JPH08225548A - Herbicidal isoxazoline derivative - Google Patents

Abstract

PURPOSE: To provide a new isoxazoline derivative having excellent herbicidal activity and especially effective against echinochloa (a harmful weed in paddy field) at a low rate of application. CONSTITUTION: This compound is expressed by formula I (R<1> is a lower alkyl replaced with 1-3 halogen atoms; R<2> is a lower alkyl; R<3> and R<4> are each H or a lower alkyl; R<5> is a halogen, a lower alkyl, a lower alkoxy, etc.; (m) is 0, 1, 2, 3, 4 or 5; (n) is 0, 1 or 2), e.g. 3-benzylthio-5-chloromethyl-5-methyl-2- isoxazoline. The compound of formula I wherein n=0 can be produced e.g. by reacting a compound of formula II with a compound of formula III (X<1> is a halogen) and reacting the reaction product with a mercaptan compound.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel isoxazoline derivative having excellent herbicidal activity and a herbicide containing the same as an active ingredient.

[0002]

2. Description of the Related Art Up to now, a compound having a 2-isoxazoline skeleton having herbicidal activity has been disclosed in EP334120A.
1 and EP 514987A1.

However, the compound described in EP334120A1 is a compound in which an alkyl, cycloalkyl, substituted phenyl, 5-membered and 6-membered heterocycle is directly bonded to the 2-isoxazoline ring 3-position, and the 2-isoxazoline ring 3-position. The structure is completely different from the compound of the present invention in which is (substituted) methylene sulfide, (substituted) methylene sulfoxide, or (substituted) methylene sulfone. Moreover, the compound described in EP514987A1 is only a compound in which a substituted phenyl group is directly bonded to the 2-position of the 2-isoxazoline ring, and the structure of the compound of the present application is completely different.

Further, a compound having a 2-isoxazoline ring is described in JP-A-5-105672, but all of these compounds are compounds in which a cyano group is directly bonded to the 5-position of the isoxazoline ring. It is completely different in structure from the compound of the present invention. Further, the Japanese Patent Laid-Open No. 5-1056
No. 72, there is no description of herbicidal activity.

[0005]

DISCLOSURE OF INVENTION Problems to be Solved by the Invention As a result of years of intensive research on the synthesis of a derivative having a 2-isoxazoline ring and its biological activity, the present inventors have found that the structure differs from that of a known compound. The present inventors have found that the novel 2-isoxazoline derivative has excellent herbicidal activity, and completed the present invention.

In the paddy field, the compound of the present invention exhibits excellent herbicidal activity at a low dose, especially against Tainubie, which is a highly damaging weed in the paddy field, and has very little phytotoxicity to paddy rice, and also konagi, azena, It also has a strong herbicidal action against broad-leaved weeds such as aphids and yellow sedges, and Cyperaceae weeds such as fireflies and cyperus.

[0007] Furthermore, even in the field, it exhibits excellent herbicidal activity against grass weeds such as crabgrass, barnyard grass, and green foxtail at a low dose, and has very little phytotoxicity against corn, beet, soybean, and cotton. It also has a strong herbicidal action against broad-leaved weeds such as Inubiyu, Akaza, mustard and Aogate.

[0008]

Configuration of the Invention

[0009]

The present invention has the following general formula (I):

[0010]

[Chemical 6]

[Wherein R ¹ represents a lower alkyl group substituted by the same or different 1 to 3 halogen atoms, R ² represents a lower alkyl group, R ³ and R ⁴ are the same or Differently, a hydrogen atom or a lower alkyl group is shown, and R ⁵ is a halogen atom, a lower alkyl group (the lower alkyl group is substituted with the same or different 1 to 3 substituents selected from the substituent group a). Or a lower alkoxy group (the lower alkoxy group may be substituted with the same or different 1 to 3 substituents selected from the substituent group a, and the lower alkoxy group adjacent thereto may be substituted. May combine with each other to form a lower alkylenedioxy group, and the lower alkylenedioxy group may be substituted with the same or different 1 to 4 halogen atoms). Alternatively, R ⁴ and R ⁵ may combine to form a lower alkylene group or a lower alkyleneoxy group (when m is 2 or more, R ⁵ may be the same or different), and m is 0, 1, 2, 3, 4 or 5 is shown, and n is 0, 1 or 2.

(Substituent group a) halogen atom, lower alcohol
Xy group (the lower alkoxy group is the same or different)
It may be substituted with up to 3 halogen atoms,
In addition, two adjacent lower alkoxy groups are bonded to form a lower
An alkylenedioxy group may be formed)]
[Wherein, R¹ Is 1 to 3 halogens which are the same or different.
Alkyl substituted by 1 to 2 carbon atoms
Group, R² Is an alkyl group having 1 or 2 carbon atoms
Show, R³ And R^Four Are the same or different and are hydrogen atoms or
Represents an alkyl group having 1 to 3 carbon atoms, R^Five Is halo
Gen atom, alkyl group having 1 to 3 carbon atoms or carbon number
1 to 3 alkoxy groups (the adjacent alkoxy groups
Are bonded to each other to form an alkylenedioxy having 1 or 2 carbon atoms.
A group may be formed) (when m is 2, R is^Five Is the same
1 or different), m is 0, 1 or 2.
However, n represents 0 or 2. ] More preferably, in the formula, R
¹ Is the number of carbon atoms substituted by 1 to 3 chlorine atoms
Represents one or two alkyl groups, R² Is a methyl group
Show, R³ And R^Four Are the same or different and are hydrogen atoms or
R represents a methyl group^Five Is a fluorine atom, chlorine atom, bromine source
Child, methyl group, ethyl group, isopropyl group, methoxy
Group, ethoxy group, isopropyloxy group (approx.
Two methoxy and ethoxy groups are bonded to form a methylene dioxy group.
Group may form an ethylenedioxy group)
(If m is 2, R^Five Can be the same or different
I), m is 0, 1 or 2, and n is 0 or 2.
You ] More preferably, in the formula, R¹ Is a chloromethyl group
Indicates R² Represents a methyl group, R³ And R^Four Is water
Indicates elementary atom, R^Five Is a fluorine atom, chlorine atom, methyl
Group, ethyl group, methoxy group, ethoxy group (approx.
Two methoxy and ethoxy groups are bonded to form a methylene dioxy group.
Group may form an ethylenedioxy group)
(If m is 2, R^Five Can be the same or different
I), m is 1 or 2, and n is 2. ] Further
Preferably, [wherein R¹ Represents a chloromethyl group, R
² Represents a methyl group, R³ And R ^Four Indicates a hydrogen atom
Then R^Five Is a chlorine atom, ethyl group, methoxy group (close
Two methoxy groups are bound to form a methylenedioxy group.
May be formed) (when m is 2, R^Five Is the same or
May be different), m is 1 or 2, and n is 2
Is shown. ] It is a compound represented by.

In the present application, the "halogen atom" is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. R ¹ is preferably a fluorine atom or a chlorine atom, and more preferably a chlorine atom.

R ⁵ is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a fluorine atom or a chlorine atom, and when R ⁵ forms a lower alkylenedioxy group, it is preferable. Is a fluorine atom. In the substituent group a, it is preferably a fluorine atom, and when the substituent group a is a lower alkoxy group, it is preferably a fluorine atom.

In the present application, the "lower alkyl group" means
For example, methyl, ethyl, n-propyl, isopropyl, n-
Butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-
Ethylpropyl, n-hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl,
3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
Carbon number 1 such as 2,3-dimethylbutyl and 2-ethylbutyl
To 6 straight or branched chain alkyl groups. R ¹ and R ² are preferably methyl and ethyl, and more preferably methyl. R ³ and R ⁴ are preferably linear or branched alkyl groups having 1 to 3 carbon atoms,
More preferably, it is methyl. R ⁵ is preferably methyl, ethyl or isopropyl, and most preferably methyl or ethyl.

In the present application, the "lower alkoxy group" means, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-.
Butoxy, n-pentyloxy, isopentyloxy, 2-
Methyl butoxy, neopentyloxy, 1-ethylpropoxy, n-hexyloxy, 4-methylpentyloxy, 3-
Methylpentyloxy, 2-methylpentyloxy, 1-methylpentyloxy, 3,3-dimethylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy A straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, such as 2,3-dimethylbutoxy and 2-ethylbutoxy. R ⁵ is preferably a linear or branched alkoxy group having 1 to 4 carbon atoms, and most preferably methoxy or ethoxy. In the substituent group a, methoxy and ethoxy are preferable, and ethoxy is more preferable.

In the present application, the "lower alkylene group" means, for example, methylene, ethylene, propylene, tetramethylene, pentamethylene, hexamethylene, methylmethylene, ethylmethylene, dimethylmethylene, n-propylmethylene, isopropylmethylene, methylethylmethylene. , N-butylmethylene, isobutylmethylene, s-butylmethylene, methyl n-propylmethylene, methylisopropylmethylene, diethylmethylene, n-pentylmethylene, isopentylmethylene, 2-methylbutylmethylene,
1 to 6 carbon atoms such as neopentylmethylene, 1-ethylpropylmethylene, methyl n-butylmethylene, methylisobutylmethylene, methyl s-butylmethylene, methyl t-butylmethylene, ethyl n-propylmethylene and ethylisopropylmethylene Is a straight chain or branched chain alkylene group. When R ⁴ and R ⁵ are taken together, it is preferably a straight chain or branched chain alkylene group having 2 to 3 carbon atoms.

In the present application, the "lower alkyleneoxy group" means, for example, methyleneoxy, ethyleneoxy, propyleneoxy, tetramethyleneoxy, pentamethyleneoxy, hexamethyleneoxy, methylmethyleneoxy, ethylmethyleneoxy, dimethylmethyleneoxy,
n-propylmethyleneoxy, isopropylmethyleneoxy, methylethylmethyleneoxy, n-butylmethyleneoxy, isobutylmethyleneoxy, s-butylmethyleneoxy, methyl n-propylmethyleneoxy, methylisopropylmethyleneoxy, diethylmethyleneoxy, n-pentyl Methyleneoxy, isopentylmethyleneoxy,
2-methylbutylmethyleneoxy, neopentylmethyleneoxy, 1-ethylpropylmethyleneoxy, methyl n-butylmethyleneoxy, methylisobutylmethyleneoxy, methyl s-butylmethyleneoxy, methyl t-butylmethyleneoxy, ethyl n-propylmethyleneoxy 1 to 6 carbon atoms such as oxy and ethyl isopropyl methylene oxy
Is a straight or branched chain alkyleneoxy group. When R ⁴ and R ⁵ are taken together, it is preferably a straight chain or branched chain alkyleneoxy group having 2 to 3 carbon atoms, and more preferably ethyleneoxy.

In the present application, the "lower alkylenedioxy group" means, for example, methylenedioxy, ethylenedioxy, propylenedioxy, tetramethylenedioxy, pentamethylenedioxy, hexamethylenedioxy, methylmethylenedioxy, ethyl. Methylenedioxy, dimethylmethylenedioxy, n-propylmethylenedioxy, isopropylmethylenedioxy, methylethylmethylenedioxy, n-butylmethylenedioxy, isobutylmethylenedioxy, s-butylmethylenedioxy, methyl n-propyl Methylenedioxy, methylisopropylmethylenedioxy, diethylmethylenedioxy, n-pentylmethylenedioxy, isopentylmethylenedioxy, 2-methylbutylmethylenedioxy, neopentylmethylenedioxy, 1-ethylpropylmehoxy Carbon such as dioxy, methyl n-butyl methylene dioxy, methyl isobutyl methylene dioxy, methyl s-butyl methylene dioxy, methyl t-butyl methylene dioxy, ethyl n-propyl methylene dioxy, ethyl isopropyl methylene dioxy It is a linear or branched alkylenedioxy group of the number 1 to 6. R ⁵ and the substituent group a preferably have 1 carbon atom.
To 3 linear or branched alkylenedioxy groups, more preferably methylenedioxy and ethylenedioxy.

In R ¹ , "a lower alkyl group substituted by the same or different 1 to 3 halogen atoms"
With, for example, chloromethyl, 2-chloroethyl, dichloromethyl, trichloromethyl, bromomethyl, 2-bromoethyl, dibromomethyl, fluoromethyl, 2-fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-
Halogen atom-substituted lower alkyl groups such as trifluoroethyl, perfluoroethyl, and perfluoropropyl are preferable, and chloromethyl and difluoromethyl are preferable, and chloromethyl is more preferable.

The “lower alkylenedioxy group substituted by 1 to 4 halogen atoms which are the same or different” in R ⁵ is a group such as fluoromethylenedioxy and difluoromethylenedioxy.

In the substituent group a, the "lower alkoxy group substituted by the same or different 1 to 3 halogen atoms" is a group such as difluoromethoxy and trifluoromethoxy.

In the general formula (I), R ¹ is preferably an alkyl group having 1 or 2 carbon atoms, which is substituted with the same or different 1 to 3 halogen atoms.
More preferred is an alkyl group having 1 or 2 carbon atoms substituted by 1 to 3 chlorine atoms, and most preferred is a chloromethyl group.

In the general formula (I), R ² is preferably an alkyl group having 1 or 2 carbon atoms, and most preferably a methyl group.

In the general formula (I), R ³ is preferably a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, and more preferably a hydrogen atom or a methyl group. And most preferably a hydrogen atom.

In the general formula (I), R ⁴ is preferably a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, and more preferably a hydrogen atom or a methyl group. And most preferably a hydrogen atom.

In the general formula (I), R ⁵ is preferably a halogen atom, an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, and when m is 2 or more, Adjacent R ⁵ may be taken together to form an alkylenedioxy group having 1 or 2 carbon atoms, and more preferably,
Fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group,
It is an isopropyl group, a methoxy group, an ethoxy group or an isopropyloxy group, and when m is 2 or more, adjacent R ^{5 s} may be combined to be a methylenedioxy group or an ethylenedioxy group, and more preferably Is a fluorine atom, a chlorine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, and when m is 2 or more, adjacent R ^5's are taken together,
It may be a methylenedioxy group or an ethylenedioxy group, and more preferably a chlorine atom, an ethyl group or a methoxy group, and when m is 2 or more, adjacent R ⁵ are taken together to form a methylene group. It may be a dioxy group.

In the general formula (I), m is preferably
0, 1 or 2, most preferably 1 or 2.

In the general formula (I), n is preferably
It is 0 or 2, and most preferably 2.

Substituent group a is preferably a halogen atom or an alkoxy group having 1 or 2 carbon atoms, more preferably a fluorine atom, a methoxy group or an ethoxy group, and most preferably It is a fluorine atom.

Representative compounds of the present invention are shown in Table 1 below, but the present invention is not limited to these compounds.

In the table, "No." indicates the compound number, M
e is a methyl group, Et is an ethyl group, nPr is an n-propyl group, iPr is an isopropyl group, nBu is an n-butyl group, iBu is an isobutyl group, and sBu is sec-.
A butyl group, tBu a tert-butyl group, nPen
Represents an n-pentyl group, Ph represents a phenyl group, Bn represents a benzyl group, and Ac represents an acetyl group.

In the (R ⁵ ) _m column, the number before the substituent indicates the substitution position in the phenyl group of the substituent, and the subscript number after the substituent indicates the number of substitutions of the substituent. . For example, 2-CF ₃ is a trifluoromethyl group substituted at the 2-position, 2,4-Cl ₂ is a 2,4-dichloro group, 3,4-OCH ₂ CH ₂ O
-Is a 3,4-ethylenedioxy group.

[0034]

[Chemical 7]

[0035]

[Table 1] ──────────────────────────────────── No. R ¹ R ² R ³ R ⁴ (R ⁵ ) _m n ──────────────────────────────────── 1 CH ₂ Cl Me HH m = 0 0 2 CH ₂ Cl Me HH 2-Me 0 3 CH ₂ Cl Me HH 3-Me 0 4 CH ₂ Cl Me HH 4-Me 0 5 CH ₂ Cl Me HH 2,3-Me ₂ 0 6 CH ₂ Cl Me HH 2,4-Me ₂ 0 7 CH ₂ Cl Me HH 2,5-Me ₂ 0 8 CH ₂ Cl Me HH 2,6-Me ₂ 0 9 CH ₂ Cl Me HH 3,4-Me ₂ 0 10 CH ₂ Cl Me HH 3,5-Me ₂ 0 11 CH ₂ Cl Me HH 2,4,6-Me ₃ 0 12 CH ₂ Cl Me HH 2-Et 0 13 CH ₂ Cl Me HH 3-Et 0 14 CH ₂ Cl Me HH 4-Et 0 15 CH ₂ Cl Me HH 2,6-Et ₂ 0 16 CH ₂ Cl Me HH 2-Me, 6-Et 0 17 CH ₂ Cl Me HH 2-nPr 0 18 CH ₂ Cl Me HH 3- nPr 0 19 CH ₂ Cl Me HH 4-nPr 0 20 CH ₂ Cl Me HH 2-iPr 0 21 CH ₂ Cl Me HH 3-iPr 0 22 CH ₂ Cl Me HH 4-iPr 0 23 CH ₂ Cl Me HH 2- iBu 0 24 CH ₂ Cl Me HH 3-iBu 0 25 CH ₂ Cl Me HH 4-iBu 0 26 CH ₂ Cl Me HH 2-sBu 0 27 CH ₂ Cl Me HH 3-sBu 0 28 CH ₂ Cl Me HH 4- sBu 0 29 CH ₂ Cl Me HH 2-tBu 0 _{30 CH 2 Cl Me HH 3-} tBu 0 31 CH 2 Cl Me HH 4-tBu 0 32 CH 2 Cl Me HH 2-nPen 0 33 CH 2 Cl Me HH 3,4-CH 2 CH 2 CH 2 CH 2 - 0 34 CH ₂ Cl Me HH 2-Cl 0 35 CH ₂ Cl Me HH 3-Cl 0 36 CH ₂ Cl Me HH 4-Cl 0 37 CH ₂ Cl Me HH 2,3-Cl ₂ 0 38 CH ₂ Cl Me HH 2 , 4-Cl ₂ 0 39 CH ₂ Cl Me HH 2,5-Cl ₂ 0 40 CH ₂ Cl Me HH 2,6-Cl ₂ 0 41 CH ₂ Cl Me HH 3,4-Cl ₂ 0 42 CH ₂ Cl Me HH 3,5-Cl ₂ 0 43 CH ₂ Cl Me HH 2,3,5-Cl ₃ 0 44 CH ₂ Cl Me HH 2,4,6-Cl ₃ 0 45 CH ₂ Cl Me HH 3-Cl, 4- Me 0 46 CH ₂ Cl Me HH 3-Me, 4-Cl 0 47 CH ₂ Cl Me HH 2-Me, 3,4-Cl ₂ 0 48 CH ₂ Cl Me HH 2,4-Cl ₂ , 3-Me 0 49 CH ₂ Cl Me HH 2,5-Cl ₂ , 4-Me 0 50 CH ₂ Cl Me HH 2-Br 0 51 CH ₂ Cl Me HH 3-Br 0 52 CH ₂ Cl Me HH 4-Br 0 53 CH ₂ Cl Me HH 2-F 0 54 CH ₂ Cl Me HH 3-F 0 55 CH ₂ Cl Me HH 4-F 0 56 CH ₂ Cl Me HH 2,3-F ₂ 0 57 CH ₂ Cl Me HH 2,4- F ₂ 0 58 CH ₂ Cl Me HH 2,5-F ₂ 0 59 CH ₂ Cl Me HH 2,6-F ₂ 0 60 CH ₂ Cl Me HH 3,4-F ₂ 0 61 CH ₂ Cl Me HH 3, _{5-F 2 0 62 CH 2} Cl Me HH 2,4,6-F 3 0 63 CH 2 Cl Me HH 2,3,4,5,6-F 5 0 64 CH 2 Cl Me HH 2-F, 3 -Me 0 65 CH ₂ Cl Me HH 3-F, 4-Me 0 66 CH ₂ Cl Me HH 2,3,5,6-F ₄ , 4-Me 0 67 CH ₂ Cl Me HH 2-F, 3-Cl 0 68 CH ₂ Cl Me HH 2-Cl, 4-F 0 69 CH ₂ Cl Me HH 2-F, 4-Cl 0 70 CH ₂ Cl Me HH 2-Cl, 6-F 0 71 CH ₂ Cl Me HH 2-CF ₃ 0 72 CH ₂ Cl Me HH 3-CF ₃ 0 73 CH ₂ Cl Me HH 4-CF ₃ 0 74 CH ₂ Cl Me HH 2,4- (CF ₃ ) ₂ 0 75 CH ₂ Cl Me HH 3,5- (CF ₃ ) ₂ 0 76 CH ₂ Cl Me HH 2- F, 4-CF ₃ 0 77 CH ₂ Cl Me HH 2-OMe 0 78 CH ₂ Cl Me HH 3-OMe 0 79 CH ₂ Cl Me HH 4-OMe 0 80 CH ₂ Cl Me HH 2,3- (OMe) ₂ 0 81 CH ₂ Cl Me HH 2,4- (OMe) ₂ 0 82 CH ₂ Cl Me HH 2,5- (OMe) ₂ 0 83 CH ₂ Cl Me HH 2,6- (OMe) ₂₀ 84 CH ₂ Cl Me HH 3,4- (OMe) ₂₀ 85 CH ₂ Cl Me HH 3,5- (OMe) ₂₀ 86 CH ₂ Cl Me HH 2,4,6- (OMe) ₃₀ 87 CH ₂ Cl Me HH 3,4,5- (OMe) ₃ 0 88 CH ₂ Cl Me HH 2-OEt 0 89 CH ₂ Cl Me HH 3-OEt 0 90 CH ₂ Cl Me HH 4-OEt 0 91 CH ₂ Cl Me HH 2,6 -(OEt) ₂ 0 92 CH ₂ Cl Me HH 2-OiPr 0 93 CH ₂ Cl Me HH 3-OiPr 0 94 CH ₂ Cl Me HH 4-OiPr 0 95 CH ₂ Cl Me HH 2-OMe, 3-Me 0 96 CH ₂ Cl Me HH 2-Me, 6-OMe 0 97 CH ₂ Cl Me HH 3-Me, 4-OMe 0 98 CH ₂ Cl Me HH 3-OMe, 4-Me 0 99 CH ₂ Cl Me HH 2- OEt, 3-Me 0 100 CH ₂ Cl Me HH 2-OiPr, 3-Me 0 101 CH ₂ Cl Me HH 2-OMe, 3-Cl 0 102 CH ₂ Cl Me HH 2-OMe, 4-Cl 0 103 CH ₂ Cl Me HH 2-Cl, 5-OMe 0 104 CH ₂ Cl Me HH 2-OMe, 5-Cl 0 105 CH ₂ Cl Me HH 3-OMe, 4-Cl 0 106 CH ₂ Cl Me HH 2-OMe, 3,5-Cl ₂ 0 107 CH ₂ Cl Me HH 2,6- (OMe) ₂ , 3-Cl 0 108 CH ₂ Cl Me HH 2-Cl, 3,4- (OMe) ₂ 0 109 CH ₂ Cl Me HH 3,5-Cl ₂ , 4-OMe 0 110 CH ₂ Cl Me HH 2-OEt, 3-Cl 0 111 CH ₂ Cl Me HH 2-OEt, 4-Cl 0 112 CH ₂ Cl Me HH 2-Cl, 5-OEt 0 113 CH ₂ Cl Me HH 2 -OEt, 5-Cl 0 114 CH ₂ Cl Me HH 3-OEt, 4-Cl 0 115 CH ₂ Cl Me HH 2-OEt, 3,5-Cl ₂ 0 116 CH ₂ Cl Me HH 2-OiPr, 4- Cl 0 117 CH ₂ Cl Me HH 2-Cl, 5-OiPr 0 118 CH ₂ Cl Me HH 2-OiPr, 5-Cl 0 119 CH ₂ Cl Me HH 3-OiPr, 4-Cl 0 120 CH ₂ Cl Me HH 2-F, 6-OMe 0 121 CH ₂ Cl Me HH 2-OEt, 3-OMe 0 122 CH ₂ Cl Me HH 2-OEt, 6-OMe 0 123 CH ₂ Cl Me HH 2-OnPr, 3-OMe 0 124 CH ₂ Cl Me HH 2-OiPr, 3-OMe 0 125 CH ₂ Cl Me HH 2,3-OCH ₂ O- 0 126 CH ₂ Cl Me HH 3,4-OCH ₂ O- 0 127 CH ₂ Cl Me HH 2,3-OCH ₂ CH ₂ O- 0 128 CH ₂ Cl Me HH 3,4-OCH ₂ CH ₂ O- 0 129 CH ₂ Cl Me HH 2,3-OCH ₂ CH ₂ CH ₂ O- 0 130 CH ₂ Cl Me HH 3 , 4-OCH ₂ CH ₂ CH ₂ O- 0 131 CH ₂ Cl Me HH 2-Me, 3,4-OCH ₂ CH ₂ O- 0 132 CH ₂ Cl Me HH 2,3-OCHFO- 0 133 CH ₂ Cl Me HH 3,4-OCHFO- 0 134 CH ₂ Cl Me HH 2,3-OCF ₂ O- 0 135 CH ₂ Cl Me HH 3,4-OCF ₂ O- 0 136 CH ₂ Cl Me HH 2,3-OCH (Me) O- 0 137 CH ₂ Cl Me HH 3,4-OCH (Me) O- 0 138 CH ₂ Cl Me HH 2,3-OC (Me) ₂ O- 0 139 CH ₂ Cl Me HH 3,4 -OC (Me) ₂ O- 0 140 CH ₂ Cl Me HH 2,3-OCH (Et) O- 0 141 CH ₂ Cl Me HH 3,4-OCH (Et) O- 0 142 CH ₂ Cl Me HH 4 -OCF ₃ 0 143 CH ₂ Cl Me HH 2-OCHF ₂ , 3-Me 0 144 CH ₂ Cl Me HH 2-OCHF ₂ , 4-Me 0 145 CH ₂ Cl Me HH 2-OCHF ₂ , 5-Me 0 146 CH ₂ Cl Me HH 3-OCHF ₂ , 4-Me 0 147 CH ₂ Cl Me HH 2-OCHF ₂ , 3-Cl 0 148 CH ₂ Cl Me HH 2-Cl, 5-OCHF ₂ 0 149 CH ₂ Cl Me HH 2-OCHF ₂ , 5-Cl 0 150 CH ₂ Cl Me HH 3-OCHF ₂ , 4-Cl 0 151 CH ₂ Cl Me HH 2-CH ₂ OMe 0 152 CH ₂ Cl Me HH 2-CH ₂ OEt 0 153 CH ₂ Cl Me HH 2-CH ₂ OCH ₂ CF ₃ 0 154 CH ₂ Cl Me HH 3-CH ₂ OCH ₂ CF ₃ 0 155 CH ₂ Cl Me HH 2-OCH ₂ CH ₂ OMe 0 156 CH ₂ Cl Me HH 3- OCH ₂ CH ₂ OMe 0 157 CH ₂ Cl Me HH 2-OCH ₂ CH (OMe) ₂ 0 158 CH ₂ Cl Me HH 3-OCH ₂ CH (OMe) ₂ 0 15 9 CH ₂ Cl Me HH 2-OCH ₂ CH (-OCH ₂ CH ₂ O-) 0 160 CH ₂ Cl Me HH 3-OCH ₂ CH (-OCH ₂ CH ₂ O-) 0 161 CH ₂ Cl Me Me H m = 0 0 162 CH ₂ Cl Me Me Me m = 0 0 163 CH ₂ Cl Me Et H m = 0 0 164 CH ₂ Cl Me Et Et m = 0 0 165 CH ₂ Cl Me iPr H m = 0 0 166 CH ₂ Cl Me Me H 2-Me 0 167 CH 2 Cl Me H α, 2-CH 2 CH 2 O- 0 168 CH 2 Cl Me H α, 2-CH 2 CH 2 - 0 169 CH 2 Cl Me H α, 2 _{-CH 2 CH 2 CH 2 - 0} 170 CH 2 CH 2 Cl Me HH m = 0 0 171 CHCl 2 Me HH m = 0 0 172 CCl 3 Me HH m = 0 0 173 CH 2 Br Me HH m = 0 0 174 CH ₂ CH ₂ Br Me HH m = 0 0 175 CHBr ₂ Me HH m = 0 0 176 CH ₂ F Me HH m = 0 0 177 CH ₂ CH ₂ F Me HH m = 0 0 178 CHF ₂ Me HH m = 0 0 179 CF ₃ Me HH m = 0 0 180 CH ₂ CF ₃ Me HH m = 0 0 181 CH ₂ Cl Et HH m = 0 0 1001 CH ₂ Cl Me HH Ph 1 2001 CH ₂ Cl Me HH m = 0 2 2002 CH ₂ Cl Me HH 2-Me 2 2003 CH ₂ Cl Me HH 3-Me 2 2004 CH ₂ Cl Me HH 4-Me 2 2005 CH ₂ Cl Me HH 2,3-Me ₂ 2 2006 CH ₂ Cl Me HH 2, 4-Me ₂ 2 2007 CH ₂ Cl Me HH 2,5-Me ₂ 2 2008 CH ₂ Cl Me HH 2,6-Me ₂ 2 2009 CH ₂ Cl Me HH 3,4-Me ₂ 2 2010 CH ₂ Cl Me HH 3,5-Me ₂ 2 2011 CH ₂ Cl Me HH 2,4,6-Me ₃ 2 2 012 CH ₂ Cl Me HH 2-Et 2 2013 CH ₂ Cl Me HH 3-Et 2 2014 CH ₂ Cl Me HH 4-Et 2 2015 CH ₂ Cl Me HH 2,6-Et ₂ 2 2016 CH ₂ Cl Me HH 2 -Me, 6-Et 2 2017 CH ₂ Cl Me HH 2-nPr 2 2018 CH ₂ Cl Me HH 3-nPr 2 2019 CH ₂ Cl Me HH 4-nPr 2 2020 CH ₂ Cl Me HH 2-iPr 2 2021 CH ₂ Cl Me HH 3-iPr 2 2022 CH ₂ Cl Me HH 4-iPr 2 2023 CH ₂ Cl Me HH 2-iBu 2 2024 CH ₂ Cl Me HH 3-iBu 2 2025 CH ₂ Cl Me HH 4-iBu 2 2026 CH ₂ Cl Me HH 2-sBu 2 2027 CH ₂ Cl Me HH 3-sBu 2 2028 CH ₂ Cl Me HH 4-sBu 2 2029 CH ₂ Cl Me HH 2-tBu 2 2030 CH ₂ Cl Me HH 3-tBu 2 2031 CH ₂ Cl Me HH 4-tBu 2 2032 CH 2 Cl Me HH 2-nPen 2 2033 CH 2 Cl Me HH 3,4-CH 2 CH 2 CH 2 CH 2 - 2 2034 CH 2 Cl Me HH 2-Cl 2 2035 CH 2 Cl Me HH 3-Cl 2 2036 CH ₂ Cl Me HH 4-Cl 2 2037 CH ₂ Cl Me HH 2,3-Cl ₂ 2 2038 CH ₂ Cl Me HH 2,4-Cl ₂ 2 2039 CH ₂ Cl Me HH 2 , 5-Cl ₂ 2 2040 CH ₂ Cl Me HH 2,6-Cl ₂ 2 2041 CH ₂ Cl Me HH 3,4-Cl ₂ 2 2042 CH ₂ Cl Me HH 3,5-Cl ₂ 2 2043 CH ₂ Cl Me HH 2,3,5-Cl ₃ 2 2044 CH ₂ Cl Me HH 2,4,6-Cl ₃ 2 2045 CH ₂ Cl Me HH 3-Cl, 4-Me 2 2046 CH ₂ Cl Me HH 3-Me, 4 -Cl 2 2047 CH ₂ Cl Me HH 2-Me, 3,4-Cl ₂ 2 2048 CH ₂ Cl Me HH 2,4-Cl ₂ , 3-Me 2 2049 CH ₂ Cl Me HH 2,5-Cl ₂ , 4- Me 2 2050 CH ₂ Cl Me HH 2-Br 2 2051 CH ₂ Cl Me HH 3-Br 2 2052 CH ₂ Cl Me HH 4-Br 2 2053 CH ₂ Cl Me HH 2-F 2 2054 CH ₂ Cl Me HH 3- F 2 2055 CH ₂ Cl Me HH 4-F 2 2056 CH ₂ Cl Me HH 2,3-F ₂ 2 2057 CH ₂ Cl Me HH 2,4-F ₂ 2 2058 CH ₂ Cl Me HH 2,5-F ₂ 2 2059 CH ₂ Cl Me HH 2,6-F ₂ 2 2060 CH ₂ Cl Me HH 3,4-F ₂ 2 2061 CH ₂ Cl Me HH 3,5-F ₂ 2 2062 CH ₂ Cl Me HH 2,4, 6-F ₃ 2 2063 CH ₂ Cl Me HH 2,3,4,5,6-F ₅ 2 2064 CH ₂ Cl Me HH 2-F, 3-Me 2 2065 CH ₂ Cl Me HH 3-F, 4- Me 2 2066 CH ₂ Cl Me HH 2,3,5,6-F ₄ , 4-Me 2 2067 CH ₂ Cl Me HH 2-F, 3-Cl 2 2068 CH ₂ Cl Me HH 2-Cl, 4-F 2 2069 CH ₂ Cl Me HH 2-F, 4-Cl 2 2070 CH ₂ Cl Me HH 2-Cl, 6-F 2 2071 CH ₂ Cl Me HH 2-CF ₃ 2 2072 CH ₂ Cl Me HH 3-CF ₃ 2 2073 CH ₂ Cl Me HH 4-CF ₃ 2 2074 CH ₂ Cl Me HH 2,4- (CF ₃ ) ₂ 2 2075 CH ₂ Cl Me HH 3,5- (CF ₃ ) ₂ 2 2076 CH ₂ Cl Me HH 2-F, 4-CF ₃ 2 2077 CH ₂ Cl Me HH 2-OMe 2 2078 CH ₂ Cl Me HH 3-OMe 2 2079 CH ₂ Cl Me HH 4-OMe 2 2080 CH ₂ Cl Me HH 2,3- (OMe) ₂ 2 2081 CH ₂ Cl Me HH 2,4- (OMe) ₂ 2 2082 CH ₂ Cl Me HH 2,5- (OMe) ₂ 2 2083 CH ₂ Cl Me HH 2,6 -(OMe) ₂ 2 2084 CH ₂ Cl Me HH 3,4- (OMe) ₂ 2 2085 CH ₂ Cl Me HH 3,5- (OMe) ₂ 2 2086 CH ₂ Cl Me HH 2,4,6- (OMe ) ₃ 2 2087 CH ₂ Cl Me HH 3,4,5- (OMe) ₃ 2 2088 CH ₂ Cl Me HH 2-OEt 2 2090 CH ₂ Cl Me HH 4-OEt 2 2091 CH ₂ Cl Me HH 2,6- (OEt) ₂ 2 2092 CH ₂ Cl Me HH 2-OiPr 2 2093 CH ₂ Cl Me HH 3-OiPr 2 2094 CH ₂ Cl Me HH 4-OiPr 2 2095 CH ₂ Cl Me HH 2-OMe, 3-Me 2 2096 CH ₂ Cl Me HH 2-Me, 6-OMe 2 2097 CH ₂ Cl Me HH 3-Me, 4-OMe 2 2098 CH ₂ Cl Me HH 3-OMe, 4-Me 2 2099 CH ₂ Cl Me HH 2-OEt , 3-Me 2 2100 CH ₂ Cl Me HH 2-OiPr, 3-Me 2 2101 CH ₂ Cl Me HH 2-OMe, 3-Cl 2 2102 CH ₂ Cl Me HH 2-OMe, 4-Cl 2 2103 CH ₂ Cl Me HH 2-Cl, 5-OMe 2 2104 CH ₂ Cl Me HH 2-OMe, 5-Cl 2 2105 CH ₂ Cl Me HH 3-OMe, 4-Cl 2 2106 CH ₂ Cl Me HH 2-OMe, 3 , 5-Cl ₂ 2 2107 CH ₂ Cl Me HH 2,6- (OMe) ₂ , 3-Cl 2 2108 CH ₂ Cl Me HH 2-Cl, 3,4- (OMe) ₂ 2 2109 CH ₂ Cl Me HH 3,5-Cl ₂ , 4-OMe 2 2110 CH ₂ Cl Me HH 2-OEt, 3-Cl 2 2111 CH ₂ Cl Me HH 2-OEt, 4-Cl 2 2112 C H ₂ Cl Me HH 2-Cl, 5-OEt 2 2113 CH ₂ Cl Me HH 2-OEt, 5-Cl 2 2114 CH ₂ Cl Me HH 3-OEt, 4-Cl 2 2115 CH ₂ Cl Me HH 2-OEt , 3,5-Cl ₂ 2 2116 CH ₂ Cl Me HH 2-OiPr, 4-Cl 2 2117 CH ₂ Cl Me HH 2-Cl, 5-OiPr 2 2119 CH ₂ Cl Me HH 3-OiPr, 4-Cl 2 2120 CH ₂ Cl Me HH 2-F, 6-OMe 2 2121 CH ₂ Cl Me HH 2-OEt, 3-OMe 2 2122 CH ₂ Cl Me HH 2-OEt, 6-OMe 2 2123 CH ₂ Cl Me HH 2- OnPr, 3-OMe 2 2124 CH ₂ Cl Me HH 2-OiPr, 3-OMe 2 2125 CH ₂ Cl Me HH 2,3-OCH ₂ O- 2 2126 CH ₂ Cl Me HH 3,4-OCH ₂ O- 2 2127 CH ₂ Cl Me HH 2,3-OCH ₂ CH ₂ O- 2 2128 CH ₂ Cl Me HH 3,4-OCH ₂ CH ₂ O- 2 2129 CH ₂ Cl Me HH 2,3-OCH ₂ CH ₂ CH ₂ O- 2 2130 CH ₂ Cl Me HH 3,4-OCH ₂ CH ₂ CH ₂ O- 2 2131 CH ₂ Cl Me HH 2-Me, 3,4-OCH ₂ CH ₂ O- 2 2132 CH ₂ Cl Me HH 2 , 3-OCHFO- 2 2133 CH ₂ Cl Me HH 3,4-OCHFO- 2 2134 CH ₂ Cl Me HH 2,3-OCF ₂ O- 2 2135 CH ₂ Cl Me HH 3,4-OCF ₂ O- 2 2136 CH ₂ Cl Me HH 2,3-OCH (Me) O- 2 2137 CH ₂ Cl Me HH 3,4-OCH (Me) O- 2 2138 CH ₂ Cl Me HH 2,3-OC (Me) ₂ O- 2 2139 CH ₂ Cl Me HH 3,4-OC (Me) ₂ O- 2 2140 CH ₂ Cl Me HH 2,3-OCH (Et) O- 2 2141 CH ₂ Cl Me HH 3, 4-OCH (Et) O- 2 2142 CH ₂ Cl Me HH 4-OCF ₃ 2 2143 CH ₂ Cl Me HH 2-OCHF ₂ , 3-Me 2 2144 CH ₂ Cl Me HH 2-OCHF ₂ , 4-Me 2 2145 CH ₂ Cl Me HH 2-OCHF ₂ , 5-Me 2 2146 CH ₂ Cl Me HH 3-OCHF ₂ , 4-Me 2 2147 CH ₂ Cl Me HH 2-OCHF ₂ , 3-Cl 2 2148 CH ₂ Cl Me HH 2-Cl, 5-OCHF ₂ 2 2149 CH ₂ Cl Me HH 2-OCHF ₂ , 5-Cl 2 2150 CH ₂ Cl Me HH 3-OCHF ₂ , 4-Cl 2 2151 CH ₂ Cl Me HH 2-CH ₂ OMe 2 2152 CH ₂ Cl Me HH 2-CH ₂ OEt 2 2153 CH ₂ Cl Me HH 2-CH ₂ OCH ₂ CF ₃ 2 2154 CH ₂ Cl Me HH 3-CH ₂ OCH ₂ CF ₃ 2 2155 CH ₂ Cl Me HH 2-OCH ₂ CH ₂ OMe 2 2156 CH ₂ Cl Me HH 3-OCH ₂ CH ₂ OMe 2 2157 CH ₂ Cl Me HH 2-OCH ₂ CH (OMe) ₂ 2 2158 CH ₂ Cl Me HH 3-OCH ₂ CH ( OMe) ₂ 2 2159 CH ₂ Cl Me HH 2-OCH ₂ CH (-OCH ₂ CH ₂ O-) 2 2160 CH ₂ Cl Me HH 3-OCH ₂ CH (-OCH ₂ CH ₂ O-) 2 2161 CH ₂ Cl Me Me H m = 0 2 2162 CH ₂ Cl Me Me Me m = 0 2 2163 CH ₂ Cl Me Et H m = 0 2 2164 CH ₂ Cl Me Et Et m = 0 2 2165 CH ₂ Cl Me iPr H m = 0 _{2 2166 CH 2 Cl Me Me H} 2-Me 2 2167 CH 2 Cl Me H α, 2-CH 2 CH 2 O- 2 2168 CH 2 Cl Me H α, 2-CH 2 CH 2 - 2 2169 CH 2 Cl Me H α, 2-CH ₂ CH ₂ CH ₂ -2 2170 CH ₂ CH ₂ Cl Me HH m = 0 2 2171 CHCl ₂ Me HH m = 0 2 2172 CCl ₃ Me HH m = 0 2 2173 CH ₂ Br Me HH m = 0 2 2174 CH ₂ CH ₂ Br Me HH m = 0 2 2175 CHBr ₂ Me HH m = 0 2 2177 CH ₂ CH ₂ F Me HH m = 0 2 2178 CHF ₂ Me HH m = 0 2 2179 CF ₃ Me HH m = 0 2 2180 CH ₂ CF ₃ Me HH m = 0 2 2181 CH ₂ Cl Et HH m = 0 2 ───────────────────────────────────── Among the above-exemplified compounds, suitable ones are 2001, 2002,
2003,2005,2006,2007,2008,2009,2010,2011,2012,2020,
2035,2040,2051,2053,2054,2055,2056,2057,2058,2059,
2060,2061,2064,2068,2070,2071,2072,2077,2078,2080,
2082,2083,2088,2089,2092,2095,2097,2098,2099,2101,
2102,2104,2105,2107,2111,2113,2114,2120,2121,2125,
The compounds of 2126,2127,2143,2145,2151,2152,2161,2166 can be mentioned.

More preferred are 2002, 2005, 200
8,2012,2054,2071,2077,2088,2099,2102,2125,2127,216
There may be mentioned 6 compounds.

The most preferable one is 2012, 2102, 2125
Compounds of

[0038]

BEST MODE FOR CARRYING OUT THE INVENTION The isoxazoline derivative having the general formula (I) of the present invention can be produced by the method described below.

Process A

[0040]

Embedded image

During the above steps, R ¹ , R ² , R ³ , R ⁴ , R
⁵ and m have the same meaning as described above, and X ¹ represents a halogen atom. X ¹ is preferably a chlorine atom.

Step A is a method for producing a compound (Ia) in which n is 0 in the general formula (I).

Step A-1 is a step of producing a compound having the general formula (II) in which a halogen atom is substituted at the 3-position of the isoxazoline ring, and the compound having the general formula (III) is treated with a base in an inert solvent. This is achieved by reacting with a compound having general formula (IV) in the presence.

The compound (III) is, for example, a compound described in Tetrahedron, Vol. 49, page 4117, 1993 (Tetrahedron 49 , 4117 (1993)), and a commercially available compound is used or Wittig ( Witti
g) It is produced by a known method such as a reaction. Further, the compound (IV) can be obtained, for example, from Liebigs Annalen de Chemie, page 985, 1989 (Liebigs Annalen de
r Chemie 985 (1989)), which is a commercially available compound, or is produced according to the method described in the literature.

The base used in the step A-1 is not particularly limited as long as it is a base having a strength capable of generating a nitrile oxide from the compound (IV), but is preferably sodium hydrogen carbonate or potassium hydrogen carbonate. Such as alkali metal hydrogen carbonates; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; sodium carbonate and potassium carbonate Alkali metal carbonates; Alkali metal acetates such as sodium acetate and potassium acetate; Alkali metal fluorinated salts such as sodium fluoride and potassium fluoride; Tertiary lower alkyl amines such as triethylamine, ethyldiisopropylamine and tributylamine 1,8-diazabicyclo [5.4.0] undecane-7-ene DBU), 1,4-diazabicyclo [2.2.2] tertiary alicyclic amines such as octane (DABCO) can be exemplified.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethyl ether, dioxane, Ethers such as tetrahydrofuran; methylene chloride, chloroform, carbon tetrachloride,
Halogenated hydrocarbons such as dichloroethane; aromatic hydrocarbons such as benzene and toluene, ethyl acetate,
Examples thereof include acetic acid esters such as butyl acetate; nitriles such as acetonitrile; a mixed solvent of the above organic solvent and water; water.

The reaction temperature and reaction time are as follows:
The reaction temperature is usually 0 ° C. to 150 ° C., preferably 15 ° C. to 80 ° C., and the reaction time is generally 15 minutes to 24 hours, preferably 3 although it depends on the kind of the solvent and the base.
0 minutes to 8 hours.

Step A-2 is a step for producing a compound having the general formula (Ia), using a base in an inert solvent,
It is achieved by reacting the mercaptan compound having the general formula (V) with the compound having the general formula (II) prepared by the step A-1.

The compound (V) can be synthesized, for example, by Synthetic Communications, Vol. 16, No. 1173.
Page, 1986 (Synthetic Communications 16 , 1
173 (1986)) as a starting material, for example, Journal of American Chemical Society, Volume 62, page 2674, 1940 (Journal of American Chemical Societies).
ty 62 , 2674 (1940)).

The base to be used is not particularly limited as long as it is a base having a strength that preferentially desorbs the protons of thiols, but is preferably sodium hydride, potassium hydride or lithium hydride. Alkali metal hydrides such as;
Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide;
Alkali metal amides such as sodium amide, lithium isopropylamide; tertiary lower alkylamines such as triethylamine, ethyldiisopropylamine, tributylamine; 1,8-diazabicyclo [5.4.
0] undecane-7-ene (DBU); 1,4-diazabicyclo [2.2.2] octane (DABCO) such as tertiary alicyclic amines.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably ethers such as dioxane and tetrahydrofuran; methylene chloride, chloroform, Halogenated hydrocarbons such as carbon tetrachloride and dichloroethane; Aromatic hydrocarbons such as benzene and toluene;
Amides such as N, N-dimethylacetamide, N, N-dimethylformamide, N-methyl-2-pyrrolidinone; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, t-butanol; acetone , Ketones such as 2-butanone; nitriles such as acetonitrile;
Mention may be made of sulfoxides such as dimethyl sulfoxide: and mixed solvents of these solvents.

The reaction temperature and reaction time are as follows:
The reaction temperature is usually 0 ° C. to 150 ° C., preferably 0 ° C. to 80 ° C., depending on the type of solvent and base,
The reaction time is usually 15 minutes to 24 hours, preferably 30 minutes to 8 hours.

Process C

[0054]

[Chemical 9]

During the above steps, R ¹ , R ² , R ³ , R ⁴ , R
⁵ and m have the same meaning as described above.

In step C, n is 1 in the general formula (I).
Is a compound (Ic2) and a compound (Ic3) in which n is 2 in the general formula (I).

The steps C-1 and C-2 are of the general formula (I
In the step of producing the compound having the formula (c2) and the compound having the formula (Ic3), a compound (Ic in which n is 0 in the formula (I) is used in an inert solvent using an oxidizing agent.
This is achieved by carrying out the oxidation reaction of 1).

Compound (Ic1) can be produced by the method described in the above step A and the following step E
It is manufactured by process and process I. The oxidizing agent used is not particularly limited as long as it is an oxidizing agent having a strength capable of oxidizing sulfides and sulfoxides.
-Organic peroxides such as chloroperbenzoic acid, formic acid, peracetic acid; inorganic peroxides such as hydrogen peroxide, potassium permanganate, sodium periodate.

The oxidizing agent is used in 1.0 to 1.1 equivalents relative to the substrate in both C-1 and C-2 steps, but the sulfones (Ic3) are directly isolated without isolation of the sulfoxides (Ic2). To obtain the compound (Ic1), 2.
It is achieved by using 0 to 3.0 equivalents.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably halogen such as methylene chloride, chloroform, carbon tetrachloride or dichloroethane. Hydrocarbons; ethers such as tetrahydrofuran, dioxane, diethyl ether; ketones such as acetone, 2-butanone; alcohols such as methanol, ethanol, t-butanol; N, N-dimethylacetamide, N, N-dimethylformamide, N-methyl-2-
Amides such as pyrrolidinone; nitriles such as acetonitrile; acetic acid; water; a mixed solvent of water and the above organic solvent.

The reaction temperature and reaction time are as follows:
When the target compound is the compound (Ic2), the reaction temperature is usually −2, although it varies depending on the kind of the solvent, the oxidizing agent and the target compound.
0 ° C to 50 ° C, preferably -5 ° C to 10 ° C, the reaction time is usually 10 minutes to 5 hours, preferably 30 minutes to 2 hours, and when the target compound is the compound (Ic3), The reaction temperature is generally 0 ° C to 100 ° C, preferably 10 ° C to 6 ° C.
It is 0 ° C., and the reaction time is usually 15 minutes to 2 days, preferably 30 minutes to 1 day.

Step E

[0063]

[Chemical 10]

During the above steps, R ² , R ³ , R ⁴ , R ⁵ and m
And n are as defined above, p is 1 to 6, and X is
⁴ represents a halogen atom.

Step E is a method for producing a compound (Ie) in which R ¹ is a lower alkyl group substituted by one halogen atom in the general formula (I).

Step E-1 is a step for producing a compound having the general formula (Ie) and is accomplished by halogenating the compound (VI) with a halogenating agent in an inert solvent. .

Compound (VI) is produced according to the above steps A and C.

The halogenating agent used is not particularly limited as long as it halogenates an alkyl alcohol, but preferably, bromine, N-bromosuccinimide (NBS), phosphorus pentabromide, chlorine, N-chlorosuccinimide (NCS), phosphorus pentachloride, sulfuryl chloride,
Examples thereof include thionyl chloride and carbon tetrachloride-triphenylphosphine.

The reaction is accelerated in the presence of base. Examples of the base used include tertiary lower alkylamines such as triethylamine, ethyldiisopropylamine and tributylamine; 1,8-diazabicyclo [5.4.0] undecane-7-ene (DBU); 1,4-diazabicyclo Mention may be made of tertiary alicyclic amines such as [2.2.2] octane (DABCO); tertiary anilines such as N, N-dimethylaniline and N, N-diethylaniline.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably aromatic hydrocarbons such as benzene and toluene; methylene chloride. , Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane; ethers such as tetrahydrofuran, i-propyl ether, dioxane, ethyl ether; bases such as pyridine; and mixed solvents of these solvents. be able to.

The reaction temperature and reaction time are as follows:
The reaction temperature varies depending on the solvent and the halogenating agent used, but the reaction temperature is generally -20 ° C to 150 ° C, preferably 0 ° C to 8 ° C.
The temperature is 0 ° C., and the reaction time is generally 5 minutes to 24 hours, preferably 10 minutes to 4 hours.

Step H

[0073]

[Chemical 11]

During the above steps, R ² , R ³ , R ⁴ , R ⁵ and m
And n have the same meaning as described above.

Step H is a method for producing a compound (VIII) having a formyl group at the 5-position of the isoxazoline ring.

Step H-1 is a step for producing a compound having the general formula (VIII), and the compound (VII) having a hydroxymethyl group at the 5-position of the isoxazoline ring is used in an inert solvent with an oxidizing agent. It is achieved by oxidation.

Compound (VII) is produced according to the above steps A and C.

The oxidizing agent to be used is not particularly limited as long as it is a relatively mild oxidizing agent, but preferably N, N-
Generated from dimethyl sulfoxide, dicyclohexylamide, oxalyl chloride, phosgene, chloroformic acid ester, acetic anhydride, phosphorus pentoxide, pyridine-sulfuric anhydride complex, methyl sulfide and chlorinating agent such as N-chlorosuccinimide or chlorine. Sulfonium salt (DMSO oxidation); Chromate such as chromic acid; Oxygen in the presence of a metal catalyst such as platinum; Permanganate such as potassium permanganate; Sodium hypochlorite,
Hypochlorite compounds such as t-butyl hypochlorite; Peroxysulfates such as Oxone; Ruthenium tetraoxide and ruthenium salts capable of generating it in the reaction system; Sodium hypochlorite and 2,2,6 An oxoammonium salt composed of a combination of 6-tetramethyl-1-piperidinyloxy free radicals can be mentioned.

The equivalent of the oxidizing agent varies greatly depending on the conditions used, but in the case of DMSO oxidation, it can be 1 to 5 equivalents of oxalyl chloride and 1 to 10 equivalents of N, N-dimethylsulfoxide to the substrate.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably ethers such as dioxane, tetrahydrofuran, ether and dimethoxyethane;
Halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane; aromatic hydrocarbons such as benzene, toluene, xylene; ketones such as acetone, 2-butanone; nitriles such as acetonitrile;
Mention may be made of esters such as ethyl acetate and butyl acetate; and mixed solvents of these solvents.

The reaction temperature and reaction time are as follows:
The reaction temperature is usually −80 ° C. to 200 ° C., preferably −70 ° C. to 150, though it varies depending on the type of the solvent and the oxidizing agent.
The reaction time is usually 10 minutes to 3 days, preferably 30 minutes to 24 hours.

Process I

[0083]

[Chemical 12]

In the above steps, R ² , R ³ , R ⁴ , R ⁵ and m
And n have the same meaning as described above, and R ⁸ represents a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms.

Step I is a method for producing a compound (Ii) in which R ¹ is a lower alkyl group substituted with two fluorine atoms in the general formula (I).

Step I-1 is a step for producing a compound having the general formula (Ii), in which an aldehyde or ketone having the general formula (IX) is fluorinated by using a fluorinating agent in an inert solvent. It is achieved by reacting.

Compound (IX) is produced according to the above Step A, Step C and Step H.

The fluorinating agent used is not particularly limited as long as it replaces the carbonyl oxygen with a fluorine atom, but is preferably a dialkyl such as diethylaminosulfur trifluoride (DAST) or dimethylaminosulfur trifluoride. Aminosulfur trifluorides; sulfur tetrafluoride can be mentioned.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably ethers such as dioxane and tetrahydrofuran; trichlorofluoromethane, chloride Mention may be made of halogenated hydrocarbons such as methylene, chloroform, carbon tetrachloride and dichloroethane; aromatic hydrocarbons such as benzene and toluene; hydrocarbons such as isooctane; and mixed solvents of these solvents. .

The reaction temperature and reaction time are as follows:
The reaction temperature depends on the type of solvent and fluorinating agent,
Usually -78 ° C to 200 ° C, preferably -60 ° C to 80
The reaction time is usually 5 minutes to 7 days, preferably 10 minutes to 10 hours.

After completion of each of the above reaction steps, the target compound of each step can be collected from the reaction mixture according to a conventional method. For example, it can be obtained by appropriately neutralizing the reaction mixture, or removing impurities by filtration, adding an organic solvent immiscible with water, washing with water, and distilling the solvent off. If necessary, the obtained target compound can be further purified by a conventional method, for example, recrystallization, reprecipitation or chromatography.

The compound of the present invention is mixed with a carrier and, if necessary, other auxiliary agents, and has a formulation form usually used as a herbicide, such as powder, coarse powder, granule, granule, wettable powder,
It is used by preparing it as an aqueous solvent, an emulsion, a liquid agent and the like. The carrier as used herein refers to a synthetic or natural inorganic or organic substance that is mixed with a herbicide to help reach the plant of the active ingredient compound or to facilitate storage, transportation or handling of the active ingredient. means.

Suitable solid carriers include, for example, clays represented by kaolinite group, montmorillonite group, attapulgite group, talc, mica, pyrophyllite, pumice, vermiculite, gypsum, dolomite, diatomaceous earth, magnesium. Lime, phosphorus lime, zeolite, silicic acid anhydride, synthetic calcium silicate, kaolin, bentonite,
Inorganic substances such as calcium carbonate, soybean flour, tobacco powder, walnut flour, wheat flour, wood flour, starch, vegetable organic substances such as crystalline cellulose, coumarone resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone Examples thereof include synthetic or natural polymer compounds such as resins, ester gums, copal gums, dammal gums, waxes such as carnauba wax, paraffin wax, and beeswax, and urea.

Suitable liquid carriers include, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil and white oil, aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene and methylnaphthalene, Carbon tetrachloride, chloroform,
Chlorinated hydrocarbons such as trichloroethylene, monochlorobenzene and chlorotoluene, ethers such as dioxane and tetrahydrofuran, acetone, methyl ethyl ketone,
Ketones such as diisobutyl ketone, cyclohexanone, acetophenone and isophorone, ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, esters such as diethyl succinate, methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclo Alcohols such as hexanol and benzyl alcohol, ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether,
Examples thereof include ether alcohols such as diethylene glycol butyl ether, polar solvents such as dimethylformamide and dimethylsulfoxide, and water.

Surfactants used for the purposes of emulsification, dispersion, wetting, spreading, binding, control of disintegration, stabilization of active ingredients, improvement of fluidity, rust prevention, promotion of absorption into plants, etc. It may be nonionic.

Suitable nonionic surfactants include, for example, sucrose esters of fatty acids, ethylene oxide polymerization adducts of higher aliphatic alcohols such as lauryl alcohol, stearyl alcohol and oleyl alcohol, and alkylphenols such as isooctylphenol and nonylphenol. Ethylene oxide polymerization adducts, butyl naphthol, octyl naphthol and other alkyl naphthol ethylene oxide polymerization adducts, palmitic acid, stearic acid, oleic acid and other higher fatty acid ethylene polymerization adducts, stearyl phosphate dilauryl phosphate mono- or dialkyl Ethylene oxide polymerization adducts of phosphoric acid, ethylene oxide polymerization adducts of higher aliphatic amines such as dodecylamine and stearic acid amide, higher fatty acid esters of polyhydric alcohols such as sorbitan, and ethylene oxide thereof. Copolymers of emissions polymerization adducts and ethylene oxide and propylene oxide can be cited.

Suitable anionic surfactants include, for example, alkyl sulphate salts such as sodium lauryl sulphate, oleyl alcohol sulphate amine salt, etc., fatty acid salts such as sodium sulfosuccinate dioctyl ester, sodium oleate, sodium stearate and the like. ,
Examples thereof include alkyl aryl sulfonates such as sodium isopropyl naphthalene sulfonate, sodium methylene bis naphthalene sulfonate, sodium lignin sulfonate, and sodium dodecylbenzene sulfonate.

Suitable cationic surfactants include, for example, higher aliphatic amines, quaternary ammonium salts, alkylpyridinium salts and the like.

Further, the herbicide of the present invention may contain other ingredients such as gelatin, gum arabic, casein, albumin, glue, sodium alginate, polyvinyl alcohol, for the purpose of improving the properties of the preparation and enhancing the biological effect. Carboxymethyl cellulose, methyl cellulose,
It may also contain a polymer compound such as hydroxymethyl cellulose, a sodium polyphosphate, a thixotropic agent such as bentonite, and other auxiliary agents.

The above-mentioned carrier and various auxiliary agents are appropriately used alone or in combination depending on the purpose in consideration of the application situation of the dosage form of the preparation.

Dusts usually contain 2 to 10 parts by weight of the active ingredient compound, the rest being a solid carrier.

The wettable powder usually contains the active ingredient in an amount of 10 to 80 parts by weight, and the rest is a solid carrier and a dispersion wetting agent, and if necessary, a protective colloid agent, a thixotropic agent, an antifoaming agent and the like are added.

Granules usually contain 0.1 to 1 of the active ingredient compound.
It contains 0 parts by weight, and the rest is mostly solid carrier. The active ingredient compound is uniformly mixed with the solid carrier or is uniformly fixed or adsorbed on the surface of the solid carrier, and the particle diameter is about 0.2 to 1.5 mm.

The emulsion usually contains 1 to 50 parts by weight of the active ingredient, contains about 5 to 20 parts by weight of the emulsion, the rest is a liquid carrier, and a rust preventive agent is added if necessary. .

When the compounds of the present invention thus prepared in various dosage forms are treated in the soil before or after germination of weeds in the paddy field, for example, 1 to 1000 g, preferably 10 to 1000 g as an active ingredient per 10 a. By treating 300 g, weeds can be effectively exterminated.

Further, when the weeds are treated with soil before germination or with foliage treatment after germination in the field, 1 to 1000 g, preferably 10 to 30 g, as an active ingredient per 10 a.
By treating 0 g, weeds can be effectively exterminated.

Other herbicides are preferably added to the herbicide of the present invention in order to broaden the herbicidal spectrum, and a synergistic effect can be expected in some cases.

The herbicide of the present invention can of course be used in combination with other plant growth regulators, fungicides, insecticides, acaricides, nematicides or fertilizers.

Examples and formulation examples of the herbicide of the present invention are shown below and specifically described, but the present invention is not limited thereto.

[0110]

【Example】

[0111]

Example 1 3-Benzylthio-5-chloromethyl-5-methyl-2
-Isoxazoline (Compound No. 1) (Step A) (1) 3-chloro-5-chloromethyl-5-methyl-
2-Isoxazoline (Step A-1) 43.2 g of 2-hydroxyiminoacetic acid and 129.6 g of N-chlorosuccinimide were added to 400 ml of dimethoxyethane.
And was heated to 80 ° C. in an oil bath and stirred. After 3 minutes, the oil bath was removed and the mixture was allowed to cool to room temperature. 48 ml of methallyl chloride, 194.4 g of potassium hydrogen carbonate,
8 ml of water was sequentially added, and the mixture was stirred at room temperature for 8 hours. After adding hexane to the reaction solution, suction filtration was performed using Celite. After distilling off the organic solvent of the filtrate, silica gel column chromatography (hexane: ethyl acetate = 30: 1)
Purification was performed to give the title compound (51.6 g, 64%) as an oil.

¹ H-NMR (CDCl ₃ ) δ: 1.59 (3H, s), 3.14 (2H,
ABq, J = 17.5, Δν = 76.4Hz), 3.57 (2H, ABq, J = 11.4Δν = 1
6.0Hz) ppm (2) 3-benzylthio-5-chloromethyl-5-methyl-2-isoxazoline (step A-2) 3-chloro-5-chloromethyl-5-obtained in (1)
Tetrahydrofuran of 176.1 mg of methyl-2-isoxazoline and 0.35 ml of benzyl mercaptan:
N, N-dimethylformamide = 8: 1 mixed solvent 9 m
125 mg of 60% sodium hydride at room temperature
Was added little by little. After stirring at room temperature for 3 hours, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration and evaporation of the solvent, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1) to obtain 182.8 mg (68%) of the desired product as an oil.

¹ H-NMR (CDCl ₃ ) δ: 1.57 (3H, s), 3.00 (2H,
ABq, J = 16.8, Δν = 75.3Hz), 3.52 (2H, d, J = 2.2Hz), 4.27
(2H, s), 7.29-7.40 (5H, m) ppm The compound produced according to the method of Example 1 is shown below.

In the following, the number in parentheses after the compound name indicates the compound number in Table 1, followed by the melting point (° C.) as “mp” or as an oily substance as “oil”. "Amorphous" or amorphous.

3- (2-Methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoo
Kisazoline (2, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2.40 (3H, s), 3.
01 (2H, ABq, J = 16.6, Δν = 74.7Hz), 3.54 (2H, d, J = 3.1H
z), 4.29 (2H, s), 7.16-7.20 (3H, m), 7.30-7.34 (1H, m) pp
m 3- (3-Methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (3, mp4
0-43) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2.35 (3H, s), 3.
00 (2H, ABq, J = 16.7, Δν = 75.3Hz), 3.53 (2H, ABq, J = 11.
2, Δν = 7.2Hz), 4.23 (2H, s), 7.08-7.31 (4H, m) ppm 3- (4-Methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (4, mp5
3-54) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.34 (3H, s), 3.
00 (2H, ABq, J = 16.7, Δν = 75.1Hz), 3.53 (2H, ABq, J = 11.
2, Δν = 7.3Hz), 4.24 (2H, s), 7.11-7.29 (4H, m) ppm 3- (2,3-Dimethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(5, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.29 (6H, br),
3.02 (2H, ABq, J = 16.6, Δν = 74.5Hz), 3.55 (2H, ABq, J = 11.
2, Δν = 9.3Hz), 4.32 (2H, s), 7.06-7.21 (3H, m) ppm 3- (2,4-Dimethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(6, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2.31 (3H, s), 2.
36 (3H, s), 3.01 (2H, ABq, J = 16.9, Δν = 74.5Hz), 3.54 (2
H, ABq, J = 11.1, Δν = 9.0Hz), 4.26 (2H, s), 6.95-7.23 (3
H, m) ppm 3- (2,5-Dimethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(7, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.30 (3H, s), 2.
35 (3H, s), 3.02 (2H, ABq, J = 16.7, Δν = 74.5Hz), 3.55 (2
H, ABq, J = 11.3, Δν = 9.1Hz), 4.26 (2H, s), 7.02-7.14 (3
H, m) ppm 3- (2,6-Dimethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(8, mp72-73) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 2.42 (6H, s), 3.
05 (2H, ABq, J = 16.8, Δν = 73.4Hz), 3.58 (2H, ABq, J = 11.
2, Δν = 11.2Hz), 4.36 (2H, s), 7.01-7.15 (3H, m) ppm 3- (3,4-Dimethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(9, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.23 (6H, s), 3.
00 (2H, ABq, J = 16.7, Δν = 74.9Hz), 3.52 (2H, ABq, J = 11.
2, Δν = 7.4Hz), 4.21 (2H, s), 7.09 (2H, s), 7.13 (1H, s)
ppm 3- (3,5-Dimethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (1
(0, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2.30 (6H, s), 3.
01 (2H, ABq, J = 16.7, Δν = 75.3Hz), 3.53 (2H, d, J = 2.2H
z), 4.20 (2H, s), 6.92 (1H, br), 6.98 (2H, br) ppm 3- (2,4,6-Trimethylbenzyl) thio-5-chloromethyl-5-methyl-2-iso Oxazoline
(11, mp90-92) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 2.26 (3H, s), 2.
38 (6H, s), 3.04 (2H, ABq, J = 16.7, Δν = 73.1Hz), 3.57 (2
H, ABq, J = 11.1, Δν = 10.9Hz), 4.33 (2H, s), 6.87 (2H, s)
ppm 3- (2-ethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (12, oi
l) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.26 (3H, t, J = 7.5Hz), 1.56 (3
H, s), 2.74 (2H, q, J = 7.5Hz), 3.02 (2H, ABq, J = 16.8, Δν
= 74.5Hz), 3.55 (2H, ABq, J = 11.3, Δν = 9.3Hz), 4.32 (2
H, s), 7.15-7.36 (4H, m) ppm 3- (4-ethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (14, oi
l) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.22 (3H, t, J = 7.5Hz), 1.54 (3
H, s), 2.64 (2H, q, J = 7.5Hz), 3.00 (2H, ABq, J = 16.7, Δν
= 74.9Hz), 3.52 (2H, d, J = 2.0Hz), 4.24 (2H, s), 7.16 (2H,
d, J = 8.0Hz), 7.28 (2H, d, J = 8.0Hz) ppm 3- (2,6-diethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (1
5, mp40-42) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.27 (6H, t, J = 7.5Hz), 1.59 (3
H, s), 2.76 (4H, q, J = 7.5Hz), 3.04 (2H, ABq, J = 16.7, Δν
= 72.7Hz), 3.58 (2H, ABq, J = 11.2, Δν = 11.6Hz), 4.39 (2
H, s), 7.06-7.26 (3H, m) ppm 3- (4-n-Propylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(19, mp34-36) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 0.93 (3H, t, J = 7.3Hz), 1.55 (3
H, s), 1.57-1.72 (2H, m), 2.57 (2H, t, J = 7.2Hz), 3.00 (2H,
ABq, J = 16.6, Δν = 74.9Hz), 3.52 (2H, ABq, J = 11.1, ν = 7.
0Hz), 4.24 (2H, s), 7.14 (2H, d, J = 8.0Hz), 7.28 (2H, d, J =
8.0Hz) ppm 3- (4-tert-butylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(31, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.30 (9H, s), 1.54 (3H, s), 3.
00 (2H, ABq, J = 16.6, Δν = 74.6Hz), 3.52 (2H, d, J = 1.7H
z), 4.24 (2H, s), 7.31-7.40 (4H, m) ppm 3- (2- (5,6,7,8-Tetrahitronaphthyl) thio) -5-chloromethyl-5-methyl-2- Iseo
Kisazoline (33, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 1.75-1.81 (4H,
m), 2.71-2.77 (4H, m), 3.00 (2H, ABq, J = 16.8, Δν = 74.9
Hz), 3.53 (2H, ABq, J = 11.2, Δν = 7.7Hz), 4.20 (2H, s),
6.99-7.11 (3H, m) ppm 3- (2-chlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (34, oi
l) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 75.2Hz), 3.52 (2H, ABq, J = 11.3, Δν = 7.2H
z), 4.22 (2H, s), 7.26 (3H, m), 7.37 (1H, m) ppm 3- (3-chlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (35, oi
l) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.9, Δν = 76.9Hz), 3.53 (2H, ABq, J = 14.6, Δν = 8.0H
z), 4.22 (2H, s), 7.27 (3H, s), 7.37 (1H, s) ppm 3- (4-chlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (36, oi
l) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
17.0, Δν = 77.0Hz), 3.51 (2H, s), 4.21 (2H, s), 7.30 (4
H, s) ppm 3- (2,3-Dichlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (3
7, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.99 (2H, ABq, J =
16.9, Δν = 76.6Hz), 3.52 (2H, ABq, J = 11.6, Δν = 6.3H
z), 4.38 (2H, s), 7.12-7.16 (1H, m), 7.38-7.46 (2H, m) pp
m 3- (2,4-Dichlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (3
(8, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.8, Δν = 74.2Hz), 3.52 (2H, d, J = 1.9Hz), 4.32 (2H,
s), 7.21 (1H, dd, J = 8.4,1.9Hz), 7.41 (1H, d, J = 1.9), 7.47
(1H, d, J = 8.4Hz) ppm 3- (2,5-Dichlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (3
9, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.00 (2H, ABq, J =
16.5, Δν = 73.9Hz), 3.53 (2H, d, J = 2.3Hz), 4.32 (2H,
s), 7.21 (1H, dd, J = 8.5,2.3Hz), 7.32 (1H, d, J = 8.5Hz),
7.52 (1H, d, J = 2.3Hz) ppm 3- (2,6-Dichlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (4
(0, mp80-81) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 3.06 (2H, ABq, J =
16.6, Δν = 73.9Hz), 3.57 (2H, ABq, J = 11.2, Δν = 11.4H
z), 4.63 (2H, s), 7.14-7.35 (3H, m) ppm 3- (3,4-dichlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (4
1, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2.99 (2H, ABq, J =
16.6, Δν = 75.4Hz), 3.52 (2H, d, J = 2.0Hz), 4.19 (2H,
s), 7.23 (1H, dd, J = 8.0,1.7Hz), 7.39 (1H, d, J = 8.0Hz),
7.48 (1H, d, J = 1.7Hz) ppm 3- (3,5-Dichlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (4
2, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
17.2, Δν = 74.9Hz), 3.53 (2H, ABq, J = 11.2, Δν = 7.3H
z), 4.18 (2H, s), 7.25 (1H, s), 7.27 (2H, s) ppm 3- (2,4,6-trichlorobenzyl) thio-5-chloromethyl-5-methyl-2-iso Oxazoline
(44, Amorphous) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 3.05 (2H, ABq, J =
16.7, Δν = 74.5Hz), 3.57 (2H, ABq, J = 11.3, Δν = 10.8H
z), 4.59 (2H, s), 7.36 (2H, s) ppm 3- (3-chloro-4-methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(45, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.36 (3H, s), 2.
99 (2H, ABq, J = 16.7, Δν = 75.2Hz), 3.52 (2H, ABq, J = 11.
2, Δν = 7.2Hz), 4.19 (2H, s), 7.11-7.36 (3H, m) ppm 3- (2,4-Dichloro-3-methylbenzyl) thio-5-chloromethyl-5-methyl-2 -Isoxa
Solin (48, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 2.49 (3H, s), 2.
99 (2H, ABq, J = 16.7, Δν = 74.0Hz), 3.52 (2H, d, J = 1.9H
z), 4.34 (2H, s), 7.21-7.34 (2H, m) ppm 3- (2,5-dichloro-4-methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxa
Solin (49, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.33 (3H, s), 3.
00 (2H, ABq, J = 16.8, Δν = 73.8Hz), 3.53 (2H, ABq, J = 11.
2, Δν = 7.8Hz), 4.30 (2H, s), 7.27 (1H, s), 7.49 (1H, s)
ppm 3- (2-Bromobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (50, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.9, Δν = 75.2Hz), 3.53 (2H, d, J = 2.1Hz), 4.38 (2H,
s), 7.14-7.18 (1H, m), 7.24-7.31 (1H, m), 7.50-7.59 (2
H, m) ppm 3- (3-Bromobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (51, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.6, Δν = 75.1Hz), 3.53 (2H, d, J = 2.1Hz), 4.21 (2H,
s), 7.15-7.34 (2H, m), 7.38-7.53 (2H, m) ppm 3- (4-Bromobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (52, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.98 (2H, ABq, J =
16.7, Δν = 75.6Hz), 3.52 (2H, d, J = 1.8Hz), 4.20 (2H,
s), 7.23-7.28 (2H, m), 7.42-7.47 (2H, m) ppm 3- (2-Fluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (53, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.01 (2H, ABq, J =
16.8, Δν = 74.5Hz), 3.53 (2H, d, J = 2.1Hz), 4.29 (2H,
s), 7.01-7.14 (2H, m), 7.23-7.31 (1H, m), 7.44 (1H, t, J =
7.7Hz) ppm 3- (3-Fluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (54, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 75.4Hz), 3.52 (2H, d, J = 2.1Hz), 4.24 (2H,
s), 6.97-7.32 (4H, m) ppm 3- (4-Fluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (55, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.8, Δν = 75.1Hz), 3.52 (2H, ABq, J = 11.1, Δν = 6.8H
z), 4.23 (2H, s), 6.96-7.05 (2H, m), 7.31-7.38 (2H, m) pp
m 3- (2,3-Difluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(56, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 74.7Hz), 3.53 (2H, ABq, J = 11.2, Δν = 7.4H
z), 4.31 (2H, d, J = 1.4Hz), 7.02-7.22 (3H, m) ppm 3- (2,4-difluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(57, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 2.99 (2H, ABq, J =
16.7, Δν = 74.1Hz), 3.51 (2H, ABq, J = 11.2, Δν = 7.2H
z), 4.24 (2H, s), 6.75-6.88 (2H, m), 7.37-7.49 (1H, m) pp
m 3- (2,5-Difluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(58, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.18 (2H, ABq, J =
16.7, Δν = 74.6Hz), 3.53 (2H, ABq, J = 11.2, Δν = 7.5H
z), 4.25 (2H, s), 6.92-7.05 (2H, m), 7.14-7.23 (1H, m) pp
m 3- (2,6-difluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(59, mp58-61) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.03 (2H, ABq, J =
16.7, Δν = 75.2Hz), 3.55 (2H, ABq, J = 11.2, Δν = 9.8H
z), 4.35 (2H, s), 6.87-6.96 (2H, m), 7.19-7.31 (1H, m) pp
m 3- (3,4-difluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(60, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.6, Δν = 75.3Hz), 3.52 (2H, ABq, J = 11.3, Δν = 6.9H
z), 4.19 (2H, s), 7.06-7.23 (3H, m) ppm 3- (3,5-difluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(61, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.19 (2H, ABq, J =
16.7, Δν = 75.4Hz), 3.52 (2H, ABq, J = 11.3, Δν = 7.3H
z), 4.21 (2H, s), 6.66-6.95 (3H, m) ppm 3- (2-fluoro-3-methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(64, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.28 (3H, d, J = 2.
1Hz), 3.00 (2H, ABq, J = 16.8, Δν = 74.5Hz), 3.52 (2H, AB
q, J = 11.2, Δν = 7.5Hz), 4.28 (2H, s), 6.98 (1H, t, J = 7.5
7Hz), 7.08-7.12 (1H, m), 7.21-7.28 (1H, m) ppm 3- (3-Fluoro-4-methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(65, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.25 (3H, d, J = 1.
9Hz), 3.00 (2H, ABq, J = 16.7, Δν = 75.2Hz), 3.52 (2H, AB
q, J = 11.2, Δν = 7.2Hz), 4.21 (2H, s), 7.01-7.17 (3H, m)
ppm 3- (2,3,5,6-tetrafluoro-4-methylbenzyl) thio-5-chloromethyl-5-methyl-2
-Isoxazoline (66, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.24 (3H, dt, J = 1
2.8,2.0Hz), 2.85 (1H, dd, J = 16.8,5.2Hz), 3.18 (1H, dd, J
= 16.8,5.9Hz), 3.53 (2H, ABq, J = 3.5, Δν = 3.0Hz), 4.35 (2
H, d, J = 22.4Hz) ppm 3- (2-Fluoro-3-chlorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(67, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 74.1Hz), 3.52 (2H, ABq, J = 11.3, Δν = 7.1H
z), 4.29 (2H, s), 7.04 (1H, t, J = 7.9Hz), 7.28-7.40 (2H,
m) ppm 3- (2-chloro-4-fluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(68, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 2.99 (2H, ABq, J =
16.8, Δν = 73.8Hz), 3.52 (2H, ABq, J = 11.2, Δν = 7.1H
z), 4.33 (2H, s), 6.95 (1H, td, J = 8.4,2.6Hz), 7.14 (1H, d
d, J = 8.4,2.6Hz), 7.50 (1H, dd, J = 8.4,6.1Hz) ppm 3- (2-chloro-6-fluorobenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(70, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.04 (2H, ABq, J =
16.7, Δν = 76.4Hz), 3.55 (2H, ABq, J = 11.2, Δν = 10.5H
z), 4.47 (2H, d, J = 1.6Hz), 6.97-7.26 (3H, m) ppm 3- (2-trifluoromethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(71, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 73.5Hz), 3.54 (2H, ABq, J = 11.2, Δν = 8.8H
z), 4.46 (2H, s), 7.35-7.43 (1H, m), 7.49-7.56 (1H, m),
7.64-7.71 (2H, m) ppm 3- (3-Trifluoromethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(72, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 75.4Hz), 3.51 (2H, d, J = 2.0Hz), 4.30 (2H,
s), 7.44-7.64 (4H, m) ppm 3- (4-trifluoromethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(73, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.8, Δν = 75.7Hz), 3.52 (2H, d, J = 1.9Hz), 4.29 (2H,
s), 7.53 (2H, d, J = 8.4Hz), 7.57 (2H, d, J = 8.4Hz) ppm 3- (2,4-bistrifluoromethylbenzyl) thio-5-chloromethyl-5-methyl- 2-isooki
Sasolin (74, Amorphous) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.01 (2H, ABq, J =
16.7, Δν = 74.4Hz), 3.55 (2H, ABq, J = 11.8, Δν = 8.9H
z), 4.49 (2H, s), 7.78 (1H, d, J = 7.9Hz), 7.90 (2H, d, J = 7.
9Hz) ppm 3- (3.5-bistrifluoromethylbenzyl) thio-5-chloromethyl-5-methyl-2-isooxy
Sazoline (75, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.01 (2H, ABq, J =
17.0, Δν = 75.6Hz), 3.52 (2H, ABq, J = 11.2, Δν = 6.8H
z), 4.34 (2H, s), 7.79 (1H, br), 7.86 (2H, br) ppm 3- (2-Fluoro-4-trifluoromethylbenzyl) thio-5-chloromethyl-5-methyl-2 -Iso
Oxazoline (76, mp46-48) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.16 (2H, ABq, J =
16.8, Δν = 74.8Hz), 3.52 (2H, ABq, J = 11.3, Δν = 6.9H
z), 4.31 (2H, s), 7.33 (1H, d, J = 9.3Hz), 7.38 (1H, d, J = 9.
3Hz), 7.62 (1H, t, J = 7.3Hz) ppm 3- (2-Methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (77, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.00 (2H, ABq, J =
16.8, Δν = 74.3Hz), 3.51 (2H, ABq, J = 18.3, Δν = 8.6H
z), 3.87 (3H, s), 4.29 (2H, s), 6.86-6.95 (2H, m), 7.23-
7.39 (2H, m) ppm 3- (3-Methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (78, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.00 (2H, ABq, J =
16.8, Δν = 75.3Hz), 3.53 (2H, ABq, J = 11.2, Δν = 7.7H
z), 3.81 (3H, s), 4.24 (2H, s), 6.80-6.97 (3H, m), 7.21-
7.28 (1H, m) ppm 3- (4-Methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (79, m
(p32-33) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.7, Δν = 74.9Hz), 3.52 (2H, d, J = 2.1Hz), 3.80 (3H,
s), 4.22 (2H, s), 6.85 (2H, d, J = 8.6Hz), 7.30 (2H, d, J = 8.
6Hz) ppm 3- (2,3-Dimethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(80, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 3.06 (2H, ABq, J =
17.0, Δν = 77.0Hz), 3.53 (2H, d, J = 2.3Hz), 3.86 (3H,
s), 3.89 (3H, s), 4.31 (2H, s), 6.83-6.91 (1H, m), 6.97-
7.05 (2H, m) ppm 3- (2,4-Dimethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(81, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2.99 (2H, ABq, J =
16.6, Δν = 73.8Hz), 3.52 (2H, ABq, J = 11.3, Δν = 7.7H
z), 3.80 (3H, s), 3.84 (3H, s), 4.24 (2H, s), 6.41-6.45
(2H, m), 7.25-7.30 (1H, m) ppm 3- (2,5-Dimethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(82, mp50-53) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.6, Δν = 73.9Hz), 3.52 (2H, ABq, J = 11.3, Δν = 7.9H
z), 3.77 (3H, s), 3.83 (3H, s), 4.26 (2H, s), 6.78-6.80
(2H, m), 6.97 (1H, d, J = 1.6Hz) ppm 3- (2,6-Dimethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(83, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.06 (2H, ABq, J =
16.6, Δν = 75.5Hz), 3.55 (2H, ABq, J = 11.2, Δν = 10.9H
z), 3.85 (6H, s), 4.40 (2H, s), 6.55 (2H, d, J = 8.4Hz), 7.
22 (1H, t, J = 8.4Hz) ppm 3- (3,4-Dimethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(84, mp95-97) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 77.5Hz), 3.53 (2H, d, J = 2.3Hz), 3.87 (3H,
s), 3.89 (3H, s), 4.20 (2H, s), 6.79-6.94 (3H, m) ppm3-
(3,5-Dimethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (8
5, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3h, s), 3.01 (2H, ABq, J =
16.7, Δν = 75.4Hz), 3.53 (2H, d, J = 2.7Hz), 3.79 (6H,
s), 4.21 (2H, s), 6.38 (1H, t, J = 2.3Hz), 6.53 (2H, d, J = 2.
2Hz) ppm 3- (3,4,5-trimethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(87, Amorphous) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.01 (2H, ABq, J =
16.7, Δν = 75.9Hz), 3.53 (2H, d, J = 2.5Hz), 3.84 (3H,
s), 3.86 (6H, s), 4.22 (2H, s), 6.61 (2H, s) ppm 3- (2-Ethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (88, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.44 (3H, t, J = 7.0Hz), 1.54 (3
H, s), 2.99 (2H, ABq, J = 16.8, Δν = 73.8Hz), 3.52 (2H, AB
q, J = 11.2, Δν = 7.2Hz), 4.09 (2H, q, J = 7.0Hz), 4.31 (2
H, s), 6.84-6.93 (2H, m), 7.20-7.29 (1H, m), 7.35-7.40
(1H, m) ppm 3- (3-Ethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (89, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.41 (3H, t, J = 7.0Hz), 1.54 (3
H, s), 3.00 (2H, ABq, J = 16.7, Δν = 75.1Hz), 3.53 (2H, AB
q, J = 11.2, Δν = 7.5Hz), 4.03 (2H, q, J = 7.0Hz), 4.23 (2
H, s), 6.78-6.95 (3H, m), 7.21 (1H, d, J = 7.3Hz) ppm 3- (4-ethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline ( 90, m
p64) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.41 (3H, t, J = 7.0Hz), 1.54 (3
H, s), 2.99 (2H, ABq, J = 16.8, Δν = 75.1Hz), 3.52 (2H, d,
J = 2.2Hz), 4.02 (2H, q, J = 7.0Hz), 4.22 (2H, s), 6.84 (2H,
d, J = 8.6Hz), 7.28 (2H, d, J = 7.6Hz) ppm 3- (2-isopropyloxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (92, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.36 (6H, d, J = 6.1Hz), 1.54 (3
H, s), 2.99 (2H, ABq, J = 16.9, Δν = 73.4Hz), 3.52 (2H, AB
q, J = 11.2, Δν = 7.7Hz), 4.28 (2H, s), 4.61 (1H, quinte
t, J = 6.3Hz), 6.83-6.91 (2H, m), 7.18-7.26 (1H, m), 7.27
-7.40 (1H, m) ppm 3- (3-Isopropyloxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (93, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 75.2Hz), 3.53 (2H, ABq, J = 11.2, Δν = 7.6H
z), 4.23 (2H, s), 4.55 (1H, quintet, J = 6.1Hz), 6.77-7.1
8 (3H, m), 7.24 (1H, d, J = 8.1Hz) ppm 3- (4-Isopropyloxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (94, mp34-36) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.33 (3H, d, J = 6.2Hz), 1.54 (3
H, s), 3.00 (2H, ABq, J = 16.6, Δν = 74.8Hz), 3.52 (2H, d,
J = 2.2Hz), 4.22 (2H, s), 4.53 (1H, septet, J = 6.2Hz), 6.8
3 (2H, d, J = 8.7Hz), 7.27 (2H, d, J = 8.7Hz) ppm 3- (2-Methoxy-3-methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(95, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2,22-2.27 (1H,
m), 2.31 (3H, s), 3.01 (2H, ABq, J = 16.8, Δν = 74.5Hz),
3.54 (2H, ABq, J = 11.2, Δν = 8.8Hz), 3.80 (3H, s), 4.32
(2H, s), 6.95-7.02 (1H, m), 7.13 (1H, d, J = 6.0Hz) ppm 3- (3-Methyl-4-methoxybenzyl) thio-5-chloromethyl-5-methyl- 2-isoxazoly
(97, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.31 (3H, s), 3.
02 (2H, ABq, J = 16.8, Δν = 74.4Hz), 3.54 (2H, ABq, J = 11.
1, Δν = 9.0Hz), 3.81 (3H, s), 4.32 (2H, s), 6.95-7.27
(3H, m) ppm 3- (3-Methoxy-4-methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(98, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.19 (3H, s), 3.
01 (2H, ABq, J = 16.8, Δν = 75.6Hz), 3.53 (2H, ABq, J = 11.
2, Δν = 7.7Hz), 3.83 (3H, s), 4.24 (2H, s), 6.86 (2H, d,
J = 5.6Hz), 7.08 (1H, d, J = 7.7Hz) ppm 3- (2-Ethoxy-3-methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(99, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.44 (3H, t, J = 7.2Hz), 1.55 (3
H, s), 2.30 (3H, s), 3.01 (2H, ABq, J = 16.9, Δν = 73.9H
z), 3.54 (2H, d, J = 3.0Hz), 3.93 (2H, q, J = 7.2Hz), 4.32 (2
H, s), 6.98-7.02 (1H, m), 7.12 (1H, d, J = 6.1Hz), 7.23-7.
26 (1H, m) ppm 3- (2-isopropyloxy-3-methylbenzyl) thio-5-chloromethyl-5-methyl-2-yl
Soxazoline (100, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.32 (6H, d, J = 6.2Hz), 1.58 (3
H, s), 2.29 (3H, s), 3.01 (2H, ABq, J = 16.7, Δν = 73.6H
z), 3.53 (2H, ABq, J = 5.9, Δν = 6.2Hz), 4.24-4.38 (1H,
m), 4.34 (2H, s) ppm 3- (3-chloro-2-methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(101, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.01 (2H, ABq, J =
16.9, Δν = 74.4Hz), 3.53 (2H, ABq, J = 11.1, Δν = 8.6H
z), 3.94 (3H, s), 4.31 (2H, s), 6.98-7.05 (1H, m), 7.29-
7.37 (2H, m) ppm 3- (4-Chloro-2-methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(102, mp63-64) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.98 (2H, ABq, J =
16.7, Δν = 74.5Hz), 3.52 (2H, ABq, J = 11.0, Δν = 7.1H
z), 3.86 (3H, s), 4.23 (2H, s), 6.85-6.92 (2H, m), 7.31 (1
H, d, J = 7.7Hz) ppm 3- (2-chloro-5-methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(103, mp50-54) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.8, Δν = 72.9Hz), 3.53 (2H, ABq, J = 11.2, Δν = 8.0H
z), 3.78 (3H, s), 4.33 (2H, s), 6.78 (1H, dd, J = 8.8,3.0H
z), 7.06 (1H, d, J = 3.0Hz), 7.26 (1H, d, J = 8.8Hz) ppm 3- (5-chloro-2-methoxybenzyl) thio-5-chloromethyl-5-methyl- 2-isoxazoly
(104, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2.99 (2H, ABq, J =
16.7, Δν = 74.3Hz), 3.53 (2H, ABq, J = 11.1, Δν = 7.6H
z), 3.85 (3H, s), 4.23 (2H, s), 6.79 (1H, d, J = 8.8Hz), 7.
22 (1H, dd, J = 8.8,2.7Hz), 7.36 (1H, d, J = 2.7Hz) ppm 3- (4-chloro-3-methoxybenzyl) thio-5-chloromethyl-5-methyl-2 -Isoxazoly
(105, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.8, Δν = 75.7Hz), 3.43 (2H, ABq, J = 11.3, Δν = 7.3H
z), 3.91 (3H, s), 4.22 (2H, s), 6.88-6.98 (2H, m), 7.30 (1
H, d, J = 8.1Hz) ppm 3- (3,5-dichloro-2-methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isooxy
Serolin (106, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.01 (2H, ABq, J =
16.8, Δν = 74.5Hz), 3.54 (2H, ABq, J = 11.3, Δν = 8.7H
z), 3.91 (3H, s), 4.26 (2H, s), 7.31-7.35 (2H, m) ppm 3- (2,6-Dimethoxy-3-chlorobenzyl) thio-5-chloromethyl-5-methyl -2-isooki
Sarrine (107, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.05 (2H, ABq, J =
16.6, Δν = 75.3Hz), 3.56 (2H, ABq, J = 11.2, Δν = 11.6H
z), 3.85 (3H, s), 3.92 (3H, s), 4.39 (2H, s), 6.63 (1H, d,
J = 8.9Hz), 7.28 (1H, d, J = 8.9Hz) ppm 3- (2-chloro-3,4-dimethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isooxy
Sarrine (108, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.6, Δν = 72.7Hz), 3.53 (2H, d, J = 2.6Hz), 3.87 (6H,
s), 4.33 (2H, s), 6.79 (1H, d, J = 8.5Hz), 7.23 (1H, d, J = 8.
5Hz) ppm 3- (3,5-dichloro-4-methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isooxy
Serolin (109, mp41-47) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.00 (2H, ABq, J =
16.8, Δν = 74.5Hz), 3.53 (2H, ABq, J = 11.3, Δν = 7.7H
z), 3.89 (3H, s), 4.15 (2H, s), 7.32 (2H, s) ppm 3- (3-chloro-2-ethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(110, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.46 (3H, t, J = 7.0Hz), 3.00 (3
H, s), (2H, ABq, J = 16.8, Δν = 74.1Hz), 3.52 (2H, d, J = 2.2H
z), 4.11 (2H, q, J = 7.0Hz), 4.32 (2H, s), 7.00 (1H, t, J = 7.
8Hz), 7.32 (2H, t, J = 2.4Hz) ppm 3- (4-chloro-2-ethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(111, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.44 (3H, t, J = 7.0Hz), 1.53 (3
H, s), 2.98 (2H, ABq, J = 16.7, Δν = 73.9Hz), 3.51 (2H, d,
J = 1.8Hz), 4.06 (2H, q, J = 7.0Hz), 4.23 (2H, s), 6.83-6.8
9 (2H, m), 7.31 (1H, d, J = 7.9Hz) ppm 3- (2-chloro-5-ethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(112, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.40 (3H, t, J = 7.0Hz), 1.54 (3
H, s), 2.99 (2H, ABq, J = 16.7, Δν = 73.0Hz), 3.53 (2H, AB
q, J = 11.3, Δν = 7.8Hz), 4.00 (2H, q, J = 7.0Hz), 4.33 (2
H, s), 6.77 (1H, dd, J = 8.8,3.0Hz), 7.05 (1H, d, J = 3.0Hz),
7.25 (1H, d, J = 8.8Hz) ppm 3- (5-Chloro-2-ethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(113, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.43 (3H, t, J = 7.0Hz), 1.54 (3
H, s), 2.99 (2H, ABq, J = 16.7, Δν = 73.8Hz), 3.53 (2H, AB
q, J = 11.3, Δν = 7.4Hz), 4.05 (2H, q, J = 7.0Hz), 4.24 (2
H, s), 6.77 (1H, d, J = 8.7Hz), 7.18 (1H, dd, J = 8.7,2.7Hz),
7.36 (1H, d, J = 2.7Hz) ppm 3- (4-chloro-3-ethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(114, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.47 (3H, t, J = 7.0Hz), 1.54 (3
H, s), 2.99 (2H, ABq, J = 16.8, Δν = 75.7Hz), 3.52 (2H, AB
q, J = 11.2, Δν = 7.9Hz), 4.11 (2H, q, J = 7.0Hz), 4.20 (2
H, s), 6.88 (1H, dd, J = 8.1,2.0Hz), 6.96 (1H, d, J = 2.0Hz),
7.29 (1H, d, J = 8.1Hz) ppm 3- (3,5-Dichloro-2-ethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isooxy
Satherine (115, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.46 (3H, t, J = 7.0Hz), 1.55 (3
H, s), 3.00 (2H, ABq, J = 16.8, Δν = 74.1Hz), 3.53 (2H, d,
J = 2.2Hz), 4.12 (2H, q, J = 7.0Hz), 4.32 (2H, s), 7.28 (1H,
d, J = 1.8Hz) ppm 3- (4-chloro-2-isopropyloxybenzyl) thio-5-chloromethyl-5-methyl-2-yl
Soxazoline (116, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.36 (6H, d, J = 6.0Hz), 1.53 (3
H, s), 2.97 (2H, ABq, J = 16.7, Δν = 73.4Hz), 3.52 (2H, d,
J = 2.0Hz), 4.21 (2H, s), 4.57 (1H, quintet, J = 6.0Hz), 6.
82-6.87 (2H, m), 7.30 (1H, d, J = 8.7Hz) ppm 3- (2-chloro-5-isopropyloxybenzyl) thio-5-chloromethyl-5-methyl-2-yl
Soxazoline (117, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.32 (6H, d, J = 6.1Hz), 1.54 (3
H, s), 2.99 (2H, ABq, J = 16.3, Δν = 73.6Hz), 3.52 (2H, d,
J = 2.4Hz), 4.32 (2H, s), 4.51 (1H, quintet, J = 6.0Hz), 6.
75 (1H, dd, J = 8.6,3.0Hz), 7.05 (1H, d, J = 3.0Hz), 7.24 (1
H, d, J = 8.6Hz) ppm 3- (5-chloro-2-isopropyloxybenzyl) thio-5-chloromethyl-5-methyl-2-yl
Soxazoline (118, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.35 (6H, d, J = 6.1Hz), 1.55 (3
H, s), 2.99 (2H, ABq, J = 16.6, Δν = 73.6Hz), 3.53 (2H, AB
q, J = 11.2, Δν = 7.8Hz), 4.22 (2H, s), 4.55 (1H, quinte
t, J = 5.9Hz), 6.78 (1H, d, J = 8.8Hz), 7.18 (1H, dd, J = 8.8,
2.7Hz), 7.35 (1H, d, J = 2.7Hz) ppm 3- (4-Chloro-3-isopropyloxybenzyl) thio-5-chloromethyl-5-methyl-2-yl
Soxazoline (119, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.38 (6H, d, J = 6.0Hz), 1.53 (3
H, s), 2.99 (2H, ABq, J = 16.8, Δν = 76.0Hz), 3.52 (2H, AB
q, J = 11.3, Δν = 7.0Hz), 4.20 (2H, s), 4.56 (1H, quinte
t, J = 6.0Hz), 6.87 (1H, dd, J = 8.1,2.0Hz), 6.99 (1H, d, J =
2.0Hz), 7.29 (1H, d, J = 8.1Hz) ppm 3- (2-Fluoro-6-methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (120, mp56-59) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.04 (2H, ABq, J =
16.8, Δν = 75.2Hz), 3.40 (2H, ABq, J = 11.2, Δν = 10.4H
z), 3.88 (3H, s), 4.36 (2H, d, J = 1.2Hz), 6.67-6.75 (2H,
m), 7.17-7.29 (1H, m) ppm 3- (2-ethoxy-3-methoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (121, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.39 (3H, t, J = 7.1Hz), 1.54 (3
H, s), 3.00 (2H, ABq, J = 16.7, Δν = 73.6Hz), 3.53 (2H, AB
q, J = 11.2, Δν = 8.6Hz), 4.19 (2H, q, J = 7.1Hz), 4.31 (2
H, s), 6.82-6.87 (1H, m), 7.00 (2H, d, J = 4.6Hz) ppm 3- (2-Ethoxy-6-methoxybenzyl) thio-5-chloromethyl-5-methyl-2 -Isoxazo
Phosphorus (122, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.42 (3H, t, J = 7.0Hz), 1.56 (3
H, s), 3.06 (2H, ABq, J = 16.8, Δν = 74.4Hz), 3.55 (2H, AB
q, J = 11.0, Δν = 10.7Hz), 3.85 (3H, s), 4.07 (2H, q, J = 7.
0Hz), 4.40 (2H, s), 6.53 (2H, d, J = 8.2Hz), 7.20 (1H, t, J =
8.2Hz) ppm 3- (3-Methoxy-2-propyloxybenzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (123, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.04 (3H, t, J = 7.45), 1.54 (3
H, s), 1.81 (2H, septet, J = 7.1Hz), 3.00 (2H, ABq, J = 16.7,
Δν = 74.0Hz), 3.53 (2H, ABq, J = 11.2, Δν = 8.2Hz), 3.
84 (3H, s), 3.99 (2H, t, J = 6.9Hz), 4.31 (2H, s), 6.99 (2H,
d, J = 5.5Hz) ppm 3- (2-isopropyloxy-3-methoxybenzyl) thio-5-chloromethyl-5-methyl-2-
Isoxazoline (124, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.29 (6H, d, J = 6.2Hz), 1.55 (3
H, s), 3.00 (2H, ABq, J = 16.7, Δν = 72.1Hz), 3.53 (2H, AB
q, J = 11.2, Δν = 9.0Hz), 3.83 (3H, s), 4.34 (2H, s), 4.5
9 (1H, quintet, J = 6.1Hz), 6.81-6.85 (1H, m), 6.94-7.03
(2H, m) ppm 3- (2,3-Methylenedioxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (125, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.02 (2H, ABq, J =
16.8, Δν = 76.4Hz), 3.52 (2H, ABq, J = 11.1, Δν = 7.3H
z), 4.28 (2H, s), 5.99 (2H, s), 6.73-6.90 (3H, m) ppm 3- (3,4-methylenedioxybenzyl) thio-5-chloromethyl-5-methyl-2 -Isoxazo
Phosphorus (126, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.6, Δν = 74.9Hz), 3.53 (2H, d, J = 2.4Hz), 4.19 (2H,
s), 5.95 (2H, s), 6.72-6.86 (3H, m) ppm 3- (2,3-ethylenedioxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (127, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 74.9Hz), 3.53 (2H, ABq, J = 11.2, Δν = 8.0H
z), 4.24-4.34 (6H, m), 6.74-6.84 (2H, m), 6.94 (1H, dd, J
= 6.1,3.2Hz) ppm 3- (2-methyl-3,4-ethylenedioxybenzyl) thio-5-chloromethyl-5-methyl-2-yl
Soxazoline (131, mp83-85) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.22 (3H, s), 3.
01 (2H, ABq, J = 16.9, Δν = 74.2Hz), 3.54 (2H, ABq, J = 11.
1, Δν = 9.2Hz), 4.20-4.31 (6H, m), 6.68 (1H, d, J = 8.4H
z), 6.83 (1H, d, J = 8.3Hz) ppm 3- (4-trifluoromethoxybenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(142, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 75.3Hz), 3.52 (2H, ABq, J = 11.3, Δν = 6.9H
z), 4.24 (2H, s), 7.16 (2H, d, J = 8.7Hz), 7.41 (2H, d, J = 8.
7Hz) ppm 3- (2-Difluoromethoxy-3-methylbenzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (143, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 2.33 (3H, s), 3.
14 (2H, ABq, J = 17.5, Δν = 76.6Hz), 4.15 (2H, ABq, J = 11.
4, Δν = 15.6Hz), 4.33 (2H, s), 6.43 (1H, t, J = 74.0Hz),
7.13-7.17 (2H, m), 7.37 (1H, dd, J = 6.3,2.3Hz) ppm 3- (2-Difluoromethoxy-4-methylbenzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (144, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 2.34 (3H, s), 2.
99 (2H, ABq, J = 16.7, Δν = 73.5Hz), 3.52 (2H, d, J = 2.1H
z), 4.27 (2H, s), 6.53 (1H, t, J = 74.0Hz), 6.94-7.01 (2H,
m), 7.37 (1H, d, J = 7.8Hz) ppm 3- (2-Difluoromethoxy-5-methylbenzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (145, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.32 (3H, s), 3.
00 (2H, ABq, J = 16.7, Δν = 73.1Hz), 3.52 (2H, ABq, J = 11.
2, Δν = 7.6Hz), 4.27 (2H, s), 6.51 (1H, t, J = 73.9Hz),
7.04-7.12 (2H, m), 7.28 (1H, d, J = 1.6Hz) ppm 3- (3-Difluoromethoxy-4-methylbenzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (146, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.27 (3H, s), 2.
99 (2H, ABq, J = 16.6, Δν = 75.1Hz), 3.52 (2H, ABq, J = 11.
3, Δν = 7.2Hz), 4.22 (2H, s), 6.50 (1H, t, J = 74.1Hz),
7.10-7.20 (3H, m) ppm 3- (3-chloro-2-difluoromethoxybenzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (147, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.8, Δν = 73.4Hz), 3.52 (2H, ABq, J = 11.2, Δν = 7.4H
z), 4.36 (2H, s), 6.06 (1H, t, J = 74.4Hz), 7.18 (1H, t, J =
7.9Hz), 7.04 (1H, dd, J = 7.9,1.7Hz), 7.50 (1H, dd, J = 1.8,
1.7Hz) ppm 3- (2-chloro-5-difluoromethoxybenzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (148, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 74.0Hz), 3.52 (2H, ABq, J = 11.3, Δν = 7.3H
z), 4.34 (2H, s), 6.49 (1H, t, J = 73.4Hz), 7.02 (1H, dd, J =
8.8,2.9Hz), 7.33 (1H, d, J = 2.9Hz), 7.37 (1H, d, J = 8.8Hz)
ppm 3- (5-chloro-2-difluoromethoxybenzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (149, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.8, Δν = 73.6Hz), 3.52 (2H, d, J = 2.3Hz), 4.25 (2H,
s), 6.53 (1H, t, J = 73.3Hz), 7.08 (1H, d, J = 8.8Hz), 7.26
(1H, dd, J = 8.8,2.5Hz), 7.50 (1H, d, J = 2.5Hz) ppm 3- (4-chloro-3-difluoromethoxybenzyl) thio-5-chloromethyl-5-methyl-2 -Iso
Oxazoline (150, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.8, Δν = 75.5Hz), 3.52 (2H, ABq, J = 10.4, Δν = 6.9H
z), 4.21 (2H, s), 6.54 (1H, t, J = 73.4Hz), 7.08-7.41 (3H,
m) ppm 3- (2-Methoxymethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (1
51, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.01 (2H, ABq, J =
16.5, Δν = 74.3Hz), 3.41 (3H, s), 3.54 (2H, ABq, J = 11.
2, Δν = 8.5Hz), 4.37 (2H, s), 4.56 (2H, s), 7.26-7.45
(4H, m) ppm 3- (2-Ethoxymethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (1
52, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.26 (3H, t, J = 7.0Hz), 1.55 (3
H, s), 3.00 (2H, ABq, J = 16.9, Δν = 74.3Hz), 3.52-3.62
(4H, m), 4.38 (2H, s), 4.60 (2H, s), 7.25-7.45 (4H, m) ppm 3- (2- (2,2,2-trifluoroethoxymethyl) benzyl) thio- 5-chloromethyl-5-methyl
-2-isoxazoline (153, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.00 (2H, ABq, J =
17.8, Δν = 82.4Hz), 3.53 (2H, d, J = 2.4Hz), 3.86 (2H, q,
J = 8.8Hz), 4.35 (2H, s), 4.80 (2H, s), 7.3-7.5 (4H, m) ppm 3- (3- (2,2,2-trifluoroethoxymethyl) benzyl) thio- 5-chloromethyl-5-methyl
-2-isoxazoline (154, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.8, Δν = 75.4Hz), 3.52 (2H, d, J = 2.0Hz), 3.84 (2H, q,
J = 8.6Hz), 4.27 (2H, s), 4.67 (2H, s), 7.29-7.36 (4H, m) p
pm 3- (2- (2-methoxyethoxy) benzyl) thio-5-chloromethyl-5-methyl-2-isoxazo
Grin (155, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.8, Δν = 73.6Hz), 3.52 (2H, ABq, J = 9.5, Δν = 6.5Hz),
3.78 (2H, t, J = 4.8Hz), 4.18 (2H, t, J = 4.8Hz), 4.31 (2H,
s), 6.86-6.96 (2H, m), 7.21-7.40 (2H, m) ppm 3- (3- (2-methoxyethoxy) benzyl) thio-5-chloromethyl-5-methyl-2-isoxazo
Grin (156, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.7, Δν = 75.1Hz), 3.52 (2H, ABq, J = 12.0, Δν = 7.5H
z), 3.45 (3H, s), 3.75 (2H, t, J = 4.7Hz), 4.12 (2H, t, J = 4.
7Hz), 4.23 (2H, s), 6.82-6.98 (3H, m), 7.23 (1H, t, J = 7.4
Hz) ppm 3- (2- (2,2-Dimethoxyethoxy) benzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (157, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 2.98 (2H, ABq, J =
17.1, Δν = 73.8Hz), 3.47 (6H, s), 3.52 (2H, s), 4.23 (2
H, d, J = 5.7Hz), 4.30 (2H, s), 4.75 (1H, t, J = 5.9Hz), 6.89
-6.93 (2H, m), 7.21-7.41 (2H, m) ppm 3- (3- (2,2-Dimethoxyethoxy) benzyl) thio-5-chloromethyl-5-methyl-2-iso
Oxazoline (158, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.00 (2H, ABq, J =
16.8, Δν = 75.1Hz), 3.46 (6H, s), 3.52 (2H, d, J = 2.4H
z), 4.00 (2H, d, J = 5.2Hz), 4.23 (2H, s), 4.72 (1H, t, J = 5.
2Hz), 6.82-6.87 (1H, m), 6.96-7.20 (2H, m), 7.23-7.28
(1H, m) ppm 3- (2- (2,2-ethylenedioxyethoxy) benzyl) thio-5-chloromethyl-5-methyl-2
-Isoxazoline (159, mp79-80.5) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 2.99 (2H, ABq, J =
16.7, Δν = 73.1Hz), 3.52 (2H, ABq, J = 11.1, Δν = 7.4H
z), 3.93-4.08 (4H, m), 4.09 (2H, d, J = 3.6Hz), 4.31 (2H,
s), 5.33 (1H, t, J = 3.7Hz), 6.86-6.96 (2H, m), 7.20-7.29
(1H, m), 7.38 (1H, dd, J = 7.5,0.8Hz) ppm 3- (3- (2,2-ethylenedioxyethoxy) benzyl) thio-5-chloromethyl-5-methyl-2
-Isoxazoline (160, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.99 (2H, ABq, J =
16.8, Δν = 74.9Hz), 3.52 (2H, ABq, J = 11.2, Δν = 7.7H
z), 3.92-4.10 (6H, m), 4.23 (2H, s), 5.29 (1H, t, J = 4.0H
z), 6.82-6.99 (3H, m), 7.19-7.27 (1H, m) ppm 3- (α-methylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (161,
oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.49 (s), 1.51 (s) (3H), 1.75
(d, J = 7.0Hz), 1.76 (d, J = 7.0Hz) (3H), 2.92 (ABq, J = 16.7,
Δν = 74.5Hz), 2.95 (ABq, J = 16.7, Δν = 74.1Hz) (2H), 3.
46 (2H, s), 4.79 (q, J = 7.0Hz), 4.79 (q, J = 7.0Hz) (1H), 7.2
3-7.42 (5H, m) ppm 3- (α, α-Dimethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazolyl
(162, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.37 (3H, s), 1.91 (6H, s), 2.
61 (2H, ABq, J = 17.1, Δν = 77.3Hz), 3.30 (2H, ABq, J = 11.
2, Δν = 11.9Hz), 7.25-7.39 (3H, m), 7.56-7.60 (2H, m) p
pm 3- (α-isopropylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(165, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 0.89 (d, J = 6.7Hz) +0.89 (d, J =
6.7Hz) (3H), 1.09 (d, J = 6.7Hz) +1.10 (d, J = 6.7Hz) (3H),
1.43 (3H, s), 2.16-2.24 (1H, m), 2.69 (1H, dd, J = 17.1,12.
1Hz), 3.07 (1H, dd, J = 16.7,14.4Hz), 3.36 (2H, ABq, J = 13.
4, Δν = 7.0Hz), 4.44 (d, J = 7.9Hz) +4.46 (d, J = 7.7Hz) (1
H), 7.22-7.32 (5H, m) ppm 3- (α, 2-Dimethylbenzyl) thio-5-chloromethyl-5-methyl-2-isoxazoline
(166, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (s) +1.56 (s) (3H), 1.76
(d, J = 6.9Hz) +1.78 (d, J = 6.9Hz) (3H), 2.42 (3H, s), 2.96
(ABq, J = 16.6, Δν = 73.0Hz) +2.96 (ABq, J = 16.8, Δν = 71.
3Hz) (2H), 3.49 (2H, d, J = 2.7Hz), 5.01 (1H, q, J = 6.9Hz),
7.16-7.23 (3H, m), 7.40-7.44 (1H, m) ppm 3- (4-chromanyl) thio-5-chloromethyl-5-methyl-2-isoxazoline (167, mp83-
84) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 2.38-2.48 (2H,
m), 2.84 (d, J = 16.9Hz) +2.92 (d, J = 16.8Hz) (1H), 3.14 (d,
J = 16.7Hz) +3.21 (d, J = 16.7Hz) (1H), 3.50-3.64 (2H, m),
4.31-4.37 (2H, m), 5.00 (1H, t, J = 6.4Hz), 6.79-6.93 (2H,
m), 7.13-7.21 (1H, m), 7.28-7.33 (1H, m) ppm 3- (1- (1,2,3,4-terolahitronaphthyl) thio) -5-chloromethyl-5-methyl -2-isoo
Kisazoline (169, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 1.89-2.32 (4H,
m), 2.74-3.65 (6H, m), 5.08 (1H, brs), 7.08-7.21 (3H,
m), 7.38-7.42 (1H, m) ppm 3-Benzylthio-5-trifluoromethyl-5-methyl-2-isoxazoline (179, mp56-
59) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.60 (3H, d, J = 1.9Hz), 2.97 (1
H, dd, J = 7.1,0.8Hz), 3.34 (1H, d, J = 17.2Hz), 4.28 (3H,
s), 7.30-7.38 (5H, m) ppm

[0116]

Example 2 3-Benzylsulfinyl-5-chloromethyl-5-me
Cyl-2-isoxazoline (Compound No. 1001) and 3-benzylsulfonyl-5-chloromethyl-5-meth
Cyl-2-isoxazoline (Compound No. 2001)
(Step C) (1) 3-Benzylsulfinyl-5-chloromethyl-5-methyl-2-isoxazoline (Step C-1) 3-Benzylthio-5-chloromethyl-5 produced by the method of Example 1. Methyl-2-isoxazoline (Compound No. 1) 926.7 mg was added to 1,2-dichloroethane 20.
Dissolve in ml and stir with m-chloroperbenzoic acid 89
2.4 mg was added at room temperature. After stirring at room temperature for 45 minutes, a saturated aqueous solution of sodium sulfite was added to the reaction solution, extraction was performed with methylene chloride, and the organic layer was washed with an aqueous solution of sodium hydrogencarbonate and brine in that order. After drying over anhydrous sodium sulfate, the mixture was filtered, the solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 4: 1) to give the desired product 710.9 having a melting point of 60-65 ° C.
mg (72%) was obtained.

¹ H-NMR (200 MHz, CDCl ₃ ) δ: 1.54 (s) +1.56
(s) (3H), 2.85 (2H, ABq, J = 17.9, Δν = 201.3Hz), 3.43-3.
57 (2H, m), 4.16-4.36 (2H, m), 7.30-7.42 (5H, m) ppm (2) 3-benzylsulfonyl-5-chloromethyl-
5-Methyl-2-isoxazoline (Steps C-1 and C-2) 3-benzylthio-5-chloromethyl-5-methyl-2-isoxazoline (Compound No. 1) 133. produced by the method of Example 1. 1 mg was dissolved in 5 ml of methylene chloride, and 5 ml of a methylene chloride solution of 385 mg of m-chloroperbenzoic acid was added dropwise at room temperature while stirring. 2 more at room temperature
After stirring for an hour, saturated aqueous sodium sulfite solution was added to the reaction solution, extraction was performed with methylene chloride, and the organic layer was washed successively with aqueous sodium hydrogen carbonate solution and brine. After drying over anhydrous sodium sulfate, the mixture was filtered and the solvent was distilled off, followed by silica gel column chromatography (hexane: ethyl acetate = 1).
Purification by 0: 1) gave 86.2 mg (58%) of the desired product having a melting point of 87-88 ° C.

¹ H-NMR (200 MHz, CDCl ₃ ) δ: 1.50 (3H, s), 2.
98 (2H, ABq, J = 17.9, Δν = 86.1Hz), 3.49 (2H, s), 4.60 (2
H, s), 7.43 (5H, m) ppm The compounds produced according to the method of Example 2 (1) and the method of Example 2 (2) are shown below.

3- (2-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-
Isoxazoline (2002, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 2.46 (3H, s), 3.
03 (2H, ABq, J = 17.7, Δν = 88.4Hz), 3.52 (2H, s), 4.69 (2
H, s), 7.23-7.40 (4H, m) ppm 3- (3-Methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (20
03, mp51-54) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.50 (3H, s), 2.37 (3H, s), 2.
97 (2H, ABq, J = 17.8, Δν = 84.9Hz), 3.48 (2H, s), 4.56 (2
H, s), 7.20-7.30 (4H, m) ppm 3- (4-Methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (20
04, mp99-101) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H.s), 2.37 (3H, s), 2.
97 (2H, ABq, J = 17.9, Δν = 78.5Hz), 3.49 (2H, s), 4.56 (2
H, s), 7.22 (2H, d, J = 8.1Hz), 7.31 (2H, d, J = 8.1Hz) ppm 3- (2,3-Dimethylbenzyl) sulfonyl-5-chloromethyl-5-methyl- 2-isoxazoly
(2005, Amorphous) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 2.33 (3H, s), 2.
34 (3H, s), 3.01 (2H, ABq, J = 17.5, Δν = 88.3Hz), 3.52 (2
H, br), 4.72 (2H, s), 7.09-7.24 (3H, m) ppm 3- (2,4-Dimethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2006, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 2.33 (3H, s), 2.
41 (3H, s), 3.02 (2H, ABq, J = 17.8, Δν = 80.6Hz), 3.51 (2
H, s), 4.64 (2H, s), 7.03-7.13 (2H, m), 7.24-7.27 (1H, m)
ppm 3- (2,5-Dimethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2007, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 2.33 (3H, s), 2.
41 (3H, s), 3.03 (2H, ABq, J = 17.9, Δν = 88.7Hz), 3.52 (2
H, s), 4.64 (2H, s), 7.14-7.17 (3H, m) ppm 3- (2,6-Dimethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2008, Amorphous) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 2.48 (6H, s), 3.
17 (2H, ABq, J = 17.8, Δν = 85.7Hz), 3.58 (2H, d, J = 1.8H
z), 4.85 (2H, s), 7.08-7.26 (3H, m) ppm 3- (3,4-Dimethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2009, mp87-88) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H, s), 2.28 (6H, s), 2.
96 (2H, ABq, J = 17.8, Δν = 75.5Hz), 3.47 (2H, s), 4.53 (2
H, s), 7.16 (3H, s) ppm 3- (3,5-Dimethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2010, mp73-75) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H, s), 2.33 (6H, s), 2.
97 (2H, ABq, J = 17.9, Δν = 84.4Hz), 3.48 (2H, s), 4.52 (2
H, s), 7.03 (3H, br) ppm 3- (2,4,6-Trimethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2011, mp121-123) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 2.29 (3H, s), 2.
43 (6H, s), 3.14 (2H, ABq, J = 17.7, Δν = 78.6Hz), 3.56 (2
H, s), 4.80 (2H, s), 6.94 (2H, s) ppm 3- (2-Ethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (20
12, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.24 (3H, t, J = 7.5Hz), 1.53 (3
H, s), 2.81 (2H, q, J = 7.5Hz), 3.02 (2H, ABq, J = 17.9, Δν
= 88.7Hz), 3.52 (2H, s), 4.71 (2H, s), 7.20-7.41 (4H, m) p
pm 3- (4-Ethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (20
14, mp112-113) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.24 (3H, t, J = 7.7Hz), 1.50 (3
H, s), 2.67 (2H, q, J = 7.7Hz), 2.96 (2H, ABq, J = 18.0, Δν
= 80.8Hz), 3.47 (2H, s), 4.57 (2H, s), 7.24 (2H, d, J = 8.1H
z), 7.34 (2H, d, J = 8.1Hz) ppm 3- (2,6-Diethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2015, mp58-61) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.24 (6H, t, J = 7.5Hz), 1.57 (3
H, s), 2.85 (4H, q, J = 7.5Hz), 3.13 (2H, ABq, J = 17.7, Δν
= 86.3Hz), 3.56 (2H, s), 4.89 (2H, s), 7.17 (2H, d, J = 7.7H
z), 7.26-7.36 (1H, m) ppm 3- (4-n propylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2019, mp101-103) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 0.94 (3H, t, J = 7.3Hz), 1.49 (3
H, s), 1.64 (2H, sextet, J = 7.3Hz), 2.61 (2H, t, J = 7.3Hz),
2.95 (2H, ABq, J = 17.9, Δν = 84.5Hz), 3.48 (2H, s), 4.56
(2H, s), 7.22 (2H, d, J = 8.3Hz), 7.34 (2H, d, J = 8.3Hz) ppm 3- (2-isopropylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2 -Isoxazo
Phosphorus (2020, mp76-78) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.08 (2H, ABq, J =
17.9, Δν = 90.9Hz), 3.23-3.36 (1H, m), 3.54 (2H, ABq, J
= 11.7, Δν = 5.8Hz), 4.75 (2H, s), 7.18-1.42 (4H, m) ppm 3- (4-tert-Butylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2031, mp108-110) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.32 (9H, s), 1.49 (3H, s), 2.
94 (2H, ABq, J = 17.8, Δν = 81.2Hz), 3.46 (2H, d, J = 1.3H
z), 4.57 (2H, s), 7.35 (2H, d, J = 8.6Hz), 7.44 (2H, d, J = 8.
6Hz) ppm 3- (2- (5,6,7,8-Tetrahitrononaphtyl) sulfonyl) -5-chloromethyl-5-methyl-2-
Isoxazoline (2033, mp69-73) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H, s), 1.76-1.82 (4H,
m), 2.74-2.77 (4H, m), 2.98 (2H, ABq, J = 18.0, Δν = 73.0
Hz), 3.47 (2H, s), 4.52 (2H, s), 7.09-7.18 (3H, m) ppm 3- (2-chlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline ( 20
34, mp92-94) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.08 (2H, ABq, J =
17.9, Δν = 83.2Hz), 3.54 (2H, ABq, J = 11.8, Δν = 7.9H
z), 4.58 (2H, s), 7.33-7.42 (4H, m) ppm 3- (3-chlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (20
35, mp95-97) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.08 (2H, ABq, J =
17.8, Δν = 83.6Hz), 3.54 (2H, d, J = 1.4Hz), 4.57 (2H,
s), 7.32-7.43 (4H, m) ppm 3- (4-chlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (20
36, mp89-90) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.10 (2H, ABq, J =
17.8, Δν = 82.4Hz), 3.54 (2H, d, J = 2.4Hz), 4.58 (2H,
s), 7.38 (4H, s) ppm 3- (2,3-Dichlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2037, mp71-73) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.17 (2H, ABq, J =
17.7, Δν = 81.4Hz), 3.57 (2H, ABq, J = 11.8, Δν = 10.1H
z), 4.90 (2H, s), 7.27 (1H, t, J = 7.9Hz), 7.46-7.57 (2H,
m) ppm 3- (2,4-dichlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2038, mp111-113) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 3.21 (2H, ABq, J =
17.7, Δν = 80.7Hz), 3.69 (2H, ABq, J = 11.8, Δν = 10.7H
z), 4.82 (2H, s), 7.33 (1H, dd, J = 8.4,2.0Hz), 7.49-7.53
(2H, m) ppm 3- (2,5-Dichlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2039, mp135-136) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 3.20 (2H, ABq, J =
17.7, Δν = 81.7Hz), 3.59 (2H, ABq, J = 11.7, Δν = 11.5H
z), 4.81 (2H, s), 7.33 (1H, dd, J = 8.6,2.2Hz), 7.42 (1H,
d, J = 8.6Hz), 7.56 (1H, d, J = 2.2Hz) ppm 3- (2,6-dichlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2040, mp147-148) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.63 (3H, s), 3.29 (2H, ABq, J =
17.8, Δν = 83.0Hz), 3.62 (2H, d, J = 4.7Hz), 5.15 (2H,
s), 7.29-7.45 (3H, m) ppm 3- (3,4-dichlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2041, mp88-90) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.17 (2H, ABq, J =
17.8, Δν = 80.5Hz), 3.56 (2H, ABq, J = 11.8, Δν = 10.7H
z), 4.56 (2H, s), 7.29 (1H, dd, J = 8.3,2.0Hz), 7.50 (1H,
d, J = 8.4Hz), 7.54 (1H, d, J = 2.0Hz) ppm 3- (3,5-dichlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2042, mp96-98) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.16 (2H, ABq, J =
18.0, Δν = 81.6Hz), 3.57 (2H, ABq, J = 11.9, Δν = 11.5H
z), 4.55 (2H, s), 7.34 (2H, d, J = 1.8Hz), 7.42 (1H, t, J = 1.
8Hz) ppm 3- (2,3,5-trichlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2043, mp124-127) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.60 (3H, s), 3.21 (2H, ABq, J =
17.9, Δν = 81.6Hz), 3.59 (2H, ABq, J = 11.7, Δν = 11.5H
z), 4.81 (2H, s), 7.31-7.56 (2H, m) ppm 3- (2,4,6-trichlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2044, mp137-139) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.64 (3H, s), 3.32 (2H, ABq, J =
17.8, Δν = 83.4Hz), 3.63 (2H, ABq, J = 11.7, Δν = 12.2H
z), 5.11 (2H, s), 7.45 (2H, s) ppm 3- (3-chloro-4-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2045, mp79-83) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.39 (3H, s), 3.
09 (2H, ABq, J = 17.8, Δν = 81.7Hz), 3.53 (2H, ABq, J = 9.6,
Δν = 6.0Hz), 4.54 (2H, s), 7.17-7.40 (3H, m) ppm 3- (3-Methyl-4-chlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2046, mp88-90) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2.39 (3H, s), 3.
09 (2H, ABq, J = 17.8, Δν = 81.3Hz), 3.53 (2H, ABq, J = 11.
7, Δν = 6.5Hz), 4.55 (2H, s), 7.17-7.40 (3H, m) ppm 3- (3,4-Dichloro-2-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2 -Iso
Oxazoline (2047, mp86-90) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 2.54 (3H, s), 3.
20 (2H, ABq, J = 17.9, Δν = 82.7Hz), 3.59 (2H, ABq, J = 11.
7, Δν = 11.5Hz), 4.72 (2H, s), 7.25 (1H, d, J = 8.0Hz),
7.37 (1H, d, J = 8.4Hz) ppm 3- (2,4-Dichloro-3-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-iso
Oxazoline (2048, mp110-112) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 2.52 (3H, s), 3.
18 (2H, ABq, J = 17.9, Δν = 77.8Hz), 3.57 (2H, ABq, J = 11.
6, Δν = 9.2Hz), 4.86 (2H, s), 7.35 (2H, s) ppm 3- (2,5-Dichloro-4-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-iso
Oxazoline (2049, mp116-118) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 2.37 (3H, s), 3.
19 (2H, ABq, J = 18.0, Δν = 78.5Hz), 3.58 (2H, ABq, J = 11.
8, Δν = 9.7Hz), 4.77 (2H, s), 7.35 (1H, s), 7.53 (1H, s)
ppm 3- (2-bromobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
050, mp73-75) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.12 (2H, ABq, J =
17.9, Δν = 81.5Hz), 3.56 (2H, ABq, J = 11.5, Δν = 9.5H
z), 4.89 (2H, s), 7.28-7.38 (2H, m), 7.57-7.68 (2H, m) pp
m 3- (3-Bromobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
051, mp90) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.09 (2H, ABq, J =
17.6, Δν = 83.5Hz), 3.54 (2H, d, J = 2.4Hz), 4.57 (2H,
s), 7.29-7.42 (2H, m), 7.56 (2H, d, J = 7.8Hz) ppm 3- (4-Bromobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
052, mp114-115) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.10 (2H, ABq, J =
17.6, Δν = 81.8Hz), 3.54 (2H, d, J = 2.4Hz), 4.57 (2H,
s), 7.31 (2H, d, J = 8.3Hz), 7.56 (2H, d, J = 8.3Hz) ppm 3- (2-Fluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
053, mp82-84) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.95 (2H, ABq, J =
17.7, Δν = 81.9Hz), 3.56 (2H, ABq, J = 11.6, Δν = 8.2H
z), 4.68 (2H, s), 7.14-7.25 (2H, m), 7.37-7.51 (2H, m) pp
m 3- (3-Fluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
054, mp95-97) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 3.09 (2H, ABq, J =
17.7, Δν = 83.3Hz), 3.53 (2H, ABq, J = 11.7, Δν = 7.6H
z), 4.60 (2H, s), 7.12-7.23 (3H, m), 7.34-7.41 (1H, m) pp
m 3- (4-Fluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
055, mp75-76) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 3.10 (2H, ABq, J =
17.8, Δν = 83.4Hz), 3.53 (2H, ABq, J = 11.7, Δν = 7.5H
z), 4.58 (2H, s), 7.06-7.15 (2H, m), 7.38-7.45 (2H, m) pp
m 3- (2,3-Difluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2056, mp83-85) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 3.22 (2H, ABq, J =
17.9, Δν = 81.2Hz), 3.59 (2H, ABq, J = 11.8, Δν = 10.6H
z), 4.70 (2H, s), 7.13-7.26 (3H, m) ppm 3- (2,4-difluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2057, mp81) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 3.21 (2H, ABq, J =
17.7, Δν = 80.6Hz), 3.58 (2H, ABq, J = 11.7, Δν = 10.6H
z), 4.64 (2H, s), 6.86-7.01 (2H, m, 7.43-7.55 (1H, m) ppm 3- (2,5-difluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2- Isoxazo
Phosphorus (2058, mp127-129) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 3.22 (2H, ABq, J =
17.7, Δν = 80.8Hz), 3.58 (2H, ABq, J = 11.7, Δν = 10.5H
z), 4.65 (2H, s), 7.08-7.25 (3H, m) ppm 3- (2,6-difluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2059, mp92-93) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.62 (3H, s), 3.27 (2H, ABq, J =
17.7, Δν = 82.3Hz), 3.61 (2H, ABq, J = 11.6, Δν = 10.6H
z), 4.37 (2H, s), 6.97-7.05 (2H, m), 7.37-7.46 (1H, m) pp
m 3- (3,4-difluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2060, mp104) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.17 (2H, ABq, J =
17.8, Δν = 80.8Hz), 3.56 (2H, ABq, J = 11.7, Δν = 10.9H
z), 4.57 (2H, s), 7.12-7.34 (3H, m) ppm 3- (3,5-difluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2061, mp108-110) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.17 (2H, ABq, J =
17.8, Δν = 81.3Hz), 3.57 (2H, ABq, J = 11.9, Δν = 11.1H
z), 4.59 (2H, s), 6.88-7.02 (3H, m) ppm 3- (2-fluoro-3-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxa
Solin (2064, mp96-97) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.31 (3H, d, J = 2.
0Hz), 3.14 (2H, ABq, J = 17.8, Δν = 84.1Hz), 3.55 (2H, AB
q, J = 11.7, Δν = 6.2Hz), 4.66 (2H, s), 7.09 (1H, t, J = 7.7
Hz), 7.28 (2H, q, J = 7.3Hz) ppm 3- (3-Fluoro-4-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2065, mp88-89) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.29 (3H, d, J = 1.
9Hz), 3.07 (2H, ABq, J = 17.9, Δν = 78.2Hz), 3.52 (2H,
s), 4.56 (2H, s), 7.08-7.27 (3H, br) ppm 3- (2,3,5,6-tetrafluoro-4-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl
Le-2-isoxazoline (2066, mp115-117) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.62 (3H, d, J = 7.1Hz), 2.29 (3
H, dt, J = 13.1,2.2Hz), 3.09 (1H, dd, J = 17.8,11.7Hz), 3.4
1-3.69 (3H, m), 4.70 (2H, d, J = 20.5Hz) ppm 3- (2-Fluoro-3-chlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2067, mp90-92) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 3.38 (2H, ABq, J =
17.8, Δν = 81.1Hz), 3.58 (2H, ABq, J = 11.7, Δν = 10.4H
z), 4.69 (2H, s), 7.12-7.20 (1H, m), 7.37-7.52 (2H, m) pp
m 3- (2-chloro-4-fluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2068, mp80-82) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 3.20 (2H, ABq, J =
17.9, Δν = 81.4Hz), 3.59 (2H, ABq, J = 11.7, Δν = 11.0H
z), 4.81 (2H, s), 7.07 (1H, td, J = 8.6,2.7Hz), 7.12-7.25
(1H, m), 7.56 (1H, dd, J = 8.6,5.9Hz) ppm 3- (2-Chloro-6-fluorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxa
Solin (2070, mp118) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.63 (3H, s), 3.27 (2H, ABq, J =
17.8, Δν = 82.8Hz), 3.62 (2H, ABq, J = 11.7, Δν = 11.1H
z), 4.91 (2H, d, J = 1.6Hz), 7.12-7.39 (3H, m) ppm 3- (2-trifluoromethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2071, mp78) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 3.21 (2H, ABq, J =
17.8, Δν = 80.3Hz), 3.58 (2H, ABq, J = 11.7, Δν = 9.8H
z), 4.87 (2H, s), 7.55-7.64 (2H, m), 7.77 (2H, d, J = 7.4H
z) ppm 3- (3-trifluoromethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2072, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.14 (2H, ABq, J =
17.8, Δν = 84.6Hz), 3.54 (2H, d, J = 2.6Hz), 4.67 (2H,
s), 7.59-7.70 (4H, m) ppm 3- (4-trifluoromethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2073, mp107-109) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.14 (2H, ABq, J =
18.0, Δν = 81.2Hz), 3.55 (2H, ABq, J = 11.8, Δν = 9.4H
z), 4.68 (2H, s), 7.58 (2H, d, J = 8.3Hz), 7.69 (2H, d, J = 8.
3Hz) ppm 3- (2,4-bistrifluoromethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-yl
Soxazoline (2074, mp84-85) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.62 (3H, s), 3.30 (2H, ABq, J =
17.6, Δν = 78.9Hz), 3.62 (2H, ABq, J = 11.8, Δν = 13.4H
z), 4.93 (2H, s), 7.91 (2H, br.d, J = 2.6Hz), 8.02 (1H, br)
ppm 3- (3,5-bistrifluoromethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-yl
Soxazoline (2075, mp105-106) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 3.23 (2H, ABq, J =
17.7, Δν = 82.3Hz), 3.58 (2H, ABq, J = 11.9, Δν = 12.7H
z), 4.75 (2H, s), 7.92 (3H, br) ppm 3- (2-fluoro-4-trifluoromethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2076, mp93-94) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 3.25 (2H, ABq, J =
17.6, Δν = 79.7Hz), 3.59 (2H, ABq, J = 11.8, Δν = 11.9H
z), 4.74 (2H, s), 7.41-7.51 (2H, m), 7.67 (1H, t, J = 7.0H
z) ppm 3- (2-Methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
077, mp85-87) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.05 (2H, ABq, J =
17.8, Δν = 85.5Hz), 3.49 (2H, s), 3.87 (3H, s), 4.71 (2
H, s), 6.93-7.00 (2H, m), 7.39-7.45 (2H, m) ppm 3- (3-Methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
078, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.50 (3H, s), 2.96 (2H, ABq, J =
17.9, Δν = 82.1Hz), 3.49 (2H, s), 3.82 (3H, s), 4.56 (2
H, s), 6.92-7.01 (3H, m), 7.27-7.34 (1H, m) ppm 3- (4-Methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
079, mp84-85) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H, s), 3.00 (2H, ABq, J =
17.6, Δν = 81.2Hz), 3.50 (2H, s), 3.82 (3H, s), 4.54 (2
H, s), 6.93 (2H, d, J = 8.7Hz), 7.34 (2H, d, J = 8.7Hz) ppm 3- (2,3-Dimethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl- 2-isoxazo
Phosphorus (2080, mp94-95) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.11 (2H, ABq, J =
17.8, Δν = 71.4Hz), 3.56 (2H, ABq, J = 11.4, Δν = 13.8H
z), 3.86 (3H, s), 3.93 (3H, s), 4.69 (2H, s), 6.95-7.13
(3H, m) ppm 3- (2,4-Dimethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2081, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.06 (2H, ABq, J =
17.8, Δν = 82.3Hz), 3.50 (2H, s), 3.83 (3H, s), 3.85 (3
H, s), 6.49-6.56 (2H, m), 4.63 (2H, s), 7.34 (1H, d, J = 8.3
Hz) ppm 3- (2,5-Dimethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2082, mp92-94) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 3.06 (2H, ABq, J =
17.9, Δν = 83.1Hz), 3.50 (2H, s), 3.78 (3H, s), 3.83 (3
H, s), 4.67 (2H, s), 6.89-7.00 (3H, m) ppm 3- (2,6-dimethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2083, mp128-130) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.13 (2H, Abq, J =
17.7, Δν = 87.9Hz), 3.53 (2H, s), 3.87 (6H, s), 4.80 (2
H, s), 6.60 (2H, d, J = 8.4Hz), 7.33 (1H, t, J = 7.3Hz) ppm 3- (3,4-dimethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl- 2-isoxazo
Phosphorus (2084, mp117-118) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H, s), 3.01 (2H, ABq, J =
17.8, Δν = 83.0Hz), 3.51 (2H, s), 3.90 (6H, s), 4.55 (2
H, s), 6.86-6.99 (3H, m) ppm 3- (3,5-dimethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2085, mp128-128.5) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H, s), 2.97 (2H, ABq, J =
17.9, Δν = 79.1Hz), 3.50 (2H, s), 3.80 (6H, s), 4.52 (2
H, s), 6.49 (1H, t, J = 2.2Hz), 6.55 (2H, d, J = 2.2Hz) ppm 3- (3,4,5-trimethoxybenzyl) sulfonyl-5-chloromethyl-5 -Methyl-2-isooxa
Solin (2087, mp105-106) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.52 (3H, s), 3.04 (2H, ABq, J =
17.9, Δν = 88.3Hz), 3.52 (2H, d, J = 1.8Hz), 3.86 (3H,
s), 3.87 (6H, s), 4.54 (2H, s), 6.63 (2H, s) ppm 3- (2-ethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
088, mp97-99) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.45 (3H, t, J = 7.0Hz), 1.51 (3
H, s), 2.99 (2H, ABq, J = 17.8, Δν = 87.0Hz), 3.48 (2H,
s), 4.09 (2H, q, J = 7.0Hz), 4.73 (2H, s), 6.91-7.03 (2H,
m), 7.33-7.46 (2H, m) ppm 3- (3-Ethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
089, mp86-88) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.42 (3H, t, J = 7.0Hz), 1.55 (3
H, s), 2.96 (2H, ABq, J = 17.9, Δν = 81.9Hz), 3.49 (2H,
s), 4.04 (2H, q, J = 7.0Hz), 4.55 (2H, s), 6.92-6.99 (3H,
m), 7.27-7.31 (1H, m) ppm 3- (4-Ethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
090, mp104-105) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.42 (3H, t, J = 7.0Hz), 1.51 (3
H, s), 2.99 (2H, ABq, J = 18.0, Δν = 82.3Hz), 3.50 (2H,
s), 4.04 (2H, d, J = 7.0Hz), 4.53 (2H, s), 6.91 (2H, d, J = 8.
6Hz), 7.32 (2H, d, J = 8.4Hz) ppm 3- (2,6-Diethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Phosphorus (2091, mp81-82) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.43 (6H, t, J = 7.0Hz), 1.55 (3
H, s), 3.02 (2H, ABq, J = 17.8, Δν = 89.8Hz), 3.50 (2H,
s), 4.08 (4H, q, J = 7.0Hz), 4.85 (2H, s), 6.55 (2H, d, J = 8.
3Hz), 7.27 (1H, t, J = 8.3Hz) ppm 3- (2-Isopropyloxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Serolin (2092, mp89-92) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.37 (6H, d, J = 6.0Hz), 1.51 (3
H, s), 2.98 (2H, ABq, J = 17.7, Δν = 83.7Hz), 3.48 (2H,
s), 4.61 (1H, quintet, J = 6.1Hz), 4.71 (2H, s), 6.91-6.9
9 (2H, m), 7.30-7.46 (2H, m) ppm 3- (3-isopropyloxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Serolin (2093, mp66-68) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.50 (3H, s), 2.68 (6H, d, J = 6.
1Hz), 2.96 (2H, ABq, J = 17.8, Δν = 83.4Hz), 3.48 (2H,
s), 4.53-4.59 (3H, m), 6.90-6.98 (3H, m), 7.30-7.34 (1
H, m) ppm 3- (4-isopropyloxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Serolin (2094, mp76-78) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.35 (3H, d, J = 6.2Hz), 1.51 (3
H, s), 3.00 (2H, ABq, J = 17.8, Δν = 82.5Hz), 3.50 (2H,
s), 4.53 (2H, s), 4.53 (1H, septet, J = 6.2Hz), 6.90 (2H,
d, J = 8.6Hz), 7.31 (2H, d, J = 8.6Hz) ppm 3- (2-Methoxy-3-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2095, mp110-113) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.34 (3H, s), 3.
08 (3H, s), 3.11 (2H, ABq, J = 17.5, Δν = 77.9Hz), 3.55 (2
H, ABq, J = 12.1, Δν = 11.1Hz), 4.67 (2H, s), 7.04-7.12
(1H, m), 7.23-7.35 (2H, m) ppm 3- (3-Methyl-4-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2097, mp110-111) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.34 (3H, s), 3.
10 (2H, ABq, J = 17.6, Δν = 77.5Hz), 3.54 (2H, ABq, J = 11.
4, Δν = 10.8Hz), 3.80 (3H, s), 4.67 (2H, s), 7.04-7.12
(1H, m), 7.23-7.34 (2H, m) ppm 3- (3-Methoxy-4-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2098, mp86-88) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.50 (3H, s), 2.22 (3H, s), 2.
96 (2H, ABq, J = 17.8, Δν = 83.2Hz), 3.48 (2H, s), 3.85 (3
H, s), 4.56 (2H, s), 6.87-6.92 (2H, m), 7.15 (1H, d, J = 7.4
Hz) ppm 3- (2-Ethoxy-3-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxa
Solin (2099, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.41 (3H, t, J = 7.1Hz), 1.56 (3
H, s), 2.31 (3H, s), 3.08 (2H, ABq, J = 17.8, Δν = 75.0H
z), 3.55 (2H, ABq, J = 11.5, Δν = 12.0Hz), 3.93 (2H, q, J =
7.1Hz), 4.65 (2H, s), 7.07 (1H, t, J = 7.5Hz), 7.25 (1H,
m), 7.34 (1H, d, J = 7.5Hz) ppm 3- (2-Isopropyloxy-3-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-
2-isoxazoline (2100, mp105-106) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.30 (6H, d, J = 6.2Hz), 1.56 (3
H, s), 2.30 (3H, s), 2.96 (2H, ABq, J = 17.7, Δν = 70.0H
z), 3.51 (2H, ABq, J = 11.4, Δν = 6.7Hz), 4.22 (1H, quint
et, J = 6.1Hz), 4.64 (2H, s), 7.07 (1H, t, J = 7.8Hz), 7.24
(1H, d, J = 7.6Hz), 7.36 (1H, d, J = 7.8Hz) ppm 3- (3-chloro-2-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2101, mp83-85) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.59 (3H, s), 3.18 (2H, ABq, J =
17.7, Δν = 81.7Hz), 3.59 (2H, ABq, J = 11.6, Δν = 14.3H
z), 3.97 (3H, s), 4.70 (2H, s), 7.07-7.15 (1H, m), 7.39-
7.46 (2H, m) ppm 3- (4-chloro-2-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2102, mp110-112) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.14 (2H, ABq, J =
17.8, Δν = 83.2Hz), 3.54 (2H, s), 3.88 (3H, s), 4.68 (2
H, s), 6.94-7.02 (2H, m), 7.36 (1H, d, J = 8.1Hz) ppm 3- (2-chloro-5-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2 -Isoxa
Solin (2103, mp101-103) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.12 (2H, ABq, J =
17.9, Δν = 80.8Hz), 3.56 (2H, ABq, J = 11.6, Δν = 8.8H
z), 3.82 (3H, s), 4.79 (2H, s), 6.91 (1H, dd, J = 8.9,3.0H
z), 7.10 (1H, d, J = 3.1Hz), 7.35 (1H, d, J = 8.9Hz) ppm 3- (5-chloro-2-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl- 2-isooxa
Solin (2104, mp109-111) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.14 (2H, ABq, J =
17.9, Δν = 83.4Hz), 3.55 (2H, ABq, J = 11.7, Δν = 5.7H
z), 3.87 (3H, s), 4.68 (2H, s), 6.89 (1H, d, J = 8.8Hz), 7.
34 (1H, dd, J = 8.8, 2.5Hz), 7.41 (1H, d, J = 2.5Hz) ppm 3- (4-chloro-3-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2 -Isoxa
Solin (2105, mp91-93) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.10 (2H, ABq, J =
17.7, Δν = 85.0Hz), 3.54 (2H, ABq, J = 11.7, Δν = 14.6H
z), 3.93 (3H, s), 4.58 (2H, s), 6.93-7.00 (2H, m), 7.40 (1
H, d, J = 8.0Hz) ppm 3- (3,5-dichloro-2-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-yl
Soxazoline (2106, mp85-87) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.61 (3H, s), 3.24 (2H, ABq, J =
17.9, Δν = 81.9Hz), 3.61 (2H, ABq, J = 11.6, Δν = 15.2H
z), 3.96 (3H, s), 4.68 (2H, s), 7.39 (1H, d, J = 2.6Hz), 7.
44 (1H, d, J = 2.6Hz) ppm 3- (2,6-Dimethoxy-3-chlorobenzyl) sulfonyl-5-chloromethyl-5-methyl-2-yl
Soxazoline (2107, mp85-88) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.61 (3H, s), 3.20 (2H, ABq, J =
17.6, Δν = 84.4Hz), 3.61 (2H, ABq, J = 11.4, Δν = 15.5H
z), 3.87 (3H, s), 3.96 (3H, s), 4.78 (2H, s), 6.70 (1H, d,
J = 8.9Hz), 7.37 (1H, d, J = 8.9Hz) ppm 3- (2-chloro-3,4-dimethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-yl
Soxazoline (2108, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 3.17 (2H, ABq, J =
17.8, Δν = 81.0Hz), 3.57 (2H, ABq, J = 11.6, Δν = 8.1H
z), 3.88 (3H, s), 3.90 (3H, s), 4.78 (2H, s), 6.89 (1H, d,
J = 8.9Hz), 7.29 (1H, d, J = 8.9Hz) ppm 3- (3,5-Dichloro-4-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-yl
Soxazoline (2109, mp126-127) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 3.38 (2H, ABq, J =
17.8, Δν = 77.9Hz), 3.58 (2H, ABq, J = 11.8, Δν = 11.5H
z), 3.92 (3H, s), 4.51 (2H, s), 7.83 (2H, s) ppm 3- (3-chloro-2-ethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2110, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.46 (3H, t, J = 7.0Hz), 1.59 (3
H, s), 3.15 (2H, ABq, J = 17.8, Δν = 79.8Hz), 3.58 (2H, AB
q, J = 11.6, Δν = 14.5Hz), 4.12 (2H, q, J = 7.2Hz), 4.68 (2
H, s), 7.17 (1H, t, J = 8.0Hz), 7.41 (1H, q, J = 1.6Hz), 7.45
(1H, q, J = 1.8Hz) ppm 3- (4-chloro-2-ethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2111, mp118) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.45 (3H, t, J = 6.9Hz), 1.54 (3
H, s), 3.09 (2H, ABq, J = 17.6, Δν = 84.2Hz), 3.53 (2H,
s), 4.08 (2H, q, J = 6.9Hz), 4.69 (2H, s), 6.92-7.00 (2H,
m), 7.36 (1H, d, J = 8.1Hz) ppm 3- (2-chloro-5-ethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxa
Solin (2112, mp113-114) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.42 (3H, t, J = 7.0Hz), 1.54 (3
H, s), 3.10 (2H, ABq, J = 17.8, Δν = 80.6Hz), 3.55 (2H, d,
J = 3.3Hz), 4.03 (2H, q, J = 7.0Hz), 4.77 (2H, s), 6.89 (1H,
dd, J = 8.8, 3.1Hz), 7.08 (1H, d, J = 3.1Hz), 7.34 (1H, d, J =
8.8Hz) ppm 3- (5-chloro-2-ethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2113, mp75-77) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.44 (3H, t, J = 7.0Hz), 1.55 (3
H, s), 3.09 (2H, ABq, J = 17.8, Δν = 84.2Hz), 3.55 (2H,
s), 4.07 (2H, q, J = 7.0Hz), 4.69 (2H, s), 6.86 (1H, d, J = 8.
8Hz), 7.31 (1H, dd, J = 8.8,2.6Hz), 7.40 (1H, d, J = 2.6Hz) p
pm 3- (4-chloro-3-ethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2114, mp85-88) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.48 (3H, t, J = 7.0Hz), 1.53 (3
H, s), 3.08 (2H, ABq, J = 17.8, Δν = 85.3Hz), 3.53 (2H, AB
q, J = 11.7, Δν = 8.2Hz), 4.13 (2H, q, J = 7.0Hz), 4.56 (2
H, s), 6.92 (1H, dd, J = 8.0,2.0Hz), 6.98 (1H, d, J = 2.0Hz),
7.38 (1H, d, J = 8.0Hz) ppm 3- (3,5-Dichloro-2-ethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-yl
Soxazoline (2115, mp78-80) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.45 (3H, t, J = 6.8Hz), 1.61 (3
H, s), 3.21 (2H, ABq, J = 17.8, Δν = 80.5Hz), 3.60 (2H, AB
q, J = 11.4, Δν = 15.2Hz), 4.15 (2H, q, J = 6.8Hz), 4.66 (2
H, s), 7.40 (1H, d, J = 2.4Hz), 7.44 (1H, d, J = 2.6Hz) ppm 3- (4-chloro-2-isopropyloxyoxybenzyl) sulfonyl-5-chloromethyl-5 -Methyl-
2-isoxazoline (2116, mp92-95) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.38 (6H, d, J = 6.0Hz), 1.54 (3
H, s), 3.09 (2H, ABq, J = 17.7, Δν = 82.3Hz), 3.53 (2H, d,
J = 1.4Hz), 4.58 (1H, m), 4.68 (2H, s), 6.92 (1H, m), 6.97
(1H, d, J = 1.9Hz), 7.35 (1H, d, J = 7.9Hz) ppm 3- (2-chloro-5-isopropyloxybenzyl) sulfonyl-5-chloromethyl-5-methyl-
2-isoxazoline (2117, mp53-57) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.33 (6H, d, J = 6.0Hz), 1.56 (3
H, s), 3.10 (2H, ABq, J = 17.8, Δν = 80.5Hz), 3.55 (2H, AB
q, J = 11.6, Δν = 7.9Hz), 4.53 (1H, quintet, J = 6.1Hz),
4.77 (2H, s), 6.87 (1H, dd, J = 8.9,3.0Hz), 7.07 (1H, d, J =
3.0Hz), 7.33 (1H, d, J = 8.9Hz) ppm 3- (5-Chloro-2-isopropyloxybenzyl) sulfonyl-5-chloromethyl-5-methyl-
2-isoxazoline (2118, mp64-66) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.36 (6H, d, J = 6.1Hz), 1.55 (3
H, s), 3.10 (2H, ABq, J = 17.8, Δν = 82.4Hz), 3.54 (2H, AB
q, J = 11.6, Δν = 7.0Hz), 4.57 (1H, quintet, J = 6.0Hz),
4.68 (2H, s), 6.86 (1H, d, J = 8.8Hz), 7.30 (1H, dd, J = 8.8,
2.6Hz), 7.40 (1H, d, J = 2.6Hz) ppm 3- (4-chloro-3-isopropyloxybenzyl) sulfonyl-5-chloromethyl-5-methyl-
2-isoxazoline (2119, mp94-95) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 3.09 (2H, ABq, J =
17.8, Δν = 85.8Hz), 3.54 (2H, ABq, J = 11.7, Δν = 7.5H
z), 4.56 (2H, s), 4.59 (1H, quintet, J = 6.3Hz), 6.91 (1H,
dd, J = 8.1,1.9Hz), 7.01 (1H, d, J = 1.9Hz), 7.38 (1H, d, J =
8.1Hz) ppm 3- (2-Fluoro-6-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Serolin (2120, mp105-107) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.60 (3H, s), 3.20 (2H, ABq, J =
17.8, Δν = 84.3Hz), 3.58 (2H, ABq, J = 11.5, Δν = 7.2H
z), 3.91 (3H, s), 4.76 (2H, d, J = 1.2Hz), 6.74-6.82 (2H,
m), 7.30-7.41 (1H, m) ppm 3- (2-Ethoxy-3-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Sazoline (2121, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.38 (3H, t, J = 7.0Hz), 1.56 (3
H, s), 3.07 (2H, ABq, J = 17.8, Δν = 67.1Hz), 3.55 (2H, AB
q, J = 11.4, Δν = 15.5Hz), 3.85 (2H, s), 4.15 (2H, q, J = 7.
0Hz), 4.68 (2H, d, J = 1.5Hz), 6.93-6.98 (1H, m), 7.05-7.
09 (2H, m) ppm 3- (2-ethoxy-6-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Serolin (2122, mp105-108) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.43 (3H, t, J = 7.0Hz), 1.50 (3
H, s), 3.08 (2H, ABq, J = 17.7, Δν = 88.6Hz), 3.52 (2H,
s), 3.86 (3H, s), 4.09 (2H, q, J = 7.0Hz), 4.82 (2H, s), 6.
57 (2H, d, J = 8.4Hz), 7.30 (1H, t, J = 8.4Hz) ppm 3- (3-Methoxy-2-propyloxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2123, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.02 (3H, t, J = 7.4Hz), 1.54 (3
H, s), 1.79 (2H, septet, J = 7.2Hz), 3.03 (2H, ABq, J = 17.6,
Δν = 63.6Hz), 3.54 (2H, ABq, J = 11.5, Δν = 14.6Hz), 3.
85 (3H, s), 4.02 (2H, t, J = 6.7Hz), 4.67 (2H, q, J = 13.8Hz),
6.92-6.99 (1H, m), 7.03-7.08 (2H, m) ppm 3- (2-isopropyloxy-3-methoxybenzyl) sulfonyl-5-chloromethyl-5-methyl
-2-isoxazoline (2124, mp95-98) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.27 (6H, dd, J = 6.1,2.7Hz),
1.53 (3H, s), 3.07 (2H, ABq, J = 17.7, Δν = 50.6Hz), 3.53
(2H, ABq, J = 11.3, Δν = 15.6Hz), 3.84 (3H, s), 4.64 (1H,
septet, J = 6.3Hz), 4.64 (2H, ABq, J = 13.8, Δν = 16.4Hz),
6.92-6.97 (1H, m), 7.07-7.10 (2H, m) ppm 3- (2,3-Methylenedioxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Serolin (2125, mp121-122) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56
(3H, s), 3.13 (2H, ABq, J = 17.8, Δν = 85.2Hz), 3.54 (2H,
ABq, J = 11.7, Δν = 6.2Hz), 4.60 (2H, s), 6.02 (2H, s),
6.85-6.95 (3H, m) ppm 3- (3,4-Methylenedioxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Serolin (2126, mp81-83) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.07 (2H, ABq, J =
17.4, Δν = 76.7Hz), 3.52 (2H, s), 4.51 (2H, s), 6.00 (2
H, s), 6.80-6.90 (3H, m) ppm 3- (2,3-ethylenedioxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Sarrine (2127, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.08 (2H, ABq, J =
17.8, Δν = 88.8Hz), 3.52 (2H, s), 4.25-4.34 (4H, m),
4.67 (2H, s), 6.82-7.01 (3H, m) ppm 3- (3,4-Ethylenedioxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxy
Serolin (2128, mp74-76) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.52 (3H, s), 2.99 (2H, ABq, J =
18.0, Δν = 71.3Hz), 3.50 (2H, s), 4.25 (4H, s), 4.46 (2
H, s), 6.88 (2H, s), 6.91 (1H, s) ppm 3- (2-Methyl-3,4-ethylenedioxybenzyl) sulfonyl-5-chloromethyl-5-methyl-
2-isoxazoline (2131, mp110-112) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.26 (3H, s), 3.
03 (2H, ABq, J = 18.0, Δν = 75.9Hz), 3.52 (2H, s), 4.24-
4.28 (4H, m), 4.61 (2H, s), 6.76 (1H, d, J = 8.4Hz), 6.87 (1
H, d, J = 8.5Hz) ppm 3- (4-trifluoromethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isooxa
Solin (2142, mp106-107) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 3.12 (2H, ABq, J =
17.6, Δν = 85.0Hz), 3.54 (2H, ABq, J = 11.8, Δν = 8.8H
z), 4.62 (2H, s), 7.27 (2H, d, J = 8.4Hz), 7.49 (2H, d, J = 8.
4Hz) ppm 3- (2-Difluoromethoxy-3-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2143, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 2.35 (3H, s), 3.
20 (2H, ABq, J = 17.7, Δν = 77.8Hz), 3.58 (2H, ABq, J = 11.
7, Δν = 8.9Hz), 4.73 (1H, s), 6.47 (1H, t, J = 73.3Hz), 7.
26-7.34 (2H, m), 7.43 (1H, dd, J = 7.0,1.8Hz) ppm 3- (2-Difluoromethoxy-4-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2144, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 2.39 (3H, s), 3.
19 (2H, ABq, J = 17.8, Δν = 77.3Hz), 3.57 (2H, ABq, J = 11.
6, Δν = 9.0Hz), 4.70 (2H, s), 6.52 (1H, t, J = 73.7Hz),
7.04-7.11 (2H, m), 7.40 (1H, d, J = 7.7Hz) ppm 3- (2-Difluoromethoxy-5-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2145, mp64) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.58 (3H, s), 2.36 (3H, s), 3.
20 (2H, ABq, J = 17.8, Δν = 80.0Hz), 3.57 (2H, ABq, J = 11.
7, Δν = 9.8Hz), 4.68 (2H, s), 6.51 (1H, t, J = 73.8Hz),
7.18 (2H, dd, J = 1.8,8.3Hz), 7.26 (1H, d, J = 1.8Hz) ppm 3- (3-Difluoromethoxy-4-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl- 2
-Isoxazoline (2146, mp63-65) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 2.31 (3H, s), 3.
10 (2H, ABq, J = 17.8, Δν = 78.8Hz), 3.53 (2H, d, J = 1.4H
z), 4.58 (2H, s), 6.54 (1H, t, J = 73.6Hz), 7.16-7.21 (3H,
m) ppm 3- (3-chloro-2-difluoromethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2147, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.60 (3H, s), 3.24 (2H, ABq, J =
17.8, Δν = 78.7Hz), 3.58 (2H, ABq, J = 11.7, Δν = 11.2H
z), 4.76 (2H, s), 6.60 (1H, t, J = 73.6Hz), 7.30-7.34 (1H,
m), 7.52-7.56 (2H, m) ppm 3- (2-chloro-5-difluoromethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2148, mp85-86) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.60 (3H, s), 3.21 (2H, ABq, J =
17.8, Δν = 80.6Hz), 3.58 (2H, ABq, J = 11.7, Δν = 10.7H
z), 4.83 (2H, s), 6.53 (1H, t, J = 72.8Hz), 7.16 (1H, dd, J =
8.8,2.8Hz), 7.36 (1H, d, J = 2.8Hz), 7.47 (1H, d, J = 8.8Hz)
ppm 3- (5-chloro-2-difluoromethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2149, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.60 (3H, s), 3.24 (2H, ABq, J =
17.8, Δν = 80.6Hz), 3.59 (2H, ABq, J = 11.7, Δν = 12.4H
z), 4.71 (2H, s), 6.52 (1H, t, J = 73.2Hz), 7.20 (1H, d, J =
8.8Hz), 7.41 (1H, dd, J = 8.8,2.6Hz), 7.52 (1H, d, J = 2.6H
z) ppm 3- (4-chloro-3-difluoromethoxybenzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2150, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.18 (2H, ABq, J =
17.8, Δν = 80.8Hz), 3.56 (2H, ABq, J = 11.9, Δν = 10.3H
z), 4.59 (2H, s), 6.57 (1H, t, J = 72.9Hz), 7.26 (1H, dd, J =
8.2,2.0Hz), 7.34 (1H, br), 7.50 (1H, d, J = 8.2Hz) ppm 3- (2-methoxymethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2151, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.54 (3H, s), 3.04 (2H, ABq, J =
18.0, Δν = 81.8Hz), 3.41 (3H, s), 3.54 (2H, ABq, J = 12.
7, Δν = 5.7Hz), 4.61 (2H, s), 4.83 (2H, s), 7.36-7.49
(4H, m) ppm 3- (2-Ethoxymethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazolyl
(2152, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.25 (3H, t, J = 7.0Hz), 1.54 (3
H, s), 3.04 (2H, ABq, J = 17.8, Δν = 81.3Hz), 3.47-4.14
(4H, m), 4.66 (2H, s), 4.86 (2H, s), 7.33-7.48 (4H, m) ppm 3- (2- (2,2,2-trifluoroethoxymethyl) benzyl) sulfonyl- 5-chloromethyl-5-
Methyl-2-isoxazoline (2153, mp <40) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.56 (3H, s), 3.13 (2H, ABq, J =
17.8, Δν = 83.7Hz), 3.56 (2H, d, J = 3.2Hz), 3.86 (2H, q,
J = 8.8Hz), 4.83 (2H, s), 4.87 (2H, s), 7.4-7.5 (4H, m) ppm 3- (3- (2,2,2-trifluoroethoxymethyl) benzyl) sulfonyl- 5-chloromethyl-5-
Methyl-2-isoxazoline (2154, mp <40) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.53 (3H, s), 3.07 (2H, ABq, J =
17.6, Δν = 80.5Hz), 3.51 (2H, d, J = 1.6Hz) 3.86 (2H, q, J
= 8.8Hz), 4.62 (2H, s), 4.70 (2H, s), 7.41-7.43 (4H, m) pp
m 3- (2- (2-methoxyethoxy) benzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoo
Kisazoline (2155, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H, s), 3.03 (2H, ABq, J =
17.8, Δν = 78.1Hz), 3.45 (3H, s), 3.50 (2H, d, J = 1.5H
z), 3.77 (2H, t, J = 4.8Hz), 4.17 (2H, t, J = 4.8Hz), 4.73 (2
H, s), 6.94-7.05 (2H, m), 7.32-7.46 (2H, m) ppm 3- (3- (2-methoxyethoxy) benzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoo
Kisazoline (2156, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.50 (3H, s), 2.96 (2H, ABq, J
= 17.7, Δν = 82.3Hz), 3.46 (3H, s), 3.49 (2H, s), 3.76 (2
H, t, J = 4.6Hz), 4.13 (2H, t, J = 4.6Hz), 4.56 (2H, s), 6.99
(3H, d, J = 3.5Hz), 7.27-7.36 (1H, m) ppm 3- (2- (2,2-dimethoxyethoxy) benzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2157, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.52 (3H, s), 3.03 (2H, ABq, J =
17.8, Δν = 80.2Hz), 3.48 (6H, s), 3.51 (2H, d, J = 1.5H
z), 4.04 (2H, d, J = 5.3Hz), 4.74 (3H, t), 6.93-7.06 (2H,
m), 7.33-7.46 (2H, m) ppm 3- (3- (2,2-dimethoxyethoxy) benzyl) sulfonyl-5-chloromethyl-5-methyl-2
-Isoxazoline (2158, mp55-58) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H, s), 2.98 (2H, ABq, J =
17.9, Δν = 81.4Hz), 3.47 (6H, s), 3.50 (2H, s), 4.02 (2
H, d, J = 5.2Hz), 4.56 (2H, s), 4.72 (1H, t, J = 5.2Hz), 6.96
-7.03 (3H, m), 7.26-7.34 (1H, m) ppm 3- (2- (2,2-Ethylenedioxyethoxy) benzyl) sulfonyl-5-chloromethyl-5-methyl
Le-2-isoxazoline (2159, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.51 (3H, s), 3.04 (2H, ABq, J =
17.7, Δν = 76.1Hz), 3.50 (2H, ABq, J = 11.6, Δν = 5.7H
z), 3.92-4.07 (4H, m), 4.09 (2H, d, J = 3.8Hz), 4.73 (2H,
s), 5.30 (1H, t, J = 3.7Hz), 6.94-7.07 (2H, m), 7.33-7.48
(2H, m) ppm 3- (3- (2,2-ethylenedioxye
Toxyl) benzyl) sulfonyl-5-chloromethyl
-5-methyl-2-isoxazoline (2160, m
p74-76) ¹ H-NMR (200 MHz, CDCl _Three ) Δ: 1.50 (3
H, s), 2.97 (2H, ABq, J = 17.9, Δν = 81.6Hz), 3.49 (2H,
s), 3.96-4.11 (6H, m), 4.55 (2H, s), 5.29 (1H, t, J = 3.8H
z), 6.97-7.03 (3H, m), 7.26-7.32 (1H, m) ppm 3- (α-methylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2
161, mp62-64) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.36 (s) +1.47 (s) (3H), 1.88
(3H, d, J = 7.2Hz), 2.69 (ABq, J = 17.9, Δν = 179.4Hz) +2.7
0 (s) (2H), 3.31 (ABq, J = 11.5, Δν = 17.7Hz) +3.45 (s) (2
H), 4.58 (q, J = 7.2Hz) +4.59 (q, J = 7.2Hz) (1H), 7.39-7.45
(5H, m) ppm 3- (α, α-Dimethylbenzylsulfonyl) -5-chloromethyl-5-methyl-2-isoxa
Solin (2162, mp102-105) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.32 (3H, s), 1.95 (6H, s), 2.
26 (2H, ABq, J = 18.0, Δν = 88.6Hz), 3.31 (2H, ABq, J = 11.
5, Δν = 10.0Hz), 7.41-7.47 (3H, m), 7.60-7.65 (2H, m) p
pm 3- (α-isopropylbenzene) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2165, mp75-80) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 0.92 (3H, d, J = 6.7Hz), 1.31
(d, J = 6.6Hz) +1.33 (d, J = 6.6Hz) (3H), 1.19 (s) +1.40 (s) (3
H), 1.82-3.38 (5H, m), 4.18 (d, J = 8.7Hz) +4.20 (d, J = 8.2H
z) (1H), 7.42 (5H, s) ppm 3- (α, 2-Dimethylbenzyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazo
Grin (2166, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.31 (s) +1.55 (s) (3H), 1.83
(3H, d, J = 7.0Hz), 2.41 (3H, d, J = 1.9Hz), 2.71 (ABq, J = 18.
0, Δν = 202.4Hz) +2.73 (ABq, J = 16.9, Δν = 25.8Hz) (2H),
3.25 (ABq, J = 11.5, Δν = 29.5Hz) +3.48 (d, J = 2.1Hz) (2H),
7.21-7.34 (3H, m), 7.56-7.61 (1H, m) ppm 3- (4-chromanyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2167, o
il) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.55 (3H, s), 2.39-2.47 (1H,
m), 2.72-2.96 (1H, m), 2.99 (d, J = 4.8Hz) +3.02 (ABq, J = 1
7.9, Δν = 143.2Hz) (2H), 3.45 (s) +3.57 (ABq, J = 11.8, Δ
ν = 15.2Hz) (2H), 4.22-4.30 (1H, m), 4.46-4.60 (1H, m),
4.66-4.72 (1H, m), 6.91-7.01 (2H, m), 7.30-7.34 (1H, m),
7.47-7.51 (1H, m) ppm 3- (1-Inenyl) sulfonyl-5-chloromethyl-5-methyl-2-isoxazoline (2168,
oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.38 (s) +1.52 (s) (3H), 2.35-
3.59 (8H, m), 4.92 (1H, dt, J = 8.9,3.3Hz), 7.28-7.37 (3H,
m), 7.64 (1H, d, J = 7.3Hz) ppm 3- (1- (1,2,3,4-terolahitoronaphthyl) sulfonyl) -5-chloromethyl-5-methyl-2-
Isoxazoline (2169, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.38 (s) +1.50 (s) (3H), 2.18
-2.29 (2H, m), 2.61-2.85 (4H, m), 2.79 (2H, ABq, J = 17.9,
Δν = 176.0Hz), 3.36 (d, J = 4.3Hz) +3.51 (d, J = 3.2Hz) (2
H), 4.67-4.72 (1H, m), 7.17-7.35 (3H, m), 7.54-7.60 (1
H, m) ppm 3-Benzylsulfonyl-5- (2-chloroethyl) -5-methyl-2-isoxazoline (2170,
(mp74-75) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.39 (3H, s), 2.13 (2H, t, J = 7.
3Hz), 2.86 (2H, ABq, J = 17.6, Δν = 32.9Hz), 3.49 (2H, t,
J = 7.3Hz), 4.61 (2H, s), 7.43 (5H, s) ppm 3-Benzylsulfonyl-5-difluoromethyl-5-methyl-2-isoxazoline (2178, m
(p78-80) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.47 (3H, s), 3.02 (2H, ABq, J =
18.1, Δν = 95.4Hz), 4.61 (2H, s), 5.65 (1H, t, J = 55.5H
z), 7.35-7.46 (5H, br) ppm 3-Benzylsulfonyl-5-trifluoromethyl-5-methyl-2-isoxazoline (2179, m
(p106-107) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 1.57 (3H, s), 3.11 (2H, ABq, J =
18.3, Δν = 79.9Hz), 4.62 (2H, s), 7.43 (5H, s) ppm 3-Benzylsulfonyl-5-chloromethyl-5-ethyl-2-isoxazoline (2181, oil) ¹ H-NMR (200MHz, CDCl ₃ ) δ: 0.92 (3H, t, J = 7.4Hz), 1.81
(2H, q, J = 7.4Hz), 3.00 (2H, ABq, J = 18.0, Δν = 51.0Hz),
3.51 (2H, ABq, J = 11.8, Δν = 7.0Hz), 4.60 (2H, s), 7.42
(5H, s) ppm

[0120]

Example 3 3-Benzylthio-5-chloromethyl-5-ethyl-2
-Isoxazoline (Compound No. 181) (Step E) 3-Benzylthio-5 produced according to the method of Example 1.
3.03 g of -hydroxymethyl-5-ethyl-2-isoxazoline and 3.38 g of triphenylphosphine were dissolved in 30 ml of carbon tetrachloride and refluxed overnight. After cooling to room temperature, the reaction solution was filtered and the solvent was distilled off, followed by silica gel column chromatography (hexane: ethyl acetate = 40:
Purified by 1), 1.13 g (28%) of oily target product
I got

¹ H-NMR (200 MHz, CDCl ₃ ) δ: 0.98 (3H, t, j = 7.
4Hz), 1.85 (2H, q, J = 7.4Hz), 2.98 (2H, ABq, J = 16.9, Δν
= 50.9Hz), 3,55 (2H, ABq, J = 11.3, Δν = 17.5Hz), 4.26 (2
H, s), 7.28-7.41 (5H, m) ppm

[0122]

Example 4 3-Benzylthio-5-difluoromethyl-5-methyl
-2-isoxazoline (Compound No. 178) (H, I
Step) (1) 3-benzylthio-5-formyl-5-methyl-
2-isoxazoline (Step H) 0.11 ml of oxalyl chloride and 3 ml of methylene chloride
After cooling to -60 ° C, a mixed solution of 0.15 ml of N, N-dimethylsulfoxide and 1.9 ml of methylene chloride was added dropwise. After stirring at -60 ° C for 20 minutes, 3-benzylthio-5-prepared according to the method of Example 1.
2 ml of a methylene chloride solution containing 244.3 mg of hydroxymethyl-5-methyl-2-isoxazoline was added dropwise,
The mixture was stirred at 60 ° C for 20 minutes. Furthermore, 0.43 ml of triethylamine was added to the reaction solution, and the mixture was stirred at −60 ° C. for 30 minutes and heated to room temperature for 1 hour and 40 minutes. Water was added to the reaction solution and the mixture was extracted with methylene chloride. The organic layer was washed with water, 1N-hydrochloric acid and saturated saline, and dried over anhydrous sodium sulfate. After filtration and evaporation of the solvent, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain 238.1 mg (98%) of the desired product as an oil.

¹ H-NMR (200 MHz, CDCl ₃ ) δ: 1.51 (3H, s), 3.
09 (2H, ABq, J = 16.5, Δν = 103.9Hz), 4.26 (2H, d, J = 1.2H
z), 7.28-7.40 (5H, m), 9.62 (1H, s) ppm (2) 3-benzylthio-5-difluoromethyl-5
Methyl-2-isoxazoline (Compound No. 178)
(Step I) 3-benzylthio-5-formyl-5-methyl-2-isoxazoline 220.8 mg produced by the method of (1)
Was dissolved in 4.4 ml of methylene chloride, and diethylaminosulfatrifluoride (DAST) 0.5 was added in an ice-water bath.
ml was added. After stirring for 2 hours, remove the ice water bath,
The temperature was raised to room temperature. After stirring for further 12 hours, ice was added to the reaction solution and the mixture was extracted with methylene chloride. The organic layer was washed with water and saturated brine in that order, and dried over anhydrous sodium sulfate.
After filtration and evaporation of the solvent, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 50: 1) to obtain 116.4 mg (48%) of the desired product as an oil.

¹ H-NMR (200 MHz, CDCl ₃ ) δ: 1.49 (3H, s), 3.
04 (2H, ABq, J = 16.9, Δν = 80.6Hz), 4.27 (2H, s), 5.68 (1
H, t, J = 56.0Hz), 7.23-7.42 (5H, m) ppm

[0125]

[Formulation example]

[0126]

[Formulation Example 1] (Wettable powder) 25% of the compound No. 2161 compound, 2.5% of dodecylbenzenesulfonic acid sodium salt, 2.5% of ligninsulfonic acid calcium salt and 70% of diatomaceous earth are well ground and mixed, and water is added. I got a Japanese medicine.

[0127]

[Formulation Example 2] (Emulsion) Compound No. 2 30%, dodecylbenzenesulfonic acid calcium salt 2.68%, polyoxyethylene alkyl ether 4.92%, polyoxyethylene nonylphenyl ether calcium phosphate 0.4
% And xylene 62% were mixed well to obtain an emulsion.

[0128]

[Formulation Example 3] (Granule) Compound No. 2011 compound 5%, white carbon 1%, ligninsulfonic acid calcium salt 5%,
Bentonite 20% and clay 69% were well pulverized and mixed, water was added and well kneaded, and then granulated and dried to obtain granules.

[0129]

[Formulation Example 4] (Hydrated granules) Compound No. 162, compound 80%, special polycarboxylic acid polymer sodium salt 1.25%, water 3.
75%, dodecylbenzene sulfonic acid sodium salt 3
%, Dextrin 7% and titanium oxide 5% were mixed, then ground in an air mill, added to a rotary mixer or fluidized bed mixer, and sprayed with water to granulate. The granules were taken out when the majority became 1.0-0.15 mm, dried, and sieved. Grind oversized material, 1.
Granules of 0-0.15 mm were obtained.

[0130]

[Formulation Example 5] (Aqueous suspension) 25 parts of compound No. 2170,
Sodium dioctyl sulfosuccinate 0.7 parts, propylene glycol 0.15 parts, lignin sulfonic acid calcium salt 10 parts, water 44.15 parts and propylene glycol 10 parts until solid particles are reduced to a diameter of 5 microns or less, Grinded together in a ball mill, sand mill or roller mill. 90 parts of this pulverized slurry was mixed with 0.
10 parts of a 05% (W / W) xanthan gum aqueous solution was added and mixed to obtain an aqueous suspension.

[0131]

Industrial Applicability The compound (I) of the present invention has a herbicidal action and can be used as a herbicide. Its action is generally stronger on monocots than on dicots. For example, in the paddy field, by treating the submerged soil before or after the germination of the weeds, it strongly exterminates grass weeds such as Tainubie, Himetainubiae, and Keiubie, which are strong weeds in the paddy field, and conventional herbicides. It is also possible to exterminate difficult-to-control pine nuts, fireflies, crocodile, perennial weeds such as Cyperaceae and perennial weeds such as Urikawa and Omodaka,
Further, weeds such as Azena, weeds, sedgeweed, scutellaria, weeds such as hornwort, weeds,
It is also possible to effectively control broad-leaved weeds of the mallow family such as water mallow.

On the other hand, the selectivity for paddy rice is high,
Transplanted paddy rice has the advantage that it does not suffer chemical damage and has a wide range of treatment applications.

In the field, by treating the soil before the germination of the weeds or by treating the foliage after germination, the strong weeds of the field, such as red weeds such as red peach, white azalea and koa kaza, and rapeseed such as mustard mustard. It is possible to effectively exterminate weeds such as family weeds, Amaranthus communis, Amaranthus chinensis, Amberjack, etc. Weeds and Cyperaceae weeds such as yellow nutsedge can be controlled extremely strongly, while crops such as corn, beet, cotton and soybean are not affected by phytotoxicity.

Next, the effects will be concretely shown by giving examples of biological tests.

[0135]

[Test example]

[0136]

[Test Example 1] Pretreatment for germination of paddy field weeds 100 cm ² pots were filled with paddy field soil, and seeds of Tainubie and firefly, which were awakened, were mixed into the surface layer of 1 cm.
In addition, seedlings of paddy rice at the two-leaf stage were transplanted into a submerged state and grown in a greenhouse. Three days later, the wettable powder prepared according to Formulation Example 1 was used to treat the submerged soil with a predetermined dose, and 21 days later, an investigation was conducted according to the following criteria. The results are shown in Table 2. (Judgment Criteria) 0: Growth inhibition rate 0-10% 1: Growth inhibition rate 11-30% 2: Growth inhibition rate 31-50% 3: Growth inhibition rate 51-70% 4: Growth inhibition rate 71-90% 5 : Growth inhibition rate 91-100%

[0137]

[Test Example 2] 1.5 leaf stage treatment of Tainubie In the same manner as in Test Example 1, a prescribed dose was submerged in the 1.5 leaf stage of Tainubie using a wettable powder prepared according to Formulation Example 1. The soil was treated and surveyed 21 days later. The results are shown in Table 2 (determination criteria are the same as in Test Example 1).

In Table 2, Comparative 1, Comparative 2 and Comparative 3 refer to Comparative Compound 1, Comparative Compound 2 and Comparative Compound 3, respectively.

Comparative compound 1 is (5-chloromethyl-3
-Phenylsulfonyl-2-isoxazoline), and Heterocycles, Vol. 22, No. 10, 218.
It is the compound described on page 7 (1984).

Comparative compound 2 is (5-cyano-5-methyl-3-benzylthio-2-isoxazoline), which is a compound described in JP-A-5-105672.

Comparative compound 3 is (5-cyano-5-methyl-3- (3-trifluoromethylbenzyl) sulfonyl-2-isoxazoline) and is disclosed in JP-A-5-105.
It is a compound described in Japanese Patent No. 672.

The fact that these comparative compounds have herbicidal activity is not described in the above literature.

[0143]

[Table 2] ──────────────────────────────────── Compound Dosage Paddy Weed Pre-emergence Treatment Tainubier 1 .5 Leaf stage treatment number (g / a) Taine broad-leaved scallop paddy rice Taine broad-leaved scallop paddy vine Louis Vie Louis ──────────────────────────── ───────── 1 5 5 1 3 0 5 1 5 0 2 5 5 0 2 0 5 0 2 0 3 5 5 1 2 0 4 0 2 0 5 5 5 2 2 0 5 1 3 0 6 5 5 1 2 0 5 0 3 0 10 5 5 1 3 0 5 1 3 0 12 5 5 1 4 0 5 0 5 0 34 5 5 3 3 0 5 4 4 0 35 5 5 3 4 0 5 2 3 0 36 5 5 1 3 0 5 0 2 0 37 5 5 4 4 0 5 3 5 0 38 5 5 1 1 0 5 1 1 1 39 5 5 3 1 0 5 4 2 0 40 5 5 5 0 0 5 4 3 0 41 5 5 3 2 0 5 1 1 0 4 4 5 5 3 1 0 4 2 2 0 50 5 5 0 2 0 3 0 2 0 51 5 5 1 2 0 5 1 2 0 52 5 5 0 4 0 5 0 2 0 53 5 5 0 5 0 5 0 5 0 54 5 5 0 5 0 5 0 4 0 55 5 5 0 5 0 5 0 5 0 56 5 5 4 4 0 5 2 5 0 57 5 5 1 5 0 5 0 5 0 59 5 5 2 4 0 5 2 5 0 60 5 5 1 5 0 5 3 5 0 61 5 5 1 3 0 5 1 3 0 6 6 5 5 4 4 0 5 4 3 0 67 5 5 5 4 0 5 3 5 0 70 5 5 2 5 0 5 3 4 0 72 5 5 4 3 0 5 0 4 0 78 5 5 2 3 0 3 2 2 0 79 5 5 0 2 0 2 0 1 0 127 5 5 0 2 0 4 0 1 0 1001 5 5 2 5 0 5 0 5 0 2001 5 5 4 5 2 5 4 5 0 2002 5 5 4 5 0 5 4 5 0 2003 5 5 4 5 2 5 2 5 0 2004 5 5 3 5 2 5 2 4 0 2005 5 5 5 5 5 2 5 5 5 2 2006 5 5 5 5 2 5 4 5 0 2007 5 5 5 5 0 5 3 5 0 2008 5 5 5 5 0 5 5 5 0 2009 5 5 4 5 0 5 5 5 0 2010 5 5 5 5 1 5 5 5 2 2011 5 5 5 5 0 5 5 4 0 2012 5 5 5 5 0 5 5 5 0 2014 5 5 3 5 0 5 2 4 0 2015 5 5 5 5 0 5 4 4 0 2019 5 3 2 0 0 3 0 3 0 2020 5 5 4 5 0 5 4 5 0 2031 5 5 2 1 0 4 1 2 0 2033 5 5 4 4 0 5 1 4 0 2034 5 5 4 5 0 5 2 3 0 2035 5 5 4 5 0 5 4 5 0 2036 5 5 4 5 0 5 4 4 0 2037 5 5 5 3 0 5 4 3 0 2038 5 5 5 3 0 5 4 2 0 2039 5 5 5 5 0 5 4 4 0 2040 5 5 5 5 0 5 4 5 0 2041 5 5 4 4 0 5 4 4 0 2042 5 5 5 2 0 5 3 4 0 2043 5 5 5 4 0 5 4 5 0 2044 5 5 5 3 0 5 4 2 0 2045 5 5 4 5 0 5 4 4 0 2046 5 5 4 4 0 5 4 2 0 2047 5 5 4 3 0 5 3 3 0 2048 5 5 5 4 0 5 5 2 0 2049 5 5 5 4 0 5 5 4 0 2050 5 5 4 4 0 5 3 4 0 2051 5 5 4 5 0 5 2 4 0 2052 5 5 3 4 0 5 4 4 0 205 3 5 5 5 5 2 5 4 5 1 2054 5 5 5 5 2 5 4 5 0 2055 5 5 5 5 2 5 4 5 0 2056 5 5 5 5 2 5 4 5 0 2057 5 5 4 5 2 5 4 5 0 2058 5 5 4 5 2 5 4 5 2 2059 5 5 5 5 2 5 4 5 2 2060 5 5 4 5 0 5 3 5 0 20 61 5 5 3 5 0 5 4 5 0 2064 5 5 5 5 0 5 5 5 0 2065 5 5 4 5 0 5 4 5 1 2066 5 5 5 5 0 5 3 4 0 2067 5 5 5 5 0 5 5 5 0 2068 5 5 4 5 0 5 4 5 1 2070 5 5 5 5 0 5 4 5 0 2071 5 5 5 5 0 5 4 5 0 2072 5 5 4 5 0 5 2 5 0 2073 5 5 4 4 1 5 3 4 0 2074 5 5 5 3 0 4 3 2 0 2075 5 5 4 4 0 5 4 5 0 2076 5 5 4 3 0 5 3 4 2 2077 5 5 5 5 2 5 4 5 2 2078 5 5 4 5 0 5 4 5 0 2079 5 5 3 5 0 5 1 5 0 2080 5 5 4 5 2 5 4 5 0 2081 5 5 4 4 0 5 3 5 0 2082 5 5 3 5 0 5 3 5 0 2083 5 5 3 5 0 5 1 4 0 2084 5 5 3 5 0 5 3 4 0 2085 5 5 3 5 0 5 4 4 2 2087 5 5 0 2 0 5 0 4 0 2088 5 5 5 5 0 5 4 5 0 2089 5 5 4 5 0 5 4 3 0 2090 5 5 4 4 0 5 3 4 0 2091 5 5 4 4 0 5 1 4 0 2092 5 5 4 5 0 5 4 5 0 2093 5 5 4 5 0 5 3 4 0 2094 5 5 4 4 0 4 3 4 0 2095 5 5 5 5 0 5 5 5 2 2097 5 5 5 5 2 5 5 5 1 2098 5 5 5 5 0 5 5 5 2 2099 5 5 5 5 0 5 5 5 0 2100 5 5 3 4 0 5 3 5 0 210 1 5 5 4 5 0 5 3 5 0 2102 5 5 5 5 0 5 4 4 0 2103 5 5 4 4 0 5 4 3 0 2104 5 5 5 5 0 5 4 5 0 2105 5 5 4 3 0 5 4 3 0 2106 5 5 4 3 0 5 4 4 0 2107 5 5 4 5 0 5 3 3 0 2108 5 5 4 5 0 5 4 4 0 2109 5 5 4 2 0 5 3 2 0 2110 5 5 5 4 0 5 4 5 0 2111 5 5 5 5 0 5 4 4 0 21 12 5 5 4 4 0 5 3 4 0 2113 5 5 5 4 0 5 4 4 0 2114 5 5 5 4 0 5 5 4 0 2115 5 5 4 4 0 5 4 4 0 2116 5 5 4 5 0 5 4 4 0 2117 5 5 4 5 0 5 2 4 0 2118 5 5 5 4 0 5 4 4 0 2119 5 5 4 5 0 5 3 4 0 2120 5 5 5 5 1 5 5 5 0 2121 5 5 5 5 0 5 4 5 0 2122 5 5 4 5 0 5 3 5 0 2123 5 5 4 5 1 5 4 5 0 2124 5 5 4 0 1 5 3 5 0 2125 5 5 4 5 0 5 4 5 0 2126 5 5 3 5 0 5 3 5 0 2127 5 5 5 5 1 5 5 4 0 2128 5 5 3 5 0 5 1 4 0 2131 5 5 4 5 0 5 4 4 0 2142 5 5 2 3 0 5 2 4 0 2143 5 5 5 5 5 1 5 4 5 0 2144 5 5 5 4 2 5 5 4 0 2145 5 5 5 5 0 5 4 5 0 2146 5 5 5 5 0 5 4 5 0 2147 5 5 5 5 0 4 4 4 0 2148 5 5 5 5 0 5 3 5 0 2149 5 5 5 4 1 5 4 4 0 2150 5 5 5 5 0 5 4 5 0 2151 5 5 3 5 0 5 3 5 0 2152 5 5 3 5 0 5 3 5 0 2153 5 5 4 5 0 5 2 5 0 2154 5 5 3 5 0 5 3 4 0 2155 5 5 3 5 0 5 3 5 0 2156 5 5 2 5 1 5 2 4 0 21 57 5 5 3 5 0 5 1 5 0 2158 5 5 3 4 0 5 3 4 0 2159 5 5 4 5 0 5 3 5 0 2160 5 5 4 3 0 5 3 4 0 2161 5 5 3 5 1 5 3 5 0 2162 5 5 0 3 0 4 0 3 0 2165 5 5 0 5 0 5 0 5 0 2166 5 5 4 5 0 5 3 5 0 2167 5 5 1 5 0 4 1 5 0 2168 5 5 3 5 0 5 2 5 0 2169 5 5 3 5 0 5 3 5 0 2170 5 5 2 4 0 4 0 4 0 2178 5 5 4 5 2 5 2 5 1 2179 5 5 4 4 0 5 4 4 0 Comparison 1 5 2 3 0 0 0 0 0 0 Comparison 2 5 2 0 0 0 1 0 0 0 Comparison 3 5 0 0 0 0----──────────────────────────── ───────── In the above table, "-" indicates untested.

[0144]

[Test Example 3] Field weed pre-emergence treatment: A square pot having a depth of 4 cm and a height of 60 cm ³ was filled with Kureha horticultural soil, and seeds of various test weeds and crops were sowed and covered with about 1 cm of soil. Emulsions prepared according to Formulation Example 2 were used in these pots, and a predetermined amount was uniformly sprayed. After the treatment, plants were grown in these pots in a greenhouse. Twenty-one days after the treatment, the herbicidal effect on each weed and the phytotoxicity to the crops were investigated according to the following criteria. Table 3 shows the results.

In the table, BG stands for barnyard grass.
rdglass, CR is crabgrass
s), FO stands for foxtail, JO stands for johnson grass, PA
Stands for Panicum, NU stands for yellow nutsedge, LA stands for lambsquarters, and MU stands for mustard (m
custom), PI is pigeon
d) is shown respectively.

(Criteria) 0: Growth inhibition rate 0-9% 1: Growth inhibition rate 10-19% 2: Growth inhibition rate 20-29% 3: Growth inhibition rate 30-39% 4: Growth inhibition rate 40- 49% 5: Growth inhibition rate 50-59% 6: Growth inhibition rate 60-69% 7: Growth inhibition rate 70-79% 8: Growth inhibition rate 80-89% 9: Growth inhibition rate 90-99% 10: Growth Suppression rate 100%

[0147]

[Table 3] ──────────────────────────────────── Compound dose BG CR FO JO PA NU LA MU PI Tomorrow Cotton Soybean number (kg / ha) Koshi ──────────────────────────────────── 2001 2.0 10 10 10 10 10 10-4 10 2 0 1 2002 2.0 10 10 10 9 10 10 6 2 10 0 0 0 2003 2.0 10 10 10 10 10 10 10 10 10 0 0 0 2004 2.0 10 10 10 10 10 10 10 10 10 0 0 0 2034 2.0 10 10 10 10 10 10 9 10 10 0 0 0 2035 2.0 10 10 10 10 10 3 9 10 10 0 3 3 2036 2.0 10 10 10 9 10 10 3 0 9 0 0 0 2050 2.0 10 9 -10 10 0 0 5 10 0 0 0 2051 2.0 9 9 10 8 10 2 0 0 5 0 0 0 2052 2.0 9 10 10 10 10 0 5 9 9 0 0 0 ───────────── ──────────────────────── In the above table, "-" indicates untested.

[0148]

[Test Example 4] Field foliage treatment A square pot of 60 cm ³ and a depth of 4 cm was filled with Kureha horticultural cultivating soil, and seeds of various test weeds and crops were sown to cover about 1 cm of soil. Plants were grown in these pots in a greenhouse. When each plant reached the 2-3 leaf stage (about 10 days after sowing), the pots were uniformly sprayed with a predetermined dose using an emulsion prepared according to Formulation Example 2 in these pots. . On the 14th day after the treatment, the herbicidal effect on each weed and the phytotoxicity to the crops were investigated. The results are shown in Table 4 (the criteria and abbreviations are the same as in Test Example 3).

[0149]

[Table 4] ──────────────────────────────────── Compound dose BG CR FO JO PA NU PI Tomorrow Cotton Soybean number (kg / ha) Kosi ──────────────────────────────────── 2004 2.0 5 7 10 8 8 2 1 0 1 1 2039 2.0 4 5 8 6 8 0 7 0 1 0 2079 2.0 4 8 6 5 7 2 0 0 1 1 ─────────────────── ──────────────────

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Junji Kadani 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga In-house (72) Inventor Toyokuni Honma 1041 Yasu-cho Yasu-cho, Yasu-gun, Shiga (72) Inventor Amasa Tadashi 1041 Yasu, Yasu-cho, Yasu-gun, Shiga Sankyo Stock Association In-house

Claims (7)

[Claims] 1. A compound represented by the following general formula (I): [In the formula, R ¹ represents a lower alkyl group substituted by the same or different 1 to 3 halogen atoms, and R ²
Represents a lower alkyl group, R ³ and R ⁴ are the same or different and represent a hydrogen atom or a lower alkyl group, and R ⁵ represents
Halogen atom, lower alkyl group (the lower alkyl group is the same or different 1 to 3 selected from the substituent group a)
Or a lower alkoxy group (the lower alkoxy group may be substituted with the same or different 1 to 3 substituents selected from the substituent group a), , Two adjacent lower alkoxy groups may be bonded to each other to form a lower alkylenedioxy group, and the lower alkylenedioxy group may be substituted with the same or different 1 to 4 halogen atoms. Or R ⁴ and R ⁵ may combine to form a lower alkylene group or a lower alkyleneoxy group (when m is 2 or more, R ⁵ may be the same or different). , M represents 0, 1, 2, 3, 4 or 5, and n represents 0, 1 or 2. (Substituent group a) halogen atom, lower alkoxy group (the lower alkoxy group may be substituted with 1 to 3 halogen atoms which are the same or different, and two lower alkoxy groups adjacent to each other may be bonded to each other. May form a lower alkylenedioxy group)]. 2. The following general formula (I): [In the formula, R ¹ represents an alkyl group having 1 or 2 carbon atoms substituted by the same or different 1 to 3 halogen atoms, and R ² represents an alkyl group having 1 or 2 carbon atoms. R ³ and R ⁴ are the same or different and each represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R ⁵ is a halogen atom, an alkyl group having 1 to 3 carbon atoms or a carbon number. 1 to 3 alkoxy groups (two adjacent alkoxy groups may be bonded to each other to form an alkylenedioxy group having 1 or 2 carbon atoms) (when m is 2, R ⁵ are the same. Or may be different), m represents 0, 1 or 2, and n represents 0 or 2. ] The compound represented by these. 3. The following general formula (I): [Wherein R ¹ represents an alkyl group having 1 or 2 carbon atoms substituted by 1 to 3 chlorine atoms, and R ² is
A methyl group, R ³ and R ⁴ are the same or different and represent a hydrogen atom or a methyl group, and R ⁵ represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, an isopropyl group,
Methoxy group, ethoxy group, isopropyloxy group (two adjacent methoxy groups and ethoxy groups may be bonded to form a methylenedioxy group, an ethylenedioxy group)
(When m is 2, R ⁵ may be the same or different), m is 0, 1 or 2, and n is 0 or 2. ] The compound represented by these. 4. The following general formula (I): [In the formula, R ¹ represents a chloromethyl group, R ² represents a methyl group, R ³ and R ⁴ represent a hydrogen atom, and R ⁵
Is a fluorine atom, a chlorine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group (two adjacent methoxy groups or ethoxy groups may be bonded to form a methylenedioxy group or an ethylenedioxy group). (When m is 2, R ⁵ may be the same or different), m is 1 or 2,
n is 2. ] The compound represented by these. 5. The following general formula (I): [In the formula, R ¹ represents a chloromethyl group, R ² represents a methyl group, R ³ and R ⁴ represent a hydrogen atom, and R ⁵
Represents a chlorine atom, an ethyl group, or a methoxy group (two adjacent methoxy groups may combine to form a methylenedioxy group) (when m is 2, R ⁵ is the same or different) , M is 1 or 2, and n is 2. ] The compound represented by these. 6. A pesticide containing the compound according to claim 1 as an active ingredient. 7. A herbicide containing the compound according to claim 1 as an active ingredient.