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WO2002066471A1 - Nouvelles 1,5-dialkyl-3-(3-oxo-3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-6-thioxo-[1,3,5]triazinan-2,4-diones - Google Patents

Nouvelles 1,5-dialkyl-3-(3-oxo-3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-6-thioxo-[1,3,5]triazinan-2,4-diones Download PDF

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Publication number
WO2002066471A1
WO2002066471A1 PCT/EP2002/001560 EP0201560W WO02066471A1 WO 2002066471 A1 WO2002066471 A1 WO 2002066471A1 EP 0201560 W EP0201560 W EP 0201560W WO 02066471 A1 WO02066471 A1 WO 02066471A1
Authority
WO
WIPO (PCT)
Prior art keywords
dialkyl
thioxo
oxo
oxazin
dihydro
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2002/001560
Other languages
German (de)
English (en)
Inventor
Ingo Sagasser
Olaf Menke
Gerhard Hamprecht
Michael Puhl
Robert Reinhard
Thomas Schmidt
Cyrill Zagar
Matthias Witschel
Andreas Landes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of WO2002066471A1 publication Critical patent/WO2002066471A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4

Definitions

  • R 3 and R 4 are independently C 1 -C 4 -alkyl.
  • the compounds I are also suitable for the desiccation / defoliation of parts of plants, for which crop plants such as cotton, potato, rapeseed, sunflower, soybean or field beans, in particular cotton, are suitable.
  • crop plants such as cotton, potato, rapeseed, sunflower, soybean or field beans, in particular cotton, are suitable.
  • alkyl, alkenyl and alkynyl radicals mentioned in the definition of R 1 , R 3 and R 4 are collective terms for individual lists of the individual group members.
  • C 3 -C 4 -alkyl-, C 3 -C 6 -alkyl- , C -C 6 alkenyl and C -Cg alkynyl radicals can be straight-chain or branched.
  • Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
  • -C-C 4 alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, CH (CH 3 ) -C 2 H 5 , 2-methylpropyl or C (CH 3 ) 3 , in particular for CH 3 , C 2 H 5 or CH (CH 3 ) 2 ;
  • Ci-Cg-alkyl for: -C ⁇ C alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2- Dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl or l-ethyl- 2-methylpropyl, in particular for CH, CHs, n-propy
  • C 2 -C 6 alkenyl for: e.g. ethenyl, prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop- 2-en-l-yl, 2-butene
  • R 2 is hydrogen
  • those compounds I are preferred in which the R 1 is C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, ethynyl or C -C 6 alkynyl.
  • C 1 -C 6 -alkyl is particularly preferred; likewise particularly preferably C 4 -C 6 alkynyl.
  • the compounds I are likewise preferred, where R 1 is propargyl and R 2 is fluorine.
  • the compounds I are particularly preferred, where R 1 is propargyl, R 2 is fluorine and R 3 and R 4 are methyl.
  • the reaction is carried out according to the information given in the specified article.
  • the isocyanates VI are reacted with the thioureas IV preferably in the presence of an activated carbonyl source such as carbonyldiimidazole, phosgene, diphosgene, triphosgene and chloroformate.
  • an activated carbonyl source such as carbonyldiimidazole, phosgene, diphosgene, triphosgene and chloroformate.
  • the cyclization is preferably carried out without isolating the intermediates VII.
  • the isocyanates VI are in turn obtainable from the corresponding 6-amino-benzoxazinones VIII:
  • Processes A), B), C) and D) are preferably carried out in the presence of a suitable reaction auxiliary.
  • reaction auxiliaries preferably include alkali metal and alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides and alkanolates, e.g.
  • butoxide also basic organic nitrogen compounds, for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylain, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldiisopropylamine, N, N-dimethylaniline, N, N- Dimethyl-benzylamine, pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2, 4-dimethylpyridine, 2, 6-dimethylpyridine, 3, 4-dimethylpyridine and 3, 5-dimethylpyridine, 5-ethyl 2-methylpyridine, 4-dimethylaminopyridine, N-methylpiperidine, 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] - non-5-ene (DBN ) or 1, 8-diazabicyclo [5, 4, 0]
  • Processes A), B), C) and D) are usually carried out in the presence of an inert diluent, generally the customary organic solvents.
  • an inert diluent generally the customary organic solvents.
  • These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, for example pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, the xylenes, chlorobenzene, dichlorobenzenes, cyclohexane, methylcyclohexane, dichloromethane, trichloromethane, dialkethloromethane, and tetrachloromethane, such as tetrachloromethane , Diisopropyl ether, methyl tert-butyl ether (MTBE), ethyl tert.
  • MTBE tert-but
  • -butyl ester Sulfoxides such as dimethyl sulfoxide; Alkanols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec. - Butanol and tert. Butanol; Glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether and diethylene glycol monoethyl ether; their mixtures with water or pure water.
  • Sulfoxides such as dimethyl sulfoxide
  • Alkanols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec. - Butanol and tert. Butanol
  • Glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glyco
  • reaction temperatures can be varied within a substantial range, for example from 0 to 200.degree. Is preferably carried out at 10 to 150 ° C, in particular at 20 ° C to the boiling point of the reaction mixture.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in an excess, up to about twice the molar amount of the other component.
  • the processes A), B), C) and D) are advantageously carried out at atmospheric pressure or under the autogenous pressure of the respective reaction mixture. However, it is also possible to carry out the processes under elevated or reduced pressure - generally at 0.1 to 10 bar.
  • the respective reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase towards the product.
  • the compounds I are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In cult Other crops such as wheat, rice, corn, soybeans and cotton act against weeds and grass weeds without significantly damaging crops. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • desiccants are particularly suitable for drying out the aerial parts of crops such as potatoes, rapeseed, sunflower and soybeans. This enables a fully mechanical harvesting of these important crops.
  • the waste promoted by the use of active compounds of the formula I according to the invention is based on the formation of separating tissue between the fruit or leaf and shoot part of the plants.
  • Cotton defoliation is of particular economic interest because it makes harvesting easier. At the same time, the shortening of the time interval in which the individual plants mature leads to an increased quality of the harvested fiber material.
  • the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the herbicidal compositions comprise a herbicidally effective amount of at least one active compound of the formula I and auxiliaries customary for the formulation of crop protection agents.
  • inert auxiliaries mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffins, tetrahydronaphthalene, alkylated n
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions can the l-aryl-4-thiouracile I as such or in an oil or solution medium solution, be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • wetting agents adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, adhesive, dispersant or emulsifier and possibly solvent or oil can also be prepared which are suitable for dilution with water.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • Formulations generally contain about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient I.
  • the active ingredients are in a purity of 90% to 100%, preferably 95% to 100% ( according to the NMR spectrum).
  • the compounds I according to the invention can be formulated, for example, as follows:
  • Dissolved mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.
  • Dissolved mixture which consists of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
  • V. 3 parts by weight of a compound I are mixed with 97 parts by weight of finely divided kaolin. In this way, a dust is obtained which contains 3% by weight of the active ingredient.
  • the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not struck wherever possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, season, target plants and growth stage.
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, unless this was affected by the active ingredients.
  • test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the application rate for post-emergence treatment was 7, 8 or 3.9 g / ha aS (active substance).
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • the plants used in the greenhouse experiments are composed of the following types:
  • the young cotton plants were treated to runoff with aqueous preparations of the active ingredients (with the addition of 0.15% by weight of the fatty alcohol alkoxylate Plurafac® LF 700 1 ', based on the spray mixture).
  • the amount of water applied was the equivalent of 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation in% were determined.

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

Abstract

La présente invention concerne de nouvelles 1,5-dialkyl-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-6-thioxo-[1,3,5]triazinan-2,4-diones de formule (I), dans laquelle R<1> représente hydrogène, alkyle C1-C6, alcényle C2-C6 ou alcynyle C2-C6, R<2> représente hydrogène ou halogène et R<3> et R<4> représentent indépendamment l'un de l'autre alkyle C1-C4. Ces composés sont utilisés en tant qu'herbicides ou servent à la dessiccation/défoliation de plantes.
PCT/EP2002/001560 2001-02-20 2002-02-14 Nouvelles 1,5-dialkyl-3-(3-oxo-3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-6-thioxo-[1,3,5]triazinan-2,4-diones Ceased WO2002066471A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10108161.8 2001-02-20
DE10108161 2001-02-20

Publications (1)

Publication Number Publication Date
WO2002066471A1 true WO2002066471A1 (fr) 2002-08-29

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Country Link
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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009115490A3 (fr) * 2008-03-17 2010-07-08 Basf Se Compositions herbicides comprenant pyroxasulfone v
WO2010145992A1 (fr) 2009-06-19 2010-12-23 Basf Se Benzoxazinones herbicides
WO2011018486A2 (fr) 2009-08-14 2011-02-17 Basf Se Composition herbicide active comprenant des benzoxazinones
WO2011057935A1 (fr) 2009-11-13 2011-05-19 Basf Se Composés de 3-(3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-1h-pyrimidin-2,4-dione en tant qu'herbicides
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides
WO2012080239A1 (fr) 2010-12-15 2012-06-21 Basf Se Compositions herbicides
WO2013089208A1 (fr) * 2011-12-15 2013-06-20 Sumitomo Chemical Company, Limited Procédé de destruction des mauvaises herbes dans un champ de canne à sucre
US9034791B2 (en) 2012-09-10 2015-05-19 Sumitomo Chemical Company, Limited Method for controlling noxious organisms
US9040454B2 (en) 2012-06-20 2015-05-26 Sumitomo Chemical Company, Limited Method for controlling pests
US9040455B2 (en) 2012-06-20 2015-05-26 Sumitomo Chemical Company, Limited Method for controlling pests
US9040456B2 (en) 2012-09-10 2015-05-26 Sumitomo Chemical Company, Limited Method for controlling noxious organisms
AU2012258419B2 (en) * 2011-12-08 2016-06-16 Sumitomo Chemical Company, Limited Method of controlling pest
AU2012261757B2 (en) * 2011-12-20 2016-07-07 Sumitomo Chemical Company, Limited Method of controlling pest
KR20160084458A (ko) * 2013-11-14 2016-07-13 바스프 에스이 1,5-디메틸-6-티옥소-3-(2,2,7-트리플루오로-3-옥소-4-(프로프-2-이닐)-3,4-디히드로-2H-벤조[ｂ][1,4]옥사진-6-일)-1,3,5-트리아지난-2,4-디온의 조성물
US9622475B2 (en) 2012-06-20 2017-04-18 Sumitomo Chemical Company, Limited Method for controlling pests
US9775352B2 (en) 2011-12-08 2017-10-03 Sumitomo Chemical Company, Limited Method of controlling pest
WO2025176562A1 (fr) 2024-02-23 2025-08-28 Syngenta Crop Protection Ag Dérivés de 2-[5-(3,5-diméthyl-2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-2-oxo-1,3-benzothiazole et dérivés de 1,3-benzoxazole et de benzimidazole correspondants utilisés en tant qu'herbicides

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0640600A1 (fr) * 1993-08-30 1995-03-01 Bayer Ag Hétérocyclylbezohétérocycles

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0640600A1 (fr) * 1993-08-30 1995-03-01 Bayer Ag Hétérocyclylbezohétérocycles

Cited By (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009115490A3 (fr) * 2008-03-17 2010-07-08 Basf Se Compositions herbicides comprenant pyroxasulfone v
US8754008B2 (en) 2009-06-19 2014-06-17 Basf Se Herbicidal benzoxazinones
US9220268B2 (en) 2009-06-19 2015-12-29 Basf Se Herbicidal benzoxazinones
WO2010145992A1 (fr) 2009-06-19 2010-12-23 Basf Se Benzoxazinones herbicides
US9066519B2 (en) 2009-06-19 2015-06-30 Basf Se Herbicidal benzoxazinones
KR101758396B1 (ko) 2009-06-19 2017-07-14 바스프 에스이 제초성 벤족사지논
CN102459205A (zh) * 2009-06-19 2012-05-16 巴斯夫欧洲公司 除草的苯并*嗪酮类
CN104447385A (zh) * 2009-06-19 2015-03-25 巴斯夫欧洲公司 除草的苯并噁嗪酮类
JP2012530098A (ja) * 2009-06-19 2012-11-29 ビーエーエスエフ ソシエタス・ヨーロピア 除草性ベンゾオキサジノン類
AU2010261874B2 (en) * 2009-06-19 2015-05-14 Basf Se Herbicidal benzoxazinones
CN102459205B (zh) * 2009-06-19 2014-11-12 巴斯夫欧洲公司 除草的苯并*嗪酮类
EA023754B1 (ru) * 2009-06-19 2016-07-29 Басф Се Гербицидные бензоксазиноны
WO2011018486A3 (fr) * 2009-08-14 2011-10-13 Basf Se Composition herbicide active comprenant des benzoxazinones
WO2011018486A2 (fr) 2009-08-14 2011-02-17 Basf Se Composition herbicide active comprenant des benzoxazinones
WO2011057935A1 (fr) 2009-11-13 2011-05-19 Basf Se Composés de 3-(3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-1h-pyrimidin-2,4-dione en tant qu'herbicides
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides
US8669208B2 (en) 2010-10-01 2014-03-11 Basf Se Herbicidal benzoxazinones
WO2012080239A1 (fr) 2010-12-15 2012-06-21 Basf Se Compositions herbicides
CN103260412B (zh) * 2010-12-15 2015-09-02 巴斯夫欧洲公司 除草组合物
US8916501B2 (en) 2010-12-15 2014-12-23 Basf Se Herbicidal compositions
CN103260412A (zh) * 2010-12-15 2013-08-21 巴斯夫欧洲公司 除草组合物
US10470462B2 (en) 2011-12-08 2019-11-12 Sumitomo Chemical Company, Limited Method of controlling pest
US10292392B2 (en) 2011-12-08 2019-05-21 Sumitomo Chemical Company, Limited Method of controlling pest
US9775352B2 (en) 2011-12-08 2017-10-03 Sumitomo Chemical Company, Limited Method of controlling pest
AU2012258419B2 (en) * 2011-12-08 2016-06-16 Sumitomo Chemical Company, Limited Method of controlling pest
WO2013089208A1 (fr) * 2011-12-15 2013-06-20 Sumitomo Chemical Company, Limited Procédé de destruction des mauvaises herbes dans un champ de canne à sucre
AU2012261757B2 (en) * 2011-12-20 2016-07-07 Sumitomo Chemical Company, Limited Method of controlling pest
US9420792B2 (en) 2012-06-20 2016-08-23 Sumitomo Chemical Company, Limited Method for controlling pests
US9040454B2 (en) 2012-06-20 2015-05-26 Sumitomo Chemical Company, Limited Method for controlling pests
US10362789B2 (en) 2012-06-20 2019-07-30 Sumitomo Chemical Company, Limited Method for controlling pests
US9040455B2 (en) 2012-06-20 2015-05-26 Sumitomo Chemical Company, Limited Method for controlling pests
US9420789B2 (en) 2012-06-20 2016-08-23 Sumitomo Chemical Company, Limited Method for controlling pests
US9622475B2 (en) 2012-06-20 2017-04-18 Sumitomo Chemical Company, Limited Method for controlling pests
US9040456B2 (en) 2012-09-10 2015-05-26 Sumitomo Chemical Company, Limited Method for controlling noxious organisms
US9420786B2 (en) 2012-09-10 2016-08-23 Sumitomo Chemical Company, Limited Method for controlling noxious organisms
US9420787B2 (en) 2012-09-10 2016-08-23 Sumitomo Chemical Company, Limited Method for controlling noxious organisms
US9034791B2 (en) 2012-09-10 2015-05-19 Sumitomo Chemical Company, Limited Method for controlling noxious organisms
CN105916379A (zh) * 2013-11-14 2016-08-31 巴斯夫欧洲公司 1,5-二甲基-6-硫代-3-(2,2,7-三氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[b][1,4]噁嗪-6-基)-1,3,5-三嗪烷-2,4-二酮的组合物
KR20160084458A (ko) * 2013-11-14 2016-07-13 바스프 에스이 1,5-디메틸-6-티옥소-3-(2,2,7-트리플루오로-3-옥소-4-(프로프-2-이닐)-3,4-디히드로-2H-벤조[ｂ][1,4]옥사진-6-일)-1,3,5-트리아지난-2,4-디온의 조성물
CN105916379B (zh) * 2013-11-14 2018-09-11 巴斯夫欧洲公司 1,5-二甲基-6-硫代-3-(2,2,7-三氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[b][1,4]噁嗪-6-基)-1,3,5-三嗪烷-2,4-二酮的组合物
KR102328765B1 (ko) 2013-11-14 2021-11-18 바스프 에스이 1,5-디메틸-6-티옥소-3-(2,2,7-트리플루오로-3-옥소-4-(프로프-2-이닐)-3,4-디히드로-2H-벤조[ｂ][1,4]옥사진-6-일)-1,3,5-트리아지난-2,4-디온의 조성물
WO2025176562A1 (fr) 2024-02-23 2025-08-28 Syngenta Crop Protection Ag Dérivés de 2-[5-(3,5-diméthyl-2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-2-oxo-1,3-benzothiazole et dérivés de 1,3-benzoxazole et de benzimidazole correspondants utilisés en tant qu'herbicides

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