WO1998049159A1 - Pyrazoles herbicides - Google Patents

Pyrazoles herbicides Download PDF

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Publication number
WO1998049159A1
WO1998049159A1 PCT/US1998/007978 US9807978W WO9849159A1 WO 1998049159 A1 WO1998049159 A1 WO 1998049159A1 US 9807978 W US9807978 W US 9807978W WO 9849159 A1 WO9849159 A1 WO 9849159A1
Authority
WO
WIPO (PCT)
Prior art keywords
phenyl
pyridinyl
alkyl
propyl
cyc
Prior art date
Application number
PCT/US1998/007978
Other languages
English (en)
Inventor
Chi-Ping Tseng
Original Assignee
E.I. Du Pont De Nemours And Company
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 E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to CA002281904A priority Critical patent/CA2281904A1/fr
Priority to EP98915643A priority patent/EP0977752A1/fr
Priority to AU69776/98A priority patent/AU6977698A/en
Publication of WO1998049159A1 publication Critical patent/WO1998049159A1/fr

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Classifications

    • 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
    • C07D409/06—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 carbon chain containing only aliphatic carbon 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems

Definitions

  • This invention relates to certain pyrazoles, their agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation.
  • the control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
  • This invention is directed to compounds of Formula I including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:
  • R 1 is C r C 3 alkyl
  • R 6 and R 7 are taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 - or
  • alkyl used either alone or in compound words such as "alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, «-propyl, /-propyl, or the different butyl, pentyl or hexyl isomers.
  • 1-2 alkyl indicates that one or two of the available positions for that substituent may be alkyl which are independently selected.
  • Alkenyl includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl” also includes polyenes such as 1 ,2-propadienyl and 2,4-hexadienyl. "Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • Alkoxy includes, for example, methoxy, ethoxy, rc-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • halogen either alone or in compound words such as “haloalkyl” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkenyl “haloalkynyl”, “haloalkoxy”, “haloalkylthio”, and the like, are defined analogously to the term “haloalkyl”.
  • C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
  • C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • alkylcarbonyl include
  • substituents When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1 , said substituents (when they exceed 1 ) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e.g. (RM, then the number of substituents may be selected from the integers between i and j inclusive.
  • Stereoisomers of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s).
  • the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the present invention comprises compounds selected from Formula I and agriculturally suitable salts thereof.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
  • the salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • the salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or phenol.
  • organic bases e.g., pyridine, ammonia, or triethylamine
  • inorganic bases e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium
  • Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1. Compounds of Formula I above, and agriculturally suitable salts thereof, wherein
  • Q is C1-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted with C j -C3 alkyl, C1-C3 alkoxy, cyano or halogen; and
  • R 2 and R 3 are each independently C1-C3 alkyl.
  • Preferred 4. Compounds of Formula I above, and agriculturally suitable salts thereof, wherein
  • Preferred 5. Compounds of Preferred 4 wherein Q is C1-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted with C j -C3 alkyl, C1-C3 alkoxy, cyano or halogen; and R 2 and R 3 are each independently C 1 -C3 alkyl.
  • Compounds of Preferred 5 wherein A is -OC( O)O-. Most preferred are compounds of Formula I selected from the group:
  • compositions comprising herbicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • a surfactant a solid diluent or a liquid diluent.
  • the preferred compositions of the present invention are those which comprise the above preferred compounds.
  • This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein).
  • the preferred methods of use are those involving the above preferred compounds.
  • Scheme 1 illustrates the preparation of compounds of Formula I whereby a compound of Formula 1 is reacted with the appropriate reagent of Formula 2, 3, A, and 5 in the presence of a suitable base.
  • This coupling method is carried out by general methods known in the art; see, for example, Nakamura, et al., WO 95/04054.
  • Compounds of Formula 1 can be prepared by methods described in the art; see, for example, Tseng, WO 97/01550.
  • Compounds of Formulae 2, 3, 4, and 5 are either commercially available or can be prepared by methods well-established in the art from commercially available starting materials.
  • Step E Preparation of 2,3-dihydro-5, 8-dimethylspiro
  • Step F Preparation of 2,3-dihvdro-5,8-dimethylspirof4H-l-benzothiopyran-4,2'- ⁇ ,3 ⁇
  • OXONE® purchased from Aldrich Chemical Company
  • Step G Preparation of l-ethyl-lH-pyrazol-5-yl 2,3-dihvdro-5,8-dimethylspiror4H-l- benzothiopyran-4,2'-[T ,31dioxolane1-6-carboxylate 1 , 1 -dioxide 1.18 g (3.8 mmol) of the title compound of Step F, 0.99 mL (0.01 1 mol) of oxalyl chloride (purchased from Janssen), and 2 drops of N ⁇ /V-dimethylformamide were added to 50 mL of methylene chloride. The mixture was refluxed under nitrogen for 2 h, and was then evaporated to dryness.
  • Step I Preparation of [4- ⁇ (2 ,3 -dihydro-5 , 8-dimethylspiro ⁇ 4H- 1 -benzothiopyran.4,2 '- fl ,31dioxolanl-6-yl)carbonyl]-l -ethyl- lH-pyrazol-5-yll (1-methylethyl) carbonate
  • S,S-dioxide 500 mg (1.23 mmol) of the title compound of Step ⁇ and 1.50 ml (1.50 mmol) of isopropylchloroformate (1.0 solution in toluene; purchased from Aldrich Chemical Co.) were added to acetonitrile, followed by the addition of 0.220 ml (1.56 mmol) of triethylamine.
  • Step A Preparation of r4-F(2,3-dihvdro-5,8-dimethylspiror4H-l-benzothiopyran,4,2'-

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

Abstract

L'invention concerne des composés de formule (I), leurs N-oxydes et leurs sels appropriés à l'agriculture, utiles pour lutter contre la végétation indésirable. Dans ladite formule (I), Q, A et R1-R5 sont tels que définis dans la description. L'invention porte aussi sur des compositions contenant les composés de formule I et sur un procédé de lutte contre la végétation indésirable, qui consiste à mettre la végétation ou son environnement avec une dose efficace d'un composé de formule (I).
PCT/US1998/007978 1997-04-25 1998-04-21 Pyrazoles herbicides WO1998049159A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CA002281904A CA2281904A1 (fr) 1997-04-25 1998-04-21 Pyrazoles herbicides
EP98915643A EP0977752A1 (fr) 1997-04-25 1998-04-21 Pyrazoles herbicides
AU69776/98A AU6977698A (en) 1997-04-25 1998-04-21 Herbicidal pyrazoles

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US4487597P 1997-04-25 1997-04-25
US60/044,875 1997-04-25
US5268297P 1997-07-16 1997-07-16
US60/052,682 1997-07-16

Publications (1)

Publication Number Publication Date
WO1998049159A1 true WO1998049159A1 (fr) 1998-11-05

Family

ID=26722100

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/007978 WO1998049159A1 (fr) 1997-04-25 1998-04-21 Pyrazoles herbicides

Country Status (4)

Country Link
EP (1) EP0977752A1 (fr)
AU (1) AU6977698A (fr)
CA (1) CA2281904A1 (fr)
WO (1) WO1998049159A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001079200A1 (fr) * 2000-04-19 2001-10-25 Idemitsu Kosan Co., Ltd. Derives de pyrazole et herbicides les contenant
WO2012123409A1 (fr) 2011-03-15 2012-09-20 Bayer Cropscience Ag Amides d'acides n-(1,2,5-oxadiazol-3-yl)-, n-(tétrazol-5-yl)- et n-(triazol-5-yl)bicycloaryl carboxyliques et utilisation desdits amides comme herbicides
JP2021517592A (ja) * 2018-04-11 2021-07-26 山▲東▼先▲達▼▲農▼▲化▼股▲ふん▼有限公司Ｓｈａｎｄｏｎｇ Ｃｙｎｄａ Ｃｈｅｍｉｃａｌ Ｃｏ．，Ｌｔｄ． キナゾリンジオン系化合物、その使用および農薬除草剤

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996000008A1 (fr) * 1994-06-27 1996-01-04 Idemitsu Kosan Co., Ltd. Composition herbicide
EP0712853A1 (fr) * 1993-08-02 1996-05-22 Idemitsu Kosan Company Limited Derive de pyrazole
EP0728756A1 (fr) * 1993-11-09 1996-08-28 Idemitsu Kosan Company Limited Derives de pyrazole et herbicide les contenant
WO1997001550A1 (fr) * 1995-06-29 1997-01-16 E.I. Du Pont De Nemours And Company Cetals et spirocycles herbicides
WO1997012885A1 (fr) * 1995-10-04 1997-04-10 Idemitsu Kosan Co., Ltd. Derives de pyrazole

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0712853A1 (fr) * 1993-08-02 1996-05-22 Idemitsu Kosan Company Limited Derive de pyrazole
EP0728756A1 (fr) * 1993-11-09 1996-08-28 Idemitsu Kosan Company Limited Derives de pyrazole et herbicide les contenant
WO1996000008A1 (fr) * 1994-06-27 1996-01-04 Idemitsu Kosan Co., Ltd. Composition herbicide
WO1997001550A1 (fr) * 1995-06-29 1997-01-16 E.I. Du Pont De Nemours And Company Cetals et spirocycles herbicides
WO1997012885A1 (fr) * 1995-10-04 1997-04-10 Idemitsu Kosan Co., Ltd. Derives de pyrazole

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001079200A1 (fr) * 2000-04-19 2001-10-25 Idemitsu Kosan Co., Ltd. Derives de pyrazole et herbicides les contenant
WO2012123409A1 (fr) 2011-03-15 2012-09-20 Bayer Cropscience Ag Amides d'acides n-(1,2,5-oxadiazol-3-yl)-, n-(tétrazol-5-yl)- et n-(triazol-5-yl)bicycloaryl carboxyliques et utilisation desdits amides comme herbicides
JP2021517592A (ja) * 2018-04-11 2021-07-26 山▲東▼先▲達▼▲農▼▲化▼股▲ふん▼有限公司Ｓｈａｎｄｏｎｇ Ｃｙｎｄａ Ｃｈｅｍｉｃａｌ Ｃｏ．，Ｌｔｄ． キナゾリンジオン系化合物、その使用および農薬除草剤

Also Published As

Publication number Publication date
CA2281904A1 (fr) 1998-11-05
EP0977752A1 (fr) 2000-02-09
AU6977698A (en) 1998-11-24

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