Composition and method for preventing or treating pine wilting disease

• US 5,945,445 A
• Filed: 07/02/1998
• Issued: 08/31/1999
• Est. Priority Date: 02/07/1994
• Status: Expired due to Term

• Current Assignee: Merck Sharp & Dohme Corporation (Merck & Co., Inc.)
• Original Assignee: Merck & Co., Inc.
• Inventors: Kumagai, Tetsuo, Barringer, George F.
• Primary Examiner(s): ROBINSON, ALLEN JAY
• Application Number:
  US09/109,190
• Time in Patent Office: 425 Days
• Field of Search: 514/453, 514/63
• US Class Current: 514/453
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A01N 47/18 containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
• CPC Class Codes: A01N 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00

Abstract

There is disclosed a composition for preventing wilting of pines which comprises as an active ingredient a compound of the formula (I): wherein

R₁ is alkyl, cycloalkyl or alkenyl;

R₂ is hydrogen, alkyl, alkanoyl or alkylsilyl;

R₃ is hydrogen or optionally substituted hydroxyl;

R₄ is hydrogen, hydroxyl or alkoxyimino;

the carbon-carbon bond X represents a single bond or double bond, provided that, when R₄ is alkoxyimino, X represents a single bond, and when R₁ is methyl or ethyl and R₂, R₃ and R₄ are hydrogen, X represents a double bond; or a salt thereof, as well as a method of preventing the pine wilt using the same.

Even if pine trees are infected with pine wilt nematodes, the pine wilt nematodes can be killed before the pine wilt nematodes start action in the trunks of the pine trees.

Claims

1. A method for preventing or treating pine wilting disease which comprises injecting into the trunk of a pine tree in need thereof a compound of the formula (I):

##STR13## wherein;

R₁ is alkyl, cycloalkyl or alkenyl;

R₂ is hydrogen, alkyl, alkanoyl or alkylsilyl;

R₃ is hydrogen or optionally substituted hydroxyl;

R₄ is hydrogen, hydroxyl or alkoxyimino;

the carbon-carbon bond X represents a single bond or double bond, provided that, when R₄ is alkoxyimino, X represents a single bond, and when R₁ is methyl or ethyl and R₂, R₃ and R₄ are hydrogen, X represents a double bond;

or a salt thereof,

in an amount which is nematocidally and insecticidally effective in controlling both the pine wilt nematode Bursaphelenchus xylophilus and the pine sawyer beetle Monochamus alternatus.

2. The method of claim 1 wherein the compound of the formula (I), R₁ is isopropyl or sec-butyl.

3. The method of claim 1 wherein the compound of the formula (I), R₂ is hydrogen.

4. The method of claim 1 wherein the compound of the formula (I), R₃ is a group of the formula (II) or formula (III):

##STR14## wherein R₅ is oxo;

optionally substituted hydroxyl;

or

--NR₆ R₇ wherein R₆ and R₇ are each independently hydrogen, lower alkyl, lower alkanoyl, optionally substituted benzenesulfonyl or lower alkylsulfonyl.

5. The method of claim 4 wherein the compound of the formula (I), R₃ is a group of the formula (II) wherein R₅ is hydroxyl or methylamino.

6. The method of claim 1 wherein the compound of the formula (I), R₄ is hydrogen.

7. The method of claim 1 wherein the compound of the formula (I), R₁ is sec-butyl or isopropyl, R₂ is hydrogen, R₃ is a group of the formula (II) ##STR15## R₄ is hydrogen, R₅ is hydroxyl, and X is a single bond.

8. The method of claim 1 wherein the compound of the formula (I), R₁ is sec-butyl or isopropyl, R₂ is hydrogen, R₃ is a group of the formula (II) ##STR16## R₄ is hydrogen, R₅ is hydroxyl, and X is a double bond.

9. The method of claim 1 wherein the compound of the formula (I), R₁ is sec-butyl or isopropyl, R₂ is hydrogen, R₃ is a group of the formula (II) ##STR17## R₄ is hydrogen, R₅ is methylamino, and x is a double bond.

10. The method of claim 1 wherein the compound is ivermectin.

11. The method of claim 1 wherein the compound is abamectin.

12. The method of claim 1 wherein the compound is emamectin benzoate.

13. The method of claim 1 wherein the compound is moxidectin.

14. The method of claim 1 wherein the compound is doramectin.