Ethylene derivatives and pesticides containing said derivatives
AssigneeNissan Chemical Industries, Ltd.
InventorsTomoyuki Ogura, Hiroshi Murakami, Akira Numata, Rika Miyachi, Toshiro Miyake, Norihiko Mimori, Shinji Takii
Life of this patent
Estimating the term…
Abstract
Ethylene derivatives of formula (I): where Q is an unsubstituted or substituted phenyl or heterocyclic group, especially a 4-thiazolyl, 1- or 3-pyrazolyl, 1,3-oxazol-4-yl, phenyl or pyridyl group; E is a substituent such as a cyano group; A is a substituent such as a 4-pyrazolyl or thiazolyl group; and B is a substituent such as an alkylcarbonyl group. Agricultural chemicals and agents for preventing the attachment of aquatic organisms containing one or more such ethylene derivatives.
Claims32
A compound of a formula:
- wherein:
- Q represents a thiazolyl group optionally substituted by R;
- A represents a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, wherein said heterocyclic group is selected from the group consisting of a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, and quinazolinyl groups;
- provided that when Q is a 2-thiazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, or quinazolinyl group);
- B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3SCH2, CH3OC2H4OCH2, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C1-C4 alkyl group, a tetrahydropyranyl group, (CH3)3Si, a C1-C4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C1-C4 alkyl group, —SO2CF3, a C1-C4 monoalkylaminosulfonyl group, a C2-C8 dialkylaminosulfonyl group, a phenylaminosulfonyl group, a C2-C5 monoalkylaminothiocarbonyl group, a C3-C9 dialkylaminothiocarbonyl group, a C2-C5 cyanoalkyl group, a C3-C9 alkoxycarbonylalkyl group, —C(═O)T1, —P(═O)T2T3, —P(═S)T2T3, an alkali metal atom, an alkaline earth metal atom, or NHT4T5T6;
- provided that, when Q is a 2-thiazolyl group, then B is a C1-C4 alkyl group, C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3SCH2, CH3OC2H4OCH2, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C1-C4 alkyl group, a tetrahydropyranyl group, (CH3)3Si, a C1-C4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C1-C4 alkyl group, —SO2CF3, a C1-C4 monoalkylaminosulfonyl group, a C2-C8 dialkylaminosulfonyl group, a phenylaminosulfonyl group, a C2-C5 monoalkylaminothiocarbonyl group, a C3-C9 dialkylaminothiocarbonyl group, a C2-C5 cyanoalkyl group, a C3-C9 alkoxycarbonylalkyl group, —C(═O)T1, —P(═O)T2T3, or —P(═S)T2T3;
- E represents CN;
- R is a substituent selected from the group consisting of a halogen atom, a C1-C10 alkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C6 halocycloalkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a C1-C6 alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C4 haloalkoxy group, a C2-C6 haloalkenyloxy group, a C2-C6 haloalkynyloxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C6 alkenylsulfenyl group, a C2-C6 alkenylsulfinyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylsulfenyl group, a C2-C6 alkynylsulfinyl group, a C2-C6 alkynylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, a C2-C6 haloalkenylsulfenyl group, a C2-C6 haloalkenylsulfinyl group, a C2-C6 haloalkenylsulfonyl group, a C2-C6 haloalkynylsulfenyl group, a C2-C6 haloalkynylsulfinyl group, a C2-C6 haloallynylsulfonyl group, NO2, CN, —NU1U2, a phenoxy group, OH, a naphthyl group, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C4 alkylcarbonyl group, a C2-C5 alkylcarbonyloxy group, a C2-C5 haloalkylcarbonyloxy group, a benzoyl group optionally substituted by X, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, and —N═CT7T8, provided that when the substituent is two or more, then said substituents may be the same or different, and the number of the substituient, R, is 1, 2, 3 or 4, or R is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;
- Y is a substituent selected from the group consisting of a halogen atom, a C1-C10 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C4 haloalkoxy group, a C2-C6 haloalkenyloxy group, a C2-C6 haloalkynyloxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C6 alkenylsulfenyl group, a C2-C6 alkenylsulfinyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylsulfenyl group, a C2-C6 alkynylsulfinyl group, a C2-C6 alkynylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, a C2-C6 haloalkenylsulfenyl group, a C2-C6 haloalkenylsulfinyl group, a C2-C6 haloalkenylsulfonyl group, a C2-C6 haloalkynylsulfenyl group, a C2-C6 haloalkynylsulfinyl group, a C2-C6 haloalkynylsulfonyl group, NO2, CN, —NU1U2, OH, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C5 alkylcarbonyloxy group, a C2-C5 haloalkylcarbonyloxy group, a C3-C7 dialkylaminocarbonyloxy group, a phenyl group optionally substituted by X, and —N═CT7T8, provided that when the substituent is two or more, then said substituents may be the same or different, and the number of the substituent, Y, is 1, 2, 3 or 4, or Y is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;
- W is a substituent selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkenyloxy group, a C2-C4 haloalkenyloxy group, a C2-C4 alkenylsulfenyl group, a C2-C4 alkenylsulfinyl group, a C2-C4 alkenylsulfonyl group, a C2-C4 haloalkenylsulfenyl group, a C2-C4 haloalkenylsulfinyl group, a C2-C4 haloalkenylsulfonyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C2-C4 alkynyloxy group, a C2-C4 haloalkynyloxy group, a C2-C4 alkynylsulfenyl group, a C2-C4 alkynylsulfinyl group, a C2-C4 alkynylsulfonyl group, a C2-C4 haloalkynylsulfenyl group, a C2-C4 haloalkynylsulfinyl group, a C2-C4 haloalkynylsulfonyl group, NO2, CN, a formyl group, a C2-C6 alkoxycarbonyl group, a C2-C6 alkylcarbonyl group, a C2-C6 haloalkylcarbonyl group, a C2-C6 alkylcarbonyloxy group, and —NU1U2, provided that when the substituent is two or more, then said substituents may be the same or different, and the number of the substituent, W, is 1, 2, 3 or 4;
- T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C6 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C3-C6 halocycloalkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group and a C1-C4 alkyl group, a C3-C4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen or a C1-C4 alkoxy group and a halogen, a cyclopropyl group substituted by both a C2-C4 alkenyl group optionally substituted by a halogen and a C1-C4 alkyl group, a C2-C4 alkenyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a C2-C5 alkenyloxy group, a C3-C6 cycloalkoxy group optionally substituted by a C1-C3 alkyl group, a benzyloxy group, a C2-C5 alkoxycarbonyl group, —NU1U2, a phenylamino group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a phenylthio group optionally substituted by Z, a naphthyl group optionally substituted by Z, or a 5-membered or 6-membered heterocyclic group optionally substituted by Z wherein said heterocyclic group is selected from the group consisting of a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, and 3(2H)-pyridazinone groups;
- T2 and T3 each independently represent OH, a phenyl, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C4 alkylsulfenyl group;
- T4, T5 and T6 each independently represent H, a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, or a benzyl group;
- or any two of T4, T5 and T6 may form , together with the nitrogen atom to which they are bonded, a 5-, 6-, 7- or 8-membered cyclic group optionally containing oxygen, nitrogen and/or sulfur atoms;
- X and Z are independently substituents selected from the group consisting of a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C5 alkenylsulfenyl group, a C2-C5 alkenylsulfinyl group, a C2-C5 alkenylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, NO2, CN, CHO, OH, —NU1U2, a phenyl group, a phenoxy group, and a C2-C5 alkoxycarbonyl group, provided that when the substituent is two or more, then said substituents may be the same or different, and the number of the substituent, X and Z,is 1,2,3, 4or 5 each;
- T7 and T8 each independently represent H, or a phenyl, benzyl, or a C1-C6 alkyl group, or T7 and T8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7-, or 8-membered ring;
- U1 and U2 each independently represent H, a C1-C6 alkyl, a C2-C6 alkylcarbonyl, phenyl or benzyl group, or U1 and U2 may, together with the nitrogen atom to which they are bonded, form a 5-, 6-, 7-, or 8-membered ring.
A compound as claimed in claim , wherein R is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C3 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, NO2, CN, —NU1U2, a naphthyl group, a C2-C4 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a phenyl group optionally substituted by X, and a pyridyl group optionally substituted by X, provided that when the substituent is two or more, then said substituents may be the same or different, and the number of the substituent, R, is 1, 2 or 3.
Dependencies are inferred from the claim text.