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IT1075276B - 2-Alkenyl-chloro-acetanilide derivs. - and alkenyl-aniline precursors, useful as herbicides with low toxicity for maize (BE 10.8.78) - Google Patents

2-Alkenyl-chloro-acetanilide derivs. - and alkenyl-aniline precursors, useful as herbicides with low toxicity for maize (BE 10.8.78)

Info

Publication number
IT1075276B
IT1075276B IT2015377A IT2015377A IT1075276B IT 1075276 B IT1075276 B IT 1075276B IT 2015377 A IT2015377 A IT 2015377A IT 2015377 A IT2015377 A IT 2015377A IT 1075276 B IT1075276 B IT 1075276B
Authority
IT
Italy
Prior art keywords
alkenyl
alkyl
herbicides
maize
derivs
Prior art date
Application number
IT2015377A
Other languages
Italian (it)
Inventor
Roberto Colle
Franco Gozzo
Giovanni Camaggi
Giorgio Siddi
Original Assignee
Montedison Spa
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 to AR271006A priority Critical patent/AR221215A1/en
Application filed by Montedison Spa filed Critical Montedison Spa
Priority to IT2015377A priority patent/IT1075276B/en
Priority to CH119378A priority patent/CH640215A5/en
Priority to EG77/78A priority patent/EG13111A/en
Priority to NL7801333A priority patent/NL7801333A/en
Priority to BG038587A priority patent/BG28975A3/en
Priority to AU33071/78A priority patent/AU522149B2/en
Priority to FR7803349A priority patent/FR2380252A1/en
Priority to US05/875,893 priority patent/US4224050A/en
Priority to RO7893145A priority patent/RO75228A/en
Priority to HU78MO1005A priority patent/HU180879B/en
Priority to IN149/CAL/78A priority patent/IN149501B/en
Priority to GB16771/79A priority patent/GB1570770A/en
Priority to GB5105/78A priority patent/GB1570769A/en
Priority to ZA00780783A priority patent/ZA78783B/en
Priority to CA000296747A priority patent/CA1121367A/en
Priority to BR7800781A priority patent/BR7800781A/en
Priority to DE19782805525 priority patent/DE2805525A1/en
Priority to ES466830A priority patent/ES466830A1/en
Priority to SU782577624A priority patent/SU1039431A3/en
Priority to BE185092A priority patent/BE863875A/en
Priority to JP1367278A priority patent/JPS53127425A/en
Priority to GR55377A priority patent/GR74890B/el
Application granted granted Critical
Publication of IT1075276B publication Critical patent/IT1075276B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen 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
    • 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
    • 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
    • A01N37/34—Nitriles
    • 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
    • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives

Landscapes

  • 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)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Chloroacetanilides of formula (I) are new: (R1=H, 1-5C alkyl or X. X is alkenyl, pref. -C(R2)2.CR2=C(R2)2 or -CH=CR2 CH(R2)2. Each R2 is same or different H or 1-3C alkyl. A is opt. substd alkylene i.e. CHR2, C(R2)2CH2 or CH2C(R2)2. Y = H, 1-5C alkyl, 2-5C alkenyl or alkynyl, phenyl, 3-8C cycloalkyl, halo, satd. or unsatd. heterocyclic with 1-3 heteroatoms, CN, OR, SR, OCOR, NHR, N(R)2, NRCOR, CON(R2), or COOR. R=H, 1-5C alkyl, 2-5C alkenyl or alkynyl, 3-8C cycloalkyl, phenyl or satd. or unsatd. heterocyclic with 1-3 heteroatoms). Also new are the intermediate anilines of formula (II) (R'1 is as R1 but not H. A'1 is as A but not CHR2. Y' is as Y but not NHR or N(R)2. AY can also together be H provided R'1 = methyl). (I) are herbicides, esp. for pre-emergence use. They have lower toxicity towards maize than known chloroacetanilides. In an example, 2-ehtyl-6-allyl-N-methoxymethylchloroacetanilide was prepd. from 2-ethyl-6-allylaniline by reacting (a) with trioxan, then (b) with chloroacetyl chloride.
IT2015377A 1977-01-20 1977-02-10 2-Alkenyl-chloro-acetanilide derivs. - and alkenyl-aniline precursors, useful as herbicides with low toxicity for maize (BE 10.8.78) IT1075276B (en)

Priority Applications (23)

Application Number Priority Date Filing Date Title
AR271006A AR221215A1 (en) 1977-02-10 1977-01-01 PROCEDURE FOR THE PREPARATION OF SUBSTITUTED CHLOROACETHANILIDES
IT2015377A IT1075276B (en) 1977-02-10 1977-02-10 2-Alkenyl-chloro-acetanilide derivs. - and alkenyl-aniline precursors, useful as herbicides with low toxicity for maize (BE 10.8.78)
CH119378A CH640215A5 (en) 1977-02-10 1978-02-03 CHLORACETANILIDES WITH SELECTIVE HERBICIDE ACTIVITY AND PREPARATION METHODS.
EG77/78A EG13111A (en) 1977-02-10 1978-02-06 New chloroacetanylides having a selective herbicides activity ortho-al kenyl-substituted anilines intermediate in the synthesis of said herbicide chloroacetanylides,and methods for their preparation
NL7801333A NL7801333A (en) 1977-02-10 1978-02-06 NEW CHLORINE ACETANILIDES WITH SELECTIVE WEEDAL ACTION, ORTHO-ALKENYLGE SUBSTITUTED ANILINS, USED AS INTERMEDIATES IN THE PREPARATION OF THESE CHLORINE ACETANILIDES, AND METHOD OF PREPARATION OF THESE.
BG038587A BG28975A3 (en) 1977-02-10 1978-02-06 Herbicide means
FR7803349A FR2380252A1 (en) 1977-02-10 1978-02-07 NEW CLASS OF HERBICIDES CONSISTING OF LOW TOXIC CHLOROACETANILIDES TO CORN AND METHODS FOR THE PREPARATION OF SUCH HERBICIDES
US05/875,893 US4224050A (en) 1977-02-10 1978-02-07 Chloroacetanilides having a selective herbicidal activity, ortho-alkenyl-substituted anilines, intermediates in the synthesis of said herbicidal chloroacetanilides, and methods for their preparation
AU33071/78A AU522149B2 (en) 1977-02-10 1978-02-07 Chloroacetanylides
IN149/CAL/78A IN149501B (en) 1977-02-10 1978-02-08
RO7893145A RO75228A (en) 1977-02-10 1978-02-08 PROCESS FOR PREPARING CHLORACETANILIDE
GB16771/79A GB1570770A (en) 1977-02-10 1978-02-08 Orthosubstituted anilines and their preparation
GB5105/78A GB1570769A (en) 1977-02-10 1978-02-08 Orthosubstituted anilides and their preparation
HU78MO1005A HU180879B (en) 1977-02-10 1978-02-08 Process for producing new chloroaceta ilide derivatives and liquide herbicide compositions containing them as active agents
CA000296747A CA1121367A (en) 1977-02-10 1978-02-09 Chloroacetanilides having herbicidal activity
ZA00780783A ZA78783B (en) 1977-02-10 1978-02-09 New chloroacetanylides having a selective herbicide activity,ortho-alkenyl-substituted anulines,intermediates in the synthesis of said herbicide chloroacetanylides,and methods for their preparation
BR7800781A BR7800781A (en) 1977-02-10 1978-02-09 PROCESS FOR THE PREPARATION OF HERBICIDES CHLORINE-ACETANILIDES, PROCESS FOR THE PREPARATION OF ANYLIDE AND PROCESS TO COMBAT MONOTYLEDONE AND DICOTHYLONEONE INFESTATIONS
DE19782805525 DE2805525A1 (en) 1977-02-10 1978-02-09 CHLORACETANILIDES AND METHOD FOR MANUFACTURING THEREOF
ES466830A ES466830A1 (en) 1977-02-10 1978-02-09 PROCEDURE FOR THE PREPARATION OF SUBSTITUTED CHLOROACETANILIDES
SU782577624A SU1039431A3 (en) 1977-02-10 1978-02-10 Method for controlling wild plants in corn plantations
BE185092A BE863875A (en) 1977-02-10 1978-02-10 NEW CLASS OF HERBICIDES CONSISTING OF LOW TOXIC CHLOROACETANILIDES TO CORN AND METHODS OF PREPARATION OF SUCH HERBICIDES
JP1367278A JPS53127425A (en) 1977-01-20 1978-02-10 Ooalkenyl substituted aniline intermediate for synthesizing novel chloroacetanilide having selective herbicidal activity and process for preparing same
GR55377A GR74890B (en) 1977-02-10 1979-12-21

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT2015377A IT1075276B (en) 1977-02-10 1977-02-10 2-Alkenyl-chloro-acetanilide derivs. - and alkenyl-aniline precursors, useful as herbicides with low toxicity for maize (BE 10.8.78)

Publications (1)

Publication Number Publication Date
IT1075276B true IT1075276B (en) 1985-04-22

Family

ID=11164236

Family Applications (1)

Application Number Title Priority Date Filing Date
IT2015377A IT1075276B (en) 1977-01-20 1977-02-10 2-Alkenyl-chloro-acetanilide derivs. - and alkenyl-aniline precursors, useful as herbicides with low toxicity for maize (BE 10.8.78)

Country Status (4)

Country Link
BE (1) BE863875A (en)
HU (1) HU180879B (en)
IT (1) IT1075276B (en)
ZA (1) ZA78783B (en)

Also Published As

Publication number Publication date
BE863875A (en) 1978-08-10
ZA78783B (en) 1979-01-31
HU180879B (en) 1983-04-29

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