GB1420243A - Cyclopropylmethyl compounnds and their use as acaricides - Google Patents
Cyclopropylmethyl compounnds and their use as acaricidesInfo
- Publication number
- GB1420243A GB1420243A GB2197473A GB2197473A GB1420243A GB 1420243 A GB1420243 A GB 1420243A GB 2197473 A GB2197473 A GB 2197473A GB 2197473 A GB2197473 A GB 2197473A GB 1420243 A GB1420243 A GB 1420243A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- reaction
- formula
- compounds
- prepared
- 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
Links
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 title abstract 2
- 230000000895 acaricidal effect Effects 0.000 title 1
- 239000000642 acaricide Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000004820 halides Chemical class 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000004450 alkenylene group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- JDMINEJTNOBFFD-UHFFFAOYSA-N cyclopropylmethanethiol Chemical compound SCC1CC1 JDMINEJTNOBFFD-UHFFFAOYSA-N 0.000 abstract 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000005504 styryl group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- 150000007970 thio esters Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon 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
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
-
- 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
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/16—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/44—Adipic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/46—Pimelic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/48—Azelaic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/50—Sebacic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F5/00—Obtaining drying-oils
- C09F5/08—Obtaining drying-oils by esterification of fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1420243 Cyclopropylmethyl compounds ZOECON CORP 8 May 1973 [22 May 1972 19 June 1972 13 April 1973] 21974/73 Heading C2C The invention comprises compounds of the Formula I wherein R<SP>2</SP> is alkyl of 10 to 22 carbon atoms; alkenyl of 10 to 22 carbon atoms; alkynyl of 10 to 22 carbon atoms; aryl of 7 to 14 carbon atoms; aralkyl of 7 to 15 carbons; styryl or the group in which A is alkenylene of 1 to 20 carbon atoms, alkenylene of 2 to 20 carbon atoms, said alkyl, alkenyl, alkynyl, aryl or aralkyl optionally having one or two substituents selected from nitro, alkoxy of 1 to 4 carbon atoms, halogen and lower alkyl thio. The compounds of Formula I can be prepared by the reaction of an acid halide of formula R<SP>2</SP>COX with cyclopropyl methyl alcohol neat or in an organic solvent inert to the reaction. The compounds of Formula II can be prepared by the reaction of an acid halide R<SP>2</SP>COX with cyclopropyl methyl mercaptan in an organic solvent inert to the reaction and usually in the presence of pyridine, Alternatively the thioesters may be prepared by the reaction of a thio acid of the formula R<SP>2</SP>-COSH with a halide of the formula in an organic solvent inert to the reaction and in the presence of a base. The compounds of the invention are used as herbicides.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25536872A | 1972-05-22 | 1972-05-22 | |
| US26390272A | 1972-06-19 | 1972-06-19 | |
| US350708A US3923871A (en) | 1972-06-19 | 1973-04-13 | Cyclopropylmethyl esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1420243A true GB1420243A (en) | 1976-01-07 |
Family
ID=27400856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2197473A Expired GB1420243A (en) | 1972-05-22 | 1973-05-08 | Cyclopropylmethyl compounnds and their use as acaricides |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS49100220A (en) |
| CA (1) | CA1015372A (en) |
| CH (1) | CH574211A5 (en) |
| DE (1) | DE2325583A1 (en) |
| ES (1) | ES414958A1 (en) |
| FR (1) | FR2185611A1 (en) |
| GB (1) | GB1420243A (en) |
| IL (1) | IL42288A0 (en) |
| NL (1) | NL7307049A (en) |
-
1973
- 1973-05-04 CA CA170,458A patent/CA1015372A/en not_active Expired
- 1973-05-08 GB GB2197473A patent/GB1420243A/en not_active Expired
- 1973-05-16 IL IL42288A patent/IL42288A0/en unknown
- 1973-05-19 DE DE2325583A patent/DE2325583A1/en active Pending
- 1973-05-19 ES ES414958A patent/ES414958A1/en not_active Expired
- 1973-05-21 FR FR7318408A patent/FR2185611A1/fr not_active Withdrawn
- 1973-05-21 NL NL7307049A patent/NL7307049A/xx unknown
- 1973-05-21 JP JP48056662A patent/JPS49100220A/ja active Pending
- 1973-05-22 CH CH728273A patent/CH574211A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2185611A1 (en) | 1974-01-04 |
| CA1015372A (en) | 1977-08-09 |
| DE2325583A1 (en) | 1973-11-29 |
| IL42288A0 (en) | 1973-07-30 |
| NL7307049A (en) | 1973-11-26 |
| ES414958A1 (en) | 1976-06-01 |
| CH574211A5 (en) | 1976-04-15 |
| JPS49100220A (en) | 1974-09-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |