EP0000324A1 - Cyclopropylméthoxyanilides substituées, leur procédé de préparation et leur application comme herbicides - Google Patents

Cyclopropylméthoxyanilides substituées, leur procédé de préparation et leur application comme herbicides Download PDF

Info

Publication number
EP0000324A1
EP0000324A1 EP78100019A EP78100019A EP0000324A1 EP 0000324 A1 EP0000324 A1 EP 0000324A1 EP 78100019 A EP78100019 A EP 78100019A EP 78100019 A EP78100019 A EP 78100019A EP 0000324 A1 EP0000324 A1 EP 0000324A1
Authority
EP
European Patent Office
Prior art keywords
compound
chloro
alkyl
hydrogen
substituted
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.)
Granted
Application number
EP78100019A
Other languages
German (de)
English (en)
Other versions
EP0000324B1 (fr
Inventor
Anthony Felix Raymond
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.)
Stauffer Chemical Co
Original Assignee
Stauffer Chemical Co
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 Stauffer Chemical Co filed Critical Stauffer Chemical Co
Publication of EP0000324A1 publication Critical patent/EP0000324A1/fr
Application granted granted Critical
Publication of EP0000324B1 publication Critical patent/EP0000324B1/fr
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic 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
    • A01N47/08—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
    • A01N47/20—N-Aryl derivatives 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis

Definitions

  • This invention relates to novel herbicidal compounds having the formula in which R 1 is alkyl, lower alkenyl, chloro-lower alkyl, lower cycloalkyl, lower alkoxy, thio-lower alkyl, or R 2 is hydrogen, lower alkoxyalkyl or lower alkanoyl; R 3 and R 4 are independently hydrogen, lower alkyl or lower alkoxy; X and Y are independently chloro, fluoro or bromo; Z is hydrogen, methyl, dimethyl, or one methyl and one chloro substituent; and n is 0 or 1, provided that if n is 1, R 1 is alkyl and R 2 -is hydrogen, then R 1 is an alkyl group having from 1 to 4 carbon atoms.
  • alkyl such groups having from 1 to 10, preferably from 1 to 6 carbon atoms, including both straight chain and branched chain groups.
  • alkyl groups are methyl, ethyl, n-propyl, isopropyl, butyl, 1-methylbutyl, and 1,1-dimethylbutyl groups.
  • lower alkyl By the terms “lower alkyl”, “chloro-lower alkyl”, “lower alkoxy”, “thio-lower alkyl”, “lower alkoxyalkyl” and “lower alkanoyl” are meant such groups having from 1 to 4 carbon atoms. Examples of such groups are methyl, ethyl, isopropyl, n-butyl, methoxy, isopropoxy, ⁇ -chloroethyl, thioethyl, ethoxymethyl, propionyl, and the like.
  • lower alkenyl such groups having from 2 to 4 carbon atoms, for example, propenyl and isopropenyl.
  • lower cycloalkyl such groups having from 3 to 5 carbon atoms.
  • a preferred member of this group is cyclopropyl.
  • the compounds are ureas; that is R 1 is .
  • R 1 is alkyl, lower alkenyl, chloro-lower alkyl or lower cycloalkyl; the compounds are mono-amides; if R 1 is lower alkoxy the compounds are carbamates; if R 1 is thio-lower alkyl, they are thiocarbamates.
  • R 1 is as defined in the previous sentence, the nitrogen-containing group is referred to as the "amide moiety”.
  • R i is an amide moiety and R 2 is lower alkanoyl, the compounds are imides.
  • R 2 is preferably hydrogen.
  • the amide or urea moiety and the halo-substituted cyclopropylmethoxy moiety are substituted on the phenyl ring in the meta position with respect, to each other.
  • the two moieties are substituted on the phenyl ring in the para position with respect to each other.
  • the two moieties are substituted on the phenyl ring in the para position with respect to each other and a mono-chloro group is substituted on the phenyl ring in the ortho position with respect to the cyclopropylmethoxy substituent.
  • This embodiment includes many of the most active compounds of this invention.
  • X and Y are both chloro.
  • X is chloro and Y is bromo or fluoro.
  • X and Y are both chloro and Z is 1-methyl.
  • Z is 3-chloro, 3-methyl.
  • the compounds of this invention have been found, in general, to be active herbicides; that is, they have been found to be herbicidally effective against various weeds. Weeds, in the broadest sense are plants which grow in locations in which they are not desired.
  • the compounds of this invention have varied herbicidal activities; that is, the effect of the compounds on weeds differs according to the structure, with regard to pre- and post-emergence activity and grassy versus broadleafed plant response, as well as varied responses between species.
  • the compounds of this invention show at best only moderate general activity as pre-emergence herbicides but are primarily active as post-emergence herbicides at rates of application of up to about 8 pounds per acre or higher.
  • the compounds are active primarily against broadleaf weeds; some of the compounds of this invention are active against both broadleaf and grass weeds as post-emergence herbicides.
  • novel compounds may be employed as both general and selective herbicides. When employed at high rates they can be used as total weedkillers in places when complete or near complete destruction of vegetation is needed, for example, on railroad trackbeds, shoulders and median strips of highways, vacant lots, etc. When used at lower rates, the compounds may be satisfactory as selective herbicides; several of these compounds have been shown selective control of broadleaf weeds in small grain crops such as wheat and barley, even when applied at low rates.
  • A. herbicide as used herein means a compound which controls or modifies the growth of plants.
  • herbicidally effective amount is meant an amount of the compound which causes a modifying effect upon the growth of plants.
  • plants is meant germinant seeds, emerging seedlings, and established vegetation, including roots and above-ground portions.
  • modifiying effects include all deviations from development, for example, killing, retardation, defoliation, desiccation, regulation, stunting,til- lering, stimulation, leaf burn, dwarfing, and the like.
  • this invention relates to herbicidal compositions of matter employing the compounds of the present invention in admixture with an inert diluent or carrier.
  • this invention relates to a method for controlling undesirable vegetation comprising applying to the locus thereof a herbicidally effective amount of a compound of the present invention.
  • the compound is applied subsequent to the emergence of the undesired vegetation at the locus.
  • the compounds of the present invention are prepared by:
  • R 2 is lower alkoxyalkyl
  • R 2 is lower alkoxyalkyl
  • a halo alkyl ether such as chloromethyl ethyl ether
  • Reaction (a) can be enhanced by the use of a phase transfer catalyst such as a quaternary onium salt.
  • a solution was formed by dissolving 6.5 g. (0.03 mole) 3-(2',2'-dichloro-1'-methylcyclopropylmethoxy)aniline, 3.2g. (0.03 mole) ethyl chloroformate and 3.1 g. (0.031 mole) triethylamine in 50 ml. benzene. The solution was refluxed for 3 hours and cooled. Methylene chloride was added and the organic layer was washed with water, dried and evaporated. There was obtained 8.7 g. of the desired product, nD 0 1.5113.
  • the flat was filled to a depth of 2" (5.08 cm) with loamy sand oil. Seeds of seven different weed species were planted in individual rows one species per row across the width of the flat. The seeds were covered with soil so that they were planted at a depth of 0.5" (1.27 cm). The seeds used were those of four grasses: hairy crabgrass (Digitaria sanguinalis), yellow foxtail (Setaria glauca), watergrass (Echinochloa crusgalli), red oat (Avena sativa), and three broadleef weeds: redroot pigweed (Amranthus retroflexus), Indian mustard (Brassica juncea) and curly dock (Rumex crispus). Ample seeds were planted to give about 20 to 50 seedlings per row after emergence depending on the size of the plants.
  • Seeds of six plant species including three grasses: hairy crabgrass, watergrass, red oat and three broadleaf weeds: mustard, curly dock and pinto beans (Phaseolus vulgaris) were planted in the flats as described above for pre-emergence screening.
  • the flats were placed in the green house at 70 bis 85°F. (21.1-29.4 0 C.) and watered daily with a sprinkler.
  • the spray was prepared byrweighing out 20 mg. of the test compound, dissolving it in 5 ml.
  • the compounds of the present invention are used primarily as post-emergence herbicides and may be applied in a variety of ways at various concentrations.
  • the compounds are formulated with an inert carrier, utilizing methods well known to those skilled in the art, thereby making them suitable for application as dusts, sprays, or drenches and the like, in the form and manner required.
  • the mixtures can be dispersed in water with the aid of a wetting agent or they can be employed in organic liquid compositions, oil and water, water in oil emulsions, etc., with or without the addition of wetting, dispersing or emulsifying agents.
  • An herbicidally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application may vary from 0.05 to approximately 50 pounds per acre or 0.056-56.2 kg/ha.
  • the phytotoxic compositions of this invention employing an herbicidally effective amount of the compounds described herein are applied to the plants in the conventional manner.
  • the dust and liquid compositions can be applied to the plant by the use of power-dusters, boom and hand sprayers and spray-dusters.
  • the compositions can also be applied from-airplanes as a dust or a spray because they are effective in very low dosages.
  • the dust and liquid compositions are applied to the soil according to conventional methods and are distributed in the soil to a depth of at least 1/2 inch below the soil surface.
  • phytotoxic compositions be admixed with the soil particles, since these compositions can be applied merely by spraying or sprinkling the surface of the soil.
  • the phytotoxic compositions of this invention can also be applied by addition to irrigation water supplied to the filled to be treated. This method of application permits the penetration of the compositions into the soil as the water is absorbed therein. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as discing, dragging or mixing operations.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical & Material Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP78100019A 1977-06-21 1978-06-01 Cyclopropylméthoxyanilides substituées, leur procédé de préparation et leur application comme herbicides Expired EP0000324B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/807,940 US4149874A (en) 1977-06-21 1977-06-21 Substituted cyclopropylmethoxy anilides and their use as herbicides
US807940 1977-06-21

Publications (2)

Publication Number Publication Date
EP0000324A1 true EP0000324A1 (fr) 1979-01-24
EP0000324B1 EP0000324B1 (fr) 1980-10-01

Family

ID=25197489

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100019A Expired EP0000324B1 (fr) 1977-06-21 1978-06-01 Cyclopropylméthoxyanilides substituées, leur procédé de préparation et leur application comme herbicides

Country Status (20)

Country Link
US (1) US4149874A (fr)
EP (1) EP0000324B1 (fr)
JP (2) JPS5838422B2 (fr)
AR (1) AR220713A1 (fr)
AU (1) AU515316B2 (fr)
BG (1) BG30613A3 (fr)
BR (1) BR7803787A (fr)
CA (1) CA1232287A (fr)
CS (1) CS199733B2 (fr)
DD (1) DD137318A5 (fr)
DE (1) DE2860186D1 (fr)
DK (1) DK266578A (fr)
HU (1) HU184675B (fr)
IL (1) IL54783A (fr)
IT (1) IT1105426B (fr)
PH (1) PH13812A (fr)
PL (1) PL110841B1 (fr)
RO (1) RO83446B (fr)
YU (2) YU143678A (fr)
ZA (1) ZA783180B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2416220A1 (fr) * 1978-02-02 1979-08-31 Schering Ag Phenyl-urees et produits herbicides qui en contiennent
EP0005066A3 (en) * 1978-04-21 1979-11-14 Stauffer Chemical Company Synergistic herbicidal compositions and use thereof
FR2453141A1 (fr) * 1979-04-05 1980-10-31 Schering Ag Esters carbaniliques substitues, procedes pour les preparer, et produits herbicides selectifs qui en contiennent
EP0037106A3 (fr) * 1980-03-27 1982-06-09 Sumitomo Chemical Company, Limited Dérivés N-(2-(cyclopropyl)éthoxy)phénylanilide, leur préparation, compositions herbicides et leur utilisation, dérivés intermédiaires N-(2-(cyclopropyl)éthoxy)-aniline et N-(2-(cyclopropyl)éthoxy)nitrobenzène

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4356026A (en) 1977-06-21 1982-10-26 Stauffer Chemical Company Substituted cyclopropylmethoxy phenyl ureas and their use as herbicides
US4230483A (en) * 1977-06-21 1980-10-28 Stauffer Chemical Company Substituted cyclopropylmethoxy phenyl carbamates and thiocarbamates and their use as herbicides
US4336062A (en) * 1977-09-19 1982-06-22 Stauffer Chemical Company Herbicidal cyclohexenone derivatives
JPS55102553A (en) * 1979-01-30 1980-08-05 Sumitomo Chem Co Ltd Substituted phenylurea derivative, its preparation, herbicide and fungicide comprising it as active constituent
US4361438A (en) * 1981-01-21 1982-11-30 Stauffer Chemical Company Substituted cyclopropyl methoxy phenyl ureas and the herbicidal use thereof
BR112015023829B1 (pt) * 2013-03-25 2020-05-12 Sumitomo Chemical Company, Limited Composto de amidina e seu uso

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1093121A (en) * 1963-05-31 1967-11-29 Wellcome Found Etherified ªÐ-hydroxyanilines
US3761592A (en) * 1969-03-18 1973-09-25 R Mizzoni Quinoline derivatives exhibiting growth promoting and anticoccidial effects

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1219947B (de) * 1963-05-22 1966-06-30 Bayer Ag Verfahren zur Herstellung von Carbonsaeureaniliden
DE1189312B (de) * 1963-12-06 1965-03-18 Schering Ag Mittel mit selektiver herbizider Wirkung
US3362992A (en) * 1965-05-27 1968-01-09 Schwartz Herbert Novel cycloalkenecarboxanilides
FR1507886A (fr) * 1967-01-13 1967-12-29 J Berthier Sa Lab Nouveaux dérivés du dipropylacétylanilide
CH536594A (de) * 1970-07-31 1973-05-15 Ciba Geigy Ag Mittel zur Regulierung der Fruchtabszission
US3839446A (en) * 1970-11-18 1974-10-01 Stauffer Chemical Co Ether and sulfide meta-substituted anilides
US3786090A (en) * 1971-09-29 1974-01-15 Interx Research Corp Alkoxyacetanilide compounds
US3875229A (en) * 1972-11-24 1975-04-01 Schering Corp Substituted carboxanilides
US3885948A (en) * 1973-01-04 1975-05-27 Stauffer Chemical Co Meta-substituted ether anilides as algicidal agents
US3987059A (en) * 1974-06-10 1976-10-19 Sandoz, Inc. 2-substituted indoles and process for their preparation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1093121A (en) * 1963-05-31 1967-11-29 Wellcome Found Etherified ªÐ-hydroxyanilines
US3761592A (en) * 1969-03-18 1973-09-25 R Mizzoni Quinoline derivatives exhibiting growth promoting and anticoccidial effects

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2416220A1 (fr) * 1978-02-02 1979-08-31 Schering Ag Phenyl-urees et produits herbicides qui en contiennent
EP0005066A3 (en) * 1978-04-21 1979-11-14 Stauffer Chemical Company Synergistic herbicidal compositions and use thereof
FR2453141A1 (fr) * 1979-04-05 1980-10-31 Schering Ag Esters carbaniliques substitues, procedes pour les preparer, et produits herbicides selectifs qui en contiennent
EP0037106A3 (fr) * 1980-03-27 1982-06-09 Sumitomo Chemical Company, Limited Dérivés N-(2-(cyclopropyl)éthoxy)phénylanilide, leur préparation, compositions herbicides et leur utilisation, dérivés intermédiaires N-(2-(cyclopropyl)éthoxy)-aniline et N-(2-(cyclopropyl)éthoxy)nitrobenzène

Also Published As

Publication number Publication date
CS199733B2 (en) 1980-07-31
PL110841B1 (en) 1980-08-30
BR7803787A (pt) 1979-01-16
AR220713A1 (es) 1980-11-28
AU515316B2 (en) 1981-03-26
RO83446B (ro) 1984-02-28
PL207767A1 (pl) 1979-04-09
DE2860186D1 (en) 1981-01-08
EP0000324B1 (fr) 1980-10-01
YU226382A (en) 1983-02-28
JPS584757A (ja) 1983-01-11
HU184675B (en) 1984-09-28
IT1105426B (it) 1985-11-04
AU3664078A (en) 1979-12-06
JPS6059901B2 (ja) 1985-12-27
IL54783A (en) 1981-07-31
YU143678A (en) 1983-02-28
US4149874A (en) 1979-04-17
DD137318A5 (de) 1979-08-29
JPS549246A (en) 1979-01-24
CA1232287A (fr) 1988-02-02
IT7849918A0 (it) 1978-06-19
ZA783180B (en) 1979-06-27
BG30613A3 (en) 1981-07-15
IL54783A0 (en) 1978-07-31
PH13812A (en) 1980-10-03
DK266578A (da) 1978-12-22
RO83446A (fr) 1984-02-21
JPS5838422B2 (ja) 1983-08-23

Similar Documents

Publication Publication Date Title
JP2753872B2 (ja) スルファモイルフェニル尿素
US4270946A (en) N-Aryl,2-phenoxy nicotinamide compounds and the herbicidal use thereof
US4123256A (en) N-(4-substituted benzyloxy)phenyl)-N-methyl-N-methoxyurea
EP0000324B1 (fr) Cyclopropylméthoxyanilides substituées, leur procédé de préparation et leur application comme herbicides
EP0116729B1 (fr) Dérivés de benzoylurées et les compositions pesticides renfermant ces composés
US4251263A (en) N-substituted, 2-phenoxynicotinamide compounds and the herbicidal use thereof
EP0117320B1 (fr) Dérivés de benzoylurées et les compositions pesticides renfermant ces composés
US4119433A (en) 3-Halo-5-(lower alkoxy) phenoxy alkyl amides
US4230483A (en) Substituted cyclopropylmethoxy phenyl carbamates and thiocarbamates and their use as herbicides
US4400202A (en) N-m-Phenyl glutarimide derivatives and their use as herbicides
US4123551A (en) 2,2-Disubstituted-phenylcarbamoyl-6-hydroxy-m-dioxin-4-one derivatives having insecticidal properties
US3872157A (en) Substituted anilide carbamates
US4018813A (en) N-carbamoyl ethyl oxanilates
CA1053148A (fr) Derives de n-3 phenylcarbamoyl hydroxy-4 coumarin comme insecticides
US4356026A (en) Substituted cyclopropylmethoxy phenyl ureas and their use as herbicides
EP0001556B1 (fr) Dérivés de la cyclohexénone, procédé de fabrication, composition herbicide les contenant et utilisation de ces dérivés ou de la composition herbicide
US4327218A (en) N-Aryl, 2-phenoxy nicotinamide compounds and the herbicidal use thereof
US4182625A (en) 3-Halo-5-(lower alkoxy) phenoxy alkyl amides
US4843177A (en) Substituted acetamide derivatives with an antidote action, antidote compositions containing such compounds, selective herbicide compositions containing these antidotes and a process for the preparation of substituted acetamide derivatives
US4073932A (en) Method of controlling insects using 1,3-dioxin-4-ones
US4202684A (en) Carbanilic acid esters, process for making the same and herbicidal compositions containing same
US4361438A (en) Substituted cyclopropyl methoxy phenyl ureas and the herbicidal use thereof
US3318675A (en) Method for inhibiting plant growth
US3266883A (en) Herbicidal method
US4265658A (en) Novel cyclohexenone amino phenyl amides and their use as herbicides

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): BE CH DE FR GB NL

17P Request for examination filed
DET De: translation of patent claims
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE CH DE FR GB NL

REF Corresponds to:

Ref document number: 2860186

Country of ref document: DE

Date of ref document: 19810108

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19840420

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19840502

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19840630

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19840720

Year of fee payment: 7

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CH

Effective date: 19850630

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19850630

Year of fee payment: 8

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19860630

BERE Be: lapsed

Owner name: STAUFFER CHEMICAL CY.

Effective date: 19860630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19870101

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19870227

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19870303

GBPC Gb: european patent ceased through non-payment of renewal fee
REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19881117

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT