GB1565226A - Creation of Inventions and Patents with Artificial Intelligence

GB1565226A – Urea derivatives processes therefor and herbicidal compositions therof
– Google Patents

GB1565226A – Urea derivatives processes therefor and herbicidal compositions therof
– Google Patents
Urea derivatives processes therefor and herbicidal compositions therof

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Publication number
GB1565226A

GB1565226A
GB5952/79A
GB595279A
GB1565226A
GB 1565226 A
GB1565226 A
GB 1565226A
GB 5952/79 A
GB5952/79 A
GB 5952/79A
GB 595279 A
GB595279 A
GB 595279A
GB 1565226 A
GB1565226 A
GB 1565226A
Authority
GB
United Kingdom
Prior art keywords
compound
compound according
formula
compounds
herbicidal compositions
Prior art date
1975-09-05
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
GB5952/79A
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.)

Sandoz AG

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Sandoz 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.)
1975-09-05
Filing date
1976-09-02
Publication date
1980-04-16

1976-09-02
Application filed by Sandoz AG
filed
Critical
Sandoz AG

1980-04-16
Publication of GB1565226A
publication
Critical
patent/GB1565226A/en

Status
Expired
legal-status
Critical
Current

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Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups

C07C275/64—Derivatives 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

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups

C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas

C07C275/48—Y being a hydrogen or a carbon atom

C07C275/50—Y being a hydrogen or an acyclic carbon atom

Description

PATENT SPECIFICATION
Application No 5952/79 ( 1 ( 22) Filed 2 Sept 1976 Divided out of No 1565225 Convention Application No 11591/75 Filed 5 Sept 1975 in Switzerland (CH) Complete Specification published 16 April 1980
INT CL 3 C 07 C 127/19 AOIN 37/26 ( 52) Index at acceptance C 2 C 220 227 22 Y 313 314 31 Y 338 341 34 Y 578 626 71 X 727 805 Y AA KD ( 72) Inventors KARL SECKINGER and RUDOLF SANDMEIER ( 54) UREA DERIVATIVES, PROCESSES T It EREFOR AND HERBICIDAL COMPOSITIONS THEREOF ( 71) We, SANDOZ LTD, of 35 Lichtstrasse, 4002 Basle, Switzerland, a Swiss Body Corporate, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:-
The present invention relates to phenyl ureas.
In our co-pending Application, No 36367/76 (Serial No 1,565,225) we describe and claim a method of selectively combating weeds in a cultivated plant locus which comprises applying thereto a selective herbicidally effective amount of a compound of formula I C 110 R C, O R 3 R C-‘3 i v N-CO-N-CH I wherein R 1 and R 2 are each, independently, H, (C,-C 4)alkyl, (C,-C 4)alkoxy, trifluoromethyl, F, Cl or Br and R 3 is H, methyl or methoxy with the provisos that a) when R 3 is H or methyl, then a maximum of one of R, and R 2 is H, is Cl or is a carbon containing group and b) when R 3 is H and either R 2 is methyl and R, is H or R 2 is Cl and R, is methyl or when R 3 is methyl and R 2 is H and R, is Cl or F or R 2 is Cl and R, is H or methyl or R 2 is H and R, is tert butyl, then the cultivated plant crop is a cereal crop.
The present invention provides compounds of formula Ia, CHO R 1, co-NH Cf 13 a R 2 ‘ wherein R,’ and R 2 ‘ are each independently (C 1-C 4)alkyl, F, Cl or Br with the provisos that a) a maximum of one of R,’ and R 2 ‘ is Cl or is a carbon containing group b) when R 2 ‘ is Cl, R,’ is other than methyl.
The U K Specification 769,613 (Du Pont de Nemours) dicloses very broad classes of substituted phenyl ureas which embrace the compounds of the present invention None of the present compounds, which possess advantageous pre and post-emergence selective herbicidal activity, are however specifically disclosed in U K Specification No 769,613
The compounds of formula Ia may be produced by condensing a compound of formula 11, ( 21) ( 62) ( 31) ( 32) ( 33) ( 44) ( 51) 1) 1 565 226 ( 1 RI N-CO I R 2 À wherein R,’ and R 2 ‘ are as defined above, with a compound of formula Ill, CH 3 NCO III, this process also forming part of the present invention.
The reaction may be effected for example in an organic solvent such as a 5 hydrocarbon, e g toluene, preferably under anhydrous conditions, at a temperature in the range 15 to 100 C.
The compounds of formula la possess a wide spectrum of herbicidal activity against both monocotyl and dicotyl weed species, e g Alopecurus spp, Amaranthus retroflexus, Capsella bursa pastoris, Chenopodium album, Stellaria media, Senecio 10 vulgaris, Echinochloa crus-galli, Poa annua, Agrostis alba, Sida spinosa, Setaria geniculata, Digitaria sanguinelis, Sisymbrium irio and Cyperia rotunda Moreover, at the dosage levels necessary to control the weeds, the compounds of formula la cause no substantial damage in cultivated crops such as cereals especially barley and wheat, particularly the latter, rice, maize, sugar-cane, cotton, leguminous 15 crops, ground nuts, soya, alfalfa, sugar beet, carrots, potato and flax.
It should be mentioned that certain of the compounds of formula la show a certain varietal dependency in their selective action in wheat Nevertheless, the degree of susceptibility of any variety in connection with any compound may be readily determined by simple greenhouse tests 20 For the above-mentioned uses, the amount of compound to be applied to the cultivated crop will naturally vary depending on the particular crop, the compound employed, the mode of application, ambient conditions and the weed species to be treated However, in general, satisfactory results are obtained when the compound is applied in the dosage range 0 5 to 5 kg/hectare, preferably I to 3 5 kglhectare 25 The compounds may be employed as herbicidal compositions in association with herbicide carriers or diluents Such compositions containing compounds of formula Ia also form part of the present invention.
Herbicidal compositions may be employed in either solid or liquid application forms Solid forms, e g dusting forms and granulates, may be produced by mixing 30 or impregnating solid herbicide carriers such as diatomaceous earth, kaolin, talc, chalk, limestone and cellulose powder, with the compounds.
Additives may be employed in the herbicidal composition Typical of such additives are wetting and dispersing agents, e g the condensation product of formaldehyde with naphthalene sulphonate, and alkyl benzene sulphonates, 35 adhesion imparting agents, e g dextrin, and emulsion stabilizers, e g ammonium caseinate Such additives are suitable for incorporation into, e g a wettable powder form of composition or together with suitable solvents, e g hydrocarbons such as benzene, toluene, xylene, tetrahydronaphthalene, alkylated naphthalenes, kerosene, aromatic petroleum hydrocarbon fractions (e g commercial product 40 Shellsol AB (Registered Trade Mark) having b pt range 187-213 ) ketones such as isophorone, acetone, cyclohexanone, diisobutylketone and methylethylketone, alcohols such as isopropanol, ethanol, and methylcyclohexanol, chlorinated hydrocarbons such as tetrachlorethylene, ethylene chloride or trichloroethylene, to form emulsion concentrates 45 The herbicidal compositions may contain, aside from a compound of formula Ia as active agent, other active agents, such as herbicides, e g of the urea class, halogen benzonitriles, carbamates and triazines.
Concentrate forms of composition generally contain between 2 and 80 %, preferably between 2 and 50 %, by weight of a compound of formula Ia as active 50 agent.
Application forms of composition generally contain between 0 01 and 10 %/, by weight of a compound of formula I as active agent.
Specific Examples 6 f herbicidal compositions will now be described.
Example A 55
Wettable Powder parts of a compound of formula la, e g 1-methyl-3-formyl-3-( 3-chloro 4 isopropylphenyl)urea, 5 parts of a condensation product from formaldehyde and naphthalene sulphonate, 2 parts of alkyl benzene sulphonate, 5 parts of dextrin, I 1,565,226 part of ammonium caseinate and 62 parts of diatomaceous earth are mixed until a homogeneous mixture is obtained and then ground until the particles are considerably smaller than 45 microns as an average.
Example B
Emulsion Concentrate 5 Parts of a compound of formula Ia, 65 parts of xylene and 10 parts of the mixed reaction product of an alkylphenol with ethylene oxide and calcium dodecylbenzene sulphonate are thoroughly mixed until homogeneous solution is obtained The resulting emulsion concentrate is diluted with water before use.
Example C 10
Granulate Kg of a compound of formula Ia, e g I methyl 3 formyl 3 ( 3 chloro 4 isopropylphenyl) urea are dissolved in 25 1 methylene chloride The solution is then added to 95 kg of granulated attapulgate (mesh size 24/48 mesh/inch) and thoroughly mixed The solvent is then evaporated off under reduced pressure with 15 warming.
The application of the compounds may be either pre or post-emergence of either the weeds or crop Preferably the compounds are applied pre or postemergence of the crop particularly pre-emergence, in conventional manner.
The preferred novel compounds of the invention are the compounds of 20 formula Iaa, CHO 1 R N-CO-?IHCH 3 Iaa wherein R,1 is (C 2-C 4)alkyl, especially (C 2-C 3)alkyl, e g isopropyl.
The invention is further illustrated by the following Examples Where temperature is referred to, this is in C and where percentages and parts are 25 referred to these are by weight.
EXAMPLE I
I -Methyl-3-formyl-3-( 3-methyl-4-chlorophenyl)-urea To a solution of 0 1 mol of 3-methyl-4-chloroformanilide in 150 ml absolute toluene are added 11 4 g ( 0 2 mol) methylisocyanate and 1 5 ml triethylamine and 30 the mixture container sealed and left to stand for 4-7 days at room temperature.
The resulting precipitate is filtered off, washed with petroleum ether and dried to yield the title compound, m pt 108-110 (ether).
In analogous manner, the compounds of formula Ia set out in Table I below are obtained If no precipitate is formed after 7 days, the solvent and excess 35 methylisocyanate is evaporated off under vacuum, the product dried under high vacuum and recrystallised.
TABLE I :’xNo R 2 R 1 ‘ M Pt (recrsstallisation solvcnt) 2 ú ’11: Br 11 117 ‘ (ethlianol) 3 + i-C 3 H 7 Cl X 4 ? 5 (ether petroleiium ether) 4 (‘I C 211 65 ( 67 (cthcrplrtolctinl othr) Cl i-C 31 t 7 99 101 (ethier) 6 Cl sec C 41 l, oil R: valuc O 4 7 CI t ert ‘4 J 9I 1 4 (ether) 8 Br i-C 3 H, 110 112 (ethianol) N.B silica gel-chloroform/acetone eluant ( 9:1) 1,565,226 EXAMPLE 9
Selective Weed Control-Pre-emergence Tretment Seed dishes are filled to a depth of 6 cm with a mixture of peat culture substrate No I'(obtainable from Torfstreuverband G m b H, 29 Oldenberge, W.
Germany) and sand The exposed surface of the peat culture and sand mixture is 5 sprayed with 50 ml of an aqueous solution of a compound of formula Ia (formulated in accordance with Example B) and various seeds (see below) are sown in each dish After sowing of the seeds, the treated surface is covered with a thin layer ( 0 5 cm) of peat culture/sand mixture The dishes are kept for 28 days at room temperature with 14 to 17 hours light per day 10 Each of the compounds of Examples 1-8 are applied in the above manner at dosages corresponding to 1 5 kg/ha and 2 5 kg/ha.
The various plant species employed are Alopercurus spp, Amaranthus retroflexus, Capsella bursa pastoris, Chemopodium album, Stellaria media, Senecio vulgaris, Echinochloa crus-galli, Poa annua, Agrostis alba, Triticum vulgare (wheat 15 variety Probus), Hordium (barley), Glycine soja (soya), Linum usitatissium (flax), Solanum tuberosum (potato) and Gossrpium hirsutum (cotton) In every case, herbicidal selectivity is observed, that is to say, significant damage to the weeds without substantial damage to the cultivated plants.
EXAMPLE 10 20
Selective Weed Control-Post-emergence Treatment A procedure similar to that employed in Example 9 is followed with the exception that the herbicide is applied when the plants are at the 2-4 leaf stage, the sowing of the plant seeds being staggered to ensure that the plants reach the 24 leaf stage at about the same time 25 Again the compounds of Examples 1-8 are applied in the above manner at dosages corresponding to 1 5 kg/ha and 2 5 kg/ha.
The various plant species employed are Chenopodium album, Stellaria media, Senecio vulgaris, Echinochloa crus-galli, Poa annua, Agrostis alba and the cultivated crops listed in Example 9 In every case, herbicidal selectivity is observed 30

Claims (14)

WHAT WE CLAIM IS:-

1 A compound of formula Ia, CHO R: ‘2 N-CO-NHCH 3 a R 2 ‘ wherein R 1 ‘ and R 2 ‘ are each independently (C,-C 4)alkyl, F, Cl or Br with the provisos that 35 a) a maximum of one of R,’ and R,’ is Cl or is a carbon containing group b) when R 2 ‘ is Cl, R 1 ‘ is other than methyl.

2 A compound according to Claim I of formula laa CHO R 11 NE-CO-11 HCH

3 Iaa wherein R 11 is (C 2-C 4)alkyl 40 3 A compound according to Claim I, wherein R 1 ‘ is Cl and R 2 ‘ is CH 3.

4 A compound according to Claim I, wherein R,’ is Br and R 2 ‘ is CH 3.

A compound according to Claim 1, wherein R,’ is Cl and R 2 ‘ is i-C 3 H 7.

6 A compound according to Claim 1, wherein R,’ is C 2 Hs and R 2 ‘ is Cl.

7 A compound according to Claim 1, wherein R,’ is i-C 3 H 7 and R 2 ‘ is Cl 45

8 A compound according to Claim 1, wherein R 1 ‘ is se -C 4 H 5 and R 2 ‘ is Cl.

9 A compound according to Claim 1, wherein R 1 ‘ is tert -C 4 H 9 and R 2 ‘ is Cl.

A compound according to Claim I, wherein R 1 ‘ is i-C 3 H 7 and R 2 ‘ is Br.

1 I 1 A herbicidal composition comprising a compound according to any one of Claims I to 10, in association with a herbicide carrier or diluent 50

12 A herbicidal composition according to Claim 11, substantially as described 50 herein.

13 A process of producing a compound as defined in Claim 1, which comprises condensing a compound of formula 11 II, 1,565,226 1,565,226 5 R 1 ‘ Nt-C-O II Rl 2, À wherein R 1 ‘ and R 2 ‘ are as defined in Claim 1 with a compound of formula III CH 3 NCO III to produce a compound of formula Ia as defined in Claim 1.

14 A process according to Claim 13, substantially as described herein with 5 reference to any one of Examples 1 to 8.
B A YORKE & CO, Chartered Patent Agents, 98, The Centre, Feltham, Middlesex, TWI 3 4 EP.
Printed for Her Majesty’s Stationery Office, by the Courier Press, Leamington Spa, 1980 Published by The Patent Office, 25 Southampton Buildings London, WC 2 A l AY, from which copies may be obtained.

GB5952/79A
1975-09-05
1976-09-02
Urea derivatives processes therefor and herbicidal compositions therof

Expired

GB1565226A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

CH1159175

1975-09-05

Publications (1)

Publication Number
Publication Date

GB1565226A
true

GB1565226A
(en)

1980-04-16

Family
ID=4374964
Family Applications (2)

Application Number
Title
Priority Date
Filing Date

GB36367/76A
Expired

GB1565225A
(en)

1975-09-05
1976-09-02
Herbicidal application of urea derivatives

GB5952/79A
Expired

GB1565226A
(en)

1975-09-05
1976-09-02
Urea derivatives processes therefor and herbicidal compositions therof

Family Applications Before (1)

Application Number
Title
Priority Date
Filing Date

GB36367/76A
Expired

GB1565225A
(en)

1975-09-05
1976-09-02
Herbicidal application of urea derivatives

Country Status (4)

Country
Link

BE
(1)

BE845862A
(en)

GB
(2)

GB1565225A
(en)

TR
(1)

TR19497A
(en)

ZA
(1)

ZA765298B
(en)

1976

1976-09-02
GB
GB36367/76A
patent/GB1565225A/en
not_active
Expired

1976-09-02
GB
GB5952/79A
patent/GB1565226A/en
not_active
Expired

1976-09-03
ZA
ZA00765298A
patent/ZA765298B/en
unknown

1976-09-03
BE
BE170363A
patent/BE845862A/en
not_active
IP Right Cessation

1978

1978-09-03
TR
TR19497A
patent/TR19497A/en
unknown

Also Published As

Publication number
Publication date

ZA765298B
(en)

1978-04-26

BE845862A
(en)

1977-03-03

TR19497A
(en)

1979-03-29

GB1565225A
(en)

1980-04-16

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