RU2000119743A

RU2000119743A - DERIVATIVES 2,2-DIMETHYL 3- (2-FLUORVINYL) CYCLOPROPANKARBARIC ACID, METHOD OF THEIR PRODUCTION AND USE AS PESTICIDES

Info

Publication number: RU2000119743A
Application number: RU2000119743/04A
Authority: RU
Inventors: Эндрю АДАМС; Жан-Пьер ДЕМУТ; Жак ДЕМАСЕЙ; Дидье Бабэн
Original assignee: Авентис Кропсайенс Гмбх
Priority date: 1997-12-22
Filing date: 1998-12-10
Publication date: 2002-06-20

Claims

1. The compound of formula (I)

in all possible stereoisomeric forms, and also in the form of their mixtures, where R represents the residue of the alcohol used in the pyrethroid series.

2. The compound of formula (I) according to claim 1, where R is: an alkyl radical containing from 1 to 18 carbon atoms; a benzyl radical optionally substituted by one or more of the radicals selected from the group consisting of alkyl radicals containing from 1 to 4 carbon atoms, alkenyl radicals containing from 2 to 6 carbon atoms, alkenyloxy radicals containing from 2 to 6 carbon atoms, alkadienyl radicals containing from 4 to 8 carbon atoms, methylenedioxy radical and halogen atoms;
or group:

where the substituent R ₁ represents a hydrogen atom or a methyl radical, and the substituent R ₂ represents a monocyclic aryl or a group —CH ₂ —C≡CH; or group:

where a represents a hydrogen atom or a methyl radical, a R ₃ represents -CH ₂ -CH = CH ₂ , -CH ₂ -C≡CH, -CH ₂ -CH = CH-CH ₃ , -CH ₂ -CH = CH-CH = CH ₂ or the radical -CH ₂ -CH = CH-CH ₂ -CH ₃ ; or group:

where a represents a hydrogen atom or a methyl radical, R ₃ is as previously defined, R ′ ₁ and R ′ _{2 are the} same or different and represent a hydrogen atom, a halogen atom, an alkyl radical containing from 1 to 6 carbon atoms, an aryl radical containing from 6 to 10 carbon atoms, an alkoxycarbonyl group containing from 2 to 5 carbon atoms or a cyano group; or group:

where B represents an oxygen or sulfur atom, —C (O) - or —CH ₂ -, R ₄ represents a hydrogen atom, —C≡N radical, methyl radical, CONH ₂ radical, —CSNH ₂ radical or —C≡CH radical, R ₅ represents a halogen atom or a methyl radical, and n represents the number 0, 1 or 2;
or group:

or group:

where the substituents R ₆ , R ₇ , R ₈ and R ₉ represent a hydrogen atom, a chlorine atom or a methyl radical, and where S / I symbolizes an aromatic cycle or a similar dihydro or tetrahydrocycle;
or group:

or group:

where R ₁₀ represents a hydrogen atom or a CH radical, R ₁₂ represents -CH ₂ - a radical, or an oxygen atom,
R ₁₁ represents a thiazyl radical or thiadiazyl, the bond of which with

may be located in any of the available positions, with R _{12 being} bound to R _{11 by} a carbon atom between the sulfur atom and the nitrogen atom;
or group:

or group:

where R ₁₃ represents a hydrogen atom or a C≡CH or CN radical, a, b, c, d, e represent a hydrogen atom, a halogen atom, an alkyl, O-alkyl, S-alkyl radical containing up to 8 carbon atoms, saturated or unsaturated, optionally substituted by one or more of the halogen atoms, CN, NO ₂ , NH ₂ or OH radical,
or R represents a radical:

where e and f represent methyl, CH ₂ F, CHF ₂ or CF ₃ radical;
or R represents an aryl group containing from 6 to 14 carbon atoms, optionally substituted by one or more of OH, O-alkyl or alkyl groups containing from 1 to 8 carbon atoms, or CF ₃ , OC F ₃ or SCF ₃ groups;
or R represents a pyridinyl, furanyl, thiophenyl oxazolyl or thiazolyl radical.

3. The compounds of formula (I) according to claim 1 or 2, where R is a radical:

where Y represents a hydrogen atom or a halogen atom, a hydroxyl, NO ₂ , CN or NH ₂ , CH ₂ OH or CH ₂ OCH ₃ radical, an alkyl, O-alkyl or S-alkyl radical containing up to 8 carbon atoms, optionally substituted by one or more of hydrogen atoms, and / or optionally separated by one or more heteroatoms.

4. The compound of formula I according to any one of paragraphs. 1-3, where R represents the radical:

5. The compounds of formula I in one of the paragraphs. 1-4, which are:
[2,5-dioxo-3- (2-propynyl) -1-imidazolidinyl] methyl [1R-trans (Z)] 2,2-dimethyl-3- (2-fluoro-1-propenyl) cyclopropanecarboxylate
[2,5-dioxo-3- (2-propynyl) -1-imidazolidinyl] methyl [1R-cis- (E)] 2,2-dimethyl-3- (2-fluoro-1-propenyl) cyclopropanecarboxylate
[2,5-dioxo-3- (2-propynyl) -1-imidazolidinyl] methyl [1R-trans (E)] 2,2-dimethyl-3- (2-fluoro-1-propenyl) cyclopropanecarboxylate.

6. The method of obtaining compounds of the formula I according to claim 1, characterized in that the acid of formula II:

or a functional derivative of this acid in all possible stereoisomeric forms, as well as mixtures thereof, is exposed to an alcohol of formula III:
ROH
where R represents the residue of the alcohol used in the pyrethroid series, or a functional derivative of this alcohol, and thus the desired compound of formula I is obtained

7. The compounds of formula II, defined in paragraph 6.

8. Pesticide compositions comprising at least one compound as defined in any of paragraphs. 1-5, as an active ingredient.

9. The pesticide composition according to claim. 8, characterized in that the active ingredient is the compound according to claim 5.

10. Insecticidal, acaricidal or nematocidal composition according to claim 8, characterized in that it includes auxiliary agents and additives that are commonly used for such applications.

11. Agent for the protection of crops, comprising at least one compound of formula I and at least one more active compound selected from the group of fungicides, insecticides, acaricides, nematocides, herbicides, plant growth regulators, sterilizers and attractants, together with auxiliary agents and additives that are commonly used for such applications.

12. Composition for protecting wood, or for use as a preservative in sealants, in paints, in cooling lubricants for working with metal, or in oils for drilling or cutting, which includes an effective amount of at least one compound of formula I, as stated in any of paragraphs. 1-5, together with auxiliary agents and additives that are commonly used for such applications.

13. The compound of formula I according to any one of paragraphs. 1-5 to combat endo- and ectoparasites of animals.

14. The method for preparing the composition according to claim 8, which comprises mixing one or more of the active compounds and other auxiliary agents and additives, and preparing them in a form suitable for use.

15. The method of combating harmful insects, mites and nematodes, which includes applying an effective amount of the compounds of formula I according to any one of paragraphs. 1-5, or the composition according to claim 8, on these harmful insects, ticks and nematodes, or on plants, on patches or substrates that are infected by them.

16. The compound of formula I according to any one of paragraphs. 1-5 for processing or coating of seeds with an effective amount.