IL34054A - Substituted phenylcarbamates - Google Patents

Substituted phenylcarbamates

Info

Publication number
IL34054A
IL34054A IL34054A IL3405470A IL34054A IL 34054 A IL34054 A IL 34054A IL 34054 A IL34054 A IL 34054A IL 3405470 A IL3405470 A IL 3405470A IL 34054 A IL34054 A IL 34054A
Authority
IL
Israel
Prior art keywords
general formula
compound
carbamoyloxy
alkyl group
group
Prior art date
Application number
IL34054A
Other versions
IL34054A0 (en
Original Assignee
Schering 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
Priority claimed from DE19691913043 external-priority patent/DE1913043C3/en
Application filed by Schering Ag filed Critical Schering Ag
Publication of IL34054A0 publication Critical patent/IL34054A0/en
Publication of IL34054A publication Critical patent/IL34054A/en

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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen 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
    • 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
    • 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
    • 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
    • A01N37/26—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 containing the group; 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Landscapes

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

Description

Substi tuted Phenyl carbamoyl The present invention is concerned with new substituted with their use as especially as selective and with processes for their The herbicidal activity of substituted has been Such for example have been for in Belgian tion While the majority of these carbamates have a pronounced activity towards dicotyledonous types of they exhibit only a slight selectivity towards cultivated The present invention provides compounds of the general formula in which or represents a hydrogen an group or an aralkyl or and together with the adjacent carbon atom represent an ene represents an alkyl group or an alkoxy group or a group of the formula in which or represents an alkyl group which may be substituted by or an aryl group which may be substituted by trifluoromethyl and an alkenyl and a cyeloalkyl group and a hydrogen or represents an group or a hydrogen and and together with the adjacent nitrogen atom represent a saturated heterocyclic The compounds according to the present invention having the general formula given above have a herbicidal activity and may be used especially for weeds in cultivated The activity of many of the phenylcarbamates of the present mainly termed herein as acid extends to both preemergent and to postemergent With some of the compounds the activity in postemergent use is especially These agents develop a strong contact effect against the leaves of established it is found that as a rule the compounds of the present invention have a selective herbicidal activity and can be for for the postemergent treatment of groundnuts and important cultivated for example in the treatment of seeds and planted rice and in the treatment of maize andother cultivated cereal Some of the compounds of the present invention enable weed grasses to be destroyed in cultivated for which purpose as little as about kg of active substance per hectare is The substituted carbamoyloxy derivatives of c acid anilides are specially suitable as herbicidally active The new compounds of the present invention may be for according to the following process which is included within the scope of the present The present invention accordingly also provides a process for the manufacture of the compounds of the general formula defined above wherein a compound of the general formula in which and have the meanings given or a salt is reacted with a halide of the general formula CO Hal in which and have the given Hal represents a halogen atom and represents an alkl group or an alkoxy or with phosgeneand with an amine of the general formula in which and have the meanings given or with an alcohol of the general formula in which represents an alkyl or with an oxime of the 5 general formula in which and have the meanings given with an isocyanate of the general formula in which has the meanings given in organic for example in tetrahydrofuran or if in the presence of a advantageously a tertiary organic for or an for example The manufacture of the new substituted phenylcarbamates according to the process of the present invention is in Examples 1 to Some of the new substituted phenylcarbamates of the present invention are listed in the following Table I TABLE I Compound Name of compound Physical constant lide lide 2 oxy11c of compound Physical constant 17 anlllde 148 18 lic anlllde 129 130 145 146 C c 159 21 22 88 23 160 24 125 126 C 25 115 26 81 27 80 G 28 0 113 114 G 29 c 71 0 109 C 1 ic 79 2 47 48 3 e No Name of compound constant 34 35 82 83 G 20 llc Compound No Name of Physical constant anilide 114 115 C 50 acid 31 resin 51 61 52 53 ox 54 acid 97 116 117 C anilide 108 58 anilide 118 119 C 59 acid ylcarbamoyloxy 77 C 60 109 61 129 62 anilide 164 165 C anilide 136 64 94 C 4 Compound of compound Physical constant 133 anlllde 20 90 48 75 128 76 anilide 77 116 C 129 C 79 opylcarbamoylox 93 C 80 81 104 106 82 127 12 of compound Physical constant 84 115 117 o de anillde 20 lox 20 89 90 0 155 158 C 91 0 136 138 C 9392 earbamoyloxyj 158 160 C 93 117 122 C l40 123 C 96 opropylcarbamoy 97 lic 0 91 94 C 9998 thy lie 99 thy 0 81 C Compound Name of Physical constant 103102 80 82 C 103 o 133 136 G 104 108 C carbamoyioxy 113 C 159 anillde 131 134 C 0 99 102 C 125 128 C 4 113 0 140 142 C 139 C carbamoyloxyj e 146 149 C e 118117 carbamoyloxy 156 158 C Compound Name of compound Physical constan1 164 165 C 131 143 145 131 134 135 G 146 143 C 107 109 C lic 119 98 101 C 100 101 127 135 138 C 140 133 anilide 144 134 anilide 110 th carbamoyloxyj 123 Compound Name of compound Physical constant anillde llde anillde anillde 128 129 166 168 180 148 2Q No Name compound Physical constant lie hen box The new phenylearbamates of the present invention are soluble organic for example in dlmeth dimethyl ethyl acetate and The acid hydroxyanllldes required as starting materials in the process of the present invention be manufactured from chloroformic acid esters oxlmes either in water or in an organic for example in dioxan or ethyl advantageously in the presence of an acid binding for example sodium or potassium carbonate or oxide or The manufacture of one of the starting materials is described 206 g of and 38 g of magnesium oxide were taken u in 1 litre of ethyl acetate and 600 ml of water and 255 g of oxi e were added dropwise while coolibng to maintain the reaction temperature at about The batch was stirred at this temperature for 20 then acidified with hydrochloric whereupon the reaction product which has crystallised out was filtered off suction and dried in 323 g of the theoretical 153 The following starting materials are obtained in a similar hydroxyanillde ic 0 hydroxyanillde G c hydrox 0 hydroxyani 121 123 C o 75 76 C carboxyllc C 17 178 C The new phenylcarbamates of the present may be used in weed control by themselves or as mixtures of or more of such carbamates with other herbicides other for example The present invention accordingly further provides a method of controlling wherein a crop area the addition of Suitable liquid vehicles for organic for dimethyl tetrahydrofurane or As solid there may be for natural synthetic attaclay and other Suitable substances for salte of llgninesulphonic salts of alkylated c sulphonated acid amides and their alcohols and Such a may for example about Q by weight of active substances and i 1 The herbicidal activity of the compounds of the present invention and their use as selective herbicides are exemplified Examples 4 to 7 The following Examples illustrate the EXAMPLE 1 sodium then taken up i 50 ml of g of acid chloride were added dropwise while stirring at about The batch was stirred for 1 hour at room then the filtrate evaporated under the residue with 200 ml of ether and the carbamate was filtered off with Yields of the theoretical Example 3 of it taken up 50 ml of mixed g of ethyl chloroformate and heated for 1 hour on a steam The batch was evaporated under the taken up in water the organic phase was successively washed hydrochloric ice cold potassium carbonate solution and ice dried over magnesium sulphate and evaporated and dried under 20 23 g of the theoretical Example 4 The compounds listed in Table II below numbers of which compounds correspond to the numbers given to the compounds listed in Table I were sprayed in an amount of 5 kg of active substance per in the form of a suspension corresponding to 600 litres per over and tomatoes as test In contrast to the control that is which was sprayed as an emulsion in 600 litres of water per the test TABLE II Compound ard 5 3 0 3 0 2 0 0 8 0 0 9 0 0 10 0 0 11 0 0 12 0 13 3 5 14 0 0 15 0 1 0 2 17 0 5 18 0 Mustard Tomatoes 31 0 0 32 1 0 0 34 0 35 0 1 0 0 370 38 0 0 0 0 6 41 1 42 0 0 43 5 44 0 45 0 46 0 47 0 0 48 0 0 49 5 5 50 6 51 3 52 0 53 3 54 0 55 0 0 56 0 0 57 1 3 58 0 0 Gompound Mustard Tomatoes 61 0 0 62 0 5 63 0 5 64 0 e 65 0 0 66 0 0 67 0 0 68 Q 1 69 0 70 3 5 0 0 72 0 0 73 0 0 74 1 3 75 3 76 0 0 Compound rd Tomatoes 91 4 o 5 0 6 5 0 0 96 0 0 97 0 0 9998 0 2 99 3 100 3 i 102 p 0 0 3 1 7 0 4 106 5 109 5 O 0 0 112 0 0 113 P 0 114 0 0 115 0 3 117 116 0 0 0 2 0 0 150 0 Tomatoes 153 3 0 0 0 0 2 2 157 1 1 2 3 1 1 0 0 161 3 2 2 8 8 10 not damaged 0 totally destroyed Example Untreated sandy soil was sprayed the active substances indicated in Table III below numbers of correspond to the given to the compound s listed Table I in an amount of kg per hectare emergence of The active substances according to the present invention were applied in the form of a whereas the control was sprayed the form of an All the preparations were applied an of water correspondin to 600 litres per As be seen the the compounds of the present invention were efficacious the tenacious types of weed camomile and dead nettle whereas the control agent had practically no effect against these Compound Dead Peas Cotto weed Ragwort nettle 21 10 10 10 0 0 0 0 0 0 67 1 10 10 0 0 0 0 0 65 10 10 0 0 0 0 0 3 6 10 10 10 3 0 0 0 4 10 10 10 0 10 10 10 7 10 not damaged 0 totally destroyed 6 In a treatment listed in Table IV below numbers of which correspond to the given to the compounds listed in Table I were sprayed in an 1 kg of active substance per hectare over cultivated plants and in an amount of active substance per hectare on emulsified in an amount of water corresponding to 600 litres per The results given the Table show elearly the better compatibility of the compounds of the present Invention with to the cultivated plants maize and while the agents damaged them some of the compounds of the present invention produced better weed Maize nuts Mustard weed Ragwort Camomile Dead 8 10 10 0 0 0 0 0 9 10 10 3 3 0 0 0 10 10 10 0 0 0 0 0 12 10 10 0 0 0 0 0 10 10 10 0 0 0 0 0 21 10 10 10 0 0 0 0 0 38 10 10 0 5 0 3 0 39 10 10 0 0 0 c 0 10 10 10 10 10 10 0 0 0 0 0 55 10 10 10 2 0 0 0 0 10 2 0 0 0 0 10 10 0 0 0 0 0 64 10 10 0 0 0 0 0 65 10 10 10 0 0 0 0 0 10 10 3 1 0 0 0 69 10 10 0 0 0 0 0 56 10 10 10 0 0 0 0 Control 7 9 4 5 2 9 6 1 10 1 0 0 0 0 0 0 totally Example 7 When the compounds listed in V below of which compounds correspond to the numbers given to the compounds listed in Table I were applied an amount of 1 of active substance per hectare to cultivate rice and of hectare to millet i a it was as is shown the that the compounds of the present invention had a better compatibility and greater activity than the herbicides used as control TABLE V Gompound Rice Millet 61 0 10 0 0 39 0 69 0 0 60 2 56 1 Control car amate propionic I not damaged 0 totally destroyed insufficientOCRQuality

Claims (1)

1. we claim A compound of the general formula in which or represents a hydrogen an alkyl group or an aralkyl or and together with the adjacent carbon atom represent an ene represents an alkyl group or an alkoxy group or a group of the formula in which or represents an alkyl group which may be substituted by furyl or an aryl group which may be substituted by t fluoimethyl and an alkenyl and a cycloalkyl group and a hydrogen or represents an alkyl group or a hydrogen and and together with the adjacent nitrogen atom represent a saturated heterocyclic 3V anilide carbamoyloxyj carbamoyloxyj phenyl carbamoylox lox lic oxy carbamoyloxyj carbamo ac car box lcarbamoylox carbamoyloxyj lcarbamoylox pentyl carbamoyloxy lide I phenyl carbamoylox carbamoyloxy t thy loxy carbarnoy lox lide hy naphthylcarbaaoyloxy 92 carbamoylox lic carbamoyloxy carbamoyloxy 0 ca carbamoyloxyj 1 carbamoyloxy carbamoyloxy carbamoyloxy 1 carbamoyloxyj carbamoyloxy dime earbamoylox lide carbamoylox llde 5 dlrne thy h 5 thy thy carbamoyloxyj e t by car th n carbarn thy lpheny A process for the manufacture of a compound of the general formula in which or represents a hydrogen an alkyl group or an aralkyl or and together with the adjacent carbon atom represent an ene represents an alkyl group or an alkoxy group or a group of the formula in represents an alkyl group which be substituted by furyl or an aryl group which be substituted by trifluormethyl and an alkenyl and a cycloalkyl group and a hydrogen or represents an alkyl group or a hydrogen and and together with the adjacent nitrogen atom represent a saturated heterocyclic wherein a compound of the general formula in which and Rg have the meanings given or a salt is reacted with a halide of the general formula or CO Hal in which and have the meanings given Hal represents a halogen atom and represents an alkyl group or an alkoxy 3 or with phosgen and with an amine of the general formula in which and have the meanings given above an alcohol of the general formula in which represents an alkyl or with an oxime of the general formula in which and have the meanings given above or with an isocyanate of the general formula C 0 in which has the meanings given A process as claimed in claim wherein reaction with the halide is carried out in the presence of an inorganic or a tertiary organic A process as claimed claim or wherein the reaction with the halide is carried out in an organic A process as claimed in claim wherein the reaction with phosgene 43 A process as claimed in claim 164 or wherein the reaction with the the or the oxime is carried out in the presence of an inorganic or a tertiary organic A process as claimed in claim wherein the reaction with the isocyanate is carried out in an organic A process as claimed in or wherein the reaction with the isocyanate is carried out in the presence of a A process as claimed in claim wherein the catalyst is a tertiary organic base or an 1 A process as claimed in claim conducted substantially as described in any one of Examples 1 to 3 A hherbicidal preparation which comprises a compound as claimed in claim 1 in admixture or conjunction with a suitable A herbicidal preparation which comprises two or more of the compounds as claimed in claim 1 in admixture or conjunction with a suitable A herbicidal preparation which comprises the compound claimed in any one of claims 2 to in admixture or conjunction with a suitable A herbicidal preparation as claimed in any one of claims 173 to which is in the form of a strewing or Any one the herbicidal preparations as claimed in claim and stantially as described in Examples 4 to 6 A method of control ing wherein a crop area is treated with a compound as claimed in claim 1 A method of controlling wherein a crop area is treated with two or more compounds as claimed in claim A method of controlling wherein a crop area is treated with the compound claimed in any one of claims 2 to 44 A as claimed in claim wherein the crop area is treated with a herbicidal preparation as claimed in any one of claims 173 to methods as claimed in claim conducted substantially as described in Examples 5 to 7 For the Bregman and Goller insufficientOCRQuality
IL34054A 1969-03-11 1970-03-10 Substituted phenylcarbamates IL34054A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691913043 DE1913043C3 (en) 1969-03-11 Substituted phenyl carbamates

Publications (2)

Publication Number Publication Date
IL34054A0 IL34054A0 (en) 1970-05-21
IL34054A true IL34054A (en) 1972-12-29

Family

ID=5728168

Family Applications (1)

Application Number Title Priority Date Filing Date
IL34054A IL34054A (en) 1969-03-11 1970-03-10 Substituted phenylcarbamates

Country Status (20)

Country Link
JP (1) JPS5343570B1 (en)
AT (1) AT301251B (en)
BE (1) BE747208A (en)
BG (1) BG17274A3 (en)
CH (1) CH563712A5 (en)
CS (1) CS165339B2 (en)
DK (1) DK126321B (en)
ES (1) ES376874A1 (en)
FI (1) FI51097C (en)
FR (1) FR2037943A5 (en)
GB (1) GB1308183A (en)
IE (1) IE34053B1 (en)
IL (1) IL34054A (en)
LU (1) LU60296A1 (en)
NL (1) NL173636C (en)
NO (1) NO131171C (en)
PL (1) PL80472B1 (en)
RO (1) RO56476A (en)
SE (1) SE350033B (en)
YU (2) YU36371B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61183135U (en) * 1985-04-30 1986-11-15
CN101631768A (en) * 2007-03-15 2010-01-20 太阳医药高级研究有限公司 Novel prodrugs

Also Published As

Publication number Publication date
DK126321B (en) 1973-07-02
ES376874A1 (en) 1972-05-16
YU37970A (en) 1981-11-13
BE747208A (en) 1970-09-11
GB1308183A (en) 1973-02-21
AT301251B (en) 1972-08-25
SE350033B (en) 1972-10-16
CH563712A5 (en) 1975-07-15
NO131171B (en) 1975-01-06
NL7003504A (en) 1970-09-15
FI51097C (en) 1976-10-11
CS165339B2 (en) 1975-12-22
LU60296A1 (en) 1970-04-06
IE34053L (en) 1970-09-11
FR2037943A5 (en) 1970-12-31
RO56476A (en) 1975-01-15
BG17274A3 (en) 1973-07-25
PL80472B1 (en) 1975-08-30
YU243875A (en) 1981-11-13
NL173636B (en) 1983-09-16
DE1913043A1 (en) 1970-09-17
YU36697B (en) 1984-08-31
IE34053B1 (en) 1975-01-22
NO131171C (en) 1975-04-16
YU36371B (en) 1983-06-30
IL34054A0 (en) 1970-05-21
NL173636C (en) 1984-02-16
DE1913043B2 (en) 1977-05-12
FI51097B (en) 1976-06-30
JPS5343570B1 (en) 1978-11-21

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