IL41472A - 1-(phenylcarbamoyl)-2-pyrazoline derivatives,their preparation and pesticidal preparations containing them - Google Patents

1-(phenylcarbamoyl)-2-pyrazoline derivatives,their preparation and pesticidal preparations containing them

Info

Publication number
IL41472A
IL41472A IL41472A IL4147273A IL41472A IL 41472 A IL41472 A IL 41472A IL 41472 A IL41472 A IL 41472A IL 4147273 A IL4147273 A IL 4147273A IL 41472 A IL41472 A IL 41472A
Authority
IL
Israel
Prior art keywords
group
pyrazoline
chlorophenyl
carbon atoms
chlorophenylcarbamoyl
Prior art date
Application number
IL41472A
Other versions
IL41472A0 (en
Original Assignee
Philips Nv
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 Philips Nv filed Critical Philips Nv
Publication of IL41472A0 publication Critical patent/IL41472A0/en
Publication of IL41472A publication Critical patent/IL41472A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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<
    • A01N47/38Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic

Landscapes

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

Claims (3)

1. CLAIMS Compounds j of the formula. where the symbols have the following meanings: A is a phenyl group, optionally substituted with 1 or 2 substituents selected from the group-comprising a halogen atom, a cyano group, an alkyl group containing from 1 to 4 carbon atoms which, may be substituted by halogen, a cyclo-alkyl-
2. Compounds of the. formula where R' is a hydrogen atom, a halogen atom, a cyano group, an alkoxy group containing from 1 to carbon atoms or an alkyl group containing from 1 to carbon atoms, B' is a hydrogen atom, a phenyl group or a phenyl group substituted by from 1 to 3 substituents selected from the group comprising a halogen atom, an alkoxy group containing from 1 to carbon atoms and an alkyl group containing from 1 to k carbon atoms, R^ is a halogen atom or an alkyl group containing from 1 to k carbon atoms, m is 1 or 2 and n is 1 or 2, with the understanding that (R1) and (R ) are not 2,6-di- ° 'm 2 n ' substitutions.
3. Compounds of the formula where. Jk., R" is a hydrogen atom, a halogen atom, a cyano group, an alkyl, alkoxy or alkylthio group containing from 1 to 4 carbon atoms, a cycloalkyl group or an amino group substituted by 1 or 2 alkyl groups, where the alkyl groups contain from 1 to.4 carbon atoms and together with the- nitrogen atom of the amino group may form a saturated closed ring which may contain a second hetero atom, selected from sulphur, oxygen or nitrogen 3 . R is a substituent m the para position and may be a halogen* atom, an alkyl group which . contains from 1 to 4 carbon atoms and which may be substituted with halogen , an alkylthio group containing from 1 to 4. carbon atoms, an alkylsulfonyl group containing from 1 to 4 carbon atoms, a cyano group or an amino group substituted by 1 or 2 alkyl groups which contain from 1 to 4 carbon atoms or 3 R is a 3,4-dichloro substituent, and X is hydrogen or a substituent in the para position which is selected from a halogen atom, an alkyl group containing from 1 to 4 carbon atoms , an alkoxy group containing from 1 to 4 carbon atoms and an amino group substituted by 1 or 2 alkyl groups which contain from 1 to 4 carbon atoms or X is a 2,4 or 3 , -disubstituent , the substituents being selected from a halogen atom, a lower alkyl group and a dioxyalkylene group, or X is a 2 , ¾ , 6-trihalogen group.
4. Compound of the formula where R" has the a orementioned meaning and -R^ is a 3>4-dichloro group or a substituent in the para position selected from the group comprising a halogen where R"'is. a hydrogen atom, a halogen atom, a cyano group methoxy group, 41472/2 PHN. 6112 B represents a hydrogen atom, a phenyl group, a 4-chlorophenyl group, a 4-me thoxyphenyl group or a 2 , ¾-dichlorophenyl group, and - . 1 - ( -chlorophenylcarbamoyl) -3- ( ^-chlorophenyl) -5-( -isopropoxyphenyl)- A -pyrazoline.
10. 1- ( 4-t .butylphenylcarbamoyl) -3- ( 4-chlorophenyl ) - 5-( 4-chlorophenyl)- Δ -pyrazoline..
11. 1 - ( h-n . propylphenylcarbamoyl ) -3- ( ¾-chlorophenyl ) -5- ( -chlorophenyl) - ^ 2-pyrazoline.
12. 1 - ( h-e thylphenylcarbamoyl ) -3- ( -chlorophenyl ) - Lchlorophenyl)-5-(^-chlorophenyl)- -pyrazoline. 1 k . 1- ( 4-chlorophenylcarbamoyl ) -3- ( ^-chlorophenyl) - A 2 v . „^ -pyrazoline.
15. 1 - ( -chlorophenylcarbamoyl ) -3- ( ^'-chlorophenyl ) - 5- ( -ethylphenyl) - Λ ^pyrazoline .
16. 1 - ( 4-chlorophenylcarbamoyl ) -3- ( 4-chlorophenyl ) - 5_( _t . butylphenyl)-. Δ 2-pyrazoline .
17. 1 - ( -chiorophenylcarbamoyl) -3- ( -chlo.rophenyl ) - 5-(2-methyl-4-chlorophenyl)- Δ 2-pyrazoline . 41472/2 PH . 6112
18. 1-(^-chlorophenylcarbamoyl)-3-(^-dimethyl- aminophenyl ) -5- ( 4-chlorophehyl ) - Ά ^-p razoline .
19. 1-(4-chlorophenylcarbamoyl)-3-(^-chlorophenyl)- 5-(2, -dichlorophenyl)-^ 2-pyrazoline .
20. 1-( -chlorop enylcarbamoyl)-3-phenyl-5-(^- methoxyphenyl)- ^ ^-pyrazoline .
21. 1- ( 4-chlorophenylcarbamoyl) -3-phenyl- -4 2- pyrazoline .
22. 1- ( -chlorophenylcarbamoyl ) -3- ( ^-chlorophenyl ) - A ^-pyrazoline .
23. 1 - ( 4-chlorophenylcarbamoyl) -3- ( fluorophenyl ) - * A■* -pyrazol1i·ne. ■ 2k. 1 - ( ¾-chlorophenylcarbamoyl ) -3- ( ^-bromophenyl ) - A 2 .. -pyrazoline .
25. 1 - ( ^-iodophenylcarbamoyl ) -3- ( ^-chlorophenyl) - λ 2 .. '<* -pyrazoline.
26. 1- ( ¾-n. propylphenylcarbamoyl ) -3- ( ^-chlorophenyl ) *-» -pyrazoline .
27. 1 - { 4-chlorophenylcarbamoyl ) -3- ( ^-isopropoxy- . phenyl)-^ ^-pyrazoline .
28. 1 - ( -e thylphenylcarbamoyl ) -3- ( ^-chlorophenyl ) - A -pyrazoline. 2 . 1-( -ethylsulfonylphenylcarbamoyl)-3-(4- chlorophenyl ) - A ^-pyrazoline,
30. 1 - ( -chlorophenylcarbamoyl ) -3- ( ¾-e thylphenyl ) - Λ 2 . -pyrazoline .
31. 1-(4-chlorophenylcarbamoyl)-3-(^-isopropyl-jhenyl)-^ 2-pyrazoline .
32. Method of preparing compounds of the general 41472/2 wherein a compound of the fom a where A and B have the meanings given in Claim 1 is reacted with a compound of the formula where and n have the meanings given in Claim 1.
33. Biocidal preparation for controlling arthropods, containing as active ingredient a compound of formula I in Claim 1, in addition to a solid or liquid inert carrier material , .
34. Preparation as claimed in Claim 33, wherein the active ingredient is a compound according to Claim 2.
35. Preparation as claimed in Claim 30, wherein the active ingredient is a compound according to Claim 3.
36. Preparation as claimed in Claim 33, wherein the active ingredient.-is a compound according to Claim 4.
37. Preparation as claimed in Claim 33, wherein the active ingredient is a compound according to Claim 5. .· .
38. " Preparation as claimed in Claim 33, wherein the active ingredient is any one of the compounds claimed in Claims 6, 9-12, 14-17, 19-28, 30 and 31. « 41472/2
39. Preparation as claimed in Claim 33, wherein the active ingredient is any one of the compounds claimed in Claims 7, 8, 13, 18 or 29.
40. Preparation as claimed in Claim 53', characterized in that it also contains another, known biocidal compound.
41. Method of producting a biocidal preparation, characterized in that a compound of the formula I in Claim 1 is mixed with a solid or liquid inert carrier material, if desired with the addition of adjuvants or another, known biocidal compound.
42. Method of controlling arthropods in agriculture and horticulture, characterized in that the infected areas are treated with a compound of formula I in Claim 1 or with a preparation as claimed in any of Claims 33 to 38 or 40 in a dosage which corresponds to from 0.5 to 5 kg of .active substance per hectare.
43. Method of controlling arthropods in agriculture and horticulture, characterized in that the infected areas are treated with a compound of formula I in Claim 1 or with a preparation as claimed in any of Claims 39. or40 in a dosage which corresponds to from 0.5 to 5 kg of active substance per hectare. - -
IL41472A 1972-02-09 1973-02-06 1-(phenylcarbamoyl)-2-pyrazoline derivatives,their preparation and pesticidal preparations containing them IL41472A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL7201674.A NL158177B (en) 1972-02-09 1972-02-09 METHOD FOR PREPARING INSECTICIDE PREPARATIONS BASED ON UNSATURATED PYRAZOLIDINE DERIVATIVES, SO PREPARED PREPARATIONS, AND METHOD FOR PREPARING UNSATURATED PYRAZOLIDIN DERIVATICIDE DERIVATICIDE.

Publications (2)

Publication Number Publication Date
IL41472A0 IL41472A0 (en) 1973-04-30
IL41472A true IL41472A (en) 1976-08-31

Family

ID=19815330

Family Applications (1)

Application Number Title Priority Date Filing Date
IL41472A IL41472A (en) 1972-02-09 1973-02-06 1-(phenylcarbamoyl)-2-pyrazoline derivatives,their preparation and pesticidal preparations containing them

Country Status (21)

Country Link
JP (1) JPS5419445B2 (en)
AR (1) AR195824A1 (en)
AT (1) AT330791B (en)
BE (1) BE795264A (en)
CA (1) CA974991A (en)
CH (1) CH590846A5 (en)
CS (1) CS193020B2 (en)
DE (1) DE2304584C2 (en)
DK (1) DK136841B (en)
EG (1) EG11009A (en)
ES (1) ES411380A1 (en)
FR (1) FR2171218B1 (en)
GB (1) GB1398196A (en)
IE (1) IE37346B1 (en)
IL (1) IL41472A (en)
IT (1) IT978847B (en)
NL (1) NL158177B (en)
PL (2) PL93536B1 (en)
SE (1) SE410187B (en)
SU (1) SU479295A3 (en)
ZA (1) ZA73576B (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL158178B (en) * 1974-07-12 1978-10-16 Philips Nv METHOD OF PREPARING INSECTICIDE PREPARATIONS CONTAINING A PYRAZOLINE DERIVATIVE, SO PREPARED PREPARATIONS, AND METHOD OF PREPARING PYRAZOLINE DERIVATIVES WITH INSECTICIDE ACTION.
US4156007A (en) * 1974-07-12 1979-05-22 U.S. Philips Corporation Pyrazoline compounds
US4174393A (en) * 1975-07-09 1979-11-13 Duphar International Research B.V. 1,3,4-Substituted pyrazoline derivatives
NL183400C (en) * 1976-01-09 1988-10-17 Duphar Int Res METHOD FOR PREPARING AN INSECTICIDE PREPARATION CONTAINING A PYRAZOLINE COMPOUND AND METHOD FOR PREPARING A PYRAZOLINE COMPOUND WITH INSECTICIDE ACTION
US4134987A (en) * 1976-01-14 1979-01-16 Huppatz John L Compounds and compositions
US4214090A (en) * 1976-01-14 1980-07-22 Commonwealth Scientific And Industrial Research Organization Fungicidal carboxamidopyrazoles
JPS57209275A (en) * 1981-06-19 1982-12-22 Nissan Chem Ind Ltd Novel pyrazoline derivative, its preparation, and vermin-controlling agent containing said derivative as active component
GB2093836B (en) * 1981-02-17 1984-09-05 Nissan Chemical Ind Ltd Insecticidal pyrazoline derivatives
US4663341A (en) 1984-02-16 1987-05-05 Rohm And Haas Company Insecticidal n-aryl-3-aryl-4,5-dihydro-1h-pyrazole-1-carboxamides
AU556949B2 (en) * 1984-10-25 1986-11-27 Fmc Corporation Pyrozoline insecticides
EP0513046B1 (en) * 1990-01-31 1997-07-09 E.I. Du Pont De Nemours And Company Arthropodicidal pyrazolines, pyrazolidines and hydrazines
DE4117076A1 (en) * 1991-05-25 1992-11-26 Bayer Ag SUBSTITUTED 4-HETARYL PYRAZOLINE
JPH05112556A (en) * 1991-10-18 1993-05-07 Nippon Bayeragrochem Kk Insecticidal pyrazolines
JPH05112555A (en) * 1991-10-18 1993-05-07 Nippon Bayeragrochem Kk Selective insecticidal pyrazolines

Also Published As

Publication number Publication date
JPS5419445B2 (en) 1979-07-16
ES411380A1 (en) 1976-07-16
NL158177B (en) 1978-10-16
DK136841C (en) 1978-05-16
AR195824A1 (en) 1973-11-09
PL93536B1 (en) 1977-06-30
IT978847B (en) 1974-09-20
NL7201674A (en) 1973-08-13
FR2171218B1 (en) 1978-09-08
CS193020B2 (en) 1979-09-17
ZA73576B (en) 1974-08-28
CA974991A (en) 1975-09-23
DE2304584C2 (en) 1983-08-11
IE37346L (en) 1973-08-09
ATA103673A (en) 1975-10-15
AT330791B (en) 1976-07-26
JPS4887028A (en) 1973-11-16
SE410187B (en) 1979-10-01
CH590846A5 (en) 1977-08-31
PL98035B1 (en) 1978-04-29
DK136841B (en) 1977-12-05
IL41472A0 (en) 1973-04-30
GB1398196A (en) 1975-06-18
DE2304584A1 (en) 1973-08-16
FR2171218A1 (en) 1973-09-21
BE795264A (en) 1973-08-09
EG11009A (en) 1976-10-31
IE37346B1 (en) 1977-07-06
AU5179773A (en) 1974-08-08
SU479295A3 (en) 1975-07-30

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