GB973352A - New substituted ureas and thioureas and herbicidal compositions containing them - Google Patents

New substituted ureas and thioureas and herbicidal compositions containing them

Info

Publication number
GB973352A
GB973352A GB37393/60A GB3739360A GB973352A GB 973352 A GB973352 A GB 973352A GB 37393/60 A GB37393/60 A GB 37393/60A GB 3739360 A GB3739360 A GB 3739360A GB 973352 A GB973352 A GB 973352A
Authority
GB
United Kingdom
Prior art keywords
methoxy
hydroxy
dichlorophenyl
methylthiourea
phenyl
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.)
Expired
Application number
GB37393/60A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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
Priority claimed from US59849A external-priority patent/US3112342A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB973352A publication Critical patent/GB973352A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/64Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises urea and thiourea derivatives of the formula <FORM:0973352/C1/1> in which Ar is a phenyl ring, Q is oxygen or sulphur, R1 is hydrogen or a hydroxy group or an alkoxy group of less than 5 carbon atoms or, when Q is sulphur, is an alkyl group, R2 is hydrogen or an alkyl or alkoxy group of less than 5 carbon atoms and R3 is an alkyl group of less than 5 carbon atoms, at least one of R1 and R2 being an alkoxy group and/or R1 being a hydroxy group and the total number of carbon atoms in R2 and R3 being less than 6. When Q is sulphur, or when Q is oxygen and R1 is a hydroxy or alkoxy group, the ring Ar may be unsubstituted or substituted with up to three substituents, one of which is a halogen atom, a nitro group or an alkyl or alkoxy group of less than 5 carbon atoms, the other substituents, if any, being halogen atoms and/or methyl groups. When Q is oxygen and R1 is hydrogen, the ring Ar may be substituted (a) with one chlorine atom and a nitro group or (b) with three chlorine atoms, in which event R2 should be an alkoxy group of 2-4 carbon atoms. In any event the ring Ar must have a free 2-position. The compounds in which R1 is a hydroxy group may be prepared by reacting phenylhydroxylamine or a suitably substituted phenylhydroxylamine with a suitable carbamyl chloride or thiocarbamyl chloride or with a suitable isocyanate or isothiocyanate. Compounds in which R1 is an alkoxy group may be prepared by alkylating compounds in which R1 is a hydroxy group or by reacting N-alkoxyanilines with aliphatic amines or with alkyl-substituted hydroxylamines. Compounds in which R1 is hydrogen may be prepared by reacting an appropriate phenylisocyanate or phenylisothiocyanate with an N-alkyl-O-alkylhydroxylamine. Examples are given in which (1) 3, 4-dichlorophenylhydroxylamine and dimethylcarbamyl chloride yield 3-(3, 4-dichlorophenyl)-3-hydroxy-1, 1-dimethylurea, (2) p-chlorophenylhydroxylamine and methyl isocyanate yield 3-(p-chlorophenyl)-3-hydroxy-1-methylurea, (3) 3, 4-dichlorophenylisothiocyanate and N, O-dimethylhydroxylamine yield 3-(3, 4-dichlorophenyl) - 1 - methoxy -1- methylthiourea; compounds similarly obtainable are 3-(m-chlorophenyl)-1-methox-1-methylthiourea, 3-(3, 4-dichlorophenyl)-3-methoxy-1-methyl-thiourea, 3-(o-chlorophenyl)-3-butoxy-1-methylthiourea and 3- (3-chloro-4-nitrophenyl) -1- methyl-1-methoxy-thiourea; (4) N-methoxy-3, 4-dichloraniline and dimethylthiocarbamyl chloride yield 3-(3, 4-dichlorophenyl)-3-methoxy-1, 1-dimethylthiourea; 3-(3, 4-dichlorophenyl)-3-methoxy-1-butyl - 1 - methylthiourea is similarly obtainable; (5) N-methyl-3, 4-dichloraniline is treated with thiophosgene in the presence of triethylamine, and the product is treated with N-methyl-O-ethylhydroxylamine; 3-(3, 4-dichlorophenyl)-1, 3-dimethyl-1-ethoxythiourea is obtained; 3-(3, 4-dichlorophenyl)-1, 3-dimethyl-1-methoxythiourea and 3-(3, 4-dichlorophenyl)-3-ethyl-1-methoxy-1-methylthiourea are similarly obtainable; (6) N-ethoxy-3, 4-dichloraniline and N, O-dimethylhydroxylamine yield 3-(3, 4-dichlorophenyl)-3-ethoxy-1-methoxy-1-methylthiourea; (7) N-ethoxy-3, 4-dichloraniline and dimethylamine yield 3-(3, 4-dichlorophenyl)-3-ethoxy-1, 1-dimethylthiourea; (8) 3-nitro-4-chloro-phenylisocyanate and N, O-dimethylhydroxylamine yield 3-(3-nitro-4-chlorophenyl)-1-methyl - 1 -methoxyurea; (8) 6-chloro-4-nitrophenylisocyanate and N, O-dimethylhydroxylamine yield 3-(6-chloro-4-nitrophenyl)-1-methyl-1-methoxyurea. Other specified products include 3-phenyl-3-hydroxy-1-methylurea, 3-phenyl-3-hydroxy-1, 1-dimethylurea, 3-phenyl-3-hydroxy-1-butyl-1-methylurea, 3-(3-bromo-4-butoxyphenol)-3-hydroxy-1, 1-dimethylurea, 3 - (p-fluorophenyl) -3- hydroxy -1- methyl-1-propylurea, 3-phenyl-3-methoxy - 1 - methylurea, 3-phenyl-3-methoxy-1, 1-dimethylurea, 3-(p-bromophenyl)-3-ethoxy-1, 1-dimethylurea, 3-(p-fluorophenyl)-3-ethoxy-1-methoxy - 1 - methylurea and 3-phenyl-3-methoxy-1, 1-dimethylthiourea. The products are useful as herbicides. Specification 973,353 is referred to.ALSO:As components of herbicidal compositions, use is made of urea and thiourea derivatives of the formula <FORM:0973352/A5-A6/1> in which Ar is a phenyl ring, Q is oxygen or sulphur, R1 is hydrogen or a hydroxy group or an alkoxy group of less than 5 carbon atoms or, when Q is sulphur, is an alkyl group, R2 is hydrogen or an alkyl or alkoxy group of less than 5 carbon atoms and R3 is an alkyl group of less than 5 carbon atoms, at least one of R1 and R2 being an alkoxy group and/or R1 being a hydroxy group and the total number of carbon atoms in R2 and R3 being less than 6 (see Division C2). When Q is sulphur, or when Q is oxygen and R1 is a hydroxy or alkoxy group, the ring Ar may be unsubstituted or substituted with up to three substituents, one of which is a halogen atom, a nitro group or an alkyl or alkoxy group of less than 5 carbon atoms, the other substituents, if any, being halogen atoms and/or methyl groups. When Q is oxygen and R1 is hydrogen, the ring Ar may be substituted (a) with one chlorine atom and a nitro group or (b) with three chlorine atoms, in which event R2 should be an alkoxy group of 2-4 carbon atoms, In any event the ring Ar must have a free 2-position. Specified products include 3-(3,4-dichlorophenyl) - 3 - hydroxy - 1,1 - dimethylurea, 3 - (p - chlorophenyl) - 3 - hydroxy - 1 - methylurea, 3 - (3,4 - dichlorophenyl) - 1 - methoxy - 1 - methylthiourea, 3 - (m - chlorophenyl) - 1 - methoxy - 1 - methylthiourea, 3 - (3,4 - dichlorophenyl) - 3 - methoxy - 1 - methylthiourea, 3 - (o - chlorophenyl) - 3 - butoxy - 1 - methylthiourea, 3 - (3 - chloro - 4 - nitrophenyl)-1 - methyl - 1 - methoxythiourea, 3 - (3 - chloro - 4 - isopropylphenyl) - 1 - methoxy - 1 - methylthiourea, 3 - (p - bromophenyl) - 1 - methoxy - 1 - methylthiourea, 3 - (3,4 - dichlorophenyl) - 3 - methoxy - 1,1 - dimethylthiourea, 3 - (3,4 - dichlorophenyl) - 3 - methoxy - 1 - butyl - 1 - methylthiourea, 3 - (3,4 - dichlorophenyl) - 3 - ethoxy - 1 - methoxy - 1 - methylthiourea, 3 - (3,4 - dichlorophenyl) - 3 - ethoxy - 1,1 - dimethylthiourea, 3 - (6 - chloro - 4 - nitrophenyl)-1 - methyl - 1 - methoxyurea, 3 - phenyl - 3 - hydroxy - 1 - methylurea, 3 - phenyl - 3 - hydroxy - 1,1 - dimethylurea, 3 - phenyl - 3 - hydroxy - 1 - butyl - 1 - methylurea, 3 - (3 - bromo - 4 - butoxyphenyl) - 3 - hydroxy - 1,1 - dimethylurea, 3 - (p - fluorophenyl) - 3 - hydroxy - 1 - methyl - 1 - propylurea, 3 - phenyl - 3 - methoxy - 1 - methylurea, 3 - phenyl - 3 - methoxy - 1,1 - dimethylurea, 3 - (p - bromophenyl) - 3 - ethoxy - 1,1 - dimethylurea, 3 - (p - fluorophenyl) - 3 - ethoxy - 1 - methoxy - 1 - methylurea and 3 - phenyl - 3 - methoxy - 1,1 - dimethylthiourea. The products may be formulated as solid or liquid compositions with the addition of solid or liquid compositions with the addition of solid or liquid diluents, a number of which are specified. The compositions may also contain surface-active agents, a number of which are specified. Other herbicides, insecticides, fungicides and fertilizers may also be included in the compositions. The p compositions may be used for the treatment of growing weeds or they may be applied to the soil in areas where a growth of weeds might otherwise have been expected. Examples of herbicidal compositions are given. Specification 973,353 is referred to.
GB37393/60A 1959-11-03 1960-10-31 New substituted ureas and thioureas and herbicidal compositions containing them Expired GB973352A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US85054759A 1959-11-03 1959-11-03
US5979960A 1960-10-03 1960-10-03
US5983160A 1960-10-03 1960-10-03
US5984860A 1960-10-03 1960-10-03
US5983260A 1960-10-03 1960-10-03
US59849A US3112342A (en) 1960-10-03 1960-10-03 1-methoxy-1-methyl-3-(3-chloro-4-cumenyl) urea

Publications (1)

Publication Number Publication Date
GB973352A true GB973352A (en) 1964-10-21

Family

ID=27556803

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37393/60A Expired GB973352A (en) 1959-11-03 1960-10-31 New substituted ureas and thioureas and herbicidal compositions containing them

Country Status (6)

Country Link
BE (1) BE596661A (en)
CH (1) CH413490A (en)
FR (1) FR1278201A (en)
GB (1) GB973352A (en)
NL (1) NL257564A (en)
OA (1) OA01572A (en)

Also Published As

Publication number Publication date
CH413490A (en) 1966-05-15
BE596661A (en)
NL257564A (en)
FR1278201A (en) 1961-12-08
OA01572A (en) 1969-09-20

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