CN102076218A - Plant growth accelerator - Google Patents

Plant growth accelerator Download PDF

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Publication number
CN102076218A
CN102076218A CN2009801246330A CN200980124633A CN102076218A CN 102076218 A CN102076218 A CN 102076218A CN 2009801246330 A CN2009801246330 A CN 2009801246330A CN 200980124633 A CN200980124633 A CN 200980124633A CN 102076218 A CN102076218 A CN 102076218A
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formula
alkyl
group
plant growth
halogen atom
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CN102076218B (en
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斎贺睦幸
藤井聪
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Nippon Soda Co Ltd
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Nippon Soda Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Disclosed is a plant growth accelerator which contains a tetrazoyloxime derivative represented by formula (1) (wherein X represents a halogen atom or the like; n represents an integer of 0-5; A represents a tetrazoyl group substituted by an alkyl group; and Het represents an optionally substituted pyridine group or an optionally substituted thiazoyl group) as an active ingredient.

Description

Plant growth promoter
Technical field
The present invention relates to plant growth promoter.Specifically, relate to make that seedling matter that case grows seedlings improves, contain of the strong seedling cultivation agent of tetrazolium 9 oxime derivate as the cereals gramineous of active ingredient.
The application requires based on Japanese Patent Application 2008-173222 number the priority of on July 2nd, 2008 in Japanese publication, with its content quotation in this.
Background technology
In the past, be purpose with the output that improves plant, used have promote the taking root of plant corpus, prevent to lodge, improve output, improve cold resistance, improve green, cultivate strong sprout, increase tiller number, promote the plant growth promoter of effects such as organ growth.For the paddy rice of conduct main cereal wherein, the strong seedling cultivation agent of paddy rice is used by popularizing of case seedling mode.
For the case seedling mode of paddy rice, the ultra dense sowing in order to adapt to growing seedlings of rice transplanter, in addition, also owing to the rice seedling degradation problem under depauperation, the seedling matter that becomes easily takes place conditions such as temperature humidity.And, when the seedling that this seedling matter is descended is transplanted to the rice field, easily by damage by disease and insect worm, pathogen invasion, so in addition because survive rate variance to meteorological condition change vulnerable, although pay a large amount of expenses and the labour sometimes also can the reduction of income.In view of this problem, developed the strong seedling cultivation agent of paddy rice.
Put down in writing in the patent documentation 1 and contained choline and hydroxyl is different
Figure BPA00001280631300011
Taking root and the strong seedling cultivation composition of the paddy rice of azoles.In addition, proposed to contain of the strong seedling cultivation agent of 3-hydroxyl pyrazine or derivatives thereof in the patent documentation 2 as the paddy rice of active ingredient.
But the material of these patent documentations is and the diverse compound of tetrazolium 9 oxime derivate structure of the present invention.
On the other hand, put down in writing in the patent documentation 3, tetrazolium 9 oxime derivate and its agricultural chemicals as active ingredient had powerful activity to various phytopathogens is to having brought into play potent preventive effect by the prevention and the treatment of the microbial plant disease of pathogenic.
But the tetrazolium 9 oxime derivate of not putting down in writing the document has the strong seedling cultivation effect of paddy rice, as the effective content of strong seedling cultivation agent of paddy rice.
The prior art document
Patent documentation
Patent documentation 1: Japanese kokai publication sho 61-212504 number
Patent documentation 2: Japanese kokai publication sho 62-167710 number
Patent documentation 3:WO03/016303
Summary of the invention
The invention reside in provides plant growth promoter.Especially, will provide strong seedling cultivation agent as problem with excellent effect.
The present invention relates to following content.
(I), a kind of plant growth promoter, it contains the tetrazolium 9 oxime derivate shown in the formula (1) as active ingredient,
Formula (1):
[in the formula (1), aryl or unsubstituted aryl that X represents halogen atom, alkyl, alkoxyl, cyano group, mesyl, nitro, trifluoromethyl, replaced by alkyl or halogen atom.N represents the arbitrary integer in 0～5, and is when n is 2 when above, identical or different between the X.
Wherein, the tetrazole radical shown in tetrazole radical shown in the A expression (2) or the formula (3).
Formula (2):
Figure BPA00001280631300022
(in the formula (2), Y represents alkyl.)
Formula (3):
Figure BPA00001280631300031
(in the formula (3), Y represents alkyl.)
Thiazolyl shown in pyridine radicals shown in the Het expression (4) or the formula (6).
Formula (4):
{ in the formula (4), R represents halogen atom.M represents integer arbitrary in 0～3, and when m represents 2 when above, identical or different between the R, Z represents the group shown in hydrogen atom, amino or the formula (5).
Formula (5): Q-C (=O)-NH-(5)
(in the formula (5), Q represents hydrogen atom, C1-8 alkyl, C1-8 haloalkyl, C3-6 cycloalkyl, C1-8 alkoxyl, C3-6 cycloalkyloxy, benzyloxy, 2-phenyl ethoxy, C1-4 alkylthio group, C1-4 alkylthio group C1-4 alkyl, C1-4 alkoxy C 1-2 alkyl, C1-5 acyl group amido C1-6 alkyl, C1-5 acyl group amido C1-6 alkoxyl, C1-8 alkyl amino, C2-6 thiazolinyl, aralkyl or phenyl.)}
Formula (6):
(in the formula (6), R ' expression hydrogen atom or halogen atom.Z represents and the same implication of described formula (4).)]
(II), as (I) described plant growth promoter, it is characterized in that, tetrazolium 9 oxime derivate shown in the formula (1): n is 0～2, X is a halogen atom, A is the tetrazole radical shown in the formula (2), Het is that the pyridine radicals shown in the formula (4) is { in the formula (4), Z is the group shown in the formula (5) (in the formula (5), Q represents C1-8 alkyl or C1-8 alkoxyl) }.
(III), as (I) or the plant growth promoter (II), it is that the strong seedling cultivation with plant is a purpose.
(IV), as each described plant growth promoter in (I)～(III), plant is cereals gramineous.
According to the present invention, can expect the growth-promoting effect of plant.Especially, it has the effect in strong sprout, by being used to transplant preceding seedling, also can increase taking root, promoting to survive of seedling after transplant in the rice field, and tiller number also can become well, can bring into play excellent effect especially when low temperature.In addition, also can significantly increase the effect that prevents to produce the lodging seedling.
Embodiment
(the tetrazolium 9 oxime derivate shown in the formula (1))
Figure BPA00001280631300041
In the tetrazolium 9 oxime derivate shown in the formula (1); for X; its the position of substitution is not particularly limited, expression halogen atom, alkyl, alkoxyl, cyano group, mesyl, nitro, trifluoromethyl or (that replaced with alkyl or halogen atom or unsubstituted) aryl.N represents arbitrary integer in 0～5, more preferably 0～2.When n is 2 when above, can be the same or different between the X.
As the halogen atom that X represents, can enumerate chlorine atom, bromine atoms, iodine atom, fluorine atom.Wherein, preferred especially X is the compound of chlorine atom or fluorine atom.
As the alkyl that X represents, the alkyl of preferred carbon number 1～4 can be enumerated methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, the tert-butyl group particularly.In them, preferred especially X is the compound of the methyl or the tert-butyl group.
In addition, as the alkoxyl that X represents, the alkoxyl of preferred carbon number 1～3 can be enumerated methoxyl group, ethyoxyl, propoxyl group, isopropoxy particularly.In them, preferred especially X is the compound of methoxy or ethoxy.
In addition, as replaced or the unsubstituted aryl that X represents, can enumerate phenyl, 4-aminomethyl phenyl, 4-chlorphenyl etc. with alkyl or halogen atom.In them, preferred especially X is the compound of phenyl.
In above-mentioned, further preferred n is 0～2, X is a halogen atom.
In above-mentioned formula (1), the tetrazole radical shown in A expression (2) or the formula (3).
Figure BPA00001280631300051
In the above-mentioned formula, Y represents alkyl.Among alkyl, the alkyl of preferred carbon number 1～3 can be enumerated methyl, ethyl, n-pro-pyl, isopropyl etc.In them, preferred especially Y is the compound of methyl or ethyl.
In the thiazolyl shown in pyridine radicals shown in the Het expression (4) in the tetrazolium 9 oxime derivate shown in the above-mentioned formula (1) or the formula (6) any.
Figure BPA00001280631300052
Figure BPA00001280631300061
Z in above-mentioned formula (4) and (6) represents the group shown in hydrogen atom, amino or the formula (5).
Q-C(＝O)-NH-(5)
R in the pyridine radicals shown in the above-mentioned formula (4) represents halogen atoms such as chlorine atom, bromine atoms, iodine atom, fluorine atom.M represents the arbitrary integer in 0～3, when m is 2 when above, can be the same or different between the R.In them, especially preferably m is that 0 compound and R are the compounds of chlorine atom.
R ' expression hydrogen atom or halogen atom in the thiazolyl shown in the above-mentioned formula (6).As halogen atom, can enumerate the halogen atom identical with the halogen atom of above-mentioned R.
Q in the group shown in the above-mentioned formula (5) represents hydrogen atom, C1-8 alkyl, C1-8 haloalkyl, C3-6 cycloalkyl, C1-8 alkoxyl, C3-6 cycloalkyloxy, benzyloxy, 2-phenyl ethoxy, C1-4 alkylthio group, C1-4 alkylthio group C1-4 alkyl, C1-4 alkoxy C 1-2 alkyl, C1-5 acyl group amido C1-6 alkyl, C1-5 acyl group amido C1-6 alkoxyl, C1-8 alkyl amino, C2-6 thiazolinyl, aralkyl or phenyl.
" the C1-8 alkyl " represented as Q, can enumerate methyl, ethyl, n-pro-pyl, isopropyl, 1,1-dimethyl propyl, normal-butyl, isobutyl group, sec-butyl, the tert-butyl group, isopentyl, 1-methyl butyl, 2-methyl butyl, neopentyl, 1-ethyl propyl, n-pentyl, hexyl, heptyl, octyl group etc.
" C1-8 haloalkyl " that Q represents meaning is the alkyl of the carbon number 1～8 that replaced with halogen atom, can enumerate chloromethyl, difluoromethyl, trifluoromethyl, difluoro chloromethyl, pentafluoroethyl group, 3,3 particularly, 3-trifluoro n-pro-pyl, 1-chlorine hexyl etc.
" C3-6 cycloalkyl " meaning that Q represents is the C3-6 alkyl with annulus, can enumerate cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, cyclopropyl methyl, cyclopentyl-methyl etc. particularly.
" the C1-8 alkoxyl " represented as Q, can enumerate methoxyl group, ethyoxyl, propoxyl group, isopropoxy, 1,1-dimethyl propoxyl group, butoxy, isobutoxy, sec-butoxy, tert-butoxy, isoamoxy, 1-methyl butoxy, 2-methyl butoxy, neopentyl oxygen, 1-ethyl propoxyl group, n-pentyloxy, own oxygen base, heptan oxygen base, octyloxy etc.
" C3-6 cycloalkyloxy " meaning that Q represents is to have the C3-6 alkyl of annulus and the group of oxygen atom bonding, can enumerate ring propoxyl group, cyclobutoxy group, cyclopentyloxy, cyclohexyloxy, cyclo propyl methoxy etc. particularly.
As " the C14 alkylthio group " that Q represents, can enumerate methyl mercapto, ethylmercapto group, butylthio etc.
As " the C1-4 alkylthio group C1-4 alkyl " that Q represents, can enumerate methylthiomethyl, ethylmercapto group ethyl, butylthio methyl etc.
As " the C1-4 alkoxy C 1-2 alkyl " that Q represents, can enumerate methoxy, ethoxyl methyl, ethoxyethyl group, butoxymethyl.
" the C1-5 acyl group amido C1-6 alkyl " that Q represents is that the C1-5 acyl group that forms of hydrogen atom or C1-4 alkyl and carbonyl bonding and amino C1-6 are alkyl linked and the group that forms can be enumerated the formoxyl aminomethyl particularly; the acetyl amine ylmethyl; 2-(propiono amido) ethyl; 3-(acetyl group amido) propyl group; 3-(propiono amido) propyl group; 3-(different propiono amido) propyl group; 3-(bytyry amido) propyl group; 3-(isobutyryl amido) propyl group; 3-(secondary bytyry amido) propyl group; 3-(uncle's bytyry amido) propyl group; 4-(acetyl group amido) butyl; 5-(acetyl group amido) amyl group and 6-(acetyl group amido) hexyl etc.
As " the C1-5 acyl group amido C1-6 alkoxyl " that Q represents, can enumerate formoxyl amido methoxyl group particularly; the acetyl amine ylmethoxy; 2-(propiono amido) ethyoxyl; 3-(acetyl group amido) propoxyl group; 3-(propiono amido) propoxyl group; 3-(different propiono amido) propoxyl group; 3-(bytyry amido) propoxyl group; 3-(isobutyryl amido) propoxyl group; 3-(secondary bytyry amido) propoxyl group; 3-(uncle's bytyry amido) propoxyl group; 4-(acetyl group amido) butoxy; 5-(acetyl group amido) amoxy and the own oxygen base of 6-(acetyl group amido) etc.
As " the C1-8 alkyl amino " that Q represents, can enumerate methylamino, ethylamino, propyl group amino, isopropyl amino, butyl amino, isobutylamino, sec-butyl amino, tert-butyl group amino, neopentyl amino, 1-ethyl propyl amino, n-pentyl amino, hexyl amino, heptyl amino, octyl group amino etc. particularly.
As " the C2-6 thiazolinyl " that Q represents, can enumerate vinyl, pi-allyl, isopropenyl, 1-cyclobutenyl, 2-cyclobutenyl, 2-pentenyl, 5-hexenyl etc. particularly.
" aralkyl " that Q represents is the alkyl linked group that forms of the aryl of aryl, preferred C6-10 and alkyl, preferred C1-4, and can enumerate benzyl, phenethyl etc. particularly.
As Q, in them, preferred C1-8 alkyl or C1-8 alkoxyl.
Below, the concrete example of the compound that comprises among the present invention is shown in the table.
[table 1]
Figure BPA00001280631300081
Table 1
The compound sequence number Z (R)m (X)n Y
1-1 H - - CH 3
1-2 H 2N - - CH 3
1-3 HC(＝O)NH - - CH 3
1-4 CH 3C(＝O)NH - - CH 3
1-5 CH 3CH 2C(＝O)NH - - CH 3
1-6 (CH 3) 2CHC(＝O)NH - - CH 3
1-7 (CH 3) 3CC(＝O)NH - - CH 3
1-8 CH 3CH 2CH 2CH 2CH 2CH 2C(＝O)NH - - CH 3
1-9 cyclo-C 6H 0-C(＝O)NH - - CH 3
1-10 CH 3OC(＝O)NH - - CH 3
1-11 CH 3CH 2OC(＝O)NH - - CH 3
1-12 (CH 3) 2CHOC(＝O)NH - - CH 3
1-13 (CH 3) SCOC(＝O)NH - - CH 3
1-14 CH 3CH 3CH 3CH ZCH 2CH 2OC(＝O)NH - - CH 3
1-15 C 6H 5CH 2OC(＝O)NH - - CH 3
1-16 cyclo-C 0H 9-OC(＝O)NH - - CH 3
1-17 CH 3CONHCH 2CH 2CH 2OC(＝O)NH - - CH 3
1-18 CH 3OCH 2C(＝O)NH - - CH 3
1-19 CH 3SCH 2C(＝O)NH - - CH 3
1-20 CH 3CH＝CHCH 2CH 2C(＝O)NH - - CH 3
1-21 C 6H 5CH 2C(＝O)NH - - CH 3
1-22 C 6H 5C(＝O)NH - - CH 3
1-23 F 3CC(＝O)NH - - CH 3
1-24 (CH 3) 3CC(＝O)NH - 3-F CH 3
1-25 (CH 3) 3CC(＝O)NH - 4-CH 3O CH 3
1-26 (CH 3) 3CC(＝O)NH - - CH 3CH 2
1-27 (CH 3) 3COC(＝O)NH - 3-F CH 3
1-28 (CH 3) 3COC(＝O)NH - 4-F CH 3
1-29 (CH 3) 3COC(＝O)NH - 4-CH 3 CH 3
1-30 (CH 3) 3COC(＝O)NH - 3-CH 3 CH 3
1-31 CH 3CH 2CH 2CH 2OC(＝O)NH - - CH 3
[table 2]
Figure BPA00001280631300091
Table 2
The compound sequence number Z (R)m (X)n Y
2-1 H - - CH 3
2-2 H 3N - - CH 3
2-3 HC(＝O)NH - - CH 3
2-4 CH 3C(＝O)NH - - CH 3
2-5 CH 3CH 2C(＝O)NH - - CH 3
2-6 (CH 3) 2CHC(＝O)NH - - CH 3
2-7 (CH 3) 3CC(＝O)NH - - CH 3
2-8 CH 3CH 2CH 2CH 2CH 2CH 2C(＝O)NH - - CH 3
2-9 cyclo-C 5H 9-C(＝O)NH - - CH 3
2-10 CH 3OC(＝O)NH - - CH 3
2-11 CH 3CH 2OC(＝O)NH - - CH 3
2-12 (CH 2) 2CHOC(＝O)NH - - CH 3
2-13 (CH 3) 3COC(＝O)NH - - CH 3
2-14 CH 3CH 2CH 2CH 2CH 2CH 2OC(＝O)NH - - CH 3
2-15 C 8H 5CH 2OC(＝O)NH - - CH 3
2-16 cyclo-C 5H 3-OC(＝O)NH - - CH 3
2-17 CH 3CONHCH 2CH 2CH 2OC(＝O)NH - - CH 3
2-18 C 6H 5CH 2C(＝O)NH - - CH 3
2-19 C 3H 5C(＝O)NH - - CH 3
2-20 F 3CC(＝O)NH - - CH 3
2-21 (CH 3) 3CC(＝O)NH - 3-F CH 3
2-22 (CH 3) 3CC(＝O)NH - 4-CH 3O CH 3
2-23 (CH 3) 2CHC(＝O)NH 3-Cl - CH 3
2-24 (CH 3) 3CHC(＝O)NH 3-Cl - CH 3CH 2
2-25 (CH 3) 3CC(＝O)NH - - CH 3CH 2
2-26 (CH 3) 3COC(＝O)NH - 3-F CH 3
2-27 (CH 3) 3COC(＝O)NH - 4-F CH 3
2-28 (CH 3) 3COC(＝O)NH - 4-CH 3 CH 3
2-29 CH 3CH 2CH 2CH 2OC(＝O)NH - 4-CN CH 3
2-30 CH 3CH 2CH 2CH 2OC(＝O)NH - 4-CH 3SO 2 CH 3
2-31 CH 3CH 2CH 2CH 2OC(＝O)NH - 4-NO 2 CH 3
2-32 CH 3CH 2CH 2CH 2OC(＝O)NH - 4-CF 3 CH 3
[table 3]
Figure BPA00001280631300101
Table 3
The compound sequence number Z R’ (X)n Y
3-1 H H - CH 3
3-2 H 2N H - CH 3
3-2 HC(＝O)NH H - CH 3
3-4 CH 3C(＝O)NH H - CH 3
3-5 CH 3CH 2C(＝O)NH H - CH 3
3-6 (CH 3) 2CHC(＝C)NH H - CH 3
3-7 (CH 3) 3CC(＝O)NH H - CH 3
3-8 CH 3CH 2CH 2CH 2CH 2CH 2C(＝O)NH H - CH 3
3-9 cyclo-C 5H 9-C(＝O)NH H - CH 3
3-10 CH 3OC(＝O)NH H - CH 3
3-11 CH 3CH 2OC(＝O)NH H - CH 3
3-12 (CH 3) 2CHOC(＝O)NH H - CH 3
3-13 (CH 3) 3COC(＝O)NH H - CH 3
3-14 CH 3CH 2CH 2CH 2CH 2CH 3OC(＝O)NH H - CH 3
3-15 C 6H 3CH 2OC(＝O)NH H - CH 3
3-16 cyclo-C 5H 9-OC(＝O)NH H - CH 3
3-17 CH 3CONHCH 2CH 2CH 2OC(＝O)NH H - CH 3
3-18 CH 3OCH 2C(＝O)NH H - CH 3
3-19 CH 3SCH 2C(＝O)NH H - CH 3
3-20 CH 3CH＝CHCH 2CH 2C(＝O)NH H - CH 3
3-21 C 6H 5CH 2C(＝O)NH H - CH 3
3-22 C 8H 5C(＝O)NH H - CH 3
3-23 F 3CC(＝O)NH H - CH 3
3-24 (CH 3) 3CC(＝O)NH H 3-F CH 3
3-25 (CH 3) 3CC(＝O)NH H 4-CH 3O CH 3
3-26 (CH 3) 3CC(＝O)NH H - CH 3CH 2
3-27 (CH 3) 3COC(＝O)NH H 3-F CH 3
3-28 (CH 3) 3COC(＝O)NH H 4-F CH 3
3-29 (CH 3) 3COC(＝O)NH H 4-CH 3 CH 3
3-30 (CH 3) 3COC(＝O)NH H 3-CH 3 CH 3
[table 4]
Figure BPA00001280631300111
Table 4
The compound sequence number Z R’ (X)n Y
4-1 H H - CH 3
4-2 H 2N H - CH 3
4-3 HC(＝O)NH H - CH 3
4-4 CH 2C(＝O)NH H - CH 3
4-5 CH 3CH 2C(＝O)NH H - CH 3
4-6 (CH 3) 2CHC(＝O)NH H - CH 3
4-7 (CH 3) 3CC(＝O)NH H - CH 3
4-8 OH 3CH 2CH 2CH 3CH 2CH 2C(＝O)NH H - CH 3
4-9 cyclo-C 5H 9-C(＝O)NH H - CH 3
4-10 CH 3OC(＝O)NH H - CH 3
4-11 CH 3CH 2OC(＝O)NH H - CH 3
4-12 (CH 3) 2CHOC(＝O)NH H - CH 3
4-13 (CH 3) SCOC(＝O)NH H - CH 3
4-14 CH 3CH 3CH 2CH 2CH 2CH 2OC(＝O)NH H - CH 3
4-15 C 6H 5CH 2OC(＝O)NH H - CH 3
4-16 eyclo-C 3H 3-OC(＝O)NH H - CH 3
4-17 CH 3CONHCH 2CH 2CH 2OC(＝O)NH H - CH 3
4-18 CH 3OCH 2C(＝O)NH H - CH 3
4-19 CH 2SCH 2C(＝O)NH H - CH 3
4-20 CH 3CH＝CHCH 2CH 2C(＝O)NH H - CH 3
4-21 C 6H 5CH 2C(＝O)NH H - CH 3
4-22 C 6H 5C(＝O)NH H - CH 3
4-23 F 3CC(＝O)NH H - CH 3
4-24 (CH 3) 2CC(＝O)NH H 3-F CH 3
4-25 (CH 3) 3CC(＝O)NH H 4-CH 3O CH 3
4-26 (CH 3) 3CC(＝O)NH H - CH 3CH 2
4-27 (CH 3) 3COC(＝C)NH H 3-F CH 3
4-28 (CH 3) 3COC(＝O)NH H 4-F CH 3
4-29 (CH 3) 3COC(＝O)NH H 4-CH 3 CH 3
4-30 (CH 3) 3COC(＝O)NH H 3-CH 3 CH 3
In the compound shown in the above-mentioned formula (1), as preferred compound, can enumerate following tetrazolium 9 oxime derivate: promptly n is 0～2, X is halogen atom, and A is the tetrazole radical shown in the above-mentioned formula (2), and Het is the pyridine radicals shown in the above-mentioned formula (4), wherein Z is the group shown in the above-mentioned formula (5) (in the formula, Q represents C1-8 alkyl or C1-8 alkoxyl).
For the oxime structure that exists in the tetrazolium oxyimino derivative of representing with the tetrazolium 9 oxime derivate shown in the above-mentioned formula (1), there are (E) configuration and (Z) stereochemical structure of configuration, these 2 kinds of stereoisomers and composition thereof all comprise in the present invention.Usually, synthetic only obtains with (Z) configuration, perhaps with (E) configuration and (Z) mixture of configuration obtain.
Can utilize separation and purification to isolate 2 isomer the mixture of configuration from (E) configuration with (Z).
For the tetrazolium 9 oxime derivate of above-mentioned formula (1), compare with (E) configuration (Z) configuration plant disease prevent and kill off superior activity.But, because (Z) configuration relies on the effect of light etc. under natural environment, some becomes (E) configuration, thereby exists as (E) configuration and (Z) mixture of configuration stable trend on a certain ratio, so two kinds of compounds and their mixture are all useful.In addition, (E) configuration is different with each compound with the stabilisation ratio of (Z) configuration, so can not determine uniformly.
(manufacture method)
Tetrazolium 9 oxime derivate shown in the above-mentioned formula (1) can be made with the described method of patent documentation 3 (WO03/016303).But the manufacture method of tetrazolium 9 oxime derivate of the present invention is not limited to this manufacture method.
(plant growth promoter)
As long as plant growth promoter of the present invention contains above-mentioned tetrazolium 9 oxime derivate as active ingredient, can suitably cooperate other composition, carrier etc.
Tetrazolium 9 oxime derivate of the present invention also can use as plant growth promoter separately, but usually, can with its with mix with assistant agents such as used habitual solid carrier, liquid-carrier, dispersant, thinner, emulsifier, solvent and tackifier in the preparation of tetrazolium 9 oxime derivate as active ingredient, preparation becomes wetting powder, liquor, finish, pulvis, granule or glue formulations such as (suspending agent (Off ロ ア Block Le drug)) to use.
As solid carrier or liquid-carrier, for example can enumerate talcum, clay, bentonite, kaolin, diatomite, montmorillonite, mica, vermiculite, gypsum, calcium carbonate, white carbon, wood chip, starch, aluminium oxide, silicate, glycopolymers, the wax class, water, alcohols (methyl alcohol, ethanol, normal propyl alcohol, isopropyl alcohol, n-butanol, ethylene glycol, benzylalcohol etc.), petroleum distillate (benzinum, kerosene, the solvent wet goods), aliphatic or ester ring type hydro carbons (n-hexane, cyclohexane etc.), aromatic hydrocarbon based (benzene, toluene, dimethylbenzene, ethylo benzene, chlorobenzene, cumene, methyl naphthalene etc.), halogenated hydrocarbons (chloroform, carrene etc.), ethers (isopropyl ether, oxirane, oxolane etc.), ketone (acetone, methyl ethyl ketone, cyclohexanone, methyl iso-butyl ketone (MIBK) etc.), ester class (ethyl acetate, butyl acetate, the ethylene glycol ethyl ethers acid esters, pentyl acetate etc.), amide-type (dimethyl formamide, dimethylated phenyl methyl ketone amine etc.), nitrile (acetonitrile, propionitrile, acrylonitrile etc.), sulfoxide class (dimethyl sulfoxide (DMSO) etc.), alcohol ethers (glycol monomethyl methyl ether, ethylene glycol monomethyl ether etc.) etc.
As assistant agent, for example can enumerate nonionic surface active agent (polyoxyethylene alkyl ether, polyxyethylated ester, polyoxyethylene alkyl phenyl ether, polyoxyethylene sorbitol acid anhydride Arrcostab, sorbitan Arrcostab etc.), anionic surfactant (alkylbenzenesulfonate, alkyl sulfo succinate, laureth sulfate, arylsulphonate etc.), cationic surface active agent (alkyl amine, the polyoxyethylene alkyl amine class, quaternary ammonium salt etc.), amphoteric surfactant (alkyl amino ethyl glycine, alkyl dimethyl betain etc.), polyvinyl alcohol, hydroxypropyl cellulose, carboxymethyl cellulose, gum Arabic, bassora gum, xanthans, polyvinyl acetate, gelatin, casein, sodium alginate etc.
Further, tetrazolium 9 oxime derivate of the present invention also can with agricultural chemicals such as various known habitual horticultural bactericides, plant growth regulator, insecticide, miticide, fertilizer etc. mix to use.The content of tetrazolium 9 oxime derivate of the present invention in plant growth promoter is with preparation form, application process, other condition and difference, but preferred 0.5～95 quality %, the scope of preferred especially 2～70 quality %.
Plant as applicable object is not particularly limited, and for example can enumerate cereals gramineous such as paddy rice, barley, wheat, barnyard grass, corn, millet; Greengroceries such as pumpkin, turnip, cabbage, radish, Chinese cabbage, spinach, green pepper, tomato; Flowers classes such as chrysanthemum, sun chrysanthemum, pansy, orchid, Chinese herbaceous peony, tulip; Beans such as red bean, French beans, soybean, peanut, broad bean, pea; Potato classes such as potato, sweet potato, fragrant taro, sweet potato, taro; Green onion classes such as green onion, onion, Hu green onion etc.
As the application process of plant growth promoter of the present invention, the using of pair plant (cauline leaf distribution) can be arranged, to the using of the soil for growth of plant (soil application), to the using of the rice field water surface (used for ponds), to the using of seed (seed treatment) etc.
Amount of application about plant growth promoter of the present invention, with suitable plant etc. and different, but situation for the cauline leaf distribution, preferably solution scope, preferred 10～1000ppm of 1～10000ppm is used by per 10 ares of 50～300L as active ingredient concentration, for the situation of soil application and used for ponds, preferably count per 10 ares of 0.1～1000g, preferred especially 10～100g and use with the active ingredient amount.In addition, for the situation of seed treatment, preferably use the active ingredient of 0.001～50g with respect to the 1Kg seed.
As long as the suitable use plant growth promoter of the present invention then healthy growth of each plant species becomes possibility.Especially, effective to the increase of the promotion of taking root of plant corpus, strong seedling cultivation, tiller number, can expect the increase of output.
Embodiment
Below, according to embodiment and test example explanation the present invention, but the present invention is not limited to these.
(embodiment 1) suspending agent
10 parts of compounds described in the table 1 (1-13)
2 parts in polyoxyethylene aryl phenyl ether ether
0.5 part of dialkyl sodium sulfosuccinate salt
5 parts of glycerine
0.3 part of xanthans
82.2 parts in water
With above mixing, carry out waterproof pulverization granularity is reached below 3 microns, obtain the suspending agent of active ingredient 10%.
(embodiment 2)
Remove replacement compound (1-13), use the compound (1-31) described in the table 1 in addition, operation obtains suspending agent similarly to Example 1.
(embodiment 3)
Remove replacement compound (1-13), use the compound (2-13) described in the table 2 in addition, operation obtains suspending agent similarly to Example 1.
The effect test in strong sprout of (test example 1) paddy rice
At first, the suspending agent that obtains in embodiment 1 or 2 is diluted with water to the concentration that active ingredient is 100ppm respectively, (pours into these soups in 15 * 10 * 4cm) equably to the small-sized seedling growing box of having filled bed soil by the about 80ml of every small-sized seedling growing box.In this seedling growing box, be treated as the rice paddy seed (kind is light (コ シ ヒ カ リ) more) of pigeon breast state through seed soaking according to the amount sowing of the dry paddy of the about 12g of every seedling growing box.It was sprouted in 30 ℃, 3 days, gave low temperature effect at 4 ℃ in 3 days afterwards.In glass greenhouse, carry out seedling management afterwards.Sow after 21 days, the longest root progress row of every case 30 seedlings of each seedling growing box is measured.
Show the result in following table.
[table 5]
Figure BPA00001280631300161
(test example 2)
" wheat effect in strong sprout "
(kind: dry seed 1kg No. 61, agricultural) packs into and mixes in the vinyl bag, smears processing at the surface of the seed with each suspending agent 10g of obtaining among the embodiment 1～3 and wheat.Smear processing through this, the active ingredient treating capacity of the every 1kg of dry seed is 1g.Above-mentioned seed after handling is sowed according to 20 in every alms bowl in No. 4 alms bowls.After planting, in glass greenhouse, carry out seedling management.Sow after 21 days the dry weight of the root of research bud ratio and seedling.Test connects system (3 Even system) according to 3 and implements.
Show the result in following table.
[table 6]
Figure BPA00001280631300162
According to above result of the test, by handling, in paddy rice, demonstrate the long remarkable increase of average the longest root with each compound, in wheat, demonstrate the raising of bud ratio and the increase of average root dry weight.
Utilizability on the industry
Utilize plant growth promoter of the present invention, can promote the growth of plant. Especially, play the effect in strong sprout, by suitably being used for transplanting front seedling, also can increase taking root, promoting to survive of seedling after transplant in the rice field, tiller number also can become well, can bring into play especially excellent growth-promoting effect when low temperature. In addition, also can significantly increase the effect that the seedling that prevents from lodging takes place.

Claims (4)

1. plant growth promoter, it contains the tetrazolium 9 oxime derivate shown in the formula (1) as active ingredient,
Formula (1):
Figure FPA00001280631200011
In the formula (1), aryl or unsubstituted aryl that X represents halogen atom, alkyl, alkoxyl, cyano group, mesyl, nitro, trifluoromethyl, replaced by alkyl or halogen atom, n represents the arbitrary integer in 0～5, and is when n is 2 when above, identical or different between the X;
Wherein, the tetrazole radical shown in tetrazole radical shown in the A expression (2) or the formula (3),
Formula (2):
Figure FPA00001280631200012
In the formula (2), Y represents alkyl,
Formula (3):
Figure FPA00001280631200013
In the formula (3), Y represents alkyl;
Thiazolyl shown in pyridine radicals shown in the Het expression (4) or the formula (6),
Formula (4):
Figure FPA00001280631200014
In the formula (4), R represents halogen atom, and m represents integer arbitrary in 0～3, and when m represents 2 when above, identical or different between the R, Z represents the group shown in hydrogen atom, amino or the formula (5),
Formula (5): Q-C (=O)-NH-(5)
In the formula (5); Q represents hydrogen atom, C1-8 alkyl, C1-8 haloalkyl, C3-6 cycloalkyl, C1-8 alkoxyl, C3-6 cycloalkyloxy, benzyloxy, 2-phenyl ethoxy, C1-4 alkylthio group, C1-4 alkylthio group C1-4 alkyl, C1-4 alkoxy C 1-2 alkyl, C1-5 acyl group amido C1-6 alkyl, C1-5 acyl group amido C1-6 alkoxyl, C1-8 alkyl amino, C2-6 thiazolinyl, aralkyl or phenyl
Formula (6):
Figure FPA00001280631200021
In the formula (6), R ' expression hydrogen atom or halogen atom, Z represents and the same implication of described formula (4).
2. plant growth promoter as claimed in claim 1 is characterized in that, the tetrazolium 9 oxime derivate shown in the formula (1) is:
N is 0～2, X is a halogen atom,
A is the tetrazole radical shown in the formula (2),
Het is the pyridine radicals shown in the formula (4), and wherein, in the formula (4), Z is the group shown in the formula (5), and in the formula (5), Q represents C1-8 alkyl or C1-8 alkoxyl.
3. the plant growth promoter described in claim 1 or 2 is characterized in that, it is that the strong seedling cultivation with plant is a purpose.
4. as each described plant growth promoter in the claim 1～3, it is characterized in that plant is cereals gramineous.
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