996-02-14

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