GB2195628A - Method of combating acarids using isoxazole compounds - Google Patents
Method of combating acarids using isoxazole compounds Download PDFInfo
- Publication number
- GB2195628A GB2195628A GB08623167A GB8623167A GB2195628A GB 2195628 A GB2195628 A GB 2195628A GB 08623167 A GB08623167 A GB 08623167A GB 8623167 A GB8623167 A GB 8623167A GB 2195628 A GB2195628 A GB 2195628A
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- Prior art keywords
- group
- isoxazole
- alkyl
- hydrogen atom
- iodophenyl
- Prior art date
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-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
A method of combating acarids at a locus, which comprises applying to the locus an acaricidally effective amount of a compound of the general formula: <IMAGE> wherein R<1> represents a phenyl group which is substituted by one or two halogen atoms, or by one C1-4 alkyl, haloalkyl, alkylthio or nitro group; R<2> represents a hydrogen atom or a C1-4 alkyl group; and R<3> represents a C<1-4> alkyl group or an acetyl or trifluoroacetyl group; or a salt thereof. Also disclosed are certain novel compounds of formula (I) and acaricial compositions containing them.
Description
SPECIFICATION
Method of combating acarids using heterocyclic compounds
This invention relates to a method of combating acarids at a locus using certain 3-amino-S- phenylisoxazole derivatives. It further relates to certain novel 3-amino-5-phenylisoxazole derivatives, to process for their preparation and to pesticidal compositions containing them.
Derivatives of 3-amino isoxazole are known. For example, Belgian Patent Specification No.
818161 describes certain 3-acylamino isoxazole derivatives having herbicidal activity. British
Patent Specification No. 1548397 describes certain N-acylamino isoxazole derivatives having pharmacological activity. European patent application, publication no. 181018 describes certain 3-aminoisoxazole derivatives having anticoccidial activity. There is no suggestion in any of these three references that such compounds may have insecticidal or acaricidal activity.
European patent application publication no. 48162 describes certain 5-aryl-3-isoxazolyl benzamides having insecticidal activity. However, there is no suggestion in this reference that such compounds may have be active against acarids, which, it will be appreciated, are very different from insects.
It has surprisingly now been found that certain 3-amino-5-phenylisoxazole derivatives, which are different in structure from the 5-aryl-3-isoxazolyl benzamides described in European patent application publication no. 48162, have acaricidal activity. Accordingly the present invention provides a method of combating acarids at a locus, which comprises applying to the locus an acaricidally effective amount of a compound of the general formula:
wherein R' represents a phenyl group which is substituted by one or two halogen atoms, or by one C14 alkyl, C14 haloalkyl, C14 alkylthio or nitro group; R2 represents a hydrogen atom or a C14 alkyl group; and R3 represents a C14 alkyl group or an acetyl or trifluoroacetyl group; or a salt thereof.
Preferably either R2 represents a C14 alkyl group and R3 represents a C14 alkyl group or an acetyl or trifluoroacetyl group, or R2 represents a hydrogen atom and R3 represents a C14 alkyl group.
preferably R' represents a phenyl group substituted by one or two chlorine, bromine or iodine atoms, or by an isopropyl, trifluoromethyl, methylthio or nitro group. For example, R' may represent a 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichloro-phenyl, 3-bromophenyl, 4-bromophenyl, 3-iodophenyl, 4-iodophenyl, 4-isopropylphenyl, 3-trifluoromethylphenyl, 4-methylthiophenyl or 3-nitrophenyl group.
Preferably R2 represents a hydrogen atom or a methyl, ethyl or propyl group.
Preferably R3 represents a methyl, ethyl or propyl group or an acetyl or trifluoroacetyl group.
In the method according to the invention, the acarids are preferably mites.
The compounds of formula I may be prepared by (A) reacting hydroxylamine with a compound of general formula II
or a tautomer thereof, wherein R1, R2 and R3 are as defined for the general formula I and R4 represents an alkyl group, or (B) reacting a compound of the general formula 111
with a compound of general formula IV
R7X IV wherein either R5 represents the group R2 and R7 represents the group R3 or R5 represents the group R3 and R7 represents the group R2; R6 represents a hydrogen atom; X represents a leaving atom or group; and R' is as defined for the general formula
The alkyl group represented by R4 may be, for example, a C, 6 alkyl group such as a methyl group.
Referring to general process (A), the reaction is convenienfly effected by treating a compound of general formula II with hydroxylamine hydrochloride in pyridine under reflux.
Referring to general proces (B), the leaving atom or group represented by X may be a halogen atom such as a chlorine or bromine atom; or a hydrocarbylsulphonyloxy group such as p-toluene sulphonyloxy. The reaction may conveniently be effected in an organic solvent such as an alcohol, e.g. ethanol, or a tertiary amine, e.g. pyridine, at a temperature of from 0 to 100"C.
In the method according to the invention, the compounds of formula (I) are generally applied at a dosage rate of, for example, 0.025 to 5 kg/ha. In general, for application to plant foliage or bark, the preferred dosage rates will be in the range 0.1 to 1.0 kg/ha.
The method according to the invention preferably comprises the application of compositions comprising a compound of general formula (I) together with a carrier.
A carrier in a composition suitable for use in the method according to the invention is any material with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant, seed or soil, or to facilitate storage, transport or handling. A carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid, and any of the carriers normally used in formulating pesticidal compositions may be used. Preferably the compositions contain 0.5 to 95% by weight of active ingredient.
Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earths; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulphate; ammonium sulphate; synthetic hydrated silicon oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulphur; natural and synthetic resins, for example coumarone resins, polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen; waxes; and solid fertilisers, for example superphosphates.
Suitable liquid carriers include water; alcohols, for example isopropanol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic- or araliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kerosine and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, perchloroethylene and trichloroethane. Mixtures of different liquids are often suitable.
Agricultural compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application. The presence of small amounts of a carrier which is a surface-active agent facilitates this process of dilution. Thus preferably at least one carrier in the composition is a surface-active agent. For example the composition may contain at least two carriers, at least one of which is a surface-active agent.
A surface-active agent may be an emulsifying agent, a dispersing agent or a wetting agent; it may be nonionic or ionic. Examples of suitable surface-active agents include the sodium or calcium salts of polyacrylic acids and lignin sulphonic acids; the condensation of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitol, sucrose or pentaerythritol; condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example poctylphenol or poctylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates such as dodecylbenzene sulphonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.
The compositions may for example be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Wettable powders usually contain 25, 50 or 75% w of active ingredient and usually contain in addition to solid inert carrier, 3-10% w of a dispersing agent and, where necessary, 0-10% of stabiliser(s) and/or other additives such as penetrants or stickers. Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and are diluted in the field with further solid carrier to give a composition usually containing 2110% w of active ingredient. Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676-0.152 mm), and may be manufactured by agglomeration or impregnation techniques.Generally, granules will contain 1~75% w active ingredient and 0-10% w of additives such as stabilisers, surfactants, slow release modifiers and binding agents. The so-called "dry flowable powders" consist of relatively small granules having a relatively high concentration of active ingredient. Emulsifiable concentrates usually contain, in addition to a solvent and, when necessary, co-solvent, 10-50% w/v active ingredient, 2-20% w/v emulsifiers and 0-20% w/v of other additives such as stabilisers, penetrants and corrosion inhibitors.Suspension concentrates are usually compounded so as to obtain a stable, non-sedimenting flowable product and usually contain 10-75% w active ingredient, 0.5-15% w of dispersing agents, 0.1-10% w of suspending agents such as protective colloids and thixotropic agents, 0-10% w of other additives such as defoamers, corrosion inhibitors, stabilisers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation or as anti-freeze agents for water.
Aqueous dispersions and emulsions, for example compositions obtained by diluting a wettable powder or a concentrate with water, are also suitable for use in the method according to the -invention.The said emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick 'mayonnaise'-like consistency.
The compositions may also contain other ingredients, for example other compounds possessing pesticidal, herbicidal, or fungicidal properties.
Certain compounds of general formula I are novel. Accordingly the invention further provides novel compounds of general formula:
wherein one of R2a and R3a represents a propyl group and the other represents a hydrogen atom or a C14 alkyl, acetyl or trifluoroacetyl group, and Ria represents a phenyl group which is substituted by one or two halogen atoms, or by one C14 alkyl, C14 haloalkyl, C14 alkylthio or nitro group; or one of R2" and R3" represents an ethyl group and the other represents a hydrogen atom or a methyl, or trifluoroacetyl group, and Rla represents a 3-bromophenyl, 3-iodophenyl, 4iodophenyl or 4-methythio group; or R2" and R3" both represent methyl groups and R1, represents a 3,4-chlorophenyl group. Particularly preferred compounds of formula la, because of their outstanding level of acaricidal activity, are: 3-n-propylamino-5-(3'-bromophenyl)isoxazole; 3-methylethylamino-5-(3'-iodophenyl)isoxazole; 3-dimethylamino-5-(3',4'-dichlorophenyl)isoxazole; 3-n-propylamino-5-(3'-iodophenyl(isoxazole; and 3-n-propylmethylamino-5-(3'-iodophenyl)isoxazole.
The invention further provides an acaricidal composition comprising a compound of formula la as defined above, together with a carrier. Preferably the composition comprises two carriers, at least one of which is a surface-active agent.
The following Examples illustrate the invention. Examples 1 to 19 illustrate the preparation of compounds of formula I. The products of Examples 2 and 4 to 19 are believed to be novel.
Example 20 provides data illustrating the acaricidal activity of compounds of formula
Example 1 3-ethylamino-5-(4'-chlorophenyl) isoxazole
1 -(4'-chlorophenyl)-3-ethylamino-3-methylthioprop-2-en- 1-one (269), and hydroxylamine hydrochloride (10g) in pyridine (15ml) were heated together under reflux for 3-4 hours. The solvent was then removed under reduced pressure and the residue dissolved in chloroform. The chloroform after washing with water was removed and the residue crystallised from methanol to give the required 3-ethylamino-5-(4'-chlorophenyi) isoxazole (mpt. 134-135"C).
Example 2 3-n, Prop ylamino-5- (3 '-bwmophen yl)isoxazole 2-propene- 1-one, 3-n,propylamino, 3-methylthio- 1 -3'-bromophenyl (2.59) and hydroxylamine hydrochloride (1.39) in pyridine (40ml) were heated at 100"C for 5 hours. The solvent was then removed under reduced pressure and the residue was dissolved in diethylether. The diethylether solution, after washing with water, was removed and the residue was purified by chromatograhy using silica gel, eluting with chloroform to give the title compound 1.59 (m.p.t. 67"C).
Analysis
Calculated for C,2H130N2Br C 51.3 H 4.7 N 9.9
Found C 51.0 H 4.8 N 9.6
Examples 3-17
By a method analogous to that described in Examples 1 and 2, further compounds of the general formula I were prepared. These compounds are described in Table I.
TABLE I
Melting
No. Compound point Analysis C H N
3 3-methylamino-5-(3'-bromophenyl)isoxazole 95 Calc. C10H9ON2Br 47.4 3.6 11.1
Found 47.1 3.5 10.6
4 3-n-propylamino-5-(4'-bromophenyl)isoxazole 125 Calc. C12H13CN2Br 51.3 4.7 10.0
Found 51.2 4.7 10.1
5 3-dimethylamino-5-(4'-bromophenyl)isoxazole 112 Calc. C11H10CN2Cl2 51.4 3.9 10.9
6 3-ethylamino-5-(4'iodophenyl)isoxazole 135-136 Calc. C11H11N2OI 42.0 3.5 8.9
Found 42.0 5.5 8.6
7 3-n-propylamino-5-(3'-chloropbenyl)isoxazole 47-48 Calc. C12H13N2OCl 60.9 5.5 11.8
Found 60.7 5.5 11.8
8 3-n-propylamino-5-(4'-isopropylphenyl)isoxazole 58-60 Calc. C15H20N2O 73.8 8.2 11.5
Found 73.5 8.3 11.2
9 3-n-propylamino-5-(3',4'-dichlorophenyl)isoxazole 80 Calc. C12H12ON2Cl2 53.1 4.4 10.3
Found 52.9 4.5 10.2 TABLE I (continued)
Melting
No. Compound point Analysis C H N 10 3-n-propylamino-5-(3'-trifluoromethylphenyl)isoxazole 73 Calc. C13H13ON2F3 57.8 4.8 10.4
Found 57.6 5.0 10.4 11 3-n-propylamino-5-(2'-chlorophenyl)isoxazole 56 Calc. C12H13CN2Cl 60.9 5.5 11.8
Found 60.6 5.7 11.8 12 3-n-propylamino-5-(3'-nitrophenyl)isoxazole 86 Calc. C12H13CO3N2 58.3 5.3 17.0
Found 58.2 5.3 16.9 13 3-n-propylamino-5-(4'-chlorophenyl)isoxazole 69-70 Calc. C12H13N2Cl 60.9 5.5 11.8
Found 60.9 5.6 11.8 14 3-methylethylamino-5-(3'-bromophenyl)isoxazole oil Calc. C12H13N2Br 51.3 4.7 10.0
Found 51.3 4.8 9.7 15 3-methylethylamino-5-(3'-iodophenyl)isoxazole oil Calc. C11H130N2I 43.9 4.0 8.5
Found 44.0 4.0 8.5 16 3-n-propylamino-5-(3'-iodophenyl)isoxazole 92 Calc. C12H13ON2I 43.9 4.0 8.5
Found 43.8 3.9 8.5 17 3-n-propylmethylamino-5-(3'-iodophenyl)isoxazole oil Calc.C13H15ON2I 45.6 4.4 8.2
44.9 4.3 8.0 Example 18 3-n-propyl,N-acetylamino-5-(3'-bromophenyl)isoxazole 5-(3'-bromophenyl)-3-(N-propylamino)isoxazole (0.89) was dissolved in pyridine (20cm3) and acetyl chloride (3cm3) was added dropwise with stirring. The mixture was heated on a steam bath for 2 minutes cooled, poured into ice water, extracted into CHCI3 and eluted down a silica/CHCI3 column. This afforded the title compound (0.49) as an oil.
Analysis
Calculated for C,4H15N202Br C 52.0 H 4.6 N 8.7
Found C 52.0 H 4.7 N 8.3
Example 19 3-N-ethyl-N-trifluoroacetylamino-(4'-methylthiophenylpisoxazole The title compound was prepared according to the method of Example 18.
Analysis
C H N
Calculated for C24H'3N202SF3 50.9 3.9 8.5
Found 50.7 4.7 8.5
Example 20
Acaricidal Activity
Leaf discs were infested with 30-60 larvae of the mite Tetranicus urticae and sprayed with solution of the test compound made up over a range of concentrations in 10% acetone/water containing 0.025% Triton X100 ("TRITON" is a registered trade mark). When dry, the discs were maintained at constant temperature for 12 days, after which mortality assessments were made.
In each test an LC50 (the dosage of active material required to kill half of the test species) for the compound was calculated from the mortality figures and compared with the corresponding
LC50 for a standard insecticide, ethyl parathion, in the same tests. The results are expressed as toxicity indices thus: LC50 (parathion) tixucuty index= - x 100
LC50 (test compound) and are set out in Table II below.
Table II
Acaricidal Activity
Compound of Example No. Toxicity dex 1 110
2 1400
3 170
4 210
5 450
6 270
7 250
8 105
9 224
10 133
11 140
12 230
13 150
14 280
15 860
16 330
17 420
18 250
19 190
Claims (10)
1. A method of combating acarids at a locus, which comprises applying to the locus an acaricidally effective amount of a compound of the general formula:
wherein R' represents a phenyl group which is substituted by one or two halogen atoms, or by one C14 alkyl, haloalkyl, alkylthio or nitro group; R2 represents a hydrogen atom or a C1-4 alkyl group; and R3 represents a C14 alkyl group or an acetyl or trifluoroacetyl group; or a salt thereof.
2. A method as claimed in claim 1 wherein either R2 represents a C14 alkyl group, and R3 represents a C14 alkyl group or an acetyl or trifluoroacetyl group or R2 represents a hydrogen atom and R3 represents a C1-4 alkyl group.
3. A method as claimed in claim 1 wherein R' represents a phenyl group substituted by one or two chlorine, bromine or iodine atoms, or by an isopropyl, trifluoromethyl, methylthio or nitro group.
4. A method as claimed in claim 1 or claim 2 wherein R2 represents a hydrogen atom or a methyl, ethyl or propyl group.
5. A method as claimed in any one of claims 1 to 3 wherein R3 represents a methyl, ethyl or propyl group or an acetyl or trifluoroacetyl group.
6. Compounds of the general formula:
wherein one of R2a and R38 represents a propyl group and the other represents a hydrogen atom or a C14 alkyl, acetyl or trifluoroacetyl group, and Ria represents a phenyl group which is substituted by one or two halogen atom, or by one C14 alkyl, C1-4 haloalkyl, C1-4 alkylthio or nitro group; or one of R2a and R3a represents an ethyl group and the other represents a hydrogen atom or a methyl or trifluoroacetyl group, and Ra represents a 3-bromophenyl 3-iodophenyl, 4iodophenyl or 4-methylthio group; or R2a and R3a both represent methyl groups and Ria represents a 3,4-dichlorophenyl group.
7. Any of the following compounds: 3-n-propylamino-5-(3'-bromophenyl)isoxazole; 3-methylethylamino-5-(3'-iodophenyl)isoxazole; 3-dimethylamino-5-(3',4'-dichlorophenyl)isoxazole ; 3-n-propylamino-5-(3'-iodophenyl)isoxazole; and 3-n-propylmethylamino-5-(3'-iodophenyl)isoxazole.
8. An acaricidal composition which comprises a compound as claimed in claim 6 or claim 7 together with a carrier.
9. An acaricidal composition as claimed in claim 8, which comprises at least two carriers, at least one of which is a surface-active agent.
10. A compound as claimed in claim 1 and named in any one of Exampels 2 and 4 to 19 herein.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08623167A GB2195628A (en) | 1986-09-26 | 1986-09-26 | Method of combating acarids using isoxazole compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08623167A GB2195628A (en) | 1986-09-26 | 1986-09-26 | Method of combating acarids using isoxazole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8623167D0 GB8623167D0 (en) | 1986-10-29 |
| GB2195628A true GB2195628A (en) | 1988-04-13 |
Family
ID=10604827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08623167A Withdrawn GB2195628A (en) | 1986-09-26 | 1986-09-26 | Method of combating acarids using isoxazole compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2195628A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0563686A1 (en) * | 1992-03-31 | 1993-10-06 | Bayer Ag | Utilization of 3 substituted amino isoxazole derivatives against endoparasites, new 3 substituted amino isoxazols and process for their preparation |
-
1986
- 1986-09-26 GB GB08623167A patent/GB2195628A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0563686A1 (en) * | 1992-03-31 | 1993-10-06 | Bayer Ag | Utilization of 3 substituted amino isoxazole derivatives against endoparasites, new 3 substituted amino isoxazols and process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8623167D0 (en) | 1986-10-29 |
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| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |